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<title>Digitoxin</title>

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</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="Digoxin" title="Digoxin">Digoxin</a>.</div>

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</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Digitoxin">Digitoxin</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"></span></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;"><a href="Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Digalen, Digitaline, Digitmerck, others</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="Oral_administration" title="Oral administration">By mouth</a>, <a href="Intravenous_injection" class="mw-redirect" title="Intravenous injection">Intravenous injection</a></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">

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</style><div class="plainlist"><ul><li><a href="ATC_code_C01" title="ATC code C01">C01AA04</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C01AA04">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>In general: ℞ (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">98–100% (oral)</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">90–97%</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">Liver (<a href="CYP3A4" title="CYP3A4">CYP3A4</a>)</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">7–8 days</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">60% via urine, 40% via faeces</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%;">(3β,5β)-3-[(O-2,6-dideoxy-<br>β-D-ribo-hexapyranosyl-(1->4)-<br>2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-<br>14-hydroxycard-20(22)-enolide</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=71-63-6">71-63-6</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/441207">441207</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=6782">6782</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/DB01396">DB01396</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">N</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.389987.html">389987</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">N</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/E90NZP2L9U">E90NZP2L9U</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/D00297">D00297</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">N</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:28544">CHEBI:28544</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">N</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/ChEMBL254219">ChEMBL254219</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">N</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/DTXSID0022933">DTXSID0022933</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/100.000.691">100.000.691</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>41</sub><span title="Hydrogen">H</span><sub>64</sub><span title="Oxygen">O</span><sub>13</sub></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">764.950</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%5C1OC%2FC%28%3DC%2F1%29%5BC%40H%5D2CC%5BC%40%40%5D8%28O%29%5BC%40%5D2%28C%29CC%5BC%40H%5D7%5BC%40H%5D8CC%5BC%40H%5D6%5BC%40%5D7%28C%29CC%5BC%40H%5D%28O%5BC%40%40H%5D5O%5BC%40H%5D%28C%29%5BC%40%40H%5D%28O%5BC%40%40H%5D4O%5BC%40%40H%5D%28%5BC%40%40H%5D%28O%5BC%40%40H%5D3O%5BC%40%40H%5D%28%5BC%40%40H%5D%28O%29%5BC%40%40H%5D%28O%29C3%29C%29%5BC%40%40H%5D%28O%29C4%29C%29%5BC%40%40H%5D%28O%29C5%29C6">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/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1<sup> <span typeof="mw:File"><span></span></span><span style="display:none">N</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:WDJUZGPOPHTGOT-XUDUSOBPSA-N<sup> <span typeof="mw:File"><span></span></span><span style="display:none">N</span></sup></div></li></ul>

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</style><span class="nobold"> <sup><span typeof="mw:File"><span></span></span><span style="display:none">N</span><span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup> (what is this?)</span><span class="nobold">  <span class="reflink nourlexpansion"><a class="external text external" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=297417192&page2=Digitoxin">(verify)</a></span></span></td></tr></tbody></table>

<p><b>Digitoxin</b> is a <a href="Cardiac_glycoside" title="Cardiac glycoside">cardiac glycoside</a> used for the treatment of <a href="Heart_failure" title="Heart failure">heart failure</a> and certain kinds of <a href="Arrhythmia" title="Arrhythmia">heart arrhythmia</a>. It is a <a href="Phytosteroid" title="Phytosteroid">phytosteroid</a> and is similar in <a href="Chemical_structure" title="Chemical structure">structure</a> and effects to <a href="Digoxin" title="Digoxin">digoxin</a>, though the effects are longer-lasting. Unlike digoxin, which is eliminated from the body via the kidneys, it is eliminated via the liver, and so can be used in patients with poor or erratic kidney function. While several controlled trials have shown digoxin to be effective in a proportion of patients treated for heart failure, the evidence base for digitoxin is not as strong, although it is presumed to be similarly effective.<sup id="cite_ref-Belz_1-0" class="reference"><a href="#cite_note-Belz-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2></div>

<p>Digitoxin is used for the treatment of heart failure, especially in people with impaired kidney function. It is also used to treat certain kinds of <a href="Heart_arrhythmia" class="mw-redirect" title="Heart arrhythmia">heart arrhythmia</a>, such as <a href="Atrial_fibrillation" title="Atrial fibrillation">atrial fibrillation</a>.<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AC_3-0" class="reference"><a href="#cite_note-AC-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>

</p>

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

<p>Contraindications include<sup id="cite_ref-AC_3-1" class="reference"><a href="#cite_note-AC-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>

</p>

<ul><li>problems with the heart rhythm, such as severe <a href="Bradycardia" title="Bradycardia">bradycardia</a> (slow heartbeat), <a href="Ventricular_tachycardia" title="Ventricular tachycardia">ventricular tachycardia</a> (fast heartbeat caused by the <a href="Ventricle_(heart)" title="Ventricle (heart)">ventricles</a>), <a href="Ventricular_fibrillation" title="Ventricular fibrillation">ventricular fibrillation</a>, or first- to second-degree <a href="Atrioventricular_block" title="Atrioventricular block">atrioventricular block</a>,</li>

<li>and certain <a href="Electrolyte_imbalance" title="Electrolyte imbalance">electrolyte imbalances</a>: <a href="Hypokalemia" title="Hypokalemia">hypokalemia</a> (low blood potassium levels), <a href="Hypomagnesemia" class="mw-redirect" title="Hypomagnesemia">hypomagnesemia</a> (low magnesium), and <a href="Hypercalcemia" class="mw-redirect" title="Hypercalcemia">hypercalcemia</a> (high calcium).</li></ul>

<div class="mw-heading mw-heading2"><h2 id="Adverse_effects_and_toxicity">Adverse effects and toxicity</h2></div>

<p>Digitoxin exhibits similar toxic effects to <a href="Digoxin" title="Digoxin">digoxin</a>, namely: <a href="Anorexia" class="mw-redirect" title="Anorexia">anorexia</a>, <a href="Nausea" title="Nausea">nausea</a>, vomiting, diarrhea, confusion, visual disturbances, and cardiac <a href="Arrhythmias" class="mw-redirect" title="Arrhythmias">arrhythmias</a>. Antidigoxin <a href="Antibody_fragment" title="Antibody fragment">antibody fragments</a>, the specific treatment for digoxin poisoning, are also effective in serious digitoxin toxicity.<sup id="cite_ref-Kurowsky_4-0" class="reference"><a href="#cite_note-Kurowsky-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>

</p>

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

<p>Drugs that can increase digitoxin toxicity include:<sup id="cite_ref-AC_3-2" class="reference"><a href="#cite_note-AC-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>

</p>

<ul><li>calcium</li>

<li>substances that lower potassium or magnesium levels, such as <a href="Diuretic" title="Diuretic">diuretics</a> and <a href="Corticosteroid" title="Corticosteroid">corticosteroids</a></li>

<li><a href="Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a> of the liver enzyme <a href="CYP3A4" title="CYP3A4">CYP3A4</a>, which slow down digitoxin <a href="Metabolism" title="Metabolism">metabolism</a>; examples are the antibiotic <a href="Clarithromycin" title="Clarithromycin">clarithromycin</a>, the antifungal <a href="Itraconazole" title="Itraconazole">itraconazole</a>, and <a href="Grapefruit_juice" title="Grapefruit juice">grapefruit juice</a></li>

<li>inhibitors of the transporter protein <a href="P-gp" class="mw-redirect" title="P-gp">P-gp</a>, such as clarithromycin</li>

<li><a href="Beta_blocker" title="Beta blocker">Beta blockers</a> add to the <a href="Bradycardia" title="Bradycardia">bradycardia</a> (slow heartbeat) caused by digitoxin.</li></ul>

<p>Drugs that can decrease the effectivity of digitoxin include:<sup id="cite_ref-AC_3-3" class="reference"><a href="#cite_note-AC-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>

</p>

<ul><li>substances that increase potassium levels, such as <a href="Potassium-sparing_diuretic" title="Potassium-sparing diuretic">Potassium-sparing diuretics</a></li>

<li><a href="Enzyme_inducer" title="Enzyme inducer">inducers</a> of CYP3A4 or P-gp, such as <a href="Phenytoin" title="Phenytoin">phenytoin</a>, <a href="Rifampicin" title="Rifampicin">rifampicin</a> and <a href="St_John's_Wort" class="mw-redirect" title="St John's Wort">St John's Wort</a></li>

<li>substances that bind digitoxin in the gut, such as aluminium containing <a href="Antacid" title="Antacid">antacids</a> or <a href="Colestyramine" title="Colestyramine">colestyramine</a></li></ul>

<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>

<div role="note" class="hatnote navigation-not-searchable">Main article: <a href="Cardiac_glycoside#Mechanism_of_action" title="Cardiac glycoside">Cardiac glycoside § Mechanism of action</a></div>

<p>Digitoxin inhibits the <a href="Sodium-potassium_ATPase" class="mw-redirect" title="Sodium-potassium ATPase">sodium-potassium ATPase</a> in heart muscle cells, resulting in increased force of contractions (positive <a href="Inotropic" class="mw-redirect" title="Inotropic">inotropic</a>), reduced speed of electric conduction (negative <a href="Dromotropic" title="Dromotropic">dromotropic</a>), increased excitability (positive <a href="Bathmotropic" title="Bathmotropic">bathmotropic</a>), and reduced frequency of heartbeat (negative <a href="Chronotropic" title="Chronotropic">chronotropic</a>).<sup id="cite_ref-AC_3-4" class="reference"><a href="#cite_note-AC-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>

</p>

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

<p>The drug is almost completely absorbed from the gut. When in the bloodstream, 90 to 97% are bound to <a href="Plasma_protein" title="Plasma protein">plasma proteins</a>. Digitoxin undergoes <a href="Enterohepatic_circulation" title="Enterohepatic circulation">enterohepatic circulation</a>. It is <a href="Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> in part by CYP3A4; metabolites include <a href="Digitoxigenin" title="Digitoxigenin">digitoxigenin</a>, <a href="Digoxin" title="Digoxin">digoxin</a> (>2%), and <a href="Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugate esters</a>. In healthy people, 60% are eliminated via the kidneys and 40% via the faeces. In people with impaired kidney function, elimination via the faeces is increased. The <a href="Biological_half-life" title="Biological half-life">biological half-life</a> is 7 to 8 days except when kidney <i>and</i> liver functions are impaired, in which case it is usually longer.<sup id="cite_ref-AC_3-5" class="reference"><a href="#cite_note-AC-3"><span class="cite-bracket">[</span>3<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>

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

<p>The first description of the use of <a href="Digitalis_purpurea" title="Digitalis purpurea">foxglove</a> dates back to 1775.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> For quite some time, the active compound was not isolated. <a href="Oswald_Schmiedeberg" title="Oswald Schmiedeberg">Oswald Schmiedeberg</a> was able to obtain a pure sample in 1875. The modern therapeutic use of this molecule was made possible by the works of the pharmacist and the French chemist Claude-Adolphe Nativelle (1812–1889). The first structural analysis was done by <a href="Adolf_Otto_Reinhold_Windaus" class="mw-redirect" title="Adolf Otto Reinhold Windaus">Adolf Otto Reinhold Windaus</a> in 1925, but the full structure with an exact determination of the sugar groups was not accomplished until 1962.<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><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>

</p>

<div class="mw-heading mw-heading2"><h2 id="Use_as_a_weapon">Use as a weapon</h2></div>

<p>Digitoxin has been used for at least 7,000 years as an <a href="Arrow_poison" title="Arrow poison">arrow poison</a>.<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> <a href="Marie_Alexandrine_Becker" title="Marie Alexandrine Becker">Marie Alexandrine Becker</a>, a Belgian serial killer, was sentenced to death for poisoning eleven people with digitoxin.

</p>

<div class="mw-heading mw-heading3"><h3 id="In_fiction">In fiction</h3></div>

<p>Digitoxin is used as a poison or murder weapon in:

</p>

<ul><li><a href="Agatha_Christie" title="Agatha Christie">Agatha Christie</a>'s <i><a href="Appointment_with_Death" title="Appointment with Death">Appointment with Death</a></i></li>

<li><a href="Elizabeth_Peters" class="mw-redirect" title="Elizabeth Peters">Elizabeth Peters</a>' <i>Die For Love</i></li>

<li><i><a href="CSI%3A_Crime_Scene_Investigation" title="CSI: Crime Scene Investigation">CSI</a></i>, season 9, episode 19: "The Descent of Man"</li>

<li><i><a href="Rosewood_(TV_series)" title="Rosewood (TV series)">Rosewood</a></i> season 2, episode 20: <i><a href="Rosewood_(TV_series)#ep42" title="Rosewood (TV series)">Calliphoridae and Country Roads</a></i></li>

<li>"Casino Royale" (2006)</li>

<li>"Uneasy Lies the Crown" on <i>Columbo</i>, season 9, episode 5 (1990)</li>

<li>"Affair of the Heart" on <i>McMillan and Wife</i>, season 6, episode 5 (1977)</li>

<li><i>Murder 101</i>: "College can be a Murder"</li>

<li>Several episodes of Murder She Wrote.</li>

<li><a href="Private_Practice_(season_4)" class="mw-redirect" title="Private Practice (season 4)">Private Practice</a>, season 4, episode 18: “The Hardest Part”</li></ul>

<p>In <a href="The_Decemberists" title="The Decemberists">The Decemberists</a>'s song, "The Rake's Song" on <i><a href="The_Hazards_of_Love" title="The Hazards of Love">The Hazards of Love</a></i> album, the narrator murders his daughter by feeding her foxglove.

</p><p>In <a href="Metal_Gear_Solid_V%3A_The_Phantom_Pain" title="Metal Gear Solid V: The Phantom Pain">Metal Gear Solid V: The Phantom Pain</a>, Venom Snake uses digitalis to obtain digoxin for tranquilizer rounds to incapacitate enemies.

</p>

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

<p>Digitoxin and related cardenolides display anticancer activity against a range of human <a href="Cancer" title="Cancer">cancer</a> cell lines in vitro but the clinical use of digitoxin to treat <a href="Cancer" title="Cancer">cancer</a> has been restricted by its narrow <a href="Therapeutic_index" title="Therapeutic index">therapeutic index</a>.<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> Digitoxin <a href="Glycorandomization" title="Glycorandomization">glycorandomization</a> led to the discovery of novel <a href="Digitoxigenin" title="Digitoxigenin">digitoxigenin</a> neoglycosides which displayed improved anticancer potency and reduced inotropic activity (the perceived mechanism of general toxicity).<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup>

</p>

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

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</style><cite id="CITEREFBelzBreithaupt-GröglerOsowski2001" class="citation journal cs1">Belz GG, Breithaupt-Grögler K, Osowski U (2001). <a rel="nofollow" class="external text" href="https://archive.today/20130105085338/http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0014-2972&date=2001&volume=31&issue=&spage=10">"Treatment of congestive heart failure--current status of use of digitoxin"</a>. <i>European Journal of Clinical Investigation</i>. <b>31</b> (Suppl 2): <span class="nowrap">10–</span>7. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1046%2Fj.1365-2362.2001.0310s2010.x">10.1046/j.1365-2362.2001.0310s2010.x</a> (inactive 12 July 2025). <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/11525233">11525233</a>. Archived from <span class="id-lock-subscription" title="Paid subscription required"><a rel="nofollow" class="external text" href="http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=0014-2972&date=2001&volume=31&issue=&spage=10">the original</a></span> on 2013-01-05.</cite><span class="cs1-maint citation-comment"><code class="cs1-code">{{cite journal}}</code>: CS1 maint: DOI inactive as of July 2025 (link)</span></span>

</li>

<li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><cite id="CITEREFErland_Erdmann2013" class="citation book cs1 cs1-prop-foreign-lang-source">Erland Erdmann, ed. (2013). <i>Therapie mit Herzglykosiden</i> (in German). Springer. p. 43. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-3-642-69046-4</bdi>.</cite></span>

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</li>

<li id="cite_note-Kurowsky-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-Kurowsky_4-0">^</a></b></span> <span class="reference-text"><cite id="CITEREFKurowskiIvenDjonlagic1992" class="citation journal cs1">Kurowski V, Iven H, Djonlagic H (1992). "Treatment of a patient with severe digitoxin intoxication by Fab fragments of anti-digitalis antibodies". <i>Intensive Care Medicine</i>. <b>18</b> (7): <span class="nowrap">439–</span>42. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF01694351">10.1007/BF01694351</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/1469187">1469187</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:2324996">2324996</a>.</cite></span>

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<li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.mediq.ch/">"mediQ: Digitoxin"</a><span class="reference-accessdate">. Retrieved <span class="nowrap">2021-09-14</span></span>.</cite></span>

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<li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><cite id="CITEREFWithering1785" class="citation book cs1">Withering W (1785). <a rel="nofollow" class="external text" href="https://archive.org/details/b21517356"><i>An Account of the Foxglove and Some of its Medical Uses: With Practical Remarks on Dropsy and other Diseases</i></a>. Classics of Medicine Library.</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="CITEREFDiefenbachMeneely1949" class="citation journal cs1">Diefenbach WC, Meneely JK (May 1949). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2598854">"Digitoxin; a critical review"</a>. <i>The Yale Journal of Biology and Medicine</i>. <b>21</b> (5): <span class="nowrap">421–</span>31. <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/PMC2598854">2598854</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/18127991">18127991</a>.</cite></span>

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<li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><cite id="CITEREFSneader2005" class="citation book cs1">Sneader W (2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=mYQxRY9umjcC&pg=PA107"><i>Drug discovery: A history</i></a>. Wiley. p. 107. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-0-471-89980-8</bdi>.</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="CITEREFBradfield2025" class="citation journal cs1">Bradfield, Justin (January 23, 2025). <a rel="nofollow" class="external text" href="https://theconversation.com/discovery-in-south-africa-holds-oldest-evidence-of-mixing-ingredients-to-make-arrow-poison-247250">"Discovery in South Africa holds oldest evidence of mixing ingredients to make arrow poison"</a>. <i>The Conversation</i><span class="reference-accessdate">. Retrieved <span class="nowrap">January 24,</span> 2025</span>.</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="CITEREFMengerVacchelliKeppEggermont2013" class="citation journal cs1">Menger L, Vacchelli E, Kepp O, Eggermont A, Tartour E, Zitvogel L, et al. (February 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3601180">"Trial watch: Cardiac glycosides and cancer therapy"</a>. <i>Oncoimmunology</i>. <b>2</b> (2): e23082. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.4161%2Fonci.23082">10.4161/onci.23082</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/PMC3601180">3601180</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/23525565">23525565</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="CITEREFElbazStueckleTseRojanasakul2012" class="citation journal cs1">Elbaz HA, Stueckle TA, Tse W, Rojanasakul Y, Dinu CZ (April 2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3506989">"Digitoxin and its analogs as novel cancer therapeutics"</a>. <i>Experimental Hematology & Oncology</i>. <b>1</b> (1) 4. <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/10.1186%2F2162-3619-1-4">10.1186/2162-3619-1-4</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/PMC3506989">3506989</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/23210930">23210930</a>.</cite></span>

</li>

<li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><cite id="CITEREFLangenhanPetersGuzeiHoffmann2005" class="citation journal cs1">Langenhan JM, Peters NR, Guzei IA, Hoffmann FM, Thorson JS (August 2005). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1194917">"Enhancing the anticancer properties of cardiac glycosides by neoglycorandomization"</a>. <i>Proceedings of the National Academy of Sciences of the United States of America</i>. <b>102</b> (35): <span class="nowrap">12305–</span>10. <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/2005PNAS..10212305L">2005PNAS..10212305L</a>. <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/10.1073%2Fpnas.0503270102">10.1073/pnas.0503270102</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/PMC1194917">1194917</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/16105948">16105948</a>.</cite></span>

</li>

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<div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2></div>

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<ul><li><cite id="CITEREFJohanssonLindholmGullboLarsson2001" class="citation journal cs1">Johansson S, Lindholm P, Gullbo J, Larsson R, Bohlin L, Claeson P (June 2001). "Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells". <i>Anti-Cancer Drugs</i>. <b>12</b> (5): <span class="nowrap">475–</span>83. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00001813-200106000-00009">10.1097/00001813-200106000-00009</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/11395576">11395576</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:19894541">19894541</a>.</cite></li>

<li><cite id="CITEREFHippiusHumaidSickerHoffmann2001" class="citation journal cs1">Hippius M, Humaid B, Sicker T, Hoffmann A, Göttler M, Hasford J (August 2001). "Adverse drug reaction monitoring--digitoxin overdosage in the elderly". <i>International Journal of Clinical Pharmacology and Therapeutics</i>. <b>39</b> (8): <span class="nowrap">336–</span>43. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.5414%2Fcpp39336">10.5414/cpp39336</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/11515708">11515708</a>.</cite></li>

<li><cite id="CITEREFHauxKleppSpigsetTretli2001" class="citation journal cs1">Haux J, Klepp O, Spigset O, Tretli S (2001). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC48150">"Digitoxin medication and cancer; case control and internal dose-response studies"</a>. <i>BMC Cancer</i>. <b>1</b> 11. <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/10.1186%2F1471-2407-1-11">10.1186/1471-2407-1-11</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/PMC48150">48150</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/11532201">11532201</a>.</cite></li>

<li><cite id="CITEREFSrivastavaEidelmanZhangPaweletz2004" class="citation journal cs1">Srivastava M, Eidelman O, Zhang J, Paweletz C, Caohuy H, Yang Q, et al. (May 2004). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC419668">"Digitoxin mimics gene therapy with CFTR and suppresses hypersecretion of IL-8 from cystic fibrosis lung epithelial cells"</a>. <i>Proceedings of the National Academy of Sciences of the United States of America</i>. <b>101</b> (20): <span class="nowrap">7693–</span>8. <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/2004PNAS..101.7693S">2004PNAS..101.7693S</a>. <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/10.1073%2Fpnas.0402030101">10.1073/pnas.0402030101</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/PMC419668">419668</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/15136726">15136726</a>.</cite></li></ul>

</div>

<div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2></div>

<p><span class="noviewer" typeof="mw:File"></span> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Digitoxin" class="extiw external" title="commons:Category:Digitoxin">Digitoxin</a> at Wikimedia Commons

</p>

<ul><li>Comparing the Toxicity of Digoxin and Digitoxin in a Geriatric Population: Should an Old Drug Be Rediscovered? on <a rel="nofollow" class="external text" href="https://www.medscape.com/viewarticle/410488">Medscape</a> <span style="font-size:0.95em; font-size:95%; color: var( --color-subtle, #555 )">(registration required)</span>, a convenience link from the <a rel="nofollow" class="external text" href="https://sma.org/southern-medical-journal/article/comparing-the-toxicity-of-digoxin-and-digitoxin-in-a-geriatric-population-should-an-old-drug-be-rediscovered-2/">original</a>. <span style="font-size:0.95em; font-size:95%; color: var( --color-subtle, #555 )">(subscription required)</span></li></ul>

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</style><div id="Glycosides90" style="font-size:114%;margin:0 4em"><a href="Glycoside" title="Glycoside">Glycosides</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Glycosidic_bond" title="Glycosidic bond">Bond</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Glycosidic_bond#S-,_N-,_C-,_and_O-glycosidic_bonds" title="Glycosidic bond"><i>O</i>-glycosidic bond</a></li>

<li><a href="Glycosidic_bond#S-,_N-,_C-,_and_O-glycosidic_bonds" title="Glycosidic bond"><i>N</i>-glycosidic bond</a></li>

<li><a href="Glycosidic_bond#S-,_N-,_C-,_and_O-glycosidic_bonds" title="Glycosidic bond"><i>S</i>-glycosidic bond</a></li>

<li><a href="Glycosidic_bond#S-,_N-,_C-,_and_O-glycosidic_bonds" title="Glycosidic bond"><i>C</i>-glycosidic bond</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Isomer" title="Isomer">Geometry</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Glycosidic_bond#Numbering,_and_α/β_distinction_of_glycosidic_bonds" title="Glycosidic bond">α-Glycoside</a></li>

<li><a href="Glycosidic_bond#Numbering,_and_α/β_distinction_of_glycosidic_bonds" title="Glycosidic bond">β-Glycoside</a></li>

<li><a href="Glycosidic_bond#Numbering,_and_α/β_distinction_of_glycosidic_bonds" title="Glycosidic bond">1,4-Glycoside</a></li>

<li><a href="Glycosidic_bond#Numbering,_and_α/β_distinction_of_glycosidic_bonds" title="Glycosidic bond">1,6-Glycoside</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Glycoside" title="Glycoside">Glycone</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

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

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

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

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

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

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

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Aglycone" title="Aglycone">Aglycone</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">

<ul><li><a href="Glycoside#Alcoholic_glycosides" title="Glycoside">Alcoholic glycoside</a></li>

<li><a href="Cardiac_glycoside" title="Cardiac glycoside">Cardiac glycoside</a>

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

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

<li><a href="Glycoside#Cyanogenic_glycosides" title="Glycoside">Cyanogenic glycoside</a></li>

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

<li><a href="Glycoside#Phenolic_glycosides" title="Glycoside">Phenolic glycoside</a>

<ul><li><a href="Glycoside#Anthraquinone_glycosides" title="Glycoside">Anthraquinone glycoside</a></li>

<li><a href="Glycoside#Coumarin_glycosides" title="Glycoside">Coumarin glycoside</a></li>

<li><a href="Glycoside#Flavonoid_glycosides" title="Glycoside">Flavonoid glycoside</a></li></ul></li>

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

<li><a href="Steviol_glycoside" title="Steviol glycoside">Steviol glycoside</a></li>

<li><a href="Glycoside#Thioglycosides" title="Glycoside">Thioglycoside</a></li></ul>

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

<div class="navbox-styles"></div><div role="navigation" class="navbox" aria-labelledby="Cardiac_glycosides_(C01A)85" 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"><div id="Cardiac_glycosides_(C01A)85" style="font-size:114%;margin:0 4em"><a href="Cardiac_glycoside" title="Cardiac glycoside">Cardiac glycosides</a> (<a href="ATC_code_C01#C01A" title="ATC code C01">C01A</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Bufadienolide" title="Bufadienolide">Bufadienolides</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="Bufo" title="Bufo">Bufo</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="Arenobufagin" title="Arenobufagin">Arenobufagin</a></li>

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

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

<li><a href="Marinobufagenin" title="Marinobufagenin">Marinobufagin</a></li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Scilla" title="Scilla">Scilla</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="Proscillaridin" title="Proscillaridin">Proscillaridin</a></li>

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

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Kalanchoe" title="Kalanchoe">Kalanchoe</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="Daigremontianin" title="Daigremontianin">Daigremontianin</a></li></ul>

</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Cardenolide" title="Cardenolide">Cardenolides</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="Digitalis" title="Digitalis">Digitalis</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="Acetyldigitoxin" title="Acetyldigitoxin">Acetyldigitoxin</a></li>

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

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

<li><a href="Lanatoside_C" title="Lanatoside C">Lanatoside C</a></li>

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

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

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

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Strophanthus" title="Strophanthus">Strophanthus</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="Ouabain" title="Ouabain">Ouabain</a> (g-Strophanthin)</li>

<li><a href="K-Strophanthidin" title="K-Strophanthidin">k-Strophanthin</a></li>

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

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="Thevetia" title="Thevetia">Thevetia</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="Peruvoside" title="Peruvoside">Peruvoside</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="Estrogen_receptor_modulators1222" 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="Estrogen_receptor_modulators1222" style="font-size:114%;margin:0 4em"><a href="Estrogen_receptor" title="Estrogen receptor">Estrogen 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="Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</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 Estrogen receptor</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:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em">

<ul><li><i>Steroidal:</i> <a href="2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li>

<li><a href="2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li>

<li><a href="3-Methyl-19-methyleneandrosta-3%2C5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li>

<li><a href="3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li>

<li>3α,5α-Dihydrolevonorgestrel</li>

<li>3β,5α-Dihydrolevonorgestrel</li>

<li><a href="3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li>

<li><a href="3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li>

<li><a href="3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li>

<li><a href="4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li>

<li><a href="4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li>

<li><a href="4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li>

<li><a href="4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li>

<li><a href="4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li>

<li><a href="4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li>

<li><a href="4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li>

<li><a href="5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li>

<li><a href="7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li>

<li><a href="7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li>

<li><a href="7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li>

<li><a href="8%2C9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li>

<li><a href="8%2C9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li>

<li><a href="10%CE%B2%2C17%CE%B2-Dihydroxyestra-1%2C4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li>

<li><a href="11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li>

<li><a href="11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li>

<li><a href="15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li>

<li><a href="16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li>

<li><a href="16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li>

<li><a href="16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li>

<li><a href="16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li>

<li><a href="16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li>

<li><a href="16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li>

<li><a href="16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li>

<li><a href="16%CE%B2%2C17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li>

<li><a href="17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li>

<li><a href="17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li>

<li><a href="17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li>

<li><a href="17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li>

<li><a href="17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li>

<li><a href="17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li>

<li><a href="17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li>

<li><a href="17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li>

<li><a href="17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li>

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

<li><a href="Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li>

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

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

<li><a href="Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="Testosterone" title="Testosterone">testosterone</a> and <a href="List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="Nandrolone" title="Nandrolone">nandrolone</a> and <a href="List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li>

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

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

<li><a href="Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li>

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

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

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

<ul><li><a href="Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li>

<li><a href="Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li>

<li><a href="Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li>

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

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

<li><a href="Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></li>

<li><a href="Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li>

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

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

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

<li><a href="Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li>

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

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

<ul><li><a href="List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li>

<li><a href="Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li>

<li><a href="Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li>

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

<li><a href="Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li>

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

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

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

<ul><li><a href="List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li>

<li><a href="Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li>

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

<li><a href="Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li>

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

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

<ul><li><a href="List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li>

<li><a href="Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li>

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

<li><a href="Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li>

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

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

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

<ul><li><a href="Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li>

<li><a href="Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li>

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

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

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

<li><a href="Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li>

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

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

<li><a href="Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li>

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

<li><a href="Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li>

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

<ul><li><i>Nonsteroidal:</i> <a href="(R%2CR)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li>

<li><a href="2%2C8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li>

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

<li><a href="Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li>

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

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

<li><a href="Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li>

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

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

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

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

<ul><li><a href="Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li>

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

<ul><li><a href="List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li>

<li><a href="Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li>

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

<li><a href="Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li>

<li><a href="Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li>

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

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

<li><a href="Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li>

<li><a href="Estrobin" title="Estrobin">Estrobin (DBE)</a></li>

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

<li><a href="Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li>

<li><a href="Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li>

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

<ul><li><a href="List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li>

<li><a href="ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li>

<li><a href="Meso-Butestrol" title="Meso-Butestrol"><i>meso</i>-Butestrol</a></li>

<li><a href="Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-Hexestrol</a></li>

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

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

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

<li><a href="Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li>

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

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

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

<li><a href="Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li>

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

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

<li><a href="SERBA-2" title="SERBA-2">SERBA-2</a></li>

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

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

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

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

<li><a href="Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li>

<ul><li><i>Unknown/unsorted:</i> <a href="ERB-26" title="ERB-26">ERB-26</a></li>

<ul><li><i>Xenoestrogens:</i> <a href="Anise" title="Anise">Anise</a>-related (e.g., <a href="Anethole" title="Anethole">anethole</a>, <a href="Anol" title="Anol">anol</a>, <a href="Dianethole" title="Dianethole">dianethole</a>, <a href="Dianol" title="Dianol">dianol</a>, <a href="Photoanethole" title="Photoanethole">photoanethole</a>)</li>

<li><a href="Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="Phloretin" title="Phloretin">phloretin</a>, <a href="Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li>

<li><a href="Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="Coumestrol" title="Coumestrol">coumestrol</a>, <a href="Psoralidin" title="Psoralidin">psoralidin</a>)</li>

<li><a href="Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="7%2C8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="Apigenin" title="Apigenin">apigenin</a>, <a href="Baicalein" title="Baicalein">baicalein</a>, <a href="Baicalin" title="Baicalin">baicalin</a>, <a href="Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="Calycosin" title="Calycosin">calycosin</a>, <a href="Catechin" title="Catechin">catechin</a>, <a href="Daidzein" title="Daidzein">daidzein</a>, <a href="Daidzin" title="Daidzin">daidzin</a>, <a href="Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="Equol" title="Equol">equol</a>, <a href="Formononetin" title="Formononetin">formononetin</a>, <a href="Glabrene" title="Glabrene">glabrene</a>, <a href="Glabridin" title="Glabridin">glabridin</a>, <a href="Genistein" title="Genistein">genistein</a>, <a href="Genistin" title="Genistin">genistin</a>, <a href="Glycitein" title="Glycitein">glycitein</a>, <a href="Kaempferol" title="Kaempferol">kaempferol</a>, <a href="Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="Mirificin" title="Mirificin">mirificin</a>, <a href="Myricetin" title="Myricetin">myricetin</a>, <a href="Naringenin" title="Naringenin">naringenin</a>, penduletin, <a href="Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="Prunetin" title="Prunetin">prunetin</a>, <a href="Puerarin" title="Puerarin">puerarin</a>, <a href="Quercetin" title="Quercetin">quercetin</a>, <a href="Tectoridin" title="Tectoridin">tectoridin</a>, <a href="Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li>

<li><a href="Lavender_oil" title="Lavender oil">Lavender oil</a></li>

<li><a href="Lignan" title="Lignan">Lignans</a> (e.g., <a href="Enterodiol" title="Enterodiol">enterodiol</a>, <a href="Enterolactone" title="Enterolactone">enterolactone</a>, <a href="Nyasol" title="Nyasol">nyasol (<i>cis</i>-hinokiresinol)</a>)</li>

<li><a href="Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="Cadmium" title="Cadmium">cadmium</a>)</li>

<li><a href="Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="Alternariol" title="Alternariol">alternariol</a>, <a href="Dieldrin" title="Dieldrin">dieldrin</a>, <a href="Endosulfan" title="Endosulfan">endosulfan</a>, <a href="Fenarimol" title="Fenarimol">fenarimol</a>, <a href="HPTE" title="HPTE">HPTE</a>, <a href="Methiocarb" title="Methiocarb">methiocarb</a>, <a href="Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="Triclocarban" title="Triclocarban">triclocarban</a>, <a href="Triclosan" title="Triclosan">triclosan</a>)</li>

<li><a href="Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., (<a href="Digitalis" title="Digitalis">digitalis</a>), <a href="Diosgenin" title="Diosgenin">diosgenin</a>, <a href="Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li>

<li><a href="Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="Campesterol" title="Campesterol">campesterol</a>, <a href="Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li>

<li><a href="Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="Zearalanone" title="Zearalanone">zearalanone</a>, <a href="%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="Zearalenone" title="Zearalenone">zearalenone</a>, <a href="Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li>

<li><a href="Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="Miroestrol" title="Miroestrol">miroestrol</a>)</li>

<li><a href="Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="Resveratrol" title="Resveratrol">resveratrol</a>, <a href="Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li>

<li><a href="Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="Paraben" title="Paraben">parabens</a>, <a href="Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li>

<li>Others (e.g., <a href="Agnuside" title="Agnuside">agnuside</a>, rotundifuran)</li></ul>

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br>(<a href="Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</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 estrogen receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em">

<ul><li><a href="2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li>

<li><a href="2-Phenyl-1-benzothiophene" title="2-Phenyl-1-benzothiophene">2-Phenyl-1-benzothiophene</a></li>

<li><a href="4'-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li>

<li><a href="27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li>

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

<li><a href="Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li>

<li><a href="Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li>

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

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

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

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

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

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

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

<li><a href="Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li>

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

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

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

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

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

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

<li>Promensil</li>

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

<li><a href="Rimostil" title="Rimostil">Rimostil (P-081)</a></li>

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

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

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

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

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

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

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em">

<li><a href="7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li>

<li>Chloroindazole</li>

<li><a href="Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li>

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

<li><a href="Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li>

<li><a href="Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="Glyceollin_I" title="Glyceollin I">I</a>, II, <a href="Glyceollin_III" title="Glyceollin III">III</a>, IV)</li>

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

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

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

<li>Oxabicycloheptene sulfonate</li>

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

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

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

<ul><li><i>Coregulator-binding modulators:</i> <a href="ERX-11" title="ERX-11">ERX-11</a></li></ul>

<ul><li><i>Noncompetitive inhibitors:</i> <a href="Trilostane" title="Trilostane">Trilostane</a></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="G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</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 G protein-coupled estrogen receptor</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:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em">

<ul><li><a href="2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li>

<li><a href="7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li>

<li><a href="Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li>

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

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

<li><a href="Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li>

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

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

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

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

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

<li><a href="Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li>

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

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

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

<li><a href="Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li>

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

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

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

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

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

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

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

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

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

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

</div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em">

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

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

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

<dd>Receptor/signaling modulators</dd>

<dd>Estrogens and antiestrogens</dd>

<dd>Androgen receptor modulators</dd>

<dd>Progesterone receptor modulators</dd>

<dd><a href="List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></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 2025-07-12" href="https://en.wikipedia.org/wiki/?title=Digitoxin&oldid=1300161026">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.

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