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<li id="toc-Topical_antifungal" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Topical_antifungal"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Topical antifungal</span> </div> </a> <ul id="toc-Topical_antifungal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Systemic_antifungal" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Systemic_antifungal"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Systemic antifungal</span> </div> </a> <ul id="toc-Systemic_antifungal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Off-label_uses" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Off-label_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Off-label uses</span> </div> </a> <ul id="toc-Off-label_uses-sublist" class="vector-toc-list"> <li id="toc-Hair_loss" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hair_loss"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3.1</span> <span>Hair loss</span> </div> </a> <ul id="toc-Hair_loss-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hormonal" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Hormonal"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3.2</span> <span>Hormonal</span> </div> </a> <ul id="toc-Hormonal-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Contraindications" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Contraindications</span> </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Side effects</span> </div> </a> <button aria-controls="toc-Side_effects-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 Side effects subsection</span> </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-Gastrointestinal" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Gastrointestinal"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Gastrointestinal</span> </div> </a> <ul id="toc-Gastrointestinal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Endocrine" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Endocrine"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Endocrine</span> </div> </a> <ul id="toc-Endocrine-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Liver" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Liver"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Liver</span> </div> </a> <ul id="toc-Liver-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Hypersensitivity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hypersensitivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.4</span> <span>Hypersensitivity</span> </div> </a> <ul id="toc-Hypersensitivity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Topical_formulations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Topical_formulations"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.5</span> <span>Topical formulations</span> </div> </a> <ul id="toc-Topical_formulations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pregnancy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pregnancy"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.6</span> <span>Pregnancy</span> </div> </a> <ul id="toc-Pregnancy-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Overdose</span> </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Interactions</span> </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</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">6.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Antifungal_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Antifungal_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.1</span> <span>Antifungal activity</span> </div> </a> <ul id="toc-Antifungal_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antihormonal_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Antihormonal_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.2</span> <span>Antihormonal activity</span> </div> </a> <ul id="toc-Antihormonal_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_activities" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other_activities"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.3</span> <span>Other activities</span> </div> </a> <ul id="toc-Other_activities-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Chemistry</span> </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Society and culture</span> </div> </a> <button aria-controls="toc-Society_and_culture-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 Society and culture subsection</span> </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Generic_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Generic_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Generic names</span> </div> </a> <ul id="toc-Generic_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brand_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brand_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Brand names</span> </div> </a> <ul id="toc-Brand_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Availability" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Availability"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.3</span> <span>Availability</span> </div> </a> <ul id="toc-Availability-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</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"> <a class="vector-toc-link" href="#Veterinary_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</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"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>References</span> </div> </a> <ul id="toc-References-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 vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Ketoconazole</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. Available in 33 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-33" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">33 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D9%8A%D8%AA%D9%88%D9%83%D9%88%D9%86%D8%A7%D8%B2%D9%88%D9%84" title="كيتوكونازول – Arabic" lang="ar" hreflang="ar" data-title="كيتوكونازول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%DA%A9%D8%AA%D9%88%DA%A9%D9%88%D9%86%D8%A7%D8%B2%D9%88%D9%84" title="کتوکونازول – South Azerbaijani" lang="azb" hreflang="azb" data-title="کتوکونازول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Cetoconasol" title="Cetoconasol – Welsh" lang="cy" hreflang="cy" data-title="Cetoconasol" 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/Ketoconazol" title="Ketoconazol – German" lang="de" hreflang="de" data-title="Ketoconazol" 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%9A%CE%B5%CF%84%CE%BF%CE%BA%CE%BF%CE%BD%CE%B1%CE%B6%CF%8C%CE%BB%CE%B7" title="Κετοκοναζόλη – Greek" lang="el" hreflang="el" data-title="Κετοκοναζόλη" 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/Ketoconazol" title="Ketoconazol – Spanish" lang="es" hreflang="es" data-title="Ketoconazol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D8%AA%D9%88%DA%A9%D9%88%D9%86%D8%A7%D8%B2%D9%88%D9%84" title="کتوکونازول – Persian" lang="fa" hreflang="fa" data-title="کتوکونازول" 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/K%C3%A9toconazole" title="Kétoconazole – French" lang="fr" hreflang="fr" data-title="Kétoconazole" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Ketoconazol" title="Ketoconazol – Galician" lang="gl" hreflang="gl" data-title="Ketoconazol" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%BC%80%ED%86%A0%EC%BD%94%EB%82%98%EC%A1%B8" title="케토코나졸 – Korean" lang="ko" hreflang="ko" data-title="케토코나졸" 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/%D4%BF%D5%A5%D5%BF%D5%B8%D5%AF%D5%B8%D5%B6%D5%A1%D5%A6%D5%B8%D5%AC" title="Կետոկոնազոլ – Armenian" lang="hy" hreflang="hy" data-title="Կետոկոնազոլ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Ketokonazol" title="Ketokonazol – Indonesian" lang="id" hreflang="id" data-title="Ketokonazol" 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/Ketoconazolo" title="Ketoconazolo – Italian" lang="it" hreflang="it" data-title="Ketoconazolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-lfn mw-list-item"><a href="https://lfn.wikipedia.org/wiki/Cetoconazol" title="Cetoconazol – Lingua Franca Nova" lang="lfn" hreflang="lfn" data-title="Cetoconazol" data-language-autonym="Lingua Franca Nova" data-language-local-name="Lingua Franca Nova" class="interlanguage-link-target"><span>Lingua Franca Nova</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ketokonazol" title="Ketokonazol – Hungarian" lang="hu" hreflang="hu" data-title="Ketokonazol" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%9A%D0%B5%D1%82%D0%BE%D0%BA%D0%BE%D0%BD%D0%B0%D0%B7%D0%BE%D0%BB" title="Кетоконазол – Macedonian" lang="mk" hreflang="mk" data-title="Кетоконазол" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Ketokonazol" title="Ketokonazol – Malay" lang="ms" hreflang="ms" data-title="Ketokonazol" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ketoconazol" title="Ketoconazol – Dutch" lang="nl" hreflang="nl" data-title="Ketoconazol" 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%B1%E3%83%88%E3%82%B3%E3%83%8A%E3%82%BE%E3%83%BC%E3%83%AB" title="ケトコナゾール – Japanese" lang="ja" hreflang="ja" data-title="ケトコナゾール" 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%95%E0%AD%87%E0%AC%9F%E0%AD%8B%E0%AC%95%E0%AD%8B%E0%AC%A8%E0%AC%BE%E0%AC%9C%E0%AD%8B%E0%AC%B2" title="କେଟୋକୋନାଜୋଲ – Odia" lang="or" hreflang="or" data-title="କେଟୋକୋନାଜୋଲ" 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/Ketokonazol" title="Ketokonazol – Polish" lang="pl" hreflang="pl" data-title="Ketokonazol" 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/Cetoconazol" title="Cetoconazol – Portuguese" lang="pt" hreflang="pt" data-title="Cetoconazol" 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/Ketoconazol" title="Ketoconazol – Romanian" lang="ro" hreflang="ro" data-title="Ketoconazol" 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%9A%D0%B5%D1%82%D0%BE%D0%BA%D0%BE%D0%BD%D0%B0%D0%B7%D0%BE%D0%BB" title="Кетоконазол – Russian" lang="ru" hreflang="ru" data-title="Кетоконазол" 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/Ketokonazol" title="Ketokonazol – Slovenian" lang="sl" hreflang="sl" data-title="Ketokonazol" 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/%D0%9A%D0%B5%D1%82%D0%BE%D0%BA%D0%BE%D0%BD%D0%B0%D0%B7%D0%BE%D0%BB" title="Кетоконазол – Serbian" lang="sr" hreflang="sr" data-title="Кетоконазол" 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/Ketokonazol" title="Ketokonazol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ketokonazol" 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/Ketokonatsoli" title="Ketokonatsoli – Finnish" lang="fi" hreflang="fi" data-title="Ketokonatsoli" 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%B8%84%E0%B8%B5%E0%B9%82%E0%B8%95%E0%B9%82%E0%B8%84%E0%B8%99%E0%B8%B2%E0%B9%82%E0%B8%8B%E0%B8%A5" title="คีโตโคนาโซล – Thai" lang="th" hreflang="th" data-title="คีโตโคนาโซล" 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/Ketokonazol" title="Ketokonazol – Turkish" lang="tr" hreflang="tr" data-title="Ketokonazol" 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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">Antifungal chemical compound</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): Ketoconazole">Ketoconazole</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Ketoconazole_enantiomers.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Ketoconazole_enantiomers.svg/250px-Ketoconazole_enantiomers.svg.png" decoding="async" width="250" height="199" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Ketoconazole_enantiomers.svg/375px-Ketoconazole_enantiomers.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a8/Ketoconazole_enantiomers.svg/500px-Ketoconazole_enantiomers.svg.png 2x" data-file-width="512" data-file-height="408" /></a></span><div class="infobox-caption">(2<i>R</i>,4<i>S</i>)-(+)-ketoconazole (top)<br />(2<i>S</i>,4<i>R</i>)-(−)-ketoconazole (bottom)</div></td></tr><tr><td colspan="2" class="infobox-image"><span class="bg-transparent" typeof="mw:File"><a href="/wiki/File:(2R,4S)-(%2B)-ketoconazole-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/%282R%2C4S%29-%28%2B%29-ketoconazole-from-xtal-3D-bs-17.png/250px-%282R%2C4S%29-%28%2B%29-ketoconazole-from-xtal-3D-bs-17.png" decoding="async" width="250" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3a/%282R%2C4S%29-%28%2B%29-ketoconazole-from-xtal-3D-bs-17.png/500px-%282R%2C4S%29-%28%2B%29-ketoconazole-from-xtal-3D-bs-17.png 1.5x" data-file-width="3000" data-file-height="1178" /></a></span><div class="infobox-caption"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Ball-and-stick model</a> of (2<i>R</i>,4<i>S</i>)-(+)-ketoconazole</div></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="/ˌ/: secondary stress follows">ˌ</span><span title="'k' in 'kind'">k</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'t' in 'tie'">t</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'k' in 'kind'">k</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="'n' in 'nigh'">n</span><span title="/ə/: 'a' in 'about'">ə</span><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'z' in 'zoom'">z</span><span title="/oʊ/: 'o' in 'code'">oʊ</span><span title="'l' in 'lie'">l</span></span>,<span class="wrap"> </span>-<span style="border-bottom:1px dotted"><span title="'z' in 'zoom'">z</span><span title="/ɒ/: 'o' in 'body'">ɒ</span><span title="'l' in 'lie'">l</span></span>/</a></span></span><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </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">Nizoral, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">R-41400; KW-1414</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/ketoconazole.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/a682816.html">a682816</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=Ketoconazole">Ketoconazole</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> B3</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/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a>), <a href="/wiki/Topical" class="mw-redirect" title="Topical">topical</a> (<a href="/wiki/Cream_(pharmaceutical)" class="mw-redirect" title="Cream (pharmaceutical)">cream</a>, <a href="/wiki/Shampoo" title="Shampoo">shampoo</a>, <a href="/wiki/Solution_(chemistry)" title="Solution (chemistry)">solution</a>)</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_J02" title="ATC code J02">J02AB02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J02AB02">WHO</a></span>) <a href="/wiki/ATC_code_D01" title="ATC code D01">D01AC08</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D01AC08">WHO</a></span>), <a href="/wiki/ATC_code_G01" title="ATC code G01">G01AF11</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G01AF11">WHO</a></span>), <a href="/wiki/ATC_code_H02" title="ATC code H02">H02CA03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=H02CA03">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="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_3-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>Rx-only<sup id="cite_ref-Ketoconazole_tablet_label_6-0" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Rx-only<sup id="cite_ref-Ketoconazole_HRA_EPAR_7-0" class="reference"><a href="#cite_note-Ketoconazole_HRA_EPAR-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li> <li>In general: ℞ (Prescription only)</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"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>: 37–97%<sup id="cite_ref-Millikan2016_8-0" class="reference"><a href="#cite_note-Millikan2016-8"><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/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">84 to 99%</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">Extensive <a href="/wiki/Liver" title="Liver">liver</a> (predominantly oxidation, <i>O</i>-dealkylation)</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"><i>N</i>-deacetyl ketoconazole</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">Biphasic</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/Bile_duct" title="Bile duct">Bile duct</a> (major) and <a href="/wiki/Kidney" title="Kidney">kidney</a><sup id="cite_ref-AR_9-0" class="reference"><a href="#cite_note-AR-9"><span class="cite-bracket">[</span>9<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-[4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone</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=65277-42-1">65277-42-1</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/3823">3823</a></span></li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/47576">47576</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=2568">2568</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/DB01026">DB01026</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.401695.html">401695</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><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.3691.html">3691</a></span></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/R9400W927I">R9400W927I</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/D00351">D00351</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:48336">CHEBI:48336</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/ChEMBL75">ChEMBL75</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><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL157101">ChEMBL157101</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB ligand</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>KTN (<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=KTN">PDBe</a></span>, <span title="www.rcsb.org"><a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/KTN">RCSB PDB</a></span>)</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/DTXSID20273956">DTXSID20273956</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407883#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/100.059.680">100.059.680</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q407883#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>26</sub><span title="Hydrogen">H</span><sub>28</sub><span title="Chlorine">Cl</span><sub>2</sub><span title="Nitrogen">N</span><sub>4</sub><span title="Oxygen">O</span><sub>4</sub></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="7002531429999999999♠"></span>531.43</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28N5CCN%28c4ccc%28OC%5BC%40%40H%5D1O%5BC%40%5D%28OC1%29%28c2ccc%28Cl%29cc2Cl%29Cn3ccnc3%29cc4%29CC5%29C">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">Chirality</a></th><td class="infobox-data"><a href="/wiki/Racemic_mixture" title="Racemic mixture">Racemic mixture</a><sup id="cite_ref-AR_9-1" class="reference"><a href="#cite_note-AR-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Arakak_10-0" class="reference"><a href="#cite_note-Arakak-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O=C(N5CCN(c4ccc(OC[C@@H]1O[C@](OC1)(c2ccc(Cl)cc2Cl)Cn3ccnc3)cc4)CC5)C</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/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1<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:XMAYWYJOQHXEEK-OZXSUGGESA-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"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><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> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=457114462&page2=Ketoconazole">(verify)</a></span></span></td></tr></tbody></table> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ketoconazole_STADA%C2%AE.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Ketoconazole_STADA%C2%AE.jpg/250px-Ketoconazole_STADA%C2%AE.jpg" decoding="async" width="150" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Ketoconazole_STADA%C2%AE.jpg/330px-Ketoconazole_STADA%C2%AE.jpg 2x" data-file-width="424" data-file-height="293" /></a><figcaption>Stada</figcaption></figure> <p><b>Ketoconazole</b>, sold under the brand name <b>Nizoral</b>, among others, is an <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogen</a>, <a href="/wiki/Antifungal_drug" class="mw-redirect" title="Antifungal drug">antifungal</a>, and <a href="/wiki/Antiglucocorticoid" title="Antiglucocorticoid">antiglucocorticoid</a> medication used to treat a number of <a href="/wiki/Fungal_infection" title="Fungal infection">fungal infections</a>.<sup id="cite_ref-AHFS2019_11-0" class="reference"><a href="#cite_note-AHFS2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Applied to the skin it is used for <a href="/wiki/Fungal_skin_infections" class="mw-redirect" title="Fungal skin infections">fungal skin infections</a> such as <a href="/wiki/Tinea" class="mw-redirect" title="Tinea">tinea</a>, <a href="/wiki/Cutaneous_candidiasis" class="mw-redirect" title="Cutaneous candidiasis">cutaneous candidiasis</a>, <a href="/wiki/Pityriasis_versicolor" class="mw-redirect" title="Pityriasis versicolor">pityriasis versicolor</a>, <a href="/wiki/Dandruff" title="Dandruff">dandruff</a>, and <a href="/wiki/Seborrhoeic_dermatitis" title="Seborrhoeic dermatitis">seborrheic dermatitis</a>.<sup id="cite_ref-BNF76_12-0" class="reference"><a href="#cite_note-BNF76-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a> it is a less preferred option and recommended for only severe infections when other agents cannot be used.<sup id="cite_ref-AHFS2019_11-1" class="reference"><a href="#cite_note-AHFS2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Other uses include treatment of <a href="/wiki/Hirsutism" title="Hirsutism">excessive male-patterned hair growth in women</a> and <a href="/wiki/Cushing%27s_syndrome" title="Cushing's syndrome">Cushing's syndrome</a>.<sup id="cite_ref-AHFS2019_11-2" class="reference"><a href="#cite_note-AHFS2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Common <a href="/wiki/Side_effect" title="Side effect">side effects</a> when <a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">applied to the skin</a> include redness.<sup id="cite_ref-BNF76_12-1" class="reference"><a href="#cite_note-BNF76-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Common side effects when taken by mouth include <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Headache" title="Headache">headache</a>, and <a href="/wiki/Liver_problems" class="mw-redirect" title="Liver problems">liver problems</a>.<sup id="cite_ref-AHFS2019_11-3" class="reference"><a href="#cite_note-AHFS2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Liver problems may result in death or the need for a <a href="/wiki/Liver_transplantation" title="Liver transplantation">liver transplantation</a>.<sup id="cite_ref-AHFS2019_11-4" class="reference"><a href="#cite_note-AHFS2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FDA2013_13-0" class="reference"><a href="#cite_note-FDA2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Other severe side effects when taken by mouth include <a href="/wiki/QT_prolongation" class="mw-redirect" title="QT prolongation">QT prolongation</a>, <a href="/wiki/Adrenocortical_insufficiency" class="mw-redirect" title="Adrenocortical insufficiency">adrenocortical insufficiency</a>, and <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylaxis</a>.<sup id="cite_ref-AHFS2019_11-5" class="reference"><a href="#cite_note-AHFS2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FDA2013_13-1" class="reference"><a href="#cite_note-FDA2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It is an <a href="/wiki/Imidazole" title="Imidazole">imidazole</a> and works by hindering the production of <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a> required for the fungal <a href="/wiki/Cell_membrane" title="Cell membrane">cell membrane</a>, thereby slowing growth.<sup id="cite_ref-AHFS2019_11-6" class="reference"><a href="#cite_note-AHFS2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Ketoconazole was patented in 1977 by Belgian pharmaceutical company <a href="/wiki/Janssen_Pharmaceuticals" title="Janssen Pharmaceuticals">Janssen</a>, and came into medical use in 1981.<sup id="cite_ref-Fis2006_14-0" class="reference"><a href="#cite_note-Fis2006-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a> and formulations that are applied to the skin are <a href="/wiki/Over_the_counter" class="mw-redirect" title="Over the counter">over the counter</a> in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>.<sup id="cite_ref-BNF76_12-2" class="reference"><a href="#cite_note-BNF76-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> In 2022, it was the 175th most commonly prescribed medication in the United States, with more than 2<span class="nowrap"> </span>million prescriptions.<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><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> The formulation that is taken by mouth was <a href="/wiki/Withdrawn_drug" class="mw-redirect" title="Withdrawn drug">withdrawn</a> in the European Union and in Australia in 2013,<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-GuptaLyons2015_18-0" class="reference"><a href="#cite_note-GuptaLyons2015-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> and in China in 2015.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> In addition, its use was restricted in the United States and Canada in 2013.<sup id="cite_ref-GuptaLyons2015_18-1" class="reference"><a href="#cite_note-GuptaLyons2015-18"><span class="cite-bracket">[</span>18<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=Ketoconazole&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Topical_antifungal">Topical antifungal</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=2" title="Edit section: Topical antifungal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Topically administered ketoconazole is usually prescribed for fungal infections of the skin and mucous membranes, such as <a href="/wiki/Athlete%27s_foot" title="Athlete's foot">athlete's foot</a>, <a href="/wiki/Ringworm" class="mw-redirect" title="Ringworm">ringworm</a>, <a href="/wiki/Candidiasis" title="Candidiasis">candidiasis</a> (yeast infection or thrush), <a href="/wiki/Jock_itch" class="mw-redirect" title="Jock itch">jock itch</a>, and <a href="/wiki/Tinea_versicolor" title="Tinea versicolor">tinea versicolor</a>.<sup id="cite_ref-phillips_20-0" class="reference"><a href="#cite_note-phillips-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Topical ketoconazole is also used as a treatment for <a href="/wiki/Dandruff" title="Dandruff">dandruff</a> (seborrheic dermatitis of the scalp) and for <a href="/wiki/Seborrheic_dermatitis" class="mw-redirect" title="Seborrheic dermatitis">seborrheic dermatitis</a> on other areas of the body, perhaps acting in these conditions by suppressing levels of the fungus <i><a href="/wiki/Malassezia_furfur" title="Malassezia furfur">Malassezia furfur</a></i> on the skin.<sup id="cite_ref-phillips_20-1" class="reference"><a href="#cite_note-phillips-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-neider_21-0" class="reference"><a href="#cite_note-neider-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Systemic_antifungal">Systemic antifungal</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=3" title="Edit section: Systemic antifungal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketoconazole has activity against many kinds of fungi that may cause human disease, such as <i><a href="/wiki/Candida_(fungus)" title="Candida (fungus)">Candida</a></i>, <i><a href="/wiki/Histoplasma" title="Histoplasma">Histoplasma</a></i>, <i><a href="/wiki/Coccidioides" title="Coccidioides">Coccidioides</a></i>, and <i><a href="/wiki/Blastomyces" title="Blastomyces">Blastomyces</a></i> (although it is not active against <i><a href="/wiki/Aspergillus" title="Aspergillus">Aspergillus</a></i>), <a href="/wiki/Chromoblastomycosis" title="Chromoblastomycosis">chromomycosis</a> and <a href="/wiki/Paracoccidioidomycosis" title="Paracoccidioidomycosis">paracoccidioidomycosis</a>.<sup id="cite_ref-finkel_23-0" class="reference"><a href="#cite_note-finkel-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FDA2013_13-2" class="reference"><a href="#cite_note-FDA2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> First made in 1977,<sup id="cite_ref-phillips_20-2" class="reference"><a href="#cite_note-phillips-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> ketoconazole was the first orally-active <a href="/wiki/Azole" title="Azole">azole</a> antifungal medication.<sup id="cite_ref-finkel_23-1" class="reference"><a href="#cite_note-finkel-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> However, ketoconazole has largely been replaced as a first-line systemic antifungal medication by other <a href="/wiki/Azole_antifungal" class="mw-redirect" title="Azole antifungal">azole antifungal</a> agents, such as <a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a> and/or <a href="/wiki/Itraconazole" title="Itraconazole">itraconazole</a>, because of ketoconazole's greater toxicity, poorer absorption, and more limited spectrum of activity.<sup id="cite_ref-finkel_23-2" class="reference"><a href="#cite_note-finkel-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Ketoconazole is used orally in dosages of 200 to 400 mg per day in the treatment of superficial and deep fungal infections.<sup id="cite_ref-Becker2001_25-0" class="reference"><a href="#cite_note-Becker2001-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Off-label_uses">Off-label uses</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=4" title="Edit section: Off-label uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Hair_loss">Hair loss</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=5" title="Edit section: Hair loss"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Ketoconazole_shampoo_skin.jpg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Ketoconazole_shampoo_skin.jpg/200px-Ketoconazole_shampoo_skin.jpg" decoding="async" width="200" height="257" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Ketoconazole_shampoo_skin.jpg/300px-Ketoconazole_shampoo_skin.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Ketoconazole_shampoo_skin.jpg/400px-Ketoconazole_shampoo_skin.jpg 2x" data-file-width="2586" data-file-height="3324" /></a><figcaption>Ketoconazole 2% gel</figcaption></figure> <p>Ketoconazole shampoo in conjunction with an oral <a href="/wiki/5%CE%B1-reductase_inhibitor" class="mw-redirect" title="5α-reductase inhibitor">5α-reductase inhibitor</a> such as <a href="/wiki/Finasteride" title="Finasteride">finasteride</a> or <a href="/wiki/Dutasteride" title="Dutasteride">dutasteride</a> has been used off label to treat <a href="/wiki/Androgenic_alopecia" class="mw-redirect" title="Androgenic alopecia">androgenic alopecia</a>. It was speculated that antifungal properties of ketoconazole reduce scalp microflora and consequently may reduce follicular inflammation that contributes to alopecia.<sup id="cite_ref-pmid22735503_26-0" class="reference"><a href="#cite_note-pmid22735503-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>Limited clinical studies suggest ketoconazole shampoo used either alone<sup id="cite_ref-pmid9669136_27-0" class="reference"><a href="#cite_note-pmid9669136-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid18498517_28-0" class="reference"><a href="#cite_note-pmid18498517-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> or in combination with other treatments<sup id="cite_ref-pmid12227482_29-0" class="reference"><a href="#cite_note-pmid12227482-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> may be useful in reducing hair loss in some cases.<sup id="cite_ref-pmid31832993_30-0" class="reference"><a href="#cite_note-pmid31832993-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Hormonal">Hormonal</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=6" title="Edit section: Hormonal"><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">See also: <a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Steroidogenesis inhibitor</a> and <a href="/wiki/CYP17A1_inhibitor" title="CYP17A1 inhibitor">CYP17A1 inhibitor</a></div> <p>The side effects of ketoconazole are sometimes harnessed in the treatment of non-fungal conditions. While ketoconazole blocks the synthesis of the sterol <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a> in fungi, in humans, at high dosages (>800 mg/day), it potently inhibits the activity of several <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> necessary for the conversion of <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> to <a href="/wiki/Steroid_hormone" title="Steroid hormone">steroid hormones</a> such as <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>.<sup id="cite_ref-finkel_23-3" class="reference"><a href="#cite_note-finkel-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Becker2001_25-1" class="reference"><a href="#cite_note-Becker2001-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Specifically, ketoconazole has been shown to inhibit <a href="/wiki/Cholesterol_side-chain_cleavage_enzyme" title="Cholesterol side-chain cleavage enzyme">cholesterol side-chain cleavage enzyme</a>, which converts cholesterol to <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone</a>, <a href="/wiki/17%CE%B1-hydroxylase" class="mw-redirect" title="17α-hydroxylase">17α-hydroxylase</a> and <a href="/wiki/17,20-lyase" class="mw-redirect" title="17,20-lyase">17,20-lyase</a>,<sup id="cite_ref-Becker2001_25-2" class="reference"><a href="#cite_note-Becker2001-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> which convert <a href="/wiki/Pregnenolone" title="Pregnenolone">pregnenolone</a> into <a href="/wiki/Androgen" title="Androgen">androgens</a>, and <a href="/wiki/11%CE%B2-hydroxylase" class="mw-redirect" title="11β-hydroxylase">11β-hydroxylase</a>, which converts <a href="/wiki/11-deoxycortisol" class="mw-redirect" title="11-deoxycortisol">11-deoxycortisol</a> to <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>.<sup id="cite_ref-Medscape-keto_31-0" class="reference"><a href="#cite_note-Medscape-keto-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> All of these enzymes are mitochondrial <a href="/wiki/Cytochrome_p450" class="mw-redirect" title="Cytochrome p450">cytochrome p450</a> enzymes.<sup id="cite_ref-pmid6304148_32-0" class="reference"><a href="#cite_note-pmid6304148-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Based on these <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogen</a> and <a href="/wiki/Antiglucocorticoid" title="Antiglucocorticoid">antiglucocorticoid</a> effects, ketoconazole has been used with some success as a second-line treatment for certain forms of advanced <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a><sup id="cite_ref-Becker2001_25-3" class="reference"><a href="#cite_note-Becker2001-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-zelefsky_33-0" class="reference"><a href="#cite_note-zelefsky-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> and for the suppression of <a href="/wiki/Glucocorticoid" title="Glucocorticoid">glucocorticoid</a> synthesis in the treatment of <a href="/wiki/Cushing%27s_syndrome" title="Cushing's syndrome">Cushing's syndrome</a>.<sup id="cite_ref-Cushing_34-0" class="reference"><a href="#cite_note-Cushing-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> However, in the treatment of prostate cancer, concomitant glucocorticoid administration is needed to prevent <a href="/wiki/Adrenal_insufficiency" title="Adrenal insufficiency">adrenal insufficiency</a>.<sup id="cite_ref-Becker2001_25-4" class="reference"><a href="#cite_note-Becker2001-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Ketoconazole has additionally been used, in lower dosages, to treat <a href="/wiki/Hirsutism" title="Hirsutism">hirsutism</a> and, in combination with a <a href="/wiki/GnRH_analogue" class="mw-redirect" title="GnRH analogue">GnRH analogue</a>, <a href="/wiki/Male-limited_precocious_puberty" class="mw-redirect" title="Male-limited precocious puberty">male-limited precocious puberty</a>.<sup id="cite_ref-Becker2001_25-5" class="reference"><a href="#cite_note-Becker2001-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> In any case, the risk of <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a> with ketoconazole limits its use in all of these indications, especially in those that are benign such as hirsutism.<sup id="cite_ref-Becker2001_25-6" class="reference"><a href="#cite_note-Becker2001-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>Ketoconazole has been used to prevent the <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> flare at the initiation of <a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonist</a> therapy in men with prostate cancer.<sup id="cite_ref-pmid16986003_35-0" class="reference"><a href="#cite_note-pmid16986003-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=7" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oral ketoconazole has various <a href="/wiki/Contraindication" title="Contraindication">contraindications</a>, such as concomitant use with certain other drugs due to known <a href="/wiki/Drug_interaction" title="Drug interaction">drug interactions</a>.<sup id="cite_ref-Ketoconazole_tablet_label_6-1" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Other contraindications of oral ketoconazole include <a href="/wiki/Liver_disease" title="Liver disease">liver disease</a>, <a href="/wiki/Adrenal_insufficiency" title="Adrenal insufficiency">adrenal insufficiency</a>, and known <a href="/wiki/Hypersensitivity" title="Hypersensitivity">hypersensitivity</a> to oral ketoconazole.<sup id="cite_ref-Ketoconazole_tablet_label_6-2" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<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=Ketoconazole&action=edit&section=8" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Gastrointestinal">Gastrointestinal</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=9" title="Edit section: Gastrointestinal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vomiting, diarrhea, nausea, constipation, abdominal pain, upper abdominal pain, dry mouth, <a href="/wiki/Dysgeusia" title="Dysgeusia">dysgeusia</a>, <a href="/wiki/Dyspepsia" class="mw-redirect" title="Dyspepsia">dyspepsia</a>, <a href="/wiki/Flatulence" title="Flatulence">flatulence</a>, tongue discoloration may occur.<sup id="cite_ref-:1_36-0" class="reference"><a href="#cite_note-:1-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Endocrine">Endocrine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=10" title="Edit section: Endocrine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The drug may cause <a href="/wiki/Adrenal_insufficiency" title="Adrenal insufficiency">adrenal insufficiency</a> so the level of the <a href="/wiki/Adrenocortical_hormone" title="Adrenocortical hormone">adrenocortical hormones</a> should be monitored while taking it.<sup id="cite_ref-FDA2013_13-3" class="reference"><a href="#cite_note-FDA2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_36-1" class="reference"><a href="#cite_note-:1-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Oral ketoconazole at a dosage range of 400 to 2,000 mg/day has been found to result in a rate of <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> of 21%.<sup id="cite_ref-DeepinderBraunstein2012_37-0" class="reference"><a href="#cite_note-DeepinderBraunstein2012-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Liver">Liver</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=11" title="Edit section: Liver"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In July 2013, the US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) issued a warning that taking ketoconazole by mouth can cause severe liver injuries and adrenal gland problems: <a href="/wiki/Adrenal_insufficiency" title="Adrenal insufficiency">adrenal insufficiency</a> and worsening of other related to the gland conditions.<sup id="cite_ref-FDA2013_13-4" class="reference"><a href="#cite_note-FDA2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It recommends oral tablets should not be a first-line treatment for any fungal infection. It should be used for the treatment of certain fungal infections, known as endemic mycoses, only when alternative antifungal therapies are not available or not tolerated.<sup id="cite_ref-FDA2013_13-5" class="reference"><a href="#cite_note-FDA2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> As contraindication it should not be used in people with acute or chronic liver disease.<sup id="cite_ref-FDA2013_13-6" class="reference"><a href="#cite_note-FDA2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Hypersensitivity">Hypersensitivity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=12" title="Edit section: Hypersensitivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Anaphylaxis" title="Anaphylaxis">Anaphylaxis</a> after the first dose may occur.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (February 2024)">medical citation needed</span></a></i>]</sup> Other cases of hypersensitivity include <a href="/wiki/Hives" title="Hives">urticaria</a>.<sup id="cite_ref-AHFS2019_11-7" class="reference"><a href="#cite_note-AHFS2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ketoconazole_tablet_label_6-3" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Topical_formulations">Topical formulations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=13" title="Edit section: Topical formulations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The topical formulations have not been associated with liver damage, adrenal problems, or drug interactions. These formulations include creams, shampoos, foams, and gels applied to the skin, unlike the ketoconazole tablets, which are taken by mouth.<sup id="cite_ref-FDA2013_13-7" class="reference"><a href="#cite_note-FDA2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pregnancy">Pregnancy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=14" title="Edit section: Pregnancy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketoconazole is categorized as <a href="/wiki/Pregnancy_category_(pharmaceutical)" class="mw-redirect" title="Pregnancy category (pharmaceutical)">pregnancy category C</a> in the US.<sup id="cite_ref-Preg2020_38-0" class="reference"><a href="#cite_note-Preg2020-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Research in animals has shown it to cause <a href="/wiki/Teratology" title="Teratology">teratogenesis</a> when administered in high doses.<sup id="cite_ref-Preg2020_38-1" class="reference"><a href="#cite_note-Preg2020-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> A subsequent trial in Europe failed to show a risk to infants of mothers receiving ketoconazole.<sup id="cite_ref-Giant_Hungarian_Human_Birth_Defects_Study_39-0" class="reference"><a href="#cite_note-Giant_Hungarian_Human_Birth_Defects_Study-39"><span class="cite-bracket">[</span>39<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=Ketoconazole&action=edit&section=15" title="Edit section: Overdose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the event of an <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a> of oral ketoconazole, treatment should be supportive and based on <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a>.<sup id="cite_ref-Ketoconazole_tablet_label_6-4" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Activated_charcoal" class="mw-redirect" title="Activated charcoal">Activated charcoal</a> may be administered within the first hour following overdose of oral ketoconazole.<sup id="cite_ref-Ketoconazole_tablet_label_6-5" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<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=Ketoconazole&action=edit&section=16" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The concomitant use of the following medications is contraindicated with ketoconazole tablets:<sup id="cite_ref-Ketoconazole_tablet_label_6-6" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_36-2" class="reference"><a href="#cite_note-:1-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Methadone" title="Methadone">methadone</a>, <a href="/wiki/Disopyramide" title="Disopyramide">disopyramide</a>, <a href="/wiki/Dronedarone" title="Dronedarone">dronedarone</a></li> <li><a href="/wiki/Irinotecan" title="Irinotecan">irinotecan</a>, <a href="/wiki/Lurasidone" title="Lurasidone">lurasidone</a>, <a href="/wiki/Colchicine" title="Colchicine">colchicine</a></li> <li><a href="/wiki/Alprazolam" title="Alprazolam">alprazolam</a>, oral <a href="/wiki/Midazolam" title="Midazolam">midazolam</a>, oral <a href="/wiki/Triazolam" title="Triazolam">triazolam</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">felodipine</a>, <a href="/wiki/Ranolazine" title="Ranolazine">ranolazine</a>, <a href="/wiki/Tolvaptan" title="Tolvaptan">tolvaptan</a>, <a href="/wiki/Eplerenone" title="Eplerenone">eplerenone</a></li> <li><a href="/wiki/HMG-CoA_reductase_inhibitor" class="mw-redirect" title="HMG-CoA reductase inhibitor">HMG-CoA reductase inhibitors</a>: <a href="/wiki/Lovastatin" title="Lovastatin">lovastatin</a>, <a href="/wiki/Simvastatin" title="Simvastatin">simvastatin</a></li> <li><a href="/wiki/Ergot_alkaloid" class="mw-redirect" title="Ergot alkaloid">ergot alkaloids</a>: <a href="/wiki/Ergotamine" title="Ergotamine">ergotamine</a>, <a href="/wiki/Dihydroergotamine" title="Dihydroergotamine">dihydroergotamine</a>, <a href="/wiki/Ergometrine" class="mw-redirect" title="Ergometrine">ergometrine</a>, <a href="/wiki/Methylergometrine" title="Methylergometrine">methylergometrine</a></li> <li>Others: <a href="/wiki/Cisapride" title="Cisapride">cisapride</a>, <a href="/wiki/Nisoldipine" title="Nisoldipine">nisoldipine</a>, <a href="/wiki/Dofetilide" title="Dofetilide">dofetilide</a>, <a href="/wiki/Pimozide" title="Pimozide">pimozide</a></li></ul> <p>And is not recommended:<sup id="cite_ref-Ketoconazole_tablet_label_6-7" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_36-3" class="reference"><a href="#cite_note-:1-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a>, <a href="/wiki/Phenytoin" title="Phenytoin">phenytoin</a></li> <li>gastric acid suppressants: <a href="/wiki/Antacid" title="Antacid">antacids</a>, <a href="/wiki/Muscarinic_antagonist" title="Muscarinic antagonist">antimuscarinics</a>, <a href="/wiki/H2_antagonist" class="mw-redirect" title="H2 antagonist">histamine H<sub>2</sub> blockers</a>, <a href="/wiki/Proton_pump_inhibitor" class="mw-redirect" title="Proton pump inhibitor">proton pump inhibitors</a></li> <li><a href="/wiki/Sucralfate" title="Sucralfate">sucralfate</a></li> <li><a href="/wiki/Rifampin" class="mw-redirect" title="Rifampin">rifampin</a>, <a href="/wiki/Rifabutin" title="Rifabutin">rifabutin</a>, <a href="/wiki/Isoniazid" title="Isoniazid">isoniazid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">efavirenz</a>, <a href="/wiki/Nevirapine" title="Nevirapine">nevirapine</a></li></ul> <p><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir</a> is known for increasing activity of the ketoconazole so it is recommended to reduce dosage.<sup id="cite_ref-Ketoconazole_tablet_label_6-8" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>There is also a list of drugs which significantly decrease systemic exposure to the ketoconazole and drugs whose systemic exposure is increased by the ketoconazole.<sup id="cite_ref-Ketoconazole_tablet_label_6-9" class="reference"><a href="#cite_note-Ketoconazole_tablet_label-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_36-4" class="reference"><a href="#cite_note-:1-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=17" 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=Ketoconazole&action=edit&section=18" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Antifungal_activity">Antifungal activity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=19" title="Edit section: Antifungal activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-More_citations_needed_section plainlinks metadata ambox ambox-content ambox-Refimprove" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>needs additional citations for <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">verification</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Ketoconazole" title="Special:EditPage/Ketoconazole">improve this article</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a> in this section. Unsourced material may be challenged and removed.</span> <span class="date-container"><i>(<span class="date">May 2013</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <p>As an antifungal, ketoconazole is structurally similar to <a href="/wiki/Imidazole" title="Imidazole">imidazole</a>, and interferes with the fungal synthesis of <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a>, a constituent of fungal <a href="/wiki/Cell_membrane" title="Cell membrane">cell membranes</a>, as well as certain <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>. As with all <a href="/wiki/Azole_antifungal" class="mw-redirect" title="Azole antifungal">azole antifungal</a> agents, ketoconazole works principally by inhibiting the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/14%CE%B1-demethylase" class="mw-redirect" title="14α-demethylase">14α-demethylase</a> (CYP51A1).<sup id="cite_ref-pmid6304148_32-1" class="reference"><a href="#cite_note-pmid6304148-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> This enzyme participates in the <a href="/wiki/Sterol" title="Sterol">sterol</a> <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> pathway that leads from <a href="/wiki/Lanosterol" title="Lanosterol">lanosterol</a> to <a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a>. Lower doses of <a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a> and <a href="/wiki/Itraconazole" title="Itraconazole">itraconazole</a> are required to kill fungi compared to ketoconazole, as they have been found to have a greater <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for fungal cell membranes. </p><p>Resistance to ketoconazole has been observed in a number of clinical fungal isolates, including <i>Candida albicans</i>. Experimentally, resistance usually arises as a result of mutations in the sterol biosynthesis pathway. Defects in the sterol 5-6 desaturase enzyme reduce the toxic effects of azole inhibition of the 14-alpha demethylation step. <a href="/wiki/Multidrug_resistance" class="mw-redirect" title="Multidrug resistance">Multidrug-resistance</a> (MDR) genes can also play a role in reducing cellular levels of the drug. As azole antifungals all act at the same point in the sterol pathway, resistant isolates are normally cross-resistant to all members of the azole family.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Antihormonal_activity">Antihormonal activity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=20" title="Edit section: Antihormonal activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As an <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogen</a>, ketoconazole operates through at least two <a href="/wiki/Mechanism_of_action" title="Mechanism of action">mechanisms</a> of action. First, and most notably, high oral doses of ketoconazole (e.g. 40 mg three times per day) block both testicular and adrenal androgen biosynthesis, leading to a reduction in circulating testosterone levels.<sup id="cite_ref-Becker2001_25-7" class="reference"><a href="#cite_note-Becker2001-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2652864_42-0" class="reference"><a href="#cite_note-pmid2652864-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> It produces this effect through inhibition of <a href="/wiki/17%CE%B1-hydroxylase" class="mw-redirect" title="17α-hydroxylase">17α-hydroxylase</a> and <a href="/wiki/17,20-lyase" class="mw-redirect" title="17,20-lyase">17,20-lyase</a>, which are involved in the synthesis and degradation of steroids, including the <a href="/wiki/Precursor_(biochemistry)" class="mw-redirect" title="Precursor (biochemistry)">precursors</a> of <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>.<sup id="cite_ref-Becker2001_25-8" class="reference"><a href="#cite_note-Becker2001-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Due to its efficacy at reducing systemic androgen levels, ketoconazole has been used with some success as a treatment for androgen-dependent prostate cancer.<sup id="cite_ref-pmid8603034_43-0" class="reference"><a href="#cite_note-pmid8603034-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Second, ketoconazole is an <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> <a href="/wiki/Antagonist" title="Antagonist">antagonist</a>, competing with androgens such as testosterone and <a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">dihydrotestosterone</a> (DHT) for binding to the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a>. This effect is thought to be quite weak however, even with high oral doses of ketoconazole.<sup id="cite_ref-pmid1526623_44-0" class="reference"><a href="#cite_note-pmid1526623-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p><p>Ketoconazole, along with <a href="/wiki/Miconazole" title="Miconazole">miconazole</a>, has been found to act as an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor">glucocorticoid receptor</a>.<sup id="cite_ref-pmid6135709_45-0" class="reference"><a href="#cite_note-pmid6135709-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16608920_46-0" class="reference"><a href="#cite_note-pmid16608920-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>Ketoconazole is a <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic mixture</a> consisting of <i>cis</i>-(2<i>S</i>,4<i>R</i>)-(−) and <i>cis</i>-(2<i>R</i>,4<i>S</i>)-(+) enantiomers.<sup id="cite_ref-Arakak_10-1" class="reference"><a href="#cite_note-Arakak-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The <i>cis</i>-(2<i>S</i>,4<i>R</i>) isomer was more potent in inhibiting <a href="/wiki/CYP17A1" title="CYP17A1">progesterone 17α,20-lyase</a> than its enantiomer (<a href="/wiki/IC50" title="IC50">IC<sub>50</sub></a> values of 0.05 and 2.38 <i>μ</i>M, respectively) and in inhibiting <a href="/wiki/Steroid_11-beta-hydroxylase" class="mw-redirect" title="Steroid 11-beta-hydroxylase">11β-hydroxylase</a> (IC<sub>50</sub> values of 0.152 and 0.608 <i>μ</i>M, respectively). Both isomers were relatively weak inhibitors of human placental <a href="/wiki/Aromatase" title="Aromatase">aromatase</a>.<sup id="cite_ref-AR_9-2" class="reference"><a href="#cite_note-AR-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Oral ketoconazole has been used clinically as a steroidogenesis inhibitor in men, women, and children at dosages of 200 to 1,200 mg/day.<sup id="cite_ref-Shaw1996_47-0" class="reference"><a href="#cite_note-Shaw1996-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sonino1986_48-0" class="reference"><a href="#cite_note-Sonino1986-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WheelerKeye2010_49-0" class="reference"><a href="#cite_note-WheelerKeye2010-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Numerous small studies have investigated the effects of oral ketoconazole on hormone levels in humans.<sup id="cite_ref-DrobnisNangia2017_50-0" class="reference"><a href="#cite_note-DrobnisNangia2017-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> It has been found in men to significantly decrease testosterone and estradiol levels and to significantly increase <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a>, <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>, and <a href="/wiki/17%CE%B1-hydroxyprogesterone" class="mw-redirect" title="17α-hydroxyprogesterone">17α-hydroxyprogesterone</a> levels, whereas levels of <a href="/wiki/Androstenedione" title="Androstenedione">androstenedione</a>, <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a>, and <a href="/wiki/Prolactin" title="Prolactin">prolactin</a> were unaffected.<sup id="cite_ref-DrobnisNangia2017_50-1" class="reference"><a href="#cite_note-DrobnisNangia2017-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Feldman1986_51-0" class="reference"><a href="#cite_note-Feldman1986-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sonino1986_48-1" class="reference"><a href="#cite_note-Sonino1986-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> The ratio of testosterone to estradiol is also decreased during oral ketoconazole therapy in men.<sup id="cite_ref-Sonino1986_48-2" class="reference"><a href="#cite_note-Sonino1986-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> Suppression of testosterone levels by ketoconazole is generally partial and has often been found to be transient.<sup id="cite_ref-DrobnisNangia2017_50-2" class="reference"><a href="#cite_note-DrobnisNangia2017-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Better effects on suppression of testosterone levels have been observed in men when ketoconazole is combined with a <a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonist</a> to suppress the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">hypothalamic–pituitary–gonadal axis</a>, which prevents compensatory upregulation of luteinizing hormone <a href="/wiki/Secretion" title="Secretion">secretion</a> and consequent activation of gonadal testosterone production.<sup id="cite_ref-Sonino1986_48-3" class="reference"><a href="#cite_note-Sonino1986-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Premenopausal" class="mw-redirect" title="Premenopausal">premenopausal</a> women with <a href="/wiki/Polycystic_ovary_syndrome" title="Polycystic ovary syndrome">polycystic ovary syndrome</a>, ketoconazole has been found to significantly decrease levels of androstenedione and testosterone and significantly increase levels of 17α-hydroxyprogesterone and estradiol.<sup id="cite_ref-WheelerKeye2010_49-1" class="reference"><a href="#cite_note-WheelerKeye2010-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GalOrly1994_52-0" class="reference"><a href="#cite_note-GalOrly1994-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Studies in <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women with breast cancer have found that ketoconazole significantly decreases androstenedione levels, slightly decreases <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> levels, and does not affect <a href="/wiki/Estrone" title="Estrone">estrone</a> levels.<sup id="cite_ref-Lønning2009_53-0" class="reference"><a href="#cite_note-Lønning2009-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> This indicates minimal inhibition of aromatase by ketoconazole <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i> in humans.<sup id="cite_ref-Lønning2009_53-1" class="reference"><a href="#cite_note-Lønning2009-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Ketoconazole has also been found to decrease levels of <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Corticosteroid" title="Corticosteroid">corticosteroids</a>, such as <a href="/wiki/Cortisol" title="Cortisol">cortisol</a>, <a href="/wiki/Corticosterone" title="Corticosterone">corticosterone</a>, and <a href="/wiki/Aldosterone" title="Aldosterone">aldosterone</a>, as well as <a href="/wiki/Vitamin_D" title="Vitamin D">vitamin D</a>.<sup id="cite_ref-TarbitRobertson1990_54-0" class="reference"><a href="#cite_note-TarbitRobertson1990-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sonino1986_48-4" class="reference"><a href="#cite_note-Sonino1986-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>Ketoconazole has been found to displace <a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">dihydrotestosterone</a> and estradiol from <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i>, but this was not found to be relevant <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i>.<sup id="cite_ref-Sonino1986_48-5" class="reference"><a href="#cite_note-Sonino1986-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Other_activities">Other activities</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=21" title="Edit section: Other activities"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketoconazole has been found to inhibit the activity of the cation channel <a href="/wiki/TRPM5" title="TRPM5">TRPM5</a>.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<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=Ketoconazole&action=edit&section=22" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When administered orally, ketoconazole is best absorbed at highly <a href="/wiki/Acid" title="Acid">acidic</a> levels, so <a href="/wiki/Antacid" title="Antacid">antacids</a> or other causes of decreased <a href="/wiki/Stomach" title="Stomach">stomach</a> acid levels will lower the drug's absorption. Absorption can be increased by taking it with an acidic beverage, such as <a href="/wiki/Cola" title="Cola">cola</a>.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> Ketoconazole is very <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilic</a> and tends to accumulate in fatty tissues. </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=23" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketoconazole is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Imidazole" title="Imidazole">imidazole</a>.<sup id="cite_ref-Elks2014_57-0" class="reference"><a href="#cite_note-Elks2014-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_58-0" class="reference"><a href="#cite_note-IndexNominum2000-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Nonsteroidal" title="Nonsteroidal">nonsteroidal</a> compound.<sup id="cite_ref-Elks2014_57-1" class="reference"><a href="#cite_note-Elks2014-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_58-1" class="reference"><a href="#cite_note-IndexNominum2000-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic mixture</a> of two <a href="/wiki/Enantiomer" title="Enantiomer">enantiomers</a>, <a href="/wiki/Levoketoconazole" title="Levoketoconazole">levoketoconazole</a> ((2<i>S</i>,4<i>R</i>)-(−)-ketoconazole) and dextroketoconazole ((2<i>R</i>,4<i>S</i>)-(+)-ketoconazole).<sup id="cite_ref-Elks2014_57-2" class="reference"><a href="#cite_note-Elks2014-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_58-2" class="reference"><a href="#cite_note-IndexNominum2000-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> Levoketoconazole is under development for potential clinical use as a steroidogenesis inhibitor with better <a href="/wiki/Tolerability" title="Tolerability">tolerability</a> and less <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> than ketoconazole. Other steroidogenesis inhibitors besides ketoconazole and levoketoconazole include the nonsteroidal compound <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">aminoglutethimide</a> and the <a href="/wiki/Steroid" title="Steroid">steroidal</a> compound <a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">abiraterone acetate</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. (December 2022)">citation needed</span></a></i>]</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=Ketoconazole&action=edit&section=24" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketoconazole was discovered in 1976 at <a href="/wiki/Janssen_Pharmaceuticals" title="Janssen Pharmaceuticals">Janssen Pharmaceuticals</a>.<sup id="cite_ref-Heeres_1979_59-0" class="reference"><a href="#cite_note-Heeres_1979-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> It was <a href="/wiki/Patent" title="Patent">patented</a> in 1977,<sup id="cite_ref-Fis2006_14-1" class="reference"><a href="#cite_note-Fis2006-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> followed by introduction in the <a href="/wiki/United_States" title="United States">United States</a> in July 1981.<sup id="cite_ref-GuptaLyons2015_18-2" class="reference"><a href="#cite_note-GuptaLyons2015-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Millikan2016_8-1" class="reference"><a href="#cite_note-Millikan2016-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Publishing2013_60-0" class="reference"><a href="#cite_note-Publishing2013-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fis2006_14-2" class="reference"><a href="#cite_note-Fis2006-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Following its introduction, ketoconazole was the only systemic antifungal available for almost a decade.<sup id="cite_ref-GuptaLyons2015_18-3" class="reference"><a href="#cite_note-GuptaLyons2015-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Ketoconazole was introduced as the prototypical medication of the imidazole group of antifungals.<sup id="cite_ref-Golan2008_61-0" class="reference"><a href="#cite_note-Golan2008-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> Oral ketoconazole has been replaced with oral <a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a> or <a href="/wiki/Itraconazole" title="Itraconazole">itraconazole</a> for many <a href="/wiki/Mycosis" class="mw-redirect" title="Mycosis">mycoses</a>.<sup id="cite_ref-Golan2008_61-1" class="reference"><a href="#cite_note-Golan2008-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>Due to incidence of serious <a href="/wiki/Liver_toxicity" class="mw-redirect" title="Liver toxicity">liver toxicity</a>, the use of oral ketoconazole was suspended in France in July 2011, following review.<sup id="cite_ref-GuptaLyons2015_18-4" class="reference"><a href="#cite_note-GuptaLyons2015-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> This event triggered an evaluation of oral ketoconazole throughout the rest of the European Union.<sup id="cite_ref-GuptaLyons2015_18-5" class="reference"><a href="#cite_note-GuptaLyons2015-18"><span class="cite-bracket">[</span>18<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> In 2013, oral ketoconazole was withdrawn in the European Union and Australia, and strict restrictions were placed on the use of oral ketoconazole in the United States and Canada.<sup id="cite_ref-GuptaLyons2015_18-6" class="reference"><a href="#cite_note-GuptaLyons2015-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Oral ketoconazole is indicated for use in these countries when the indication is a severe or life-threatening systemic infection and alternatives are unavailable.<sup id="cite_ref-GuptaLyons2015_18-7" class="reference"><a href="#cite_note-GuptaLyons2015-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> However, topical ketoconazole, which does not distribute systemically, is safe and widely used still.<sup id="cite_ref-GuptaLyons2015_18-8" class="reference"><a href="#cite_note-GuptaLyons2015-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>Ketoconazole HRA was approved for use in the European Union for treatment of <a href="/wiki/Cushing%27s_syndrome" title="Cushing's syndrome">Cushing's syndrome</a> in November 2013.<sup id="cite_ref-Ketoconazole_HRA_EPAR_7-1" class="reference"><a href="#cite_note-Ketoconazole_HRA_EPAR-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><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> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=25" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=26" title="Edit section: Generic names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketoconazole is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</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 International Nonproprietary Name</span>, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</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 United States Adopted Name</span>, <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</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 British Approved Name</span>, and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</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 Japanese Accepted Name</span>.<sup id="cite_ref-Elks2014_57-3" class="reference"><a href="#cite_note-Elks2014-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_58-3" class="reference"><a href="#cite_note-IndexNominum2000-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_64-0" class="reference"><a href="#cite_note-MortonHall2012-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_65-0" class="reference"><a href="#cite_note-Drugs.com-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=27" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketoconazole has been marketed under a large number of brand names.<sup id="cite_ref-Elks2014_57-4" class="reference"><a href="#cite_note-Elks2014-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IndexNominum2000_58-4" class="reference"><a href="#cite_note-IndexNominum2000-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_64-1" class="reference"><a href="#cite_note-MortonHall2012-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_65-1" class="reference"><a href="#cite_note-Drugs.com-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ketoconazole&action=edit&section=28" title="Edit section: Availability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketoconazole is available widely throughout the world.<sup id="cite_ref-IndexNominum2000_58-5" class="reference"><a href="#cite_note-IndexNominum2000-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_65-2" class="reference"><a href="#cite_note-Drugs.com-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> </p><p>In 2013, the <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a>'s <a href="/wiki/Committee_for_Medicinal_Products_for_Human_Use" title="Committee for Medicinal Products for Human Use">Committee for Medicinal Products for Human Use</a> (CHMP) recommended that a ban be imposed on the use of oral ketoconazole for systemic use in humans throughout the European Union, after concluding that the risk of serious <a href="/wiki/Liver_injury" title="Liver injury">liver injury</a> from systemic ketoconazole outweighs its benefits.<sup id="cite_ref-url_ema_66-0" class="reference"><a href="#cite_note-url_ema-66"><span class="cite-bracket">[</span>66<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=Ketoconazole&action=edit&section=29" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As of March 2019, oral <a href="/wiki/Levoketoconazole" title="Levoketoconazole">levoketoconazole</a> (developmental code name COR-003, tentative brand name Recorlev) is <a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">phase III</a> <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a> for the treatment of <a href="/wiki/Cushing%27s_syndrome" title="Cushing's syndrome">Cushing's syndrome</a>.<sup id="cite_ref-Levoketoconazole-AdisInsight_67-0" class="reference"><a href="#cite_note-Levoketoconazole-AdisInsight-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Oral levoketoconazole may have a lower risk of liver toxicity than oral ketoconazole.<sup id="cite_ref-FleseriuCastinetti2016_68-0" class="reference"><a href="#cite_note-FleseriuCastinetti2016-68"><span class="cite-bracket">[</span>68<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=Ketoconazole&action=edit&section=30" title="Edit section: Veterinary use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ketoconazole is sometimes prescribed as an antifungal by <a href="/wiki/Veterinarian" title="Veterinarian">veterinarians</a> for use in pets, often as unflavored tablets that may need to be cut to smaller size for correct dosage.<sup id="cite_ref-KuKanich_2008_69-0" class="reference"><a href="#cite_note-KuKanich_2008-69"><span class="cite-bracket">[</span>69<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=Ketoconazole&action=edit&section=31" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.merriam-webster.com/dictionary/Ketoconazole">"Ketoconazole"</a>. <i><a href="/wiki/Merriam-Webster" title="Merriam-Webster">Merriam-Webster.com Dictionary</a></i>. Merriam-Webster.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Merriam-Webster.com+Dictionary&rft.atitle=Ketoconazole&rft_id=https%3A%2F%2Fwww.merriam-webster.com%2Fdictionary%2FKetoconazole&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation encyclopaedia cs1"><a rel="nofollow" class="external text" href="https://www.dictionary.com/browse/Ketoconazole">"Ketoconazole"</a>. <i><a href="/wiki/Dictionary.com" title="Dictionary.com">Dictionary.com Unabridged</a></i> (Online). n.d.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Ketoconazole&rft.btitle=Dictionary.com+Unabridged&rft_id=https%3A%2F%2Fwww.dictionary.com%2Fbrowse%2FKetoconazole&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-FDA-AllBoxedWarnings-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-FDA-AllBoxedWarnings_3-0">^</a></b></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://nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802">"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"</a>. <i>nctr-crs.fda.gov</i>. <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a><span class="reference-accessdate">. Retrieved <span class="nowrap">22 October</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=nctr-crs.fda.gov&rft.atitle=FDA-sourced+list+of+all+drugs+with+black+box+warnings+%28Use+Download+Full+Results+and+View+Query+links.%29&rft_id=https%3A%2F%2Fnctr-crs.fda.gov%2Ffdalabel%2Fui%2Fspl-summaries%2Fcriteria%2F343802&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.medicines.org.uk/emc/product/1767/smpc">"Ketoconazole HRA 200mg Tablets - Summary of Product Characteristics (SmPC)"</a>. <i>(emc)</i>. 18 September 2017. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200802215412/https://www.medicines.org.uk/emc/product/1767/smpc">Archived</a> from the original on 2 August 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">1 April</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=%28emc%29&rft.atitle=Ketoconazole+HRA+200mg+Tablets+-+Summary+of+Product+Characteristics+%28SmPC%29&rft.date=2017-09-18&rft_id=https%3A%2F%2Fwww.medicines.org.uk%2Femc%2Fproduct%2F1767%2Fsmpc&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.medicines.org.uk/emc/product/4559/smpc">"Ketoconazole 2% w/w Shampoo - Summary of Product Characteristics (SmPC)"</a>. <i>(emc)</i>. 5 October 2015. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200803021950/https://www.medicines.org.uk/emc/product/4559/smpc">Archived</a> from the original on 3 August 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">1 April</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=%28emc%29&rft.atitle=Ketoconazole+2%25+w%2Fw+Shampoo+-+Summary+of+Product+Characteristics+%28SmPC%29&rft.date=2015-10-05&rft_id=https%3A%2F%2Fwww.medicines.org.uk%2Femc%2Fproduct%2F4559%2Fsmpc&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-Ketoconazole_tablet_label-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ketoconazole_tablet_label_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ketoconazole_tablet_label_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ketoconazole_tablet_label_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ketoconazole_tablet_label_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Ketoconazole_tablet_label_6-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Ketoconazole_tablet_label_6-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Ketoconazole_tablet_label_6-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Ketoconazole_tablet_label_6-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Ketoconazole_tablet_label_6-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Ketoconazole_tablet_label_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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6d4be760-c723-4f54-a854-12c61cf91703">"Ketoconazole tablet"</a>. <i>DailyMed</i>. 26 June 2018. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200805193136/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=6d4be760-c723-4f54-a854-12c61cf91703">Archived</a> from the original on 5 August 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">5 January</span> 2020</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=Ketoconazole+tablet&rft.date=2018-06-26&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D6d4be760-c723-4f54-a854-12c61cf91703&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-Ketoconazole_HRA_EPAR-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ketoconazole_HRA_EPAR_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ketoconazole_HRA_EPAR_7-1"><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://www.ema.europa.eu/en/medicines/human/EPAR/ketoconazole-hra">"Ketoconazole HRA EPAR"</a>. <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA). 23 April 2012. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200803001830/https://www.ema.europa.eu/en/medicines/human/EPAR/ketoconazole-hra">Archived</a> from the original on 3 August 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">1 April</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Ketoconazole+HRA+EPAR&rft.pub=European+Medicines+Agency+%28EMA%29&rft.date=2012-04-23&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fmedicines%2Fhuman%2FEPAR%2Fketoconazole-hra&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-Millikan2016-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Millikan2016_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Millikan2016_8-1"><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="CITEREFMillikan2016" class="citation book cs1">Millikan LE (19 April 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=3TDMBQAAQBAJ&pg=PA82"><i>Drug Therapy in Dermatology</i></a>. CRC Press. pp. 82–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-203-90831-0" title="Special:BookSources/978-0-203-90831-0"><bdi>978-0-203-90831-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drug+Therapy+in+Dermatology&rft.pages=82-&rft.pub=CRC+Press&rft.date=2016-04-19&rft.isbn=978-0-203-90831-0&rft.aulast=Millikan&rft.aufirst=LE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D3TDMBQAAQBAJ%26pg%3DPA82&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-AR-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-AR_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AR_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-AR_9-2"><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 class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003906/WC500181493.pdf">"Assessment report: Ketoconazole HRA"</a> <span class="cs1-format">(PDF)</span>. <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160827011824/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/003906/WC500181493.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 27 August 2016<span class="reference-accessdate">. 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American Society of Health-System Pharmacists. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20101228050612/https://www.drugs.com/monograph/ketoconazole.html">Archived</a> from the original on 28 December 2010<span class="reference-accessdate">. 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Retrieved <span class="nowrap">23 March</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Therapeutic+Goods+Administration+%28TGA%29&rft.atitle=Oral+ketoconazole+%28Nizoral%29+200+mg+tablets&rft.date=2013-10-10&rft_id=https%3A%2F%2Fwww.tga.gov.au%2Falert%2Foral-ketoconazole-nizoral-200-mg-tablets&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-GuptaLyons2015-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-GuptaLyons2015_18-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-GuptaLyons2015_18-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-GuptaLyons2015_18-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-GuptaLyons2015_18-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-GuptaLyons2015_18-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-GuptaLyons2015_18-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-GuptaLyons2015_18-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-GuptaLyons2015_18-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-GuptaLyons2015_18-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGuptaLyons2015" class="citation journal cs1">Gupta AK, Lyons DC (2015). 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Retrieved <span class="nowrap">2 July</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=%E5%9B%BD%E5%AE%B6%E9%A3%9F%E5%93%81%E8%8D%AF%E5%93%81%E7%9B%91%E7%9D%A3%E7%AE%A1%E7%90%86%E6%80%BB%E5%B1%80%E5%85%B3%E4%BA%8E%E5%81%9C%E6%AD%A2%E7%94%9F%E4%BA%A7%E9%94%80%E5%94%AE%E4%BD%BF%E7%94%A8%E9%85%AE%E5%BA%B7%E5%94%91%E5%8F%A3%E6%9C%8D%E5%88%B6%E5%89%82%E7%9A%84%E5%85%AC%E5%91%8A%EF%BC%882015%E5%B9%B4%E7%AC%AC85%E5%8F%B7%EF%BC%89&rft.pub=China+Food+and+Drug+Administration&rft.date=2015-06-25&rft_id=http%3A%2F%2Fwww.sfda.gov.cn%2FWS01%2FCL0087%2F122883.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-phillips-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-phillips_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-phillips_20-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-phillips_20-2"><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="CITEREFPhillipsRosen2013" class="citation book cs1">Phillips RM, Rosen T (2013). "Topical Antifungal Agents". In Wolverton SE (ed.). <i>Comprehensive Dermatologic Therapy</i> (3rd ed.). 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"Other Eczematous Eruptions". In Bolognia JL (ed.). <i>Dermatology</i> (3rd ed.). Philadelphia: Saunders. pp. <span class="nowrap">219–</span>221. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780723435716" title="Special:BookSources/9780723435716"><bdi>9780723435716</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Other+Eczematous+Eruptions&rft.btitle=Dermatology&rft.place=Philadelphia&rft.pages=%3Cspan+class%3D%22nowrap%22%3E219-%3C%2Fspan%3E221&rft.edition=3rd&rft.pub=Saunders&rft.date=2012&rft.isbn=9780723435716&rft.aulast=Neider&rft.aufirst=R&rft.au=Fritsch%2C+PO&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFYoungBrodellCooper2013" class="citation book cs1">Young BK, Brodell RT, Cooper KD (2013). 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Antimicrobial+Agents+and+Chemotherapy&rft.atitle=Effects+of+an+acidic+beverage+%28Coca-Cola%29+on+absorption+of+ketoconazole&rft.volume=39&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1671-%3C%2Fspan%3E5&rft.date=1995-08&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC162805%23id-name%3DPMC&rft_id=info%3Apmid%2F7486898&rft_id=info%3Adoi%2F10.1128%2FAAC.39.8.1671&rft.aulast=Chin&rft.aufirst=TW&rft.au=Loeb%2C+M&rft.au=Fong%2C+IW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC162805&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-Elks2014-57"><span class="mw-cite-backlink">^ <a href="#cite_ref-Elks2014_57-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Elks2014_57-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Elks2014_57-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Elks2014_57-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Elks2014_57-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><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=PA720"><i>The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</i></a>. Springer. pp. 720–. <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>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110131052/https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA720">Archived</a> from the original on 10 January 2023<span class="reference-accessdate">. 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Elsevier. pp. 1997–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8155-1856-3" title="Special:BookSources/978-0-8155-1856-3"><bdi>978-0-8155-1856-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110131025/https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1997">Archived</a> from the original on 10 January 2023<span class="reference-accessdate">. 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Lippincott Williams & Wilkins. pp. 624–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-8355-2" title="Special:BookSources/978-0-7817-8355-2"><bdi>978-0-7817-8355-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110131048/https://books.google.com/books?id=az8uSDkB0mgC&pg=PA624">Archived</a> from the original on 10 January 2023<span class="reference-accessdate">. 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Retrieved <span class="nowrap">22 February</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Ketoconazole-containing+medicines&rft.pub=European+Medicines+Agency+%28EMA%29&rft.date=2013-07-25&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fmedicines%2Fhuman%2Freferrals%2Fketoconazole-containing-medicines&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-63">^</a></b></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://www.ema.europa.eu/en/news/ketoconazole-hra-recommended-approval-cushings-syndrome">"Ketoconazole HRA recommended for approval in Cushing's syndrome"</a>. <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA). 26 September 2014. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240222030047/https://www.ema.europa.eu/en/news/ketoconazole-hra-recommended-approval-cushings-syndrome">Archived</a> from the original on 22 February 2024<span class="reference-accessdate">. Retrieved <span class="nowrap">22 February</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Ketoconazole+HRA+recommended+for+approval+in+Cushing%27s+syndrome&rft.pub=European+Medicines+Agency+%28EMA%29&rft.date=2014-09-26&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fnews%2Fketoconazole-hra-recommended-approval-cushings-syndrome&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-MortonHall2012-64"><span class="mw-cite-backlink">^ <a href="#cite_ref-MortonHall2012_64-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MortonHall2012_64-1"><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="CITEREFMortonHall2012" class="citation book cs1">Morton IK, Hall JM (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA159"><i>Concise Dictionary of Pharmacological Agents: Properties and Synonyms</i></a>. 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Retrieved <span class="nowrap">14 June</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Levoketoconazole+-+Strongbridge+Biopharma+-+AdisInsight&rft_id=https%3A%2F%2Fadisinsight.springer.com%2Fdrugs%2F800037965&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-FleseriuCastinetti2016-68"><span class="mw-cite-backlink"><b><a href="#cite_ref-FleseriuCastinetti2016_68-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFleseriuCastinetti2016" class="citation journal cs1">Fleseriu M, Castinetti F (December 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5080363">"Updates on the role of adrenal steroidogenesis inhibitors in Cushing's syndrome: a focus on novel therapies"</a>. <i>Pituitary</i>. <b>19</b> (6): <span class="nowrap">643–</span>653. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2Fs11102-016-0742-1">10.1007/s11102-016-0742-1</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5080363">5080363</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/27600150">27600150</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pituitary&rft.atitle=Updates+on+the+role+of+adrenal+steroidogenesis+inhibitors+in+Cushing%27s+syndrome%3A+a+focus+on+novel+therapies&rft.volume=19&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E643-%3C%2Fspan%3E653&rft.date=2016-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5080363%23id-name%3DPMC&rft_id=info%3Apmid%2F27600150&rft_id=info%3Adoi%2F10.1007%2Fs11102-016-0742-1&rft.aulast=Fleseriu&rft.aufirst=M&rft.au=Castinetti%2C+F&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5080363&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> <li id="cite_note-KuKanich_2008-69"><span class="mw-cite-backlink"><b><a href="#cite_ref-KuKanich_2008_69-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKuKanich2008" class="citation journal cs1">KuKanich B (January 2008). <a rel="nofollow" class="external text" href="http://veterinarymedicine.dvm360.com/vetmed/Medicine/ArticleStandard/Article/detail/483478">"A review of selected systemic antifungal drugs for use in dogs and cats"</a>. <i>Veterinary Medicine</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20131005093333/http://veterinarymedicine.dvm360.com/vetmed/Medicine/ArticleStandard/Article/detail/483478">Archived</a> from the original on 5 October 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Veterinary+Medicine&rft.atitle=A+review+of+selected+systemic+antifungal+drugs+for+use+in+dogs+and+cats&rft.date=2008-01&rft.aulast=KuKanich&rft.aufirst=B&rft_id=http%3A%2F%2Fveterinarymedicine.dvm360.com%2Fvetmed%2FMedicine%2FArticleStandard%2FArticle%2Fdetail%2F483478&rfr_id=info%3Asid%2Fen.wikipedia.org%3AKetoconazole" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output 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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:Antifungals" title="Template:Antifungals"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antifungals" title="Template talk:Antifungals"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antifungals" title="Special:EditPage/Template:Antifungals"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antifungals_(D01_and_J02)425" style="font-size:114%;margin:0 4em"><a href="/wiki/Antifungal" title="Antifungal">Antifungals</a> (<a href="/wiki/ATC_code_D01" title="ATC code D01">D01</a> and <a href="/wiki/ATC_code_J02" title="ATC code J02">J02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Wall/<br />membrane</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a><br />inhibitors</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%"><a href="/wiki/Azole" title="Azole">Azoles</a> (<a href="/wiki/Lanosterol_14%CE%B1-demethylase" class="mw-redirect" title="Lanosterol 14α-demethylase">lanosterol 14α-<br />demethylase</a> inhibitors)</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%"><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Bifonazole" title="Bifonazole">bifonazole</a><sup>‡</sup></li> <li><a href="/wiki/Butoconazole" title="Butoconazole">butoconazole</a></li> <li><a href="/wiki/Chlormidazole" title="Chlormidazole">chlormidazole</a><sup>‡</sup></li> <li><a href="/wiki/Climbazole" title="Climbazole">climbazole</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">clotrimazole</a><sup>#</sup></li> <li><a href="/wiki/Croconazole" title="Croconazole">croconazole</a><sup>‡</sup></li> <li><a href="/wiki/Eberconazole" title="Eberconazole">eberconazole</a></li> <li><a href="/wiki/Econazole" title="Econazole">econazole</a></li> <li><a href="/wiki/Fenticonazole" title="Fenticonazole">fenticonazole</a><sup>‡</sup></li> <li><a href="/wiki/Flutrimazole" title="Flutrimazole">flutrimazole</a></li> <li><a href="/wiki/Isoconazole" title="Isoconazole">isoconazole</a></li> <li><a class="mw-selflink selflink">ketoconazole</a></li> <li><a href="/wiki/Luliconazole" title="Luliconazole">luliconazole</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">miconazole</a><sup>#</sup></li> <li><a href="/wiki/Neticonazole" title="Neticonazole">neticonazole</a><sup>‡</sup></li> <li><a href="/wiki/Omoconazole" title="Omoconazole">omoconazole</a><sup>‡</sup></li> <li><a href="/wiki/Oxiconazole" title="Oxiconazole">oxiconazole</a></li> <li><a href="/wiki/Sertaconazole" title="Sertaconazole">sertaconazole</a></li> <li><a href="/wiki/Sulconazole" title="Sulconazole">sulconazole</a></li> <li><a href="/wiki/Tioconazole" title="Tioconazole">tioconazole</a></li></ul> <ul><li>Systemic: ketoconazole</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triazole" title="Triazole">Triazoles</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Efinaconazole" title="Efinaconazole">efinaconazole</a></li> <li><a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a><sup>#</sup></li> <li><a href="/wiki/Terconazole" title="Terconazole">terconazole</a></li></ul> <ul><li>Systemic: <a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a><sup>#</sup></li> <li><a href="/wiki/Fosfluconazole" title="Fosfluconazole">fosfluconazole</a></li> <li><a href="/wiki/Fosravuconazole" title="Fosravuconazole">fosravuconazole</a></li> <li><a href="/wiki/Hexaconazole" title="Hexaconazole">hexaconazole</a><sup>‡</sup></li> <li><a href="/wiki/Isavuconazonium" title="Isavuconazonium">isavuconazole</a></li> <li><a href="/wiki/Itraconazole" title="Itraconazole">itraconazole</a><sup>#</sup></li> <li><a href="/wiki/Oteseconazole" title="Oteseconazole">oteseconazole</a></li> <li><a href="/wiki/Posaconazole" title="Posaconazole">posaconazole</a></li> <li><a href="/wiki/Voriconazole" title="Voriconazole">voriconazole</a><sup>#</sup></li></ul> <ul><li>Unknown: <a href="/wiki/Albaconazole" title="Albaconazole">albaconazole</a><sup>‡</sup></li> <li><a href="/wiki/Ravuconazole" title="Ravuconazole">ravuconazole</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thiazole" title="Thiazole">Thiazoles</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Abafungin" title="Abafungin">abafungin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polyene_antimycotic" title="Polyene antimycotic">Polyene antimycotics</a><br />(<a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a> binding)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Hamycin" title="Hamycin">hamycin</a><sup>‡</sup></li> <li><a href="/wiki/Natamycin" title="Natamycin">natamycin</a></li> <li><a href="/wiki/Nystatin" title="Nystatin">nystatin</a><sup>#</sup><br />Systemic: <a href="/wiki/Amphotericin_B" title="Amphotericin B">amphotericin B</a><sup>#</sup>, hamycin<sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Squalene_monooxygenase" title="Squalene monooxygenase">Squalene monooxygenase</a><br />inhibitors</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%"><a href="/wiki/Allylamine" title="Allylamine">Allylamines</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Naftifine" title="Naftifine">naftifine</a></li> <li><a href="/wiki/Terbinafine" title="Terbinafine">terbinafine</a><br />Systemic: terbinafine</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzylamine" title="Benzylamine">Benzylamines</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Butenafine" title="Butenafine">butenafine</a></li></ul> </div></td></tr></tbody></table><div></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" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Amorolfine" title="Amorolfine">amorolfine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/1,3-Beta-glucan_synthase" title="1,3-Beta-glucan synthase">β-glucan synthase</a><br />inhibitors</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Systemic: <a href="/wiki/Echinocandin" title="Echinocandin">echinocandins</a> (<a href="/wiki/Anidulafungin" title="Anidulafungin">anidulafungin</a></li> <li><a href="/wiki/Caspofungin" title="Caspofungin">caspofungin</a></li> <li><a href="/wiki/Cilofungin" title="Cilofungin">cilofungin</a></li> <li><a href="/wiki/Micafungin" title="Micafungin">micafungin</a></li> <li><a href="/wiki/Rezafungin" title="Rezafungin">rezafungin</a>)</li> <li><a href="/wiki/Ibrexafungerp" title="Ibrexafungerp">ibrexafungerp</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intracellular</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrimidine_analogue" title="Pyrimidine analogue">Pyrimidine analogues</a>/<br /><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">thymidylate synthase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Systemic: <a href="/wiki/Flucytosine" title="Flucytosine">flucytosine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mitotic_inhibitor" title="Mitotic inhibitor">Mitotic inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Systemic: <a href="/wiki/Griseofulvin" title="Griseofulvin">griseofulvin</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aminoacyl_tRNA_synthetase" title="Aminoacyl tRNA synthetase">Aminoacyl tRNA synthetase</a> inhibitors</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Tavaborole" title="Tavaborole">tavaborole</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</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/Bromochlorosalicylanilide" title="Bromochlorosalicylanilide">bromochlorosalicylanilide</a></li> <li><a href="/wiki/Chlorophetanol" title="Chlorophetanol">chlorophetanol</a></li> <li><a href="/wiki/Chlorphenesin" class="mw-redirect" title="Chlorphenesin">chlorphenesin</a></li> <li><a href="/wiki/Ciclopirox" title="Ciclopirox">ciclopirox</a></li> <li><a href="/wiki/Crystal_violet" title="Crystal violet">crystal violet</a></li> <li><a href="/wiki/Dimazole" title="Dimazole">dimazole</a></li> <li><a href="/wiki/Ethylparaben" title="Ethylparaben">ethylparaben</a></li> <li><a href="/wiki/Haloprogin" title="Haloprogin">haloprogin</a><sup>‡</sup></li> <li><a href="/wiki/Polynoxylin" title="Polynoxylin">polynoxylin</a></li> <li><a href="/wiki/Potassium_iodide" title="Potassium iodide">potassium iodide</a><sup>#</sup></li> <li><a href="/wiki/Salicylic_acid" title="Salicylic acid">salicylic acid</a></li> <li><a href="/wiki/Selenium_disulfide" title="Selenium disulfide">selenium disulfide</a><sup>#</sup></li> <li><a href="/wiki/Sodium_thiosulfate" title="Sodium thiosulfate">sodium thiosulfate</a><sup>#</sup></li> <li><a href="/wiki/Sulbentine" title="Sulbentine">sulbentine</a></li> <li><a href="/wiki/Taurolidine" title="Taurolidine">taurolidine</a></li> <li><a href="/wiki/Ticlatone" title="Ticlatone">ticlatone</a></li> <li><a href="/wiki/Tolciclate" title="Tolciclate">tolciclate</a></li> <li><a href="/wiki/Tolnaftate" title="Tolnaftate">tolnaftate</a></li> <li><a href="/wiki/Tribromometacresol" title="Tribromometacresol">tribromometacresol</a></li> <li><a href="/wiki/Undecylenic_acid" title="Undecylenic acid">undecylenic acid</a></li> <li><a href="/wiki/Whitfield%27s_ointment" title="Whitfield's ointment">Whitfield's ointment</a><sup>#</sup></li></ul> <ul><li><a href="/wiki/Citronella_oil" title="Citronella oil">citronella oil</a></li> <li><a href="/wiki/Lemon_grass" class="mw-redirect" title="Lemon grass">lemon grass</a></li> <li><a href="/wiki/Lemon_myrtle" class="mw-redirect" title="Lemon myrtle">lemon myrtle</a></li> <li><a href="/wiki/Orange_oil" title="Orange oil">orange oil</a></li> <li><a href="/wiki/Patchouli" title="Patchouli">patchouli</a></li> <li><a href="/wiki/Tea_tree_oil" title="Tea tree oil">tea tree oil</a></li> <li><a href="/wiki/Pneumocystis_pneumonia" title="Pneumocystis pneumonia">PCP</a>: <a href="/wiki/Atovaquone" title="Atovaquone">atovaquone</a></li> <li><a href="/wiki/Dapsone" title="Dapsone">dapsone</a></li> <li><a href="/wiki/Pentamidine" title="Pentamidine">pentamidine</a></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="Gynecological_anti-infectives_and_antiseptics_(G01)265" 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" /><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:Gynecological_anti-infectives_and_antiseptics" title="Template:Gynecological anti-infectives and antiseptics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Gynecological_anti-infectives_and_antiseptics" title="Template talk:Gynecological anti-infectives and antiseptics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Gynecological_anti-infectives_and_antiseptics" title="Special:EditPage/Template:Gynecological anti-infectives and antiseptics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Gynecological_anti-infectives_and_antiseptics_(G01)265" style="font-size:114%;margin:0 4em"><a href="/wiki/Gynaecology" title="Gynaecology">Gynecological</a> <a href="/wiki/Anti-infective" class="mw-redirect" title="Anti-infective">anti-infectives</a> and <a href="/wiki/Antiseptic" title="Antiseptic">antiseptics</a> (<a href="/wiki/ATC_code_G01" title="ATC code G01">G01</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antibacterial" class="mw-redirect" title="Antibacterial">Antibiotics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Candicidin" title="Candicidin">Candicidin</a></li> <li><a href="/wiki/Chloramphenicol" title="Chloramphenicol">Chloramphenicol</a></li> <li><a href="/wiki/Hachimycin" title="Hachimycin">Hachimycin</a></li> <li><a href="/wiki/Oxytetracycline" title="Oxytetracycline">Oxytetracycline</a></li> <li><a href="/wiki/Carfecillin" title="Carfecillin">Carfecillin</a></li> <li><a href="/wiki/Mepartricin" title="Mepartricin">Mepartricin</a></li> <li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Pentamycin" title="Pentamycin">Pentamycin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arsenic" title="Arsenic">Arsenic</a> compounds</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/Acetarsol" title="Acetarsol">Acetarsol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinoline" title="Quinoline">Quinoline</a> derivatives</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/Diiodohydroxyquinoline" title="Diiodohydroxyquinoline">Diiodohydroxyquinoline</a></li> <li><a href="/wiki/Clioquinol" title="Clioquinol">Clioquinol</a></li> <li><a href="/wiki/Chlorquinaldol" title="Chlorquinaldol">Chlorquinaldol</a></li> <li><a href="/wiki/Dequalinium" title="Dequalinium">Dequalinium</a></li> <li><a href="/wiki/Broxyquinoline" title="Broxyquinoline">Broxyquinoline</a></li> <li><a href="/wiki/8-Hydroxyquinoline" title="8-Hydroxyquinoline">Oxyquinoline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_acid" title="Organic acid">Organic acids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lactic_acid" title="Lactic acid">Lactic acid</a></li> <li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">Ascorbic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfonamide_(medicine)" title="Sulfonamide (medicine)">Sulfonamides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sulfatolamide" title="Sulfatolamide">Sulfatolamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antifungal_medication" class="mw-redirect" title="Antifungal medication">Antifungals</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Metronidazole" title="Metronidazole">Metronidazole</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">Miconazole</a></li> <li><a href="/wiki/Econazole" title="Econazole">Econazole</a></li> <li><a href="/wiki/Ornidazole" title="Ornidazole">Ornidazole</a></li> <li><a href="/wiki/Isoconazole" title="Isoconazole">Isoconazole</a></li> <li><a href="/wiki/Tioconazole" title="Tioconazole">Tioconazole</a></li> <li><a class="mw-selflink selflink">Ketoconazole</a></li> <li><a href="/wiki/Fenticonazole" title="Fenticonazole">Fenticonazole</a></li> <li><a href="/wiki/Azanidazole" title="Azanidazole">Azanidazole</a></li> <li><a href="/wiki/Propenidazole" title="Propenidazole">Propenidazole</a></li> <li><a href="/wiki/Butoconazole" title="Butoconazole">Butoconazole</a></li> <li><a href="/wiki/Omoconazole" title="Omoconazole">Omoconazole</a></li> <li><a href="/wiki/Oxiconazole" title="Oxiconazole">Oxiconazole</a></li> <li><a href="/wiki/Flutrimazole" title="Flutrimazole">Flutrimazole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triazole" title="Triazole">Triazoles</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Terconazole" title="Terconazole">Terconazole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polyene_antimycotic" title="Polyene antimycotic">Polyenes</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nystatin" title="Nystatin">Nystatin</a></li> <li><a href="/wiki/Natamycin" title="Natamycin">Natamycin</a></li> <li><a href="/wiki/Amphotericin_B" title="Amphotericin B">Amphotericin B</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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ciclopirox" title="Ciclopirox">Ciclopirox</a></li> <li><a href="/wiki/Crystal_violet" title="Crystal violet">Methylrosaniline</a></li></ul> </div></td></tr></tbody></table><div></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 hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Clodantoin" class="mw-redirect" title="Clodantoin">Clodantoin</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Policresulen" title="Policresulen">Policresulen</a></li> <li><a href="/wiki/Nifuratel" title="Nifuratel">Nifuratel</a></li> <li><a href="/wiki/Furazolidone" title="Furazolidone">Furazolidone</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a></li> <li><a href="/wiki/Protiofate" title="Protiofate">Protiofate</a></li> <li><i><a href="/wiki/Lactobacillus_fermentum" class="mw-redirect" title="Lactobacillus fermentum">Lactobacillus fermentum</a></i></li> <li><a href="/wiki/Copper_usnate" title="Copper usnate">Copper usnate</a></li></ul> </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="Other_dermatological_preparations_(D11)246" style="padding:3px"><table class="nowraplinks 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:Other_dermatological_preparations" title="Template:Other dermatological preparations"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Other_dermatological_preparations" title="Template talk:Other dermatological preparations"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Other_dermatological_preparations" title="Special:EditPage/Template:Other dermatological preparations"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Other_dermatological_preparations_(D11)246" style="font-size:114%;margin:0 4em">Other <a href="/wiki/Dermatological" class="mw-redirect" title="Dermatological">dermatological</a> preparations (<a href="/wiki/ATC_code_D11" title="ATC code D11">D11</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anti-seborrheic" title="Anti-seborrheic">Anti-seborrheics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a></i> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul></li> <li><i><a href="/wiki/Antifungal" title="Antifungal">Antifungals</a></i> <ul><li><a href="/wiki/Bifonazole" title="Bifonazole">Bifonazole</a></li> <li><a href="/wiki/Cetrimonium_bromide" title="Cetrimonium bromide">Cetrimonium bromide</a> (<a href="/wiki/Cetrimide" title="Cetrimide">cetrimide</a>)</li> <li><a href="/wiki/Ciclopirox_olamine" class="mw-redirect" title="Ciclopirox olamine">Ciclopirox olamine (ciclopirox)</a></li> <li><a href="/wiki/Climbazole" title="Climbazole">Climbazole</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a class="mw-selflink selflink">Ketoconazole</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">Miconazole</a></li> <li><a href="/wiki/Piroctone_olamine" title="Piroctone olamine">Piroctone olamine</a></li> <li><a href="/wiki/Selenium_disulfide" title="Selenium disulfide">Selenium disulfide (selenium sulfide)</a></li> <li><a href="/w/index.php?title=Xenysalate&action=edit&redlink=1" class="new" title="Xenysalate (page does not exist)">Xenysalate</a></li> <li><a href="/wiki/Zinc_pyrithione" title="Zinc pyrithione">Zinc pyrithione (pyrithione zinc)</a></li></ul></li> <li><i><a href="/wiki/Antihistamine" title="Antihistamine">Antihistamines</a></i></li> <li><i><a href="/wiki/Calcineurin_inhibitor" class="mw-redirect" title="Calcineurin inhibitor">Calcineurin inhibitors</a></i> <ul><li><a href="/wiki/Cyclosporin" class="mw-redirect" title="Cyclosporin">Cyclosporin</a></li> <li><a href="/wiki/Pimecrolimus" title="Pimecrolimus">Pimecrolimus</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li></ul></li> <li><a href="/wiki/Isotretinoin" title="Isotretinoin">Isotretinoin</a></li> <li><i><a href="/wiki/Keratolytic" title="Keratolytic">Keratolytics</a></i> <ul><li><a href="/wiki/Coal_tar" title="Coal tar">Coal tar</a></li> <li><a href="/wiki/Resorcinol" title="Resorcinol">Resorcinol</a></li> <li><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylic acid</a></li> <li><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></li> <li><a href="/wiki/Urea" title="Urea">Urea</a> (<a href="/wiki/Urea-containing_cream" title="Urea-containing cream">urea-containing cream</a>)</li></ul></li> <li><i><a href="/wiki/Lithium_(medication)" title="Lithium (medication)">Lithium salts</a></i> <ul><li><a href="/wiki/Lithium_gluconate" class="mw-redirect" title="Lithium gluconate">Lithium gluconate</a></li> <li><a href="/wiki/Lithium_succinate" title="Lithium succinate">Lithium succinate</a></li></ul></li> <li><i><a href="/wiki/Topical_steroid" title="Topical steroid">Topical corticosteroids</a></i> (e.g., <a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Skin_whitening" title="Skin whitening">Skin lightening</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Hydroquinone" title="Hydroquinone">Hydroquinone</a></li> <li><a href="/wiki/Mequinol" title="Mequinol">Mequinol</a></li> <li><a href="/wiki/Monobenzone" title="Monobenzone">Monobenzone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sun_tanning" title="Sun tanning">Skin darkening</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Afamelanotide" title="Afamelanotide">Afamelanotide</a></li> <li><a href="/wiki/Melanotan_II" title="Melanotan II">Melanotan II</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anti-inflammatories" class="mw-redirect" title="Anti-inflammatories">Anti-inflammatories</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/%CE%93-Linolenic_acid" title="Γ-Linolenic acid">Gamolenic acid</a></li> <li><a href="/wiki/Oxaceprol" title="Oxaceprol">Oxaceprol</a></li> <li><a href="/wiki/Pimecrolimus" title="Pimecrolimus">Pimecrolimus</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li></ul> <ul><li><i><a href="/wiki/Topical_steroid" title="Topical steroid">Topical corticosteroids</a></i> (e.g., <a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Management_of_hair_loss" title="Management of hair loss">Alopecia treatments</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase inhibitors</a></i> <ul><li><a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></li></ul></li> <li><i><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a></i> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li></ul></li> <li><i><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium channel openers</a></i> <ul><li><a href="/wiki/Minoxidil" title="Minoxidil">Minoxidil</a></li></ul></li> <li><i>Others</i> <ul><li><a href="/wiki/Nepidermin" title="Nepidermin">Nepidermin</a></li> <li><a href="/wiki/Ritlecitinib" title="Ritlecitinib">Ritlecitinib</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hair_growth_inhibitor" class="mw-redirect" title="Hair growth inhibitor">Hair growth inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase inhibitors</a></i> <ul><li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li></ul></li> <li><i><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a></i> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul></li> <li><a href="/wiki/Eflornithine" title="Eflornithine">Eflornithine</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/Abrocitinib" title="Abrocitinib">Abrocitinib</a></li> <li><a href="/wiki/Aminobenzoate" class="mw-redirect" title="Aminobenzoate">Aminobenzoate potassium</a></li> <li><a href="/wiki/Androgen" title="Androgen">Androgens</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>)</li> <li><a href="/wiki/Benzoylperoxide" class="mw-redirect" title="Benzoylperoxide">Benzoylperoxide</a></li> <li><a href="/wiki/Brimonidine" title="Brimonidine">Brimonidine</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Calcium_gluconate" title="Calcium gluconate">Calcium gluconate</a></li> <li><a href="/wiki/Collagen" title="Collagen">Collagen</a></li> <li><a href="/wiki/Crisaborole" title="Crisaborole">Crisaborole</a></li> <li><a href="/wiki/Cromoglicic_acid" title="Cromoglicic acid">Cromoglicic acid</a></li> <li><a href="/wiki/Delgocitinib" title="Delgocitinib">Delgocitinib</a></li> <li><a href="/wiki/Deoxycholic_acid" title="Deoxycholic acid">Deoxycholic acid</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></li> <li><a href="/wiki/Dupilumab" title="Dupilumab">Dupilumab</a></li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a> (e.g., <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>)</li> <li><a href="/wiki/Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a></li> <li><a href="/wiki/Glycopyrronium_tosylate" title="Glycopyrronium tosylate">Glycopyrronium tosylate</a></li> <li><a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">Hyaluronic acid</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Lebrikizumab" title="Lebrikizumab">Lebrikizumab</a></li> <li><a href="/wiki/Lokivetmab" title="Lokivetmab">Lokivetmab</a></li> <li><a href="/wiki/Medical_uses_of_magnesium_sulfate" title="Medical uses of magnesium sulfate">Magnesium sulfate</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a></li> <li><a href="/wiki/Nemolizumab" title="Nemolizumab">Nemolizumab</a></li> <li><a href="/wiki/Oclacitinib" title="Oclacitinib">Oclacitinib</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a></li> <li><a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">Pregnenolone acetate</a></li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>)</li> <li><a href="/wiki/Ruxolitinib" title="Ruxolitinib">Ruxolitinib</a></li> <li><a href="/wiki/Sofpironium_bromide" title="Sofpironium bromide">Sofpironium bromide</a></li> <li><a href="/wiki/Tiratricol" title="Tiratricol">Tiratricol</a></li> <li><a href="/wiki/Tralokinumab" title="Tralokinumab">Tralokinumab</a></li></ul> </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" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Androgens_and_antiandrogens491" style="padding:3px"><table class="nowraplinks 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:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgens_and_antiandrogens" title="Template talk:Androgens and antiandrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgens_and_antiandrogens" title="Special:EditPage/Template:Androgens and antiandrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgens_and_antiandrogens491" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen" title="Androgen">Androgens</a> and <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Androgen" title="Androgen">Androgens</a><br />(incl. <a href="/wiki/Anabolic%E2%80%93androgenic_steroid" class="mw-redirect" title="Anabolic–androgenic steroid"><abbr title="anabolic–androgenic steroid">AAS</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 anabolic–androgenic steroid</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:9em;;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> <a href="/wiki/Agonist" title="Agonist">agonists</a></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/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li> <li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a></li> <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> <li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone, DHEA)</a></li> <li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate (DHEA enanthate)</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate (DHEA sulfate)</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a><sup>#</sup></li> <li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a> (e.g., <a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">testosterone cypionate</a>, <a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">testosterone enanthate</a>, <a href="/wiki/Testosterone_propionate" title="Testosterone propionate">testosterone propionate</a>, <a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">testosterone undecanoate</a>, <a href="/wiki/Testosterone_ester_mixture" class="mw-redirect" title="Testosterone ester mixture">testosterone ester mixtures</a> (<a href="/wiki/Deposterona" class="mw-redirect" title="Deposterona">Deposterona</a>, <a href="/wiki/Omnadren" class="mw-redirect" title="Omnadren">Omnadren</a>, <a href="/wiki/Testosterone_propionate/testosterone_phenylpropionate/testosterone_isocaproate/testosterone_decanoate" title="Testosterone propionate/testosterone phenylpropionate/testosterone isocaproate/testosterone decanoate">Sustanon</a>, <a href="/wiki/Testoviron_depot" class="mw-redirect" title="Testoviron depot">Testoviron Depot</a>))</li></ul> <ul><li><i>Dihydrotestosterone derivatives:</i> <a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone (stanolone, dihydrotestosterone, DHT)</a></li> <li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Androstanolone esters</a></li> <li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li> <li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate (dromostanolone propionate)</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/Mesterolone" title="Mesterolone">Mesterolone</a></li> <li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate (methenolone acetate)</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate (methenolone enanthate)</a></li> <li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul> <ul><li><i>19-Nortestosterone derivatives:</i> <a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a></li> <li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li> <li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li> <li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)</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/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</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/Metandienone" title="Metandienone">Metandienone (methandienone, methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a></li> <li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</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> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></li> <li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></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 (thiomesterone)</a></li></ul> <ul><li><i>17α-Alkylated dihydrotestosterone derivatives:</i> <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</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/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/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol (propethandrol)</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-Ethynyltestosterone derivatives:</i> <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Progestin" class="mw-redirect" title="Progestin">Progestins</a> (e.g., <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone (ethynyltestosterone)</a>, <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a>, <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a>, <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone (norethindrone)</a>, <a href="/wiki/Lynestrenol" title="Lynestrenol">lynestrenol</a>, <a href="/wiki/Norgestrienone" title="Norgestrienone">norgestrienone</a>)</li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Progesterone derivatives:</i> <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></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/Antiestrogen" title="Antiestrogen">Antiestrogens</a> (e.g., <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>, <a href="/wiki/Clomifene" title="Clomifene">clomifene</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone">GnRH (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</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 luteinizing hormone</span>, <a href="/wiki/Human_chorionic_gonadotropin" title="Human chorionic gonadotropin"><abbr title="human chorionic gonadotropin">hCG</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 human chorionic gonadotropin</span>)</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/Antiandrogen" title="Antiandrogen">Antiandrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:9em;;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> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a></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/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+niraparib</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/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</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/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</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/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a class="mw-selflink selflink">Ketoconazole</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a><sup>†</sup></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Steroidogenesis<br />inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Epristeride" title="Epristeride">Epristeride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</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/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+niraparib</a></li> <li><a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a class="mw-selflink selflink">Ketoconazole</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a><sup>†</sup></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></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/D2_receptor" class="mw-redirect" title="D2 receptor">D<sub>2</sub> receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin_releaser" class="mw-redirect" title="Prolactin releaser">prolactin releasers</a>) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a> (e.g., <a href="/wiki/Bifluranol" title="Bifluranol">bifluranol</a>, <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>, <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, <a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">estradiol esters</a>, <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>, <a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">ethinylestradiol sulfonate</a>, <a href="/wiki/Paroxypropione" title="Paroxypropione">paroxypropione</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist">GnRH antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (incl., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Androstenedione immunogens:</i> <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_androgens/anabolic_steroids" class="mw-redirect" title="List of androgens/anabolic steroids">List of androgens/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" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Glucocorticoids_and_antiglucocorticoids_(D07,_H02)183" style="padding:3px"><table class="nowraplinks 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:Glucocorticoids_and_antiglucocorticoids" title="Template:Glucocorticoids and antiglucocorticoids"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glucocorticoids_and_antiglucocorticoids" title="Template talk:Glucocorticoids and antiglucocorticoids"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glucocorticoids_and_antiglucocorticoids" title="Special:EditPage/Template:Glucocorticoids and antiglucocorticoids"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glucocorticoids_and_antiglucocorticoids_(D07,_H02)183" style="font-size:114%;margin:0 4em"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids</a> and <a href="/wiki/Antiglucocorticoid" title="Antiglucocorticoid">antiglucocorticoids</a> (<a href="/wiki/ATC_code_D07" title="ATC code D07">D07</a>, <a href="/wiki/ATC_code_H02" title="ATC code H02">H02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Glucocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Natural_product" title="Natural product">Natural</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a> <ul><li><a href="/wiki/Cortisone_acetate" title="Cortisone acetate">Cortisone acetate</a></li></ul></li> <li><a href="/wiki/Cortodoxone" class="mw-redirect" title="Cortodoxone">Cortodoxone (cortexolone, 11-deoxycortisol)</a></li> <li><a href="/wiki/Desoxycortone" class="mw-redirect" title="Desoxycortone">Desoxycortone (deoxycortone, cortexone, 11-deoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/Hydrocortisone" title="Hydrocortisone">Hydrocortisone</a> (<a href="/wiki/Cortisol" title="Cortisol">cortisol</a>)<sup>#</sup> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Hydrocortisone_aceponate" title="Hydrocortisone aceponate">Hydrocortisone aceponate</a></li> <li><a href="/wiki/Prebediolone_acetate" title="Prebediolone acetate">Prebediolone acetate</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a> <ul><li><a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">Pregnenolone acetate</a></li> <li><a href="/wiki/Pregnenolone_succinate" title="Pregnenolone succinate">Pregnenolone succinate</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">Synthetic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Cortisol-like and related (16-unsubstituted):</i> <a href="/wiki/Chloroprednisone" title="Chloroprednisone">Chloroprednisone</a></li> <li><a href="/wiki/Cloprednol" title="Cloprednol">Cloprednol</a></li> <li><a href="/wiki/Difluprednate" title="Difluprednate">Difluprednate</a></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate (flurogestone acetate)</a></li> <li><a href="/wiki/Fluocinolone" title="Fluocinolone">Fluocinolone</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a> <ul><li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li></ul></li> <li><a href="/wiki/Fluperolone" title="Fluperolone">Fluperolone</a> <ul><li><a href="/wiki/Fluperolone_acetate" title="Fluperolone acetate">Fluperolone acetate</a></li></ul></li> <li><a href="/wiki/Fluprednisolone" title="Fluprednisolone">Fluprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Fluprednisolone_esters" title="List of corticosteroid esters">Fluprednisolone esters</a></li></ul></li> <li><a href="/wiki/Loteprednol" title="Loteprednol">Loteprednol</a> (<a href="/wiki/Loteprednol/tobramycin" title="Loteprednol/tobramycin">+tobramycin</a>)</li> <li><a href="/wiki/Medrysone" title="Medrysone">Medrysone</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Methylprednisolone_esters" title="List of corticosteroid esters">Methylprednisolone esters</a></li></ul></li> <li><a href="/wiki/Methylprednisolone_aceponate" title="Methylprednisolone aceponate">Methylprednisolone aceponate</a></li> <li><a href="/wiki/Prednicarbate" title="Prednicarbate">Prednicarbate</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a><sup>#</sup></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a></li> <li><a href="/wiki/Tixocortol" title="Tixocortol">Tixocortol</a> <ul><li><a href="/wiki/Tixocortol_pivalate" title="Tixocortol pivalate">Tixocortol pivalate</a></li></ul></li></ul> <ul><li><i>Methasones and related (16-substituted):</i> <a href="/wiki/Alclometasone" title="Alclometasone">Alclometasone</a></li> <li><a href="/wiki/Beclometasone" title="Beclometasone">Beclometasone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Beclometasone_esters" title="List of corticosteroid esters">Beclometasone esters</a></li></ul></li> <li><a href="/wiki/Betamethasone" title="Betamethasone">Betamethasone</a><sup>#</sup> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Betamethasone_esters" title="List of corticosteroid esters">Betamethasone esters</a></li></ul></li> <li><a href="/wiki/Clobetasol" title="Clobetasol">Clobetasol</a> <ul><li><a href="/wiki/Clobetasol_propionate" title="Clobetasol propionate">Clobetasol propionate</a></li></ul></li> <li><a href="/wiki/Clobetasone" title="Clobetasone">Clobetasone</a></li> <li><a href="/wiki/Clocortolone" title="Clocortolone">Clocortolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Clocortolone_esters" title="List of corticosteroid esters">Clocortolone esters</a></li></ul></li> <li><a href="/wiki/Cortivazol" title="Cortivazol">Cortivazol</a></li> <li><a href="/wiki/Desoximetasone" title="Desoximetasone">Desoximetasone</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a><sup>#</sup> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Dexamethasone_esters" title="List of corticosteroid esters">Dexamethasone esters</a></li></ul></li> <li><a href="/wiki/Diflorasone" title="Diflorasone">Diflorasone</a></li> <li><a href="/wiki/Diflucortolone" title="Diflucortolone">Diflucortolone</a> <ul><li><a href="/wiki/Diflucortolone_valerate" title="Diflucortolone valerate">Diflucortolone valerate</a></li></ul></li> <li><a href="/wiki/Fluclorolone" title="Fluclorolone">Fluclorolone</a></li> <li><a href="/wiki/Flumetasone" title="Flumetasone">Flumetasone</a></li> <li><a href="/wiki/Fluocortin" title="Fluocortin">Fluocortin</a></li> <li><a href="/wiki/Fluocortolone" title="Fluocortolone">Fluocortolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Fluocortolone_esters" title="List of corticosteroid esters">Fluocortolone esters</a></li></ul></li> <li><a href="/wiki/Fluprednidene_acetate" title="Fluprednidene acetate">Fluprednidene acetate</a></li> <li>Fluticasone <ul><li><a href="/wiki/Fluticasone_furoate" title="Fluticasone furoate">Fluticasone furoate</a></li> <li><a href="/wiki/Fluticasone_propionate" title="Fluticasone propionate">Fluticasone propionate</a></li></ul></li> <li><a href="/wiki/Halometasone" title="Halometasone">Halometasone</a></li> <li><a href="/wiki/Meprednisone" title="Meprednisone">Meprednisone</a></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a> <ul><li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li></ul></li> <li><a href="/wiki/Paramethasone" title="Paramethasone">Paramethasone</a></li> <li><a href="/wiki/Prednylidene" title="Prednylidene">Prednylidene</a></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Triamcinolone" title="Triamcinolone">Triamcinolone</a></li> <li><a href="/wiki/Ulobetasol" title="Ulobetasol">Ulobetasol (halobetasol)</a></li></ul> <ul><li><i>Cyclic ketals (16,17-cyclized):</i> <a href="/wiki/Amcinonide" title="Amcinonide">Amcinonide</a></li> <li><a href="/wiki/Budesonide" title="Budesonide">Budesonide</a></li> <li><a href="/wiki/Ciclesonide" title="Ciclesonide">Ciclesonide</a></li> <li><a href="/wiki/Deflazacort" title="Deflazacort">Deflazacort</a></li> <li><a href="/wiki/Desonide" title="Desonide">Desonide</a></li> <li><a href="/wiki/Fluclorolone_acetonide" title="Fluclorolone acetonide">Fluclorolone acetonide (flucloronide)</a></li> <li><a href="/wiki/Fludroxycortide" title="Fludroxycortide">Fludroxycortide (flurandrenolone, flurandrenolide)</a></li> <li><a href="/wiki/Flunisolide" title="Flunisolide">Flunisolide</a></li> <li><a href="/wiki/Fluocinolone_acetonide" title="Fluocinolone acetonide">Fluocinolone acetonide</a></li> <li><a href="/wiki/Fluocinonide" title="Fluocinonide">Fluocinonide</a></li> <li><a href="/wiki/Formocortal" title="Formocortal">Formocortal (fluoroformylone)</a></li> <li><a href="/wiki/Halcinonide" title="Halcinonide">Halcinonide</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Triamcinolone_acetonide_esters" title="List of corticosteroid esters">Triamcinolone acetonide esters</a></li></ul></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/Antiglucocorticoid" title="Antiglucocorticoid">Antiglucocorticoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antagonists:</i> <a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a class="mw-selflink selflink">Ketoconazole</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Steroidogenesis_modulator" class="mw-redirect" title="Steroidogenesis modulator">Synthesis modifiers</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetoxolone" title="Acetoxolone">Acetoxolone</a></li> <li><a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Carbenoxolone" title="Carbenoxolone">Carbenoxolone</a></li> <li><a href="/wiki/Enoxolone" title="Enoxolone">Enoxolone</a></li> <li><a class="mw-selflink selflink">Ketoconazole</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mitotane" title="Mitotane">Mitotane</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</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"><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> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Glucocorticoid_receptor_modulators" title="Template:Glucocorticoid receptor modulators">Glucocorticoid receptor modulators</a></dd> <dd><a href="/wiki/Template:Mineralocorticoids_and_antimineralocorticoids" title="Template:Mineralocorticoids and antimineralocorticoids">Mineralocorticoids and antimineralocorticoids</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Pharmacodynamics105" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#e8e8ff;background:#ccccff"><div id="Pharmacodynamics105" style="font-size:114%;margin:0 4em"><a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">Pharmacodynamics</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;font-size:114%"><div style="padding:0px"> <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 href="/wiki/Cimetidine" title="Cimetidine">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 class="mw-selflink selflink">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="Glucocorticoid_receptor_modulators752" 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:Glucocorticoid_receptor_modulators" title="Template:Glucocorticoid receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Glucocorticoid_receptor_modulators" title="Template talk:Glucocorticoid receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Glucocorticoid_receptor_modulators" title="Special:EditPage/Template:Glucocorticoid receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Glucocorticoid_receptor_modulators752" style="font-size:114%;margin:0 4em"><a href="/wiki/Glucocorticoid_receptor" title="Glucocorticoid receptor">Glucocorticoid 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/Glucocorticoid_receptor" title="Glucocorticoid receptor"><abbr title="Glucocorticoid receptor">GR</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 Glucocorticoid 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"><a href="/wiki/Glucocorticoid" title="Glucocorticoid">Agonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Cortisol-like and related (16-unsubstituted):</i> <a href="/wiki/Tetrahydrocorticosterone" title="Tetrahydrocorticosterone">3α,5α-Tetrahydrocorticosterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydrocorticosterone" title="5α-Dihydrocorticosterone">5α-Dihydrocorticosterone</a></li> <li><a href="/wiki/9%CE%B1-Fluorocortisone" title="9α-Fluorocortisone">9α-Fluorocortisone (alfluorone)</a></li> <li><a href="/wiki/11-Dehydrocorticosterone" title="11-Dehydrocorticosterone">11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)</a> <ul><li><a href="/w/index.php?title=11-Dehydrocorticosterone_acetate&action=edit&redlink=1" class="new" title="11-Dehydrocorticosterone acetate (page does not exist)">11-Dehydrocorticosterone acetate</a></li></ul></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Desoxycortone_esters" title="List of corticosteroid esters">Desoxycortone esters</a></li></ul></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (cortodoxone, cortexolone)</a> <ul><li><a href="/wiki/Cortifen" title="Cortifen">Cortifen (cortiphen, kortifen)</a></li> <li><a href="/w/index.php?title=Cortodoxone_acetate&action=edit&redlink=1" class="new" title="Cortodoxone acetate (page does not exist)">Cortodoxone acetate</a></li></ul></li> <li><a href="/wiki/21-Deoxycortisol" title="21-Deoxycortisol">21-Deoxycortisol</a></li> <li><a href="/wiki/%CE%947-Prednisolone" title="Δ7-Prednisolone">Δ<sup>7</sup>-Prednisolone</a> <ul><li><a href="/w/index.php?title=%CE%947-Prednisolone_21-acetate&action=edit&redlink=1" class="new" title="Δ7-Prednisolone 21-acetate (page does not exist)">Δ<sup>7</sup>-Prednisolone 21-acetate</a></li></ul></li> <li><a href="/wiki/Amebucort" title="Amebucort">Amebucort</a></li> <li><a href="/wiki/Chloroprednisone" title="Chloroprednisone">Chloroprednisone</a> <ul><li><a href="/wiki/Chloroprednisone_acetate" title="Chloroprednisone acetate">Chloroprednisone acetate</a></li></ul></li> <li><a href="/wiki/Cloprednol" title="Cloprednol">Cloprednol</a> <ul><li><a href="/w/index.php?title=Cloprednol_acetate&action=edit&redlink=1" class="new" title="Cloprednol acetate (page does not exist)">Cloprednol acetate</a></li></ul></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a> <ul><li><a href="/w/index.php?title=Corticosterone_acetate&action=edit&redlink=1" class="new" title="Corticosterone acetate (page does not exist)">Corticosterone acetate</a></li> <li><a href="/w/index.php?title=Corticosterone_benzoate&action=edit&redlink=1" class="new" title="Corticosterone benzoate (page does not exist)">Corticosterone benzoate</a></li></ul></li> <li><a href="/wiki/Cortisol" title="Cortisol">Cortisol</a> (<a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>) <ul><li><a href="/wiki/Benzodrocortisone" title="Benzodrocortisone">Benzodrocortisone (hydrocortisone benzoate)</a></li> <li><a href="/wiki/Hydrocortamate" title="Hydrocortamate">Hydrocortamate (hydrocortisone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Hydrocortisone_esters" title="List of corticosteroid esters">Hydrocortisone esters</a></li></ul></li> <li><a href="/wiki/Cortisone" title="Cortisone">Cortisone</a> <ul><li><a href="/wiki/Cortisone_acetate" title="Cortisone acetate">Cortisone acetate</a></li></ul></li> <li><a href="/wiki/Deprodone" title="Deprodone">Deprodone</a> <ul><li><a href="/w/index.php?title=Deprodone_propionate&action=edit&redlink=1" class="new" title="Deprodone propionate (page does not exist)">Deprodone propionate</a></li></ul></li> <li><a href="/wiki/Dichlorisone" title="Dichlorisone">Dichlorisone</a> <ul><li><a href="/w/index.php?title=Dichlorisone_acetate&action=edit&redlink=1" class="new" title="Dichlorisone acetate (page does not exist)">Dichlorisone acetate</a></li> <li><a href="/w/index.php?title=Dichlorisone_diacetate&action=edit&redlink=1" class="new" title="Dichlorisone diacetate (page does not exist)">Dichlorisone diacetate</a></li></ul></li> <li><a href="/wiki/Difluprednate" title="Difluprednate">Difluprednate</a></li> <li><a href="/wiki/Endrisone" title="Endrisone">Endrisone (endrysone)</a></li> <li><a href="/wiki/Etiprednol" title="Etiprednol">Etiprednol</a> <ul><li><a href="/w/index.php?title=Etiprednol_dicloacetate&action=edit&redlink=1" class="new" title="Etiprednol dicloacetate (page does not exist)">Etiprednol dicloacetate (etiprednol dichloroacetate)</a></li></ul></li> <li><a href="/wiki/Fludrocortisone" title="Fludrocortisone">Fludrocortisone (fludrocortone)</a> <ul><li><a href="/wiki/Fludrocortisone_acetate" class="mw-redirect" title="Fludrocortisone acetate">Fludrocortisone acetate</a></li></ul></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a> <ul><li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li></ul></li> <li><a href="/wiki/Fluperolone" title="Fluperolone">Fluperolone</a> <ul><li><a href="/wiki/Fluperolone_acetate" title="Fluperolone acetate">Fluperolone acetate</a></li></ul></li> <li><a href="/wiki/Fluprednisolone" title="Fluprednisolone">Fluprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Fluprednisolone_esters" title="List of corticosteroid esters">Fluprednisolone esters</a></li></ul></li> <li><a href="/wiki/Halopredone" title="Halopredone">Halopredone</a> <ul><li><a href="/w/index.php?title=Halopredone_acetate&action=edit&redlink=1" class="new" title="Halopredone acetate (page does not exist)">Halopredone acetate (halopredone diacetate)</a></li></ul></li> <li><a href="/wiki/Isoflupredone" title="Isoflupredone">Isoflupredone (9α-fluoroprednisolone)</a> <ul><li><a href="/w/index.php?title=Isoflupredone_acetate&action=edit&redlink=1" class="new" title="Isoflupredone acetate (page does not exist)">Isoflupredone acetate</a></li></ul></li> <li><a href="/wiki/Loteprednol" title="Loteprednol">Loteprednol</a></li> <li><a href="/wiki/Mazipredone" title="Mazipredone">Mazipredone (depersolone)</a></li> <li><a href="/wiki/Medrysone" title="Medrysone">Medrysone</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Methylprednisolone_esters" title="List of corticosteroid esters">Methylprednisolone esters</a></li></ul></li> <li><a href="/wiki/Prebediolone" class="mw-redirect" title="Prebediolone">Prebediolone</a> <ul><li><a href="/wiki/Prebediolone_acetate" title="Prebediolone acetate">Prebediolone acetate</a></li></ul></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a> <ul><li><a href="/wiki/Prednazate" title="Prednazate">Prednazate</a></li> <li><a href="/wiki/Prednazoline" title="Prednazoline">Prednazoline</a></li> <li><a href="/wiki/Prednicarbate" title="Prednicarbate">Prednicarbate (prednisolone ethylcarbonate propionate)</a></li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Prednisolamate" title="Prednisolamate">Prednisolamate (prednisolone diethylaminoacetate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Prednisolone_esters" title="List of corticosteroid esters">Prednisolone esters</a></li></ul></li> <li><a href="/wiki/Prednisone" title="Prednisone">Prednisone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Prednisone_esters" title="List of corticosteroid esters">Prednisone esters</a></li></ul></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a> <ul><li><a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">Pregnenolone acetate</a></li> <li><a href="/wiki/Pregnenolone_succinate" title="Pregnenolone succinate">Pregnenolone succinate (pregnenolone hemisuccinate)</a></li></ul></li> <li><a href="/wiki/Resocortol" title="Resocortol">Resocortol</a></li> <li><a href="/wiki/Tipredane" title="Tipredane">Tipredane</a></li> <li><a href="/wiki/Tixocortol" title="Tixocortol">Tixocortol</a> <ul><li><a href="/wiki/Butixocort" title="Butixocort">Butixocort (tixocortol butyrate)</a> <ul><li><a href="/w/index.php?title=Butixocort_propionate&action=edit&redlink=1" class="new" title="Butixocort propionate (page does not exist)">Butixocort propionate</a></li></ul></li> <li><a href="/wiki/Tixocortol_pivalate" title="Tixocortol pivalate">Tixocortol pivalate</a></li></ul></li></ul> <ul><li><i>Methasones and related (16-substituted):</i> <a href="/wiki/16%CE%B1-Methyl-11-oxoprednisolone" title="16α-Methyl-11-oxoprednisolone">16α-Methyl-11-oxoprednisolone</a></li> <li><a href="/wiki/Alclometasone" title="Alclometasone">Alclometasone</a> <ul><li><a href="/wiki/Alclometasone_dipropionate" title="Alclometasone dipropionate">Alclometasone dipropionate</a></li></ul></li> <li><a href="/wiki/Amelometasone" title="Amelometasone">Amelometasone</a></li> <li><a href="/wiki/Beclometasone" title="Beclometasone">Beclometasone (beclomethasone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Beclometasone_esters" title="List of corticosteroid esters">Beclometasone esters</a></li></ul></li> <li><a href="/wiki/Betamethasone" title="Betamethasone">Betamethasone (betametasone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Betamethasone_esters" title="List of corticosteroid esters">Betamethasone esters</a></li> <li><a href="/wiki/Cortobenzolone" title="Cortobenzolone">Cortobenzolone (betamethasone salicylate)</a></li></ul></li> <li><a href="/wiki/Ciclometasone" title="Ciclometasone">Ciclometasone (ciclomethasone, cyclomethasone)</a></li> <li><a href="/wiki/Clobetasol" title="Clobetasol">Clobetasol</a> <ul><li><a href="/wiki/Clobetasol_propionate" title="Clobetasol propionate">Clobetasol propionate</a></li></ul></li> <li><a href="/wiki/Clobetasone" title="Clobetasone">Clobetasone</a> <ul><li><a href="/wiki/Clobetasone_butyrate" title="Clobetasone butyrate">Clobetasone butyrate</a></li></ul></li> <li><a href="/wiki/Clocortolone" title="Clocortolone">Clocortolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Clocortolone_esters" title="List of corticosteroid esters">Clocortolone esters</a></li></ul></li> <li><a href="/wiki/Cloticasone" title="Cloticasone">Cloticasone</a> <ul><li><a href="/w/index.php?title=Cloticasone_propionate&action=edit&redlink=1" class="new" title="Cloticasone propionate (page does not exist)">Cloticasone propionate</a></li></ul></li> <li><a href="/wiki/Cormetasone" title="Cormetasone">Cormetasone (cormethasone)</a> <ul><li><a href="/w/index.php?title=Cormetasone_acetate&action=edit&redlink=1" class="new" title="Cormetasone acetate (page does not exist)">Cormetasone acetate</a></li></ul></li> <li><a href="/wiki/Descinolone" title="Descinolone">Descinolone</a></li> <li><a href="/wiki/Desoximetasone" title="Desoximetasone">Desoximetasone (desoxymethasone)</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone (dexametasone)</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Dexamethasone_esters" title="List of corticosteroid esters">Dexamethasone esters</a></li></ul></li> <li><a href="/wiki/Diflorasone" title="Diflorasone">Diflorasone</a> <ul><li><a href="/wiki/Diflorasone_diacetate" title="Diflorasone diacetate">Diflorasone diacetate</a></li></ul></li> <li><a href="/wiki/Diflucortolone" title="Diflucortolone">Diflucortolone</a> <ul><li><a href="/w/index.php?title=Diflucortolone_pivalate&action=edit&redlink=1" class="new" title="Diflucortolone pivalate (page does not exist)">Diflucortolone pivalate</a></li> <li><a href="/wiki/Diflucortolone_valerate" title="Diflucortolone valerate">Diflucortolone valerate</a></li></ul></li> <li><a href="/wiki/Dimesone" title="Dimesone">Dimesone</a> <ul><li><a href="/w/index.php?title=Dimesone_acetate&action=edit&redlink=1" class="new" title="Dimesone acetate (page does not exist)">Dimesone acetate</a></li></ul></li> <li><a href="/wiki/Doxibetasol" title="Doxibetasol">Doxibetasol (doxybetasol)</a></li> <li><a href="/wiki/Fluclorolone" title="Fluclorolone">Fluclorolone</a></li> <li><a href="/wiki/Flumetasone" title="Flumetasone">Flumetasone (flumethasone)</a> <ul><li><a href="/w/index.php?title=Flumetasone_acetate&action=edit&redlink=1" class="new" title="Flumetasone acetate (page does not exist)">Flumetasone acetate</a></li> <li><a href="/wiki/Flumetasone_pivalate" title="Flumetasone pivalate">Flumetasone pivalate</a></li></ul></li> <li><a href="/wiki/Fluocinolone" title="Fluocinolone">Fluocinolone</a></li> <li><a href="/wiki/Fluocortin" title="Fluocortin">Fluocortin</a> <ul><li><a href="/wiki/Fluocortin_butyl" title="Fluocortin butyl">Fluocortin butyl (fluocortin butylate)</a></li></ul></li> <li><a href="/wiki/Fluocortolone" title="Fluocortolone">Fluocortolone</a> <ul><li><a href="/wiki/List_of_corticosteroid_esters#Fluocortolone_esters" title="List of corticosteroid esters">Fluocortolone esters</a></li></ul></li> <li><a href="/wiki/Fluprednidene" title="Fluprednidene">Fluprednidene (fluprednylidene)</a> <ul><li><a href="/wiki/Fluprednidene_acetate" title="Fluprednidene acetate">Fluprednidene acetate</a></li></ul></li> <li>Fluticasone <ul><li><a href="/wiki/Fluticasone_furoate" title="Fluticasone furoate">Fluticasone furoate</a></li> <li><a href="/wiki/Fluticasone_propionate" title="Fluticasone propionate">Fluticasone propionate</a></li></ul></li> <li><a href="/wiki/Halocortolone" title="Halocortolone">Halocortolone</a></li> <li><a href="/wiki/Halometasone" title="Halometasone">Halometasone</a></li> <li><a href="/wiki/Icometasone" title="Icometasone">Icometasone</a> <ul><li><a href="/w/index.php?title=Icometasone_enbutate&action=edit&redlink=1" class="new" title="Icometasone enbutate (page does not exist)">Icometasone enbutate (icometasone butyrate acetate)</a></li></ul></li> <li><a href="/wiki/Isoprednidene" title="Isoprednidene">Isoprednidene</a></li> <li><a href="/wiki/Locicortolone" title="Locicortolone">Locicortolone (locicortone)</a> <ul><li><a href="/w/index.php?title=Locicortolone_dicibate&action=edit&redlink=1" class="new" title="Locicortolone dicibate (page does not exist)">Locicortolone dicibate (locicortone dicibate)</a></li></ul></li> <li><a href="/wiki/Meclorisone" title="Meclorisone">Meclorisone</a> <ul><li><a href="/w/index.php?title=Meclorisone_dibutyrate&action=edit&redlink=1" class="new" title="Meclorisone dibutyrate (page does not exist)">Meclorisone dibutyrate</a></li></ul></li> <li><a href="/wiki/Meprednisone" title="Meprednisone">Meprednisone (methylprednisone)</a> <ul><li><a href="/w/index.php?title=Meprednisone_acetate&action=edit&redlink=1" class="new" title="Meprednisone acetate (page does not exist)">Meprednisone acetate</a></li> <li><a href="/w/index.php?title=Meprednisone_hydrogen_succinate&action=edit&redlink=1" class="new" title="Meprednisone hydrogen succinate (page does not exist)">Meprednisone hydrogen succinate (methylprednisone hemisuccinate)</a></li></ul></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a> <ul><li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</a></li></ul></li> <li><a href="/wiki/Paramethasone" title="Paramethasone">Paramethasone</a> <ul><li><a href="/wiki/Paramethasone_acetate" title="Paramethasone acetate">Paramethasone acetate</a></li> <li><a href="/w/index.php?title=Paramethasone_disodium_phosphate&action=edit&redlink=1" class="new" title="Paramethasone disodium phosphate (page does not exist)">Paramethasone disodium phosphate</a></li> <li><a href="/w/index.php?title=Paramethasone_phosphate&action=edit&redlink=1" class="new" title="Paramethasone phosphate (page does not exist)">Paramethasone phosphate</a></li></ul></li> <li><a href="/wiki/Prednylidene" title="Prednylidene">Prednylidene</a> <ul><li><a href="/w/index.php?title=Prednylidene_diethylaminoacetate&action=edit&redlink=1" class="new" title="Prednylidene diethylaminoacetate (page does not exist)">Prednylidene diethylaminoacetate</a></li></ul></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Ticabesone" title="Ticabesone">Ticabesone</a> <ul><li><a href="/w/index.php?title=Ticabesone_propionate&action=edit&redlink=1" class="new" title="Ticabesone propionate (page does not exist)">Ticabesone propionate</a></li></ul></li> <li><a href="/wiki/Timobesone" title="Timobesone">Timobesone</a> <ul><li><a href="/w/index.php?title=Timobesone_acetate&action=edit&redlink=1" class="new" title="Timobesone acetate (page does not exist)">Timobesone acetate</a></li></ul></li> <li><a href="/wiki/Triamcinolone" title="Triamcinolone">Triamcinolone</a> <ul><li><a href="/wiki/Triamcinolone_diacetate" title="Triamcinolone diacetate">Triamcinolone diacetate</a></li></ul></li> <li><a href="/wiki/Ulobetasol" title="Ulobetasol">Ulobetasol (halobetasol)</a> <ul><li><a href="/wiki/Ulobetasol_propionate" title="Ulobetasol propionate">Ulobetasol propionate</a></li></ul></li> <li><a href="/wiki/Vamorolone" title="Vamorolone">Vamorolone</a></li></ul> <ul><li><i>Cyclic ketals (16,17-cyclized):</i> <a href="/wiki/Acrocinonide" title="Acrocinonide">Acrocinonide (triamcinolone acroleinide)</a></li> <li><a href="/wiki/Amcinafal" title="Amcinafal">Amcinafal (triamcinolone pentanonide)</a></li> <li><a href="/wiki/Amcinafide" title="Amcinafide">Amcinafide (triamcinolone acetophenide)</a></li> <li><a href="/wiki/Amcinonide" title="Amcinonide">Amcinonide (triamcinolone acetate cyclopentanonide)</a></li> <li><a href="/wiki/Budesonide" title="Budesonide">Budesonide</a></li> <li><a href="/wiki/Ciclesonide" title="Ciclesonide">Ciclesonide</a></li> <li><a href="/wiki/Cicortonide" title="Cicortonide">Cicortonide</a></li> <li><a href="/wiki/Deflazacort" title="Deflazacort">Deflazacort (azacort)</a></li> <li><a href="/wiki/Descinolone_acetonide" title="Descinolone acetonide">Descinolone acetonide</a></li> <li><a href="/wiki/Desonide" title="Desonide">Desonide (hydroxyprednisolone acetonide)</a> <ul><li><a href="/w/index.php?title=Desonide_disodium_phosphate&action=edit&redlink=1" class="new" title="Desonide disodium phosphate (page does not exist)">Desonide disodium phosphate</a></li> <li><a href="/w/index.php?title=Desonide_pivalate&action=edit&redlink=1" class="new" title="Desonide pivalate (page does not exist)">Desonide pivalate</a></li></ul></li> <li><a href="/wiki/Dexbudesonide" title="Dexbudesonide">Dexbudesonide</a></li> <li><a href="/wiki/Drocinonide" title="Drocinonide">Drocinonide</a> <ul><li><a href="/w/index.php?title=Drocinonide_phosphate&action=edit&redlink=1" class="new" title="Drocinonide phosphate (page does not exist)">Drocinonide phosphate</a></li></ul></li> <li><a href="/wiki/Fluazacort" title="Fluazacort">Fluazacort</a></li> <li><a href="/wiki/Fluclorolone_acetonide" title="Fluclorolone acetonide">Fluclorolone acetonide (flucloronide)</a></li> <li><a href="/wiki/Fludroxycortide" title="Fludroxycortide">Fludroxycortide (flurandrenolone, flurandrenolide)</a></li> <li><a href="/wiki/Flumoxonide" title="Flumoxonide">Flumoxonide</a></li> <li><a href="/wiki/Flunisolide" title="Flunisolide">Flunisolide</a> <ul><li><a href="/w/index.php?title=Flunisolide_acetate&action=edit&redlink=1" class="new" title="Flunisolide acetate (page does not exist)">Flunisolide acetate</a></li></ul></li> <li><a href="/wiki/Fluocinolone_acetonide" title="Fluocinolone acetonide">Fluocinolone acetonide</a> <ul><li><a href="/wiki/Ciprocinonide" title="Ciprocinonide">Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate)</a></li> <li><a href="/wiki/Fluocinonide" title="Fluocinonide">Fluocinonide (fluocinolide, fluocinolone acetonide acetate)</a></li> <li><a href="/wiki/Procinonide" title="Procinonide">Procinonide (fluocinolone acetonide propionate)</a></li></ul></li> <li><a href="/wiki/Formocortal" title="Formocortal">Formocortal</a></li> <li><a href="/wiki/Halcinonide" title="Halcinonide">Halcinonide</a></li> <li><a href="/wiki/Itrocinonide" title="Itrocinonide">Itrocinonide</a></li> <li><a href="/wiki/Rofleponide" title="Rofleponide">Rofleponide</a> <ul><li><a href="/wiki/Rofleponide_palmitate" class="mw-redirect" title="Rofleponide palmitate">Rofleponide palmitate</a></li></ul></li> <li><a href="/wiki/Tralonide" title="Tralonide">Tralonide</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a> <ul><li><a href="/wiki/Flupamesone" title="Flupamesone">Flupamesone (triamcinolone acetonide metembonate)</a></li> <li><a href="/wiki/List_of_corticosteroid_esters#Triamcinolone_acetonide_esters" title="List of corticosteroid esters">Triamcinolone acetonide esters</a></li></ul></li> <li><a href="/wiki/Triamcinolone_aminobenzal_benzamidoisobutyrate" title="Triamcinolone aminobenzal benzamidoisobutyrate">Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB)</a></li> <li><a href="/wiki/Triclonide" title="Triclonide">Triclonide</a></li></ul> <ul><li><i>Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids):</i> <a href="/wiki/Cortisuzol" title="Cortisuzol">Cortisuzol</a></li> <li><a href="/wiki/Cortivazol" title="Cortivazol">Cortivazol</a></li> <li><a href="/wiki/Domoprednate" title="Domoprednate">Domoprednate</a></li> <li><a href="/wiki/Naflocort" title="Naflocort">Naflocort</a></li> <li><a href="/wiki/Nicocortonide" title="Nicocortonide">Nicocortonide</a> <ul><li><a href="/w/index.php?title=Nicocortonide_acetate&action=edit&redlink=1" class="new" title="Nicocortonide acetate (page does not exist)">Nicocortonide acetate</a></li></ul></li> <li><a href="/wiki/Nivacortol" title="Nivacortol">Nivacortol (nivazol)</a></li> <li><a href="/wiki/Oxisopred" title="Oxisopred">Oxisopred</a></li> <li><a href="/w/index.php?title=RU-26988&action=edit&redlink=1" class="new" title="RU-26988 (page does not exist)">RU-26988</a></li> <li><a href="/wiki/RU-28362" title="RU-28362">RU-28362</a></li></ul> <ul><li><i>Non-corticosteroids with some glucocorticoid activity:</i> <a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Bromoketoprogesterone" title="Bromoketoprogesterone">Bromoketoprogesterone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</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/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Flugestone" title="Flugestone">Flugestone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate (flurogestone acetate)</a></li> <li><a href="/wiki/Fluoromedroxyprogesterone_acetate" title="Fluoromedroxyprogesterone acetate">Fluoromedroxyprogesterone acetate</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</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> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Segesterone_acetate" title="Segesterone acetate">Segesterone acetate (nestorone)</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li></ul> <ul><li><i>Nonsteroidal glucocorticoids:</i> <a href="/wiki/AZD-5423" title="AZD-5423">AZD-5423</a></li> <li><a href="/w/index.php?title=GSK-9027&action=edit&redlink=1" class="new" title="GSK-9027 (page does not exist)">GSK-9027</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed<br />(<a href="/wiki/Selective_glucocorticoid_receptor_agonists" class="mw-redirect" title="Selective glucocorticoid receptor agonists"><abbr title="Selective glucocorticoid receptor agonists">SEGRMs</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 glucocorticoid receptor agonists</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dagrocorat" title="Dagrocorat">Dagrocorat</a></li> <li><a href="/wiki/Fosdagrocorat" title="Fosdagrocorat">Fosdagrocorat</a></li> <li><a href="/wiki/Mapracorat" title="Mapracorat">Mapracorat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Antiglucocorticoid" title="Antiglucocorticoid">Antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Asoprisnil" title="Asoprisnil">Asoprisnil</a></li> <li><a href="/wiki/Asoprisnil_ecamate" title="Asoprisnil ecamate">Asoprisnil ecamate</a></li> <li><a href="/w/index.php?title=C108297&action=edit&redlink=1" class="new" title="C108297 (page does not exist)">C108297</a></li> <li><a href="/w/index.php?title=C113176&action=edit&redlink=1" class="new" title="C113176 (page does not exist)">C113176</a></li> <li><a href="/w/index.php?title=CORT-108297&action=edit&redlink=1" class="new" title="CORT-108297 (page does not exist)">CORT-108297</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/w/index.php?title=Dazucorilant&action=edit&redlink=1" class="new" title="Dazucorilant (page does not exist)">Dazucorilant</a></li> <li><a href="/w/index.php?title=Exicorilant&action=edit&redlink=1" class="new" title="Exicorilant (page does not exist)">Exicorilant (CORT-125281)</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a class="mw-selflink selflink">Ketoconazole</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/w/index.php?title=LLY-2707&action=edit&redlink=1" class="new" title="LLY-2707 (page does not exist)">LLY-2707</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">Miconazole</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/wiki/Miricorilant" title="Miricorilant">Miricorilant (CORT-118335)</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-34116&action=edit&redlink=1" class="new" title="ORG-34116 (page does not exist)">ORG-34116</a></li> <li><a href="/w/index.php?title=ORG-34517&action=edit&redlink=1" class="new" title="ORG-34517 (page does not exist)">ORG-34517 (SCH-900636)</a></li> <li><a href="/w/index.php?title=Org_34850&action=edit&redlink=1" class="new" title="Org 34850 (page does not exist)">ORG-34850</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Relacorilant" title="Relacorilant">Relacorilant (CORT-125134)</a></li> <li><a href="/wiki/RTI_3021%E2%80%93012" class="mw-redirect" title="RTI 3021–012">RTI 3021–012</a></li> <li><a href="/w/index.php?title=RTI_3021%E2%80%93022&action=edit&redlink=1" class="new" title="RTI 3021–022 (page does not exist)">RTI 3021–022</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/w/index.php?title=Zavacorilant&action=edit&redlink=1" class="new" title="Zavacorilant (page does not exist)">Zavacorilant</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antisense oligonucleotides:</i> <a href="/wiki/IONIS-GCCRRx" title="IONIS-GCCRRx">IONIS-GCCR<sub>Rx</sub> (ISIS-426115)</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:Glucocorticoids_and_antiglucocorticoids" title="Template:Glucocorticoids and antiglucocorticoids">Glucocorticoids and antiglucocorticoids</a></dd> <dd><a href="/wiki/Template:Mineralocorticoid_receptor_modulators" title="Template:Mineralocorticoid receptor modulators">Mineralocorticoid receptor modulators</a></dd> <dd><a href="/wiki/List_of_corticosteroids" title="List of corticosteroids">List of corticosteroids</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="Ion_channel_modulators357" style="padding:3px"><table class="nowraplinks 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:Ion_channel_modulators" title="Template:Ion channel modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Ion_channel_modulators" title="Template talk:Ion channel modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Ion_channel_modulators" title="Special:EditPage/Template:Ion channel modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Ion_channel_modulators357" style="font-size:114%;margin:0 4em"><a href="/wiki/Channel_modulator" title="Channel modulator">Ion channel modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Calcium_channel" title="Calcium channel">Calcium</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="VDCCsTooltip_Voltage-dependent_calcium_channels424" scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Voltage-dependent_calcium_channels" class="mw-redirect" title="Voltage-dependent calcium channels"><abbr title="Voltage-dependent calcium channels">VDCCs</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 Voltage-dependent calcium channels</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/L-type_calcium_channel" title="L-type calcium channel">L-type-selective</a>:</b> <i><a href="/wiki/Dihydropyridine" class="mw-redirect" title="Dihydropyridine">Dihydropyridines</a>:</i> <a href="/wiki/Amlodipine" title="Amlodipine">Amlodipine</a></li> <li><a href="/wiki/Aranidipine" title="Aranidipine">Aranidipine</a></li> <li><a href="/wiki/Azelnidipine" title="Azelnidipine">Azelnidipine</a></li> <li><a href="/wiki/Barnidipine" title="Barnidipine">Barnidipine</a></li> <li><a href="/wiki/Clevidipine" title="Clevidipine">Clevidipine</a></li> <li><a href="/w/index.php?title=Cronidipine&action=edit&redlink=1" class="new" title="Cronidipine (page does not exist)">Cronidipine</a></li> <li><a href="/wiki/Darodipine" title="Darodipine">Darodipine</a></li> <li><a href="/w/index.php?title=Dexniguldipine&action=edit&redlink=1" class="new" title="Dexniguldipine (page does not exist)">Dexniguldipine</a></li> <li><a href="/w/index.php?title=Elgodipine&action=edit&redlink=1" class="new" title="Elgodipine (page does not exist)">Elgodipine</a></li> <li><a href="/w/index.php?title=Elnadipine&action=edit&redlink=1" class="new" title="Elnadipine (page does not exist)">Elnadipine</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/w/index.php?title=Flordipine&action=edit&redlink=1" class="new" title="Flordipine (page does not exist)">Flordipine</a></li> <li><a href="/w/index.php?title=Furnidipine&action=edit&redlink=1" class="new" title="Furnidipine (page does not exist)">Furnidipine</a></li> <li><a href="/w/index.php?title=Iganidipine&action=edit&redlink=1" class="new" title="Iganidipine (page does not exist)">Iganidipine</a></li> <li><a href="/wiki/Isradipine" title="Isradipine">Isradipine</a></li> <li><a href="/wiki/Lacidipine" title="Lacidipine">Lacidipine</a></li> <li><a href="/w/index.php?title=Lemildipine&action=edit&redlink=1" class="new" title="Lemildipine (page does not exist)">Lemildipine</a></li> <li><a href="/wiki/Lercanidipine" title="Lercanidipine">Lercanidipine</a></li> <li><a href="/wiki/Levamlodipine" title="Levamlodipine">Levamlodipine</a></li> <li><a href="/w/index.php?title=Levniguldipine&action=edit&redlink=1" class="new" title="Levniguldipine (page does not exist)">Levniguldipine</a></li> <li><a href="/wiki/Manidipine" title="Manidipine">Manidipine</a></li> <li><a href="/wiki/Barnidipine" title="Barnidipine">Mepirodipine</a></li> <li><a href="/w/index.php?title=Mesudipine&action=edit&redlink=1" class="new" title="Mesudipine (page does not exist)">Mesudipine</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Niguldipine" title="Niguldipine">Niguldipine</a></li> <li><a href="/wiki/Niludipine" title="Niludipine">Niludipine</a></li> <li><a href="/wiki/Nilvadipine" title="Nilvadipine">Nilvadipine</a></li> <li><a href="/wiki/Nimodipine" title="Nimodipine">Nimodipine</a></li> <li><a href="/wiki/Nisoldipine" title="Nisoldipine">Nisoldipine</a></li> <li><a href="/wiki/Nitrendipine" title="Nitrendipine">Nitrendipine</a></li> <li><a href="/w/index.php?title=Olradipine&action=edit&redlink=1" class="new" title="Olradipine (page does not exist)">Olradipine</a></li> <li><a href="/wiki/Oxodipine" title="Oxodipine">Oxodipine</a></li> <li><a href="/w/index.php?title=Palonidipine&action=edit&redlink=1" class="new" title="Palonidipine (page does not exist)">Palonidipine</a></li> <li><a href="/wiki/Pranidipine" title="Pranidipine">Pranidipine</a></li> <li><a href="/wiki/Riodipine" title="Riodipine">Ryodipine (riodipine)</a></li> <li><a href="/w/index.php?title=Sagandipine&action=edit&redlink=1" class="new" title="Sagandipine (page does not exist)">Sagandipine</a></li> <li><a href="/w/index.php?title=Sornidipine&action=edit&redlink=1" class="new" title="Sornidipine (page does not exist)">Sornidipine</a></li> <li><a href="/w/index.php?title=Teludipine&action=edit&redlink=1" class="new" title="Teludipine (page does not exist)">Teludipine</a></li> <li><a href="/w/index.php?title=Tiamdipine&action=edit&redlink=1" class="new" title="Tiamdipine (page does not exist)">Tiamdipine</a></li> <li><a href="/w/index.php?title=Trombodipine&action=edit&redlink=1" class="new" title="Trombodipine (page does not exist)">Trombodipine</a></li> <li><a href="/w/index.php?title=Vatanidipine&action=edit&redlink=1" class="new" title="Vatanidipine (page does not exist)">Vatanidipine</a>; <i><a href="/wiki/Diltiazem" title="Diltiazem">Diltiazem</a> derivatives:</i> <a href="/wiki/Clentiazem" title="Clentiazem">Clentiazem</a></li> <li><a href="/wiki/Diltiazem" title="Diltiazem">Diltiazem</a></li> <li><a href="/w/index.php?title=Iprotiazem&action=edit&redlink=1" class="new" title="Iprotiazem (page does not exist)">Iprotiazem</a></li> <li><a href="/w/index.php?title=Nictiazem&action=edit&redlink=1" class="new" title="Nictiazem (page does not exist)">Nictiazem</a></li> <li><a href="/w/index.php?title=Siratiazem&action=edit&redlink=1" class="new" title="Siratiazem (page does not exist)">Siratiazem</a>; <i><a href="/wiki/Arylalkylamine" title="Arylalkylamine">Phenylalkylamines</a>:</i> <a href="/wiki/Anipamil" title="Anipamil">Anipamil</a></li> <li><a href="/w/index.php?title=Dagapamil&action=edit&redlink=1" class="new" title="Dagapamil (page does not exist)">Dagapamil</a></li> <li><a href="/wiki/Devapamil" title="Devapamil">Devapamil</a></li> <li><a href="/w/index.php?title=Dexverapamil&action=edit&redlink=1" class="new" title="Dexverapamil (page does not exist)">Dexverapamil</a></li> <li><a href="/wiki/Emopamil" title="Emopamil">Emopamil</a></li> <li><a href="/w/index.php?title=Etripamil&action=edit&redlink=1" class="new" title="Etripamil (page does not exist)">Etripamil</a></li> <li><a href="/wiki/Falipamil" title="Falipamil">Falipamil</a></li> <li><a href="/wiki/Gallopamil" title="Gallopamil">Gallopamil</a></li> <li><a href="/w/index.php?title=Levemopamil&action=edit&redlink=1" class="new" title="Levemopamil (page does not exist)">Levemopamil</a></li> <li><a href="/w/index.php?title=Nexopamil&action=edit&redlink=1" class="new" title="Nexopamil (page does not exist)">Nexopamil</a></li> <li><a href="/wiki/Norverapamil" title="Norverapamil">Norverapamil</a></li> <li><a href="/w/index.php?title=Ronipamil&action=edit&redlink=1" class="new" title="Ronipamil (page does not exist)">Ronipamil</a></li> <li><a href="/wiki/Tiapamil" title="Tiapamil">Tiapamil</a></li> <li><a href="/wiki/Verapamil" title="Verapamil">Verapamil</a>; <i>Others:</i> <a href="/wiki/AH-1058" title="AH-1058">AH-1058</a></li> <li><a href="/w/index.php?title=Brinazarone&action=edit&redlink=1" class="new" title="Brinazarone (page does not exist)">Brinazarone</a></li> <li><a href="/wiki/Budiodarone" title="Budiodarone">Budiodarone</a></li> <li><a href="/wiki/Celivarone" title="Celivarone">Celivarone</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Dronedarone" title="Dronedarone">Dronedarone</a></li> <li><a href="/wiki/Fantofarone" title="Fantofarone">Fantofarone</a></li> <li><a href="/w/index.php?title=SR-33805&action=edit&redlink=1" class="new" title="SR-33805 (page does not exist)">SR-33805</a></li> <li><a href="/wiki/Tetrahydropalmatine" title="Tetrahydropalmatine">Tetrahydropalmatine</a></li></ul> <ul><li><b><a href="/wiki/N-type_calcium_channel" title="N-type calcium channel">N-type-selective</a>:</b> <a href="/wiki/%CE%A9-Conotoxin" class="mw-redirect" title="Ω-Conotoxin">ω-Conotoxins</a></li> <li><a href="/w/index.php?title=%CE%A9-Conotoxin_GVIA&action=edit&redlink=1" class="new" title="Ω-Conotoxin GVIA (page does not exist)">ω-Conotoxin GVIA</a></li> <li><a href="/wiki/Caroverine" title="Caroverine">Caroverine</a></li> <li><a href="/w/index.php?title=Huwentoxin_XVI&action=edit&redlink=1" class="new" title="Huwentoxin XVI (page does not exist)">Huwentoxin XVI</a></li> <li><a href="/wiki/Leconotide" title="Leconotide">Leconotide (ω-conotoxin CVID)</a></li> <li><a href="/w/index.php?title=PD-173212&action=edit&redlink=1" class="new" title="PD-173212 (page does not exist)">PD-173212</a></li> <li><a href="/wiki/Ralfinamide" title="Ralfinamide">Ralfinamide</a></li> <li><a href="/wiki/Safinamide" title="Safinamide">Safinamide</a></li> <li><a href="/w/index.php?title=Z160&action=edit&redlink=1" class="new" title="Z160 (page does not exist)">Z160</a></li> <li><a href="/wiki/Ziconotide" title="Ziconotide">Ziconotide (ω-conotoxin MVIIA)</a></li></ul> <ul><li><b><a href="/wiki/P-type_calcium_channel" title="P-type calcium channel">P-type-selective</a>:</b> <a href="/w/index.php?title=%CE%A9-Agatoxin_IVA&action=edit&redlink=1" class="new" title="Ω-Agatoxin IVA (page does not exist)">ω-Agatoxin IVA</a></li> <li><a href="/w/index.php?title=%CE%A9-Agatoxin_IVB&action=edit&redlink=1" class="new" title="Ω-Agatoxin IVB (page does not exist)">ω-Agatoxin IVB</a></li></ul> <ul><li><b><a href="/wiki/R-type_calcium_channel" title="R-type calcium channel">R-type-selective</a>:</b> <a href="/wiki/SNX-482" title="SNX-482">SNX-482</a></li></ul> <ul><li><b><a href="/wiki/T-type_calcium_channel" title="T-type calcium channel">T-type-selective</a>:</b> <a href="/w/index.php?title=ABT-639&action=edit&redlink=1" class="new" title="ABT-639 (page does not exist)">ABT-639</a></li> <li><a href="/w/index.php?title=ML-218&action=edit&redlink=1" class="new" title="ML-218 (page does not exist)">ML-218</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/w/index.php?title=NNC_55-0396&action=edit&redlink=1" class="new" title="NNC 55-0396 (page does not exist)">NNC 55-0396</a></li> <li><a href="/w/index.php?title=ProTx_I&action=edit&redlink=1" class="new" title="ProTx I (page does not exist)">ProTx I</a></li> <li><a href="/w/index.php?title=Z944&action=edit&redlink=1" class="new" title="Z944 (page does not exist)">Z944</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> <ul><li><b>Non-selective:</b> <a href="/w/index.php?title=%CE%A9-Agatoxin_TK&action=edit&redlink=1" class="new" title="Ω-Agatoxin TK (page does not exist)">ω-Agatoxin TK</a></li> <li><a href="/w/index.php?title=%CE%A9-Conotoxin_MVIIC&action=edit&redlink=1" class="new" title="Ω-Conotoxin MVIIC (page does not exist)">ω-Conotoxin MVIIC</a></li> <li><a href="/wiki/Benidipine" title="Benidipine">Benidipine</a></li> <li><a href="/wiki/Bepridil" title="Bepridil">Bepridil</a></li> <li><a href="/wiki/Cilnidipine" title="Cilnidipine">Cilnidipine</a></li> <li><a href="/wiki/Cinnarizine" title="Cinnarizine">Cinnarizine</a></li> <li><a href="/wiki/Dotarizine" title="Dotarizine">Dotarizine</a></li> <li><a href="/wiki/Efonidipine" title="Efonidipine">Efonidipine</a></li> <li><a href="/wiki/Flunarizine" title="Flunarizine">Flunarizine</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a></li> <li><a href="/wiki/Levetiracetam" title="Levetiracetam">Levetiracetam</a></li> <li><a href="/wiki/Lomerizine" title="Lomerizine">Lomerizine</a></li> <li><a href="/wiki/Loperamide" title="Loperamide">Loperamide</a></li> <li><a href="/wiki/Mibefradil" title="Mibefradil">Mibefradil</a></li> <li><a href="/w/index.php?title=NP078585&action=edit&redlink=1" class="new" title="NP078585 (page does not exist)">NP078585</a></li> <li><a href="/wiki/Ruthenium_red" title="Ruthenium red">Ruthenium red</a></li> <li><a href="/wiki/TROX-1" title="TROX-1">TROX-1</a></li></ul> <ul><li><b><a href="/wiki/Voltage-dependent_calcium_channel#α2δ_Subunit" class="mw-redirect" title="Voltage-dependent calcium channel">α<sub>2</sub>δ subunit</a>-selective (<a href="/wiki/Gabapentinoid" title="Gabapentinoid">gabapentinoids</a>):</b> <a href="/wiki/4-Methylpregabalin" title="4-Methylpregabalin">4-Methylpregabalin</a></li> <li><a href="/wiki/Arbaclofen" class="mw-redirect" title="Arbaclofen">Arbaclofen</a></li> <li><a href="/wiki/Arbaclofen_placarbil" title="Arbaclofen placarbil">Arbaclofen placarbil</a></li> <li><a href="/wiki/Atagabalin" title="Atagabalin">Atagabalin</a></li> <li><a href="/wiki/Baclofen" title="Baclofen">Baclofen</a></li> <li><a href="/wiki/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Gabapentin_enacarbil" title="Gabapentin enacarbil">Gabapentin enacarbil</a></li> <li><a href="/wiki/Imagabalin" title="Imagabalin">Imagabalin</a></li> <li><a href="/wiki/Mirogabalin" title="Mirogabalin">Mirogabalin</a></li> <li><a href="/w/index.php?title=PD-200,347&action=edit&redlink=1" class="new" title="PD-200,347 (page does not exist)">PD-200,347</a></li> <li><a href="/wiki/PD-217,014" title="PD-217,014">PD-217,014</a></li> <li><a href="/w/index.php?title=PD-299,685&action=edit&redlink=1" class="new" title="PD-299,685 (page does not exist)">PD-299,685</a></li> <li><a href="/wiki/Phenibut" title="Phenibut">Phenibut</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a></li></ul> <ul><li><b>Others/unsorted:</b> <a href="/wiki/Bencyclane" title="Bencyclane">Bencyclane</a></li> <li><a href="/wiki/Berbamine" title="Berbamine">Berbamine</a></li> <li><a href="/wiki/Bevantolol" title="Bevantolol">Bevantolol</a></li> <li><a href="/wiki/Canadine" title="Canadine">Canadine</a></li> <li><a href="/wiki/Carboxyamidotriazole" title="Carboxyamidotriazole">Carboxyamidotriazole</a></li> <li><a href="/wiki/Cycleanine" title="Cycleanine">Cycleanine</a></li> <li><a href="/wiki/Dauricine" title="Dauricine">Dauricine</a></li> <li><a href="/wiki/Dimeditiapramine" class="mw-redirect" title="Dimeditiapramine">Dimeditiapramine</a></li> <li><a href="/wiki/Diproteverine" title="Diproteverine">Diproteverine</a></li> <li><a href="/wiki/Enpiperate" title="Enpiperate">Enpiperate</a></li> <li><a href="/wiki/Eperisone" title="Eperisone">Eperisone</a></li> <li><a href="/w/index.php?title=Elpetrigine&action=edit&redlink=1" class="new" title="Elpetrigine (page does not exist)">Elpetrigine</a></li> <li><a href="/wiki/Ethadione" title="Ethadione">Ethadione</a></li> <li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/Ethosuximide" title="Ethosuximide">Ethosuximide</a></li> <li><a href="/wiki/Fasudil" title="Fasudil">Fasudil</a></li> <li><a href="/wiki/Fendiline" title="Fendiline">Fendiline</a></li> <li><a href="/wiki/Fostedil" title="Fostedil">Fostedil</a></li> <li><a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/JTV-519" title="JTV-519">JTV-519</a></li> <li><a href="/wiki/Lidoflazine" title="Lidoflazine">Lidoflazine</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/wiki/Manoalide" title="Manoalide">Manoalide</a></li> <li><a href="/wiki/Mesuximide" title="Mesuximide">Mesuximide</a></li> <li><a href="/wiki/Monatepil" title="Monatepil">Monatepil</a></li> <li><a href="/wiki/Naftopidil" title="Naftopidil">Naftopidil</a></li> <li><a href="/wiki/Ochratoxin_A" title="Ochratoxin A">Ochratoxin A</a></li> <li><a href="/wiki/Osthol" title="Osthol">Osthol</a></li> <li><a href="/wiki/Otilonium_bromide" title="Otilonium bromide">Otilonium bromide</a></li> <li><a href="/wiki/Paramethadione" title="Paramethadione">Paramethadione</a></li> <li><a href="/wiki/Phensuximide" title="Phensuximide">Phensuximide</a></li> <li><a href="/wiki/Pinaverium_bromide" title="Pinaverium bromide">Pinaverium bromide</a></li> <li><a href="/wiki/Prenylamine" title="Prenylamine">Prenylamine</a></li> <li><a href="/wiki/Rhynchophylline" title="Rhynchophylline">Rhynchophylline</a></li> <li><a href="/wiki/Sesamodil" title="Sesamodil">Sesamodil</a></li> <li><a href="/wiki/Silperisone" title="Silperisone">Silperisone</a></li> <li><a href="/w/index.php?title=Sipatrigine&action=edit&redlink=1" class="new" title="Sipatrigine (page does not exist)">Sipatrigine</a></li> <li><a href="/wiki/Terodiline" title="Terodiline">Terodiline</a></li> <li><a href="/wiki/Tetrandrine" title="Tetrandrine">Tetrandrine</a></li> <li><a href="/wiki/Tolperisone" title="Tolperisone">Tolperisone</a></li> <li><a href="/wiki/Trimethadione" title="Trimethadione">Trimethadione</a></li> <li><a href="/wiki/Valperinol" title="Valperinol">Valperinol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Calcium_channel_opener" title="Calcium channel opener">Activators</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/L-type_calcium_channel" title="L-type calcium channel">L-type-selective</a>:</b> <a href="/wiki/Bay_K8644" title="Bay K8644">Bay K8644</a></li></ul> </div></td></tr></tbody></table><div></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/Potassium_channel" title="Potassium channel">Potassium</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Voltage-gated_potassium_channels" class="mw-redirect" title="Voltage-gated potassium channels"><abbr title="Voltage-gated potassium channels">VGKCs</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 Voltage-gated potassium channels</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Potassium_channel_blocker" title="Potassium channel blocker">Blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3,4-Diaminopyridine" class="mw-redirect" title="3,4-Diaminopyridine">3,4-Diaminopyridine (amifampridine)</a></li> <li><a href="/wiki/4-Aminopyridine" title="4-Aminopyridine">4-Aminopyridine (fampridine/dalfampridine)</a></li> <li><a href="/w/index.php?title=Adekalant&action=edit&redlink=1" class="new" title="Adekalant (page does not exist)">Adekalant</a></li> <li><a href="/wiki/Almokalant" title="Almokalant">Almokalant</a></li> <li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Azimilide" title="Azimilide">Azimilide</a></li> <li><a href="/wiki/Bretylium" title="Bretylium">Bretylium</a></li> <li><a href="/wiki/Bunaftine" title="Bunaftine">Bunaftine</a></li> <li><a href="/wiki/Charybdotoxin" title="Charybdotoxin">Charybdotoxin</a></li> <li><a href="/w/index.php?title=Clamikalant&action=edit&redlink=1" class="new" title="Clamikalant (page does not exist)">Clamikalant</a></li> <li><a href="/wiki/Conotoxin" title="Conotoxin">Conotoxins</a></li> <li><a href="/w/index.php?title=Dalazatide&action=edit&redlink=1" class="new" title="Dalazatide (page does not exist)">Dalazatide</a></li> <li><a href="/wiki/Dendrotoxin" title="Dendrotoxin">Dendrotoxin</a></li> <li><a href="/wiki/Dofetilide" title="Dofetilide">Dofetilide</a></li> <li><a href="/wiki/Dronedarone" title="Dronedarone">Dronedarone</a></li> <li><a href="/wiki/E-4031" title="E-4031">E-4031</a></li> <li><a href="/wiki/Hanatoxin" title="Hanatoxin">Hanatoxin</a></li> <li><a href="/wiki/HgeTx1" title="HgeTx1">HgeTx1</a></li> <li><a href="/wiki/HsTx1" title="HsTx1">HsTx1</a></li> <li><a href="/wiki/Ibutilide" title="Ibutilide">Ibutilide</a></li> <li><a href="/w/index.php?title=Inakalant&action=edit&redlink=1" class="new" title="Inakalant (page does not exist)">Inakalant</a></li> <li><a href="/wiki/Kaliotoxin" title="Kaliotoxin">Kaliotoxin</a></li> <li><a href="/wiki/Linopirdine" title="Linopirdine">Linopirdine</a></li> <li><a href="/wiki/Lolitrem_B" title="Lolitrem B">Lolitrem B</a></li> <li><a href="/wiki/Maurotoxin" title="Maurotoxin">Maurotoxin</a></li> <li><a href="/wiki/Nifekalant" title="Nifekalant">Nifekalant</a></li> <li><a href="/w/index.php?title=Notoxin&action=edit&redlink=1" class="new" title="Notoxin (page does not exist)">Notoxin</a></li> <li><a href="/wiki/Paxilline" title="Paxilline">Paxilline</a></li> <li><a href="/w/index.php?title=Pinokalant&action=edit&redlink=1" class="new" title="Pinokalant (page does not exist)">Pinokalant</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/w/index.php?title=ShK-186&action=edit&redlink=1" class="new" title="ShK-186 (page does not exist)">ShK-186</a></li> <li><a href="/wiki/Sotalol" title="Sotalol">Sotalol</a></li> <li><a href="/wiki/Tedisamil" title="Tedisamil">Tedisamil</a></li> <li><a href="/w/index.php?title=Terikalant&action=edit&redlink=1" class="new" title="Terikalant (page does not exist)">Terikalant</a></li> <li><a href="/wiki/Tetraethylammonium" title="Tetraethylammonium">Tetraethylammonium</a></li> <li><a href="/wiki/Vernakalant" title="Vernakalant">Vernakalant</a></li></ul> <ul><li><b><a href="/wiki/HERG" title="HERG">hERG</a> (KCNH2, K<sub>v</sub>11.1)-specific:</b> <a href="/wiki/Ajmaline" title="Ajmaline">Ajmaline</a></li> <li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/AmmTX3" title="AmmTX3">AmmTX3</a></li> <li><a href="/wiki/Astemizole" title="Astemizole">Astemizole</a></li> <li><a href="/wiki/Azaspiracid" title="Azaspiracid">Azaspiracid</a></li> <li><a href="/wiki/AZD1305" title="AZD1305">AZD1305</a></li> <li><a href="/wiki/Azimilide" title="Azimilide">Azimilide</a></li> <li><a href="/wiki/Bedaquiline" title="Bedaquiline">Bedaquiline</a></li> <li><a href="/wiki/BeKm-1_toxin" title="BeKm-1 toxin">BeKm-1</a></li> <li><a href="/wiki/BmTx3" title="BmTx3">BmTx3</a></li> <li><a href="/wiki/BRL-32872" title="BRL-32872">BRL-32872</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Cisapride" title="Cisapride">Cisapride</a></li> <li><a href="/wiki/Clarithromycin" title="Clarithromycin">Clarithromycin</a></li> <li><a href="/wiki/Darifenacin" title="Darifenacin">Darifenacin</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Diallyl_trisulfide" title="Diallyl trisulfide">Diallyl trisulfide</a></li> <li><a href="/wiki/Domperidone" title="Domperidone">Domperidone</a></li> <li><a href="/wiki/E-4031" title="E-4031">E-4031</a></li> <li><a href="/wiki/Ergtoxin" title="Ergtoxin">Ergtoxins</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Gigactonine" title="Gigactonine">Gigactonine</a></li> <li><a href="/wiki/Haloperidol" title="Haloperidol">Haloperidol</a></li> <li><a class="mw-selflink selflink">Ketoconazole</a></li> <li><a href="/wiki/Norpropoxyphene" title="Norpropoxyphene">Norpropoxyphene</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li> <li><a href="/wiki/Pimozide" title="Pimozide">Pimozide</a></li> <li><a href="/wiki/PNU-282,987" title="PNU-282,987">PNU-282,987</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">Promethazine</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/Ranolazine" title="Ranolazine">Ranolazine</a></li> <li><a href="/wiki/Roxithromycin" title="Roxithromycin">Roxithromycin</a></li> <li><a href="/wiki/Sertindole" title="Sertindole">Sertindole</a></li> <li><a href="/wiki/Solifenacin" title="Solifenacin">Solifenacin</a></li> <li><a href="/wiki/Tamulotoxin" title="Tamulotoxin">Tamulotoxin</a></li> <li><a href="/wiki/Terodiline" title="Terodiline">Terodiline</a></li> <li><a href="/wiki/Terfenadine" title="Terfenadine">Terfenadine</a></li> <li><a href="/wiki/Thioridazine" title="Thioridazine">Thioridazine</a></li> <li><a href="/wiki/Tolterodine" title="Tolterodine">Tolterodine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li> <li><a href="/wiki/Vernakalant" title="Vernakalant">Vernakalant</a></li></ul> <ul><li><b><a href="/wiki/KCNQ" title="KCNQ">KCNQ (K<sub>v</sub>7)</a>-specific:</b> <a href="/wiki/Linopirdine" title="Linopirdine">Linopirdine</a></li> <li><a href="/w/index.php?title=XE-991&action=edit&redlink=1" class="new" title="XE-991 (page does not exist)">XE-991</a></li> <li><a href="/wiki/Ssm_spooky_toxin" title="Ssm spooky toxin">Spooky toxin (SsTx)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Activators</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/KCNQ" title="KCNQ">KCNQ (K<sub>v</sub>7)</a>-specific:</b> <a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a></li> <li><a href="/wiki/Retigabine" title="Retigabine">Retigabine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Inwardly_rectifying_potassium_channel" class="mw-redirect" title="Inwardly rectifying potassium channel"><abbr title="Inwardly rectifying potassium channel">IRKs</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 Inwardly rectifying potassium channel</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Potassium_channel_blocker" title="Potassium channel blocker">Blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/ATP-sensitive_potassium_channel" title="ATP-sensitive potassium channel"><abbr title="ATP-sensitive potassium channel">K<sub>ATP</sub></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 ATP-sensitive potassium channel</span>-specific:</b> <a href="/wiki/Acetohexamide" title="Acetohexamide">Acetohexamide</a></li> <li><a href="/wiki/Carbutamide" title="Carbutamide">Carbutamide</a></li> <li><a href="/wiki/Chlorpropamide" title="Chlorpropamide">Chlorpropamide</a></li> <li><a href="/wiki/Glibenclamide" title="Glibenclamide">Glibenclamide (glyburide)</a></li> <li><a href="/wiki/Glibornuride" title="Glibornuride">Glibornuride</a></li> <li><a href="/wiki/Glicaramide" title="Glicaramide">Glicaramide</a></li> <li><a href="/wiki/Gliclazide" title="Gliclazide">Gliclazide</a></li> <li><a href="/wiki/Glimepiride" title="Glimepiride">Glimepiride</a></li> <li><a href="/wiki/Glipizide" title="Glipizide">Glipizide</a></li> <li><a href="/wiki/Gliquidone" title="Gliquidone">Gliquidone</a></li> <li><a href="/wiki/Glisoxepide" title="Glisoxepide">Glisoxepide</a></li> <li><a href="/wiki/Glyclopyramide" title="Glyclopyramide">Glyclopyramide</a></li> <li><a href="/w/index.php?title=Glycyclamide&action=edit&redlink=1" class="new" title="Glycyclamide (page does not exist)">Glycyclamide</a></li> <li><a href="/wiki/Metahexamide" title="Metahexamide">Metahexamide</a></li> <li><a href="/wiki/Mitiglinide" title="Mitiglinide">Mitiglinide</a></li> <li><a href="/wiki/Nateglinide" title="Nateglinide">Nateglinide</a></li> <li><a href="/wiki/Repaglinide" title="Repaglinide">Repaglinide</a></li> <li><a href="/wiki/Tolazamide" title="Tolazamide">Tolazamide</a></li> <li><a href="/wiki/Tolbutamide" title="Tolbutamide">Tolbutamide</a></li></ul> <ul><li><b><a href="/wiki/G_protein-coupled_inwardly_rectifying_potassium_channel" title="G protein-coupled inwardly rectifying potassium channel"><abbr title="G protein-coupled inwardly rectifying potassium channel">GIRK</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled inwardly rectifying potassium channel</span>-specific:</b> <a href="/wiki/Barium" title="Barium">Barium</a></li> <li><a href="/wiki/Caramiphen" title="Caramiphen">Caramiphen</a></li> <li><a href="/wiki/Cloperastine" title="Cloperastine">Cloperastine</a></li> <li><a href="/wiki/Clozapine" title="Clozapine">Clozapine</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Ethosuximide" title="Ethosuximide">Ethosuximide</a></li> <li><a href="/wiki/Ifenprodil" title="Ifenprodil">Ifenprodil</a></li> <li><a href="/wiki/Tertiapin" title="Tertiapin">Tertiapin</a></li> <li><a href="/wiki/Tipepidine" title="Tipepidine">Tipepidine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Activators</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/ATP-sensitive_potassium_channel" title="ATP-sensitive potassium channel"><abbr title="ATP-sensitive potassium channel">K<sub>ATP</sub></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 ATP-sensitive potassium channel</span>-specific:</b> <a href="/w/index.php?title=Aprikalim&action=edit&redlink=1" class="new" title="Aprikalim (page does not exist)">Aprikalim</a></li> <li><a href="/wiki/Bimakalim" title="Bimakalim">Bimakalim</a></li> <li><a href="/wiki/Cromakalim" title="Cromakalim">Cromakalim</a></li> <li><a href="/wiki/Diazoxide" title="Diazoxide">Diazoxide</a></li> <li><a href="/w/index.php?title=Emakalim&action=edit&redlink=1" class="new" title="Emakalim (page does not exist)">Emakalim</a></li> <li><a href="/wiki/Levcromakalim" class="mw-redirect" title="Levcromakalim">Levcromakalim</a></li> <li><a href="/w/index.php?title=Mazokalim&action=edit&redlink=1" class="new" title="Mazokalim (page does not exist)">Mazokalim</a></li> <li><a href="/wiki/Minoxidil" title="Minoxidil">Minoxidil</a></li> <li><a href="/wiki/Minoxidil_sulfate" title="Minoxidil sulfate">Minoxidil sulfate</a></li> <li><a href="/w/index.php?title=Naminidil&action=edit&redlink=1" class="new" title="Naminidil (page does not exist)">Naminidil</a></li> <li><a href="/wiki/Nicorandil" title="Nicorandil">Nicorandil</a></li> <li><a href="/wiki/Pinacidil" title="Pinacidil">Pinacidil</a></li> <li><a href="/w/index.php?title=Rilmakalim&action=edit&redlink=1" class="new" title="Rilmakalim (page does not exist)">Rilmakalim</a></li> <li><a href="/w/index.php?title=Sarakalim&action=edit&redlink=1" class="new" title="Sarakalim (page does not exist)">Sarakalim</a></li></ul> <ul><li><b><a href="/wiki/G_protein-coupled_inwardly_rectifying_potassium_channel" title="G protein-coupled inwardly rectifying potassium channel"><abbr title="G protein-coupled inwardly rectifying potassium channel">GIRK</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled inwardly rectifying potassium channel</span>-specific:</b> <a href="/w/index.php?title=ML-297&action=edit&redlink=1" class="new" title="ML-297 (page does not exist)">ML-297 (VU0456810)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Calcium-activated_potassium_channel" title="Calcium-activated potassium channel"><abbr title="Calcium-activated potassium channel">K<sub>Ca</sub></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 Calcium-activated potassium channel</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Potassium_channel_blocker" title="Potassium channel blocker">Blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/BK_channel" title="BK channel">BK<sub>Ca</sub></a>-specific:</b> <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Ethanol (alcohol)</a></li> <li><a href="/wiki/GAL-021" class="mw-redirect" title="GAL-021">GAL-021</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Activators</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/BK_channel" title="BK channel">BK<sub>Ca</sub></a>-specific:</b> <a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/wiki/Nimesulide" title="Nimesulide">Nimesulide</a></li> <li><a href="/wiki/Rottlerin" title="Rottlerin">Rottlerin (mallotoxin)</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Tandem_pore_domain_potassium_channel" class="mw-redirect" title="Tandem pore domain potassium channel"><abbr title="Tandem pore domain potassium channel">K2Ps</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 Tandem pore domain potassium channel</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Potassium_channel_blocker" title="Potassium channel blocker">Blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/12-O-Tetradecanoylphorbol-13-acetate" title="12-O-Tetradecanoylphorbol-13-acetate">12-O-Tetradecanoylphorbol-13-acetate</a></li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Norfluoxetine" class="mw-redirect" title="Norfluoxetine">Norfluoxetine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Activators</a></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/Riluzole" title="Riluzole">Riluzole</a></li></ul> </div></td></tr></tbody></table><div></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/Sodium_channel" title="Sodium channel">Sodium</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Voltage-gated_sodium_channels" class="mw-redirect" title="Voltage-gated sodium channels"><abbr title="Voltage-gated sodium channels">VGSCs</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 Voltage-gated sodium channels</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Antianginals:</i> <a href="/wiki/Ranolazine" title="Ranolazine">Ranolazine</a></li></ul> <ul><li><i>Antiarrhythmics (class I):</i> <a href="/wiki/Ajmaline" title="Ajmaline">Ajmaline</a></li> <li><a href="/wiki/Aprindine" title="Aprindine">Aprindine</a></li> <li><a href="/wiki/Disopyramide" title="Disopyramide">Disopyramide</a></li> <li><a href="/wiki/Dronedarone" title="Dronedarone">Dronedarone</a></li> <li><a href="/wiki/Encainide" title="Encainide">Encainide</a></li> <li><a href="/wiki/Flecainide" title="Flecainide">Flecainide</a></li> <li><a href="/wiki/Lidocaine" title="Lidocaine">Lidocaine</a></li> <li><a href="/wiki/Lorajmine" title="Lorajmine">Lorajmine</a></li> <li><a href="/wiki/Lorcainide" title="Lorcainide">Lorcainide</a></li> <li><a href="/wiki/Mexiletine" title="Mexiletine">Mexiletine</a></li> <li><a href="/wiki/Moracizine" title="Moracizine">Moricizine</a></li> <li><a href="/wiki/Pilsicainide" title="Pilsicainide">Pilsicainide</a></li> <li><a href="/wiki/Prajmaline" title="Prajmaline">Prajmaline</a></li> <li><a href="/wiki/Procainamide" title="Procainamide">Procainamide</a></li> <li><a href="/wiki/Propafenone" title="Propafenone">Propafenone</a></li> <li><a href="/wiki/Quinidine" title="Quinidine">Quinidine</a></li> <li><a href="/wiki/Sparteine" title="Sparteine">Sparteine</a></li> <li><a href="/wiki/Tocainide" title="Tocainide">Tocainide</a></li></ul> <ul><li><i>Anticonvulsants:</i> <a href="/w/index.php?title=Acetylpheneturide&action=edit&redlink=1" class="new" title="Acetylpheneturide (page does not exist)">Acetylpheneturide</a></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Cenobamate" title="Cenobamate">Cenobamate</a></li> <li><a href="/wiki/Chlorphenacemide" title="Chlorphenacemide">Chlorphenacemide</a></li> <li><a href="/w/index.php?title=Elpetrigine&action=edit&redlink=1" class="new" title="Elpetrigine (page does not exist)">Elpetrigine</a></li> <li><a href="/wiki/Eslicarbazepine_acetate" title="Eslicarbazepine acetate">Eslicarbazepine acetate</a></li> <li><a href="/wiki/Ethotoin" title="Ethotoin">Ethotoin</a></li> <li><a href="/wiki/Fosphenytoin" title="Fosphenytoin">Fosphenytoin</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a></li> <li><a href="/wiki/Lacosamide" title="Lacosamide">Lacosamide</a></li> <li><a href="/wiki/Licarbazepine" title="Licarbazepine">Licarbazepine</a></li> <li><a href="/wiki/Mephenytoin" title="Mephenytoin">Mephenytoin</a></li> <li><a href="/wiki/Oxcarbazepine" title="Oxcarbazepine">Oxcarbazepine</a></li> <li><a href="/wiki/Oxitriptyline" title="Oxitriptyline">Oxitriptyline</a></li> <li><a href="/wiki/Phenacemide" title="Phenacemide">Phenacemide</a></li> <li><a href="/wiki/Pheneturide" title="Pheneturide">Pheneturide</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/Rufinamide" title="Rufinamide">Rufinamide</a></li> <li><a href="/w/index.php?title=Sipatrigine&action=edit&redlink=1" class="new" title="Sipatrigine (page does not exist)">Sipatrigine</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Sodium_valproate" class="mw-redirect" title="Sodium valproate">Sodium valproate</a></li> <li><a href="/wiki/Valnoctamide" title="Valnoctamide">Valnoctamide</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a></li> <li><a href="/wiki/Valproate_semisodium" class="mw-redirect" title="Valproate semisodium">Valproate semisodium</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> <ul><li><i>Local anesthetics:</i> <a href="/wiki/3-(p-Fluorobenzoyloxy)tropane" title="3-(p-Fluorobenzoyloxy)tropane"><i>p</i>FBT</a></li> <li><a href="/wiki/Amylocaine" title="Amylocaine">Amylocaine</a></li> <li><a href="/wiki/Articaine" title="Articaine">Articaine</a></li> <li><a href="/wiki/Benzocaine" title="Benzocaine">Benzocaine</a></li> <li><a href="/wiki/Bupivacaine" title="Bupivacaine">Bupivacaine</a> (<a href="/wiki/Levobupivacaine" title="Levobupivacaine">Levobupivacaine</a>, <a href="/wiki/Ropivacaine" title="Ropivacaine">Ropivacaine</a>)</li> <li><a href="/wiki/Butacaine" title="Butacaine">Butacaine</a></li> <li><a href="/wiki/Butamben" title="Butamben">Butamben</a></li> <li><a href="/wiki/Chloroprocaine" title="Chloroprocaine">Chloroprocaine</a></li> <li><a href="/wiki/Cinchocaine" title="Cinchocaine">Cinchocaine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Cyclomethycaine" title="Cyclomethycaine">Cyclomethycaine</a></li> <li><a href="/wiki/Dimethocaine" title="Dimethocaine">Dimethocaine</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Etidocaine" title="Etidocaine">Etidocaine</a></li> <li><a href="/wiki/Hexylcaine" title="Hexylcaine">Hexylcaine</a></li> <li><a href="/wiki/Iontocaine" title="Iontocaine">Iontocaine</a></li> <li><a href="/wiki/Lidocaine" title="Lidocaine">Lidocaine</a></li> <li><a href="/wiki/Mepivacaine" title="Mepivacaine">Mepivacaine</a></li> <li><a href="/wiki/Meprylcaine" title="Meprylcaine">Meprylcaine</a></li> <li><a href="/wiki/Metabutoxycaine" title="Metabutoxycaine">Metabutoxycaine</a></li> <li><a href="/wiki/Orthocaine" title="Orthocaine">Orthocaine</a></li> <li><a href="/wiki/Piperocaine" title="Piperocaine">Piperocaine</a></li> <li><a href="/wiki/Prilocaine" title="Prilocaine">Prilocaine</a></li> <li><a href="/wiki/Procaine" title="Procaine">Procaine</a></li> <li><a href="/wiki/Propoxycaine" title="Propoxycaine">Propoxycaine</a></li> <li><a href="/wiki/Proxymetacaine" title="Proxymetacaine">Proxymetacaine</a></li> <li><a href="/wiki/Risocaine" title="Risocaine">Risocaine</a></li> <li><a href="/wiki/Tetracaine" title="Tetracaine">Tetracaine</a></li> <li><a href="/wiki/Trimecaine" title="Trimecaine">Trimecaine</a></li></ul> <ul><li><i>Analgesics:</i> <a href="/w/index.php?title=AZD-3161&action=edit&redlink=1" class="new" title="AZD-3161 (page does not exist)">AZD-3161</a></li> <li><a href="/wiki/DSP-2230" title="DSP-2230">DSP-2230</a></li> <li><a href="/wiki/Funapide" title="Funapide">Funapide</a></li> <li><a href="/w/index.php?title=GDC-0276&action=edit&redlink=1" class="new" title="GDC-0276 (page does not exist)">GDC-0276</a></li> <li><a href="/w/index.php?title=NKTR-171&action=edit&redlink=1" class="new" title="NKTR-171 (page does not exist)">NKTR-171</a></li> <li><a href="/w/index.php?title=PF-04531083&action=edit&redlink=1" class="new" title="PF-04531083 (page does not exist)">PF-04531083</a></li> <li><a href="/wiki/PF-05089771" title="PF-05089771">PF-05089771</a></li> <li><a href="/wiki/Ralfinamide" title="Ralfinamide">Ralfinamide</a></li> <li><a href="/wiki/Raxatrigine" class="mw-redirect" title="Raxatrigine">Raxatrigine</a></li> <li><a href="/w/index.php?title=RG7893&action=edit&redlink=1" class="new" title="RG7893 (page does not exist)">RG7893 (GDC-0287)</a></li> <li><a href="/wiki/Suzetrigine" title="Suzetrigine">Suzetrigine</a></li></ul> <ul><li><i>Toxins:</i> <a href="/wiki/Conotoxin" title="Conotoxin">Conotoxins</a></li> <li><a href="/wiki/Neosaxitoxin" title="Neosaxitoxin">Neosaxitoxin</a></li> <li><a href="/wiki/Saxitoxin" title="Saxitoxin">Saxitoxin</a></li> <li><a href="/wiki/Tetrodotoxin" title="Tetrodotoxin">Tetrodotoxin</a></li> <li><a href="/wiki/Zetekitoxin_AB" title="Zetekitoxin AB">Zetekitoxin AB</a></li></ul> <ul><li><i>Others:</i> <a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a></li> <li><a href="/wiki/Evenamide" title="Evenamide">Evenamide</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a> (<a href="/wiki/Mentha" title="Mentha">mint</a>)</li> <li><a href="/wiki/Safinamide" title="Safinamide">Safinamide</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Sodium_channel_opener" title="Sodium channel opener">Activators</a></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/Aconitine" title="Aconitine">Aconitine</a></li> <li>Atracotoxins (<a href="/wiki/Omega-Atracotoxin" title="Omega-Atracotoxin">ω-Atracotoxin</a>, <a href="/wiki/Robustoxin" class="mw-redirect" title="Robustoxin">Robustoxin</a>, <a href="/wiki/Versutoxin" title="Versutoxin">Versutoxin</a>)</li> <li><a href="/wiki/Batrachotoxin" title="Batrachotoxin">Batrachotoxin</a></li> <li><a href="/wiki/Ciguatoxin" title="Ciguatoxin">Ciguatoxins</a></li> <li><a href="/wiki/Grayanotoxin" title="Grayanotoxin">Grayanotoxins</a></li> <li><a href="/wiki/Poneratoxin" title="Poneratoxin">Poneratoxin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Epithelial_sodium_channel" title="Epithelial sodium channel"><abbr title="Epithelial sodium channel">ENaC</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 Epithelial sodium channel</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Benzamil" title="Benzamil">Benzamil</a></li> <li><a href="/wiki/Triamterene" title="Triamterene">Triamterene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Sodium_channel_opener" title="Sodium channel opener">Activators</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Solnatide&action=edit&redlink=1" class="new" title="Solnatide (page does not exist)">Solnatide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Acid-sensing_ion_channel" title="Acid-sensing ion channel"><abbr title="Acid-sensing ion channel">ASICs</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 Acid-sensing ion channel</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=A-317567&action=edit&redlink=1" class="new" title="A-317567 (page does not exist)">A-317567</a></li> <li><a href="/wiki/Amiloride" title="Amiloride">Amiloride</a></li> <li><a href="/wiki/Aspirin" title="Aspirin">Aspirin</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a></li> <li><a href="/w/index.php?title=PcTX1&action=edit&redlink=1" class="new" title="PcTX1 (page does not exist)">PcTX1</a></li></ul> </div></td></tr></tbody></table><div></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/Chloride_channel" title="Chloride channel">Chloride</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Calcium-activated_chloride_channel" class="mw-redirect" title="Calcium-activated chloride channel"><abbr title="Calcium-activated chloride channel">CaCCs</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 Calcium-activated chloride channel</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Chloride_channel_blocker" title="Chloride channel blocker">Blockers</a></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/Crofelemer" title="Crofelemer">Crofelemer</a></li> <li><a href="/wiki/DIDS" title="DIDS">DIDS</a></li> <li><a href="/wiki/Ethacrynic_acid" class="mw-redirect" title="Ethacrynic acid">Ethacrynic acid</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Furosemide" title="Furosemide">Furosemide</a></li> <li><a href="/wiki/Glibenclamide" title="Glibenclamide">Glibenclamide</a></li> <li><a href="/wiki/Mefloquine" title="Mefloquine">Mefloquine</a></li> <li><a href="/wiki/Mibefradil" title="Mibefradil">Mibefradil</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Chloride_channel_opener" title="Chloride channel opener">Activators</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carbachol" title="Carbachol">Carbachol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Cystic_fibrosis_transmembrane_conductance_regulator" title="Cystic fibrosis transmembrane conductance regulator"><abbr title="Cystic fibrosis transmembrane conductance regulator">CFTR</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 Cystic fibrosis transmembrane conductance regulator</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Chloride_channel_blocker" title="Chloride channel blocker">Blockers</a></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/Glibenclamide" title="Glibenclamide">Glibenclamide</a></li> <li><a href="/wiki/Lonidamine" title="Lonidamine">Lonidamine</a></li> <li><a href="/wiki/Piretanide" title="Piretanide">Piretanide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Chloride_channel_opener" title="Chloride channel opener">Activators</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=1,7-Phenanthroline&action=edit&redlink=1" class="new" title="1,7-Phenanthroline (page does not exist)">1,7-Phenanthroline</a></li> <li><a href="/wiki/1,10-Phenanthroline" title="1,10-Phenanthroline">1,10-Phenanthroline</a></li> <li><a href="/w/index.php?title=4,7-Phenanthroline&action=edit&redlink=1" class="new" title="4,7-Phenanthroline (page does not exist)">4,7-Phenanthroline</a></li> <li><a href="/w/index.php?title=7,8-Benzoquinoline&action=edit&redlink=1" class="new" title="7,8-Benzoquinoline (page does not exist)">7,8-Benzoquinoline</a></li> <li><a href="/wiki/Ivacaftor" title="Ivacaftor">Ivacaftor</a></li> <li><a href="/wiki/Phenanthridine" title="Phenanthridine">Phenanthridine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd" style="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:5em;;text-align:center;"><a href="/wiki/Chloride_channel_blocker" title="Chloride channel blocker">Blockers</a></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/Bumetanide" title="Bumetanide">Bumetanide</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid</a></li> <li><a href="/wiki/Mepacrine" title="Mepacrine">Mepacrine</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid</a></li> <li><a href="/w/index.php?title=Talniflumate&action=edit&redlink=1" class="new" title="Talniflumate (page does not exist)">Talniflumate</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li> <li><a href="/wiki/Trifluoperazine" title="Trifluoperazine">Trifluoperazine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Transient_receptor_potential_channels" class="mw-redirect" title="Transient receptor potential channels"><abbr title="Transient receptor potential channels">TRPs</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 Transient receptor potential channels</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Transient_receptor_potential_channel_modulators" title="Template:Transient receptor potential channel modulators">here</a> instead.</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Ligand_gated_ion_channels" class="mw-redirect" title="Ligand gated ion channels"><abbr title="Ligand gated ion channels">LGICs</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 Ligand gated ion channels</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>See <a href="/wiki/Template:Pharmacomodulation" title="Template:Pharmacomodulation">here</a> instead.</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Transient_receptor_potential_channel_modulators" title="Template:Transient receptor potential channel modulators">Transient receptor potential channel modulators</a></i></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="Xenobiotic-sensing_receptor_modulators953" 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:Xenobiotic-sensing_receptor_modulators" title="Template:Xenobiotic-sensing receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Xenobiotic-sensing_receptor_modulators" title="Template talk:Xenobiotic-sensing receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Xenobiotic-sensing_receptor_modulators" title="Special:EditPage/Template:Xenobiotic-sensing receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Xenobiotic-sensing_receptor_modulators953" style="font-size:114%;margin:0 4em"><a href="/wiki/Xenobiotic-sensing_receptor" title="Xenobiotic-sensing receptor">Xenobiotic-sensing 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/Constitutive_androstane_receptor" title="Constitutive androstane receptor"><abbr title="Constitutive androstane receptor">CAR</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 Constitutive androstane receptor</span></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>Agonists:</i> <a href="/w/index.php?title=6,7-Dimethylesculetin&action=edit&redlink=1" class="new" title="6,7-Dimethylesculetin (page does not exist)">6,7-Dimethylesculetin</a></li> <li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/w/index.php?title=Benfuracarb&action=edit&redlink=1" class="new" title="Benfuracarb (page does not exist)">Benfuracarb</a></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chrysin" title="Chrysin">Chrysin</a></li> <li><a href="/w/index.php?title=CITCO_(drug)&action=edit&redlink=1" class="new" title="CITCO (drug) (page does not exist)">CITCO</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cypermethrin" title="Cypermethrin">Cypermethrin</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Nevirapine" title="Nevirapine">Nevirapine</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/w/index.php?title=Octicizer&action=edit&redlink=1" class="new" title="Octicizer (page does not exist)">Octicizer</a></li> <li><a href="/wiki/Permethrin" title="Permethrin">Permethrin</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/w/index.php?title=TCPOBOP&action=edit&redlink=1" class="new" title="TCPOBOP (page does not exist)">TCPOBOP</a></li> <li><a href="/wiki/Telmisartan" title="Telmisartan">Telmisartan</a></li> <li><a href="/wiki/Tolnaftate" title="Tolnaftate">Tolnaftate</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=3,17%CE%B2-Estradiol&action=edit&redlink=1" class="new" title="3,17β-Estradiol (page does not exist)">3,17β-Estradiol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B1-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3α-ol (page does not exist)">3α-Androstanol</a></li> <li><a href="/wiki/5%CE%B1-Androst-16-en-3%CE%B1-ol" class="mw-redirect" title="5α-Androst-16-en-3α-ol">3α-Androstenol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B2-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3β-ol (page does not exist)">3β-Androstanol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-17-ol&action=edit&redlink=1" class="new" title="5α-Androstan-17-ol (page does not exist)">17-Androstanol</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">AITC</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/w/index.php?title=Nigramide_J&action=edit&redlink=1" class="new" title="Nigramide J (page does not exist)">Nigramide J</a></li> <li><a href="/wiki/Okadaic_acid" title="Okadaic acid">Okadaic acid</a></li> <li><a href="/wiki/PK-11195" class="mw-redirect" title="PK-11195">PK-11195</a></li> <li><a href="/w/index.php?title=S-07662&action=edit&redlink=1" class="new" title="S-07662 (page does not exist)">S-07662</a></li> <li><a href="/w/index.php?title=T-0901317&action=edit&redlink=1" class="new" title="T-0901317 (page does not exist)">T-0901317</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor"><abbr title="Pregnane X receptor">PXR</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 Pregnane X receptor</span></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>Agonists:</i> <a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/%CE%944-Androstenedione" class="mw-redirect" title="Δ4-Androstenedione">Δ<sup>4</sup>-Androstenedione</a></li> <li><a href="/wiki/%CE%945-Androstenediol" class="mw-redirect" title="Δ5-Androstenediol">Δ<sup>5</sup>-Androstenediol</a></li> <li><a href="/wiki/%CE%945-Androstenedione" class="mw-redirect" title="Δ5-Androstenedione">Δ<sup>5</sup>-Androstenedione</a></li> <li><a href="/w/index.php?title=AA-861&action=edit&redlink=1" class="new" title="AA-861 (page does not exist)">AA-861</a></li> <li><a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">Allopregnanedione (5α-dihydroprogesterone)</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alpha-Lipoic_acid" class="mw-redirect" title="Alpha-Lipoic acid">Alpha-Lipoic acid</a></li> <li><a href="/wiki/Ambrisentan" title="Ambrisentan">Ambrisentan</a></li> <li><a href="/wiki/AMI-193" class="mw-redirect" title="AMI-193">AMI-193</a></li> <li><a href="/wiki/Amlodipine_besylate" class="mw-redirect" title="Amlodipine besylate">Amlodipine besylate</a></li> <li><a href="/wiki/Antimycotic" class="mw-redirect" title="Antimycotic">Antimycotics</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Aurothioglucose" title="Aurothioglucose">Aurothioglucose</a></li> <li><a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a></li> <li><a href="/wiki/Bithionol" title="Bithionol">Bithionol</a></li> <li><a href="/wiki/Bosentan" title="Bosentan">Bosentan</a></li> <li><a href="/w/index.php?title=Bumecaine&action=edit&redlink=1" class="new" title="Bumecaine (page does not exist)">Bumecaine</a></li> <li><a href="/wiki/Cafestol" title="Cafestol">Cafestol</a></li> <li><a href="/wiki/Cephaloridine" title="Cephaloridine">Cephaloridine</a></li> <li><a href="/wiki/Cephradine" class="mw-redirect" title="Cephradine">Cephradine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Ciglitazone" title="Ciglitazone">Ciglitazone</a></li> <li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Clofenvinfos" class="mw-redirect" title="Clofenvinfos">Clofenvinfos</a></li> <li><a href="/wiki/Chloroxine" title="Chloroxine">Chloroxine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Colforsin" class="mw-redirect" title="Colforsin">Colforsin</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/wiki/Dibunate_sodium" class="mw-redirect" title="Dibunate sodium">Dibunate sodium</a></li> <li><a href="/wiki/Diclazuril" title="Diclazuril">Diclazuril</a></li> <li><a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Dimercaprol" title="Dimercaprol">Dimercaprol</a></li> <li><a href="/w/index.php?title=Dinaline&action=edit&redlink=1" class="new" title="Dinaline (page does not exist)">Dinaline</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a></li> <li><a href="/wiki/Docusate_calcium" class="mw-redirect" title="Docusate calcium">Docusate calcium</a></li> <li><a href="/wiki/Dodecylbenzenesulfonic_acid" class="mw-redirect" title="Dodecylbenzenesulfonic acid">Dodecylbenzenesulfonic acid</a></li> <li><a href="/wiki/Dronabinol" title="Dronabinol">Dronabinol</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa</a></li> <li><a href="/wiki/Eburnamonine" class="mw-redirect" title="Eburnamonine">Eburnamonine</a></li> <li><a href="/wiki/Ecopipam" title="Ecopipam">Ecopipam</a></li> <li><a href="/wiki/Enzacamene" title="Enzacamene">Enzacamene</a></li> <li><a href="/wiki/Epothilone_B" class="mw-redirect" title="Epothilone B">Epothilone B</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/w/index.php?title=Febantel&action=edit&redlink=1" class="new" title="Febantel (page does not exist)">Febantel</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Fenbendazole" title="Fenbendazole">Fenbendazole</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Flucloxacillin" title="Flucloxacillin">Flucloxacillin</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Haloprogin" title="Haloprogin">Haloprogin</a></li> <li><a href="/wiki/Hetacillin_potassium" class="mw-redirect" title="Hetacillin potassium">Hetacillin potassium</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum"><i>Hypericum perforatum</i> (St John's wort)</a></li> <li><a href="/wiki/Indinavir_sulfate" class="mw-redirect" title="Indinavir sulfate">Indinavir sulfate</a></li> <li><a href="/wiki/Lasalocid_sodium" class="mw-redirect" title="Lasalocid sodium">Lasalocid sodium</a></li> <li><a href="/wiki/Levothyroxine" title="Levothyroxine">Levothyroxine</a></li> <li>Linolenic acid: <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic acid</a> and <a href="/wiki/%CE%93-Linolenic_acid" title="Γ-Linolenic acid">γ-Linolenic acid</a></li> <li><a href="/w/index.php?title=LOE-908&action=edit&redlink=1" class="new" title="LOE-908 (page does not exist)">LOE-908</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/wiki/Lovastatin" title="Lovastatin">Lovastatin</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mevastatin" title="Mevastatin">Mevastatin</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nilvadipine" title="Nilvadipine">Nilvadipine</a></li> <li><a href="/wiki/Nisoldipine" title="Nisoldipine">Nisoldipine</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a></li> <li><a href="/wiki/Orlistat" title="Orlistat">Orlistat</a></li> <li><a href="/wiki/Oxatomide" title="Oxatomide">Oxatomide</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Proadifen" title="Proadifen">Proadifen</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a 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exist)">SR-12813</a></li> <li><a href="/w/index.php?title=Suberoylanilide&action=edit&redlink=1" class="new" title="Suberoylanilide (page does not exist)">Suberoylanilide</a></li> <li><a href="/wiki/Sulfisoxazole" class="mw-redirect" title="Sulfisoxazole">Sulfisoxazole</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a href="/wiki/Tacrolimus" title="Tacrolimus">Tacrolimus</a></li> <li><a href="/w/index.php?title=Tenylidone&action=edit&redlink=1" class="new" title="Tenylidone (page does not exist)">Tenylidone</a></li> <li><a href="/wiki/Terconazole" title="Terconazole">Terconazole</a></li> <li><a href="/wiki/Testosterone_isocaproate" title="Testosterone isocaproate">Testosterone isocaproate</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li> <li><a href="/wiki/Thiamylal_sodium" class="mw-redirect" title="Thiamylal sodium">Thiamylal sodium</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" 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