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class="vector-toc-numb">5</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Histamine_H2_receptor_antagonism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Histamine_H2_receptor_antagonism"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.1</span> <span>Histamine H<sub>2</sub> receptor antagonism</span> </div> </a> <ul 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<div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Research</span> </div> </a> <ul id="toc-Research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Veterinary_use" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Veterinary_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Veterinary use</span> </div> </a> <ul id="toc-Veterinary_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header 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</div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Cimetidine</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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href="https://azb.wikipedia.org/wiki/%D8%B3%D8%A7%DB%8C%D9%85%D8%AA%DB%8C%D8%AF%DB%8C%D9%86" title="سایمتیدین – South Azerbaijani" lang="azb" hreflang="azb" data-title="سایمتیدین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cimetidina" title="Cimetidina – Catalan" lang="ca" hreflang="ca" data-title="Cimetidina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Cimetidin" title="Cimetidin – Welsh" lang="cy" hreflang="cy" data-title="Cimetidin" 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/Cimetidin" title="Cimetidin – German" lang="de" hreflang="de" data-title="Cimetidin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A3%CE%B9%CE%BC%CE%B5%CF%84%CE%B9%CE%B4%CE%AF%CE%BD%CE%B7" title="Σιμετιδίνη – Greek" lang="el" hreflang="el" data-title="Σιμετιδίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cimetidina" title="Cimetidina – Spanish" lang="es" hreflang="es" data-title="Cimetidina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Cimetidino" title="Cimetidino – Esperanto" lang="eo" hreflang="eo" data-title="Cimetidino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%D8%A7%DB%8C%D9%85%D8%AA%DB%8C%D8%AF%DB%8C%D9%86" title="سایمتیدین – Persian" lang="fa" hreflang="fa" data-title="سایمتیدین" 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/Cim%C3%A9tidine" title="Cimétidine – French" lang="fr" hreflang="fr" data-title="Cimétidine" 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/%EC%8B%9C%EB%A9%94%ED%8B%B0%EB%94%98" title="시메티딘 – Korean" lang="ko" hreflang="ko" data-title="시메티딘" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%91%D5%AB%D5%B4%D5%A5%D5%BF%D5%AB%D5%A4%D5%AB%D5%B6" title="Ցիմետիդին – Armenian" lang="hy" hreflang="hy" data-title="Ցիմետիդին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Cimeditin" title="Cimeditin – Croatian" lang="hr" hreflang="hr" data-title="Cimeditin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Simetidin" title="Simetidin – Indonesian" lang="id" hreflang="id" data-title="Simetidin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cimetidina" title="Cimetidina – Italian" lang="it" hreflang="it" data-title="Cimetidina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Cimetidin" title="Cimetidin – Hungarian" lang="hu" hreflang="hu" data-title="Cimetidin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cimetidine" title="Cimetidine – Dutch" lang="nl" hreflang="nl" data-title="Cimetidine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B7%E3%83%A1%E3%83%81%E3%82%B8%E3%83%B3" title="シメチジン – Japanese" lang="ja" hreflang="ja" data-title="シメチジン" 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%B8%E0%AC%BF%E0%AC%AE%E0%AD%87%E0%AC%9F%E0%AC%BF%E0%AC%A1%E0%AC%BE%E0%AC%87%E0%AC%A8" title="ସିମେଟିଡାଇନ – Odia" lang="or" hreflang="or" data-title="ସିମେଟିଡାଇନ" 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/Cymetydyna" title="Cymetydyna – Polish" lang="pl" hreflang="pl" data-title="Cymetydyna" 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/Cimetidina" title="Cimetidina – Portuguese" lang="pt" hreflang="pt" data-title="Cimetidina" 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/Cimetidin%C4%83" title="Cimetidină – Romanian" lang="ro" hreflang="ro" data-title="Cimetidină" 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%A6%D0%B8%D0%BC%D0%B5%D1%82%D0%B8%D0%B4%D0%B8%D0%BD" title="Циметидин – Russian" lang="ru" hreflang="ru" data-title="Циметидин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Cimetidin" title="Cimetidin – Slovenian" lang="sl" hreflang="sl" data-title="Cimetidin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cimetidin" title="Cimetidin – Serbian" lang="sr" hreflang="sr" data-title="Cimetidin" 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/Cimetidin" title="Cimetidin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cimetidin" 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/Simetidiini" title="Simetidiini – Finnish" lang="fi" hreflang="fi" data-title="Simetidiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%84%E0%B8%8B%E0%B9%80%E0%B8%A1%E0%B8%97%E0%B8%B4%E0%B8%94%E0%B8%B5%E0%B8%99" title="ไซเมทิดีน – Thai" lang="th" hreflang="th" data-title="ไซเมทิดีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Simetidin" title="Simetidin – Turkish" lang="tr" hreflang="tr" data-title="Simetidin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A6%D0%B8%D0%BC%D0%B5%D1%82%D0%B8%D0%B4%D0%B8%D0%BD" title="Циметидин – Ukrainian" lang="uk" hreflang="uk" data-title="Циметидин" 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/%E8%A5%BF%E5%92%AA%E6%9B%BF%E4%B8%81" title="西咪替丁 – Chinese" lang="zh" hreflang="zh" data-title="西咪替丁" data-language-autonym="中文" data-language-local-name="Chinese" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Medication</div> <p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <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): Cimetidine">Cimetidine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Cimetidine_Structural_Formula_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Cimetidine_Structural_Formula_V.1.svg/250px-Cimetidine_Structural_Formula_V.1.svg.png" decoding="async" width="250" height="94" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/25/Cimetidine_Structural_Formula_V.1.svg/375px-Cimetidine_Structural_Formula_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/25/Cimetidine_Structural_Formula_V.1.svg/500px-Cimetidine_Structural_Formula_V.1.svg.png 2x" data-file-width="601" data-file-height="225" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Cimetidine-xtal-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Cimetidine-xtal-3D-balls.png/250px-Cimetidine-xtal-3D-balls.png" decoding="async" width="250" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Cimetidine-xtal-3D-balls.png/375px-Cimetidine-xtal-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Cimetidine-xtal-3D-balls.png/500px-Cimetidine-xtal-3D-balls.png 2x" data-file-width="1100" data-file-height="667" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">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="'s' in 'sigh'">s</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'m' in 'my'">m</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="'t' in 'tie'">t</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'d' in 'dye'">d</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> or <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="'s' in 'sigh'">s</span><span title="/aɪ/: 'i' in 'tide'">aɪ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'m' in 'my'">m</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="'t' in 'tie'">t</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'d' in 'dye'">d</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</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">Tagamet, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">SKF-92334<sup id="cite_ref-Elks2014_1-0" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></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/cimetidine.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a682256.html">a682256</a></span></td></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">License data</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><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Cimetidine">Cimetidine</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</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="Australia">AU</abbr>:</small> B1</li> <li class="mw-empty-elt"></li></ul> </div></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/Oral_administration" title="Oral administration">By mouth</a>, <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous infusion</a><sup id="cite_ref-GuptaSingh-Radcliff2013_2-0" class="reference"><a href="#cite_note-GuptaSingh-Radcliff2013-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_A02" title="ATC code A02">A02BA01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=A02BA01">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/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="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)</li> <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> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a> / OTC<sup id="cite_ref-Cimetidine_FDA_label_3-0" class="reference"><a href="#cite_note-Cimetidine_FDA_label-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Tagamet_FDA_label_4-0" class="reference"><a href="#cite_note-Tagamet_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><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">60–70%<sup id="cite_ref-DowdJohnson2016_5-0" class="reference"><a href="#cite_note-DowdJohnson2016-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LeikinPaloucek1995_6-0" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></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">13–25%<sup id="cite_ref-LeikinPaloucek1995_6-1" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AcademicPress1984_7-0" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></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><sup id="cite_ref-LeikinPaloucek1995_6-5" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• Cimetidine sulfoxide<sup id="cite_ref-LeikinPaloucek1995_6-2" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><br />• Hydroxycimetidine<sup id="cite_ref-LeikinPaloucek1995_6-3" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><br />• Guanyl urea cimetidine<sup id="cite_ref-LeikinPaloucek1995_6-4" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Onset_of_action" title="Onset of action">Onset of action</a></th><td class="infobox-data">30 minutes<sup id="cite_ref-VallerandSanoski2016_8-0" class="reference"><a href="#cite_note-VallerandSanoski2016-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></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">123 minutes (~2 hours)<sup id="cite_ref-AcademicPress1984_7-1" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data">4–8 hours<sup id="cite_ref-GuptaSingh-Radcliff2013_2-1" class="reference"><a href="#cite_note-GuptaSingh-Radcliff2013-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></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/Urine" title="Urine">Urine</a><sup id="cite_ref-AcademicPress1984_7-2" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/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%;">1-cyano-2-methyl-3-[2-[(5-methyl-1<i>H</i>-imidazol-4-yl)methylsulfanyl]ethyl]guanidine</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=51481-61-9">51481-61-9</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/2756">2756</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=1231">1231</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/DB00501">DB00501</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.2654.html">2654</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/80061L1WGD">80061L1WGD</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/D00295">D00295</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:3699">CHEBI:3699</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/chembl/explore/compound/ChEMBL30">ChEMBL30</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/DTXSID4020329">DTXSID4020329</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409492#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/100.052.012">100.052.012</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q409492#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;color:inherit;">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>10</sub><span title="Hydrogen">H</span><sub>16</sub><span title="Nitrogen">N</span><sub>6</sub><span title="Sulfur">S</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="7002252340000000000♠"></span>252.34</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=CC1%3DC%28N%3DCN1%29CSCCNC%28%3DNC%29NC%23N">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%;">CC1=C(N=CN1)CSCCNC(=NC)NC#N</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/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)<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:AQIXAKUUQRKLND-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=456484490&page2=Cimetidine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Cimetidine</b>, sold under the brand name <b>Tagamet</b> among others, is a <a href="/wiki/Histamine" title="Histamine">histamine</a> <a href="/wiki/H2-receptor_antagonist" class="mw-redirect" title="H2-receptor antagonist">H<sub>2</sub> receptor antagonist</a> that inhibits <a href="/wiki/Stomach_acid" class="mw-redirect" title="Stomach acid">stomach acid</a> production.<sup id="cite_ref-Elks2014_1-1" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_9-0" class="reference"><a href="#cite_note-IndexNominum2000-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonMorton1999_10-0" class="reference"><a href="#cite_note-MortonMorton1999-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is mainly used in the treatment of <a href="/wiki/Heartburn" title="Heartburn">heartburn</a> and <a href="/wiki/Peptic_ulcer" class="mw-redirect" title="Peptic ulcer">peptic ulcers</a>.<sup id="cite_ref-Elks2014_1-2" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonMorton1999_10-1" class="reference"><a href="#cite_note-MortonMorton1999-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BurchumRosenthal2014_11-0" class="reference"><a href="#cite_note-BurchumRosenthal2014-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>With the development of proton pump inhibitors, such as omeprazole, approved for the same indications, cimetidine is available as an over-the-counter formulation to prevent heartburn or acid indigestion, along with the other H2-receptor antagonists.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Cimetidine was developed in 1971 and came into commercial use in 1977.<sup id="cite_ref-FischerGanellin2010_13-0" class="reference"><a href="#cite_note-FischerGanellin2010-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><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> Cimetidine was approved in the United Kingdom in 1976,<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2023)">citation needed</span></a></i>]</sup> and was approved in the United States by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> in 1979.<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> </p> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/H2_antagonist" class="mw-redirect" title="H2 antagonist">H2 antagonist</a></div> <p>Cimetidine is indicated for the treatment of <a href="/wiki/Duodenal_ulcer" class="mw-redirect" title="Duodenal ulcer">duodenal ulcers</a>, <a href="/wiki/Gastric_ulcer" class="mw-redirect" title="Gastric ulcer">gastric ulcers</a>, <a href="/wiki/Gastroesophageal_reflux_disease" title="Gastroesophageal reflux disease">gastroesophageal reflux disease</a>, and pathological hypersecretory conditions.<sup id="cite_ref-Cimetidine_FDA_label_3-1" class="reference"><a href="#cite_note-Cimetidine_FDA_label-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Cimetidine is also used to relieve or prevent heartburn.<sup id="cite_ref-Tagamet_FDA_label_4-1" class="reference"><a href="#cite_note-Tagamet_FDA_label-4"><span class="cite-bracket">[</span>4<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=Cimetidine&action=edit&section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Reported <a href="/wiki/Side_effect" title="Side effect">side effects</a> of cimetidine include <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, <a href="/wiki/Rash" title="Rash">rashes</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Fatigue_(medical)" class="mw-redirect" title="Fatigue (medical)">fatigue</a>, <a href="/wiki/Constipation" title="Constipation">constipation</a>, and <a href="/wiki/Myalgia" title="Myalgia">muscle pain</a>, all of which are usually mild and transient.<sup id="cite_ref-RitterLewis2008_16-0" class="reference"><a href="#cite_note-RitterLewis2008-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> It has been reported that <a href="/wiki/Mental_confusion" class="mw-redirect" title="Mental confusion">mental confusion</a> may occur in the elderly.<sup id="cite_ref-RitterLewis2008_16-1" class="reference"><a href="#cite_note-RitterLewis2008-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Because of its hormonal effects, cimetidine rarely may cause <a href="/wiki/Sexual_dysfunction" title="Sexual dysfunction">sexual dysfunction</a> including loss of <a href="/wiki/Libido" title="Libido">libido</a> and <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a> and <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> (0.1–0.2%) in males during long-term treatment.<sup id="cite_ref-RitterLewis2008_16-2" class="reference"><a href="#cite_note-RitterLewis2008-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><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><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Rarely, <a href="/wiki/Interstitial_nephritis" title="Interstitial nephritis">interstitial nephritis</a>, <a href="/wiki/Urticaria" class="mw-redirect" title="Urticaria">urticaria</a>, and <a href="/wiki/Angioedema" title="Angioedema">angioedema</a> have been reported with cimetidine treatment.<sup id="cite_ref-RitterLewis2008_16-3" class="reference"><a href="#cite_note-RitterLewis2008-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Cimetidine is also commonly associated with transient raised <a href="/wiki/Aminotransferase" class="mw-redirect" title="Aminotransferase">aminotransferase</a> activity; <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a> is rare.<sup id="cite_ref-Kelly2009_19-0" class="reference"><a href="#cite_note-Kelly2009-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=3" title="Edit section: Overdose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cimetidine appears to be very safe in <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a>, producing no <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a> even with massive overdoses (e.g., 20 g).<sup id="cite_ref-Dart2004_20-0" class="reference"><a href="#cite_note-Dart2004-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=4" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Due to its non-selective <a href="/wiki/Enzyme_inhibition" class="mw-redirect" title="Enzyme inhibition">inhibition</a> of <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>, cimetidine has numerous <a href="/wiki/Drug_interaction" title="Drug interaction">drug interactions</a>. Examples of specific interactions include, but are not limited to, the following: </p> <ul><li>Cimetidine affects the metabolism of <a href="/wiki/Methadone" title="Methadone">methadone</a>, sometimes resulting in higher blood levels and a higher incidence of side effects, and may interact with the <a href="/wiki/Antimalarial" class="mw-redirect" title="Antimalarial">antimalarial</a> medication <a href="/wiki/Hydroxychloroquine" title="Hydroxychloroquine">hydroxychloroquine</a>.<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></li> <li>Cimetidine can also interact with a number of psychoactive medications, including <a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">tricyclic antidepressants</a> and <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitors</a>, causing increased blood levels of these drugs and the potential of subsequent toxicity.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (August 2016)">citation needed</span></a></i>]</sup></li> <li>Following administration of cimetidine, the elimination half-life and <a href="/wiki/Area_under_the_curve_(pharmacokinetics)" title="Area under the curve (pharmacokinetics)">area-under-curve</a> of <a href="/wiki/Zolmitriptan" title="Zolmitriptan">zolmitriptan</a> and its <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolites</a> were roughly doubled.<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></li> <li>Cimetidine is a potent inhibitor of tubular <a href="/wiki/Creatinine" title="Creatinine">creatinine</a> secretion. Creatinine is a metabolic byproduct of <a href="/wiki/Creatine" title="Creatine">creatine</a> breakdown. Accumulation of creatinine is associated with <a href="/wiki/Uremia" title="Uremia">uremia</a>, but the symptoms of creatinine accumulation are unknown, as they are hard to separate from other nitrogenous waste buildups.<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></li> <li>Like several other medications (e.g., <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a>), cimetidine interferes with the body's metabolization of <a href="/wiki/Sildenafil" title="Sildenafil">sildenafil</a>, causing its strength and duration to increase and making its side effects more likely and prominent.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (August 2016)">citation needed</span></a></i>]</sup></li> <li>Clinically significant drug interactions with the CYP1A2 substrate <a href="/wiki/Theophylline" title="Theophylline">theophylline</a>, the CYP2C9 substrate <a href="/wiki/Tolbutamide" title="Tolbutamide">tolbutamide</a>, the CYP2D6 substrate <a href="/wiki/Desipramine" title="Desipramine">desipramine</a>, and the CYP3A4 substrate <a href="/wiki/Triazolam" title="Triazolam">triazolam</a> have all been demonstrated with cimetidine, and interactions with other substrates of these enzymes are likely as well.<sup id="cite_ref-Rodrigues2008_24-0" class="reference"><a href="#cite_note-Rodrigues2008-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup></li> <li>Cimetidine has been shown clinically to reduce the clearance of <a href="/wiki/Mirtazapine" title="Mirtazapine">mirtazapine</a>, <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>, <a href="/wiki/Timolol" title="Timolol">timolol</a>, <a href="/wiki/Nebivolol" title="Nebivolol">nebivolol</a>, <a href="/wiki/Sparteine" title="Sparteine">sparteine</a>, <a href="/wiki/Loratadine" title="Loratadine">loratadine</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="/wiki/Gabapentin" title="Gabapentin">gabapentin</a>, and <a href="/wiki/Desipramine" title="Desipramine">desipramine</a> in humans.<sup id="cite_ref-Zhou2016_25-0" class="reference"><a href="#cite_note-Zhou2016-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></li> <li>Cimetidine inhibits the <a href="/wiki/Renal" class="mw-redirect" title="Renal">renal</a> <a href="/wiki/Excretion" title="Excretion">excretion</a> of <a href="/wiki/Metformin" title="Metformin">metformin</a> and <a href="/wiki/Procainamide" title="Procainamide">procainamide</a>, resulting in increased circulating levels of these drugs.<sup id="cite_ref-RitterLewis2008_16-4" class="reference"><a href="#cite_note-RitterLewis2008-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></li> <li>Interactions of potential clinical importance with cimetidine include <a href="/wiki/Warfarin" title="Warfarin">warfarin</a>, <a href="/wiki/Theophylline" title="Theophylline">theophylline</a>, <a href="/wiki/Phenytoin" title="Phenytoin">phenytoin</a>, <a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine</a> and other <a href="/wiki/Opioid" title="Opioid">opioid</a> <a href="/wiki/Analgesic" title="Analgesic">analgesics</a>, <a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">tricyclic antidepressants</a>, <a href="/wiki/Lidocaine" title="Lidocaine">lidocaine</a>, <a href="/wiki/Terfenadine" title="Terfenadine">terfenadine</a>, <a href="/wiki/Amiodarone" title="Amiodarone">amiodarone</a>, <a href="/wiki/Flecainide" title="Flecainide">flecainide</a>, <a href="/wiki/Quinidine" title="Quinidine">quinidine</a>, <a href="/wiki/Fluorouracil" title="Fluorouracil">fluorouracil</a>, and <a href="/wiki/Benzodiazepine" title="Benzodiazepine">benzodiazepines</a>.<sup id="cite_ref-RitterLewis2008_16-5" class="reference"><a href="#cite_note-RitterLewis2008-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RosenfeldLoose2007_26-0" class="reference"><a href="#cite_note-RosenfeldLoose2007-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup></li> <li>Cimetidine may decrease the effects of CYP2D6 substrates that are <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a>, such as <a href="/wiki/Codeine" title="Codeine">codeine</a>, <a href="/wiki/Tramadol" title="Tramadol">tramadol</a>, and <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>.<sup id="cite_ref-FullerSajatovic2005_27-0" class="reference"><a href="#cite_note-FullerSajatovic2005-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup></li> <li>Cimetidine reduces the <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> of <a href="/wiki/Ketoconazole" title="Ketoconazole">ketoconazole</a> and <a href="/wiki/Itraconazole" title="Itraconazole">itraconazole</a> (which require a low <a href="/wiki/PH" title="PH">pH</a>).<sup id="cite_ref-RitterLewis2008_16-6" class="reference"><a href="#cite_note-RitterLewis2008-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup></li> <li>Cimetidine has a theoretical but unproven benefit in <a href="/wiki/Paracetamol_toxicity" class="mw-redirect" title="Paracetamol toxicity">paracetamol toxicity</a>.<sup id="cite_ref-Kelly2009_19-1" class="reference"><a href="#cite_note-Kelly2009-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> This is because <a href="/wiki/N-acetyl-p-benzoquinone_imine" class="mw-redirect" title="N-acetyl-p-benzoquinone imine">N-acetyl-p-benzoquinone imine</a> (NAPQI), a <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> (acetaminophen) that is responsible for its <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>, is formed from it by the cytochrome P450 system (specifically, CYP1A2, CYP2E1, and CYP3A4).<sup id="cite_ref-CameronFeuer2012_28-0" class="reference"><a href="#cite_note-CameronFeuer2012-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup></li> <li>Cimetidine is used in cancer metastasis research as a blocker of E-selectin.<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></li></ul> <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=Cimetidine&action=edit&section=5" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=6" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Histamine_H2_receptor_antagonism">Histamine H<sub>2</sub> receptor antagonism</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=7" title="Edit section: Histamine H2 receptor antagonism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Mechanism_of_action" title="Mechanism of action">mechanism of action</a> of cimetidine as an <a href="/wiki/Antacid" title="Antacid">antacid</a> is as a <a href="/wiki/Histamine" title="Histamine">histamine</a> <a href="/wiki/H2_receptor" class="mw-redirect" title="H2 receptor">H<sub>2</sub> receptor</a> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a>.<sup id="cite_ref-pmid6317740_30-0" class="reference"><a href="#cite_note-pmid6317740-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> It has been found to bind to the H<sub>2</sub> receptor with a K<sub>d</sub> of 42 nM.<sup id="cite_ref-Osborne2013_31-0" class="reference"><a href="#cite_note-Osborne2013-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Cytochrome_P450_inhibition">Cytochrome P450 inhibition</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=8" title="Edit section: Cytochrome P450 inhibition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cimetidine is a <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a> of certain <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> (CYP) <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>,<sup id="cite_ref-Dart2004_20-1" class="reference"><a href="#cite_note-Dart2004-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LemkeWilliams2008_32-0" class="reference"><a href="#cite_note-LemkeWilliams2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> including <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a>, <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a>, <a href="/wiki/CYP2C19" title="CYP2C19">CYP2C19</a>, <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a>, <a href="/wiki/CYP2E1" title="CYP2E1">CYP2E1</a>, and <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>.<sup id="cite_ref-Dart2004_20-2" class="reference"><a href="#cite_note-Dart2004-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LemkeWilliams2008_32-1" class="reference"><a href="#cite_note-LemkeWilliams2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KarallieddeClarke2010_33-0" class="reference"><a href="#cite_note-KarallieddeClarke2010-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The drug appears to primarily inhibit CYP1A2, CYP2D6, and CYP3A4,<sup id="cite_ref-PriskornLarsen1997_34-0" class="reference"><a href="#cite_note-PriskornLarsen1997-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> of which it is described as a moderate inhibitor.<sup id="cite_ref-VallerandSanoski2016_8-1" class="reference"><a href="#cite_note-VallerandSanoski2016-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> This is notable since these three CYP <a href="/wiki/Isoenzyme" class="mw-redirect" title="Isoenzyme">isoenzymes</a> are involved in CYP-mediated drug <a href="/wiki/Biotransformation" title="Biotransformation">biotransformations</a>;<sup id="cite_ref-MartinezAlbet1999_35-0" class="reference"><a href="#cite_note-MartinezAlbet1999-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> however, CYP1A2, CYP2C9, CYP2C19, CYP2D6, CYP2E1, and CYP3A4 are also involved in the oxidative <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of many commonly used drugs.<sup id="cite_ref-Delafuente2003_36-0" class="reference"><a href="#cite_note-Delafuente2003-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> As a result, cimetidine has the potential for a large number of <a href="/wiki/Pharmacokinetic_interactions" class="mw-redirect" title="Pharmacokinetic interactions">pharmacokinetic interactions</a>.<sup id="cite_ref-Dart2004_20-3" class="reference"><a href="#cite_note-Dart2004-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LemkeWilliams2008_32-2" class="reference"><a href="#cite_note-LemkeWilliams2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-KarallieddeClarke2010_33-1" class="reference"><a href="#cite_note-KarallieddeClarke2010-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Cimetidine is reported to be a <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitive</a> and <a href="/wiki/Enzyme_inhibitor#Reversible_inhibitors" title="Enzyme inhibitor">reversible inhibitor</a> of several CYP enzymes,<sup id="cite_ref-Kelly2009_19-2" class="reference"><a href="#cite_note-Kelly2009-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RosenfeldLoose2007_26-1" class="reference"><a href="#cite_note-RosenfeldLoose2007-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LemkeWilliams2008_32-3" class="reference"><a href="#cite_note-LemkeWilliams2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cairns2012_37-0" class="reference"><a href="#cite_note-Cairns2012-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> although <a href="/wiki/Suicide_inhibition" title="Suicide inhibition">mechanism-based</a> (suicide) <a href="/wiki/Enzyme_inhibitor#Irreversible_inhibitors" title="Enzyme inhibitor">irreversible inhibition</a> has also been identified for cimetidine's inhibition of CYP2D6.<sup id="cite_ref-Zhou2016_25-1" class="reference"><a href="#cite_note-Zhou2016-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> It reversibly inhibits CYP enzymes by binding directly with the complexed <a href="/wiki/Heme" title="Heme">heme</a>-<a href="/wiki/Iron" title="Iron">iron</a> of the <a href="/wiki/Active_site" title="Active site">active site</a> via one of its <a href="/wiki/Imidazole" title="Imidazole">imidazole</a> <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> <a href="/wiki/Atom" title="Atom">atoms</a>, thereby blocking the oxidation of other drugs.<sup id="cite_ref-LemkeWilliams2008_32-4" class="reference"><a href="#cite_note-LemkeWilliams2008-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cairns2012_37-1" class="reference"><a href="#cite_note-Cairns2012-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid9630736_38-0" class="reference"><a href="#cite_note-pmid9630736-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Antiandrogenic_and_estrogenic_effects">Antiandrogenic and estrogenic effects</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=9" title="Edit section: Antiandrogenic and estrogenic effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cimetidine has been found to possess weak <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogenic</a> activity at high doses.<sup id="cite_ref-pmid6317740_30-1" class="reference"><a href="#cite_note-pmid6317740-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Becker2001_39-0" class="reference"><a href="#cite_note-Becker2001-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid6150641_40-0" class="reference"><a href="#cite_note-pmid6150641-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid3921876_41-0" class="reference"><a href="#cite_note-pmid3921876-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> It directly and <a href="/wiki/Competitive_antagonist" class="mw-redirect" title="Competitive antagonist">competitively</a> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonizes</a> the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (AR), the <a href="/wiki/Biological_target" title="Biological target">biological target</a> of <a href="/wiki/Androgen" title="Androgen">androgens</a> like <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">dihydrotestosterone</a> (DHT).<sup id="cite_ref-pmid428705_42-0" class="reference"><a href="#cite_note-pmid428705-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid6123322_43-0" class="reference"><a href="#cite_note-pmid6123322-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> However, the <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> of cimetidine for the AR is very weak; in one study, it showed only 0.00084% of the <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> of the <a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroid</a> <a href="/wiki/Metribolone" title="Metribolone">metribolone</a> (100%) for the human AR (K<sub>i</sub> = 140 μM and 1.18 nM, respectively).<sup id="cite_ref-pmid6725525_b_44-0" class="reference"><a href="#cite_note-pmid6725525_b-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> In any case, at sufficiently high doses, cimetidine has demonstrated weak but significant antiandrogenic effects in animals, including antiandrogenic effects in the rat <a href="/wiki/Ventral_prostate" class="mw-redirect" title="Ventral prostate">ventral prostate</a> and mouse <a href="/wiki/Kidney" title="Kidney">kidney</a>, reductions in the weights of the <a href="/wiki/Male_accessory_gland" title="Male accessory gland">male accessory glands</a> like the <a href="/wiki/Prostate_gland" class="mw-redirect" title="Prostate gland">prostate gland</a> and <a href="/wiki/Seminal_vesicle" class="mw-redirect" title="Seminal vesicle">seminal vesicles</a> in rats, and elevated <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropin</a> levels in male rats (due to reduced <a href="/wiki/Negative_feedback" title="Negative feedback">negative feedback</a> on the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis"><abbr title="hypothalamic–pituitary–gonadal">HPG</abbr> axis</a> by androgens).<sup id="cite_ref-GerallMoltz2013_45-0" class="reference"><a href="#cite_note-GerallMoltz2013-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PlessisAgarwal2014_46-0" class="reference"><a href="#cite_note-PlessisAgarwal2014-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> In addition to AR antagonism, cimetidine has been found to inhibit the 2-<a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> of <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> (via inhibition of CYP450 enzymes, which are involved in the metabolic inactivation of estradiol), resulting in increased <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> levels.<sup id="cite_ref-GalbraithMichnovicz1989_47-0" class="reference"><a href="#cite_note-GalbraithMichnovicz1989-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid1988774_48-0" class="reference"><a href="#cite_note-pmid1988774-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PescovitzWalvoord2007_49-0" class="reference"><a href="#cite_note-PescovitzWalvoord2007-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PolatCuhaci2014_50-0" class="reference"><a href="#cite_note-PolatCuhaci2014-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RendicCarlo2010_51-0" class="reference"><a href="#cite_note-RendicCarlo2010-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> The medication has also been reported to reduce testosterone <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> and increase <a href="/wiki/Prolactin" title="Prolactin">prolactin</a> levels in individual <a href="/wiki/Case_report" title="Case report">case reports</a>, effects which might be secondary to increased estrogen levels.<sup id="cite_ref-pmid22862307_52-0" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>At typical therapeutic levels, cimetidine has either no effect on or causes small increases in circulating testosterone concentrations in men.<sup id="cite_ref-GerallMoltz2013_45-1" class="reference"><a href="#cite_note-GerallMoltz2013-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Any increases in testosterone levels with cimetidine have been attributed to the loss of negative feedback on the HPG axis that results due to AR antagonism.<sup id="cite_ref-GerallMoltz2013_45-2" class="reference"><a href="#cite_note-GerallMoltz2013-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PlessisAgarwal2014_46-1" class="reference"><a href="#cite_note-PlessisAgarwal2014-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> At typical clinical dosages, such as those used to treat peptic ulcer disease, the incidence of <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> (breast development) with cimetidine is very low at less than 1%.<sup id="cite_ref-WattsFaingold2009_53-0" class="reference"><a href="#cite_note-WattsFaingold2009-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GerallMoltz2013_45-3" class="reference"><a href="#cite_note-GerallMoltz2013-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> In one survey of over 9,000 patients taking cimetidine, gynecomastia was the most frequent <a href="/wiki/Endocrine_system" title="Endocrine system">endocrine</a>-related complaint but was reported in only 0.2% of patients.<sup id="cite_ref-GerallMoltz2013_45-4" class="reference"><a href="#cite_note-GerallMoltz2013-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> At high doses however, such as those used to treat <a href="/wiki/Zollinger%E2%80%93Ellison_syndrome" title="Zollinger–Ellison syndrome">Zollinger–Ellison syndrome</a>, there may be a higher incidence of gynecomastia with cimetidine.<sup id="cite_ref-WattsFaingold2009_53-1" class="reference"><a href="#cite_note-WattsFaingold2009-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> In one small study, a 20% incidence of gynecomastia was observed in 25 male patients with duodenal ulcers who were treated with 1,600 mg/day cimetidine.<sup id="cite_ref-pmid22862307_52-1" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> The symptoms appeared after 4 months of treatment and regressed within a month following discontinuation of cimetidine.<sup id="cite_ref-pmid22862307_52-2" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> In another small study, cimetidine was reported to have induced <a href="/wiki/Breast" title="Breast">breast</a> changes and <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a> in 60% of 22 men treated with it.<sup id="cite_ref-pmid22862307_52-3" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> These adverse effects completely resolved in all cases when the men were switched from cimetidine to <a href="/wiki/Ranitidine" title="Ranitidine">ranitidine</a>.<sup id="cite_ref-pmid22862307_52-4" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> A study of the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> <a href="/wiki/Clinical_Practice_Research_Datalink#General_Practice_Research_Database" title="Clinical Practice Research Datalink">General Practice Research Database</a>, which contains over 80,000 men, found that the <a href="/wiki/Relative_risk" title="Relative risk">relative risk</a> of gynecomastia in cimetidine users was 7.2 relative to non-users.<sup id="cite_ref-pmid22862307_52-5" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> People taking a dosage of cimetidine of greater than or equal to 1,000 mg showed more than 40 times the risk of gynecomastia than non-users.<sup id="cite_ref-pmid22862307_52-6" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> The risk was highest during the period of time of 7 to 12 months after starting cimetidine.<sup id="cite_ref-pmid22862307_52-7" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> The gynecomastia associated with cimetidine is thought to be due to blockade of ARs in the breasts, which results in estrogen action unopposed by androgens in this <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissue</a>, although increased levels of estrogens due to inhibition of estrogen metabolism is another possible mechanism.<sup id="cite_ref-pmid22862307_52-8" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Cimetidine has also been associated with <a href="/wiki/Oligospermia" title="Oligospermia">oligospermia</a> (decreased <a href="/wiki/Sperm_count" class="mw-redirect" title="Sperm count">sperm count</a>) and <a href="/wiki/Sexual_dysfunction" title="Sexual dysfunction">sexual dysfunction</a> (e.g., <a href="/wiki/Decreased_libido" class="mw-redirect" title="Decreased libido">decreased libido</a>, erectile dysfunction) in men in some research, which are hormonally related similarly.<sup id="cite_ref-PlessisAgarwal2014_46-2" class="reference"><a href="#cite_note-PlessisAgarwal2014-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GerallMoltz2013_45-5" class="reference"><a href="#cite_note-GerallMoltz2013-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid22862307_52-9" class="reference"><a href="#cite_note-pmid22862307-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>In accordance with the very weak nature of its AR antagonistic activity, cimetidine has shown minimal effectiveness in the treatment of <a href="/wiki/Androgen-dependent_condition" title="Androgen-dependent condition">androgen-dependent conditions</a> such as <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a> (excessive hair growth), and <a href="/wiki/Hyperandrogenism" title="Hyperandrogenism">hyperandrogenism</a> (high androgen levels) in women.<sup id="cite_ref-AltchekDeligdisch2003_54-0" class="reference"><a href="#cite_note-AltchekDeligdisch2003-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PreglerDeCherney2002_55-0" class="reference"><a href="#cite_note-PreglerDeCherney2002-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WattsFaingold2009_53-2" class="reference"><a href="#cite_note-WattsFaingold2009-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid20082945_56-0" class="reference"><a href="#cite_note-pmid20082945-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> As such, its use for such indications is not recommended.<sup id="cite_ref-PreglerDeCherney2002_55-1" class="reference"><a href="#cite_note-PreglerDeCherney2002-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid20082945_56-1" class="reference"><a href="#cite_note-pmid20082945-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=10" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cimetidine is rapidly <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorbed</a> regardless of <a href="/wiki/Route_of_administration" title="Route of administration">route of administration</a>.<sup id="cite_ref-AcademicPress1984_7-3" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of cimetidine is 60 to 70%.<sup id="cite_ref-DowdJohnson2016_5-1" class="reference"><a href="#cite_note-DowdJohnson2016-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-LeikinPaloucek1995_6-6" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Onset_of_action" title="Onset of action">onset of action</a> of cimetidine when taken orally is 30 minutes,<sup id="cite_ref-VallerandSanoski2016_8-2" class="reference"><a href="#cite_note-VallerandSanoski2016-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">peak levels</a> occur within 1 to 3 hours.<sup id="cite_ref-DowdJohnson2016_5-2" class="reference"><a href="#cite_note-DowdJohnson2016-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Cimetidine is widely <a href="/wiki/Distribution_(pharmacology)" title="Distribution (pharmacology)">distributed</a> throughout all <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>.<sup id="cite_ref-AcademicPress1984_7-4" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> It is able to cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> and can produce effects in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> (e.g., <a href="/wiki/Headache" title="Headache">headaches</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Somnolence" title="Somnolence">somnolence</a>).<sup id="cite_ref-GuptaSingh-Radcliff2013_2-2" class="reference"><a href="#cite_note-GuptaSingh-Radcliff2013-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Volume_of_distribution" title="Volume of distribution">volume of distribution</a> of cimetidine is 0.8 L/kg in adults and 1.2 to 2.1 L/kg in children.<sup id="cite_ref-LeikinPaloucek1995_6-7" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Its <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> is 13 to 25% and is said to be without pharmacological significance.<sup id="cite_ref-LeikinPaloucek1995_6-8" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AcademicPress1984_7-5" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Cimetidine undergoes relatively little <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>, with 56 to 85% <a href="/wiki/Excretion" title="Excretion">excreted</a> unchanged.<sup id="cite_ref-AcademicPress1984_7-6" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> It is metabolized in the <a href="/wiki/Liver" title="Liver">liver</a> into cimetidine sulfoxide, hydroxycimetidine, and guanyl urea cimetidine.<sup id="cite_ref-LeikinPaloucek1995_6-9" class="reference"><a href="#cite_note-LeikinPaloucek1995-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The major <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of cimetidine is the <a href="/wiki/Sulfoxide" title="Sulfoxide">sulfoxide</a>, which accounts for about 30% of excreted material.<sup id="cite_ref-AcademicPress1984_7-7" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Cimetidine is rapidly <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a>, with an <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of 123 minutes, or about 2 hours.<sup id="cite_ref-AcademicPress1984_7-8" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> It has been said to have a <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration of action</a> of 4 to 8 hours.<sup id="cite_ref-GuptaSingh-Radcliff2013_2-3" class="reference"><a href="#cite_note-GuptaSingh-Radcliff2013-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The medication is mainly <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a> in <a href="/wiki/Urine" title="Urine">urine</a>.<sup id="cite_ref-AcademicPress1984_7-9" class="reference"><a href="#cite_note-AcademicPress1984-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </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=Cimetidine&action=edit&section=11" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cimetidine, approved by the FDA for inhibition of gastric acid secretion, has been advocated for a number of dermatological diseases.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Cimetidine was the prototypical histamine <a href="/wiki/H2-receptor_antagonist" class="mw-redirect" title="H2-receptor antagonist">H<sub>2</sub> receptor antagonist</a> from which the later members of the class were developed. Cimetidine was the culmination of a project at Smith, Kline and French (SK&F) Laboratories in Welwyn Garden City (now part of <a href="/wiki/GlaxoSmithKline" class="mw-redirect" title="GlaxoSmithKline">GlaxoSmithKline</a>) by <a href="/wiki/James_W._Black" class="mw-redirect" title="James W. Black">James W. Black</a>, <a href="/wiki/C._Robin_Ganellin" title="C. Robin Ganellin">C. Robin Ganellin</a>, and others to develop a <a href="/wiki/Histamine_receptor" title="Histamine receptor">histamine receptor</a> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> to suppress stomach acid secretion.<sup id="cite_ref-ACS_Landmarks_58-0" class="reference"><a href="#cite_note-ACS_Landmarks-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> This was one of the first drugs discovered using a <a href="/wiki/Rational_drug_design" class="mw-redirect" title="Rational drug design">rational drug design</a> approach. Sir James W. Black shared the 1988 Nobel Prize in Physiology or Medicine for the discovery of <a href="/wiki/Propranolol" title="Propranolol">propranolol</a> and also is credited for the discovery of cimetidine. </p><p>At the time (1964), <a href="/wiki/Histamine" title="Histamine">histamine</a> was known to stimulate the secretion of stomach acid, but also that traditional <a href="/wiki/Antihistamine" title="Antihistamine">antihistamines</a> had no effect on acid production. In the process, the SK&F scientists also proved the existence of histamine H<sub>2</sub> receptors. </p><p>The SK&F team used a rational drug-design structure starting from the structure of histamine — the only design lead, since nothing was known of the then hypothetical H<sub>2</sub> receptor. Hundreds of modified compounds were synthesized in an effort to develop a model of the receptor. The first breakthrough was <i>N<sup>α</sup></i>-guanylhistamine, a partial H<sub>2</sub> receptor antagonist. From this lead, the receptor model was further refined and eventually led to the development of <a href="/wiki/Burimamide" title="Burimamide">burimamide</a>, the first H<sub>2</sub> receptor antagonist. Burimamide, a specific <a href="/wiki/Competitive_antagonist" class="mw-redirect" title="Competitive antagonist">competitive antagonist</a> at the H<sub>2</sub> receptor, 100 times more potent than <i>N<sup>α</sup></i>-guanylhistamine, proved the existence of the H<sub>2</sub> receptor. </p><p>Burimamide was still insufficiently potent for oral administration, and further modification of the structure, based on modifying the <a href="/wiki/PKa" class="mw-redirect" title="PKa">pKa</a> of the compound, led to the development of <a href="/wiki/Metiamide" title="Metiamide">metiamide</a>. Metiamide was an effective agent; it was associated, however, with unacceptable <a href="/wiki/Nephrotoxicity" title="Nephrotoxicity">nephrotoxicity</a> and <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>.<sup id="cite_ref-ACS_Landmarks_58-1" class="reference"><a href="#cite_note-ACS_Landmarks-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> The toxicity was proposed to arise from the <a href="/wiki/Thiourea" title="Thiourea">thiourea</a> group, and similar <a href="/wiki/Guanidine" title="Guanidine">guanidine</a> analogues were investigated until the ultimate discovery of cimetidine. The compound was synthesized in 1972 and evaluated for toxicology by 1973. It passed all trials. </p><p>Cimetidine was first marketed in the United Kingdom in 1976, and in the U.S. in August 1977; therefore, it took 12 years from initiation of the H<sub>2</sub> receptor antagonist program to commercialization. By 1979, Tagamet was being sold in more than 100 countries and became the top-selling prescription product in the U.S., Canada, and several other countries. In November 1997, the American Chemical Society and the Royal Society of Chemistry in the U.K. jointly recognized the work as a milestone in drug discovery by designating it an International Historic Chemical Landmark during a ceremony at SmithKline Beecham's New Frontiers Science Park research facilities in Harlow, England.<sup id="cite_ref-Freemantle_59-0" class="reference"><a href="#cite_note-Freemantle-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p><p>The commercial name "Tagamet" was decided upon by fusing the two words "an<b>tag</b>onist" and "ci<b>met</b>idine".<sup id="cite_ref-ACS_Landmarks_58-2" class="reference"><a href="#cite_note-ACS_Landmarks-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> Subsequent to the introduction onto the U.S. drug market, two other H<sub>2</sub> receptor antagonists were approved, <a href="/wiki/Ranitidine" title="Ranitidine">ranitidine</a> (Zantac, Glaxo Labs) and <a href="/wiki/Famotidine" title="Famotidine">famotidine</a> (Pepcid, Yamanouchi, Ltd.) Cimetidine became the first drug ever to reach more than $1 billion a year in sales, thus making it the first <a href="/wiki/Pharmaceutical_drug#Blockbuster_drug" class="mw-redirect" title="Pharmaceutical drug">blockbuster drug</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (March 2023)">citation needed</span></a></i>]</sup> </p><p>Tagamet has been largely replaced by proton pump inhibitors for treating peptic ulcers, but is available as an over-the-counter medicine for heartburn in many countries.<sup id="cite_ref-Freemantle_59-1" class="reference"><a href="#cite_note-Freemantle-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=12" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some evidence suggests cimetidine could be effective in the treatment of common warts, but more rigorous double-blind clinical trials found it to be no more effective than a placebo.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p><p>Tentative evidence supports a beneficial role as add-on therapy in colorectal cancer.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p><p>Cimetidine inhibits <a href="/wiki/ALA_synthase" class="mw-redirect" title="ALA synthase">ALA synthase</a> activity and hence may have some therapeutic value in preventing and treating <a href="/wiki/Acute_porphyria" class="mw-redirect" title="Acute porphyria">acute porphyria</a> attacks.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p><p>There is some evidence supporting the use of Cimetidine in the treatment of <a href="/wiki/Periodic_fever,_aphthous_stomatitis,_pharyngitis_and_adenitis" title="Periodic fever, aphthous stomatitis, pharyngitis and adenitis">PFAPA</a>.<sup id="cite_ref-ped-rheum_66-0" class="reference"><a href="#cite_note-ped-rheum-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Veterinary_use">Veterinary use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=13" title="Edit section: Veterinary use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In dogs, cimetidine is used as an antiemetic when treating chronic gastritis.<sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<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=Cimetidine&action=edit&section=14" 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-Elks2014-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Elks2014_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Elks2014_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Elks2014_1-2"><sup><i><b>c</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="CITEREFElks2014" class="citation book cs1">Elks J (14 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA275"><i>The Dictionary of Drugs: Chemical Data: Chemical Data, Bibliographies</i></a>. Springer. pp. 275–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Bibliographies&rft.pages=275-&rft.pub=Springer&rft.date=2014-11-14&rft.isbn=978-1-4757-2085-3&rft.aulast=Elks&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DPA275&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-GuptaSingh-Radcliff2013-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-GuptaSingh-Radcliff2013_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GuptaSingh-Radcliff2013_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-GuptaSingh-Radcliff2013_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-GuptaSingh-Radcliff2013_2-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGuptaSingh-Radcliff2013" class="citation book cs1">Gupta A, Singh-Radcliff N (12 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=a85oAgAAQBAJ&pg=PT177"><i>Pharmacology in Anesthesia Practice</i></a>. Oxford University Press. pp. 177–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-934399-7" title="Special:BookSources/978-0-19-934399-7"><bdi>978-0-19-934399-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology+in+Anesthesia+Practice&rft.pages=177-&rft.pub=Oxford+University+Press&rft.date=2013-03-12&rft.isbn=978-0-19-934399-7&rft.aulast=Gupta&rft.aufirst=A&rft.au=Singh-Radcliff%2C+N&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Da85oAgAAQBAJ%26pg%3DPT177&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-Cimetidine_FDA_label-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Cimetidine_FDA_label_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Cimetidine_FDA_label_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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=496e258d-a5fd-42da-9a86-73afc8be359b">"Cimetidine tablet, film coated"</a>. <i>DailyMed</i>. 30 November 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">24 June</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Cimetidine+tablet%2C+film+coated&rft.date=2022-11-30&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D496e258d-a5fd-42da-9a86-73afc8be359b&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-Tagamet_FDA_label-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Tagamet_FDA_label_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Tagamet_FDA_label_4-1"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e6401e0a-8612-42e8-bf89-2d67243f28dc">"Tagamet - cimetidine tablet"</a>. <i>DailyMed</i>. 10 June 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">24 June</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Tagamet+-+cimetidine+tablet&rft.date=2024-06-10&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3De6401e0a-8612-42e8-bf89-2d67243f28dc&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-DowdJohnson2016-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-DowdJohnson2016_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-DowdJohnson2016_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-DowdJohnson2016_5-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDowdJohnsonMariotti2016" class="citation book cs1">Dowd FJ, Johnson B, Mariotti A (3 September 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=6xT7DAAAQBAJ&pg=PA406"><i>Pharmacology and Therapeutics for Dentistry - E-Book</i></a>. Elsevier Health Sciences. pp. 406–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-44595-5" title="Special:BookSources/978-0-323-44595-5"><bdi>978-0-323-44595-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology+and+Therapeutics+for+Dentistry+-+E-Book&rft.pages=406-&rft.pub=Elsevier+Health+Sciences&rft.date=2016-09-03&rft.isbn=978-0-323-44595-5&rft.aulast=Dowd&rft.aufirst=FJ&rft.au=Johnson%2C+B&rft.au=Mariotti%2C+A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D6xT7DAAAQBAJ%26pg%3DPA406&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-LeikinPaloucek1995-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-LeikinPaloucek1995_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-LeikinPaloucek1995_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-LeikinPaloucek1995_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-LeikinPaloucek1995_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-LeikinPaloucek1995_6-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-LeikinPaloucek1995_6-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-LeikinPaloucek1995_6-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-LeikinPaloucek1995_6-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-LeikinPaloucek1995_6-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-LeikinPaloucek1995_6-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLeikinPaloucek1995" class="citation book cs1">Leikin JB, Paloucek FP (1995). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JpZrAAAAMAAJ"><i>Poisoning & Toxicology Handbook, 1995-1996</i></a>. Lexi-Comp, Incorporated. p. 184. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-916589-08-0" title="Special:BookSources/978-0-916589-08-0"><bdi>978-0-916589-08-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Poisoning+%26+Toxicology+Handbook%2C+1995-1996&rft.pages=184&rft.pub=Lexi-Comp%2C+Incorporated&rft.date=1995&rft.isbn=978-0-916589-08-0&rft.aulast=Leikin&rft.aufirst=JB&rft.au=Paloucek%2C+FP&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJpZrAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-AcademicPress1984-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-AcademicPress1984_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AcademicPress1984_7-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-AcademicPress1984_7-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-AcademicPress1984_7-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-AcademicPress1984_7-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-AcademicPress1984_7-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-AcademicPress1984_7-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-AcademicPress1984_7-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-AcademicPress1984_7-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-AcademicPress1984_7-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=Fz6X-GmS-GgC&pg=PA176"><i>Profiles of Drug Substances, Excipients and Related Methodology</i></a>. Academic Press. 24 October 1984. pp. 176–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-086108-1" title="Special:BookSources/978-0-08-086108-1"><bdi>978-0-08-086108-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Profiles+of+Drug+Substances%2C+Excipients+and+Related+Methodology&rft.pages=176-&rft.pub=Academic+Press&rft.date=1984-10-24&rft.isbn=978-0-08-086108-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFz6X-GmS-GgC%26pg%3DPA176&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-VallerandSanoski2016-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-VallerandSanoski2016_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-VallerandSanoski2016_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-VallerandSanoski2016_8-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFVallerandSanoskiDeglin2016" class="citation book cs1">Vallerand AH, Sanoski CA, Deglin JH (25 May 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ORa1DAAAQBAJ&pg=PA636"><i>Davis's Drug Guide for Nurses</i></a>. 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Davis. pp. 636–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8036-5779-3" title="Special:BookSources/978-0-8036-5779-3"><bdi>978-0-8036-5779-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Davis%27s+Drug+Guide+for+Nurses&rft.pages=636-&rft.pub=F.A.+Davis&rft.date=2016-05-25&rft.isbn=978-0-8036-5779-3&rft.aulast=Vallerand&rft.aufirst=AH&rft.au=Sanoski%2C+CA&rft.au=Deglin%2C+JH&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DORa1DAAAQBAJ%26pg%3DPA636&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-IndexNominum2000-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-IndexNominum2000_9-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA234"><i>Index Nominum 2000: International Drug Directory</i></a>. 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In Dart RC (ed.). <i>Medical Toxicology</i>. Lippincott Williams & Wilkins. pp. 402–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-2845-4" title="Special:BookSources/978-0-7817-2845-4"><bdi>978-0-7817-2845-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Histaminde+H%3Csub%3E2%3C%2Fsub%3E+Antagonists&rft.btitle=Medical+Toxicology&rft.pages=402-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2004&rft.isbn=978-0-7817-2845-4&rft.aulast=Whyte&rft.aufirst=IM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBfdighlyGiwC%26pg%3DPA402&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFurst1996" class="citation journal cs1">Furst DE (June 1996). "Pharmacokinetics of hydroxychloroquine and chloroquine during treatment of rheumatic diseases". <i>Lupus</i>. <b>5</b> (Suppl 1): <span class="nowrap">S11 –</span> <span class="nowrap">S15</span>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F096120339600500104">10.1177/096120339600500104</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/8803904">8803904</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:44999237">44999237</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Lupus&rft.atitle=Pharmacokinetics+of+hydroxychloroquine+and+chloroquine+during+treatment+of+rheumatic+diseases&rft.volume=5&rft.issue=Suppl+1&rft.pages=%3Cspan+class%3D%22nowrap%22%3ES11+-%3C%2Fspan%3E+%3Cspan+class%3D%22nowrap%22%3ES15%3C%2Fspan%3E&rft.date=1996-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A44999237%23id-name%3DS2CID&rft_id=info%3Apmid%2F8803904&rft_id=info%3Adoi%2F10.1177%2F096120339600500104&rft.aulast=Furst&rft.aufirst=DE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text">See complete drug interactions for Zomig (zolmitriptan succinate used for migraine relief) in package insert: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150218190357/http://www1.astrazeneca-us.com/pi/Zomig.pdf">"Highlights of Zomig Prescribing Information"</a> <span class="cs1-format">(PDF)</span>. AstraZeneca. Archived from <a rel="nofollow" class="external text" href="http://www1.astrazeneca-us.com/pi/Zomig.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 18 February 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">28 January</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Highlights+of+Zomig+Prescribing+Information&rft.pub=AstraZeneca&rft_id=http%3A%2F%2Fwww1.astrazeneca-us.com%2Fpi%2FZomig.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUrakamiKimuraOkudaMasuda2005" class="citation journal cs1">Urakami Y, Kimura N, Okuda M, Masuda S, Katsura T, Inui K (June 2005). "Transcellular transport of creatinine in renal tubular epithelial cell line LLC-PK1". <i>Drug Metabolism and Pharmacokinetics</i>. <b>20</b> (3): <span class="nowrap">200–</span>205. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2133%2Fdmpk.20.200">10.2133/dmpk.20.200</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/15988122">15988122</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:13857940">13857940</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Metabolism+and+Pharmacokinetics&rft.atitle=Transcellular+transport+of+creatinine+in+renal+tubular+epithelial+cell+line+LLC-PK1&rft.volume=20&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E200-%3C%2Fspan%3E205&rft.date=2005-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A13857940%23id-name%3DS2CID&rft_id=info%3Apmid%2F15988122&rft_id=info%3Adoi%2F10.2133%2Fdmpk.20.200&rft.aulast=Urakami&rft.aufirst=Y&rft.au=Kimura%2C+N&rft.au=Okuda%2C+M&rft.au=Masuda%2C+S&rft.au=Katsura%2C+T&rft.au=Inui%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-Rodrigues2008-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-Rodrigues2008_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOgilvieUsukiYerinoParkinson2008" class="citation book cs1">Ogilvie BW, Usuki E, Yerino P, Parkinson A (8 February 2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=rmCGQ8qAv8AC&pg=PA294">"In vitro approaches for studying the inhibition of drug-metabolizing enzymes and identifying the drug-metabolizing enzymes responsible for the metabolism of drugs (reaction phenotyping) with emphasis on cytochrome P450"</a>. In Rodrigues DA (ed.). <i>Drug-Drug Interactions</i> (Second ed.). CRC Press. pp. 277, 294. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8493-7594-1" title="Special:BookSources/978-0-8493-7594-1"><bdi>978-0-8493-7594-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=In+vitro+approaches+for+studying+the+inhibition+of+drug-metabolizing+enzymes+and+identifying+the+drug-metabolizing+enzymes+responsible+for+the+metabolism+of+drugs+%28reaction+phenotyping%29+with+emphasis+on+cytochrome+P450&rft.btitle=Drug-Drug+Interactions&rft.pages=277%2C+294&rft.edition=Second&rft.pub=CRC+Press&rft.date=2008-02-08&rft.isbn=978-0-8493-7594-1&rft.aulast=Ogilvie&rft.aufirst=BW&rft.au=Usuki%2C+E&rft.au=Yerino%2C+P&rft.au=Parkinson%2C+A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DrmCGQ8qAv8AC%26pg%3DPA294&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-Zhou2016-25"><span class="mw-cite-backlink">^ <a href="#cite_ref-Zhou2016_25-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Zhou2016_25-1"><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="CITEREFZhou2016" class="citation book cs1">Zhou S (6 April 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=UJqmCwAAQBAJ&pg=PA299">"Inhibitors of Human CYP2D6"</a>. <i>Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism</i>. CRC Press. pp. 299–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4665-9788-4" title="Special:BookSources/978-1-4665-9788-4"><bdi>978-1-4665-9788-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Inhibitors+of+Human+CYP2D6&rft.btitle=Cytochrome+P450+2D6%3A+Structure%2C+Function%2C+Regulation+and+Polymorphism&rft.pages=299-&rft.pub=CRC+Press&rft.date=2016-04-06&rft.isbn=978-1-4665-9788-4&rft.aulast=Zhou&rft.aufirst=S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DUJqmCwAAQBAJ%26pg%3DPA299&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-RosenfeldLoose2007-26"><span class="mw-cite-backlink">^ <a href="#cite_ref-RosenfeldLoose2007_26-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-RosenfeldLoose2007_26-1"><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="CITEREFRosenfeldLoose2007" class="citation book cs1">Rosenfeld GC, Loose DS (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=fm8kmMDjdiAC&pg=PA202"><i>Pharmacology</i></a>. Lippincott Williams & Wilkins. pp. 202–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-8074-2" title="Special:BookSources/978-0-7817-8074-2"><bdi>978-0-7817-8074-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology&rft.pages=202-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2007&rft.isbn=978-0-7817-8074-2&rft.aulast=Rosenfeld&rft.aufirst=GC&rft.au=Loose%2C+DS&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dfm8kmMDjdiAC%26pg%3DPA202&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-FullerSajatovic2005-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-FullerSajatovic2005_27-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFullerSajatovic2005" class="citation book cs1">Fuller MA, Sajatovic M (2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=LzBtAAAAMAAJ"><i>Drug Information Handbook for Psychiatry</i></a>. Lexi-Comp. p. 285. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781591951148" title="Special:BookSources/9781591951148"><bdi>9781591951148</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drug+Information+Handbook+for+Psychiatry&rft.pages=285&rft.pub=Lexi-Comp&rft.date=2005&rft.isbn=9781591951148&rft.aulast=Fuller&rft.aufirst=MA&rft.au=Sajatovic%2C+M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DLzBtAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-CameronFeuer2012-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-CameronFeuer2012_28-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLeederOkey2012" class="citation book cs1">Leeder JS, Okey AB (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=xZf-CAAAQBAJ&pg=PA140">"Cytochrome P450 and Liver injury"</a>. In Cameron R, Feuer G, de la Iglesias F (eds.). <i>Drug-Induced Hepatotoxicity</i>. Springer Science & Business Media. pp. 140–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-61013-4" title="Special:BookSources/978-3-642-61013-4"><bdi>978-3-642-61013-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cytochrome+P450+and+Liver+injury&rft.btitle=Drug-Induced+Hepatotoxicity&rft.pages=140-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-61013-4&rft.aulast=Leeder&rft.aufirst=JS&rft.au=Okey%2C+AB&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DxZf-CAAAQBAJ%26pg%3DPA140&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCoppoOrsoVirgaDalmasso2021" class="citation journal cs1">Coppo R, Orso F, Virga F, Dalmasso A, Baruffaldi D, Nie L, et al. (July 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8581997">"ESDN inhibits melanoma progression by blocking E-selectin expression in endothelial cells via STAT3"</a>. <i>Cancer Letters</i>. <b>510</b>: <span class="nowrap">13–</span>23. <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%2Fj.canlet.2021.04.005">10.1016/j.canlet.2021.04.005</a>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/2318%2F1791282">2318/1791282</a></span>. <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/PMC8581997">8581997</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/33862151">33862151</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer+Letters&rft.atitle=ESDN+inhibits+melanoma+progression+by+blocking+E-selectin+expression+in+endothelial+cells+via+STAT3&rft.volume=510&rft.pages=%3Cspan+class%3D%22nowrap%22%3E13-%3C%2Fspan%3E23&rft.date=2021-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8581997%23id-name%3DPMC&rft_id=info%3Apmid%2F33862151&rft_id=info%3Ahdl%2F2318%2F1791282&rft_id=info%3Adoi%2F10.1016%2Fj.canlet.2021.04.005&rft.aulast=Coppo&rft.aufirst=R&rft.au=Orso%2C+F&rft.au=Virga%2C+F&rft.au=Dalmasso%2C+A&rft.au=Baruffaldi%2C+D&rft.au=Nie%2C+L&rft.au=Clapero%2C+F&rft.au=Dettori%2C+D&rft.au=Quirico%2C+L&rft.au=Grassi%2C+E&rft.au=Defilippi%2C+P&rft.au=Provero%2C+P&rft.au=Valdembri%2C+D&rft.au=Serini%2C+G&rft.au=Sadeghi%2C+MM&rft.au=Mazzone%2C+M&rft.au=Taverna%2C+D&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8581997&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-pmid6317740-30"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid6317740_30-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid6317740_30-1"><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="CITEREFRichards1983" class="citation journal cs1">Richards DA (1983). "Comparative pharmacodynamics and pharmacokinetics of cimetidine and ranitidine". <i>Journal of Clinical Gastroenterology</i>. <b>5</b> (Suppl 1): <span class="nowrap">81–</span>90. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00004836-198312001-00008">10.1097/00004836-198312001-00008</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/6317740">6317740</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:24909853">24909853</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Clinical+Gastroenterology&rft.atitle=Comparative+pharmacodynamics+and+pharmacokinetics+of+cimetidine+and+ranitidine&rft.volume=5&rft.issue=Suppl+1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E81-%3C%2Fspan%3E90&rft.date=1983&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24909853%23id-name%3DS2CID&rft_id=info%3Apmid%2F6317740&rft_id=info%3Adoi%2F10.1097%2F00004836-198312001-00008&rft.aulast=Richards&rft.aufirst=DA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-Osborne2013-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-Osborne2013_31-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTaylor2013" class="citation journal cs1">Taylor JE (22 October 2013). Osborne NN (ed.). <span class="id-lock-subscription" title="Paid subscription required"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=ldnWAgAAQBAJ&pg=PA297">"Neurochemical and neuropharmacological aspects of histamine receptors"</a></span>. <i>Neurochemistry International</i>. <b>4</b> (<span class="nowrap">2–</span>3). 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Pharmaceutical Press. pp. 110–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85369-979-8" title="Special:BookSources/978-0-85369-979-8"><bdi>978-0-85369-979-8</bdi></a>. <q>Drugs interacting in this way with CYP include the histamine H2-receptor antagonist cimetidine, [...] Reversible inhibitors, such as cimetidine, which interact with the complexed iron at the active site of the enzyme to inhibit oxidation of other drugs. 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Review of the literature and personal observations]". <i>Minerva Medica</i> (in Italian). <b>76</b> (12): <span class="nowrap">579–</span>586. <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/3921876">3921876</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Minerva+Medica&rft.atitle=%5BDysfunction+of+the+hypothalamo-hypophyseal-gonadal+axis+induced+by+histamine+H2+antagonists.+Review+of+the+literature+and+personal+observations%5D&rft.volume=76&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E579-%3C%2Fspan%3E586&rft.date=1985-03&rft_id=info%3Apmid%2F3921876&rft.aulast=Biagi&rft.aufirst=P&rft.au=Milani%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-pmid428705-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid428705_42-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWintersBanksLoriaux1979" class="citation journal cs1">Winters SJ, Banks JL, Loriaux DL (March 1979). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0016-5085%2879%2980217-6">"Cimetidine is an antiandrogen in the rat"</a>. <i>Gastroenterology</i>. <b>76</b> (3): <span class="nowrap">504–</span>508. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0016-5085%2879%2980217-6">10.1016/S0016-5085(79)80217-6</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/428705">428705</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gastroenterology&rft.atitle=Cimetidine+is+an+antiandrogen+in+the+rat&rft.volume=76&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E504-%3C%2Fspan%3E508&rft.date=1979-03&rft_id=info%3Adoi%2F10.1016%2FS0016-5085%2879%2980217-6&rft_id=info%3Apmid%2F428705&rft.aulast=Winters&rft.aufirst=SJ&rft.au=Banks%2C+JL&rft.au=Loriaux%2C+DL&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0016-5085%252879%252980217-6&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-pmid6123322-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid6123322_43-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSivelleUnderwoodJelly1982" class="citation journal cs1">Sivelle PC, Underwood AH, Jelly JA (March 1982). "The effects of histamine H2 receptor antagonists on androgen action in vivo and dihydrotestosterone binding to the rat prostate androgen receptor in vitro". <i>Biochemical Pharmacology</i>. <b>31</b> (5): <span class="nowrap">677–</span>684. <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%2F0006-2952%2882%2990449-X">10.1016/0006-2952(82)90449-X</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/6123322">6123322</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemical+Pharmacology&rft.atitle=The+effects+of+histamine+H2+receptor+antagonists+on+androgen+action+in+vivo+and+dihydrotestosterone+binding+to+the+rat+prostate+androgen+receptor+in+vitro&rft.volume=31&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E677-%3C%2Fspan%3E684&rft.date=1982-03&rft_id=info%3Adoi%2F10.1016%2F0006-2952%2882%2990449-X&rft_id=info%3Apmid%2F6123322&rft.aulast=Sivelle&rft.aufirst=PC&rft.au=Underwood%2C+AH&rft.au=Jelly%2C+JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-pmid6725525_b-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid6725525_b_44-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEilEdelson1984" class="citation journal cs1">Eil C, Edelson SK (July 1984). "The use of human skin fibroblasts to obtain potency estimates of drug binding to androgen receptors". <i>The Journal of Clinical Endocrinology and Metabolism</i>. <b>59</b> (1): <span class="nowrap">51–</span>55. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjcem-59-1-51">10.1210/jcem-59-1-51</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/6725525">6725525</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Clinical+Endocrinology+and+Metabolism&rft.atitle=The+use+of+human+skin+fibroblasts+to+obtain+potency+estimates+of+drug+binding+to+androgen+receptors&rft.volume=59&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E51-%3C%2Fspan%3E55&rft.date=1984-07&rft_id=info%3Adoi%2F10.1210%2Fjcem-59-1-51&rft_id=info%3Apmid%2F6725525&rft.aulast=Eil&rft.aufirst=C&rft.au=Edelson%2C+SK&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-GerallMoltz2013-45"><span class="mw-cite-backlink">^ <a href="#cite_ref-GerallMoltz2013_45-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GerallMoltz2013_45-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-GerallMoltz2013_45-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-GerallMoltz2013_45-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-GerallMoltz2013_45-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-GerallMoltz2013_45-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWard2013" class="citation book cs1">Ward OB (11 November 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4nb1BwAAQBAJ&pg=PA207">"Fetal drug exposure and sexual differentiation of males."</a>. In Gerall AA, Moltz H, Ward EL (eds.). <i>Sexual Differentiation</i>. Springer Science & Business Media. pp. 207–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4899-2453-7" title="Special:BookSources/978-1-4899-2453-7"><bdi>978-1-4899-2453-7</bdi></a>. <q>In high concentrations cimetidine acts as a weak antiandrogen by competitively binding to cytosol androgen receptors, as has been demonstrated in rat ventral prostate (Foldesy, Vanderhoof, & Hahn, 1985; Sivelle, Underwood, & Jelly, 1982) and mouse kidney tissue (Funder & Mercer, 1979). In vivo, cimetidine, in high dose levels, causes reductions in prostate and seminal vesicle weights in male rats (Foldesy et al., 1985; Leslie & Walker, 1977; Sivelle et al., 1982). After 6 weeks of daily cimetidine administration to male rats, reduced weights of accessory sexual organs were accompanied by elevated gonadotropin levels (Baba, Paul, Pollow, Janetschek, & Jacobi, 1981). At therapeutic levels in men, cimetidine either has no effect on plasma T levels (Spona et al., 1987; Stubbs et al., 1983) or causes small increases in T (Peden, Boyd, Browning, Saunders, & Wormsley, 1981; Van Thiel, Gavaler, Smith, & Paul, 1979; Wang, Lai, Lam, & Yeung, 1982). The increases in T have been attributed to cimetidine's antagonism of the normal negative feedback that androgens exert on gonadotropin secretion (Peden, Cargill, Browning, Saunders, & Wormsley, 1979). Gynecomastia and even loss of libido that progressed to impotence have occasionally been reported in men taking cimetidine (Peden et al., 1979; Spence & Celestin, 1979), but the occurrence of these disorders is very rare (Gifford, Aeugle, Myerson, & Tannenbaum, 1980). In one survey, gynecomastia, the most frequent endocrine-related complaint, was reported in only 0.2% of over 9,000 patients taking cimetidine (Gifford et al., 1980).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Fetal+drug+exposure+and+sexual+differentiation+of+males.&rft.btitle=Sexual+Differentiation&rft.pages=207-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2013-11-11&rft.isbn=978-1-4899-2453-7&rft.aulast=Ward&rft.aufirst=OB&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4nb1BwAAQBAJ%26pg%3DPA207&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-PlessisAgarwal2014-46"><span class="mw-cite-backlink">^ <a href="#cite_ref-PlessisAgarwal2014_46-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PlessisAgarwal2014_46-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-PlessisAgarwal2014_46-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBarazaniSabanegh_Jr2014" class="citation book cs1">Barazani Y, Sabanegh Jr ES (26 July 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=-I4kBAAAQBAJ&pg=PA233">"Risks from Medical and Therapeutic Treatments"</a>. In du Plessis SS, Agarwal A, Sabanegh Jr ES (eds.). <i>Male Infertility: A Complete Guide to Lifestyle and Environmental Factors</i>. Springer. pp. 233–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4939-1040-3" title="Special:BookSources/978-1-4939-1040-3"><bdi>978-1-4939-1040-3</bdi></a>. <q>Like other antiandrogens, [cimetidine] leads to elevated gonadotropin levels by antagonizing the negative feedback control of gonadotropin secretion by testosterone [1, 34]. Cimetidine has been reported to have antiandrogenic effects ranging from gynecomastia to oligospermia [4]. In one clinical study, men administered cimetidine exhibited a significant reduction in sperm concentration compared to placebo-treated controls [35]. In another study of men receiving cimetidine for chronic duodenal ulcers, testosterone and FSH were elevated during treatment with cimetidine compared to both pre- and posttreatment levels. Moreover, these hormonal effects were associated with a reduction in mean sperm count compared to the period after drug withdrawal [34].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Risks+from+Medical+and+Therapeutic+Treatments&rft.btitle=Male+Infertility%3A+A+Complete+Guide+to+Lifestyle+and+Environmental+Factors&rft.pages=233-&rft.pub=Springer&rft.date=2014-07-26&rft.isbn=978-1-4939-1040-3&rft.aulast=Barazani&rft.aufirst=Y&rft.au=Sabanegh+Jr%2C+ES&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D-I4kBAAAQBAJ%26pg%3DPA233&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-GalbraithMichnovicz1989-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-GalbraithMichnovicz1989_47-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGalbraithMichnovicz1989" class="citation journal cs1">Galbraith RA, Michnovicz JJ (August 1989). "The effects of cimetidine on the oxidative metabolism of estradiol". <i>The New England Journal of Medicine</i>. <b>321</b> (5): <span class="nowrap">269–</span>274. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1056%2FNEJM198908033210501">10.1056/NEJM198908033210501</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/2747769">2747769</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+England+Journal+of+Medicine&rft.atitle=The+effects+of+cimetidine+on+the+oxidative+metabolism+of+estradiol&rft.volume=321&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E269-%3C%2Fspan%3E274&rft.date=1989-08&rft_id=info%3Adoi%2F10.1056%2FNEJM198908033210501&rft_id=info%3Apmid%2F2747769&rft.aulast=Galbraith&rft.aufirst=RA&rft.au=Michnovicz%2C+JJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-pmid1988774-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid1988774_48-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMichnoviczGalbraith1991" class="citation journal cs1">Michnovicz JJ, Galbraith RA (February 1991). "Cimetidine inhibits catechol estrogen metabolism in women". <i>Metabolism</i>. <b>40</b> (2): <span class="nowrap">170–</span>174. <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%2F0026-0495%2891%2990169-W">10.1016/0026-0495(91)90169-W</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/1988774">1988774</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Metabolism&rft.atitle=Cimetidine+inhibits+catechol+estrogen+metabolism+in+women&rft.volume=40&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E170-%3C%2Fspan%3E174&rft.date=1991-02&rft_id=info%3Adoi%2F10.1016%2F0026-0495%2891%2990169-W&rft_id=info%3Apmid%2F1988774&rft.aulast=Michnovicz&rft.aufirst=JJ&rft.au=Galbraith%2C+RA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-PescovitzWalvoord2007-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-PescovitzWalvoord2007_49-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPescovitzWalvoord2007" class="citation book cs1">Pescovitz OH, Walvoord EC (6 June 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=seYO1f1JgzYC&pg=PA203"><i>When Puberty is Precocious: Scientific and Clinical Aspects</i></a>. Springer Science & Business Media. pp. 203–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-59745-499-5" title="Special:BookSources/978-1-59745-499-5"><bdi>978-1-59745-499-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=When+Puberty+is+Precocious%3A+Scientific+and+Clinical+Aspects&rft.pages=203-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2007-06-06&rft.isbn=978-1-59745-499-5&rft.aulast=Pescovitz&rft.aufirst=OH&rft.au=Walvoord%2C+EC&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DseYO1f1JgzYC%26pg%3DPA203&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-PolatCuhaci2014-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-PolatCuhaci2014_50-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCuhaciPolatEvranosErsoy2014" class="citation journal cs1">Cuhaci N, Polat SB, Evranos B, Ersoy R, Cakir B (March 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3987263">"Gynecomastia: Clinical evaluation and management"</a>. <i>Indian Journal of Endocrinology and Metabolism</i>. <b>18</b> (2): <span class="nowrap">150–</span>158. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.4103%2F2230-8210.129104">10.4103/2230-8210.129104</a></span>. <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/PMC3987263">3987263</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/24741509">24741509</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Indian+Journal+of+Endocrinology+and+Metabolism&rft.atitle=Gynecomastia%3A+Clinical+evaluation+and+management&rft.volume=18&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E150-%3C%2Fspan%3E158&rft.date=2014-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3987263%23id-name%3DPMC&rft_id=info%3Apmid%2F24741509&rft_id=info%3Adoi%2F10.4103%2F2230-8210.129104&rft.aulast=Cuhaci&rft.aufirst=N&rft.au=Polat%2C+SB&rft.au=Evranos%2C+B&rft.au=Ersoy%2C+R&rft.au=Cakir%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3987263&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-RendicCarlo2010-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-RendicCarlo2010_51-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRendicDi_Carlo2010" class="citation journal cs1">Rendic S, Di Carlo FJ (2010). "Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers, and inhibitors". <i>Drug Metabolism Reviews</i>. <b>29</b> (<span class="nowrap">1–</span>2): <span class="nowrap">413–</span>580. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F03602539709037591">10.3109/03602539709037591</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/9187528">9187528</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Metabolism+Reviews&rft.atitle=Human+cytochrome+P450+enzymes%3A+a+status+report+summarizing+their+reactions%2C+substrates%2C+inducers%2C+and+inhibitors&rft.volume=29&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E413-%3C%2Fspan%3E580&rft.date=2010&rft_id=info%3Adoi%2F10.3109%2F03602539709037591&rft_id=info%3Apmid%2F9187528&rft.aulast=Rendic&rft.aufirst=S&rft.au=Di+Carlo%2C+FJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-pmid22862307-52"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid22862307_52-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid22862307_52-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid22862307_52-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pmid22862307_52-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pmid22862307_52-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pmid22862307_52-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-pmid22862307_52-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-pmid22862307_52-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-pmid22862307_52-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-pmid22862307_52-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDeepinderBraunstein2012" class="citation journal cs1">Deepinder F, Braunstein GD (September 2012). "Drug-induced gynecomastia: an evidence-based review". <i>Expert Opinion on Drug Safety</i>. <b>11</b> (5): <span class="nowrap">779–</span>795. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1517%2F14740338.2012.712109">10.1517/14740338.2012.712109</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/22862307">22862307</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:22938364">22938364</a>. <q>Cimetidine. Spence and Celestin reported a 20% incidence of gynecomastia in a prospective study of 25 male duodenal ulcer patients treated with cimetidine 1.6 g/day [13]. Symptoms developed after 4 months of treatment and regressed within a month of stopping therapy. In another prospective cohort study involving 22 patients, cimetidine caused breast changes and erectile dysfunction in 60% of men which resolved completely in all cases when switched to ranitidine [14]. In the UK general practice database of over 80,000 men, the relative risk (RR) of gynecomastia among cimetidine users was 7.2 (95% confidence interval (CI 4.5 -- 11.3)) as compared with the non-users. Users with a daily dose ‡ 1000 mg had more than 40 times the risk of developing gynecomastia than the non-users. The period of highest risk was 7 -- 12 months after starting cimetidine treatment [15]. Cimetidine blocks the androgen receptors in the breast leading to decreased androgen action causing the growth of breast tissue because of 'unopposed' estrogen action [16]. Another possible mechanism includes decreased 2-hydroxylation of estrogen leading to elevated serum estrogen levels [17]. There also are reports of cimetidine blocking testosterone biosynthesis and causing elevated prolactin levels in individual cases [18].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opinion+on+Drug+Safety&rft.atitle=Drug-induced+gynecomastia%3A+an+evidence-based+review&rft.volume=11&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E779-%3C%2Fspan%3E795&rft.date=2012-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A22938364%23id-name%3DS2CID&rft_id=info%3Apmid%2F22862307&rft_id=info%3Adoi%2F10.1517%2F14740338.2012.712109&rft.aulast=Deepinder&rft.aufirst=F&rft.au=Braunstein%2C+GD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-WattsFaingold2009-53"><span class="mw-cite-backlink">^ <a href="#cite_ref-WattsFaingold2009_53-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-WattsFaingold2009_53-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-WattsFaingold2009_53-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDunaway2009" class="citation book cs1">Dunaway G (1 April 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=kfsrz_-OrMQC&pg=PA472">"Androgens and Antiandrogens"</a>. In Watts S, Faingold C, Dunaway G, Crespo L (eds.). <i>Brody's Human Pharmacology - E-Book</i>. Elsevier Health Sciences. pp. 472–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-07575-6" title="Special:BookSources/978-0-323-07575-6"><bdi>978-0-323-07575-6</bdi></a>. <q>The histamine receptor antagonist cimetidine, used to decrease gastric acid secretion in treatment of peptic ulcer disease and esophagitis (see Chapter 14), also acts as an antiandrogen. Thus it has been reported to produce gynecomastia when given in large doses, such as those used in the treatment of patients with Zollinger-Ellison syndrome. Gynecomastia occurs in less than 1% of patients treated with the doses used in peptic ulcer disease. Cimetidine interacts with ARs approximately 0.01% as effectively as testosterone and has been used with limited effectiveness to treat hirsutism in women.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Androgens+and+Antiandrogens&rft.btitle=Brody%27s+Human+Pharmacology+-+E-Book&rft.pages=472-&rft.pub=Elsevier+Health+Sciences&rft.date=2009-04-01&rft.isbn=978-0-323-07575-6&rft.aulast=Dunaway&rft.aufirst=G&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dkfsrz_-OrMQC%26pg%3DPA472&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-AltchekDeligdisch2003-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-AltchekDeligdisch2003_54-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCoppermanMukherjeeKase2003" class="citation book cs1">Copperman AB, Mukherjee T, Kase NG (4 September 2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=vds_TQpTIhoC&pg=PA351">"Polycystic Ovarian Syndrome"</a>. In Altchek A, Deligdisch L, Kase N (eds.). <i>Diagnosis and Management of Ovarian Disorders</i>. Academic Press. pp. 351–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-049451-7" title="Special:BookSources/978-0-08-049451-7"><bdi>978-0-08-049451-7</bdi></a>. <q>Cimetidine is a weak androgen receptor antagonist. A controlled clinical study has not found cimetidine to be effective in the treatment of hyperandrogenism.[123, 124] 5.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Polycystic+Ovarian+Syndrome&rft.btitle=Diagnosis+and+Management+of+Ovarian+Disorders&rft.pages=351-&rft.pub=Academic+Press&rft.date=2003-09-04&rft.isbn=978-0-08-049451-7&rft.aulast=Copperman&rft.aufirst=AB&rft.au=Mukherjee%2C+T&rft.au=Kase%2C+NG&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dvds_TQpTIhoC%26pg%3DPA351&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-PreglerDeCherney2002-55"><span class="mw-cite-backlink">^ <a href="#cite_ref-PreglerDeCherney2002_55-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-PreglerDeCherney2002_55-1"><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="CITEREFPreglerDeCherney2002" class="citation book cs1">Pregler JP, DeCherney AH (2002). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zC99_it1C5YC&pg=PA595">"Approach to the Patient with Hirsutism"</a>. <i>Women's Health: Principles and Clinical Practice</i>. PMPH-USA. pp. 595–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-55009-170-0" title="Special:BookSources/978-1-55009-170-0"><bdi>978-1-55009-170-0</bdi></a>. <q>Cimetidine is a histamine type 2 blocker, which also binds to the androgen receptor to inhibit its function." However, this antiandrogen activity of cimetidine is weak, and the clinical benefit of its use in women with hirsutism is minimal. Thus, this drug is not recommended for the treatment of hyperandrogenism.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Approach+to+the+Patient+with+Hirsutism&rft.btitle=Women%27s+Health%3A+Principles+and+Clinical+Practice&rft.pages=595-&rft.pub=PMPH-USA&rft.date=2002&rft.isbn=978-1-55009-170-0&rft.aulast=Pregler&rft.aufirst=JP&rft.au=DeCherney%2C+AH&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzC99_it1C5YC%26pg%3DPA595&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-pmid20082945-56"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid20082945_56-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid20082945_56-1"><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="CITEREFKatsambasDessinioti2010" class="citation journal cs1">Katsambas AD, Dessinioti C (2010). "Hormonal therapy for acne: why not as first line therapy? facts and controversies". <i>Clinics in Dermatology</i>. <b>28</b> (1): <span class="nowrap">17–</span>23. <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%2Fj.clindermatol.2009.03.006">10.1016/j.clindermatol.2009.03.006</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/20082945">20082945</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinics+in+Dermatology&rft.atitle=Hormonal+therapy+for+acne%3A+why+not+as+first+line+therapy%3F+facts+and+controversies&rft.volume=28&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E17-%3C%2Fspan%3E23&rft.date=2010&rft_id=info%3Adoi%2F10.1016%2Fj.clindermatol.2009.03.006&rft_id=info%3Apmid%2F20082945&rft.aulast=Katsambas&rft.aufirst=AD&rft.au=Dessinioti%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> <li id="cite_note-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-57">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFScheinfeld2003" class="citation journal cs1">Scheinfeld N (March 2003). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Veterinary+Pharmacology+and+Therapeutics&rft.atitle=Pharmacokinetics+of+cimetidine+in+dogs+after+oral+administration+of+cimetidine+tablets&rft.volume=32&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E213-%3C%2Fspan%3E218&rft.date=2009-06&rft_id=info%3Adoi%2F10.1111%2Fj.1365-2885.2008.01026.x&rft_id=info%3Apmid%2F19646084&rft.aulast=Le+Traon&rft.aufirst=G&rft.au=Burgaud%2C+S&rft.au=Horspool%2C+LJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACimetidine" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cimetidine&action=edit&section=15" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" 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td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Drugs_for_peptic_ulcer_and_GERD/GORD_(A02B)716" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Drugs_for_peptic_ulcer_and_GORD" title="Template:Drugs for peptic ulcer and GORD"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Drugs_for_peptic_ulcer_and_GORD" title="Template talk:Drugs for peptic ulcer and GORD"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Drugs_for_peptic_ulcer_and_GORD" title="Special:EditPage/Template:Drugs for peptic ulcer and GORD"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Drugs_for_peptic_ulcer_and_GERD/GORD_(A02B)716" style="font-size:114%;margin:0 4em">Drugs for <a href="/wiki/Peptic_ulcer" class="mw-redirect" title="Peptic ulcer">peptic ulcer</a> and <a href="/wiki/Gastroesophageal_reflux_disease" title="Gastroesophageal reflux disease">GERD/GORD</a> (<a href="/wiki/ATC_code_A02#A02B" title="ATC code A02">A02B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/H2_antagonist" class="mw-redirect" title="H2 antagonist">H<sub>2</sub> antagonists</a> ("-tidine")</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Cimetidine</a></li> <li><a href="/wiki/Famotidine" title="Famotidine">Famotidine</a></li> <li><a href="/wiki/Lafutidine" title="Lafutidine">Lafutidine</a></li> <li><a href="/wiki/Lavoltidine" title="Lavoltidine">Lavoltidine (loxtidine)</a></li> <li><a href="/wiki/Niperotidine" title="Niperotidine">Niperotidine</a></li> <li><a href="/wiki/Nizatidine" title="Nizatidine">Nizatidine</a></li> <li><a href="/wiki/Ranitidine" title="Ranitidine">Ranitidine</a><sup>#‡</sup></li> <li><a href="/wiki/Roxatidine_acetate" title="Roxatidine acetate">Roxatidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prostaglandin" title="Prostaglandin">Prostaglandins</a> (E)/<br /><a href="/wiki/Prostaglandin_analogue" title="Prostaglandin analogue">analogues</a> ("-prost-")</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Misoprostol" title="Misoprostol">Misoprostol</a></li> <li><a href="/wiki/Enprostil" title="Enprostil">Enprostil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Proton-pump_inhibitor" title="Proton-pump inhibitor">Proton-pump inhibitors</a> <br />("-prazole")</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anaprazole" title="Anaprazole">Anaprazole</a></li> <li><a href="/wiki/Azeloprazole" title="Azeloprazole">Azeloprazole</a></li> <li><a href="/wiki/Dexlansoprazole" title="Dexlansoprazole">Dexlansoprazole</a></li> <li><a href="/w/index.php?title=Dexrabeprazole&action=edit&redlink=1" class="new" title="Dexrabeprazole (page does not exist)">Dexrabeprazole</a></li> <li><a href="/wiki/Esomeprazole" title="Esomeprazole">Esomeprazole</a></li> <li><a href="/wiki/Ilaprazole" title="Ilaprazole">Ilaprazole</a></li> <li><a href="/wiki/Lansoprazole" title="Lansoprazole">Lansoprazole</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a><sup>#</sup></li> <li><a href="/wiki/Pantoprazole" title="Pantoprazole">Pantoprazole</a></li> <li><a href="/w/index.php?title=Picoprazole&action=edit&redlink=1" class="new" title="Picoprazole (page does not exist)">Picoprazole</a></li> <li><a href="/wiki/Rabeprazole" title="Rabeprazole">Rabeprazole</a></li> <li><a href="/wiki/Tenatoprazole" title="Tenatoprazole">Tenatoprazole</a></li> <li><a href="/wiki/Timoprazole" title="Timoprazole">Timoprazole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium-competitive_acid_blocker" class="mw-redirect" title="Potassium-competitive acid blocker">Potassium-competitive <br />acid blockers</a> ("-prazan")</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Fexuprazan" title="Fexuprazan">Fexuprazan</a></li> <li><a href="/wiki/Linaprazan" title="Linaprazan">Linaprazan</a></li> <li><a href="/wiki/Revaprazan" title="Revaprazan">Revaprazan</a></li> <li><a href="/w/index.php?title=Soraprazan&action=edit&redlink=1" class="new" title="Soraprazan (page does not exist)">Soraprazan</a></li> <li><a href="/w/index.php?title=Tegoprazan&action=edit&redlink=1" class="new" title="Tegoprazan (page does not exist)">Tegoprazan</a></li> <li><a href="/wiki/Vonoprazan" title="Vonoprazan">Vonoprazan</a></li> <li><a href="/wiki/Zastaprazan" title="Zastaprazan">Zastaprazan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aceglutamide_aluminum" class="mw-redirect" title="Aceglutamide aluminum">Aceglutamide aluminum</a></li> <li><a href="/wiki/Acetoxolone" title="Acetoxolone">Acetoxolone</a></li> <li><a href="/wiki/Alginic_acid" title="Alginic acid">Alginic acid</a></li> <li><a href="/wiki/Arbaclofen_placarbil" title="Arbaclofen placarbil">Arbaclofen placarbil</a></li> <li><a href="/wiki/Bismuth_subcitrate" title="Bismuth subcitrate">Bismuth subcitrate</a></li> <li><a href="/wiki/Carbenoxolone" title="Carbenoxolone">Carbenoxolone</a></li> <li><a href="/wiki/Cetraxate" title="Cetraxate">Cetraxate</a></li> <li><a href="/wiki/Gefarnate" title="Gefarnate">Gefarnate</a></li> <li><a href="/wiki/Irsogladine" title="Irsogladine">Irsogladine</a></li> <li><a href="/wiki/Lesogaberan" title="Lesogaberan">Lesogaberan</a></li> <li><a href="/wiki/Pirenzepine" title="Pirenzepine">Pirenzepine</a></li> <li><a href="/wiki/Proglumide" title="Proglumide">Proglumide</a></li> <li><a href="/wiki/Rebamipide" title="Rebamipide">Rebamipide</a></li> <li><a href="/wiki/Sucralfate" title="Sucralfate">Sucralfate</a></li> <li><a href="/wiki/Sulglicotide" title="Sulglicotide">Sulglicotide</a></li> <li><a href="/wiki/Telenzepine" title="Telenzepine">Telenzepine</a></li> <li><a href="/wiki/Teprenone" title="Teprenone">Teprenone</a></li> <li><a href="/wiki/Troxipide" title="Troxipide">Troxipide</a></li> <li><a href="/wiki/Zinc_L-carnosine" title="Zinc L-carnosine">Zinc L-carnosine</a></li> <li><a href="/wiki/Zolimidine" title="Zolimidine">Zolimidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bismuth_subcitrate/metronidazole/tetracycline" title="Bismuth subcitrate/metronidazole/tetracycline">Bismuth subcitrate/metronidazole/tetracycline</a></li> <li><a href="/wiki/Omeprazole/amoxicillin/rifabutin" title="Omeprazole/amoxicillin/rifabutin">Omeprazole/amoxicillin/rifabutin</a></li> <li><a href="/wiki/Vonoprazan/amoxicillin" title="Vonoprazan/amoxicillin">Vonoprazan/amoxicillin</a></li> <li><a href="/wiki/Vonoprazan/amoxicillin/clarithromycin" title="Vonoprazan/amoxicillin/clarithromycin">Vonoprazan/amoxicillin/clarithromycin</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>See also: <a href="/wiki/Helicobacter_pylori_eradication_protocols" title="Helicobacter pylori eradication protocols"><i>Helicobacter pylori</i> eradication protocols</a></i></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><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="Histamine_receptor_modulators440" 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:Histamine_receptor_modulators" title="Template:Histamine receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Histamine_receptor_modulators" title="Template talk:Histamine receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Histamine_receptor_modulators" title="Special:EditPage/Template:Histamine receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Histamine_receptor_modulators440" style="font-size:114%;margin:0 4em"><a href="/wiki/Histamine_receptor" title="Histamine receptor">Histamine 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/Histamine_H1_receptor" title="Histamine H1 receptor">H<sub>1</sub></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%">Agonists</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/2-Pyridylethylamine" title="2-Pyridylethylamine">2-Pyridylethylamine</a></li> <li><a href="/wiki/Betahistine" title="Betahistine">Betahistine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Histamine_trifluoromethyl_toluidide" title="Histamine trifluoromethyl toluidide">HTMT</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><span style="font-size:85%;">L</span>-Histidine</a></li> <li><a href="/wiki/UR-AK49" title="UR-AK49">UR-AK49</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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>First-generation:</i> <a href="/wiki/4-Methyldiphenhydramine" title="4-Methyldiphenhydramine">4-Methyldiphenhydramine</a></li> <li><a href="/wiki/Alimemazine" title="Alimemazine">Alimemazine</a></li> <li><a href="/wiki/Antazoline" title="Antazoline">Antazoline</a></li> <li><a href="/wiki/Azatadine" title="Azatadine">Azatadine</a></li> <li><a href="/wiki/Bamipine" title="Bamipine">Bamipine</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine (benztropine)</a></li> <li><a href="/wiki/Bepotastine" title="Bepotastine">Bepotastine</a></li> <li><a href="/wiki/Bromazine" title="Bromazine">Bromazine</a></li> <li><a href="/wiki/Brompheniramine" title="Brompheniramine">Brompheniramine</a></li> <li><a href="/wiki/Buclizine" title="Buclizine">Buclizine</a></li> <li><a href="/wiki/Captodiame" title="Captodiame">Captodiame</a></li> <li><a href="/wiki/Carbinoxamine" title="Carbinoxamine">Carbinoxamine</a></li> <li><a href="/wiki/Chlorcyclizine" title="Chlorcyclizine">Chlorcyclizine</a></li> <li><a href="/wiki/Chloropyramine" title="Chloropyramine">Chloropyramine</a></li> <li><a href="/wiki/Chlorothen" title="Chlorothen">Chlorothen</a></li> <li><a href="/wiki/Chlorphenamine" title="Chlorphenamine">Chlorphenamine</a></li> <li><a href="/wiki/Chlorphenoxamine" title="Chlorphenoxamine">Chlorphenoxamine</a></li> <li><a href="/wiki/Cinnarizine" title="Cinnarizine">Cinnarizine</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/Clobenzepam" title="Clobenzepam">Clobenzepam</a></li> <li><a href="/wiki/Clocinizine" title="Clocinizine">Clocinizine</a></li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/Cyclizine" title="Cyclizine">Cyclizine</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dacemazine" title="Dacemazine">Dacemazine</a></li> <li><a href="/w/index.php?title=Decloxizine&action=edit&redlink=1" class="new" title="Decloxizine (page does not exist)">Decloxizine</a></li> <li><a href="/wiki/Deptropine" title="Deptropine">Deptropine</a></li> <li><a href="/wiki/Dexbrompheniramine" title="Dexbrompheniramine">Dexbrompheniramine</a></li> <li><a href="/wiki/Dexchlorpheniramine" title="Dexchlorpheniramine">Dexchlorpheniramine</a></li> <li><a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">Dimenhydrinate</a></li> <li><a href="/wiki/Dimetindene" title="Dimetindene">Dimetindene</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Diphenylpyraline" title="Diphenylpyraline">Diphenylpyraline</a></li> <li><a href="/wiki/Doxylamine" title="Doxylamine">Doxylamine</a></li> <li><a href="/wiki/Embramine" title="Embramine">Embramine</a></li> <li><a href="/wiki/Etodroxizine" title="Etodroxizine">Etodroxizine</a></li> <li><a href="/wiki/Etybenzatropine" title="Etybenzatropine">Etybenzatropine (ethylbenztropine)</a></li> <li><a href="/wiki/Etymemazine" title="Etymemazine">Etymemazine</a></li> <li><a href="/wiki/Fenethazine" title="Fenethazine">Fenethazine</a></li> <li><a href="/wiki/Flunarizine" title="Flunarizine">Flunarizine</a></li> <li><a href="/wiki/Histapyrrodine" title="Histapyrrodine">Histapyrrodine</a></li> <li><a href="/wiki/Homochlorcyclizine" title="Homochlorcyclizine">Homochlorcyclizine</a></li> <li><a href="/wiki/Hydroxyethylpromethazine" title="Hydroxyethylpromethazine">Hydroxyethylpromethazine</a></li> <li><a href="/wiki/Hydroxyzine" title="Hydroxyzine">Hydroxyzine</a></li> <li><a href="/wiki/Isopromethazine" title="Isopromethazine">Isopromethazine</a></li> <li><a href="/wiki/Isothipendyl" title="Isothipendyl">Isothipendyl</a></li> <li><a href="/wiki/Meclozine" class="mw-redirect" title="Meclozine">Meclozine</a></li> <li><a href="/wiki/Medrylamine" title="Medrylamine">Medrylamine</a></li> <li><a href="/wiki/Mepyramine" title="Mepyramine">Mepyramine (pyrilamine)</a></li> <li><a href="/wiki/Mequitazine" title="Mequitazine">Mequitazine</a></li> <li><a href="/wiki/Methafurylene" title="Methafurylene">Methafurylene</a></li> <li><a href="/wiki/Methapyrilene" title="Methapyrilene">Methapyrilene</a></li> <li><a href="/wiki/Methdilazine" title="Methdilazine">Methdilazine</a></li> <li><a href="/wiki/Moxastine" title="Moxastine">Moxastine</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Oxatomide" title="Oxatomide">Oxatomide</a></li> <li><a href="/wiki/Oxomemazine" title="Oxomemazine">Oxomemazine</a></li> <li><a href="/wiki/Perlapine" title="Perlapine">Perlapine</a></li> <li><a href="/wiki/Phenindamine" title="Phenindamine">Phenindamine</a></li> <li><a href="/wiki/Pheniramine" title="Pheniramine">Pheniramine</a></li> <li><a href="/wiki/Phenyltoloxamine" title="Phenyltoloxamine">Phenyltoloxamine</a></li> <li><a href="/wiki/Pimethixene" title="Pimethixene">Pimethixene</a></li> <li><a href="/wiki/Piperoxan" title="Piperoxan">Piperoxan</a></li> <li><a href="/wiki/Pipoxizine" title="Pipoxizine">Pipoxizine</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Propiomazine" title="Propiomazine">Propiomazine</a></li> <li><a href="/wiki/Pyrrobutamine" title="Pyrrobutamine">Pyrrobutamine</a></li> <li><a href="/wiki/Talastine" title="Talastine">Talastine</a></li> <li><a href="/wiki/Thenalidine" title="Thenalidine">Thenalidine</a></li> <li><a href="/wiki/Thenyldiamine" title="Thenyldiamine">Thenyldiamine</a></li> <li><a href="/wiki/Thiazinamium" class="mw-redirect" title="Thiazinamium">Thiazinamium</a></li> <li><a href="/wiki/Thonzylamine" title="Thonzylamine">Thonzylamine</a></li> <li><a href="/wiki/Tolpropamine" title="Tolpropamine">Tolpropamine</a></li> <li><a href="/wiki/Tripelennamine" title="Tripelennamine">Tripelennamine</a></li> <li><a href="/wiki/Triprolidine" title="Triprolidine">Triprolidine</a></li></ul> <ul><li><i>Second/third-generation:</i> <a href="/wiki/Acrivastine" title="Acrivastine">Acrivastine</a></li> <li><a href="/w/index.php?title=Alinastine&action=edit&redlink=1" class="new" title="Alinastine (page does not exist)">Alinastine</a></li> <li><a href="/wiki/Astemizole" title="Astemizole">Astemizole</a></li> <li><a href="/wiki/Azelastine" title="Azelastine">Azelastine</a></li> <li><a href="/w/index.php?title=Bamirastine&action=edit&redlink=1" class="new" title="Bamirastine (page does not exist)">Bamirastine</a></li> <li><a href="/w/index.php?title=Barmastine&action=edit&redlink=1" class="new" title="Barmastine (page does not exist)">Barmastine</a></li> <li><a href="/w/index.php?title=Bepiastine&action=edit&redlink=1" class="new" title="Bepiastine (page does not exist)">Bepiastine</a></li> <li><a href="/wiki/Bepotastine" title="Bepotastine">Bepotastine</a></li> <li><a href="/wiki/Bilastine" title="Bilastine">Bilastine</a></li> <li><a href="/w/index.php?title=Cabastinen&action=edit&redlink=1" class="new" title="Cabastinen (page does not exist)">Cabastinen</a></li> <li><a href="/w/index.php?title=Carebastine&action=edit&redlink=1" class="new" title="Carebastine (page does not exist)">Carebastine</a></li> <li><a href="/wiki/Cetirizine" title="Cetirizine">Cetirizine</a></li> <li><a href="/wiki/Clemastine" title="Clemastine">Clemastine</a></li> <li><a href="/wiki/Clemizole" title="Clemizole">Clemizole</a></li> <li><a href="/wiki/Clobenztropine" title="Clobenztropine">Clobenztropine</a></li> <li><a href="/wiki/Desloratadine" title="Desloratadine">Desloratadine</a></li> <li><a href="/w/index.php?title=Dorastine&action=edit&redlink=1" class="new" title="Dorastine (page does not exist)">Dorastine</a></li> <li><a href="/wiki/Ebastine" title="Ebastine">Ebastine</a></li> <li><a href="/w/index.php?title=Efletirizine&action=edit&redlink=1" class="new" title="Efletirizine (page does not exist)">Efletirizine</a></li> <li><a href="/wiki/Emedastine" title="Emedastine">Emedastine</a></li> <li><a href="/wiki/Epinastine" title="Epinastine">Epinastine</a></li> <li><a href="/wiki/Fexofenadine" title="Fexofenadine">Fexofenadine</a></li> <li><a href="/w/index.php?title=Flezelastine&action=edit&redlink=1" class="new" title="Flezelastine (page does not exist)">Flezelastine</a></li> <li><a href="/wiki/Ketotifen" title="Ketotifen">Ketotifen</a></li> <li><a href="/wiki/Latrepirdine" title="Latrepirdine">Latrepirdine</a></li> <li><a href="/wiki/Levocabastine" title="Levocabastine">Levocabastine</a></li> <li><a href="/wiki/Levocetirizine" title="Levocetirizine">Levocetirizine</a></li> <li><a href="/w/index.php?title=Linetastine&action=edit&redlink=1" class="new" title="Linetastine (page does not exist)">Linetastine</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/w/index.php?title=Mapinastine&action=edit&redlink=1" class="new" title="Mapinastine (page does not exist)">Mapinastine</a></li> <li><a href="/wiki/Mebhydrolin" title="Mebhydrolin">Mebhydrolin</a></li> <li><a href="/wiki/Mizolastine" title="Mizolastine">Mizolastine</a></li> <li><a href="/wiki/Moxastine" title="Moxastine">Moxastine</a></li> <li><a href="/w/index.php?title=Noberastine&action=edit&redlink=1" class="new" title="Noberastine (page does not exist)">Noberastine</a></li> <li><a href="/w/index.php?title=Octastine&action=edit&redlink=1" class="new" title="Octastine (page does not exist)">Octastine</a></li> <li><a href="/wiki/Olopatadine" title="Olopatadine">Olopatadine</a></li> <li><a href="/w/index.php?title=Perastine&action=edit&redlink=1" class="new" title="Perastine (page does not exist)">Perastine</a></li> <li><a href="/w/index.php?title=Pibaxizine&action=edit&redlink=1" class="new" title="Pibaxizine (page does not exist)">Pibaxizine</a></li> <li><a href="/w/index.php?title=Piclopastine&action=edit&redlink=1" class="new" title="Piclopastine (page does not exist)">Piclopastine</a></li> <li><a href="/wiki/Quifenadine" title="Quifenadine">Quifenadine (phencarol)</a></li> <li><a href="/w/index.php?title=Rocastine&action=edit&redlink=1" class="new" title="Rocastine (page does not exist)">Rocastine</a></li> <li><a href="/wiki/Rupatadine" title="Rupatadine">Rupatadine</a></li> <li><a href="/wiki/Setastine" title="Setastine">Setastine</a></li> <li><a href="/w/index.php?title=Sequifenadine&action=edit&redlink=1" class="new" title="Sequifenadine (page does not exist)">Sequifenadine (bicarphen)</a></li> <li><a href="/wiki/Talastine" title="Talastine">Talastine</a></li> <li><a href="/w/index.php?title=Temelastine&action=edit&redlink=1" class="new" title="Temelastine (page does not exist)">Temelastine</a></li> <li><a href="/wiki/Terfenadine" title="Terfenadine">Terfenadine</a></li> <li><a href="/w/index.php?title=Vapitadine&action=edit&redlink=1" class="new" title="Vapitadine (page does not exist)">Vapitadine</a></li> <li><a href="/w/index.php?title=Zepastine&action=edit&redlink=1" class="new" title="Zepastine (page does not exist)">Zepastine</a></li></ul> <ul><li><i>Others:</i> <a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</a> (e.g., <a href="/wiki/Aripiprazole" title="Aripiprazole">aripiprazole</a>, <a href="/wiki/Asenapine" title="Asenapine">asenapine</a>, <a href="/wiki/Brexpiprazole" title="Brexpiprazole">brexpiprazole</a>, <a href="/wiki/Brilaroxazine" title="Brilaroxazine">brilaroxazine</a>, <a href="/wiki/Clozapine" title="Clozapine">clozapine</a>, <a href="/wiki/Iloperidone" title="Iloperidone">iloperidone</a>, <a href="/wiki/Olanzapine" title="Olanzapine">olanzapine</a>, <a href="/wiki/Paliperidone" title="Paliperidone">paliperidone</a>, <a href="/wiki/Quetiapine" title="Quetiapine">quetiapine</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>, <a href="/wiki/Zotepine" title="Zotepine">zotepine</a>)</li> <li><a href="/wiki/Phenylpiperazine" title="Phenylpiperazine">Phenylpiperazine</a> <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a> (e.g., <a href="/wiki/Hydroxynefazodone" title="Hydroxynefazodone">hydroxynefazodone</a>, <a href="/wiki/Nefazodone" title="Nefazodone">nefazodone</a>, <a href="/wiki/Trazodone" title="Trazodone">trazodone</a>, <a href="/wiki/Triazoledione" title="Triazoledione">triazoledione</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/Loxapine" title="Loxapine">loxapine</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>, <a href="/wiki/Oxaprotiline" title="Oxaprotiline">oxaprotiline</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/Butriptyline" title="Butriptyline">butriptyline</a>, <a href="/wiki/Clomipramine" title="Clomipramine">clomipramine</a>, <a href="/wiki/Desipramine" title="Desipramine">desipramine</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/Iprindole" title="Iprindole">iprindole</a>, <a href="/wiki/Lofepramine" title="Lofepramine">lofepramine</a>, <a href="/wiki/Nortriptyline" title="Nortriptyline">nortriptyline</a>, <a href="/wiki/Protriptyline" title="Protriptyline">protriptyline</a>, <a href="/wiki/Trimipramine" title="Trimipramine">trimipramine</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/Flupenthixol" class="mw-redirect" title="Flupenthixol">flupenthixol</a>, <a href="/wiki/Fluphenazine" title="Fluphenazine">fluphenazine</a>, <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Perphenazine" title="Perphenazine">perphenazine</a>, <a href="/wiki/Prochlorperazine" title="Prochlorperazine">prochlorperazine</a>, <a href="/wiki/Thioridazine" title="Thioridazine">thioridazine</a>, <a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">thiothixene</a>)</li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/w/index.php?title=Azanator&action=edit&redlink=1" class="new" title="Azanator (page does not exist)">Azanator</a></li> <li><a href="/w/index.php?title=Belarizine&action=edit&redlink=1" class="new" title="Belarizine (page does not exist)">Belarizine</a></li> <li><a href="/w/index.php?title=Elbanizine&action=edit&redlink=1" class="new" title="Elbanizine (page does not exist)">Elbanizine</a></li> <li><a href="/w/index.php?title=Flotrenizine&action=edit&redlink=1" class="new" title="Flotrenizine (page does not exist)">Flotrenizine</a></li> <li><a href="/w/index.php?title=GSK1004723&action=edit&redlink=1" class="new" title="GSK1004723 (page does not exist)">GSK1004723</a></li> <li><a href="/wiki/Napactadine" title="Napactadine">Napactadine</a></li> <li><a href="/w/index.php?title=Tagorizine&action=edit&redlink=1" class="new" title="Tagorizine (page does not exist)">Tagorizine</a></li> <li><a href="/w/index.php?title=Trelnarizine&action=edit&redlink=1" class="new" title="Trelnarizine (page does not exist)">Trelnarizine</a></li> <li><a href="/w/index.php?title=Trenizine&action=edit&redlink=1" class="new" title="Trenizine (page does not exist)">Trenizine</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/Histamine_H2_receptor" title="Histamine H2 receptor">H<sub>2</sub></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%">Agonists</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/Amthamine" title="Amthamine">Amthamine</a></li> <li><a href="/wiki/Betazole" title="Betazole">Betazole</a></li> <li><a href="/wiki/Dimaprit" title="Dimaprit">Dimaprit</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Histamine_trifluoromethyl_toluidide" title="Histamine trifluoromethyl toluidide">HTMT</a></li> <li><a href="/wiki/Impromidine" title="Impromidine">Impromidine</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><span style="font-size:85%;">L</span>-Histidine</a></li> <li><a href="/wiki/UR-AK49" title="UR-AK49">UR-AK49</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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="/w/index.php?title=Bisfentidine&action=edit&redlink=1" class="new" title="Bisfentidine (page does not exist)">Bisfentidine</a></li> <li><a href="/wiki/Burimamide" title="Burimamide">Burimamide</a></li> <li><a class="mw-selflink selflink">Cimetidine</a></li> <li><a href="/w/index.php?title=Dalcotidine&action=edit&redlink=1" class="new" title="Dalcotidine (page does not exist)">Dalcotidine</a></li> <li><a href="/w/index.php?title=Donetidine&action=edit&redlink=1" class="new" title="Donetidine (page does not exist)">Donetidine</a></li> <li><a href="/wiki/Ebrotidine" title="Ebrotidine">Ebrotidine</a></li> <li><a href="/w/index.php?title=Etintidine&action=edit&redlink=1" class="new" title="Etintidine (page does not exist)">Etintidine</a></li> <li><a href="/wiki/Famotidine" title="Famotidine">Famotidine</a></li> <li><a href="/w/index.php?title=Isolamtidine&action=edit&redlink=1" class="new" title="Isolamtidine (page does not exist)">Isolamtidine</a></li> <li><a href="/wiki/Lafutidine" title="Lafutidine">Lafutidine</a></li> <li><a href="/w/index.php?title=Lamtidine&action=edit&redlink=1" class="new" title="Lamtidine (page does not exist)">Lamtidine</a></li> <li><a href="/wiki/Lavoltidine" title="Lavoltidine">Lavoltidine (loxtidine)</a></li> <li><a href="/wiki/Lupitidine" title="Lupitidine">Lupitidine</a></li> <li><a href="/wiki/Metiamide" title="Metiamide">Metiamide</a></li> <li><a href="/w/index.php?title=Mifentidine&action=edit&redlink=1" class="new" title="Mifentidine (page does not exist)">Mifentidine</a></li> <li><a href="/wiki/Niperotidine" title="Niperotidine">Niperotidine</a></li> <li><a href="/wiki/Nizatidine" title="Nizatidine">Nizatidine</a></li> <li><a href="/w/index.php?title=Osutidine&action=edit&redlink=1" class="new" title="Osutidine (page does not exist)">Osutidine</a></li> <li><a href="/wiki/Oxmetidine" title="Oxmetidine">Oxmetidine</a></li> <li><a href="/w/index.php?title=Pibutidine&action=edit&redlink=1" class="new" title="Pibutidine (page does not exist)">Pibutidine</a></li> <li><a href="/w/index.php?title=Quisultazine&action=edit&redlink=1" class="new" title="Quisultazine (page does not exist)">Quisultazine (quisultidine)</a></li> <li><a href="/w/index.php?title=Ramixotidine&action=edit&redlink=1" class="new" title="Ramixotidine (page does not exist)">Ramixotidine</a></li> <li><a href="/wiki/Ranitidine" title="Ranitidine">Ranitidine</a></li> <li><a href="/wiki/Roxatidine" class="mw-redirect" title="Roxatidine">Roxatidine</a></li> <li><a href="/wiki/Sufotidine" title="Sufotidine">Sufotidine</a></li> <li><a href="/w/index.php?title=Tiotidine&action=edit&redlink=1" class="new" title="Tiotidine (page does not exist)">Tiotidine</a></li> <li><a href="/w/index.php?title=Tuvatidine&action=edit&redlink=1" class="new" title="Tuvatidine (page does not exist)">Tuvatidine</a></li> <li><a href="/w/index.php?title=Venritidine&action=edit&redlink=1" class="new" title="Venritidine (page does not exist)">Venritidine</a></li> <li><a href="/w/index.php?title=Xaltidine&action=edit&redlink=1" class="new" title="Xaltidine (page does not exist)">Xaltidine</a></li> <li><a href="/wiki/Zolantidine" title="Zolantidine">Zolantidine</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/Histamine_H3_receptor" title="Histamine H3 receptor">H<sub>3</sub></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%">Agonists</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/Alpha-Methylhistamine" class="mw-redirect" title="Alpha-Methylhistamine">α-Methylhistamine</a></li> <li><a href="/wiki/Cipralisant" title="Cipralisant">Cipralisant</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Imetit" title="Imetit">Imetit</a></li> <li><a href="/wiki/Immepip" title="Immepip">Immepip</a></li> <li><a href="/wiki/Immethridine" title="Immethridine">Immethridine</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><span style="font-size:85%;">L</span>-Histidine</a></li> <li><a href="/wiki/Methimepip" title="Methimepip">Methimepip</a></li> <li><a href="/wiki/Proxyfan" title="Proxyfan">Proxyfan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/A-349821" title="A-349821">A-349821</a></li> <li><a href="/wiki/A-423579" title="A-423579">A-423579</a></li> <li><a href="/wiki/ABT-239" title="ABT-239">ABT-239</a></li> <li><a href="/w/index.php?title=ABT-652&action=edit&redlink=1" class="new" title="ABT-652 (page does not exist)">ABT-652</a></li> <li><a href="/w/index.php?title=AZD5213&action=edit&redlink=1" class="new" title="AZD5213 (page does not exist)">AZD5213</a></li> <li><a href="/w/index.php?title=Bavisant&action=edit&redlink=1" class="new" title="Bavisant (page does not exist)">Bavisant</a></li> <li><a href="/wiki/Betahistine" title="Betahistine">Betahistine</a></li> <li><a href="/wiki/Burimamide" title="Burimamide">Burimamide</a></li> <li><a href="/wiki/Ciproxifan" title="Ciproxifan">Ciproxifan</a></li> <li><a href="/wiki/Clobenpropit" title="Clobenpropit">Clobenpropit</a></li> <li><a href="/wiki/Conessine" title="Conessine">Conessine</a></li> <li><a href="/wiki/Enerisant" title="Enerisant">Enerisant</a></li> <li><a href="/wiki/GSK-189254" title="GSK-189254">GSK-189254</a></li> <li><a href="/wiki/Impentamine" title="Impentamine">Impentamine</a></li> <li><a href="/wiki/Iodophenpropit" title="Iodophenpropit">Iodophenpropit</a></li> <li><a href="/w/index.php?title=Irdabisant&action=edit&redlink=1" class="new" title="Irdabisant (page does not exist)">Irdabisant</a></li> <li><a href="/wiki/JNJ-5207852" title="JNJ-5207852">JNJ-5207852</a></li> <li><a href="/wiki/NNC_38-1049" title="NNC 38-1049">NNC 38-1049</a></li> <li><a href="/wiki/PF-03654746" title="PF-03654746">PF-03654746</a></li> <li><a href="/wiki/Pitolisant" title="Pitolisant">Pitolisant</a></li> <li><a href="/wiki/SCH-79687" title="SCH-79687">SCH-79687</a></li> <li><a href="/wiki/Thioperamide" title="Thioperamide">Thioperamide</a></li> <li><a href="/wiki/VUF-5681" title="VUF-5681">VUF-5681</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/Histamine_H4_receptor" title="Histamine H4 receptor">H<sub>4</sub></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%">Agonists</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/4-Methylhistamine" title="4-Methylhistamine">4-Methylhistamine</a></li> <li><a href="/wiki/Alpha-Methylhistamine" class="mw-redirect" title="Alpha-Methylhistamine">α-Methylhistamine</a></li> <li><a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><span style="font-size:85%;">L</span>-Histidine</a></li> <li><a href="/wiki/OUP-16" title="OUP-16">OUP-16</a></li> <li><a href="/wiki/VUF-8430" title="VUF-8430">VUF-8430</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Antagonists</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/JNJ-7777120" title="JNJ-7777120">JNJ-7777120</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/w/index.php?title=Seliforant&action=edit&redlink=1" class="new" title="Seliforant (page does not exist)">Seliforant</a></li> <li><a href="/wiki/Thioperamide" title="Thioperamide">Thioperamide</a></li> <li><a href="/wiki/Toreforant" title="Toreforant">Toreforant</a></li> <li><a href="/wiki/VUF-6002" title="VUF-6002">VUF-6002</a></li></ul> </div></td></tr></tbody></table><div></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:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a></dd> <dd><a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a></dd></dl> </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="Androgen_receptor_modulators801" 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:Androgen_receptor_modulators" title="Template:Androgen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgen_receptor_modulators" title="Template talk:Androgen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgen_receptor_modulators" title="Special:EditPage/Template:Androgen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgen_receptor_modulators801" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen_receptor" title="Androgen receptor">Androgen 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/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">AR</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 Androgen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Testosterone derivatives:</i> <a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Dehydroepiandrosterone" title="4-Dehydroepiandrosterone">4-Dehydroepiandrosterone (4-DHEA)</a></li> <li><a href="/wiki/4-Hydroxytestosterone" title="4-Hydroxytestosterone">4-Hydroxytestosterone</a></li> <li><a href="/w/index.php?title=4,17%CE%B1-Dimethyltestosterone&action=edit&redlink=1" class="new" title="4,17α-Dimethyltestosterone (page does not exist)">4,17α-Dimethyltestosterone</a></li> <li><a href="/wiki/5-Androstenedione" title="5-Androstenedione">5-Androstenedione</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyandrostenedione" title="11β-Hydroxyandrostenedione">11β-Hydroxyandrostenedione</a></li> <li><a href="/wiki/Adrenosterone" title="Adrenosterone">Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">Androstenediol (5-androstenediol)</a> <ul><li><a href="/wiki/Androstenediol_3%CE%B2-acetate" title="Androstenediol 3β-acetate">Androstenediol 3β-acetate</a></li> <li><a href="/wiki/Androstenediol_17%CE%B2-acetate" title="Androstenediol 17β-acetate">Androstenediol 17β-acetate</a></li> <li><a href="/wiki/Androstenediol_diacetate" title="Androstenediol diacetate">Androstenediol diacetate</a></li> <li><a href="/wiki/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li></ul></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">Androstenedione (4-androstenedione)</a></li> <li><a href="/wiki/Atamestane" title="Atamestane">Atamestane</a></li> <li><a href="/wiki/Boldenone" title="Boldenone">Boldenone</a> <ul><li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li></ul></li> <li><a href="/wiki/Boldione" title="Boldione">Boldione (1,4-androstadienedione)</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a> <ul><li><a href="/wiki/Clostebol_acetate" title="Clostebol acetate">Clostebol acetate</a></li> <li><a href="/wiki/Clostebol_caproate" title="Clostebol caproate">Clostebol caproate</a></li> <li><a href="/wiki/Clostebol_propionate" title="Clostebol propionate">Clostebol propionate</a></li></ul></li> <li><a href="/wiki/Cloxotestosterone" title="Cloxotestosterone">Cloxotestosterone</a> <ul><li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li></ul></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA (androstenolone, prasterone; 5-DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">DHEA enanthate (prasterone enanthate)</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li></ul></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li> <li><a href="/wiki/Plomestane" title="Plomestane">Plomestane</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Silandrone" title="Silandrone">Silandrone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a><sup>#</sup> (<a href="/wiki/Testosterone/dutasteride" title="Testosterone/dutasteride">+dutasteride</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a></li> <li><a href="/wiki/Polytestosterone_phloretin_phosphate" title="Polytestosterone phloretin phosphate">Polytestosterone phloretin phosphate</a></li></ul></li></ul> <ul><li><i>5α-Dihydrotestosterone derivatives:</i> <a href="/wiki/1-Androstenediol" title="1-Androstenediol">1-Androstenediol</a></li> <li><a href="/wiki/1-Androstenedione" title="1-Androstenedione">1-Androstenedione</a></li> <li><a href="/wiki/1-Androsterone" title="1-Androsterone">1-Androsterone (1-andro, 1-DHEA)</a></li> <li><a href="/wiki/1-Testosterone" title="1-Testosterone">1-Testosterone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/5%CE%B1-Androst-2-en-17-one" class="mw-redirect" title="5α-Androst-2-en-17-one">5α-Androst-2-en-17-one</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Bolazine" title="Bolazine">Bolazine</a> <ul><li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li></ul></li> <li><a href="/w/index.php?title=Dihydroethyltestosterone&action=edit&redlink=1" class="new" title="Dihydroethyltestosterone (page does not exist)">Dihydroethyltestosterone</a></li> <li><a href="/wiki/Dihydrofluoxymesterone" title="Dihydrofluoxymesterone">Dihydrofluoxymesterone</a></li> <li><a href="/w/index.php?title=Dihydromethylandrostenediol&action=edit&redlink=1" class="new" title="Dihydromethylandrostenediol (page does not exist)">Dihydromethylandrostenediol</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone (DHT)</a> (<a href="/wiki/Androstanolone" title="Androstanolone">androstanolone, stanolone</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Dihydrotestosterone esters</a></li></ul></li> <li><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a> <ul><li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate</a></li></ul></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Mesabolone" title="Mesabolone">Mesabolone</a></li> <li><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a> <ul><li><a href="/wiki/Mesterolone_cipionate" title="Mesterolone cipionate">Mesterolone cipionate</a></li></ul></li> <li><a href="/wiki/Methyldiazinol" title="Methyldiazinol">Methyldiazinol</a></li> <li><a href="/wiki/Nisterime" title="Nisterime">Nisterime</a> <ul><li><a href="/wiki/Nisterime_acetate" title="Nisterime acetate">Nisterime acetate</a></li></ul></li> <li><a href="/wiki/Prostanozol" title="Prostanozol">Prostanozol</a></li> <li><a href="/wiki/Stenbolone" title="Stenbolone">Stenbolone</a> <ul><li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul></li> <li><a href="/wiki/Testifenon" title="Testifenon">Testifenon (testiphenon, testiphenone)</a></li></ul> <ul><li><i>19-Nortestosterone derivatives:</i> <a href="/wiki/7%CE%B1-Methyl-19-norandrostenedione" title="7α-Methyl-19-norandrostenedione">7α-Methyl-19-norandrostenedione (MENT dione, trestione)</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a> <ul><li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li></ul></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a> <ul><li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li></ul></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione (19-nor-4-androstenedione)</a></li> <li><a href="/wiki/Bolmantalate" title="Bolmantalate">Bolmantalate (nandrolone adamantoate)</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a> <ul><li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li></ul></li> <li><a href="/wiki/LS-1727" title="LS-1727">LS-1727 (nandrolone 17β-<i>N</i>-(2-chloroethyl)-<i>N</i>-nitrosocarbamate)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a> <ul><li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">Nandrolone esters</a></li></ul></li> <li><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a> <ul><li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li></ul></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Oxabolone" title="Oxabolone">Oxabolone</a> <ul><li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li></ul></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone</a> <ul><li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">Trenbolone enanthate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate</a></li> <li><a href="/wiki/Trenbolone_undecanoate" title="Trenbolone undecanoate">Trenbolone undecanoate</a></li></ul></li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone (MENT)</a> <ul><li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li> <li><a href="/wiki/Trestolone_enanthate" title="Trestolone enanthate">Trestolone enanthate</a></li></ul></li></ul> <ul><li><i>5α-Dihydro-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydronandrolone" title="5α-Dihydronandrolone">5α-Dihydronandrolone</a></li> <li><a href="/w/index.php?title=5%CE%B1-Dihydrotrestolone&action=edit&redlink=1" class="new" title="5α-Dihydrotrestolone (page does not exist)">5α-Dihydrotrestolone</a></li> <li><a href="/wiki/19-Norandrosterone" title="19-Norandrosterone">19-Norandrosterone</a></li></ul> <ul><li><i>17α-Alkylated testosterone derivatives:</i> <a href="/wiki/Bolasterone" title="Bolasterone">Bolasterone</a></li> <li><a href="/wiki/Calusterone" title="Calusterone">Calusterone</a></li> <li><a href="/wiki/Chlorodehydromethylandrostenediol" title="Chlorodehydromethylandrostenediol">Chlorodehydromethylandrostenediol (CDMA)</a></li> <li><a href="/wiki/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</a></li> <li><a href="/wiki/Chloromethylandrostenediol" title="Chloromethylandrostenediol">Chloromethylandrostenediol (CMA)</a></li> <li><a href="/wiki/Enestebol" title="Enestebol">Enestebol</a></li> <li><a href="/wiki/Ethyltestosterone" title="Ethyltestosterone">Ethyltestosterone</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Formebolone" title="Formebolone">Formebolone</a></li> <li><a href="/wiki/Hydroxystenozole" title="Hydroxystenozole">Hydroxystenozole</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone (methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a> <ul><li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</a></li> <li><a href="/wiki/Methandriol_diacetate" title="Methandriol diacetate">Methandriol diacetate</a></li> <li><a href="/wiki/Methandriol_dipropionate" title="Methandriol dipropionate">Methandriol dipropionate</a></li> <li><a href="/wiki/Methandriol_propionate" title="Methandriol propionate">Methandriol propionate</a></li></ul></li> <li><a href="/wiki/Methylclostebol" title="Methylclostebol">Methylclostebol (chloromethyltestosterone)</a></li> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a> (<a href="/wiki/Esterified_estrogens/methyltestosterone" title="Esterified estrogens/methyltestosterone">+esterified estrogens</a>) <ul><li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></li></ul></li> <li><a href="/wiki/Oxymesterone" title="Oxymesterone">Oxymesterone</a></li> <li><a href="/wiki/Penmesterol" title="Penmesterol">Penmesterol</a></li> <li><a href="/wiki/Tiomesterone" title="Tiomesterone">Tiomesterone</a></li></ul> <ul><li><i>17α-Alkylated 5α-dihydrotestosterone derivatives:</i> <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</a></li> <li><a href="/wiki/Desoxymethyltestosterone" title="Desoxymethyltestosterone">Desoxymethyltestosterone</a></li> <li><a href="/wiki/Furazabol" title="Furazabol">Furazabol</a></li> <li><a href="/wiki/Mebolazine" title="Mebolazine">Mebolazine (dimethazine)</a></li> <li><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></li> <li><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a> <ul><li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a></li></ul></li> <li><a href="/wiki/Methasterone" title="Methasterone">Methasterone</a></li> <li><a href="/wiki/Methyl-1-testosterone" title="Methyl-1-testosterone">Methyl-1-testosterone</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylstenbolone" title="Methylstenbolone">Methylstenbolone</a></li> <li><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></li> <li><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></li> <li><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></li></ul> <ul><li><i>17α-Alkylated 19-nortestosterone derivatives:</i> <a href="/wiki/Bolenol" title="Bolenol">Bolenol</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Methylhydroxynandrolone" title="Methylhydroxynandrolone">Methylhydroxynandrolone (MOHN, MHN)</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norboletone" title="Norboletone">Norboletone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li></ul> <ul><li><i>17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydronorethandrolone" title="5α-Dihydronorethandrolone">5α-Dihydronorethandrolone</a></li> <li><a href="/wiki/5%CE%B1-Dihydronormethandrone" title="5α-Dihydronormethandrone">5α-Dihydronormethandrone</a></li></ul> <ul><li><i>17α-Vinyltestosterone derivatives:</i> <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li><i>17α-Vinyl-19-nortestosterone derivatives:</i> <a href="/wiki/Vinyltestosterone" title="Vinyltestosterone">Vinyltestosterone</a></li></ul> <ul><li><i>17α-Ethynyltestosterone derivatives:</i> <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethisterone" title="Ethisterone">Ethisterone (ethynyltestosterone)</a></li></ul> <ul><li><i>5α-Dihydro-17α-ethynyltestosterone derivatives:</i> <a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li></ul> <ul><li><i>17α-Ethynyl-19-nortestosterone derivatives:</i> <a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ<sup>4</sup>-Tibolone</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a> <ul><li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li></ul></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a> <ul><li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li></ul></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a> <ul><li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li></ul></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:</i> <a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li></ul> <ul><li><i>Progesterone derivatives:</i> <a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li></ul> <ul><li><i>Others/unsorted:</i> <a href="/wiki/3-Keto-5%CE%B1-abiraterone" title="3-Keto-5α-abiraterone">3-Keto-5α-abiraterone</a></li> <li><a href="/wiki/5%CE%B1-Androstane" class="mw-redirect" title="5α-Androstane">5α-Androstane</a></li> <li><a href="/wiki/Alternariol" title="Alternariol">Alternariol</a></li> <li><a href="/wiki/Cl-4AS-1" title="Cl-4AS-1">Cl-4AS-1</a></li> <li><a href="/wiki/Drupanol" title="Drupanol">Drupanol</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Selective_androgen_receptor_modulator" title="Selective androgen receptor modulator"><abbr title="Selective androgen receptor modulator">SARMs</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 androgen receptor modulator</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Nonsteroidal:</i> <a href="/w/index.php?title=198RL26&action=edit&redlink=1" class="new" title="198RL26 (page does not exist)">198RL26</a></li> <li><a href="/wiki/ACP-105" title="ACP-105">ACP-105</a></li> <li><a href="/wiki/AC-262,536" title="AC-262,536">AC-262,536</a></li> <li><a href="/wiki/Acetothiolutamide" title="Acetothiolutamide">Acetothiolutamide</a></li> <li><a href="/wiki/Acetoxolutamide" title="Acetoxolutamide">Acetoxolutamide</a></li> <li><a href="/wiki/Andarine" title="Andarine">Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)</a></li> <li><a href="/wiki/BMS-564,929" title="BMS-564,929">BMS-564,929</a></li> <li><a href="/w/index.php?title=DTIB&action=edit&redlink=1" class="new" title="DTIB (page does not exist)">DTIB</a></li> <li><a href="/wiki/Enobosarm" title="Enobosarm">Enobosarm (ostarine, MK-2866, GTx-024, S-22)</a></li> <li><a href="/w/index.php?title=FTBU-1&action=edit&redlink=1" class="new" title="FTBU-1 (page does not exist)">FTBU-1</a></li> <li><a href="/wiki/GLPG-0492" title="GLPG-0492">GLPG-0492</a></li> <li><a href="/wiki/GSK2881078" title="GSK2881078">GSK2881078</a></li> <li><a href="/wiki/GSK-4336A" title="GSK-4336A">GSK-4336A</a></li> <li><a href="/w/index.php?title=GSK-8698&action=edit&redlink=1" class="new" title="GSK-8698 (page does not exist)">GSK-8698</a></li> <li><a href="/wiki/LG121071" title="LG121071">LG121071 (LGD-121071)</a></li> <li><a href="/wiki/LGD-2226" title="LGD-2226">LGD-2226</a></li> <li><a href="/wiki/LGD-2941" title="LGD-2941">LGD-2941 (LGD-122941)</a></li> <li><a href="/wiki/LGD-3303" title="LGD-3303">LGD-3303</a></li> <li><a href="/wiki/LGD-4033" class="mw-redirect" title="LGD-4033">LGD-4033</a></li> <li><a href="/wiki/LY305" title="LY305">LY305</a></li> <li><a href="/wiki/JNJ-26146900" title="JNJ-26146900">JNJ-26146900</a></li> <li><a href="/wiki/JNJ-28330835" title="JNJ-28330835">JNJ-28330835</a></li> <li><a href="/wiki/JNJ-37654032" title="JNJ-37654032">JNJ-37654032</a></li> <li><a href="/wiki/OPK-88004" title="OPK-88004">OPK-88004 (LY-2452473, TT-701)</a></li> <li><a href="/w/index.php?title=ORM-11984&action=edit&redlink=1" class="new" title="ORM-11984 (page does not exist)">ORM-11984</a></li> <li><a href="/wiki/PF-06260414" title="PF-06260414">PF-06260414</a></li> <li><a href="/w/index.php?title=R-1_(drug)&action=edit&redlink=1" class="new" title="R-1 (drug) (page does not exist)">R-1</a></li> <li><a href="/wiki/RU-59063" title="RU-59063">RU-59063</a></li> <li><a href="/w/index.php?title=S-1_(drug)&action=edit&redlink=1" class="new" title="S-1 (drug) (page does not exist)">S-1</a></li> <li><a href="/wiki/S-23_(drug)" title="S-23 (drug)">S-23</a></li> <li><a href="/wiki/S-40503" title="S-40503">S-40503</a></li> <li><a href="/w/index.php?title=S-101479&action=edit&redlink=1" class="new" title="S-101479 (page does not exist)">S-101479</a></li> <li><a href="/wiki/Vosilasarm" title="Vosilasarm">Vosilasarm</a></li></ul> <ul><li><i>Steroidal:</i> <a href="/w/index.php?title=EM-9017&action=edit&redlink=1" class="new" title="EM-9017 (page does not exist)">EM-9017</a></li> <li><a href="/wiki/MK-0773" title="MK-0773">MK-0773</a></li> <li><a href="/wiki/TFM-4AS-1" title="TFM-4AS-1">TFM-4AS-1</a></li> <li><a href="/wiki/YK-11" title="YK-11">YK-11</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Allyltestosterone" title="Allyltestosterone">Allyltestosterone</a></li> <li><a href="/wiki/Benorterone" title="Benorterone">Benorterone</a></li> <li><a href="/wiki/BOMT" title="BOMT">BOMT</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Clascoterone" title="Clascoterone">Clascoterone</a></li> <li><a href="/wiki/Clometerone" title="Clometerone">Clometerone</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Cyproterone" title="Cyproterone">Cyproterone</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delanterone" title="Delanterone">Delanterone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/w/index.php?title=EM-4350&action=edit&redlink=1" class="new" title="EM-4350 (page does not exist)">EM-4350</a></li> <li><a href="/wiki/EM-5854" title="EM-5854">EM-5854</a></li> <li><a href="/w/index.php?title=EM-5855&action=edit&redlink=1" class="new" title="EM-5855 (page does not exist)">EM-5855</a></li> <li><a href="/w/index.php?title=EM-6537&action=edit&redlink=1" class="new" title="EM-6537 (page does not exist)">EM-6537</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/Galeterone" title="Galeterone">Galeterone</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=Ludaterone&action=edit&redlink=1" class="new" title="Ludaterone (page does not exist)">Ludaterone</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metogest" title="Metogest">Metogest</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Nordinone" title="Nordinone">Nordinone</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/Rosterolone" title="Rosterolone">Rosterolone</a></li> <li><a href="/w/index.php?title=RU-15328&action=edit&redlink=1" class="new" title="RU-15328 (page does not exist)">RU-15328</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Topterone" title="Topterone">Topterone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Trimethyltrienolone" title="Trimethyltrienolone">Trimethyltrienolone (R-2956)</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/5N-Bicalutamide" title="5N-Bicalutamide">5<i>N</i>-Bicalutamide</a></li> <li><a href="/wiki/AA560" title="AA560">AA560</a></li> <li><a href="/w/index.php?title=Antarlide&action=edit&redlink=1" class="new" title="Antarlide (page does not exist)">Antarlides</a></li> <li><a href="/w/index.php?title=Arabilin&action=edit&redlink=1" class="new" title="Arabilin (page does not exist)">Arabilin</a></li> <li><a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Atraric_acid" title="Atraric acid">Atraric acid</a></li> <li><a href="/w/index.php?title=AZD-3514&action=edit&redlink=1" class="new" title="AZD-3514 (page does not exist)">AZD-3514</a></li> <li><a href="/wiki/Bakuchiol" title="Bakuchiol">Bakuchiol</a></li> <li><a href="/wiki/Bavdegalutamide" title="Bavdegalutamide">Bavdegalutamide</a></li> <li><a href="/w/index.php?title=BAY-1024767&action=edit&redlink=1" class="new" title="BAY-1024767 (page does not exist)">BAY-1024767</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Bisphenol" title="Bisphenol">Bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A_diglycidyl_ether" title="Bisphenol A diglycidyl ether">BADGE</a>, <a href="/w/index.php?title=Bisphenol_F_diglycidyl_ether&action=edit&redlink=1" class="new" title="Bisphenol F diglycidyl ether (page does not exist)">BFDGE</a>, <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol A</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">bisphenol F</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">bisphenol S</a>)</li> <li><a href="/w/index.php?title=BMS-501949&action=edit&redlink=1" class="new" title="BMS-501949 (page does not exist)">BMS-501949</a></li> <li><a href="/w/index.php?title=BMS-570511&action=edit&redlink=1" class="new" title="BMS-570511 (page does not exist)">BMS-570511</a></li> <li><a href="/wiki/BMS-641988" title="BMS-641988">BMS-641988</a></li> <li><a href="/w/index.php?title=CH5137291&action=edit&redlink=1" class="new" title="CH5137291 (page does not exist)">CH5137291</a></li> <li><a class="mw-selflink selflink">Cimetidine</a></li> <li><a href="/wiki/Cioteronel" title="Cioteronel">Cioteronel</a></li> <li><a href="/wiki/Cyanonilutamide" title="Cyanonilutamide">Cyanonilutamide</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (via metabolite <a href="/wiki/Dichlorodiphenyldichloroethylene" title="Dichlorodiphenyldichloroethylene">p,p’-DDE</a>)</li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/DIMP_(antiandrogen)" title="DIMP (antiandrogen)">DIMP</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/EPI-001" title="EPI-001">EPI-001</a></li> <li><a href="/wiki/Fenarimol" title="Fenarimol">Fenarimol</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Hydroxyflutamide" title="Hydroxyflutamide">Hydroxyflutamide</a></li> <li><a href="/wiki/Inocoterone" title="Inocoterone">Inocoterone</a></li> <li><a href="/wiki/Inocoterone_acetate" title="Inocoterone acetate">Inocoterone acetate</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Ketodarolutamide" title="Ketodarolutamide">Ketodarolutamide</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/w/index.php?title=LG-105&action=edit&redlink=1" class="new" title="LG-105 (page does not exist)">LG-105</a></li> <li><a href="/wiki/LG-120907" title="LG-120907">LG-120907</a></li> <li><a href="/w/index.php?title=LGD-1331&action=edit&redlink=1" class="new" title="LGD-1331 (page does not exist)">LGD-1331</a></li> <li><a href="/wiki/Linuron" title="Linuron">Linuron</a></li> <li><a href="/wiki/Masofaniten" title="Masofaniten">Masofaniten</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/w/index.php?title=N-Butylbenzenesulfonamide&action=edit&redlink=1" class="new" title="N-Butylbenzenesulfonamide (page does not exist)"><i>N</i>-Butylbenzenesulfonamide</a></li> <li><a href="/wiki/N-Desmethylapalutamide" title="N-Desmethylapalutamide"><i>N</i>-Desmethylapalutamide</a></li> <li><a href="/wiki/N-Desmethylenzalutamide" title="N-Desmethylenzalutamide"><i>N</i>-Desmethylenzalutamide</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/w/index.php?title=ONC1-13B&action=edit&redlink=1" class="new" title="ONC1-13B (page does not exist)">ONC1-13B</a></li> <li><a href="/wiki/Pentomone" title="Pentomone">Pentomone</a></li> <li><a href="/w/index.php?title=PF-998425&action=edit&redlink=1" class="new" title="PF-998425 (page does not exist)">PF-998425</a></li> <li><a href="/wiki/Phenothrin" title="Phenothrin">Phenothrin</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/wiki/Procymidone" title="Procymidone">Procymidone</a></li> <li><a href="/wiki/Proxalutamide" title="Proxalutamide">Proxalutamide</a></li> <li><a href="/wiki/Pyrilutamide" title="Pyrilutamide">Pyrilutamide</a></li> <li><a href="/wiki/Ralaniten" title="Ralaniten">Ralaniten (EPI-002)</a></li> <li><a href="/wiki/Ralaniten_acetate" title="Ralaniten acetate">Ralaniten acetate (EPI-506)</a></li> <li><a href="/wiki/RD-162" title="RD-162">RD-162</a></li> <li><a href="/wiki/Rezvilutamide" title="Rezvilutamide">Rezvilutamide</a></li> <li><a href="/w/index.php?title=Ro_2-7239&action=edit&redlink=1" class="new" title="Ro 2-7239 (page does not exist)">Ro 2-7239</a></li> <li><a href="/w/index.php?title=Ro_5-2537&action=edit&redlink=1" class="new" title="Ro 5-2537 (page does not exist)">Ro 5-2537</a></li> <li><a href="/wiki/RU-22930" title="RU-22930">RU-22930</a></li> <li><a href="/wiki/RU-56187" title="RU-56187">RU-56187</a></li> <li><a href="/wiki/RU-57073" title="RU-57073">RU-57073</a></li> <li><a href="/wiki/RU-58642" title="RU-58642">RU-58642</a></li> <li><a href="/wiki/RU-58841" title="RU-58841">RU-58841</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a></li> <li><a href="/wiki/Thalidomide" title="Thalidomide">Thalidomide</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/wiki/Vinclozolin" title="Vinclozolin">Vinclozolin</a></li> <li><a href="/w/index.php?title=YM-580&action=edit&redlink=1" class="new" title="YM-580 (page does not exist)">YM-580</a></li> <li><a href="/w/index.php?title=YM-92088&action=edit&redlink=1" class="new" title="YM-92088 (page does not exist)">YM-92088</a></li> <li><a href="/w/index.php?title=YM-175735&action=edit&redlink=1" class="new" title="YM-175735 (page does not exist)">YM-175735</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/GPRC6A" title="GPRC6A">GPRC6A</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:6em;;text-align:center;">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cation" class="mw-redirect" title="Cation">Cations</a> (incl. <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Gadolinium" title="Gadolinium">gadolinium</a>, <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, <a href="/wiki/Strontium" title="Strontium">strontium</a>, <a href="/wiki/Zinc" title="Zinc">zinc</a>)</li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Amino_acid" title="Amino acid"><small>L</small>-α-Amino acids</a> (incl. <a href="/wiki/Arginine" title="Arginine"><small>L</small>-arginine</a>, <a href="/wiki/Lysine" title="Lysine"><small>L</small>-lysine</a>, <a href="/wiki/Ornithine" title="Ornithine"><small>L</small>-ornithine</a>)</li> <li><a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a></li> <li><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</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 Sex hormone-binding globulin</span></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> </div></td></tr></tbody></table><div></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:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_androgens_and_anabolic_steroids" title="List of androgens and anabolic steroids">List of androgens and anabolic steroids</a></dd></dl> </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="GSK201" 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:GSK" title="Template:GSK"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GSK" title="Template talk:GSK"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GSK" title="Special:EditPage/Template:GSK"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GSK201" style="font-size:114%;margin:0 4em"><a href="/wiki/GSK_plc" title="GSK plc">GSK</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Subsidiaries</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%">Current</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/GlaxoSmithKline_Pakistan" class="mw-redirect" title="GlaxoSmithKline Pakistan">GlaxoSmithKline Pakistan</a></li> <li><a href="/wiki/GlaxoSmithKline_Pharmaceuticals_Ltd" class="mw-redirect" title="GlaxoSmithKline Pharmaceuticals Ltd">GlaxoSmithKline Pharmaceuticals Ltd</a></li> <li><a href="/wiki/Stiefel_Laboratories" title="Stiefel Laboratories">Stiefel Laboratories</a></li> <li><a href="/wiki/Tesaro" title="Tesaro">Tesaro</a></li> <li><a href="/wiki/ViiV_Healthcare" title="ViiV Healthcare">ViiV Healthcare</a> (85%)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Former</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Haleon" title="Haleon">Haleon</a></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Predecessors,<br />acquisitions</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/Allen_%26_Hanburys" title="Allen & Hanburys">Allen & Hanburys</a></li> <li><a href="/wiki/Beecham_Group" title="Beecham Group">Beecham Group</a></li> <li><a href="/wiki/Block_Drug" title="Block Drug">Block Drug</a></li> <li><a href="/wiki/GSK_plc#Glaxo_Wellcome" title="GSK plc">Burroughs Wellcome</a></li> <li><a href="/wiki/GSK_plc#Glaxo_Wellcome" title="GSK plc">Glaxo</a></li> <li><a href="/wiki/GSK_plc#Glaxo_Wellcome" title="GSK plc">Glaxo Wellcome</a></li> <li><a href="/wiki/Human_Genome_Sciences" title="Human Genome Sciences">Human Genome Sciences</a></li> <li><a href="/wiki/Recherche_et_Industrie_Th%C3%A9rapeutiques" title="Recherche et Industrie Thérapeutiques">Recherche et Industrie Thérapeutiques</a></li> <li><a href="/wiki/Reliant_Pharmaceuticals" title="Reliant Pharmaceuticals">Reliant Pharmaceuticals</a></li> <li><a href="/wiki/S._E._Massengill_Company" title="S. E. Massengill Company">S. E. Massengill Company</a></li> <li><a href="/wiki/GSK_plc#SmithKline_Beecham" title="GSK plc">SmithKline Beecham</a></li> <li><a href="/wiki/Smith,_Kline_%26_French" title="Smith, Kline & French">Smith, Kline & French</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</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%">Current</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%">Pharma</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/Fluticasone/salmeterol" title="Fluticasone/salmeterol">Advair</a></li> <li><a href="/wiki/Orlistat" title="Orlistat">Alli</a></li> <li><a href="/wiki/Amoxicillin/clavulanic_acid" title="Amoxicillin/clavulanic acid">Augmentin</a></li> <li><a href="/wiki/Rosiglitazone" title="Rosiglitazone">Avandia</a></li> <li><a href="/wiki/Beclometasone" title="Beclometasone">Beconase</a></li> <li><a href="/wiki/Ibandronic_acid" title="Ibandronic acid">Boniva</a></li> <li><a href="/wiki/Fluticasone_propionate" title="Fluticasone propionate">Flixonase</a></li> <li><a href="/wiki/Topotecan" title="Topotecan">Hycamtin</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamictal</a></li> <li><a href="/wiki/Paroxetine" title="Paroxetine">Paxil/Seroxat</a></li> <li><a href="/wiki/Piboserod" title="Piboserod">Serlipet</a></li> <li><a class="mw-selflink selflink">Tagamet</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Ventolin</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Wellbutrin/Zyban</a></li> <li><a href="/wiki/Ranitidine" title="Ranitidine">Zantac</a> … <a href="/wiki/List_of_GSK_plc_products" title="List of GSK plc products"><b>more</b></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Vaccines</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/Respiratory_syncytial_virus_vaccine" title="Respiratory syncytial virus vaccine">Arexvy</a></li> <li><a href="/wiki/Bexsero" class="mw-redirect" title="Bexsero">Bexsero</a></li> <li><a href="/wiki/Boostrix" class="mw-redirect" title="Boostrix">Boostrix</a></li> <li><a href="/wiki/Cervarix" title="Cervarix">Cervarix</a></li> <li><a href="/wiki/Engerix-B" class="mw-redirect" title="Engerix-B">Engerix-B </a></li> <li><a href="/wiki/Fluarix" class="mw-redirect" title="Fluarix">Fluarix</a></li> <li><a href="/wiki/FluLaval" class="mw-redirect" title="FluLaval">FluLaval</a></li> <li><a href="/wiki/Havrix" class="mw-redirect" title="Havrix">Havrix</a></li> <li><a href="/wiki/Hepatyrix" class="mw-redirect" title="Hepatyrix">Hepatyrix</a></li> <li><a href="/wiki/Hiberix" class="mw-redirect" title="Hiberix">Hiberix</a></li> <li><a href="/wiki/Infanrix" class="mw-redirect" title="Infanrix">Infanrix</a></li> <li><a href="/wiki/H5N1_vaccine" title="H5N1 vaccine">H5N1 vaccine</a></li> <li><a href="/wiki/Kinrix" class="mw-redirect" title="Kinrix">Kinrix</a></li> <li><a href="/wiki/Menveo" class="mw-redirect" title="Menveo">Menveo</a></li> <li><a href="/wiki/Pandemrix" title="Pandemrix">Pandemrix</a></li> <li><a href="/wiki/Pediarix" class="mw-redirect" title="Pediarix">Pediarix</a></li> <li><a href="/wiki/Rabavert" class="mw-redirect" title="Rabavert">Rabavert</a></li> <li><a href="/wiki/Rotarix" class="mw-redirect" title="Rotarix">Rotarix</a></li> <li><a href="/wiki/Zoster_vaccine#Shingrix" title="Zoster vaccine">Shingrix</a></li> <li><a href="/wiki/Hepatitis_A_and_B_vaccine" title="Hepatitis A and B vaccine">Twinrix</a> … <a href="/wiki/List_of_GSK_plc_products" title="List of GSK plc products"><b>more</b></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Former</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/Actifed" title="Actifed">Actifed</a></li> <li>Advil</li> <li><a href="/wiki/Aquafresh" class="mw-redirect" title="Aquafresh">Aquafresh</a></li> <li><a href="/wiki/BC_Powder" title="BC Powder">BC Powder</a></li> <li><a href="/wiki/Biotene" title="Biotene">Biotene</a></li> <li><a href="/wiki/Caltrate" title="Caltrate">Caltrate</a></li> <li><a href="/wiki/Centrum_(multivitamin)" title="Centrum (multivitamin)">Centrum</a></li> <li><a href="/wiki/ChapStick" title="ChapStick">ChapStick</a></li> <li><a href="/wiki/Emergen-C" title="Emergen-C">Emergen-C</a></li> <li><a href="/wiki/Eno_(drug)" title="Eno (drug)">Eno</a></li> <li><a href="/wiki/Excedrin_(brand)" title="Excedrin (brand)">Excedrin</a></li> <li>Flonase</li> <li><a href="/wiki/Geritol" title="Geritol">Geritol</a></li> <li><a href="/wiki/Goody%27s_Powder" title="Goody's Powder">Goody's Powder</a></li> <li><a href="/wiki/Horlicks" title="Horlicks">Horlicks</a></li> <li><a href="/wiki/Lucozade" title="Lucozade">Lucozade</a></li> <li><a href="/wiki/Nicoderm" class="mw-redirect" title="Nicoderm">Nicoderm</a></li> <li><a href="/wiki/Nicorette" title="Nicorette">Nicorette</a></li> <li><a href="/wiki/Niquitin" title="Niquitin">NiQuitin</a></li> <li><a href="/wiki/Parodontax" title="Parodontax">Parodontax</a></li> <li><a href="/wiki/Ribena" title="Ribena">Ribena</a></li> <li><a href="/wiki/Sensodyne" title="Sensodyne">Sensodyne</a></li> <li><a href="/wiki/Tums" title="Tums">Tums</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">People</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%">Board of <br />Directors</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/Philip_Hampton" title="Philip Hampton">Philip Hampton</a></li> <li><a href="/wiki/Emma_Walmsley" title="Emma Walmsley">Emma Walmsley</a></li> <li><a href="/wiki/Simon_Dingemans" title="Simon Dingemans">Simon Dingemans</a></li> <li><a href="/wiki/Roy_M._Anderson" title="Roy M. Anderson">Roy M. Anderson</a></li> <li><a href="/wiki/M._S._Banga" title="M. S. Banga">Manvinder Banga</a></li> <li><a href="/wiki/Patrick_Vallance" title="Patrick Vallance">Patrick Vallance</a></li> <li><a href="/wiki/Vivienne_Cox" title="Vivienne Cox">Vivienne Cox</a></li> <li><a href="/wiki/Lynn_Elsenhans" title="Lynn Elsenhans">Lynn Elsenhans</a></li> <li>Jesse Goodman</li> <li><a href="/wiki/Judy_Lewent" title="Judy Lewent">Judy Lewent</a></li> <li><a href="/wiki/Urs_Rohner" title="Urs Rohner">Urs Rohner</a></li> <li><a href="/wiki/Laurie_Glimcher" title="Laurie Glimcher">Laurie Glimcher</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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/Thomas_Beecham_(chemist)" title="Thomas Beecham (chemist)">Thomas Beecham</a></li> <li><a href="/wiki/Silas_M._Burroughs_(pharmacist)" title="Silas M. Burroughs (pharmacist)">Silas M. Burroughs</a></li> <li><a href="/wiki/Mahlon_Kline" title="Mahlon Kline">Mahlon Kline</a></li> <li><a href="/wiki/John_K._Smith" title="John K. Smith">John K. Smith</a></li> <li><a href="/wiki/Henry_Wellcome" title="Henry Wellcome">Henry Wellcome</a></li> <li><a href="/wiki/Andrew_Witty" title="Andrew Witty">Andrew Witty</a></li> <li><a href="/wiki/Chris_Gent" title="Chris Gent">Chris Gent</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Litigation</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Canada_v._GlaxoSmithKline_Inc." class="mw-redirect" title="Canada v. GlaxoSmithKline Inc.">Canada v. GlaxoSmithKline Inc.</a></i></li> <li><i><a href="/wiki/Christopher_v._SmithKline_Beecham_Corp." title="Christopher v. SmithKline Beecham Corp.">Christopher v. SmithKline Beecham Corp.</a></i></li> <li><i><a href="/wiki/GlaxoSmithKline_Services_Unlimited_v_Commission" title="GlaxoSmithKline Services Unlimited v Commission">GlaxoSmithKline Services Unlimited v Commission</a></i></li> <li><i><a href="/wiki/United_States_v._Glaxo_Group_Ltd." title="United States v. Glaxo Group Ltd.">United States v. Glaxo Group Ltd.</a></i></li> <li><i><a href="/wiki/United_States_v._GlaxoSmithKline" title="United States v. GlaxoSmithKline">United States v. 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