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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Ciclesonid</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><table class="wikitable infobox float-right" id="Vorlage_Infobox_Chemikalie" style="font-size:90%; margin-top:0; width:350px;" summary="Infobox Chemikalie">
<tbody><tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Strukturformel
</th></tr>
<tr>
<td colspan="2" class="hintergrundfarbe-basis skin-invert-image" style="text-align:center;"><span typeof="mw:File"></span>
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<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Allgemeines
</th></tr>
<tr>
<td style="width:33%;"><a href="Internationaler_Freiname" title="Internationaler Freiname">Freiname</a>
</td>
<td>Ciclesonid
</td></tr>
<tr>
<td>Andere Namen
</td>
<td>
<p>{16α,17-[(<i>R</i>)-Cyclohexylmethylendioxy]-11β-hydroxy-3,20-dioxopregn-1,4-dien-21-yl}isobutyrat<sup id="cite_ref-Rot_1-0" class="reference"><a href="#cite_note-Rot-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Summenformel" title="Summenformel">Summenformel</a>
</td>
<td>C<sub>32</sub>H<sub>44</sub>O<sub>7</sub>
</td></tr>
<tr>
<td>Kurzbeschreibung
</td>
<td>
<p>weißes Pulver<sup id="cite_ref-Sigma_2-0" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Externe Identifikatoren/Datenbanken
</th></tr>
<tr>
<td colspan="2" style="padding:0;">
<table class="mw-collapsible mw-collapsed wikitable" data-expandtext="+" data-collapsetext="−" style="border-top:none; margin:-1px; width:calc(100% + 2px);">
<tbody><tr>
<td style="width:33%;"><a href="CAS-Nummer" title="CAS-Nummer">CAS-Nummer</a>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=126544-47-6">126544-47-6</a><span class="editoronly" style="display:none;"></span>
</td>
<td style="background:#FFDEAD; color:#202122; border-top:1px solid #FFDEAD; padding:0.2em 0; vertical-align:bottom; width:5%;">
</td></tr>
<tr>
<td><a href="EG-Nummer" title="EG-Nummer">EG-Nummer</a> (<a href="EG-Nummer#Listennummern" title="EG-Nummer">Listennummer</a>)
</td>
<td colspan="2">685-344-5
</td></tr>
<tr>
<td><a href="Europ%C3%A4ische_Chemikalienagentur" title="Europäische Chemikalienagentur">ECHA</a>-InfoCard
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.echa.europa.eu/de/substance-information/-/substanceinfo/100.210.908">100.210.908</a>
</td></tr>
<tr>
<td><a href="PubChem" title="PubChem">PubChem</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/6918155">6918155</a>
</td></tr>
<tr>
<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5293368.html">5293368</a>
</td></tr>
<tr>
<td><a href="DrugBank" title="DrugBank">DrugBank</a>
</td>
<td colspan="2"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01410">DB01410</a>
</td></tr>
<tr>
<td style="border-right:1px solid #a2a9b1;"><a href="Wikidata" title="Wikidata">Wikidata</a>
</td>
<td colspan="2"><a href="https://www.wikidata.org/wiki/Q5119448" class="extiw external" title="d:Q5119448">Q5119448</a>
</td></tr></tbody></table>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Arzneistoffangaben
</th></tr>
<tr>
<td><a href="Anatomisch-Therapeutisch-Chemisches_Klassifikationssystem" title="Anatomisch-Therapeutisch-Chemisches Klassifikationssystem">ATC-Code</a>
</td>
<td>
<p>R03<a rel="nofollow" class="external text" href="https://atcddd.fhi.no/atc_ddd_index/?code=R03BA08">BA08</a><span class="editoronly" style="display:none;"></span>
</p>
</td></tr>
<tr>
<td><a href="Wirkstoffklasse" title="Wirkstoffklasse">Wirkstoffklasse</a>
</td>
<td>
<p><a href="Glucocorticoid" class="mw-redirect" title="Glucocorticoid">Glucocorticoid</a>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Eigenschaften
</th></tr>
<tr>
<td><a href="Molare_Masse" title="Molare Masse">Molare Masse</a>
</td>
<td>540,70 g·<a href="Mol" title="Mol">mol</a><sup>−1</sup>
</td></tr>
<tr>
<td><a href="Aggregatzustand" title="Aggregatzustand">Aggregatzustand</a>
</td>
<td>
<p>fest<sup id="cite_ref-Sigma_2-1" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<td><a href="Schmelzpunkt" title="Schmelzpunkt">Schmelzpunkt</a>
</td>
<td>
<p>209–211 °C<sup id="cite_ref-Sigma_2-2" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
</td></tr>
<tr>
<th colspan="2" style="background:#FFDEAD; color:#202122;">Sicherheitshinweise
</th></tr>
<tr>
<td colspan="2">
<table cellspacing="0" cellpadding="2" style="width:100%;">
<tbody><tr>
<td colspan="2" style="border-bottom:1px #A7A7A7 dashed; text-align:center;">Bitte die Befreiung von der Kennzeichnungspflicht für Arzneimittel, Medizinprodukte, Kosmetika, Lebensmittel und Futtermittel beachten
</td></tr>
<tr>
<td colspan="2" style="text-align:center"><b><a href="Global_harmonisiertes_System_zur_Einstufung_und_Kennzeichnung_von_Chemikalien" title="Global harmonisiertes System zur Einstufung und Kennzeichnung von Chemikalien">GHS-Gefahrstoffkennzeichnung</a></b><sup id="cite_ref-Sigma_2-3" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
<table class="hintergrundfarbe-neutral" style="text-align:center; margin-left:auto; margin-right:auto; display:flex; justify-content:center;">
<tbody><tr>
<td><i>keine GHS-Piktogramme</i>
</td></tr></tbody></table>
<p>
</p>
</td></tr>
<tr>
<td rowspan="2" width="33%" style="border-top:1px #A7A7A7 dashed; border-right:1px #A7A7A7 dashed;"><a href="H-_und_P-S%C3%A4tze" title="H- und P-Sätze">H- und P-Sätze</a>
</td>
<td style="border-top:1px #A7A7A7 dashed;">H: <span title="Untervorlage eingebunden: H-Sätze"></span><i>keine H-Sätze</i>
</td></tr>
<tr>
<td style="border-top:1px #A7A7A7 dashed;">P: <span title="Untervorlage eingebunden: P-Sätze"></span><i>keine P-Sätze</i><sup id="cite_ref-Sigma_2-4" class="reference"><a href="#cite_note-Sigma-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</td></tr>
</tbody></table>
</td></tr>
<tr>
<td colspan="2" style="background:#FFDEAD; color:#202122; font-size:80%; text-align:center; line-height:150%; padding:.25em;">Wenn nicht anders vermerkt, gelten die angegebenen Daten bei <a href="Standardbedingungen" title="Standardbedingungen">Standardbedingungen</a> (0 °C, 1000 hPa).
</td></tr></tbody></table><p><span class="editoronly" style="display:none;"></span>
</p><p><b>Ciclesonid</b> ist <a href="Arzneistoff" title="Arzneistoff">Arzneistoff</a> aus der Gruppe der <a href="Corticosteroide" title="Corticosteroide">Corticosteroide</a> mit entzündungshemmenden Eigenschaften.<sup id="cite_ref-Klee_3-0" class="reference"><a href="#cite_note-Klee-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Es handelt sich um ein inhalatives Corticosteroid, das zur vorbeugenden Behandlung von persistierendem <a href="Asthma_bronchiale" title="Asthma bronchiale">Asthma bronchiale</a> bei Erwachsenen, Jugendlichen und – in einigen Ländern – bei Kindern eingesetzt wird.<sup id="cite_ref-Drugs_4-0" class="reference"><a href="#cite_note-Drugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Pharmakologie">Pharmakologie</h2></div>
<p>Ciclesonid ist ein <a href="Prodrug" title="Prodrug">Prodrug</a> und somit selbst inaktiv. Es muss zunächst gespalten werden, um seine entzündungshemmende Wirkung zu entfalten.<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> Dabei entsteht in der Lunge der aktive <a href="Metabolit" title="Metabolit">Metabolit</a> Desisobutyryl-Ciclesonid, der für die Wirkungen des Arzneistoffs bei Asthmapatienten verantwortlich ist. Ciclesonid steigert die <a href="Lungenfunktion" title="Lungenfunktion">Lungenfunktion</a> und mindert die Asthmasymptome und den Einsatz von Notfallmedikamenten bei Patienten mit Asthma unterschiedlichen Schweregrades. Ciclesonid hat sich auch bei pädiatrischen Patienten mit Asthma als wirksam erwiesen.<sup id="cite_ref-Drugs_4-1" class="reference"><a href="#cite_note-Drugs-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Neil_6-0" class="reference"><a href="#cite_note-Neil-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>
</p><p>In Studien an Asthmapatienten war Ciclesonid mindestens so wirksam wie <a href="Budesonid" title="Budesonid">Budesonid</a> bei der Erhöhung des forcierten Ausatmungsvolumens in einer Sekunde und der forcierten <a href="Vitalkapazit%C3%A4t" title="Vitalkapazität">Vitalkapazität</a> gegenüber dem Ausgangswert. Ciclesonid beeinflusste die Asthmasymptome positiv und verringerte den Einsatz von Notfallmedikamenten vergleichbar mit Budesonid.<sup id="cite_ref-Neil_6-1" class="reference"><a href="#cite_note-Neil-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Synthese">Synthese</h2></div>
<p>Die Synthese von Ciclesonid ist in der folgenden Reaktionssequenz beschrieben:<sup id="cite_ref-Klee_3-1" class="reference"><a href="#cite_note-Klee-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Handelsnamen">Handelsnamen</h2></div>
<p><i>Alvesco</i> (D)<sup id="cite_ref-Rot_1-1" class="reference"><a href="#cite_note-Rot-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>, <i>CicloBronch</i><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-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-Rot-1"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Rot_1-0">a</a></sup> <sup><a href="#cite_ref-Rot_1-1">b</a></sup></span> <span class="reference-text">Rote Liste Service GmbH, Rote Liste Service GmbH: <cite style="font-style:italic">ROTE LISTE 2021 Arzneimittelverzeichnis für Deutschland (einschließlich EU-Zulassungen und bestimmter Medizinprodukte).</cite> 1. Auflage. Frankfurt am Main 2021, ISBN 978-3-946057-64-2.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:Ciclesonid&rft.au=Rote+Liste+Service+GmbH%2C+Rote+Liste+Service+GmbH&rft.btitle=ROTE+LISTE+2021+Arzneimittelverzeichnis+f%C3%BCr+Deutschland+%28einschlie%C3%9Flich+EU-Zulassungen+und+bestimmter+Medizinprodukte%29.&rft.date=2021&rft.edition=1.+Auflage&rft.genre=book&rft.isbn=9783946057642&rft.place=Frankfurt+am+Main" style="display:none"> </span></span>
</li>
<li id="cite_note-Sigma-2"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Sigma_2-0">a</a></sup> <sup><a href="#cite_ref-Sigma_2-1">b</a></sup> <sup><a href="#cite_ref-Sigma_2-2">c</a></sup> <sup><a href="#cite_ref-Sigma_2-3">d</a></sup> <sup><a href="#cite_ref-Sigma_2-4">e</a></sup></span> <span class="reference-text">Datenblatt <span style="font-style:italic;"><a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/SIAL/Y0001553">Ciclesonide</a></span> bei <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a>, abgerufen am 24. Juni 2022 (<a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/DE/de/sds/SIAL/Y0001553?userType=anonymous">PDF</a>).<span class="editoronly" style="display:none;"></span></span>
</li>
<li id="cite_note-Klee-3"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Klee_3-0">a</a></sup> <sup><a href="#cite_ref-Klee_3-1">b</a></sup></span> <span class="reference-text"><a href="Axel_Kleemann" title="Axel Kleemann">A. Kleemann</a>, J. Engel, B. Kutscher, D. Reichert: <cite style="font-style:italic">Pharmaceutical Substances, 5th Edition: Syntheses, Patents and Applications of the most relevant APIs</cite>. Georg Thieme Verlag, 2014, ISBN 978-3-13-179525-0, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>283</span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:Ciclesonid&rft.au=A.+Kleemann%2C+J.+Engel%2C+B.+Kutscher%2C+...&rft.btitle=Pharmaceutical+Substances%2C+5th+Edition%3A+Syntheses%2C+Patents+and+Applications+of+the+most+relevant+APIs&rft.date=2014-05-14&rft.genre=book&rft.isbn=9783131795250&rft.pages=283&rft.pub=Georg+Thieme+Verlag" style="display:none"> </span></span>
</li>
<li id="cite_note-Drugs-4"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Drugs_4-0">a</a></sup> <sup><a href="#cite_ref-Drugs_4-1">b</a></sup></span> <span class="reference-text">Emma D. Deeks, Caroline M. Perry: <cite style="font-style:italic">Ciclesonide</cite>. In: <cite style="font-style:italic">Drugs</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>68</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>12</span>, 1. August 2008, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>1741–1770</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.2165/00003495-200868120-00010">10.2165/00003495-200868120-00010</a></span>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Ciclesonid&rft.atitle=Ciclesonide&rft.au=Emma+D.+Deeks%2C+Caroline+M.+Perry&rft.date=2008-08-01&rft.doi=10.2165%2F00003495-200868120-00010&rft.genre=journal&rft.issue=12&rft.jtitle=Drugs&rft.pages=1741-1770&rft.volume=68" style="display:none"> </span></span>
</li>
<li id="cite_note-5"><span class="mw-cite-backlink"><a href="#cite_ref-5">↑</a></span> <span class="reference-text">Andrzej Chciałowski, Tadeusz Płusa: <cite style="font-style:italic">[Ciclesonid--new generation of inhaled glucocorticosteroid]</cite>. In: <cite style="font-style:italic">Wiadomosci lekarskie (Warsaw, Poland)</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>57</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>1–2</span>, 1. Januar 2004, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>70–73</span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/15181753?dopt=Abstract">PMID 15181753</a>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Ciclesonid&rft.atitle=%5BCiclesonid--new+generation+of+inhaled+glucocorticosteroid%5D&rft.au=Andrzej+Chcia%C5%82owski%2C+Tadeusz+P%C5%82usa&rft.date=2004-01-01&rft.genre=journal&rft.issue=1-2&rft.jtitle=Wiadomosci+lekarskie+%28Warsaw%2C+Poland%29&rft.pages=70-73&rft.pmid=15181753&rft.volume=57" style="display:none"> </span></span>
</li>
<li id="cite_note-Neil-6"><span class="mw-cite-backlink">↑ <sup><a href="#cite_ref-Neil_6-0">a</a></sup> <sup><a href="#cite_ref-Neil_6-1">b</a></sup></span> <span class="reference-text">Neil A. Reynolds, Lesley J. Scott: <cite style="font-style:italic">Ciclesonide</cite>. In: <cite style="font-style:italic">Drugs</cite>. <span style="white-space:nowrap">Band<span style="display:inline-block;width:.2em"> </span>64</span>, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>5</span>, 2004, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>511–519</span>, <a href="Digital_Object_Identifier" title="Digital Object Identifier">doi</a>:<span class="uri-handle" style="white-space:nowrap"><a rel="nofollow" class="external text" href="https://doi.org/10.2165/00003495-200464050-00005">10.2165/00003495-200464050-00005</a></span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/14977388?dopt=Abstract">PMID 14977388</a>.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Ciclesonid&rft.atitle=Ciclesonide&rft.au=Neil+A.+Reynolds%2C+Lesley+J.+Scott&rft.date=2004&rft.doi=10.2165%2F00003495-200464050-00005&rft.genre=journal&rft.issue=5&rft.jtitle=Drugs&rft.pages=511-519&rft.pmid=14977388&rft.volume=64" style="display:none"> </span></span>
</li>
<li id="cite_note-7"><span class="mw-cite-backlink"><a href="#cite_ref-7">↑</a></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://www.gelbe-liste.de/produkte/CicloBronch-160-Mikrogramm-Dosis-Druckgasinhalation-Loesung_1419529">Gelbe Liste - CicloBronch-160-Mikrogramm-Dosis-Druckgasinhalation-Loesung</a></span>
</li>
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