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.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">Conjugated estrogens</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Estrone_sulfate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Estrone_sulfate.svg/225px-Estrone_sulfate.svg.png" decoding="async" width="225" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/15/Estrone_sulfate.svg/338px-Estrone_sulfate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/15/Estrone_sulfate.svg/450px-Estrone_sulfate.svg.png 2x" data-file-width="512" data-file-height="268" /></a><div class="infobox-caption"><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a>, the primary active component in conjugated estrogens (constitutes about 50 to 70% of total content)</div></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Equilin_sulfate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Equilin_sulfate.svg/225px-Equilin_sulfate.svg.png" decoding="async" width="225" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Equilin_sulfate.svg/338px-Equilin_sulfate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/df/Equilin_sulfate.svg/450px-Equilin_sulfate.svg.png 2x" data-file-width="512" data-file-height="268" /></a><div class="infobox-caption"><a href="/wiki/Equilin_sulfate" class="mw-redirect" title="Equilin sulfate">Equilin sulfate</a>, the second most major active component in conjugated estrogens (constitutes about 20 to 30% of total content)</div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Combination of</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone 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/Equilin_sulfate" class="mw-redirect" title="Equilin sulfate">Equilin 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/17%CE%B1-Dihydro-equilin_sulfate" class="mw-redirect" title="17α-Dihydro-equilin sulfate">17α-Dihydro-equilin sulfate</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">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">Cenestin, Enjuvia, Premarin, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">CEs; Conjugated equine estrogens; CEEs; Pregnant mares' urine; Estrogens, conjugated</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://www.drugs.com/mtm/conjugated-estrogens-vaginal.html">Multum Consumer Information</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>, <a href="/wiki/Topical_medication" title="Topical medication">topical</a>, <a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">vaginal</a>, <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">intravenous injection</a>, <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a><a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-Drugs@FDA-2">[2]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><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><a href="/wiki/ATC_code_G03" title="ATC code G03">G03CA57</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03CA57">WHO</a>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Boxed_warning" title="Boxed warning">WARNING</a><a href="#cite_note-FDA-AllBoxedWarnings-3">[3]</a></li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">Variable<a href="#cite_note-PremarinLabel-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">High (to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> and <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip sex hormone-binding globulin)<a href="#cite_note-PremarinLabel-4">[4]</a><a href="#cite_note-pmid16112947-1">[1]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a><a href="#cite_note-PremarinLabel-4">[4]</a><a href="#cite_note-pmid16112947-1">[1]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination half-life</a></th><td class="infobox-data"><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a>: 26.7 hours Estrone (<abbr title="baseline-adjusted">BA</abbr>): 14.8 hours <a href="/wiki/Equilin" title="Equilin">Equilin</a>: 11.4 hours<a href="#cite_note-DrugBank-5">[5]</a>[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">unreliable medical source?</a>]</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a><a href="#cite_note-PremarinLabel-4">[4]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=12126-59-9">12126-59-9</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/656613">656613</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00286">DB00286</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.570974.html">570974</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/IU5QR144QX">IU5QR144QX</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D04070">D04070</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8389">CHEBI:8389</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1201649">ChEMBL1201649</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9021186">DTXSID9021186</a> <a href="https://www.wikidata.org/wiki/Q4118295#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.031.987">100.031.987</a> <a href="https://www.wikidata.org/wiki/Q4118295#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=455284681&page2=Conjugated+estrogens">(verify)</a></td></tr></tbody></table> Conjugated estrogens (CEs), or conjugated equine estrogens (CEEs), sold under the brand name Premarin among others, is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> medication which is used in <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a> and for various other indications.<a href="#cite_note-Martindale-6">[6]</a><a href="#cite_note-PremarinLabel-4">[4]</a><a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a> It is a <a href="/wiki/Combination_drug" title="Combination drug">mixture</a> of the <a href="/wiki/Sodium" title="Sodium">sodium</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> of <a href="/wiki/Estrogen_conjugate" title="Estrogen conjugate">estrogen conjugates</a> found in <a href="/wiki/Equine" class="mw-redirect" title="Equine">horses</a>, such as <a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">estrone sulfate</a> and <a href="/wiki/Equilin_sulfate" class="mw-redirect" title="Equilin sulfate">equilin sulfate</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a><a href="#cite_note-Martindale-6">[6]</a> CEEs are available in the form of both <a href="/wiki/Natural_product" title="Natural product">natural</a> preparations manufactured from the <a href="/wiki/Urine" title="Urine">urine</a> of <a href="/wiki/Pregnancy_(mammals)" title="Pregnancy (mammals)">pregnant</a> <a href="/wiki/Mare" title="Mare">mares</a> and fully <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthetic</a> replications of the natural preparations.<a href="#cite_note-MoscouSnipe2012-8">[8]</a><a href="#cite_note-HumansOrganization2007-9">[9]</a> They are formulated both alone and in combination with <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> such as <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>.<a href="#cite_note-Martindale-6">[6]</a> CEEs are usually taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>, but can also be given by <a href="/wiki/Topical_medication" title="Topical medication">application to the skin</a> or <a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">vagina</a> as a <a href="/wiki/Cream_(pharmaceutical)" class="mw-redirect" title="Cream (pharmaceutical)">cream</a> or by <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">injection into a blood vessel</a> or <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">muscle</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-Drugs@FDA-2">[2]</a> <a href="/wiki/Side_effect" title="Side effect">Side effects</a> of CEEs include <a href="/wiki/Breast_pain" title="Breast pain">breast tenderness</a> and <a href="/wiki/Mammoplasia" title="Mammoplasia">enlargement</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a>, and <a href="/wiki/Nausea" title="Nausea">nausea</a> among others.<a href="#cite_note-PremarinLabel-4">[4]</a><a href="#cite_note-pmid16112947-1">[1]</a> It may increase the risk of <a href="/wiki/Endometrial_hyperplasia" title="Endometrial hyperplasia">endometrial hyperplasia</a> and <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> in women with an intact <a href="/wiki/Uterus" title="Uterus">uterus</a> if it is not taken together with a <a href="/wiki/Progestogen" title="Progestogen">progestogen</a> like <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>.<a href="#cite_note-PremarinLabel-4">[4]</a><a href="#cite_note-pmid16112947-1">[1]</a> The medication may also increase the risk of <a href="/wiki/Blood_clot" class="mw-redirect" title="Blood clot">blood clots</a>, <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a>, and, when combined with most progestogens, <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>.<a href="#cite_note-pmid28664754-10">[10]</a> CEEs are estrogens, or <a href="/wiki/Agonist" title="Agonist">agonists</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a>, the <a href="/wiki/Biological_target" title="Biological target">biological target</a> of <a href="/wiki/Estrogen" title="Estrogen">estrogens</a> like <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-PremarinLabel-4">[4]</a> Compared to estradiol, certain estrogens in CEEs are more resistant to metabolism, and the medication shows relatively increased effects in certain parts of the body like the <a href="/wiki/Liver" title="Liver">liver</a>.<a href="#cite_note-pmid16112947-1">[1]</a> This results in an increased risk of blood clots and cardiovascular problems with CEEs relative to estradiol.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-pmid25223916-11">[11]</a> Premarin, the major brand of CEEs in use, is manufactured by <a href="/wiki/Pfizer" title="Pfizer">Pfizer</a> and was first marketed in 1941 in <a href="/wiki/Canada" title="Canada">Canada</a> and in 1942 in the <a href="/wiki/United_States" title="United States">United States</a>.<a href="#cite_note-FritzSperoff2012-7">[7]</a> It is the most commonly used form of estrogen in menopausal hormone therapy in the United States.<a href="#cite_note-pmid24176763-12">[12]</a><a href="#cite_note-Quereda2017-13">[13]</a> However, it has begun to fall out of favor relative to <a href="/wiki/Bioidentical_hormone_therapy" class="mw-redirect" title="Bioidentical hormone therapy">bioidentical</a> <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>, which is the most widely used form of estrogen in <a href="/wiki/Europe" title="Europe">Europe</a> for menopausal hormone therapy.<a href="#cite_note-Quereda2017-13">[13]</a><a href="#cite_note-pmid28301216-14">[14]</a><a href="#cite_note-pmid24398406-15">[15]</a><a href="#cite_note-pmid19179815-16">[16]</a> CEEs are available widely throughout the world.<a href="#cite_note-Martindale-6">[6]</a> An estrogen preparation very similar to CEEs but differing in source and composition is <a href="/wiki/Esterified_estrogens" title="Esterified estrogens">esterified estrogens</a>.<a href="#cite_note-pmid16112947-1">[1]</a> In 2020, it was the 283rd most commonly prescribed medication in the United States, with more than 1 million prescriptions.<a href="#cite_note-DrugStats2017-17">[17]</a><a href="#cite_note-18">[18]</a> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> CEEs are a form of <a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">hormone therapy</a> used in women.<a href="#cite_note-19">[19]</a> It is used most commonly in <a href="/wiki/Postmenopausal" class="mw-redirect" title="Postmenopausal">postmenopausal</a> women who have had a <a href="/wiki/Hysterectomy" title="Hysterectomy">hysterectomy</a> to treat <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>, and burning, itching, and dryness of the vagina and surrounding areas.<a href="#cite_note-20">[20]</a> It must be used in combination with a <a href="/wiki/Progestogen" title="Progestogen">progestogen</a> in women who have not had a <a href="/wiki/Hysterectomy" title="Hysterectomy">hysterectomy</a>.<a href="#cite_note-pmid16112947-1">[1]</a> For women already taking the medication, it can be used to treat <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>, although it is not recommended solely for this use.<a href="#cite_note-21">[21]</a> Some lesser known uses are as a means of <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">high-dose estrogen</a> therapy in the treatment of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in both women and men and in the treatment of <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> in men.<a href="#cite_note-22">[22]</a><a href="#cite_note-23">[23]</a> It has been used at a dosage of 2.5 mg three times per day (7.5 mg/day total) for prostate cancer.<a href="#cite_note-OettelSchillinger2012-24">[24]</a><a href="#cite_note-DenisGriffiths1999-25">[25]</a> CEEs are specifically approved in countries such as the <a href="/wiki/United_States" title="United States">United States</a> and <a href="/wiki/Canada" title="Canada">Canada</a> for the treatment of moderate to severe <a href="/wiki/Vasomotor" title="Vasomotor">vasomotor</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a> (hot flashes) and <a href="/wiki/Vaginal_atrophy" class="mw-redirect" title="Vaginal atrophy">vulvovaginal atrophy</a> (atrophic vaginitis, atrophic urethritis) associated with <a href="/wiki/Menopause" title="Menopause">menopause</a>, <a href="/wiki/Hypoestrogenism" title="Hypoestrogenism">hypoestrogenism</a> due to <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>, <a href="/wiki/Ovariectomy" class="mw-redirect" title="Ovariectomy">ovariectomy</a>, or <a href="/wiki/Primary_ovarian_failure" class="mw-redirect" title="Primary ovarian failure">primary ovarian failure</a>, <a href="/wiki/Abnormal_uterine_bleeding" title="Abnormal uterine bleeding">abnormal uterine bleeding</a>, the <a href="/wiki/Palliative_care" title="Palliative care">palliative</a> treatment of <a href="/wiki/Metastatic_breast_cancer" title="Metastatic breast cancer">metastatic breast cancer</a> in women, the palliative treatment of <a href="/wiki/Metastasis" title="Metastasis">advanced</a> <a href="/wiki/Androgen-dependent_condition" title="Androgen-dependent condition">androgen-dependent</a> <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> in men, and the prevention of <a href="/wiki/Menopause" title="Menopause">postmenopausal</a> <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>.<a href="#cite_note-DrugBank-5">[5]</a><a href="#cite_note-Drugs.com-Premarin-26">[26]</a><a href="#cite_note-Martindale-6">[6]</a> The intravenous formulation of CEEs is specifically used to rapidly <a href="/wiki/Hemostasis" title="Hemostasis">limit bleeding</a> in women with <a href="/wiki/Hemorrhage" class="mw-redirect" title="Hemorrhage">hemorrhage</a> due to <a href="/wiki/Dysfunctional_uterine_bleeding" class="mw-redirect" title="Dysfunctional uterine bleeding">dysfunctional uterine bleeding</a>.<a href="#cite_note-Drugs@FDA-2">[2]</a><a href="#cite_note-HorskyPresl1981e-27">[27]</a>: 318 <a href="#cite_note-Piersol1975-28">[28]</a>: 60  <table class="wikitable mw-collapsible mw-collapsed" style="font-size: small; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap" style="font-size: 105%;"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_dosages_for_menopausal_hormone_therapy" title="Template:Estrogen dosages for menopausal hormone therapy"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_dosages_for_menopausal_hormone_therapy" title="Template talk:Estrogen dosages for menopausal hormone therapy"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_dosages_for_menopausal_hormone_therapy" title="Special:EditPage/Template:Estrogen dosages for menopausal hormone therapy"><abbr title="Edit this template">e</abbr></a></li></ul></div> Estrogen dosages for menopausal hormone therapy </caption> <tbody><tr> <th>Route/form</th> <th>Estrogen</th> <th>Low</th> <th>Standard</th> <th>High </th></tr> <tr> <td rowspan="8"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>0.5–1 mg/day</td> <td>1–2 mg/day</td> <td>2–4 mg/day </td></tr> <tr> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></td> <td>0.5–1 mg/day</td> <td>1–2 mg/day</td> <td>2–4 mg/day </td></tr> <tr> <td><a href="/wiki/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a></td> <td>0.45–0.9 mg/day</td> <td>0.9–1.8 mg/day</td> <td>1.8–3.6 mg/day </td></tr> <tr> <td>Conjugated estrogens</td> <td>0.3–0.45 mg/day</td> <td>0.625 mg/day</td> <td>0.9–1.25 mg/day </td></tr> <tr> <td><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></td> <td>0.3–0.45 mg/day</td> <td>0.625 mg/day</td> <td>0.9–1.25 mg/day </td></tr> <tr> <td><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></td> <td>0.75 mg/day</td> <td>1.5 mg/day</td> <td>3 mg/day </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>1–2 mg/day</td> <td>2–4 mg/day</td> <td>4–8 mg/day </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a>a</td> <td>2.5–10 μg/day</td> <td>5–20 μg/day</td> <td>– </td></tr> <tr> <td><a href="/wiki/Nasal_spray" title="Nasal spray">Nasal spray</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>150 μg/day</td> <td>300 μg/day</td> <td>600 μg/day </td></tr> <tr> <td><a href="/wiki/Transdermal_patch" title="Transdermal patch">Transdermal patch</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>25 μg/dayb</td> <td>50 μg/dayb</td> <td>100 μg/dayb </td></tr> <tr> <td><a href="/wiki/Transdermal_gel" class="mw-redirect" title="Transdermal gel">Transdermal gel</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>0.5 mg/day</td> <td>1–1.5 mg/day</td> <td>2–3 mg/day </td></tr> <tr> <td rowspan="2"><a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">Vaginal</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>25 μg/day</td> <td>–</td> <td>– </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>30 μg/day</td> <td>0.5 mg 2x/week</td> <td>0.5 mg/day </td></tr> <tr> <td rowspan="3"><a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular"><abbr title="Intramuscular">IM</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 Intramuscular or <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection"><abbr title="subcutaneous">SC</abbr> injection</a></td> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></td> <td>–</td> <td>–</td> <td>4 mg 1x/4 weeks </td></tr> <tr> <td><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></td> <td>1 mg 1x/3–4 weeks</td> <td>3 mg 1x/3–4 weeks</td> <td>5 mg 1x/3–4 weeks </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>0.5 mg 1x/week</td> <td>1 mg 1x/week</td> <td>1.5 mg 1x/week </td></tr> <tr> <td><a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant"><abbr title="Subcutaneous">SC</abbr> implant</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>25 mg 1x/6 months</td> <td>50 mg 1x/6 months</td> <td>100 mg 1x/6 months </td></tr> <tr class="sortbottom"> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = No longer used or recommended, due to health concerns. b = As a single patch applied once or twice per week (worn for 3–4 days or 7 days), depending on the formulation. Note: Dosages are not necessarily equivalent. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=2" title="Edit section: Available forms">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Conjugated_estrogens/medroxyprogesterone_acetate" title="Conjugated estrogens/medroxyprogesterone acetate">Conjugated estrogens/medroxyprogesterone acetate</a>, <a href="/wiki/Conjugated_estrogens/norgestrel" title="Conjugated estrogens/norgestrel">Conjugated estrogens/norgestrel</a>, <a href="/wiki/Conjugated_estrogens/methyltestosterone" title="Conjugated estrogens/methyltestosterone">Conjugated estrogens/methyltestosterone</a>, and <a href="/wiki/Conjugated_estrogens/bazedoxifene" class="mw-redirect" title="Conjugated estrogens/bazedoxifene">Conjugated estrogens/bazedoxifene</a></div> Natural CEEs, as Premarin, are available in the form of <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a> (0.3 mg, 0.625 mg, 0.9 mg, 1.25 mg, or 2.5 mg), <a href="/wiki/Cream_(pharmaceutical)" class="mw-redirect" title="Cream (pharmaceutical)">creams</a> for <a href="/wiki/Topical_medication" title="Topical medication">topical</a> or <a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">vaginal administration</a> (0.625 mg/g), and <a href="/wiki/Vial" title="Vial">vials</a> for <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">intravenous</a> or <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> (25 mg/vial).<a href="#cite_note-Drugs@FDA-2">[2]</a><a href="#cite_note-MorleyBerg1999-29">[29]</a> Synthetic CEEs, such as Cenestin (Synthetic A), Enjuvia (Synthetic B), and generic formulations, are available in the form of oral tablets (0.3 mg, 0.45 mg, 0.625 mg, 0.9 mg, or 1.25 mg) and creams for topical or vaginal administration (0.625 mg/g).<a href="#cite_note-Drugs@FDA-2">[2]</a><a href="#cite_note-Shorr2007-30">[30]</a> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=3" title="Edit section: Contraindications">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estrogen_(medication)#Contraindications" title="Estrogen (medication)">Estrogen (medication) § Contraindications</a></div> <a href="/wiki/Contraindication" title="Contraindication">Contraindications</a> of CEEs include <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> and a history of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a>, among others.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=4" title="Edit section: Side effects">edit</a>]</div> The most common <a href="/wiki/Side_effect" title="Side effect">side effects</a> associated with CEEs are vaginal <a href="/wiki/Yeast_infection" class="mw-redirect" title="Yeast infection">yeast infections</a>, <a href="/wiki/Metrorrhagia" class="mw-redirect" title="Metrorrhagia">vaginal spotting or bleeding</a>, <a href="/wiki/Dysmenorrhea" title="Dysmenorrhea">painful menses</a>, and <a href="/wiki/Cramp" title="Cramp">cramping</a> of the legs. While there are some contradictory data, estrogen alone does not appear to increase the risk of <a href="/wiki/Coronary_heart_disease" class="mw-redirect" title="Coronary heart disease">coronary heart disease</a> or breast cancer, unlike the case of estrogen in combination with certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> such as <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a> or <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>.<a href="#cite_note-31">[31]</a> Only a few clinical studies have assessed differences between oral CEEs and oral estradiol in terms of health parameters.<a href="#cite_note-pmid26327865-32">[32]</a> Oral CEEs have been found to possess a significantly greater risk of <a href="/wiki/Thromboembolism" title="Thromboembolism">thromboembolic</a> and <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> complications than oral estradiol (<a href="/wiki/Odds_ratio" title="Odds ratio"><abbr title="Odds ratio">OR</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 Odds ratio = 2.08) and oral <a href="/wiki/Esterified_estrogens" title="Esterified estrogens">esterified estrogens</a> (<a href="/wiki/Odds_ratio" title="Odds ratio"><abbr title="Odds ratio">OR</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 Odds ratio = 1.78).<a href="#cite_note-pmid26327865-32">[32]</a><a href="#cite_note-pmid24081194-33">[33]</a><a href="#cite_note-pmid15467060-34">[34]</a> However, in another study, the increase in <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> risk with oral CEEs plus medroxyprogesterone acetate and oral estradiol plus <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a> was found to be equivalent (<a href="/wiki/Relative_risk" title="Relative risk"><abbr title="Relative risk">RR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Relative risk = 4.0 and 3.9, respectively).<a href="#cite_note-pmid27998619-35">[35]</a><a href="#cite_note-pmid23136837-36">[36]</a> As of present, there are no <a href="/wiki/Randomized_controlled_trial" title="Randomized controlled trial">randomized controlled trials</a> that would allow for unambiguous conclusions.<a href="#cite_note-pmid26327865-32">[32]</a> <table class="wikitable mw-collapsible mw-collapsed" style="font-size: small; margin-left: auto; margin-right: auto; border: none; text-align:center;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Results_of_the_Women%27s_Health_Initiative_menopausal_hormone_therapy_randomized_controlled_trials" title="Template:Results of the Women's Health Initiative menopausal hormone therapy randomized controlled trials"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Results_of_the_Women%27s_Health_Initiative_menopausal_hormone_therapy_randomized_controlled_trials" title="Template talk:Results of the Women's Health Initiative menopausal hormone therapy randomized controlled trials"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Results_of_the_Women%27s_Health_Initiative_menopausal_hormone_therapy_randomized_controlled_trials" title="Special:EditPage/Template:Results of the Women's Health Initiative menopausal hormone therapy randomized controlled trials"><abbr title="Edit this template">e</abbr></a></li></ul></div> Results of the Women's Health Initiative (WHI) menopausal hormone therapy randomized controlled trials </caption> <tbody><tr> <th rowspan="2">Clinical outcome </th> <th rowspan="2">Hypothesized effect on risk </th> <th colspan="3"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a> and <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> (<a class="mw-selflink selflink"><abbr title="conjugated estrogens">CEs</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 conjugated estrogens 0.625 mg/day p.o. + <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate"><abbr title="medroxyprogesterone acetate">MPA</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 medroxyprogesterone acetate 2.5 mg/day p.o.) (n = 16,608, with uterus, 5.2–5.6 years follow up) </th> <th colspan="3"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a> alone (<a class="mw-selflink selflink"><abbr title="Conjugated estrogens">CEs</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 Conjugated estrogens 0.625 mg/day p.o.) (n = 10,739, no uterus, 6.8–7.1 years follow up) </th></tr> <tr> <th width="100px"><a href="/wiki/Hazard_ratio" title="Hazard ratio"><abbr title="Hazard ratio">HR</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 Hazard ratio </th> <th width="100px">95% <a href="/wiki/Confidence_interval" title="Confidence interval"><abbr title="Confidence interval">CI</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 Confidence interval </th> <th width="100px"><a href="/wiki/Attributable_risk" class="mw-redirect" title="Attributable risk"><abbr title="Attributable risk">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Attributable risk </th> <th width="100px"><a href="/wiki/Hazard_ratio" title="Hazard ratio"><abbr title="Hazard ratio">HR</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 Hazard ratio </th> <th width="100px">95% <a href="/wiki/Confidence_interval" title="Confidence interval"><abbr title="Confidence interval">CI</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 Confidence interval </th> <th width="100px"><a href="/wiki/Attributable_risk" class="mw-redirect" title="Attributable risk"><abbr title="Attributable risk">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Attributable risk </th></tr> <tr> <td style="text-align: left;"><a href="/wiki/Coronary_heart_disease" class="mw-redirect" title="Coronary heart disease">Coronary heart disease</a> </td> <td>Decreased </td> <td style="background: #ffcccb;">1.24 </td> <td>1.00–1.54 </td> <td style="background: #ffcccb;">+6 / 10,000 PYs </td> <td style="background: #cffbd4;">0.95 </td> <td>0.79–1.15 </td> <td style="background: #cffbd4;">−3 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Stroke" title="Stroke">Stroke</a> </td> <td>Decreased </td> <td style="background: #ffcccb;">1.31 </td> <td>1.02–1.68 </td> <td style="background: #ffcccb;">+8 / 10,000 PYs </td> <td style="background: #ffcccb;">1.37 </td> <td>1.09–1.73 </td> <td style="background: #ffcccb;">+12 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">Pulmonary embolism</a> </td> <td>Increased </td> <td style="background: #ffcccb;">2.13 </td> <td>1.45–3.11 </td> <td style="background: #ffcccb;">+10 / 10,000 PYs </td> <td style="background: #ffcccb;">1.37 </td> <td>0.90–2.07 </td> <td style="background: #ffcccb;">+4 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">Venous thromboembolism</a> </td> <td>Increased </td> <td style="background: #ffcccb;">2.06 </td> <td>1.57–2.70 </td> <td style="background: #ffcccb;">+18 / 10,000 PYs </td> <td style="background: #ffcccb;">1.32 </td> <td>0.99–1.75 </td> <td style="background: #ffcccb;">+8 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Breast_cancer" title="Breast cancer">Breast cancer</a> </td> <td>Increased </td> <td style="background: #ffcccb;">1.24 </td> <td>1.02–1.50 </td> <td style="background: #ffcccb;">+8 / 10,000 PYs </td> <td style="background: #cffbd4;">0.80 </td> <td>0.62–1.04 </td> <td style="background: #cffbd4;">−6 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Colorectal_cancer" title="Colorectal cancer">Colorectal cancer</a> </td> <td>Decreased </td> <td style="background: #cffbd4;">0.56 </td> <td>0.38–0.81 </td> <td style="background: #cffbd4;">−7 / 10,000 PYs </td> <td style="background: #ffcccb;">1.08 </td> <td>0.75–1.55 </td> <td style="background: #ffcccb;">+1 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Endometrial_cancer" title="Endometrial cancer">Endometrial cancer</a> </td> <td>– </td> <td style="background: #cffbd4;">0.81 </td> <td>0.48–1.36 </td> <td style="background: #cffbd4;">−1 / 10,000 PYs </td> <td>– </td> <td>– </td> <td>– </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Hip_fracture" title="Hip fracture">Hip fractures</a> </td> <td>Decreased </td> <td style="background: #cffbd4;">0.67 </td> <td>0.47–0.96 </td> <td style="background: #cffbd4;">−5 / 10,000 PYs </td> <td style="background: #cffbd4;">0.65 </td> <td>0.45–0.94 </td> <td style="background: #cffbd4;">−7 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;">Total <a href="/wiki/Bone_fracture" title="Bone fracture">fractures</a> </td> <td>Decreased </td> <td style="background: #cffbd4;">0.76 </td> <td>0.69–0.83 </td> <td style="background: #cffbd4;">−47 / 10,000 PYs </td> <td style="background: #cffbd4;">0.71 </td> <td>0.64–0.80 </td> <td style="background: #cffbd4;">−53 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;">Total <a href="/wiki/Mortality_rate" title="Mortality rate">mortality</a> </td> <td>Decreased </td> <td style="background: #cffbd4;">0.98 </td> <td>0.82–1.18 </td> <td style="background: #cffbd4;">−1 / 10,000 PYs </td> <td style="background: #ffcccb;">1.04 </td> <td>0.91–1.12 </td> <td style="background: #ffcccb;">+3 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;">Global index </td> <td>– </td> <td style="background: #ffcccb;">1.15 </td> <td>1.03–1.28 </td> <td style="background: #ffcccb;">+19 / 10,000 PYs </td> <td style="background: #ffcccb;">1.01 </td> <td>1.09–1.12 </td> <td style="background: #ffcccb;">+2 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Diabetes" title="Diabetes">Diabetes</a> </td> <td>– </td> <td style="background: #cffbd4;">0.79 </td> <td>0.67–0.93 </td> <td> </td> <td style="background: #cffbd4;">0.88 </td> <td>0.77–1.01 </td> <td> </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Gallbladder_disease" title="Gallbladder disease">Gallbladder disease</a> </td> <td>Increased </td> <td style="background: #ffcccb;">1.59 </td> <td>1.28–1.97 </td> <td> </td> <td style="background: #ffcccb;">1.67 </td> <td>1.35–2.06 </td> <td> </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Stress_incontinence" title="Stress incontinence">Stress incontinence</a> </td> <td>– </td> <td style="background: #ffcccb;">1.87 </td> <td>1.61–2.18 </td> <td> </td> <td style="background: #ffcccb;">2.15 </td> <td>1.77–2.82 </td> <td> </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Urge_incontinence" class="mw-redirect" title="Urge incontinence">Urge incontinence</a> </td> <td>– </td> <td style="background: #ffcccb;">1.15 </td> <td>0.99–1.34 </td> <td> </td> <td style="background: #ffcccb;">1.32 </td> <td>1.10–1.58 </td> <td> </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Peripheral_artery_disease" title="Peripheral artery disease">Peripheral artery disease</a> </td> <td>– </td> <td style="background: #cffbd4;">0.89 </td> <td>0.63–1.25 </td> <td> </td> <td style="background: #ffcccb;">1.32 </td> <td>0.99–1.77 </td> <td> </td></tr> <tr> <td style="text-align: left;">Probable <a href="/wiki/Dementia" title="Dementia">dementia</a> </td> <td>Decreased </td> <td style="background: #ffcccb;">2.05 </td> <td>1.21–3.48 </td> <td> </td> <td style="background: #ffcccb;">1.49 </td> <td>0.83–2.66 </td> <td> </td></tr> <tr> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;">Abbreviations: CEs = <a class="mw-selflink selflink">conjugated estrogens</a>. MPA = <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>. p.o. = <a href="/wiki/Per_oral" class="mw-redirect" title="Per oral">per oral</a>. HR = <a href="/wiki/Hazard_ratio" title="Hazard ratio">hazard ratio</a>. AR = <a href="/wiki/Attributable_risk" class="mw-redirect" title="Attributable risk">attributable risk</a>. PYs = <a href="/wiki/Person%E2%80%93years" class="mw-redirect" title="Person–years">person–years</a>. CI = <a href="/wiki/Confidence_interval" title="Confidence interval">confidence interval</a>. Notes: <a href="/wiki/Sample_size" class="mw-redirect" title="Sample size">Sample sizes</a> (n) include <a href="/wiki/Placebo" title="Placebo">placebo</a> recipients, which were about half of patients. "Global index" is defined for each woman as the time to earliest diagnosis for <a href="/wiki/Coronary_heart_disease" class="mw-redirect" title="Coronary heart disease">coronary heart disease</a>, <a href="/wiki/Stroke" title="Stroke">stroke</a>, <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a>, <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, <a href="/wiki/Colorectal_cancer" title="Colorectal cancer">colorectal cancer</a>, <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> (estrogen plus progestogen group only), <a href="/wiki/Hip_fracture" title="Hip fracture">hip fractures</a>, and <a href="/wiki/Death" title="Death">death</a> from other causes. Sources: See template. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="margin: 1em auto;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)" title="Template:Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)" title="Template talk:Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)" title="Special:EditPage/Template:Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)"><abbr title="Edit this template">e</abbr></a></li></ul></div> Risk of venous thromboembolism (VTE) with hormone therapy and birth control (QResearch/CPRD) </caption> <tbody><tr> <th class="unsortable">Type</th> <th class="unsortable">Route</th> <th class="unsortable">Medications</th> <th><a href="/wiki/Odds_ratio" title="Odds ratio">Odds ratio</a> (95% <a href="/wiki/Confidence_interval" title="Confidence interval"><abbr title="confidence interval">CI</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 confidence interval) </th></tr> <tr> <td rowspan="14"><a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">Menopausal hormone therapy</a></td> <td rowspan="10"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> alone     ≤1 mg/day     >1 mg/day</td> <td>1.27 (1.16–1.39)* 1.22 (1.09–1.37)* 1.35 (1.18–1.55)* </td></tr> <tr> <td>Conjugated estrogens alone     ≤0.625 mg/day     >0.625 mg/day</td> <td>1.49 (1.39–1.60)* 1.40 (1.28–1.53)* 1.71 (1.51–1.93)* </td></tr> <tr> <td><a href="/wiki/Estradiol/medroxyprogesterone_acetate" title="Estradiol/medroxyprogesterone acetate">Estradiol/medroxyprogesterone acetate</a></td> <td>1.44 (1.09–1.89)* </td></tr> <tr> <td><a href="/wiki/Estradiol/dydrogesterone" title="Estradiol/dydrogesterone">Estradiol/dydrogesterone</a>     ≤1 mg/day <abbr title="estradiol">E2</abbr>     >1 mg/day <abbr title="estradiol">E2</abbr></td> <td>1.18 (0.98–1.42) 1.12 (0.90–1.40) 1.34 (0.94–1.90) </td></tr> <tr> <td><a href="/wiki/Estradiol/norethisterone" title="Estradiol/norethisterone">Estradiol/norethisterone</a>     ≤1 mg/day <abbr title="estradiol">E2</abbr>     >1 mg/day <abbr title="estradiol">E2</abbr></td> <td>1.68 (1.57–1.80)* 1.38 (1.23–1.56)* 1.84 (1.69–2.00)* </td></tr> <tr> <td><a href="/wiki/Estradiol/norgestrel" class="mw-redirect" title="Estradiol/norgestrel">Estradiol/norgestrel</a> or <a href="/wiki/Estradiol/drospirenone" title="Estradiol/drospirenone">estradiol/drospirenone</a></td> <td>1.42 (1.00–2.03) </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens/medroxyprogesterone_acetate" title="Conjugated estrogens/medroxyprogesterone acetate">Conjugated estrogens/medroxyprogesterone acetate</a></td> <td>2.10 (1.92–2.31)* </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens/norgestrel" title="Conjugated estrogens/norgestrel">Conjugated estrogens/norgestrel</a>     ≤0.625 mg/day <abbr title="conjugated estrogens">CEEs</abbr>     >0.625 mg/day <abbr title="conjugated estrogens">CEEs</abbr></td> <td>1.73 (1.57–1.91)* 1.53 (1.36–1.72)* 2.38 (1.99–2.85)* </td></tr> <tr> <td><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a> alone</td> <td>1.02 (0.90–1.15) </td></tr> <tr> <td><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a> alone</td> <td>1.49 (1.24–1.79)* </td></tr> <tr> <td rowspan="2"><a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">Transdermal</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> alone    ≤50 μg/day    >50 μg/day</td> <td>0.96 (0.88–1.04) 0.94 (0.85–1.03) 1.05 (0.88–1.24) </td></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a>/<a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a></td> <td>0.88 (0.73–1.01) </td></tr> <tr> <td rowspan="2"><a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">Vaginal</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> alone</td> <td>0.84 (0.73–0.97) </td></tr> <tr> <td>Conjugated estrogens alone</td> <td>1.04 (0.76–1.43) </td></tr> <tr> <td rowspan="7"><a href="/wiki/Combined_birth_control" class="mw-redirect" title="Combined birth control">Combined birth control</a></td> <td rowspan="7"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td><a href="/wiki/Ethinylestradiol/norethisterone" title="Ethinylestradiol/norethisterone">Ethinylestradiol/norethisterone</a></td> <td>2.56 (2.15–3.06)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/levonorgestrel" title="Ethinylestradiol/levonorgestrel">Ethinylestradiol/levonorgestrel</a></td> <td>2.38 (2.18–2.59)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/norgestimate" class="mw-redirect" title="Ethinylestradiol/norgestimate">Ethinylestradiol/norgestimate</a></td> <td>2.53 (2.17–2.96)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/desogestrel" title="Ethinylestradiol/desogestrel">Ethinylestradiol/desogestrel</a></td> <td>4.28 (3.66–5.01)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/gestodene" title="Ethinylestradiol/gestodene">Ethinylestradiol/gestodene</a></td> <td>3.64 (3.00–4.43)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/drospirenone" title="Ethinylestradiol/drospirenone">Ethinylestradiol/drospirenone</a></td> <td>4.12 (3.43–4.96)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/cyproterone_acetate" title="Ethinylestradiol/cyproterone acetate">Ethinylestradiol/cyproterone acetate</a></td> <td>4.27 (3.57–5.11)* </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: (1) <a href="/wiki/Nested_case%E2%80%93control_study" title="Nested case–control study">Nested case–control studies</a> (2015, 2019) based on data from the <a href="/wiki/QResearch" title="QResearch">QResearch</a> and <a href="/wiki/Clinical_Practice_Research_Datalink" title="Clinical Practice Research Datalink">Clinical Practice Research Datalink</a> (CPRD) databases. (2) <a href="/wiki/Bioidentical_hormone_therapy" class="mw-redirect" title="Bioidentical hormone therapy">Bioidentical</a> <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> was not included, but is known to be associated with no additional risk relative to estrogen alone. Footnotes: * = <a href="/wiki/Statistical_significance" title="Statistical significance">Statistically significant</a> (p < 0.01). Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=5" title="Edit section: Overdose">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estrogen_(medication)#Overdose" title="Estrogen (medication)">Estrogen (medication) § Overdose</a></div> Estrogens, including CEEs, are relatively safe in acute <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=6" title="Edit section: Interactions">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estrogen_(medication)#Interactions" title="Estrogen (medication)">Estrogen (medication) § Interactions</a></div> <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">Inhibitors</a> and <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">inducers</a> of <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> may <a href="/wiki/Drug_interaction" title="Drug interaction">interact</a> with CEEs.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=7" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=8" title="Edit section: Pharmacodynamics">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Pharmacodynamics_of_estradiol" title="Pharmacodynamics of estradiol">Pharmacodynamics of estradiol</a></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Estradiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/225px-Estradiol.svg.png" decoding="async" width="225" height="142" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/338px-Estradiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/450px-Estradiol.svg.png 2x" data-file-width="512" data-file-height="324" /></a><figcaption><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a>, the main <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> of <a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">estrone sulfate</a> and the major active estrogen with CEEs<a href="#cite_note-pmid16112947-1">[1]</a></figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:17%CE%B2-Dihydroequilin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/17%CE%B2-Dihydroequilin.svg/225px-17%CE%B2-Dihydroequilin.svg.png" decoding="async" width="225" height="150" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/17%CE%B2-Dihydroequilin.svg/338px-17%CE%B2-Dihydroequilin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/17%CE%B2-Dihydroequilin.svg/450px-17%CE%B2-Dihydroequilin.svg.png 2x" data-file-width="1170" data-file-height="780" /></a><figcaption><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a>, the main <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> of <a href="/wiki/Equilin_sulfate" class="mw-redirect" title="Equilin sulfate">equilin sulfate</a> and the second major active estrogen with CEEs<a href="#cite_note-pmid16112947-1">[1]</a></figcaption></figure> CEEs are a combination of <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogens</a>, or <a href="/wiki/Agonist" title="Agonist">agonists</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a>.<a href="#cite_note-pmid16112947-1">[1]</a> The major estrogen in CEEs, <a href="/wiki/Sodium_estrone_sulfate" class="mw-redirect" title="Sodium estrone sulfate">sodium estrone sulfate</a>, itself is inactive, and rather serves as a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a> and then of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-Buchsbaum2012-37">[37]</a><a href="#cite_note-FalconeHurd2013-38">[38]</a> The transformation of estrone sulfate to estrone is catalyzed by <a href="/wiki/Steroid_sulfatase" title="Steroid sulfatase">steroid sulfatase</a>, and of estrone into estradiol by <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenase</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-Sanfilippo1998-39">[39]</a> CEEs (as Premarin) and estrone have been found to be equivalent in <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> in an <a href="/wiki/Animal_model" class="mw-redirect" title="Animal model">animal model</a> of estrogenic activity.<a href="#cite_note-FritzSperoff2012-7">[7]</a> On the other hand, the active forms of the equine estrogens in CEEs, such as <a href="/wiki/Equilin" title="Equilin">equilin</a> and <a href="/wiki/17%CE%B2-dihydroequilin" class="mw-redirect" title="17β-dihydroequilin">17β-dihydroequilin</a>, have greater <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> in the <a href="/wiki/Liver" title="Liver">liver</a> relative to <a href="/wiki/Bioidentical_hormone_therapy" class="mw-redirect" title="Bioidentical hormone therapy">bioidentical</a> <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>, similarly to <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> estrogens like <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> and <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>.<a href="#cite_note-pmid16112947-1">[1]</a> This results in disproportionate effects on <a href="/wiki/Liver_protein_production" class="mw-redirect" title="Liver protein production">liver protein production</a> compared to estradiol, although to a lesser extent than ethinylestradiol and diethylstilbestrol.<a href="#cite_note-pmid16112947-1">[1]</a> In addition, <a href="/wiki/17%CE%B2-dihydroequilenin" class="mw-redirect" title="17β-dihydroequilenin">17β-dihydroequilenin</a> has shown a <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a> (SERM)-like profile of estrogenic activity in studies with monkeys, in which beneficial effects on <a href="/wiki/Bone" title="Bone">bone</a> and the <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> system were observed but <a href="/wiki/Cell_proliferation" title="Cell proliferation">proliferative</a> responses in <a href="/wiki/Breast" title="Breast">breast</a> or <a href="/wiki/Endometrium" title="Endometrium">endometrium</a> were not seen, although the clinical significance of this is unknown.<a href="#cite_note-pmid17443713-40">[40]</a> CEEs consists of the <a href="/wiki/Sodium" title="Sodium">sodium</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> of the <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> <a href="/wiki/Ester" title="Ester">esters</a> of equine estrogens in a specific and consistent composition (see the table).<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a> The major estrogens in CEEs are <a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">sodium estrone sulfate</a> and <a href="/wiki/Sodium_equilin_sulfate" class="mw-redirect" title="Sodium equilin sulfate">sodium equilin sulfate</a>, which together account for approximately 71.5–92.0% of the total content of CEEs.<a href="#cite_note-Martindale-6">[6]</a><a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a> CEEs are <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a> of the active forms of the estrogens.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a><a href="#cite_note-Martindale-6">[6]</a> Sodium estrone sulfate is a prodrug of <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a>, which in turn is a prodrug of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>, while sodium equilin sulfate is a prodrug of <a href="/wiki/Equilin" title="Equilin">equilin</a> and then of 17β-dihydroequilin.<a href="#cite_note-pmid16112947-1">[1]</a> As such, the major active estrogens with CEEs are estradiol and 17β-dihydroequilin, which have <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> estrogenic activity and account for most of the effects of CEEs.<a href="#cite_note-pmid16112947-1">[1]</a> The 17α-estrogens in CEEs such as <a href="/wiki/17%CE%B1-estradiol" class="mw-redirect" title="17α-estradiol">17α-estradiol</a> and <a href="/wiki/17%CE%B1-dihydroequilin" class="mw-redirect" title="17α-dihydroequilin">17α-dihydroequilin</a> have low estrogenicity and are thought to contribute minimally to its effects.<a href="#cite_note-pmid16112947-1">[1]</a> There are many different <a href="/wiki/Steroid" title="Steroid">steroids</a> in natural CEE products like Premarin, as many as 230 compounds and including even <a href="/wiki/Androgen" title="Androgen">androgens</a> and <a href="/wiki/Progestogen" title="Progestogen">progestogens</a>, but only the estrogens are present in sufficient amounts to produce clinically-relevant effects.<a href="#cite_note-FritzSperoff2012-7">[7]</a><a href="#cite_note-pmid16915215-41">[41]</a><a href="#cite_note-pmid24176763-12">[12]</a> A dosage of 0.625 mg/day oral CEEs has been found to increase SHBG levels by 100%.<a href="#cite_note-pmid16915215-41">[41]</a><a href="#cite_note-pmid10914617-42">[42]</a> For comparison, 1 mg/day oral estradiol increased SHBG levels by 45%, while 50 μg/day transdermal estradiol increased SHBG levels by 12%.<a href="#cite_note-pmid16915215-41">[41]</a><a href="#cite_note-pmid10914617-42">[42]</a> <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> is more potent in its effects on liver protein synthesis than either CEEs or estradiol, with 10 μg/day oral ethinylestradiol having been found to be approximately equivalent to 1.25 mg/day CEEs.<a href="#cite_note-pmid16915215-41">[41]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Composition_of_conjugated_estrogens_and_properties_of_constituents" title="Template:Composition of conjugated estrogens and properties of constituents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Composition_of_conjugated_estrogens_and_properties_of_constituents" title="Template talk:Composition of conjugated estrogens and properties of constituents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Composition_of_conjugated_estrogens_and_properties_of_constituents" title="Special:EditPage/Template:Composition of conjugated estrogens and properties of constituents"><abbr title="Edit this template">e</abbr></a></li></ul></div> Composition of conjugated estrogens and properties of constituents </caption> <tbody><tr> <th>Compound</th> <th>Synonym</th> <th data-sort-type="number">Proportion (%)</th> <th>Relative <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> in the <a href="/wiki/Vagina" title="Vagina">vagina</a> (%)</th> <th data-sort-type="number">Relative potency in the <a href="/wiki/Uterus" title="Uterus">uterus</a> (%)</th> <th data-sort-type="number"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="Relative binding affinity">RBA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Relative binding affinity for <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> (%)</th> <th data-sort-type="number"><abbr title="Relative binding affinity">RBA</abbr> for <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> (%)</th> <th data-sort-type="number">ERα / ERβ <abbr title="Relative binding affinity">RBA</abbr> ratio </th></tr> <tr> <td>Conjugated estrogens</td> <td>–</td> <td>100</td> <td>38</td> <td>100</td> <td>–</td> <td>–</td> <td>– </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>–</td> <td>49.1–61.5</td> <td>30</td> <td>32</td> <td>26</td> <td>52</td> <td>0.50 </td></tr> <tr> <td><a href="/wiki/Equilin" title="Equilin">Equilin</a></td> <td>Δ7-Estrone</td> <td>22.4–30.5</td> <td>42</td> <td>80</td> <td>13</td> <td>49</td> <td>0.26 </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></td> <td>Δ7-17α-Estradiol</td> <td>13.5–19.5</td> <td>0.06</td> <td>2.6</td> <td>41</td> <td>32</td> <td>1.30 </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a></td> <td>–</td> <td>2.5–9.5</td> <td>0.11</td> <td>3.5</td> <td>19</td> <td>42</td> <td>0.45 </td></tr> <tr> <td><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">Δ8-Estrone</a></td> <td>–</td> <td>3.5–3.9</td> <td>?</td> <td>?</td> <td>19</td> <td>32</td> <td>0.60 </td></tr> <tr> <td><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></td> <td>Δ6,8-Estrone</td> <td>2.2–2.8</td> <td>1.3</td> <td>11.4</td> <td>15</td> <td>20–29</td> <td>0.50–0.75 </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></td> <td>Δ7-17β-Estradiol</td> <td>0.5–4.0</td> <td>83</td> <td>200</td> <td>113</td> <td>108</td> <td>1.05 </td></tr> <tr> <td><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></td> <td>Δ6,8-17α-Estradiol</td> <td>1.2–1.6</td> <td>0.018</td> <td>1.3</td> <td>20</td> <td>49</td> <td>0.40 </td></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">17β-Estradiol</a></td> <td>–</td> <td>0.56–0.9</td> <td>100</td> <td>?</td> <td>100</td> <td>100</td> <td>1.00 </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></td> <td>Δ6,8-17β-Estradiol</td> <td>0.5–0.7</td> <td>0.21</td> <td>9.4</td> <td>68</td> <td>90</td> <td>0.75 </td></tr> <tr> <td><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">Δ8-17β-Estradiol</a></td> <td>–</td> <td data-sort-value="0">Small amounts</td> <td>?</td> <td>?</td> <td>68</td> <td>72</td> <td>0.94 </td></tr> <tr class="sortbottom"> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: All listed compounds are present in conjugated estrogen products specifically in the form of the <a href="/wiki/Sodium" title="Sodium">sodium</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> of the <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> <a href="/wiki/Ester" title="Ester">esters</a> (i.e., as sodium estrone sulfate, sodium equilin sulfate, etc.). Sources: See template. </td></tr></tbody></table> <table class="wikitable plainrowheaders floatright" style="font-size: small; margin: 1em auto;"> <caption class="nowrap" style="font-size: 105%"><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:Oral_potencies_of_estrogens" title="Template:Oral potencies of estrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Oral_potencies_of_estrogens" title="Template talk:Oral potencies of estrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Oral_potencies_of_estrogens" title="Special:EditPage/Template:Oral potencies of estrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Potencies of oral estrogens<a href="#cite_note-62">[data sources 1]</a> </caption> <tbody><tr> <th scope="col" style="width=100px;" rowspan="2">Compound </th> <th scope="col" colspan="6">Dosage for specific uses (mg usually)<a href="#cite_note-63">[a]</a> </th></tr> <tr> <th scope="col" style="width=100px;"><abbr title="Endometrial threshold dose">ETD</abbr><a href="#cite_note-2-3-64">[b]</a> </th> <th scope="col" style="width=100px;"><abbr title="Endometrial proliferation dose">EPD</abbr><a href="#cite_note-2-3-64">[b]</a> </th> <th scope="col" style="width=100px;"><abbr title="Menopausal substitution dose">MSD</abbr><a href="#cite_note-2-3-64">[b]</a> </th> <th scope="col" style="width=100px;"><abbr title="Menopausal substitution dose">MSD</abbr><a href="#cite_note-daily-65">[c]</a> </th> <th scope="col" style="width=100px;"><abbr title="Ovulation-inhibiting dose">OID</abbr><a href="#cite_note-daily-65">[c]</a> </th> <th scope="col" style="width=100px;"><abbr title="Testosterone suppression dose">TSD</abbr><a href="#cite_note-daily-65">[c]</a> </th></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol (non-micronized)</a> </th> <td>30</td> <td>≥120–300</td> <td>120</td> <td>6</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol (micronized)</a> </th> <td>6–12</td> <td>60–80</td> <td>14–42</td> <td>1–2</td> <td>>5</td> <td>>8 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a> </th> <td>6–12</td> <td>60–80</td> <td>14–42</td> <td>1–2</td> <td>-</td> <td>>8 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a> </th> <td>-</td> <td>60–140</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a> </th> <td>≥20</td> <td>120–150<a href="#cite_note-div-66">[d]</a></td> <td>28–126</td> <td>1–6</td> <td>>5</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estriol_succinate" title="Estriol succinate">Estriol succinate</a> </th> <td>-</td> <td>140–150<a href="#cite_note-div-66">[d]</a></td> <td>28–126</td> <td>2–6</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a> </th> <td>12</td> <td>60</td> <td>42</td> <td>2</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;">Conjugated estrogens </th> <td>5–12</td> <td>60–80</td> <td>8.4–25</td> <td>0.625–1.25</td> <td>>3.75</td> <td>7.5 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> </th> <td>200 μg</td> <td>1–2</td> <td>280 μg</td> <td>20–40 μg</td> <td>100 μg</td> <td>100 μg </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a> </th> <td>300 μg</td> <td>1.5–3.0</td> <td>300–600 μg</td> <td>25–30 μg</td> <td>>80 μg</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a> </th> <td>300 μg</td> <td>2–4</td> <td>500 μg</td> <td>25–50 μg</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a> </th> <td>-</td> <td>2</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> </th> <td>2.5</td> <td>20–30</td> <td>11</td> <td>0.5–2.0</td> <td>>5</td> <td>3 </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Diethylstilbestrol_dipropionate" title="Diethylstilbestrol dipropionate">DES dipropionate</a> </th> <td>-</td> <td>15–30</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> </th> <td>5</td> <td>30–40</td> <td>42</td> <td>0.5–4.0</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a> </th> <td>3–5</td> <td>30–60</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> </th> <td>-</td> <td>70–110</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a> </th> <td>-</td> <td>>100</td> <td>-</td> <td>-</td> <td>>48</td> <td>- </td></tr> <tr> <th scope="row" style="background: #f8f9fa;"><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a> </th> <td>-</td> <td>400</td> <td>-</td> <td>-</td> <td>-</td> <td>- </td></tr> <tr class="sortbottom"> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;"><style data-mw-deduplicate="TemplateStyles:r1214851843">.mw-parser-output .hidden-begin{box-sizing:border-box;width:100%;padding:5px;border:none;font-size:95%}.mw-parser-output .hidden-title{font-weight:bold;line-height:1.6;text-align:left}.mw-parser-output .hidden-content{text-align:left}@media all and (max-width:500px){.mw-parser-output .hidden-begin{width:auto!important;clear:none!important;float:none!important}}</style><div class="hidden-begin mw-collapsible mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="text-align:center;">Sources and footnotes:</div><div class="hidden-content mw-collapsible-content" style=""> <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"><ol class="references"> <li id="cite_note-62"><a href="#cite_ref-62">^</a> <a href="#cite_note-pmid2215269-43">[43]</a><a href="#cite_note-pmid559617-44">[44]</a><a href="#cite_note-WolfSchneider2013-45">[45]</a><a href="#cite_note-GöretzlehnerLauritzen2012-46">[46]</a><a href="#cite_note-KnörrBeller2013-47">[47]</a><a href="#cite_note-HorskyPresl1981-48">[48]</a> <a href="#cite_note-Pschyrembel1968-49">[49]</a><a href="#cite_note-pmid779393-50">[50]</a><a href="#cite_note-Lauritzen1975-51">[51]</a><a href="#cite_note-Kopera1991-52">[52]</a> <a href="#cite_note-pmid29603164-53">[53]</a><a href="#cite_note-pmid29756046-54">[54]</a><a href="#cite_note-Rydén1950-55">[55]</a><a href="#cite_note-pmid14902290-56">[56]</a><a href="#cite_note-Kottmeier1947-57">[57]</a><a href="#cite_note-RietbrockStaib2013-58">[58]</a><a href="#cite_note-Greenblatt1966-59">[59]</a><a href="#cite_note-HerrRevesz1970-60">[60]</a><a href="#cite_note-pmid13370006-61">[61]</a> </li> </ol></div></div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-63"><a href="#cite_ref-63">^</a> Dosages are given in milligrams unless otherwise noted. </li> <li id="cite_note-2-3-64">^ <a href="#cite_ref-2-3_64-0">a</a> <a href="#cite_ref-2-3_64-1">b</a> <a href="#cite_ref-2-3_64-2">c</a> Dosed every 2 to 3 weeks </li> <li id="cite_note-daily-65">^ <a href="#cite_ref-daily_65-0">a</a> <a href="#cite_ref-daily_65-1">b</a> <a href="#cite_ref-daily_65-2">c</a> Dosed daily </li> <li id="cite_note-div-66">^ <a href="#cite_ref-div_66-0">a</a> <a href="#cite_ref-div_66-1">b</a> In divided doses, 3x/day; irregular and atypical proliferation. </li> </ol></div></div></div></div> </td></tr></tbody></table> <table style="font-size: small; margin-left: auto; margin-right: auto; border: none;" class="wikitable sortable mw-collapsible mw-collapsed"> <caption class="nowrap" style="font-size: 105%;"><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:Relative_oral_potencies_of_estrogens" title="Template:Relative oral potencies of estrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_oral_potencies_of_estrogens" title="Template talk:Relative oral potencies of estrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_oral_potencies_of_estrogens" title="Special:EditPage/Template:Relative oral potencies of estrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Relative oral potencies of estrogens </caption> <tbody><tr> <th>Estrogen</th> <th data-sort-type="number"><a href="/wiki/Hot_flashes" class="mw-redirect" title="Hot flashes"><abbr title="Hot flashes">HF</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 Hot flashes</th> <th data-sort-type="number"><a href="/wiki/Vaginal_epithelium" title="Vaginal epithelium"><abbr title="Vaginal epithelium">VE</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 Vaginal epithelium</th> <th data-sort-type="number"><a href="/wiki/Urinary_calcium" title="Urinary calcium"><abbr title="Urinary calcium">UCa</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 Urinary calcium</th> <th data-sort-type="number"><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</th> <th data-sort-type="number"><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</th> <th data-sort-type="number"><a href="/wiki/High-density_lipoprotein" title="High-density lipoprotein"><abbr title="High-density lipoprotein">HDL</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 High-density lipoprotein-<a href="/wiki/Cholesterol" title="Cholesterol"><abbr title="Cholesterol">C</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 Cholesterol</th> <th data-sort-type="number"><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</th> <th data-sort-type="number"><a href="/wiki/Corticosteroid-binding_globulin" class="mw-redirect" title="Corticosteroid-binding globulin"><abbr title="Corticosteroid-binding globulin">CBG</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 Corticosteroid-binding globulin</th> <th data-sort-type="number"><a href="/wiki/Angiotensinogen" class="mw-redirect" title="Angiotensinogen"><abbr title="Angiotensinogen">AGT</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 Angiotensinogen</th> <th data-sort-type="number"><abbr title="Ratio of liver estrogenic effects to general/systemic estrogenic effects)">Liver</abbr> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0</td> <td>1.0 </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>?</td> <td>?</td> <td>?</td> <td>0.3</td> <td>0.3</td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>? </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>0.3</td> <td>0.3</td> <td>0.1</td> <td>0.3</td> <td>0.3</td> <td>0.2</td> <td>?</td> <td>?</td> <td>?</td> <td>0.67 </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></td> <td>?</td> <td>0.9</td> <td>0.9</td> <td>0.8–0.9</td> <td>0.9</td> <td>0.5</td> <td>0.9</td> <td>0.5–0.7</td> <td>1.4–1.5</td> <td>0.56–1.7 </td></tr> <tr> <td>Conjugated estrogens</td> <td>1.2</td> <td>1.5</td> <td>2.0</td> <td>1.1–1.3</td> <td>1.0</td> <td>1.5</td> <td>3.0–3.2</td> <td>1.3–1.5</td> <td>5.0</td> <td>1.3–4.5 </td></tr> <tr> <td><a href="/wiki/Equilin_sulfate" class="mw-redirect" title="Equilin sulfate">Equilin sulfate</a></td> <td>?</td> <td>?</td> <td>1.0</td> <td>?</td> <td>?</td> <td>6.0</td> <td>7.5</td> <td>6.0</td> <td>7.5</td> <td>? </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></td> <td>120</td> <td>150</td> <td>400</td> <td>60–150</td> <td>100</td> <td>400</td> <td>500–600</td> <td>500–600</td> <td>350</td> <td>2.9–5.0 </td></tr> <tr> <td><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></td> <td>?</td> <td>?</td> <td>?</td> <td>2.9–3.4</td> <td>?</td> <td>?</td> <td>26–28</td> <td>25–37</td> <td>20</td> <td>5.7–7.5 </td></tr> <tr class="sortbottom"> <td colspan="11" style="width: 1px; background-color:#eaecf0; text-align: center;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1214851843"><div class="hidden-begin mw-collapsible mw-collapsed" style=""><div class="hidden-title skin-nightmode-reset-color" style="text-align:center;">Sources and footnotes</div><div class="hidden-content mw-collapsible-content" style=""> Notes: Values are ratios, with estradiol as standard (i.e., 1.0). Abbreviations: <abbr title="Hot flashes">HF</abbr> = Clinical relief of <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>. <abbr title="Vaginal epithelium">VE</abbr> = Increased <a href="/wiki/Cell_proliferation" title="Cell proliferation">proliferation</a> of <a href="/wiki/Vaginal_epithelium" title="Vaginal epithelium">vaginal epithelium</a>. <abbr title="Urinary calcium">UCa</abbr> = Decrease in <a href="/wiki/Urinary_calcium" title="Urinary calcium"><abbr title="urinary calcium">UCa</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 urinary calcium. <abbr title="follicle-stimulating hormone">FSH</abbr> = Suppression of <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 levels. <abbr title="luteinizing hormone">LH</abbr> = Suppression of <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 levels. <abbr title="high-density lipoprotein">HDL</abbr>-<abbr title="cholesterol">C</abbr>, <abbr title="sex hormone-binding globulin">SHBG</abbr>, <abbr title="corticosteroid-binding globulin">CBG</abbr>, and <abbr title="angiotensinogen">AGT</abbr> = Increase in the serum levels of these <a href="/wiki/Liver_protein" class="mw-redirect" title="Liver protein">liver proteins</a>. Liver = Ratio of liver estrogenic effects to general/systemic estrogenic effects (hot flashes/<a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropins</a>). Sources: See template.</div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Antigonadotropic_effects">Antigonadotropic effects</h4>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=9" title="Edit section: Antigonadotropic effects">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png/300px-Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png" decoding="async" width="300" height="198" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png/450px-Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f6/Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png/600px-Testosterone_levels_with_different_estrogen_therapies_in_men_with_prostate_cancer.png 2x" data-file-width="2046" data-file-height="1348" /></a><figcaption>Testosterone levels with no treatment and with various estrogens in men with prostate cancer.<a href="#cite_note-pmid4359746-67">[62]</a> Determinations were made with an early <a href="/wiki/Radioimmunoassay" title="Radioimmunoassay">radioimmunoassay</a> (RIA).<a href="#cite_note-pmid4359746-67">[62]</a></figcaption></figure> A preliminary study of <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> inhibition in women found that oral CEEs was 33% effective at 1.25 mg/day and 94% at 3.75 mg/day.<a href="#cite_note-Greenblatt1966e-68">[63]</a><a href="#cite_note-HerrRevesz19702-69">[64]</a> A dosage of oral CEEs of 2.5 mg three times daily (7.5 mg/day total) has been found to suppress total testosterone levels in men to an equivalent extent as 3 mg/day oral <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>, which is the minimum dosage of diethylstilbestrol required to consistently suppress total testosterone levels into the castrate range (<50 ng/dL).<a href="#cite_note-pmid29603164e-70">[65]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=10" title="Edit section: Pharmacokinetics">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Pharmacokinetics_of_estradiol" title="Pharmacokinetics of estradiol">Pharmacokinetics of estradiol</a></div> CEEs are <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> in the <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestines</a> during first-pass metabolism upon <a href="/wiki/Oral_administration" title="Oral administration">oral administration</a>.<a href="#cite_note-pmid8842581-71">[66]</a><a href="#cite_note-Martindale-6">[6]</a> Following their <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a>, they are <a href="/wiki/Sulfation" title="Sulfation">resulfated</a> mainly in the <a href="/wiki/Liver" title="Liver">liver</a> also during the first pass.<a href="#cite_note-pmid8842581-71">[66]</a> Following this, they serve as a circulating reservoir and are slowly rehydrolyzed into their unconjugated active forms.<a href="#cite_note-pmid8842581-71">[66]</a> Oral CEEs, at a daily dosage of 0.625 mg, achieve estrone and estradiol levels of 150 pg/mL and 30–50 pg/mL, respectively, while a daily oral dosage of 1.25 mg achieves levels of 120–200 pg/mL and 40–60 pg/mL of estrone and estradiol, respectively.<a href="#cite_note-Lobo2007-72">[67]</a> The oral ingestion of 10 mg CEEs, which contains about 4.5 mg sodium estrone sulfate and 2.5 mg sodium equilin sulfate, produces maximal plasma concentrations of estrone and equilin of 1,400 pg/mL and 560 pg/mL within three and five hours, respectively.<a href="#cite_note-Lobo2007-72">[67]</a> By 24 hours post-dose of 10 mg, the levels of estrone and equilin fall to 280 pg/mL and 125 pg/mL, respectively.<a href="#cite_note-Lobo2007-72">[67]</a> Oral CEEs 1.25 mg/daily and oral micronized estradiol 1 mg/daily result in similar plasma concentrations of estrone and estradiol (150–300 pg/mL and 30–50 pg/mL for micronized estradiol, respectively) (oral estradiol is extensively metabolized into estrone during <a href="/wiki/Hepatic" class="mw-redirect" title="Hepatic">hepatic</a> <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a>),<a href="#cite_note-Lobo2007-72">[67]</a> although this does not account for equilin and other equine estrogens involved in the effects of CEEs, which may be significantly more potent in comparison to estrone.<a href="#cite_note-NotelovitzKeep2012-73">[68]</a><a href="#cite_note-Seidel1974-74">[69]</a> The <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of vaginal CEEs<a href="#cite_note-pmid7231202-75">[70]</a> and of intravenous CEEs have been studied as well.<a href="#cite_note-pmid3653846-76">[71]</a> Eoncentrations of equilin that are very high relative to those of other estrogens are produced by typical clinical doses of CEEs.<a href="#cite_note-WallachHammond1982-77">[72]</a> With a dosage of 1.25 mg oral CEEs, equilin levels of 1,082 to 2,465 pg/mL have been observed.<a href="#cite_note-WallachHammond1982-77">[72]</a> The clinical significance of these levels of equilin is unknown.<a href="#cite_note-WallachHammond1982-77">[72]</a> The active forms are <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> primarily in the liver.<a href="#cite_note-Martindale-6">[6]</a> There is some <a href="/wiki/Enterohepatic_recirculation" class="mw-redirect" title="Enterohepatic recirculation">enterohepatic recirculation</a> of CEEs.<a href="#cite_note-Martindale-6">[6]</a> Following a single oral dose of 0.625 CEEs, the <a href="/wiki/Biological_half-life" title="Biological half-life">biological half-life</a> of estrone was 26.7 hours, of baseline-adjusted estrone was 14.8 hours, and of equilin was 11.4 hours.<a href="#cite_note-DrugBank-5">[5]</a>[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">unreliable medical source?</a>] <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Plasma_estrogen_levels_after_a_single_dose_of_conjugated_estrogens_by_different_routes" title="Template:Plasma estrogen levels after a single dose of conjugated estrogens by different routes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Plasma_estrogen_levels_after_a_single_dose_of_conjugated_estrogens_by_different_routes" title="Template talk:Plasma estrogen levels after a single dose of conjugated estrogens by different routes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Plasma_estrogen_levels_after_a_single_dose_of_conjugated_estrogens_by_different_routes" title="Special:EditPage/Template:Plasma estrogen levels after a single dose of conjugated estrogens by different routes"><abbr title="Edit this template">e</abbr></a></li></ul></div> Plasma estrogen levels after a single dose of conjugated estrogens by different routes </caption> <tbody><tr> <th>Route</th> <th>Dose</th> <th><abbr title="Time (at which estrogen levels were assessed after last dose)">Time</abbr></th> <th><abbr title="Estradiol">E2</abbr> (<abbr title="increase or change">↑Δ</abbr>)</th> <th><abbr title="Estrone">E1</abbr> (<abbr title="increase or change">↑Δ</abbr>)</th> <th><abbr title="Ratio (E2:E1)">Ratio</abbr> </th></tr> <tr> <td><a href="/wiki/Oral_administration" title="Oral administration">Oral</a>  </td> <td>0.3 mg 0.625 mg 1.25 mg 1.25 mg 2.5 mg</td> <td>6 hours 6 hours 6 hours 1 hour 6 hours</td> <td>+20 pg/mL +50 pg/mL +70 pg/mL +35–58 pg/mL +160 pg/mL</td> <td><abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr> 110 pg/mL <abbr title="No data">ND</abbr></td> <td><abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr> 0.32–0.52 <abbr title="No data">ND</abbr> </td></tr> <tr> <td><a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">Vaginal</a> (<a href="/wiki/Cream_(pharmaceutical)" class="mw-redirect" title="Cream (pharmaceutical)">cream</a>)</td> <td>0.3 mg 0.625 mg 0.625 mg 1.25 mg 1.25 mg 2.5 mg</td> <td><abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr> 2 hours <abbr title="No data">ND</abbr> <abbr title="No data">ND</abbr></td> <td>+4 pg/mL +13–29 pg/mL +17 pg/mL +25 pg/mL +27 pg/mL +32 pg/mL</td> <td>+20 pg/mL +29–55 pg/mL +45 pg/mL +50 pg/mL +110 pg/mL +40 pg/mL</td> <td>0.2 0.24–1.0 0.38 0.5 0.25 0.8 </td></tr> <tr> <td><a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">Intravenous</a>a</td> <td>20 mg</td> <td>5 min 30 min 60 min 120 min</td> <td>800 pg/mL 3000 pg/mL 3500 pg/mL 3100 pg/mL</td> <td>4500 pg/mL 24000 pg/mL 19000 pg/mL 10500 pg/mL</td> <td>1:5.3 1:8.1 1:5.5 1:3.4 </td></tr> <tr class="sortbottom"> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: a = Absolute levels, not change. Sources: See template. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Protein_binding_and_metabolic_clearance_rates_of_estrogens" title="Template:Protein binding and metabolic clearance rates of estrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Protein_binding_and_metabolic_clearance_rates_of_estrogens" title="Template talk:Protein binding and metabolic clearance rates of estrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Protein_binding_and_metabolic_clearance_rates_of_estrogens" title="Special:EditPage/Template:Protein binding and metabolic clearance rates of estrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Protein binding and metabolic clearance rates of estrogens </caption> <tbody><tr> <th>Compound</th> <th data-sort-type="number"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="Relative binding affinity">RBA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Relative binding affinity to <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip sex hormone-binding globulin (%)</th> <th data-sort-type="number">Bound to <abbr title="sex hormone-binding globulin">SHBG</abbr> (%)</th> <th data-sort-type="number">Bound to <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> (%)</th> <th data-sort-type="number"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Total bound</a> (%)</th> <th data-sort-type="number"><a href="/wiki/Metabolic_clearance_rate" class="mw-redirect" title="Metabolic clearance rate"><abbr title="Metabolic clearance rate">MCR</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 Metabolic clearance rate (L/day/m2) </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">17β-Estradiol</a></td> <td>50</td> <td>37</td> <td>61</td> <td>98</td> <td>580 </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>12</td> <td>16</td> <td>80</td> <td>96</td> <td>1050 </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>0.3</td> <td>1</td> <td>91</td> <td>92</td> <td>1110 </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></td> <td>0</td> <td>0</td> <td>99</td> <td>99</td> <td>80 </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></td> <td>30</td> <td>?</td> <td>?</td> <td>?</td> <td>1250 </td></tr> <tr> <td><a href="/wiki/Equilin" title="Equilin">Equilin</a></td> <td>8</td> <td>26</td> <td>13</td> <td>?</td> <td>2640 </td></tr> <tr> <td><a href="/wiki/17%CE%B2-Dihydroequilin_sulfate" class="mw-redirect" title="17β-Dihydroequilin sulfate">17β-Dihydroequilin sulfate</a></td> <td>0</td> <td>?</td> <td>?</td> <td>?</td> <td>375 </td></tr> <tr> <td><a href="/wiki/Equilin_sulfate" class="mw-redirect" title="Equilin sulfate">Equilin sulfate</a></td> <td>0</td> <td>?</td> <td>?</td> <td>?</td> <td>175 </td></tr> <tr> <td><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">Δ8-Estrone</a></td> <td>?</td> <td>?</td> <td>?</td> <td>?</td> <td>1710 </td></tr> <tr class="sortbottom"> <td colspan="6" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: <abbr title="Relative binding affinity">RBA</abbr> for <abbr title="sex hormone-binding globulin">SHBG</abbr> (%) is compared to 100% for <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=11" title="Edit section: Chemistry">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_estrogens" title="List of estrogens">List of estrogens</a>, <a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a>, and <a href="/wiki/Estrogen_conjugate" title="Estrogen conjugate">Estrogen conjugate</a></div> CEEs are <a href="/wiki/Natural_product" title="Natural product">naturally occurring</a> <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroids</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a> They are in <a href="/wiki/Conjugate_(biochemistry)" class="mw-redirect" title="Conjugate (biochemistry)">conjugate</a> form, as the <a href="/wiki/Sodium" title="Sodium">sodium</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salts</a> of the C17β <a href="/wiki/Sulfate" title="Sulfate">sulfate</a> <a href="/wiki/Ester" title="Ester">esters</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a> The estrogens in CEEs, in their unconjugated active forms, include <a href="/wiki/Bioidentical_hormone_therapy" class="mw-redirect" title="Bioidentical hormone therapy">bioidentical</a> human estrogens like <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> and <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a> as well as <a href="/wiki/Equine_estrogen" title="Equine estrogen">equine-specific estrogens</a> such as <a href="/wiki/Equilin" title="Equilin">equilin</a> and <a href="/wiki/17%CE%B2-dihydroequilin" class="mw-redirect" title="17β-dihydroequilin">17β-dihydroequilin</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a> The equine estrogens differ from human estrogens in that they have additional <a href="/wiki/Double_bond" title="Double bond">double bonds</a> in the B <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> of the steroid <a href="/wiki/Ring_system_(chemistry)" class="mw-redirect" title="Ring system (chemistry)">nucleus</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a> CEEs contain both 17β-estrogens like estradiol and 17β-dihydroequilin and the C17α <a href="/wiki/Epimer" title="Epimer">epimers</a> like <a href="/wiki/17%CE%B1-estradiol" class="mw-redirect" title="17α-estradiol">17α-estradiol</a> and <a href="/wiki/17%CE%B1-dihydroequilin" class="mw-redirect" title="17α-dihydroequilin">17α-dihydroequilin</a>.<a href="#cite_note-pmid16112947-1">[1]</a><a href="#cite_note-FritzSperoff2012-7">[7]</a> <table role="presentation" cellpadding="0" style="border-spacing:0; margin-left: auto; margin-right: auto; border: none;"> <tbody><tr> <td><div class="thumb center" style="margin: 1em auto;"> <div class="thumbinner" style="width:802px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: aliceblue;margin-bottom:3px;"><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:Chemical_structures_of_equine_estrogens" title="Template:Chemical structures of equine estrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_structures_of_equine_estrogens" title="Template talk:Chemical structures of equine estrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_structures_of_equine_estrogens" title="Special:EditPage/Template:Chemical structures of equine estrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div> Chemical structures of equine estrogens<a href="#cite_note-pmid24176763-12">[12]</a><a href="#cite_note-pmid18599548-78">[73]</a></div> <div style="position:relative; width:800px; height:477px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:800px; position:absolute"> <img alt="Chemical structures of equine estrogens" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Chemical_structures_of_equine_estrogens_no_labels.png/800px-Chemical_structures_of_equine_estrogens_no_labels.png" decoding="async" width="800" height="477" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/db/Chemical_structures_of_equine_estrogens_no_labels.png/1200px-Chemical_structures_of_equine_estrogens_no_labels.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/db/Chemical_structures_of_equine_estrogens_no_labels.png/1600px-Chemical_structures_of_equine_estrogens_no_labels.png 2x" data-file-width="3435" data-file-height="2050" /> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_205x185" style="position:absolute; left:205px; top:185px; line-height:110%;"><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></div> <div id="annotation_190x315" style="position:absolute; left:190px; top:315px; line-height:110%;"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">17β-Estradiol</a></div> <div id="annotation_190x443" style="position:absolute; left:190px; top:443px; line-height:110%;"><a href="/wiki/Alfatradiol" title="Alfatradiol">17α-Estradiol</a></div> <div id="annotation_375x185" style="position:absolute; left:375px; top:185px; line-height:110%;"><a href="/wiki/Equilin" title="Equilin">Equilin</a></div> <div id="annotation_332x315" style="position:absolute; left:332px; top:315px; line-height:110%;"><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></div> <div id="annotation_332x443" style="position:absolute; left:332px; top:443px; line-height:110%;"><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></div> <div id="annotation_533x185" style="position:absolute; left:533px; top:185px; line-height:110%;"><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></div> <div id="annotation_487x315" style="position:absolute; left:487px; top:315px; line-height:110%;"><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></div> <div id="annotation_487x443" style="position:absolute; left:487px; top:443px; line-height:110%;"><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></div> <div id="annotation_685x185" style="position:absolute; left:685px; top:185px; line-height:110%;"><a href="/wiki/%CE%948-Estrone" class="mw-redirect" title="Δ8-Estrone">Δ8-Estrone</a></div> <div id="annotation_666x315" style="position:absolute; left:666px; top:315px; line-height:110%;"><a href="/wiki/%CE%948-17%CE%B2-Estradiol" class="mw-redirect" title="Δ8-17β-Estradiol">Δ8-17β-Estradiol</a></div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/18px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/27px-Interactive_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/36px-Interactive_icon.svg.png 2x" data-file-width="133" data-file-height="200" /></div>This diagram illustrates the chemical structures of the active/unconjugated forms of the equine estrogens present in conjugated estrogens.</div> </div> </div> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=12" title="Edit section: History">edit</a>]</div> <a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a>, an <a href="/wiki/Extract" title="Extract">extract</a> of the <a href="/wiki/Urine" title="Urine">urine</a> of <a href="/wiki/Pregnancy" title="Pregnancy">pregnant</a> women and sold under the brand names Progynon and Emmenin in the 1930s, was the predecessor of Premarin.<a href="#cite_note-FeldbergLadd-Taylor2003-79">[74]</a> Both of these products contained conjugated estrogens similarly to Premarin, but the estrogens were human estrogens as opposed to equine estrogens and the composition differed. The major active ingredient in Progynon and Emmenin was <a href="/wiki/Estriol_glucuronide" title="Estriol glucuronide">estriol glucuronide</a>. Estrone sulfate was first isolated from the urine of pregnant mares in the late 1930s by researchers in the Department of Biochemistry at <a href="/wiki/University_of_Toronto" title="University of Toronto">University of Toronto</a>.<a href="#cite_note-SchachterMarrian1938-80">[75]</a> Premarin was first introduced in 1941 by Wyeth Ayerst as a treatment for <a href="/wiki/Hot_flashes" class="mw-redirect" title="Hot flashes">hot flashes</a> and other symptoms of menopause; at that time, Wyeth Ayerst only had to prove its safety, and not its efficacy.<a href="#cite_note-MDD-81">[76]</a> In response to the 1962 <a href="/wiki/Kefauver_Harris_Amendment" class="mw-redirect" title="Kefauver Harris Amendment">Kefauver Harris Amendment</a> the FDA had its efficacy reviewed, and in 1972 found it effective for menopausal symptoms and probably effective for osteoporosis.<a href="#cite_note-82">[77]</a> The review also determined that two estrogens – estrone sulfate and equilin sulfate – were primarily responsible for the activity of Premarin, and it laid the groundwork for Abbreviated New Drug Application (ANDA) submissions of generic versions.<a href="#cite_note-MDD-81">[76]</a> In 1984 an NIH consensus panel found that estrogens were effective for preventing osteoporosis<a href="#cite_note-83">[78]</a> and 1986 the FDA announced in the Federal Register that Premarin was effective for preventing osteoporosis.<a href="#cite_note-Woodcock1997-84">[79]</a> This announcement led to a rapid growth in sales, and interest from generic manufacturers to introduce generic versions.<a href="#cite_note-MDD-81">[76]</a> Conjugated estrogens was introduced for medical use under the brand name Premarin in <a href="/wiki/Canada" title="Canada">Canada</a> in 1941, in the <a href="/wiki/United_States" title="United States">United States</a> in 1942, and in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> in 1956.<a href="#cite_note-PanayBriggs2015-85">[80]</a> The manufacturer of Premarin secretly paid <a href="/wiki/Gynecologist" class="mw-redirect" title="Gynecologist">gynecologist</a> <a href="/wiki/Robert_A._Wilson_(gynecologist)" title="Robert A. Wilson (gynecologist)">Robert A. Wilson</a> to promote its use by <a href="/wiki/Menopause" title="Menopause">menopausal</a> women in his 1966 book, <a href="/wiki/Feminine_Forever" title="Feminine Forever">Feminine Forever</a>, leading to increased sales.<a href="#cite_note-Dominus2023-86">[81]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=13" title="Edit section: Society and culture">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Names">Names</h3>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=14" title="Edit section: Names">edit</a>]</div> Estrogens, conjugated is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/United_States_Pharmacopeia" title="United States Pharmacopeia"><abbr title="United States Pharmacopeia">USP</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 Pharmacopeia and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name.<a href="#cite_note-ChemIDplus-87">[82]</a> It is also known as conjugated estrogens or as conjugated equine estrogens.<a href="#cite_note-DrugBank-5">[5]</a>[<a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)">unreliable medical source?</a>] The brand name Premarin is a contraction of "pregnant mares' urine".<a href="#cite_note-pmid23217066-88">[83]</a><a href="#cite_note-pmid15845914-89">[84]</a><a href="#cite_note-pmid21189221-90">[85]</a> CEEs are marketed under a large number of brand names throughout the world.<a href="#cite_note-Martindale-6">[6]</a> The major brand name of the natural form of CEEs manufactured from the urine of pregnant mares is Premarin.<a href="#cite_note-Martindale-6">[6]</a> Major brand names of fully synthetic versions of CEEs include Cenestin and Enjuvia in the <a href="/wiki/United_States" title="United States">United States</a> and C.E.S. and Congest in <a href="/wiki/Canada" title="Canada">Canada</a>.<a href="#cite_note-Martindale-6">[6]</a><a href="#cite_note-MoscouSnipe2012-8">[8]</a><a href="#cite_note-HumansOrganization2007-9">[9]</a> CEEs are also formulated in combination with progestins.<a href="#cite_note-Martindale-6">[6]</a> Major brand names of CEEs in combination with <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a> include Prempro and Premphase in the United States, Premplus in Canada, Premique in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> and <a href="/wiki/Ireland" title="Ireland">Ireland</a>, Premia in <a href="/wiki/Australia" title="Australia">Australia</a> and <a href="/wiki/New_Zealand" title="New Zealand">New Zealand</a>, and Premelle in <a href="/wiki/South_Africa" title="South Africa">South Africa</a>.<a href="#cite_note-Martindale-6">[6]</a><a href="#cite_note-HochadelAvorn2007-91">[86]</a> Prempak-C is a combination of CEEs and <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a> which is used in the United Kingdom and Ireland, and Prempak N is a combination of CEEs and <a href="/wiki/Medrogestone" title="Medrogestone">medrogestone</a> which is used in South Africa.<a href="#cite_note-Martindale-6">[6]</a> Many of the aforementioned brand names are also used in other, non-English-speaking countries.<a href="#cite_note-Martindale-6">[6]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=15" title="Edit section: Availability">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_estrogens_available_in_the_United_States" title="List of estrogens available in the United States">List of estrogens available in the United States</a></div> CEEs are marketed and available widely throughout the world.<a href="#cite_note-Martindale-6">[6]</a><a href="#cite_note-Drugs.com-Premarin-26">[26]</a> This includes in all English-speaking countries, throughout the European Union, Latin America, Asia, and elsewhere in the world.<a href="#cite_note-Martindale-6">[6]</a><a href="#cite_note-Drugs.com-Premarin-26">[26]</a> <div class="mw-heading mw-heading3"><h3 id="Health_effects">Health effects</h3>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=16" title="Edit section: Health effects">edit</a>]</div> Research starting in 1975 showed substantially increased risk of <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a>.<a href="#cite_note-92">[87]</a><a href="#cite_note-93">[88]</a> Since 1976, the drug has carried a label warning about the risk.<a href="#cite_note-Singer-94">[89]</a> As part of the <a href="/wiki/Women%27s_Health_Initiative" title="Women's Health Initiative">Women's Health Initiative</a> sponsored by the <a href="/wiki/National_Institutes_of_Health" title="National Institutes of Health">National Institutes of Health</a>, a large-scale <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trial</a> of menopausal HRT showed that long-term use of estrogen and a progestin may increase the risk of <a href="/wiki/Stroke" title="Stroke">strokes</a>, <a href="/wiki/Heart_attack" class="mw-redirect" title="Heart attack">heart attacks</a>, <a href="/wiki/Blood_clot" class="mw-redirect" title="Blood clot">blood clots</a>, and breast cancer.<a href="#cite_note-Brunner-95">[90]</a> Following these results, Wyeth experienced a significant decline in its sales of Premarin, Prempro (CEEs and <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>), and related products, from over $2 billion in 2002 to just over $1 billion in 2006.<a href="#cite_note-96">[91]</a> <div class="mw-heading mw-heading3"><h3 id="Litigation">Litigation</h3>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=17" title="Edit section: Litigation">edit</a>]</div> This drug has been the subject of litigation; more than 13,000 people have sued Wyeth between 2002 and 2009. Wyeth and Pharmacia & Upjohn prevailed in the vast majority of hormone therapy cases previously set for trial through a combination of rulings by judges, verdicts by juries, and dismissals by plaintiffs themselves.<a href="#cite_note-97">[92]</a> Of the company's losses, two of the jury verdicts were reversed post-trial and others are being challenged on appeal. Wyeth also won five summary judgments on Prempro cases and had 15 cases voluntarily dismissed by plaintiffs. The company won dismissals in another 3,000 cases.<a href="#cite_note-Bloomberg_2010-98">[93]</a> In 2006, Mary Daniel, in a trial in Philadelphia, was awarded $1.5 million in compensatory damages as well as undisclosed punitive damages. As of 2010, Wyeth had won the last four of five cases, most recently in Virginia, finding that they were not responsible for the breast cancer of plaintiff Georgia Torkie-Tork.<a href="#cite_note-99">[94]</a> Wyeth has been quoted as saying "many risk factors associated with breast cancer have been identified, but science cannot establish what role any particular risk factor or combination play in any individual woman's breast cancer."<a href="#cite_note-100">[95]</a> Wyeth's counsel in the case also noted that in the WHI trial, 99.62% of women took the drug and "did not get breast cancer".<a href="#cite_note-Bloomberg_2010-98">[93]</a> <div class="mw-heading mw-heading3"><h3 id="Animal_welfare">Animal welfare</h3>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=18" title="Edit section: Animal welfare">edit</a>]</div> <a href="/wiki/Animal_welfare" title="Animal welfare">Animal welfare</a> groups claim that animal husbandry and urine collection methods used in the production of CEEs cause undue stress and suffering to the <a href="/wiki/Mare_(horse)" class="mw-redirect" title="Mare (horse)">mares</a> involved. Animal activists have made claims of abuses ranging from inadequate stall size, long periods of confinement, cumbersome urine collection, and continuous breeding cycles. After reaching advanced age, many of the mares are adopted for recreation use, while some are sent to feed lots for slaughter. Despite the controversy, the USDA called the CEEs HRT industry a model of self-regulation.<a href="#cite_note-101">[96]</a> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=19" title="Edit section: Notes">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist reflist-lower-alpha"> </div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> </div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Conjugated_estrogens&action=edit&section=20" title="Edit section: References">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-pmid16112947-1">^ <a href="#cite_ref-pmid16112947_1-0">a</a> <a href="#cite_ref-pmid16112947_1-1">b</a> <a href="#cite_ref-pmid16112947_1-2">c</a> <a href="#cite_ref-pmid16112947_1-3">d</a> <a href="#cite_ref-pmid16112947_1-4">e</a> <a href="#cite_ref-pmid16112947_1-5">f</a> <a href="#cite_ref-pmid16112947_1-6">g</a> <a href="#cite_ref-pmid16112947_1-7">h</a> <a href="#cite_ref-pmid16112947_1-8">i</a> <a href="#cite_ref-pmid16112947_1-9">j</a> <a href="#cite_ref-pmid16112947_1-10">k</a> <a href="#cite_ref-pmid16112947_1-11">l</a> <a href="#cite_ref-pmid16112947_1-12">m</a> <a href="#cite_ref-pmid16112947_1-13">n</a> <a href="#cite_ref-pmid16112947_1-14">o</a> <a href="#cite_ref-pmid16112947_1-15">p</a> <a href="#cite_ref-pmid16112947_1-16">q</a> <a href="#cite_ref-pmid16112947_1-17">r</a> <a href="#cite_ref-pmid16112947_1-18">s</a> <a href="#cite_ref-pmid16112947_1-19">t</a> <a href="#cite_ref-pmid16112947_1-20">u</a> <a href="#cite_ref-pmid16112947_1-21">v</a> <a href="#cite_ref-pmid16112947_1-22">w</a> <a href="#cite_ref-pmid16112947_1-23">x</a> <a href="#cite_ref-pmid16112947_1-24">y</a> <a href="#cite_ref-pmid16112947_1-25">z</a> <a href="#cite_ref-pmid16112947_1-26">aa</a> <a href="#cite_ref-pmid16112947_1-27">ab</a> <a href="#cite_ref-pmid16112947_1-28">ac</a> <a href="#cite_ref-pmid16112947_1-29">ad</a> <a href="#cite_ref-pmid16112947_1-30">ae</a> <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="CITEREFKuhl2005" class="citation journal cs1">Kuhl H (August 2005). 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"The risk of venous thrombosis in women over 50 years old using oral contraception or postmenopausal hormone therapy". Journal of Thrombosis and Haemostasis. 11 (1): 124–131. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fjth.12060">10.1111/jth.12060</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/23136837">23136837</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:22306721">22306721</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Thrombosis+and+Haemostasis&rft.atitle=The+risk+of+venous+thrombosis+in+women+over+50+years+old+using+oral+contraception+or+postmenopausal+hormone+therapy&rft.volume=11&rft.issue=1&rft.pages=124-131&rft.date=2013-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A22306721%23id-name%3DS2CID&rft_id=info%3Apmid%2F23136837&rft_id=info%3Adoi%2F10.1111%2Fjth.12060&rft.aulast=Roach&rft.aufirst=RE&rft.au=Lijfering%2C+WM&rft.au=Helmerhorst%2C+FM&rft.au=Cannegieter%2C+SC&rft.au=Rosendaal%2C+FR&rft.au=van+Hylckama+Vlieg%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-Buchsbaum2012-37"><a href="#cite_ref-Buchsbaum2012_37-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBuchsbaum2012" class="citation book cs1">Buchsbaum HJ (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=z0LuBwAAQBAJ&pg=PA64">The Menopause</a>. 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Fortschritte Der Medizin (in German). 95 (21): 1388–92. <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/559617">559617</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Fortschritte+Der+Medizin&rft.atitle=%5BEstrogen+thearpy+in+practice.+3.+Estrogen+preparations+and+combination+preparations%5D&rft.volume=95&rft.issue=21&rft.pages=1388-92&rft.date=1977-06&rft_id=info%3Apmid%2F559617&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-WolfSchneider2013-45"><a href="#cite_ref-WolfSchneider2013_45-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWolfSchneider2013" class="citation book cs1">Wolf AS, Schneider HP (12 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=IArLBgAAQBAJ&pg=PA78">Östrogene in Diagnostik und Therapie</a>. Springer-Verlag. pp. 78–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-75101-1" title="Special:BookSources/978-3-642-75101-1"><bdi>978-3-642-75101-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=%C3%96strogene+in+Diagnostik+und+Therapie&rft.pages=78-&rft.pub=Springer-Verlag&rft.date=2013-03-12&rft.isbn=978-3-642-75101-1&rft.aulast=Wolf&rft.aufirst=AS&rft.au=Schneider%2C+HP&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DIArLBgAAQBAJ%26pg%3DPA78&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-GöretzlehnerLauritzen2012-46"><a href="#cite_ref-GöretzlehnerLauritzen2012_46-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGöretzlehnerLauritzenRömerRossmanith2012" class="citation book cs1">Göretzlehner G, Lauritzen C, Römer T, Rossmanith W (1 January 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=TIs2WhfYzZ4C&pg=PA44">Praktische Hormontherapie in der Gynäkologie</a>. Walter de Gruyter. pp. 44–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-024568-4" title="Special:BookSources/978-3-11-024568-4"><bdi>978-3-11-024568-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Praktische+Hormontherapie+in+der+Gyn%C3%A4kologie&rft.pages=44-&rft.pub=Walter+de+Gruyter&rft.date=2012-01-01&rft.isbn=978-3-11-024568-4&rft.aulast=G%C3%B6retzlehner&rft.aufirst=G&rft.au=Lauritzen%2C+C&rft.au=R%C3%B6mer%2C+T&rft.au=Rossmanith%2C+W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DTIs2WhfYzZ4C%26pg%3DPA44&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-KnörrBeller2013-47"><a href="#cite_ref-KnörrBeller2013_47-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKnörrBellerLauritzen2013" class="citation book cs1">Knörr K, Beller FK, Lauritzen C (17 April 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=ACybBwAAQBAJ&pg=PA212">Lehrbuch der Gynäkologie</a>. Springer-Verlag. pp. 212–213. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-662-00942-0" title="Special:BookSources/978-3-662-00942-0"><bdi>978-3-662-00942-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lehrbuch+der+Gyn%C3%A4kologie&rft.pages=212-213&rft.pub=Springer-Verlag&rft.date=2013-04-17&rft.isbn=978-3-662-00942-0&rft.aulast=Kn%C3%B6rr&rft.aufirst=K&rft.au=Beller%2C+FK&rft.au=Lauritzen%2C+C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DACybBwAAQBAJ%26pg%3DPA212&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-HorskyPresl1981-48"><a href="#cite_ref-HorskyPresl1981_48-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHorskýPresl1981" class="citation book cs1">Horský J, Presl J (1981). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7IrpCAAAQBAJ&pg=PA310">"Hormonal Treatment of Disorders of the Menstrual Cycle"</a>. In Horsky J, Presl J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 309–332. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-94-009-8195-9_11">10.1007/978-94-009-8195-9_11</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-009-8195-9" title="Special:BookSources/978-94-009-8195-9"><bdi>978-94-009-8195-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormonal+Treatment+of+Disorders+of+the+Menstrual+Cycle&rft.btitle=Ovarian+Function+and+its+Disorders%3A+Diagnosis+and+Therapy&rft.pages=309-332&rft.pub=Springer+Science+%26+Business+Media&rft.date=1981&rft_id=info%3Adoi%2F10.1007%2F978-94-009-8195-9_11&rft.isbn=978-94-009-8195-9&rft.aulast=Horsk%C3%BD&rft.aufirst=J&rft.au=Presl%2C+J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7IrpCAAAQBAJ%26pg%3DPA310&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-Pschyrembel1968-49"><a href="#cite_ref-Pschyrembel1968_49-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPschyrembel1968" class="citation book cs1">Pschyrembel W (1968). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=vVaTnHDFzZ0C&pg=PA598">Praktische Gynäkologie: für Studierende und Ärzte</a>. Walter de Gruyter. pp. 598–599. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-150424-7" title="Special:BookSources/978-3-11-150424-7"><bdi>978-3-11-150424-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Praktische+Gyn%C3%A4kologie%3A+f%C3%BCr+Studierende+und+%C3%84rzte&rft.pages=598-599&rft.pub=Walter+de+Gruyter&rft.date=1968&rft.isbn=978-3-11-150424-7&rft.aulast=Pschyrembel&rft.aufirst=W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks-id%3DvVaTnHDFzZ0C%26pg%3DPA598&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-pmid779393-50"><a href="#cite_ref-pmid779393_50-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1976" class="citation journal cs1">Lauritzen CH (January 1976). "The female climacteric syndrome: significance, problems, treatment". Acta Obstetricia Et Gynecologica Scandinavica. Supplement. 51: 47–61. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00016347509156433">10.3109/00016347509156433</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/779393">779393</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+Et+Gynecologica+Scandinavica.+Supplement&rft.atitle=The+female+climacteric+syndrome%3A+significance%2C+problems%2C+treatment&rft.volume=51&rft.pages=47-61&rft.date=1976-01&rft_id=info%3Adoi%2F10.3109%2F00016347509156433&rft_id=info%3Apmid%2F779393&rft.aulast=Lauritzen&rft.aufirst=CH&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-Lauritzen1975-51"><a href="#cite_ref-Lauritzen1975_51-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1975" class="citation journal cs1">Lauritzen C (1975). "The Female Climacteric Syndrome: Significance, Problems, Treatment". Acta Obstetricia et Gynecologica Scandinavica. 54 (s51): 48–61. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00016347509156433">10.3109/00016347509156433</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/0001-6349">0001-6349</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+et+Gynecologica+Scandinavica&rft.atitle=The+Female+Climacteric+Syndrome%3A+Significance%2C+Problems%2C+Treatment&rft.volume=54&rft.issue=s51&rft.pages=48-61&rft.date=1975&rft_id=info%3Adoi%2F10.3109%2F00016347509156433&rft.issn=0001-6349&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-Kopera1991-52"><a href="#cite_ref-Kopera1991_52-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKopera1991" class="citation book cs1">Kopera H (1991). "Hormone der Gonaden". Hormonelle Therapie für die Frau. Kliniktaschenbücher. pp. 59–124. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-95670-6_6">10.1007/978-3-642-95670-6_6</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-54554-5" title="Special:BookSources/978-3-540-54554-5"><bdi>978-3-540-54554-5</bdi></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/0172-777X">0172-777X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormone+der+Gonaden&rft.btitle=Hormonelle+Therapie+f%C3%BCr+die+Frau&rft.series=Kliniktaschenb%C3%BCcher&rft.pages=59-124&rft.date=1991&rft.issn=0172-777X&rft_id=info%3Adoi%2F10.1007%2F978-3-642-95670-6_6&rft.isbn=978-3-540-54554-5&rft.aulast=Kopera&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-pmid29603164-53"><a href="#cite_ref-pmid29603164_53-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFScottMenonWalsh1980" class="citation journal cs1">Scott WW, Menon M, Walsh PC (April 1980). "Hormonal Therapy of Prostatic Cancer". Cancer. 45 (Suppl 7): 1929–1936. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcncr.1980.45.s7.1929">10.1002/cncr.1980.45.s7.1929</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/29603164">29603164</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer&rft.atitle=Hormonal+Therapy+of+Prostatic+Cancer&rft.volume=45&rft.issue=Suppl+7&rft.pages=1929-1936&rft.date=1980-04&rft_id=info%3Adoi%2F10.1002%2Fcncr.1980.45.s7.1929&rft_id=info%3Apmid%2F29603164&rft.aulast=Scott&rft.aufirst=WW&rft.au=Menon%2C+M&rft.au=Walsh%2C+PC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-pmid29756046-54"><a href="#cite_ref-pmid29756046_54-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeinungFeustelJoseph2018" class="citation journal cs1">Leinung MC, Feustel PJ, Joseph J (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5944393">"Hormonal Treatment of Transgender Women with Oral Estradiol"</a>. Transgender Health. 3 (1): 74–81. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1089%2Ftrgh.2017.0035">10.1089/trgh.2017.0035</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5944393">5944393</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/29756046">29756046</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Transgender+Health&rft.atitle=Hormonal+Treatment+of+Transgender+Women+with+Oral+Estradiol&rft.volume=3&rft.issue=1&rft.pages=74-81&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5944393%23id-name%3DPMC&rft_id=info%3Apmid%2F29756046&rft_id=info%3Adoi%2F10.1089%2Ftrgh.2017.0035&rft.aulast=Leinung&rft.aufirst=MC&rft.au=Feustel%2C+PJ&rft.au=Joseph%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5944393&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-Rydén1950-55"><a href="#cite_ref-Rydén1950_55-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRyden1950" class="citation journal cs1">Ryden AB (1950). "Natural and synthetic oestrogenic substances; their relative effectiveness when administered orally". Acta Endocrinologica. 4 (2): 121–39. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.0040121">10.1530/acta.0.0040121</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/15432047">15432047</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Endocrinologica&rft.atitle=Natural+and+synthetic+oestrogenic+substances%3B+their+relative+effectiveness+when+administered+orally&rft.volume=4&rft.issue=2&rft.pages=121-39&rft.date=1950&rft_id=info%3Adoi%2F10.1530%2Facta.0.0040121&rft_id=info%3Apmid%2F15432047&rft.aulast=Ryden&rft.aufirst=AB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-pmid14902290-56"><a href="#cite_ref-pmid14902290_56-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRyden1951" class="citation journal cs1">Ryden AB (1951). "The effectiveness of natural and synthetic oestrogenic substances in women". Acta Endocrinologica. 8 (2): 175–91. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1530%2Facta.0.0080175">10.1530/acta.0.0080175</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/14902290">14902290</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Endocrinologica&rft.atitle=The+effectiveness+of+natural+and+synthetic+oestrogenic+substances+in+women&rft.volume=8&rft.issue=2&rft.pages=175-91&rft.date=1951&rft_id=info%3Adoi%2F10.1530%2Facta.0.0080175&rft_id=info%3Apmid%2F14902290&rft.aulast=Ryden&rft.aufirst=AB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-Kottmeier1947-57"><a href="#cite_ref-Kottmeier1947_57-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKottmeier1947" class="citation journal cs1">Kottmeier HL (1947). "Ueber blutungen in der menopause: Speziell der klinischen bedeutung eines endometriums mit zeichen hormonaler beeinflussung: Part I". Acta Obstetricia et Gynecologica Scandinavica. 27 (s6): 1–121. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F00016344709154486">10.3109/00016344709154486</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/0001-6349">0001-6349</a>. <q>There is no doubt that the conversion of the endometrium with injections of both synthetic and native estrogenic hormone preparations succeeds, but the opinion whether native, orally administered preparations can produce a proliferation mucosa changes with different authors. PEDERSEN-BJERGAARD (1939) was able to show that 90% of the folliculin taken up in the blood of the vena portae is inactivated in the liver. Neither KAUFMANN (1933, 1935), RAUSCHER (1939, 1942) nor HERRNBERGER (1941) succeeded in bringing a castration endometrium into proliferation using large doses of orally administered preparations of estrone or estradiol. Other results are reported by NEUSTAEDTER (1939), LAUTERWEIN (1940) and FERIN (1941); they succeeded in converting an atrophic castration endometrium into an unambiguous proliferation mucosa with 120–300 oestradiol or with 380 oestrone.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Obstetricia+et+Gynecologica+Scandinavica&rft.atitle=Ueber+blutungen+in+der+menopause%3A+Speziell+der+klinischen+bedeutung+eines+endometriums+mit+zeichen+hormonaler+beeinflussung%3A+Part+I&rft.volume=27&rft.issue=s6&rft.pages=1-121&rft.date=1947&rft_id=info%3Adoi%2F10.3109%2F00016344709154486&rft.issn=0001-6349&rft.aulast=Kottmeier&rft.aufirst=HL&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-RietbrockStaib2013-58"><a href="#cite_ref-RietbrockStaib2013_58-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRietbrockStaibLoew2013" class="citation book cs1">Rietbrock N, Staib AH, Loew D (11 March 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books-id=FkwEBgAAQBAJ&pg=PA426">Klinische Pharmakologie: Arzneitherapie</a>. 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Endocrinology. 149 (10): 4857–70. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fen.2008-0304">10.1210/en.2008-0304</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/18599548">18599548</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrinology&rft.atitle=Structure+activity+relationships+and+differential+interactions+and+functional+activity+of+various+equine+estrogens+mediated+via+estrogen+receptors+%28ERs%29+ERalpha+and+ERbeta&rft.volume=149&rft.issue=10&rft.pages=4857-70&rft.date=2008-10&rft_id=info%3Adoi%2F10.1210%2Fen.2008-0304&rft_id=info%3Apmid%2F18599548&rft.aulast=Bhavnani&rft.aufirst=BR&rft.au=Tam%2C+SP&rft.au=Lu%2C+X&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-FeldbergLadd-Taylor2003-79"><a href="#cite_ref-FeldbergLadd-Taylor2003_79-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFeldbergLadd-TaylorLi2003" class="citation book cs1">Feldberg GD, Ladd-Taylor M, Li A (2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=CRjtHlq1INcC&pg=PA103">Women, Health and Nation: Canada and the United States Since 1945</a>. McGill-Queen's Press - MQUP. pp. 103–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7735-2501-6" title="Special:BookSources/978-0-7735-2501-6"><bdi>978-0-7735-2501-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Women%2C+Health+and+Nation%3A+Canada+and+the+United+States+Since+1945&rft.pages=103-&rft.pub=McGill-Queen%27s+Press+-+MQUP&rft.date=2003&rft.isbn=978-0-7735-2501-6&rft.aulast=Feldberg&rft.aufirst=GD&rft.au=Ladd-Taylor%2C+M&rft.au=Li%2C+A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DCRjtHlq1INcC%26pg%3DPA103&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-SchachterMarrian1938-80"><a href="#cite_ref-SchachterMarrian1938_80-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchachterMarrian1938" class="citation journal cs1">Schachter B, Marrian GF (1938). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2973874-X">"The isolation of estrone sulfate from the urine of pregnant mares"</a>. Journal of Biological Chemistry. 126 (2): 663–669. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2818%2973874-X">10.1016/S0021-9258(18)73874-X</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Biological+Chemistry&rft.atitle=The+isolation+of+estrone+sulfate+from+the+urine+of+pregnant+mares&rft.volume=126&rft.issue=2&rft.pages=663-669&rft.date=1938&rft_id=info%3Adoi%2F10.1016%2FS0021-9258%2818%2973874-X&rft.aulast=Schachter&rft.aufirst=B&rft.au=Marrian%2C+GF&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0021-9258%252818%252973874-X&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-MDD-81">^ <a href="#cite_ref-MDD_81-0">a</a> <a href="#cite_ref-MDD_81-1">b</a> <a href="#cite_ref-MDD_81-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKling2000" class="citation journal cs1">Kling J (October 2000). <a rel="nofollow" class="external text" href="http://pubs.acs.org/subscribe/archive/mdd/v03/i08/html/kling.html">"The Strange Case of Premarin"</a>. Modern Drug Discovery. 3 (8): 46–52.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Modern+Drug+Discovery&rft.atitle=The+Strange+Case+of+Premarin&rft.volume=3&rft.issue=8&rft.pages=46-52&rft.date=2000-10&rft.aulast=Kling&rft.aufirst=J&rft_id=http%3A%2F%2Fpubs.acs.org%2Fsubscribe%2Farchive%2Fmdd%2Fv03%2Fi08%2Fhtml%2Fkling.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-82"><a href="#cite_ref-82">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://archive.org/details/federalregister37gunit">"Federal register [microform]"</a>. Washington : [Office of the Federal Register, National Archives and Records Service, General Services Administration : Distributed by the Supt. of Docs., U.S. G.P.O.] 3 June 1972 – via Internet Archive.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Federal+register+%5Bmicroform%5D&rft.pub=Washington+%3A+%5BOffice+of+the+Federal+Register%2C+National+Archives+and+Records+Service%2C+General+Services+Administration+%3A+Distributed+by+the+Supt.+of+Docs.%2C+U.S.+G.P.O.%5D&rft.date=1972-06-03&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Ffederalregister37gunit&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-83"><a href="#cite_ref-83">^</a> National Institutes of Health Consensus Development Conference Statement. 2–4 April 1984 <a rel="nofollow" class="external text" href="http://consensus.nih.gov/1984/1984Osteoporosis043html.htm">Osteoporosis</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20051121042455/http://consensus.nih.gov/1984/1984Osteoporosis043html.htm">Archived</a> 21 November 2005 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> </li> <li id="cite_note-Woodcock1997-84"><a href="#cite_ref-Woodcock1997_84-0">^</a> Food and Drug Administration. 5 May 1997 <a rel="nofollow" class="external text" href="https://www.fda.gov/Drugs/DrugSafety/InformationbyDrugClass/ucm168836.htm">Conjugated Estrogens - Letter from Dr. Janet Woodcock: Approvability of a Synthetic Generic Version of Premarin</a> </li> <li id="cite_note-PanayBriggs2015-85"><a href="#cite_ref-PanayBriggs2015_85-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPanayBriggsKovacs2015" class="citation book cs1">Panay N, Briggs P, Kovacs G (20 August 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=l0pLCgAAQBAJ&pg=PA118">Managing the Menopause</a>. Cambridge University Press. pp. 118–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-107-45182-7" title="Special:BookSources/978-1-107-45182-7"><bdi>978-1-107-45182-7</bdi></a>. <q>Premarin (Pregnant Mares Urine) was introduced in Canada in 1941, in the USA in 1942 and in the UK in 1956.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Managing+the+Menopause&rft.pages=118-&rft.pub=Cambridge+University+Press&rft.date=2015-08-20&rft.isbn=978-1-107-45182-7&rft.aulast=Panay&rft.aufirst=N&rft.au=Briggs%2C+P&rft.au=Kovacs%2C+G&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dl0pLCgAAQBAJ%26pg%3DPA118&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-Dominus2023-86"><a href="#cite_ref-Dominus2023_86-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDominus2023" class="citation news cs1">Dominus S (1 February 2023). <a rel="nofollow" class="external text" href="https://www.nytimes.com/2023/02/01/magazine/menopause-hot-flashes-hormone-therapy.html">"Women Have Been Misled About Menopause"</a>. The New York Times. <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/0362-4331">0362-4331</a>. Retrieved 7 February 2023. <q>Every woman has the right — indeed the duty — to counteract the chemical castration that befalls her during her middle years," the gynecologist Robert Wilson wrote in 1966. The U.S. Food and Drug Administration approved the first hormone-therapy drug in 1942, but Wilson's blockbuster book, "Feminine Forever," can be considered a kind of historical landmark...Within a decade of the book's publication, Premarin — a mix of estrogens derived from the urine of pregnant horses — was the fifth-most-prescribed drug in the United States. (Decades later, it was revealed that Wilson received funding from the pharmaceutical company that sold Premarin.)</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+York+Times&rft.atitle=Women+Have+Been+Misled+About+Menopause&rft.date=2023-02-01&rft.issn=0362-4331&rft.aulast=Dominus&rft.aufirst=S&rft_id=https%3A%2F%2Fwww.nytimes.com%2F2023%2F02%2F01%2Fmagazine%2Fmenopause-hot-flashes-hormone-therapy.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-ChemIDplus-87"><a href="#cite_ref-ChemIDplus_87-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://chem.nlm.nih.gov/chemidplus/rn/12126-59-9">"ChemIDplus - 12126-59-9 - QTTMOCOWZLSYSV-QWAPEVOJSA-M - Estrogens, conjugated [USP:JAN] - Similar structures search, synonyms, formulas, resource links, and other chemical information"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=ChemIDplus+-+12126-59-9+-+QTTMOCOWZLSYSV-QWAPEVOJSA-M+-+Estrogens%2C+conjugated+%5BUSP%3AJAN%5D+-+Similar+structures+search%2C+synonyms%2C+formulas%2C+resource+links%2C+and+other+chemical+information&rft_id=https%3A%2F%2Fchem.nlm.nih.gov%2Fchemidplus%2Frn%2F12126-59-9&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-pmid23217066-88"><a href="#cite_ref-pmid23217066_88-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAlexander2012" class="citation journal cs1">Alexander IM (2012). 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The Journal of Endocrinology. 185 (2): 207–222. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1677%2Fjoe.1.05847">10.1677/joe.1.05847</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/15845914">15845914</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+Endocrinology&rft.atitle=Postmenopausal+hormone+therapy%3A+from+monkey+glands+to+transdermal+patches&rft.volume=185&rft.issue=2&rft.pages=207-222&rft.date=2005-05&rft_id=info%3Adoi%2F10.1677%2Fjoe.1.05847&rft_id=info%3Apmid%2F15845914&rft.aulast=Davis&rft.aufirst=SR&rft.au=Dinatale%2C+I&rft.au=Rivera-Woll%2C+L&rft.au=Davison%2C+S&rft_id=https%3A%2F%2Fdoi.org%2F10.1677%252Fjoe.1.05847&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"> </li> <li id="cite_note-pmid21189221-90"><a href="#cite_ref-pmid21189221_90-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSmithWein2010" class="citation journal cs1">Smith AL, Wein AJ (December 2010). 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"The saga of the ring B unsaturated equine estrogens". Endocrine Reviews. 9 (4): 396–416. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fedrv-9-4-396">10.1210/edrv-9-4-396</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/3065072">3065072</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Endocrine+Reviews&rft.atitle=The+saga+of+the+ring+B+unsaturated+equine+estrogens&rft.volume=9&rft.issue=4&rft.pages=396-416&rft.date=1988-11&rft_id=info%3Adoi%2F10.1210%2Fedrv-9-4-396&rft_id=info%3Apmid%2F3065072&rft.aulast=Bhavnani&rft.aufirst=BR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AConjugated+estrogens" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAnsbacher1993" class="citation journal cs1">Ansbacher R (April 1993). 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Critical Reviews in Toxicology. 44 (8): 696–724. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.3109%2F10408444.2014.930813">10.3109/10408444.2014.930813</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/25099693">25099693</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:11212469">11212469</a>.</cite><span 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href="https://web.archive.org/web/20081218203608/http://public.nhlbi.nih.gov/newsroom/home/GetPressRelease.aspx?id=2554">WHI Follow-up Study Confirms Health Risks of Long-Term Combination Hormone Therapy Outweigh Benefits for Postmenopausal Women</a> NIH press release, 4 March 2008</li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 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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:Estradiol" title="Template:Estradiol"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estradiol" title="Template talk:Estradiol"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estradiol" title="Special:EditPage/Template:Estradiol"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estradiol" style="font-size:114%;margin:0 4em"><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Topics</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Estradiol" title="Estradiol">Estradiol (as a hormone)</a></li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol (as a medication)</a></li> <li><a href="/wiki/Pharmacodynamics_of_estradiol" title="Pharmacodynamics of estradiol">Pharmacodynamics of estradiol</a></li> <li><a href="/wiki/Pharmacokinetics_of_estradiol" title="Pharmacokinetics of estradiol">Pharmacokinetics of estradiol</a></li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogen (as a hormone)</a></li> <li><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen (as a medication)</a></li> <li><a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">Menopausal hormone therapy</a></li> <li><a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">Feminizing hormone therapy</a></li> <li><a href="/wiki/Estradiol-containing_birth_control_pill" title="Estradiol-containing birth control pill">Estradiol-containing birth control pill</a></li> <li><a href="/wiki/Combined_injectable_birth_control" title="Combined injectable birth control">Combined injectable birth control</a></li> <li><a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">High-dose estrogen</a></li> <li><a href="/wiki/Hydroxylation_of_estradiol" title="Hydroxylation of estradiol">Hydroxylation of estradiol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_ester" title="Estrogen ester">Esters</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a></li> <li><a href="/wiki/Estradiol_acetylsalicylate" title="Estradiol acetylsalicylate">Estradiol acetylsalicylate</a></li> <li><a href="/wiki/Estradiol_anthranilate" title="Estradiol anthranilate">Estradiol anthranilate</a></li> <li><a href="/wiki/Estradiol_benzoate_butyrate" title="Estradiol benzoate butyrate">Estradiol benzoate butyrate</a></li> <li><a href="/wiki/Estradiol_benzoate_cyclooctenyl_ether" title="Estradiol benzoate cyclooctenyl ether">Estradiol benzoate cyclooctenyl ether</a></li> <li><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></li> <li><a href="/wiki/Estradiol_butyrylacetate" title="Estradiol butyrylacetate">Estradiol butyrylacetate</a></li> <li><a href="/wiki/Estradiol_cyclooctyl_acetate" title="Estradiol cyclooctyl acetate">Estradiol cyclooctyl acetate</a></li> <li><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></li> <li><a href="/wiki/Estradiol_decanoate" title="Estradiol decanoate">Estradiol decanoate</a></li> <li><a href="/wiki/Estradiol_diacetate" title="Estradiol diacetate">Estradiol diacetate</a></li> <li><a href="/wiki/Estradiol_dibutyrate" title="Estradiol dibutyrate">Estradiol dibutyrate</a></li> <li><a href="/wiki/Estradiol_dienantate" title="Estradiol dienantate">Estradiol dienantate</a></li> <li><a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">Estradiol dipropionate</a></li> <li><a href="/wiki/Estradiol_distearate" title="Estradiol distearate">Estradiol distearate</a></li> <li><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></li> <li><a href="/wiki/Estradiol_diundecylate" title="Estradiol diundecylate">Estradiol diundecylate</a></li> <li><a href="/wiki/Estradiol_diundecylenate" title="Estradiol diundecylenate">Estradiol diundecylenate</a></li> <li><a href="/wiki/Estradiol_enantate" title="Estradiol enantate">Estradiol enantate</a></li> <li><a href="/wiki/Estradiol_furoate" title="Estradiol furoate">Estradiol furoate</a></li> <li><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></li> <li><a href="/wiki/Estradiol_hemisuccinate" title="Estradiol hemisuccinate">Estradiol hemisuccinate</a></li> <li><a href="/wiki/Estradiol_hexahydrobenzoate" title="Estradiol hexahydrobenzoate">Estradiol hexahydrobenzoate</a></li> <li><a href="/wiki/Estradiol_monopropionate" title="Estradiol monopropionate">Estradiol monopropionate</a></li> <li><a href="/wiki/Estradiol_mustard" title="Estradiol mustard">Estradiol mustard</a></li> <li><a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">Estradiol palmitate</a></li> <li><a href="/wiki/Estradiol_phenylpropionate" title="Estradiol phenylpropionate">Estradiol phenylpropionate</a></li> <li><a href="/wiki/Estradiol_phosphate" title="Estradiol phosphate">Estradiol phosphate</a></li> <li><a href="/wiki/Estradiol_pivalate" title="Estradiol pivalate">Estradiol pivalate</a></li> <li><a href="/wiki/Estradiol_propoxyphenylpropionate" title="Estradiol propoxyphenylpropionate">Estradiol propoxyphenylpropionate</a></li> <li><a href="/wiki/Estradiol_salicylate" title="Estradiol salicylate">Estradiol salicylate</a></li> <li><a href="/wiki/Estradiol_stearate" title="Estradiol stearate">Estradiol stearate</a></li> <li><a href="/wiki/Estradiol_sulfamate" title="Estradiol sulfamate">Estradiol sulfamate</a></li> <li><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></li> <li><a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">Estradiol undecylate</a></li> <li><a href="/wiki/Estradiol_undecylenate" title="Estradiol undecylenate">Estradiol undecylenate</a></li> <li><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate (estradiol normustine phosphate)</a></li> <li><a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a class="mw-selflink selflink">Conjugated estrogens</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Estrogens_and_antiestrogens" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogens_and_antiestrogens" title="Template talk:Estrogens and antiestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogens_and_antiestrogens" title="Special:EditPage/Template:Estrogens and antiestrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogens_and_antiestrogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a class="mw-selflink selflink">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a>†</li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, <a href="/wiki/Estradiol_ester_mixture" class="mw-redirect" title="Estradiol ester mixture">estradiol ester mixtures</a> (<a href="/wiki/Climacteron" class="mw-redirect" title="Climacteron">Climacteron</a>))</li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a> (e.g., <a href="/wiki/Estriol_succinate" title="Estriol succinate">estriol succinate</a>, <a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">polyestriol phosphate</a>)</li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a> <ul><li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a># <ul><li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone; DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate</a></li></ul></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol (stilbestrol)</a></li> <li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters/ethers</a> <ul><li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (diethylstilbestrol dimethyl ether)</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol (diethylstilbestrol monomethyl ether)</a></li></ul></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol (promethestrol)</a> <ul><li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate (promethestrol dipropionate)</a></li></ul></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> (e.g., <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip follicle-stimulating hormone, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip luteinizing hormone)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor antagonists (incl. <a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor modulators/<a href="/wiki/Selective_estrogen_receptor_downregulators" class="mw-redirect" title="Selective estrogen receptor downregulators"><abbr title="selective estrogen receptor downregulators">SERDs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor downregulators)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a>†</li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a>#</li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a>†</li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a>#</li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li></ul> <ul><li>Exclusively antagonistic: <a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li></ul> <ul><li>Noncompetitive inhibitors: <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">Aromatase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>First-generation: <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Testolactone" title="Testolactone">Testolactone</a></li></ul> <ul><li>Second-generation: <a href="/wiki/Fadrozole" title="Fadrozole">Fadrozole</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li></ul> <ul><li>Third-generation: <a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Letrozole" title="Letrozole">Letrozole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Androgen" title="Androgen">Androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>)</li> <li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D2 receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin" title="Prolactin">prolactin</a> releasers) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>, <a href="/wiki/Goserelin" title="Goserelin">goserelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>, <a href="/wiki/Elagolix" title="Elagolix">elagolix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Mixed mechanism of action: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li></ul> <ul><li>Androstenedione immunogens: <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Estrogen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a class="mw-selflink selflink">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol">ent-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol">meso-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol">meso-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li>Unknown/unsorted: <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li>Xenoestrogens: <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (cis-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a 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>Coregulator-binding modulators: <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li>Noncompetitive inhibitors: <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/w/index.php?title=G-1_(drug)&action=edit&redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output .portal-bar-content-related{margin:0;list-style:none}.mw-parser-output .portal-bar-item{display:inline-block;margin:0.15em 0.2em;min-height:24px;line-height:24px}@media screen and (max-width:768px){.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;flex-flow:column wrap;align-items:baseline}.mw-parser-output .portal-bar-header{text-align:center;flex:0;padding-left:0.5em;margin:0 auto}.mw-parser-output .portal-bar-related{font-size:100%;align-items:flex-start}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;align-items:center;flex:0;column-gap:1em;border-top:1px solid #a2a9b1;margin:0 auto;list-style:none}.mw-parser-output .portal-bar-content-related{border-top:none;margin:0;list-style:none}}.mw-parser-output .navbox+link+.portal-bar,.mw-parser-output .navbox+style+.portal-bar,.mw-parser-output .navbox+link+.portal-bar-bordered,.mw-parser-output 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