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<li id="toc-Epilepsy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Epilepsy"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Epilepsy</span> </div> </a> <ul id="toc-Epilepsy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mental_illness" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mental_illness"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Mental illness</span> </div> </a> <ul id="toc-Mental_illness-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_neurological_indications" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_neurological_indications"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Other neurological indications</span> </div> </a> <ul id="toc-Other_neurological_indications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </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-Adverse_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Adverse_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Adverse effects</span> </div> </a> <button aria-controls="toc-Adverse_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 Adverse effects subsection</span> </button> <ul id="toc-Adverse_effects-sublist" class="vector-toc-list"> <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">3.1</span> <span>Pregnancy</span> </div> </a> <ul id="toc-Pregnancy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Elderly" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Elderly"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Elderly</span> </div> </a> <ul id="toc-Elderly-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Overdose_and_toxicity" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose_and_toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Overdose and toxicity</span> </div> </a> <ul id="toc-Overdose_and_toxicity-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-Endocrine_actions" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Endocrine_actions"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.1</span> <span>Endocrine actions</span> </div> </a> <ul id="toc-Endocrine_actions-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-Approval_status" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Approval_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Approval status</span> </div> </a> <ul id="toc-Approval_status-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">9.2</span> <span>Off-label uses</span> </div> </a> <ul id="toc-Off-label_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Formulations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Formulations"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.3</span> <span>Formulations</span> </div> </a> <ul id="toc-Formulations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Terminology" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Terminology"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4</span> <span>Terminology</span> </div> </a> <ul id="toc-Terminology-sublist" class="vector-toc-list"> <li id="toc-Brand_names_of_valproic_acid" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Brand_names_of_valproic_acid"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.1</span> <span>Brand names of valproic acid</span> </div> </a> <ul id="toc-Brand_names_of_valproic_acid-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brand_names_of_sodium_valproate" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Brand_names_of_sodium_valproate"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2</span> <span>Brand names of sodium valproate</span> </div> </a> <ul id="toc-Brand_names_of_sodium_valproate-sublist" class="vector-toc-list"> <li id="toc-Portugal" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Portugal"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.1</span> <span>Portugal</span> </div> </a> <ul id="toc-Portugal-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-United_States" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#United_States"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.2</span> <span>United States</span> </div> </a> <ul id="toc-United_States-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Australia" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Australia"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.3</span> <span>Australia</span> </div> </a> <ul id="toc-Australia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-New_Zealand" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#New_Zealand"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.4</span> <span>New Zealand</span> </div> </a> <ul id="toc-New_Zealand-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-UK" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#UK"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.5</span> <span>UK</span> </div> </a> <ul id="toc-UK-sublist" class="vector-toc-list"> <li id="toc-UK_only" class="vector-toc-list-item vector-toc-level-5"> <a class="vector-toc-link" href="#UK_only"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.5.1</span> <span>UK only</span> </div> </a> <ul id="toc-UK_only-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Germany,_Switzerland,_Norway,_Finland,_Sweden" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Germany,_Switzerland,_Norway,_Finland,_Sweden"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.6</span> <span>Germany, Switzerland, Norway, Finland, Sweden</span> </div> </a> <ul id="toc-Germany,_Switzerland,_Norway,_Finland,_Sweden-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-South_Africa" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#South_Africa"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.7</span> <span>South Africa</span> </div> </a> <ul id="toc-South_Africa-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Malaysia" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Malaysia"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.8</span> <span>Malaysia</span> </div> </a> <ul id="toc-Malaysia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Romania" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Romania"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.9</span> <span>Romania</span> </div> </a> <ul id="toc-Romania-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Canada" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Canada"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.10</span> <span>Canada</span> </div> </a> <ul id="toc-Canada-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Japan" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Japan"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.11</span> <span>Japan</span> </div> </a> <ul id="toc-Japan-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Europe" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Europe"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.12</span> <span>Europe</span> </div> </a> <ul id="toc-Europe-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Taiwan" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Taiwan"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.13</span> <span>Taiwan</span> </div> </a> <ul id="toc-Taiwan-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Iran" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Iran"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.14</span> <span>Iran</span> </div> </a> <ul id="toc-Iran-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Israel" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Israel"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.15</span> <span>Israel</span> </div> </a> <ul id="toc-Israel-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-India,_Russia_and_CIS_countries" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#India,_Russia_and_CIS_countries"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.16</span> <span>India, Russia and CIS countries</span> </div> </a> <ul id="toc-India,_Russia_and_CIS_countries-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uruguay" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Uruguay"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.2.17</span> <span>Uruguay</span> </div> </a> <ul id="toc-Uruguay-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Brand_names_of_valproate_semisodium" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Brand_names_of_valproate_semisodium"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.4.3</span> <span>Brand names of valproate semisodium</span> </div> </a> <ul id="toc-Brand_names_of_valproate_semisodium-sublist" class="vector-toc-list"> </ul> </li> </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-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">11</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" 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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 41 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-41" 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">41 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%81%D8%A7%D9%84%D8%A8%D8%B1%D9%88%D8%A7%D8%AA" title="فالبروات – Arabic" lang="ar" hreflang="ar" data-title="فالبروات" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%88%D8%A7%D9%84%D9%BE%D8%B1%D9%88%D8%A7%D8%AA" title="والپروات – South Azerbaijani" lang="azb" hreflang="azb" data-title="والپروات" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%92%D0%B0%D0%BB%D0%BF%D1%80%D0%BE%D0%B5%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Валпроева киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Валпроева киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_valproic" title="Àcid valproic – Catalan" lang="ca" hreflang="ca" data-title="Àcid valproic" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Valpro%C3%A1t" title="Valproát – Czech" lang="cs" hreflang="cs" data-title="Valproát" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Falporad" title="Falporad – Welsh" lang="cy" hreflang="cy" data-title="Falporad" 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/Valproins%C3%A4ure" title="Valproinsäure – German" lang="de" hreflang="de" data-title="Valproinsäure" 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%92%CE%B1%CE%BB%CF%80%CF%81%CE%BF%CF%8A%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Βαλπροϊκό οξύ – Greek" lang="el" hreflang="el" data-title="Βαλπροϊκό οξύ" 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/%C3%81cido_valproico" title="Ácido valproico – Spanish" lang="es" hreflang="es" data-title="Ácido valproico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Valproata_acido" title="Valproata acido – Esperanto" lang="eo" hreflang="eo" data-title="Valproata acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido_balproiko" title="Azido balproiko – Basque" lang="eu" hreflang="eu" data-title="Azido balproiko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%88%D8%A7%D9%84%D9%BE%D8%B1%D9%88%D8%A7%D8%AA" title="والپروات – Persian" lang="fa" hreflang="fa" data-title="والپروات" 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/Acide_valpro%C3%AFque" title="Acide valproïque – French" lang="fr" hreflang="fr" data-title="Acide valproïque" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B0%B8%ED%94%84%EB%A1%9C%EC%97%90%EC%9D%B4%ED%8A%B8" title="밸프로에이트 – Korean" lang="ko" hreflang="ko" data-title="밸프로에이트" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-ha mw-list-item"><a href="https://ha.wikipedia.org/wiki/Valproate" title="Valproate – Hausa" lang="ha" hreflang="ha" data-title="Valproate" data-language-autonym="Hausa" data-language-local-name="Hausa" class="interlanguage-link-target"><span>Hausa</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8E%D5%A1%D5%AC%D5%BA%D6%80%D5%B8%D5%A1%D5%BF" title="Վալպրոատ – Armenian" lang="hy" hreflang="hy" data-title="Վալպրոատ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%AD%E0%A5%87%E0%A4%B2%E0%A4%AA%E0%A5%8D%E0%A4%B0%E0%A5%8B%E0%A4%87%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="भेलप्रोइक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="भेलप्रोइक अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_valproat" title="Asam valproat – Indonesian" lang="id" hreflang="id" data-title="Asam valproat" 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/Acido_valproico" title="Acido valproico – Italian" lang="it" hreflang="it" data-title="Acido valproico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%97%D7%95%D7%9E%D7%A6%D7%94_%D7%95%D7%9C%D7%A4%D7%A8%D7%95%D7%90%D7%99%D7%AA" title="חומצה ולפרואית – Hebrew" lang="he" hreflang="he" data-title="חומצה ולפרואית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Acidum_valproicum" title="Acidum valproicum – Latin" lang="la" hreflang="la" data-title="Acidum valproicum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Valproinsav" title="Valproinsav – Hungarian" lang="hu" hreflang="hu" data-title="Valproinsav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-min mw-list-item"><a href="https://min.wikipedia.org/wiki/Asam_valproat" title="Asam valproat – Minangkabau" lang="min" hreflang="min" data-title="Asam valproat" data-language-autonym="Minangkabau" data-language-local-name="Minangkabau" class="interlanguage-link-target"><span>Minangkabau</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Valpro%C3%AFnezuur" title="Valproïnezuur – Dutch" lang="nl" hreflang="nl" data-title="Valproïnezuur" 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%83%90%E3%83%AB%E3%83%97%E3%83%AD%E9%85%B8%E3%83%8A%E3%83%88%E3%83%AA%E3%82%A6%E3%83%A0" title="バルプロ酸ナトリウム – Japanese" lang="ja" hreflang="ja" data-title="バルプロ酸ナトリウム" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Valproat" title="Valproat – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Valproat" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%AD%E0%AC%BE%E0%AC%B2%E0%AC%AA%E0%AD%8D%E0%AC%B0%E0%AD%8B%E0%AC%8F%E0%AC%9F" title="ଭାଲପ୍ରୋଏଟ – Odia" lang="or" hreflang="or" data-title="ଭାଲପ୍ରୋଏଟ" 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/Kwas_walproinowy" title="Kwas walproinowy – Polish" lang="pl" hreflang="pl" data-title="Kwas walproinowy" 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/Valproato" title="Valproato – Portuguese" lang="pt" hreflang="pt" data-title="Valproato" 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/Acid_valproic" title="Acid valproic – Romanian" lang="ro" hreflang="ro" data-title="Acid valproic" 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%92%D0%B0%D0%BB%D1%8C%D0%BF%D1%80%D0%BE%D0%B5%D0%B2%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Вальпроевая кислота – Russian" lang="ru" hreflang="ru" data-title="Вальпроевая кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Valproate" title="Valproate – Simple English" lang="en-simple" hreflang="en-simple" data-title="Valproate" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Valproinska_kiselina" title="Valproinska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Valproinska kiselina" 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/Valproinska_kiselina" title="Valproinska kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Valproinska kiselina" 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/Valproaatti" title="Valproaatti – Finnish" lang="fi" hreflang="fi" data-title="Valproaatti" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Valproinsyra" title="Valproinsyra – Swedish" lang="sv" hreflang="sv" data-title="Valproinsyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Valproik_asit" title="Valproik asit – Turkish" lang="tr" hreflang="tr" data-title="Valproik asit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%92%D0%B0%D0%BB%D1%8C%D0%BF%D1%80%D0%BE%D1%94%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Вальпроєва кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Вальпроєва кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Valproate" title="Valproate – Vietnamese" lang="vi" hreflang="vi" data-title="Valproate" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E4%B8%99%E6%88%8A%E9%85%B8" title="丙戊酸 – Wu" lang="wuu" hreflang="wuu" data-title="丙戊酸" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E4%B8%99%E6%88%8A%E9%85%B8" title="丙戊酸 – Chinese" lang="zh" hreflang="zh" data-title="丙戊酸" data-language-autonym="中文" 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href="/w/index.php?title=Valproic_acid&redirect=no" class="mw-redirect" title="Valproic acid">Valproic acid</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Medication used for epilepsy, bipolar disorder and migraine</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">Valproate<br /><span style="font-size:85%; font-weight:normal;"><abbr title="International nonproprietary name">INN</abbr>:</span> valproic acid</caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2-propylpentanoic_acid_200.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/2-propylpentanoic_acid_200.svg/250px-2-propylpentanoic_acid_200.svg.png" decoding="async" width="250" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/2-propylpentanoic_acid_200.svg/375px-2-propylpentanoic_acid_200.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/2-propylpentanoic_acid_200.svg/500px-2-propylpentanoic_acid_200.svg.png 2x" data-file-width="211" data-file-height="81" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Valproic_acid-optimized-ball-and-stick-model.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Valproic_acid-optimized-ball-and-stick-model.png/250px-Valproic_acid-optimized-ball-and-stick-model.png" decoding="async" width="250" height="187" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/67/Valproic_acid-optimized-ball-and-stick-model.png/375px-Valproic_acid-optimized-ball-and-stick-model.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/67/Valproic_acid-optimized-ball-and-stick-model.png/500px-Valproic_acid-optimized-ball-and-stick-model.png 2x" data-file-width="3189" data-file-height="2381" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Depakote, Epilim, Convulex, <a href="#Formulations">others</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">VPA; valproic acid; sodium valproate (sodium); valproate semisodium (semisodium); 2-propylvaleric acid</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/valproic_acid.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/a682412.html">a682412</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=Valproic+acid">Valproic acid</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> D</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/Intravenous_therapy" title="Intravenous therapy">intravenous</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_N03" title="ATC code N03">N03AG01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N03AG01">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)</li> <li><small><abbr class="country-name" title="Brazil">BR</abbr>:</small> <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act#Class_C1" title="Brazilian Controlled Drugs and Substances Act">Class C1</a> (Other controlled substances)<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></li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_1-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>Rx-only<sup id="cite_ref-Depakote_FDA_label_4-0" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Depakote_ER_FDA_label_5-0" class="reference"><a href="#cite_note-Depakote_ER_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">Rapid absorption</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">80–90%<sup id="cite_ref-MSR_6-0" class="reference"><a href="#cite_note-MSR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a>—<a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronide conjugation</a> 30–50%, <a href="/wiki/Mitochondrial_%CE%B2-oxidation" class="mw-redirect" title="Mitochondrial β-oxidation">mitochondrial β-oxidation</a> over 40%</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">9–16 hours<sup id="cite_ref-MSR_6-1" class="reference"><a href="#cite_note-MSR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data">Urine (30–50%)<sup id="cite_ref-MSR_6-2" class="reference"><a href="#cite_note-MSR-6"><span class="cite-bracket">[</span>6<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%;">2-propylpentanoic acid</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=99-66-1">99-66-1</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/3121">3121</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=7009">7009</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/DB00313">DB00313</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.3009.html">3009</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/614OI1Z5WI">614OI1Z5WI</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/D00399">D00399</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:39867">CHEBI:39867</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/ChEMBL109">ChEMBL109</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/NIAID_ChemDB" title="NIAID ChemDB">NIAID ChemDB</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemdb.niaid.nih.gov"><a rel="nofollow" class="external text" href="https://chemdb.niaid.nih.gov/CompoundDetails.aspx?AIDSNO=057177">057177</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/DTXSID6023733">DTXSID6023733</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q240642#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/100.002.525">100.002.525</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q240642#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>8</sub><span title="Hydrogen">H</span><sub>16</sub><span title="Oxygen">O</span><sub>2</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="7002144214000000000♠"></span>144.214</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%28O%29C%28CCC%29CCC">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O=C(O)C(CCC)CCC</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/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)<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:NIJJYAXOARWZEE-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477003327&page2=Valproate">(verify)</a></span></span></td></tr></tbody></table> <p><b>Valproate</b> (<b>valproic acid</b>, <b>VPA</b>, <b>sodium valproate</b>, and <b>valproate semisodium</b> forms) are medications primarily used to treat <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a> and <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a> and prevent <a href="/wiki/Migraine_headache" class="mw-redirect" title="Migraine headache">migraine headaches</a>.<sup id="cite_ref-AHFS2015_7-0" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> They are useful for the prevention of seizures in those with <a href="/wiki/Absence_seizure" title="Absence seizure">absence seizures</a>, <a href="/wiki/Partial_seizure" class="mw-redirect" title="Partial seizure">partial seizures</a>, and <a href="/wiki/Generalized_seizure" class="mw-redirect" title="Generalized seizure">generalized seizures</a>.<sup id="cite_ref-AHFS2015_7-1" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> They can be given <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenously</a> or by mouth, and the tablet forms exist in both long- and short-acting formulations.<sup id="cite_ref-AHFS2015_7-2" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Common side effects of valproate include nausea, vomiting, <a href="/wiki/Somnolence" title="Somnolence">somnolence</a>, and dry mouth.<sup id="cite_ref-AHFS2015_7-3" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Serious side effects can include <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">liver failure</a>, and regular monitoring of <a href="/wiki/Liver_function_test" class="mw-redirect" title="Liver function test">liver function tests</a> is therefore recommended.<sup id="cite_ref-AHFS2015_7-4" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Other serious risks include <a href="/wiki/Pancreatitis" title="Pancreatitis">pancreatitis</a> and an increased <a href="/wiki/Suicide" title="Suicide">suicide</a> risk.<sup id="cite_ref-AHFS2015_7-5" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Valproate is known to cause serious abnormalities or birth defects in the unborn child if taken during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>,<sup id="cite_ref-AHFS2015_7-6" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> and is contra-indicated for women of childbearing age unless the drug is essential to their medical condition and the person is also prescribed a <a href="/wiki/Contraceptive" class="mw-redirect" title="Contraceptive">contraceptive</a>.<sup id="cite_ref-AHFS2015_7-7" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Depakote_FDA_label_4-1" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Reproductive warnings have also been issued for men using the drug.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/United_States_Food_and_Drug_Administration" class="mw-redirect" title="United States Food and Drug Administration">United States Food and Drug Administration</a> has indicated a <a href="/wiki/Black_box_warning" class="mw-redirect" title="Black box warning">black box warning</a> given the frequency and severity of the side effects and <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogenicity</a>.<sup id="cite_ref-Depakote_FDA_label_4-2" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Additionally, there is also a black box warning due to risk of <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a> and pancreatitis.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> As of 2022 the drug was still prescribed in the UK to potentially pregnant women, but use declined by 51% from 2018–19 to 2020–21.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Valproate's precise mechanism of action is unclear.<sup id="cite_ref-AHFS2015_7-8" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Owen2003_13-0" class="reference"><a href="#cite_note-Owen2003-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Proposed mechanisms include affecting <a href="/wiki/GABA" title="GABA">GABA</a> levels, blocking <a href="/wiki/Voltage-gated_sodium_channel" title="Voltage-gated sodium channel">voltage-gated sodium channels</a>, inhibiting <a href="/wiki/Histone_deacetylase" title="Histone deacetylase">histone deacetylases</a>, and increasing <a href="/wiki/Lymphoid_enhancer-binding_factor_1" title="Lymphoid enhancer-binding factor 1">LEF1</a>.<sup id="cite_ref-Gh2013_14-0" class="reference"><a href="#cite_note-Gh2013-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><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> Valproic acid is a branched <a href="/wiki/Short-chain_fatty_acid" title="Short-chain fatty acid">short-chain fatty acid</a> (SCFA), a <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivative</a> of <a href="/wiki/Valeric_acid" title="Valeric acid">valeric acid</a>.<sup id="cite_ref-Gh2013_14-1" class="reference"><a href="#cite_note-Gh2013-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Valproate was originally synthesized in 1881 and came into medical use in 1962.<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> It is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<sup id="cite_ref-WHO23rd_18-0" class="reference"><a href="#cite_note-WHO23rd-18"><span class="cite-bracket">[</span>18<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>.<sup id="cite_ref-AHFS2015_7-9" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In 2022, it was the 174th most commonly prescribed medication in the United States, with more than 2<span class="nowrap"> </span>million prescriptions.<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><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </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=Valproate&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Depakote_500mg_ER.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Depakote_500mg_ER.jpg/250px-Depakote_500mg_ER.jpg" decoding="async" width="250" height="250" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Depakote_500mg_ER.jpg/375px-Depakote_500mg_ER.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Depakote_500mg_ER.jpg/500px-Depakote_500mg_ER.jpg 2x" data-file-width="2248" data-file-height="2248" /></a><figcaption>500mg tablets of Depakote extended-release</figcaption></figure> <p>Valproate or valproic acid is used primarily to treat <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a> and <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a> and to prevent <a href="/wiki/Migraine_headache" class="mw-redirect" title="Migraine headache">migraine headaches</a>.<sup id="cite_ref-AMH_21-0" class="reference"><a href="#cite_note-AMH-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Epilepsy">Epilepsy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=2" title="Edit section: Epilepsy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Valproate has a broad spectrum of <a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a> activity, although it is primarily used as a first-line treatment for <a href="/wiki/Tonic%E2%80%93clonic_seizures" class="mw-redirect" title="Tonic–clonic seizures">tonic–clonic seizures</a>, <a href="/wiki/Absence_seizures" class="mw-redirect" title="Absence seizures">absence seizures</a> and <a href="/wiki/Myoclonic_seizures" class="mw-redirect" title="Myoclonic seizures">myoclonic seizures</a> and as a second-line treatment for <a href="/wiki/Partial_seizures" class="mw-redirect" title="Partial seizures">partial seizures</a> and <a href="/wiki/Infantile_spasms" class="mw-redirect" title="Infantile spasms">infantile spasms</a>.<sup id="cite_ref-AMH_21-1" class="reference"><a href="#cite_note-AMH-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> It has also been successfully given <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenously</a> to treat <a href="/wiki/Status_epilepticus" title="Status epilepticus">status epilepticus</a>.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><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>In the US, valproic acid is also prescribed as an anti-epileptic drug <a href="/wiki/Indicated" class="mw-redirect" title="Indicated">indicated</a> for the treatment of manic episodes associated with bipolar disorder; monotherapy and adjunctive therapy of complex partial seizures and simple and complex absence seizures; adjunctive therapy in people with multiple seizure types that include absence seizures.<sup id="cite_ref-Depakote_FDA_label_4-3" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Depakote_ER_FDA_label_5-1" class="reference"><a href="#cite_note-Depakote_ER_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Mental_illness">Mental illness</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=3" title="Edit section: Mental illness"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Valproate products are used to treat manic or mixed episodes of <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a>.<sup id="cite_ref-:1_25-0" class="reference"><a href="#cite_note-:1-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>A 2016 <a href="/wiki/Systematic_review" title="Systematic review">systematic review</a> compared the efficacy of valproate as an add-on for people with <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a>:<sup id="cite_ref-Wan2016_27-0" class="reference"><a href="#cite_note-Wan2016-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <tbody><tr> <td>There is limited evidence that adding valproate to <a href="/wiki/Antipsychotic" title="Antipsychotic">antipsychotics</a> may be effective for overall response and also for specific symptoms, especially in terms of excitement and aggression. Valproate was associated with a number of adverse events among which sedation and dizziness appeared more frequently than in the control groups.<sup id="cite_ref-Wan2016_27-1" class="reference"><a href="#cite_note-Wan2016-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding:0;"> <table class="wikitable collapsible collapsed" style="width:100%;"> <tbody><tr> <th scope="col" style="text-align: left;">Outcome </th> <th scope="col" style="text-align: left;">Findings in words </th> <th scope="col" style="text-align: left;">Findings in numbers </th> <th scope="col" style="text-align: left;">Quality of evidence </th></tr> <tr> <th colspan="4" style="text-align: left;">Global outcome </th></tr> <tr> <td>Clinically significant response</td> <td>When added to antipsychotic drugs valproate probably increases the chance of improvement. Data are based on moderate quality evidence. </td> <td><a href="/wiki/Relative_risk" title="Relative risk">RR</a> 1.31 (1.16 to 1.47)</td> <td><a href="/wiki/The_Grading_of_Recommendations_Assessment,_Development_and_Evaluation_(GRADE)_approach" class="mw-redirect" title="The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach">Moderate</a> </td></tr> <tr> <td>Leaving the study early for any reason</td> <td>Valproate in combination with antipsychotics may slightly reduce the chance of leaving the study early, but the difference between the two treatments is not clear. Data supporting this finding are based on moderate quality evidence. </td> <td>RR 0.76 (0.47 to 1.24)</td> <td><a href="/wiki/The_Grading_of_Recommendations_Assessment,_Development_and_Evaluation_(GRADE)_approach" class="mw-redirect" title="The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach">Moderate</a> </td></tr> <tr> <td>Use of additional medication for sedation</td> <td>The combination of valproate and antipsychotic drugs may increase the chance of being given additional sedating medication, but, at present it is not possible to be confident about the difference between the two treatments and data supporting this finding are very limited. </td> <td>RR 3.65 (0.11 to 122.31)</td> <td><a href="/wiki/The_Grading_of_Recommendations_Assessment,_Development_and_Evaluation_(GRADE)_approach" class="mw-redirect" title="The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach">Very low</a> </td></tr> <tr> <th colspan="4" style="text-align: left;"><a href="/wiki/Mental_health" title="Mental health">Mental state</a> </th></tr> <tr> <td>Average score (<a href="/wiki/Positive_and_Negative_Syndrome_Scale" title="Positive and Negative Syndrome Scale">PANSS</a> total, high = poor)</td> <td>On average, people receiving the valproate combination scored lower (better) than people treated with antipsychotics in combination with placebo or antipsychotic drugs alone. There was a clear difference between the groups, but the meaning of this in day-to-day care is unclear.</td> <td><a href="/wiki/Mean_absolute_difference" title="Mean absolute difference">MD</a> 5.85 lower (7.8 lower to 3.91 lower)</td> <td><a href="/wiki/The_Grading_of_Recommendations_Assessment,_Development_and_Evaluation_(GRADE)_approach" class="mw-redirect" title="The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach">Moderate</a> </td></tr> <tr> <th colspan="4" style="text-align: left;"><a href="/wiki/Adverse_event" title="Adverse event">Adverse events</a> </th></tr> <tr> <td>Abnormal liver function (blood test changes)*</td> <td>Adding valproate to antipsychotic drug treatment does not clearly cause liver problems. Data supporting this finding are based on moderate quality evidence. </td> <td>RR 1.26 (0.72 to 2.22)</td> <td><a href="/wiki/The_Grading_of_Recommendations_Assessment,_Development_and_Evaluation_(GRADE)_approach" class="mw-redirect" title="The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach">Moderate</a> </td></tr> <tr> <td>Nausea</td> <td>Adding valproate to antipsychotic drugs probably causes little or no increase to the chance of feeling sick, but the difference between the two treatments is not clear. Data supporting this finding are based on moderate quality evidence. </td> <td>RR 1.22 (0.80 to 1.86)</td> <td><a href="/wiki/The_Grading_of_Recommendations_Assessment,_Development_and_Evaluation_(GRADE)_approach" class="mw-redirect" title="The Grading of Recommendations Assessment, Development and Evaluation (GRADE) approach">Moderate</a> </td></tr> <tr> <th colspan="4" style="text-align: left;">Missing outcomes and notes </th></tr> <tr> <td></td> <td><a href="/wiki/Quality_of_life" title="Quality of life">Quality of life</a> outcomes were not reported in the included studies. <br />*Increase in alanine transaminase/gamma-glutamyl transpeptidase</td> <td></td> <td> </td></tr> </tbody></table> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Other_neurological_indications">Other neurological indications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=4" title="Edit section: Other neurological indications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Based upon five case reports, valproic acid may have efficacy in controlling the symptoms of the <a href="/wiki/Dopamine_dysregulation_syndrome" title="Dopamine dysregulation syndrome">dopamine dysregulation syndrome</a> that arise from the treatment of <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a> with <a href="/wiki/Levodopa" title="Levodopa">levodopa</a>.<sup id="cite_ref-pmid25114917_28-0" class="reference"><a href="#cite_note-pmid25114917-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid24288035_29-0" class="reference"><a href="#cite_note-pmid24288035-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid24313567_30-0" class="reference"><a href="#cite_note-pmid24313567-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>Valproate is not commonly used to prevent or treat <a href="/wiki/Migraine" title="Migraine">migraine headaches</a>, but it may be prescribed if other medications are not effective.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=5" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The medication has been tested in the treatment of <a href="/wiki/AIDS" class="mw-redirect" title="AIDS">AIDS</a> and <a href="/wiki/Cancer" title="Cancer">cancer</a>, owing to its <a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">histone-deacetylase-inhibiting effects</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. (November 2024)">citation needed</span></a></i>]</sup> It has cardioprotective, kidney protective, antiinflammatory, and antimicrobial effects.<sup id="cite_ref-elsevier_32-0" class="reference"><a href="#cite_note-elsevier-32"><span class="cite-bracket">[</span>32<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=Valproate&action=edit&section=6" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Contraindications include: </p> <ul><li>Pre-existing acute or chronic liver dysfunction or family history of severe <a href="/wiki/Hepatitis" title="Hepatitis">liver inflammation</a> (hepatitis), particularly medicine related.<sup id="cite_ref-TGA_33-0" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Pregnancy" title="Pregnancy">Pregnancy</a> 11% risk of birth defects and 30-40% risk of neuro-developmental disabilities which can be permanent<sup id="cite_ref-Birth_defects_34-0" class="reference"><a href="#cite_note-Birth_defects-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup></li> <li>Known <a href="/wiki/Hypersensitivity" title="Hypersensitivity">hypersensitivity</a> to valproate or any of the ingredients used in the preparation<sup id="cite_ref-TGA_33-1" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Urea_cycle_disorders" class="mw-redirect" title="Urea cycle disorders">Urea cycle disorders</a><sup id="cite_ref-TGA_33-2" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li>Hepatic <a href="/wiki/Porphyria" title="Porphyria">porphyria</a><sup id="cite_ref-TGA_33-3" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li>Hepatotoxicity<sup id="cite_ref-TGA_33-4" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Mitochondrial_disease" title="Mitochondrial disease">Mitochondrial disease</a><sup id="cite_ref-TGA_33-5" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Pancreatitis" title="Pancreatitis">Pancreatitis</a><sup id="cite_ref-TGA_33-6" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Porphyria" title="Porphyria">Porphyria</a><sup id="cite_ref-EMC_35-0" class="reference"><a href="#cite_note-EMC-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=7" title="Edit section: Adverse effects"><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/List_of_adverse_effects_of_valproate" title="List of adverse effects of valproate">List of adverse effects of valproate</a> and <a href="/wiki/List_of_adverse_effects_of_valproate_semisodium" title="List of adverse effects of valproate semisodium">List of adverse effects of valproate semisodium</a></div> <style data-mw-deduplicate="TemplateStyles:r1184024115">.mw-parser-output .div-col{margin-top:0.3em;column-width:30em}.mw-parser-output .div-col-small{font-size:90%}.mw-parser-output .div-col-rules{column-rule:1px solid #aaa}.mw-parser-output .div-col dl,.mw-parser-output .div-col ol,.mw-parser-output .div-col ul{margin-top:0}.mw-parser-output .div-col li,.mw-parser-output .div-col dd{page-break-inside:avoid;break-inside:avoid-column}</style><div class="div-col" style="column-width: 30em;"> <p>Most common adverse effects include:<sup id="cite_ref-Depakote_FDA_label_4-4" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Nausea (22%)</li> <li><a href="/wiki/Somnolence" title="Somnolence">Drowsiness</a> (19%)</li> <li>Dizziness (12%)</li> <li>Vomiting (12%)</li> <li><a href="/wiki/Weakness" title="Weakness">Weakness</a> (10%)</li></ul> <p>Serious adverse effects include:<sup id="cite_ref-Depakote_FDA_label_4-5" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Bleeding</li> <li><a href="/wiki/Thrombocytopenia" title="Thrombocytopenia">Low blood platelets</a></li> <li><a href="/wiki/Encephalopathy" title="Encephalopathy">Encephalopathy</a></li> <li>Suicidal behavior and thoughts</li> <li><a href="/wiki/Hypothermia" title="Hypothermia">Low body temperature</a></li></ul> </div> <p>Valproic acid has a <a href="/wiki/Black_box_warning" class="mw-redirect" title="Black box warning">black box warning</a> for <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>, <a href="/wiki/Pancreatitis" title="Pancreatitis">pancreatitis</a>, and fetal abnormalities.<sup id="cite_ref-Depakote_FDA_label_4-6" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>There is evidence that valproic acid may cause premature growth plate <a href="/wiki/Ossification" title="Ossification">ossification</a> in children and adolescents, resulting in decreased height.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Valproic acid can also cause <a href="/wiki/Mydriasis" title="Mydriasis">mydriasis</a>, a dilation of the pupils.<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> There is evidence that shows valproic acid may increase the chance of <a href="/wiki/Polycystic_ovary_syndrome" title="Polycystic ovary syndrome">polycystic ovary syndrome</a> (PCOS) in women with epilepsy or bipolar disorder. Studies have shown this risk of PCOS is higher in women with epilepsy compared to those with bipolar disorder.<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> Weight gain is also possible.<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-heading3"><h3 id="Pregnancy">Pregnancy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=8" title="Edit section: Pregnancy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="excerpt-block"><style data-mw-deduplicate="TemplateStyles:r1066933788">.mw-parser-output .excerpt-hat .mw-editsection-like{font-style:normal}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable dablink excerpt-hat selfref">This section is an excerpt from <a href="/wiki/Fetal_valproate_spectrum_disorder" title="Fetal valproate spectrum disorder">Fetal valproate spectrum disorder</a>.<span class="mw-editsection-like plainlinks"><span class="mw-editsection-bracket">[</span><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Fetal_valproate_spectrum_disorder&action=edit">edit</a><span class="mw-editsection-bracket">]</span></span></div><div class="excerpt"> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Minor_Limb_Malformations_Seen_After_Valproate_Exposure.webp" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Minor_Limb_Malformations_Seen_After_Valproate_Exposure.webp/220px-Minor_Limb_Malformations_Seen_After_Valproate_Exposure.webp.png" decoding="async" width="220" height="56" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Minor_Limb_Malformations_Seen_After_Valproate_Exposure.webp/330px-Minor_Limb_Malformations_Seen_After_Valproate_Exposure.webp.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Minor_Limb_Malformations_Seen_After_Valproate_Exposure.webp/440px-Minor_Limb_Malformations_Seen_After_Valproate_Exposure.webp.png 2x" data-file-width="1946" data-file-height="498" /></a><figcaption>Minor limb <a href="/wiki/Malformations" class="mw-redirect" title="Malformations">malformations</a> seen after valproate exposure</figcaption></figure> <a href="/wiki/Fetal_valproate_spectrum_disorder" title="Fetal valproate spectrum disorder">Fetal valproate spectrum disorder</a> (FVSD), previously known as fetal valproate syndrome (FVS), is a <a href="/wiki/Rare_disease" title="Rare disease">rare disease</a> caused by prenatal exposure to <a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">valproic acid</a> (VPA), a medication commonly used to treat <a href="/wiki/Epilepsy" title="Epilepsy">epilepsy</a>, <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a>, and <a href="/wiki/Migraine" title="Migraine">migraines</a>. This exposure can lead to a range of <a href="/wiki/Neurodevelopmental" class="mw-redirect" title="Neurodevelopmental">neurodevelopmental</a> and physical symptoms, including <a href="/wiki/Cognitive_impairment" title="Cognitive impairment">cognitive impairments</a>, <a href="/wiki/Developmental_delays" class="mw-redirect" title="Developmental delays">developmental delays</a>, <a href="/wiki/Autism_spectrum_disorder" class="mw-redirect" title="Autism spectrum disorder">autism spectrum disorder</a> (ASD), <a href="/wiki/Attention_deficit_hyperactivity_disorder" title="Attention deficit hyperactivity disorder">attention deficit hyperactivity disorder</a> (ADHD), and <a href="/wiki/Congenital_malformations" class="mw-redirect" title="Congenital malformations">congenital malformations</a>.<sup id="cite_ref-Fetal_valproate_spectrum_disorder_GARD_42-0" class="reference"><a href="#cite_note-Fetal_valproate_spectrum_disorder_GARD-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fetal_valproate_spectrum_disorder_Orphanet_43-0" class="reference"><a href="#cite_note-Fetal_valproate_spectrum_disorder_Orphanet-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Fetal_valproate_spectrum_disorder_Clayton-Smith_-_2019_44-0" class="reference"><a href="#cite_note-Fetal_valproate_spectrum_disorder_Clayton-Smith_-_2019-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup></div></div> <div class="mw-heading mw-heading3"><h3 id="Elderly">Elderly</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=9" title="Edit section: Elderly"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Valproate may cause increased somnolence in the elderly. In a trial of valproate in elderly patients with <a href="/wiki/Dementia" title="Dementia">dementia</a>, a significantly higher portion of valproate patients had somnolence compared to placebo. In approximately one-half of such patients, there was associated reduced nutritional intake and weight loss.<sup id="cite_ref-Depakote_FDA_label_4-7" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Overdose_and_toxicity">Overdose and toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=10" title="Edit section: Overdose and toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable" align="right"> <caption>Therapeutic range of valproic acid </caption> <tbody><tr> <td><b>Form</b> </td> <td><b>Lower limit</b> </td> <td><b>Upper limit</b> </td> <td><b>Unit</b> </td></tr> <tr> <td rowspan="2">Total (including<br /> <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">protein bound</a>) </td> <td>50<sup id="cite_ref-mass_45-0" class="reference"><a href="#cite_note-mass-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></td> <td>125<sup id="cite_ref-mass_45-1" class="reference"><a href="#cite_note-mass-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></td> <td>μg/mL or mg/L </td></tr> <tr> <td>350<sup id="cite_ref-molar_46-0" class="reference"><a href="#cite_note-molar-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup></td> <td>700<sup id="cite_ref-molar_46-1" class="reference"><a href="#cite_note-molar-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup></td> <td>μmol/L </td></tr> <tr> <td rowspan="2">Free </td> <td>6<sup id="cite_ref-mass_45-2" class="reference"><a href="#cite_note-mass-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></td> <td>22<sup id="cite_ref-mass_45-3" class="reference"><a href="#cite_note-mass-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup></td> <td>μg/mL or mg/L </td></tr> <tr> <td>35<sup id="cite_ref-molar_46-2" class="reference"><a href="#cite_note-molar-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup></td> <td>70<sup id="cite_ref-molar_46-3" class="reference"><a href="#cite_note-molar-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup></td> <td>μmol/L </td></tr></tbody></table> <p>Excessive amounts of valproic acid can result in somnolence, <a href="/wiki/Tremor" title="Tremor">tremor</a>, <a href="/wiki/Stupor" title="Stupor">stupor</a>, <a href="/wiki/Respiratory_depression" class="mw-redirect" title="Respiratory depression">respiratory depression</a>, <a href="/wiki/Coma" title="Coma">coma</a>, <a href="/wiki/Metabolic_acidosis" title="Metabolic acidosis">metabolic acidosis</a>, and death. In general, serum or plasma valproic acid concentrations are in a range of 20–100 mg/L during controlled therapy, but may reach 150–1500 mg/L following acute poisoning. Monitoring of the serum level is often accomplished using commercial immunoassay techniques, although some laboratories employ <a href="/wiki/Chromatography" title="Chromatography">gas or liquid chromatography.</a><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> In contrast to other <a href="/wiki/Antiepileptic_drugs" class="mw-redirect" title="Antiepileptic drugs">antiepileptic drugs</a>, at present there is little favorable evidence for salivary therapeutic drug monitoring. Salivary levels of valproic acid correlate poorly with serum levels, partly due to valproate's weak acid property (p<i>K</i>a of 4.9).<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>In severe intoxication, <a href="/wiki/Hemoperfusion" title="Hemoperfusion">hemoperfusion</a> or <a href="/wiki/Hemofiltration" title="Hemofiltration">hemofiltration</a> can be an effective means of hastening elimination of the drug from the body.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Supportive therapy should be given to all patients experiencing an overdose and urine output should be monitored.<sup id="cite_ref-Depakote_FDA_label_4-8" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Supplemental <a href="/wiki/Carnitine" title="Carnitine"><small>L</small>-carnitine</a> is indicated in patients having an acute overdose<sup id="cite_ref-pmid16277730_51-0" class="reference"><a href="#cite_note-pmid16277730-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> and also <a href="/wiki/Preventive_medicine" class="mw-redirect" title="Preventive medicine">prophylactically</a><sup id="cite_ref-pmid16277730_51-1" class="reference"><a href="#cite_note-pmid16277730-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> in high risk patients. <a href="/wiki/Acetylcarnitine" title="Acetylcarnitine">Acetyl-<small>L</small>-carnitine</a> lowers <a href="/wiki/Hyperammonemia" title="Hyperammonemia">hyperammonemia</a> less markedly<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> than <a href="/wiki/Carnitine" title="Carnitine"><small>L</small>-carnitine</a>. </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=Valproate&action=edit&section=11" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Valproate inhibits <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a>, <a href="/wiki/Glucuronyl_transferase" class="mw-redirect" title="Glucuronyl transferase">glucuronyl transferase</a>, and <a href="/wiki/Epoxide_hydrolase" title="Epoxide hydrolase">epoxide hydrolase</a> and is highly protein bound and hence may interact with drugs that are substrates for any of these enzymes or are highly protein bound themselves.<sup id="cite_ref-TGA_33-7" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> It may also potentiate the CNS depressant effects of alcohol.<sup id="cite_ref-TGA_33-8" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> It should not be given in conjunction with other antiepileptics due to the potential for reduced clearance of other antiepileptics (including <a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a>, <a href="/wiki/Lamotrigine" title="Lamotrigine">lamotrigine</a>, <a href="/wiki/Phenytoin" title="Phenytoin">phenytoin</a> and <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbitone</a>) and itself.<sup id="cite_ref-TGA_33-9" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> It may also interact with:<sup id="cite_ref-Depakote_FDA_label_4-9" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-TGA_33-10" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Aspirin" title="Aspirin">Aspirin</a>: may increase valproate concentrations. May also interfere with valproate's metabolism.</li> <li><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a>: may cause CNS depression and there are possible pharmacokinetic interactions.</li> <li><a href="/wiki/Carbapenem" title="Carbapenem">Carbapenem</a> antibiotics: reduce valproate levels, potentially leading to seizures.</li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a>: inhibits valproate's metabolism in the liver, leading to increased valproate concentrations.</li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a>: inhibits valproate's metabolism in the liver, leading to increased valproate concentrations.</li> <li><a href="/wiki/Ethosuximide" title="Ethosuximide">Ethosuximide</a>: valproate may increase ethosuximide concentrations and lead to toxicity.</li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a>: may increase plasma concentrations of valproate.</li> <li><a href="/wiki/Mefloquine" title="Mefloquine">Mefloquine</a>: may increase valproate metabolism combined with the direct <a href="/wiki/Epileptogenic" class="mw-redirect" title="Epileptogenic">epileptogenic</a> effects of mefloquine.</li> <li><a href="/wiki/Oral_contraceptive_pill" title="Oral contraceptive pill">Oral contraceptives</a>: may reduce plasma concentrations of valproate.</li> <li><a href="/wiki/Primidone" title="Primidone">Primidone</a>: may accelerate metabolism of valproate, leading to a decline of serum levels and potential <a href="/wiki/Breakthrough_seizure" class="mw-redirect" title="Breakthrough seizure">breakthrough seizure</a>.</li> <li><a href="/wiki/Rifampicin" title="Rifampicin">Rifampicin</a>: increases the clearance of valproate, leading to decreased valproate concentrations.</li> <li><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a>: valproate may increase free warfarin concentration and prolong bleeding time.</li> <li><a href="/wiki/Zidovudine" title="Zidovudine">Zidovudine</a>: valproate may increase zidovudine serum concentration and lead to toxicity.</li></ul> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=12" 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=Valproate&action=edit&section=13" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although the mechanism of action of valproate is not fully understood,<sup id="cite_ref-TGA_33-11" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> traditionally, its anticonvulsant effect has been attributed to the blockade of <a href="/wiki/Voltage-gated_sodium_channel" title="Voltage-gated sodium channel">voltage-gated sodium channels</a> and increased brain levels of the inhibitory synaptic neurotransmitter <a href="/wiki/Gamma-Aminobutyric_acid" class="mw-redirect" title="Gamma-Aminobutyric acid">gamma-aminobutyric acid</a> (GABA).<sup id="cite_ref-TGA_33-12" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The GABAergic effect is also believed to contribute towards the anti-manic properties of valproate.<sup id="cite_ref-TGA_33-13" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> In animals, sodium valproate raises cerebral and cerebellar levels of GABA, possibly by inhibiting GABA degradative enzymes, such as <a href="/wiki/GABA_transaminase" class="mw-redirect" title="GABA transaminase">GABA transaminase</a>, <a href="/wiki/Succinate-semialdehyde_dehydrogenase" title="Succinate-semialdehyde dehydrogenase">succinate-semialdehyde dehydrogenase</a> and by inhibiting the re-uptake of GABA by neuronal cells.<sup id="cite_ref-TGA_33-14" class="reference"><a href="#cite_note-TGA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Prevention of neurotransmitter-induced hyperexcitability of nerve cells via <a href="/wiki/KvLQT2" title="KvLQT2">Kv7.2 channel</a> and <a href="/wiki/AKAP5" title="AKAP5">AKAP5</a> may also contribute to its mechanism.<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> Valproate has been shown to protect against a seizure-induced reduction in <a href="/wiki/Phosphatidylinositol_(3,4,5)-trisphosphate" title="Phosphatidylinositol (3,4,5)-trisphosphate">phosphatidylinositol (3,4,5)-trisphosphate</a> (PIP3) as a potential therapeutic mechanism.<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> </p><p>Valproate is a <a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">histone deacetylase inhibitor</a>. By inhibition of <a href="/wiki/Histone_deacetylase" title="Histone deacetylase">histone deacetylase</a>, it promotes more transcriptionally active chromatin structures, that is it exerts an epigenetic effect. This has been proven in mice: Valproic acid induced histone hyperacetylation had brain function effects on the next generation of mice through changes in sperm DNA methylation.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Intermediate molecules include <a href="/wiki/VEGF" class="mw-redirect" title="VEGF">VEGF</a>, <a href="/wiki/BDNF" class="mw-redirect" title="BDNF">BDNF</a>, and <a href="/wiki/GDNF" class="mw-redirect" title="GDNF">GDNF</a>.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Therapeutic_potential_of_mood_stabi_59-0" class="reference"><a href="#cite_note-Therapeutic_potential_of_mood_stabi-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Endocrine_actions">Endocrine actions</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=14" title="Edit section: Endocrine actions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Valproic acid has been found to be an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen</a> and <a href="/wiki/Progesterone_receptor" title="Progesterone receptor">progesterone receptors</a>, and hence as a <a href="/wiki/Nonsteroidal" title="Nonsteroidal">nonsteroidal</a> <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogen</a> and <a href="/wiki/Antiprogestogen" title="Antiprogestogen">antiprogestogen</a>, at concentrations much lower than therapeutic serum levels.<sup id="cite_ref-pmid16165177_60-0" class="reference"><a href="#cite_note-pmid16165177-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> In addition, the drug has been identified as a potent <a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">aromatase inhibitor</a>, and suppresses <a href="/wiki/Estrogen" title="Estrogen">estrogen</a> concentrations.<sup id="cite_ref-WyllieCascino2012_61-0" class="reference"><a href="#cite_note-WyllieCascino2012-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> These actions are likely to be involved in the reproductive endocrine disturbances seen with valproic acid treatment.<sup id="cite_ref-pmid16165177_60-1" class="reference"><a href="#cite_note-pmid16165177-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WyllieCascino2012_61-1" class="reference"><a href="#cite_note-WyllieCascino2012-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>Valproic acid has been found to directly stimulate androgen biosynthesis in the <a href="/wiki/Gonad" title="Gonad">gonads</a> via inhibition of histone deacetylases and has been associated with <a href="/wiki/Hyperandrogenism" title="Hyperandrogenism">hyperandrogenism</a> in women and increased <a href="/wiki/4-androstenedione" class="mw-redirect" title="4-androstenedione">4-androstenedione</a> levels in men.<sup id="cite_ref-UchidaMaruyama2005_62-0" class="reference"><a href="#cite_note-UchidaMaruyama2005-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-IsojärviTaubøll2005_63-0" class="reference"><a href="#cite_note-IsojärviTaubøll2005-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> High rates of <a href="/wiki/Polycystic_ovary_syndrome" title="Polycystic ovary syndrome">polycystic ovary syndrome</a> and <a href="/wiki/Menstrual_disorder" title="Menstrual disorder">menstrual disorders</a> have also been observed in women treated with valproic acid.<sup id="cite_ref-IsojärviTaubøll2005_63-1" class="reference"><a href="#cite_note-IsojärviTaubøll2005-63"><span class="cite-bracket">[</span>63<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=Valproate&action=edit&section=15" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Valproic_acid_metabolism.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Valproic_acid_metabolism.svg/250px-Valproic_acid_metabolism.svg.png" decoding="async" width="250" height="319" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Valproic_acid_metabolism.svg/375px-Valproic_acid_metabolism.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Valproic_acid_metabolism.svg/500px-Valproic_acid_metabolism.svg.png 2x" data-file-width="349" data-file-height="446" /></a><figcaption>Some <a href="/wiki/Metabolites" class="mw-redirect" title="Metabolites">metabolites</a> of valproic acid. <a href="/wiki/Glucuronidation" title="Glucuronidation">Glucuronidation</a> and <a href="/wiki/%CE%92-oxidation" class="mw-redirect" title="Β-oxidation">β-oxidation</a> are the main metabolic pathways; <a href="/wiki/%CE%A9-oxidation" class="mw-redirect" title="Ω-oxidation">ω-oxidation</a> metabolites are considered <a href="/wiki/Hepatotoxic" class="mw-redirect" title="Hepatotoxic">hepatotoxic</a>.<sup id="cite_ref-AC_64-0" class="reference"><a href="#cite_note-AC-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> Details see text.</figcaption></figure> <p>Taken by mouth, valproate is rapidly and virtually completely absorbed from the gut.<sup id="cite_ref-AC_64-1" class="reference"><a href="#cite_note-AC-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> When in the bloodstream, 80–90% of the substance are bound to <a href="/wiki/Plasma_protein" title="Plasma protein">plasma proteins</a>, mainly <a href="/wiki/Albumin" title="Albumin">albumin</a>. Protein binding is saturable: it decreases with increasing valproate concentration, low albumin concentrations, the patient's age, additional use of other drugs such as <a href="/wiki/Aspirin" title="Aspirin">aspirin</a>, as well as liver and kidney impairment.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_67-0" class="reference"><a href="#cite_note-Drugs.com-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Concentrations in the <a href="/wiki/Cerebrospinal_fluid" title="Cerebrospinal fluid">cerebrospinal fluid</a> and in breast milk are 1 to 10% of blood plasma concentrations.<sup id="cite_ref-AC_64-2" class="reference"><a href="#cite_note-AC-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p><p>The vast majority of valproate <a href="/wiki/Drug_metabolism" title="Drug metabolism">metabolism</a> occurs in the <a href="/wiki/Liver" title="Liver">liver</a>.<sup id="cite_ref-Drugbank-Valproate_68-0" class="reference"><a href="#cite_note-Drugbank-Valproate-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> Valproate is known to be metabolized by the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> enzymes <a href="/wiki/CYP2A6" title="CYP2A6">CYP2A6</a>, <a href="/wiki/CYP2B6" title="CYP2B6">CYP2B6</a>, <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a>, and <a href="/wiki/CYP3A5" title="CYP3A5">CYP3A5</a>.<sup id="cite_ref-Drugbank-Valproate_68-1" class="reference"><a href="#cite_note-Drugbank-Valproate-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> It is also known to be metabolized by the <a href="/wiki/UDP-glucuronosyltransferase" class="mw-redirect" title="UDP-glucuronosyltransferase">UDP-glucuronosyltransferase</a> enzymes <a href="/wiki/UGT1A3" title="UGT1A3">UGT1A3</a>, <a href="/wiki/UGT1A4" title="UGT1A4">UGT1A4</a>, <a href="/wiki/UGT1A6" title="UGT1A6">UGT1A6</a>, <a href="/wiki/UGT1A8" title="UGT1A8">UGT1A8</a>, <a href="/wiki/UGT1A9" title="UGT1A9">UGT1A9</a>, <a href="/wiki/UGT1A10" title="UGT1A10">UGT1A10</a>, <a href="/wiki/UGT2B7" title="UGT2B7">UGT2B7</a>, and <a href="/wiki/UGT2B15" title="UGT2B15">UGT2B15</a>.<sup id="cite_ref-Drugbank-Valproate_68-2" class="reference"><a href="#cite_note-Drugbank-Valproate-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> Some of the known metabolites of valproate by these enzymes and uncharacterized enzymes include (see image):<sup id="cite_ref-Drugbank-Valproate_68-3" class="reference"><a href="#cite_note-Drugbank-Valproate-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p> <ul><li>via <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> (30–50%): valproic acid β-O-<a href="/wiki/Glucuronide" title="Glucuronide">glucuronide</a></li> <li>via <a href="/wiki/Beta_oxidation" title="Beta oxidation">beta oxidation</a> (>40%): 2<i>E</i>-ene-valproic acid, 2<i>Z</i>-ene-valproic acid, 3-hydroxyvalproic acid, 3-oxovalproic acid</li> <li>via <a href="/wiki/Omega_oxidation" title="Omega oxidation">omega oxidation</a>: 5-hydroxyvalproic acid, 2-propyl-glutaric acid</li> <li>some others: 3<i>E</i>-ene-valproic acid, 3<i>Z</i>-ene-valproic acid, 4-ene-valproic acid, 4-hydroxyvalproic acid</li></ul> <p>All in all, over 20 metabolites are known.<sup id="cite_ref-AC_64-3" class="reference"><a href="#cite_note-AC-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p><p>In adult patients taking valproate alone, 30–50% of an administered dose is excreted in <a href="/wiki/Urine" title="Urine">urine</a> as the glucuronide conjugate.<sup id="cite_ref-Drugbank-Valproate_68-4" class="reference"><a href="#cite_note-Drugbank-Valproate-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> The other major pathway in the metabolism of valproate is <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondrial</a> beta oxidation, which typically accounts for over 40% of an administered dose.<sup id="cite_ref-Drugbank-Valproate_68-5" class="reference"><a href="#cite_note-Drugbank-Valproate-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> Typically, less than 20% of an administered dose is eliminated by other oxidative mechanisms.<sup id="cite_ref-Drugbank-Valproate_68-6" class="reference"><a href="#cite_note-Drugbank-Valproate-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> Less than 3% of an administered dose of valproate is excreted unchanged (i.e., as valproate) in urine.<sup id="cite_ref-Drugbank-Valproate_68-7" class="reference"><a href="#cite_note-Drugbank-Valproate-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> Only a small amount is excreted via the faeces.<sup id="cite_ref-AC_64-4" class="reference"><a href="#cite_note-AC-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">Elimination half-life</a> is 16±3 hours and can decrease to 4–9 hours when combined with <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">enzyme inducers</a>.<sup id="cite_ref-AC_64-5" class="reference"><a href="#cite_note-AC-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_67-1" class="reference"><a href="#cite_note-Drugs.com-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=16" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Valproic acid is a branched <a href="/wiki/Short-chain_fatty_acid" title="Short-chain fatty acid">short-chain fatty acid</a> and the 2-<i>n</i>-<a href="/wiki/Propyl" class="mw-redirect" title="Propyl">propyl</a> derivative of <a href="/wiki/Valeric_acid" title="Valeric acid">valeric acid</a>.<sup id="cite_ref-Gh2013_14-2" class="reference"><a href="#cite_note-Gh2013-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=17" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Valproic acid was first synthesized in 1882 by <a href="/w/index.php?title=Beverly_S._Burton&action=edit&redlink=1" class="new" title="Beverly S. Burton (page does not exist)">Beverly S. Burton</a> as an <a href="/wiki/Analog_(chemistry)" class="mw-redirect" title="Analog (chemistry)">analogue</a> of <a href="/wiki/Valeric_acid" title="Valeric acid">valeric acid</a>, found naturally in <a href="/wiki/Valerian_(herb)" title="Valerian (herb)">valerian</a>.<sup id="cite_ref-69" class="reference"><a href="#cite_note-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> Valproic acid is a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a>, a clear liquid at room temperature. For many decades, its only use was in laboratories as a "metabolically inert" solvent for organic compounds. In 1962, the French researcher Pierre Eymard serendipitously discovered the anticonvulsant properties of valproic acid while using it as a vehicle for a number of other compounds that were being screened for antiseizure activity. He found it prevented <a href="/wiki/Pentylenetetrazol" title="Pentylenetetrazol">pentylenetetrazol</a>-induced convulsions in <a href="/wiki/Laboratory_rats" class="mw-redirect" title="Laboratory rats">laboratory rats</a>.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> It was approved as an antiepileptic drug in 1967 in France and has become the most widely prescribed antiepileptic drug worldwide.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> Valproic acid has also been used for migraine <a href="/wiki/Preventive_healthcare" title="Preventive healthcare">prophylaxis</a> and bipolar disorder.<sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>72<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=Valproate&action=edit&section=18" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Valproate is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<sup id="cite_ref-AHFS2015_7-10" class="reference"><a href="#cite_note-AHFS2015-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Approval_status">Approval status</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=19" title="Edit section: Approval status"><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-Update plainlinks metadata ambox ambox-content ambox-Update" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Ambox_current_red_Americas.svg/42px-Ambox_current_red_Americas.svg.png" decoding="async" width="42" height="34" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/53/Ambox_current_red_Americas.svg/63px-Ambox_current_red_Americas.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/53/Ambox_current_red_Americas.svg/84px-Ambox_current_red_Americas.svg.png 2x" data-file-width="360" data-file-height="290" /></span></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section needs to be <b>updated</b>.<span class="hide-when-compact"> Please help update this article to reflect recent events or newly available information.</span> <span class="date-container"><i>(<span class="date">February 2024</span>)</i></span></div></td></tr></tbody></table> <table class="wikitable"> <tbody><tr> <th>Indications </th> <th><span class="flagicon"><span class="mw-image-border" typeof="mw:File"><a href="/wiki/United_States" title="United States"><img alt="United States" src="//upload.wikimedia.org/wikipedia/en/thumb/a/a4/Flag_of_the_United_States.svg/23px-Flag_of_the_United_States.svg.png" decoding="async" width="23" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/a/a4/Flag_of_the_United_States.svg/35px-Flag_of_the_United_States.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/a/a4/Flag_of_the_United_States.svg/46px-Flag_of_the_United_States.svg.png 2x" data-file-width="1235" data-file-height="650" /></a></span></span><br /><a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">FDA</a>-labelled indication?<sup id="cite_ref-MSR_6-3" class="reference"><a href="#cite_note-MSR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </th> <th><span class="flagicon"><span class="mw-image-border" typeof="mw:File"><a href="/wiki/Australia" title="Australia"><img alt="Australia" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Flag_of_Australia_%28converted%29.svg/23px-Flag_of_Australia_%28converted%29.svg.png" decoding="async" width="23" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Flag_of_Australia_%28converted%29.svg/35px-Flag_of_Australia_%28converted%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/88/Flag_of_Australia_%28converted%29.svg/46px-Flag_of_Australia_%28converted%29.svg.png 2x" data-file-width="512" data-file-height="256" /></a></span></span><br /><a href="/wiki/Therapeutic_Goods_Administration" title="Therapeutic Goods Administration">TGA</a>-labelled indication?<sup id="cite_ref-AMH_21-2" class="reference"><a href="#cite_note-AMH-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </th> <th scope="col"><span class="flagicon"><span class="mw-image-border" typeof="mw:File"><a href="/wiki/United_Kingdom" title="United Kingdom"><img alt="United Kingdom" src="//upload.wikimedia.org/wikipedia/en/thumb/a/ae/Flag_of_the_United_Kingdom.svg/23px-Flag_of_the_United_Kingdom.svg.png" decoding="async" width="23" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/a/ae/Flag_of_the_United_Kingdom.svg/35px-Flag_of_the_United_Kingdom.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/a/ae/Flag_of_the_United_Kingdom.svg/46px-Flag_of_the_United_Kingdom.svg.png 2x" data-file-width="1200" data-file-height="600" /></a></span></span><br /><a href="/wiki/Medicines_and_Healthcare_products_Regulatory_Agency" title="Medicines and Healthcare products Regulatory Agency">MHRA</a>-labelled indication?<sup id="cite_ref-BNF_73-0" class="reference"><a href="#cite_note-BNF-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </th> <th>Literature support </th></tr> <tr> <td>Epilepsy</td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes</td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes</td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes</td> <td>Limited (depends on the seizure type; it can help with certain kinds of seizures: drug-resistant epilepsy, partial and absence seizures, can be used against <a href="/wiki/Glioblastoma" title="Glioblastoma">glioblastoma</a> and other tumors both to improve survival and treat seizures, and against <a href="/wiki/Tonic%E2%80%93clonic_seizures" class="mw-redirect" title="Tonic–clonic seizures">tonic–clonic seizures</a> and status epilepticus).<sup id="cite_ref-74" class="reference"><a href="#cite_note-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-76" class="reference"><a href="#cite_note-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-77" class="reference"><a href="#cite_note-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Bipolar mania</td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes</td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes</td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes</td> <td>Limited.<sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup><sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability"><span title="Cited source contains "Design/methodology/approach: Case notes from 43 (42 percent male) patients" which does not support the claim that there is limited literature support. (November 2023)">failed verification</span></a></i>]</sup> </td></tr> <tr> <td>Bipolar depression</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Moderate.<sup id="cite_ref-79" class="reference"><a href="#cite_note-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Bipolar maintenance</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Limited.<sup id="cite_ref-80" class="reference"><a href="#cite_note-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Migraine prophylaxis</td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes</td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes (accepted)</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Limited. </td></tr> <tr> <td>Acute migraine management</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Only negative results.<sup id="cite_ref-81" class="reference"><a href="#cite_note-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Schizophrenia</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Weak evidence.<sup id="cite_ref-82" class="reference"><a href="#cite_note-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Agitation in dementia</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Weak evidence. Not recommended for agitation in people with dementia.<sup id="cite_ref-:2_83-0" class="reference"><a href="#cite_note-:2-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> Increased rate of adverse effects, including a risk of serious adverse effects.<sup id="cite_ref-:2_83-1" class="reference"><a href="#cite_note-:2-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Fragile_X_syndrome" title="Fragile X syndrome">Fragile X syndrome</a></td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes (orphan)</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Limited.<sup id="cite_ref-Therapeutic_potential_of_mood_stabi_59-1" class="reference"><a href="#cite_note-Therapeutic_potential_of_mood_stabi-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Familial_adenomatous_polyposis" title="Familial adenomatous polyposis">Familial adenomatous polyposis</a></td> <td style="background:#9EFF9E;color:black;vertical-align:middle;text-align:center;" class="table-yes">Yes (orphan)</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Limited. </td></tr> <tr> <td>Chronic pain & fibromyalgia</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Limited.<sup id="cite_ref-84" class="reference"><a href="#cite_note-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Alcohol hallucinosis</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>One randomised double-blind placebo-controlled trial.<sup id="cite_ref-85" class="reference"><a href="#cite_note-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Intractable hiccups</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Limited, five case reports support its efficacy, however.<sup id="cite_ref-86" class="reference"><a href="#cite_note-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Non-epileptic myoclonus</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Limited, three case reports support its efficacy, however.<sup id="cite_ref-87" class="reference"><a href="#cite_note-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>Cluster headaches</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Limited, two case reports support its efficacy.<sup id="cite_ref-88" class="reference"><a href="#cite_note-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/West_syndrome" class="mw-redirect" title="West syndrome">West syndrome</a></td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>A prospective clinical trial supported its efficacy in treating infantile spasms.<sup id="cite_ref-89" class="reference"><a href="#cite_note-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td>HIV infection eradication</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Double-blind placebo-controlled trials have been negative.<sup id="cite_ref-90" class="reference"><a href="#cite_note-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-91" class="reference"><a href="#cite_note-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Myelodysplastic_syndrome" title="Myelodysplastic syndrome">Myelodysplastic syndrome</a></td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Several clinical trials have confirmed its efficacy as a monotherapy,<sup id="cite_ref-m2001_93-0" class="reference"><a href="#cite_note-m2001-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> as an adjunct to <a href="/wiki/Tretinoin" title="Tretinoin">tretinoin</a><sup id="cite_ref-m2001_93-1" class="reference"><a href="#cite_note-m2001-93"><span class="cite-bracket">[</span>93<span class="cite-bracket">]</span></a></sup> and as an adjunct to hydralazine.<sup id="cite_ref-94" class="reference"><a href="#cite_note-94"><span class="cite-bracket">[</span>94<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acute_myeloid_leukaemia" class="mw-redirect" title="Acute myeloid leukaemia">Acute myeloid leukaemia</a></td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Two clinical trials have confirmed its efficacy in this indication as both a monotherapy and as an adjunct to <a href="/wiki/Tretinoin" title="Tretinoin">tretinoin</a>.<sup id="cite_ref-95" class="reference"><a href="#cite_note-95"><span class="cite-bracket">[</span>95<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-96" class="reference"><a href="#cite_note-96"><span class="cite-bracket">[</span>96<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-97" class="reference"><a href="#cite_note-97"><span class="cite-bracket">[</span>97<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Cervical_cancer" title="Cervical cancer">Cervical cancer</a></td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>One clinical trial supports its use here.<sup id="cite_ref-98" class="reference"><a href="#cite_note-98"><span class="cite-bracket">[</span>98<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Malignant_melanoma" class="mw-redirect" title="Malignant melanoma">Malignant melanoma</a></td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>One phase II study has seemed to discount its efficacy.<sup id="cite_ref-99" class="reference"><a href="#cite_note-99"><span class="cite-bracket">[</span>99<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Breast_cancer" title="Breast cancer">Breast cancer</a></td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>A phase II study has supported its efficacy.<sup id="cite_ref-100" class="reference"><a href="#cite_note-100"><span class="cite-bracket">[</span>100<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Impulse_control_disorder" class="mw-redirect" title="Impulse control disorder">Impulse control disorder</a></td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td style="background:#FFC7C7;color:black;vertical-align:middle;text-align:center;" class="table-no">No</td> <td>Limited.<sup id="cite_ref-Hicks_101-0" class="reference"><a href="#cite_note-Hicks-101"><span class="cite-bracket">[</span>101<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-102" class="reference"><a href="#cite_note-102"><span class="cite-bracket">[</span>102<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <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=Valproate&action=edit&section=20" title="Edit section: Off-label uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2012, pharmaceutical company <a href="/wiki/Abbott_Laboratories" title="Abbott Laboratories">Abbott</a> paid $1.6 billion in fines to US federal and state governments for illegal promotion of off-label uses for Depakote, including the sedation of elderly nursing home residents.<sup id="cite_ref-103" class="reference"><a href="#cite_note-103"><span class="cite-bracket">[</span>103<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-104" class="reference"><a href="#cite_note-104"><span class="cite-bracket">[</span>104<span class="cite-bracket">]</span></a></sup> </p><p>Some studies have suggested that valproate may reopen the <a href="/wiki/Critical_period" title="Critical period">critical period</a> for learning <a href="/wiki/Absolute_pitch" title="Absolute pitch">absolute pitch</a> and possibly other skills such as language.<sup id="cite_ref-105" class="reference"><a href="#cite_note-105"><span class="cite-bracket">[</span>105<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-106" class="reference"><a href="#cite_note-106"><span class="cite-bracket">[</span>106<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Formulations">Formulations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=21" title="Edit section: Formulations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1269284339"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1257001546"><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Sodium valproate">Sodium valproate</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Sodium-valproate-2D-skeletal.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Sodium-valproate-2D-skeletal.png/250px-Sodium-valproate-2D-skeletal.png" decoding="async" width="250" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/36/Sodium-valproate-2D-skeletal.png/375px-Sodium-valproate-2D-skeletal.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/36/Sodium-valproate-2D-skeletal.png/500px-Sodium-valproate-2D-skeletal.png 2x" data-file-width="1100" data-file-height="791" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Valproato_S%C3%B3dico.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Valproato_S%C3%B3dico.png/250px-Valproato_S%C3%B3dico.png" decoding="async" width="250" height="196" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Valproato_S%C3%B3dico.png/375px-Valproato_S%C3%B3dico.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5d/Valproato_S%C3%B3dico.png/500px-Valproato_S%C3%B3dico.png 2x" data-file-width="825" data-file-height="646" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">valproate sodium (<a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name">USAN</a> <small><abbr title="United States">US</abbr></small>)</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><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=Valproate+sodium">Valproate sodium</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 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_1-1" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>Rx-only<sup id="cite_ref-107" class="reference"><a href="#cite_note-107"><span class="cite-bracket">[</span>107<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-108" class="reference"><a href="#cite_note-108"><span class="cite-bracket">[</span>108<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Depakote_FDA_label_4-10" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Depakote_ER_FDA_label_5-2" class="reference"><a href="#cite_note-Depakote_ER_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li></ul></div> </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%;">sodium 2-propylpentanoate</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=1069-66-5">1069-66-5</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/16760703">16760703</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/DBSALT001257">DBSALT001257</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.13428.html">13428</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/5VOM6GYJ0D">5VOM6GYJ0D</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/D00710">D00710</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:9925">CHEBI:9925</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/ChEMBL433">ChEMBL433</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID6023733">DTXSID6023733</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q240642#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/100.002.525">100.002.525</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q240642#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>8</sub><span title="Hydrogen">H</span><sub>15</sub><span title="Sodium">Na</span><span title="Oxygen">O</span><sub>2</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="7002166196000000000♠"></span>166.196</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=CCCC%28CCC%29C%28%3DO%29%5BO-%5D.%5BNa%2B%5D">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCCC(CCC)C(=O)[O-].[Na+]</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/C8H16O2.Na/c1-3-5-7(6-4-2)8(9)10;/h7H,3-6H2,1-2H3,(H,9,10);/q;+1/p-1<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:AEQFSUDEHCCHBT-UHFFFAOYSA-M<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"><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=464404696&page2=Valproate">(verify)</a></span></span></td></tr></tbody></table> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1269284339"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1257001546"><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Valproate semisodium">Valproate semisodium</span></caption><tbody><tr><td colspan="2" class="infobox-image"><table style="width:100%; margin:0;"><tbody><tr> <td style="vertical-align:top; text-align:center; width:50%;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Sodium_valproate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Sodium_valproate.svg/250px-Sodium_valproate.svg.png" decoding="async" width="250" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Sodium_valproate.svg/375px-Sodium_valproate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/Sodium_valproate.svg/500px-Sodium_valproate.svg.png 2x" data-file-width="283" data-file-height="123" /></a></span></td> <td style="vertical-align:top; text-align:center; width:50%;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:2-propylpentanoic_acid_200.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/2-propylpentanoic_acid_200.svg/250px-2-propylpentanoic_acid_200.svg.png" decoding="async" width="250" height="96" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/2-propylpentanoic_acid_200.svg/375px-2-propylpentanoic_acid_200.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/2-propylpentanoic_acid_200.svg/500px-2-propylpentanoic_acid_200.svg.png 2x" data-file-width="211" data-file-height="81" /></a></span></td> </tr></tbody></table></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Depakote, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">semisodium valproate, divalproex sodium (<a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name">USAN</a> <small><abbr title="United States">US</abbr></small>)</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><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=Divalproex+sodium">Divalproex sodium</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 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_1-2" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>Rx-only<sup id="cite_ref-Depakote_FDA_label_4-11" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Depakote_ER_FDA_label_5-3" class="reference"><a href="#cite_note-Depakote_ER_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li></ul></div> </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%;">sodium 2-propylpentanoate;2-propylpentanoic acid</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=76584-70-8">76584-70-8</a></span></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/23663956">23663956</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/DBSALT000185">DBSALT000185</a></span></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.48337.html">48337</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/644VL95AO6">644VL95AO6</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/D00304">D00304</a></span></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:4667">CHEBI:4667</a></span></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/ChEMBL2105613">ChEMBL2105613</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/DTXSID6023733">DTXSID6023733</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q240642#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/100.002.525">100.002.525</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q240642#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>16</sub><span title="Hydrogen">H</span><sub>31</sub><span title="Sodium">Na</span><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="7002310410000000000♠"></span>310.410</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=CCCC%28CCC%29C%28%3DO%29O.CCCC%28CCC%29C%28%3DO%29%5BO-%5D.%5BNa%2B%5D">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCCC(CCC)C(=O)O.CCCC(CCC)C(=O)[O-].[Na+]</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/2C8H16O2.Na/c2*1-3-5-7(6-4-2)8(9)10;/h2*7H,3-6H2,1-2H3,(H,9,10);/q;;+1/p-1<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:MSRILKIQRXUYCT-UHFFFAOYSA-M<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></tbody></table> <p>Valproate exists in two main molecular variants: <i>sodium valproate</i> and <i>valproic acid without sodium</i> (often implied by simply <i>valproate</i>). A mixture between these two is termed <i>semisodium valproate</i>. It is unclear whether there is any difference in efficacy between these variants, except from the fact that about 10% more mass of <i>sodium valproate</i> is needed than <i>valproic acid without sodium</i> to compensate for the sodium itself.<sup id="cite_ref-109" class="reference"><a href="#cite_note-109"><span class="cite-bracket">[</span>109<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Terminology">Terminology</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=22" title="Edit section: Terminology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Valproate is a negative ion. The <a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate acid</a> of valproate is valproic acid (VPA). Valproic acid is fully ionized into valproate at the physiologic pH of the human body, and valproate is the active form of the drug. Sodium valproate is the sodium <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> of valproic acid. Divalproex sodium is a <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complex</a> composed of equal parts of valproic acid and sodium valproate.<sup id="cite_ref-110" class="reference"><a href="#cite_note-110"><span class="cite-bracket">[</span>110<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Brand_names_of_valproic_acid">Brand names of valproic acid</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=23" title="Edit section: Brand names of valproic acid"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Branded products include: </p> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1184024115"><div class="div-col" style="column-width: 30em;"> <ul><li>Absenor (<a href="/wiki/Orion_Corporation_(pharmaceutical_company)" class="mw-redirect" title="Orion Corporation (pharmaceutical company)">Orion Corporation</a> Finland)</li> <li>Convulex (<a href="/w/index.php?title=G.L._Pharma_GmbH&action=edit&redlink=1" class="new" title="G.L. Pharma GmbH (page does not exist)">G.L. Pharma GmbH</a> Austria)</li> <li>Depakene (<a href="/wiki/Abbott_Laboratories" title="Abbott Laboratories">Abbott Laboratories</a> in US and Canada)<sup id="cite_ref-Depakene_FDA_label_111-0" class="reference"><a href="#cite_note-Depakene_FDA_label-111"><span class="cite-bracket">[</span>111<span class="cite-bracket">]</span></a></sup></li> <li>Depakin (<a href="/wiki/Sanofi" title="Sanofi">Sanofi S.R.L.</a> Italy)<sup id="cite_ref-Depakin_AIFA_112-0" class="reference"><a href="#cite_note-Depakin_AIFA-112"><span class="cite-bracket">[</span>112<span class="cite-bracket">]</span></a></sup></li> <li>Depakine (<a href="/wiki/Sanofi_Aventis" class="mw-redirect" title="Sanofi Aventis">Sanofi Aventis</a> France)</li> <li>Depakine (<a href="/wiki/Sanofi_Synthelabo" class="mw-redirect" title="Sanofi Synthelabo">Sanofi Synthelabo</a> Romania)</li> <li>Depalept (<a href="/wiki/Sanofi_Aventis" class="mw-redirect" title="Sanofi Aventis">Sanofi Aventis</a> Israel)</li> <li>Deprakine (<a href="/wiki/Sanofi_Aventis" class="mw-redirect" title="Sanofi Aventis">Sanofi Aventis</a> Finland)</li> <li>Encorate (<a href="/wiki/Sun_Pharmaceuticals" class="mw-redirect" title="Sun Pharmaceuticals">Sun Pharmaceuticals</a> India)</li> <li>Epilim (<a href="/wiki/Sanofi_Synthelabo" class="mw-redirect" title="Sanofi Synthelabo">Sanofi Synthelabo</a> Australia and South Africa)</li> <li>Stavzor (<a href="/w/index.php?title=Noven_Pharmaceuticals&action=edit&redlink=1" class="new" title="Noven Pharmaceuticals (page does not exist)">Noven Pharmaceuticals Inc.</a>)</li> <li>Valcote (<a href="/wiki/Abbott_Laboratories" title="Abbott Laboratories">Abbott Laboratories</a> Argentina)</li> <li>Valpakine (<a href="/wiki/Sanofi_Aventis" class="mw-redirect" title="Sanofi Aventis">Sanofi Aventis</a> Brazil)</li> <li>Orfiril (Desitin Arzneimittel GmbH Norway)</li></ul> </div> <div class="mw-heading mw-heading4"><h4 id="Brand_names_of_sodium_valproate">Brand names of sodium valproate</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=24" title="Edit section: Brand names of sodium valproate"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading5"><h5 id="Portugal">Portugal</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=25" title="Edit section: Portugal"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Tablets –  Diplexil-R by <a href="/wiki/Bial" title="Bial">Bial</a>.</li></ul> <div class="mw-heading mw-heading5"><h5 id="United_States">United States</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=26" title="Edit section: United States"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Intravenous injection –  Depacon by Abbott Laboratories.</li> <li>Syrup –  Depakene by Abbott Laboratories. (Note: Depakene <i>capsules</i> are valproic acid).</li> <li>Depakote tablets are a mixture of sodium valproate and valproic acid.</li> <li>Tablets –  Eliaxim by Bial.</li></ul> <div class="mw-heading mw-heading5"><h5 id="Australia">Australia</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=27" title="Edit section: Australia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Epilim Crushable Tablets Sanofi<sup id="cite_ref-Epilim_TGA_PI_113-0" class="reference"><a href="#cite_note-Epilim_TGA_PI-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup></li> <li>Epilim Sugar Free Liquid Sanofi<sup id="cite_ref-Epilim_TGA_PI_113-1" class="reference"><a href="#cite_note-Epilim_TGA_PI-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup></li> <li>Epilim Syrup Sanofi<sup id="cite_ref-Epilim_TGA_PI_113-2" class="reference"><a href="#cite_note-Epilim_TGA_PI-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup></li> <li>Epilim Tablets Sanofi<sup id="cite_ref-Epilim_TGA_PI_113-3" class="reference"><a href="#cite_note-Epilim_TGA_PI-113"><span class="cite-bracket">[</span>113<span class="cite-bracket">]</span></a></sup></li> <li>Sodium Valproate Sandoz Tablets Sanofi</li> <li>Valpro Tablets Alphapharm</li> <li>Valproate Winthrop Tablets Sanofi</li> <li>Valprease tablets Sigma</li></ul> <div class="mw-heading mw-heading5"><h5 id="New_Zealand">New Zealand</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=28" title="Edit section: New Zealand"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Epilim by Sanofi-Aventis</li></ul> <p>All the above formulations are <a href="/wiki/Pharmaceutical_Management_Agency" class="mw-redirect" title="Pharmaceutical Management Agency">Pharmac</a>-subsidised.<sup id="cite_ref-114" class="reference"><a href="#cite_note-114"><span class="cite-bracket">[</span>114<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading5"><h5 id="UK">UK</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=29" title="Edit section: UK"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Depakote Tablets (as in USA)</li> <li>Tablets –  Orlept by Wockhardt and Epilim by Sanofi</li> <li>Oral solution –  Orlept Sugar Free by Wockhardt and Epilim by Sanofi</li> <li>Syrup –  Epilim by Sanofi-Aventis</li> <li>Intravenous injection –  Epilim Intravenous by Sanofi</li> <li>Extended release tablets –  Epilim Chrono by Sanofi is a combination of sodium valproate and valproic acid in a 2.3:1 ratio.</li> <li>Enteric-coated tablets –  Epilim EC200 by Sanofi is a 200 mg sodium valproate <a href="/wiki/Enteric_coating" title="Enteric coating">enteric-coated</a> tablet.</li></ul> <div class="mw-heading mw-heading6"><h6 id="UK_only">UK only</h6><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=30" title="Edit section: UK only"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Capsules –  Episenta prolonged release by Beacon</li> <li>Sachets –  Episenta prolonged release by Beacon</li> <li>Intravenous solution for injection –  Episenta solution for injection by Beacon</li></ul> <div class="mw-heading mw-heading5"><h5 id="Germany,_Switzerland,_Norway,_Finland,_Sweden"><span id="Germany.2C_Switzerland.2C_Norway.2C_Finland.2C_Sweden"></span>Germany, Switzerland, Norway, Finland, Sweden</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=31" title="Edit section: Germany, Switzerland, Norway, Finland, Sweden"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Tablets –  Orfiril by Desitin Pharmaceuticals</li> <li>Intravenous injection –  Orfiril IV by Desitin Pharmaceuticals</li></ul> <div class="mw-heading mw-heading5"><h5 id="South_Africa">South Africa</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=32" title="Edit section: South Africa"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Syrup –  Convulex by Byk Madaus<sup id="cite_ref-115" class="reference"><a href="#cite_note-115"><span class="cite-bracket">[</span>115<span class="cite-bracket">]</span></a></sup></li> <li>Tablets –  Epilim by Sanofi-synthelabo</li></ul> <div class="mw-heading mw-heading5"><h5 id="Malaysia">Malaysia</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=33" title="Edit section: Malaysia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Tablets –  Epilim (<i>200 ENTERIC COATED</i>) by Sanofi-Aventis</li> <li>Controlled release tablets –  Epilim Chrono (<i>500 CONTROLLED RELEASE</i>) by Sanofi-Aventis<sup id="cite_ref-Sanofi_in_Malaysia_Products_-_Epilim_&_Epilim_Chrono_116-0" class="reference"><a href="#cite_note-Sanofi_in_Malaysia_Products_-_Epilim_&_Epilim_Chrono-116"><span class="cite-bracket">[</span>116<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading5"><h5 id="Romania">Romania</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=34" title="Edit section: Romania"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Companies are SANOFI-AVENTIS FRANCE, GEROT PHARMAZEUTIKA GMBH and DESITIN ARZNEIMITTEL GMBH</li> <li>Types are Syrup, Extended release mini tablets, Gastric resistant coated tablets, Gastric resistant soft capsules, Extended release capsules, Extended release tablets and Extended release coated tablets</li></ul> <div class="mw-heading mw-heading5"><h5 id="Canada">Canada</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=35" title="Edit section: Canada"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Intravenous injection –  Epival or Epiject by <a href="/wiki/Abbott_Laboratories" title="Abbott Laboratories">Abbott Laboratories</a>.</li> <li>Syrup –  Depakene by <a href="/wiki/Abbott_Laboratories" title="Abbott Laboratories">Abbott Laboratories</a> its generic formulations include <a rel="nofollow" class="external text" href="https://web.archive.org/web/20070928082043/http://www.apotex.ca/Products/EN/Detail.asp?MaterialNumber=000000000000042290">Apo-Valproic</a> and <a rel="nofollow" class="external text" href="https://web.archive.org/web/20080115210712/http://www.ratiopharm.ca/e/Products/productSearch.asp?Cap=V">ratio-Valproic</a>.</li></ul> <div class="mw-heading mw-heading5"><h5 id="Japan">Japan</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=36" title="Edit section: Japan"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Tablets –  Depakene by <a href="/wiki/Kyowa_Hakko_Kirin" class="mw-redirect" title="Kyowa Hakko Kirin">Kyowa Hakko Kirin</a></li> <li>Extended release tablets –  Depakene-R by Kyowa Hakko Kogyo and Selenica-R by <a href="/wiki/Kowa_Co." class="mw-redirect" title="Kowa Co.">Kowa</a></li> <li>Syrup –  Depakene by Kyowa Hakko Kogyo</li></ul> <div class="mw-heading mw-heading5"><h5 id="Europe">Europe</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=37" title="Edit section: Europe"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In much of Europe, Dépakine and Depakine Chrono (tablets) are equivalent to Epilim and Epilim Chrono above. </p> <div class="mw-heading mw-heading5"><h5 id="Taiwan">Taiwan</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=38" title="Edit section: Taiwan"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Tablets (white round tablet) –  Depakine (<a href="/wiki/Chinese_language" title="Chinese language">Chinese</a>: <span lang="zh">帝拔癲</span>; <a href="/wiki/Pinyin" title="Pinyin">pinyin</a>: <i><span lang="zh-Latn">di-ba-dian</span></i>) by <a href="/wiki/Sanofi-Aventis" class="mw-redirect" title="Sanofi-Aventis">Sanofi Winthrop Industrie</a> (France)</li></ul> <div class="mw-heading mw-heading5"><h5 id="Iran">Iran</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=39" title="Edit section: Iran"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Tablets –  Epival 200 (enteric coated tablet) and Epival 500 (extended release tablet) by Iran Najo</li> <li>Slow release tablets –  Depakine Chrono by <a href="/wiki/Sanofi-Aventis" class="mw-redirect" title="Sanofi-Aventis">Sanofi Winthrop Industrie</a> (France)</li></ul> <div class="mw-heading mw-heading5"><h5 id="Israel">Israel</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=40" title="Edit section: Israel"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Depalept and Depalept Chrono (extended release tablets) are equivalent to Epilim and Epilim Chrono above. Manufactured and distributed by <a href="/wiki/Sanofi-Aventis" class="mw-redirect" title="Sanofi-Aventis">Sanofi-Aventis</a>. </p> <div class="mw-heading mw-heading5"><h5 id="India,_Russia_and_CIS_countries"><span id="India.2C_Russia_and_CIS_countries"></span>India, Russia and <a href="/wiki/Commonwealth_of_Independent_States" title="Commonwealth of Independent States">CIS</a> countries</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=41" title="Edit section: India, Russia and CIS countries"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Valparin Chrono by Sanofi India</li> <li>Valprol CR by Intas Pharmaceutical (India)</li> <li>Encorate Chrono by Sun Pharmaceutical (India)</li> <li>Serven Chrono by Leeven APL Biotech (India)</li></ul> <div class="mw-heading mw-heading5"><h5 id="Uruguay">Uruguay</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=42" title="Edit section: Uruguay"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Tablets –  DI DPA by Megalabs</li></ul> <div class="mw-heading mw-heading4"><h4 id="Brand_names_of_valproate_semisodium">Brand names of valproate semisodium</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Valproate&action=edit&section=43" title="Edit section: Brand names of valproate semisodium"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Brazil –  Depakote by <a href="/wiki/Abbott_Laboratories" title="Abbott Laboratories">Abbott Laboratories</a> and Torval CR by Torrent do Brasil</li> <li>Canada –  Epival by Abbott Laboratories</li> <li>Mexico –  Epival and Epival ER (extended release) by Abbott Laboratories</li> <li>United Kingdom –  Depakote (for psychiatric conditions) and Epilim (for epilepsy) by <a href="/wiki/Sanofi-Aventis" class="mw-redirect" title="Sanofi-Aventis">Sanofi-Aventis</a> and generics</li> <li>United States –  Depakote and Depakote ER (extended release) by Abbott Laboratories and generics<sup id="cite_ref-Depakote_FDA_label_4-12" class="reference"><a href="#cite_note-Depakote_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li> <li>India –  Valance and Valance OD by Abbott Healthcare Pvt Ltd, Divalid ER by Linux laboratories Pvt Ltd, Valex ER by Sigmund Promedica, Dicorate by Sun Pharma</li> <li>Germany –  Ergenyl Chrono by Sanofi-Aventis and generics</li> <li>Chile –  Valcote and Valcote ER by Abbott Laboratories</li> <li>France and other European countries –  Depakote</li> <li>Peru –  Divalprax by AC Farma Laboratories</li> <li>China –  Diprate OD</li></ul> <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=Valproate&action=edit&section=44" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 2023 systematic review of the literature identified only one study in which valproate was evaluated in the treatment of seizures in infants aged 1 to 36 months. In a randomized control trial, valproate alone was found to show poorer outcomes for infants than valproate plus levetiracetam in terms of reduction of seizures, freedom from seizures, daily living ability, quality of life, and cognitive abilities.<sup id="cite_ref-117" class="reference"><a href="#cite_note-117"><span class="cite-bracket">[</span>117<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=Valproate&action=edit&section=45" 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-FDA-AllBoxedWarnings-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-FDA-AllBoxedWarnings_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FDA-AllBoxedWarnings_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-FDA-AllBoxedWarnings_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite 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">. 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Retrieved <span class="nowrap">3 August</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=RDC+N%C2%BA+784+-+Listas+de+Subst%C3%A2ncias+Entorpecentes%2C+Psicotr%C3%B3picas%2C+Precursoras+e+Outras+sob+Controle+Especial&rft.pub=Di%C3%A1rio+Oficial+da+Uni%C3%A3o&rft.date=2023-03-31&rft.au=Anvisa&rft_id=https%3A%2F%2Fwww.in.gov.br%2Fen%2Fweb%2Fdou%2F-%2Fresolucao-rdc-n-784-de-31-de-marco-de-2023-474904992&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</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.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html">"Product monograph brand safety updates"</a>. <i><a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a></i>. 7 July 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">13 July</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Health+Canada&rft.atitle=Product+monograph+brand+safety+updates&rft.date=2016-07-07&rft_id=https%3A%2F%2Fwww.canada.ca%2Fen%2Fhealth-canada%2Fservices%2Fdrugs-health-products%2Fdrug-products%2Fdrug-product-database%2Flabel-safety-assessment-update%2Fproduct-monograph-brand-safety-updates.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-Depakote_FDA_label-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Depakote_FDA_label_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-Depakote_FDA_label_4-12"><sup><i><b>m</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=08a65cf4-7749-4ceb-6895-8f4805e2b01f">"Depakote- divalproex sodium tablet, delayed release"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160305202922/http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=08a65cf4-7749-4ceb-6895-8f4805e2b01f">Archived</a> from the original on 5 March 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">10 November</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=Depakote-+divalproex+sodium+tablet%2C+delayed+release&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D08a65cf4-7749-4ceb-6895-8f4805e2b01f&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-Depakote_ER_FDA_label-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Depakote_ER_FDA_label_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Depakote_ER_FDA_label_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Depakote_ER_FDA_label_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Depakote_ER_FDA_label_5-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0dc024ce-efc8-4690-7cb5-639c728fccac">"Depakote ER- divalproex sodium tablet, extended release"</a>. <i>DailyMed</i>. 24 February 2023. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230128143053/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0dc024ce-efc8-4690-7cb5-639c728fccac">Archived</a> from the original on 28 January 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">19 February</span> 2024</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Depakote+ER-+divalproex+sodium+tablet%2C+extended+release&rft.date=2023-02-24&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3D0dc024ce-efc8-4690-7cb5-639c728fccac&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-MSR-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-MSR_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MSR_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MSR_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-MSR_6-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://reference.medscape.com/drug/depakene-stavzor-valproic-acid-343024#showall">"Depakene, Stavzor (valproic acid) dosing, indications, interactions, adverse effects, and more"</a>. <i>Medscape Reference</i>. WebMD. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140221222153/http://reference.medscape.com/drug/depakene-stavzor-valproic-acid-343024#showall">Archived</a> from the original on 21 February 2014<span class="reference-accessdate">. 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Retrieved <span class="nowrap">27 June</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=New+York+Times&rft.atitle=Abbott+settles+marketing+lawsuit&rft.date=2012-05-08&rft.aulast=Schmidt&rft.aufirst=M&rft.au=Thomas%2C+K&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2012%2F05%2F08%2Fbusiness%2Fabbott-to-pay-1-6-billion-over-illegal-marketing.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-105"><span class="mw-cite-backlink"><b><a href="#cite_ref-105">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGervainVinesChenSeo2013" class="citation journal cs1">Gervain J, Vines BW, Chen LM, Seo RJ, Hensch TK, Werker JF, et al. 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Retrieved <span class="nowrap">3 March</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Martindale%3A+The+Complete+Drug+Reference&rft.place=London&rft.pub=Pharmaceutical+Press&rft_id=https%3A%2F%2Fwww.medicinescomplete.com%2Fmc%2Fmartindale%2Fcurrent%2Fms-10447-z.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-Depakene_FDA_label-111"><span class="mw-cite-backlink"><b><a href="#cite_ref-Depakene_FDA_label_111-0">^</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://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a0288919-75bf-4752-975f-40579572c0f7">"Depakene- valproic acid capsule, liquid filled"</a>. <i>DailyMed</i>. 19 September 2019. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200711130306/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a0288919-75bf-4752-975f-40579572c0f7">Archived</a> from the original on 11 July 2020<span class="reference-accessdate">. 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Retrieved <span class="nowrap">6 June</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=farmaci.agenziafarmaco.gov.it&rft.atitle=Depakin+-+Banca+Dati+Farmaci+dell%27AIFA&rft.date=2023-06-06&rft_id=https%3A%2F%2Ffarmaci.agenziafarmaco.gov.it%2Fbancadatifarmaci%2Ffarmaco%3Ffarmaco%3D022483&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-Epilim_TGA_PI-113"><span class="mw-cite-backlink">^ <a href="#cite_ref-Epilim_TGA_PI_113-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Epilim_TGA_PI_113-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Epilim_TGA_PI_113-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Epilim_TGA_PI_113-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-05620-3">"Australian product information epilim (sodium valproate) crushable tablets, enteric-coated tablets, syrup, liquid"</a> <span class="cs1-format">(PDF)</span>. <i>TGA eBS</i>. 15 April 2020. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200315112531/https://www.ebs.tga.gov.au/ebs/picmi/picmirepository.nsf/pdf?OpenAgent&id=CP-2010-PI-05620-3">Archived</a> from the original on 15 March 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">15 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=TGA+eBS&rft.atitle=Australian+product+information+epilim+%28sodium+valproate%29+crushable+tablets%2C+enteric-coated+tablets%2C+syrup%2C+liquid&rft.date=2020-04-15&rft_id=http%3A%2F%2Fwww.ebs.tga.gov.au%2Febs%2Fpicmi%2Fpicmirepository.nsf%2Fpdf%3FOpenAgent%26id%3DCP-2010-PI-05620-3&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-114"><span class="mw-cite-backlink"><b><a href="#cite_ref-114">^</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://web.archive.org/web/20160304081454/http://www.pharmac.govt.nz/Schedule?osq=Sodium%20valproate">"Sodium valproate -- Pharmaceutical Schedule"</a>. Pharmaceutical Management Agency. Archived from <a rel="nofollow" class="external text" href="http://www.pharmac.govt.nz/Schedule?osq=Sodium%20valproate">the original</a> on 4 March 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">22 June</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Sodium+valproate+--+Pharmaceutical+Schedule&rft.pub=Pharmaceutical+Management+Agency&rft_id=http%3A%2F%2Fwww.pharmac.govt.nz%2FSchedule%3Fosq%3DSodium%2520valproate&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-115"><span class="mw-cite-backlink"><b><a href="#cite_ref-115">^</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://web.archive.org/web/20100812052527/http://home.intekom.com/pharm/byk/convulex.html">"South African Electronic Package Inserts: Convulex"</a>. Archived from <a rel="nofollow" class="external text" href="http://home.intekom.com/pharm/byk/convulex.html">the original</a> on 12 August 2010<span class="reference-accessdate">. Retrieved <span class="nowrap">2 January</span> 2006</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=South+African+Electronic+Package+Inserts%3A+Convulex&rft_id=http%3A%2F%2Fhome.intekom.com%2Fpharm%2Fbyk%2Fconvulex.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-Sanofi_in_Malaysia_Products_-_Epilim_&_Epilim_Chrono-116"><span class="mw-cite-backlink"><b><a href="#cite_ref-Sanofi_in_Malaysia_Products_-_Epilim_&_Epilim_Chrono_116-0">^</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://www.sanofi.com.my/en/products/epilim">"Malaysian Package Inserts: Epilim"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230605142828/https://www.sanofi.com.my/en/products/epilim">Archived</a> from the original on 5 June 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">5 June</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Malaysian+Package+Inserts%3A+Epilim&rft_id=https%3A%2F%2Fwww.sanofi.com.my%2Fen%2Fproducts%2Fepilim&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" class="Z3988"></span></span> </li> <li id="cite_note-117"><span class="mw-cite-backlink"><b><a href="#cite_ref-117">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTreadwellWuTsou2022" class="citation report cs1">Treadwell JR, Wu M, Tsou AY (October 2022). <span class="id-lock-subscription" title="Paid subscription required"><a rel="nofollow" class="external text" href="https://effectivehealthcare.ahrq.gov/products/management-infantile-epilepsy/research">Management of Infantile Epilepsies</a></span>. <i>effectivehealthcare.ahrq.gov</i> (Report). Rockville (MD): Agency for Healthcare Research and Quality (US). <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.23970%2Fahrqepccer252">10.23970/ahrqepccer252</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/36383706">36383706</a>. Report No.: 22(23)-EHC004 Report No.: 2021-SR-01. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230705073433/https://effectivehealthcare.ahrq.gov/products/management-infantile-epilepsy/research">Archived</a> from the original on 5 July 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">12 July</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=Management+of+Infantile+Epilepsies&rft.place=Rockville+%28MD%29&rft.pub=Agency+for+Healthcare+Research+and+Quality+%28US%29&rft.date=2022-10&rft_id=info%3Adoi%2F10.23970%2Fahrqepccer252&rft_id=info%3Apmid%2F36383706&rft.aulast=Treadwell&rft.aufirst=JR&rft.au=Wu%2C+M&rft.au=Tsou%2C+AY&rft_id=https%3A%2F%2Feffectivehealthcare.ahrq.gov%2Fproducts%2Fmanagement-infantile-epilepsy%2Fresearch&rfr_id=info%3Asid%2Fen.wikipedia.org%3AValproate" 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 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navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Anticonvulsants" title="Template:Anticonvulsants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Anticonvulsants" title="Template talk:Anticonvulsants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Anticonvulsants" title="Special:EditPage/Template:Anticonvulsants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Anticonvulsants_(N03)431" style="font-size:114%;margin:0 4em"><a href="/wiki/Anticonvulsant" title="Anticonvulsant">Anticonvulsants</a> (<a href="/wiki/ATC_code_N03" title="ATC code N03">N03</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABAergic" title="GABAergic">GABAergics</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/GABAA_receptor" title="GABAA receptor">GABA<sub>A</sub>R</a> <a href="/wiki/Allosteric_modulator" title="Allosteric modulator">PAMs</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><b><a href="/wiki/Barbiturate" title="Barbiturate">Barbiturates</a>:</b> <a href="/wiki/Barbexaclone" title="Barbexaclone">Barbexaclone</a></li> <li><a href="/wiki/Metharbital" title="Metharbital">Metharbital</a></li> <li><a href="/wiki/Methylphenobarbital" title="Methylphenobarbital">Methylphenobarbital</a></li> <li><a href="/wiki/Pentobarbital" title="Pentobarbital">Pentobarbital</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a><sup>#</sup></li> <li><a href="/wiki/Primidone" title="Primidone">Primidone</a>; <b><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></b>: <a href="/wiki/Cenobamate" title="Cenobamate">Cenobamate</a></li> <li><a href="/wiki/Felbamate" title="Felbamate">Felbamate</a>; <b><a href="/wiki/Benzodiazepine" title="Benzodiazepine">Benzodiazepines</a></b>: <a href="/wiki/Clobazam" title="Clobazam">Clobazam</a></li> <li><a href="/wiki/Clonazepam" title="Clonazepam">Clonazepam</a></li> <li><a href="/wiki/Clorazepate" title="Clorazepate">Clorazepate</a></li> <li><a href="/wiki/Diazepam" title="Diazepam">Diazepam</a><sup>#</sup></li> <li><a href="/wiki/Lorazepam" title="Lorazepam">Lorazepam</a><sup>#</sup></li> <li><a href="/wiki/Midazolam" title="Midazolam">Midazolam</a></li> <li><a href="/wiki/Nimetazepam" title="Nimetazepam">Nimetazepam</a></li> <li><a href="/wiki/Nitrazepam" title="Nitrazepam">Nitrazepam</a></li> <li><a href="/wiki/Temazepam" title="Temazepam">Temazepam</a>; <b>Others:</b> <a href="/wiki/Bromide" title="Bromide">Bromide</a> (<a href="/wiki/Potassium_bromide" title="Potassium bromide">potassium bromide</a>, <a href="/wiki/Sodium_bromide" title="Sodium bromide">sodium bromide</a>)</li> <li><a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/Paraldehyde" title="Paraldehyde">Paraldehyde</a></li> <li><a href="/wiki/Stiripentol" title="Stiripentol">Stiripentol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/GABA_transaminase_inhibitor" title="GABA transaminase inhibitor">GABA-T 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><b><a href="/wiki/Fatty_acid" title="Fatty acid">Fatty acids</a> (and related):</b> <a class="mw-selflink selflink">Valproate</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a></li> <li><a href="/wiki/Vigabatrin" title="Vigabatrin">Vigabatrin</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" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/GABA_receptor_agonist" title="GABA receptor agonist">GABAR agonists</a></b>: <a href="/wiki/Progabide" title="Progabide">Progabide</a>; <b><a href="/wiki/GABA_reuptake_inhibitor" title="GABA reuptake inhibitor">GAT-1 inhibitors</a>:</b> <a href="/wiki/Tiagabine" title="Tiagabine">Tiagabine</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/Channel_modulator" title="Channel modulator">Channel<br />modulators</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/Sodium_channel_blocker" title="Sodium channel blocker">Sodium blockers</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Hydantoin" title="Hydantoin">Hydantoins</a>:</b> <a href="/wiki/Ethotoin" title="Ethotoin">Ethotoin</a></li> <li><a href="/wiki/Fosphenytoin" title="Fosphenytoin">Fosphenytoin</a></li> <li><a href="/wiki/Mephenytoin" title="Mephenytoin">Mephenytoin</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a><sup>#</sup>; <b><a href="/wiki/Acylurea" title="Acylurea">Ureides</a>:</b> <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/Chlorphenacemide" title="Chlorphenacemide">Chlorphenacemide</a></li> <li><a href="/wiki/Phenacemide" title="Phenacemide">Phenacemide</a><sup>‡</sup></li> <li><a href="/wiki/Pheneturide" title="Pheneturide">Pheneturide</a>; <b><a href="/wiki/Fatty_acid" title="Fatty acid">Fatty acids</a>:</b> <a class="mw-selflink selflink">Valproate</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a>; <b><a href="/wiki/Carboxamide" class="mw-redirect" title="Carboxamide">Carboxamides</a>:</b></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a><sup>#</sup></li> <li><a href="/wiki/Eslicarbazepine_acetate" title="Eslicarbazepine acetate">Eslicarbazepine acetate</a></li> <li><a href="/wiki/Oxcarbazepine" title="Oxcarbazepine">Oxcarbazepine</a>; <b>Others:</b> <a href="/wiki/Lacosamide" title="Lacosamide">Lacosamide</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a><sup>#</sup></li> <li><a href="/wiki/Rufinamide" title="Rufinamide">Rufinamide</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Calcium blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/2,4-Oxazolidinedione" title="2,4-Oxazolidinedione">Oxazolidinediones</a>:</b> <a href="/wiki/Ethadione" title="Ethadione">Ethadione</a></li> <li><a href="/wiki/Paramethadione" title="Paramethadione">Paramethadione</a></li> <li><a href="/wiki/Trimethadione" title="Trimethadione">Trimethadione</a>; <b><a href="/wiki/Succinimide" title="Succinimide">Succinimides</a></b>: <a href="/wiki/Ethosuximide" title="Ethosuximide">Ethosuximide</a><sup>#</sup></li> <li><a href="/wiki/Mesuximide" title="Mesuximide">Mesuximide</a></li> <li><a href="/wiki/Phensuximide" title="Phensuximide">Phensuximide</a>; <b><a href="/wiki/Gabapentinoid" title="Gabapentinoid">Gabapentinoids</a>:</b> <a href="/wiki/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a>; <b>Others:</b> <a href="/wiki/Imepitoin" title="Imepitoin">Imepitoin</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a><sup>#</sup></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium openers</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/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: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"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbonic_anhydrase_inhibitor" title="Carbonic anhydrase inhibitor">CA 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><b><a href="/wiki/Sulfonamide_(medicine)#Anticonvulsant" title="Sulfonamide (medicine)">Sulfonamides</a>:</b> <a href="/wiki/Acetazolamide" title="Acetazolamide">Acetazolamide</a></li> <li><a href="/wiki/Ethoxzolamide" title="Ethoxzolamide">Ethoxzolamide</a></li> <li><a href="/wiki/Sultiame" title="Sultiame">Sultiame</a></li> <li><a href="/wiki/Topiramate" title="Topiramate">Topiramate</a></li> <li><a href="/wiki/Zonisamide" title="Zonisamide">Zonisamide</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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Albutoin" title="Albutoin">Albutoin</a></li> <li><a href="/wiki/Beclamide" title="Beclamide">Beclamide</a></li> <li><a href="/wiki/Brivaracetam" title="Brivaracetam">Brivaracetam</a></li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Carisbamate" title="Carisbamate">Carisbamate</a></li> <li><a href="/wiki/Etiracetam" title="Etiracetam">Etiracetam</a></li> <li><a href="/wiki/Fenfluramine" title="Fenfluramine">Fenfluramine</a></li> <li><a href="/wiki/Ganaxolone" title="Ganaxolone">Ganaxolone</a></li> <li><a href="/wiki/Levetiracetam" title="Levetiracetam">Levetiracetam</a></li> <li><a href="/wiki/Perampanel" title="Perampanel">Perampanel</a></li></ul> </div></td></tr></tbody></table><div></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="Mood_stabilizers88" 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:Mood_stabilizers" title="Template:Mood stabilizers"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Mood_stabilizers" title="Template talk:Mood stabilizers"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Mood_stabilizers" title="Special:EditPage/Template:Mood stabilizers"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Mood_stabilizers88" style="font-size:114%;margin:0 4em"><a href="/wiki/Mood_stabilizer" title="Mood stabilizer">Mood stabilizers</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticonvulsant" title="Anticonvulsant">Anticonvulsants</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/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamotrigine</a></li> <li><a href="/wiki/Oxcarbazepine" title="Oxcarbazepine">Oxcarbazepine</a></li> <li><a class="mw-selflink selflink">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/Valpromide" title="Valpromide">Valpromide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Atypical_antipsychotic" title="Atypical antipsychotic">Atypical antipsychotics</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/Aripiprazole" title="Aripiprazole">Aripiprazole</a></li> <li><a href="/wiki/Asenapine" title="Asenapine">Asenapine</a></li> <li><a href="/wiki/Cariprazine" title="Cariprazine">Cariprazine</a></li> <li><a href="/wiki/Clozapine" title="Clozapine">Clozapine</a></li> <li><a href="/wiki/Lurasidone" title="Lurasidone">Lurasidone</a></li> <li><a href="/wiki/Olanzapine" title="Olanzapine">Olanzapine</a> (<a href="/wiki/Olanzapine/fluoxetine" title="Olanzapine/fluoxetine">+fluoxetine</a>)</li> <li><a href="/wiki/Paliperidone" title="Paliperidone">Paliperidone</a></li> <li><a href="/wiki/Quetiapine" title="Quetiapine">Quetiapine</a></li> <li><a href="/wiki/Risperidone" title="Risperidone">Risperidone</a></li> <li><a href="/wiki/Ziprasidone" title="Ziprasidone">Ziprasidone</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/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Lithium_(medication)" title="Lithium (medication)">Lithium</a> (<a href="/wiki/Lithium_acetate" title="Lithium acetate">lithium acetate</a>, <a href="/wiki/Lithium_carbonate" title="Lithium carbonate">lithium carbonate</a>, <a href="/wiki/Lithium_chloride" title="Lithium chloride">lithium chloride</a>, <a href="/wiki/Lithium_citrate" title="Lithium citrate">lithium citrate</a>, <a href="/wiki/Lithium_hydroxide" title="Lithium hydroxide">lithium hydroxide</a>, <a href="/wiki/Lithium_orotate" title="Lithium orotate">lithium orotate</a>)</li> <li><a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">Omega-3 fatty acids</a> (<a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">docosahexaenoic acid</a>, <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a>)</li></ul> </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 href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Ketodarolutamide" title="Ketodarolutamide">Ketodarolutamide</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/w/index.php?title=LG-105&action=edit&redlink=1" class="new" title="LG-105 (page does not exist)">LG-105</a></li> <li><a href="/wiki/LG-120907" title="LG-120907">LG-120907</a></li> <li><a href="/w/index.php?title=LGD-1331&action=edit&redlink=1" class="new" title="LGD-1331 (page does not exist)">LGD-1331</a></li> <li><a href="/wiki/Linuron" title="Linuron">Linuron</a></li> <li><a href="/wiki/Masofaniten" title="Masofaniten">Masofaniten</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/w/index.php?title=N-Butylbenzenesulfonamide&action=edit&redlink=1" class="new" title="N-Butylbenzenesulfonamide (page does not exist)"><i>N</i>-Butylbenzenesulfonamide</a></li> <li><a href="/wiki/N-Desmethylapalutamide" title="N-Desmethylapalutamide"><i>N</i>-Desmethylapalutamide</a></li> <li><a href="/wiki/N-Desmethylenzalutamide" title="N-Desmethylenzalutamide"><i>N</i>-Desmethylenzalutamide</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/w/index.php?title=ONC1-13B&action=edit&redlink=1" class="new" title="ONC1-13B (page does not exist)">ONC1-13B</a></li> <li><a href="/wiki/Pentomone" title="Pentomone">Pentomone</a></li> <li><a href="/w/index.php?title=PF-998425&action=edit&redlink=1" class="new" title="PF-998425 (page does not exist)">PF-998425</a></li> <li><a href="/wiki/Phenothrin" title="Phenothrin">Phenothrin</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/wiki/Procymidone" title="Procymidone">Procymidone</a></li> <li><a href="/wiki/Proxalutamide" title="Proxalutamide">Proxalutamide</a></li> <li><a href="/wiki/Pyrilutamide" title="Pyrilutamide">Pyrilutamide</a></li> <li><a href="/wiki/Ralaniten" title="Ralaniten">Ralaniten (EPI-002)</a></li> <li><a href="/wiki/Ralaniten_acetate" title="Ralaniten acetate">Ralaniten acetate (EPI-506)</a></li> <li><a href="/wiki/RD-162" title="RD-162">RD-162</a></li> <li><a href="/wiki/Rezvilutamide" title="Rezvilutamide">Rezvilutamide</a></li> <li><a href="/w/index.php?title=Ro_2-7239&action=edit&redlink=1" class="new" title="Ro 2-7239 (page does not exist)">Ro 2-7239</a></li> <li><a href="/w/index.php?title=Ro_5-2537&action=edit&redlink=1" class="new" title="Ro 5-2537 (page does not exist)">Ro 5-2537</a></li> <li><a href="/wiki/RU-22930" title="RU-22930">RU-22930</a></li> <li><a href="/wiki/RU-56187" title="RU-56187">RU-56187</a></li> <li><a href="/wiki/RU-57073" title="RU-57073">RU-57073</a></li> <li><a href="/wiki/RU-58642" title="RU-58642">RU-58642</a></li> <li><a href="/wiki/RU-58841" title="RU-58841">RU-58841</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a></li> <li><a href="/wiki/Thalidomide" title="Thalidomide">Thalidomide</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/wiki/Vinclozolin" title="Vinclozolin">Vinclozolin</a></li> <li><a href="/w/index.php?title=YM-580&action=edit&redlink=1" class="new" title="YM-580 (page does not exist)">YM-580</a></li> <li><a href="/w/index.php?title=YM-92088&action=edit&redlink=1" class="new" title="YM-92088 (page does not exist)">YM-92088</a></li> <li><a href="/w/index.php?title=YM-175735&action=edit&redlink=1" class="new" title="YM-175735 (page does not exist)">YM-175735</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/GPRC6A" title="GPRC6A">GPRC6A</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cation" class="mw-redirect" title="Cation">Cations</a> (incl. <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Gadolinium" title="Gadolinium">gadolinium</a>, <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, <a href="/wiki/Strontium" title="Strontium">strontium</a>, <a href="/wiki/Zinc" title="Zinc">zinc</a>)</li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Amino_acid" title="Amino acid"><small>L</small>-α-Amino acids</a> (incl. <a href="/wiki/Arginine" title="Arginine"><small>L</small>-arginine</a>, <a href="/wiki/Lysine" title="Lysine"><small>L</small>-lysine</a>, <a href="/wiki/Ornithine" title="Ornithine"><small>L</small>-ornithine</a>)</li> <li><a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a></li> <li><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</span></li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_androgens_and_anabolic_steroids" title="List of androgens and anabolic steroids">List of androgens and anabolic steroids</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="GABATooltip_γ-Aminobutyric_acid_metabolism_and_transport_modulators899" 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:GABA_metabolism_and_transport_modulators" title="Template:GABA metabolism and transport modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GABA_metabolism_and_transport_modulators" title="Template talk:GABA metabolism and transport modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GABA_metabolism_and_transport_modulators" title="Special:EditPage/Template:GABA metabolism and transport modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GABATooltip_γ-Aminobutyric_acid_metabolism_and_transport_modulators899" style="font-size:114%;margin:0 4em"><a href="/wiki/%CE%93-Aminobutyric_acid" class="mw-redirect" title="Γ-Aminobutyric acid"><abbr title="γ-Aminobutyric acid">GABA</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 γ-Aminobutyric acid</span> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/GABA_transporter" title="GABA transporter">transport</a> <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</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:5em;text-align:center;"><a href="/wiki/GABA_transporter" title="GABA transporter"><abbr title="GABA transporter">GAT</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 GABA transporter</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/w/index.php?title=4-Aminovaleric_acid&action=edit&redlink=1" class="new" title="4-Aminovaleric acid (page does not exist)">4-Aminovaleric acid</a></li> <li><a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Arecaidine" title="Arecaidine">Arecaidine</a></li> <li><a href="/wiki/CI-966" title="CI-966">CI-966</a></li> <li><a href="/wiki/2,4-Diaminobutyric_acid" title="2,4-Diaminobutyric acid">DABA</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane (EGIS-3886, EGYT-3886)</a></li> <li><a href="/wiki/EF-1502" title="EF-1502">EF-1502</a></li> <li><a href="/wiki/Gabaculine" title="Gabaculine">Gabaculine</a></li> <li><a href="/wiki/Guvacine" title="Guvacine">Guvacine</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/w/index.php?title=NNC_05-2090&action=edit&redlink=1" class="new" title="NNC 05-2090 (page does not exist)">NNC 05-2090</a></li> <li><a href="/wiki/NO-711" class="mw-redirect" title="NO-711">NO-711</a></li> <li><a href="/wiki/Riluzole" title="Riluzole">Riluzole</a></li> <li><a href="/wiki/SKF-89976A" title="SKF-89976A">SKF-89976A</a></li> <li><a href="/w/index.php?title=SNAP-5114&action=edit&redlink=1" class="new" title="SNAP-5114 (page does not exist)">SNAP-5114</a></li> <li><a href="/w/index.php?title=Trans-4-Aminocrotonic_acid&action=edit&redlink=1" class="new" title="Trans-4-Aminocrotonic acid (page does not exist)">TACA</a></li> <li><a href="/wiki/Tiagabine" title="Tiagabine">Tiagabine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;text-align:center;"><a href="/wiki/Vesicular_inhibitory_amino_acid_transporter" title="Vesicular inhibitory amino acid transporter"><abbr title="Vesicular inhibitory amino acid transporter">VIAAT</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 Vesicular inhibitory amino acid transporter</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Bafilomycin_A1" class="mw-redirect" title="Bafilomycin A1">Bafilomycin A1</a></li> <li><a href="/w/index.php?title=Chicago_sky_blue_6B&action=edit&redlink=1" class="new" title="Chicago sky blue 6B (page does not exist)">Chicago sky blue 6B</a></li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/GABA" title="GABA">GABA</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/N-Butyric_acid" class="mw-redirect" title="N-Butyric acid">N-Butyric acid</a></li> <li><a href="/wiki/Nigericin" title="Nigericin">Nigericin</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/wiki/Valinomycin" title="Valinomycin">Valinomycin</a></li> <li><a href="/wiki/Vigabatrin" title="Vigabatrin">Vigabatrin</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/Enzyme" title="Enzyme">Enzyme</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:5em;text-align:center;"><a href="/wiki/Glutamate_decarboxylase" title="Glutamate decarboxylase"><abbr title="Glutamate decarboxylase">GAD</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 Glutamate decarboxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/wiki/3-Mercaptopropionic_acid" title="3-Mercaptopropionic acid">3-Mercaptopropionic acid</a></li> <li><a href="/wiki/Aminooxyacetic_acid" title="Aminooxyacetic acid">AAOA</a></li> <li><a href="/wiki/L-Allylglycine" class="mw-redirect" title="L-Allylglycine"><span style="font-size:85%;">L</span>-Allylglycine</a></li> <li><a href="/wiki/Semicarbazide" title="Semicarbazide">Semicarbazide</a></li></ul> <ul><li><i>Activators:</i> <a href="/wiki/3-Methyl-GABA" title="3-Methyl-GABA">3-Methyl-GABA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;text-align:center;"><a href="/wiki/%CE%93-Aminobutyrate_aminotransferase" class="mw-redirect" title="Γ-Aminobutyrate aminotransferase"><abbr title="γ-Aminobutyrate aminotransferase">GABA-T</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 γ-Aminobutyrate aminotransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/w/index.php?title=3-Hydrazinopropionic_acid&action=edit&redlink=1" class="new" title="3-Hydrazinopropionic acid (page does not exist)">3-Hydrazinopropionic acid</a></li> <li><a href="/wiki/2,4-Diaminobutyric_acid" title="2,4-Diaminobutyric acid">DABA</a></li> <li><a href="/wiki/%CE%93-Acetylenic-GABA" class="mw-redirect" title="Γ-Acetylenic-GABA">γ-Acetylenic-GABA</a></li> <li><a href="/wiki/Aminooxyacetic_acid" title="Aminooxyacetic acid">AOAA</a></li> <li><a href="/wiki/Ethanolamine-O-sulfate" title="Ethanolamine-O-sulfate">EOS</a></li> <li><a href="/wiki/Gabaculine" title="Gabaculine">Gabaculine</a></li> <li><a href="/wiki/Isoniazid" title="Isoniazid">Isoniazid</a></li> <li><a href="/wiki/L-Cycloserine" class="mw-redirect" title="L-Cycloserine"><small>L</small>-Cycloserine</a></li> <li><a href="/wiki/Phenelzine" title="Phenelzine">Phenelzine</a></li> <li><a href="/wiki/Phenylethylidenehydrazine" title="Phenylethylidenehydrazine">PEH</a></li> <li><a href="/wiki/Rosmarinic_acid" title="Rosmarinic acid">Rosmarinic acid</a> (<a href="/wiki/Lemon_balm" title="Lemon balm">lemon balm</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 (divalproex sodium)</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/Vigabatrin" title="Vigabatrin">Vigabatrin</a></li></ul> <ul><li><i>Activators:</i> <a href="/wiki/3-Methyl-GABA" title="3-Methyl-GABA">3-Methyl-GABA</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;">Other</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:5em;text-align:center;"><a href="/wiki/Antivitamin" class="mw-redirect" title="Antivitamin">Antivitamin B6</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/Ginkgotoxin" title="Ginkgotoxin">Ginkgotoxin</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><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> </i></dd> <dd><i><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a> </i></dd> <dd><i><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators">GABA<sub>A</sub> receptor positive modulators</a> </i></dd> <dd><i><a href="/wiki/Template:Glutamate_metabolism_and_transport_modulators" title="Template:Glutamate metabolism and transport modulators">Glutamate metabolism/transport modulators</a> </i></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="Histone_deacetylase_inhibitors116" 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:Histone_deacetylase_inhibitors" title="Template:Histone deacetylase inhibitors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Histone_deacetylase_inhibitors" title="Template talk:Histone deacetylase inhibitors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Histone_deacetylase_inhibitors" title="Special:EditPage/Template:Histone deacetylase inhibitors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Histone_deacetylase_inhibitors116" style="font-size:114%;margin:0 4em"><a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">Histone deacetylase inhibitors</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/3,3%27-Diindolylmethane" title="3,3'-Diindolylmethane">3,3'-Diindolylmethane</a></li> <li><a href="/wiki/Beta-Hydroxybutyric_acid" class="mw-redirect" title="Beta-Hydroxybutyric acid">β-Hydroxybutyric acid (β-hydroxybutyrate)</a></li> <li><a href="/wiki/Abexinostat" title="Abexinostat">Abexinostat</a></li> <li><a href="/wiki/Acetoacetic_acid" title="Acetoacetic acid">Acetoacetic acid (acetoacetate)</a></li> <li><a href="/wiki/Allyl_mercaptan" title="Allyl mercaptan">Allyl mercaptan</a></li> <li><a href="/wiki/Apicidin" title="Apicidin">Apicidin</a></li> <li><a href="/wiki/Belinostat" title="Belinostat">Belinostat</a></li> <li><a href="/wiki/Butyric_acid" title="Butyric acid">Butyric acid (butyrate)</a></li> <li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a></li> <li><a href="/w/index.php?title=Citarinostat&action=edit&redlink=1" class="new" title="Citarinostat (page does not exist)">Citarinostat</a></li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/wiki/Diallyl_disulfide" title="Diallyl disulfide">Diallyl disulfide</a></li> <li><a href="/wiki/Entinostat" title="Entinostat">Entinostat</a></li> <li><a href="/w/index.php?title=Fimepinostat&action=edit&redlink=1" class="new" title="Fimepinostat (page does not exist)">Fimepinostat</a></li> <li><a href="/wiki/Givinostat" title="Givinostat">Givinostat</a></li> <li><a href="/wiki/Indole-3-carbinol" title="Indole-3-carbinol">Indole-3-carbinol</a></li> <li><a href="/w/index.php?title=Kevetrin&action=edit&redlink=1" class="new" title="Kevetrin (page does not exist)">Kevetrin</a></li> <li><a href="/wiki/Martinostat" title="Martinostat">Martinostat</a></li> <li><a href="/wiki/Mocetinostat" title="Mocetinostat">Mocetinostat</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Panobinostat" title="Panobinostat">Panobinostat</a></li> <li><a href="/wiki/Parthenolide" title="Parthenolide">Parthenolide</a></li> <li><a href="/wiki/Phenylbutyrate" class="mw-redirect" title="Phenylbutyrate">Phenylbutyrate</a></li> <li><a href="/wiki/Pracinostat" title="Pracinostat">Pracinostat</a></li> <li><a href="/wiki/Quisinostat" title="Quisinostat">Quisinostat</a></li> <li><a href="/wiki/Resminostat" title="Resminostat">Resminostat</a></li> <li><a href="/wiki/Romidepsin" title="Romidepsin">Romidepsin</a></li> <li><a href="/wiki/Scriptaid" title="Scriptaid">Scriptaid</a></li> <li><a href="/wiki/Sodium_butyrate" title="Sodium butyrate">Sodium butyrate</a></li> <li><a href="/wiki/Sodium_oxybate" title="Sodium oxybate">Sodium oxybate (GHB sodium)</a></li> <li><a href="/wiki/Sodium_phenylbutyrate" title="Sodium phenylbutyrate">Sodium phenylbutyrate</a></li> <li><a href="/wiki/Sodium_valproate" class="mw-redirect" title="Sodium valproate">Sodium valproate</a></li> <li><a href="/wiki/Sulforaphane" title="Sulforaphane">Sulforaphane</a></li> <li><a href="/w/index.php?title=Trapoxin_B&action=edit&redlink=1" class="new" title="Trapoxin B (page does not exist)">Trapoxin B</a></li> <li><a href="/wiki/Trichostatin_A" title="Trichostatin A">Trichostatin A</a></li> <li><a href="/wiki/Tucidinostat" title="Tucidinostat">Tucidinostat</a></li> <li><a href="/wiki/Valnoctamide" title="Valnoctamide">Valnoctamide</a></li> <li><a class="mw-selflink selflink">Valproic acid (valproate)</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/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Vorinostat" title="Vorinostat">Vorinostat (SAHA)</a></li></ul> </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></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="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 href="/wiki/Ketoconazole" title="Ketoconazole">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="Progesterone_receptor_modulators1654" 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:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Progesterone_receptor_modulators" title="Template talk:Progesterone receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Progesterone_receptor_modulators" title="Special:EditPage/Template:Progesterone receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Progesterone_receptor_modulators1654" style="font-size:114%;margin:0 4em"><a href="/wiki/Progesterone_receptor" title="Progesterone receptor">Progesterone 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/Progesterone_receptor" title="Progesterone receptor"><abbr title="Progesterone receptor">PR</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 Progesterone 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>Progesterone derivatives:</i> <a href="/wiki/3%CE%B2-Dihydroprogesterone" title="3β-Dihydroprogesterone">3β-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/9%CE%B1-Bromo-11-ketoprogesterone" class="mw-redirect" title="9α-Bromo-11-ketoprogesterone">9α-Bromo-11-ketoprogesterone</a></li> <li><a href="/wiki/11-Dehydroprogesterone" title="11-Dehydroprogesterone">11-Dehydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycorticosterone</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyprogesterone" title="16α-Hydroxyprogesterone">16α-Hydroxyprogesterone</a></li> <li><a href="/w/index.php?title=17%CE%B1-Methyl-11-deoxycorticosterone_acetate&action=edit&redlink=1" class="new" title="17α-Methyl-11-deoxycorticosterone acetate (page does not exist)">17α-Methyl-11-deoxycorticosterone acetate</a></li> <li><a href="/wiki/20%CE%B1-Dihydroprogesterone" title="20α-Dihydroprogesterone">20α-Dihydroprogesterone</a></li> <li><a href="/wiki/20%CE%B2-Dihydroprogesterone" title="20β-Dihydroprogesterone">20β-Dihydroprogesterone</a></li> <li><a href="/wiki/Dimepregnen" title="Dimepregnen">Dimepregnen</a></li> <li><a href="/wiki/Diosgenin" title="Diosgenin">Diosgenin</a></li> <li><a href="/wiki/P1-185" title="P1-185">P1-185</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Progesterone_3-acetyl_enol_ether" title="Progesterone 3-acetyl enol ether">Progesterone 3-acetyl enol ether</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li></ul> <ul><li><i>Retroprogesterone derivatives:</i> <a href="/wiki/20%CE%B1-Dihydrodydrogesterone" title="20α-Dihydrodydrogesterone">20α-Dihydrodydrogesterone</a></li> <li><a href="/wiki/20%CE%B1-Dihydrotrengestone" title="20α-Dihydrotrengestone">20α-Dihydrotrengestone</a></li> <li><a href="/wiki/DU-41164" title="DU-41164">DU-41164</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a></li> <li><a href="/wiki/Retroprogesterone" title="Retroprogesterone">Retroprogesterone</a></li> <li><a href="/wiki/Ro_6-3129" title="Ro 6-3129">Ro 6-3129</a></li> <li><a href="/wiki/Trengestone" title="Trengestone">Trengestone</a></li></ul> <ul><li><i>17α-Substituted progesterone derivatives:</i> <a href="/wiki/6%CE%B1-Methyl-17%CE%B1-bromoprogesterone" title="6α-Methyl-17α-bromoprogesterone">6α-Methyl-17α-bromoprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</a></li> <li><a href="/wiki/16-Methylene-17%CE%B1-hydroxyprogesterone_acetate" title="16-Methylene-17α-hydroxyprogesterone acetate">16-Methylene-17α-hydroxyprogesterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Bromoprogesterone" title="17α-Bromoprogesterone">17α-Bromoprogesterone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone (hydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Methylprogesterone" title="17α-Methylprogesterone">17α-Methylprogesterone</a></li> <li><a href="/wiki/Acetomepregenol" title="Acetomepregenol">Acetomepregenol (mepregenol diacetate)</a></li> <li><a href="/wiki/Algestone" title="Algestone">Algestone</a></li> <li><a href="/wiki/Algestone_acetonide" title="Algestone acetonide">Algestone acetonide</a></li> <li><a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">Algestone acetophenide</a></li> <li><a href="/wiki/Anagestone" title="Anagestone">Anagestone</a></li> <li><a href="/wiki/Anagestone_acetate" title="Anagestone acetate">Anagestone acetate</a></li> <li><a href="/w/index.php?title=Bromethenmadinone&action=edit&redlink=1" class="new" title="Bromethenmadinone (page does not exist)">Bromethenmadinone</a></li> <li><a href="/wiki/Bromethenmadinone_acetate" title="Bromethenmadinone acetate">Bromethenmadinone acetate</a></li> <li><a href="/wiki/Butagest" title="Butagest">Butagest (buterol)</a></li> <li><a href="/wiki/Chlormadinone" title="Chlormadinone">Chlormadinone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Chlormadinone_caproate" title="Chlormadinone caproate">Chlormadinone caproate</a></li> <li><a href="/w/index.php?title=Chlormethenmadinone&action=edit&redlink=1" class="new" title="Chlormethenmadinone (page does not exist)">Chlormethenmadinone</a></li> <li><a href="/wiki/Chlormethenmadinone_acetate" title="Chlormethenmadinone acetate">Chlormethenmadinone acetate</a></li> <li><a href="/wiki/Cismadinone" title="Cismadinone">Cismadinone</a></li> <li><a href="/wiki/Cismadinone_acetate" title="Cismadinone acetate">Cismadinone acetate</a></li> <li><a href="/wiki/Clogestone" title="Clogestone">Clogestone</a></li> <li><a href="/wiki/Clogestone_acetate" title="Clogestone acetate">Clogestone acetate</a></li> <li><a href="/wiki/Clomegestone" title="Clomegestone">Clomegestone</a></li> <li><a href="/wiki/Clomegestone_acetate" title="Clomegestone acetate">Clomegestone acetate</a></li> <li><a href="/wiki/Cymegesolate" title="Cymegesolate">Cymegesolate</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone" title="Delmadinone">Delmadinone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/wiki/Flugestone" title="Flugestone">Flugestone</a></li> <li><a href="/wiki/Flugestone_acetate" title="Flugestone acetate">Flugestone acetate</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Fluorometholone_acetate" title="Fluorometholone acetate">Fluorometholone acetate</a></li> <li><a href="/wiki/Flumedroxone" title="Flumedroxone">Flumedroxone</a></li> <li><a href="/wiki/Flumedroxone_acetate" title="Flumedroxone acetate">Flumedroxone acetate</a></li> <li><a href="/wiki/Fluoromedroxyprogesterone_acetate" title="Fluoromedroxyprogesterone acetate">Fluoromedroxyprogesterone acetate</a></li> <li><a href="/wiki/Gestaclone" title="Gestaclone">Gestaclone</a></li> <li><a href="/w/index.php?title=Gestobutanoyl&action=edit&redlink=1" class="new" title="Gestobutanoyl (page does not exist)">Gestobutanoyl</a></li> <li><a href="/wiki/Haloprogesterone" title="Haloprogesterone">Haloprogesterone</a></li> <li><a href="/wiki/Hydromadinone" title="Hydromadinone">Hydromadinone</a></li> <li><a href="/wiki/Hydromadinone_acetate" title="Hydromadinone acetate">Hydromadinone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_acetate" title="Hydroxyprogesterone acetate">Hydroxyprogesterone acetate</a></li> <li><a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate" title="Hydroxyprogesterone heptanoate">Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)</a></li> <li><a href="/wiki/Hydroxyprogesterone_heptanoate_benzilic_acid_hydrazone" title="Hydroxyprogesterone heptanoate benzilic acid hydrazone">Hydroxyprogesterone heptanoate benzilic acid hydrazone</a></li> <li><a href="/wiki/Mecigestone" title="Mecigestone">Mecigestone (pentarane B)</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Medroxyprogesterone" title="Medroxyprogesterone">Medroxyprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Medroxyprogesterone_caproate" title="Medroxyprogesterone caproate">Medroxyprogesterone caproate</a></li> <li><a href="/wiki/Megestrol" title="Megestrol">Megestrol</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Megestrol_caproate" title="Megestrol caproate">Megestrol caproate</a></li> <li><a href="/wiki/Melengestrol" title="Melengestrol">Melengestrol</a></li> <li><a href="/wiki/Melengestrol_acetate" title="Melengestrol acetate">Melengestrol acetate</a></li> <li><a href="/wiki/Methenmadinone" title="Methenmadinone">Methenmadinone</a></li> <li><a href="/wiki/Methenmadinone_acetate" title="Methenmadinone acetate">Methenmadinone acetate</a></li> <li><a href="/wiki/Methenmadinone_caproate" title="Methenmadinone caproate">Methenmadinone caproate</a></li> <li><a href="/wiki/Mometasone" title="Mometasone">Mometasone</a></li> <li><a href="/wiki/Mometasone_furoate" class="mw-redirect" title="Mometasone furoate">Mometasone furoate</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/Pentagestrone" title="Pentagestrone">Pentagestrone</a></li> <li><a href="/wiki/Pentagestrone_acetate" title="Pentagestrone acetate">Pentagestrone acetate</a></li> <li><a href="/wiki/Pentarane_A" title="Pentarane A">Pentarane A</a></li> <li><a href="/wiki/Proligestone" title="Proligestone">Proligestone</a></li> <li><a href="/wiki/Triamcinolone_acetonide" title="Triamcinolone acetonide">Triamcinolone acetonide</a></li></ul> <ul><li><i>19-Norprogesterone derivatives:</i> <a href="/wiki/17%CE%B1-Methyl-19-norprogesterone" title="17α-Methyl-19-norprogesterone">17α-Methyl-19-norprogesterone</a></li> <li><a href="/wiki/18-Methylsegesterone_acetate" title="18-Methylsegesterone acetate">18-Methylsegesterone acetate</a></li> <li><a href="/wiki/19-Norprogesterone" title="19-Norprogesterone">19-Norprogesterone</a></li> <li><a href="/wiki/Amadinone" title="Amadinone">Amadinone</a></li> <li><a href="/wiki/Amadinone_acetate" title="Amadinone acetate">Amadinone acetate</a></li> <li><a href="/wiki/Demegestone" title="Demegestone">Demegestone</a></li> <li><a href="/w/index.php?title=Fluoro_ethyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro ethyl norprogesterone (page does not exist)">Fluoro ethyl norprogesterone</a></li> <li><a href="/w/index.php?title=Fluoro_furanyl_norprogesterone&action=edit&redlink=1" class="new" title="Fluoro furanyl norprogesterone (page does not exist)">Fluoro furanyl norprogesterone</a></li> <li><a href="/wiki/Gestadienol" title="Gestadienol">Gestadienol</a></li> <li><a href="/wiki/Gestadienol_acetate" title="Gestadienol acetate">Gestadienol acetate</a></li> <li><a href="/wiki/Gestonorone_acetate" title="Gestonorone acetate">Gestonorone acetate (gestronol acetate)</a></li> <li><a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">Gestonorone caproate (gestronol hexanoate)</a></li> <li><a href="/wiki/Gestronol" title="Gestronol">Gestronol (gestonorone)</a></li> <li><a href="/wiki/Nomegestrol" title="Nomegestrol">Nomegestrol</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Norgestomet" title="Norgestomet">Norgestomet</a></li> <li><a href="/wiki/ORG-2058" title="ORG-2058">ORG-2058</a></li> <li><a href="/wiki/Oxogestone" title="Oxogestone">Oxogestone</a></li> <li><a href="/wiki/Oxogestone_phenpropionate" title="Oxogestone phenpropionate">Oxogestone phenpropionate (xinogestone)</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Segesterone" title="Segesterone">Segesterone</a></li> <li><a href="/wiki/Nestorone" class="mw-redirect" title="Nestorone">Segesterone acetate (nestorone)</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li></ul> <ul><li><i>Testosterone derivatives:</i> Progestins: <a href="/wiki/6,6-Difluoronorethisterone" title="6,6-Difluoronorethisterone">6,6-Difluoronorethisterone</a></li> <li><a href="/wiki/6,6-Difluoronorethisterone_acetate" title="6,6-Difluoronorethisterone acetate">6,6-Difluoronorethisterone acetate</a></li> <li><a href="/wiki/17%CE%B1-Allyl-19-nortestosterone" title="17α-Allyl-19-nortestosterone">17α-Allyl-19-nortestosterone</a></li> <li><a href="/wiki/Allylestrenol" title="Allylestrenol">Allylestrenol</a></li> <li><a href="/wiki/Altrenogest" title="Altrenogest">Altrenogest</a></li> <li><a href="/wiki/Chloroethynylnorgestrel" title="Chloroethynylnorgestrel">Chloroethynylnorgestrel</a></li> <li><a href="/wiki/Cingestol" title="Cingestol">Cingestol</a></li> <li><a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</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</a></li> <li><a href="/wiki/Ethynerone" title="Ethynerone">Ethynerone</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></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></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Metynodiol" title="Metynodiol">Metynodiol</a></li> <li><a href="/wiki/Metynodiol_diacetate" title="Metynodiol diacetate">Metynodiol diacetate</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone (norethindrone)</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/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Norgesterone" title="Norgesterone">Norgesterone</a></li> <li><a href="/wiki/Norgestimate" title="Norgestimate">Norgestimate</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/Norvinisterone" title="Norvinisterone">Norvinisterone</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a></li> <li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li> <li><a href="/wiki/Tigestol" title="Tigestol">Tigestol</a></li> <li><a href="/wiki/Tosagestin" title="Tosagestin">Tosagestin</a>; Anabolic–androgenic steroids: <a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></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></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione</a></li> <li><a href="/wiki/Dimethisterone" title="Dimethisterone">Dimethisterone</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></li> <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> <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 (ethylnandrol)</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone (R-1881)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a></li> <li><a href="/wiki/Nandrolone_ester" class="mw-redirect" title="Nandrolone ester">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/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethandrolone, normethisterone)</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> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone (trienolone)</a></li> <li><a href="/wiki/Trenbolone_ester" class="mw-redirect" title="Trenbolone ester">Trenbolone esters</a> (e.g., <a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">trenbolone acetate</a>, <a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">trenbolone enanthate</a>)</li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone</a></li> <li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li></ul> <ul><li><i>Spirolactone derivatives:</i> <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/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/SC-8109" title="SC-8109">SC-8109</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/3,8-Dihydrodiligustilide" title="3,8-Dihydrodiligustilide">3,8-Dihydrodiligustilide</a></li> <li><a href="/wiki/LG-2527" title="LG-2527">LG-2527</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/wiki/Riligustilide" title="Riligustilide">Riligustilide</a></li> <li><a href="/w/index.php?title=RWJ-26819&action=edit&redlink=1" class="new" title="RWJ-26819 (page does not exist)">RWJ-26819</a></li> <li><a href="/w/index.php?title=RWJ-49853&action=edit&redlink=1" class="new" title="RWJ-49853 (page does not exist)">RWJ-49853</a></li> <li><a href="/w/index.php?title=RWJ-60130&action=edit&redlink=1" class="new" title="RWJ-60130 (page does not exist)">RWJ-60130</a></li> <li><a href="/wiki/Tanaproget" title="Tanaproget">Tanaproget</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> <ul><li><i>Unknown:</i> <a href="/wiki/ORG-47241" title="ORG-47241">ORG-47241</a></li> <li><a href="/wiki/ORG-201745" title="ORG-201745">ORG-201745</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_progesterone_receptor_modulators" class="mw-redirect" title="Selective progesterone receptor modulators"><abbr title="Selective progesterone receptor modulators">SPRMs</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 progesterone receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li> <li><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> <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="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=J1042&action=edit&redlink=1" class="new" title="J1042 (page does not exist)">J1042</a></li> <li><a href="/w/index.php?title=LG-120838&action=edit&redlink=1" class="new" title="LG-120838 (page does not exist)">LG-120838</a></li> <li><a href="/wiki/Metapristone" title="Metapristone">Metapristone (RU-42633)</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone (RU-486)</a></li> <li><a href="/w/index.php?title=ORF-9371&action=edit&redlink=1" class="new" title="ORF-9371 (page does not exist)">ORF-9371</a></li> <li><a href="/wiki/ORF-9326" class="mw-redirect" title="ORF-9326">ORF-9326</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</a></li> <li><a href="/w/index.php?title=RMI-12936&action=edit&redlink=1" class="new" title="RMI-12936 (page does not exist)">RMI-12936</a></li> <li><a href="/wiki/Telapristone" title="Telapristone">Telapristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal acetate</a></li> <li><a href="/wiki/Vilaprisan" title="Vilaprisan">Vilaprisan</a></li> <li><a href="/w/index.php?title=ZK-137316&action=edit&redlink=1" class="new" title="ZK-137316 (page does not exist)">ZK-137316</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Apigenin" title="Apigenin">Apigenin</a></li> <li><a href="/wiki/Kaempferol" title="Kaempferol">Kaempferol</a></li> <li><a href="/w/index.php?title=LG-120920&action=edit&redlink=1" class="new" title="LG-120920 (page does not exist)">LG-120920</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/w/index.php?title=PRA-910&action=edit&redlink=1" class="new" title="PRA-910 (page does not exist)">PRA-910</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</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/Aglepristone" title="Aglepristone">Aglepristone</a></li> <li><a href="/wiki/Lilopristone" title="Lilopristone">Lilopristone</a></li> <li><a href="/wiki/Lonaprisan" title="Lonaprisan">Lonaprisan</a></li> <li><a href="/wiki/Onapristone" title="Onapristone">Onapristone</a></li> <li><a href="/w/index.php?title=ORG-31710&action=edit&redlink=1" class="new" title="ORG-31710 (page does not exist)">ORG-31710</a></li> <li><a href="/w/index.php?title=ORG-31806&action=edit&redlink=1" class="new" title="ORG-31806 (page does not exist)">ORG-31806</a></li> <li><a href="/w/index.php?title=ORG-33628&action=edit&redlink=1" class="new" title="ORG-33628 (page does not exist)">ORG-33628</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/Toripristone" title="Toripristone">Toripristone</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/w/index.php?title=LG-001447&action=edit&redlink=1" class="new" title="LG-001447 (page does not exist)">LG-001447</a></li> <li><a href="/w/index.php?title=LG-100127&action=edit&redlink=1" class="new" title="LG-100127 (page does not exist)">LG-100127</a></li> <li><a href="/w/index.php?title=LG-100128&action=edit&redlink=1" class="new" title="LG-100128 (page does not exist)">LG-100128</a></li> <li><a href="/w/index.php?title=LG-120830&action=edit&redlink=1" class="new" title="LG-120830 (page does not exist)">LG-120830</a></li> <li><a href="/w/index.php?title=LG-121046&action=edit&redlink=1" class="new" title="LG-121046 (page does not exist)">LG-121046</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/w/index.php?title=ZM-150271&action=edit&redlink=1" class="new" title="ZM-150271 (page does not exist)">ZM-150271</a></li> <li><a href="/w/index.php?title=ZM-172406&action=edit&redlink=1" class="new" title="ZM-172406 (page does not exist)">ZM-172406</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/Membrane_progesterone_receptor" title="Membrane progesterone receptor"><abbr title="Membrane progesterone receptor">mPR</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 Membrane progesterone receptor</span><br />(<a href="/wiki/Progestin_and_adipoQ_receptor" title="Progestin and adipoQ receptor"><abbr title="Progestin and adipoQ receptor">PAQR</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 Progestin and adipoQ receptor</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">5α-Dihydroprogesterone</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">5β-Dihydroprogesterone</a></li> <li><a href="/wiki/11-Deoxycorticosterone" title="11-Deoxycorticosterone">11-Deoxycortisone (21-hydroxyprogesterone)</a></li> <li><a href="/wiki/11-Deoxycortisol" title="11-Deoxycortisol">11-Deoxycortisol (17α,21-dihydroxyprogesterone)</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</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><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</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:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_progestogens" class="mw-redirect" title="List of steroidal progestogens">List of progestogens</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="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 href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/wiki/Reverse_triiodothyronine" title="Reverse triiodothyronine">Reverse triiodothyronine</a></li> <li><a href="/wiki/Rifampicin" title="Rifampicin">Rifampicin</a></li> <li><a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Riodipine" title="Riodipine">Riodipine</a></li> <li><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir</a></li> <li><a href="/wiki/Simvastatin" title="Simvastatin">Simvastatin</a></li> <li><a href="/wiki/Sirolimus" title="Sirolimus">Sirolimus</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/w/index.php?title=SR-12813&action=edit&redlink=1" class="new" title="SR-12813 (page does not 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" title="Thiothixene">Thiothixene</a></li> <li><a href="/wiki/Thonzonium_bromide" title="Thonzonium bromide">Thonzonium bromide</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/w/index.php?title=Tropanyl_3,5-dimethulbenzoate&action=edit&redlink=1" class="new" title="Tropanyl 3,5-dimethulbenzoate (page does not exist)">Tropanyl 3,5-dimethulbenzoate</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Sesamin" title="Sesamin">Sesamin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd></dl> </div></td></tr></tbody></table></div></div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output .portal-bar-content-related{margin:0;list-style:none}.mw-parser-output .portal-bar-item{display:inline-block;margin:0.15em 0.2em;min-height:24px;line-height:24px}@media screen and (max-width:768px){.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;flex-flow:column wrap;align-items:baseline}.mw-parser-output .portal-bar-header{text-align:center;flex:0;padding-left:0.5em;margin:0 auto}.mw-parser-output .portal-bar-related{font-size:100%;align-items:flex-start}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;align-items:center;flex:0;column-gap:1em;border-top:1px solid #a2a9b1;margin:0 auto;list-style:none}.mw-parser-output .portal-bar-content-related{border-top:none;margin:0;list-style:none}}.mw-parser-output .navbox+link+.portal-bar,.mw-parser-output .navbox+style+.portal-bar,.mw-parser-output .navbox+link+.portal-bar-bordered,.mw-parser-output .navbox+style+.portal-bar-bordered,.mw-parser-output .sister-bar+link+.portal-bar,.mw-parser-output .sister-bar+style+.portal-bar,.mw-parser-output .portal-bar+.navbox-styles+.navbox,.mw-parser-output .portal-bar+.navbox-styles+.sister-bar{margin-top:-1px}</style><div class="portal-bar noprint metadata noviewer portal-bar-bordered" role="navigation" aria-label="Portals"><span class="portal-bar-header"><a href="/wiki/Wikipedia:Contents/Portals" title="Wikipedia:Contents/Portals">Portal</a>:</span><ul class="portal-bar-content"><li class="portal-bar-item"><span class="nowrap"><span typeof="mw:File"><span><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/8px-WHO_Rod.svg.png" decoding="async" width="8" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/12px-WHO_Rod.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/16px-WHO_Rod.svg.png 2x" data-file-width="107" data-file-height="250" /></span></span> </span><a href="/wiki/Portal:Medicine" title="Portal:Medicine">Medicine</a></li></ul></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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox1129" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q240642#identifiers" 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></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Valproic acid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85141922">United States</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Valproïque, Acide"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb122625973">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Valproïque, Acide"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb122625973">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://www.nli.org.il/en/authorities/987007531852805171">Israel</a></span></li></ul></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" 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