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Available in 21 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-21" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">21 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A8%D8%B1%D9%88%D9%83%D8%A7%D9%8A%D9%8A%D9%86%D8%A7%D9%85%D9%8A%D8%AF" title="بروكاييناميد – Arabic" lang="ar" hreflang="ar" data-title="بروكاييناميد" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%BE%D8%B1%D9%88%DA%A9%D8%A7%D8%A6%DB%8C%D9%86_%D8%A2%D9%85%DB%8C%D8%AF" title="پروکائین آمید – South Azerbaijani" lang="azb" hreflang="azb" data-title="پروکائین آمید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Procainamid" title="Procainamid – Welsh" lang="cy" hreflang="cy" data-title="Procainamid" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Procainamid" title="Procainamid – German" lang="de" hreflang="de" data-title="Procainamid" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Procainamida" title="Procainamida – Spanish" lang="es" hreflang="es" data-title="Procainamida" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%D8%B1%D9%88%DA%A9%D8%A7%D8%A6%DB%8C%D9%86_%D8%A2%D9%85%DB%8C%D8%AF" title="پروکائین آمید – Persian" lang="fa" hreflang="fa" data-title="پروکائین آمید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Proca%C3%AFnamide" title="Procaïnamide – French" lang="fr" hreflang="fr" data-title="Procaïnamide" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%94%84%EB%A1%9C%EC%B9%B4%EC%9D%B8%EC%95%84%EB%A7%88%EC%9D%B4%EB%93%9C" title="프로카인아마이드 – Korean" lang="ko" hreflang="ko" data-title="프로카인아마이드" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Procainamide" title="Procainamide – Italian" lang="it" hreflang="it" data-title="Procainamide" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9D%D0%BE%D0%B2%D0%BE%D0%BA%D0%B0%D0%B8%D0%BD%D0%B0%D0%BC%D0%B8%D0%B4" title="Новокаинамид – Kyrgyz" lang="ky" hreflang="ky" data-title="Новокаинамид" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%97%E3%83%AD%E3%82%AB%E3%82%A4%E3%83%B3%E3%82%A2%E3%83%9F%E3%83%89" title="プロカインアミド – Japanese" lang="ja" hreflang="ja" data-title="プロカインアミド" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%AA%E0%AD%8D%E0%AC%B0%E0%AD%8B%E0%AC%95%E0%AD%87%E0%AC%A8%E0%AC%BE%E0%AC%AE%E0%AC%BE%E0%AC%87%E0%AC%A1" title="ପ୍ରୋକେନାମାଇଡ – Odia" lang="or" hreflang="or" data-title="ପ୍ରୋକେନାମାଇଡ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Prokainamid" title="Prokainamid – Polish" lang="pl" hreflang="pl" data-title="Prokainamid" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Procainamida" title="Procainamida – Portuguese" lang="pt" hreflang="pt" data-title="Procainamida" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Procainamid%C4%83" title="Procainamidă – Romanian" lang="ro" hreflang="ro" data-title="Procainamidă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BA%D0%B0%D0%B8%D0%BD%D0%B0%D0%BC%D0%B8%D0%B4" title="Прокаинамид – Russian" lang="ru" hreflang="ru" data-title="Прокаинамид" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Prokainamid" title="Prokainamid – Serbian" lang="sr" hreflang="sr" data-title="Prokainamid" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Prokainamid" title="Prokainamid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Prokainamid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Prokainamidi" title="Prokainamidi – Finnish" lang="fi" hreflang="fi" data-title="Prokainamidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9F%D1%80%D0%BE%D0%BA%D0%B0%D1%97%D0%BD%D0%B0%D0%BC%D1%96%D0%B4" title="Прокаїнамід – Ukrainian" lang="uk" hreflang="uk" data-title="Прокаїнамід" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E6%99%AE%E9%B2%81%E5%8D%A1%E5%9B%A0%E8%83%BA" title="普鲁卡因胺 – Chinese" lang="zh" hreflang="zh" data-title="普鲁卡因胺" data-language-autonym="中文" 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Medication to treat cardiac arrhythmias</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Procainamide">Procainamide</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Procainamide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Procainamide.svg/220px-Procainamide.svg.png" decoding="async" width="220" height="93" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Procainamide.svg/330px-Procainamide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/Procainamide.svg/440px-Procainamide.svg.png 2x" data-file-width="145" data-file-height="61" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="'p' in 'pie'">p</span><span title="'r' in 'rye'">r</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'k' in 'kind'">k</span><span title="/eɪ/: 'a' in 'face'">eɪ</span><span title="'n' in 'nigh'">n</span><span title="/əm/: 'm' in 'rhythm'">əm</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="'d' in 'dye'">d</span></span>/</a></span></span> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Pronestyl, Procan, Procanbid, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/procainamide-hydrochloride.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Intravenous_therapy" title="Intravenous therapy">IV</a>, <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">IM</a>, by mouth</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/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">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a href="/wiki/ATC_code_C01" title="ATC code C01">C01BA02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=C01BA02">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">85% (by mouth)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">15 to 20%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> (<a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a>-mediated)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">~2.5 to 4.5 hours</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">4-amino-<i>N</i>-(2-diethylaminoethyl) benzamide</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=51-06-9">51-06-9</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></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="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/4913">4913</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=4811">4811</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01035">DB01035</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></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="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4744.html">4744</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></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="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/L39WTC366D">L39WTC366D</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D08421">D08421</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></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="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8428">CHEBI:8428</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></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="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL640">ChEMBL640</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></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="/wiki/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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID7023512">DTXSID7023512</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q417597#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.072">100.000.072</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q417597#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>13</sub><span title="Hydrogen">H</span><sub>21</sub><span title="Nitrogen">N</span><sub>3</sub><span title="Oxygen">O</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002235331000000000♠"></span>235.331</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28c1ccc%28N%29cc1%29NCCN%28CC%29CC">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</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%;">O=C(c1ccc(N)cc1)NCCN(CC)CC</div></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="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:REQCZEXYDRLIBE-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477172111&page2=Procainamide">(verify)</a></span></span></td></tr></tbody></table> <p><b>Procainamide</b> (<b>PCA</b>) is a medication of the <a href="/wiki/Antiarrhythmic_agent" title="Antiarrhythmic agent">antiarrhythmic class</a> used for the treatment of <a href="/wiki/Cardiac_arrhythmia" class="mw-redirect" title="Cardiac arrhythmia">cardiac arrhythmias</a>. It is a <a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">sodium channel blocker</a> of <a href="/wiki/Cardiac_muscle_cell" class="mw-redirect" title="Cardiac muscle cell">cardiomyocytes</a>; thus it is classified by the <a href="/wiki/Vaughan_Williams_classification" class="mw-redirect" title="Vaughan Williams classification">Vaughan Williams classification</a> system as class Ia. In addition to blocking the <i>I</i><sub>Na</sub> current, it inhibits the <i>I</i><sub>Kr</sub> rectifier K+ current.<sup id="cite_ref-Osadchii_1-0" class="reference"><a href="#cite_note-Osadchii-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Procainamide is also known to induce a voltage-dependent open channel block on the batrachotoxin (BTX)-activated sodium channels in cardiomyocytes.<sup id="cite_ref-Zamponi_2-0" class="reference"><a href="#cite_note-Zamponi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=1" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Medical">Medical</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=2" title="Edit section: Medical"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Procainamide is used for treating ventricular <a href="/wiki/Arrhythmias" class="mw-redirect" title="Arrhythmias">arrhythmias</a>: ventricular <a href="/wiki/Ectopia_(medicine)" title="Ectopia (medicine)">ectopy</a> and <a href="/wiki/Tachycardia" title="Tachycardia">tachycardia</a> and supraventricular arrhythmias: <a href="/wiki/Atrial_fibrillation" title="Atrial fibrillation">atrial fibrillation</a>, and re-entrant and automatic supraventricular tachycardia.<sup id="cite_ref-Gould_3-0" class="reference"><a href="#cite_note-Gould-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> For example, it can be used to convert new-onset <a href="/wiki/Atrial_fibrillation" title="Atrial fibrillation">atrial fibrillation</a>, and although was initially thought to be suboptimal for this purpose, a growing body of literature is amounting in support for this exact cause.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>It is administered by mouth, by intramuscular injection, or intravenously.<sup id="cite_ref-ten_6-0" class="reference"><a href="#cite_note-ten-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Others">Others</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=3" title="Edit section: Others"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It has also been used as a <a href="/wiki/Chromatography" title="Chromatography">chromatography</a> resin because it somewhat binds protein.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=4" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There are many side effects following the induction of procainamide. These adverse effects are <a href="/wiki/Ventricular_dysrhythmia" class="mw-redirect" title="Ventricular dysrhythmia">ventricular dysrhythmia</a>, <a href="/wiki/Bradycardia" title="Bradycardia">bradycardia</a>, <a href="/wiki/Hypotension" title="Hypotension">hypotension</a> and <a href="/wiki/Shock_(circulatory)" title="Shock (circulatory)">shock</a>. The adverse effects occur even more often if the daily doses are increased. Procainamide may also lead to <a href="/wiki/Drug_fever" class="mw-redirect" title="Drug fever">drug fever</a> and other <a href="/wiki/Allergic_response" title="Allergic response">allergic responses</a>. There is also a chance that <a href="/wiki/Drug-induced_lupus_erythematosus" title="Drug-induced lupus erythematosus">drug-induced lupus erythematosus</a> occurs, which at the same time leads to <a href="/wiki/Arthralgia" title="Arthralgia">arthralgia</a>, <a href="/wiki/Myalgia" title="Myalgia">myalgia</a> and <a href="/wiki/Pleurisy" title="Pleurisy">pleurisy</a>. Most of these side effects may occur due to the <a href="/wiki/Acetylation" title="Acetylation">acetylation</a> of procainamide.<sup id="cite_ref-adverse_12-0" class="reference"><a href="#cite_note-adverse-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Toxicity">Toxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=5" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There is a close line between the plasma concentrations of the therapeutic and toxic effect, therefore a high risk for toxicity.<sup id="cite_ref-adverse_12-1" class="reference"><a href="#cite_note-adverse-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Many symptoms resemble <a href="/wiki/Systemic_lupus_erythematosus" class="mw-redirect" title="Systemic lupus erythematosus">systemic lupus erythematosus</a> because procainamide reactivates <a href="/wiki/Hydroxylamine" title="Hydroxylamine">hydroxylamine</a> and <a href="/wiki/Nitroso" title="Nitroso">nitroso</a> metabolites, which bind to <a href="/wiki/Histone" title="Histone">histone proteins</a> and are toxic to <a href="/wiki/Lymphocytes" class="mw-redirect" title="Lymphocytes">lymphocytes</a>. The hydroxylamine and nitroso metabolites are also toxic to bone marrow cells and can cause <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>. These metabolites are formed due to the activation of <a href="/wiki/Polymorphonuclear_leukocytes" class="mw-redirect" title="Polymorphonuclear leukocytes">polymorphonuclear leukocytes</a>. These leukocytes release <a href="/wiki/Myeloperoxidase" title="Myeloperoxidase">myeloperoxidase</a> and <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a>, which oxidize the primary aromatic amine of procainamide to form procainamide hydroxylamine. The release of hydrogen peroxide is also called a <a href="/wiki/Respiratory_burst" title="Respiratory burst">respiratory burst</a>, which occurs for procainamide in <a href="/wiki/Monocytes" class="mw-redirect" title="Monocytes">monocytes</a> but not in <a href="/wiki/Lymphocytes" class="mw-redirect" title="Lymphocytes">lymphocytes</a>. Furthermore, the metabolites can be formed by activated <a href="/wiki/Neutrophils" class="mw-redirect" title="Neutrophils">neutrophils</a>. These metabolites could then bind to their cell membranes and cause a release of <a href="/wiki/Autoantibodies" class="mw-redirect" title="Autoantibodies">autoantibodies</a> which would react with the neutrophils.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Procainamide hydroxylamine has more <a href="/wiki/Cytotoxicity" title="Cytotoxicity">cytotoxicity</a> by hindering the response of lymphocytes to <a href="/wiki/T-cell" class="mw-redirect" title="T-cell">T-cell</a> and B-cell <a href="/wiki/Mitogens" class="mw-redirect" title="Mitogens">mitogens</a>. Hydroxylamine can also generate <a href="/wiki/Methemoglobin" title="Methemoglobin">methemoglobin</a>, a protein that could hinder further oxygen exchange.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>It was also detected that the antiarrhythmic drug procainamide interferes with pacemakers. A toxic level of procainamide leads to decrease in ventricular conduction velocity and increase of the ventricular refractory period. This results in a disturbance in the artificial membrane potential and leads to a <a href="/wiki/Supraventricular_tachycardia" title="Supraventricular tachycardia">supraventricular tachycardia</a> which induces failure of the <a href="/wiki/Pacemaker" class="mw-redirect" title="Pacemaker">pacemaker</a> and death.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Thus, it prolongs QT interval of action potential and increases the risk of <a href="/wiki/Torsade_de_pointes" class="mw-redirect" title="Torsade de pointes">torsade de pointes</a>.<sup id="cite_ref-Osadchii_1-1" class="reference"><a href="#cite_note-Osadchii-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Procainamide could initiate <a href="/wiki/Leukopenia" title="Leukopenia">leukopenia</a> and/or <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>, which are serious hematologic disorders, and is also known for causing gastrointestinal disturbances and aggravating pre-existing abnormalities in impulse initiation and propagation.<sup id="cite_ref-Gould_3-1" class="reference"><a href="#cite_note-Gould-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=6" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=7" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Procainamide works as an <a href="/wiki/Anti-arrhythmic" class="mw-redirect" title="Anti-arrhythmic">anti-arrhythmic</a> agent and is used to treat <a href="/wiki/Cardiac_arrhythmia" class="mw-redirect" title="Cardiac arrhythmia">cardiac arrhythmia</a>. It induces rapid block of the <a href="/wiki/Batrachotoxin" title="Batrachotoxin">batrachotoxin (BTX)-activated</a> <a href="/wiki/Sodium_channels" class="mw-redirect" title="Sodium channels">sodium channels</a> of the heart muscle and acts as antagonist to long-gating closures. The block is voltage-dependent and can occur from both sides; either from the intracellular or the extracellular side. Blocking from the extracellular side is weaker than from the intracellular side because it occurs via the <a href="/w/index.php?title=Hydrophobic_pathway&action=edit&redlink=1" class="new" title="Hydrophobic pathway (page does not exist)">hydrophobic pathway</a>. Procainamide is present in charged form and probably requires a direct hydrophobic access to the binding site for blocking of the channel. Furthermore, blocking of the channel shows a decreased voltage sensitivity, which may result from the loss of voltage dependence of the blocking rate. Due to its charged and hydrophilic form, procainamide has its effect from the internal side, where it causes blockage of voltage-dependent, open channels. With increasing concentration of procainamide, the frequency of long blockage becomes less without the duration of blockage being affected. The rate of fast blocking is determined by the membrane depolarization. Membrane <a href="/wiki/Depolarization" title="Depolarization">depolarization</a> leads to increased blocking and decreased unblocking of the channels. Procainamide slows the conduction velocity and increases the <a href="/wiki/Refractory_period_(physiology)" title="Refractory period (physiology)">refractory period</a>, such that the maximal rate of depolarization is reduced.<sup id="cite_ref-Zamponi_2-1" class="reference"><a href="#cite_note-Zamponi-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is also said to be a <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">muscarinic acetylcholine</a> <a href="/wiki/M3_receptor" class="mw-redirect" title="M3 receptor">M<sub>3</sub> receptor</a> antagonist.<sup id="cite_ref-LavradorCabralVeríssimo2023_16-0" class="reference"><a href="#cite_note-LavradorCabralVeríssimo2023-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=8" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Procainamide is metabolized via different pathways. The most common one is the <a href="/wiki/Acetylation" title="Acetylation">acetylation</a> of procainamide to the less-toxic <a href="/wiki/N-acetylprocainamide" class="mw-redirect" title="N-acetylprocainamide">N-acetylprocainamide</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The rate of acetylation is genetically determined. There are two phenotypes that result from the acetylation process, namely the slow and rapid acetylator. Procainamide can also be oxidized by the <a href="/wiki/Cytochrome_P-450" class="mw-redirect" title="Cytochrome P-450">cytochrome P-450</a> to a reactive oxide metabolite. But it seems that acetylation of the nitrogen group of procainamide decrease the amount of the chemical that would be available for the oxidative route.<sup id="cite_ref-Uetrecht,_J._P._1981_18-0" class="reference"><a href="#cite_note-Uetrecht,_J._P._1981-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Other metabolites of procainamide include desethyl-N-acetylprocainamide, desethylprocainamide, p-aminobenzoic acid, which are excreted via the urine. N-acetyl-4-aminobenzoic acid as well as N-acetyl-3-hydroxyprocainamide, N-acetylprocainamide-N-oxide and N-acetyl-4-aminohippuric acid are also metabolites of procainamide.<sup id="cite_ref-Uetrecht,_J._P._1981_18-1" class="reference"><a href="#cite_note-Uetrecht,_J._P._1981-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=9" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>4-amino-N-2-(diethylamino)ethyl-benzamide (also known as <a href="/wiki/Diethylethanolamine" title="Diethylethanolamine">para-amino-N-2-(diethylamino)ethyl-benzamide</a> because the amino substituent is attached to the para-position, <a href="/wiki/Arene_substitution_patterns" class="mw-redirect" title="Arene substitution patterns">Arene substitution patterns</a> of the <a href="/wiki/Benzene_ring" class="mw-redirect" title="Benzene ring">benzene ring</a>) is a synthetic <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the chemical formula C13-H21-N3-O.<sup id="cite_ref-Drug_19-0" class="reference"><a href="#cite_note-Drug-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Procainamide is structurally similar to <a href="/wiki/Procaine" title="Procaine">procaine</a>, but in place of an ester group, procainamide contains an amide group. This substitution is the reason why procainamide exhibits a longer half-life time than procaine.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Procainamide belongs to the <a href="/wiki/Benzamides" class="mw-redirect" title="Benzamides">aminobenzamides</a>. These are <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> derivatives consisting of an amide with a <a href="/wiki/Benzamide" title="Benzamide">benzamide</a> moiety and a <a href="/wiki/Triethylamine" title="Triethylamine">triethylamine</a> attached to the <a href="/wiki/Amide" title="Amide">amide</a> <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a>.<sup id="cite_ref-Drug_19-1" class="reference"><a href="#cite_note-Drug-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>In certain lines, the <i>para</i>-amino group might become a target site to attach further paraphernalia, e.g. <i>ref.</i> Ex18 in <span><a rel="nofollow" class="external text" href="https://patents.google.com/patent/US7115750">U.S. patent 7,115,750</a></span>. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=10" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Procainamide was approved by the US FDA on June 2, 1950, under the brand name "Pronestyl".<sup id="cite_ref-dafda_24-0" class="reference"><a href="#cite_note-dafda-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> It was launched by <a href="/wiki/Bristol-Myers_Squibb" class="mw-redirect" title="Bristol-Myers Squibb">Bristol-Myers Squibb</a> in 1951.<sup id="cite_ref-pmid18610401_25-0" class="reference"><a href="#cite_note-pmid18610401-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Due to the <a href="/wiki/Japanese_occupation_of_the_Dutch_East_Indies" title="Japanese occupation of the Dutch East Indies">loss of Indonesia</a> in <a href="/wiki/World_War_II" title="World War II">World War II</a>, the source for <a href="/wiki/Cinchona_alkaloids" class="mw-redirect" title="Cinchona alkaloids">cinchona alkaloids</a>, a precursor of <a href="/wiki/Quinidine" title="Quinidine">quinidine</a>, was reduced. This led to research for a new <a href="/wiki/Antiarrhythmic_drug" class="mw-redirect" title="Antiarrhythmic drug">antiarrhythmic drug</a>. As a result, <a href="/wiki/Procaine" title="Procaine">procaine</a> was discovered, which has similar cardiac effects as quinidine.<sup id="cite_ref-one_26-0" class="reference"><a href="#cite_note-one-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> In 1936 it was found by Mautz that by applying it directly on the <a href="/wiki/Myocardium" class="mw-redirect" title="Myocardium">myocardium</a>, the ventricular threshold for electrical stimulation was elevated.<sup id="cite_ref-pmid18610401_25-1" class="reference"><a href="#cite_note-pmid18610401-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> This mechanism is responsible for the antiarrhythmic effect. However, due to the short duration of action, caused by rapid enzymatic hydrolysis, its therapeutic applications were limited.<sup id="cite_ref-three_27-0" class="reference"><a href="#cite_note-three-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> In addition, procaine also caused tremors and <a href="/wiki/Respiratory_depression" class="mw-redirect" title="Respiratory depression">respiratory depression</a>.<sup id="cite_ref-three_27-1" class="reference"><a href="#cite_note-three-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-two_28-0" class="reference"><a href="#cite_note-two-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> All these adverse features stimulated the search for an alternative to procaine. Studies were done on various congeners and metabolites and this ultimately led to the discovery of procainamide by Mark <i>et al</i>. It was found that procainamide was effective for treating <a href="/wiki/Ventricular_arrhythmias" class="mw-redirect" title="Ventricular arrhythmias">ventricular arrhythmias</a>, but it had the same toxicity profile as quinidine, and it could cause <a href="/wiki/Systemic_lupus_erythematosus" class="mw-redirect" title="Systemic lupus erythematosus">systemic lupus erythematosus</a>-like syndrome.<sup id="cite_ref-one_26-1" class="reference"><a href="#cite_note-one-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-two_28-1" class="reference"><a href="#cite_note-two-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> These negative characteristics slowed the search for new antiarrhythmics based on the chemical structure of procainamide. In 1970 only five drugs were reported. These were the <a href="/wiki/Cardiac_glycosides" class="mw-redirect" title="Cardiac glycosides">cardiac glycosides</a>, <a href="/wiki/Quinidine" title="Quinidine">quinidine</a>, <a href="/wiki/Propranolol" title="Propranolol">propranolol</a>, <a href="/wiki/Lidocaine" title="Lidocaine">lidocaine</a> and <a href="/wiki/Diphenylhydantoin" class="mw-redirect" title="Diphenylhydantoin">diphenylhydantoin</a>. In January 1996, extended release procainamide hydrochloride (Procanbid extended-release tablets) was approved by the FDA.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Procainamide&action=edit&section=11" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Osadchii-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Osadchii_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Osadchii_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFOsadchii2014" class="citation journal cs1">Osadchii OE (August 2014). "Procainamide and lidocaine produce dissimilar changes in ventricular repolarization and arrhythmogenicity in guinea-pig". <i>Fundamental & Clinical Pharmacology</i>. <b>28</b> (4): 382–393. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Ffcp.12046">10.1111/fcp.12046</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23952942">23952942</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:5086017">5086017</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fundamental+%26+Clinical+Pharmacology&rft.atitle=Procainamide+and+lidocaine+produce+dissimilar+changes+in+ventricular+repolarization+and+arrhythmogenicity+in+guinea-pig&rft.volume=28&rft.issue=4&rft.pages=382-393&rft.date=2014-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5086017%23id-name%3DS2CID&rft_id=info%3Apmid%2F23952942&rft_id=info%3Adoi%2F10.1111%2Ffcp.12046&rft.aulast=Osadchii&rft.aufirst=OE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProcainamide" class="Z3988"></span></span> </li> <li id="cite_note-Zamponi-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Zamponi_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Zamponi_2-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZamponiSuiCoddingFrench1993" class="citation journal cs1">Zamponi GW, Sui X, Codding PW, French RJ (December 1993). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1225974">"Dual actions of procainamide on batrachotoxin-activated sodium channels: open channel block and prevention of inactivation"</a>. <i>Biophysical Journal</i>. <b>65</b> (6): 2324–2334. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1993BpJ....65.2324Z">1993BpJ....65.2324Z</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0006-3495%2893%2981291-8">10.1016/S0006-3495(93)81291-8</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1225974">1225974</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8312472">8312472</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biophysical+Journal&rft.atitle=Dual+actions+of+procainamide+on+batrachotoxin-activated+sodium+channels%3A+open+channel+block+and+prevention+of+inactivation&rft.volume=65&rft.issue=6&rft.pages=2324-2334&rft.date=1993-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1225974%23id-name%3DPMC&rft_id=info%3Apmid%2F8312472&rft_id=info%3Adoi%2F10.1016%2FS0006-3495%2893%2981291-8&rft_id=info%3Abibcode%2F1993BpJ....65.2324Z&rft.aulast=Zamponi&rft.aufirst=GW&rft.au=Sui%2C+X&rft.au=Codding%2C+PW&rft.au=French%2C+RJ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1225974&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProcainamide" class="Z3988"></span></span> </li> <li id="cite_note-Gould-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Gould_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Gould_3-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGould1983" class="citation book cs1">Gould LA, ed. 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class="cs1-format">(PDF)</span>. <i>Clinical Pharmacology and Bioharmaceutics Review</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Clinical+Pharmacology+and+Bioharmaceutics+Review&rft.atitle=Center+for+Drug+Evaluation+and+Research+Approval+Package+For%3A+Application+Number+NDA+20-545%2FS007&rft.date=2002&rft.aulast=Mishina&rft.aufirst=E&rft.au=Marroum%2C+P&rft_id=https%3A%2F%2Fwww.accessdata.fda.gov%2Fdrugsatfda_docs%2Fnda%2F2002%2F20545s007_Procanbid_biopharmr.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProcainamide" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output 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navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Antiarrhythmic_agents" title="Template:Antiarrhythmic agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antiarrhythmic_agents" title="Template talk:Antiarrhythmic agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antiarrhythmic_agents" title="Special:EditPage/Template:Antiarrhythmic agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antiarrhythmic_agents_(C01B)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antiarrhythmic_agent" title="Antiarrhythmic agent">Antiarrhythmic agents</a> (<a href="/wiki/ATC_code_C01#C01B" title="ATC code C01">C01B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Channel_blocker" title="Channel blocker">Channel blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="class_I(Na+_channel_blockers)" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiarrhythmic_agent#Class_I_agents" title="Antiarrhythmic agent">class I</a><br />(<a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Na<sup>+</sup> channel blockers</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">class Ia (<a href="/wiki/Cardiac_action_potential#Phase_0" title="Cardiac action potential">Phase 0</a>→ and <a href="/wiki/Cardiac_action_potential#Phase_3" title="Cardiac action potential">Phase 3</a>→)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ajmaline" title="Ajmaline">Ajmaline</a></li> <li><a href="/wiki/Disopyramide" title="Disopyramide">Disopyramide</a></li> <li><a href="/wiki/Dihydroquinidine" title="Dihydroquinidine">Hydroquinidine</a></li> <li><a href="/wiki/Lorajmine" title="Lorajmine">Lorajmine</a></li> <li><a href="/wiki/Prajmaline" title="Prajmaline">Prajmaline</a></li> <li><a class="mw-selflink selflink">Procainamide</a><sup>#</sup></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a><sup>#</sup></li> <li><a href="/wiki/Sparteine" title="Sparteine">Sparteine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">class Ib (<a href="/wiki/Cardiac_action_potential#Phase_3" title="Cardiac action potential">Phase 3</a>←)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Intravenous_therapy" title="Intravenous therapy">IV</a></i> <ul><li><a href="/wiki/Lidocaine" title="Lidocaine">Lidocaine</a><sup>#</sup></li></ul></li> <li><i><a href="/wiki/Enteral" class="mw-redirect" title="Enteral">enteral</a></i> <ul><li><a href="/wiki/Aprindine" title="Aprindine">Aprindine</a></li> <li><a href="/wiki/Mexiletine" title="Mexiletine">Mexiletine</a></li> <li><a href="/wiki/Tocainide" title="Tocainide">Tocainide</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">class Ic (<a href="/wiki/Cardiac_action_potential#Phase_0" title="Cardiac action potential">Phase 0</a>→)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Encainide" title="Encainide">Encainide</a><sup>‡</sup></li> <li><a href="/wiki/Ethacizine" title="Ethacizine">Ethacizine</a></li> <li><a href="/wiki/Flecainide" title="Flecainide">Flecainide</a></li> <li><a href="/wiki/Indecainide" title="Indecainide">Indecainide</a><sup>‡</sup></li> <li><a href="/wiki/Lorcainide" title="Lorcainide">Lorcainide</a></li> <li><a href="/wiki/Moracizine" title="Moracizine">Moracizine</a><sup>‡</sup></li> <li><a href="/wiki/Propafenone" title="Propafenone">Propafenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiarrhythmic_agent#Class_III_agents" title="Antiarrhythmic agent">class III</a><br />(<a href="/wiki/Cardiac_action_potential#Phase_3" title="Cardiac action potential">Phase 3</a>→, <a href="/wiki/Potassium_channel_blocker" title="Potassium channel blocker">K<sup>+</sup> channel blockers</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Bunaftine" title="Bunaftine">Bunaftine</a></li> <li><a href="/wiki/Celivarone" title="Celivarone">Celivarone</a><sup>†</sup></li> <li><a href="/wiki/Dofetilide" title="Dofetilide">Dofetilide</a></li> <li><a href="/wiki/Dronedarone" title="Dronedarone">Dronedarone</a></li> <li><a href="/wiki/E-4031" title="E-4031">E-4031</a><sup>†</sup></li> <li><a href="/wiki/Ibutilide" title="Ibutilide">Ibutilide</a></li> <li><a href="/wiki/Nifekalant" title="Nifekalant">Nifekalant</a></li> <li><a href="/wiki/Sotalol" title="Sotalol">Sotalol</a></li> <li><a href="/wiki/Tedisamil" title="Tedisamil">Tedisamil</a></li> <li><a href="/wiki/Vernakalant" title="Vernakalant">Vernakalant</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiarrhythmic_agent#Class_IV_agents" title="Antiarrhythmic agent">class IV</a><br />(<a href="/wiki/Cardiac_action_potential#Phase_4" title="Cardiac action potential">Phase 4</a>→, <a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Ca<sup>2+</sup> channel blockers</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diltiazem" title="Diltiazem">Diltiazem</a></li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a><sup>#</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a> <a href="/wiki/Agonist" title="Agonist">agonists</a><br />and <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiarrhythmic_agent#Class_II_agents" title="Antiarrhythmic agent">class II</a><br />(<a href="/wiki/Cardiac_action_potential#Phase_4" title="Cardiac action potential">Phase 4</a>→, <a href="/wiki/Beta_blocker" title="Beta blocker">β blockers</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nadolol" title="Nadolol">Nadolol</a></li> <li><a href="/wiki/Pindolol" title="Pindolol">Pindolol</a></li> <li><a href="/wiki/Propranolol" title="Propranolol">Propranolol</a></li> <li><i>cardioselective</i> <ul><li><a href="/wiki/Acebutolol" title="Acebutolol">Acebutolol</a></li> <li><a href="/wiki/Atenolol" title="Atenolol">Atenolol</a></li> <li><a href="/wiki/Esmolol" title="Esmolol">Esmolol</a></li> <li><a href="/wiki/Landiolol" title="Landiolol">Landiolol</a></li> <li><a href="/wiki/Metoprolol" title="Metoprolol">Metoprolol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adenosine_A1_receptor" title="Adenosine A1 receptor">A<sub>1</sub> agonist</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine" title="Adenosine">Adenosine</a></li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></li> <li><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Muscarinic_acetylcholine_receptor_M2" title="Muscarinic acetylcholine receptor M2">M<sub>2</sub></a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Muscarinic_antagonist" title="Muscarinic antagonist">muscarinic antagonist</a>: <a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Disopyramide" title="Disopyramide">Disopyramide</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a><br /><a href="/wiki/Muscarinic_agonist" title="Muscarinic agonist">muscarinic agonist</a>: <a href="/wiki/Digoxin" title="Digoxin">Digoxin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adrenergic_receptor#.CE.B1_receptors" title="Adrenergic receptor">α receptors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ion_transporter" title="Ion transporter">Ion transporters</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Na+/_K+-ATPase" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Na%2B/K%2B-ATPase" class="mw-redirect" title="Na+/K+-ATPase">Na<sup>+</sup>/ K<sup>+</sup>-ATPase</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Digitoxin" title="Digitoxin">Digitoxin</a></li> <li><a href="/wiki/Digoxin" title="Digoxin">Digoxin</a></li> <li><a href="/wiki/Ouabain" title="Ouabain">Ouabain</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Muscarinic_acetylcholine_receptor_modulators" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Muscarinic_acetylcholine_receptor_modulators" title="Template talk:Muscarinic acetylcholine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Muscarinic_acetylcholine_receptor_modulators" title="Special:EditPage/Template:Muscarinic acetylcholine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Muscarinic_acetylcholine_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">Muscarinic acetylcholine receptor</a> <a href="/wiki/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="/wiki/Muscarinic_acetylcholine_receptors" class="mw-redirect" title="Muscarinic acetylcholine receptors"><abbr title="Muscarinic acetylcholine receptors">mAChRs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Muscarinic acetylcholine receptors</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_agonist" title="Muscarinic agonist">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/77-LH-28-1" title="77-LH-28-1">77-LH-28-1</a></li> <li><a href="/wiki/AC-42" title="AC-42">AC-42</a></li> <li><a href="/w/index.php?title=AC-260,584&action=edit&redlink=1" class="new" title="AC-260,584 (page does not exist)">AC-260,584</a></li> <li><a href="/wiki/Aceclidine" title="Aceclidine">Aceclidine</a></li> <li><a href="/wiki/Acetylcholine" title="Acetylcholine">Acetylcholine</a></li> <li><a href="/w/index.php?title=AF30&action=edit&redlink=1" class="new" title="AF30 (page does not exist)">AF30</a></li> <li><a href="/w/index.php?title=AF150(S)&action=edit&redlink=1" class="new" title="AF150(S) (page does not exist)">AF150(S)</a></li> <li><a href="/w/index.php?title=AF267B&action=edit&redlink=1" class="new" title="AF267B (page does not exist)">AF267B</a></li> <li><a href="/wiki/Alvameline" title="Alvameline">Alvameline</a></li> <li><a href="/w/index.php?title=AQRA-741&action=edit&redlink=1" class="new" title="AQRA-741 (page does not exist)">AQRA-741</a></li> <li><a href="/wiki/Arecoline" title="Arecoline">Arecoline</a></li> <li><a href="/wiki/Bethanechol" title="Bethanechol">Bethanechol</a></li> <li><a href="/wiki/Butyrylcholine" title="Butyrylcholine">Butyrylcholine</a></li> <li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li> <li><a href="/w/index.php?title=CDD-0034&action=edit&redlink=1" class="new" title="CDD-0034 (page does not exist)">CDD-0034</a></li> <li><a href="/w/index.php?title=CDD-0078&action=edit&redlink=1" class="new" title="CDD-0078 (page does not exist)">CDD-0078</a></li> <li><a href="/w/index.php?title=CDD-0097&action=edit&redlink=1" class="new" title="CDD-0097 (page does not exist)">CDD-0097</a></li> <li><a href="/w/index.php?title=CDD-0098&action=edit&redlink=1" class="new" title="CDD-0098 (page does not exist)">CDD-0098</a></li> <li><a href="/w/index.php?title=CDD-0102&action=edit&redlink=1" class="new" title="CDD-0102 (page does not exist)">CDD-0102</a></li> <li><a href="/wiki/Cevimeline" title="Cevimeline">Cevimeline</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Cis-Dioxolane" class="mw-redirect" title="Cis-Dioxolane">cis-Dioxolane</a></li> <li><a href="/wiki/Clozapine" title="Clozapine">Clozapine</a></li> <li><a href="/wiki/Desmethylclozapine" title="Desmethylclozapine">Desmethylclozapine (norclozapine)</a></li> <li><a href="/w/index.php?title=Ethoxysebacylcholine&action=edit&redlink=1" class="new" title="Ethoxysebacylcholine (page does not exist)">Ethoxysebacylcholine</a></li> <li><a href="/wiki/Itameline" title="Itameline">Itameline</a></li> <li><a href="/w/index.php?title=LY-593,039&action=edit&redlink=1" class="new" title="LY-593,039 (page does not exist)">LY-593,039</a></li> <li><a href="/w/index.php?title=L-689,660&action=edit&redlink=1" class="new" title="L-689,660 (page does not exist)">L-689,660</a></li> <li><a href="/w/index.php?title=LY-2,033,298&action=edit&redlink=1" class="new" title="LY-2,033,298 (page does not exist)">LY-2,033,298</a></li> <li><a href="/w/index.php?title=McNA343&action=edit&redlink=1" class="new" title="McNA343 (page does not exist)">McNA343</a></li> <li><a href="/wiki/Methacholine" title="Methacholine">Methacholine</a></li> <li><a href="/wiki/Milameline" title="Milameline">Milameline</a></li> <li><a href="/wiki/Muscarine" title="Muscarine">Muscarine</a></li> <li><a href="/w/index.php?title=NGX-267&action=edit&redlink=1" class="new" title="NGX-267 (page does not exist)">NGX-267</a></li> <li><a href="/w/index.php?title=Ocvimeline&action=edit&redlink=1" class="new" title="Ocvimeline (page does not exist)">Ocvimeline</a></li> <li><a href="/wiki/Oxotremorine" title="Oxotremorine">Oxotremorine</a></li> <li><a href="/w/index.php?title=PD-151,832&action=edit&redlink=1" class="new" title="PD-151,832 (page does not exist)">PD-151,832</a></li> <li><a href="/wiki/Pilocarpine" title="Pilocarpine">Pilocarpine</a></li> <li><a href="/w/index.php?title=RS86&action=edit&redlink=1" class="new" title="RS86 (page does not exist)">RS86</a></li> <li><a href="/wiki/Sabcomeline" title="Sabcomeline">Sabcomeline</a></li> <li><a href="/w/index.php?title=SDZ_210-086&action=edit&redlink=1" class="new" title="SDZ 210-086 (page does not exist)">SDZ 210-086</a></li> <li><a href="/w/index.php?title=Sebacylcholine&action=edit&redlink=1" class="new" title="Sebacylcholine (page does not exist)">Sebacylcholine</a></li> <li><a href="/w/index.php?title=Suberyldicholine&action=edit&redlink=1" class="new" title="Suberyldicholine (page does not exist)">Suberyldicholine</a></li> <li><a href="/wiki/Talsaclidine" title="Talsaclidine">Talsaclidine</a></li> <li><a href="/wiki/Tazomeline" title="Tazomeline">Tazomeline</a></li> <li><a href="/w/index.php?title=Thiopilocarpine&action=edit&redlink=1" class="new" title="Thiopilocarpine (page does not exist)">Thiopilocarpine</a></li> <li><a href="/wiki/Vedaclidine" title="Vedaclidine">Vedaclidine</a></li> <li><a href="/w/index.php?title=VU-0029767&action=edit&redlink=1" class="new" title="VU-0029767 (page does not exist)">VU-0029767</a></li> <li><a href="/w/index.php?title=VU-0090157&action=edit&redlink=1" class="new" title="VU-0090157 (page does not exist)">VU-0090157</a></li> <li><a href="/wiki/VU-0152099" title="VU-0152099">VU-0152099</a></li> <li><a href="/wiki/VU-0152100" title="VU-0152100">VU-0152100</a></li> <li><a href="/wiki/VU-0238429" title="VU-0238429">VU-0238429</a></li> <li><a href="/w/index.php?title=WAY-132,983&action=edit&redlink=1" class="new" title="WAY-132,983 (page does not exist)">WAY-132,983</a></li> <li><a href="/wiki/Xanomeline" title="Xanomeline">Xanomeline</a></li> <li><a href="/w/index.php?title=YM-796&action=edit&redlink=1" class="new" title="YM-796 (page does not exist)">YM-796</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Muscarinic_antagonist" title="Muscarinic antagonist">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3-Quinuclidinyl_benzilate" title="3-Quinuclidinyl benzilate">3-Quinuclidinyl benzilate</a></li> <li><a href="/wiki/4-DAMP" title="4-DAMP">4-DAMP</a></li> <li><a href="/wiki/Aclidinium_bromide" title="Aclidinium bromide">Aclidinium bromide</a> (<a href="/wiki/Aclidinium_bromide/formoterol" title="Aclidinium bromide/formoterol">+formoterol</a>)</li> <li><a href="/wiki/Abediterol" title="Abediterol">Abediterol</a></li> <li><a href="/w/index.php?title=AF-DX_250&action=edit&redlink=1" class="new" title="AF-DX 250 (page does not exist)">AF-DX 250</a></li> <li><a href="/wiki/AFDX-384" title="AFDX-384">AF-DX 384</a></li> <li><a href="/wiki/Ambutonium_bromide" title="Ambutonium bromide">Ambutonium bromide</a></li> <li><a href="/wiki/Anisodamine" title="Anisodamine">Anisodamine</a></li> <li><a href="/wiki/Anisodine" title="Anisodine">Anisodine</a></li> <li><a href="/wiki/First-generation_antihistamine" class="mw-redirect" title="First-generation antihistamine">Antihistamines (first-generation)</a> (e.g., <a href="/wiki/Brompheniramine" title="Brompheniramine">brompheniramine</a>, <a href="/wiki/Buclizine" title="Buclizine">buclizine</a>, <a href="/wiki/Captodiame" title="Captodiame">captodiame</a>, <a href="/wiki/Chlorphenamine" title="Chlorphenamine">chlorphenamine (chlorpheniramine)</a>, <a href="/wiki/Cinnarizine" title="Cinnarizine">cinnarizine</a>, <a href="/wiki/Clemastine" title="Clemastine">clemastine</a>, <a href="/wiki/Cyproheptadine" title="Cyproheptadine">cyproheptadine</a>, <a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">dimenhydrinate</a>, <a href="/wiki/Dimetindene" title="Dimetindene">dimetindene</a>, <a href="/wiki/Diphenhydramine" title="Diphenhydramine">diphenhydramine</a>, <a href="/wiki/Doxylamine" title="Doxylamine">doxylamine</a>, <a href="/wiki/Meclizine" title="Meclizine">meclizine</a>, <a href="/wiki/Mequitazine" title="Mequitazine">mequitazine</a>, <a href="/wiki/Perlapine" title="Perlapine">perlapine</a>, <a href="/wiki/Phenindamine" title="Phenindamine">phenindamine</a>, <a href="/wiki/Pheniramine" title="Pheniramine">pheniramine</a>, <a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">phenyltoloxamine</a>, <a href="/wiki/Promethazine" title="Promethazine">promethazine</a>, <a href="/wiki/Propiomazine" title="Propiomazine">propiomazine</a>, <a href="/wiki/Triprolidine" title="Triprolidine">triprolidine</a>)</li> <li><a href="/w/index.php?title=AQ-RA_741&action=edit&redlink=1" class="new" title="AQ-RA 741 (page does not exist)">AQ-RA 741</a></li> <li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Atropine_methonitrate" class="mw-redirect" title="Atropine methonitrate">Atropine methonitrate</a></li> <li><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Fluperlapine" title="Fluperlapine">fluperlapine</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a> (<a href="/wiki/Olanzapine/fluoxetine" title="Olanzapine/fluoxetine">+fluoxetine</a>), <a href="/w/index.php?title=Rilapine&action=edit&redlink=1" class="new" title="Rilapine (page does not exist)">rilapine</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Tenilapine" title="Tenilapine">tenilapine</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Benactyzine" title="Benactyzine">Benactyzine</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine (benztropine)</a></li> <li><a href="/wiki/Benzilone" title="Benzilone">Benzilone</a></li> <li><a href="/wiki/Benzilylcholine_mustard" title="Benzilylcholine mustard">Benzilylcholine mustard</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Bevonium" title="Bevonium">Bevonium</a></li> <li><a href="/w/index.php?title=BIBN_99&action=edit&redlink=1" class="new" title="BIBN 99 (page does not exist)">BIBN 99</a></li> <li><a href="/wiki/Biperiden" title="Biperiden">Biperiden</a></li> <li><a href="/wiki/Bornaprine" title="Bornaprine">Bornaprine</a></li> <li><a href="/wiki/Camylofin" title="Camylofin">Camylofin</a></li> <li><a href="/wiki/CAR-226,086" title="CAR-226,086">CAR-226,086</a></li> <li><a href="/wiki/CAR-301,060" title="CAR-301,060">CAR-301,060</a></li> <li><a href="/wiki/CAR-302,196" title="CAR-302,196">CAR-302,196</a></li> <li><a href="/wiki/CAR-302,282" title="CAR-302,282">CAR-302,282</a></li> <li><a href="/w/index.php?title=CAR-302,368&action=edit&redlink=1" class="new" title="CAR-302,368 (page does not exist)">CAR-302,368</a></li> <li><a href="/w/index.php?title=CAR-302,537&action=edit&redlink=1" class="new" title="CAR-302,537 (page does not exist)">CAR-302,537</a></li> <li><a href="/wiki/CAR-302,668" title="CAR-302,668">CAR-302,668</a></li> <li><a href="/wiki/Caramiphen" title="Caramiphen">Caramiphen</a></li> <li><a href="/wiki/Cimetropium_bromide" title="Cimetropium bromide">Cimetropium bromide</a></li> <li><a href="/wiki/Clidinium_bromide" title="Clidinium bromide">Clidinium bromide</a></li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/CS-27349" title="CS-27349">CS-27349</a></li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/wiki/Cyclopentolate" title="Cyclopentolate">Cyclopentolate</a></li> <li><a href="/wiki/Darifenacin" title="Darifenacin">Darifenacin</a></li> <li><a href="/w/index.php?title=DAU-5884&action=edit&redlink=1" class="new" title="DAU-5884 (page does not exist)">DAU-5884</a></li> <li><a href="/wiki/Desfesoterodine" title="Desfesoterodine">Desfesoterodine</a></li> <li><a href="/wiki/Dexetimide" title="Dexetimide">Dexetimide</a></li> <li><a href="/w/index.php?title=DIBD&action=edit&redlink=1" class="new" title="DIBD (page does not exist)">DIBD</a></li> <li><a href="/wiki/Dicycloverine" title="Dicycloverine">Dicycloverine (dicyclomine)</a></li> <li><a href="/wiki/Dihexyverine" title="Dihexyverine">Dihexyverine</a></li> <li><a href="/wiki/Difemerine" title="Difemerine">Difemerine</a></li> <li><a href="/wiki/Diphemanil_metilsulfate" title="Diphemanil metilsulfate">Diphemanil metilsulfate</a></li> <li><a href="/wiki/Ditran" title="Ditran">Ditran</a></li> <li><a href="/wiki/Drofenine" title="Drofenine">Drofenine</a></li> <li><a href="/wiki/EA-3167" title="EA-3167">EA-3167</a></li> <li><a href="/wiki/EA-3443" title="EA-3443">EA-3443</a></li> <li><a href="/wiki/EA-3580" title="EA-3580">EA-3580</a></li> <li><a href="/wiki/EA-3834" title="EA-3834">EA-3834</a></li> <li><a href="/wiki/Emepronium_bromide" title="Emepronium bromide">Emepronium bromide</a></li> <li><a href="/wiki/Etanautine" title="Etanautine">Etanautine</a></li> <li><a href="/wiki/Etybenzatropine" title="Etybenzatropine">Etybenzatropine (ethybenztropine)</a></li> <li><a href="/wiki/Fenpiverinium" title="Fenpiverinium">Fenpiverinium</a></li> <li><a href="/wiki/Fentonium_bromide" title="Fentonium bromide">Fentonium bromide</a></li> <li><a href="/wiki/Fesoterodine" title="Fesoterodine">Fesoterodine</a></li> <li><a href="/wiki/Flavoxate" title="Flavoxate">Flavoxate</a></li> <li><a href="/wiki/Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a> (<a href="/wiki/Beclometasone/formoterol/glycopyrronium_bromide" title="Beclometasone/formoterol/glycopyrronium bromide">+beclometasone/formoterol</a>, <a href="/wiki/Indacaterol/glycopyrronium_bromide" title="Indacaterol/glycopyrronium bromide">+indacaterol</a>, <a href="/wiki/Neostigmine/glycopyrronium_bromide" title="Neostigmine/glycopyrronium bromide">+neostigmine</a>)</li> <li><a href="/w/index.php?title=Hexahydrodifenidol&action=edit&redlink=1" class="new" title="Hexahydrodifenidol (page does not exist)">Hexahydrodifenidol</a></li> <li><a href="/w/index.php?title=Hexahydrosiladifenidol&action=edit&redlink=1" class="new" title="Hexahydrosiladifenidol (page does not exist)">Hexahydrosiladifenidol</a></li> <li><a href="/w/index.php?title=Hexbutinol&action=edit&redlink=1" class="new" title="Hexbutinol (page does not exist)">Hexbutinol</a></li> <li><a href="/wiki/Hexocyclium" title="Hexocyclium">Hexocyclium</a></li> <li><a href="/wiki/Himbacine" title="Himbacine">Himbacine</a></li> <li><a href="/w/index.php?title=HL-031,120&action=edit&redlink=1" class="new" title="HL-031,120 (page does not exist)">HL-031,120</a></li> <li><a href="/wiki/Homatropine" title="Homatropine">Homatropine</a></li> <li><a href="/wiki/Imidafenacin" title="Imidafenacin">Imidafenacin</a></li> <li><a href="/wiki/Ipratropium_bromide" title="Ipratropium bromide">Ipratropium bromide</a> (<a href="/wiki/Ipratropium_bromide/salbutamol" title="Ipratropium bromide/salbutamol">+salbutamol</a>)</li> <li><a href="/wiki/Isopropamide" title="Isopropamide">Isopropamide</a></li> <li><a href="/w/index.php?title=J-104,129&action=edit&redlink=1" class="new" title="J-104,129 (page does not exist)">J-104,129</a></li> <li><a href="/wiki/Hyoscyamine" title="Hyoscyamine">Hyoscyamine</a></li> <li><a href="/wiki/Mamba#Mamba_toxins" title="Mamba">Mamba toxin 3</a></li> <li><a href="/wiki/Mamba#Mamba_toxins" title="Mamba">Mamba toxin 7</a></li> <li><a href="/wiki/Mazaticol" title="Mazaticol">Mazaticol</a></li> <li><a href="/wiki/Mebeverine" title="Mebeverine">Mebeverine</a></li> <li><a href="/wiki/Meladrazine" title="Meladrazine">Meladrazine</a></li> <li><a href="/wiki/Mepenzolate" title="Mepenzolate">Mepenzolate</a></li> <li><a href="/wiki/Methantheline" title="Methantheline">Methantheline</a></li> <li><a href="/wiki/Methoctramine" title="Methoctramine">Methoctramine</a></li> <li><a href="/wiki/Methylatropine" title="Methylatropine">Methylatropine</a></li> <li><a href="/wiki/Methylhomatropine" class="mw-redirect" title="Methylhomatropine">Methylhomatropine</a></li> <li><a href="/wiki/Methylscopolamine_bromide" title="Methylscopolamine bromide">Methylscopolamine</a></li> <li><a href="/wiki/Metixene" title="Metixene">Metixene</a></li> <li><a href="/wiki/Muscarinic_toxin_7" title="Muscarinic toxin 7">Muscarinic toxin 7</a></li> <li><a href="/wiki/N-Ethyl-3-piperidyl_benzilate" title="N-Ethyl-3-piperidyl benzilate">N-Ethyl-3-piperidyl benzilate</a></li> <li><a href="/wiki/N-Methyl-3-piperidyl_benzilate" title="N-Methyl-3-piperidyl benzilate">N-Methyl-3-piperidyl benzilate</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Octatropine_methylbromide" title="Octatropine methylbromide">Octatropine methylbromide (anisotropine methylbromide)</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Otenzepad" title="Otenzepad">Otenzepad (AF-DX 116)</a></li> <li><a href="/wiki/Otilonium_bromide" title="Otilonium bromide">Otilonium bromide</a></li> <li><a href="/wiki/Oxapium_iodide" title="Oxapium iodide">Oxapium iodide</a></li> <li><a href="/wiki/Oxitropium_bromide" title="Oxitropium bromide">Oxitropium bromide</a></li> <li><a href="/wiki/Oxybutynin" title="Oxybutynin">Oxybutynin</a></li> <li><a href="/wiki/Oxyphencyclimine" title="Oxyphencyclimine">Oxyphencyclimine</a></li> <li><a href="/wiki/Oxyphenonium_bromide" title="Oxyphenonium bromide">Oxyphenonium bromide</a></li> <li><a href="/w/index.php?title=PBID&action=edit&redlink=1" class="new" title="PBID (page does not exist)">PBID</a></li> <li><a href="/wiki/PD-102,807" title="PD-102,807">PD-102,807</a></li> <li><a href="/wiki/PD-0298029" title="PD-0298029">PD-0298029</a></li> <li><a href="/wiki/Penthienate" title="Penthienate">Penthienate</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine</a></li> <li><a href="/w/index.php?title=PFHHSiD&action=edit&redlink=1" class="new" title="PFHHSiD (page does not exist)">pFHHSiD</a></li> <li><a href="/wiki/Phenglutarimide" title="Phenglutarimide">Phenglutarimide</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Pipenzolate_bromide" title="Pipenzolate bromide">Pipenzolate bromide</a></li> <li><a href="/wiki/Piperidolate" title="Piperidolate">Piperidolate</a></li> <li><a href="/wiki/Pirenzepine" title="Pirenzepine">Pirenzepine</a></li> <li><a href="/wiki/Piroheptine" title="Piroheptine">Piroheptine</a></li> <li><a href="/wiki/Pizotifen" title="Pizotifen">Pizotifen</a></li> <li><a href="/wiki/Poldine" title="Poldine">Poldine</a></li> <li><a href="/wiki/Pridinol" title="Pridinol">Pridinol</a></li> <li><a href="/wiki/Prifinium_bromide" title="Prifinium bromide">Prifinium bromide</a></li> <li><a href="/wiki/Procyclidine" title="Procyclidine">Procyclidine</a></li> <li><a href="/wiki/Profenamine" title="Profenamine">Profenamine (ethopropazine)</a></li> <li><a href="/wiki/Propantheline_bromide" title="Propantheline bromide">Propantheline bromide</a></li> <li><a href="/wiki/Propiverine" title="Propiverine">Propiverine</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/3-Quinuclidinyl_thiochromane-4-carboxylate" title="3-Quinuclidinyl thiochromane-4-carboxylate">3-Quinuclidinyl thiochromane-4-carboxylate</a></li> <li><a href="/wiki/Revefenacin" title="Revefenacin">Revefenacin</a></li> <li><a href="/wiki/Rociverine" title="Rociverine">Rociverine</a></li> <li><a href="/w/index.php?title=RU-47,213&action=edit&redlink=1" class="new" title="RU-47,213 (page does not exist)">RU-47,213</a></li> <li><a href="/w/index.php?title=SCH-57,790&action=edit&redlink=1" class="new" title="SCH-57,790 (page does not exist)">SCH-57,790</a></li> <li><a href="/w/index.php?title=SCH-72,788&action=edit&redlink=1" class="new" title="SCH-72,788 (page does not exist)">SCH-72,788</a></li> <li><a href="/w/index.php?title=SCH-217,443&action=edit&redlink=1" class="new" title="SCH-217,443 (page does not exist)">SCH-217,443</a></li> <li><a href="/wiki/Hyoscine" class="mw-redirect" title="Hyoscine">Scopolamine (hyoscine)</a></li> <li><a href="/wiki/Hyoscine_butylbromide" title="Hyoscine butylbromide">Scopolamine butylbromide (hyoscine butylbromide)</a></li> <li><a href="/w/index.php?title=Silahexacyclium&action=edit&redlink=1" class="new" title="Silahexacyclium (page does not exist)">Silahexacyclium</a></li> <li><a href="/wiki/Sofpironium_bromide" title="Sofpironium bromide">Sofpironium bromide</a></li> <li><a href="/wiki/Solifenacin" title="Solifenacin">Solifenacin</a></li> <li><a href="/wiki/Selective_serotonin_reuptake_inhibitors" class="mw-redirect" title="Selective serotonin reuptake inhibitors"><abbr title="Selective serotonin reuptake inhibitors">SSRIs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective serotonin reuptake inhibitors</span> (e.g., <a href="/wiki/Femoxetine" title="Femoxetine">femoxetine</a>, <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a>)</li> <li><a href="/wiki/Telenzepine" title="Telenzepine">Telenzepine</a></li> <li><a href="/wiki/Terodiline" title="Terodiline">Terodiline</a></li> <li><a href="/wiki/Tetracyclic_antidepressant" title="Tetracyclic antidepressant">Tetracyclic antidepressants</a> (e.g., <a href="/wiki/Amoxapine" title="Amoxapine">amoxapine</a>, <a href="/wiki/Maprotiline" title="Maprotiline">maprotiline</a>, <a href="/wiki/Mianserin" title="Mianserin">mianserin</a>, <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>)</li> <li><a href="/wiki/Tiemonium_iodide" title="Tiemonium iodide">Tiemonium iodide</a></li> <li><a href="/wiki/Timepidium_bromide" title="Timepidium bromide">Timepidium bromide</a></li> <li><a href="/wiki/Tiotropium_bromide" title="Tiotropium bromide">Tiotropium bromide</a></li> <li><a href="/w/index.php?title=Tiquizium_bromide&action=edit&redlink=1" class="new" title="Tiquizium bromide (page does not exist)">Tiquizium bromide</a></li> <li><a href="/wiki/Tofenacin" title="Tofenacin">Tofenacin</a></li> <li><a href="/wiki/Tolterodine" title="Tolterodine">Tolterodine</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a> (<a href="/wiki/Amitriptyline/perphenazine" title="Amitriptyline/perphenazine">+perphenazine</a>), <a href="/wiki/Amitriptylinoxide" title="Amitriptylinoxide">amitriptylinoxide</a>, <a href="/wiki/Butriptyline" title="Butriptyline">butriptyline</a>, <a href="/wiki/Cidoxepin" title="Cidoxepin">cidoxepin</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Desipramine" title="Desipramine">desipramine</a>, <a href="/w/index.php?title=Desmethyldesipramine&action=edit&redlink=1" class="new" title="Desmethyldesipramine (page does not exist)">desmethyldesipramine</a>, <a href="/wiki/Dibenzepin" title="Dibenzepin">dibenzepin</a>, <a href="/wiki/Dosulepin" title="Dosulepin">dosulepin (dothiepin)</a>, <a href="/wiki/Doxepin" title="Doxepin">doxepin</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Lofepramine" title="Lofepramine">lofepramine</a>, <a href="/wiki/Nitroxazepine" title="Nitroxazepine">nitroxazepine</a>, <a href="/wiki/Northiaden" title="Northiaden">northiaden (desmethyldosulepin)</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="/wiki/Protriptyline" title="Protriptyline">protriptyline</a>, <a href="/wiki/Quinupramine" title="Quinupramine">quinupramine</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</a>)</li> <li><a href="/wiki/Tridihexethyl" title="Tridihexethyl">Tridihexethyl</a></li> <li><a href="/wiki/Trihexyphenidyl" title="Trihexyphenidyl">Trihexyphenidyl</a></li> <li><a href="/wiki/Trimebutine" title="Trimebutine">Trimebutine</a></li> <li><a href="/wiki/Tripitamine" class="mw-redirect" title="Tripitamine">Tripitamine (tripitramine)</a></li> <li><a href="/w/index.php?title=Tropacine&action=edit&redlink=1" class="new" title="Tropacine (page does not exist)">Tropacine</a></li> <li><a href="/wiki/Tropatepine" title="Tropatepine">Tropatepine</a></li> <li><a href="/wiki/Tropicamide" title="Tropicamide">Tropicamide</a></li> <li><a href="/wiki/Trospium_chloride" title="Trospium chloride">Trospium chloride</a></li> <li><a href="/wiki/Typical_antipsychotic" title="Typical antipsychotic">Typical antipsychotics</a> (e.g., <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Chlorprothixene" title="Chlorprothixene">chlorprothixene</a>, <a href="/wiki/Cyamemazine" title="Cyamemazine">cyamemazine (cyamepromazine)</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Mesoridazine" title="Mesoridazine">mesoridazine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>)</li> <li><a href="/wiki/Umeclidinium_bromide" title="Umeclidinium bromide">Umeclidinium bromide</a> (<a href="/wiki/Umeclidinium_bromide/vilanterol" title="Umeclidinium bromide/vilanterol">+vilanterol</a>)</li> <li><a href="/wiki/WIN-2299" title="WIN-2299">WIN-2299</a></li> <li><a href="/wiki/Xanomeline" title="Xanomeline">Xanomeline</a></li> <li><a href="/w/index.php?title=Zamifenacin&action=edit&redlink=1" class="new" title="Zamifenacin (page does not exist)">Zamifenacin</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="/wiki/Precursor_(chemistry)" title="Precursor (chemistry)">Precursors</a><br /><small>(and <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyl-coA" class="mw-redirect" title="Acetyl-coA">Acetyl-coA</a></li> <li><a href="/wiki/Adafenoxate" title="Adafenoxate">Adafenoxate</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a> (<a href="/wiki/Lecithin" title="Lecithin">lecithin</a>)</li> <li><a href="/wiki/Citicoline" title="Citicoline">Citicoline</a></li> <li><a href="/wiki/Cyprodenate" title="Cyprodenate">Cyprodenate</a></li> <li><a href="/wiki/Dimethylethanolamine" title="Dimethylethanolamine">Dimethylethanolamine</a></li> <li><a href="/wiki/Glycerophosphocholine" class="mw-redirect" title="Glycerophosphocholine">Glycerophosphocholine</a></li> <li><a href="/wiki/Meclofenoxate" title="Meclofenoxate">Meclofenoxate (centrophenoxine)</a></li> <li><a href="/wiki/Phosphatidylcholine" title="Phosphatidylcholine">Phosphatidylcholine</a></li> <li><a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">Phosphatidylethanolamine</a></li> <li><a href="/wiki/Phosphorylcholine" title="Phosphorylcholine">Phosphorylcholine</a></li> <li><a href="/wiki/Pirisudanol" title="Pirisudanol">Pirisudanol</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators">Nicotinic acetylcholine receptor modulators</a></dd> <dd><a 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