SherbyNet - /page/wikibook/entry.mu

Micron Document

<!DOCTYPE html>

<title>Procainamide</title>

</head>

<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Procainamide</span></span>

</h1>

</header>

</p>

/* start https://en.wikipedia.org/ */

@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}

/* end https://en.wikipedia.org/ */

</style>

/* start https://en.wikipedia.org/ */

.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}

/* end https://en.wikipedia.org/ */

</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Procainamide">Procainamide</span></caption><tbody><tr><td colspan="2" class="infobox-image"></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa">/<span style="border-bottom:1px dotted"><span title="'p' in 'pie'">p</span><span title="'r' in 'rye'">r</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'k' in 'kind'">k</span><span title="/eɪ/: 'a' in 'face'">eɪ</span><span title="'n' in 'nigh'">n</span><span title="/əm/: 'm' in 'rhythm'">əm</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="'d' in 'dye'">d</span></span>/</span></span> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Pronestyl, Procan, Procanbid, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/procainamide-hydrochloride.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Route_of_administration" title="Route of administration">Routes of<br>administration</a></th><td class="infobox-data"><a href="Intravenous_therapy" title="Intravenous therapy">IV</a>, <a href="Intramuscular_injection" title="Intramuscular injection">IM</a>, by mouth</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">

/* start https://en.wikipedia.org/ */

.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}

/* end https://en.wikipedia.org/ */

</style><div class="plainlist"><ul><li><a href="ATC_code_C01" title="ATC code C01">C01BA02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C01BA02">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><div class="plainlist">

<ul><li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li></ul></div>

</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">85% (by mouth)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">15 to 20%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="Liver" title="Liver">Liver</a> (<a href="CYP2D6" title="CYP2D6">CYP2D6</a>-mediated)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">~2.5 to 4.5 hours</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="Kidney" title="Kidney">Kidney</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;">

<div style="line-height: 1.6em; font-weight: bold;"><div><a href="IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div>

<ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">4-amino-<i>N</i>-(2-diethylaminoethyl) benzamide</div></li></ul>

</div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=51-06-9">51-06-9</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/4913">4913</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=4811">4811</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01035">DB01035</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4744.html">4744</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/L39WTC366D">L39WTC366D</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D08421">D08421</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8428">CHEBI:8428</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL640">ChEMBL640</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID7023512">DTXSID7023512</a> </span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.072">100.000.072</a> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>13</sub><span title="Hydrogen">H</span><sub>21</sub><span title="Nitrogen">N</span><sub>3</sub><span title="Oxygen">O</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap">235.331</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28c1ccc%28N%29cc1%29NCCN%28CC%29CC">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;">

<div style="line-height: 1.6em; font-weight: bold;"><div><a href="Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div>

</div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;">

<div style="line-height: 1.6em; font-weight: bold;"><div><a href="International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div>

<ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)<sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:REQCZEXYDRLIBE-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></div></li></ul>

</div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">

/* start https://en.wikipedia.org/ */

.mw-parser-output .nobold{font-weight:normal}

/* end https://en.wikipedia.org/ */

</style><span class="nobold">  <span class="reflink nourlexpansion"><a class="external text external" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477172111&page2=Procainamide">(verify)</a></span></span></td></tr></tbody></table>

<p><b>Procainamide</b> (<b>PCA</b>) is a medication of the <a href="Antiarrhythmic_agent" title="Antiarrhythmic agent">antiarrhythmic class</a> used for the treatment of <a href="Cardiac_arrhythmia" class="mw-redirect" title="Cardiac arrhythmia">cardiac arrhythmias</a>. It is a <a href="Sodium_channel_blocker" title="Sodium channel blocker">sodium channel blocker</a> of <a href="Cardiac_muscle_cell" class="mw-redirect" title="Cardiac muscle cell">cardiomyocytes</a>; thus it is classified by the <a href="Vaughan_Williams_classification" class="mw-redirect" title="Vaughan Williams classification">Vaughan Williams classification</a> system as class Ia. In addition to blocking the <i>I</i><sub>Na</sub> current, it inhibits the <i>I</i><sub>Kr</sub> rectifier K+ current.<sup id="cite_ref-Osadchii_1-0" class="reference"><a href="#cite_note-Osadchii-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Procainamide is also known to induce a voltage-dependent open channel block on the batrachotoxin (BTX)-activated sodium channels in cardiomyocytes.<sup id="cite_ref-Zamponi_2-0" class="reference"><a href="#cite_note-Zamponi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading3"><h3 id="Medical">Medical</h3></div>

<p>Procainamide is used for treating ventricular <a href="Arrhythmias" class="mw-redirect" title="Arrhythmias">arrhythmias</a>: ventricular <a href="Ectopia_(medicine)" title="Ectopia (medicine)">ectopy</a> and <a href="Tachycardia" title="Tachycardia">tachycardia</a> and supraventricular arrhythmias: <a href="Atrial_fibrillation" title="Atrial fibrillation">atrial fibrillation</a>, and re-entrant and automatic supraventricular tachycardia.<sup id="cite_ref-Gould_3-0" class="reference"><a href="#cite_note-Gould-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> For example, it can be used to convert new-onset <a href="Atrial_fibrillation" title="Atrial fibrillation">atrial fibrillation</a>, and although was initially thought to be suboptimal for this purpose, a growing body of literature is amounting in support for this exact cause.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>

</p><p>It is administered by mouth, by intramuscular injection, or intravenously.<sup id="cite_ref-ten_6-0" class="reference"><a href="#cite_note-ten-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading3"><h3 id="Others">Others</h3></div>

<p>It has also been used as a <a href="Chromatography" title="Chromatography">chromatography</a> resin because it somewhat binds protein.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2></div>

<p>There are many side effects following the induction of procainamide. These adverse effects are <a href="Ventricular_dysrhythmia" class="mw-redirect" title="Ventricular dysrhythmia">ventricular dysrhythmia</a>, <a href="Bradycardia" title="Bradycardia">bradycardia</a>, <a href="Hypotension" title="Hypotension">hypotension</a> and <a href="Shock_(circulatory)" title="Shock (circulatory)">shock</a>. The adverse effects occur even more often if the daily doses are increased. Procainamide may also lead to <a href="Drug_fever" class="mw-redirect" title="Drug fever">drug fever</a> and other <a href="Allergic_response" title="Allergic response">allergic responses</a>. There is also a chance that <a href="Drug-induced_lupus_erythematosus" title="Drug-induced lupus erythematosus">drug-induced lupus erythematosus</a> occurs, which at the same time leads to <a href="Arthralgia" title="Arthralgia">arthralgia</a>, <a href="Myalgia" title="Myalgia">myalgia</a> and <a href="Pleurisy" title="Pleurisy">pleurisy</a>. Most of these side effects may occur due to the <a href="Acetylation" title="Acetylation">acetylation</a> of procainamide.<sup id="cite_ref-adverse_12-0" class="reference"><a href="#cite_note-adverse-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading3"><h3 id="Toxicity">Toxicity</h3></div>

<p>There is a close line between the plasma concentrations of the therapeutic and toxic effect, therefore a high risk for toxicity.<sup id="cite_ref-adverse_12-1" class="reference"><a href="#cite_note-adverse-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Many symptoms resemble <a href="Systemic_lupus_erythematosus" class="mw-redirect" title="Systemic lupus erythematosus">systemic lupus erythematosus</a> because procainamide reactivates <a href="Hydroxylamine" title="Hydroxylamine">hydroxylamine</a> and <a href="Nitroso" title="Nitroso">nitroso</a> metabolites, which bind to <a href="Histone" title="Histone">histone proteins</a> and are toxic to <a href="Lymphocytes" class="mw-redirect" title="Lymphocytes">lymphocytes</a>. The hydroxylamine and nitroso metabolites are also toxic to bone marrow cells and can cause <a href="Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>. These metabolites are formed due to the activation of <a href="Polymorphonuclear_leukocytes" class="mw-redirect" title="Polymorphonuclear leukocytes">polymorphonuclear leukocytes</a>. These leukocytes release <a href="Myeloperoxidase" title="Myeloperoxidase">myeloperoxidase</a> and <a href="Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a>, which oxidize the primary aromatic amine of procainamide to form procainamide hydroxylamine. The release of hydrogen peroxide is also called a <a href="Respiratory_burst" title="Respiratory burst">respiratory burst</a>, which occurs for procainamide in <a href="Monocytes" class="mw-redirect" title="Monocytes">monocytes</a> but not in <a href="Lymphocytes" class="mw-redirect" title="Lymphocytes">lymphocytes</a>. Furthermore, the metabolites can be formed by activated <a href="Neutrophils" class="mw-redirect" title="Neutrophils">neutrophils</a>. These metabolites could then bind to their cell membranes and cause a release of <a href="Autoantibodies" class="mw-redirect" title="Autoantibodies">autoantibodies</a> which would react with the neutrophils.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Procainamide hydroxylamine has more <a href="Cytotoxicity" title="Cytotoxicity">cytotoxicity</a> by hindering the response of lymphocytes to <a href="T-cell" class="mw-redirect" title="T-cell">T-cell</a> and B-cell <a href="Mitogens" class="mw-redirect" title="Mitogens">mitogens</a>. Hydroxylamine can also generate <a href="Methemoglobin" title="Methemoglobin">methemoglobin</a>, a protein that could hinder further oxygen exchange.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup>

</p><p>It was also detected that the antiarrhythmic drug procainamide interferes with pacemakers. A toxic level of procainamide leads to decrease in ventricular conduction velocity and increase of the ventricular refractory period. This results in a disturbance in the artificial membrane potential and leads to a <a href="Supraventricular_tachycardia" title="Supraventricular tachycardia">supraventricular tachycardia</a> which induces failure of the <a href="Pacemaker" title="Pacemaker">pacemaker</a> and death.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Thus, it prolongs QT interval of action potential and increases the risk of <a href="Torsade_de_pointes" class="mw-redirect" title="Torsade de pointes">torsade de pointes</a>.<sup id="cite_ref-Osadchii_1-1" class="reference"><a href="#cite_note-Osadchii-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

</p><p>Procainamide could initiate <a href="Leukopenia" title="Leukopenia">leukopenia</a> and/or <a href="Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>, which are serious hematologic disorders, and is also known for causing gastrointestinal disturbances and aggravating pre-existing abnormalities in impulse initiation and propagation.<sup id="cite_ref-Gould_3-1" class="reference"><a href="#cite_note-Gould-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3></div>

<p>Procainamide works as an <a href="Anti-arrhythmic" class="mw-redirect" title="Anti-arrhythmic">anti-arrhythmic</a> agent and is used to treat <a href="Cardiac_arrhythmia" class="mw-redirect" title="Cardiac arrhythmia">cardiac arrhythmia</a>. It induces rapid block of the <a href="Batrachotoxin" title="Batrachotoxin">batrachotoxin (BTX)-activated</a> <a href="Sodium_channels" class="mw-redirect" title="Sodium channels">sodium channels</a> of the heart muscle and acts as antagonist to long-gating closures. The block is voltage-dependent and can occur from both sides; either from the intracellular or the extracellular side. Blocking from the extracellular side is weaker than from the intracellular side because it occurs via the hydrophobic pathway. Procainamide is present in charged form and probably requires a direct hydrophobic access to the binding site for blocking of the channel. Furthermore, blocking of the channel shows a decreased voltage sensitivity, which may result from the loss of voltage dependence of the blocking rate. Due to its charged and hydrophilic form, procainamide has its effect from the internal side, where it causes blockage of voltage-dependent, open channels. With increasing concentration of procainamide, the frequency of long blockage becomes less without the duration of blockage being affected. The rate of fast blocking is determined by the membrane depolarization. Membrane <a href="Depolarization" title="Depolarization">depolarization</a> leads to increased blocking and decreased unblocking of the channels. Procainamide slows the conduction velocity and increases the <a href="Refractory_period_(physiology)" title="Refractory period (physiology)">refractory period</a>, such that the maximal rate of depolarization is reduced.<sup id="cite_ref-Zamponi_2-1" class="reference"><a href="#cite_note-Zamponi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is also said to be a <a href="Binding_selectivity" title="Binding selectivity">selective</a> <a href="Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">muscarinic acetylcholine</a> <a href="M3_receptor" class="mw-redirect" title="M3 receptor">M<sub>3</sub> receptor</a> antagonist.<sup id="cite_ref-LavradorCabralVeríssimo2023_16-0" class="reference"><a href="#cite_note-LavradorCabralVeríssimo2023-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3></div>

<p>Procainamide is metabolized via different pathways. The most common one is the <a href="Acetylation" title="Acetylation">acetylation</a> of procainamide to the less-toxic <a href="N-acetylprocainamide" class="mw-redirect" title="N-acetylprocainamide">N-acetylprocainamide</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The rate of acetylation is genetically determined. There are two phenotypes that result from the acetylation process, namely the slow and rapid acetylator. Procainamide can also be oxidized by the <a href="Cytochrome_P-450" class="mw-redirect" title="Cytochrome P-450">cytochrome P-450</a> to a reactive oxide metabolite. But it seems that acetylation of the nitrogen group of procainamide decrease the amount of the chemical that would be available for the oxidative route.<sup id="cite_ref-Uetrecht,_J._P._1981_18-0" class="reference"><a href="#cite_note-Uetrecht,_J._P._1981-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Other metabolites of procainamide include desethyl-N-acetylprocainamide, desethylprocainamide, p-aminobenzoic acid, which are excreted via the urine. N-acetyl-4-aminobenzoic acid as well as N-acetyl-3-hydroxyprocainamide, N-acetylprocainamide-N-oxide and N-acetyl-4-aminohippuric acid are also metabolites of procainamide.<sup id="cite_ref-Uetrecht,_J._P._1981_18-1" class="reference"><a href="#cite_note-Uetrecht,_J._P._1981-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2></div>

<p>4-amino-N-2-(diethylamino)ethyl-benzamide (also known as <a href="Diethylethanolamine" title="Diethylethanolamine">para-amino-N-2-(diethylamino)ethyl-benzamide</a> because the amino substituent is attached to the para-position, <a href="Arene_substitution_patterns" class="mw-redirect" title="Arene substitution patterns">Arene substitution patterns</a> of the <a href="Benzene_ring" class="mw-redirect" title="Benzene ring">benzene ring</a>) is a synthetic <a href="Organic_compound" title="Organic compound">organic compound</a> with the chemical formula C13-H21-N3-O.<sup id="cite_ref-Drug_19-0" class="reference"><a href="#cite_note-Drug-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup>

</p><p>Procainamide is structurally similar to <a href="Procaine" title="Procaine">procaine</a>, but in place of an ester group, procainamide contains an amide group. This substitution is the reason why procainamide exhibits a longer half-life time than procaine.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup>

</p><p>Procainamide belongs to the <a href="Benzamides" class="mw-redirect" title="Benzamides">aminobenzamides</a>. These are <a href="Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> <a href="Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> derivatives consisting of an amide with a <a href="Benzamide" title="Benzamide">benzamide</a> moiety and a <a href="Triethylamine" title="Triethylamine">triethylamine</a> attached to the <a href="Amide" title="Amide">amide</a> <a href="Nitrogen" title="Nitrogen">nitrogen</a>.<sup id="cite_ref-Drug_19-1" class="reference"><a href="#cite_note-Drug-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup>

</p><p>In certain lines, the <i>para</i>-amino group might become a target site to attach further paraphernalia, e.g. <i>ref.</i> Ex18 in <span><a rel="nofollow" class="external text" href="https://patents.google.com/patent/US7115750">U.S. patent 7,115,750</a></span>.

</p>

<div class="mw-heading mw-heading2"><h2 id="History">History</h2></div>

<p>Procainamide was approved by the US FDA on June 2, 1950, under the brand name "Pronestyl".<sup id="cite_ref-dafda_24-0" class="reference"><a href="#cite_note-dafda-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> It was launched by <a href="Bristol-Myers_Squibb" class="mw-redirect" title="Bristol-Myers Squibb">Bristol-Myers Squibb</a> in 1951.<sup id="cite_ref-pmid18610401_25-0" class="reference"><a href="#cite_note-pmid18610401-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup>

Due to the <a href="Japanese_occupation_of_the_Dutch_East_Indies" title="Japanese occupation of the Dutch East Indies">loss of Indonesia</a> in <a href="World_War_II" title="World War II">World War II</a>, the source for <a href="Cinchona_alkaloids" class="mw-redirect" title="Cinchona alkaloids">cinchona alkaloids</a>, a precursor of <a href="Quinidine" title="Quinidine">quinidine</a>, was reduced. This led to research for a new <a href="Antiarrhythmic_drug" class="mw-redirect" title="Antiarrhythmic drug">antiarrhythmic drug</a>. As a result, <a href="Procaine" title="Procaine">procaine</a> was discovered, which has similar cardiac effects as quinidine.<sup id="cite_ref-one_26-0" class="reference"><a href="#cite_note-one-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> In 1936 it was found by Mautz that by applying it directly on the <a href="Myocardium" class="mw-redirect" title="Myocardium">myocardium</a>, the ventricular threshold for electrical stimulation was elevated.<sup id="cite_ref-pmid18610401_25-1" class="reference"><a href="#cite_note-pmid18610401-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> This mechanism is responsible for the antiarrhythmic effect. However, due to the short duration of action, caused by rapid enzymatic hydrolysis, its therapeutic applications were limited.<sup id="cite_ref-three_27-0" class="reference"><a href="#cite_note-three-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> In addition, procaine also caused tremors and <a href="Respiratory_depression" class="mw-redirect" title="Respiratory depression">respiratory depression</a>.<sup id="cite_ref-three_27-1" class="reference"><a href="#cite_note-three-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-two_28-0" class="reference"><a href="#cite_note-two-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> All these adverse features stimulated the search for an alternative to procaine. Studies were done on various congeners and metabolites and this ultimately led to the discovery of procainamide by Mark <i>et al</i>. It was found that procainamide was effective for treating <a href="Ventricular_arrhythmias" class="mw-redirect" title="Ventricular arrhythmias">ventricular arrhythmias</a>, but it had the same toxicity profile as quinidine, and it could cause <a href="Systemic_lupus_erythematosus" class="mw-redirect" title="Systemic lupus erythematosus">systemic lupus erythematosus</a>-like syndrome.<sup id="cite_ref-one_26-1" class="reference"><a href="#cite_note-one-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-two_28-1" class="reference"><a href="#cite_note-two-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> These negative characteristics slowed the search for new antiarrhythmics based on the chemical structure of procainamide. In 1970 only five drugs were reported. These were the <a href="Cardiac_glycosides" class="mw-redirect" title="Cardiac glycosides">cardiac glycosides</a>, <a href="Quinidine" title="Quinidine">quinidine</a>, <a href="Propranolol" title="Propranolol">propranolol</a>, <a href="Lidocaine" title="Lidocaine">lidocaine</a> and <a href="Diphenylhydantoin" class="mw-redirect" title="Diphenylhydantoin">diphenylhydantoin</a>. In January 1996, extended release procainamide hydrochloride (Procanbid extended-release tablets) was approved by the FDA.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

/* start https://en.wikipedia.org/ */

.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}

/* end https://en.wikipedia.org/ */

</style><div class="reflist">

/* start https://en.wikipedia.org/ */

.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("./mw/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("./mw/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("./mw/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("./mw/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}

/* end https://en.wikipedia.org/ */

</style><cite id="CITEREFOsadchii2014" class="citation journal cs1">Osadchii OE (August 2014). "Procainamide and lidocaine produce dissimilar changes in ventricular repolarization and arrhythmogenicity in guinea-pig". <i>Fundamental & Clinical Pharmacology</i>. <b>28</b> (4): <span class="nowrap">382–</span>393. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Ffcp.12046">10.1111/fcp.12046</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23952942">23952942</a>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:5086017">5086017</a>.</cite></span>

</li>

<li id="cite_note-Zamponi-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Zamponi_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Zamponi_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFZamponiSuiCoddingFrench1993" class="citation journal cs1">Zamponi GW, Sui X, Codding PW, French RJ (December 1993). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1225974">"Dual actions of procainamide on batrachotoxin-activated sodium channels: open channel block and prevention of inactivation"</a>. <i>Biophysical Journal</i>. <b>65</b> (6): <span class="nowrap">2324–</span>2334. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1993BpJ....65.2324Z">1993BpJ....65.2324Z</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0006-3495%2893%2981291-8">10.1016/S0006-3495(93)81291-8</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1225974">1225974</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8312472">8312472</a>.</cite></span>

</li>

<li id="cite_note-Gould-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Gould_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Gould_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFGould1983" class="citation book cs1">Gould LA, ed. (1983). <i>Drug Treatment of Cardiac Arrhythmias</i>. Mount Kisco: Futura Publishing Company. pp. <span class="nowrap">73–</span>74. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>0879931906</bdi>.</cite></span>

</li>

<li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><cite id="CITEREFStiellSivilottiTaljaardBirnie2020" class="citation journal cs1">Stiell IG, Sivilotti ML, Taljaard M, Birnie D, Vadeboncoeur A, Hohl CM, et al. (February 2020). "Electrical versus pharmacological cardioversion for emergency department patients with acute atrial fibrillation (RAFF2): a partial factorial randomised trial". <i>Lancet</i>. <b>395</b> (10221): <span class="nowrap">339–</span>349. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0140-6736%2819%2932994-0">10.1016/S0140-6736(19)32994-0</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32007169">32007169</a>. <a href="S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:210978499">210978499</a>.</cite></span>

</li>

<li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><cite id="CITEREFFensterComessMarshKatzenberg1983" class="citation journal cs1">Fenster PE, Comess KA, Marsh R, Katzenberg C, Hager WD (September 1983). "Conversion of atrial fibrillation to sinus rhythm by acute intravenous procainamide infusion". <i>American Heart Journal</i>. <b>106</b> (3): <span class="nowrap">501–</span>504. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0002-8703%2883%2990692-0">10.1016/0002-8703(83)90692-0</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6881022">6881022</a>.</cite></span>

</li>

<li id="cite_note-ten-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-ten_6-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFKoch-WeserKlein1971" class="citation journal cs1">Koch-Weser J, Klein SW (March 1971). "Procainamide dosage schedules, plasma concentrations, and clinical effects". <i>JAMA</i>. <b>215</b> (9): <span class="nowrap">1454–</span>1460. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1001%2Fjama.1971.03180220036006">10.1001/jama.1971.03180220036006</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5107621">5107621</a>.</cite></span>

</li>

<li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><cite id="CITEREFAntmanSabatine2013" class="citation book cs1">Antman EM, Sabatine MS, eds. (2013). <i>Cardiovascular Therapeutics: A companion to Braunwald's heart disease</i> (4th ed.). Philadelphia, PA: Elsevier/Saunders. p. 410. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-1-4557-0101-8</bdi>.</cite></span>

</li>

<li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20210829162220/https://www.cytivalifesciences.com/country-selection?originalItemPath=%2fshop%2fchromatography%2fresins%2faffinity-specific-groups%2fprocainamide-sepharose-4-fast-flow-p-03714">"Procainamide Sepharose 4 Fast Flow"</a>. <i>GE Healthcare Life Sciences</i>. Archived from <a rel="nofollow" class="external text" href="http://www.gelifesciences.com/webapp/wcs/stores/servlet/catalog/en/GELifeSciences-cz/products/AlternativeProductStructure_17319/28411101">the original</a> on 2021-08-29<span class="reference-accessdate">. Retrieved <span class="nowrap">2017-07-24</span></span>.</cite></span>

</li>

<li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><cite id="CITEREFDe_la_HozDoctorRalstonRush1986" class="citation journal cs1">De la Hoz D, Doctor BP, Ralston JS, Rush RS, Wolfe AD (July 1986). "A simplified procedure for the purification of large quantities of fetal bovine serum acetylcholinesterase". <i>Life Sciences</i>. <b>39</b> (3): <span class="nowrap">195–</span>199. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0024-3205%2886%2990530-8">10.1016/0024-3205(86)90530-8</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3736320">3736320</a>.</cite></span>

</li>

<li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><cite id="CITEREFRalstonMainKilpatrickChasson1983" class="citation journal cs1">Ralston JS, Main AR, Kilpatrick BF, Chasson AL (April 1983). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1154348">"Use of procainamide gels in the purification of human and horse serum cholinesterases"</a>. <i>The Biochemical Journal</i>. <b>211</b> (1): <span class="nowrap">243–</span>250. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1042%2Fbj2110243">10.1042/bj2110243</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1154348">1154348</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6870822">6870822</a>.</cite></span>

</li>

<li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><cite id="CITEREFSaxenaLuoDoctor2008" class="citation journal cs1">Saxena A, Luo C, Doctor BP (October 2008). "Developing procedures for the large-scale purification of human serum butyrylcholinesterase". <i>Protein Expression and Purification</i>. <b>61</b> (2): <span class="nowrap">191–</span>196. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.pep.2008.05.021">10.1016/j.pep.2008.05.021</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18602477">18602477</a>.</cite></span>

</li>

<li id="cite_note-adverse-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-adverse_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-adverse_12-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFLawsonJick1977" class="citation journal cs1">Lawson DH, Jick H (October 1977). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1429167">"Adverse reactions to procainamide"</a>. <i>British Journal of Clinical Pharmacology</i>. <b>4</b> (5): <span class="nowrap">507–</span>511. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1365-2125.1977.tb00777.x">10.1111/j.1365-2125.1977.tb00777.x</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1429167">1429167</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/911600">911600</a>.</cite></span>

</li>

<li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><cite id="CITEREFUetrechtZahidRubin1988" class="citation journal cs1">Uetrecht J, Zahid N, Rubin R (January 1988). "Metabolism of procainamide to a hydroxylamine by human neutrophils and mononuclear leukocytes". <i>Chemical Research in Toxicology</i>. <b>1</b> (1): <span class="nowrap">74–</span>78. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Ftx00001a013">10.1021/tx00001a013</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2979715">2979715</a>.</cite></span>

</li>

<li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><cite id="CITEREFRobertsAdamsDonovan-BrandBudinsky1989" class="citation journal cs1">Roberts SM, Adams LE, Donovan-Brand R, Budinsky R, Skoulis NP, Zimmer H, et al. (1989). "Procainamide hydroxylamine lymphocyte toxicity--I. Evidence for participation by hemoglobin". <i>International Journal of Immunopharmacology</i>. <b>11</b> (4): <span class="nowrap">419–</span>427. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0192-0561%2889%2990089-1">10.1016/0192-0561(89)90089-1</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/2476407">2476407</a>.</cite></span>

</li>

<li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><cite id="CITEREFGayBrown1974" class="citation journal cs1">Gay RJ, Brown DF (November 1974). "Pacemaker failure due to procainamide toxicity". <i>The American Journal of Cardiology</i>. <b>34</b> (6): <span class="nowrap">728–</span>732. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0002-9149%2874%2990164-7">10.1016/0002-9149(74)90164-7</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4422040">4422040</a>.</cite></span>

</li>

<li id="cite_note-LavradorCabralVeríssimo2023-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-LavradorCabralVeríssimo2023_16-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFLavradorCabralVeríssimoFernandez-Llimos2023" class="citation journal cs1">Lavrador M, Cabral AC, Veríssimo MT, Fernandez-Llimos F, Figueiredo IV, Castel-Branco MM (January 2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9863833">"A Universal Pharmacological-Based List of Drugs with Anticholinergic Activity"</a>. <i>Pharmaceutics</i>. <b>15</b> (1): 230. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fpharmaceutics15010230">10.3390/pharmaceutics15010230</a></span>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9863833">9863833</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/36678858">36678858</a>.</cite></span>

</li>

<li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><cite id="CITEREFRodenReeleHigginsWilkinson1980" class="citation journal cs1">Roden DM, Reele SB, Higgins SB, Wilkinson GR, Smith RF, Oates JA, et al. (September 1980). "Antiarrhythmic efficacy, pharmacokinetics and safety of N-acetylprocainamide in human subjects: comparison with procainamide". <i>The American Journal of Cardiology</i>. <b>46</b> (3): <span class="nowrap">463–</span>468. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0002-9149%2880%2990016-8">10.1016/0002-9149(80)90016-8</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6158263">6158263</a>.</cite></span>

</li>

<li id="cite_note-Uetrecht,_J._P._1981-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-Uetrecht,_J._P._1981_18-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Uetrecht,_J._P._1981_18-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFUetrechtFreemanWoosley1981" class="citation journal cs1">Uetrecht JP, Freeman RW, Woosley RL (August 1981). "The implications of procainamide metabolism to its induction of lupus". <i>Arthritis and Rheumatism</i>. <b>24</b> (8): <span class="nowrap">994–</span>1003. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fart.1780240803">10.1002/art.1780240803</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6169352">6169352</a>.</cite></span>

</li>

<li id="cite_note-Drug-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-Drug_19-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Drug_19-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.drugbank.ca/drugs/DB01035">"Procainamide"</a>. <i>www.drugbank.ca</i>. 27 June 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">28 June</span> 2018</span>.</cite></span>

</li>

<li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><cite id="CITEREFAdams1995" class="citation book cs1">Adams HR (1995). <i>Drugs Acting on the Cardiovascular System. Veterinary Pharmacology and Therapeutics</i> (7th ed.). pp. <span class="nowrap">451–</span>500.</cite></span>

</li>

<li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><cite id="CITEREFPlumb1999" class="citation book cs1">Plumb DC (1999). <i>Veterinary Drug Handbook</i>. White Bear Lake, USA: PharmaVet Publishing.</cite></span>

</li>

<li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><cite id="CITEREFEBI_Web_Team" class="citation web cs1">EBI Web Team. <a rel="nofollow" class="external text" href="http://www.ebi.ac.uk/chebi/searchFreeText.do?searchString=51-06-9">"CHEBI:8428 - procainamide"</a>. <i>www.ebi.ac.uk</i><span class="reference-accessdate">. Retrieved <span class="nowrap">28 June</span> 2018</span>.</cite></span>

</li>

<li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><cite id="CITEREFDeRuiter2005" class="citation book cs1">DeRuiter J (2005). "Amides and Related Functional Groups". <i>Principles of Drug Action</i>. p. 1.</cite></span>

</li>

<li id="cite_note-dafda-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-dafda_24-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFUS_Food_and_Drug_Administration" class="citation web cs1"><a href="US_Food_and_Drug_Administration" class="mw-redirect" title="US Food and Drug Administration">US Food and Drug Administration</a>. <a rel="nofollow" class="external text" href="https://www.accessdata.fda.gov/scripts/cder/daf/">"Drugs at FDA: FDA Approved Drug Products"</a>. USA: <a href="Food_and_Drug_Administration_(United_States)" class="mw-redirect" title="Food and Drug Administration (United States)">U.S. Food and Drug Administration</a> (FDA)<span class="reference-accessdate">. Retrieved <span class="nowrap">2012-08-13</span></span>.</cite></span>

</li>

<li id="cite_note-pmid18610401-25"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid18610401_25-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid18610401_25-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFHollman1992" class="citation journal cs1">Hollman A (February 1992). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1024743">"Procaine and procainamide"</a>. <i>British Heart Journal</i>. <b>67</b> (2): 143. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1136%2Fhrt.67.2.143">10.1136/hrt.67.2.143</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1024743">1024743</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/18610401">18610401</a>.</cite></span>

</li>

<li id="cite_note-one-26"><span class="mw-cite-backlink">^ <a href="#cite_ref-one_26-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-one_26-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFWalker2006" class="citation journal cs1">Walker MJ (January 2006). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1760742">"Antiarrhythmic drug research"</a>. <i>British Journal of Pharmacology</i>. <b>147</b> (Suppl 1): <span class="nowrap">S222 –</span> <span class="nowrap">S231</span>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fsj.bjp.0706500">10.1038/sj.bjp.0706500</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1760742">1760742</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16402108">16402108</a>.</cite></span>

</li>

<li id="cite_note-three-27"><span class="mw-cite-backlink">^ <a href="#cite_ref-three_27-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-three_27-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFMoeAbildskov1965" class="citation book cs1">Moe GK, Abildskov A (1965). "Antiarrhythmic drugs". In Goodman LS, Gilman A (eds.). <i>Goodman and Gilman's The Pharmacological Basis of Therapeutics</i> (3rd ed.). New York: Macmillan. pp. <span class="nowrap">699–</span>715.</cite></span>

</li>

<li id="cite_note-two-28"><span class="mw-cite-backlink">^ <a href="#cite_ref-two_28-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-two_28-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFLüderitz2002" class="citation book cs1">Lüderitz BB, ed. (2002). "Historical development of antiarrhythmic drug therapy". <i>History of Disorders of Cardiac Rhythm</i> (3rd ed.). New York: Wiley-Blackwell. pp. <span class="nowrap">87–</span>114.</cite></span>

</li>

<li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><cite id="CITEREFMishinaMarroum2002" class="citation web cs1">Mishina E, Marroum P (2002). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170218125158/http://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/20545s007_Procanbid_biopharmr.pdf">"Center for Drug Evaluation and Research Approval Package For: Application Number NDA 20-545/S007"</a> <span class="cs1-format">(PDF)</span>. <i>Clinical Pharmacology and Bioharmaceutics Review</i>. Archived from <a rel="nofollow" class="external text" href="https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/20545s007_Procanbid_biopharmr.pdf">the original</a> <span class="cs1-format">(PDF)</span> on February 18, 2017.</cite></span>

</li>

</ol></div></div>

/* start https://en.wikipedia.org/ */

.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}

/* end https://en.wikipedia.org/ */

</style><style data-mw-deduplicate="TemplateStyles:r1236075235">

/* start https://en.wikipedia.org/ */

.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}

/* end https://en.wikipedia.org/ */

</style></div><div role="navigation" class="navbox" aria-labelledby="Antiarrhythmic_agents_(C01B)186" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><style data-mw-deduplicate="TemplateStyles:r1239400231">

/* start https://en.wikipedia.org/ */

.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}

/* end https://en.wikipedia.org/ */

</style><div id="Antiarrhythmic_agents_(C01B)186" style="font-size:114%;margin:0 4em"><a href="Antiarrhythmic_agent" title="Antiarrhythmic agent">Antiarrhythmic agents</a> (<a href="ATC_code_C01#C01B" title="ATC code C01">C01B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Channel_blocker" title="Channel blocker">Channel blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="class_I(Na+_channel_blockers)442" scope="row" class="navbox-group" style="width:1%"><a href="Antiarrhythmic_agent#Class_I_agents" title="Antiarrhythmic agent">class I</a><br>(<a href="Sodium_channel_blocker" title="Sodium channel blocker">Na<sup>+</sup> channel blockers</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">class Ia (<a href="Cardiac_action_potential#Phase_0" title="Cardiac action potential">Phase 0</a>→ and <a href="Cardiac_action_potential#Phase_3" title="Cardiac action potential">Phase 3</a>→)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Ajmaline" title="Ajmaline">Ajmaline</a></li>

<li><a href="Disopyramide" title="Disopyramide">Disopyramide</a></li>

<li><a href="Dihydroquinidine" title="Dihydroquinidine">Hydroquinidine</a></li>

<li><a href="Lorajmine" title="Lorajmine">Lorajmine</a></li>

<li><a href="Prajmaline" title="Prajmaline">Prajmaline</a></li>

<li><a href="Quinidine" title="Quinidine">Quinidine</a><sup>#</sup></li>

<li><a href="Sparteine" title="Sparteine">Sparteine</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">class Ib (<a href="Cardiac_action_potential#Phase_3" title="Cardiac action potential">Phase 3</a>←)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Lidocaine" title="Lidocaine">Lidocaine</a><sup>#</sup></li></ul></li>

<li><i><a href="Enteral" class="mw-redirect" title="Enteral">enteral</a></i>

<ul><li><a href="Aprindine" title="Aprindine">Aprindine</a></li>

<li><a href="Mexiletine" title="Mexiletine">Mexiletine</a></li>

<li><a href="Tocainide" title="Tocainide">Tocainide</a></li></ul></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">class Ic (<a href="Cardiac_action_potential#Phase_0" title="Cardiac action potential">Phase 0</a>→)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Encainide" title="Encainide">Encainide</a><sup>‡</sup></li>

<li><a href="Ethacizine" title="Ethacizine">Ethacizine</a></li>

<li><a href="Flecainide" title="Flecainide">Flecainide</a></li>

<li><a href="Indecainide" title="Indecainide">Indecainide</a><sup>‡</sup></li>

<li><a href="Lorcainide" title="Lorcainide">Lorcainide</a></li>

<li><a href="Moracizine" title="Moracizine">Moracizine</a><sup>‡</sup></li>

<li><a href="Propafenone" title="Propafenone">Propafenone</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Antiarrhythmic_agent#Class_III_agents" title="Antiarrhythmic agent">class III</a><br>(<a href="Cardiac_action_potential#Phase_3" title="Cardiac action potential">Phase 3</a>→, <a href="Potassium_channel_blocker" title="Potassium channel blocker">K<sup>+</sup> channel blockers</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Amiodarone" title="Amiodarone">Amiodarone</a></li>

<li><a href="Bretylium" title="Bretylium">Bretylium</a></li>

<li><a href="Bunaftine" title="Bunaftine">Bunaftine</a></li>

<li><a href="Celivarone" title="Celivarone">Celivarone</a><sup>†</sup></li>

<li><a href="Dofetilide" title="Dofetilide">Dofetilide</a></li>

<li><a href="Dronedarone" title="Dronedarone">Dronedarone</a></li>

<li><a href="Ibutilide" title="Ibutilide">Ibutilide</a></li>

<li><a href="Nifekalant" title="Nifekalant">Nifekalant</a></li>

<li><a href="Sotalol" title="Sotalol">Sotalol</a></li>

<li><a href="Tedisamil" title="Tedisamil">Tedisamil</a></li>

<li><a href="Vernakalant" title="Vernakalant">Vernakalant</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Antiarrhythmic_agent#Class_IV_agents" title="Antiarrhythmic agent">class IV</a><br>(<a href="Cardiac_action_potential#Phase_4" title="Cardiac action potential">Phase 4</a>→, <a href="Calcium_channel_blocker" title="Calcium channel blocker">Ca<sup>2+</sup> channel blockers</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Diltiazem" title="Diltiazem">Diltiazem</a></li>

<li><a href="Verapamil" title="Verapamil">Verapamil</a><sup>#</sup></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a> <a href="Agonist" title="Agonist">agonists</a><br>and <a href="Receptor_antagonist" title="Receptor antagonist">antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Antiarrhythmic_agent#Class_II_agents" title="Antiarrhythmic agent">class II</a><br>(<a href="Cardiac_action_potential#Phase_4" title="Cardiac action potential">Phase 4</a>→, <a href="Beta_blocker" title="Beta blocker">β blockers</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Nadolol" title="Nadolol">Nadolol</a></li>

<li><a href="Pindolol" title="Pindolol">Pindolol</a></li>

<li><a href="Propranolol" title="Propranolol">Propranolol</a></li>

<li><i>cardioselective</i>

<ul><li><a href="Acebutolol" title="Acebutolol">Acebutolol</a></li>

<li><a href="Atenolol" title="Atenolol">Atenolol</a></li>

<li><a href="Esmolol" title="Esmolol">Esmolol</a></li>

<li><a href="Landiolol" title="Landiolol">Landiolol</a></li>

<li><a href="Metoprolol" title="Metoprolol">Metoprolol</a></li></ul></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Adenosine_A1_receptor" title="Adenosine A1 receptor">A<sub>1</sub> agonist</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Adenosine" title="Adenosine">Adenosine</a></li>

<li><a href="Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li>

<li><a href="Barbiturate" title="Barbiturate">Barbiturates</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Muscarinic_acetylcholine_receptor_M2" title="Muscarinic acetylcholine receptor M2">M<sub>2</sub></a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Muscarinic_antagonist" title="Muscarinic antagonist">muscarinic antagonist</a>: <a href="Atropine" title="Atropine">Atropine</a></li>

<li><a href="Disopyramide" title="Disopyramide">Disopyramide</a></li>

<li><a href="Quinidine" title="Quinidine">Quinidine</a><br><a href="Muscarinic_agonist" title="Muscarinic agonist">muscarinic agonist</a>: <a href="Digoxin" title="Digoxin">Digoxin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Adrenergic_receptor#.CE.B1_receptors" title="Adrenergic receptor">α receptors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Amiodarone" title="Amiodarone">Amiodarone</a></li>

<li><a href="Bretylium" title="Bretylium">Bretylium</a></li>

<li><a href="Quinidine" title="Quinidine">Quinidine</a></li>

<li><a href="Verapamil" title="Verapamil">Verapamil</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Ion_transporter" title="Ion transporter">Ion transporters</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Na+/_K+-ATPase54" scope="row" class="navbox-group" style="width:1%"><a href="Na%2B/K%2B-ATPase" class="mw-redirect" title="Na+/K+-ATPase">Na<sup>+</sup>/ K<sup>+</sup>-ATPase</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Digitoxin" title="Digitoxin">Digitoxin</a></li>

<li><a href="Digoxin" title="Digoxin">Digoxin</a></li>

<li><a href="Ouabain" title="Ouabain">Ouabain</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist">

<li><sup>‡</sup><a href="List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li>

<li><a href="Clinical_trial" title="Clinical trial">Clinical trials</a>:

<ul><li><sup>†</sup><a href="Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li>

<li><sup>§</sup>Never to phase III</li></ul></li></ul>

</div></div></td></tr></tbody></table></div>

<div class="navbox-styles"></div><div role="navigation" class="navbox" aria-labelledby="Muscarinic_acetylcholine_receptor_modulators859" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><div id="Muscarinic_acetylcholine_receptor_modulators859" style="font-size:114%;margin:0 4em"><a href="Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">Muscarinic acetylcholine receptor</a> <a href="Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="Muscarinic_acetylcholine_receptors" class="mw-redirect" title="Muscarinic acetylcholine receptors"><abbr title="Muscarinic acetylcholine receptors">mAChRs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Muscarinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="Muscarinic_agonist" title="Muscarinic agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<li><a href="Aceclidine" title="Aceclidine">Aceclidine</a></li>

<li><a href="Acetylcholine" title="Acetylcholine">Acetylcholine</a></li>

<li><a href="Alvameline" title="Alvameline">Alvameline</a></li>

<li><a href="Arecoline" title="Arecoline">Arecoline</a></li>

<li><a href="Bethanechol" title="Bethanechol">Bethanechol</a></li>

<li><a href="Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li>

<li><a href="Carbachol" title="Carbachol">Carbachol</a></li>

<li><a href="Cevimeline" title="Cevimeline">Cevimeline</a></li>

<li><a href="Choline" title="Choline">Choline</a></li>

<li><a href="Cis-Dioxolane" class="mw-redirect" title="Cis-Dioxolane">cis-Dioxolane</a></li>

<li><a href="Desmethylclozapine" title="Desmethylclozapine">Desmethylclozapine (norclozapine)</a></li>

<li>Ethoxysebacylcholine</li>

<li><a href="Itameline" title="Itameline">Itameline</a></li>

<li><a href="Methacholine" title="Methacholine">Methacholine</a></li>

<li><a href="Milameline" title="Milameline">Milameline</a></li>

<li><a href="Muscarine" title="Muscarine">Muscarine</a></li>

<li>Ocvimeline</li>

<li><a href="Oxotremorine" title="Oxotremorine">Oxotremorine</a></li>

<li><a href="Pilocarpine" title="Pilocarpine">Pilocarpine</a></li>

<li><a href="Sabcomeline" title="Sabcomeline">Sabcomeline</a></li>

<li>Sebacylcholine</li>

<li>Suberyldicholine</li>

<li><a href="Talsaclidine" title="Talsaclidine">Talsaclidine</a></li>

<li><a href="Tazomeline" title="Tazomeline">Tazomeline</a></li>

<li>Thiopilocarpine</li>

<li><a href="Vedaclidine" title="Vedaclidine">Vedaclidine</a></li>

<li><a href="Xanomeline" title="Xanomeline">Xanomeline</a></li>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="Muscarinic_antagonist" title="Muscarinic antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">3-Quinuclidinyl benzilate</a></li>

<li><a href="Aclidinium_bromide" title="Aclidinium bromide">Aclidinium bromide</a> (<a href="Aclidinium_bromide/formoterol" title="Aclidinium bromide/formoterol">+formoterol</a>)</li>

<li><a href="Abediterol" title="Abediterol">Abediterol</a></li>

<li><a href="Ambutonium_bromide" title="Ambutonium bromide">Ambutonium bromide</a></li>

<li><a href="Anisodamine" title="Anisodamine">Anisodamine</a></li>

<li><a href="Anisodine" title="Anisodine">Anisodine</a></li>

<li><a href="First-generation_antihistamine" class="mw-redirect" title="First-generation antihistamine">Antihistamines (first-generation)</a> (e.g., <a href="Brompheniramine" title="Brompheniramine">brompheniramine</a>, <a href="Buclizine" title="Buclizine">buclizine</a>, <a href="Captodiame" title="Captodiame">captodiame</a>, <a href="Chlorphenamine" title="Chlorphenamine">chlorphenamine (chlorpheniramine)</a>, <a href="Cinnarizine" title="Cinnarizine">cinnarizine</a>, <a href="Clemastine" title="Clemastine">clemastine</a>, <a href="Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, <a href="Dimenhydrinate" title="Dimenhydrinate">dimenhydrinate</a>, <a href="Dimetindene" title="Dimetindene">dimetindene</a>, <a href="Diphenhydramine" title="Diphenhydramine">diphenhydramine</a>, <a href="Doxylamine" title="Doxylamine">doxylamine</a>, <a href="Meclizine" title="Meclizine">meclizine</a>, <a href="Mequitazine" title="Mequitazine">mequitazine</a>, <a href="Perlapine" title="Perlapine">perlapine</a>, <a href="Phenindamine" title="Phenindamine">phenindamine</a>, <a href="Pheniramine" title="Pheniramine">pheniramine</a>, <a href="Phenyltoloxamine" title="Phenyltoloxamine">phenyltoloxamine</a>, <a href="Promethazine" title="Promethazine">promethazine</a>, <a href="Propiomazine" title="Propiomazine">propiomazine</a>, <a href="Triprolidine" title="Triprolidine">triprolidine</a>)</li>

<li><a href="Atropine" title="Atropine">Atropine</a></li>

<li><a href="Atropine_methonitrate" class="mw-redirect" title="Atropine methonitrate">Atropine methonitrate</a></li>

<li><a href="Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="Clozapine" title="Clozapine">clozapine</a>, <a href="Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="Olanzapine" title="Olanzapine">olanzapine</a> (<a href="Olanzapine/fluoxetine" title="Olanzapine/fluoxetine">+fluoxetine</a>), rilapine, <a href="Quetiapine" title="Quetiapine">quetiapine</a>, <a href="Tenilapine" title="Tenilapine">tenilapine</a>, <a href="Zotepine" title="Zotepine">zotepine</a>)</li>

<li><a href="Benactyzine" title="Benactyzine">Benactyzine</a></li>

<li><a href="Benzatropine" title="Benzatropine">Benzatropine (benztropine)</a></li>

<li><a href="Benzilone" title="Benzilone">Benzilone</a></li>

<li><a href="Benzilylcholine_mustard" title="Benzilylcholine mustard">Benzilylcholine mustard</a></li>

<li><a href="Benzydamine" title="Benzydamine">Benzydamine</a></li>

<li><a href="Bevonium" title="Bevonium">Bevonium</a></li>

<li><a href="Biperiden" title="Biperiden">Biperiden</a></li>

<li><a href="Bornaprine" title="Bornaprine">Bornaprine</a></li>

<li><a href="Camylofin" title="Camylofin">Camylofin</a></li>

<li><a href="Caramiphen" title="Caramiphen">Caramiphen</a></li>

<li><a href="Cimetropium_bromide" title="Cimetropium bromide">Cimetropium bromide</a></li>

<li><a href="Clidinium_bromide" title="Clidinium bromide">Clidinium bromide</a></li>

<li><a href="Cloperastine" title="Cloperastine">Cloperastine</a></li>

<li><a href="Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li>

<li><a href="Cyclopentolate" title="Cyclopentolate">Cyclopentolate</a></li>

<li><a href="Darifenacin" title="Darifenacin">Darifenacin</a></li>

<li><a href="Desfesoterodine" title="Desfesoterodine">Desfesoterodine</a></li>

<li><a href="Dexetimide" title="Dexetimide">Dexetimide</a></li>

<li><a href="Dicycloverine" title="Dicycloverine">Dicycloverine (dicyclomine)</a></li>

<li><a href="Dihexyverine" title="Dihexyverine">Dihexyverine</a></li>

<li><a href="Difemerine" title="Difemerine">Difemerine</a></li>

<li><a href="Diphemanil_metilsulfate" title="Diphemanil metilsulfate">Diphemanil metilsulfate</a></li>

<li><a href="Ditran" title="Ditran">Ditran</a></li>

<li><a href="Drofenine" title="Drofenine">Drofenine</a></li>

<li><a href="Emepronium_bromide" title="Emepronium bromide">Emepronium bromide</a></li>

<li><a href="Etanautine" title="Etanautine">Etanautine</a></li>

<li><a href="Etybenzatropine" title="Etybenzatropine">Etybenzatropine (ethybenztropine)</a></li>

<li><a href="Fenpiverinium" title="Fenpiverinium">Fenpiverinium</a></li>

<li><a href="Fentonium_bromide" title="Fentonium bromide">Fentonium bromide</a></li>

<li><a href="Fesoterodine" title="Fesoterodine">Fesoterodine</a></li>

<li><a href="Flavoxate" title="Flavoxate">Flavoxate</a></li>

<li><a href="Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a> (<a href="Beclometasone/formoterol/glycopyrronium_bromide" title="Beclometasone/formoterol/glycopyrronium bromide">+beclometasone/formoterol</a>, <a href="Indacaterol/glycopyrronium_bromide" title="Indacaterol/glycopyrronium bromide">+indacaterol</a>, <a href="Neostigmine/glycopyrronium_bromide" title="Neostigmine/glycopyrronium bromide">+neostigmine</a>)</li>

<li>Hexahydrodifenidol</li>

<li>Hexahydrosiladifenidol</li>

<li>Hexbutinol</li>

<li><a href="Hexocyclium" title="Hexocyclium">Hexocyclium</a></li>

<li><a href="Himbacine" title="Himbacine">Himbacine</a></li>

<li><a href="Homatropine" title="Homatropine">Homatropine</a></li>

<li><a href="Imidafenacin" title="Imidafenacin">Imidafenacin</a></li>

<li><a href="Ipratropium_bromide" title="Ipratropium bromide">Ipratropium bromide</a> (<a href="Ipratropium_bromide/salbutamol" title="Ipratropium bromide/salbutamol">+salbutamol</a>)</li>

<li><a href="Isopropamide" title="Isopropamide">Isopropamide</a></li>

<li><a href="Hyoscyamine" title="Hyoscyamine">Hyoscyamine</a></li>

<li><a href="Mamba#Mamba_toxins" title="Mamba">Mamba toxin 3</a></li>

<li><a href="Mamba#Mamba_toxins" title="Mamba">Mamba toxin 7</a></li>

<li><a href="Mazaticol" title="Mazaticol">Mazaticol</a></li>

<li><a href="Mebeverine" title="Mebeverine">Mebeverine</a></li>

<li><a href="Meladrazine" title="Meladrazine">Meladrazine</a></li>

<li><a href="Mepenzolate" title="Mepenzolate">Mepenzolate</a></li>

<li><a href="Methantheline" title="Methantheline">Methantheline</a></li>

<li><a href="Methoctramine" title="Methoctramine">Methoctramine</a></li>

<li><a href="Methylatropine" title="Methylatropine">Methylatropine</a></li>

<li><a href="Methylhomatropine" class="mw-redirect" title="Methylhomatropine">Methylhomatropine</a></li>

<li><a href="Methylscopolamine_bromide" title="Methylscopolamine bromide">Methylscopolamine</a></li>

<li><a href="Metixene" title="Metixene">Metixene</a></li>

<li><a href="Muscarinic_toxin_7" title="Muscarinic toxin 7">Muscarinic toxin 7</a></li>

<li><a href="N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">N-Ethyl-3-piperidyl benzilate</a></li>

<li><a href="N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">N-Methyl-3-piperidyl benzilate</a></li>

<li><a href="Nefopam" title="Nefopam">Nefopam</a></li>

<li><a href="Octatropine_methylbromide" title="Octatropine methylbromide">Octatropine methylbromide (anisotropine methylbromide)</a></li>

<li><a href="Orphenadrine" title="Orphenadrine">Orphenadrine</a></li>

<li><a href="Otenzepad" title="Otenzepad">Otenzepad (AF-DX 116)</a></li>

<li><a href="Otilonium_bromide" title="Otilonium bromide">Otilonium bromide</a></li>

<li><a href="Oxapium_iodide" title="Oxapium iodide">Oxapium iodide</a></li>

<li><a href="Oxitropium_bromide" title="Oxitropium bromide">Oxitropium bromide</a></li>

<li><a href="Oxybutynin" title="Oxybutynin">Oxybutynin</a></li>

<li><a href="Oxyphencyclimine" title="Oxyphencyclimine">Oxyphencyclimine</a></li>

<li><a href="Oxyphenonium_bromide" title="Oxyphenonium bromide">Oxyphenonium bromide</a></li>

<li><a href="Penthienate" title="Penthienate">Penthienate</a></li>

<li><a href="Pethidine" title="Pethidine">Pethidine</a></li>

<li>pFHHSiD</li>

<li><a href="Phenglutarimide" title="Phenglutarimide">Phenglutarimide</a></li>

<li><a href="Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li>

<li><a href="Pipenzolate_bromide" title="Pipenzolate bromide">Pipenzolate bromide</a></li>

<li><a href="Piperidolate" title="Piperidolate">Piperidolate</a></li>

<li><a href="Pirenzepine" title="Pirenzepine">Pirenzepine</a></li>

<li><a href="Piroheptine" title="Piroheptine">Piroheptine</a></li>

<li><a href="Pizotifen" title="Pizotifen">Pizotifen</a></li>

<li><a href="Poldine" title="Poldine">Poldine</a></li>

<li><a href="Pridinol" title="Pridinol">Pridinol</a></li>

<li><a href="Prifinium_bromide" title="Prifinium bromide">Prifinium bromide</a></li>

<li><a href="Procyclidine" title="Procyclidine">Procyclidine</a></li>

<li><a href="Profenamine" title="Profenamine">Profenamine (ethopropazine)</a></li>

<li><a href="Propantheline_bromide" title="Propantheline bromide">Propantheline bromide</a></li>

<li><a href="Propiverine" title="Propiverine">Propiverine</a></li>

<li><a href="Quinidine" title="Quinidine">Quinidine</a></li>

<li><a href="3-Quinuclidinyl_thiochromane-4-carboxylate" title="3-Quinuclidinyl thiochromane-4-carboxylate">3-Quinuclidinyl thiochromane-4-carboxylate</a></li>

<li><a href="Revefenacin" title="Revefenacin">Revefenacin</a></li>

<li><a href="Rociverine" title="Rociverine">Rociverine</a></li>

<li><a href="Hyoscine" class="mw-redirect" title="Hyoscine">Scopolamine (hyoscine)</a></li>

<li><a href="Hyoscine_butylbromide" title="Hyoscine butylbromide">Scopolamine butylbromide (hyoscine butylbromide)</a></li>

<li>Silahexacyclium</li>

<li><a href="Sofpironium_bromide" title="Sofpironium bromide">Sofpironium bromide</a></li>

<li><a href="Solifenacin" title="Solifenacin">Solifenacin</a></li>

<li><a href="Selective_serotonin_reuptake_inhibitors" class="mw-redirect" title="Selective serotonin reuptake inhibitors"><abbr title="Selective serotonin reuptake inhibitors">SSRIs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective serotonin reuptake inhibitors</span> (e.g., <a href="Femoxetine" title="Femoxetine">femoxetine</a>, <a href="Paroxetine" title="Paroxetine">paroxetine</a>)</li>

<li><a href="Telenzepine" title="Telenzepine">Telenzepine</a></li>

<li><a href="Terodiline" title="Terodiline">Terodiline</a></li>

<li><a href="Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="Amoxapine" title="Amoxapine">amoxapine</a>, <a href="Maprotiline" title="Maprotiline">maprotiline</a>, <a href="Mianserin" title="Mianserin">mianserin</a>, <a href="Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li>

<li><a href="Tiemonium_iodide" title="Tiemonium iodide">Tiemonium iodide</a></li>

<li><a href="Timepidium_bromide" title="Timepidium bromide">Timepidium bromide</a></li>

<li><a href="Tiotropium_bromide" title="Tiotropium bromide">Tiotropium bromide</a></li>

<li>Tiquizium bromide</li>

<li><a href="Tofenacin" title="Tofenacin">Tofenacin</a></li>

<li><a href="Tolterodine" title="Tolterodine">Tolterodine</a></li>

<li><a href="Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="Amitriptyline" title="Amitriptyline">amitriptyline</a> (<a href="Amitriptyline/perphenazine" title="Amitriptyline/perphenazine">+perphenazine</a>), <a href="Amitriptylinoxide" title="Amitriptylinoxide">amitriptylinoxide</a>, <a href="Butriptyline" title="Butriptyline">butriptyline</a>, <a href="Cidoxepin" title="Cidoxepin">cidoxepin</a>, <a href="Clomipramine" title="Clomipramine">clomipramine</a>, <a href="Desipramine" title="Desipramine">desipramine</a>, desmethyldesipramine, <a href="Dibenzepin" title="Dibenzepin">dibenzepin</a>, <a href="Dosulepin" title="Dosulepin">dosulepin (dothiepin)</a>, <a href="Doxepin" title="Doxepin">doxepin</a>, <a href="Imipramine" title="Imipramine">imipramine</a>, <a href="Lofepramine" title="Lofepramine">lofepramine</a>, <a href="Nitroxazepine" title="Nitroxazepine">nitroxazepine</a>, <a href="Northiaden" title="Northiaden">northiaden (desmethyldosulepin)</a>, <a href="Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="Protriptyline" title="Protriptyline">protriptyline</a>, <a href="Quinupramine" title="Quinupramine">quinupramine</a>, <a href="Trimipramine" title="Trimipramine">trimipramine</a>)</li>

<li><a href="Tridihexethyl" title="Tridihexethyl">Tridihexethyl</a></li>

<li><a href="Trihexyphenidyl" title="Trihexyphenidyl">Trihexyphenidyl</a></li>

<li><a href="Trimebutine" title="Trimebutine">Trimebutine</a></li>

<li><a href="Tripitamine" class="mw-redirect" title="Tripitamine">Tripitamine (tripitramine)</a></li>

<li>Tropacine</li>

<li><a href="Tropatepine" title="Tropatepine">Tropatepine</a></li>

<li><a href="Tropicamide" title="Tropicamide">Tropicamide</a></li>

<li><a href="Tropine_benzilate" title="Tropine benzilate">Tropine benzilate</a></li>

<li><a href="Trospium_chloride" title="Trospium chloride">Trospium chloride</a></li>

<li><a href="Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="Chlorprothixene" title="Chlorprothixene">chlorprothixene</a>, <a href="Cyamemazine" title="Cyamemazine">cyamemazine (cyamepromazine)</a>, <a href="Loxapine" title="Loxapine">loxapine</a>, <a href="Mesoridazine" title="Mesoridazine">mesoridazine</a>, <a href="Thioridazine" title="Thioridazine">thioridazine</a>)</li>

<li><a href="Umeclidinium_bromide" title="Umeclidinium bromide">Umeclidinium bromide</a> (<a href="Umeclidinium_bromide/vilanterol" title="Umeclidinium bromide/vilanterol">+vilanterol</a>)</li>

<li><a href="Xanomeline" title="Xanomeline">Xanomeline</a></li>

<li>Zamifenacin</li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br><small>(and <a href="Prodrug" title="Prodrug">prodrugs</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li>

<li><a href="Adafenoxate" title="Adafenoxate">Adafenoxate</a></li>

<li><a href="Choline" title="Choline">Choline</a> (<a href="Lecithin" title="Lecithin">lecithin</a>)</li>

<li><a href="Citicoline" title="Citicoline">Citicoline</a></li>

<li><a href="Cyprodenate" title="Cyprodenate">Cyprodenate</a></li>

<li><a href="Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li>

<li><a href="Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li>

<li><a href="Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li>

<li><a href="Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li>

<li><a href="Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li>

<li><a href="Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li>

<li><a href="Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul>

</div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div>

<dd>Receptor/signaling modulators</dd>

<dd>Nicotinic acetylcholine receptor modulators</dd>

<dd>Acetylcholine metabolism/transport modulators</dd></dl>

</div></td></tr></tbody></table></div></div><div><div class="zim-footer">

This article is issued from <a class="external text" title="Last edited on 2025-05-29" href="https://en.wikipedia.org/wiki/?title=Procainamide&oldid=1292969726">Wikipedia</a>. The text is available under <a class="external text" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en">Creative Commons Attribution-Share Alike 4.0</a> unless otherwise noted. Additional terms may apply for the media files.

</div>

</div></div>

</div>

</main>

</div>

</body></html>