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<a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> 5.1 Pharmacodynamics </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> 5.1.1 Mechanism of action </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Clinical_effects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Clinical_effects"> <div class="vector-toc-text"> 5.1.2 Clinical effects </div> </a> <ul id="toc-Clinical_effects-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"> 5.2 Pharmacokinetics </div> </a> <ul id="toc-Pharmacokinetics-sublist" 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subsection </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Names"> <div class="vector-toc-text"> 8.1 Names </div> </a> <ul id="toc-Names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Availability" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Availability"> <div class="vector-toc-text"> 8.2 Availability </div> </a> <ul id="toc-Availability-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Controversy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Controversy"> <div class="vector-toc-text"> 8.3 Controversy </div> </a> <ul id="toc-Controversy-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research"> <div 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Available in 24 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-24" aria-hidden="true" > 24 languages </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%B1%D8%A7%D9%84%D9%88%D9%83%D8%B3%D9%8A%D9%81%D9%8A%D9%86" title="رالوكسيفين – Arabic" lang="ar" hreflang="ar" data-title="رالوكسيفين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B1%D8%A7%D9%84%D9%88%DA%A9%D8%B3%DB%8C%D9%81%D9%86" title="رالوکسیفن – South Azerbaijani" lang="azb" hreflang="azb" data-title="رالوکسیفن" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Raloxifen" title="Raloxifen – Czech" lang="cs" hreflang="cs" data-title="Raloxifen" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Raloxifen" title="Raloxifen – German" lang="de" hreflang="de" data-title="Raloxifen" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Raloxifeno" title="Raloxifeno – Spanish" lang="es" hreflang="es" data-title="Raloxifeno" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B1%D8%A7%D9%84%D9%88%DA%A9%D8%B3%DB%8C%D9%81%D9%86" title="رالوکسیفن – Persian" lang="fa" hreflang="fa" data-title="رالوکسیفن" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Raloxif%C3%A8ne" title="Raloxifène – French" lang="fr" hreflang="fr" data-title="Raloxifène" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Raloxifeno" title="Raloxifeno – Galician" lang="gl" hreflang="gl" data-title="Raloxifeno" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%9E%84%EB%A1%9D%EC%8B%9C%ED%8E%9C" title="랄록시펜 – Korean" lang="ko" hreflang="ko" data-title="랄록시펜" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Raloksifen" title="Raloksifen – Indonesian" lang="id" hreflang="id" data-title="Raloksifen" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Raloxifene" title="Raloxifene – Italian" lang="it" hreflang="it" data-title="Raloxifene" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A8%D7%9C%D7%95%D7%A7%D7%A1%D7%99%D7%A4%D7%9F" title="רלוקסיפן – Hebrew" lang="he" hreflang="he" data-title="רלוקסיפן" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Raloxifen" title="Raloxifen – Hungarian" lang="hu" hreflang="hu" data-title="Raloxifen" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B1%E0%B4%B2%E0%B5%8B%E0%B4%95%E0%B5%8D%E0%B4%B8%E0%B4%BF%E0%B4%AB%E0%B5%80%E0%B5%BB" title="റലോക്സിഫീൻ – Malayalam" lang="ml" hreflang="ml" data-title="റലോക്സിഫീൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target">മലയാളം</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%A9%E3%83%AD%E3%82%AD%E3%82%B7%E3%83%95%E3%82%A7%E3%83%B3" title="ラロキシフェン – Japanese" lang="ja" hreflang="ja" data-title="ラロキシフェン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%B0%E0%AC%BE%E0%AC%B2%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="ରାଲୋକ୍ସିଫେନ – Odia" lang="or" hreflang="or" data-title="ରାଲୋକ୍ସିଫେନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target">ଓଡ଼ିଆ</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Raloksyfen" title="Raloksyfen – Polish" lang="pl" hreflang="pl" data-title="Raloksyfen" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Raloxifeno" title="Raloxifeno – Portuguese" lang="pt" hreflang="pt" data-title="Raloxifeno" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Raloxifen" title="Raloxifen – Romanian" lang="ro" hreflang="ro" data-title="Raloxifen" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Raloksifen" title="Raloksifen – Serbian" lang="sr" hreflang="sr" data-title="Raloksifen" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Raloksifen" title="Raloksifen – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Raloksifen" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Raloksifen" title="Raloksifen – Turkish" lang="tr" hreflang="tr" data-title="Raloksifen" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Raloxifene" title="Raloxifene – Vietnamese" lang="vi" hreflang="vi" data-title="Raloxifene" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li 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compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Raloxifene</caption><tbody><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Raloxifene_Chemical_Structure_V.1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Raloxifene_Chemical_Structure_V.1.svg/250px-Raloxifene_Chemical_Structure_V.1.svg.png" decoding="async" width="250" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Raloxifene_Chemical_Structure_V.1.svg/500px-Raloxifene_Chemical_Structure_V.1.svg.png 1.5x" data-file-width="768" data-file-height="391" /></a></td></tr><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Raloxifene_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Raloxifene_molecule_ball.png/250px-Raloxifene_molecule_ball.png" decoding="async" width="250" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Raloxifene_molecule_ball.png/500px-Raloxifene_molecule_ball.png 1.5x" data-file-width="2412" data-file-height="1584" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Evista, Optruma, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Keoxifene; Pharoxifene; LY-139481; LY-156758; CCRIS-7129</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"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/raloxifene-hydrochloride.html">Monograph</a></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"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a698007.html">a698007</a></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><abbr class="country-name" title="United States">US</abbr> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Raloxifene">Raloxifene</a></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 category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: X (High risk)</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 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_G03" title="ATC code G03">G03XC01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03XC01">WHO</a>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Boxed_warning" title="Boxed warning">WARNING</a><a href="#cite_note-FDA-AllBoxedWarnings-1">[1]</a>Rx-only</li> <li><abbr class="country-name" title="European Union">EU</abbr>: Rx-only<a href="#cite_note-2">[2]</a></li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">2%<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a></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">>95%<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a></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/Intestine" class="mw-redirect" title="Intestine">intestines</a> (<a href="/wiki/Glucuronidation" title="Glucuronidation">glucuro- nidation</a>);<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a><a href="#cite_note-Jeong-5">[5]</a> <a href="/wiki/Cytochrome_P450_oxidase" class="mw-redirect" title="Cytochrome P450 oxidase">CYP450 system</a> not involved<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a></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 half-life</a></th><td class="infobox-data">Single-dose: 28 hours<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a> Multi-dose: 33 hours<a href="#cite_note-MorelloWurz2003-3">[3]</a></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><a href="#cite_note-pmid10428318-4">[4]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">[6-hydroxy-2-(4-hydroxyphenyl)-benzothiophen-3-yl]-[4-[2-(1-piperidyl)ethoxy]phenyl]-methanone</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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=84449-90-1">84449-90-1</a> <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" />Y</li><li>as HCl: <a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=82640-04-8">82640-04-8</a></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> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5035">5035</a></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><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2820">2820</a></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><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00481">DB00481</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4859.html">4859</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/YX9162EO3I">YX9162EO3I</a></li><li>as HCl: <a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/4F86W47BR6">4F86W47BR6</a></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><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D08465">D08465</a></li><li>as HCl: <a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D02217">D02217</a></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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8772">CHEBI:8772</a> <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" />Y</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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL81">ChEMBL81</a> <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" />Y</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>RAL (<a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=RAL">PDBe</a>, <a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/RAL">RCSB PDB</a>)</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> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3023550">DTXSID3023550</a> <a href="https://www.wikidata.org/wiki/Q425223#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></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">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.212.655">100.212.655</a> <a href="https://www.wikidata.org/wiki/Q425223#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></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C28H27NO4S</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">473.59 g·mol−1</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><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28c1c3ccc%28O%29cc3sc1c2ccc%28O%29cc2%29c5ccc%28OCCN4CCCCC4%29cc5">Interactive image</a></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O=C(c1c3ccc(O)cc3sc1c2ccc(O)cc2)c5ccc(OCCN4CCCCC4)cc5</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/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2 <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" />Y</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:GZUITABIAKMVPG-UHFFFAOYSA-N <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" />Y</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>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464379874&page2=Raloxifene">(verify)</a></td></tr></tbody></table> Raloxifene, sold under the brand name Evista among others, is a medication used to prevent and treat <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a> in <a href="/wiki/Menopause" title="Menopause">postmenopausal</a> women and those on <a href="/wiki/Glucocorticoids" class="mw-redirect" title="Glucocorticoids">glucocorticoids</a>.<a href="#cite_note-AHFS2019-6">[6]</a> For osteoporosis it is less preferred than <a href="/wiki/Bisphosphonates" class="mw-redirect" title="Bisphosphonates">bisphosphonates</a>.<a href="#cite_note-AHFS2019-6">[6]</a> It is also used to reduce the risk of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in those at high risk.<a href="#cite_note-AHFS2019-6">[6]</a> It is taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>.<a href="#cite_note-AHFS2019-6">[6]</a> Common <a href="/wiki/Side_effect" title="Side effect">side effects</a> include <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>, <a href="/wiki/Leg_cramp" class="mw-redirect" title="Leg cramp">leg cramps</a>, <a href="/wiki/Swelling_(medical)" class="mw-redirect" title="Swelling (medical)">swelling</a>, and <a href="/wiki/Joint_pain" class="mw-redirect" title="Joint pain">joint pain</a>.<a href="#cite_note-AHFS2019-6">[6]</a> Severe side effects may include <a href="/wiki/Blood_clots" class="mw-redirect" title="Blood clots">blood clots</a> and <a href="/wiki/Stroke" title="Stroke">stroke</a>.<a href="#cite_note-AHFS2019-6">[6]</a> Use during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> may harm the baby.<a href="#cite_note-AHFS2019-6">[6]</a> The medication may worsen <a href="/wiki/Menstrual_symptoms" class="mw-redirect" title="Menstrual symptoms">menstrual symptoms</a>.<a href="#cite_note-7">[7]</a> Raloxifene is a <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a> (SERM) and therefore a mixed <a href="/wiki/Agonist" title="Agonist">agonist</a>–<a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a> (ER).<a href="#cite_note-AHFS2019-6">[6]</a> It has <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> effects in <a href="/wiki/Bone" title="Bone">bone</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogenic</a> effects in the <a href="/wiki/Breast" title="Breast">breasts</a> and <a href="/wiki/Uterus" title="Uterus">uterus</a>.<a href="#cite_note-AHFS2019-6">[6]</a> Raloxifene was approved for medical use in the United States in 1997.<a href="#cite_note-AHFS2019-6">[6]</a> It is available as a <a href="/wiki/Generic_drug" title="Generic drug">generic medication</a>.<a href="#cite_note-AHFS2019-6">[6]</a><a href="#cite_note-BNF76-8">[8]</a> In 2020, it was the 292nd most commonly prescribed medication in the United States, with more than 1 million prescriptions.<a href="#cite_note-9">[9]</a><a href="#cite_note-10">[10]</a> <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>[<a href="/w/index.php?title=Raloxifene&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> Raloxifene is used for the treatment and prevention of <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a> in <a href="/wiki/Menopause" title="Menopause">postmenopausal</a> women.<a href="#cite_note-:0-11">[11]</a> It is used at a dosage of 60 mg/day for both the prevention and treatment of osteoporosis.<a href="#cite_note-Mosby2013-12">[12]</a> In the case of either osteoporosis prevention or treatment, supplemental <a href="/wiki/Calcium" title="Calcium">calcium</a> and <a href="/wiki/Vitamin_D" title="Vitamin D">vitamin D</a> should be added to the diet if daily intake is inadequate.<a href="#cite_note-13">[13]</a> Raloxifene is used to reduce the risk of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in postmenopausal women. It is used at a dosage of 60 mg/day for this indication.<a href="#cite_note-Mosby2013-12">[12]</a> In the Multiple Outcomes of Raloxifene (MORE) <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trial</a>, raloxifene decreased the risk of all types of breast cancer by 62%, of invasive breast cancer by 72%, and of invasive <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a>-positive breast cancer by 84%.<a href="#cite_note-pmid15755972-14">[14]</a> Conversely, it does not reduce the risk of estrogen receptor-negative breast cancer.<a href="#cite_note-pmid15755972-14">[14]</a> There were no obvious differences in effectiveness of raloxifene in the MORE trial for prevention of breast cancer at a dosage of 60 mg/m2/day relative to 120 mg/m2/day.<a href="#cite_note-pmid15755972-14">[14]</a> In the <a href="/wiki/Study_of_Tamoxifen_and_Raloxifene" title="Study of Tamoxifen and Raloxifene">Study of Tamoxifen and Raloxifene</a> (STAR) trial, 60 mg/day raloxifene was 78% as effective as 20 mg/day <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a> in preventing non-invasive breast cancer.<a href="#cite_note-BlandCopeland2017-15">[15]</a> Women with undetectable levels of estradiol (<2.7 pg/mL) have a naturally low risk of breast cancer and, in contrast to women with detectable levels of estradiol, do not experience significant benefit from raloxifene in terms of reduction of breast cancer risk.<a href="#cite_note-pmid15755972-14">[14]</a> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Raloxifene&action=edit&section=2" title="Edit section: Contraindications">edit</a>]</div> Raloxifene is <a href="/wiki/Contraindication" title="Contraindication">contraindicated</a> in <a href="/wiki/Lactation" title="Lactation">lactating</a> women or women who are or who may become <a href="/wiki/Pregnant" class="mw-redirect" title="Pregnant">pregnant</a>.<a href="#cite_note-Label-16">[16]</a> It also may be of concern to women with active or past history of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolic events</a>, including <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/Retinal_vein_thrombosis" class="mw-redirect" title="Retinal vein thrombosis">retinal vein thrombosis</a>.<a href="#cite_note-pmid23942473-17">[17]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Raloxifene&action=edit&section=3" title="Edit section: Side effects">edit</a>]</div> Common side effects of raloxifene include <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a> (25–28% vs. 18–21% for <a href="/wiki/Placebo" title="Placebo">placebo</a>),<a href="#cite_note-pmid15755972-14">[14]</a> <a href="/wiki/Vaginal_dryness" class="mw-redirect" title="Vaginal dryness">vaginal dryness</a>, and <a href="/wiki/Leg_cramp" class="mw-redirect" title="Leg cramp">leg cramps</a> (generally mild; 5.5% vs. 1.9% for placebo).<a href="#cite_note-Label-16">[16]</a><a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-Goldstein2000-18">[18]</a> Raloxifene does not cause <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Endometrial_hyperplasia" title="Endometrial hyperplasia">endometrial hyperplasia</a>, <a href="/wiki/Menstrual_bleeding" class="mw-redirect" title="Menstrual bleeding">menstrual bleeding</a>, or <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a>.<a href="#cite_note-pmid11281162-19">[19]</a> It does not appear to affect <a href="/wiki/Cognition" title="Cognition">cognition</a> or <a href="/wiki/Memory" title="Memory">memory</a>.<a href="#cite_note-pmid23942473-17">[17]</a><a href="#cite_note-pmid15755972-14">[14]</a> Raloxifene is a <a href="/wiki/Teratology" title="Teratology">teratogen</a>; i.e., it can cause developmental abnormalities such as <a href="/wiki/Birth_defect" title="Birth defect">birth defects</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Raloxifene may infrequently cause serious <a href="/wiki/Thrombus" title="Thrombus">blood clots</a> to form in the <a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">legs</a>, <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">lungs</a>, or <a href="/wiki/Retinal_vein_thrombosis" class="mw-redirect" title="Retinal vein thrombosis">eyes</a>.<a href="#cite_note-MorelloWurz2003-3">[3]</a> Other reactions experienced include leg swelling/pain, trouble breathing, chest pain, and vision changes. Black box warnings were added to the label of raloxifene in 2007 warning of increased risk of death due to stroke for postmenopausal women with documented coronary heart disease or at increased risk for major coronary events, as well as increased risk for <a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">deep vein thrombosis</a> and <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a>.<a href="#cite_note-Label-16">[16]</a> The risk of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> with raloxifene is increased by several-fold in postmenopausal women (<a href="/wiki/Relative_risk" title="Relative risk"><abbr title="relative risk">RR</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 relative risk = 3.1).<a href="#cite_note-Park2002-20">[20]</a><a href="#cite_note-pmid15755972-14">[14]</a> Raloxifene has a lower risk of thromboembolism than tamoxifen.<a href="#cite_note-BlandCopeland2017-15">[15]</a> In the MORE trial, raloxifene caused a 40% decrease in risk of cardiovascular events in women who were at increased risk for <a href="/wiki/Coronary_artery_disease" title="Coronary artery disease">coronary artery disease</a>, although there was no decrease in cardiovascular events for the group as a whole.<a href="#cite_note-pmid15755972-14">[14]</a> A report in September 2009, from Health and Human Services' Agency for Healthcare Research and Quality suggests that tamoxifen and raloxifene used to treat breast cancer, significantly reduce invasive breast cancer in midlife and older women, but also increase the risk of adverse side effects.<a href="#cite_note-21">[21]</a> A human case report in July 2016, suggests that raloxifene may in fact, at some point, also stimulate breast cancer growth leading to a reduction of advanced breast cancer disease upon the withdrawal of the drug.<a href="#cite_note-Lemmo2016-22">[22]</a> Unlike other SERMs, such as <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>, raloxifene has no risk of <a href="/wiki/Uterine_hyperplasia" title="Uterine hyperplasia">uterine hyperplasia</a> or <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> (<a href="/wiki/Relative_risk" title="Relative risk"><abbr title="relative risk">RR</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 relative risk = 0.8).<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-Park2002-20">[20]</a><a href="#cite_note-BlandCopeland2017-15">[15]</a> Raloxifene does not increase the incidence of <a href="/wiki/Breast_pain" title="Breast pain">breast pain</a> or <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">tenderness</a> in postmenopausal women.<a href="#cite_note-Goldstein2000-18">[18]</a><a href="#cite_note-Haskell2003-23">[23]</a> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Raloxifene&action=edit&section=4" title="Edit section: Overdose">edit</a>]</div> Raloxifene has been studied in <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a> across a dosage range of 30 to 600 mg/day, and was well-tolerated at all dosages.<a href="#cite_note-Goldstein2000-18">[18]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Raloxifene&action=edit&section=5" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Raloxifene&action=edit&section=6" title="Edit section: Pharmacodynamics">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Mechanism_of_action">Mechanism of action</h4>[<a href="/w/index.php?title=Raloxifene&action=edit&section=7" title="Edit section: Mechanism of action">edit</a>]</div> Raloxifene is a <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a> (SERM) and hence is a mixed <a href="/wiki/Agonist" title="Agonist">agonist</a> and <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a> (ER) in different <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>.<a href="#cite_note-AHFS2019-6">[6]</a> It has <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> activity in some tissues, such as <a href="/wiki/Bone" title="Bone">bone</a> and the <a href="/wiki/Liver" title="Liver">liver</a>, and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogenic</a> activity in other tissues, such as the <a href="/wiki/Breast" title="Breast">breasts</a> and <a href="/wiki/Uterus" title="Uterus">uterus</a>.<a href="#cite_note-AHFS2019-6">[6]</a> Its <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> (Kd) for the <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> is approximately 50 pM, which is similar to that of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<a href="#cite_note-Goldstein2000-18">[18]</a> Relative to estradiol, raloxifene has been reported to possess about 8 to 34% of the <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for the ERα and 0.5 to 76% of the affinity for the <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a>.<a href="#cite_note-WeathermanClegg2001-24">[24]</a><a href="#cite_note-pmid16554039-25">[25]</a> Raloxifene acts as a <a href="/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> of the ERα and as a <a href="/wiki/Silent_antagonist" class="mw-redirect" title="Silent antagonist">pure antagonist</a> of the ERβ.<a href="#cite_note-GreeneShiau2004-26">[26]</a><a href="#cite_note-BarkhemCarlsson1998-27">[27]</a> In contrast to the classical ERs, raloxifene is an agonist 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) (<a href="/wiki/Half-maximal_effective_concentration" class="mw-redirect" title="Half-maximal effective concentration"><abbr title="half-maximal effective concentration">EC50</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 half-maximal effective concentration = 10–100 nM), a <a href="/wiki/Membrane_estrogen_receptor" title="Membrane estrogen receptor">membrane estrogen receptor</a>.<a href="#cite_note-pmid26023144-28">[28]</a><a href="#cite_note-pmid24379833-29">[29]</a> <div class="mw-heading mw-heading4"><h4 id="Clinical_effects">Clinical effects</h4>[<a href="/w/index.php?title=Raloxifene&action=edit&section=8" title="Edit section: Clinical effects">edit</a>]</div> Raloxifene has antiestrogenic effects in the <a href="/wiki/Mammary_gland" title="Mammary gland">mammary glands</a> in <a href="/wiki/Preclinical_research" class="mw-redirect" title="Preclinical research">preclinical studies</a>.<a href="#cite_note-Goldstein2000-18">[18]</a> In accordance, raloxifene reduces <a href="/wiki/Mammographic_density" class="mw-redirect" title="Mammographic density">breast density</a> in <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women, a known risk factor for <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>.<a href="#cite_note-pmid20832226-30">[30]</a> It does not stimulate the <a href="/wiki/Uterus" title="Uterus">uterus</a> in postmenopausal women, and results in no increase in risk of <a href="/wiki/Endometrium" title="Endometrium">endometrial</a> thickening, <a href="/wiki/Vaginal_bleeding" title="Vaginal bleeding">vaginal bleeding</a>, <a href="/wiki/Endometrial_hyperplasia" title="Endometrial hyperplasia">endometrial hyperplasia</a>, or <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a>.<a href="#cite_note-DraperChin2003-31">[31]</a><a href="#cite_note-Goldstein2000-18">[18]</a><a href="#cite_note-Haskell2003-23">[23]</a> At the same time, raloxifene has minimal antiestrogenic effect in the uterus in <a href="/wiki/Premenopausal" class="mw-redirect" title="Premenopausal">premenopausal</a> women.<a href="#cite_note-DraperChin2003-31">[31]</a> This may possibly be due to inadequate tissue exposure of the uterus to raloxifene in these estrogen-rich individuals.<a href="#cite_note-DraperChin2003-31">[31]</a> In premenopausal women, raloxifene increases levels of <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> (FSH) and <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>.<a href="#cite_note-pmid15755972-14">[14]</a> Conversely, in postmenopausal women, raloxifene has been found to reduce levels of the <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropins</a>, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH) and FSH, while not affecting levels of estradiol.<a href="#cite_note-pmid15755972-14">[14]</a><a href="#cite_note-DraperChin2003-31">[31]</a> Raloxifene also decreases <a href="/wiki/Prolactin" title="Prolactin">prolactin</a> levels in postmenopausal women.<a href="#cite_note-DraperChin2003-31">[31]</a> In men, raloxifene has been found to disinhibit the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">hypothalamic–pituitary–gonadal axis</a> (HPG axis) and thereby increase total <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> levels.<a href="#cite_note-pmid25523084-32">[32]</a><a href="#cite_note-pmid27704479-33">[33]</a><a href="#cite_note-pmid22319035-34">[34]</a><a href="#cite_note-pmid15312253-35">[35]</a> Due to the simultaneous increase in <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG) levels however, free testosterone levels often remain unchanged in men during therapy with raloxifene.<a href="#cite_note-pmid25523084-32">[32]</a> Raloxifene has <a href="/wiki/Estrogen" title="Estrogen">estrogenic</a> effects on <a href="/wiki/Liver_protein_synthesis" class="mw-redirect" title="Liver protein synthesis">liver protein synthesis</a>.<a href="#cite_note-pmid15755972-14">[14]</a> It increases SHBG levels in both <a href="/wiki/Premenopausal" class="mw-redirect" title="Premenopausal">pre-</a> and <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women as well as in men.<a href="#cite_note-pmid15755972-14">[14]</a><a href="#cite_note-pmid25523084-32">[32]</a> The medication decreases levels of <a href="/wiki/Total_cholesterol" class="mw-redirect" title="Total cholesterol">total</a> and <a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">low-density lipoprotein</a> (LDL) <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a>, <a href="/wiki/C-reactive_protein" title="C-reactive protein">C-reactive protein</a>, <a href="/wiki/Apolipoprotein_B" title="Apolipoprotein B">apolipoprotein B</a>, and <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a>.<a href="#cite_note-pmid15755972-14">[14]</a><a href="#cite_note-DraperChin2003-31">[31]</a> Conversely, it has little effect on levels of <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a> and <a href="/wiki/High-density_lipoprotein" title="High-density lipoprotein">high-density lipoprotein</a> (HDL).<a href="#cite_note-pmid15755972-14">[14]</a> Raloxifene has been shown to inhibit the <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidation</a> of LDL cholesterol <a href="/wiki/In_vitro" title="In vitro">in vitro</a>.<a href="#cite_note-Goldstein2000-18">[18]</a> The medication 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 in pre- and postmenopausal women as well as in men.<a href="#cite_note-pmid27704479-33">[33]</a> It has also been found to increase <a href="/wiki/Insulin-like_growth_factor_binding_protein_3" class="mw-redirect" title="Insulin-like growth factor binding protein 3">insulin-like growth factor binding protein 3</a> (IGFBP-3) levels in pre- and postmenopausal women.<a href="#cite_note-pmid15755972-14">[14]</a> Due to activation of <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> in the liver, raloxifene has <a href="/wiki/Procoagulatory" class="mw-redirect" title="Procoagulatory">procoagulatory</a> effects, such as decreasing levels of <a href="/wiki/Fibrinogen" title="Fibrinogen">fibrinogen</a> and influencing levels of other <a href="/wiki/Coagulation_factor" class="mw-redirect" title="Coagulation factor">coagulation factors</a>.<a href="#cite_note-pmid15755972-14">[14]</a><a href="#cite_note-DraperChin2003-31">[31]</a><a href="#cite_note-Goldstein2000-18">[18]</a> For these reasons, raloxifene increases the risk of <a href="/wiki/Thrombosis" title="Thrombosis">thrombosis</a>.<a href="#cite_note-pmid15755972-14">[14]</a><a href="#cite_note-DraperChin2003-31">[31]</a> Raloxifene increases <a href="/wiki/Bone_mineral_density" class="mw-redirect" title="Bone mineral density">bone mineral density</a> in postmenopausal women but decreases it in premenopausal women.<a href="#cite_note-pmid15755972-14">[14]</a> In the MORE trial, the risk of <a href="/wiki/Vertebral_fracture" class="mw-redirect" title="Vertebral fracture">vertebral fractures</a> was decreased by 30%, and bone mineral density was increased in the <a href="/wiki/Vertebral_column" class="mw-redirect" title="Vertebral column">spine</a> (by 2.1% at 60 mg, 2.4% at 120 mg) and <a href="/wiki/Femoral_neck" title="Femoral neck">femoral neck</a> (2.6% at 60 mg, 2.7% at 120 mg).<a href="#cite_note-Park2002-20">[20]</a> It has been found to possess estrogenic effects in <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a> in postmenopausal women, promoting a shift from an <a href="/wiki/Android_fat_distribution" title="Android fat distribution">android fat distribution</a> to a <a href="/wiki/Gynoid_fat_distribution" title="Gynoid fat distribution">gynoid fat distribution</a>.<a href="#cite_note-XuLovre2016-36">[36]</a><a href="#cite_note-FrancucciPantaleo2014-37">[37]</a> The medication has been found to increase levels of <a href="/wiki/Leptin" title="Leptin">leptin</a>, an <a href="/wiki/Adipokine" title="Adipokine">adipokine</a>.<a href="#cite_note-pmid15755972-14">[14]</a> <table class="wikitable mw-collapsible mw-collapsed" style="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 .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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</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</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>+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+ </td></tr> <tr> <td>"Ideal SERM"</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />± </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" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</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" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />± </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" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td>?</td> <td>?</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</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" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />± </td></tr> <tr> <td>Raloxifene</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />±</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />± </td></tr> <tr> <td><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />± </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" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />–</td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />± </td></tr> <tr class="sortbottom"> <td colspan="15" style="width: 1px; background-color:#eaecf0; text-align: center;">Effect: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />+ = <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" />± = Mixed or neutral. <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239334494" />– = <a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogenic</a> / <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonistic</a>. Note: SERMs generally increase gonadotropin levels in hypogonadal and eugonadal men as well as premenopausal women (antiestrogenic) but decrease gonadotropin levels in postmenopausal women (estrogenic). Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Raloxifene&action=edit&section=9" title="Edit section: Pharmacokinetics">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Absorption">Absorption</h4>[<a href="/w/index.php?title=Raloxifene&action=edit&section=10" title="Edit section: Absorption">edit</a>]</div> The <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> of raloxifene is approximately 60%.<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a> However, due to extensive <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a>, the <a href="/wiki/Absolute_bioavailability" class="mw-redirect" title="Absolute bioavailability">absolute bioavailability</a> of raloxifene is only 2.0%.<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a> Raloxifene is rapidly <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> upon <a href="/wiki/Oral_administration" title="Oral administration">oral administration</a>.<a href="#cite_note-MorelloWurz2003-3">[3]</a> <a href="/wiki/Peak_plasma_levels" class="mw-redirect" title="Peak plasma levels">Peak plasma levels</a> of raloxifene occur 0.5 to 6 hours after an oral dose.<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a> In healthy postmenopausal women treated with 60 mg/day raloxifene, peak circulating raloxifene levels normalized by dose and body weight were (i.e., divided by (mg/kg)), 0.50 ng/mL (500 pg/mL) after a single dose and 1.36 ng/mL (1,360 pg/mL after multiple doses).<a href="#cite_note-Label-16">[16]</a> <div class="mw-heading mw-heading4"><h4 id="Distribution">Distribution</h4>[<a href="/w/index.php?title=Raloxifene&action=edit&section=11" title="Edit section: Distribution">edit</a>]</div> Raloxifene is widely <a href="/wiki/Distribution_(pharmacokinetics)" class="mw-redirect" title="Distribution (pharmacokinetics)">distributed</a> throughout the body.<a href="#cite_note-MorelloWurz2003-3">[3]</a> There is extensive distribution of raloxifene into the <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Blood_serum" class="mw-redirect" title="Blood serum">serum</a>, <a href="/wiki/Lung" title="Lung">lungs</a>, and <a href="/wiki/Kidney" title="Kidney">kidneys</a>.<a href="#cite_note-MorelloWurz2003-3">[3]</a> The <a href="/wiki/Volume_of_distribution" title="Volume of distribution">volume of distribution</a> of raloxifene with a single 30 to 150 mg oral dose is approximately 2348 L/kg, which corresponds to ~170,000 L for a 72 kg person.<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid11006795-38">[38]</a> Both raloxifene and its glucuronide <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> show high <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> (>95%), including to both <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> and <a href="/wiki/Orosomucoid" title="Orosomucoid">α1 acid glycoprotein</a>, but not to <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a>.<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a> More specifically, raloxifene is 98.2 ± 0.4% bound to plasma proteins.<a href="#cite_note-pmid11496940-39">[39]</a> <div class="mw-heading mw-heading4"><h4 id="Metabolism">Metabolism</h4>[<a href="/w/index.php?title=Raloxifene&action=edit&section=12" title="Edit section: Metabolism">edit</a>]</div> Raloxifene is <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> in the <a href="/wiki/Liver" title="Liver">liver</a> and undergoes <a href="/wiki/Enterohepatic_recycling" class="mw-redirect" title="Enterohepatic recycling">enterohepatic recycling</a>.<a href="#cite_note-pmid10428318-4">[4]</a> It is metabolized exclusively by <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a> and is not metabolized by the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> system.<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a> Less than 1% of radiolabeled material in plasma comprises unconjugated raloxifene.<a href="#cite_note-pmid10428318-4">[4]</a> The metabolites of raloxifene include several <a href="/wiki/Glucuronide" title="Glucuronide">glucuronides</a>.<a href="#cite_note-MorelloWurz2003-3">[3]</a> The <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of raloxifene after a single dose is 27.7 hours (1.2 days), whereas its half-life at steady state at a dosage of 60 mg/day is 15.8 to 86.6 hours (0.7–3.6 days), with an average of 32.5 hours (1.4 days).<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a><a href="#cite_note-Label-16">[16]</a> The extended half-life of raloxifene is attributed to enterohepatic recirculation and its high plasma protein binding.<a href="#cite_note-MorelloWurz2003-3">[3]</a> Raloxifene and its <a href="/wiki/Glucuronide" title="Glucuronide">glucuronide</a> <a href="/wiki/Conjugate_(biochemistry)" class="mw-redirect" title="Conjugate (biochemistry)">conjugates</a> are interconverted by reversible metabolism and enterohepatic recycling, which prolongs the elimination half-life of raloxifene with oral administration.<a href="#cite_note-pmid10428318-4">[4]</a> The medication is <a href="/wiki/Deconjugation" class="mw-redirect" title="Deconjugation">deconjugated</a> into its active form in a variety of tissues, including liver, lungs, <a href="/wiki/Spleen" title="Spleen">spleen</a>, <a href="/wiki/Bone" title="Bone">bone</a>, <a href="/wiki/Uterus" title="Uterus">uterus</a>, and kidneys.<a href="#cite_note-MorelloWurz2003-3">[3]</a> <div class="mw-heading mw-heading4"><h4 id="Elimination">Elimination</h4>[<a href="/w/index.php?title=Raloxifene&action=edit&section=13" title="Edit section: Elimination">edit</a>]</div> Raloxifene is mainly <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>.<a href="#cite_note-MorelloWurz2003-3">[3]</a><a href="#cite_note-pmid10428318-4">[4]</a> Less than 0.2% of a dose is excreted unchanged in <a href="/wiki/Urine" title="Urine">urine</a> and less than 6% of a dose is excreted in urine as glucuronide conjugates.<a href="#cite_note-pmid10428318-4">[4]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Raloxifene&action=edit&section=14" title="Edit section: Chemistry">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_selective_estrogen_receptor_modulators" title="List of selective estrogen receptor modulators">List of selective estrogen receptor modulators</a> and <a href="/wiki/Benzothiophene" title="Benzothiophene">Benzothiophene</a></div> Raloxifene <a href="/wiki/Hydrochloride" title="Hydrochloride">hydrochloride</a> has the empirical formula C28H27NO4S•HCl, which corresponds to a molecular weight of 510.05 g/mol. Raloxifene hydrochloride is an off-white to pale-yellow solid that is slightly soluble in water.<a href="#cite_note-Label-16">[16]</a> Raloxifene is a <a href="/wiki/Benzothiophene" title="Benzothiophene">benzothiophene</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> and is structurally distinct from the <a href="/wiki/Triphenylethylene" title="Triphenylethylene">triphenylethylene</a> SERMs like <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>, <a href="/wiki/Clomifene" title="Clomifene">clomifene</a>, and <a href="/wiki/Toremifene" title="Toremifene">toremifene</a>.<a href="#cite_note-OrwollBliziotes2002-40">[40]</a> It is the only benzothiophene SERM to have been marketed.<a href="#cite_note-OrwollBliziotes2002-40">[40]</a> A benzothiophene SERM that was not marketed is <a href="/wiki/Arzoxifene" title="Arzoxifene">arzoxifene</a> (LY-353381).<a href="#cite_note-SilvermanAbrahamsen2015-41">[41]</a> <a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a> (Duavee, Viviant) and <a href="/wiki/Pipendoxifene" title="Pipendoxifene">pipendoxifene</a> (ERA-923) are structurally related to raloxifene but are technically not benzothiophenes and instead are <a href="/wiki/Indole" title="Indole">indoles</a>.<a href="#cite_note-SilvermanAbrahamsen2015-41">[41]</a> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Raloxifene&action=edit&section=15" title="Edit section: History">edit</a>]</div> Raloxifene was approved in the <a href="/wiki/United_States" title="United States">United States</a> for the prevention of postmenopausal osteoporosis in 1997, the treatment of postmenopausal osteoporosis in 1999, and to prevent or reduce the risk of breast cancer in certain postmenopausal women in 2007.<a href="#cite_note-MedicinePolicy2011-42">[42]</a><a href="#cite_note-AmCnclonScience2011-43">[43]</a><a href="#cite_note-Bonnick2007-44">[44]</a><a href="#cite_note-LiJohnson2013-45">[45]</a> It received <a href="/wiki/Orphan_drug" title="Orphan drug">orphan designation</a> in 2005.<a href="#cite_note-MedicinePolicy2011-42">[42]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Raloxifene&action=edit&section=16" title="Edit section: Society and culture">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Rolaxifene.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Rolaxifene.jpg/250px-Rolaxifene.jpg" decoding="async" width="200" height="242" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Rolaxifene.jpg/330px-Rolaxifene.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Rolaxifene.jpg/500px-Rolaxifene.jpg 2x" data-file-width="1461" data-file-height="1770" /></a><figcaption>A bottle of raloxifene.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Names">Names</h3>[<a href="/w/index.php?title=Raloxifene&action=edit&section=17" title="Edit section: Names">edit</a>]</div> Raloxifene is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name and <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name, while raloxifène is its <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</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 Dénomination Commune Française and raloxifene hydrochloride is its <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name, <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BANM</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name, and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name.<a href="#cite_note-Elks2014-46">[46]</a><a href="#cite_note-IndexNominum2000-47">[47]</a><a href="#cite_note-MortonHall1999-48">[48]</a><a href="#cite_note-Drugs.com-49">[49]</a> It has also been known by the name keoxifene.<a href="#cite_note-Elks2014-46">[46]</a><a href="#cite_note-IndexNominum2000-47">[47]</a><a href="#cite_note-Drugs.com-49">[49]</a> Raloxifene is sold mainly under the brand name Evista and to a lesser extent the brand name Optruma.<a href="#cite_note-Drugs.com-49">[49]</a><a href="#cite_note-IndexNominum2000-47">[47]</a> It is also sold under a variety of other brand names in various countries.<a href="#cite_note-Drugs.com-49">[49]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Raloxifene&action=edit&section=18" title="Edit section: Availability">edit</a>]</div> Raloxifene is available widely throughout the world, including in the <a href="/wiki/United_States" title="United States">United States</a>, <a href="/wiki/Canada" title="Canada">Canada</a>, the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>, <a href="/wiki/Ireland" title="Ireland">Ireland</a>, elsewhere throughout <a href="/wiki/Europe" title="Europe">Europe</a>, <a href="/wiki/Australia" title="Australia">Australia</a>, <a href="/wiki/New_Zealand" title="New Zealand">New Zealand</a>, <a href="/wiki/South_Africa" title="South Africa">South Africa</a>, <a href="/wiki/Latin_America" title="Latin America">Latin America</a>, <a href="/wiki/South_Asia" title="South Asia">Southern</a>, <a href="/wiki/Eastern_Asia" class="mw-redirect" title="Eastern Asia">Eastern</a>, and <a href="/wiki/Southeastern_Asia" class="mw-redirect" title="Southeastern Asia">Southeastern Asia</a>, and elsewhere in the world such as in <a href="/wiki/Israel" title="Israel">Israel</a> and <a href="/wiki/Egypt" title="Egypt">Egypt</a>.<a href="#cite_note-Drugs.com-49">[49]</a><a href="#cite_note-IndexNominum2000-47">[47]</a> Raloxifene is provided in the form of 60 mg <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a>.<a href="#cite_note-Mosby2013-12">[12]</a> <div class="mw-heading mw-heading3"><h3 id="Controversy">Controversy</h3>[<a href="/w/index.php?title=Raloxifene&action=edit&section=19" title="Edit section: Controversy">edit</a>]</div> An editorial in <a href="/wiki/Lancet_Oncology" class="mw-redirect" title="Lancet Oncology">Lancet Oncology</a> criticized the way that research about the medication for breast cancer prevention was released.<a href="#cite_note-50">[50]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Raloxifene&action=edit&section=20" title="Edit section: Research">edit</a>]</div> Clinical studies of raloxifene for <a href="/wiki/Metastatic_breast_cancer" title="Metastatic breast cancer">metastatic breast cancer</a> in women have been conducted but found little effectiveness at 60 mg/day in those previously treated with tamoxifen, though modest effectiveness has been observed at higher doses.<a href="#cite_note-pmid15755972-14">[14]</a><a href="#cite_note-pmid27583816-51">[51]</a> In contrast to tamoxifen, raloxifene is not approved for the treatment of breast cancer.<a href="#cite_note-HollandPollock2010-52">[52]</a> Raloxifene has been studied in men for a variety of uses, such as for treatment of <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a>, <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>, and <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>.<a href="#cite_note-pmid10856400-53">[53]</a><a href="#cite_note-pmid11697809-54">[54]</a><a href="#cite_note-pmid15080777-55">[55]</a><a href="#cite_note-pmid15080785-56">[56]</a><a href="#cite_note-pmid15292315-57">[57]</a><a href="#cite_note-pmid15312253-35">[35]</a><a href="#cite_note-pmid22319035-34">[34]</a><a href="#cite_note-pmid27771244-58">[58]</a><a href="#cite_note-pmid26069170-59">[59]</a><a href="#cite_note-pmid25980345-60">[60]</a><a href="#cite_note-FujimuraTakayama2018-61">[61]</a> It has been studied in combination with <a href="/wiki/Castration" title="Castration">castration</a> and <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>, a <a href="/wiki/Nonsteroidal_antiandrogen" title="Nonsteroidal antiandrogen">nonsteroidal antiandrogen</a>, for the treatment of prostate cancer.<a href="#cite_note-FujimuraTakayama2018-61">[61]</a><a href="#cite_note-pmid27771244-58">[58]</a> Raloxifene has been studied as an <a href="/wiki/Adjunct_therapy" class="mw-redirect" title="Adjunct therapy">adjunct</a> in the treatment of <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a> in <a href="/wiki/Menopause" title="Menopause">postmenopausal women</a>.<a href="#cite_note-pmid28849318-62">[62]</a> A 2017 <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analysis</a> concluded that it was safe and effective for this indication, although further studies with larger <a href="/wiki/Sample_size" class="mw-redirect" title="Sample size">sample sizes</a> are needed for confirmation.<a href="#cite_note-pmid28849318-62">[62]</a> It may be effective in women with less severe symptoms.<a href="#cite_note-pmid28849318-62">[62]</a> A tissue-selective estrogen-receptor complex (TSEC) of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> and raloxifene has been studied in postmenopausal women.<a href="#cite_note-pmid22549172-63">[63]</a> Raloxifene (60 mg/day) was reported to be effective in the treatment of <a href="/wiki/Pubertal_gynecomastia" class="mw-redirect" title="Pubertal gynecomastia">pubertal gynecomastia</a> in adolescent boys in a small <a href="/wiki/Retrospective_chart_review" class="mw-redirect" title="Retrospective chart review">retrospective chart review</a>.<a href="#cite_note-pmid18622190-64">[64]</a><a href="#cite_note-pmid28260521-65">[65]</a><a href="#cite_note-pmid15238910-66">[66]</a> Other SERMs are also known to be effective in the treatment of gynecomastia.<a href="#cite_note-KanakisNordkap2019-67">[67]</a> Raloxifene has been reported to augment the <a href="/wiki/Antidepressant" title="Antidepressant">antidepressant</a> effects of <a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">selective serotonin reuptake inhibitors</a> (SSRIs).<a href="#cite_note-SugiyamaBarros2010-68">[68]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Raloxifene&action=edit&section=21" title="Edit section: References">edit</a>]</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 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Expert Rev Anticancer Ther. 9 (1): 51–60. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1586%2F14737140.9.1.51">10.1586/14737140.9.1.51</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2785111">2785111</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19105706">19105706</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Rev+Anticancer+Ther&rft.atitle=The+NSABP+Study+of+Tamoxifen+and+Raloxifene+%28STAR%29+trial&rft.volume=9&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E51-%3C%2Fspan%3E60&rft.date=2009&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2785111%23id-name%3DPMC&rft_id=info%3Apmid%2F19105706&rft_id=info%3Adoi%2F10.1586%2F14737140.9.1.51&rft.aulast=Vogel&rft.aufirst=VG&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2785111&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARaloxifene" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWickerhamCostantinoVogelCronin2009" class="citation book cs1">Wickerham DL, Costantino JP, Vogel VG, Cronin WM, Cecchini RS, Ford LG, et al. (2009). "The Use of Tamoxifen and Raloxifene for the Prevention of Breast Cancer". Cancer Prevention II. Recent Results in Cancer Research. Vol. 181. pp. 113–9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-540-69297-3_12">10.1007/978-3-540-69297-3_12</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-69296-6" title="Special:BookSources/978-3-540-69296-6"><bdi>978-3-540-69296-6</bdi></a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5110043">5110043</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19213563">19213563</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=The+Use+of+Tamoxifen+and+Raloxifene+for+the+Prevention+of+Breast+Cancer&rft.btitle=Cancer+Prevention+II&rft.series=Recent+Results+in+Cancer+Research&rft.pages=%3Cspan+class%3D%22nowrap%22%3E113-%3C%2Fspan%3E9&rft.date=2009&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5110043%23id-name%3DPMC&rft_id=info%3Apmid%2F19213563&rft_id=info%3Adoi%2F10.1007%2F978-3-540-69297-3_12&rft.isbn=978-3-540-69296-6&rft.aulast=Wickerham&rft.aufirst=DL&rft.au=Costantino%2C+JP&rft.au=Vogel%2C+VG&rft.au=Cronin%2C+WM&rft.au=Cecchini%2C+RS&rft.au=Ford%2C+LG&rft.au=Wolmark%2C+N&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARaloxifene" class="Z3988"> <code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: <code class="cs1-code">|work=</code> ignored (<a href="/wiki/Help:CS1_errors#periodical_ignored" title="Help:CS1 errors">help</a>)</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFVogel2011" class="citation journal cs1">Vogel VG (2011). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3846694">"Update on raloxifene: role in reducing the risk of invasive breast cancer in postmenopausal women"</a>. Breast Cancer: Targets and Therapy. 3: 127–37. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2147%2FBCTT.S11288">10.2147/BCTT.S11288</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3846694">3846694</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24367182">24367182</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Breast+Cancer%3A+Targets+and+Therapy&rft.atitle=Update+on+raloxifene%3A+role+in+reducing+the+risk+of+invasive+breast+cancer+in+postmenopausal+women&rft.volume=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E127-%3C%2Fspan%3E37&rft.date=2011&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3846694%23id-name%3DPMC&rft_id=info%3Apmid%2F24367182&rft_id=info%3Adoi%2F10.2147%2FBCTT.S11288&rft.aulast=Vogel&rft.aufirst=VG&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3846694&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARaloxifene" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFYangYuZhang2013" class="citation journal cs1">Yang ZD, Yu J, Zhang Q (2013). "Effects of raloxifene on cognition, mental health, sleep and sexual function in menopausal women: a systematic review of randomized controlled trials". Maturitas. 75 (4): 341–8. <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.maturitas.2013.05.010">10.1016/j.maturitas.2013.05.010</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23764354">23764354</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Maturitas&rft.atitle=Effects+of+raloxifene+on+cognition%2C+mental+health%2C+sleep+and+sexual+function+in+menopausal+women%3A+a+systematic+review+of+randomized+controlled+trials&rft.volume=75&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E341-%3C%2Fspan%3E8&rft.date=2013&rft_id=info%3Adoi%2F10.1016%2Fj.maturitas.2013.05.010&rft_id=info%3Apmid%2F23764354&rft.aulast=Yang&rft.aufirst=ZD&rft.au=Yu%2C+J&rft.au=Zhang%2C+Q&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARaloxifene" class="Z3988"></li></ul> </div> <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 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role="navigation" class="navbox" aria-labelledby="Estrogens_and_antiestrogens109" 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: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_antiestrogens109" 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"><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 agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <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>†</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># <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>Nonsteroidal: <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, <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)</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"><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 antagonists (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/<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)</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>†</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>#</li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a>†</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 class="mw-selflink selflink">Raloxifene</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a>#</li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li></ul> <ul><li>Exclusively antagonistic: <a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li></ul> <ul><li>Noncompetitive inhibitors: <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>First-generation: <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Testolactone" title="Testolactone">Testolactone</a></li></ul> <ul><li>Second-generation: <a href="/wiki/Fadrozole" title="Fadrozole">Fadrozole</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li></ul> <ul><li>Third-generation: <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">D2 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>Mixed mechanism of action: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li></ul> <ul><li>Androstenedione immunogens: <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"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<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>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§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="Other_sex_hormones_and_modulators_of_the_genital_system_(G03X)248" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Other_sex_hormones_and_modulators_of_the_genital_system" title="Template:Other sex hormones and modulators of the genital system"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Other_sex_hormones_and_modulators_of_the_genital_system" title="Template talk:Other sex hormones and modulators of the genital system"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Other_sex_hormones_and_modulators_of_the_genital_system" title="Special:EditPage/Template:Other sex hormones and modulators of the genital system"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Other_sex_hormones_and_modulators_of_the_genital_system_(G03X)248" style="font-size:114%;margin:0 4em">Other sex hormones and modulators of the genital system (<a href="/wiki/ATC_code_G03#G03X" title="ATC code G03">G03X</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a> (G03XA)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li>Anti-<a href="/wiki/Equine_chorionic_gonadotropin" title="Equine chorionic gonadotropin">Pmsg</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiprogestogen" title="Antiprogestogen">Antiprogestogens</a> (G03XB)</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/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Ulipristal_acetate" title="Ulipristal acetate">Ulipristal</a></li> <li><a href="/wiki/Aglepristone" title="Aglepristone">Aglepristone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">Selective estrogen receptor modulators</a> (G03XC)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Raloxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others (G03XX)</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/Prasterone" title="Prasterone">Prasterone</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Estrogen_receptor_modulators1222" 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_modulators1222" 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</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>Steroidal: <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&action=edit&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&action=edit&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">ent-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>Nonsteroidal: <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&action=edit&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&action=edit&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">meso-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol">meso-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&action=edit&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&action=edit&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>Unknown/unsorted: <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>Xenoestrogens: <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&action=edit&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 (cis-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&action=edit&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 (<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)</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&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-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&action=edit&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&action=edit&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&action=edit&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&action=edit&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&action=edit&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&action=edit&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&action=edit&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&action=edit&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&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a class="mw-selflink selflink">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&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">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&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&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&action=edit&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&action=edit&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&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&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&action=edit&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&action=edit&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&action=edit&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&action=edit&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&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&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&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li>Coregulator-binding modulators: <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li>Noncompetitive inhibitors: <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</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'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-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="/wiki/G-1_(drug)" class="mw-redirect" title="G-1 (drug)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&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/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</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&action=edit&redlink=1" class="new" title="2,2',5'-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 class="mw-selflink selflink">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">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)&action=edit&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)&action=edit&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="Eli_Lilly_and_Company91" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Eli_Lilly_and_Company" title="Template:Eli Lilly and Company"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Eli_Lilly_and_Company" title="Template talk:Eli Lilly and Company"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Eli_Lilly_and_Company" title="Special:EditPage/Template:Eli Lilly and Company"><abbr title="Edit this 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