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Tamoxifen - Wikipedia

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<li id="toc-Dysmenorrhea" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dysmenorrhea"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Dysmenorrhea</span> </div> </a> <ul id="toc-Dysmenorrhea-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Breast_cancer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Breast_cancer"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Breast cancer</span> </div> </a> <ul id="toc-Breast_cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Infertility" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Infertility"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Infertility</span> </div> </a> <ul id="toc-Infertility-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gynecomastia" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Gynecomastia"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Gynecomastia</span> </div> </a> <ul id="toc-Gynecomastia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Early_puberty" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Early_puberty"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5</span> <span>Early puberty</span> </div> </a> <ul id="toc-Early_puberty-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Available_forms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Available_forms"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.6</span> <span>Available forms</span> </div> </a> <ul id="toc-Available_forms-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-Side_effects" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Side effects</span> </div> </a> <button aria-controls="toc-Side_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Side effects subsection</span> </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-Endometrial_cancer" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Endometrial_cancer"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Endometrial cancer</span> </div> </a> <ul id="toc-Endometrial_cancer-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular_and_metabolic" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiovascular_and_metabolic"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Cardiovascular and metabolic</span> </div> </a> <ul id="toc-Cardiovascular_and_metabolic-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Liver_toxicity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Liver_toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.3</span> <span>Liver toxicity</span> </div> </a> <ul id="toc-Liver_toxicity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Overdose</span> </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Interactions</span> </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Selective_estrogen_receptor_modulator_activity" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Selective_estrogen_receptor_modulator_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.1</span> <span>Selective estrogen receptor modulator activity</span> </div> </a> <ul id="toc-Selective_estrogen_receptor_modulator_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_activities" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other_activities"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1.2</span> <span>Other activities</span> </div> </a> <ul id="toc-Other_activities-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> <li id="toc-Absorption" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Absorption"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.1</span> <span>Absorption</span> </div> </a> <ul id="toc-Absorption-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Distribution" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Distribution"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.2</span> <span>Distribution</span> </div> </a> <ul id="toc-Distribution-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.3</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Elimination" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Elimination"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2.4</span> <span>Elimination</span> </div> </a> <ul id="toc-Elimination-sublist" class="vector-toc-list"> </ul> </li> </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-Brand_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brand_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Brand names</span> </div> </a> <ul id="toc-Brand_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Economics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Economics"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Economics</span> </div> </a> <ul id="toc-Economics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Research</span> </div> </a> <ul id="toc-Research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-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> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header 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" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Tamoxifen</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" 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Available in 38 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-38" 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">38 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AA%D8%A7%D9%85%D9%88%D9%83%D8%B3%D9%8A%D9%81%D9%8A%D9%86" title="تاموكسيفين – Arabic" lang="ar" hreflang="ar" data-title="تاموكسيفين" 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/%D8%AA%D8%A7%D9%85%D9%88%DA%A9%D8%B3%DB%8C%D9%81%D9%86" title="تاموکسیفن – South Azerbaijani" lang="azb" hreflang="azb" data-title="تاموکسیفن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Tamoxifen" title="Tamoxifen – Czech" lang="cs" hreflang="cs" data-title="Tamoxifen" 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/Tamocsiffen" title="Tamocsiffen – Welsh" lang="cy" hreflang="cy" data-title="Tamocsiffen" 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/Tamoxifen" title="Tamoxifen – German" lang="de" hreflang="de" data-title="Tamoxifen" 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%A4%CE%B1%CE%BC%CE%BF%CE%BE%CE%B9%CF%86%CE%B1%CE%AF%CE%BD%CE%B7" title="Ταμοξιφαίνη – Greek" lang="el" hreflang="el" data-title="Ταμοξιφαίνη" 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/Tamoxifeno" title="Tamoxifeno – Spanish" lang="es" hreflang="es" data-title="Tamoxifeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Tamoxifeno" title="Tamoxifeno – Basque" lang="eu" hreflang="eu" data-title="Tamoxifeno" 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/%D8%AA%D8%A7%D9%85%D9%88%DA%A9%D8%B3%DB%8C%D9%81%D9%86" title="تاموکسیفن – Persian" lang="fa" hreflang="fa" data-title="تاموکسیفن" 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/Tamoxif%C3%A8ne" title="Tamoxifène – French" lang="fr" hreflang="fr" data-title="Tamoxifène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Tamocsaifein" title="Tamocsaifein – Irish" lang="ga" hreflang="ga" data-title="Tamocsaifein" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Tamoxifeno" title="Tamoxifeno – Galician" lang="gl" hreflang="gl" data-title="Tamoxifeno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%ED%83%80%EB%AA%A9%EC%8B%9C%ED%8E%9C" title="타목시펜 – Korean" lang="ko" hreflang="ko" data-title="타목시펜" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8F%D5%A1%D5%B4%D5%B8%D6%84%D5%BD%D5%AB%D6%86%D5%A5%D5%B6" title="Տամոքսիֆեն – Armenian" lang="hy" hreflang="hy" data-title="Տամոքսիֆեն" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Tamoksifen" title="Tamoksifen – Indonesian" lang="id" hreflang="id" data-title="Tamoksifen" 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/Tamoxifene" title="Tamoxifene – Italian" lang="it" hreflang="it" data-title="Tamoxifene" 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%98%D7%9E%D7%95%D7%A7%D7%A1%D7%99%D7%A4%D7%9F" title="טמוקסיפן – Hebrew" lang="he" hreflang="he" data-title="טמוקסיפן" 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/Tamoxifenum" title="Tamoxifenum – Latin" lang="la" hreflang="la" data-title="Tamoxifenum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Tamoksifenas" title="Tamoksifenas – Lithuanian" lang="lt" hreflang="lt" data-title="Tamoksifenas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A2%D0%B0%D0%BC%D0%BE%D0%BA%D1%81%D0%B8%D1%84%D0%B5%D0%BD" title="Тамоксифен – Macedonian" lang="mk" hreflang="mk" data-title="Тамоксифен" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%A2%D0%B0%D0%BC%D0%BE%D0%BA%D1%81%D0%B8%D1%84%D0%B5%D0%BD" title="Тамоксифен – Mongolian" lang="mn" hreflang="mn" data-title="Тамоксифен" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Tamoxifen" title="Tamoxifen – Dutch" lang="nl" hreflang="nl" data-title="Tamoxifen" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%BF%E3%83%A2%E3%82%AD%E3%82%B7%E3%83%95%E3%82%A7%E3%83%B3" title="タモキシフェン – Japanese" lang="ja" hreflang="ja" data-title="タモキシフェン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%9F%E0%AC%BE%E0%AC%AE%E0%AD%8B%E0%AC%95%E0%AD%8D%E0%AC%B8%E0%AC%BF%E0%AC%AB%E0%AD%87%E0%AC%A8" title="ଟାମୋକ୍ସିଫେନ – Odia" lang="or" hreflang="or" data-title="ଟାମୋକ୍ସିଫେନ" 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/Tamoksyfen" title="Tamoksyfen – Polish" lang="pl" hreflang="pl" data-title="Tamoksyfen" 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/Tamoxifeno" title="Tamoxifeno – Portuguese" lang="pt" hreflang="pt" data-title="Tamoxifeno" 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/Tamoxifen" title="Tamoxifen – Romanian" lang="ro" hreflang="ro" data-title="Tamoxifen" 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%A2%D0%B0%D0%BC%D0%BE%D0%BA%D1%81%D0%B8%D1%84%D0%B5%D0%BD" title="Тамоксифен – Russian" lang="ru" hreflang="ru" data-title="Тамоксифен" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Tamoksifen" title="Tamoksifen – Slovenian" lang="sl" hreflang="sl" data-title="Tamoksifen" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Tamoksifen" title="Tamoksifen – Serbian" lang="sr" hreflang="sr" data-title="Tamoksifen" 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/Tamoksifen" title="Tamoksifen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Tamoksifen" 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/Tamoksifeeni" title="Tamoksifeeni – Finnish" lang="fi" hreflang="fi" data-title="Tamoksifeeni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%A2%D0%B0%D0%BC%D0%BE%D0%BA%D1%81%D0%B8%D1%84%D0%B5%D0%BD" title="Тамоксифен – Tatar" lang="tt" hreflang="tt" data-title="Тамоксифен" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%97%E0%B8%B2%E0%B8%A1%E0%B9%87%E0%B8%AD%E0%B8%81%E0%B8%8B%E0%B8%B4%E0%B9%80%E0%B8%9F%E0%B8%99" title="ทาม็อกซิเฟน – Thai" lang="th" hreflang="th" data-title="ทาม็อกซิเฟน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Tamoksifen" title="Tamoksifen – Turkish" lang="tr" hreflang="tr" data-title="Tamoksifen" 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%A2%D0%B0%D0%BC%D0%BE%D0%BA%D1%81%D0%B8%D1%84%D0%B5%D0%BD" title="Тамоксифен – Ukrainian" lang="uk" hreflang="uk" data-title="Тамоксифен" data-language-autonym="Українська" data-language-local-name="Ukrainian" 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searchaux" style="display:none">Medication</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Tamoxifen">Tamoxifen</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Tamoxifen2DACS.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Tamoxifen2DACS.svg/250px-Tamoxifen2DACS.svg.png" decoding="async" width="250" height="185" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Tamoxifen2DACS.svg/375px-Tamoxifen2DACS.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Tamoxifen2DACS.svg/500px-Tamoxifen2DACS.svg.png 2x" data-file-width="708" data-file-height="524" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Tamoxifen-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Tamoxifen-3D-balls.png/175px-Tamoxifen-3D-balls.png" decoding="async" width="175" height="253" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/07/Tamoxifen-3D-balls.png/263px-Tamoxifen-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/07/Tamoxifen-3D-balls.png/350px-Tamoxifen-3D-balls.png 2x" data-file-width="760" data-file-height="1100" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Nolvadex, Genox, Tamifen, others<sup id="cite_ref-drug_dictionary_1-0" class="reference"><a href="#cite_note-drug_dictionary-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">TMX; ICI-46474</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/tamoxifen-citrate.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/a682414.html">a682414</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>&#160;<a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>:&#160;<span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&amp;query=Tamoxifen">Tamoxifen</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>&#x20;B3<sup id="cite_ref-Drugs.com_pregnancy_2-0" class="reference"><a href="#cite_note-Drugs.com_pregnancy-2"><span class="cite-bracket">&#91;</span>2<span class="cite-bracket">&#93;</span></a></sup></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></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">Selective estrogen receptor modulator</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_L02" title="ATC code L02">L02BA01</a>&#x20;(<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L02BA01">WHO</a></span>)&#x20;</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small>&#x20;<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="Canada">CA</abbr></small>:&#x20;<a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small>&#x20;<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>&#x20;<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">&#91;</span>3<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">&#91;</span>4<span class="cite-bracket">&#93;</span></a></sup></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">~100%<sup id="cite_ref-MorelloWurz2003_5-0" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-BrennerStevens2017_6-0" class="reference"><a href="#cite_note-BrennerStevens2017-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">&gt;99% (<a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a>)<sup id="cite_ref-MorelloWurz2003_5-1" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-ChabnerLongo2011_7-0" class="reference"><a href="#cite_note-ChabnerLongo2011-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</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/CYP3A4" title="CYP3A4">CYP3A4</a>, <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a>, <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a>)<sup id="cite_ref-MorelloWurz2003_5-3" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Nolvadex-Label_12-0" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Sanchez-SpitmanSwen2019_8-7" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• <a href="/wiki/N-Desmethyltamoxifen" title="N-Desmethyltamoxifen"><i>N</i>-Desmethyltamoxifen</a><sup id="cite_ref-Sanchez-SpitmanSwen2019_8-0" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid23962908_9-0" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><br />• <a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a> (4-hydroxy-<i>N</i>-desmethyltamoxifen)<sup id="cite_ref-Sanchez-SpitmanSwen2019_8-1" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid23962908_9-1" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><br />• <a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a> (4-hydroxytamoxifen)<sup id="cite_ref-Sanchez-SpitmanSwen2019_8-2" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid23962908_9-2" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><br />• <a href="/wiki/N,N-Didesmethyltamoxifen" title="N,N-Didesmethyltamoxifen"><i>N</i>,<i>N</i>-Didesmethyltamoxifen</a><sup id="cite_ref-Sanchez-SpitmanSwen2019_8-3" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><br />• <a href="/wiki/Norendoxifen" title="Norendoxifen">Norendoxifen</a> (4-hydroxy-<i>N</i>,<i>N</i>-didesmethyltamoxifen)<sup id="cite_ref-Sanchez-SpitmanSwen2019_8-4" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><br />• Others, <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugates</a><sup id="cite_ref-Sanchez-SpitmanSwen2019_8-5" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid21451508_10-0" class="reference"><a href="#cite_note-pmid21451508-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Nagar2010_11-0" class="reference"><a href="#cite_note-Nagar2010-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">5–7 days<sup id="cite_ref-MorelloWurz2003_5-2" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Sanchez-SpitmanSwen2019_8-6" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Feces" title="Feces">Feces</a>: 65%<br /><a href="/wiki/Urine" title="Urine">Urine</a>: 9%</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(<i>Z</i>)-2-[4-(1,2-Diphenylbut-1-enyl)phenoxy]-<i>N</i>,<i>N</i>-dimethylethanamine</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=10540-29-1">10540-29-1</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li>citrate:&#160;<span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=54965-24-1">54965-24-1</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/2733526">2733526</a></span></li><li>citrate:&#x20;<span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/2733525">2733525</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=1016">1016</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/DB00675">DB00675</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li>citrate:&#160;<span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DBSALT000168">DBSALT000168</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.2015313.html">2015313</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li>citrate:&#x20;<span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.2015312.html">2015312</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/094ZI81Y45">094ZI81Y45</a></span></li><li>citrate:&#160;<span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/7FRV7310N6">7FRV7310N6</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/D08559">D08559</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li>citrate:&#160;<span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00966">D00966</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:41774">CHEBI:41774</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li>citrate:&#160;<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9397">CHEBI:9397</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/chembldb/index.php/compound/inspect/ChEMBL83">ChEMBL83</a></span><sup>&#160;<span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li>citrate:&#160;<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL786">ChEMBL786</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB ligand</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>CTX (<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=CTX">PDBe</a></span>, <span title="www.rcsb.org"><a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/CTX">RCSB&#160;PDB</a></span>)</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID1034187">DTXSID1034187</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q412178#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/100.031.004">100.031.004</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q412178#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>26</sub><span title="Hydrogen">H</span><sub>29</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002371524000000000♠"></span>371.524</span>&#160;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=CN%28C%29CCOc1ccc%28cc1%29%2FC%28c2ccccc2%29%3DC%28%2FCC%29c3ccccc3">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%;">CN(C)CCOc1ccc(cc1)/C(c2ccccc2)=C(/CC)c3ccccc3</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/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25-<sup>&#160;<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:NKANXQFJJICGDU-QPLCGJKRSA-N<sup>&#160;<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">&#160;&#160;<span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&amp;rev1=470477095&amp;page2=Tamoxifen">(verify)</a></span></span></td></tr></tbody></table> <p><b>Tamoxifen</b>, sold under the brand name <b>Nolvadex</b> among others, is a <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a> used to prevent <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in women and men.<sup id="cite_ref-NCI2015_13-0" class="reference"><a href="#cite_note-NCI2015-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> It is also being studied for other types of <a href="/wiki/Cancer" title="Cancer">cancer</a>.<sup id="cite_ref-NCI2015_13-1" class="reference"><a href="#cite_note-NCI2015-13"><span class="cite-bracket">&#91;</span>13<span class="cite-bracket">&#93;</span></a></sup> It has been used for <a href="/wiki/Albright_syndrome" class="mw-redirect" title="Albright syndrome">Albright syndrome</a>.<sup id="cite_ref-AHFS2015_14-0" class="reference"><a href="#cite_note-AHFS2015-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen is typically taken daily <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a> for five years for breast cancer.<sup id="cite_ref-AHFS2015_14-1" class="reference"><a href="#cite_note-AHFS2015-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> </p><p>Serious side effects include a small increased risk of <a href="/wiki/Uterine_cancer" title="Uterine cancer">uterine cancer</a>, <a href="/wiki/Stroke" title="Stroke">stroke</a>, vision problems, and <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a>.<sup id="cite_ref-AHFS2015_14-2" class="reference"><a href="#cite_note-AHFS2015-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> Common side effects include <a href="/wiki/Irregular_menstruation" title="Irregular menstruation">irregular periods</a>, weight loss, and <a href="/wiki/Hot_flashes" class="mw-redirect" title="Hot flashes">hot flashes</a>.<sup id="cite_ref-AHFS2015_14-3" class="reference"><a href="#cite_note-AHFS2015-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> It may cause harm to the baby if taken during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> or <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a>.<sup id="cite_ref-AHFS2015_14-4" class="reference"><a href="#cite_note-AHFS2015-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> It is a <a href="/wiki/Selective_estrogen-receptor_modulator" class="mw-redirect" title="Selective estrogen-receptor modulator">selective estrogen-receptor modulator</a> (SERM) and works by decreasing the growth of breast cancer cells.<sup id="cite_ref-AHFS2015_14-5" class="reference"><a href="#cite_note-AHFS2015-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">&#91;</span>15<span class="cite-bracket">&#93;</span></a></sup> It is a member of the <a href="/wiki/Triphenylethylene" title="Triphenylethylene">triphenylethylene</a> group of <a href="/wiki/Chemical_compound" title="Chemical compound">compounds</a>.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">&#91;</span>16<span class="cite-bracket">&#93;</span></a></sup> </p><p>Tamoxifen was initially made in 1962, by chemist <a href="/wiki/Dora_Richardson" title="Dora Richardson">Dora Richardson</a>.<sup id="cite_ref-Viviane_M_2017_17-0" class="reference"><a href="#cite_note-Viviane_M_2017-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Jordan_2006_18-0" class="reference"><a href="#cite_note-Jordan_2006-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</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-WHO21st_19-0" class="reference"><a href="#cite_note-WHO21st-19"><span class="cite-bracket">&#91;</span>19<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<sup id="cite_ref-AHFS2015_14-6" class="reference"><a href="#cite_note-AHFS2015-14"><span class="cite-bracket">&#91;</span>14<span class="cite-bracket">&#93;</span></a></sup> In 2020, it was the 317th most commonly prescribed medication in the United States, with more than 900<span class="nowrap">&#160;</span>thousand prescriptions.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">&#91;</span>20<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">&#91;</span>21<span class="cite-bracket">&#93;</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=Tamoxifen&amp;action=edit&amp;section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Dysmenorrhea">Dysmenorrhea</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=2" title="Edit section: Dysmenorrhea"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Dysmenorrhea is the term for menstrual pain, usually centered in the lower abdomen but often spreading to the back and inner thighs. It’s a common gynecological condition that can seriously affect daily activities and well-being.Tamoxifen has been identified and used to effectively improve blood flow, reduce uterine contractility and pain in <a href="/wiki/Dysmenorrhea" title="Dysmenorrhea">dysmenorrhea</a> patients.<sup id="cite_ref-modern_22-0" class="reference"><a href="#cite_note-modern-22"><span class="cite-bracket">&#91;</span>22<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">&#91;</span>23<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Breast_cancer">Breast cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=3" title="Edit section: Breast cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen is used for the treatment of both early and advanced <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a>-positive (ER-positive or ER+) breast cancer in <a href="/wiki/Premenopausal" class="mw-redirect" title="Premenopausal">pre-</a> and <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women.<sup id="cite_ref-Jordan_1993_24-0" class="reference"><a href="#cite_note-Jordan_1993-24"><span class="cite-bracket">&#91;</span>24<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen increases the risk of <a href="/wiki/Vaginal_bleeding" title="Vaginal bleeding">postmenopausal bleeding</a>, <a href="/wiki/Endometrial_polyp" title="Endometrial polyp">endometrial polyps</a>, <a href="/wiki/Hyperplasia" title="Hyperplasia">hyperplasia</a>, and <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a>; using tamoxifen with an <a href="/wiki/IntraUterine_System" class="mw-redirect" title="IntraUterine System">intrauterine system</a> releasing <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a> might increase vaginal bleeding after 1 to 2 years, but reduces somewhat endometrial polyps and hyperplasia, but not necessarily endometrial cancer.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">&#91;</span>25<span class="cite-bracket">&#93;</span></a></sup> Additionally, it is the most common hormone treatment for male breast cancer.<sup id="cite_ref-urlBreast_cancer_in_men:_Cancer_Research_UK:_CancerHelp_UK_26-0" class="reference"><a href="#cite_note-urlBreast_cancer_in_men:_Cancer_Research_UK:_CancerHelp_UK-26"><span class="cite-bracket">&#91;</span>26<span class="cite-bracket">&#93;</span></a></sup> It is also approved by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">FDA</a> for the prevention of breast cancer in women at high risk of developing the disease.<sup id="cite_ref-FDA_27-0" class="reference"><a href="#cite_note-FDA-27"><span class="cite-bracket">&#91;</span>27<span class="cite-bracket">&#93;</span></a></sup> The effectiveness of tamoxifen is primarily influenced by estrogen receptor (ER) status, which was the key predictor of the proportional benefits observed. It has been further approved for the reduction of <a href="/wiki/Contralateral" class="mw-redirect" title="Contralateral">contralateral</a> (in the opposite breast) cancer. Five years of adjuvant tamoxifen treatment significantly lowers the 15-year risk of breast cancer recurrence and mortality. The overall use of tamoxifen is recommended for 10 years.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">&#91;</span>28<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">&#91;</span>29<span class="cite-bracket">&#93;</span></a></sup> </p><p>In 2006, the large STAR clinical study concluded that <a href="/wiki/Raloxifene" title="Raloxifene">raloxifene</a> is also effective in reducing the incidence of breast cancer. Updated results after an average of 6.75 years of follow up found that raloxifene retains 76% of tamoxifen's effectiveness in preventing invasive breast cancer, with 45% fewer <a href="/wiki/Uterine_cancer" title="Uterine cancer">uterine cancers</a> and 25% fewer blood clots in women taking raloxifene than in women taking tamoxifen.<sup id="cite_ref-NCI_30-0" class="reference"><a href="#cite_note-NCI-30"><span class="cite-bracket">&#91;</span>30<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-STAR_31-0" class="reference"><a href="#cite_note-STAR-31"><span class="cite-bracket">&#91;</span>31<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">&#91;</span>32<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Infertility">Infertility</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=4" title="Edit section: Infertility"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen is used for <a href="/wiki/Ovulation_induction" title="Ovulation induction">ovulation induction</a> to treat infertility in women with <a href="/wiki/Anovulatory_cycle" title="Anovulatory cycle">anovulatory</a> disorders. It is given at days three to seven of a woman's cycle.<sup id="cite_ref-Steiner_2005_33-0" class="reference"><a href="#cite_note-Steiner_2005-33"><span class="cite-bracket">&#91;</span>33<span class="cite-bracket">&#93;</span></a></sup> </p><p>Tamoxifen improves fertility in males with infertility by disinhibiting the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">hypothalamic–pituitary–gonadal axis</a> (HPG axis) via ER antagonism and thereby increasing the secretion of <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH) and <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> (FSH) and increasing testicular <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> production.<sup id="cite_ref-pmid23970453_34-0" class="reference"><a href="#cite_note-pmid23970453-34"><span class="cite-bracket">&#91;</span>34<span class="cite-bracket">&#93;</span></a></sup> Some animal studies have suggested tamoxifen could have negative effects on sperm quality and prostatic and gonadal health.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">&#91;</span>35<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">&#91;</span>36<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Gynecomastia">Gynecomastia</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=5" title="Edit section: Gynecomastia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Benign enlargement of the male breast, whether <a href="/wiki/Asymptomatic" title="Asymptomatic">asymptomatic</a> or painful, is a common condition thought to result from an increased estrogen/testosterone ratio or from heightened <a href="/wiki/Estrogen" title="Estrogen">estrogenic</a> or reduced <a href="/wiki/Androgen" title="Androgen">androgenic</a> activity via receptor interactions.Tamoxifen is used to prevent and treat <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a>.<sup id="cite_ref-Lapidvan_Wingerden2013_37-0" class="reference"><a href="#cite_note-Lapidvan_Wingerden2013-37"><span class="cite-bracket">&#91;</span>37<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-VianiBernardes_da_Silva2012_38-0" class="reference"><a href="#cite_note-VianiBernardes_da_Silva2012-38"><span class="cite-bracket">&#91;</span>38<span class="cite-bracket">&#93;</span></a></sup> It is taken as a preventative measure in small doses, or used at the onset of any symptoms such as nipple soreness or sensitivity. Current treatments typically involve pain relief through medication or surgery. However, targeting the underlying estrogenic stimulation may offer a more specific therapeutic approach. In a double-blind crossover study, patients were given either a placebo or tamoxifen (10 mg orally twice daily) for one month, in random order. Seven out of ten patients saw a reduction in gynecomastia size with tamoxifen (P &lt; 0.005), and the overall reduction for the group was statistically significant (P &lt; 0.01).<sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">&#91;</span>39<span class="cite-bracket">&#93;</span></a></sup> No benefits were observed with the placebo (P &gt; 0.1). Additionally, all four patients with painful gynecomastia experienced relief of their symptoms, and no toxicity was noted. Although the breast size reduction was partial, this suggests that longer treatment may be necessary. Follow-up examinations conducted 9 to 12 months after treatment revealed no significant changes, except in two cases: one tamoxifen responder had a recurrence of breast tenderness after six months, and one non-responder developed increased breast size and new tenderness after ten months. Other medications are taken for similar purposes such as <a href="/wiki/Clomifene" title="Clomifene">clomifene</a> and <a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">aromatase inhibitor</a> drugs; which are used in order to try to avoid the hormone-related adverse effects. Overall, tamoxifen appears to be a safe and effective treatment option for selected cases of gynecomastia. </p> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist 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ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tamoxifen_dosage_and_incidence_of_breast_symptoms_with_bicalutamide_in_men" title="Template:Tamoxifen dosage and incidence of breast symptoms with bicalutamide in men"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tamoxifen_dosage_and_incidence_of_breast_symptoms_with_bicalutamide_in_men" title="Template talk:Tamoxifen dosage and incidence of breast symptoms with bicalutamide in men"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tamoxifen_dosage_and_incidence_of_breast_symptoms_with_bicalutamide_in_men" title="Special:EditPage/Template:Tamoxifen dosage and incidence of breast symptoms with bicalutamide in men"><abbr title="Edit this template">e</abbr></a></li></ul></div> Tamoxifen doses and rates of bicalutamide-induced breast symptoms in men </caption> <tbody><tr> <th rowspan="2">Follow-up<br />timepoint</th> <th colspan="6">Tamoxifen dosage </th></tr> <tr> <th>Placebo</th> <th>1&#160;mg/day</th> <th>2.5&#160;mg/day</th> <th>5&#160;mg/day</th> <th>10&#160;mg/day</th> <th>20&#160;mg/day </th></tr> <tr> <td>0 months</td> <td colspan="6"><div class="center" style="width:auto; margin-left:auto; margin-right:auto;">–</div> </td></tr> <tr> <td>6 months</td> <td>98%</td> <td>90%</td> <td>80%</td> <td>54%</td> <td>22%</td> <td>10% </td></tr> <tr> <td>12 months</td> <td>99%</td> <td>95%</td> <td>84%</td> <td>56%</td> <td>38%</td> <td>19% </td></tr> <tr class="sortbottom"> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Notes:</b> Prevention of <a href="/wiki/Breast" title="Breast">breast</a> symptoms—specifically <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> and <a href="/wiki/Breast_pain" title="Breast pain">breast pain</a>—induced by 150&#160;mg/day <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a> monotherapy with tamoxifen in 282&#160;men with <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>. Bicalutamide and tamoxifen were initiated at the same time (0&#160;months). Estradiol levels were in the range of about 22 to 47 pg/mL in the treated group.<sup id="cite_ref-pmid17270340_40-0" class="reference"><a href="#cite_note-pmid17270340-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup> <b>Sources:</b> <sup id="cite_ref-pmid29322112_41-0" class="reference"><a href="#cite_note-pmid29322112-41"><span class="cite-bracket">&#91;</span>41<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid17270340_40-1" class="reference"><a href="#cite_note-pmid17270340-40"><span class="cite-bracket">&#91;</span>40<span class="cite-bracket">&#93;</span></a></sup> </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Early_puberty">Early puberty</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=6" title="Edit section: Early puberty"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen is useful in the treatment of <a href="/wiki/Peripheral_precocious_puberty" class="mw-redirect" title="Peripheral precocious puberty">peripheral precocious puberty</a>, for instance due to <a href="/wiki/McCune%E2%80%93Albright_syndrome" title="McCune–Albright syndrome">McCune–Albright syndrome</a>, in both girls and boys.<sup id="cite_ref-pmid29292624_42-0" class="reference"><a href="#cite_note-pmid29292624-42"><span class="cite-bracket">&#91;</span>42<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HaddadEugster2019_43-0" class="reference"><a href="#cite_note-HaddadEugster2019-43"><span class="cite-bracket">&#91;</span>43<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Zacharin2019_44-0" class="reference"><a href="#cite_note-Zacharin2019-44"><span class="cite-bracket">&#91;</span>44<span class="cite-bracket">&#93;</span></a></sup> It has been found to decrease <a href="/wiki/Growth_velocity" class="mw-redirect" title="Growth velocity">growth velocity</a> and the rate of <a href="/wiki/Bone_maturation" class="mw-redirect" title="Bone maturation">bone maturation</a> in girls with precocious puberty, and hence to improve final <a href="/wiki/Human_height" title="Human height">height</a> in these individuals.<sup id="cite_ref-pmid29292624_42-1" class="reference"><a href="#cite_note-pmid29292624-42"><span class="cite-bracket">&#91;</span>42<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HaddadEugster2019_43-1" class="reference"><a href="#cite_note-HaddadEugster2019-43"><span class="cite-bracket">&#91;</span>43<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=7" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Nolvadex.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Nolvadex.jpg/250px-Nolvadex.jpg" decoding="async" width="250" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Nolvadex.jpg/375px-Nolvadex.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/Nolvadex.jpg/500px-Nolvadex.jpg 2x" data-file-width="2119" data-file-height="1423" /></a><figcaption>Nolvadex (tamoxifen) 20 mg tablets.</figcaption></figure> <p>Tamoxifen is available as a tablet or oral solution.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">&#91;</span>45<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">&#91;</span>46<span class="cite-bracket">&#93;</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=Tamoxifen&amp;action=edit&amp;section=8" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen has a number of <a href="/wiki/Contraindication" title="Contraindication">contraindications</a>, including known <a href="/wiki/Hypersensitivity" title="Hypersensitivity">hypersensitivity</a> to tamoxifen or other ingredients, individuals taking concomitant <a href="/wiki/Coumarin" title="Coumarin">coumarin</a>-type <a href="/wiki/Anticoagulant" title="Anticoagulant">anticoagulant</a> therapy, and women with a history of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> (<a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">deep vein thrombosis</a> or <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a>).<sup id="cite_ref-Nolvadex-Label_12-1" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=9" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A report in September 2009 from Health and Human Services' Agency for Healthcare Research and Quality suggests that tamoxifen, raloxifene, and tibolone used to treat breast cancer significantly reduce invasive breast cancer in midlife and older women, but also increase the risk of adverse side effects.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">&#91;</span>47<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Endometrial_cancer">Endometrial cancer</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=10" title="Edit section: Endometrial cancer"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen is a <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a> (SERM).<sup id="cite_ref-Gallo_1997_48-0" class="reference"><a href="#cite_note-Gallo_1997-48"><span class="cite-bracket">&#91;</span>48<span class="cite-bracket">&#93;</span></a></sup> Even though it is an <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> in breast tissue it acts as <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> on the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a> and has been linked to <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> in some women. Therefore, endometrial changes, including cancer, are among tamoxifen's side effects.<sup id="cite_ref-Grilli_2006_49-0" class="reference"><a href="#cite_note-Grilli_2006-49"><span class="cite-bracket">&#91;</span>49<span class="cite-bracket">&#93;</span></a></sup> With time, risk of endometrial cancer may be doubled to quadrupled, which is a reason tamoxifen is typically only used for five years.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">&#91;</span>50<span class="cite-bracket">&#93;</span></a></sup> </p><p>The <a href="/wiki/American_Cancer_Society" title="American Cancer Society">American Cancer Society</a> lists tamoxifen as a known <a href="/wiki/Carcinogen" title="Carcinogen">carcinogen</a>, stating that it increases the risk of some types of uterine cancer while lowering the risk of breast cancer recurrence.<sup id="cite_ref-ACS_51-0" class="reference"><a href="#cite_note-ACS-51"><span class="cite-bracket">&#91;</span>51<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cardiovascular_and_metabolic">Cardiovascular and metabolic</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=11" title="Edit section: Cardiovascular and metabolic"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen treatment of postmenopausal women is associated with beneficial effects on serum lipid profiles. However, long-term data from clinical trials have failed to demonstrate a cardioprotective effect.<sup id="cite_ref-pmid16230014_52-0" class="reference"><a href="#cite_note-pmid16230014-52"><span class="cite-bracket">&#91;</span>52<span class="cite-bracket">&#93;</span></a></sup> For some women, tamoxifen can cause a rapid increase in <a href="/wiki/Triglyceride" title="Triglyceride">triglyceride</a> concentration in the blood. In addition, there is an increased risk of <a href="/wiki/Thromboembolism" title="Thromboembolism">thromboembolism</a> especially during and immediately after major surgery or periods of immobility.<sup id="cite_ref-pmid15699284_53-0" class="reference"><a href="#cite_note-pmid15699284-53"><span class="cite-bracket">&#91;</span>53<span class="cite-bracket">&#93;</span></a></sup> Use of tamoxifen has been shown to slightly increase risk of <a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">deep vein thrombosis</a>, <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a>, and <a href="/wiki/Stroke" title="Stroke">stroke</a>.<sup id="cite_ref-Harvey_2006_54-0" class="reference"><a href="#cite_note-Harvey_2006-54"><span class="cite-bracket">&#91;</span>54<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Liver_toxicity">Liver toxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=12" title="Edit section: Liver toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen has been associated with a number of cases of <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>.<sup id="cite_ref-CameronFeuer2012_55-0" class="reference"><a href="#cite_note-CameronFeuer2012-55"><span class="cite-bracket">&#91;</span>55<span class="cite-bracket">&#93;</span></a></sup> Several different varieties of hepatotoxicity have been reported.<sup id="cite_ref-CameronFeuer2012_55-1" class="reference"><a href="#cite_note-CameronFeuer2012-55"><span class="cite-bracket">&#91;</span>55<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen can also precipitate <a href="/wiki/Non-alcoholic_fatty_liver_disease" class="mw-redirect" title="Non-alcoholic fatty liver disease">non-alcoholic fatty liver disease</a> in obese and overweight women (not in normal weight women) at an average rate of 40% after a year use with 20&#160;mg/day.<sup id="cite_ref-pmid17181445_56-0" class="reference"><a href="#cite_note-pmid17181445-56"><span class="cite-bracket">&#91;</span>56<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=13" title="Edit section: Overdose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Acute <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a> of tamoxifen has not been reported in humans.<sup id="cite_ref-Nolvadex-Label_12-2" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> In <a href="/wiki/Dose-ranging_study" title="Dose-ranging study">dose-ranging studies</a>, tamoxifen was administered at very high doses in women (e.g., 300&#160;mg/m<sup>2</sup>) and was found to produce acute <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a> including <a href="/wiki/Tremor" title="Tremor">tremor</a>, <a href="/wiki/Hyperreflexia" title="Hyperreflexia">hyperreflexia</a>, <a href="/wiki/Gait_abnormality" title="Gait abnormality">unsteady gait</a>, and <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>.<sup id="cite_ref-Nolvadex-Label_12-3" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> These symptoms occurred within three to five days of therapy and disappeared within two to five days of discontinuation of therapy.<sup id="cite_ref-Nolvadex-Label_12-4" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> No indications of permanent neurotoxicity were observed.<sup id="cite_ref-Nolvadex-Label_12-5" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/QT_prolongation" class="mw-redirect" title="QT prolongation">QT prolongation</a> was also observed with very high doses of tamoxifen.<sup id="cite_ref-Nolvadex-Label_12-6" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> There is no specific <a href="/wiki/Antidote" title="Antidote">antidote</a> for overdose of tamoxifen.<sup id="cite_ref-Nolvadex-Label_12-7" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> Instead, treatment should be based on <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a>.<sup id="cite_ref-Nolvadex-Label_12-8" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=14" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Patients with variant forms of the gene <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> may not receive full benefit from tamoxifen because of too slow metabolism of the tamoxifen prodrug into its active metabolites.<sup id="cite_ref-Goetz_2005_57-0" class="reference"><a href="#cite_note-Goetz_2005-57"><span class="cite-bracket">&#91;</span>57<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Beverage_2007_58-0" class="reference"><a href="#cite_note-Beverage_2007-58"><span class="cite-bracket">&#91;</span>58<span class="cite-bracket">&#93;</span></a></sup> On 18 October 2006, the Subcommittee for Clinical Pharmacology recommended relabeling tamoxifen to include information about this gene in the package insert.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">&#91;</span>59<span class="cite-bracket">&#93;</span></a></sup> Certain CYP2D6 variations in breast cancer patients lead to a worse clinical outcome for tamoxifen treatment.<sup id="cite_ref-pmid19809024_60-0" class="reference"><a href="#cite_note-pmid19809024-60"><span class="cite-bracket">&#91;</span>60<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Genotyping" title="Genotyping">Genotyping</a> therefore has the potential for identification of women who have these CYP2D6 phenotypes and for whom the use of tamoxifen is associated with poor outcomes. Recent research has shown that 7–10% of women with breast cancer may not receive the full medical benefit from taking tamoxifen due to their genetic make-up. DNA Drug Safety Testing can examine DNA variations in the CYP2D6 and other important drug processing pathways. More than 20% of all clinically used medications are metabolized by CYP2D6 and knowing the CYP2D6 status of a person can help the doctor with the future selection of medications.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">&#91;</span>61<span class="cite-bracket">&#93;</span></a></sup> Other molecular biomarkers may also be used to select appropriate patients likely to benefit from tamoxifen.<sup id="cite_ref-pmid21552410_62-0" class="reference"><a href="#cite_note-pmid21552410-62"><span class="cite-bracket">&#91;</span>62<span class="cite-bracket">&#93;</span></a></sup> </p><p>Recent studies suggest that taking the <a href="/wiki/Selective_serotonin_reuptake_inhibitors" class="mw-redirect" title="Selective serotonin reuptake inhibitors">selective serotonin reuptake inhibitors</a> (SSRIs) antidepressants <a href="/wiki/Paroxetine" title="Paroxetine">paroxetine</a> (Paxil), <a href="/wiki/Fluoxetine" title="Fluoxetine">fluoxetine</a> (Prozac), and <a href="/wiki/Sertraline" title="Sertraline">sertraline</a> (Zoloft) can decrease the effectiveness of tamoxifen, as these drugs compete for the CYP2D6 enzyme which is needed to metabolize tamoxifen into its active forms.<sup id="cite_ref-Jin_2005_63-0" class="reference"><a href="#cite_note-Jin_2005-63"><span class="cite-bracket">&#91;</span>63<span class="cite-bracket">&#93;</span></a></sup> A U.S. study presented at the American Society of Clinical Oncology's annual meeting in 2009 found that after two years, 7.5% of women who took only tamoxifen had a recurrence, compared with 16% who took either paroxetine, fluoxetine or sertraline, drugs considered to be the most potent CYP2D6 inhibitors. That difference translates to a 120% increase in the risk of breast cancer recurrence. Patients taking the SSRIs Celexa (<a href="/wiki/Citalopram" title="Citalopram">citalopram</a>), Lexapro (<a href="/wiki/Escitalopram" title="Escitalopram">escitalopram</a>), and Luvox (<a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</a>) did not have an increased risk of recurrence, due to their lack of competitive metabolism for the CYP2D6 enzyme.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">&#91;</span>64<span class="cite-bracket">&#93;</span></a></sup> A newer study demonstrated a clearer and stronger effect from paroxetine in causing the worst outcomes. Patients treated with both paroxetine and tamoxifen have a 67% increased risk of death from breast cancer, from 24% to 91%, depending on the duration of coadministration.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">&#91;</span>65<span class="cite-bracket">&#93;</span></a></sup> </p><p>Tamoxifen interacts with certain other <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a>.<sup id="cite_ref-MorelloWurz2003_5-4" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> The <a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">aromatase inhibitor</a> <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">aminoglutethimide</a> induces the metabolism of tamoxifen.<sup id="cite_ref-MorelloWurz2003_5-5" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Conversely, the aromatase inhibitor <a href="/wiki/Letrozole" title="Letrozole">letrozole</a> does not affect the metabolism of tamoxifen.<sup id="cite_ref-MorelloWurz2003_5-6" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> However, tamoxifen induces the metabolism of letrozole and significantly reduces its concentrations.<sup id="cite_ref-MorelloWurz2003_5-7" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=15" 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=Tamoxifen&amp;action=edit&amp;section=16" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Selective_estrogen_receptor_modulator_activity">Selective estrogen receptor modulator activity</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=17" title="Edit section: Selective estrogen receptor modulator activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:3ert.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/3ert.png/220px-3ert.png" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/3ert.png/330px-3ert.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/3ert.png/440px-3ert.png 2x" data-file-width="960" data-file-height="720" /></a><figcaption><a href="/wiki/X-ray_crystallography#Biological_macromolecular_crystallography" title="X-ray crystallography">Crystallographic structure</a> of afimoxifene (<a href="/wiki/Carbon" title="Carbon">carbon</a> = white, <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> = red, <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> = blue) complexed with <a href="/wiki/Nuclear_receptor#Structure" title="Nuclear receptor">ligand binding domain</a> of <a href="/wiki/Estrogen_receptor_alpha" title="Estrogen receptor alpha">estrogen receptor alpha</a> (ERα) (cyan ribbon).<sup id="cite_ref-pmid9875847_66-0" class="reference"><a href="#cite_note-pmid9875847-66"><span class="cite-bracket">&#91;</span>66<span class="cite-bracket">&#93;</span></a></sup></figcaption></figure> <p>Tamoxifen acts as a <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a> (SERM), or as a <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> (ERs). It has mixed <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogenic</a> activity, with its profile of effects differing by <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissue</a>. For instance, tamoxifen has predominantly antiestrogenic effects in the <a href="/wiki/Breast" title="Breast">breasts</a> but predominantly estrogenic effects in the <a href="/wiki/Uterus" title="Uterus">uterus</a> and <a href="/wiki/Liver" title="Liver">liver</a>. In breast tissue, tamoxifen acts as an ER <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> so that <a href="/wiki/Gene_transcription" class="mw-redirect" title="Gene transcription">transcription</a> of estrogen-responsive genes is inhibited.<sup id="cite_ref-Wang_2004_67-0" class="reference"><a href="#cite_note-Wang_2004-67"><span class="cite-bracket">&#91;</span>67<span class="cite-bracket">&#93;</span></a></sup> A beneficial side effect of tamoxifen is that it prevents bone loss by acting as an ER <a href="/wiki/Agonist" title="Agonist">agonist</a> (i.e., mimicking the effects of estrogen) in this cell type. Therefore, by inhibiting <a href="/wiki/Osteoclasts" class="mw-redirect" title="Osteoclasts">osteoclasts</a>, it prevents <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>.<sup id="cite_ref-pmid17803905_68-0" class="reference"><a href="#cite_note-pmid17803905-68"><span class="cite-bracket">&#91;</span>68<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid18219273_69-0" class="reference"><a href="#cite_note-pmid18219273-69"><span class="cite-bracket">&#91;</span>69<span class="cite-bracket">&#93;</span></a></sup> When tamoxifen was launched as a drug, it was thought that tamoxifen would act as an ER antagonist in all tissues, including bone, and therefore it was feared that it would contribute to osteoporosis. It was therefore very surprising that the opposite effect was observed clinically. Hence tamoxifen's tissue selective action directly led to the formulation of the concept of SERMs.<sup id="cite_ref-Mincey_2000_70-0" class="reference"><a href="#cite_note-Mincey_2000-70"><span class="cite-bracket">&#91;</span>70<span class="cite-bracket">&#93;</span></a></sup> </p> <table class="wikitable mw-collapsible mw-collapsed" style="margin-left: auto; margin-right: auto; border: none;"> <caption class="nowrap"><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:Tissue-specific_estrogenic_and_antiestrogenic_activity_of_SERMs" title="Template:Tissue-specific estrogenic and antiestrogenic activity of SERMs"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tissue-specific_estrogenic_and_antiestrogenic_activity_of_SERMs" title="Template talk:Tissue-specific estrogenic and antiestrogenic activity of SERMs"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tissue-specific_estrogenic_and_antiestrogenic_activity_of_SERMs" title="Special:EditPage/Template:Tissue-specific estrogenic and antiestrogenic activity of SERMs"><abbr title="Edit this template">e</abbr></a></li></ul></div> Tissue-specific estrogenic and antiestrogenic activity of <abbr title="selective estrogen receptor modulators">SERMs</abbr> </caption> <tbody><tr> <th rowspan="2">Medication</th> <th rowspan="2"><a href="/wiki/Breast" title="Breast">Breast</a></th> <th rowspan="2"><a href="/wiki/Bone" title="Bone">Bone</a></th> <th colspan="4"><a href="/wiki/Liver" title="Liver">Liver</a></th> <th rowspan="2"><a href="/wiki/Uterus" title="Uterus">Uterus</a></th> <th rowspan="2"><a href="/wiki/Vagina" title="Vagina">Vagina</a></th> <th colspan="3"><a href="/wiki/Brain" title="Brain">Brain</a> </th></tr> <tr> <th><a href="/wiki/Lipids" class="mw-redirect" title="Lipids">Lipids</a></th> <th><a href="/wiki/Coagulation" title="Coagulation">Coagulation</a></th> <th><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></th> <th><a href="/wiki/Insulin-like_growth_factor_1" title="Insulin-like growth factor 1"><abbr title="Insulin-like growth factor 1">IGF-1</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 Insulin-like growth factor 1</span></th> <th><a href="/wiki/Hot_flash" title="Hot flash">Hot flashes</a></th> <th><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td><style data-mw-deduplicate="TemplateStyles:r1239334494">@media screen{html.skin-theme-clientpref-night .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-night .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output div:not(.notheme)>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output p>.tmp-color,html.skin-theme-clientpref-os .mw-parser-output table:not(.notheme) .tmp-color{color:inherit!important}}</style><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span> </td></tr> <tr> <td>"Ideal SERM"</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td>? </td></tr> <tr> <td><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td>?</td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td>? </td></tr> <tr> <td><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td>Tamoxifen</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr> <td><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> </td></tr> <tr class="sortbottom"> <td colspan="15" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Effect:</b> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Blue">+</span> = <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogenic</a> / <a href="/wiki/Agonist" title="Agonist">agonistic</a>. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Limegreen">±</span> = Mixed or neutral. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494"><span class="tmp-color" style="color:Red">–</span> = <a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogenic</a> / <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonistic</a>. <b>Note:</b> SERMs generally increase gonadotropin levels in hypogonadal and eugonadal men as well as premenopausal women (antiestrogenic) but decrease gonadotropin levels in postmenopausal women (estrogenic). <b>Sources:</b> See template. </td></tr></tbody></table> <p>Tamoxifen is a long-acting SERM, with a <a href="/wiki/Nuclear_retention" class="mw-redirect" title="Nuclear retention">nuclear retention</a> of the ER–tamoxifen (or metabolite) complex of greater than 48&#160;hours.<sup id="cite_ref-RunnebaumRabe2013_71-0" class="reference"><a href="#cite_note-RunnebaumRabe2013-71"><span class="cite-bracket">&#91;</span>71<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-WallachHammond1982_72-0" class="reference"><a href="#cite_note-WallachHammond1982-72"><span class="cite-bracket">&#91;</span>72<span class="cite-bracket">&#93;</span></a></sup> It has relatively little <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for the ERs itself and instead acts as a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolites</a> such as <a href="/wiki/Endoxifen" title="Endoxifen">endoxifen</a> (4-hydroxy-<i>N</i>-desmethyltamoxifen) and <a href="/wiki/Afimoxifene" title="Afimoxifene">afimoxifene</a> (4-hydroxytamoxifen; 4-OHT).<sup id="cite_ref-pmid23962908_9-3" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> These metabolites have approximately 30 to 100 times greater affinity for the ERs than tamoxifen itself.<sup id="cite_ref-Sanchez-SpitmanSwen2019_8-8" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid20981001_73-0" class="reference"><a href="#cite_note-pmid20981001-73"><span class="cite-bracket">&#91;</span>73<span class="cite-bracket">&#93;</span></a></sup> Per one study, tamoxifen had 7% and 6% of the affinity of <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> for the <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> and <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a>, respectively, whereas afimoxifene had 178% and 338% of the affinity of estradiol for the ERα and ERβ, respectively.<sup id="cite_ref-pmid16112947_74-0" class="reference"><a href="#cite_note-pmid16112947-74"><span class="cite-bracket">&#91;</span>74<span class="cite-bracket">&#93;</span></a></sup> Hence, afimoxifene showed 25-fold higher affinity for the ERα and 56-fold higher affinity for the ERβ than tamoxifen.<sup id="cite_ref-pmid15863530_75-0" class="reference"><a href="#cite_note-pmid15863530-75"><span class="cite-bracket">&#91;</span>75<span class="cite-bracket">&#93;</span></a></sup> The antiestrogenic potencies of endoxifen and afimoxifene are very similar.<sup id="cite_ref-pmid23962908_9-4" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> However, endoxifen occurs in much higher concentrations than afimoxifene and is now thought to be the major active form of tamoxifen in the body.<sup id="cite_ref-Sanchez-SpitmanSwen2019_8-9" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid23962908_9-5" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid25618289_76-0" class="reference"><a href="#cite_note-pmid25618289-76"><span class="cite-bracket">&#91;</span>76<span class="cite-bracket">&#93;</span></a></sup> </p><p>Tamoxifen binds to ER competitively (with respect to the endogenous agonist estrogen) in tumor cells and other tissue targets, producing a nuclear complex that decreases DNA synthesis and inhibits estrogen effects. It is a nonsteroidal agent with potent antiestrogenic properties which compete with estrogen for <a href="/wiki/Cell_signaling" title="Cell signaling">binding sites</a> in breast and other tissues. Tamoxifen causes cells to remain in the G<sub>0</sub> and G<sub>1</sub> phases of the <a href="/wiki/Cell_cycle" title="Cell cycle">cell cycle</a>. Because it prevents (pre)cancerous cells from dividing but does not cause cell death, tamoxifen is cytostatic rather than cytocidal. Tamoxifen binds to ER, the ER/tamoxifen complex recruits other proteins known as <a href="/wiki/Corepressor_(genetics)" class="mw-redirect" title="Corepressor (genetics)">co-repressors</a>, and the complex then binds to DNA to modulate gene expression. Some of these proteins include <a href="/wiki/Nuclear_receptor_co-repressor_1" title="Nuclear receptor co-repressor 1">NCoR</a> and <a href="/wiki/Nuclear_receptor_co-repressor_2" title="Nuclear receptor co-repressor 2">SMRT</a>.<sup id="cite_ref-pmid11136970_77-0" class="reference"><a href="#cite_note-pmid11136970-77"><span class="cite-bracket">&#91;</span>77<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen function can be regulated by a number of different variables including growth factors.<sup id="cite_ref-pmid18245484_78-0" class="reference"><a href="#cite_note-pmid18245484-78"><span class="cite-bracket">&#91;</span>78<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen needs to block growth factor proteins such as <a href="/wiki/ERBB2" class="mw-redirect" title="ERBB2">ErbB2/HER2</a><sup id="cite_ref-Hurtado_2008_79-0" class="reference"><a href="#cite_note-Hurtado_2008-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup> because high levels of ErbB2 have been shown to occur in tamoxifen resistant cancers.<sup id="cite_ref-pmid12618500_80-0" class="reference"><a href="#cite_note-pmid12618500-80"><span class="cite-bracket">&#91;</span>80<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen seems to require a protein <a href="/wiki/PAX2" title="PAX2">PAX2</a> for its full anticancer effect.<sup id="cite_ref-Hurtado_2008_79-1" class="reference"><a href="#cite_note-Hurtado_2008-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-urlwww.modernmedicine.com_81-0" class="reference"><a href="#cite_note-urlwww.modernmedicine.com-81"><span class="cite-bracket">&#91;</span>81<span class="cite-bracket">&#93;</span></a></sup> In the presence of high PAX2 expression, the tamoxifen/ER complex is able to suppress the expression of the pro-proliferative <a href="/wiki/HER2/neu" class="mw-redirect" title="HER2/neu">ERBB2</a> protein. In contrast, when <a href="/wiki/AIB-1" class="mw-redirect" title="AIB-1">AIB-1</a> expression is higher than PAX2, tamoxifen/ER complex upregulates the expression of ERBB2 resulting in stimulation of breast cancer growth.<sup id="cite_ref-Hurtado_2008_79-2" class="reference"><a href="#cite_note-Hurtado_2008-79"><span class="cite-bracket">&#91;</span>79<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-urlCORDIS_:_News_82-0" class="reference"><a href="#cite_note-urlCORDIS_:_News-82"><span class="cite-bracket">&#91;</span>82<span class="cite-bracket">&#93;</span></a></sup> </p><p>Tamoxifen is <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> in <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women and partially suppresses levels of the <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropins</a>, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH) and <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> (FSH) in such women.<sup id="cite_ref-pmid23687971_83-0" class="reference"><a href="#cite_note-pmid23687971-83"><span class="cite-bracket">&#91;</span>83<span class="cite-bracket">&#93;</span></a></sup> However, it has <a href="/wiki/Progonadotropic" class="mw-redirect" title="Progonadotropic">progonadotropic</a> effects in <a href="/wiki/Premenopausal" class="mw-redirect" title="Premenopausal">premenopausal</a> women and increases estrogen levels by 6-fold in them.<sup id="cite_ref-pmid23687971_83-1" class="reference"><a href="#cite_note-pmid23687971-83"><span class="cite-bracket">&#91;</span>83<span class="cite-bracket">&#93;</span></a></sup> Due to the nature of tamoxifen as a competitive ER ligand, this increase in estrogen levels is liable to interfere with the antiestrogenic efficacy of tamoxifen.<sup id="cite_ref-pmid23687971_83-2" class="reference"><a href="#cite_note-pmid23687971-83"><span class="cite-bracket">&#91;</span>83<span class="cite-bracket">&#93;</span></a></sup> The effects of tamoxifen on <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> <a href="/wiki/Ki-67_(protein)" title="Ki-67 (protein)">Ki-67</a> <a href="/wiki/Gene_expression" title="Gene expression">expression</a>, <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG) levels, and IGF-1 levels are <a href="/wiki/Dose%E2%80%93response_relationship" title="Dose–response relationship">dose-dependent</a> across a dosage range of 1 to 20&#160;mg/day in women with breast cancer.<sup id="cite_ref-pmid15755972_84-0" class="reference"><a href="#cite_note-pmid15755972-84"><span class="cite-bracket">&#91;</span>84<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen has been found to decrease <a href="/wiki/Insulin-like_growth_factor_1" title="Insulin-like growth factor 1">insulin-like growth factor 1</a> (IGF-1) levels by 17 to 38% in women and men.<sup id="cite_ref-pmid27704479_85-0" class="reference"><a href="#cite_note-pmid27704479-85"><span class="cite-bracket">&#91;</span>85<span class="cite-bracket">&#93;</span></a></sup> Suppression of IGF-1 production in the liver is a well-known action of estrogens and SERMs.<sup id="cite_ref-pmid27704479_85-1" class="reference"><a href="#cite_note-pmid27704479-85"><span class="cite-bracket">&#91;</span>85<span class="cite-bracket">&#93;</span></a></sup> A 10&#160;mg/day dosage of tamoxifen is nearly as effective as a 20&#160;mg/day dosage in suppressing IGF-1 levels.<sup id="cite_ref-MorelloWurz2003_5-8" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Other_activities">Other activities</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=18" title="Edit section: Other activities"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Afimoxifene is an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor">G protein-coupled estrogen receptor</a> (GPER) with relatively low <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a>.<sup id="cite_ref-pmid26023144_86-0" class="reference"><a href="#cite_note-pmid26023144-86"><span class="cite-bracket">&#91;</span>86<span class="cite-bracket">&#93;</span></a></sup> Its affinity for the receptor is in the range of 100 to 1,000&#160;nM, relative to 3 to 6&#160;nM for estradiol.<sup id="cite_ref-pmid26023144_86-1" class="reference"><a href="#cite_note-pmid26023144-86"><span class="cite-bracket">&#91;</span>86<span class="cite-bracket">&#93;</span></a></sup> </p><p>In addition to its activity as a SERM, afimoxifene binds to both the <a href="/wiki/Estrogen-related_receptor_%CE%B2" class="mw-redirect" title="Estrogen-related receptor β">estrogen-related receptor β</a> and <a href="/wiki/Estrogen-related_receptor_%CE%B3" class="mw-redirect" title="Estrogen-related receptor γ">estrogen-related receptor γ</a> and is an antagonist of the <a href="/wiki/Estrogen-related_receptor_%CE%B3" class="mw-redirect" title="Estrogen-related receptor γ">estrogen-related receptor γ</a> (ERRγ).<sup id="cite_ref-pmid16515477_87-0" class="reference"><a href="#cite_note-pmid16515477-87"><span class="cite-bracket">&#91;</span>87<span class="cite-bracket">&#93;</span></a></sup> </p><p><a href="/wiki/Norendoxifen" title="Norendoxifen">Norendoxifen</a> (4-hydroxy-<i>N</i>,<i>N</i>-didesmethyltamoxifen), another <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolite</a> of tamoxifen, has been found to act as a <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitive</a> <a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">aromatase inhibitor</a> (<a href="/wiki/IC50" title="IC50">IC<sub>50</sub></a> = 90&#160;nM), and may also be involved in the antiestrogenic activity of tamoxifen.<sup id="cite_ref-pmid23824607_88-0" class="reference"><a href="#cite_note-pmid23824607-88"><span class="cite-bracket">&#91;</span>88<span class="cite-bracket">&#93;</span></a></sup> </p><p>In addition to its activity as a SERM, tamoxifen is a <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> and <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/Protein_kinase_C" title="Protein kinase C">protein kinase C</a> <a href="/wiki/Protein_kinase_inhibitor" title="Protein kinase inhibitor">inhibitor</a>, and is active in this regard at therapeutic concentrations.<sup id="cite_ref-ZarateManji2009_89-0" class="reference"><a href="#cite_note-ZarateManji2009-89"><span class="cite-bracket">&#91;</span>89<span class="cite-bracket">&#93;</span></a></sup> This action is thought to underlie the efficacy of tamoxifen in the treatment of <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a>.<sup id="cite_ref-ZarateManji2009_89-1" class="reference"><a href="#cite_note-ZarateManji2009-89"><span class="cite-bracket">&#91;</span>89<span class="cite-bracket">&#93;</span></a></sup> </p><p>Tamoxifen is an inhibitor of <a href="/wiki/P-glycoprotein" title="P-glycoprotein">P-glycoprotein</a>.<sup id="cite_ref-Nolvadex-Label_12-9" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup> </p><p>In 2018, it was discovered that tamoxifen directly interacts with the <a href="/wiki/Dopamine_transporter" title="Dopamine transporter">dopamine transporter</a> (DAT) and acts as an atypical <a href="/wiki/Dopamine_reuptake_inhibitor" title="Dopamine reuptake inhibitor">dopamine reuptake inhibitor</a> (DRI).<sup id="cite_ref-NepalDasReith2023_90-0" class="reference"><a href="#cite_note-NepalDasReith2023-90"><span class="cite-bracket">&#91;</span>90<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MikelmanGuptaroySchmitt2018_91-0" class="reference"><a href="#cite_note-MikelmanGuptaroySchmitt2018-91"><span class="cite-bracket">&#91;</span>91<span class="cite-bracket">&#93;</span></a></sup> It has weak <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> (54% inhibition of dopamine uptake at 10<span class="nowrap">&#160;</span>μM) and lacks any <a href="/wiki/Psychostimulant" class="mw-redirect" title="Psychostimulant">stimulant</a> or <a href="/wiki/Central_depressant" class="mw-redirect" title="Central depressant">depressant</a> effects when administered by itself.<sup id="cite_ref-NepalDasReith2023_90-1" class="reference"><a href="#cite_note-NepalDasReith2023-90"><span class="cite-bracket">&#91;</span>90<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MikelmanGuptaroySchmitt2018_91-1" class="reference"><a href="#cite_note-MikelmanGuptaroySchmitt2018-91"><span class="cite-bracket">&#91;</span>91<span class="cite-bracket">&#93;</span></a></sup> However, tamoxifen <a href="/wiki/Dose_dependence" class="mw-redirect" title="Dose dependence">dose-dependently</a> blocks <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>-mediated <a href="/wiki/Dopamine_releasing_agent" title="Dopamine releasing agent">dopamine release</a> and psychostimulant-like effects in animals.<sup id="cite_ref-NepalDasReith2023_90-2" class="reference"><a href="#cite_note-NepalDasReith2023-90"><span class="cite-bracket">&#91;</span>90<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MikelmanGuptaroySchmitt2018_91-2" class="reference"><a href="#cite_note-MikelmanGuptaroySchmitt2018-91"><span class="cite-bracket">&#91;</span>91<span class="cite-bracket">&#93;</span></a></sup> This unusual profile of DRI activity has made tamoxifen of potential interest as a starting point for <a href="/wiki/Structural_modification" class="mw-redirect" title="Structural modification">structural modification</a> to develop novel pharmaceutical drugs for treatment of <a href="/wiki/Stimulant_use_disorder" title="Stimulant use disorder">stimulant use disorder</a>.<sup id="cite_ref-NepalDasReith2023_90-3" class="reference"><a href="#cite_note-NepalDasReith2023-90"><span class="cite-bracket">&#91;</span>90<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MikelmanGuptaroySchmitt2018_91-3" class="reference"><a href="#cite_note-MikelmanGuptaroySchmitt2018-91"><span class="cite-bracket">&#91;</span>91<span class="cite-bracket">&#93;</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=Tamoxifen&amp;action=edit&amp;section=19" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=20" title="Edit section: Absorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen is rapidly and extensively <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorbed</a> from the <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestines</a> with <a href="/wiki/Oral_administration" title="Oral administration">oral administration</a>.<sup id="cite_ref-MorelloWurz2003_5-9" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-BrennerStevens2017_6-1" class="reference"><a href="#cite_note-BrennerStevens2017-6"><span class="cite-bracket">&#91;</span>6<span class="cite-bracket">&#93;</span></a></sup> The <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of tamoxifen is approximately 100%, which is suggestive of minimal <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a> in the intestines and <a href="/wiki/Liver" title="Liver">liver</a>.<sup id="cite_ref-MorelloWurz2003_5-10" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Following intake, <a href="/wiki/Peak_levels" class="mw-redirect" title="Peak levels">peak levels</a> of tamoxifen occur after three to seven hours.<sup id="cite_ref-DeVitaLawrence2016_92-0" class="reference"><a href="#cite_note-DeVitaLawrence2016-92"><span class="cite-bracket">&#91;</span>92<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MorelloWurz2003_5-11" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> <a href="/wiki/Steady_state_levels" class="mw-redirect" title="Steady state levels">Steady state levels</a> of tamoxifen are reached typically after 3 to 4&#160;weeks but possibly up to 16&#160;weeks of daily administration.<sup id="cite_ref-MorelloWurz2003_5-12" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Nagar2010_11-1" class="reference"><a href="#cite_note-Nagar2010-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> Steady state levels of afimoxifene are achieved after 8&#160;weeks of daily tamoxifen administration.<sup id="cite_ref-Nagar2010_11-2" class="reference"><a href="#cite_note-Nagar2010-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-ChabnerLongo2011_7-1" class="reference"><a href="#cite_note-ChabnerLongo2011-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Peak levels of tamoxifen after a single 40&#160;mg oral dose were 65&#160;ng/mL and steady state levels at 20&#160;mg/day were 310&#160;ng/mL.<sup id="cite_ref-MorelloWurz2003_5-13" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Levels of tamoxifen show clear <a href="/wiki/Dose_dependency" class="mw-redirect" title="Dose dependency">dose dependency</a> across a dosage range of 1 to 20&#160;mg/day.<sup id="cite_ref-MorelloWurz2003_5-14" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid15073109_93-0" class="reference"><a href="#cite_note-pmid15073109-93"><span class="cite-bracket">&#91;</span>93<span class="cite-bracket">&#93;</span></a></sup> Endoxifen levels are approximately 5 to 10 times higher than afimoxifene levels, with large <a href="/wiki/Interindividual_variability" class="mw-redirect" title="Interindividual variability">interindividual variability</a>.<sup id="cite_ref-Sanchez-SpitmanSwen2019_8-10" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid23962908_9-6" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> Endoxifen levels have been reported as 10.8 to 15.9&#160;ng/mL at steady state in <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> normal metabolizers during therapy with 20&#160;mg/day tamoxifen.<sup id="cite_ref-Sanchez-SpitmanSwen2019_8-11" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> The most abundant <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of tamoxifen in terms of circulating concentrations are <a href="/wiki/N-desmethyltamoxifen" class="mw-redirect" title="N-desmethyltamoxifen"><i>N</i>-desmethyltamoxifen</a>, <a href="/wiki/N,N-didesmethyltamoxifen" class="mw-redirect" title="N,N-didesmethyltamoxifen"><i>N</i>,<i>N</i>-didesmethyltamoxifen</a>, <a href="/wiki/Endoxifen" title="Endoxifen">(<i>Z</i>)-endoxifen</a>, and tamoxifen <i>N</i>-oxide.<sup id="cite_ref-pmid21451508_10-1" class="reference"><a href="#cite_note-pmid21451508-10"><span class="cite-bracket">&#91;</span>10<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid6184101_94-0" class="reference"><a href="#cite_note-pmid6184101-94"><span class="cite-bracket">&#91;</span>94<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=21" title="Edit section: Distribution"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Volume_of_distribution" title="Volume of distribution">volume of distribution</a> of tamoxifen is 50 to 60&#160;L/kg and its <a href="/wiki/Clearance_(pharmacology)" title="Clearance (pharmacology)">clearance</a> has been estimated as 1.2 to 5.1&#160;L/hour.<sup id="cite_ref-MorelloWurz2003_5-15" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-DeVitaLawrence2016_92-1" class="reference"><a href="#cite_note-DeVitaLawrence2016-92"><span class="cite-bracket">&#91;</span>92<span class="cite-bracket">&#93;</span></a></sup> High concentrations of tamoxifen have been found in <a href="/wiki/Breast" title="Breast">breast</a>, <a href="/wiki/Uterus" title="Uterus">uterus</a>, liver, <a href="/wiki/Kidney" title="Kidney">kidney</a>, <a href="/wiki/Lung" title="Lung">lung</a>, <a href="/wiki/Pancreas" title="Pancreas">pancreas</a>, and <a href="/wiki/Ovary" title="Ovary">ovary</a> tissue in animals and humans.<sup id="cite_ref-MorelloWurz2003_5-16" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Levels of tamoxifen in the uterus have been found to be 2- to 3-fold higher than in the circulation<sup id="cite_ref-MorelloWurz2003_5-17" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> and in the breasts 10-fold higher than in the circulation.<sup id="cite_ref-pmid15073109_93-1" class="reference"><a href="#cite_note-pmid15073109-93"><span class="cite-bracket">&#91;</span>93<span class="cite-bracket">&#93;</span></a></sup> The <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> of tamoxifen and afimoxifene is greater than 99%.<sup id="cite_ref-ChabnerLongo2011_7-2" class="reference"><a href="#cite_note-ChabnerLongo2011-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> A majority of tamoxifen is bound to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a>.<sup id="cite_ref-MorelloWurz2003_5-18" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> Albumin alone binds 98.8% of tamoxifen while other <a href="/wiki/Plasma_protein" title="Plasma protein">plasma proteins</a> are not greatly involved.<sup id="cite_ref-pmid2702659_95-0" class="reference"><a href="#cite_note-pmid2702659-95"><span class="cite-bracket">&#91;</span>95<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=22" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <table class="wikitable floatright"> <caption>Tamoxifen and its metabolites in humans<sup id="cite_ref-pmid19574470_96-0" class="reference"><a href="#cite_note-pmid19574470-96"><span class="cite-bracket">&#91;</span>96<span class="cite-bracket">&#93;</span></a></sup> </caption> <tbody><tr> <th>Compound </th> <th>Mean plasma<br />concentrations </th> <th>Effect on ER / affinity for ER<sup>a</sup> </th></tr> <tr> <td>Tamoxifen </td> <td>190–420 nmol/L </td> <td>Weak antagonist / 2% </td></tr> <tr> <td><a href="/wiki/N-Desmethyltamoxifen" title="N-Desmethyltamoxifen"><i>N</i>-Desmethyltamoxifen</a> </td> <td>280–800 nmol/L </td> <td>Weak antagonist / 1% </td></tr> <tr> <td><a href="/wiki/N,N-Desmethyltamoxifen" class="mw-redirect" title="N,N-Desmethyltamoxifen"><i>N</i>,<i>N</i>-Desmethyltamoxifen</a> </td> <td>90–120 nmol/L </td> <td>Weak antagonist </td></tr> <tr> <td><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a> </td> <td>14–130 nmol/L </td> <td>Strong antagonist / equal to afimoxifene </td></tr> <tr> <td><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a> </td> <td>3–17 nmol/L<sup>b</sup> </td> <td>Strong antagonist / 188% </td></tr> <tr> <td>α-Hydroxytamoxifen </td> <td>1 nmol/L </td> <td>None </td></tr> <tr> <td>3,4-Dihydroxytamoxifen </td> <td>? </td> <td>Weak antagonist / high affinity </td></tr> <tr> <td>Tamoxifen <i>N</i>-oxide </td> <td>15–24 nmol/L </td> <td>Weak antagonist<sup>c</sup> </td></tr> <tr> <td colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Footnotes:</b> <sup>a</sup> = Estradiol is 100%. <sup>b</sup> = One study reported a much higher concentration (67 nmol/L). <sup>c</sup> = Might be due to reduction to tamoxifen. </td></tr></tbody></table> <p>Tamoxifen is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> and is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> in the <a href="/wiki/Liver" title="Liver">liver</a> by the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Isoform" class="mw-redirect" title="Isoform">isoforms</a> <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>, <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a>, and <a href="/wiki/CYP2D6" title="CYP2D6">CYP2D6</a> into <a href="/wiki/Active_metabolite" title="Active metabolite">active metabolites</a> such as <a href="/wiki/Endoxifen" title="Endoxifen">endoxifen</a> (4-hydroxy-<i>N</i>-desmethyltamoxifen) and <a href="/wiki/Afimoxifene" title="Afimoxifene">afimoxifene</a> (4-hydroxytamoxifen).<sup id="cite_ref-MorelloWurz2003_5-19" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Nolvadex-Label_12-10" class="reference"><a href="#cite_note-Nolvadex-Label-12"><span class="cite-bracket">&#91;</span>12<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Sanchez-SpitmanSwen2019_8-12" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> Conversion of tamoxifen by <i>N</i>-demethylation into <a href="/wiki/N-desmethyltamoxifen" class="mw-redirect" title="N-desmethyltamoxifen"><i>N</i>-desmethyltamoxifen</a>, which is catalyzed primarily by CYP3A4 and <a href="/wiki/CYP3A5" title="CYP3A5">CYP3A5</a>, is responsible for approximately 92% of tamoxifen metabolism.<sup id="cite_ref-pmid23962908_9-7" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> Conversely, 4-hydroxylation of tamoxifen into afimoxifene is responsible for only about 7% of tamoxifen metabolism.<sup id="cite_ref-pmid23962908_9-8" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> Following its formation, <i>N</i>-desmethyltamoxifen is <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a> into several other metabolites, the most notable of which is endoxifen.<sup id="cite_ref-pmid23962908_9-9" class="reference"><a href="#cite_note-pmid23962908-9"><span class="cite-bracket">&#91;</span>9<span class="cite-bracket">&#93;</span></a></sup> Another active metabolite, <a href="/wiki/Norendoxifen" title="Norendoxifen">norendoxifen</a> (4-hydroxy-<i>N</i>,<i>N</i>-didesmethyltamoxifen), is formed via <i>N</i>-demethylation of endoxifen or 4-hydroxylation of <a href="/wiki/N,N-didesmethyltamoxifen" class="mw-redirect" title="N,N-didesmethyltamoxifen"><i>N</i>,<i>N</i>-didesmethyltamoxifen</a>.<sup id="cite_ref-Sanchez-SpitmanSwen2019_8-13" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen and its metabolites undergo <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugation</a>, including <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>.<sup id="cite_ref-Nagar2010_11-3" class="reference"><a href="#cite_note-Nagar2010-11"><span class="cite-bracket">&#91;</span>11<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen may inhibit its own metabolism.<sup id="cite_ref-MorelloWurz2003_5-20" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Elimination">Elimination</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=23" title="Edit section: Elimination"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen has a long <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of typically 5 to 7&#160;days, with a range of 4 to 11&#160;days.<sup id="cite_ref-MorelloWurz2003_5-21" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Sanchez-SpitmanSwen2019_8-14" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-DeVitaLawrence2016_92-2" class="reference"><a href="#cite_note-DeVitaLawrence2016-92"><span class="cite-bracket">&#91;</span>92<span class="cite-bracket">&#93;</span></a></sup> Similarly, the half-life of afimoxifene is 14&#160;days.<sup id="cite_ref-ChabnerLongo2011_7-3" class="reference"><a href="#cite_note-ChabnerLongo2011-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Conversely, the half-life of <a href="/wiki/Endoxifen" title="Endoxifen">endoxifen</a> is 50 to 70&#160;hours (2–3&#160;days).<sup id="cite_ref-Sanchez-SpitmanSwen2019_8-15" class="reference"><a href="#cite_note-Sanchez-SpitmanSwen2019-8"><span class="cite-bracket">&#91;</span>8<span class="cite-bracket">&#93;</span></a></sup> The long half-lives of tamoxifen and afimoxifene are attributed to their high plasma protein binding as well as to <a href="/wiki/Enterohepatic_recirculation" class="mw-redirect" title="Enterohepatic recirculation">enterohepatic recirculation</a>.<sup id="cite_ref-ChabnerLongo2011_7-4" class="reference"><a href="#cite_note-ChabnerLongo2011-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Upon discontinuation of treatment, levels of tamoxifen and its metabolites persist in the circulation for at least 6&#160;weeks.<sup id="cite_ref-ChabnerLongo2011_7-5" class="reference"><a href="#cite_note-ChabnerLongo2011-7"><span class="cite-bracket">&#91;</span>7<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen is <a href="/wiki/Excretion" title="Excretion">excreted</a> in <a href="/wiki/Bile" title="Bile">bile</a> and is <a href="/wiki/Elimination_(pharmacology)" title="Elimination (pharmacology)">eliminated</a> in <a href="/wiki/Feces" title="Feces">feces</a>, while small amounts are eliminated in <a href="/wiki/Urine" title="Urine">urine</a>.<sup id="cite_ref-MorelloWurz2003_5-22" class="reference"><a href="#cite_note-MorelloWurz2003-5"><span class="cite-bracket">&#91;</span>5<span class="cite-bracket">&#93;</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=Tamoxifen&amp;action=edit&amp;section=24" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen is a <a href="/wiki/Nonsteroidal" title="Nonsteroidal">nonsteroidal</a> SERM of the <a href="/wiki/Triphenylethylene" title="Triphenylethylene">triphenylethylene</a> family and was structurally derived from <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>-like estrogens and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a> such as <a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">chlorotrianisene</a> and <a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">ethamoxytriphetol</a>.<sup id="cite_ref-Jordan1986_97-0" class="reference"><a href="#cite_note-Jordan1986-97"><span class="cite-bracket">&#91;</span>97<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Pratt1994_98-0" class="reference"><a href="#cite_note-Pratt1994-98"><span class="cite-bracket">&#91;</span>98<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MaximovMcDaniel2013_99-0" class="reference"><a href="#cite_note-MaximovMcDaniel2013-99"><span class="cite-bracket">&#91;</span>99<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Ravina2011_100-0" class="reference"><a href="#cite_note-Ravina2011-100"><span class="cite-bracket">&#91;</span>100<span class="cite-bracket">&#93;</span></a></sup> Initially, <a href="/wiki/Clomifene" title="Clomifene">clomifene</a> was synthesized, and tamoxifen was developed subsequently.<sup id="cite_ref-Jordan1986_97-1" class="reference"><a href="#cite_note-Jordan1986-97"><span class="cite-bracket">&#91;</span>97<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-MaximovMcDaniel2013_99-1" class="reference"><a href="#cite_note-MaximovMcDaniel2013-99"><span class="cite-bracket">&#91;</span>99<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Ravina2011_100-1" class="reference"><a href="#cite_note-Ravina2011-100"><span class="cite-bracket">&#91;</span>100<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen is closely related structurally to other triphenylethylenes, such as clomifene, <a href="/wiki/Nafoxidine" title="Nafoxidine">nafoxidine</a>, <a href="/wiki/Ospemifene" title="Ospemifene">ospemifene</a>, <a href="/wiki/Toremifene" title="Toremifene">toremifene</a>, and numerous others.<sup id="cite_ref-CanoAlsina2006_101-0" class="reference"><a href="#cite_note-CanoAlsina2006-101"><span class="cite-bracket">&#91;</span>101<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-OrwollBilezikian2009_102-0" class="reference"><a href="#cite_note-OrwollBilezikian2009-102"><span class="cite-bracket">&#91;</span>102<span class="cite-bracket">&#93;</span></a></sup> Other SERMs, like <a href="/wiki/Raloxifene" title="Raloxifene">raloxifene</a>, are structurally distinct from tamoxifen and other triphenylethylenes.<sup id="cite_ref-OrwollBilezikian2009_102-1" class="reference"><a href="#cite_note-OrwollBilezikian2009-102"><span class="cite-bracket">&#91;</span>102<span class="cite-bracket">&#93;</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=Tamoxifen&amp;action=edit&amp;section=25" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the late 1950s, pharmaceutical companies were actively researching a newly discovered class of anti-estrogen compounds in the hope of developing a morning-after contraceptive pill. Arthur L Walpole was a reproductive <a href="/wiki/Endocrinologist" class="mw-redirect" title="Endocrinologist">endocrinologist</a> who led such a team at the <a href="/wiki/Alderley_Park" title="Alderley Park">Alderley Park</a> research laboratories of <a href="/wiki/Imperial_Chemical_Industries" title="Imperial Chemical Industries">ICI</a> Pharmaceuticals.<sup id="cite_ref-Jordan_2006_18-1" class="reference"><a href="#cite_note-Jordan_2006-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup> It was there in 1962 that chemist Dora Richardson first synthesized tamoxifen, back then known as ICI-46,474, when she was looking to create triphenylethylene derivatives for the contraceptive pill project that her team was researching.<sup id="cite_ref-isbn0-471-89979-8_103-0" class="reference"><a href="#cite_note-isbn0-471-89979-8-103"><span class="cite-bracket">&#91;</span>103<span class="cite-bracket">&#93;</span></a></sup> </p><p>This compound was originally created to work as an estrogen inhibitor, but instead was found to stimulate ovulation in participants of the drug testing trial.<sup id="cite_ref-Viviane_M_2017_17-1" class="reference"><a href="#cite_note-Viviane_M_2017-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> Walpole and his colleagues filed a UK patent covering this compound in 1962, but patent protection on this compound was repeatedly denied in the US until the 1980s.<sup id="cite_ref-Jordan_2003_104-0" class="reference"><a href="#cite_note-Jordan_2003-104"><span class="cite-bracket">&#91;</span>104<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen did eventually receive marketing approval as a fertility treatment, but the class of compounds never proved useful in human contraception. A link between estrogen and breast cancer had been known for many years, but cancer treatments were not a corporate priority at the time, and Walpole's personal interests were important in keeping support for the compound alive in the face of this and the lack of patent protection.<sup id="cite_ref-Jordan_2006_18-2" class="reference"><a href="#cite_note-Jordan_2006-18"><span class="cite-bracket">&#91;</span>18<span class="cite-bracket">&#93;</span></a></sup> It was only when Walpole threatened to leave his position that corporate decided to allow trials and testing for tamoxifen as a drug that could be used to treat breast cancer. Without Walpole's effort towards defending the work that his team had done in discovering a possibly revolutionary source for breast cancer treatment, tamoxifen could have become a discarded or under-researched idea. Walpole's team consisted of Dora Richardson and G. A. Snow, who worked on the chemistry portion of the project, along with G. E. Paget and J. K. Walley, who focused primarily on the biological side.<sup id="cite_ref-Viviane_M_2017_17-2" class="reference"><a href="#cite_note-Viviane_M_2017-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> </p><p>Tamoxifen is one of three drugs in an <a href="/wiki/Angiogenesis_inhibitor" title="Angiogenesis inhibitor">anti-angiogenetic</a> protocol developed by <a href="/wiki/Judah_Folkman" title="Judah Folkman">Dr. Judah Folkman</a>, a researcher at Children's Hospital at Harvard Medical School in Boston. Folkman discovered in the 1970s that <a href="/wiki/Angiogenesis" title="Angiogenesis">angiogenesis</a> – the growth of new blood vessels – plays a significant role in the development of cancer. Since his discovery, an entirely new field of cancer research has developed. Clinical trials on <a href="/wiki/Angiogenesis_inhibitor" title="Angiogenesis inhibitor">angiogenesis inhibitors</a> have been underway since 1992 using many different drugs. The Harvard researchers developed a specific protocol for a golden retriever named Navy who was cancer-free after receiving the prescribed cocktail of <a href="/wiki/Celecoxib" title="Celecoxib">celecoxib</a>, <a href="/wiki/Doxycycline" title="Doxycycline">doxycycline</a>, and tamoxifen – the treatment subsequently became known as the Navy Protocol.<sup id="cite_ref-urlUSA_Today_105-0" class="reference"><a href="#cite_note-urlUSA_Today-105"><span class="cite-bracket">&#91;</span>105<span class="cite-bracket">&#93;</span></a></sup> Furthermore, tamoxifen treatment alone has been shown to have anti-angiogenetic effects in animal models of cancer which appear to be, at least in part, independent of tamoxifen's ER antagonist properties.<sup id="cite_ref-pmid11106254_106-0" class="reference"><a href="#cite_note-pmid11106254-106"><span class="cite-bracket">&#91;</span>106<span class="cite-bracket">&#93;</span></a></sup> </p><p>Other antiestrogens, such as <a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">ethamoxytriphetol</a> (MER-25) and <a href="/wiki/Clomifene" title="Clomifene">clomifene</a> (MRL-41), were assessed for treatment of breast cancer and found to be effective before tamoxifen, but were plagued with <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> issues.<sup id="cite_ref-pmid12796359_107-0" class="reference"><a href="#cite_note-pmid12796359-107"><span class="cite-bracket">&#91;</span>107<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HowellJordan2013B_108-0" class="reference"><a href="#cite_note-HowellJordan2013B-108"><span class="cite-bracket">&#91;</span>108<span class="cite-bracket">&#93;</span></a></sup> The first clinical study of tamoxifen took place at the <a href="/wiki/Christie_Hospital" class="mw-redirect" title="Christie Hospital">Christie Hospital</a> in 1971, and showed a convincing effect in advanced breast cancer, but nevertheless ICI's development programme came close to termination when it was reviewed in 1972.<sup id="cite_ref-Cole_1971_109-0" class="reference"><a href="#cite_note-Cole_1971-109"><span class="cite-bracket">&#91;</span>109<span class="cite-bracket">&#93;</span></a></sup> In an unpublished article from the early days of the trial, Dora Richardson documented her team's excitement about tamoxifen's effects in counteracting infertility problems and the early positive effects found in breast cancer patients. Unfortunately, this work was not well received by everyone, as the team was supposed to be looking for a contraceptive pill.<sup id="cite_ref-Viviane_M_2017_17-3" class="reference"><a href="#cite_note-Viviane_M_2017-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> Tamoxifen's further development may have been bolstered by a second clinical study by Harold W.C. Ward <sup id="cite_ref-Ward_1973_110-0" class="reference"><a href="#cite_note-Ward_1973-110"><span class="cite-bracket">&#91;</span>110<span class="cite-bracket">&#93;</span></a></sup> at the <a href="/wiki/Queen_Elizabeth_Hospital_Birmingham" title="Queen Elizabeth Hospital Birmingham">Queen Elizabeth Hospital, Birmingham</a>. Ward's study showed a more definitive response to the drug at a higher dosage. Walpole also may have helped to convince the company to market tamoxifen for late stage breast cancer in 1973.<sup id="cite_ref-Jordan_2003_104-1" class="reference"><a href="#cite_note-Jordan_2003-104"><span class="cite-bracket">&#91;</span>104<span class="cite-bracket">&#93;</span></a></sup> He was also instrumental in funding <a href="/wiki/V._Craig_Jordan" title="V. Craig Jordan">V. Craig Jordan</a> to work on tamoxifen. In 1972, ICI Pharmaceuticals Division abandoned development of tamoxifen for financial reasons. The drug was subsequently reinvented from a failed contraceptive, to become tamoxifen, the gold standard for the adjuvant treatment of breast cancer and the pioneering medicine for chemprevention for high-risk women.<sup id="cite_ref-111" class="reference"><a href="#cite_note-111"><span class="cite-bracket">&#91;</span>111<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-112" class="reference"><a href="#cite_note-112"><span class="cite-bracket">&#91;</span>112<span class="cite-bracket">&#93;</span></a></sup> Two books, <i>Estrogen Action, Selective Estrogen Receptor Modulators and Women's Health</i> (Imperial College Press 2013) and <i>Tamoxifen: Pioneering Medicine in Breast Cancer</i> (Springer 2013) tell this story. </p> <table class="wikitable" style="font-size:small; margin: 1em auto;"> <caption class="nowrap"><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:Comparison_of_early_clinical_experience_with_antiestrogens_for_advanced_breast_cancer" title="Template:Comparison of early clinical experience with antiestrogens for advanced breast cancer"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Comparison_of_early_clinical_experience_with_antiestrogens_for_advanced_breast_cancer" title="Template talk:Comparison of early clinical experience with antiestrogens for advanced breast cancer"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Comparison_of_early_clinical_experience_with_antiestrogens_for_advanced_breast_cancer" title="Special:EditPage/Template:Comparison of early clinical experience with antiestrogens for advanced breast cancer"><abbr title="Edit this template">e</abbr></a></li></ul></div> <span style="font-size:105%;">Comparison of early clinical experience with antiestrogens for advanced breast cancer</span> </caption> <tbody><tr> <th>Antiestrogen </th> <th>Dosage </th> <th>Year(s) </th> <th>Response rate </th> <th>Adverse effects </th></tr> <tr> <td><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol</a> </td> <td>500–4,500 mg/day </td> <td>1960 </td> <td>25% </td> <td><a href="/wiki/Acute_psychotic_episode" class="mw-redirect" title="Acute psychotic episode">Acute psychotic episodes</a> </td></tr> <tr> <td><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a> </td> <td>100–300 mg/day </td> <td>1964–1974 </td> <td>34% </td> <td>Risks of <a href="/wiki/Cataract" title="Cataract">cataracts</a> </td></tr> <tr> <td><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a> </td> <td>180–240 mg/day </td> <td>1976 </td> <td>31% </td> <td><a href="/wiki/Cataract" title="Cataract">Cataracts</a>, <a href="/wiki/Ichthyosis" title="Ichthyosis">ichthyosis</a>, <a href="/wiki/Photophobia" title="Photophobia">photophobia</a> </td></tr> <tr> <td>Tamoxifen </td> <td>20–40 mg/day </td> <td>1971–1973 </td> <td>31% </td> <td>Transient <a href="/wiki/Thrombocytopenia" title="Thrombocytopenia">thrombocytopenia</a><sup>a</sup> </td></tr> <tr> <td colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;"><b>Footnotes:</b> <sup>a</sup> = "The particular advantage of this drug is the low incidence of troublesome side effects (25)." "Side effects were usually trivial (26)." <b>Sources:</b> <sup id="cite_ref-pmid12796359_107-1" class="reference"><a href="#cite_note-pmid12796359-107"><span class="cite-bracket">&#91;</span>107<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-HowellJordan2013_113-0" class="reference"><a href="#cite_note-HowellJordan2013-113"><span class="cite-bracket">&#91;</span>113<span class="cite-bracket">&#93;</span></a></sup> </td></tr></tbody></table> <p>1980 saw the publication of the first trial to show that tamoxifen given in addition to chemotherapy improved survival for patients with early breast cancer.<sup id="cite_ref-Baum_2003_114-0" class="reference"><a href="#cite_note-Baum_2003-114"><span class="cite-bracket">&#91;</span>114<span class="cite-bracket">&#93;</span></a></sup> In advanced disease, tamoxifen is now only recognized as effective in ER+ patients, but the early trials did not select ER+ patients, and by the mid-1980s the clinical trial picture was not showing a major advantage for tamoxifen.<sup id="cite_ref-FURR_1984_115-0" class="reference"><a href="#cite_note-FURR_1984-115"><span class="cite-bracket">&#91;</span>115<span class="cite-bracket">&#93;</span></a></sup> Nevertheless, tamoxifen had a relatively mild side-effect profile, and a number of large trials continued. </p><p>The pharmacology of SERMs was discovered, defined, and deciphered during the 1980s.<sup id="cite_ref-116" class="reference"><a href="#cite_note-116"><span class="cite-bracket">&#91;</span>116<span class="cite-bracket">&#93;</span></a></sup> A clinical strategy was described<sup id="cite_ref-117" class="reference"><a href="#cite_note-117"><span class="cite-bracket">&#91;</span>117<span class="cite-bracket">&#93;</span></a></sup> that led to the creation of SERMs as a group of multifunctional medicines aimed at the treatment or prevention of many conditions in postmenopausal women, e.g. osteoporosis and breast cancer.<sup id="cite_ref-118" class="reference"><a href="#cite_note-118"><span class="cite-bracket">&#91;</span>118<span class="cite-bracket">&#93;</span></a></sup> </p><p>The early sales of tamoxifen in both the UK and in the U.S. far exceeded ICI's original estimate, but despite this, at the annual portfolio review ICI's board members still asserted that "there was no market for cancer", leaving the drug's marketing success to rely on its clinical results and clinicians' and scientists' interests in it. Shortly after, Dora Richardson published a history of tamoxifen that, unusually for that type of paper, included personal accounts and letters from patients who attributed their healing to the drug. This testimony from cancer patients using tamoxifen helped to shape and push forward research, by justifying it both morally and scientifically to corporations.<sup id="cite_ref-Viviane_M_2017_17-4" class="reference"><a href="#cite_note-Viviane_M_2017-17"><span class="cite-bracket">&#91;</span>17<span class="cite-bracket">&#93;</span></a></sup> </p><p>It was not until 1998 that the meta-analysis of the Oxford-based Early Breast Cancer Trialists' Collaborative Group showed definitively that tamoxifen was effective for early breast cancer.<sup id="cite_ref-pmid9605801_119-0" class="reference"><a href="#cite_note-pmid9605801-119"><span class="cite-bracket">&#91;</span>119<span class="cite-bracket">&#93;</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=Tamoxifen&amp;action=edit&amp;section=26" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=27" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tamoxifen is marketed under the brand names Nolvadex and Soltamox, and a variety of other brand names throughout the world.<sup id="cite_ref-drug_dictionary_1-1" class="reference"><a href="#cite_note-drug_dictionary-1"><span class="cite-bracket">&#91;</span>1<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-Drugs.com_120-0" class="reference"><a href="#cite_note-Drugs.com-120"><span class="cite-bracket">&#91;</span>120<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Economics">Economics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=28" title="Edit section: Economics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Global sales of tamoxifen in 2001 were approximately $1.02 billion.<sup id="cite_ref-urlCancer_the_generic_impact_121-0" class="reference"><a href="#cite_note-urlCancer_the_generic_impact-121"><span class="cite-bracket">&#91;</span>121<span class="cite-bracket">&#93;</span></a></sup> Since the expiration of the patent in 2002, it is widely available as a <a href="/wiki/Generic_drug" title="Generic drug">generic drug</a> around the world. As of 2004<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Tamoxifen&amp;action=edit">&#91;update&#93;</a></sup>, tamoxifen was the world's largest selling hormonal drug for the treatment of breast cancer.<sup id="cite_ref-urlwww.astrazeneca.se_122-0" class="reference"><a href="#cite_note-urlwww.astrazeneca.se-122"><span class="cite-bracket">&#91;</span>122<span class="cite-bracket">&#93;</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=29" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In <a href="/wiki/McCune-Albright_syndrome" class="mw-redirect" title="McCune-Albright syndrome">McCune-Albright syndrome</a> (MAS) tamoxifen has been used to treat <a href="/wiki/Premature_puberty" class="mw-redirect" title="Premature puberty">premature puberty</a> and the consequences of premature puberty. Tamoxifen has been seen to decrease rapid <a href="/wiki/Bone_maturation" class="mw-redirect" title="Bone maturation">bone maturation</a> which is the result of <a href="/wiki/Hyperestrogenism" title="Hyperestrogenism">excessive estrogen</a> and alter predicted adult height (PAH).<sup id="cite_ref-123" class="reference"><a href="#cite_note-123"><span class="cite-bracket">&#91;</span>123<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-124" class="reference"><a href="#cite_note-124"><span class="cite-bracket">&#91;</span>124<span class="cite-bracket">&#93;</span></a></sup> The same effects have also been seen in short pubertal boys.<sup id="cite_ref-125" class="reference"><a href="#cite_note-125"><span class="cite-bracket">&#91;</span>125<span class="cite-bracket">&#93;</span></a></sup> However, one <i>in vitro</i> study in 2007 and later an <i>in vivo</i> study in 2008 have shown that tamoxifen induces apoptosis in growth plate chondrocytes, reduces serum <a href="/wiki/Insulin-like_growth_factor_1" title="Insulin-like growth factor 1">insulin-like growth factor 1</a> (IGF-1) levels and causes persistent retardation of longitudinal and cortical radial bone growth in young male rats, leading the researchers to express concern giving tamoxifen to growing individuals.<sup id="cite_ref-pmid18348701_126-0" class="reference"><a href="#cite_note-pmid18348701-126"><span class="cite-bracket">&#91;</span>126<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-127" class="reference"><a href="#cite_note-127"><span class="cite-bracket">&#91;</span>127<span class="cite-bracket">&#93;</span></a></sup> </p><p>Tamoxifen has been studied in the treatment of the rare conditions of <a href="/wiki/Retroperitoneal_fibrosis" title="Retroperitoneal fibrosis">retroperitoneal fibrosis</a><sup id="cite_ref-pmid16418409_128-0" class="reference"><a href="#cite_note-pmid16418409-128"><span class="cite-bracket">&#91;</span>128<span class="cite-bracket">&#93;</span></a></sup> and <a href="/wiki/Idiopathic_sclerosing_mesenteritis" title="Idiopathic sclerosing mesenteritis">idiopathic sclerosing mesenteritis</a>.<sup id="cite_ref-pmid17478346_129-0" class="reference"><a href="#cite_note-pmid17478346-129"><span class="cite-bracket">&#91;</span>129<span class="cite-bracket">&#93;</span></a></sup> It has also been proposed as part of a treatment plan for <a href="/wiki/Riedel%27s_thyroiditis" title="Riedel&#39;s thyroiditis">Riedel's thyroiditis</a>.<sup id="cite_ref-pmid12698518_130-0" class="reference"><a href="#cite_note-pmid12698518-130"><span class="cite-bracket">&#91;</span>130<span class="cite-bracket">&#93;</span></a></sup> </p><p>Tamoxifen is used as a research tool to trigger tissue-specific gene expression in many conditional expression constructs in <a href="/wiki/Genetically_modified_animal" title="Genetically modified animal">genetically modified animals</a> including a version of the <a href="/wiki/Cre-Lox_recombination" title="Cre-Lox recombination">Cre-Lox recombination</a> technique.<sup id="cite_ref-pmid8855277_131-0" class="reference"><a href="#cite_note-pmid8855277-131"><span class="cite-bracket">&#91;</span>131<span class="cite-bracket">&#93;</span></a></sup> While widely used in transgenic research, the strong anabolic effect of tamoxifen on bone might confound this approach, especially as it relates to bone-targeted constructs. </p><p>Tamoxifen may be effective in the treatment of <a href="/wiki/Mania" title="Mania">mania</a> in people with <a href="/wiki/Bipolar_disorder" title="Bipolar disorder">bipolar disorder</a>.<sup id="cite_ref-TalaeiPourgholami2016_132-0" class="reference"><a href="#cite_note-TalaeiPourgholami2016-132"><span class="cite-bracket">&#91;</span>132<span class="cite-bracket">&#93;</span></a></sup> This is thought to be due to blockade of <a href="/wiki/Protein_kinase_C" title="Protein kinase C">protein kinase C</a> (PKC), an <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> that regulates <a href="/wiki/Neuron" title="Neuron">neuron</a> activity in the <a href="/wiki/Brain" title="Brain">brain</a>.<sup id="cite_ref-TalaeiPourgholami2016_132-1" class="reference"><a href="#cite_note-TalaeiPourgholami2016-132"><span class="cite-bracket">&#91;</span>132<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-SaxenaScaini2017_133-0" class="reference"><a href="#cite_note-SaxenaScaini2017-133"><span class="cite-bracket">&#91;</span>133<span class="cite-bracket">&#93;</span></a></sup> Researchers believe PKC is overactive during the mania in bipolar patients.<sup id="cite_ref-TalaeiPourgholami2016_132-2" class="reference"><a href="#cite_note-TalaeiPourgholami2016-132"><span class="cite-bracket">&#91;</span>132<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-SaxenaScaini2017_133-1" class="reference"><a href="#cite_note-SaxenaScaini2017-133"><span class="cite-bracket">&#91;</span>133<span class="cite-bracket">&#93;</span></a></sup> As of September 2019<sup class="plainlinks noexcerpt noprint asof-tag update" style="display:none;"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Tamoxifen&amp;action=edit">&#91;update&#93;</a></sup>, <a href="/wiki/Endoxifen" title="Endoxifen">endoxifen</a>, a major active metabolite of tamoxifen with a 4-fold more potent PKC inhibition, was in <a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">phase III</a> clinical trials for bipolar disorder.<sup id="cite_ref-AdisInsight-Endoxifen_134-0" class="reference"><a href="#cite_note-AdisInsight-Endoxifen-134"><span class="cite-bracket">&#91;</span>134<span class="cite-bracket">&#93;</span></a></sup><sup id="cite_ref-pmid29207335_135-0" class="reference"><a href="#cite_note-pmid29207335-135"><span class="cite-bracket">&#91;</span>135<span class="cite-bracket">&#93;</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=Tamoxifen&amp;action=edit&amp;section=30" 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-drug_dictionary-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-drug_dictionary_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-drug_dictionary_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em 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(February 2005). <a rel="nofollow" class="external text" href="https://doi.org/10.1161%2F01.CIR.0000154545.84124.AC">"Effect of tamoxifen on venous thromboembolic events in a breast cancer prevention trial"</a>. <i>Circulation</i>. <b>111</b> (5): 650–656. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1161%2F01.CIR.0000154545.84124.AC">10.1161/01.CIR.0000154545.84124.AC</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15699284">15699284</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Circulation&amp;rft.atitle=Effect+of+tamoxifen+on+venous+thromboembolic+events+in+a+breast+cancer+prevention+trial&amp;rft.volume=111&amp;rft.issue=5&amp;rft.pages=650-656&amp;rft.date=2005-02&amp;rft_id=info%3Adoi%2F10.1161%2F01.CIR.0000154545.84124.AC&amp;rft_id=info%3Apmid%2F15699284&amp;rft.aulast=Decensi&amp;rft.aufirst=A&amp;rft.au=Maisonneuve%2C+P&amp;rft.au=Rotmensz%2C+N&amp;rft.au=Bettega%2C+D&amp;rft.au=Costa%2C+A&amp;rft.au=Sacchini%2C+V&amp;rft.au=Salvioni%2C+A&amp;rft.au=Travaglini%2C+R&amp;rft.au=Oliviero%2C+P&amp;rft.au=D%27Aiuto%2C+G&amp;rft.au=Gulisano%2C+M&amp;rft.au=Gucciardo%2C+G&amp;rft.au=del+Turco%2C+MR&amp;rft.au=Pizzichetta%2C+MA&amp;rft.au=Conforti%2C+S&amp;rft.au=Bonanni%2C+B&amp;rft.au=Boyle%2C+P&amp;rft.au=Veronesi%2C+U&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1161%252F01.CIR.0000154545.84124.AC&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-Harvey_2006-54"><span class="mw-cite-backlink"><b><a href="#cite_ref-Harvey_2006_54-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHarveyKimuraHajba2006" class="citation journal cs1">Harvey HA, Kimura M, Hajba A (April 2006). "Toremifene: an evaluation of its safety profile". <i>Breast</i>. <b>15</b> (2): 142–157. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.breast.2005.09.007">10.1016/j.breast.2005.09.007</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16289904">16289904</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Breast&amp;rft.atitle=Toremifene%3A+an+evaluation+of+its+safety+profile&amp;rft.volume=15&amp;rft.issue=2&amp;rft.pages=142-157&amp;rft.date=2006-04&amp;rft_id=info%3Adoi%2F10.1016%2Fj.breast.2005.09.007&amp;rft_id=info%3Apmid%2F16289904&amp;rft.aulast=Harvey&amp;rft.aufirst=HA&amp;rft.au=Kimura%2C+M&amp;rft.au=Hajba%2C+A&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-CameronFeuer2012-55"><span class="mw-cite-backlink">^ <a href="#cite_ref-CameronFeuer2012_55-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-CameronFeuer2012_55-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCameronFeuerde_la_Iglesia2012" class="citation book cs1">Cameron R, Feuer G, de la Iglesia F (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=xZf-CAAAQBAJ&amp;pg=PA565"><i>Drug-Induced Hepatotoxicity</i></a>. Springer Science &amp; Business Media. pp.&#160;565–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-3-642-61013-4" title="Special:BookSources/978-3-642-61013-4"><bdi>978-3-642-61013-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Drug-Induced+Hepatotoxicity&amp;rft.pages=565-&amp;rft.pub=Springer+Science+%26+Business+Media&amp;rft.date=2012-12-06&amp;rft.isbn=978-3-642-61013-4&amp;rft.aulast=Cameron&amp;rft.aufirst=R&amp;rft.au=Feuer%2C+G&amp;rft.au=de+la+Iglesia%2C+F&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DxZf-CAAAQBAJ%26pg%3DPA565&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-pmid17181445-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid17181445_56-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOsmanOsmanAhmed2007" class="citation journal cs1">Osman KA, Osman MM, Ahmed MH (January 2007). 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(December 2005). <a rel="nofollow" class="external text" href="https://doi.org/10.1200%2FJCO.2005.03.3266">"Pharmacogenetics of tamoxifen biotransformation is associated with clinical outcomes of efficacy and hot flashes"</a>. <i>Journal of Clinical Oncology</i>. <b>23</b> (36): 9312–9318. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1200%2FJCO.2005.03.3266">10.1200/JCO.2005.03.3266</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16361630">16361630</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Clinical+Oncology&amp;rft.atitle=Pharmacogenetics+of+tamoxifen+biotransformation+is+associated+with+clinical+outcomes+of+efficacy+and+hot+flashes&amp;rft.volume=23&amp;rft.issue=36&amp;rft.pages=9312-9318&amp;rft.date=2005-12&amp;rft_id=info%3Adoi%2F10.1200%2FJCO.2005.03.3266&amp;rft_id=info%3Apmid%2F16361630&amp;rft.aulast=Goetz&amp;rft.aufirst=MP&amp;rft.au=Rae%2C+JM&amp;rft.au=Suman%2C+VJ&amp;rft.au=Safgren%2C+SL&amp;rft.au=Ames%2C+MM&amp;rft.au=Visscher%2C+DW&amp;rft.au=Reynolds%2C+C&amp;rft.au=Couch%2C+FJ&amp;rft.au=Lingle%2C+WL&amp;rft.au=Flockhart%2C+DA&amp;rft.au=Desta%2C+Z&amp;rft.au=Perez%2C+EA&amp;rft.au=Ingle%2C+JN&amp;rft_id=https%3A%2F%2Fdoi.org%2F10.1200%252FJCO.2005.03.3266&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-Beverage_2007-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-Beverage_2007_58-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBeverageSissungSionDanesi2007" class="citation journal cs1">Beverage JN, Sissung TM, Sion AM, Danesi R, Figg WD (September 2007). 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Academic Press. pp.&#160;717–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-0-08-092346-8" title="Special:BookSources/978-0-08-092346-8"><bdi>978-0-08-092346-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=book&amp;rft.btitle=Osteoporosis+in+Men%3A+The+Effects+of+Gender+on+Skeletal+Health&amp;rft.pages=717-&amp;rft.pub=Academic+Press&amp;rft.date=2009-11-30&amp;rft.isbn=978-0-08-092346-8&amp;rft.aulast=Orwoll&amp;rft.aufirst=ES&amp;rft.au=Bilezikian%2C+JP&amp;rft.au=Vanderschueren%2C+D&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DnfWNYFdOsCsC%26pg%3DPA717&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-isbn0-471-89979-8-103"><span class="mw-cite-backlink"><b><a href="#cite_ref-isbn0-471-89979-8_103-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSneader2005" class="citation book cs1">Sneader W (2005). <i>Drug Discovery: A History</i>. 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Retrieved <span class="nowrap">24 June</span> 2008</span>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=Health+and+Behavior&amp;rft.atitle=Dog%27s+tale+of+survival+opens+door+in+cancer+research&amp;rft.date=2002-07-24&amp;rft.aulast=Kirk&amp;rft.aufirst=E&amp;rft_id=https%3A%2F%2Fwww.usatoday.com%2Fnews%2Fhealth%2F2002-07-24-cover-cancer_x.htm&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-pmid11106254-106"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid11106254_106-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBlackwellHaroonShanSaito2000" class="citation journal cs1">Blackwell KL, Haroon ZA, Shan S, Saito W, Broadwater G, Greenberg CS, et&#160;al. (November 2000). <a rel="nofollow" class="external text" href="http://clincancerres.aacrjournals.org/cgi/content/abstract/6/11/4359">"Tamoxifen inhibits angiogenesis in estrogen receptor-negative animal models"</a>. <i>Clinical Cancer Research</i>. <b>6</b> (11): 4359–4364. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11106254">11106254</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20080906195254/http://clincancerres.aacrjournals.org/cgi/content/abstract/6/11/4359">Archived</a> from the original on 6 September 2008.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Clinical+Cancer+Research&amp;rft.atitle=Tamoxifen+inhibits+angiogenesis+in+estrogen+receptor-negative+animal+models&amp;rft.volume=6&amp;rft.issue=11&amp;rft.pages=4359-4364&amp;rft.date=2000-11&amp;rft_id=info%3Apmid%2F11106254&amp;rft.aulast=Blackwell&amp;rft.aufirst=KL&amp;rft.au=Haroon%2C+ZA&amp;rft.au=Shan%2C+S&amp;rft.au=Saito%2C+W&amp;rft.au=Broadwater%2C+G&amp;rft.au=Greenberg%2C+CS&amp;rft.au=Dewhirst%2C+MW&amp;rft_id=http%3A%2F%2Fclincancerres.aacrjournals.org%2Fcgi%2Fcontent%2Fabstract%2F6%2F11%2F4359&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-pmid12796359-107"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid12796359_107-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid12796359_107-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJensenJordan2003" class="citation journal cs1">Jensen EV, Jordan VC (June 2003). <a rel="nofollow" class="external text" href="https://clincancerres.aacrjournals.org/content/9/6/1980.short">"The estrogen receptor: a model for molecular medicine"</a>. <i>Clin. Cancer Res</i>. <b>9</b> (6): 1980–9. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12796359">12796359</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Clin.+Cancer+Res.&amp;rft.atitle=The+estrogen+receptor%3A+a+model+for+molecular+medicine&amp;rft.volume=9&amp;rft.issue=6&amp;rft.pages=1980-9&amp;rft.date=2003-06&amp;rft_id=info%3Apmid%2F12796359&amp;rft.aulast=Jensen&amp;rft.aufirst=EV&amp;rft.au=Jordan%2C+VC&amp;rft_id=https%3A%2F%2Fclincancerres.aacrjournals.org%2Fcontent%2F9%2F6%2F1980.short&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-HowellJordan2013B-108"><span class="mw-cite-backlink"><b><a href="#cite_ref-HowellJordan2013B_108-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHowellJordan2013" class="citation book cs1">Howell A, Jordan VC (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ZM26CgAAQBAJ&amp;pg=PA229">"Adjuvant Antihormone Therapy"</a>. In Jordon VC (ed.). <i>Estrogen Action, Selective Estrogen Receptor Modulators And Women's Health: Progress And Promise</i>. World Scientific. pp.&#160;229–254. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1142%2F9781848169586_0010">10.1142/9781848169586_0010</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a>&#160;<a href="/wiki/Special:BookSources/978-1-84816-959-3" title="Special:BookSources/978-1-84816-959-3"><bdi>978-1-84816-959-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Adjuvant+Antihormone+Therapy&amp;rft.btitle=Estrogen+Action%2C+Selective+Estrogen+Receptor+Modulators+And+Women%27s+Health%3A+Progress+And+Promise&amp;rft.pages=229-254&amp;rft.pub=World+Scientific&amp;rft.date=2013&amp;rft_id=info%3Adoi%2F10.1142%2F9781848169586_0010&amp;rft.isbn=978-1-84816-959-3&amp;rft.aulast=Howell&amp;rft.aufirst=A&amp;rft.au=Jordan%2C+VC&amp;rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DZM26CgAAQBAJ%26pg%3DPA229&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-Cole_1971-109"><span class="mw-cite-backlink"><b><a href="#cite_ref-Cole_1971_109-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFColeJonesTodd1971" class="citation journal cs1">Cole MP, Jones CT, Todd ID (June 1971). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2008453">"A new anti-oestrogenic agent in late breast cancer. 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href="#cite_ref-TalaeiPourgholami2016_132-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-TalaeiPourgholami2016_132-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-TalaeiPourgholami2016_132-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTalaeiPourgholamiKhatibi-MoghadamFaridhosseini2016" class="citation journal cs1">Talaei A, Pourgholami M, Khatibi-Moghadam H, Faridhosseini F, Farhoudi F, Askari-Noghani A, et&#160;al. 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"Tamoxifen: A Protein Kinase C Inhibitor to Treat Mania: A Systematic Review and Meta-Analysis of Randomized, Placebo-Controlled Trials". <i>Journal of Clinical Psychopharmacology</i>. <b>36</b> (3): 272–275. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2FJCP.0000000000000492">10.1097/JCP.0000000000000492</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/27088436">27088436</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a>&#160;<a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:39792641">39792641</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Journal+of+Clinical+Psychopharmacology&amp;rft.atitle=Tamoxifen%3A+A+Protein+Kinase+C+Inhibitor+to+Treat+Mania%3A+A+Systematic+Review+and+Meta-Analysis+of+Randomized%2C+Placebo-Controlled+Trials&amp;rft.volume=36&amp;rft.issue=3&amp;rft.pages=272-275&amp;rft.date=2016-06&amp;rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A39792641%23id-name%3DS2CID&amp;rft_id=info%3Apmid%2F27088436&amp;rft_id=info%3Adoi%2F10.1097%2FJCP.0000000000000492&amp;rft.aulast=Talaei&amp;rft.aufirst=A&amp;rft.au=Pourgholami%2C+M&amp;rft.au=Khatibi-Moghadam%2C+H&amp;rft.au=Faridhosseini%2C+F&amp;rft.au=Farhoudi%2C+F&amp;rft.au=Askari-Noghani%2C+A&amp;rft.au=Sadeghi%2C+R&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-SaxenaScaini2017-133"><span class="mw-cite-backlink">^ <a href="#cite_ref-SaxenaScaini2017_133-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-SaxenaScaini2017_133-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSaxenaScainiBavarescoLeite2017" class="citation journal cs1">Saxena A, Scaini G, Bavaresco DV, Leite C, Valvassori SS, Carvalho AF, et&#160;al. (November 2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5701269">"Role of Protein Kinase C in Bipolar Disorder: A Review of the Current Literature"</a>. <i>Molecular Neuropsychiatry</i>. <b>3</b> (2): 108–124. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000480349">10.1159/000480349</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a>&#160;<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5701269">5701269</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29230399">29230399</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=Molecular+Neuropsychiatry&amp;rft.atitle=Role+of+Protein+Kinase+C+in+Bipolar+Disorder%3A+A+Review+of+the+Current+Literature&amp;rft.volume=3&amp;rft.issue=2&amp;rft.pages=108-124&amp;rft.date=2017-11&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5701269%23id-name%3DPMC&amp;rft_id=info%3Apmid%2F29230399&amp;rft_id=info%3Adoi%2F10.1159%2F000480349&amp;rft.aulast=Saxena&amp;rft.aufirst=A&amp;rft.au=Scaini%2C+G&amp;rft.au=Bavaresco%2C+DV&amp;rft.au=Leite%2C+C&amp;rft.au=Valvassori%2C+SS&amp;rft.au=Carvalho%2C+AF&amp;rft.au=Quevedo%2C+J&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5701269&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-AdisInsight-Endoxifen-134"><span class="mw-cite-backlink"><b><a href="#cite_ref-AdisInsight-Endoxifen_134-0">^</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://adisinsight.springer.com/drugs/800036114">"Endoxifen - Intas Pharmaceuticals/Jina pharmaceuticals"</a>. <i>AdisInsight</i>. Springer Nature Switzerland AG.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=AdisInsight&amp;rft.atitle=Endoxifen+-+Intas+Pharmaceuticals%2FJina+pharmaceuticals&amp;rft_id=https%3A%2F%2Fadisinsight.springer.com%2Fdrugs%2F800036114&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> <li id="cite_note-pmid29207335-135"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid29207335_135-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAhmad2018" class="citation journal cs1">Ahmad I (January 2018). "Tamoxifen a pioneering drug: An update on the therapeutic potential of tamoxifen derivatives". <i>European Journal of Medicinal Chemistry</i>. <b>143</b>: 515–531. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ejmech.2017.11.056">10.1016/j.ejmech.2017.11.056</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29207335">29207335</a>.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=article&amp;rft.jtitle=European+Journal+of+Medicinal+Chemistry&amp;rft.atitle=Tamoxifen+a+pioneering+drug%3A+An+update+on+the+therapeutic+potential+of+tamoxifen+derivatives&amp;rft.volume=143&amp;rft.pages=515-531&amp;rft.date=2018-01&amp;rft_id=info%3Adoi%2F10.1016%2Fj.ejmech.2017.11.056&amp;rft_id=info%3Apmid%2F29207335&amp;rft.aulast=Ahmad&amp;rft.aufirst=I&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=31" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDean2014" class="citation book cs1">Dean L (2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK247013/">"Tamoxifen Therapy and CYP2D6 Genotype"</a>. In Pratt VM, McLeod HL, Rubinstein WS, et&#160;al. (eds.). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK61999/"><i>Medical Genetics Summaries</i></a>. <a href="/wiki/National_Center_for_Biotechnology_Information" title="National Center for Biotechnology Information">National Center for Biotechnology Information</a> (NCBI). <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a>&#160;<a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/28520357">28520357</a>. Bookshelf ID: NBK247013.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&amp;rft.genre=bookitem&amp;rft.atitle=Tamoxifen+Therapy+and+CYP2D6+Genotype&amp;rft.btitle=Medical+Genetics+Summaries&amp;rft.pub=National+Center+for+Biotechnology+Information+%28NCBI%29&amp;rft.date=2014&amp;rft_id=info%3Apmid%2F28520357&amp;rft.aulast=Dean&amp;rft.aufirst=L&amp;rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fbooks%2FNBK247013%2F&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tamoxifen&amp;action=edit&amp;section=32" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/2733526">"Tamoxifen"</a>. <i>PubChem</i>. U.S. National Library of Medicine.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=PubChem&amp;rft.atitle=Tamoxifen&amp;rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F2733526&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/2733525">"Tamoxifen citrate"</a>. <i>PubChem</i>. U.S. National Library of Medicine.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=PubChem&amp;rft.atitle=Tamoxifen+citrate&amp;rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F2733525&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></li> <li><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.cancer.gov/about-cancer/treatment/drugs/tamoxifencitrate">"Tamoxifen citrate"</a>. <i>National Cancer Institute</i>. 5 October 2006.</cite><span title="ctx_ver=Z39.88-2004&amp;rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&amp;rft.genre=unknown&amp;rft.jtitle=National+Cancer+Institute&amp;rft.atitle=Tamoxifen+citrate&amp;rft.date=2006-10-05&amp;rft_id=https%3A%2F%2Fwww.cancer.gov%2Fabout-cancer%2Ftreatment%2Fdrugs%2Ftamoxifencitrate&amp;rfr_id=info%3Asid%2Fen.wikipedia.org%3ATamoxifen" class="Z3988"></span></li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output 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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:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogens_and_antiestrogens" title="Template talk:Estrogens and antiestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogens_and_antiestrogens" title="Special:EditPage/Template:Estrogens and antiestrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogens_and_antiestrogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><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:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</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 Estrogen receptor</span> agonists</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/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a><sup>†</sup></li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, <a href="/wiki/Estradiol_ester_mixture" class="mw-redirect" title="Estradiol ester mixture">estradiol ester mixtures</a> (<a href="/wiki/Climacteron" class="mw-redirect" title="Climacteron">Climacteron</a>))</li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a> (e.g., <a href="/wiki/Estriol_succinate" title="Estriol succinate">estriol succinate</a>, <a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">polyestriol phosphate</a>)</li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a> <ul><li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a><sup>#</sup> <ul><li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone; DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate</a></li></ul></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol (stilbestrol)</a></li> <li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters/ethers</a> <ul><li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (diethylstilbestrol dimethyl ether)</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol (diethylstilbestrol monomethyl ether)</a></li></ul></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol (promethestrol)</a> <ul><li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate (promethestrol dipropionate)</a></li></ul></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> (e.g., <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</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 follicle-stimulating hormone</span>, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip luteinizing hormone</span>)</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/Antiestrogen" title="Antiestrogen">Antiestrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><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:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</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 Estrogen receptor</span> antagonists<br />(incl. <a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="selective estrogen receptor modulators">SERMs</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 estrogen receptor modulators</span>/<a href="/wiki/Selective_estrogen_receptor_downregulators" class="mw-redirect" title="Selective estrogen receptor downregulators"><abbr title="selective estrogen receptor downregulators">SERDs</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 estrogen receptor downregulators</span>)</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/Acolbifene" title="Acolbifene">Acolbifene</a><sup>†</sup></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a><sup>#</sup></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a><sup>†</sup></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a class="mw-selflink selflink">Tamoxifen</a><sup>#</sup></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li></ul> <ul><li><i>Exclusively antagonistic:</i> <a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">Aromatase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>First-generation:</i> <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Testolactone" title="Testolactone">Testolactone</a></li></ul> <ul><li><i>Second-generation:</i> <a href="/wiki/Fadrozole" title="Fadrozole">Fadrozole</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li></ul> <ul><li><i>Third-generation:</i> <a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Letrozole" title="Letrozole">Letrozole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</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/Androgen" title="Androgen">Androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>)</li> <li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D<sub>2</sub> receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin" title="Prolactin">prolactin</a> releasers) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>, <a href="/wiki/Goserelin" title="Goserelin">goserelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>, <a href="/wiki/Elagolix" title="Elagolix">elagolix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Mixed mechanism of action:</i> <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li></ul> <ul><li><i>Androstenedione immunogens:</i> <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor 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:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</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="Estrogen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen 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/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</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 Estrogen 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>Steroidal:</i> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&amp;action=edit&amp;redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&amp;action=edit&amp;redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><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/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</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/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</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/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol"><i>ent</i>-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</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/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</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/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</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/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&amp;action=edit&amp;redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&amp;action=edit&amp;redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol"><i>meso</i>-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&amp;action=edit&amp;redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&amp;action=edit&amp;redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li><i>Unknown/unsorted:</i> <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li><i>Xenoestrogens:</i> <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&amp;action=edit&amp;redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (<i>cis</i>-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&amp;action=edit&amp;redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</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_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</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 estrogen 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><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&amp;action=edit&amp;redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4&#39;-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&amp;action=edit&amp;redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&amp;action=edit&amp;redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&amp;action=edit&amp;redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&amp;action=edit&amp;redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&amp;action=edit&amp;redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&amp;action=edit&amp;redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&amp;action=edit&amp;redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&amp;action=edit&amp;redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&amp;action=edit&amp;redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&amp;action=edit&amp;redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a class="mw-selflink selflink">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&amp;action=edit&amp;redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&amp;action=edit&amp;redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&amp;action=edit&amp;redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&amp;action=edit&amp;redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</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/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&amp;action=edit&amp;redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&amp;action=edit&amp;redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&amp;action=edit&amp;redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&amp;action=edit&amp;redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&amp;action=edit&amp;redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&amp;action=edit&amp;redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&amp;action=edit&amp;redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&amp;action=edit&amp;redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&amp;action=edit&amp;redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&amp;action=edit&amp;redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&amp;action=edit&amp;redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&amp;action=edit&amp;redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&amp;action=edit&amp;redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</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/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</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 estrogen 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/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p&#39;-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&amp;action=edit&amp;redlink=1" class="new" title="O&#39;,p&#39;-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/w/index.php?title=G-1_(drug)&amp;action=edit&amp;redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&amp;action=edit&amp;redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&amp;action=edit&amp;redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&amp;action=edit&amp;redlink=1" class="new" title="2,2&#39;,5&#39;-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&amp;action=edit&amp;redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a class="mw-selflink selflink">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</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/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&amp;action=edit&amp;redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&amp;action=edit&amp;redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</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/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</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:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</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:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</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="Monoamine_reuptake_inhibitors" 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:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_reuptake_inhibitors" title="Template talk:Monoamine reuptake inhibitors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_reuptake_inhibitors" title="Special:EditPage/Template:Monoamine reuptake inhibitors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_reuptake_inhibitors" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_reuptake_inhibitor" title="Monoamine reuptake inhibitor">Monoamine reuptake inhibitors</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Dopamine_transporter" title="Dopamine transporter"><abbr title="Dopamine transporter">DAT</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 Dopamine transporter</span><br /><small>(<a href="/wiki/Dopamine_reuptake_inhibitors" class="mw-redirect" title="Dopamine reuptake inhibitors"><abbr title="Dopamine reuptake inhibitors">DRIs</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 Dopamine reuptake inhibitors</span>)</small></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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Piperazines:</i> <a href="/wiki/DBL-583" title="DBL-583">DBL-583</a></li> <li><a href="/wiki/GBR-12783" title="GBR-12783">GBR-12783</a></li> <li><a href="/wiki/GBR-12935" title="GBR-12935">GBR-12935</a></li> <li><a href="/wiki/GBR-13069" title="GBR-13069">GBR-13069</a></li> <li><a href="/wiki/GBR-13098" title="GBR-13098">GBR-13098</a></li> <li><a href="/wiki/JJC8-088" title="JJC8-088">JJC8-088</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Piperidines:</i> <a href="/wiki/4-Fluoropethidine" title="4-Fluoropethidine">4-Fluoropethidine</a></li> <li><a href="/wiki/Benocyclidine" title="Benocyclidine">Benocyclidine (BTCP)</a></li> <li><a href="/wiki/Desoxypipradrol" title="Desoxypipradrol">Desoxypipradrol</a></li> <li><a href="/wiki/Dexmethylphenidate" title="Dexmethylphenidate">Dexmethylphenidate</a></li> <li><a href="/wiki/Difemetorex" title="Difemetorex">Difemetorex</a></li> <li><a href="/wiki/Ethylphenidate" title="Ethylphenidate">Ethylphenidate</a></li> <li><a href="/wiki/HDMP-28" title="HDMP-28">HDMP-28</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Phencyclidine" title="Phencyclidine">Phencyclidine</a></li> <li><a href="/wiki/Pipradrol" title="Pipradrol">Pipradrol</a></li> <li><a href="/wiki/Serdexmethylphenidate" title="Serdexmethylphenidate">Serdexmethylphenidate</a></li> <li><a href="/wiki/Tenocyclidine" title="Tenocyclidine">Tenocyclidine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Pyrrolidines:</i> <a href="/wiki/Diphenylprolinol" title="Diphenylprolinol">Diphenylprolinol</a></li> <li><a href="/wiki/Methylenedioxypyrovalerone" title="Methylenedioxypyrovalerone">MDPV</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Prolintane" title="Prolintane">Prolintane</a></li> <li><a href="/wiki/Pyrovalerone" title="Pyrovalerone">Pyrovalerone</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Tropanes:</i> <a href="/wiki/Altropane" title="Altropane">Altropane</a></li> <li><a href="/wiki/Benzatropine" title="Benzatropine">Benzatropine (benztropine)</a></li> <li><a href="/wiki/Brasofensine" title="Brasofensine">Brasofensine</a></li> <li><a href="/wiki/WIN_35428" class="mw-redirect" title="WIN 35428">CFT</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Dichloropane" title="Dichloropane">Dichloropane</a></li> <li><a href="/wiki/Difluoropine" title="Difluoropine">Difluoropine</a></li> <li><a href="/wiki/Etybenzatropine" title="Etybenzatropine">Etybenzatropine (ethybenztropine)</a></li> <li><a href="/wiki/FE-%CE%B2-CPPIT" title="FE-β-CPPIT">FE-β-CPPIT</a></li> <li><a href="/wiki/FP-%CE%B2-CPPIT" title="FP-β-CPPIT">FP-β-CPPIT</a></li> <li><a href="/wiki/Ioflupane_(123I)" title="Ioflupane (123I)">Ioflupane (<sup>123</sup>I)</a></li> <li><a href="/wiki/RTI-55" title="RTI-55">RTI-55</a></li> <li><a href="/wiki/RTI-112" title="RTI-112">RTI-112</a></li> <li><a href="/wiki/RTI-113" title="RTI-113">RTI-113</a></li> <li><a href="/wiki/RTI-121" title="RTI-121">RTI-121</a></li> <li><a href="/wiki/RTI-126" title="RTI-126">RTI-126</a></li> <li><a href="/wiki/RTI-150" title="RTI-150">RTI-150</a></li> <li><a href="/wiki/RTI-177" title="RTI-177">RTI-177</a></li> <li><a href="/wiki/RTI-229" title="RTI-229">RTI-229</a></li> <li><a href="/wiki/(-)-2%CE%B2-(3-(4-Methylphenyl)isoxazol-5-yl)-3%CE%B2-(4-chlorophenyl)tropane" class="mw-redirect" title="(-)-2β-(3-(4-Methylphenyl)isoxazol-5-yl)-3β-(4-chlorophenyl)tropane">RTI-336</a></li> <li><a href="/wiki/Tesofensine" title="Tesofensine">Tesofensine</a></li> <li><a href="/wiki/Troparil" title="Troparil">Troparil</a></li> <li><a href="/wiki/Tropoxane" title="Tropoxane">Tropoxane</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(4-tolyl)-tropane" title="2β-Propanoyl-3β-(4-tolyl)-tropane">WF-11</a></li> <li><a href="/wiki/2%CE%B2-Propanoyl-3%CE%B2-(2-naphthyl)-tropane" title="2β-Propanoyl-3β-(2-naphthyl)-tropane">WF-23</a></li> <li><a href="/wiki/2-Propanoyl-3-(4-isopropylphenyl)-tropane" title="2-Propanoyl-3-(4-isopropylphenyl)-tropane">WF-31</a></li> <li><a href="/wiki/2%CE%B1-(Propanoyl)-3%CE%B2-(2-(6-methoxynaphthyl))-tropane" title="2α-(Propanoyl)-3β-(2-(6-methoxynaphthyl))-tropane">WF-33</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/Adrafinil" title="Adrafinil">Adrafinil</a></li> <li><a href="/wiki/Amifitadine" class="mw-redirect" title="Amifitadine">Amifitadine</a></li> <li><a href="/wiki/Armodafinil" title="Armodafinil">Armodafinil</a></li> <li><a href="/wiki/Amfonelic_acid" title="Amfonelic acid">Amfonelic acid</a></li> <li><a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Ansofaxine" title="Ansofaxine">Ansofaxine</a></li> <li><a href="/wiki/Butyltolylquinuclidine" title="Butyltolylquinuclidine">BTQ</a></li> <li><a href="/wiki/BTS_74,398" title="BTS 74,398">BTS 74,398</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><i><a href="/wiki/Chaenomeles_speciosa" title="Chaenomeles speciosa">Chaenomeles speciosa</a></i></li> <li><a href="/wiki/Ciclazindol" title="Ciclazindol">Ciclazindol</a></li> <li><a href="/wiki/Dasotraline" title="Dasotraline">Dasotraline</a></li> <li><a href="/wiki/Desmethylsertraline" title="Desmethylsertraline">Desmethylsertraline</a></li> <li><a href="/wiki/Desmethylsibutramine" title="Desmethylsibutramine">Desmethylsibutramine (BTS-54354)</a></li> <li><a href="/wiki/Diclofensine" title="Diclofensine">Diclofensine</a></li> <li><a href="/wiki/Didesmethylsibutramine" title="Didesmethylsibutramine">Didesmethylsibutramine (BTS-54505)</a></li> <li><a href="/wiki/Dimethocaine" title="Dimethocaine">Dimethocaine</a></li> <li><a href="/wiki/Diphenylpyraline" title="Diphenylpyraline">Diphenylpyraline</a></li> <li><a href="/wiki/Dizocilpine" title="Dizocilpine">Dizocilpine (MK-801)</a></li> <li><a href="/wiki/DOV-102,677" title="DOV-102,677">DOV-102,677</a></li> <li><a href="/wiki/DOV-216,303" title="DOV-216,303">DOV-216,303</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><a href="/wiki/Esketamine" title="Esketamine">Esketamine</a></li> <li><a href="/wiki/EXP-561" title="EXP-561">EXP-561</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Fezolamine" title="Fezolamine">Fezolamine</a></li> <li><a href="/wiki/Fluorenol" title="Fluorenol">Fluorenol</a></li> <li><a href="/wiki/GYKI-52895" class="mw-redirect" title="GYKI-52895">GYKI-52895</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Indatraline" title="Indatraline">Indatraline</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Levophacetoperane" title="Levophacetoperane">Levophacetoperane</a></li> <li><a href="/wiki/Liafensine" title="Liafensine">Liafensine</a></li> <li><a href="/wiki/LR-5182" title="LR-5182">LR-5182</a></li> <li><a href="/wiki/Manifaxine" title="Manifaxine">Manifaxine</a></li> <li><a href="/wiki/Mazindol" title="Mazindol">Mazindol</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Mesocarb" title="Mesocarb">Mesocarb</a></li> <li><a href="/wiki/Metaphit" title="Metaphit">Metaphit</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/Modafinil" title="Modafinil">Modafinil</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/NS-2359" title="NS-2359">NS-2359</a></li> <li><a href="/wiki/O-2172" title="O-2172">O-2172</a></li> <li><a href="/wiki/Oroxylin_A" title="Oroxylin A">Oroxylin A</a></li> <li><a href="/wiki/Perafensine" title="Perafensine">Perafensine</a></li> <li><a href="/wiki/Pridefine" title="Pridefine">Pridefine</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Rimcazole" title="Rimcazole">Rimcazole</a></li> <li><a href="/wiki/Sertraline" title="Sertraline">Sertraline</a></li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li> <li><a href="/wiki/Tametraline" title="Tametraline">Tametraline</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Tripelennamine" title="Tripelennamine">Tripelennamine</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</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/Norepinephrine_transporter" title="Norepinephrine transporter"><abbr title="Norepinephrine transporter">NET</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 Norepinephrine transporter</span><br /><small>(<a href="/wiki/Norepinephrine_reuptake_inhibitors" class="mw-redirect" title="Norepinephrine reuptake inhibitors"><abbr title="Norepinephrine reuptake inhibitors">NRIs</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 Norepinephrine reuptake inhibitors</span>)</small></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><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Selective norepinephrine reuptake inhibitors:</i> <a href="/wiki/Amedalin" title="Amedalin">Amedalin</a></li> <li><a href="/wiki/Alseroxylon" title="Alseroxylon">Alseroxylon</a></li> <li><a href="/wiki/Ciclazindol" title="Ciclazindol">Ciclazindol</a></li> <li><a href="/wiki/Daledalin" title="Daledalin">Daledalin</a></li> <li><a href="/wiki/Edivoxetine" title="Edivoxetine">Edivoxetine</a></li> <li><a href="/wiki/Esreboxetine" title="Esreboxetine">Esreboxetine</a></li> <li><a href="/wiki/Lortalamine" title="Lortalamine">Lortalamine</a></li> <li><a href="/wiki/Mazindol" title="Mazindol">Mazindol</a></li> <li><a href="/wiki/Nisoxetine" title="Nisoxetine">Nisoxetine</a></li> <li><a href="/wiki/Reboxetine" title="Reboxetine">Reboxetine</a></li> <li><a href="/wiki/Talopram" title="Talopram">Talopram</a></li> <li><a href="/wiki/Talsupram" title="Talsupram">Talsupram</a></li> <li><a href="/wiki/Tandamine" title="Tandamine">Tandamine</a></li> <li><a href="/wiki/Teniloxazine" title="Teniloxazine">Teniloxazine</a></li> <li><a href="/wiki/Viloxazine" title="Viloxazine">Viloxazine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Norepinephrine–dopamine reuptake inhibitors:</i> <a href="/wiki/Amineptine" title="Amineptine">Amineptine</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Bupropion</a></li> <li><a href="/wiki/Fencamine" title="Fencamine">Fencamine</a></li> <li><a href="/wiki/Fencamfamin" title="Fencamfamin">Fencamfamin</a></li> <li><a href="/wiki/Hydroxybupropion" title="Hydroxybupropion">Hydroxybupropion</a></li> <li><a href="/wiki/Lefetamine" title="Lefetamine">Lefetamine</a></li> <li><a href="/wiki/Levophacetoperane" title="Levophacetoperane">Levophacetoperane</a></li> <li><a href="/wiki/LR-5182" title="LR-5182">LR-5182</a></li> <li><a href="/wiki/Manifaxine" title="Manifaxine">Manifaxine</a></li> <li><a href="/wiki/Methylphenidate" title="Methylphenidate">Methylphenidate</a></li> <li><a href="/wiki/Nomifensine" title="Nomifensine">Nomifensine</a></li> <li><a href="/wiki/O-2172" title="O-2172">O-2172</a></li> <li><a href="/wiki/Radafaxine" title="Radafaxine">Radafaxine</a></li> <li><a href="/wiki/Serdexmethylphenidate" title="Serdexmethylphenidate">Serdexmethylphenidate</a></li> <li><a href="/wiki/Solriamfetol" title="Solriamfetol">Solriamfetol</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Serotonin–norepinephrine reuptake inhibitors:</i> <a href="/wiki/Atomoxetine" title="Atomoxetine">Atomoxetine (tomoxetine)</a></li> <li><a href="/wiki/CP-39,332" title="CP-39,332">CP-39,332</a></li> <li><a href="/wiki/Desvenlafaxine" title="Desvenlafaxine">Desvenlafaxine</a></li> <li><a href="/wiki/Duloxetine" title="Duloxetine">Duloxetine</a></li> <li><a href="/wiki/Eclanamine" title="Eclanamine">Eclanamine</a></li> <li><a href="/wiki/Levomilnacipran" title="Levomilnacipran">Levomilnacipran</a></li> <li><a href="/wiki/McN5652" title="McN5652">McN5652</a></li> <li><a href="/wiki/Milnacipran" title="Milnacipran">Milnacipran</a></li> <li><a href="/wiki/N-Methyl-PPPA" title="N-Methyl-PPPA">N-Methyl-PPPA</a></li> <li><a href="/w/index.php?title=Nafenodone&amp;action=edit&amp;redlink=1" class="new" title="Nafenodone (page does not exist)">Nafenodone</a></li> <li><a href="/wiki/PPPA_(drug)" title="PPPA (drug)">PPPA</a></li> <li><a href="/wiki/Tofenacin" title="Tofenacin">Tofenacin</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Serotonin–norepinephrine–dopamine reuptake inhibitors:</i> <a href="/wiki/3,3-Diphenylcyclobutanamine" title="3,3-Diphenylcyclobutanamine">3,3-Diphenylcyclobutanamine</a></li> <li><a href="/wiki/Amifitadine" class="mw-redirect" title="Amifitadine">Amifitadine</a></li> <li><a href="/wiki/Ansofaxine" title="Ansofaxine">Ansofaxine</a></li> <li><a href="/wiki/Bicifadine" title="Bicifadine">Bicifadine</a></li> <li><a href="/wiki/Brasofensine" title="Brasofensine">Brasofensine</a></li> <li><a href="/wiki/Centanafadine" title="Centanafadine">Centanafadine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Dasotraline" title="Dasotraline">Dasotraline</a></li> <li><a href="/wiki/Desmethylsertraline" title="Desmethylsertraline">Desmethylsertraline</a></li> <li><a href="/wiki/Desmethylsibutramine" title="Desmethylsibutramine">Desmethylsibutramine (BTS-54354)</a></li> <li><a href="/wiki/Diclofensine" title="Diclofensine">Diclofensine</a></li> <li><a href="/wiki/Didesmethylsibutramine" title="Didesmethylsibutramine">Didesmethylsibutramine (BTS-54505)</a></li> <li><a href="/wiki/DOV-102677" class="mw-redirect" title="DOV-102677">DOV-102677</a></li> <li><a href="/wiki/DOV-216303" class="mw-redirect" title="DOV-216303">DOV-216303</a></li> <li><a href="/wiki/EXP-561" title="EXP-561">EXP-561</a></li> <li><a href="/wiki/Fezolamine" title="Fezolamine">Fezolamine</a></li> <li><a href="/wiki/HDMP-28" title="HDMP-28">HDMP-28</a></li> <li><a href="/wiki/HP-505" title="HP-505">HP-505</a></li> <li><a href="/wiki/Indatraline" title="Indatraline">Indatraline</a></li> <li><a href="/wiki/JNJ-7925476" title="JNJ-7925476">JNJ-7925476</a></li> <li><a href="/wiki/JZ-IV-10" title="JZ-IV-10">JZ-IV-10</a></li> <li><a href="/wiki/Liafensine" title="Liafensine">Liafensine</a></li> <li><a href="/wiki/Mazindol" title="Mazindol">Mazindol</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/NS-2359" title="NS-2359">NS-2359</a></li> <li><a href="/wiki/Perafensine" title="Perafensine">Perafensine</a></li> <li><a href="/wiki/PRC200" class="mw-redirect" title="PRC200">PRC200</a></li> <li><a href="/wiki/Pridefine" title="Pridefine">Pridefine</a></li> <li><a href="/w/index.php?title=SEP-228431&amp;action=edit&amp;redlink=1" class="new" title="SEP-228431 (page does not exist)">SEP-228431</a></li> <li><a href="/w/index.php?title=SEP-228432&amp;action=edit&amp;redlink=1" class="new" title="SEP-228432 (page does not exist)">SEP-228432</a></li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tesofensine" title="Tesofensine">Tesofensine</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Tropane" title="Tropane">Tropanes</a> (e.g., <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Tricyclic antidepressants:</i> <a href="/wiki/Amitriptyline" title="Amitriptyline">Amitriptyline</a></li> <li><a href="/wiki/Butriptyline" title="Butriptyline">Butriptyline</a></li> <li><a href="/wiki/Cianopramine" title="Cianopramine">Cianopramine</a></li> <li><a href="/wiki/Clomipramine" title="Clomipramine">Clomipramine</a></li> <li><a href="/wiki/Desipramine" title="Desipramine">Desipramine</a></li> <li><a href="/wiki/Dosulepin" title="Dosulepin">Dosulepin (dothiepin)</a></li> <li><a href="/wiki/Doxepin" title="Doxepin">Doxepin</a></li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/Lofepramine" title="Lofepramine">Lofepramine</a></li> <li><a href="/wiki/Melitracen" title="Melitracen">Melitracen</a></li> <li><a href="/wiki/Nortriptyline" title="Nortriptyline">Nortriptyline</a></li> <li><a href="/wiki/Protriptyline" title="Protriptyline">Protriptyline</a></li> <li><a href="/wiki/Trimipramine" title="Trimipramine">Trimipramine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Tetracyclic antidepressants:</i> <a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Maprotiline" title="Maprotiline">Maprotiline</a></li> <li><a href="/wiki/Mianserin" title="Mianserin">Mianserin</a></li> <li><a href="/wiki/Oxaprotiline" title="Oxaprotiline">Oxaprotiline</a></li> <li><a href="/wiki/Setiptiline" title="Setiptiline">Setiptiline</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/wiki/Histamine_antagonist" class="mw-redirect" title="Histamine antagonist">Antihistamines</a> (e.g., <a href="/wiki/Brompheniramine" title="Brompheniramine">brompheniramine</a>, <a href="/wiki/Chlorphenamine" title="Chlorphenamine">chlorphenamine</a>, <a href="/wiki/Pheniramine" title="Pheniramine">pheniramine</a>, <a href="/wiki/Tripelennamine" title="Tripelennamine">tripelennamine</a>)</li> <li><a href="/wiki/Antipsychotic" title="Antipsychotic">Antipsychotics</a> (e.g., <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</a> (e.g., <a href="/wiki/Ketamine" title="Ketamine">ketamine</a>, <a href="/wiki/Phencyclidine" title="Phencyclidine">phencyclidine</a>)</li> <li><a href="/wiki/Dopexamine" title="Dopexamine">Dopexamine</a></li> <li><a href="/wiki/Ephenidine" title="Ephenidine">Ephenidine</a></li> <li><i><a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo biloba</a></i></li> <li><a href="/wiki/Indeloxazine" title="Indeloxazine">Indeloxazine</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Desmetramadol" title="Desmetramadol">desmetramadol</a>, <a href="/wiki/Methadone" title="Methadone">methadone</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine (meperidine)</a>, <a href="/wiki/Tapentadol" title="Tapentadol">tapentadol</a>, <a href="/wiki/Tramadol" title="Tramadol">tramadol</a>, <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</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/Serotonin_transporter" title="Serotonin transporter"><abbr title="Serotonin transporter">SERT</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 Serotonin transporter</span><br /><small>(<a href="/wiki/Serotonin_reuptake_inhibitors" class="mw-redirect" title="Serotonin reuptake inhibitors"><abbr title="Serotonin reuptake inhibitors">SRIs</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 Serotonin reuptake inhibitors</span>)</small></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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Selective serotonin reuptake inhibitors:</i> <a href="/wiki/6-Nitroquipazine" title="6-Nitroquipazine">6-Nitroquipazine</a></li> <li><a href="/wiki/Alaproclate" title="Alaproclate">Alaproclate</a></li> <li><a href="/wiki/Centpropazine" title="Centpropazine">Centpropazine</a></li> <li><a href="/wiki/Cericlamine" title="Cericlamine">Cericlamine</a></li> <li><a href="/wiki/Citalopram" title="Citalopram">Citalopram</a></li> <li><a href="/wiki/Dapoxetine" title="Dapoxetine">Dapoxetine</a></li> <li><a href="/wiki/Desmethylcitalopram" title="Desmethylcitalopram">Desmethylcitalopram</a></li> <li><a href="/wiki/Didesmethylcitalopram" title="Didesmethylcitalopram">Didesmethylcitalopram</a></li> <li><a href="/wiki/Escitalopram" title="Escitalopram">Escitalopram</a></li> <li><a href="/wiki/Femoxetine" title="Femoxetine">Femoxetine</a></li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">Fluoxetine</a></li> <li><a href="/wiki/Fluvoxamine" title="Fluvoxamine">Fluvoxamine</a></li> <li><a href="/wiki/Indalpine" title="Indalpine">Indalpine</a></li> <li><a href="/wiki/Ifoxetine" title="Ifoxetine">Ifoxetine</a></li> <li><a href="/wiki/Norfluoxetine" class="mw-redirect" title="Norfluoxetine">Norfluoxetine</a></li> <li><a href="/wiki/Omiloxetine" title="Omiloxetine">Omiloxetine</a></li> <li><a href="/wiki/Panuramine" title="Panuramine">Panuramine</a></li> <li><a href="/wiki/Paroxetine" title="Paroxetine">Paroxetine</a></li> <li><a href="/wiki/PIM-35" title="PIM-35">PIM-35</a></li> <li><a href="/wiki/Pirandamine" title="Pirandamine">Pirandamine</a></li> <li><a href="/wiki/RTI-353" title="RTI-353">RTI-353</a></li> <li><a href="/wiki/Seproxetine" title="Seproxetine">Seproxetine</a></li> <li><a href="/wiki/Sertraline" title="Sertraline">Sertraline</a></li> <li><a href="/wiki/Zimelidine" title="Zimelidine">Zimelidine</a></li></ul> <ul><li><i>Selective serotonin reuptake inhibitors and serotonin receptor modulators:</i> <a href="/wiki/Etoperidone" title="Etoperidone">Etoperidone</a></li> <li><a href="/wiki/Litoxetine" title="Litoxetine">Litoxetine</a></li> <li><a href="/wiki/Lubazodone" title="Lubazodone">Lubazodone</a></li> <li><a href="/wiki/LY-393558" title="LY-393558">LY-393558</a></li> <li><a href="/wiki/Quipazine" title="Quipazine">Quipazine</a></li> <li><a href="/wiki/SB-649915" class="mw-redirect" title="SB-649915">SB-649915</a></li> <li><a href="/wiki/TGBA01AD" title="TGBA01AD">TGBA01AD</a></li> <li><a href="/wiki/Trazodone" title="Trazodone">Trazodone</a></li> <li><a href="/wiki/Vilazodone" title="Vilazodone">Vilazodone</a></li> <li><a href="/wiki/Vortioxetine" title="Vortioxetine">Vortioxetine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Serotonin–norepinephrine reuptake inhibitors:</i> <a href="/wiki/Atomoxetine" title="Atomoxetine">Atomoxetine (tomoxetine)</a></li> <li><a href="/wiki/Bicifadine" title="Bicifadine">Bicifadine</a></li> <li><a href="/w/index.php?title=CP-39332&amp;action=edit&amp;redlink=1" class="new" title="CP-39332 (page does not exist)">CP-39332</a></li> <li><a href="/wiki/Desvenlafaxine" title="Desvenlafaxine">Desvenlafaxine</a></li> <li><a href="/wiki/Duloxetine" title="Duloxetine">Duloxetine</a></li> <li><a href="/wiki/Eclanamine" title="Eclanamine">Eclanamine</a></li> <li><a href="/wiki/Levomilnacipran" title="Levomilnacipran">Levomilnacipran</a></li> <li><a href="/wiki/McN5652" title="McN5652">McN5652</a></li> <li><a href="/wiki/Milnacipran" title="Milnacipran">Milnacipran</a></li> <li><a href="/wiki/N-Methyl-PPPA" title="N-Methyl-PPPA">N-Methyl-PPPA</a></li> <li><a href="/wiki/PPPA_(drug)" title="PPPA (drug)">PPPA</a></li> <li><a href="/wiki/Tofenacin" title="Tofenacin">Tofenacin</a></li> <li><a href="/wiki/Venlafaxine" title="Venlafaxine">Venlafaxine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Serotonin–norepinephrine–dopamine reuptake inhibitors:</i> <a href="/wiki/3,3-Diphenylcyclobutanamine" title="3,3-Diphenylcyclobutanamine">3,3-Diphenylcyclobutanamine</a></li> <li><a href="/wiki/Amifitadine" class="mw-redirect" title="Amifitadine">Amifitadine</a></li> <li><a href="/wiki/Ansofaxine" title="Ansofaxine">Ansofaxine</a></li> <li><a href="/wiki/Bicifadine" title="Bicifadine">Bicifadine</a></li> <li><a href="/wiki/Brasofensine" title="Brasofensine">Brasofensine</a></li> <li><a href="/wiki/Centanafadine" title="Centanafadine">Centanafadine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Dasotraline" title="Dasotraline">Dasotraline</a></li> <li><a href="/wiki/Desmethylsertraline" title="Desmethylsertraline">Desmethylsertraline</a></li> <li><a href="/wiki/Desmethylsibutramine" title="Desmethylsibutramine">Desmethylsibutramine (BTS-54354)</a></li> <li><a href="/wiki/Diclofensine" title="Diclofensine">Diclofensine</a></li> <li><a href="/wiki/Didesmethylsibutramine" title="Didesmethylsibutramine">Didesmethylsibutramine (BTS-54505)</a></li> <li><a href="/wiki/DOV-102677" class="mw-redirect" title="DOV-102677">DOV-102677</a></li> <li><a href="/wiki/DOV-216303" class="mw-redirect" title="DOV-216303">DOV-216303</a></li> <li><a href="/wiki/EXP-561" title="EXP-561">EXP-561</a></li> <li><a href="/wiki/Fezolamine" title="Fezolamine">Fezolamine</a></li> <li><a href="/wiki/HDMP-28" title="HDMP-28">HDMP-28</a></li> <li><a href="/wiki/HP-505" title="HP-505">HP-505</a></li> <li><a href="/wiki/Indatraline" title="Indatraline">Indatraline</a></li> <li><a href="/wiki/JNJ-7925476" title="JNJ-7925476">JNJ-7925476</a></li> <li><a href="/wiki/JZ-IV-10" title="JZ-IV-10">JZ-IV-10</a></li> <li><a href="/wiki/Liafensine" title="Liafensine">Liafensine</a></li> <li><a href="/wiki/Mazindol" title="Mazindol">Mazindol</a></li> <li><a href="/wiki/Naphyrone" title="Naphyrone">Naphyrone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/NS-2359" title="NS-2359">NS-2359</a></li> <li><a href="/wiki/Perafensine" title="Perafensine">Perafensine</a></li> <li><a href="/wiki/PRC200" class="mw-redirect" title="PRC200">PRC200</a></li> <li><a href="/wiki/Pridefine" title="Pridefine">Pridefine</a></li> <li><a href="/w/index.php?title=SEP-228431&amp;action=edit&amp;redlink=1" class="new" title="SEP-228431 (page does not exist)">SEP-228431</a></li> <li><a href="/w/index.php?title=SEP-228432&amp;action=edit&amp;redlink=1" class="new" title="SEP-228432 (page does not exist)">SEP-228432</a></li> <li><a href="/wiki/Sibutramine" title="Sibutramine">Sibutramine</a></li> <li><a href="/wiki/Tedatioxetine" title="Tedatioxetine">Tedatioxetine</a></li> <li><a href="/wiki/Tesofensine" title="Tesofensine">Tesofensine</a></li> <li><a href="/wiki/Threohydrobupropion" title="Threohydrobupropion">Threohydrobupropion</a></li> <li><a href="/wiki/Tropane" title="Tropane">Tropanes</a> (e.g., <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>)</li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Tricyclic antidepressants:</i> <a href="/wiki/Amitriptyline" title="Amitriptyline">Amitriptyline</a></li> <li><a href="/wiki/Cianopramine" title="Cianopramine">Cianopramine</a></li> <li><a href="/wiki/Clomipramine" title="Clomipramine">Clomipramine</a></li> <li><a href="/wiki/Cyanodothiepin" title="Cyanodothiepin">Cyanodothiepin</a></li> <li><a href="/wiki/Desipramine" title="Desipramine">Desipramine</a></li> <li><a href="/wiki/Dosulepin" title="Dosulepin">Dosulepin (dothiepin)</a></li> <li><a href="/wiki/Doxepin" title="Doxepin">Doxepin</a></li> <li><a href="/wiki/Imipramine" title="Imipramine">Imipramine</a></li> <li><a href="/wiki/Lofepramine" title="Lofepramine">Lofepramine</a></li> <li><a href="/wiki/Nortriptyline" title="Nortriptyline">Nortriptyline</a></li> <li><a href="/wiki/Pipofezine" title="Pipofezine">Pipofezine</a></li> <li><a href="/wiki/Protriptyline" title="Protriptyline">Protriptyline</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Others:</i> <a href="/w/index.php?title=A-80426&amp;action=edit&amp;redlink=1" class="new" title="A-80426 (page does not exist)">A-80426</a></li> <li><a href="/wiki/Amoxapine" title="Amoxapine">Amoxapine</a></li> <li><a href="/wiki/Antihistamine" title="Antihistamine">Antihistamines</a> (e.g., <a href="/wiki/Brompheniramine" title="Brompheniramine">brompheniramine</a>, <a href="/wiki/Chlorphenamine" title="Chlorphenamine">chlorphenamine</a>, <a href="/wiki/Dimenhydrinate" title="Dimenhydrinate">dimenhydrinate</a>, <a href="/wiki/Diphenhydramine" title="Diphenhydramine">diphenhydramine</a>, <a href="/wiki/Mepyramine" title="Mepyramine">mepyramine (pyrilamine)</a>, <a href="/wiki/Pheniramine" title="Pheniramine">pheniramine</a>, <a href="/wiki/Tripelennamine" title="Tripelennamine">tripelennamine</a>)</li> <li><a href="/wiki/Antipsychotic" title="Antipsychotic">Antipsychotics</a> (e.g., <a href="/wiki/Loxapine" title="Loxapine">loxapine</a>, <a href="/wiki/Ziprasidone" title="Ziprasidone">ziprasidone</a>)</li> <li><a href="/wiki/Arylcyclohexylamine" title="Arylcyclohexylamine">Arylcyclohexylamines</a> (e.g., <a href="/wiki/3-MeO-PCP" title="3-MeO-PCP">3-MeO-PCP</a>, <a href="/wiki/Esketamine" title="Esketamine">esketamine</a>, <a href="/wiki/Ketamine" title="Ketamine">ketamine</a>, <a href="/wiki/Methoxetamine" title="Methoxetamine">methoxetamine</a>, <a href="/wiki/Phencyclidine" title="Phencyclidine">phencyclidine</a>)</li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/wiki/Delucemine" title="Delucemine">Delucemine</a></li> <li><a href="/wiki/Dextromethorphan" title="Dextromethorphan">Dextromethorphan</a></li> <li><a href="/wiki/Dextrorphan" title="Dextrorphan">Dextrorphan</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Hypidone" title="Hypidone">Hypidone</a></li> <li><a href="/wiki/Medifoxamine" title="Medifoxamine">Medifoxamine</a></li> <li><a href="/wiki/Mesembrine" title="Mesembrine">Mesembrine</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/MIN-117" title="MIN-117">MIN-117 (WF-516)</a></li> <li><a href="/wiki/N-Methylserotonin" title="N-Methylserotonin">N-Me-5-HT</a></li> <li><a href="/wiki/Opioid" title="Opioid">Opioids</a> (e.g., <a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">dextropropoxyphene</a>, <a href="/wiki/Methadone" title="Methadone">methadone</a>, <a href="/wiki/Pethidine" title="Pethidine">pethidine (meperidine)</a>, <a href="/wiki/Levorphanol" title="Levorphanol">levorphanol</a>, <a href="/wiki/Tapentadol" title="Tapentadol">tapentadol</a>, <a href="/wiki/Tramadol" title="Tramadol">tramadol</a>)</li> <li><a href="/wiki/Roxindole" title="Roxindole">Roxindole</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/Vesicular_monoamine_transporters" class="mw-redirect" title="Vesicular monoamine transporters"><abbr title="Vesicular monoamine transporters">VMATs</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 monoamine transporters</span></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/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Substituted_amphetamine" title="Substituted amphetamine">Amphetamines</a> (e.g., <a href="/wiki/Amphetamine" title="Amphetamine">amphetamine</a>, <a href="/wiki/Methamphetamine" title="Methamphetamine">methamphetamine</a>, <a href="/wiki/MDMA" title="MDMA">MDMA</a>)</li> <li><a href="/w/index.php?title=3-Amino-2-phenylpropene&amp;action=edit&amp;redlink=1" class="new" title="3-Amino-2-phenylpropene (page does not exist)">APP</a></li> <li><a href="/w/index.php?title=7-Azido-8-iodoketanserin&amp;action=edit&amp;redlink=1" class="new" title="7-Azido-8-iodoketanserin (page does not exist)">AZIK</a></li> <li><a href="/wiki/Bietaserpine" title="Bietaserpine">Bietaserpine</a></li> <li><a href="/wiki/Deserpidine" title="Deserpidine">Deserpidine</a></li> <li><a href="/wiki/Deutetrabenazine" title="Deutetrabenazine">Deutetrabenazine</a></li> <li><a href="/wiki/Dihydrotetrabenazine" title="Dihydrotetrabenazine">Dihydrotetrabenazine</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/GBR-12935" title="GBR-12935">GBR-12935</a></li> <li><a href="/w/index.php?title=GZ-793A&amp;action=edit&amp;redlink=1" class="new" title="GZ-793A (page does not exist)">GZ-793A</a></li> <li><a href="/wiki/Ibogaine" title="Ibogaine">Ibogaine</a></li> <li><a href="/wiki/Ketanserin" title="Ketanserin">Ketanserin</a></li> <li><a href="/wiki/Lobeline" title="Lobeline">Lobeline</a></li> <li><a href="/w/index.php?title=Methoxytetrabenazine&amp;action=edit&amp;redlink=1" class="new" title="Methoxytetrabenazine (page does not exist)">Methoxytetrabenazine</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/wiki/Rose_bengal" title="Rose bengal">Rose bengal</a></li> <li><a href="/wiki/Tetrabenazine" title="Tetrabenazine">Tetrabenazine</a></li> <li><a href="/wiki/Valbenazine" title="Valbenazine">Valbenazine</a></li> <li><a href="/wiki/Vanoxerine" title="Vanoxerine">Vanoxerine (GBR-12909)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>DAT enhancers:</i> <a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li></ul> <ul><li><i>DAT modulators:</i> <i>Agonist-like:</i> <a href="/wiki/SoRI-9804" title="SoRI-9804">SoRI-9804</a></li> <li><a href="/w/index.php?title=SoRI-20040&amp;action=edit&amp;redlink=1" class="new" title="SoRI-20040 (page does not exist)">SoRI-20040</a>; <i>Antagonist-like:</i> <a href="/wiki/SoRI-20041" title="SoRI-20041">SoRI-20041</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators">Monoamine metabolism modulators</a> • <a href="/wiki/Template:Monoamine_neurotoxins" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></small></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="AstraZeneca" 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:AstraZeneca" title="Template:AstraZeneca"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:AstraZeneca" title="Template talk:AstraZeneca"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:AstraZeneca" title="Special:EditPage/Template:AstraZeneca"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="AstraZeneca" style="font-size:114%;margin:0 4em"><a href="/wiki/AstraZeneca" title="AstraZeneca">AstraZeneca</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acalabrutinib" title="Acalabrutinib">Acalabrutinib</a></li> <li><a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Andexanet_alfa" title="Andexanet alfa">Andexanet alfa</a></li> <li><a href="/wiki/Anifrolumab" title="Anifrolumab">Anifrolumab</a></li> <li><a href="/wiki/Asfotase_alfa" title="Asfotase alfa">Asfotase alfa</a></li> <li><a href="/wiki/Atenolol" title="Atenolol">Atenolol</a></li> <li><a href="/wiki/Benralizumab" title="Benralizumab">Benralizumab</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Brompheniramine" title="Brompheniramine">Brompheniramine</a></li> <li><a href="/wiki/Budesonide" title="Budesonide">Budesonide</a></li> <li><a href="/wiki/Budesonide/formoterol" title="Budesonide/formoterol">Budesonide/formoterol</a></li> <li><a href="/wiki/Budesonide/glycopyrronium_bromide/formoterol" title="Budesonide/glycopyrronium bromide/formoterol">Budesonide/glycopyrronium bromide/formoterol</a></li> <li><a href="/wiki/Candesartan" title="Candesartan">Candesartan</a></li> <li><a href="/wiki/Dapagliflozin" title="Dapagliflozin">Dapagliflozin</a></li> <li><a href="/wiki/Disufenton_sodium" title="Disufenton sodium">Disufenton sodium</a></li> <li><a href="/wiki/Durvalumab" title="Durvalumab">Durvalumab</a></li> <li><a href="/wiki/Eculizumab" title="Eculizumab">Eculizumab</a></li> <li><a href="/wiki/Esomeprazole" title="Esomeprazole">Esomeprazole</a></li> <li><a href="/wiki/Exenatide" title="Exenatide">Exenatide</a></li> <li><a href="/wiki/Live_attenuated_influenza_vaccine" title="Live attenuated influenza vaccine">FluMist</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li> <li><a href="/wiki/Gefitinib" title="Gefitinib">Gefitinib</a></li> <li><a href="/wiki/Glycopyrronium_bromide/formoterol" title="Glycopyrronium bromide/formoterol">Glycopyrronium bromide/formoterol</a></li> <li><a href="/wiki/Goserelin" title="Goserelin">Goserelin</a></li> <li><a href="/wiki/Isosorbide_mononitrate" title="Isosorbide mononitrate">Isosorbide mononitrate</a></li> <li><a href="/wiki/Metoprolol" title="Metoprolol">Metoprolol</a></li> <li><a href="/wiki/Motavizumab" title="Motavizumab">Motavizumab</a></li> <li><a href="/wiki/Olaparib" title="Olaparib">Olaparib</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a></li> <li><a href="/wiki/Osimertinib" title="Osimertinib">Osimertinib</a></li> <li><a href="/wiki/Palivizumab" title="Palivizumab">Palivizumab</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Quetiapine" title="Quetiapine">Quetiapine</a></li> <li><a href="/wiki/Ravulizumab" title="Ravulizumab">Ravulizumab</a></li> <li><a href="/wiki/Roflumilast" title="Roflumilast">Roflumilast</a></li> <li><a href="/wiki/Rosuvastatin" title="Rosuvastatin">Rosuvastatin</a></li> <li><a href="/wiki/Roxadustat" title="Roxadustat">Roxadustat</a></li> <li><a href="/wiki/Salbutamol/budesonide" title="Salbutamol/budesonide">Salbutamol/budesonide</a></li> <li><a href="/wiki/Savolitinib" title="Savolitinib">Savolitinib</a></li> <li><a href="/wiki/Saxagliptin" title="Saxagliptin">Saxagliptin</a></li> <li><a href="/wiki/Sebelipase_alfa" title="Sebelipase alfa">Sebelipase alfa</a></li> <li><a href="/wiki/Selumetinib" title="Selumetinib">Selumetinib</a></li> <li><a href="/wiki/Sodium_zirconium_cyclosilicate" title="Sodium zirconium cyclosilicate">Sodium zirconium cyclosilicate</a></li> <li><a class="mw-selflink selflink">Tamoxifen</a></li> <li><a href="/wiki/Ticagrelor" title="Ticagrelor">Ticagrelor</a></li> <li><a href="/wiki/Tixagevimab/cilgavimab" title="Tixagevimab/cilgavimab">Tixagevimab/cilgavimab</a></li> <li><a href="/wiki/Trastuzumab_deruxtecan" title="Trastuzumab deruxtecan">Trastuzumab deruxtecan</a></li> <li><a href="/wiki/Vandetanib" title="Vandetanib">Vandetanib</a></li> <li><a href="/wiki/Oxford%E2%80%93AstraZeneca_COVID-19_vaccine" title="Oxford–AstraZeneca COVID-19 vaccine">Vaxzevria</a></li> <li><a href="/wiki/Ximelagatran" title="Ximelagatran">Ximelagatran</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Predecessors and<br />acquired companies</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/Astra_AB" title="Astra AB">Astra AB</a></li> <li><a href="/wiki/Alexion_Pharmaceuticals" title="Alexion Pharmaceuticals">Alexion Pharmaceuticals</a></li> <li><a href="/wiki/Cambridge_Antibody_Technology" title="Cambridge Antibody Technology">Cambridge Antibody Technology</a></li> <li><a href="/wiki/MedImmune" title="MedImmune">MedImmune</a></li> <li><a href="/wiki/Zeneca" title="Zeneca">Zeneca</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">People</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tom_McKillop" title="Tom McKillop">Tom McKillop</a></li> <li><a href="/wiki/Louis_Schweitzer_(CEO)" class="mw-redirect" title="Louis Schweitzer (CEO)">Louis Schweitzer</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><span class="noviewer" typeof="mw:File"><span 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