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.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">Not to be confused with <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Estradiol hexahydrobenzoate">Estradiol hexahydrobenzoate</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span typeof="mw:File"><a href="/wiki/File:Estradiol_hexahydrobenzoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Estradiol_hexahydrobenzoate.svg/250px-Estradiol_hexahydrobenzoate.svg.png" decoding="async" width="250" height="152" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Estradiol_hexahydrobenzoate.svg/375px-Estradiol_hexahydrobenzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Estradiol_hexahydrobenzoate.svg/500px-Estradiol_hexahydrobenzoate.svg.png 2x" data-file-width="765" data-file-height="465" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, Tardoginestryl</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">EHHB; Estradiol cyclohexanecarboxylate; ECHC; Oestradiol hexahydrobenzoate; Estradiol 17β-hexahydrobenzoate; Estradiol 17β-cyclohexanecarboxylate; Estradiol hexabenzoate</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Intramuscular_injection" title="Intramuscular injection">Intramuscular injection</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/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a>; <a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl) cyclohexanecarboxylate</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"><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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=15140-27-9">15140-27-9</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/85808">85808</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.77397.html">77397</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/DI3496530P">DI3496530P</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID80934253">DTXSID80934253</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27276403#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.035.623">100.035.623</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q27276403#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>25</sub><span title="Hydrogen">H</span><sub>34</sub><span title="Oxygen">O</span><sub>3</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002382544000000000♠"></span>382.544</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC12CCC3C%28CCc4cc%28O%29ccc34%29C1CCC2OC%28%3DO%29C5CCCCC5">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CC12CCC3C(CCc4cc(O)ccc34)C1CCC2OC(=O)C5CCCCC5</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/C25H34O3/c1-25-14-13-20-19-10-8-18(26)15-17(19)7-9-21(20)22(25)11-12-23(25)28-24(27)16-5-3-2-4-6-16/h8,10,15-16,20-23,26H,2-7,9,11-14H2,1H3</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:IVRCALGRJCHPRV-UHFFFAOYSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>Estradiol hexahydrobenzoate</b> (<b>EHHB</b>), sold under a number of brand names including <b>Benzo-Ginoestril A.P.</b>, <b>BenzoGynoestryl Retard</b>, <b>Ginestryl-15-Depot</b>, <b>Menodin</b>, and <b>Tardoginestryl</b>, is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> medication which was previously used for indications such as <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a> and <a href="/wiki/Gynecological_disorder" class="mw-redirect" title="Gynecological disorder">gynecological disorders</a>.<sup id="cite_ref-Elks2014_1-0" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-0" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Muller1998_3-0" class="reference"><a href="#cite_note-Muller1998-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MartindaleSciences1993_4-0" class="reference"><a href="#cite_note-MartindaleSciences1993-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HumansOrganization2007_5-0" class="reference"><a href="#cite_note-HumansOrganization2007-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> EHHB is given by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">injection into muscle</a> at regular intervals, for instance once every few weeks.<sup id="cite_ref-Muller1998_3-1" class="reference"><a href="#cite_note-Muller1998-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HumansOrganization2007_5-1" class="reference"><a href="#cite_note-HumansOrganization2007-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-France1957_6-0" class="reference"><a href="#cite_note-France1957-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-France1976_7-0" class="reference"><a href="#cite_note-France1976-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Side_effect" title="Side effect">Side effects</a> of EHHB include <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Breast_enlargement" title="Breast enlargement">breast enlargement</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Headache" title="Headache">headache</a>, and <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a>.<sup id="cite_ref-Ghosh2010_8-0" class="reference"><a href="#cite_note-Ghosh2010-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> EHHB is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> and hence is an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a>, the <a href="/wiki/Biological_target" title="Biological target">biological target</a> of <a href="/wiki/Estrogen" title="Estrogen">estrogens</a> like <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>.<sup id="cite_ref-pmid16112947_9-0" class="reference"><a href="#cite_note-pmid16112947-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-OettelSchillinger2012_10-0" class="reference"><a href="#cite_note-OettelSchillinger2012-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is an <a href="/wiki/Estrogen_ester" title="Estrogen ester">estrogen ester</a> and a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> in the body.<sup id="cite_ref-OettelSchillinger2012_10-1" class="reference"><a href="#cite_note-OettelSchillinger2012-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16112947_9-1" class="reference"><a href="#cite_note-pmid16112947-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Because of this, it is considered to be a <a href="/wiki/Natural_product" title="Natural product">natural</a> and <a href="/wiki/Bioidentical_hormone_replacement_therapy" title="Bioidentical hormone replacement therapy">bioidentical</a> form of estrogen.<sup id="cite_ref-OettelSchillinger2012_10-2" class="reference"><a href="#cite_note-OettelSchillinger2012-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>EHHB was first described in 1956,<sup id="cite_ref-pmid13427258_11-0" class="reference"><a href="#cite_note-pmid13427258-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid13350115_12-0" class="reference"><a href="#cite_note-pmid13350115-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> and was introduced for medical use by 1957.<sup id="cite_ref-France1957_6-1" class="reference"><a href="#cite_note-France1957-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It was used in <a href="/wiki/France" title="France">France</a>.<sup id="cite_ref-France1957_6-2" class="reference"><a href="#cite_note-France1957-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The medication should not be confused with <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a> (EB), which has been marketed under similar brand names including Benzo-Ginestryl, Benzo-Ginoestril, and Benzo-Gynoestryl.<sup id="cite_ref-Muller1998_3-2" class="reference"><a href="#cite_note-Muller1998-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-France1957_6-3" class="reference"><a href="#cite_note-France1957-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lewis2008_13-0" class="reference"><a href="#cite_note-Lewis2008-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>EHHB was marketed in <a href="/wiki/France" title="France">France</a> in a 5 mg/mL <a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</a> in <a href="/wiki/Ampoule" title="Ampoule">ampoules</a> for <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> at regular intervals, for instance once every few weeks.<sup id="cite_ref-Muller1998_3-3" class="reference"><a href="#cite_note-Muller1998-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HumansOrganization2007_5-2" class="reference"><a href="#cite_note-HumansOrganization2007-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-France1957_6-4" class="reference"><a href="#cite_note-France1957-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-France1976_7-1" class="reference"><a href="#cite_note-France1976-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Use of EHHB for <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">feminizing hormone therapy</a> in <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a> has been reported.<sup id="cite_ref-Kulick2009_14-0" class="reference"><a href="#cite_note-Kulick2009-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> A combination of 3 mg EHHB, 75 mg <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, and 100 mg <a href="/wiki/Testosterone_hexahydrobenzoate" title="Testosterone hexahydrobenzoate">testosterone hexahydrobenzoate</a> in 2 mL <a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</a> provided in <a href="/wiki/Ampoule" title="Ampoule">ampoules</a> has been marketed under the brand name Trinestril AP in Brazil.<sup id="cite_ref-Trinestril_AP-Label_15-0" class="reference"><a href="#cite_note-Trinestril_AP-Label-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Martindale2009_16-0" class="reference"><a href="#cite_note-Martindale2009-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-GoPonto_17-0" class="reference"><a href="#cite_note-GoPonto-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Its indications include <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a> and the treatment of <a href="/wiki/Functional_uterine_bleeding" class="mw-redirect" title="Functional uterine bleeding">functional uterine bleeding</a>.<sup id="cite_ref-Trinestril_AP-Label_15-1" class="reference"><a href="#cite_note-Trinestril_AP-Label-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The combination is administered typically once per month by intramuscular injection.<sup id="cite_ref-Trinestril_AP-Label_15-2" class="reference"><a href="#cite_note-Trinestril_AP-Label-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=2" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Estradiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/225px-Estradiol.svg.png" decoding="async" width="225" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/338px-Estradiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/450px-Estradiol.svg.png 2x" data-file-width="512" data-file-height="324" /></a><figcaption><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a>, the <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> of EHHB.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=3" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Pharmacodynamics_of_estradiol" title="Pharmacodynamics of estradiol">Pharmacodynamics of estradiol</a></div> <p>EHHB is an <a href="/wiki/Estradiol_ester" class="mw-redirect" title="Estradiol ester">estradiol ester</a>, or a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<sup id="cite_ref-OettelSchillinger2012_10-3" class="reference"><a href="#cite_note-OettelSchillinger2012-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16112947_9-2" class="reference"><a href="#cite_note-pmid16112947-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-OOPEC1996_18-0" class="reference"><a href="#cite_note-OOPEC1996-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> As such, it is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a>, or an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a>.<sup id="cite_ref-OettelSchillinger2012_10-4" class="reference"><a href="#cite_note-OettelSchillinger2012-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16112947_9-3" class="reference"><a href="#cite_note-pmid16112947-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> EHHB is of about 40% higher <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> than estradiol due to the presence of its C17β <a href="/wiki/Cyclohexanecarboxylate" class="mw-redirect" title="Cyclohexanecarboxylate">cyclohexanecarboxylate</a> ester.<sup id="cite_ref-Elks2014_1-1" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Because EHHB is a prodrug of estradiol, it is considered to be a <a href="/wiki/Natural_product" title="Natural product">natural</a> and <a href="/wiki/Bioidentical_hormone_replacement_therapy" title="Bioidentical hormone replacement therapy">bioidentical</a> form of estrogen.<sup id="cite_ref-OettelSchillinger2012_10-5" class="reference"><a href="#cite_note-OettelSchillinger2012-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=4" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Pharmacokinetics_of_estradiol" title="Pharmacokinetics of estradiol">Pharmacokinetics of estradiol</a></div> <p>A combination of EHHB and <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a> as a <a href="/wiki/Combined_injectable_contraceptive" class="mw-redirect" title="Combined injectable contraceptive">combined injectable contraceptive</a> reportedly has a <a href="/wiki/Duration_of_action" class="mw-redirect" title="Duration of action">duration of action</a> of about 3 weeks.<sup id="cite_ref-HawkinsElder2013_19-0" class="reference"><a href="#cite_note-HawkinsElder2013-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=5" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a> and <a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">List of estrogen esters § Estradiol esters</a></div> <p>EHHB, also known as estradiol cyclohexanecarboxylate (ECHC) as well as estradiol 17β-hexahydrobenzoate or estradiol 17β-cyclohexanecarboxylate, is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> and an <a href="/wiki/Estrogen_ester" title="Estrogen ester">estrogen ester</a>.<sup id="cite_ref-Elks2014_1-2" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-1" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Muller1998_3-4" class="reference"><a href="#cite_note-Muller1998-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MartindaleSciences1993_4-1" class="reference"><a href="#cite_note-MartindaleSciences1993-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is specifically the C17β <a href="/wiki/Cyclohexanecarboxylate" class="mw-redirect" title="Cyclohexanecarboxylate">cyclohexanecarboxylate</a> (hexahydrobenzoate) <a href="/wiki/Ester" title="Ester">ester</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<sup id="cite_ref-Elks2014_1-3" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-2" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=6" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>EHHB was first described and characterized in 1956.<sup id="cite_ref-pmid13427258_11-1" class="reference"><a href="#cite_note-pmid13427258-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid13350115_12-1" class="reference"><a href="#cite_note-pmid13350115-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> It was developed in France.<sup id="cite_ref-pmid13427258_11-2" class="reference"><a href="#cite_note-pmid13427258-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid13350115_12-2" class="reference"><a href="#cite_note-pmid13350115-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The medication was introduced for medical use in France by 1957.<sup id="cite_ref-France1957_6-5" class="reference"><a href="#cite_note-France1957-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> A publicized <a href="/wiki/Case_report" title="Case report">case report</a> of a rapidly growing <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> <a href="/wiki/Tumor" class="mw-redirect" title="Tumor">tumor</a> in a 53-year-old woman 10 days after initiation of therapy with 5 mg/month EHHB by intramuscular injection for <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a> was published in 1962.<sup id="cite_ref-pmid13958106_20-0" class="reference"><a href="#cite_note-pmid13958106-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ExcerptaMedica1964_21-0" class="reference"><a href="#cite_note-ExcerptaMedica1964-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NCI1973_22-0" class="reference"><a href="#cite_note-NCI1973-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> The woman died due to breast cancer 10 months after the diagnosis.<sup id="cite_ref-pmid13958106_20-1" class="reference"><a href="#cite_note-pmid13958106-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NCI1973_22-1" class="reference"><a href="#cite_note-NCI1973-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=7" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=8" title="Edit section: Generic names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>Estradiol hexahydrobenzoate</i> is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name</span>), while <i>oestradiol hexahydrobenzoate</i> is its <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</span>.<sup id="cite_ref-Elks2014_1-4" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-3" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Muller1998_3-5" class="reference"><a href="#cite_note-Muller1998-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MartindaleSciences1993_4-2" class="reference"><a href="#cite_note-MartindaleSciences1993-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The medication is also known as estradiol cyclohexanecarboxylate (ECHC).<sup id="cite_ref-Elks2014_1-5" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-4" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Muller1998_3-6" class="reference"><a href="#cite_note-Muller1998-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MartindaleSciences1993_4-3" class="reference"><a href="#cite_note-MartindaleSciences1993-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=9" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>EHHB has been marketed under the brand names Benzo-Ginoestril A.P., BenzoGynoestryl Retard, Ginestryl-15-Depot, Menodin, and Tardoginestryl.<sup id="cite_ref-Elks2014_1-6" class="reference"><a href="#cite_note-Elks2014-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MortonHall2012_2-5" class="reference"><a href="#cite_note-MortonHall2012-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Muller1998_3-7" class="reference"><a href="#cite_note-Muller1998-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MartindaleSciences1993_4-4" class="reference"><a href="#cite_note-MartindaleSciences1993-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HumansOrganization2007_5-3" class="reference"><a href="#cite_note-HumansOrganization2007-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=10" title="Edit section: Availability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>EHHB was previously marketed in <a href="/wiki/France" title="France">France</a>.<sup id="cite_ref-France1957_6-6" class="reference"><a href="#cite_note-France1957-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=11" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A combination of 5 mg EHHB in <a href="/wiki/Peanut_oil" title="Peanut oil">peanut oil</a> solution and 25 mg <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a> in <a href="/wiki/Aqueous_suspension" class="mw-redirect" title="Aqueous suspension">aqueous suspension</a> as a once-monthly <a href="/wiki/Combined_injectable_contraceptive" class="mw-redirect" title="Combined injectable contraceptive">combined injectable contraceptive</a> was studied, but this formulation was ultimately never marketed.<sup id="cite_ref-pmid4650657_23-0" class="reference"><a href="#cite_note-pmid4650657-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid8013216_24-0" class="reference"><a href="#cite_note-pmid8013216-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid12290848_25-0" class="reference"><a href="#cite_note-pmid12290848-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Toppozada1983_26-0" class="reference"><a href="#cite_note-Toppozada1983-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid865726_27-0" class="reference"><a href="#cite_note-pmid865726-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-HawkinsElder2013_19-1" class="reference"><a href="#cite_note-HawkinsElder2013-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Estradiol_hexahydrobenzoate&action=edit&section=12" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Elks2014-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Elks2014_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Elks2014_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Elks2014_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Elks2014_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Elks2014_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Elks2014_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Elks2014_1-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFElks2014" class="citation book cs1">Elks J (14 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA129"><i>The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</i></a>. Springer. p. 898. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Structures+and+Bibliographies&rft.pages=898&rft.pub=Springer&rft.date=2014-11-14&rft.isbn=978-1-4757-2085-3&rft.aulast=Elks&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DRA1-PA129&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-MortonHall2012-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-MortonHall2012_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MortonHall2012_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MortonHall2012_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-MortonHall2012_2-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-MortonHall2012_2-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-MortonHall2012_2-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMortonHall2012" class="citation book cs1">Morton IK, Hall JM (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA114"><i>Concise Dictionary of Pharmacological Agents: Properties and Synonyms</i></a>. Springer Science & Business Media. pp. 114, 206. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-4439-1" title="Special:BookSources/978-94-011-4439-1"><bdi>978-94-011-4439-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Concise+Dictionary+of+Pharmacological+Agents%3A+Properties+and+Synonyms&rft.pages=114%2C+206&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-011-4439-1&rft.aulast=Morton&rft.aufirst=IK&rft.au=Hall%2C+JM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtsjrCAAAQBAJ%26pg%3DPA114&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-Muller1998-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Muller1998_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Muller1998_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Muller1998_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Muller1998_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Muller1998_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Muller1998_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Muller1998_3-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Muller1998_3-7"><sup><i><b>h</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMuller1998" class="citation book cs1">Muller A (19 June 1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2HBPHmclMWIC&pg=PA150"><i>European Drug Index: European Drug Registrations, Fourth Edition</i></a>. CRC Press. pp. 150–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-7692-2114-5" title="Special:BookSources/978-3-7692-2114-5"><bdi>978-3-7692-2114-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=European+Drug+Index%3A+European+Drug+Registrations%2C+Fourth+Edition&rft.pages=150-&rft.pub=CRC+Press&rft.date=1998-06-19&rft.isbn=978-3-7692-2114-5&rft.aulast=Muller&rft.aufirst=A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2HBPHmclMWIC%26pg%3DPA150&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-MartindaleSciences1993-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-MartindaleSciences1993_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MartindaleSciences1993_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MartindaleSciences1993_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-MartindaleSciences1993_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-MartindaleSciences1993_4-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartindaleReynolds1993" class="citation book cs1">Martindale W, Reynolds JE (1993). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=EGZWAAAAYAAJ"><i>The Extra Pharmacopoeia</i></a>. Pharmaceutical Press. p. 1191. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85369-300-0" title="Special:BookSources/978-0-85369-300-0"><bdi>978-0-85369-300-0</bdi></a>. <q>Oestradiol Hexahydrobenzoate (13039-d) Oestradiol Hexahydrobenzoate (BANM). Estradiol Hexzihydrobcnzoate (rlNNM). Estra-1,3,5(10)-triene-3,17β-diol 17-cyclohexanecarboxylate. C25H34O3 = 382.5. CAS — 15140-27-9.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Extra+Pharmacopoeia&rft.pages=1191&rft.pub=Pharmaceutical+Press&rft.date=1993&rft.isbn=978-0-85369-300-0&rft.aulast=Martindale&rft.aufirst=W&rft.au=Reynolds%2C+JE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DEGZWAAAAYAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-HumansOrganization2007-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-HumansOrganization2007_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HumansOrganization2007_5-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-HumansOrganization2007_5-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-HumansOrganization2007_5-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIARC_Working_Group_on_the_Evaluation_of_Carcinogenic_Risks_to_HumansWorld_Health_OrganizationInternational_Agency_for_Research_on_Cancer2007" class="citation book cs1">IARC Working Group on the Evaluation of Carcinogenic Risks to Humans; World Health Organization; International Agency for Research on Cancer (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aGDU5xibtNgC&pg=PA388"><i>Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy</i></a>. World Health Organization. pp. 388–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-832-1291-1" title="Special:BookSources/978-92-832-1291-1"><bdi>978-92-832-1291-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Combined+Estrogen-progestogen+Contraceptives+and+Combined+Estrogen-progestogen+Menopausal+Therapy&rft.pages=388-&rft.pub=World+Health+Organization&rft.date=2007&rft.isbn=978-92-832-1291-1&rft.au=IARC+Working+Group+on+the+Evaluation+of+Carcinogenic+Risks+to+Humans&rft.au=World+Health+Organization&rft.au=International+Agency+for+Research+on+Cancer&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DaGDU5xibtNgC%26pg%3DPA388&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-France1957-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-France1957_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-France1957_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-France1957_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-France1957_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-France1957_6-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-France1957_6-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-France1957_6-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFrance1957" class="citation book cs1">France (August 1957). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JREkAQAAMAAJ"><i>Journal officiel de la République française</i></a>. <q>BENZOGYNOESTRYL 1, ampoules injectables de 1 cm* A 1 mg (2 ou 10). BENZOGYNOESTRYL 5, ampoules injectables de 1 cm3 à 5 mg (1 ou 10). BENZOGYNOESTRYL-RETARD 5 mg, ampoules injectables Ci/1 cm3).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Journal+officiel+de+la+R%C3%A9publique+fran%C3%A7aise&rft.date=1957-08&rft.au=France&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJREkAQAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-France1976-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-France1976_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-France1976_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFrance1976" class="citation book cs1">France (1976). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=yhELAQAAMAAJ"><i>Journal officiel de la République française. Édition des lois et décrets</i></a>. p. 1843. <q>Spécialité dénommée BENZO-GYNOESTRYL RETARD, soluté injectable : Laboratoires Roussel, 75323 Paris CEDEX 07. — A. M. M. n" 301063.1 (1 ampoule de 1 ml) [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Journal+officiel+de+la+R%C3%A9publique+fran%C3%A7aise.+%C3%89dition+des+lois+et+d%C3%A9crets&rft.pages=1843&rft.date=1976&rft.au=France&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DyhELAQAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-Ghosh2010-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ghosh2010_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcIverTebbenShah2010" class="citation book cs1">McIver B, Tebben PJ, Shah P (23 September 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=LS65jBzoD40C&pg=PA222">"Endocrinology"</a>. In Ghosh AK (ed.). <i>Mayo Clinic Internal Medicine Board Review</i>. OUP USA. pp. 222–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-975569-1" title="Special:BookSources/978-0-19-975569-1"><bdi>978-0-19-975569-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Endocrinology&rft.btitle=Mayo+Clinic+Internal+Medicine+Board+Review&rft.pages=222-&rft.pub=OUP+USA&rft.date=2010-09-23&rft.isbn=978-0-19-975569-1&rft.aulast=McIver&rft.aufirst=B&rft.au=Tebben%2C+PJ&rft.au=Shah%2C+P&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DLS65jBzoD40C%26pg%3DPA222&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-pmid16112947-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid16112947_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid16112947_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid16112947_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pmid16112947_9-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhl2005" class="citation journal cs1">Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". <i>Climacteric</i>. <b>8</b> (Suppl 1): 3–63. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13697130500148875">10.1080/13697130500148875</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/16112947">16112947</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:24616324">24616324</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Pharmacology+of+estrogens+and+progestogens%3A+influence+of+different+routes+of+administration&rft.volume=8&rft.issue=Suppl+1&rft.pages=3-63&rft.date=2005-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24616324%23id-name%3DS2CID&rft_id=info%3Apmid%2F16112947&rft_id=info%3Adoi%2F10.1080%2F13697130500148875&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-OettelSchillinger2012-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-OettelSchillinger2012_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-OettelSchillinger2012_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-OettelSchillinger2012_10-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-OettelSchillinger2012_10-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-OettelSchillinger2012_10-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-OettelSchillinger2012_10-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhnzBlodeZimmermann2012" class="citation book cs1">Kuhnz W, Blode H, Zimmermann H (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wBvyCAAAQBAJ&pg=PA261">"Pharmacokinetics of exogenous natural and synthetic estrogens and antiestrogens"</a>. In Oettel M, Schillinger E (eds.). <i>Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen</i>. Springer Science & Business Media. p. 261. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-60107-1" title="Special:BookSources/978-3-642-60107-1"><bdi>978-3-642-60107-1</bdi></a>. <q>Natural estrogens considered here include: [...] Esters of 17β-estradiol, such as estradiol valerate, estradiol benzoate and estradiol cypionate. Esterification aims at either better absorption after oral administration or a sustained release from the depot after intramuscular administration. During absorption, the esters are cleaved by endogenous esterases and the pharmacologically active 17β-estradiol is released; therefore, the esters are considered as natural estrogens.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Pharmacokinetics+of+exogenous+natural+and+synthetic+estrogens+and+antiestrogens&rft.btitle=Estrogens+and+Antiestrogens+II%3A+Pharmacology+and+Clinical+Application+of+Estrogens+and+Antiestrogen&rft.pages=261&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-60107-1&rft.aulast=Kuhnz&rft.aufirst=W&rft.au=Blode%2C+H&rft.au=Zimmermann%2C+H&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwBvyCAAAQBAJ%26pg%3DPA261&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-pmid13427258-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid13427258_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid13427258_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid13427258_11-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFeyel-Cabanes1956" class="citation journal cs1 cs1-prop-foreign-lang-source">Feyel-Cabanes T (1956). "[A new estrogen with retarded action, estradiol-17-hexahydrobenzoate]" [A new estrogen with retarded action, estradiol-17-hexahydrobenzoate]. <i>Comptes Rendus des Séances de la Société de Biologie et de Ses Filiales</i> (in French). <b>150</b> (11): 1881–1883. <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/13427258">13427258</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Comptes+Rendus+des+S%C3%A9ances+de+la+Soci%C3%A9t%C3%A9+de+Biologie+et+de+Ses+Filiales&rft.atitle=%5BA+new+estrogen+with+retarded+action%2C+estradiol-17-hexahydrobenzoate%5D&rft.volume=150&rft.issue=11&rft.pages=1881-1883&rft.date=1956&rft_id=info%3Apmid%2F13427258&rft.aulast=Feyel-Cabanes&rft.aufirst=T&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-pmid13350115-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid13350115_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid13350115_12-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pmid13350115_12-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGuiard1956" class="citation journal cs1 cs1-prop-foreign-lang-source">Guiard E (June 1956). "[Physiologic and clinical action of long-acting hormones; 1. testosterone hexahydrobenzoate, 2. estradiol hexahydrobenzoate]" [Physiologic and clinical action of long-acting hormones; 1. testosterone hexahydrobenzoate, 2. estradiol hexahydrobenzoate]. <i>La Presse Médicale</i> (in French). <b>64</b> (52): 1223–1224. <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/13350115">13350115</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=La+Presse+M%C3%A9dicale&rft.atitle=%5BPhysiologic+and+clinical+action+of+long-acting+hormones%3B+1.+testosterone+hexahydrobenzoate%2C+2.+estradiol+hexahydrobenzoate%5D&rft.volume=64&rft.issue=52&rft.pages=1223-1224&rft.date=1956-06&rft_id=info%3Apmid%2F13350115&rft.aulast=Guiard&rft.aufirst=E&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-Lewis2008-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-Lewis2008_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLewis2008" class="citation book cs1">Lewis RJ (13 June 2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=WZeBDwAAQBAJ&pg=PA593"><i>Hazardous Chemicals Desk Reference</i></a>. John Wiley & Sons. pp. 593–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-18024-2" title="Special:BookSources/978-0-470-18024-2"><bdi>978-0-470-18024-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hazardous+Chemicals+Desk+Reference&rft.pages=593-&rft.pub=John+Wiley+%26+Sons&rft.date=2008-06-13&rft.isbn=978-0-470-18024-2&rft.aulast=Lewis&rft.aufirst=RJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DWZeBDwAAQBAJ%26pg%3DPA593&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-Kulick2009-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-Kulick2009_14-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKulick2009" class="citation book cs1">Kulick D (12 January 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=jbZyBfio-hcC&pg=PA64">"Becoming a Travesti"</a>. <i>Travesti: Sex, Gender, and Culture among Brazilian Transgendered Prostitutes</i>. University of Chicago Press. pp. 64, 244. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-226-46101-4" title="Special:BookSources/978-0-226-46101-4"><bdi>978-0-226-46101-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Becoming+a+Travesti&rft.btitle=Travesti%3A+Sex%2C+Gender%2C+and+Culture+among+Brazilian+Transgendered+Prostitutes&rft.pages=64%2C+244&rft.pub=University+of+Chicago+Press&rft.date=2009-01-12&rft.isbn=978-0-226-46101-4&rft.aulast=Kulick&rft.aufirst=D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DjbZyBfio-hcC%26pg%3DPA64&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-Trinestril_AP-Label-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-Trinestril_AP-Label_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Trinestril_AP-Label_15-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Trinestril_AP-Label_15-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/save/http://xock.org/b/bulas/medicamentos/trinestril-a-p/">"Trinestril AP-Label"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Trinestril+AP-Label&rft_id=https%3A%2F%2Fweb.archive.org%2Fsave%2Fhttp%3A%2F%2Fxock.org%2Fb%2Fbulas%2Fmedicamentos%2Ftrinestril-a-p%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-Martindale2009-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-Martindale2009_16-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSweetman2009" class="citation book cs1">Sweetman SC, ed. (2009). "Sex hormones and their modulators". <i>Martindale: The Complete Drug Reference</i> (36th ed.). London: Pharmaceutical Press. pp. 2100, 2124–2125. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85369-840-1" title="Special:BookSources/978-0-85369-840-1"><bdi>978-0-85369-840-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Sex+hormones+and+their+modulators&rft.btitle=Martindale%3A+The+Complete+Drug+Reference&rft.place=London&rft.pages=2100%2C+2124-2125&rft.edition=36th&rft.pub=Pharmaceutical+Press&rft.date=2009&rft.isbn=978-0-85369-840-1&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-GoPonto-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-GoPonto_17-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20190623181304/http://www.drcarlos.med.br/climamed.html">"Climatério - Medicamentos"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.drcarlos.med.br/climamed.html">the original</a> on 2019-06-23<span class="reference-accessdate">. Retrieved <span class="nowrap">2019-06-11</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Climat%C3%A9rio+-+Medicamentos&rft_id=http%3A%2F%2Fwww.drcarlos.med.br%2Fclimamed.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-OOPEC1996-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-OOPEC1996_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=-00vAAAAYAAJ"><i>The Rules Governing Medicinal Products in the European Union</i></a>. Office for Official Publications of the European Communities. 1996. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-827-6427-5" title="Special:BookSources/978-92-827-6427-5"><bdi>978-92-827-6427-5</bdi></a>. <q>Oestradiol benzoate, oestradiol valerate and oestradiol hexahydrobenzoate are synthetic esters of the naturally occurring oestrogen oestradiol. After administration the esters are absorbed and subsequently hydrolysed to the active compound oestradiol. Oestradiol is the most active natural oestrogen, which can act at many different sites in both female and male animals.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Rules+Governing+Medicinal+Products+in+the+European+Union&rft.pub=Office+for+Official+Publications+of+the+European+Communities&rft.date=1996&rft.isbn=978-92-827-6427-5&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D-00vAAAAYAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-HawkinsElder2013-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-HawkinsElder2013_19-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-HawkinsElder2013_19-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHawkinsElder2013" class="citation book cs1">Hawkins DF, Elder MG (22 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=1lL0AgAAQBAJ&pg=PA110">"Other hormonal Contraceptive Procedures"</a>. <i>Human Fertility Control: Theory and Practice</i>. Elsevier Science. pp. 110–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4831-6361-1" title="Special:BookSources/978-1-4831-6361-1"><bdi>978-1-4831-6361-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Other+hormonal+Contraceptive+Procedures&rft.btitle=Human+Fertility+Control%3A+Theory+and+Practice&rft.pages=110-&rft.pub=Elsevier+Science&rft.date=2013-10-22&rft.isbn=978-1-4831-6361-1&rft.aulast=Hawkins&rft.aufirst=DF&rft.au=Elder%2C+MG&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D1lL0AgAAQBAJ%26pg%3DPA110&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-pmid13958106-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid13958106_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid13958106_20-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJuretAutissier1962" class="citation journal cs1 cs1-prop-foreign-lang-source">Juret P, Autissier P (September 1962). "[Breast cancer of subacute development discovered after injections of estradiol hexahydrobenzoate]" [Breast cancer of subacute development discovered after injections of estradiol hexahydrobenzoate]. <i>La Presse Médicale</i> (in French). <b>70</b> (30): 1813. <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/13958106">13958106</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=La+Presse+M%C3%A9dicale&rft.atitle=%5BBreast+cancer+of+subacute+development+discovered+after+injections+of+estradiol+hexahydrobenzoate%5D&rft.volume=70&rft.issue=30&rft.pages=1813&rft.date=1962-09&rft_id=info%3Apmid%2F13958106&rft.aulast=Juret&rft.aufirst=P&rft.au=Autissier%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-ExcerptaMedica1964-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-ExcerptaMedica1964_21-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=75QTAQAAMAAJ"><i>Evaluation of the Potential Carcinogenic Action of a Drug: Proceedings of the Symposium in Lausanne, January 1964</i></a>. Excerpta Medica Foundation. 1964. p. 96. <q>In 1962, Juret and Antissier described a woman aged 53 who, 10 days after an injection of 5 mg. oestradiol hexahydrobenzoate, showed a rapidly growing mammary carcinoma.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Evaluation+of+the+Potential+Carcinogenic+Action+of+a+Drug%3A+Proceedings+of+the+Symposium+in+Lausanne%2C+January+1964&rft.pages=96&rft.pub=Excerpta+Medica+Foundation&rft.date=1964&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D75QTAQAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-NCI1973-22"><span class="mw-cite-backlink">^ <a href="#cite_ref-NCI1973_22-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-NCI1973_22-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=4Ump-8w0m28C"><i>Carcinogenesis Abstracts</i></a>. National Cancer Institute. 1973. p. 900. <q>A rapidly growing lump developed in a 53yr-old woman 1 wk after she had been given estradiol hexahydrobenzoate (5 mg/month) for hot flashes. The patient died of breast cancer 10 months later.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Carcinogenesis+Abstracts&rft.pages=900&rft.pub=National+Cancer+Institute.&rft.date=1973&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4Ump-8w0m28C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-pmid4650657-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid4650657_23-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFde_SouzaCoutinho1972" class="citation journal cs1">de Souza JC, Coutinho EM (May 1972). "Control of fertility by monthyl injections of a mixture of norgestrel and a long-acting estrogen. 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"Existing once-a-month combined injectable contraceptives". <i>Contraception</i>. <b>49</b> (4): 293–301. <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%2F0010-7824%2894%2990029-9">10.1016/0010-7824(94)90029-9</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/8013216">8013216</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Existing+once-a-month+combined+injectable+contraceptives&rft.volume=49&rft.issue=4&rft.pages=293-301&rft.date=1994-04&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2894%2990029-9&rft_id=info%3Apmid%2F8013216&rft.aulast=Toppozada&rft.aufirst=MK&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-pmid12290848-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid12290848_25-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNewtonD'arcanguesHall1994" class="citation journal cs1">Newton JR, D'arcangues C, Hall PE (1994). "A review of "once-a-month" combined injectable contraceptives". <i>Journal of Obstetrics and Gynaecology</i>. <b>4</b> (Suppl 1): S1-34. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F01443619409027641">10.3109/01443619409027641</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/12290848">12290848</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Obstetrics+and+Gynaecology&rft.atitle=A+review+of+%22once-a-month%22+combined+injectable+contraceptives&rft.volume=4&rft.issue=Suppl+1&rft.pages=S1-34&rft.date=1994&rft_id=info%3Adoi%2F10.3109%2F01443619409027641&rft_id=info%3Apmid%2F12290848&rft.aulast=Newton&rft.aufirst=JR&rft.au=D%27arcangues%2C+C&rft.au=Hall%2C+PE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+hexahydrobenzoate" class="Z3988"></span></span> </li> <li id="cite_note-Toppozada1983-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-Toppozada1983_26-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFToppozada1983" class="citation book cs1">Toppozada MK (1983). 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"The clinical use of monthly injectable contraceptive preparations". <i>Obstetrical & Gynecological Survey</i>. <b>32</b> (6): 335–347. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00006254-197706000-00001">10.1097/00006254-197706000-00001</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/865726">865726</a>.</cite><span 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title="Estrogen">Estrogen (as a hormone)</a></li> <li><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen (as a medication)</a></li> <li><a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">Menopausal hormone therapy</a></li> <li><a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">Feminizing hormone therapy</a></li> <li><a href="/wiki/Estradiol-containing_birth_control_pill" title="Estradiol-containing birth control pill">Estradiol-containing birth control pill</a></li> <li><a href="/wiki/Combined_injectable_birth_control" title="Combined injectable birth control">Combined injectable birth control</a></li> <li><a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">High-dose estrogen</a></li> <li><a href="/wiki/Hydroxylation_of_estradiol" title="Hydroxylation of estradiol">Hydroxylation of estradiol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_ester" title="Estrogen ester">Esters</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a></li> <li><a href="/wiki/Estradiol_acetylsalicylate" title="Estradiol acetylsalicylate">Estradiol acetylsalicylate</a></li> <li><a href="/wiki/Estradiol_anthranilate" title="Estradiol anthranilate">Estradiol anthranilate</a></li> <li><a href="/wiki/Estradiol_benzoate_butyrate" title="Estradiol benzoate butyrate">Estradiol benzoate butyrate</a></li> <li><a href="/wiki/Estradiol_benzoate_cyclooctenyl_ether" title="Estradiol benzoate cyclooctenyl ether">Estradiol benzoate cyclooctenyl ether</a></li> <li><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></li> <li><a href="/wiki/Estradiol_butyrylacetate" title="Estradiol butyrylacetate">Estradiol butyrylacetate</a></li> <li><a href="/wiki/Estradiol_cyclooctyl_acetate" title="Estradiol cyclooctyl acetate">Estradiol cyclooctyl acetate</a></li> <li><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></li> <li><a href="/wiki/Estradiol_decanoate" title="Estradiol decanoate">Estradiol decanoate</a></li> <li><a href="/wiki/Estradiol_diacetate" title="Estradiol diacetate">Estradiol diacetate</a></li> <li><a href="/wiki/Estradiol_dibutyrate" title="Estradiol dibutyrate">Estradiol dibutyrate</a></li> <li><a href="/wiki/Estradiol_dienantate" title="Estradiol dienantate">Estradiol dienantate</a></li> <li><a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">Estradiol dipropionate</a></li> <li><a href="/wiki/Estradiol_distearate" title="Estradiol distearate">Estradiol distearate</a></li> <li><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></li> <li><a href="/wiki/Estradiol_diundecylate" title="Estradiol diundecylate">Estradiol diundecylate</a></li> <li><a href="/wiki/Estradiol_diundecylenate" title="Estradiol diundecylenate">Estradiol diundecylenate</a></li> <li><a href="/wiki/Estradiol_enantate" title="Estradiol enantate">Estradiol enantate</a></li> <li><a href="/wiki/Estradiol_furoate" title="Estradiol furoate">Estradiol furoate</a></li> <li><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></li> <li><a href="/wiki/Estradiol_hemisuccinate" title="Estradiol hemisuccinate">Estradiol hemisuccinate</a></li> <li><a class="mw-selflink selflink">Estradiol hexahydrobenzoate</a></li> <li><a href="/wiki/Estradiol_monopropionate" title="Estradiol monopropionate">Estradiol monopropionate</a></li> <li><a href="/wiki/Estradiol_mustard" title="Estradiol mustard">Estradiol mustard</a></li> <li><a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">Estradiol palmitate</a></li> <li><a href="/wiki/Estradiol_phenylpropionate" title="Estradiol phenylpropionate">Estradiol phenylpropionate</a></li> <li><a href="/wiki/Estradiol_phosphate" title="Estradiol phosphate">Estradiol phosphate</a></li> <li><a href="/wiki/Estradiol_pivalate" title="Estradiol pivalate">Estradiol pivalate</a></li> <li><a href="/wiki/Estradiol_propoxyphenylpropionate" title="Estradiol propoxyphenylpropionate">Estradiol propoxyphenylpropionate</a></li> <li><a href="/wiki/Estradiol_salicylate" title="Estradiol salicylate">Estradiol salicylate</a></li> <li><a href="/wiki/Estradiol_stearate" title="Estradiol stearate">Estradiol stearate</a></li> <li><a href="/wiki/Estradiol_sulfamate" title="Estradiol sulfamate">Estradiol sulfamate</a></li> <li><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></li> <li><a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">Estradiol undecylate</a></li> <li><a href="/wiki/Estradiol_undecylenate" title="Estradiol undecylenate">Estradiol undecylenate</a></li> <li><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate (estradiol normustine phosphate)</a></li> <li><a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related</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/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <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> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Estrogens_and_antiestrogens" 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_antiestrogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span> agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a><sup>†</sup></li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, <a href="/wiki/Estradiol_ester_mixture" class="mw-redirect" title="Estradiol ester mixture">estradiol ester mixtures</a> (<a href="/wiki/Climacteron" class="mw-redirect" title="Climacteron">Climacteron</a>))</li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a> (e.g., <a href="/wiki/Estriol_succinate" title="Estriol succinate">estriol succinate</a>, <a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">polyestriol phosphate</a>)</li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a> <ul><li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a><sup>#</sup> <ul><li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone; DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate</a></li></ul></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol (stilbestrol)</a></li> <li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters/ethers</a> <ul><li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (diethylstilbestrol dimethyl ether)</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol (diethylstilbestrol monomethyl ether)</a></li></ul></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol (promethestrol)</a> <ul><li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate (promethestrol dipropionate)</a></li></ul></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> (e.g., <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip follicle-stimulating hormone</span>, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip luteinizing hormone</span>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span> antagonists<br />(incl. <a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor modulators</span>/<a href="/wiki/Selective_estrogen_receptor_downregulators" class="mw-redirect" title="Selective estrogen receptor downregulators"><abbr title="selective estrogen receptor downregulators">SERDs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor downregulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a><sup>†</sup></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a><sup>#</sup></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a><sup>†</sup></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a><sup>#</sup></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li></ul> <ul><li><i>Exclusively antagonistic:</i> <a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">Aromatase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>First-generation:</i> <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Testolactone" title="Testolactone">Testolactone</a></li></ul> <ul><li><i>Second-generation:</i> <a href="/wiki/Fadrozole" title="Fadrozole">Fadrozole</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li></ul> <ul><li><i>Third-generation:</i> <a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Letrozole" title="Letrozole">Letrozole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Androgen" title="Androgen">Androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>)</li> <li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D<sub>2</sub> receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin" title="Prolactin">prolactin</a> releasers) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>, <a href="/wiki/Goserelin" title="Goserelin">goserelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>, <a href="/wiki/Elagolix" title="Elagolix">elagolix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Mixed mechanism of action:</i> <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li></ul> <ul><li><i>Androstenedione immunogens:</i> <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Estrogen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Steroidal:</i> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&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"><i>ent</i>-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li><i>Nonsteroidal:</i> <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&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"><i>meso</i>-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol"><i>meso</i>-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&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><i>Unknown/unsorted:</i> <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li><i>Xenoestrogens:</i> <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&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 (<i>cis</i>-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&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<br />(<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators</span>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&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 href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&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><i>Coregulator-binding modulators:</i> <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li><i>Noncompetitive inhibitors:</i> <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-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="/w/index.php?title=G-1_(drug)&action=edit&redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&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/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&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 href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&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><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Estradiol_hexahydrobenzoate&oldid=1228928918">https://en.wikipedia.org/w/index.php?title=Estradiol_hexahydrobenzoate&oldid=1228928918</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Abandoned_drugs" title="Category:Abandoned drugs">Abandoned drugs</a></li><li><a href="/wiki/Category:Estradiol_esters" 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