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class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical drug</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a> or <a href="/wiki/Estrogen_conjugate" title="Estrogen conjugate">Estrogen conjugate</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Conjugated estriol">Conjugated estriol</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Estriol_glucuronide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Estriol_glucuronide.svg/250px-Estriol_glucuronide.svg.png" decoding="async" width="250" height="125" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Estriol_glucuronide.svg/375px-Estriol_glucuronide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Estriol_glucuronide.svg/500px-Estriol_glucuronide.svg.png 2x" data-file-width="1830" data-file-height="915" /></a></span><div class="infobox-caption"><a href="/wiki/Estriol_16%CE%B1-glucuronide" class="mw-redirect" title="Estriol 16α-glucuronide">Estriol 16α-glucuronide</a>, the primary active component in conjugated estriol (estriol glucuronides constitute about 35 to 46% of total content).</div></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Estriol_3-sulfate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Estriol_3-sulfate.svg/250px-Estriol_3-sulfate.svg.png" decoding="async" width="250" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Estriol_3-sulfate.svg/375px-Estriol_3-sulfate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Estriol_3-sulfate.svg/500px-Estriol_3-sulfate.svg.png 2x" data-file-width="1595" data-file-height="780" /></a></span><div class="infobox-caption"><a href="/wiki/Estriol_3-sulfate" class="mw-redirect" title="Estriol 3-sulfate">Estriol 3-sulfate</a>, the second major active component in conjugated estriol (constitutes about 15 to 22% of total content).</div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Combination of</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">Estriol glucuronide</a></th><td class="infobox-data"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Estriol_sulfate" title="Estriol sulfate">Estriol sulfate</a></th><td class="infobox-data"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Estriol_sulfate_glucuronide" title="Estriol sulfate glucuronide">Estriol sulfate glucuronide</a></th><td class="infobox-data"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Progynon, Emmenin</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Conjugated human estriol; Conjugated oestriol; Conjugated human oestriol; CE3; CHE3; Conjugated human estrogens; Conjugated human oestrogens; CHEs</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></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=113-38-2">113-38-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/NIG5418BXB">NIG5418BXB</a></span></li></ul></div></td></tr></tbody></table> <p><b>Conjugated estriol</b>, sold under the brand names <b>Progynon</b> and <b>Emmenin</b>, is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> medication which was previously used for estrogen-type indications such as the treatment of <a href="/wiki/Menopausal_symptoms" class="mw-redirect" title="Menopausal symptoms">menopausal symptoms</a> in women. The term specifically refers to <a href="/wiki/Drug_formulation" class="mw-redirect" title="Drug formulation">formulations</a> of <a href="/wiki/Estriol_conjugate" class="mw-redirect" title="Estriol conjugate">estriol conjugates</a> which were manufactured from the estrogen-rich <a href="/wiki/Urine" title="Urine">urine</a> of <a href="/wiki/Pregnancy" title="Pregnancy">pregnant</a> women and were used as medications in the 1920s and 1930s. Conjugated estriol is analogous to and was superseded by <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a> (brand name Premarin), which is manufactured from the urine of pregnant <a href="/wiki/Mare" title="Mare">mares</a>. Conjugated estriol was among the first forms of <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical</a> estrogen to be used in medicine. It was taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>. </p><p>The main components of conjugated estriol are <a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">estriol glucuronides</a> and to a lesser extent <a href="/wiki/Estriol_sulfate" title="Estriol sulfate">estriol sulfates</a>. Estrogen glucuronides can be deglucuronidated into the corresponding free estrogens by <a href="/wiki/%CE%92-glucuronidase" class="mw-redirect" title="Β-glucuronidase">β-glucuronidase</a> in <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a> that express this <a href="/wiki/Enzyme" title="Enzyme">enzyme</a>, such as the <a href="/wiki/Mammary_gland" title="Mammary gland">mammary gland</a>, <a href="/wiki/Liver" title="Liver">liver</a>, and <a href="/wiki/Kidney" title="Kidney">kidney</a>, among others.<sup id="cite_ref-pmid9472688_1-0" class="reference"><a href="#cite_note-pmid9472688-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Likewise, estrogen sulfates can be desulfated into the corresponding free estrogens by <a href="/wiki/Steroid_sulfatase" title="Steroid sulfatase">steroid sulfatase</a> in tissues that express this enzyme.<sup id="cite_ref-pmid16112947_2-0" class="reference"><a href="#cite_note-pmid16112947-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Consequently, estrogen conjugates have estrogenic activity via conversion into unconjugated estrogens.<sup id="cite_ref-pmid9472688_1-1" class="reference"><a href="#cite_note-pmid9472688-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Progynon">Progynon</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Conjugated_estriol&action=edit&section=1" title="Edit section: Progynon"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Glass_bottle_for_%27Progynon%27_pills,_United_Kingdom,_1928-1948_Wellcome_L0058274.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Glass_bottle_for_%27Progynon%27_pills%2C_United_Kingdom%2C_1928-1948_Wellcome_L0058274.jpg/200px-Glass_bottle_for_%27Progynon%27_pills%2C_United_Kingdom%2C_1928-1948_Wellcome_L0058274.jpg" decoding="async" width="200" height="265" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Glass_bottle_for_%27Progynon%27_pills%2C_United_Kingdom%2C_1928-1948_Wellcome_L0058274.jpg/300px-Glass_bottle_for_%27Progynon%27_pills%2C_United_Kingdom%2C_1928-1948_Wellcome_L0058274.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/Glass_bottle_for_%27Progynon%27_pills%2C_United_Kingdom%2C_1928-1948_Wellcome_L0058274.jpg/400px-Glass_bottle_for_%27Progynon%27_pills%2C_United_Kingdom%2C_1928-1948_Wellcome_L0058274.jpg 2x" data-file-width="3474" data-file-height="4611" /></a><figcaption>Progynon (Schering).</figcaption></figure> <p>Progynon was an <a href="/wiki/Oral_administration" title="Oral administration">orally active</a> <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">formulation</a> of <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> that was developed by <a href="/wiki/Adolf_Butenandt" title="Adolf Butenandt">Adolf Butenandt</a> at <a href="/wiki/Schering_AG" title="Schering AG">Schering</a> and introduced in <a href="/wiki/Germany" title="Germany">Germany</a> in 1928.<sup id="cite_ref-Seaman_2011_3-0" class="reference"><a href="#cite_note-Seaman_2011-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rooke_2012_4-0" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Veler_1930_5-0" class="reference"><a href="#cite_note-Veler_1930-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kobrak_2002_6-0" class="reference"><a href="#cite_note-Kobrak_2002-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Streck_1928_7-0" class="reference"><a href="#cite_note-Streck_1928-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Regitz-Zagrosek_2012_8-0" class="reference"><a href="#cite_note-Regitz-Zagrosek_2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It was reportedly the first <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormone</a> product and hence also the first estrogen product to be introduced for medical use.<sup id="cite_ref-Regitz-Zagrosek_2012_8-1" class="reference"><a href="#cite_note-Regitz-Zagrosek_2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Progynon was originally an <a href="/wiki/Ovary" title="Ovary">ovarian</a> or <a href="/wiki/Placenta" title="Placenta">placental</a> extract,<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Alstead_2013_10-0" class="reference"><a href="#cite_note-Alstead_2013-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> but Schering soon switched for economic reasons to using the <a href="/wiki/Urine" title="Urine">urine</a> of women who were in late <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>.<sup id="cite_ref-Kobrak_2002_6-1" class="reference"><a href="#cite_note-Kobrak_2002-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This form of Progynon was essentially the same product as Emmenin, which was developed by <a href="/wiki/James_Collip" title="James Collip">James Collip</a> at <a href="/wiki/Ayerst" title="Ayerst">Ayerst</a> and introduced in <a href="/wiki/Canada" title="Canada">Canada</a> in 1930 (and in the <a href="/wiki/United_States" title="United States"><abbr title="United States">U.S.</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States</span> in 1934).<sup id="cite_ref-Seaman_2011_3-1" class="reference"><a href="#cite_note-Seaman_2011-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rooke_2012_4-1" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>To further reduce the costs of manufacturing Progynon, Schering eventually switched to using the urine of pregnant <a href="/wiki/Mare" title="Mare">mares</a> and called its new product Progynon 2.<sup id="cite_ref-Seaman_2011_3-2" class="reference"><a href="#cite_note-Seaman_2011-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rooke_2012_4-2" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Chopra_2013_11-0" class="reference"><a href="#cite_note-Chopra_2013-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Ayerst followed suit, with the introduction of <a href="/wiki/Premarin" class="mw-redirect" title="Premarin">Premarin</a> (<a href="/wiki/Conjugated_equine_estrogen" class="mw-redirect" title="Conjugated equine estrogen">conjugated equine estrogens</a>) in 1941.<sup id="cite_ref-Rooke_2012_4-3" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Premarin soon superseded Emmenin and has since become not only a very widely used estrogen, but one of the most widely prescribed drugs in <a href="/wiki/North_America" title="North America">North America</a>.<sup id="cite_ref-Bolton_2006_12-0" class="reference"><a href="#cite_note-Bolton_2006-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Both Progynon and Emmenin contained a mixture of <a href="/wiki/Solubility" title="Solubility">water-soluble</a> estrogens, which was determined later to be mostly <a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">estriol glucuronide</a>.<sup id="cite_ref-Rooke_2012_4-4" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pincus_2013_13-0" class="reference"><a href="#cite_note-Pincus_2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Conjugate_(biochemistry)" class="mw-redirect" title="Conjugate (biochemistry)">Conjugates</a> of <a href="/wiki/Estriol" title="Estriol">estriol</a> like estriol glucuronide and <a href="/wiki/Estriol_sulfate" title="Estriol sulfate">estriol sulfate</a> constitute more than 90% of the estrogens in the urine of pregnant women.<sup id="cite_ref-CreasyResnik2013_14-0" class="reference"><a href="#cite_note-CreasyResnik2013-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Of these conjugates, 35 to 46% are estriol glucuronides and 15 to 22% are estriol 3-sulfate in late pregnancy; the double conjugate <a href="/wiki/Estriol_sulfate_glucuronide" title="Estriol sulfate glucuronide">estriol sulfate glucuronide</a> (probably estriol 3-sulfate 16α-glucuronide) also occurs.<sup id="cite_ref-Assali_2013_15-0" class="reference"><a href="#cite_note-Assali_2013-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sies_2005_16-0" class="reference"><a href="#cite_note-Sies_2005-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid14296256_17-0" class="reference"><a href="#cite_note-pmid14296256-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Progynon was also the name that Butenandt originally gave <a href="/wiki/Estrone" title="Estrone">estrone</a> (which he had isolated in 1929) in his first publication on the substance (and later referred to as folliculine, with the name estrone not finally being adopted until 1935).<sup id="cite_ref-Laylin1993_18-0" class="reference"><a href="#cite_note-Laylin1993-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Aside from Progynon and Progynon 2, the Progynon name has also been used in a variety of other estrogenic products marketed by Schering, including Progynon-B (<a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>), Progynon-DH (<a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>; "dihydroxyestrin"), Progynon-DP (<a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">estradiol dipropionate</a>), Progynon-C (<a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>), Progynova (<a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>), and Progynon Depot (estradiol valerate, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>). </p> <div class="mw-heading mw-heading2"><h2 id="Emmenin">Emmenin</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Conjugated_estriol&action=edit&section=2" title="Edit section: Emmenin"><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:Emmenin_tablets.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/8/81/Emmenin_tablets.jpg/300px-Emmenin_tablets.jpg" decoding="async" width="300" height="200" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/8/81/Emmenin_tablets.jpg 1.5x" data-file-width="387" data-file-height="258" /></a><figcaption>Emmenin (Ayerst).</figcaption></figure> <p>Emmenin was an <a href="/wiki/Oral_administration" title="Oral administration">orally active</a> <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">formulation</a> of <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> that was developed by <a href="/wiki/James_Collip" title="James Collip">James Collip</a> at <a href="/wiki/Ayerst" title="Ayerst">Ayerst</a> and introduced in <a href="/wiki/Canada" title="Canada">Canada</a> in 1930 and the <a href="/wiki/United_States" title="United States">United States</a> in 1934.<sup id="cite_ref-Seaman_2011_3-3" class="reference"><a href="#cite_note-Seaman_2011-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rooke_2012_4-5" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It was originally an extract obtained from human <a href="/wiki/Placenta" title="Placenta">placenta</a>.<sup id="cite_ref-Collip_1934_20-0" class="reference"><a href="#cite_note-Collip_1934-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Macfarlane_1936_21-0" class="reference"><a href="#cite_note-Macfarlane_1936-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Campbell_1933_22-0" class="reference"><a href="#cite_note-Campbell_1933-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CampbellCollip1930_23-0" class="reference"><a href="#cite_note-CampbellCollip1930-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-McCullagh_1935_24-0" class="reference"><a href="#cite_note-McCullagh_1935-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> At some point, it seems to have been changed to an extract of the <a href="/wiki/Urine" title="Urine">urine</a> of women who were in late <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>, which was equivalent in composition but was less expensive to source,<sup id="cite_ref-pmid17648157_25-0" class="reference"><a href="#cite_note-pmid17648157-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> and was essentially the same product as Progynon, a related estrogen developed by <a href="/wiki/Adolf_Butenandt" title="Adolf Butenandt">Adolf Butenandt</a> at <a href="/wiki/Schering_AG" title="Schering AG">Schering</a> and introduced in <a href="/wiki/Germany" title="Germany">Germany</a>.<sup id="cite_ref-Seaman_2011_3-4" class="reference"><a href="#cite_note-Seaman_2011-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rooke_2012_4-6" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Veler_1930_5-1" class="reference"><a href="#cite_note-Veler_1930-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Kobrak_2002_6-2" class="reference"><a href="#cite_note-Kobrak_2002-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Streck_1928_7-1" class="reference"><a href="#cite_note-Streck_1928-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Regitz-Zagrosek_2012_8-2" class="reference"><a href="#cite_note-Regitz-Zagrosek_2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> These estrogen products were the first orally active estrogens to be marketed for medical use.<sup id="cite_ref-Rooke_2012_4-7" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Regitz-Zagrosek_2012_8-3" class="reference"><a href="#cite_note-Regitz-Zagrosek_2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Li2003_26-0" class="reference"><a href="#cite_note-Li2003-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Gluck_2010_27-0" class="reference"><a href="#cite_note-Gluck_2010-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>To reduce the costs of manufacturing Emmenin and Progynon, Ayerst and Schering eventually switched to using the urine of pregnant <a href="/wiki/Mare" title="Mare">mares</a> (which contains <a href="/wiki/Conjugated_equine_estrogen" class="mw-redirect" title="Conjugated equine estrogen">conjugated equine estrogens</a>, primarily <a href="/wiki/Estrone_sulfate" title="Estrone sulfate">estrone sulfate</a>)<sup id="cite_ref-pmid16112947_2-1" class="reference"><a href="#cite_note-pmid16112947-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and called their new products <a href="/wiki/Premarin" class="mw-redirect" title="Premarin">Premarin</a> and Progynon 2, respectively.<sup id="cite_ref-Seaman_2011_3-5" class="reference"><a href="#cite_note-Seaman_2011-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rooke_2012_4-8" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Chopra_2013_11-1" class="reference"><a href="#cite_note-Chopra_2013-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Premarin was introduced by Ayerst in 1941<sup id="cite_ref-Rooke_2012_4-9" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and has become not only a very widely used estrogen, but one of the most widely prescribed drugs in <a href="/wiki/North_America" title="North America">North America</a>.<sup id="cite_ref-Bolton_2006_12-1" class="reference"><a href="#cite_note-Bolton_2006-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Both Emmenin and Progynon contained a mixture of <a href="/wiki/Solubility" title="Solubility">water-soluble</a> <a href="/wiki/Conjugation_(biochemistry)" class="mw-redirect" title="Conjugation (biochemistry)">conjugated</a> estrogens, later determined to be mostly <a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">estriol glucuronide</a>.<sup id="cite_ref-Rooke_2012_4-10" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pincus_2013_13-1" class="reference"><a href="#cite_note-Pincus_2013-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Conjugate_(biochemistry)" class="mw-redirect" title="Conjugate (biochemistry)">Conjugates</a> of <a href="/wiki/Estriol" title="Estriol">estriol</a> like estriol glucuronide and <a href="/wiki/Estriol_sulfate" title="Estriol sulfate">estriol sulfate</a> constitute more than 90% of the estrogens in the urine of pregnant women.<sup id="cite_ref-CreasyResnik2013_14-1" class="reference"><a href="#cite_note-CreasyResnik2013-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Of these conjugates, 35 to 46% are estriol glucuronides and 15 to 22% are estriol 3-sulfate in late pregnancy; the double conjugate <a href="/wiki/Estriol_sulfate_glucuronide" title="Estriol sulfate glucuronide">estriol sulfate glucuronide</a> (probably estriol 3-sulfate 16α-glucuronide) also occurs.<sup id="cite_ref-Assali_2013_15-1" class="reference"><a href="#cite_note-Assali_2013-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Sies_2005_16-1" class="reference"><a href="#cite_note-Sies_2005-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid14296256_17-1" class="reference"><a href="#cite_note-pmid14296256-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Unlike unconjugated estrogens like <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> and <a href="/wiki/Estrone" title="Estrone">estrone</a>, these estrogens were orally active.<sup id="cite_ref-Rooke_2012_4-11" class="reference"><a href="#cite_note-Rooke_2012-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Regitz-Zagrosek_2012_8-4" class="reference"><a href="#cite_note-Regitz-Zagrosek_2012-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Li2003_26-1" class="reference"><a href="#cite_note-Li2003-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Gluck_2010_27-1" class="reference"><a href="#cite_note-Gluck_2010-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Conjugated_estriol&action=edit&section=3" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</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/Estrogen_conjugate" title="Estrogen conjugate">Estrogen conjugate</a></li> <li><a href="/wiki/List_of_combined_sex-hormonal_preparations" title="List of combined sex-hormonal preparations">List of combined sex-hormonal preparations</a></li></ul> <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=Conjugated_estriol&action=edit&section=4" 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-pmid9472688-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid9472688_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid9472688_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em 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="CITEREFZhuConney1998" class="citation journal cs1">Zhu BT, Conney AH (January 1998). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fcarcin%2F19.1.1">"Functional role of estrogen metabolism in target cells: review and perspectives"</a>. <i>Carcinogenesis</i>. <b>19</b> (1): <span class="nowrap">1–</span>27. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fcarcin%2F19.1.1">10.1093/carcin/19.1.1</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9472688">9472688</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Carcinogenesis&rft.atitle=Functional+role+of+estrogen+metabolism+in+target+cells%3A+review+and+perspectives&rft.volume=19&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E27&rft.date=1998-01&rft_id=info%3Adoi%2F10.1093%2Fcarcin%2F19.1.1&rft_id=info%3Apmid%2F9472688&rft.aulast=Zhu&rft.aufirst=BT&rft.au=Conney%2C+AH&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fcarcin%252F19.1.1&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-pmid16112947-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid16112947_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid16112947_2-1"><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="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): <span class="nowrap">3–</span>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=%3Cspan+class%3D%22nowrap%22%3E3-%3C%2Fspan%3E63&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%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Seaman_2011-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Seaman_2011_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Seaman_2011_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Seaman_2011_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Seaman_2011_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Seaman_2011_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Seaman_2011_3-5"><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="CITEREFSeaman2011" class="citation book cs1">Seaman B (4 January 2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=HHm1qkcgFSUC&pg=PA22"><i>The Greatest Experiment Ever Performed on Women: Exploding the Estrogen Myth</i></a>. Seven Stories Press. pp. 22–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60980-062-8" title="Special:BookSources/978-1-60980-062-8"><bdi>978-1-60980-062-8</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+Greatest+Experiment+Ever+Performed+on+Women%3A+Exploding+the+Estrogen+Myth&rft.pages=22-&rft.pub=Seven+Stories+Press&rft.date=2011-01-04&rft.isbn=978-1-60980-062-8&rft.aulast=Seaman&rft.aufirst=B&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DHHm1qkcgFSUC%26pg%3DPA22&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Rooke_2012-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Rooke_2012_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Rooke_2012_4-11"><sup><i><b>l</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRooke2012" class="citation book cs1">Rooke T (1 January 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=70vvFrtpePoC&pg=PT54"><i>The Quest for Cortisone</i></a>. MSU Press. pp. 54–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60917-326-5" title="Special:BookSources/978-1-60917-326-5"><bdi>978-1-60917-326-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Quest+for+Cortisone&rft.pages=54-&rft.pub=MSU+Press&rft.date=2012-01-01&rft.isbn=978-1-60917-326-5&rft.aulast=Rooke&rft.aufirst=T&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D70vvFrtpePoC%26pg%3DPT54&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Veler_1930-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Veler_1930_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Veler_1930_5-1"><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="CITEREFVelerThayerDoisy1930" class="citation journal cs1">Veler CD, Thayer S, Doisy EA (1930). <a rel="nofollow" class="external text" href="http://www.jbc.org/content/87/2/357.short">"The Preparation of the Crystalline Follicular Ovarian Hormone: Theelin"</a>. <i>Journal of Biological Chemistry</i>. <b>87</b> (2): <span class="nowrap">357–</span>371. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2976871-3">10.1016/S0021-9258(18)76871-3</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Biological+Chemistry&rft.atitle=The+Preparation+of+the+Crystalline+Follicular+Ovarian+Hormone%3A+Theelin&rft.volume=87&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E357-%3C%2Fspan%3E371&rft.date=1930&rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2818%2976871-3&rft.aulast=Veler&rft.aufirst=CD&rft.au=Thayer%2C+S&rft.au=Doisy%2C+EA&rft_id=http%3A%2F%2Fwww.jbc.org%2Fcontent%2F87%2F2%2F357.short&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Kobrak_2002-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-Kobrak_2002_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Kobrak_2002_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Kobrak_2002_6-2"><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="CITEREFKobrak2002" class="citation book cs1">Kobrak C (7 October 2002). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Z3iTsU6_mHsC&pg=PA119"><i>National Cultures and International Competition: The Experience of Schering AG, 1851-1950</i></a>. Cambridge University Press. pp. 119–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-521-81481-2" title="Special:BookSources/978-0-521-81481-2"><bdi>978-0-521-81481-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=National+Cultures+and+International+Competition%3A+The+Experience+of+Schering+AG%2C+1851-1950&rft.pages=119-&rft.pub=Cambridge+University+Press&rft.date=2002-10-07&rft.isbn=978-0-521-81481-2&rft.aulast=Kobrak&rft.aufirst=C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DZ3iTsU6_mHsC%26pg%3DPA119&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Streck_1928-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-Streck_1928_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Streck_1928_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="CITEREFStreck1928" class="citation journal cs1 cs1-prop-foreign-lang-source">Streck A (1928). "<span class="cs1-kern-left"></span>"Progynon"-Schering, ein Neues Zyklus-Hormonpräparat" ["Progynon"-Schering, a new cycle hormone preparation]. <i>Klinische Wochenschrift</i> (in German). <b>7</b> (25): <span class="nowrap">1172–</span>1178. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF01738283">10.1007/BF01738283</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0023-2173">0023-2173</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:35945534">35945534</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Klinische+Wochenschrift&rft.atitle=%22Progynon%22-Schering%2C+ein+Neues+Zyklus-Hormonpr%C3%A4parat&rft.volume=7&rft.issue=25&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1172-%3C%2Fspan%3E1178&rft.date=1928&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A35945534%23id-name%3DS2CID&rft.issn=0023-2173&rft_id=info%3Adoi%2F10.1007%2FBF01738283&rft.aulast=Streck&rft.aufirst=A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Regitz-Zagrosek_2012-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Regitz-Zagrosek_2012_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Regitz-Zagrosek_2012_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Regitz-Zagrosek_2012_8-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Regitz-Zagrosek_2012_8-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Regitz-Zagrosek_2012_8-4"><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="CITEREFRegitz-Zagrosek2012" class="citation book cs1">Regitz-Zagrosek V (2 October 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=J3VxihGDh9wC&pg=PA549"><i>Sex and Gender Differences in Pharmacology</i></a>. Springer Science & Business Media. pp. 549–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-30725-6" title="Special:BookSources/978-3-642-30725-6"><bdi>978-3-642-30725-6</bdi></a>. <q>The first sex steroid used as pharmacological agent was Progynon, first sold by Schering AG in 1928. [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sex+and+Gender+Differences+in+Pharmacology&rft.pages=549-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-10-02&rft.isbn=978-3-642-30725-6&rft.aulast=Regitz-Zagrosek&rft.aufirst=V&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJ3VxihGDh9wC%26pg%3DPA549&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBatisweiler1928" class="citation journal cs1 cs1-prop-foreign-lang-source">Batisweiler J (1928). "Placentaextrakt Progynon (Schering-Kahlbaum) bei Menstruationsstörungen und Kastrationsfolgen" [Placenta extract Progynon (Schering-Kahlbaum) for menstrual disorders and the consequences of castration.]. <i>ZBL. 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Elsevier. pp. 195–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-2584-5" title="Special:BookSources/978-1-4832-2584-5"><bdi>978-1-4832-2584-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Poulsson%27s+Text-Book+of+Pharmacology+and+Therapeutics&rft.pages=195-&rft.pub=Elsevier&rft.date=2013-10-22&rft.isbn=978-1-4832-2584-5&rft.aulast=Alstead&rft.aufirst=S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBRIlBQAAQBAJ%26pg%3DPA195&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Chopra_2013-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Chopra_2013_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Chopra_2013_11-1"><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="CITEREFChopraNanda2013" class="citation book cs1">Chopra HK, Nanda NC (15 December 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=3UPHBAAAQBAJ&pg=PA326"><i>Textbook of Cardiology: A Clinical and Historical Perspective</i></a>. 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Elsevier. pp. 4–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-046538-8" title="Special:BookSources/978-0-08-046538-8"><bdi>978-0-08-046538-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Bioactivation+of+Estrogens+to+Toxic+Quinones&rft.btitle=Advances+in+Molecular+Toxicology&rft.pages=4-&rft.pub=Elsevier&rft.date=2006-10-13&rft.isbn=978-0-08-046538-8&rft.aulast=Bolton&rft.aufirst=JL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DW-mN1jfBIIwC%26pg%3DPA4&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Pincus_2013-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-Pincus_2013_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Pincus_2013_13-1"><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="CITEREFPincus2013" class="citation book cs1">Pincus G (22 October 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=jgTgBAAAQBAJ&pg=PA307"><i>Recent Progress in Hormone Research: The Proceedings of the Laurentian Hormone Conference</i></a>. Elsevier Science. pp. 307–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-1945-5" title="Special:BookSources/978-1-4832-1945-5"><bdi>978-1-4832-1945-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Recent+Progress+in+Hormone+Research%3A+The+Proceedings+of+the+Laurentian+Hormone+Conference&rft.pages=307-&rft.pub=Elsevier+Science&rft.date=2013-10-22&rft.isbn=978-1-4832-1945-5&rft.aulast=Pincus&rft.aufirst=G&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DjgTgBAAAQBAJ%26pg%3DPA307&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-CreasyResnik2013-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-CreasyResnik2013_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-CreasyResnik2013_14-1"><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="CITEREFCreasyResnikLockwoodIams2013" class="citation book cs1">Creasy RK, Resnik R, Lockwood CJ, Iams JD, Greene MF, Moore T (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=AbMKAQAAQBAJ&pg=PA104"><i>Creasy and Resnik's Maternal-Fetal Medicine: Principles and Practice</i></a>. Elsevier Health Sciences. pp. 104–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4557-1137-6" title="Special:BookSources/978-1-4557-1137-6"><bdi>978-1-4557-1137-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Creasy+and+Resnik%27s+Maternal-Fetal+Medicine%3A+Principles+and+Practice&rft.pages=104-&rft.pub=Elsevier+Health+Sciences&rft.date=2013&rft.isbn=978-1-4557-1137-6&rft.aulast=Creasy&rft.aufirst=RK&rft.au=Resnik%2C+R&rft.au=Lockwood%2C+CJ&rft.au=Iams%2C+JD&rft.au=Greene%2C+MF&rft.au=Moore%2C+T&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DAbMKAQAAQBAJ%26pg%3DPA104&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Assali_2013-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-Assali_2013_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Assali_2013_15-1"><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="CITEREFAssali2013" class="citation book cs1">Assali NS (3 September 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=mSzLBAAAQBAJ&pg=PA339"><i>The Maternal Organism</i></a>. Elsevier. pp. 339–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-6380-9" title="Special:BookSources/978-1-4832-6380-9"><bdi>978-1-4832-6380-9</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+Maternal+Organism&rft.pages=339-&rft.pub=Elsevier&rft.date=2013-09-03&rft.isbn=978-1-4832-6380-9&rft.aulast=Assali&rft.aufirst=NS&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DmSzLBAAAQBAJ%26pg%3DPA339&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Sies_2005-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-Sies_2005_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Sies_2005_16-1"><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="CITEREFSiesPacker2005" class="citation book cs1">Sies H, Packer L (2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tlm-C-H3DtIC&pg=PA294"><i>Phase II Conjugation Enzymes and Transport Systems</i></a>. Gulf Professional Publishing. pp. 294–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-182805-9" title="Special:BookSources/978-0-12-182805-9"><bdi>978-0-12-182805-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Phase+II+Conjugation+Enzymes+and+Transport+Systems&rft.pages=294-&rft.pub=Gulf+Professional+Publishing&rft.date=2005&rft.isbn=978-0-12-182805-9&rft.aulast=Sies&rft.aufirst=H&rft.au=Packer%2C+L&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dtlm-C-H3DtIC%26pg%3DPA294&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-pmid14296256-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid14296256_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid14296256_17-1"><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="CITEREFSmithHagerman1965" class="citation journal cs1">Smith OW, Hagerman DD (June 1965). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjcem-25-6-732">"Quantitative estimation of estrogen conjugates in late pregnancy plasma"</a>. <i>The Journal of Clinical Endocrinology and Metabolism</i>. <b>25</b> (6): <span class="nowrap">732–</span>741. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjcem-25-6-732">10.1210/jcem-25-6-732</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14296256">14296256</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Clinical+Endocrinology+and+Metabolism&rft.atitle=Quantitative+estimation+of+estrogen+conjugates+in+late+pregnancy+plasma&rft.volume=25&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E732-%3C%2Fspan%3E741&rft.date=1965-06&rft_id=info%3Adoi%2F10.1210%2Fjcem-25-6-732&rft_id=info%3Apmid%2F14296256&rft.aulast=Smith&rft.aufirst=OW&rft.au=Hagerman%2C+DD&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fjcem-25-6-732&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Laylin1993-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-Laylin1993_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLaylin1993" class="citation book cs1">Laylin JK (30 October 1993). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=jEy67gEvIuMC&pg=PA254"><i>Nobel Laureates in Chemistry, 1901-1992</i></a>. Chemical Heritage Foundation. pp. <span class="nowrap">253–</span>254. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8412-2690-6" title="Special:BookSources/978-0-8412-2690-6"><bdi>978-0-8412-2690-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Nobel+Laureates+in+Chemistry%2C+1901-1992&rft.pages=%3Cspan+class%3D%22nowrap%22%3E253-%3C%2Fspan%3E254&rft.pub=Chemical+Heritage+Foundation&rft.date=1993-10-30&rft.isbn=978-0-8412-2690-6&rft.aulast=Laylin&rft.aufirst=JK&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DjEy67gEvIuMC%26pg%3DPA254&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBooth1983" class="citation book cs1">Booth D (2 November 1983). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DIKsW_b2GSoC&pg=PA136">"Estrone"</a>. 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"Concerning Placental Hormones and Menstrual Disorders". <i>Annals of Internal Medicine</i>. <b>7</b> (3): 330. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.7326%2F0003-4819-7-3-330">10.7326/0003-4819-7-3-330</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0003-4819">0003-4819</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annals+of+Internal+Medicine&rft.atitle=Concerning+Placental+Hormones+and+Menstrual+Disorders&rft.volume=7&rft.issue=3&rft.pages=330&rft.date=1933&rft_id=info%3Adoi%2F10.7326%2F0003-4819-7-3-330&rft.issn=0003-4819&rft.aulast=Campbell&rft.aufirst=AD&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-CampbellCollip1930-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-CampbellCollip1930_23-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCampbellCollip1930" class="citation journal cs1">Campbell AD, Collip JB (1930). "Treatment of menopausal symptoms and menstrual disorders with extracts of human placenta and pregnancy urine". <i>Canadian Medical Association Journal</i>. <b>23</b>: <span class="nowrap">633–</span>641.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Canadian+Medical+Association+Journal&rft.atitle=Treatment+of+menopausal+symptoms+and+menstrual+disorders+with+extracts+of+human+placenta+and+pregnancy+urine.&rft.volume=23&rft.pages=%3Cspan+class%3D%22nowrap%22%3E633-%3C%2Fspan%3E641&rft.date=1930&rft.aulast=Campbell&rft.aufirst=AD&rft.au=Collip%2C+JB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-McCullagh_1935-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-McCullagh_1935_24-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcCullagh1935" class="citation journal cs1">McCullagh EP (1935). <a rel="nofollow" class="external text" href="https://www.mdedge.com/ccjm/article/90505/management-functional-menstrual-disorders">"The Management of Functional Menstrual Disorders"</a>. <i>Cleveland Clinic Quarterly</i>. <b>2</b> (4): <span class="nowrap">52–</span>64. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3949%2Fccjm.2.4.52">10.3949/ccjm.2.4.52</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cleveland+Clinic+Quarterly&rft.atitle=The+Management+of+Functional+Menstrual+Disorders&rft.volume=2&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E52-%3C%2Fspan%3E64&rft.date=1935&rft_id=info%3Adoi%2F10.3949%2Fccjm.2.4.52&rft.aulast=McCullagh&rft.aufirst=EP&rft_id=https%3A%2F%2Fwww.mdedge.com%2Fccjm%2Farticle%2F90505%2Fmanagement-functional-menstrual-disorders&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-pmid17648157-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid17648157_25-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStevenson1945" class="citation journal cs1">Stevenson WG (November 1945). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1661006">"Pregnant Mares' Urine and Oestrogens"</a>. <i>Canadian Journal of Comparative Medicine and Veterinary Science</i>. <b>9</b> (11): <span class="nowrap">293–</span>301. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1661006">1661006</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17648157">17648157</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Canadian+Journal+of+Comparative+Medicine+and+Veterinary+Science&rft.atitle=Pregnant+Mares%27+Urine+and+Oestrogens&rft.volume=9&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E293-%3C%2Fspan%3E301&rft.date=1945-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1661006%23id-name%3DPMC&rft_id=info%3Apmid%2F17648157&rft.aulast=Stevenson&rft.aufirst=WG&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1661006&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Li2003-26"><span class="mw-cite-backlink">^ <a href="#cite_ref-Li2003_26-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Li2003_26-1"><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="CITEREFLi2003" class="citation book cs1">Li A (27 October 2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=cUcZQ2l1E7wC&pg=PA86"><i>J.B. Collip and the Development of Medical Research in Canada: Extracts and Enterprise</i></a>. McGill-Queen's Press - MQUP. pp. 86–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7735-2609-9" title="Special:BookSources/978-0-7735-2609-9"><bdi>978-0-7735-2609-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=J.B.+Collip+and+the+Development+of+Medical+Research+in+Canada%3A+Extracts+and+Enterprise&rft.pages=86-&rft.pub=McGill-Queen%27s+Press+-+MQUP&rft.date=2003-10-27&rft.isbn=978-0-7735-2609-9&rft.aulast=Li&rft.aufirst=A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DcUcZQ2l1E7wC%26pg%3DPA86&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> <li id="cite_note-Gluck_2010-27"><span class="mw-cite-backlink">^ <a href="#cite_ref-Gluck_2010_27-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Gluck_2010_27-1"><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="CITEREFGluck2010" class="citation book cs1">Gluck M (1 February 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=z6jBB0kD1nYC&pg=PT25"><i>It Must Be My Hormones</i></a>. Penguin Books Limited. pp. 25–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85796-510-3" title="Special:BookSources/978-0-85796-510-3"><bdi>978-0-85796-510-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=It+Must+Be+My+Hormones&rft.pages=25-&rft.pub=Penguin+Books+Limited&rft.date=2010-02-01&rft.isbn=978-0-85796-510-3&rft.aulast=Gluck&rft.aufirst=M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dz6jBB0kD1nYC%26pg%3DPT25&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estriol" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist 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href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</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 class="mw-selflink selflink">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"><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"><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_modulators1222" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators1222" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</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 class="mw-selflink selflink">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/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a 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 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