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href="https://azb.wikipedia.org/wiki/%D9%88%D8%A7%D9%84%D8%B1%D8%A7%D8%AA_%D8%A7%D8%B3%D8%AA%D8%B1%D8%A7%D8%AF%DB%8C%D9%88%D9%84" title="والرات استرادیول – South Azerbaijani" lang="azb" hreflang="azb" data-title="والرات استرادیول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Valerato_de_estradiol" title="Valerato de estradiol – Spanish" lang="es" hreflang="es" data-title="Valerato de estradiol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%88%D8%A7%D9%84%D8%B1%D8%A7%D8%AA_%D8%A7%D8%B3%D8%AA%D8%B1%D8%A7%D8%AF%DB%8C%D9%88%D9%84" title="والرات استرادیول – Persian" lang="fa" hreflang="fa" data-title="والرات استرادیول" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Estradiol_valerat" title="Estradiol valerat – Indonesian" lang="id" hreflang="id" data-title="Estradiol valerat" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%AD%D1%81%D1%82%D1%80%D0%B0%D0%B4%D0%B8%D0%BE%D0%BB%D0%B0_%D0%B2%D0%B0%D0%BB%D0%B5%D1%80%D0%B0%D1%82" title="Эстрадиола валерат – Russian" lang="ru" hreflang="ru" data-title="Эстрадиола валерат" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Estradiol_valerat" title="Estradiol valerat – Serbian" lang="sr" hreflang="sr" data-title="Estradiol valerat" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Estradiol_valerat" title="Estradiol valerat – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Estradiol valerat" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Estradiolivaleraatti" title="Estradiolivaleraatti – Finnish" lang="fi" hreflang="fi" data-title="Estradiolivaleraatti" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a 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dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Estradiol valerate</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Estradiol_valerate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Estradiol_valerate.svg/250px-Estradiol_valerate.svg.png" decoding="async" width="250" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Estradiol_valerate.svg/375px-Estradiol_valerate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Estradiol_valerate.svg/500px-Estradiol_valerate.svg.png 2x" data-file-width="512" data-file-height="268" /></a></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Estradiol_valerate_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Estradiol_valerate_molecule_ball.png/250px-Estradiol_valerate_molecule_ball.png" decoding="async" width="250" height="134" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Estradiol_valerate_molecule_ball.png/375px-Estradiol_valerate_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Estradiol_valerate_molecule_ball.png/500px-Estradiol_valerate_molecule_ball.png 2x" data-file-width="2000" data-file-height="1073" /></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;">Pronunciation</th><td class="infobox-data"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌɛstrəˈdaɪoʊl ˈvæləreɪt/</a> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key">ES-trə-DY-ohl VAL-ə-rayt</a><a href="#cite_note-Drugs.com2-1">[1]</a> </td></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">Delestrogen, Progynon Depot, Progynova, many others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">EV; E2V; Oestradiol valerate; Estradiol pentanoate; Estradiol valerianate</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/Sublingual_administration" title="Sublingual administration">sublingual</a>, <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>,<a href="#cite_note-Zink-1988-2">[2]</a> <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous injection</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a>; <a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a></td></tr><tr><th 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">G03CA03</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G03CA03">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>Rx-only</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">Oral: 3–5%<a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-pmid16112947-5">[5]</a> <abbr title="Intramuscular injection">IM</abbr> injection: 100%<a href="#cite_note-pmid8013217-6">[6]</a><a href="#cite_note-pmid7169965-4">[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">Estradiol: ~98% (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-pmid23375353-7">[7]</a><a href="#cite_note-Falcone-2007-8">[8]</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/Bond_cleavage" title="Bond cleavage">Cleavage</a> via <a href="/wiki/Esterase" title="Esterase">esterases</a> in the <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Blood" title="Blood">blood</a>, and <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a><a href="#cite_note-pmid7169965-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a>, <a href="/wiki/Valeric_acid" title="Valeric acid">valeric acid</a>, and <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of estradiol<a href="#cite_note-pmid7169965-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination half-life</a></th><td class="infobox-data">Oral: 12–20 hours (as <abbr title="estradiol">E2</abbr>)<a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-pmid23375353-7">[7]</a> <abbr title="Intramuscular injection">IM</abbr> injection: 3.5 (1.2–7.2) days<a href="#cite_note-pmid22257576-9">[9]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data"><abbr title="Intramuscular injection">IM</abbr> injection: • 5 mg: 7–8 days<a href="#cite_note-pmid7389356-10">[10]</a> • 10 mg: 10–14 days<a href="#cite_note-Lauritzen-1988-11">[11]</a><a href="#cite_note-Labhart-2012-12">[12]</a> • 40 mg: 2–3 weeks<a href="#cite_note-Lauritzen-1988-11">[11]</a> • 100 mg: 3–4 weeks<a href="#cite_note-Lauritzen-1988-11">[11]</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/Urine" title="Urine">Urine</a> (80%)<a href="#cite_note-pmid7169965-4">[4]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">[(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] pentanoate</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=979-32-8">979-32-8</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/13791">13791</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/DB13956">DB13956</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.13194.html">13194</a></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/OKG364O896">OKG364O896</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/D01413">D01413</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:31561">CHEBI:31561</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/ChEMBL1511">ChEMBL1511</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/DTXSID8023004">DTXSID8023004</a> <a href="https://www.wikidata.org/wiki/Q5401768#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/100.012.327">100.012.327</a> <a href="https://www.wikidata.org/wiki/Q5401768#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C23H32O3</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data">356.506 g·mol−1</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CCCCC%28%3DO%29O%5BC%40H%5D1CC%5BC%40%40H%5D2%5BC%40%40%5D1%28CC%5BC%40H%5D3%5BC%40H%5D2CCC4%3DC3C%3DCC%28%3DC4%29O%29C">Interactive image</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">144 to 145 °C (291 to 293 °F)</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:RSEPBGGWRJCQGY-RBRWEJTLSA-N</div></li></ul> </div></td></tr></tbody></table> Estradiol valerate (EV), sold for use <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a> under the brand name Progynova and for use by <a href="/wiki/Injection_(medicine)" title="Injection (medicine)">injection</a> under the brand names Delestrogen and Progynon Depot among others, is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> medication. It is used in <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">hormone therapy</a> for <a href="/wiki/Menopausal_symptoms" class="mw-redirect" title="Menopausal symptoms">menopausal symptoms</a> and <a href="/wiki/Hypoestrogenism" title="Hypoestrogenism">low estrogen levels</a>, <a href="/wiki/Transgender_hormone_therapy_(male-to-female)" class="mw-redirect" title="Transgender hormone therapy (male-to-female)">hormone therapy</a> for <a href="/wiki/Transgender" title="Transgender">transgender</a> people, and in <a href="/wiki/Hormonal_contraception" title="Hormonal contraception">hormonal birth control</a>.<a href="#cite_note-pmid16112947-5">[5]</a><a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-Delestrogen-Label-13">[13]</a><a href="#cite_note-Progynova-Label-14">[14]</a> It is also used in the treatment of <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>.<a href="#cite_note-Delestrogen-Label-13">[13]</a> The medication is taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a> or by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">injection into muscle</a> or <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">fat</a> once every 1 to 4 weeks.<a href="#cite_note-Delestrogen-Label-13">[13]</a><a href="#cite_note-Progynova-Label-14">[14]</a><figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Progynova_(estradiol_valerate)_tablets_in_the_Chinese_mainland.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/Progynova_%28estradiol_valerate%29_tablets_in_the_Chinese_mainland.jpg/220px-Progynova_%28estradiol_valerate%29_tablets_in_the_Chinese_mainland.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/91/Progynova_%28estradiol_valerate%29_tablets_in_the_Chinese_mainland.jpg/330px-Progynova_%28estradiol_valerate%29_tablets_in_the_Chinese_mainland.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/91/Progynova_%28estradiol_valerate%29_tablets_in_the_Chinese_mainland.jpg/440px-Progynova_%28estradiol_valerate%29_tablets_in_the_Chinese_mainland.jpg 2x" data-file-width="4624" data-file-height="3472" /></a><figcaption>Progynova (estradiol valerate) 1 mg oral tablets in the Chinese mainland</figcaption></figure> <a href="/wiki/Side_effect" title="Side effect">Side effects</a> of estradiol valerate include <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Breast_enlargement" title="Breast enlargement">breast enlargement</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Headache" title="Headache">headache</a>, and <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a>.<a href="#cite_note-Ghosh-2010-15">[15]</a><a href="#cite_note-Delestrogen-Label-13">[13]</a><a href="#cite_note-Progynova-Label-14">[14]</a> Estradiol valerate is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> and hence is an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a>, the <a href="/wiki/Biological_target" title="Biological target">biological target</a> of <a href="/wiki/Estrogen" title="Estrogen">estrogens</a> like <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>.<a href="#cite_note-pmid16112947-5">[5]</a><a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-Oettel-2012-16">[16]</a> It is an <a href="/wiki/Estrogen_ester" title="Estrogen ester">estrogen ester</a> and a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> in the body.<a href="#cite_note-Oettel-2012-16">[16]</a><a href="#cite_note-pmid16112947-5">[5]</a><a href="#cite_note-pmid7169965-4">[4]</a> Because of this, it is considered to be a <a href="/wiki/Natural_product" title="Natural product">natural</a> and <a href="/wiki/Bioidentical_hormone_replacement_therapy" title="Bioidentical hormone replacement therapy">bioidentical</a> form of estrogen.<a href="#cite_note-Oettel-2012-16">[16]</a><a href="#cite_note-pmid17627398-17">[17]</a><a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-Seth-2012-18">[18]</a> Estradiol valerate was first described in 1940 and was introduced for medical use in 1954.<a href="#cite_note-Kleemann-2014-19">[19]</a><a href="#cite_note-Publishing2013-20">[20]</a><a href="#cite_note-Duetsch-1969-21">[21]</a> Along with <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, it is one of the most widely used esters of estradiol.<a href="#cite_note-Yen-1991-22">[22]</a> Estradiol valerate is used in the <a href="/wiki/United_States" title="United States">United States</a>, <a href="/wiki/Canada" title="Canada">Canada</a>, <a href="/wiki/Europe" title="Europe">Europe</a>, and throughout much of the rest of the world.<a href="#cite_note-Elks-2014-23">[23]</a><a href="#cite_note-IndexNominum2000-24">[24]</a> It is available as a <a href="/wiki/Generic_drug" title="Generic drug">generic medication</a>.<a href="#cite_note-Drugs.com-Generic-25">[25]</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=Estradiol_valerate&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estradiol_(medication)#Medical_uses" title="Estradiol (medication)">Estradiol (medication) § Medical uses</a></div> The <a href="/wiki/Medical_use" class="mw-redirect" title="Medical use">medical uses</a> of estradiol valerate are the same as those of estradiol and other estrogens. Examples of indications for the medication include <a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">hormone therapy</a> and <a href="/wiki/Hormonal_contraception" title="Hormonal contraception">hormonal contraception</a>. In regard to the latter, estradiol valerate is available in combination with a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> as a <a href="/wiki/Combined_oral_contraceptive" class="mw-redirect" title="Combined oral contraceptive">combined</a> <a href="/wiki/Estradiol-containing_oral_contraceptive" class="mw-redirect" title="Estradiol-containing oral contraceptive">estradiol-containing oral contraceptive</a> (with <a href="/wiki/Dienogest" title="Dienogest">dienogest</a>)<a href="#cite_note-pmid21151673-26">[26]</a> and as a <a href="/wiki/Combined_injectable_contraceptive" class="mw-redirect" title="Combined injectable contraceptive">combined injectable contraceptive</a>.<a href="#cite_note-pmid12290848-27">[27]</a><a href="#cite_note-pmid19076955-28">[28]</a> Along with <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, and <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, estradiol valerate is used as a form of <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">high-dose estrogen</a> therapy in <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">feminizing hormone therapy</a> for <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a>.<a href="#cite_note-pmid28159148-29">[29]</a><a href="#cite_note-pmid25220381-30">[30]</a><a href="#cite_note-Ettner-2016-31">[31]</a><a href="#cite_note-Israel-2001-32">[32]</a> It is also used as a form of high-dose estrogen therapy in the treatment of prostate cancer in men.<a href="#cite_note-Delestrogen-Label-13">[13]</a> Low-dose oral estradiol valerate (2–6 mg/day) has been used in the treatment of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in women who were previously treated with and benefited from but acquired resistance to <a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">aromatase inhibitors</a> as well.<a href="#cite_note-pmid27889048-33">[33]</a><a href="#cite_note-pmid23933149-34">[34]</a> Injectable estradiol valerate has been used to suppress <a href="/wiki/Sex_drive" class="mw-redirect" title="Sex drive">sex drive</a> in <a href="/wiki/Sex_offender" title="Sex offender">sex offenders</a>.<a href="#cite_note-Chatz-1972-35">[35]</a> In the <a href="/wiki/United_States" title="United States">United States</a>, the approved indications of estradiol valerate injections include the treatment of moderate to severe <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a> and <a href="/wiki/Vaginal_atrophy" class="mw-redirect" title="Vaginal atrophy">vaginal atrophy</a> associated with <a href="/wiki/Menopause" title="Menopause">menopause</a> in women, the treatment of <a href="/wiki/Hypoestrogenism" title="Hypoestrogenism">hypoestrogenism</a> due to <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>, <a href="/wiki/Castration" title="Castration">castration</a>, or <a href="/wiki/Primary_ovarian_failure" class="mw-redirect" title="Primary ovarian failure">primary ovarian failure</a> in women, and the <a href="/wiki/Palliative_care" title="Palliative care">palliative</a> treatment of <a href="/wiki/Advanced_prostate_cancer" class="mw-redirect" title="Advanced prostate cancer">advanced prostate cancer</a> in men.<a href="#cite_note-Delestrogen-Label-13">[13]</a> Elsewhere in the world, oral estradiol valerate is similarly approved for the treatment of symptoms associated with menopause or hypoestrogenism due to castration in women.<a href="#cite_note-Progynova-Label-14">[14]</a> Such symptoms may include hot flashes, <a href="/wiki/Sweating" class="mw-redirect" title="Sweating">outbreaks of sweat</a>, <a href="/wiki/Sleep_disturbance" class="mw-redirect" title="Sleep disturbance">sleep disturbances</a>, <a href="/wiki/Depression_(mood)" title="Depression (mood)">depressive moods</a>, <a href="/wiki/Irritability" title="Irritability">irritability</a>, <a href="/wiki/Headache" title="Headache">headaches</a>, and <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>.<a href="#cite_note-Progynova-Label-14">[14]</a> Estradiol valerate by intramuscular injection is usually used at a dosage of 10 to 20 mg every 4 weeks in the treatment of menopausal symptoms and hypoestrogenism due to hypogonadism, castration, or primary ovarian failure in women.<a href="#cite_note-Delestrogen-Label-13">[13]</a> In the past, it was used at even higher doses of 10 to 40 every 1 to 4 weeks for estrogen replacement.<a href="#cite_note-AMA1977-36">[36]</a> Estradiol valerate is usually used in the treatment of advanced prostate cancer in men at a dosage of 30 mg or more every 1 to 2 weeks by intramuscular injection.<a href="#cite_note-Delestrogen-Label-13">[13]</a> In transgender women, estradiol valerate given by intramuscular injection is usually used at a dosage of 5 to 20 mg, but up to 30 to 40 mg, once every 2 weeks.<a href="#cite_note-pmid25220381-30">[30]</a><a href="#cite_note-Ettner-2016-31">[31]</a><a href="#cite_note-pmid28159148-29">[29]</a> Estradiol valerate has also been used at a dose of 10 to 40 mg by intramuscular injection to <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-Horský-1981-37">[37]</a>: 318 <a href="#cite_note-Piersol-1975-38">[38]</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 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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>Estradiol valerate</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><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated 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/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>Estradiol valerate</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=Estradiol_valerate&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/Estradiol_valerate/norethisterone_enantate" title="Estradiol valerate/norethisterone enantate">Estradiol valerate/norethisterone enantate</a>, <a href="/wiki/Estradiol_valerate/hydroxyprogesterone_caproate" title="Estradiol valerate/hydroxyprogesterone caproate">Estradiol valerate/hydroxyprogesterone caproate</a>, and <a href="/wiki/Estradiol_valerate/prasterone_enanthate" title="Estradiol valerate/prasterone enanthate">Estradiol valerate/prasterone enanthate</a></div> Estradiol valerate is and has been available in the form of <a href="/wiki/Vial" title="Vial">vials</a> and <a href="/wiki/Ampoule" title="Ampoule">ampoules</a> of <a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</a> for intramuscular injection in concentrations of 4, 5, 10, 20, and 40 mg/mL and in the form of oral <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a> at doses of 0.5, 1, 2, and 4 mg per tablet.<a href="#cite_note-Drugs@FDA2-39">[39]</a><a href="#cite_note-Kleemann-2014-19">[19]</a><a href="#cite_note-Muller1998b-40">[40]</a><a href="#cite_note-Becker-2001-41">[41]</a> In the <a href="/wiki/United_States" title="United States">United States</a>, it is specifically available in formulations of 10, 20, and 40 mg/mL in oil solution (as Delestrogen, as well as <a href="/wiki/Generic_drug" title="Generic drug">generics</a>).<a href="#cite_note-Drugs@FDA2-39">[39]</a> Aside from estradiol valerate, the only other injectable estrogen formulations that remain available in the United States are <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a> (5 mg/mL in oil solution) and <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a> (25 mg/vial in solution).<a href="#cite_note-Drugs@FDA2-39">[39]</a> Some or all oral estradiol valerate tablets are <a href="/wiki/Micronization" title="Micronization">micronized</a>, similarly to oral estradiol tablets.<a href="#cite_note-pmid10098476-42">[42]</a> In addition to single-drug formulations, oral estradiol valerate is available in combination with the <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> <a href="/wiki/Dienogest" title="Dienogest">dienogest</a> as a <a href="/wiki/Combined_oral_contraceptive" class="mw-redirect" title="Combined oral contraceptive">combined oral contraceptive</a> and intramuscular estradiol valerate is marketed at a concentration of 5 mg/mL in combination with the progestin <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a> and with the progestin <a href="/wiki/Norethisterone_enantate" class="mw-redirect" title="Norethisterone enantate">norethisterone enantate</a> as <a href="/wiki/Combined_injectable_contraceptive" class="mw-redirect" title="Combined injectable contraceptive">combined injectable contraceptives</a>.<a href="#cite_note-Drugs@FDA2-39">[39]</a><a href="#cite_note-pmid21151673-26">[26]</a><a href="#cite_note-pmid12290848-27">[27]</a><a href="#cite_note-pmid19076955-28">[28]</a><a href="#cite_note-Drugs.com2-1">[1]</a> Intramuscular estradiol valerate is also marketed at a concentration of 4 mg/mL in combination with the weak <a href="/wiki/Androgen" title="Androgen">androgen</a> and <a href="/wiki/Neurosteroid" title="Neurosteroid">neurosteroid</a> <a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">prasterone enanthate</a> (<abbr title="dehydroepiandrosterone">DHEA</abbr> enanthate) and with the androgen <a href="/wiki/Testosterone_enantate" class="mw-redirect" title="Testosterone enantate">testosterone enantate</a> for use in menopausal hormone therapy, but the latter formulation has been discontinued.<a href="#cite_note-Notelovitz-2012-43">[43]</a><a href="#cite_note-Drugs@FDA2-39">[39]</a> The availability of estradiol valerate-containing products varies throughout the world.<a href="#cite_note-Drugs.com2-1">[1]</a> <table class="wikitable floatright plainrowheaders" style="width: 400px; font-size: 85%;"> <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:Available_forms_of_estradiol" title="Template:Available forms of estradiol"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Available_forms_of_estradiol" title="Template talk:Available forms of estradiol"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Available_forms_of_estradiol" title="Special:EditPage/Template:Available forms of estradiol"><abbr title="Edit this template">e</abbr></a></li></ul></div> Available forms of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a><a href="#cite_note-44">[a]</a> </caption> <tbody><tr> <th scope="col">Route </th> <th scope="col">Ingredient </th> <th scope="col">Form </th> <th scope="col" style="width: 165px">Dose<a href="#cite_note-45">[b]</a> </th> <th scope="col">Brand names<a href="#cite_note-46">[c]</a> </th></tr> <tr> <th scope="row" rowspan="2"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a> </th> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>Tablet</td> <td>0.1, 0.2, 0.5, 1, 2, 4 mg</td> <td>Estrace, Ovocyclin </td></tr> <tr> <td>Estradiol valerate</td> <td>Tablet</td> <td>0.5, 1, 2, 4 mg</td> <td>Progynova </td></tr> <tr> <th scope="row" rowspan="5"><a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">Transdermal</a> </th> <td rowspan="5"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> </td> <td>Patch</td> <td style="font-size: 85%;">14, 25, 37.5, 50, 60, 75, 100 µg/d</td> <td>Climara, Vivelle </td></tr> <tr> <td>Gel pump</td> <td>0.06% (0.52, 0.75 mg/pump)</td> <td>Elestrin, EstroGel </td></tr> <tr> <td>Gel packet</td> <td>0.1% (0.25, 0.5, 1.0 mg/pk.)</td> <td>DiviGel, Sandrena </td></tr> <tr> <td>Emulsion</td> <td>0.25% (25 µg/pouch)</td> <td>Estrasorb </td></tr> <tr> <td>Spray</td> <td>1.53 mg/spray</td> <td>Evamist, Lenzetto </td></tr> <tr> <th scope="row" rowspan="5"><a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">Vaginal</a> </th> <td rowspan="4"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> </td> <td>Tablet</td> <td>10, 25 µg</td> <td>Vagifem </td></tr> <tr> <td>Cream</td> <td>0.01% (0.1 mg/gram)</td> <td>Estrace </td></tr> <tr> <td>Insert</td> <td>4, 10 µg</td> <td>Imvexxy </td></tr> <tr> <td>Ring</td> <td>2 mg/ring (7.5 µg/d, 3 <abbr title="months">mon.</abbr>)</td> <td>Estring </td></tr> <tr> <td><a href="/wiki/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a></td> <td>Ring</td> <td>50, 100 µg/d, 3 months</td> <td>Femring </td></tr> <tr> <th scope="row" rowspan="4"><a href="/wiki/Injection_(medicine)" title="Injection (medicine)">Injection</a><a href="#cite_note-47">[d]</a> </th> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>Microspheres</td> <td>1 mg/mL</td> <td>Juvenum E </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>Oil solution</td> <td>0.167, 0.2, 0.333, 1, 1.67, 2, 5, 10, 20, 25 mg/mL</td> <td>Progynon-B </td></tr> <tr> <td><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></td> <td>Oil solution</td> <td>1, 3, 5 mg/mL</td> <td>Depo-Estradiol </td></tr> <tr> <td>Estradiol valerate</td> <td>Oil solution</td> <td>5, 10, 20, 40 mg/mL</td> <td>Progynon Depot </td></tr> <tr> <th scope="row" rowspan="1"><a href="/wiki/Subcutaneous_implantation" class="mw-redirect" title="Subcutaneous implantation">Implant</a> </th> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>Pellet</td> <td>20, 25, 50, 100 mg, 6 <abbr title="months">mon.</abbr></td> <td>Estradiol Implants </td></tr> <tr class="sortbottom"> <td colspan="5" 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;">Notes and sources:</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 reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-44"><a href="#cite_ref-44">^</a> This table includes primarily products available as a single-ingredient estradiol preparation—thus excluding compounds with progestogens or other ingredients included. The table furthermore does not include <a href="/wiki/Compounded_drug" class="mw-redirect" title="Compounded drug">compounded drugs</a>—only commercially produced products. Availability of each product varies by country. </li> <li id="cite_note-45"><a href="#cite_ref-45">^</a> Doses are given per unit (ex: per tablet, per mL). </li> <li id="cite_note-46"><a href="#cite_ref-46">^</a> Other brand names may be manufactured or previously manufactured. </li> <li id="cite_note-47"><a href="#cite_ref-47">^</a> By intramuscular or subcutaneous injection. </li> </ol></div></div> Sources: <a href="#cite_note-Drugs@FDA-estdose-48">[44]</a><a href="#cite_note-Lobo_2007-49">[45]</a><a href="#cite_note-FalconeHurd2017-50">[46]</a><a href="#cite_note-Becker_2001-51">[47]</a><a href="#cite_note-KleemannEngel2014-52">[48]</a><a href="#cite_note-Muller1998-53">[49]</a><a href="#cite_note-KrishnaShah1996-54">[50]</a><a href="#cite_note-NNR1949-55">[51]</a><a href="#cite_note-AerodiolLabel-56">[52]</a><a href="#cite_note-Drugs.com-57">[53]</a><a href="#cite_note-pmid18382901-58">[54]</a><a href="#cite_note-PlouffeRavnikar2012-59">[55]</a><a href="#cite_note-UC1952-60">[56]</a><a href="#cite_note-Leidenberger2013-61">[57]</a></div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Estradiol_valerate&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/Estradiol_(medication)#Contraindications" title="Estradiol (medication)">Estradiol (medication) § Contraindications</a></div> <a href="/wiki/Contraindication" title="Contraindication">Contraindications</a> of estrogens include <a href="/wiki/Coagulation" title="Coagulation">coagulation</a> problems, <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular diseases</a>, <a href="/wiki/Liver_disease" title="Liver disease">liver disease</a>, and certain <a href="/wiki/Hormone-sensitive_cancer" title="Hormone-sensitive cancer">hormone-sensitive cancers</a> such as <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> and <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a>, among others.<a href="#cite_note-pmid2215269-62">[58]</a><a href="#cite_note-Lauritzen-2005-63">[59]</a><a href="#cite_note-Laurtizen-2001-64">[60]</a><a href="#cite_note-Midwinter-1976-65">[61]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=4" title="Edit section: Side effects">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/Estradiol_(medication)#Side_effects" title="Estradiol (medication)">Estradiol (medication) § Side effects</a></div> The <a href="/wiki/Side_effect" title="Side effect">side effects</a> of estradiol valerate are the same as those of estradiol. Examples of such side effects include <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a> and <a href="/wiki/Breast_enlargement" title="Breast enlargement">enlargement</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Bloating" title="Bloating">bloating</a>, <a href="/wiki/Edema" title="Edema">edema</a>, <a href="/wiki/Headache" title="Headache">headache</a>, and <a href="/wiki/Melasma" title="Melasma">melasma</a>.<a href="#cite_note-Ghosh-2010-15">[15]</a><a href="#cite_note-pmid26684553-66">[62]</a> <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">High-dose estrogen</a> therapy with estradiol valerate injections may also cause an increased risk of <a href="/wiki/Thromboembolism" title="Thromboembolism">thromboembolism</a>, changes in <a href="/wiki/Blood_lipids" title="Blood lipids">blood lipid</a> <a href="/wiki/Lipid_profile" title="Lipid profile">profile</a>, increased <a href="/wiki/Insulin_resistance" title="Insulin resistance">insulin resistance</a>, and increased levels of <a href="/wiki/Prolactin" title="Prolactin">prolactin</a>.<a href="#cite_note-pmid26684553-66">[62]</a> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Estradiol_valerate&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/Estradiol_(medication)#Overdose" title="Estradiol (medication)">Estradiol (medication) § Overdose</a></div> Estradiol valerate has been used at very high doses of 40 to 100 mg once per week in women and men, without overt signs of acute <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> observed.<a href="#cite_note-Göretzlehner-2008-67">[63]</a><a href="#cite_note-pmid7835827-68">[64]</a><a href="#cite_note-pmid6014870-69">[65]</a><a href="#cite_note-pmid5529652-70">[66]</a><a href="#cite_note-Berndt-71">[67]</a><a href="#cite_note-pmid1202923-72">[68]</a><a href="#cite_note-pmid968923-73">[69]</a><a href="#cite_note-pmid4142204-74">[70]</a><a href="#cite_note-pmid4142482-75">[71]</a><a href="#cite_note-Benjamin-1966-76">[72]</a><a href="#cite_note-Benjamin-1967-77">[73]</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">Symptoms</a> of estrogen <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdosage</a> may include <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, <a href="/wiki/Bloating" title="Bloating">bloating</a>, <a href="/wiki/Weight_gain" title="Weight gain">increased weight</a>, <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">water retention</a>, <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Vaginal_discharge" title="Vaginal discharge">vaginal discharge</a>, <a href="/wiki/Heavy_legs" title="Heavy legs">heavy legs</a>, and <a href="/wiki/Leg_cramps" class="mw-redirect" title="Leg cramps">leg cramps</a>.<a href="#cite_note-pmid2215269-62">[58]</a> These side effects can be diminished by reducing the estrogen dosage.<a href="#cite_note-pmid2215269-62">[58]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Estradiol_valerate&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/Estradiol_(medication)#Interactions" title="Estradiol (medication)">Estradiol (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> may influence the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of estradiol and by extension circulating estradiol levels.<a href="#cite_note-pmid11741520-78">[74]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=7" title="Edit section: Pharmacology">edit</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 <a href="/wiki/Active_metabolite" title="Active metabolite">active form</a> of estradiol valerate.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Estradiol_valerate&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> Estradiol valerate is an <a href="/wiki/Estradiol_ester" class="mw-redirect" title="Estradiol ester">estradiol ester</a>, or a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<a href="#cite_note-Oettel-2012-16">[16]</a><a href="#cite_note-pmid16112947-5">[5]</a> As such, it is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a>, or an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a>.<a href="#cite_note-pmid16112947-5">[5]</a><a href="#cite_note-Oettel-2012-16">[16]</a> The <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> of estradiol valerate for the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptor</a> is approximately 50 times lower than that of estradiol.<a href="#cite_note-pmid7169965-4">[4]</a> In addition, estradiol valerate is rapidly cleaved into estradiol and is unable to reach target tissues in concentrations of significance, if at all.<a href="#cite_note-pmid7169965-4">[4]</a> As such, estradiol valerate is essentially inactive in terms of estrogenic effect itself, acting solely as a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> to estradiol.<a href="#cite_note-pmid7169965-4">[4]</a> The <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> of estradiol valerate is about 131% of that of estradiol due to the presence of its C17β <a href="/wiki/Valeric_acid" title="Valeric acid">valerate</a> ester, and hence estradiol valerate contains about 76% of the amount of estradiol of an equal dose of estradiol.<a href="#cite_note-Elks-2014-23">[23]</a><a href="#cite_note-IndexNominum2000-24">[24]</a> Aside from dose adjustment to account for the difference in molecular weight, oral estradiol valerate is considered to be equivalent to oral estradiol.<a href="#cite_note-pmid7169965-4">[4]</a> Because estradiol valerate is a prodrug of estradiol, it is considered to be a <a href="/wiki/Natural_product" title="Natural product">natural</a> and <a href="/wiki/Bioidentical_hormone_replacement_therapy" title="Bioidentical hormone replacement therapy">bioidentical</a> form of estrogen.<a href="#cite_note-Oettel-2012-16">[16]</a><a href="#cite_note-pmid17627398-17">[17]</a><a href="#cite_note-Seth-2012-18">[18]</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:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors" title="Template:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors" title="Template talk:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Affinities_and_estrogenic_potencies_of_estrogen_esters_and_ethers_at_the_estrogen_receptors" title="Special:EditPage/Template:Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors"><abbr title="Edit this template">e</abbr></a></li></ul></div> Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors </caption> <tbody><tr> <th rowspan="2"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a> </th> <th rowspan="2" class="unsortable">Other names </th> <th><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 (%)a </th> <th colspan="2"><a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)"><abbr title="Relative estrogenic potency">REP</abbr></a> (%)b </th></tr> <tr> <th><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">ER</a> </th> <th><a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> </th> <th><a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a> </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> </td> <td>E2 </td> <td>100 </td> <td>100 </td> <td>100 </td></tr> <tr> <td><a href="/wiki/Estradiol_3-sulfate" class="mw-redirect" title="Estradiol 3-sulfate">Estradiol 3-sulfate</a> </td> <td>E2S; E2-3S </td> <td>? </td> <td>0.02 </td> <td>0.04 </td></tr> <tr> <td><a href="/wiki/Estradiol_3-glucuronide" title="Estradiol 3-glucuronide">Estradiol 3-glucuronide</a> </td> <td>E2-3G </td> <td>? </td> <td>0.02 </td> <td>0.09 </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-glucuronide" class="mw-redirect" title="Estradiol 17β-glucuronide">Estradiol 17β-glucuronide</a> </td> <td>E2-17G </td> <td>? </td> <td>0.002 </td> <td>0.0002 </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a> </td> <td>EB; Estradiol 3-benzoate </td> <td>10 </td> <td>1.1 </td> <td>0.52 </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-acetate" title="Estradiol 17β-acetate">Estradiol 17β-acetate</a> </td> <td>E2-17A </td> <td>31–45 </td> <td>24 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_diacetate" title="Estradiol diacetate">Estradiol diacetate</a> </td> <td>EDA; Estradiol 3,17β-diacetate </td> <td>? </td> <td>0.79 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_17%CE%B2-propionate" class="mw-redirect" title="Estradiol 17β-propionate">Estradiol propionate</a> </td> <td>EP; Estradiol 17β-propionate </td> <td>19–26 </td> <td>2.6 </td> <td>? </td></tr> <tr> <td>Estradiol valerate </td> <td>EV; Estradiol 17β-valerate </td> <td>2–11 </td> <td>0.04–21 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a> </td> <td>EC; Estradiol 17β-cypionate </td> <td>?c </td> <td>4.0 </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">Estradiol palmitate</a> </td> <td>Estradiol 17β-palmitate </td> <td>0 </td> <td>? </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estradiol_stearate" title="Estradiol stearate">Estradiol stearate</a> </td> <td>Estradiol 17β-stearate </td> <td>0 </td> <td>? </td> <td>? </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a> </td> <td>E1; 17-Ketoestradiol </td> <td>11 </td> <td>5.3–38 </td> <td>14 </td></tr> <tr> <td><a href="/wiki/Estrone_sulfate" title="Estrone sulfate">Estrone sulfate</a> </td> <td>E1S; Estrone 3-sulfate </td> <td>2 </td> <td>0.004 </td> <td>0.002 </td></tr> <tr> <td><a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a> </td> <td>E1G; Estrone 3-glucuronide </td> <td>? </td> <td><0.001 </td> <td>0.0006 </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> </td> <td>EE; 17α-Ethynylestradiol </td> <td>100 </td> <td>17–150 </td> <td>129 </td></tr> <tr> <td><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a> </td> <td>EE 3-methyl ether </td> <td>1 </td> <td>1.3–8.2 </td> <td>0.16 </td></tr> <tr> <td><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a> </td> <td>EE 3-cyclopentyl ether </td> <td>? </td> <td>0.37 </td> <td>? </td></tr> <tr class="sortbottom"> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = <a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity">Relative binding affinities</a> (RBAs) were determined via <a href="/wiki/In_vitro" title="In vitro">in-vitro</a> displacement of <a href="/wiki/Radiolabel" class="mw-redirect" title="Radiolabel">labeled</a> <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> from <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a> (ERs) generally of <a href="/wiki/Rodent" title="Rodent">rodent</a> <a href="/wiki/Uterus" title="Uterus">uterine</a> <a href="/wiki/Cytosol" title="Cytosol">cytosol</a>. <a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen esters</a> are variably <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolyzed</a> into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. b = Relative estrogenic potencies (REPs) were calculated from <a href="/wiki/Half-maximal_effective_concentration" class="mw-redirect" title="Half-maximal effective concentration">half-maximal effective concentrations</a> (EC50) that were determined via in-vitro <a href="/wiki/%CE%92%E2%80%90galactosidase" class="mw-redirect" title="Β‐galactosidase">β‐galactosidase</a> (β-gal) and <a href="/wiki/Green_fluorescent_protein" title="Green fluorescent protein">green fluorescent protein</a> (GFP) <a href="/wiki/Biosynthesis" title="Biosynthesis">production</a> <a href="/wiki/Bioassay" title="Bioassay">assays</a> in <a href="/wiki/Yeast" title="Yeast">yeast</a> expressing human <a href="/wiki/ER%CE%B1" class="mw-redirect" title="ERα">ERα</a> and human <a href="/wiki/ER%CE%B2" class="mw-redirect" title="ERβ">ERβ</a>. Both <a href="/wiki/Mammal" title="Mammal">mammalian</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> and yeast have the capacity to hydrolyze estrogen esters. c = The affinities of <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a> for the ERs are similar to those of estradiol valerate and <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a> (<a href="/wiki/File:Inhibition_of_estradiol_binding_by_selected_estrogens,_antiestrogens,_and_estrogen_esters_to_human_aortic_tissue_in_vitro.png" title="File:Inhibition of estradiol binding by selected estrogens, antiestrogens, and estrogen esters to human aortic tissue in vitro.png">figure</a>). Sources: See template page. </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-97">[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-98">[a]</a> </th></tr> <tr> <th scope="col" style="width=100px;"><abbr title="Endometrial threshold dose">ETD</abbr><a href="#cite_note-2-3-99">[b]</a> </th> <th scope="col" style="width=100px;"><abbr title="Endometrial proliferation dose">EPD</abbr><a href="#cite_note-2-3-99">[b]</a> </th> <th scope="col" style="width=100px;"><abbr title="Menopausal substitution dose">MSD</abbr><a href="#cite_note-2-3-99">[b]</a> </th> <th scope="col" style="width=100px;"><abbr title="Menopausal substitution dose">MSD</abbr><a href="#cite_note-daily-100">[c]</a> </th> <th scope="col" style="width=100px;"><abbr title="Ovulation-inhibiting dose">OID</abbr><a href="#cite_note-daily-100">[c]</a> </th> <th scope="col" style="width=100px;"><abbr title="Testosterone suppression dose">TSD</abbr><a href="#cite_note-daily-100">[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;">Estradiol valerate </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-101">[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-101">[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;"><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a> </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;"><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=""> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-97"><a href="#cite_ref-97">^</a> <a href="#cite_note-pmid2215269-62">[58]</a><a href="#cite_note-pmid559617-79">[75]</a><a href="#cite_note-WolfSchneider2013-80">[76]</a><a href="#cite_note-GöretzlehnerLauritzen2012-81">[77]</a><a href="#cite_note-KnörrBeller2013-82">[78]</a><a href="#cite_note-HorskyPresl1981-83">[79]</a> <a href="#cite_note-Pschyrembel1968-84">[80]</a><a href="#cite_note-pmid779393-85">[81]</a><a href="#cite_note-Lauritzen1975-86">[82]</a><a href="#cite_note-Kopera1991-87">[83]</a> <a href="#cite_note-pmid29603164-88">[84]</a><a href="#cite_note-pmid29756046-89">[85]</a><a href="#cite_note-Rydén1950-90">[86]</a><a href="#cite_note-pmid14902290-91">[87]</a><a href="#cite_note-Kottmeier1947-92">[88]</a><a href="#cite_note-RietbrockStaib2013-93">[89]</a><a href="#cite_note-Greenblatt1966-94">[90]</a><a href="#cite_note-HerrRevesz1970-95">[91]</a><a href="#cite_note-pmid13370006-96">[92]</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-98"><a href="#cite_ref-98">^</a> Dosages are given in milligrams unless otherwise noted. </li> <li id="cite_note-2-3-99">^ <a href="#cite_ref-2-3_99-0">a</a> <a href="#cite_ref-2-3_99-1">b</a> <a href="#cite_ref-2-3_99-2">c</a> Dosed every 2 to 3 weeks </li> <li id="cite_note-daily-100">^ <a href="#cite_ref-daily_100-0">a</a> <a href="#cite_ref-daily_100-1">b</a> <a href="#cite_ref-daily_100-2">c</a> Dosed daily </li> <li id="cite_note-div-101">^ <a href="#cite_ref-div_101-0">a</a> <a href="#cite_ref-div_101-1">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><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></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> <table class="wikitable floatright mw-collapsible mw-collapsed" style="font-size:small; margin: 1em auto;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Potencies_and_durations_of_natural_estrogens_by_intramuscular_injection" title="Template:Potencies and durations of natural estrogens by intramuscular injection"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Potencies_and_durations_of_natural_estrogens_by_intramuscular_injection" title="Template talk:Potencies and durations of natural estrogens by intramuscular injection"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Potencies_and_durations_of_natural_estrogens_by_intramuscular_injection" title="Special:EditPage/Template:Potencies and durations of natural estrogens by intramuscular injection"><abbr title="Edit this template">e</abbr></a></li></ul></div> Potencies and durations of natural estrogens by intramuscular injection </caption> <tbody><tr> <th rowspan="2">Estrogen</th> <th rowspan="2">Form</th> <th colspan="2">Dose (mg)</th> <th rowspan="2">Duration by dose (mg) </th></tr> <tr> <th><abbr title="Total endometrial proliferation dose over 14 days">EPD</abbr></th> <th><abbr title="Once-monthly combined injectable contraceptive dose">CICD</abbr> </th></tr> <tr> <td rowspan="4"><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>Aq. soln.</td> <td>?</td> <td>–</td> <td><1 d </td></tr> <tr> <td>Oil soln.</td> <td>40–60</td> <td>–</td> <td>1–2 ≈ 1–2 d </td></tr> <tr> <td>Aq. susp.</td> <td>?</td> <td>3.5</td> <td>0.5–2 ≈ 2–7 d; 3.5 ≈ >5 d </td></tr> <tr> <td>Microsph.</td> <td>?</td> <td>–</td> <td>1 ≈ 30 d </td></tr> <tr> <td rowspan="3"><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>Oil soln.</td> <td>25–35</td> <td>–</td> <td>1.66 ≈ 2–3 d; 5 ≈ 3–6 d </td></tr> <tr> <td>Aq. susp.</td> <td>20</td> <td>–</td> <td>10 ≈ 16–21 d </td></tr> <tr> <td>Emulsion</td> <td>?</td> <td>–</td> <td>10 ≈ 14–21 d </td></tr> <tr> <td><a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">Estradiol dipropionate</a></td> <td>Oil soln.</td> <td>25–30</td> <td>–</td> <td>5 ≈ 5–8 d </td></tr> <tr> <td>Estradiol valerate</td> <td>Oil soln.</td> <td>20–30</td> <td>5</td> <td style="font-size: 88%">5 ≈ 7–8 d; 10 ≈ 10–14 d; 40 ≈ 14–21 d; 100 ≈ 21–28 d </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate_butyrate" title="Estradiol benzoate butyrate">Estradiol benz. butyrate</a></td> <td>Oil soln.</td> <td>?</td> <td>10</td> <td>10 ≈ 21 d </td></tr> <tr> <td rowspan="2"><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></td> <td>Oil soln.</td> <td>20–30</td> <td>–</td> <td>5 ≈ 11–14 d </td></tr> <tr> <td>Aq. susp.</td> <td>?</td> <td>5</td> <td>5 ≈ 14–24 d </td></tr> <tr> <td><a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">Estradiol enanthate</a></td> <td>Oil soln.</td> <td>?</td> <td>5–10</td> <td>10 ≈ 20–30 d </td></tr> <tr> <td><a href="/wiki/Estradiol_dienanthate" class="mw-redirect" title="Estradiol dienanthate">Estradiol dienanthate</a></td> <td>Oil soln.</td> <td>?</td> <td>–</td> <td>7.5 ≈ >40 d </td></tr> <tr> <td><a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">Estradiol undecylate</a></td> <td>Oil soln.</td> <td>?</td> <td>–</td> <td>10–20 ≈ 40–60 d; 25–50 ≈ 60–120 d </td></tr> <tr> <td><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></td> <td>Aq. soln.</td> <td>40–60</td> <td>–</td> <td>40 ≈ 30 d; 80 ≈ 60 d; 160 ≈ 120 d </td></tr> <tr> <td rowspan="2"><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>Oil soln.</td> <td>?</td> <td>–</td> <td>1–2 ≈ 2–3 d </td></tr> <tr> <td>Aq. susp.</td> <td>?</td> <td>–</td> <td>0.1–2 ≈ 2–7 d </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>Oil soln.</td> <td>?</td> <td>–</td> <td>1–2 ≈ 1–4 d </td></tr> <tr> <td><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></td> <td>Aq. soln.</td> <td>?</td> <td>–</td> <td>50 ≈ 30 d; 80 ≈ 60 d </td></tr> <tr class="sortbottom"> <td colspan="6" 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;">Notes and sources</div><div class="hidden-content mw-collapsible-content" style=""> Notes: All <a href="/wiki/Aqueous_suspension" class="mw-redirect" title="Aqueous suspension">aqueous suspensions</a> are of <a href="/wiki/Microcrystalline" title="Microcrystalline">microcrystalline</a> <a href="/wiki/Particle_size" title="Particle size">particle size</a>. <a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> production during the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a> is 30–640 µg/d (6.4–8.6 mg total per month or cycle). The <a href="/wiki/Vagina" title="Vagina">vaginal</a> <a href="/wiki/Epithelium" title="Epithelium">epithelium</a> maturation dosage of <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a> or <a class="mw-selflink selflink">estradiol valerate</a> has been reported as 5 to 7 mg/week. An effective <a href="/wiki/Ovulation-inhibiting_dose" class="mw-redirect" title="Ovulation-inhibiting dose">ovulation-inhibiting dose</a> of <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a> is 20–30 mg/month. Sources: See template.</div></div> </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Effects_on_liver_protein_synthesis">Effects on liver protein synthesis</h4>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=9" title="Edit section: Effects on liver protein synthesis">edit</a>]</div> The influence of 2 mg/day oral estradiol valerate on <a href="/wiki/Coagulation_factor" class="mw-redirect" title="Coagulation factor">coagulation factors</a> is less than that of 10 μg/day oral <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>.<a href="#cite_note-pmid23239397-102">[93]</a><a href="#cite_note-pmid21151673-26">[26]</a><a href="#cite_note-pmid19524378-103">[94]</a><a href="#cite_note-pmid2526387-104">[95]</a><a href="#cite_note-pmid15288212-105">[96]</a> Oral ethinylestradiol at 10 μg/day has been found to have about 1.5- to 2.5-fold the impact of 2 mg/day oral estradiol valerate on <a href="/wiki/HDL_cholesterol" class="mw-redirect" title="HDL cholesterol">HDL cholesterol</a> and <a href="/wiki/Triglyceride" title="Triglyceride">triglycerides</a>.<a href="#cite_note-pmid22244780-106">[97]</a><a href="#cite_note-pmid2170823-107">[98]</a><a href="#cite_note-pmid3817605-108">[99]</a> The influence of 20 or 50 μg/day oral ethinylestradiol on coagulation factors and HDL cholesterol is markedly greater than that of 2 mg/day oral estradiol valerate.<a href="#cite_note-pmid22244780-106">[97]</a><a href="#cite_note-pmid3173937-109">[100]</a> <a href="/wiki/Estradiol-containing_birth_control_pill" title="Estradiol-containing birth control pill">Estradiol-containing birth control pills</a>, which contain 1 to 3 mg/day estradiol or estradiol valerate, have been found to increase <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG) levels by 1.5-fold.<a href="#cite_note-pmid21538049-110">[101]</a><a href="#cite_note-pmid22468839-111">[102]</a> Oral estradiol valerate at 6 mg/day has been found to increase SHBG levels by 2.5- to 3-fold in <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a>.<a href="#cite_note-pmid15994752-112">[103]</a><a href="#cite_note-pmid16673210-113">[104]</a> For comparison, <a href="/wiki/Combined_birth_control_pill" class="mw-redirect" title="Combined birth control pill">combined birth control pills</a> containing ethinylestradiol and a progestin with minimal androgenic or antiandrogenic activity have been found to increase SHBG levels by about 3- to 4-fold.<a href="#cite_note-pmid12047300-114">[105]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Estradiol_valerate&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> Regardless of the <a href="/wiki/Route_of_administration" title="Route of administration">route of administration</a>, estradiol valerate behaves as a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of estradiol via <a href="/wiki/Bond_cleavage" title="Bond cleavage">cleavage</a> by <a href="/wiki/Esterase" title="Esterase">esterases</a> into estradiol and the natural <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> <a href="/wiki/Valeric_acid" title="Valeric acid">valeric acid</a>.<a href="#cite_note-pmid16112947-5">[5]</a><a href="#cite_note-Oettel-2012-16">[16]</a><a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-Progynova-115">[106]</a> This cleavage occurs not only in the <a href="/wiki/Liver" title="Liver">liver</a>, but also in the <a href="/wiki/Blood" title="Blood">blood</a> and in <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>, and the <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of estradiol valerate into estradiol and valeric acid is complete regardless of whether the medication is administered <a href="/wiki/Oral_administration" title="Oral administration">orally</a> or <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenterally</a>.<a href="#cite_note-pmid7169965-4">[4]</a> High levels of circulating estradiol are found after an <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">intravenous injection</a> of estradiol valerate, and this indicates very rapid cleavage of the medication upon entering circulation.<a href="#cite_note-pmid7169965-4">[4]</a> <div class="mw-heading mw-heading4"><h4 id="Oral_administration">Oral administration</h4>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=11" title="Edit section: Oral administration">edit</a>]</div> <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">Esterification</a> of the C17β position of estradiol as in estradiol valerate reduces the <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> of estradiol valerate by <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenase</a> (17β-HSD).<a href="#cite_note-pmid16112947-5">[5]</a> As approximately 80% of estradiol is metabolized into estrone (and estrone sulfate) by 17β-HSD during <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass metabolism</a>, this improves the <a href="/wiki/Metabolic_stability" class="mw-redirect" title="Metabolic stability">metabolic stability</a> and hence <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of estradiol valerate.<a href="#cite_note-Oettel-2012-16">[16]</a> However, estradiol valerate is hydrolyzed into estradiol and valeric acid in the <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestines</a>, and hence, is still subject to extensive first-pass metabolism.<a href="#cite_note-pmid16112947-5">[5]</a> As such, the oral bioavailability of estradiol valerate is only around 3 to 5%, and is similar to that of oral estradiol.<a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-pmid16112947-5">[5]</a><a href="#cite_note-Shellenberger-1986-116">[107]</a> All oral tablets in the cases of both estradiol and estradiol valerate seem to be micronized.<a href="#cite_note-pmid10098476-42">[42]</a> Due to its nature as a rapidly converted prodrug of estradiol, the <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of oral estradiol valerate are similar to those of oral estradiol.<a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-pmid16112947-5">[5]</a> Moreover, the <a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">pharmacodynamics</a> and <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> (after differences in <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> are taken into account) of oral estradiol valerate are considered to be equivalent to those of oral estradiol.<a href="#cite_note-pmid7169965-4">[4]</a> This is also notably true for effects on <a href="/wiki/Hepatic_protein_synthesis" class="mw-redirect" title="Hepatic protein synthesis">hepatic protein synthesis</a> (e.g., of <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), again after differences in molecular weight between the two compounds are considered.<a href="#cite_note-pmid7169965-4">[4]</a> A dosage of 1 mg/day oral estradiol valerate has been found to produce approximate circulating concentrations of 50 pg/mL estradiol and 160 pg/mL estrone, while a dosage of 2 mg/day results in circulating levels of 60 pg/mL estradiol and 300 pg/mL estrone.<a href="#cite_note-pmid8530713-117">[108]</a> These concentrations of estradiol and estrone are comparable to those observed with 1 and 2 mg/day oral estradiol.<a href="#cite_note-pmid8530713-117">[108]</a> A review of selected studies reported a range of mean peak estradiol levels of 24 to 140 pg/mL occurring 1 to 12 hours after administration of 2 mg oral estradiol valerate.<a href="#cite_note-pmid7169965-4">[4]</a> A study found that, in accordance with their differences in molecular weights, oral estradiol produced higher levels of estradiol than oral estradiol valerate.<a href="#cite_note-pmid11709743-118">[109]</a> Likewise, other studies found that levels of estradiol and estrone are very similar after oral administration of roughly equimolar doses of estradiol (1.5 mg) and estradiol valerate (2 mg).<a href="#cite_note-pmid20004267-119">[110]</a><a href="#cite_note-pmid9751449-120">[111]</a><a href="#cite_note-pmid10412891-121">[112]</a> A study of high-dose oral estradiol valerate found levels of estradiol of about 250 pg/mL after a single 10-mg dose in three women.<a href="#cite_note-Shellenberger-1986-116">[107]</a> <style data-mw-deduplicate="TemplateStyles:r1248256098">@media all and (max-width:720px){.mw-parser-output .mod-gallery{width:100%!important}}.mw-parser-output .mod-gallery{display:table}.mw-parser-output .mod-gallery-default{background:transparent;margin-top:4px}.mw-parser-output .mod-gallery-center{margin-left:auto;margin-right:auto}.mw-parser-output .mod-gallery-left{float:left}.mw-parser-output .mod-gallery-right{float:right}.mw-parser-output .mod-gallery-none{float:none}.mw-parser-output .mod-gallery-collapsible{width:100%}.mw-parser-output .mod-gallery .title,.mw-parser-output .mod-gallery .main,.mw-parser-output .mod-gallery .footer{display:table-row}.mw-parser-output .mod-gallery .title>div{display:table-cell;padding:0 4px 4px;text-align:center;font-weight:bold}.mw-parser-output .mod-gallery .main>div{display:table-cell}.mw-parser-output .mod-gallery .gallery{line-height:1.35em}.mw-parser-output .mod-gallery .footer>div{display:table-cell;padding:4px;text-align:right;font-size:85%;line-height:1em}.mw-parser-output .mod-gallery .title>div *,.mw-parser-output .mod-gallery .footer>div *{overflow:visible}.mw-parser-output .mod-gallery .gallerybox img{background:none!important}.mw-parser-output .mod-gallery .bordered-images .thumb img{border:solid var(--background-color-neutral,#eaecf0)1px}.mw-parser-output .mod-gallery .whitebg .thumb{background:var(--background-color-base,#fff)!important}</style><div class="mod-gallery mod-gallery-center" style=""font-size:small;""><div class="title"><div>Hormone levels with oral estradiol valerate</div></div><div class="main"><div><ul class="gallery mw-gallery-traditional nochecker bordered-images whitebg"> <li class="gallerybox" style="width: 435px"> <div class="thumb" style="width: 430px; height: 330px;"><a href="/wiki/File:Estradiol_levels_with_oral_micronized_estradiol_and_oral_estradiol_valerate_in_postmenopausal_women.png" class="mw-file-description" title="Baseline-adjusted estradiol levels after a single oral dose of 1.5 mg micronized estradiol or 2.0 mg estradiol valerate in postmenopausal women.[113][112] Source was Timmer & Geurts (1999).[112]"><img alt="Baseline-adjusted estradiol levels after a single oral dose of 1.5 mg micronized estradiol or 2.0 mg estradiol valerate in postmenopausal women.[113][112] Source was Timmer & Geurts (1999).[112]" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_levels_with_oral_micronized_estradiol_and_oral_estradiol_valerate_in_postmenopausal_women.png/400px-Estradiol_levels_with_oral_micronized_estradiol_and_oral_estradiol_valerate_in_postmenopausal_women.png" decoding="async" width="400" height="259" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_levels_with_oral_micronized_estradiol_and_oral_estradiol_valerate_in_postmenopausal_women.png/600px-Estradiol_levels_with_oral_micronized_estradiol_and_oral_estradiol_valerate_in_postmenopausal_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_levels_with_oral_micronized_estradiol_and_oral_estradiol_valerate_in_postmenopausal_women.png/800px-Estradiol_levels_with_oral_micronized_estradiol_and_oral_estradiol_valerate_in_postmenopausal_women.png 2x" data-file-width="2204" data-file-height="1425" /></a></div> <div class="gallerytext">Baseline-adjusted estradiol levels after a single oral dose of 1.5 mg micronized estradiol or 2.0 mg estradiol valerate in postmenopausal women.<a href="#cite_note-Jensen-2013-122">[113]</a><a href="#cite_note-pmid10412891-121">[112]</a> Source was Timmer & Geurts (1999).<a href="#cite_note-pmid10412891-121">[112]</a></div> </li> <li class="gallerybox" style="width: 435px"> <div class="thumb" style="width: 430px; height: 330px;"><a href="/wiki/File:Estradiol_levels_after_a_single_dose_and_with_continuous_administration_of_oral_estradiol_or_oral_estradiol_valerate_in_women.png" class="mw-file-description" title="Estradiol levels after a single oral dose of 2 mg micronized estradiol or 2 mg estradiol valerate and with continuous oral administration of 2 mg/day micronized estradiol or 2 mg/day estradiol valerate (at steady state) in postmenopausal women.[109] Source was Wiegratz et al. (2001).[109]"><img alt="Estradiol levels after a single oral dose of 2 mg micronized estradiol or 2 mg estradiol valerate and with continuous oral administration of 2 mg/day micronized estradiol or 2 mg/day estradiol valerate (at steady state) in postmenopausal women.[109] Source was Wiegratz et al. (2001).[109]" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Estradiol_levels_after_a_single_dose_and_with_continuous_administration_of_oral_estradiol_or_oral_estradiol_valerate_in_women.png/377px-Estradiol_levels_after_a_single_dose_and_with_continuous_administration_of_oral_estradiol_or_oral_estradiol_valerate_in_women.png" decoding="async" width="377" height="300" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Estradiol_levels_after_a_single_dose_and_with_continuous_administration_of_oral_estradiol_or_oral_estradiol_valerate_in_women.png/565px-Estradiol_levels_after_a_single_dose_and_with_continuous_administration_of_oral_estradiol_or_oral_estradiol_valerate_in_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2c/Estradiol_levels_after_a_single_dose_and_with_continuous_administration_of_oral_estradiol_or_oral_estradiol_valerate_in_women.png/754px-Estradiol_levels_after_a_single_dose_and_with_continuous_administration_of_oral_estradiol_or_oral_estradiol_valerate_in_women.png 2x" data-file-width="1442" data-file-height="1148" /></a></div> <div class="gallerytext">Estradiol levels after a single oral dose of 2 mg micronized estradiol or 2 mg estradiol valerate and with continuous oral administration of 2 mg/day micronized estradiol or 2 mg/day estradiol valerate (at steady state) in postmenopausal women.<a href="#cite_note-pmid11709743-118">[109]</a> Source was Wiegratz et al. (2001).<a href="#cite_note-pmid11709743-118">[109]</a></div> </li> </ul></div></div></div> <div class="mw-heading mw-heading4"><h4 id="Sublingual_administration">Sublingual administration</h4>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=12" title="Edit section: Sublingual administration">edit</a>]</div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Hormone_levels_with_oral_estradiol_valerate_tablets_(Progynova)_taken_sublingually_in_premenopausal_women.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Hormone_levels_with_oral_estradiol_valerate_tablets_%28Progynova%29_taken_sublingually_in_premenopausal_women.png/425px-Hormone_levels_with_oral_estradiol_valerate_tablets_%28Progynova%29_taken_sublingually_in_premenopausal_women.png" decoding="async" width="425" height="330" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Hormone_levels_with_oral_estradiol_valerate_tablets_%28Progynova%29_taken_sublingually_in_premenopausal_women.png/638px-Hormone_levels_with_oral_estradiol_valerate_tablets_%28Progynova%29_taken_sublingually_in_premenopausal_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Hormone_levels_with_oral_estradiol_valerate_tablets_%28Progynova%29_taken_sublingually_in_premenopausal_women.png/850px-Hormone_levels_with_oral_estradiol_valerate_tablets_%28Progynova%29_taken_sublingually_in_premenopausal_women.png 2x" data-file-width="1409" data-file-height="1093" /></a><figcaption>Hormone levels with 2-mg oral micronized estradiol valerate tablets (Progynova, Schering) taken continuously 3 or 4 times per day by the <a href="/wiki/Sublingual_administration" title="Sublingual administration">sublingual</a> route in premenopausal women.<a href="#cite_note-pmid2566746-123">[114]</a><a href="#cite_note-pmid2207608-124">[115]</a></figcaption></figure> Estradiol valerate has been studied by <a href="/wiki/Sublingual_administration" title="Sublingual administration">sublingual administration</a> in premenopausal women for the purpose of <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">cycle</a> control and <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> suppression in <a href="/wiki/Egg_donation" title="Egg donation">egg donation</a> and <a href="/wiki/Surrogacy" title="Surrogacy">surrogacy</a>.<a href="#cite_note-pmid2566746-123">[114]</a><a href="#cite_note-pmid2207608-124">[115]</a> It has been investigated for this indication, along with <a href="/wiki/Vaginal_estradiol" class="mw-redirect" title="Vaginal estradiol">vaginal</a> and <a href="/wiki/Transdermal_estradiol" class="mw-redirect" title="Transdermal estradiol">transdermal estradiol</a>, because oral estradiol valerate is sometimes unable to achieve adequate estradiol levels and hence proper cycle control in this situation.<a href="#cite_note-pmid2566746-123">[114]</a><a href="#cite_note-pmid2207608-124">[115]</a> Sublingual administration of estradiol valerate bypasses the <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first pass</a> that occurs with the oral route and results in higher levels of estradiol and improved cycle control.<a href="#cite_note-pmid2566746-123">[114]</a><a href="#cite_note-pmid2207608-124">[115]</a> Sublingual estradiol valerate is also used in hormone therapy for transgender women.<a href="#cite_note-pmid30671393-125">[116]</a> The administration of 2 mg oral micronized estradiol valerate tablets (Progynova, Schering) sublingually 3 or 4 times per day has been found to result in circulating estradiol levels of about 290 pg/mL to 460 pg/mL in premenopausal women (time of measurements not given).<a href="#cite_note-pmid2566746-123">[114]</a><a href="#cite_note-pmid2207608-124">[115]</a> <a href="/wiki/Steady-state_levels" class="mw-redirect" title="Steady-state levels">Steady-state levels</a> of estradiol were achieved within about 2 or 3 days.<a href="#cite_note-pmid2566746-123">[114]</a><a href="#cite_note-pmid2207608-124">[115]</a> Levels of <a href="/wiki/Progesterone" title="Progesterone">progesterone</a>, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a>, and <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> were all considerably suppressed, and ovulation, as well as the associated mid-cycle hormonal surges, were prevented.<a href="#cite_note-pmid2566746-123">[114]</a><a href="#cite_note-pmid2207608-124">[115]</a> Similarly to oral administration of estradiol, but in contrast to the vaginal and transdermal routes, the ratio of estradiol to estrone is decreased with sublingual administration of either estradiol valerate or estradiol.<a href="#cite_note-pmid2566746-123">[114]</a><a href="#cite_note-pmid2207608-124">[115]</a><a href="#cite_note-pmid10585176-126">[117]</a> <div class="mw-heading mw-heading4"><h4 id="Intramuscular_injection">Intramuscular injection</h4>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=13" title="Edit section: Intramuscular injection">edit</a>]</div> In contrast to oral administration, the bioavailability of estradiol valerate is complete (i.e., 100%) via intramuscular injection.<a href="#cite_note-pmid8013217-6">[6]</a><a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-pmid16112947-5">[5]</a> Due to the far greater bioavailability of intramuscular estradiol valerate relative to oral, the former is substantially stronger (in terms of potency) than the latter.<a href="#cite_note-pmid7169965-4">[4]</a> As an example, a single 4 mg intramuscular injection is said to be approximately equivalent to 2 mg/day of the medication administered orally over the course of 3 weeks.<a href="#cite_note-pmid7169965-4">[4]</a> Estradiol valerate, when given intramuscularly in <a href="/wiki/Oil" title="Oil">oil</a>, has a relatively long duration due to the formation of an intramuscular <a href="/wiki/Depot_injection" title="Depot injection">depot</a> from which the medication is slowly released and absorbed.<a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-Sriram-2007-127">[118]</a> Upon intramuscular injection of estradiol valerate in an oil solution, the solvent (i.e., oil) is absorbed, and a primary <a href="/wiki/Microcrystalline" title="Microcrystalline">microcrystalline</a> depot is formed within the <a href="/wiki/Muscle" title="Muscle">muscle</a> at the site of injection.<a href="#cite_note-pmid16112947-5">[5]</a> In addition, a secondary depot may also be formed in <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a>.<a href="#cite_note-pmid16112947-5">[5]</a> The slow release of estradiol valerate is caused by the increased <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a> of the medication, which in turn is due to its long fatty acid valeric acid ester <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a>.<a href="#cite_note-pmid7169965-4">[4]</a> The <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of estradiol valerate in oil by intramuscular injection (brand names Estradiol-Depot 10 mg, Progynon Depot-10) is about 3.5 days, with a range of 1.2 days to 7.2 days in different individuals.<a href="#cite_note-pmid22257576-9">[9]</a> Α couple of older studies from the 1980s with <a href="/wiki/Sample_size" class="mw-redirect" title="Sample size">sample sizes</a> of only 2 or 3 individuals reported an elimination half-life of 4 to 5 days.<a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-pmid6220949-128">[119]</a><a href="#cite_note-pmid2987096-129">[120]</a> A single intramuscular injection of 4 mg estradiol valerate has been found to result in maximal circulating levels of estradiol of about 390 pg/mL within 3 days of administration, with levels declining to 100 pg/mL (baseline, in the study) by 12 to 13 days.<a href="#cite_note-Notelovitz-2012-43">[43]</a> Studies in general have found that a single intramuscular injection of 4 mg estradiol valerate results in peak levels of estradiol of 240 to 540 pg/mL after 1 to 5 days following administration.<a href="#cite_note-pmid2987096-129">[120]</a> A study found that a single intramuscular injection of 5 mg estradiol valerate resulted in peak circulating levels of 667 pg/mL estradiol and 324 pg/mL estrone within approximately 2 and 3 days, respectively.<a href="#cite_note-pmid7389356-10">[10]</a> The duration of estradiol valerate at this dose and in this study was considered to be 7 to 8 days.<a href="#cite_note-pmid7389356-10">[10]</a> Other studies have found that larger doses of intramuscular estradiol valerate exceeding 20 mg have a duration of more than 15 days.<a href="#cite_note-pmid7389356-10">[10]</a> A third study, in contrast to the preceding study, found that a single 10 mg intramuscular injection of estradiol valerate resulted in maximal estradiol levels of 506 to 544 pg/mL and maximal estrone levels of 205 to 219 pg/mL in postmenopausal women.<a href="#cite_note-pmid22257576-9">[9]</a> With intramuscular injections of estradiol valerate, it has been reported that a dose of 5 mg has a duration of 7 to 8 days, 10 mg a duration of 10 to 14 days, 40 mg a duration of 2 to 3 weeks (14 to 21 days), and 100 mg a duration of 3 to 4 weeks (21 to 28 days).<a href="#cite_note-Lauritzen-1988-11">[11]</a><a href="#cite_note-Labhart-2012-12">[12]</a><a href="#cite_note-pmid7389356-10">[10]</a> A study of <a href="/wiki/Pseudopregnancy" title="Pseudopregnancy">pseudopregnancy</a> with <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injections</a> of 40 mg/week estradiol valerate and 250 mg/week <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a> in women with <a href="/wiki/Estrogen_deficiency" class="mw-redirect" title="Estrogen deficiency">estrogen deficiency</a> observed estradiol levels of about 3,100 pg/mL at 3 months of therapy and 2,500 pg/mL at 6 months of therapy.<a href="#cite_note-pmid7835827-68">[64]</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:Pharmacokinetics_of_three_estradiol_esters_by_intramuscular_injection" title="Template:Pharmacokinetics of three estradiol esters by intramuscular injection"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Pharmacokinetics_of_three_estradiol_esters_by_intramuscular_injection" title="Template talk:Pharmacokinetics of three estradiol esters by intramuscular injection"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Pharmacokinetics_of_three_estradiol_esters_by_intramuscular_injection" title="Special:EditPage/Template:Pharmacokinetics of three estradiol esters by intramuscular injection"><abbr title="Edit this template">e</abbr></a></li></ul></div> Pharmacokinetics of three estradiol esters by intramuscular injection </caption> <tbody><tr> <th>Estrogen</th> <th>Dose</th> <th><a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">Cmax</a></th> <th><a href="/wiki/Tmax_(pharmacology)" class="mw-redirect" title="Tmax (pharmacology)">Tmax</a></th> <th><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration</a> </th></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>5 mg</td> <td><abbr title="Estradiol">E2</abbr>: 940 pg/mL <abbr title="Estrone">E1</abbr>: 343 pg/mL</td> <td><abbr title="Estradiol">E2</abbr>: 1.8 days <abbr title="Estrone">E1</abbr>: 2.4 days</td> <td>4–5 days </td></tr> <tr> <td>Estradiol valerate</td> <td>5 mg</td> <td><abbr title="Estradiol">E2</abbr>: 667 pg/mL <abbr title="Estrone">E1</abbr>: 324 pg/mL</td> <td><abbr title="Estradiol">E2</abbr>: 2.2 days <abbr title="Estrone">E1</abbr>: 2.7 days</td> <td>7–8 days </td></tr> <tr> <td><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></td> <td>5 mg</td> <td><abbr title="Estradiol">E2</abbr>: 338 pg/mL <abbr title="Estrone">E1</abbr>: 145 pg/mL</td> <td><abbr title="Estradiol">E2</abbr>: 3.9 days <abbr title="Estrone">E1</abbr>: 5.1 days</td> <td>11 days </td></tr> <tr class="sortbottom"> <td colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: All via <a href="/wiki/Intramuscular_injection" title="Intramuscular injection"><abbr title="intramuscular">i.m.</abbr> injection</a> of <a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</a>. Determinations via <a href="/wiki/Radioimmunoassay" title="Radioimmunoassay">radioimmunoassay</a> with <a href="/wiki/Chromatographic_separation" class="mw-redirect" title="Chromatographic separation">chromatographic separation</a>. Sources: See template. </td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1248256098"><div class="mod-gallery mod-gallery-center" style=""font-size:small;""><div class="title"><div>Hormone levels with estradiol valerate by intramuscular injection</div></div><div class="main"><div><ul class="gallery mw-gallery-traditional nochecker bordered-images whitebg"> <li class="gallerybox" style="width: 335px"> <div class="thumb" style="width: 330px; height: 240px;"><a href="/wiki/File:Estrogen_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_in_postmenopausal_women.png" class="mw-file-description" title="Estrogen levels after a single intramuscular injection of 10 mg estradiol valerate in oil in 24 postmenopausal women.[9] Determinations were made for both Progynon Depot 10 and Estradiol Depot 10, for a total of 48 measurements per point.[9] Assays were performed using GC/MS-NCI/SIM.[9] Source was Schug et al. (2012).[9]"><img alt="Estrogen levels after a single intramuscular injection of 10 mg estradiol valerate in oil in 24 postmenopausal women.[9] Determinations were made for both Progynon Depot 10 and Estradiol Depot 10, for a total of 48 measurements per point.[9] Assays were performed using GC/MS-NCI/SIM.[9] Source was Schug et al. (2012).[9]" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Estrogen_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_in_postmenopausal_women.png/300px-Estrogen_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_in_postmenopausal_women.png" decoding="async" width="300" height="194" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Estrogen_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_in_postmenopausal_women.png/450px-Estrogen_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_in_postmenopausal_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d0/Estrogen_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_in_postmenopausal_women.png/600px-Estrogen_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_in_postmenopausal_women.png 2x" data-file-width="1697" data-file-height="1099" /></a></div> <div class="gallerytext">Estrogen levels after a single intramuscular injection of 10 mg estradiol valerate in oil in 24 postmenopausal women.<a href="#cite_note-pmid22257576-9">[9]</a> Determinations were made for both Progynon Depot 10 and Estradiol Depot 10, for a total of 48 measurements per point.<a href="#cite_note-pmid22257576-9">[9]</a> Assays were performed using <a href="/wiki/Gas_chromatography%E2%80%93mass_spectrometry" title="Gas chromatography–mass spectrometry">GC/MS</a>-<a href="/wiki/Negative_chemical_ionization" class="mw-redirect" title="Negative chemical ionization">NCI</a>/<a href="/wiki/Selected_ion_monitoring" title="Selected ion monitoring">SIM</a>.<a href="#cite_note-pmid22257576-9">[9]</a> Source was Schug et al. (2012).<a href="#cite_note-pmid22257576-9">[9]</a></div> </li> <li class="gallerybox" style="width: 335px"> <div class="thumb" style="width: 330px; height: 240px;"><a href="/wiki/File:Hormone_levels_after_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_in_postmenopausal_women.png" class="mw-file-description" title="Hormone levels after a single intramuscular injection of 5 mg estradiol valerate in oil in 17 postmenopausal women.[121] Assays were performed using EIA.[121] Estrone levels were likely overestimated, possibly due to cross reactivity of the assay with estrogen conjugates.[9] Source was Göretzlehner et al. (2002).[121]"><img alt="Hormone levels after a single intramuscular injection of 5 mg estradiol valerate in oil in 17 postmenopausal women.[121] Assays were performed using EIA.[121] Estrone levels were likely overestimated, possibly due to cross reactivity of the assay with estrogen conjugates.[9] Source was Göretzlehner et al. (2002).[121]" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Hormone_levels_after_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_in_postmenopausal_women.png/300px-Hormone_levels_after_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_in_postmenopausal_women.png" decoding="async" width="300" height="208" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Hormone_levels_after_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_in_postmenopausal_women.png/450px-Hormone_levels_after_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_in_postmenopausal_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0c/Hormone_levels_after_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_in_postmenopausal_women.png/600px-Hormone_levels_after_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_in_postmenopausal_women.png 2x" data-file-width="1593" data-file-height="1105" /></a></div> <div class="gallerytext">Hormone levels after a single intramuscular injection of 5 mg estradiol valerate in oil in 17 postmenopausal women.<a href="#cite_note-Göretzlehner-2002-130">[121]</a> Assays were performed using <a href="/wiki/ELISA" title="ELISA">EIA</a>.<a href="#cite_note-Göretzlehner-2002-130">[121]</a> Estrone levels were likely overestimated, possibly due to cross reactivity of the assay with <a href="/wiki/Estrogen_conjugate" title="Estrogen conjugate">estrogen conjugates</a>.<a href="#cite_note-pmid22257576-9">[9]</a> Source was Göretzlehner et al. (2002).<a href="#cite_note-Göretzlehner-2002-130">[121]</a></div> </li> <li class="gallerybox" style="width: 335px"> <div class="thumb" style="width: 330px; height: 240px;"><a href="/wiki/File:Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png" class="mw-file-description" title="Hormone levels after a single intramuscular injection of estradiol valerate/norethisterone enanthate (5 mg/50 mg) (Mesigyna) in healthy young men.[122] Testosterone decreased from ~503 ng/dL to ~30 ng/dL (–94%).[122] Source was Valle Alvarez (2011).[122]"><img alt="Hormone levels after a single intramuscular injection of estradiol valerate/norethisterone enanthate (5 mg/50 mg) (Mesigyna) in healthy young men.[122] Testosterone decreased from ~503 ng/dL to ~30 ng/dL (–94%).[122] Source was Valle Alvarez (2011).[122]" src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png/300px-Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png" decoding="async" width="300" height="193" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png/450px-Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4a/Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png/600px-Hormone_levels_in_men_with_a_single_intramuscular_injection_of_5_mg_estradiol_valerate_and_50_mg_norethisterone_enanthate_in_oil.png 2x" data-file-width="1894" data-file-height="1218" /></a></div> <div class="gallerytext">Hormone levels after a single intramuscular injection of <a href="/wiki/Estradiol_valerate/norethisterone_enanthate" class="mw-redirect" title="Estradiol valerate/norethisterone enanthate">estradiol valerate/norethisterone enanthate</a> (5 mg/50 mg) (Mesigyna) in healthy young men.<a href="#cite_note-del_Cisne_Valle_Alvarez-2011-131">[122]</a> Testosterone decreased from ~503 ng/dL to ~30 ng/dL (–94%).<a href="#cite_note-del_Cisne_Valle_Alvarez-2011-131">[122]</a> Source was Valle Alvarez (2011).<a href="#cite_note-del_Cisne_Valle_Alvarez-2011-131">[122]</a></div> </li> <li class="gallerybox" style="width: 335px"> <div class="thumb" style="width: 330px; height: 240px;"><a href="/wiki/File:Estradiol_levels_after_a_single_5_mg_intramuscular_injection_of_estradiol_esters.png" class="mw-file-description" title="Estradiol levels after single intramuscular injections of 5 mg of different estradiol esters in oil in about 10 premenopausal women each.[10] Assays were performed using RIA with CS.[10] Source was Oriowo et al. (1980).[10]"><img alt="Estradiol levels after single intramuscular injections of 5 mg of different estradiol esters in oil in about 10 premenopausal women each.[10] Assays were performed using RIA with CS.[10] Source was Oriowo et al. (1980).[10]" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Estradiol_levels_after_a_single_5_mg_intramuscular_injection_of_estradiol_esters.png/300px-Estradiol_levels_after_a_single_5_mg_intramuscular_injection_of_estradiol_esters.png" decoding="async" width="300" height="190" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Estradiol_levels_after_a_single_5_mg_intramuscular_injection_of_estradiol_esters.png/450px-Estradiol_levels_after_a_single_5_mg_intramuscular_injection_of_estradiol_esters.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/33/Estradiol_levels_after_a_single_5_mg_intramuscular_injection_of_estradiol_esters.png/600px-Estradiol_levels_after_a_single_5_mg_intramuscular_injection_of_estradiol_esters.png 2x" data-file-width="1983" data-file-height="1256" /></a></div> <div class="gallerytext">Estradiol levels after single intramuscular injections of 5 mg of different estradiol esters in oil in about 10 premenopausal women each.<a href="#cite_note-pmid7389356-10">[10]</a> Assays were performed using <a href="/wiki/Radioimmunoassay" title="Radioimmunoassay">RIA</a> with <a href="/wiki/Chromatographic_separation" class="mw-redirect" title="Chromatographic separation">CS</a>.<a href="#cite_note-pmid7389356-10">[10]</a> Source was Oriowo et al. (1980).<a href="#cite_note-pmid7389356-10">[10]</a></div> </li> <li class="gallerybox" style="width: 335px"> <div class="thumb" style="width: 330px; height: 240px;"><a href="/wiki/File:Estradiol_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_and_100_mg_estradiol_undecylate.png" class="mw-file-description" title="Estradiol levels after a single intramuscular injection of 10 mg estradiol valerate or 100 mg estradiol undecylate in oil both in 4 individuals each.[123] Subject characteristics and assay method were not described.[123] Source was Vermeulen (1975).[123]"><img alt="Estradiol levels after a single intramuscular injection of 10 mg estradiol valerate or 100 mg estradiol undecylate in oil both in 4 individuals each.[123] Subject characteristics and assay method were not described.[123] Source was Vermeulen (1975).[123]" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Estradiol_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_and_100_mg_estradiol_undecylate.png/300px-Estradiol_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_and_100_mg_estradiol_undecylate.png" decoding="async" width="300" height="149" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Estradiol_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_and_100_mg_estradiol_undecylate.png/450px-Estradiol_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_and_100_mg_estradiol_undecylate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Estradiol_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_and_100_mg_estradiol_undecylate.png/600px-Estradiol_levels_after_a_single_intramuscular_injection_of_10_mg_estradiol_valerate_and_100_mg_estradiol_undecylate.png 2x" data-file-width="2213" data-file-height="1099" /></a></div> <div class="gallerytext">Estradiol levels after a single intramuscular injection of 10 mg estradiol valerate or 100 mg <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a> in oil both in 4 individuals each.<a href="#cite_note-pmid1231448-132">[123]</a> Subject characteristics and assay method were not described.<a href="#cite_note-pmid1231448-132">[123]</a> Source was Vermeulen (1975).<a href="#cite_note-pmid1231448-132">[123]</a></div> </li> <li class="gallerybox" style="width: 335px"> <div class="thumb" style="width: 330px; height: 240px;"><a href="/wiki/File:Estradiol_and_dehydroepiandrosterone_levels_after_a_single_intramuscular_injection_of_Gynodian_Depot_in_women.png" class="mw-file-description" title="Estradiol and DHEA levels after a single intramuscular injection of Gynodian Depot (4 mg estradiol valerate, 200 mg prasterone enanthate in oil) or Primogyn Depot (10 mg estradiol valerate in oil) in women.[124][119][125] Assays were performed using RIA.[119][125] Sources were Düsterberg & Wendt (1983) and Rauramo et al. (1980).[124][119][125]"><img alt="Estradiol and DHEA levels after a single intramuscular injection of Gynodian Depot (4 mg estradiol valerate, 200 mg prasterone enanthate in oil) or Primogyn Depot (10 mg estradiol valerate in oil) in women.[124][119][125] Assays were performed using RIA.[119][125] Sources were Düsterberg & Wendt (1983) and Rauramo et al. (1980).[124][119][125]" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Estradiol_and_dehydroepiandrosterone_levels_after_a_single_intramuscular_injection_of_Gynodian_Depot_in_women.png/300px-Estradiol_and_dehydroepiandrosterone_levels_after_a_single_intramuscular_injection_of_Gynodian_Depot_in_women.png" decoding="async" width="300" height="180" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Estradiol_and_dehydroepiandrosterone_levels_after_a_single_intramuscular_injection_of_Gynodian_Depot_in_women.png/450px-Estradiol_and_dehydroepiandrosterone_levels_after_a_single_intramuscular_injection_of_Gynodian_Depot_in_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dd/Estradiol_and_dehydroepiandrosterone_levels_after_a_single_intramuscular_injection_of_Gynodian_Depot_in_women.png/600px-Estradiol_and_dehydroepiandrosterone_levels_after_a_single_intramuscular_injection_of_Gynodian_Depot_in_women.png 2x" data-file-width="1828" data-file-height="1097" /></a></div> <div class="gallerytext">Estradiol and <abbr title="dehydroepiandrosterone">DHEA</abbr> levels after a single intramuscular injection of <a href="/wiki/Estradiol_valerate/prasterone_enanthate" title="Estradiol valerate/prasterone enanthate">Gynodian Depot</a> (4 mg estradiol valerate, 200 mg <a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">prasterone enanthate</a> in oil) or Primogyn Depot (10 mg estradiol valerate in oil) in women.<a href="#cite_note-Kuhl-1987-133">[124]</a><a href="#cite_note-pmid6220949-128">[119]</a><a href="#cite_note-pmid7402086-134">[125]</a> Assays were performed using <a href="/wiki/Radioimmunoassay" title="Radioimmunoassay">RIA</a>.<a href="#cite_note-pmid6220949-128">[119]</a><a href="#cite_note-pmid7402086-134">[125]</a> Sources were Düsterberg & Wendt (1983) and Rauramo et al. (1980).<a href="#cite_note-Kuhl-1987-133">[124]</a><a href="#cite_note-pmid6220949-128">[119]</a><a href="#cite_note-pmid7402086-134">[125]</a></div> </li> <li class="gallerybox" style="width: 335px"> <div class="thumb" style="width: 330px; height: 240px;"><a href="/wiki/File:Estradiol_levels_after_injections_of_estradiol,_estradiol_benzoate,_estradiol_valerate,_and_estradiol_undecylate_in_women.png" class="mw-file-description" title="Estradiol levels after a short intravenous infusion of 20 mg estradiol in aqueous solution or an intramuscular injection of equimolar doses of estradiol esters in oil solution in postmenopausal women.[126][127] Assays were performed using RIA with CS.[126][127] Source was Geppert (1975).[126][127]"><img alt="Estradiol levels after a short intravenous infusion of 20 mg estradiol in aqueous solution or an intramuscular injection of equimolar doses of estradiol esters in oil solution in postmenopausal women.[126][127] Assays were performed using RIA with CS.[126][127] Source was Geppert (1975).[126][127]" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Estradiol_levels_after_injections_of_estradiol%2C_estradiol_benzoate%2C_estradiol_valerate%2C_and_estradiol_undecylate_in_women.png/300px-Estradiol_levels_after_injections_of_estradiol%2C_estradiol_benzoate%2C_estradiol_valerate%2C_and_estradiol_undecylate_in_women.png" decoding="async" width="300" height="197" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Estradiol_levels_after_injections_of_estradiol%2C_estradiol_benzoate%2C_estradiol_valerate%2C_and_estradiol_undecylate_in_women.png/450px-Estradiol_levels_after_injections_of_estradiol%2C_estradiol_benzoate%2C_estradiol_valerate%2C_and_estradiol_undecylate_in_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b1/Estradiol_levels_after_injections_of_estradiol%2C_estradiol_benzoate%2C_estradiol_valerate%2C_and_estradiol_undecylate_in_women.png/600px-Estradiol_levels_after_injections_of_estradiol%2C_estradiol_benzoate%2C_estradiol_valerate%2C_and_estradiol_undecylate_in_women.png 2x" data-file-width="2196" data-file-height="1442" /></a></div> <div class="gallerytext">Estradiol levels after a short intravenous infusion of 20 mg estradiol in aqueous solution or an intramuscular injection of equimolar doses of estradiol esters in oil solution in postmenopausal women.<a href="#cite_note-Geppert-1975-135">[126]</a><a href="#cite_note-pmid1150068-136">[127]</a> Assays were performed using <a href="/wiki/Radioimmunoassay" title="Radioimmunoassay">RIA</a> with <a href="/wiki/Chromatographic_separation" class="mw-redirect" title="Chromatographic separation">CS</a>.<a href="#cite_note-Geppert-1975-135">[126]</a><a href="#cite_note-pmid1150068-136">[127]</a> Source was Geppert (1975).<a href="#cite_note-Geppert-1975-135">[126]</a><a href="#cite_note-pmid1150068-136">[127]</a></div> </li> <li class="gallerybox" style="width: 335px"> <div class="thumb" style="width: 330px; height: 240px;"><a href="/wiki/File:Estradiol_levels_after_an_intramuscular_injection_of_Climacteron_or_estradiol_valerate_in_ovariectomized_women.png" class="mw-file-description" title="Estradiol levels after an intramuscular injection of 10 mg estradiol valerate in oil, Climacteron (150 mg testosterone enanthate, 1 mg estradiol benzoate, 7.5 mg estradiol dienanthate in oil), and control group in 20, 11, and 11 ovariectomized women, respectively.[128] Assays were performed using RIA.[128] Source was Sherwin et al. (1987).[128]"><img alt="Estradiol levels after an intramuscular injection of 10 mg estradiol valerate in oil, Climacteron (150 mg testosterone enanthate, 1 mg estradiol benzoate, 7.5 mg estradiol dienanthate in oil), and control group in 20, 11, and 11 ovariectomized women, respectively.[128] Assays were performed using RIA.[128] Source was Sherwin et al. (1987).[128]" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Estradiol_levels_after_an_intramuscular_injection_of_Climacteron_or_estradiol_valerate_in_ovariectomized_women.png/300px-Estradiol_levels_after_an_intramuscular_injection_of_Climacteron_or_estradiol_valerate_in_ovariectomized_women.png" decoding="async" width="300" height="200" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Estradiol_levels_after_an_intramuscular_injection_of_Climacteron_or_estradiol_valerate_in_ovariectomized_women.png/450px-Estradiol_levels_after_an_intramuscular_injection_of_Climacteron_or_estradiol_valerate_in_ovariectomized_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e5/Estradiol_levels_after_an_intramuscular_injection_of_Climacteron_or_estradiol_valerate_in_ovariectomized_women.png/600px-Estradiol_levels_after_an_intramuscular_injection_of_Climacteron_or_estradiol_valerate_in_ovariectomized_women.png 2x" data-file-width="1694" data-file-height="1131" /></a></div> <div class="gallerytext">Estradiol levels after an intramuscular injection of 10 mg estradiol valerate in oil, <a href="/wiki/Climacteron" class="mw-redirect" title="Climacteron">Climacteron</a> (150 mg <a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">testosterone enanthate</a>, 1 mg <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, 7.5 mg <a href="/wiki/Estradiol_dienanthate" class="mw-redirect" title="Estradiol dienanthate">estradiol dienanthate</a> in oil), and control group in 20, 11, and 11 ovariectomized women, respectively.<a href="#cite_note-pmid3826177-137">[128]</a> Assays were performed using <a href="/wiki/Radioimmunoassay" title="Radioimmunoassay">RIA</a>.<a href="#cite_note-pmid3826177-137">[128]</a> Source was Sherwin et al. (1987).<a href="#cite_note-pmid3826177-137">[128]</a></div> </li> <li class="gallerybox" style="width: 335px"> <div class="thumb" style="width: 330px; height: 240px;"><a href="/wiki/File:Idealized_curves_of_estradiol_levels_after_injection_of_different_estradiol_esters_in_women.png" class="mw-file-description" title="Simplified curves of estradiol levels after injection of different estradiol esters in women.[129] Source was Garza-Flores (1994).[129]"><img alt="Simplified curves of estradiol levels after injection of different estradiol esters in women.[129] Source was Garza-Flores (1994).[129]" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Idealized_curves_of_estradiol_levels_after_injection_of_different_estradiol_esters_in_women.png/293px-Idealized_curves_of_estradiol_levels_after_injection_of_different_estradiol_esters_in_women.png" decoding="async" width="293" height="210" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Idealized_curves_of_estradiol_levels_after_injection_of_different_estradiol_esters_in_women.png/440px-Idealized_curves_of_estradiol_levels_after_injection_of_different_estradiol_esters_in_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8c/Idealized_curves_of_estradiol_levels_after_injection_of_different_estradiol_esters_in_women.png/586px-Idealized_curves_of_estradiol_levels_after_injection_of_different_estradiol_esters_in_women.png 2x" data-file-width="1759" data-file-height="1261" /></a></div> <div class="gallerytext">Simplified curves of estradiol levels after injection of different estradiol esters in women.<a href="#cite_note-pmid8013219-138">[129]</a> Source was Garza-Flores (1994).<a href="#cite_note-pmid8013219-138">[129]</a></div> </li> </ul></div></div></div> <div class="mw-heading mw-heading4"><h4 id="Subcutaneous_injection">Subcutaneous injection</h4>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=14" title="Edit section: Subcutaneous injection">edit</a>]</div> Estradiol esters like estradiol valerate and <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a> can be given by <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous injection</a> instead of intramuscular injection.<a href="#cite_note-pmid28078219-139">[130]</a><a href="#cite_note-pmid22078184-140">[131]</a> <div class="mw-heading mw-heading4"><h4 id="Intravenous_injection">Intravenous injection</h4>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=15" title="Edit section: Intravenous injection">edit</a>]</div> The administration of estradiol valerate by intravenous injection has been studied.<a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-pmid2987096-129">[120]</a> It has been found to be very rapidly cleaved into estradiol.<a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-pmid2987096-129">[120]</a> The bioavailability and metabolism of estradiol valerate does not differ with intravenous versus intramuscular injection.<a href="#cite_note-pmid2987096-129">[120]</a> Conversely, intravenous injection of estradiol valerate has a very short duration, whereas intramuscular injection has a long duration and <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a>.<a href="#cite_note-pmid2987096-129">[120]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=16" 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/Estrogen_ester" title="Estrogen ester">Estrogen ester</a> and <a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">List of estrogen esters § Estradiol esters</a></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Estradiol_esterification_into_estradiol_valerate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Estradiol_esterification_into_estradiol_valerate.png/325px-Estradiol_esterification_into_estradiol_valerate.png" decoding="async" width="325" height="320" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/Estradiol_esterification_into_estradiol_valerate.png/488px-Estradiol_esterification_into_estradiol_valerate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/Estradiol_esterification_into_estradiol_valerate.png/650px-Estradiol_esterification_into_estradiol_valerate.png 2x" data-file-width="3050" data-file-height="3007" /></a><figcaption><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a> plus the <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> <a href="/wiki/Valeric_acid" title="Valeric acid">valeric acid</a> (valerate) equals estradiol valerate, a C17β ester of estradiol.<a href="#cite_note-Shellenberger-1986-116">[107]</a></figcaption></figure> Estradiol valerate is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> and the C17β <a href="/wiki/Valeric_acid" title="Valeric acid">valerate</a> (pentanoate) <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> <a href="/wiki/Ester" title="Ester">ester</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<a href="#cite_note-Elks-2014-23">[23]</a><a href="#cite_note-IndexNominum2000-24">[24]</a> It is also known as estradiol 17β-valerate or as estra-1,3,5(10)-triene-3,17β-diol 17β-pentanoate.<a href="#cite_note-Elks-2014-23">[23]</a><a href="#cite_note-IndexNominum2000-24">[24]</a> Other common esters of estradiol in use include <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enantate" title="Estradiol enantate">estradiol enantate</a>, and <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, the former two of which are C17β esters of estradiol similarly to estradiol valerate and the latter of which is the C3 <a href="/wiki/Acetate" title="Acetate">acetate</a> ester of estradiol.<a href="#cite_note-Elks-2014-23">[23]</a><a href="#cite_note-IndexNominum2000-24">[24]</a> The experimental log <a href="/wiki/Octanol/water_partition_coefficient" class="mw-redirect" title="Octanol/water partition coefficient">octanol/water partition coefficient</a> (log P) of estradiol valerate is 5.6.<a href="#cite_note-ChemSpider-141">[132]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="font-size:small; 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:Structural_properties_of_selected_estradiol_esters" title="Template:Structural properties of selected estradiol esters"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Structural_properties_of_selected_estradiol_esters" title="Template talk:Structural properties of selected estradiol esters"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Structural_properties_of_selected_estradiol_esters" title="Special:EditPage/Template:Structural properties of selected estradiol esters"><abbr title="Edit this template">e</abbr></a></li></ul></div> Structural properties of selected estradiol esters </caption> <tbody><tr> <th rowspan="2">Estrogen</th> <th rowspan="2" class="unsortable">Structure</th> <th colspan="4">Ester(s)</th> <th rowspan="2">Relative <abbr title="molecular weight">mol. weight</abbr></th> <th rowspan="2">Relative <abbr title="estradiol">E2</abbr> contentb</th> <th rowspan="2">log Pc </th></tr> <tr> <th>Position(s)</th> <th class="unsortable">Moiet(ies)</th> <th>Type</th> <th>Lengtha </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/35px-Estradiol.svg.png" decoding="async" width="35" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/53px-Estradiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/70px-Estradiol.svg.png 2x" data-file-width="512" data-file-height="324" /></a><figcaption></figcaption></figure></td> <td>–</td> <td>–</td> <td>–</td> <td>–</td> <td>1.00</td> <td>1.00</td> <td>4.0 </td></tr> <tr> <td><a href="/wiki/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_3-acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_3-acetate.svg/35px-Estradiol_3-acetate.svg.png" decoding="async" width="35" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_3-acetate.svg/53px-Estradiol_3-acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_3-acetate.svg/70px-Estradiol_3-acetate.svg.png 2x" data-file-width="1350" data-file-height="810" /></a><figcaption></figcaption></figure></td> <td>C3</td> <td><a href="/wiki/Ethanoic_acid" class="mw-redirect" title="Ethanoic acid">Ethanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>2</td> <td>1.15</td> <td>0.87</td> <td>4.2 </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_benzoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_benzoate.svg/35px-Estradiol_benzoate.svg.png" decoding="async" width="35" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_benzoate.svg/53px-Estradiol_benzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_benzoate.svg/70px-Estradiol_benzoate.svg.png 2x" data-file-width="512" data-file-height="292" /></a><figcaption></figcaption></figure></td> <td>C3</td> <td><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a></td> <td>Aromatic fatty acid</td> <td>– (~4–5)</td> <td>1.38</td> <td>0.72</td> <td>4.7 </td></tr> <tr> <td><a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">Estradiol dipropionate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_dipropionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Estradiol_dipropionate.svg/35px-Estradiol_dipropionate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Estradiol_dipropionate.svg/53px-Estradiol_dipropionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/16/Estradiol_dipropionate.svg/70px-Estradiol_dipropionate.svg.png 2x" data-file-width="512" data-file-height="263" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Propanoic_acid" class="mw-redirect" title="Propanoic acid">Propanoic acid</a> (×2)</td> <td>Straight-chain fatty acid</td> <td>3 (×2)</td> <td>1.41</td> <td>0.71</td> <td>4.9 </td></tr> <tr> <td>Estradiol valerate</td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_valerate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Estradiol_valerate.svg/35px-Estradiol_valerate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Estradiol_valerate.svg/53px-Estradiol_valerate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/66/Estradiol_valerate.svg/70px-Estradiol_valerate.svg.png 2x" data-file-width="512" data-file-height="268" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Pentanoic_acid" class="mw-redirect" title="Pentanoic acid">Pentanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>5</td> <td>1.31</td> <td>0.76</td> <td>5.6–6.3 </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate_butyrate" title="Estradiol benzoate butyrate">Estradiol benzoate butyrate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_butyrate_benzoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_butyrate_benzoate.svg/35px-Estradiol_butyrate_benzoate.svg.png" decoding="async" width="35" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_butyrate_benzoate.svg/53px-Estradiol_butyrate_benzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_butyrate_benzoate.svg/70px-Estradiol_butyrate_benzoate.svg.png 2x" data-file-width="965" data-file-height="540" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a>, <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a></td> <td>Mixed fatty acid</td> <td>– (~6, 2)</td> <td>1.64</td> <td>0.61</td> <td>6.3 </td></tr> <tr> <td><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_17_beta-cypionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Estradiol_17_beta-cypionate.svg/35px-Estradiol_17_beta-cypionate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Estradiol_17_beta-cypionate.svg/53px-Estradiol_17_beta-cypionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Estradiol_17_beta-cypionate.svg/70px-Estradiol_17_beta-cypionate.svg.png 2x" data-file-width="512" data-file-height="269" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Cyclopentylpropanoic_acid" class="mw-redirect" title="Cyclopentylpropanoic acid">Cyclopentylpropanoic acid</a></td> <td>Cyclic fatty acid</td> <td>– (~6)</td> <td>1.46</td> <td>0.69</td> <td>6.9 </td></tr> <tr> <td><a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">Estradiol enanthate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_enanthate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Estradiol_enanthate.png/35px-Estradiol_enanthate.png" decoding="async" width="35" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Estradiol_enanthate.png/53px-Estradiol_enanthate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Estradiol_enanthate.png/70px-Estradiol_enanthate.png 2x" data-file-width="2407" data-file-height="1144" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Heptanoic_acid" class="mw-redirect" title="Heptanoic acid">Heptanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>7</td> <td>1.41</td> <td>0.71</td> <td>6.7–7.3 </td></tr> <tr> <td><a href="/wiki/Estradiol_dienanthate" class="mw-redirect" title="Estradiol dienanthate">Estradiol dienanthate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_dienanthate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Estradiol_dienanthate.svg/35px-Estradiol_dienanthate.svg.png" decoding="async" width="35" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Estradiol_dienanthate.svg/53px-Estradiol_dienanthate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Estradiol_dienanthate.svg/70px-Estradiol_dienanthate.svg.png 2x" data-file-width="2605" data-file-height="900" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Heptanoic_acid" class="mw-redirect" title="Heptanoic acid">Heptanoic acid</a> (×2)</td> <td>Straight-chain fatty acid</td> <td>7 (×2)</td> <td>1.82</td> <td>0.55</td> <td>8.1–10.4 </td></tr> <tr> <td><a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">Estradiol undecylate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_undecylate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Estradiol_undecylate.svg/35px-Estradiol_undecylate.svg.png" decoding="async" width="35" height="13" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Estradiol_undecylate.svg/53px-Estradiol_undecylate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Estradiol_undecylate.svg/70px-Estradiol_undecylate.svg.png 2x" data-file-width="512" data-file-height="186" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Undecanoic_acid" class="mw-redirect" title="Undecanoic acid">Undecanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>11</td> <td>1.62</td> <td>0.62</td> <td>9.2–9.8 </td></tr> <tr> <td><a href="/wiki/Estradiol_stearate" title="Estradiol stearate">Estradiol stearate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_stearate_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Estradiol_stearate_structure.svg/35px-Estradiol_stearate_structure.svg.png" decoding="async" width="35" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Estradiol_stearate_structure.svg/53px-Estradiol_stearate_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/Estradiol_stearate_structure.svg/70px-Estradiol_stearate_structure.svg.png 2x" data-file-width="3160" data-file-height="900" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Octadecanoic_acid" class="mw-redirect" title="Octadecanoic acid">Octadecanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>18</td> <td>1.98</td> <td>0.51</td> <td>12.2–12.4 </td></tr> <tr> <td><a href="/wiki/Estradiol_distearate" title="Estradiol distearate">Estradiol distearate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_distearate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Estradiol_distearate.svg/35px-Estradiol_distearate.svg.png" decoding="async" width="35" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Estradiol_distearate.svg/53px-Estradiol_distearate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Estradiol_distearate.svg/70px-Estradiol_distearate.svg.png 2x" data-file-width="1615" data-file-height="705" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Octadecanoic_acid" class="mw-redirect" title="Octadecanoic acid">Octadecanoic acid</a> (×2)</td> <td>Straight-chain fatty acid</td> <td>18 (×2)</td> <td>2.96</td> <td>0.34</td> <td>20.2 </td></tr> <tr> <td><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_sulfate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/35px-Estradiol_sulfate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/53px-Estradiol_sulfate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/70px-Estradiol_sulfate.svg.png 2x" data-file-width="690" data-file-height="360" /></a><figcaption></figcaption></figure></td> <td>C3</td> <td><a href="/wiki/Sulfuric_acid" title="Sulfuric acid">Sulfuric acid</a></td> <td>Water-soluble conjugate</td> <td>–</td> <td>1.29</td> <td>0.77</td> <td>0.3–3.8 </td></tr> <tr> <td><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_sulfate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/35px-Estradiol_sulfate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/53px-Estradiol_sulfate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/70px-Estradiol_sulfate.svg.png 2x" data-file-width="690" data-file-height="360" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Glucuronic_acid" title="Glucuronic acid">Glucuronic acid</a></td> <td>Water-soluble conjugate</td> <td>–</td> <td>1.65</td> <td>0.61</td> <td>2.1–2.7 </td></tr> <tr> <td><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a>d</td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estramustine_phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/35px-Estramustine_phosphate.svg.png" decoding="async" width="35" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/53px-Estramustine_phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/70px-Estramustine_phosphate.svg.png 2x" data-file-width="1995" data-file-height="1285" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Normustine" title="Normustine">Normustine</a>, <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a></td> <td>Water-soluble conjugate</td> <td>–</td> <td>1.91</td> <td>0.52</td> <td>2.9–5.0 </td></tr> <tr> <td><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a>e</td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Polyestradiol_phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Polyestradiol_phosphate.svg/35px-Polyestradiol_phosphate.svg.png" decoding="async" width="35" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Polyestradiol_phosphate.svg/53px-Polyestradiol_phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Polyestradiol_phosphate.svg/70px-Polyestradiol_phosphate.svg.png 2x" data-file-width="1550" data-file-height="1050" /></a><figcaption></figcaption></figure></td> <td>C3–C17β</td> <td><a href="/wiki/Phosphoric_acid" title="Phosphoric acid">Phosphoric acid</a></td> <td>Water-soluble conjugate</td> <td>–</td> <td>1.23f</td> <td>0.81f</td> <td>2.9g </td></tr> <tr class="sortbottom"> <td colspan="10" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = Length of <a href="/wiki/Ester" title="Ester">ester</a> in <a href="/wiki/Carbon" title="Carbon">carbon</a> <a href="/wiki/Atom" title="Atom">atoms</a> for <a href="/wiki/Straight-chain_fatty_acid" class="mw-redirect" title="Straight-chain fatty acid">straight-chain fatty acids</a> or approximate length of ester in carbon atoms for <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> or <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a> fatty acids. b = Relative estradiol content by weight (i.e., relative <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> exposure). c = Experimental or predicted <a href="/wiki/Partition_coefficient" title="Partition coefficient">octanol/water partition coefficient</a> (i.e., <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a>/<a href="/wiki/Hydrophobicity" class="mw-redirect" title="Hydrophobicity">hydrophobicity</a>). Retrieved from <a href="/wiki/PubChem" title="PubChem">PubChem</a>, <a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a>, and <a href="/wiki/DrugBank" title="DrugBank">DrugBank</a>. d = Also known as estradiol normustine phosphate. e = <a href="/wiki/Polymer" title="Polymer">Polymer</a> of <a href="/wiki/Estradiol_phosphate" title="Estradiol phosphate">estradiol phosphate</a> (~13 <a href="/wiki/Repeat_unit" title="Repeat unit">repeat units</a>). f = Relative molecular weight or estradiol content per repeat unit. g = log P of repeat unit (i.e., estradiol phosphate). Sources: See individual articles. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=17" title="Edit section: History">edit</a>]</div> Estradiol valerate was <a href="/wiki/Patent" title="Patent">patented</a> by <a href="/wiki/Ciba_Specialty_Chemicals" title="Ciba Specialty Chemicals">Ciba</a> in 1940 and 1941, with a <a href="/wiki/Priority_date" title="Priority date">priority date</a> of 1936.<a href="#cite_note-Kleemann-2014-19">[19]</a><a href="#cite_note-US2205627A-142">[133]</a> It was <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> and studied, along with a variety of other <a href="/wiki/Estradiol_ester" class="mw-redirect" title="Estradiol ester">estradiol esters</a>, by Karl Junkmann of <a href="/wiki/Schering_AG" title="Schering AG">Schering AG</a> in 1953.<a href="#cite_note-pmid15193460-143">[134]</a><a href="#cite_note-Junkmann-1953-144">[135]</a> The medication was first introduced for medical use via <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> in 1954 by Schering in <a href="/wiki/Europe" title="Europe">Europe</a> under the brand name Progynon Depot and by <a href="/wiki/Bristol-Myers_Squibb" class="mw-redirect" title="Bristol-Myers Squibb">Squibb</a> in the <a href="/wiki/United_States" title="United States">United States</a> under the brand name Delestrogen.<a href="#cite_note-Publishing2013-20">[20]</a><a href="#cite_note-Duetsch-1969-21">[21]</a><a href="#cite_note-Ehrengut-1954-145">[136]</a> In 1966, oral estradiol valerate was introduced by Schering for medical use in Europe under the brand name Progynova.<a href="#cite_note-Kuhl-2008-146">[137]</a><a href="#cite_note-Klinische_Wochenschrift-1966-147">[138]</a><a href="#cite_note-pmid5593020-148">[139]</a><a href="#cite_note-pmid5728263-149">[140]</a><a href="#cite_note-pmid5045321-150">[141]</a> A report of its metabolism was published in 1967.<a href="#cite_note-Kolb-1967-151">[142]</a> <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">Esterification</a> of estradiol, as in estradiol valerate, has been claimed to improve its <a href="/wiki/Metabolic_stability" class="mw-redirect" title="Metabolic stability">metabolic stability</a> with oral administration.<a href="#cite_note-pmid16112947-5">[5]</a><a href="#cite_note-pmid7169965-4">[4]</a><a href="#cite_note-Estrace-FDA-152">[143]</a> In 1968, <a href="/wiki/Micronized" class="mw-redirect" title="Micronized">micronized</a> preparations of oral estradiol valerate were first introduced under the brand names Progynova 21 and Progynova 21 mite.<a href="#cite_note-Kuhl-2008-146">[137]</a> Along with <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a> (1933)<a href="#cite_note-Kaufman-1933-153">[144]</a><a href="#cite_note-Buschbeck-2009-154">[145]</a><a href="#cite_note-Biskind-1935-155">[146]</a> and <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a> (1952),<a href="#cite_note-Sittig-1988-156">[147]</a> estradiol valerate is one of the most widely used esters of estradiol.<a href="#cite_note-Yen-1991-22">[22]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=18" title="Edit section: Society and culture">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Generic_names">Generic names</h3>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=19" title="Edit section: Generic names">edit</a>]</div> Estradiol valerate is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name, <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BANM</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name, and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name, while oestradiol valerate was formerly its <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BANM</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name.<a href="#cite_note-Elks-2014-23">[23]</a><a href="#cite_note-IndexNominum2000-24">[24]</a><a href="#cite_note-Drugs.com-2-157">[148]</a> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=20" title="Edit section: Brand names">edit</a>]</div> Estradiol valerate has been marketed under the brand names Altadiol, Androtardyl-Oestradiol, Ardefem, Climaval, Cyclabil, Cyclocur, Deladiol, Delahormone Unimatic, Delestrogen, Delestrogen 4X, Depogen, Diol-20, Dioval, Ditate, Dura-Estate, Dura-Estradiol, Duratrad, Duragen, Estate, Estra-L, Estradiol Depot, Estraval, Estraval Depot, Estraval PA, Estravel, Femogen, Femogex, Gynogen L.A., Gynokadin, Lastrogen, Menaval, Merimono, Neofollin, Nuvelle, Oestrogynal, Ostrin Depo, Pelanin, Pharlon, Postoval, Primogyna, Primogyn, Primogyn Depot, Progynon, Progynon Depot, Progynova, Repestrogen, Repo-Estra, Reposo-E, Retestrin, Ronfase, Span-Est, Testaval, and Valergen, among others.<a href="#cite_note-Elks-2014-23">[23]</a><a href="#cite_note-IndexNominum2000-24">[24]</a><a href="#cite_note-Publishing2013-20">[20]</a><a href="#cite_note-Lewis-2008-158">[149]</a><a href="#cite_note-Drugs.com-2-157">[148]</a> Neofollin is an <a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</a> of estradiol valerate.<a href="#cite_note-Kubíková-2014-159">[150]</a><a href="#cite_note-Neofollin-Label-160">[151]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=21" 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> Oral estradiol valerate is used primarily in <a href="/wiki/Europe" title="Europe">Europe</a>, under the brand name Progynova.<a href="#cite_note-Sanfilippo-1998-161">[152]</a> Although oral estradiol valerate was previously available in the <a href="/wiki/United_States" title="United States">United States</a>,<a href="#cite_note-IndexNominum2000-24">[24]</a> it is no longer available in this country except in combination with <a href="/wiki/Dienogest" title="Dienogest">dienogest</a> as a <a href="/wiki/Combined_oral_contraceptive" class="mw-redirect" title="Combined oral contraceptive">combined oral contraceptive</a> (under the brand name Natazia).<a href="#cite_note-Drugs@FDA2-39">[39]</a> Estradiol valerate by intramuscular injection is available under the brand name Delestrogen in the United States and <a href="/wiki/Canada" title="Canada">Canada</a> and under the brand name Progynon Depot in Europe and elsewhere in the world.<a href="#cite_note-Drugs@FDA2-39">[39]</a><a href="#cite_note-IndexNominum2000-24">[24]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=22" title="Edit section: Research">edit</a>]</div> <a href="/wiki/SH-834" class="mw-redirect" title="SH-834">SH-834</a> was a combination of 90 mg estradiol valerate and 300 mg <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a> for weekly intramuscular injection that was developed by Schering in the 1970s.<a href="#cite_note-pmid1202923-72">[68]</a><a href="#cite_note-pmid4555897-162">[153]</a><a href="#cite_note-pmid5088730-163">[154]</a> It was investigated clinically as a treatment for <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> and was found to be effective, but was never marketed.<a href="#cite_note-pmid1202923-72">[68]</a><a href="#cite_note-pmid5529652-70">[66]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=23" title="Edit section: See also">edit</a>]</div> <ul><li><a href="/wiki/Estradiol_valerate/hydroxyprogesterone_caproate" title="Estradiol valerate/hydroxyprogesterone caproate">Estradiol valerate/hydroxyprogesterone caproate</a></li> <li><a href="/wiki/Estradiol_valerate/norethisterone_enantate" title="Estradiol valerate/norethisterone enantate">Estradiol valerate/norethisterone enantate</a></li> <li><a href="/wiki/Estradiol_valerate/prasterone_enanthate" title="Estradiol valerate/prasterone enanthate">Estradiol valerate/prasterone enanthate</a></li> <li><a href="/wiki/Estradiol_valerate/testosterone_enanthate" title="Estradiol valerate/testosterone enanthate">Estradiol valerate/testosterone enanthate</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=24" 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-Drugs.com2-1">^ <a href="#cite_ref-Drugs.com2_1-0">a</a> <a href="#cite_ref-Drugs.com2_1-1">b</a> <a href="#cite_ref-Drugs.com2_1-2">c</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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/cons/estradiol-and-dienogest.html">"Estradiol and dienogest Advanced Patient Information"</a>. 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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&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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Piersol-1975-38"><a href="#cite_ref-Piersol-1975_38-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPiersol1975" class="citation book cs1">Piersol G (1975). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=RiE9K5bgKcsC">The Cyclopedia of Medicine, Surgery, Specialties</a>. F. A. Davis Company.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Cyclopedia+of+Medicine%2C+Surgery%2C+Specialties&rft.pub=F.+A.+Davis+Company&rft.date=1975&rft.aulast=Piersol&rft.aufirst=G&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DRiE9K5bgKcsC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Drugs@FDA2-39">^ <a href="#cite_ref-Drugs@FDA2_39-0">a</a> <a href="#cite_ref-Drugs@FDA2_39-1">b</a> <a href="#cite_ref-Drugs@FDA2_39-2">c</a> <a href="#cite_ref-Drugs@FDA2_39-3">d</a> <a href="#cite_ref-Drugs@FDA2_39-4">e</a> <a href="#cite_ref-Drugs@FDA2_39-5">f</a> <a href="#cite_ref-Drugs@FDA2_39-6">g</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.accessdata.fda.gov/scripts/cder/daf/">"Drugs@FDA: FDA Approved Drug Products"</a>. 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CRC Press. pp. 276, 313, 379, 561, 566. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-7692-2114-5" title="Special:BookSources/978-3-7692-2114-5"><bdi>978-3-7692-2114-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=European+Drug+Index%3A+European+Drug+Registrations&rft.pages=276%2C+313%2C+379%2C+561%2C+566&rft.edition=Fourth&rft.pub=CRC+Press&rft.date=1998-06-19&rft.isbn=978-3-7692-2114-5&rft.au=Muller&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2HBPHmclMWIC%26pg%3DPA276&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Becker-2001-41"><a href="#cite_ref-Becker-2001_41-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBecker2001" class="citation book cs1">Becker KL (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FVfzRvaucq8C&pg=PA2153">Principles and Practice of Endocrinology and Metabolism</a>. Lippincott Williams & Wilkins. pp. 2153–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-1750-2" title="Special:BookSources/978-0-7817-1750-2"><bdi>978-0-7817-1750-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+and+Practice+of+Endocrinology+and+Metabolism&rft.pages=2153-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2001&rft.isbn=978-0-7817-1750-2&rft.aulast=Becker&rft.aufirst=KL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFVfzRvaucq8C%26pg%3DPA2153&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid10098476-42">^ <a href="#cite_ref-pmid10098476_42-0">a</a> <a href="#cite_ref-pmid10098476_42-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDevroeyPados1998" class="citation journal cs1">Devroey P, Pados G (1998). "Preparation of endometrium for egg donation". Human Reproduction Update. 4 (6): 856–861. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fhumupd%2F4.6.856">10.1093/humupd/4.6.856</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/10098476">10098476</a>. <q>Oestradiol valerate and oestradiol in a micronized form are the most widely used oestrogen per os for steroid substitution therapy. Our regimen, as of most other groups [...] is oestradiol valerate (Progynova; Schering, Berlin, Germany) given in various concentrations throughout the cycle [...]. According to Norfolk's protocol, 2 mg of micronized oestradiol valerate are given on cycle days 1–5. [...] In tablet form, micronized oestradiol valerate is also efficiently absorbed [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Human+Reproduction+Update&rft.atitle=Preparation+of+endometrium+for+egg+donation&rft.volume=4&rft.issue=6&rft.pages=856-861&rft.date=1998&rft_id=info%3Adoi%2F10.1093%2Fhumupd%2F4.6.856&rft_id=info%3Apmid%2F10098476&rft.aulast=Devroey&rft.aufirst=P&rft.au=Pados%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Notelovitz-2012-43">^ <a href="#cite_ref-Notelovitz-2012_43-0">a</a> <a href="#cite_ref-Notelovitz-2012_43-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNotelovitzvan_Keep2012" class="citation book cs1">Notelovitz M, van Keep PA (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=VM0hBQAAQBAJ&pg=PA397">The Climacteric in Perspective: Proceedings of the Fourth International Congress on the Menopause, held at Lake Buena Vista, Florida, October 28–November 2, 1984</a>. Springer Science & Business Media. pp. 397, 399. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-009-4145-8" title="Special:BookSources/978-94-009-4145-8"><bdi>978-94-009-4145-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Climacteric+in+Perspective%3A+Proceedings+of+the+Fourth+International+Congress+on+the+Menopause%2C+held+at+Lake+Buena+Vista%2C+Florida%2C+October+28%E2%80%93November+2%2C+1984&rft.pages=397%2C+399&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-009-4145-8&rft.aulast=Notelovitz&rft.aufirst=M&rft.au=van+Keep%2C+PA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DVM0hBQAAQBAJ%26pg%3DPA397&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Drugs@FDA-estdose-48"><a href="#cite_ref-Drugs@FDA-estdose_48-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.accessdata.fda.gov/scripts/cder/daf/">"Drugs@FDA: FDA Approved Drug Products"</a>. United States Food and Drug Administration. Retrieved 26 July 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Drugs%40FDA%3A+FDA+Approved+Drug+Products&rft.pub=United+States+Food+and+Drug+Administration&rft_id=http%3A%2F%2Fwww.accessdata.fda.gov%2Fscripts%2Fcder%2Fdaf%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Lobo_2007-49"><a href="#cite_ref-Lobo_2007_49-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLobo2007" class="citation book cs1">Lobo RA (5 June 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=gywV9hkcyOMC&pg=PA217">Treatment of the Postmenopausal Woman: Basic and Clinical Aspects</a>. Academic Press. pp. 177, 217–226, 770–771. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-055309-2" title="Special:BookSources/978-0-08-055309-2"><bdi>978-0-08-055309-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Treatment+of+the+Postmenopausal+Woman%3A+Basic+and+Clinical+Aspects&rft.pages=177%2C+217-226%2C+770-771&rft.pub=Academic+Press&rft.date=2007-06-05&rft.isbn=978-0-08-055309-2&rft.aulast=Lobo&rft.aufirst=RA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DgywV9hkcyOMC%26pg%3DPA217&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-FalconeHurd2017-50"><a href="#cite_ref-FalconeHurd2017_50-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFalconeHurd2017" class="citation book cs1">Falcone T, Hurd WW (14 June 2017). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=pzgoDwAAQBAJ&pg=PA179">Clinical Reproductive Medicine and Surgery: A Practical Guide</a>. Springer. pp. 179–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-319-52210-4" title="Special:BookSources/978-3-319-52210-4"><bdi>978-3-319-52210-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Reproductive+Medicine+and+Surgery%3A+A+Practical+Guide&rft.pages=179-&rft.pub=Springer&rft.date=2017-06-14&rft.isbn=978-3-319-52210-4&rft.aulast=Falcone&rft.aufirst=T&rft.au=Hurd%2C+WW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DpzgoDwAAQBAJ%26pg%3DPA179&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Becker_2001-51"><a href="#cite_ref-Becker_2001_51-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBecker2001" class="citation book cs1">Becker KL (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1059">Principles and Practice of Endocrinology and Metabolism</a>. Lippincott Williams & Wilkins. pp. 889, 1059–1060, 2153. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-1750-2" title="Special:BookSources/978-0-7817-1750-2"><bdi>978-0-7817-1750-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+and+Practice+of+Endocrinology+and+Metabolism&rft.pages=889%2C+1059-1060%2C+2153&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2001&rft.isbn=978-0-7817-1750-2&rft.aulast=Becker&rft.aufirst=KL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFVfzRvaucq8C%26pg%3DPA1059&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-KleemannEngel2014-52"><a href="#cite_ref-KleemannEngel2014_52-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKleemannEngelKutscherReichert2014" class="citation book cs1">Kleemann A, Engel J, Kutscher B, Reichert D (14 May 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=fO2IAwAAQBAJ&pg=PA1167">Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs</a>. Thieme. pp. 1167–1174. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-13-179525-0" title="Special:BookSources/978-3-13-179525-0"><bdi>978-3-13-179525-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmaceutical+Substances%2C+5th+Edition%2C+2009%3A+Syntheses%2C+Patents+and+Applications+of+the+most+relevant+APIs&rft.pages=1167-1174&rft.pub=Thieme&rft.date=2014-05-14&rft.isbn=978-3-13-179525-0&rft.aulast=Kleemann&rft.aufirst=A&rft.au=Engel%2C+J&rft.au=Kutscher%2C+B&rft.au=Reichert%2C+D&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DfO2IAwAAQBAJ%26pg%3DPA1167&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Muller1998-53"><a href="#cite_ref-Muller1998_53-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMuller1998" class="citation book cs1">Muller (19 June 1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2HBPHmclMWIC&pg=PA276">European Drug Index: European Drug Registrations, Fourth Edition</a>. CRC Press. pp. 276, 454–455, 566–567. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-7692-2114-5" title="Special:BookSources/978-3-7692-2114-5"><bdi>978-3-7692-2114-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=European+Drug+Index%3A+European+Drug+Registrations%2C+Fourth+Edition&rft.pages=276%2C+454-455%2C+566-567&rft.pub=CRC+Press&rft.date=1998-06-19&rft.isbn=978-3-7692-2114-5&rft.au=Muller&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2HBPHmclMWIC%26pg%3DPA276&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-KrishnaShah1996-54"><a href="#cite_ref-KrishnaShah1996_54-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKrishnaSheriar1996" class="citation book cs1">Krishna UR, Sheriar NK (1996). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=n16P1r9cBG8C&pg=PA70">Menopause</a>. Orient Blackswan. pp. 70–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-250-0910-8" title="Special:BookSources/978-81-250-0910-8"><bdi>978-81-250-0910-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Menopause&rft.pages=70-&rft.pub=Orient+Blackswan&rft.date=1996&rft.isbn=978-81-250-0910-8&rft.aulast=Krishna&rft.aufirst=UR&rft.au=Sheriar%2C+NK&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dn16P1r9cBG8C%26pg%3DPA70&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-NNR1949-55"><a href="#cite_ref-NNR1949_55-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">"NNR: Products Recently Accepted by the A. M. A. Council on Pharmacy and Chemistry". Journal of the American Pharmaceutical Association (Practical Pharmacy ed.). 10 (11): 692–694. 1949. <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%2FS0095-9561%2816%2931995-8">10.1016/S0095-9561(16)31995-8</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/0095-9561">0095-9561</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+the+American+Pharmaceutical+Association+%28Practical+Pharmacy+ed.%29&rft.atitle=NNR%3A+Products+Recently+Accepted+by+the+A.+M.+A.+Council+on+Pharmacy+and+Chemistry&rft.volume=10&rft.issue=11&rft.pages=692-694&rft.date=1949&rft_id=info%3Adoi%2F10.1016%2FS0095-9561%2816%2931995-8&rft.issn=00959561&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-AerodiolLabel-56"><a href="#cite_ref-AerodiolLabel_56-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.medicines.org.au/files/secaerod.pdf">"AERODIOL (Oestradiol hemihydrate 150 micrograms/actuation)"</a> (PDF). Servier Laboratories (Aust) Pty Ltd.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Servier+Laboratories+%28Aust%29+Pty+Ltd&rft.atitle=AERODIOL+%28Oestradiol+hemihydrate+150+micrograms%2Factuation%29&rft_id=http%3A%2F%2Fwww.medicines.org.au%2Ffiles%2Fsecaerod.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Drugs.com-57"><a href="#cite_ref-Drugs.com_57-0">^</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://www.drugs.com/international/estradiol.html">"Estradiol"</a>. Drugs.com.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Drugs.com&rft.atitle=Estradiol&rft_id=https%3A%2F%2Fwww.drugs.com%2Finternational%2Festradiol.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid18382901-58"><a href="#cite_ref-pmid18382901_58-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSahinKokenCosarArioz2008" class="citation journal cs1">Sahin FK, Koken G, Cosar E, Arioz DT, Degirmenci B, Albayrak R, Acar M (2008). "Effect of Aerodiol administration on ocular arteries in postmenopausal women". Gynecol. Endocrinol. 24 (4): 173–7. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F09513590701807431">10.1080/09513590701807431</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/18382901">18382901</a>. <q>300 μg 17β-estradiol (Aerodiol®; Servier, Chambrayles-Tours, France) was administered via the nasal route by a gynecologist. This product is unavailable after March 31, 2007 because its manufacturing and marketing are being discontinued.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gynecol.+Endocrinol.&rft.atitle=Effect+of+Aerodiol+administration+on+ocular+arteries+in+postmenopausal+women&rft.volume=24&rft.issue=4&rft.pages=173-7&rft.date=2008&rft_id=info%3Adoi%2F10.1080%2F09513590701807431&rft_id=info%3Apmid%2F18382901&rft.aulast=Sahin&rft.aufirst=FK&rft.au=Koken%2C+G&rft.au=Cosar%2C+E&rft.au=Arioz%2C+DT&rft.au=Degirmenci%2C+B&rft.au=Albayrak%2C+R&rft.au=Acar%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-PlouffeRavnikar2012-59"><a href="#cite_ref-PlouffeRavnikar2012_59-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPlouffe_JrRavnikarSperoffWatts2012" class="citation book cs1">Plouffe Jr L, Ravnikar VA, Speroff L, Watts NB (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2MjcBwAAQBAJ&pg=PA271">Comprehensive Management of Menopause</a>. Springer Science & Business Media. pp. 271–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4612-4330-4" title="Special:BookSources/978-1-4612-4330-4"><bdi>978-1-4612-4330-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Comprehensive+Management+of+Menopause&rft.pages=271-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4612-4330-4&rft.aulast=Plouffe+Jr&rft.aufirst=L&rft.au=Ravnikar%2C+VA&rft.au=Speroff%2C+L&rft.au=Watts%2C+NB&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2MjcBwAAQBAJ%26pg%3DPA271&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-UC1952-60"><a href="#cite_ref-UC1952_60-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=t7VW3PucgboC&pg=PA49">Hospital Formulary and Compendium of Useful Information</a>. University of California Press. 1952. pp. 49–. GGKEY:2UAAZRZ5LN0.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hospital+Formulary+and+Compendium+of+Useful+Information&rft.pages=49-&rft.pub=University+of+California+Press&rft.date=1952&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dt7VW3PucgboC%26pg%3DPA49&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Leidenberger2013-61"><a href="#cite_ref-Leidenberger2013_61-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeidenberger2013" class="citation book cs1">Leidenberger FA (17 April 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=YTiuBgAAQBAJ&pg=PA527">Klinische Endokrinologie für Frauenärzte</a>. Springer-Verlag. pp. 527–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-662-08110-5" title="Special:BookSources/978-3-662-08110-5"><bdi>978-3-662-08110-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Klinische+Endokrinologie+f%C3%BCr+Frauen%C3%A4rzte&rft.pages=527-&rft.pub=Springer-Verlag&rft.date=2013-04-17&rft.isbn=978-3-662-08110-5&rft.aulast=Leidenberger&rft.aufirst=FA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DYTiuBgAAQBAJ%26pg%3DPA527&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid2215269-62">^ <a href="#cite_ref-pmid2215269_62-0">a</a> <a href="#cite_ref-pmid2215269_62-1">b</a> <a href="#cite_ref-pmid2215269_62-2">c</a> <a href="#cite_ref-pmid2215269_62-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1990" class="citation journal cs1">Lauritzen C (September 1990). "Clinical use of oestrogens and progestogens". Maturitas. 12 (3): 199–214. <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%2F0378-5122%2890%2990004-P">10.1016/0378-5122(90)90004-P</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/2215269">2215269</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Maturitas&rft.atitle=Clinical+use+of+oestrogens+and+progestogens&rft.volume=12&rft.issue=3&rft.pages=199-214&rft.date=1990-09&rft_id=info%3Adoi%2F10.1016%2F0378-5122%2890%2990004-P&rft_id=info%3Apmid%2F2215269&rft.aulast=Lauritzen&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Lauritzen-2005-63"><a href="#cite_ref-Lauritzen-2005_63-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzenStudd2005" class="citation book cs1">Lauritzen C, Studd JW (22 June 2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=WD7S7677xUUC&pg=PA95">Current Management of the Menopause</a>. CRC Press. pp. 95–98, 488. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-203-48612-2" title="Special:BookSources/978-0-203-48612-2"><bdi>978-0-203-48612-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Current+Management+of+the+Menopause&rft.pages=95-98%2C+488&rft.pub=CRC+Press&rft.date=2005-06-22&rft.isbn=978-0-203-48612-2&rft.aulast=Lauritzen&rft.aufirst=C&rft.au=Studd%2C+JW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DWD7S7677xUUC%26pg%3DPA95&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Laurtizen-2001-64"><a href="#cite_ref-Laurtizen-2001_64-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLaurtizen2001" class="citation book cs1">Laurtizen C (2001). <a rel="nofollow" class="external text" href="https://www.kup.at/kup/pdf/4978.pdf">"Hormone Substitution Before, During and After Menopause"</a> (PDF). 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Krause & Pachernegg: Gablitz. pp. 67–88. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-901299-34-6" title="Special:BookSources/978-3-901299-34-6"><bdi>978-3-901299-34-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormone+Substitution+Before%2C+During+and+After+Menopause&rft.btitle=Menopause+%E2%80%93+Andropause%3A+Hormone+Replacement+Therapy+Through+the+Ages&rft.pages=67-88&rft.pub=Krause+%26+Pachernegg%3A+Gablitz&rft.date=2001&rft.isbn=978-3-901299-34-6&rft.aulast=Laurtizen&rft.aufirst=C&rft_id=https%3A%2F%2Fwww.kup.at%2Fkup%2Fpdf%2F4978.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Midwinter-1976-65"><a href="#cite_ref-Midwinter-1976_65-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMidwinter1976" class="citation book cs1">Midwinter A (1976). 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MTP Press Limited. pp. 377–382. <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%2F978-94-011-6165-7_33">10.1007/978-94-011-6165-7_33</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-6167-1" title="Special:BookSources/978-94-011-6167-1"><bdi>978-94-011-6167-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Contraindications+to+estrogen+therapy+and+management+of+the+menopausal+syndrome+in+these+cases&rft.btitle=The+Management+of+the+Menopause+%26+Post-Menopausal+Years%3A+The+Proceedings+of+the+International+Symposium+held+in+London+24%E2%80%9326+November+1975+Arranged+by+the+Institute+of+Obstetrics+and+Gynaecology%2C+The+University+of+London&rft.pages=377-382&rft.pub=MTP+Press+Limited&rft.date=1976&rft_id=info%3Adoi%2F10.1007%2F978-94-011-6165-7_33&rft.isbn=978-94-011-6167-1&rft.aulast=Midwinter&rft.aufirst=A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid26684553-66">^ <a href="#cite_ref-pmid26684553_66-0">a</a> <a href="#cite_ref-pmid26684553_66-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBishop2015" class="citation journal cs1">Bishop BM (December 2015). 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Abstand zwischen 2 Injektionen auf 2 Wochen erweitern (Abb. 6.2).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Hormontherapie+bei+gyn%C3%A4kologischen+Erkrankungen&rft.btitle=Praktische+Hormontherapie+in+der+Gyn%C3%A4kologie&rft.pages=245-314&rft.pub=Walter+de+Gruyter&rft.date=2008-12-10&rft.isbn=978-3-11-020864-1&rft.aulast=G%C3%B6retzlehner&rft.aufirst=G&rft.au=Lauritzen%2C+C&rft.au=G%C3%B6retzlehner%2C+U&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DE3SuivmVMnQC%26pg%3DPA245&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid7835827-68">^ <a href="#cite_ref-pmid7835827_68-0">a</a> <a href="#cite_ref-pmid7835827_68-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFUlrichPfeiferLauritzen1994" class="citation journal cs1">Ulrich U, Pfeifer T, Lauritzen C (September 1994). "Rapid increase in lumbar spine bone density in osteopenic women by high-dose intramuscular estrogen-progestogen injections. A preliminary report". Hormone and Metabolic Research = Hormon- und Stoffwechselforschung = Hormones et Métabolisme. 26 (9): 428–431. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-2007-1001723">10.1055/s-2007-1001723</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/7835827">7835827</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:260169203">260169203</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hormone+and+Metabolic+Research+%3D+Hormon-+und+Stoffwechselforschung+%3D+Hormones+et+M%C3%A9tabolisme&rft.atitle=Rapid+increase+in+lumbar+spine+bone+density+in+osteopenic+women+by+high-dose+intramuscular+estrogen-progestogen+injections.+A+preliminary+report&rft.volume=26&rft.issue=9&rft.pages=428-431&rft.date=1994-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A260169203%23id-name%3DS2CID&rft_id=info%3Apmid%2F7835827&rft_id=info%3Adoi%2F10.1055%2Fs-2007-1001723&rft.aulast=Ulrich&rft.aufirst=U&rft.au=Pfeifer%2C+T&rft.au=Lauritzen%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid6014870-69"><a href="#cite_ref-pmid6014870_69-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNotterKaigas1966" class="citation journal cs1 cs1-prop-foreign-lang-source">Notter G, Kaigas M (September 1966). "[The treatment of inoperable and metastasizing breast carcinoma with gestational and estrogenci hormones]" [The treatment of inoperable and metastasizing breast carcinoma with gestational and estrogenic hormones]. Munchener Medizinische Wochenschrift (in German). 108 (39): 1920–1923. <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/6014870">6014870</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Munchener+Medizinische+Wochenschrift&rft.atitle=%5BThe+treatment+of+inoperable+and+metastasizing+breast+carcinoma+with+gestational+and+estrogenci+hormones%5D&rft.volume=108&rft.issue=39&rft.pages=1920-1923&rft.date=1966-09&rft_id=info%3Apmid%2F6014870&rft.aulast=Notter&rft.aufirst=G&rft.au=Kaigas%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid5529652-70">^ <a href="#cite_ref-pmid5529652_70-0">a</a> <a href="#cite_ref-pmid5529652_70-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBerndtStender1970" class="citation journal cs1 cs1-prop-foreign-lang-source">Berndt G, Stender HS (November 1970). "[The combined estrogen-gestagen treatment of metastasizing mammary carcinoma using with SH 834]" [The combined estrogen-gestagen treatment of metastasizing mammary carcinoma using with SH 834]. Deutsche Medizinische Wochenschrift (in German). 95 (48): 2399+. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-0028-1108843">10.1055/s-0028-1108843</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/5529652">5529652</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:70908169">70908169</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Deutsche+Medizinische+Wochenschrift&rft.atitle=%5BThe+combined+estrogen-gestagen+treatment+of+metastasizing+mammary+carcinoma+using+with+SH+834%5D&rft.volume=95&rft.issue=48&rft.pages=2399%2B&rft.date=1970-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A70908169%23id-name%3DS2CID&rft_id=info%3Apmid%2F5529652&rft_id=info%3Adoi%2F10.1055%2Fs-0028-1108843&rft.aulast=Berndt&rft.aufirst=G&rft.au=Stender%2C+HS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Berndt-71"><a href="#cite_ref-Berndt_71-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBerndtEckelNotterStender" class="citation journal cs1 cs1-prop-foreign-lang-source">Berndt G, Eckel H, Notter G, Stender HS. <a rel="nofollow" class="external text" href="https://www.popline.org/node/485956">"Die Wirkung einer Ostrogen-Gestagen-Kombinationstherapie beim fortgeschrittenen Mammakarzinom mit besonderer Berucksichtigung der Lungenmetastasen"</a> [Effect of combined estrogen-gestagen therapy on advanced breast carcinoma with special consideration of lung metastases]. Strahlentherapie (in German). 141 (5): 540–548. <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/0039-2073">0039-2073</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Strahlentherapie&rft.atitle=Die+Wirkung+einer+Ostrogen-Gestagen-Kombinationstherapie+beim+fortgeschrittenen+Mammakarzinom+mit+besonderer+Berucksichtigung+der+Lungenmetastasen&rft.volume=141&rft.issue=5&rft.pages=540-548&rft.issn=0039-2073&rft.aulast=Berndt&rft.aufirst=G&rft.au=Eckel%2C+H&rft.au=Notter%2C+G&rft.au=Stender%2C+HS&rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F485956&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid1202923-72">^ <a href="#cite_ref-pmid1202923_72-0">a</a> <a href="#cite_ref-pmid1202923_72-1">b</a> <a href="#cite_ref-pmid1202923_72-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNotterBerndt1975" class="citation journal cs1">Notter G, Berndt G (October 1975). "Hormonal treatment of mammary carcinoma with Progynon-Depot and Depostat". Acta Radiologica. 14 (5): 433–442. <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%2F02841867509132684">10.3109/02841867509132684</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/1202923">1202923</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Radiologica&rft.atitle=Hormonal+treatment+of+mammary+carcinoma+with+Progynon-Depot+and+Depostat&rft.volume=14&rft.issue=5&rft.pages=433-442&rft.date=1975-10&rft_id=info%3Adoi%2F10.3109%2F02841867509132684&rft_id=info%3Apmid%2F1202923&rft.aulast=Notter&rft.aufirst=G&rft.au=Berndt%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid968923-73"><a href="#cite_ref-pmid968923_73-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFirusianSchietzel1976" class="citation journal cs1 cs1-prop-foreign-lang-source">Firusian N, Schietzel M (September 1976). "[Additive treatment of metastasizing breast cancer with special reference to postmenopausal age (results of a randomized study)]" [Additive treatment of metastasizing breast cancer with special reference to postmenopausal age (results of a randomized study)]. Strahlentherapie (in German). 152 (3): 235–247. <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/968923">968923</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Strahlentherapie&rft.atitle=%5BAdditive+treatment+of+metastasizing+breast+cancer+with+special+reference+to+postmenopausal+age+%28results+of+a+randomized+study%29%5D&rft.volume=152&rft.issue=3&rft.pages=235-247&rft.date=1976-09&rft_id=info%3Apmid%2F968923&rft.aulast=Firusian&rft.aufirst=N&rft.au=Schietzel%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid4142204-74"><a href="#cite_ref-pmid4142204_74-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchubertZieglerVölter1973" class="citation journal cs1 cs1-prop-foreign-lang-source">Schubert GE, Ziegler H, Völter D (1973). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20181123201118/https://www.popline.org/node/508573">"[Comparison of histological and cytological studies of the prostate with special reference to oestrogene induced changes (author's transl)]"</a> [Comparison of histological and cytological studies of the prostate with special reference to oestrogene induced changes]. Verhandlungen der Deutschen Gesellschaft für Pathologie (in German). 57: 315–318. <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/4142204">4142204</a>. Archived from <a rel="nofollow" class="external text" href="https://www.popline.org/node/508573">the original</a> on 23 November 2018. Retrieved 11 June 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Verhandlungen+der+Deutschen+Gesellschaft+f%C3%BCr+Pathologie&rft.atitle=%5BComparison+of+histological+and+cytological+studies+of+the+prostate+with+special+reference+to+oestrogene+induced+changes+%28author%27s+transl%29%5D&rft.volume=57&rft.pages=315-318&rft.date=1973&rft_id=info%3Apmid%2F4142204&rft.aulast=Schubert&rft.aufirst=GE&rft.au=Ziegler%2C+H&rft.au=V%C3%B6lter%2C+D&rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F508573&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid4142482-75"><a href="#cite_ref-pmid4142482_75-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFZieglerVölterSchubert1974" class="citation journal cs1">Ziegler H, Völter D, Schubert GE (1974). "Morphological criteria for the control of carcinoma of the prostate with estrogen therapy". International Urology and Nephrology. 6 (3–4): 195–200. <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%2FBF02089265">10.1007/BF02089265</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/4142482">4142482</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:39028149">39028149</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Urology+and+Nephrology&rft.atitle=Morphological+criteria+for+the+control+of+carcinoma+of+the+prostate+with+estrogen+therapy&rft.volume=6&rft.issue=3%E2%80%934&rft.pages=195-200&rft.date=1974&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A39028149%23id-name%3DS2CID&rft_id=info%3Apmid%2F4142482&rft_id=info%3Adoi%2F10.1007%2FBF02089265&rft.aulast=Ziegler&rft.aufirst=H&rft.au=V%C3%B6lter%2C+D&rft.au=Schubert%2C+GE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Benjamin-1966-76"><a href="#cite_ref-Benjamin-1966_76-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBenjaminLalGreenMasters1966" class="citation book cs1">Benjamin H, Lal GB, Green R, Masters RE (1966). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=hArbAAAAMAAJ">The Transsexual Phenomenon</a>. Ace Publishing Company. p. 107. <q>In my own practice, Squibb's Delestrogen for intramuscular injections was employed with much satisfaction and positive results. This is a slowly absorbing, well-tolerated, potent preparation (chemically, Estradiol Valerate), and was applied in doses of 20 to 60 mg. (½ to 1 ½ cc.). Usually 30 to 60 mg. of Delalutin (Squibb) was added, an equally potent progesterone. This combination was given once a week or once in two to three weeks, according to the response as measured by the patient's emotional balance and physical feminization symptoms. Generally I found that dosage seems less important than length and regularity of administration.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Transsexual+Phenomenon&rft.pages=107&rft.pub=Ace+Publishing+Company&rft.date=1966&rft.aulast=Benjamin&rft.aufirst=H&rft.au=Lal%2C+GB&rft.au=Green%2C+R&rft.au=Masters%2C+RE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DhArbAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Benjamin-1967-77"><a href="#cite_ref-Benjamin-1967_77-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBenjamin1967" class="citation journal cs1">Benjamin H (1967). "Transvestism and Transsexualism in the male and female1". Journal of Sex Research. 3 (2): 107–127. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F00224496709550519">10.1080/00224496709550519</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/0022-4499">0022-4499</a>. <q>Estrogen treatment—as already indicated—helps greatly but does not cure. I have employed either Squibb's Delestrogen, a slowly absorbing, highly potent preparation which is, chemically, estradiol valerate (40 mg. to 1 cc); or the still more potent Delestrec, which is estradiol undecylate (100 mg. to 1 cc). This preparation, however, is not yet on the market in this country, though it is widely used in Europe. In the majority of cases, I used from 30 to 100 mg. weekly, or every two to three weeks, by intramuscular injection.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Sex+Research&rft.atitle=Transvestism+and+Transsexualism+in+the+male+and+female1&rft.volume=3&rft.issue=2&rft.pages=107-127&rft.date=1967&rft_id=info%3Adoi%2F10.1080%2F00224496709550519&rft.issn=0022-4499&rft.aulast=Benjamin&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid11741520-78"><a href="#cite_ref-pmid11741520_78-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChengShuLiuWang2001" class="citation journal cs1">Cheng ZN, Shu Y, Liu ZQ, Wang LS, Ou-Yang DS, Zhou HH (February 2001). "Role of cytochrome P450 in estradiol metabolism in vitro". Acta Pharmacologica Sinica. 22 (2): 148–154. <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/11741520">11741520</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Pharmacologica+Sinica&rft.atitle=Role+of+cytochrome+P450+in+estradiol+metabolism+in+vitro&rft.volume=22&rft.issue=2&rft.pages=148-154&rft.date=2001-02&rft_id=info%3Apmid%2F11741520&rft.aulast=Cheng&rft.aufirst=ZN&rft.au=Shu%2C+Y&rft.au=Liu%2C+ZQ&rft.au=Wang%2C+LS&rft.au=Ou-Yang%2C+DS&rft.au=Zhou%2C+HH&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid559617-79"><a href="#cite_ref-pmid559617_79-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLauritzen1977" class="citation journal cs1 cs1-prop-foreign-lang-source">Lauritzen C (June 1977). "[Estrogen thearpy in practice. 3. Estrogen preparations and combination preparations]" [Estrogen therapy in practice. 3. Estrogen preparations and combination preparations]. 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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-WolfSchneider2013-80"><a href="#cite_ref-WolfSchneider2013_80-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-GöretzlehnerLauritzen2012-81"><a href="#cite_ref-GöretzlehnerLauritzen2012_81-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-KnörrBeller2013-82"><a href="#cite_ref-KnörrBeller2013_82-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-HorskyPresl1981-83"><a href="#cite_ref-HorskyPresl1981_83-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Pschyrembel1968-84"><a href="#cite_ref-Pschyrembel1968_84-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid779393-85"><a href="#cite_ref-pmid779393_85-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Lauritzen1975-86"><a href="#cite_ref-Lauritzen1975_86-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Kopera1991-87"><a href="#cite_ref-Kopera1991_87-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid29603164-88"><a href="#cite_ref-pmid29603164_88-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid29756046-89"><a href="#cite_ref-pmid29756046_89-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Rydén1950-90"><a href="#cite_ref-Rydén1950_90-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid14902290-91"><a href="#cite_ref-pmid14902290_91-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Kottmeier1947-92"><a href="#cite_ref-Kottmeier1947_92-0">^</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%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-RietbrockStaib2013-93"><a href="#cite_ref-RietbrockStaib2013_93-0">^</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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Zeitschrift für Kinderheilkunde. 75 (3): 224–234. <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%2FBF00439822">10.1007/BF00439822</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/0340-6199">0340-6199</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:29364660">29364660</a>. <q>Um die "Menarche" sollte eine verstärkte Substitutionstherapie (20 Tage lang tgl. 0,1 mg Follikelhormon per os oder einmalig Progynon-Depot (10 mg i.m.), [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Zeitschrift+f%C3%BCr+Kinderheilkunde&rft.atitle=%C3%9Cber+ovarielle+Agenesie&rft.volume=75&rft.issue=3&rft.pages=224-234&rft.date=1954&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A29364660%23id-name%3DS2CID&rft.issn=0340-6199&rft_id=info%3Adoi%2F10.1007%2FBF00439822&rft.aulast=Ehrengut&rft.aufirst=W&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Kuhl-2008-146">^ <a href="#cite_ref-Kuhl-2008_146-0">a</a> <a href="#cite_ref-Kuhl-2008_146-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhlWiegratz2008" class="citation book cs1 cs1-prop-foreign-lang-source">Kuhl H, Wiegratz I (1 January 2008). 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The first Schering preparation containing micronized estradiol was marketed in 1968 as Progynova 21 (2 mg) and Progynova 21 mite (1 mg).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Klimakterium%2C+Postmenopause+und+Hormonsubstitution&rft.pages=18&rft.edition=4&rft.pub=UNI-MED-Verlag&rft.date=2008-01-01&rft.isbn=978-3-83742-043-2&rft.aulast=Kuhl&rft.aufirst=H&rft.au=Wiegratz%2C+I&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Klinische_Wochenschrift-1966-147"><a href="#cite_ref-Klinische_Wochenschrift-1966_147-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1">"Neue Spezialitäten". 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Praktické Lékárenství (in Czech). 10 (2): 68–73. <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/1801-2434">1801-2434</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Praktick%C3%A9+L%C3%A9k%C3%A1renstv%C3%AD&rft.atitle=Menopauz%C3%A1ln%C3%AD+symptomy+a+hormon%C3%A1ln%C3%AD+substitu%C4%8Dn%C3%AD+terapie&rft.volume=10&rft.issue=2&rft.pages=68-73&rft.date=2014&rft.issn=1801-2434&rft.aulast=Kub%C3%ADkov%C3%A1&rft.aufirst=D&rft_id=http%3A%2F%2Fwww.medvik.cz%2Flink%2Fbmc14059249&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Neofollin-Label-160"><a href="#cite_ref-Neofollin-Label_160-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.sukl.cz/download/pil/PI16359.pdf">"NEOFOLLIN Injekční roztok (Estradioli valeras)"</a> (PDF).</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=NEOFOLLIN+Injek%C4%8Dn%C3%AD+roztok+%28Estradioli+valeras%29&rft_id=http%3A%2F%2Fwww.sukl.cz%2Fdownload%2Fpil%2FPI16359.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-Sanfilippo-1998-161"><a href="#cite_ref-Sanfilippo-1998_161-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSanfilippo1998" class="citation book cs1">Sanfilippo JS (January 1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=jfmB3aNSGfoC&pg=PA227">Primary Care in Obstetrics and Gynecology: A Handbook for Clinicians</a>. 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The Journal of Obstetrics and Gynaecology of the British Commonwealth. 79 (6): 555–559. <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%2Fj.1471-0528.1972.tb14200.x">10.1111/j.1471-0528.1972.tb14200.x</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/4555897">4555897</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:2586346">2586346</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+Obstetrics+and+Gynaecology+of+the+British+Commonwealth&rft.atitle=Progestogen+therapy+for+ovarian+carcinoma&rft.volume=79&rft.issue=6&rft.pages=555-559&rft.date=1972-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A2586346%23id-name%3DS2CID&rft_id=info%3Apmid%2F4555897&rft_id=info%3Adoi%2F10.1111%2Fj.1471-0528.1972.tb14200.x&rft.aulast=Ward&rft.aufirst=HW&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> <li id="cite_note-pmid5088730-163"><a href="#cite_ref-pmid5088730_163-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBerndtEckelNotterSt_Stender1971" class="citation journal cs1 cs1-prop-foreign-lang-source">Berndt G, Eckel H, Notter G, St Stender H (May 1971). <a rel="nofollow" class="external text" href="https://www.popline.org/node/485956">"[Effect of estrogen-gestagen combination therapy in advanced breast carcinoma with special reference to pulmonary metastases]"</a> [Effect of Estrogen-Gestagen Combination Therapy in Advanced Breast Carcinoma with Special Reference to Pulmonary Metastases]. Strahlentherapie (in German). 141 (5): 540–548. <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/5088730">5088730</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Strahlentherapie&rft.atitle=%5BEffect+of+estrogen-gestagen+combination+therapy+in+advanced+breast+carcinoma+with+special+reference+to+pulmonary+metastases%5D&rft.volume=141&rft.issue=5&rft.pages=540-548&rft.date=1971-05&rft_id=info%3Apmid%2F5088730&rft.aulast=Berndt&rft.aufirst=G&rft.au=Eckel%2C+H&rft.au=Notter%2C+G&rft.au=St+Stender%2C+H&rft_id=https%3A%2F%2Fwww.popline.org%2Fnode%2F485956&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2>[<a href="/w/index.php?title=Estradiol_valerate&action=edit&section=25" title="Edit section: Further reading">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVermeulen1975" class="citation journal cs1">Vermeulen A (1975). "Longacting steroid preparations". Acta Clinica Belgica. 30 (1): 48–55. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F17843286.1975.11716973">10.1080/17843286.1975.11716973</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/1231448">1231448</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Clinica+Belgica&rft.atitle=Longacting+steroid+preparations&rft.volume=30&rft.issue=1&rft.pages=48-55&rft.date=1975&rft_id=info%3Adoi%2F10.1080%2F17843286.1975.11716973&rft_id=info%3Apmid%2F1231448&rft.aulast=Vermeulen&rft.aufirst=A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDüsterbergNishino1982" class="citation journal cs1">Düsterberg B, Nishino Y (December 1982). 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Contraception. 49 (4): 361–385. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0010-7824%2894%2990033-7">10.1016/0010-7824(94)90033-7</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/8013220">8013220</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Pharmacodynamic+effects+of+once-a-month+combined+injectable+contraceptives&rft.volume=49&rft.issue=4&rft.pages=361-385&rft.date=1994-04&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2894%2990033-7&rft_id=info%3Apmid%2F8013220&rft.aulast=Sang&rft.aufirst=GW&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFO'Connell1995" class="citation journal cs1">O'Connell MB (September 1995). 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Journal of Clinical Pharmacology. 35 (9S): 18S–24S. <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%2Fj.1552-4604.1995.tb04143.x">10.1002/j.1552-4604.1995.tb04143.x</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/8530713">8530713</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:10159196">10159196</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+Clinical+Pharmacology&rft.atitle=Pharmacokinetic+and+pharmacologic+variation+between+different+estrogen+products&rft.volume=35&rft.issue=9S&rft.pages=18S-24S&rft.date=1995-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A10159196%23id-name%3DS2CID&rft_id=info%3Apmid%2F8530713&rft_id=info%3Adoi%2F10.1002%2Fj.1552-4604.1995.tb04143.x&rft.aulast=O%27Connell&rft.aufirst=MB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhl2005" class="citation journal cs1">Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13697130500148875">10.1080/13697130500148875</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16112947">16112947</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:24616324">24616324</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Pharmacology+of+estrogens+and+progestogens%3A+influence+of+different+routes+of+administration&rft.volume=8&rft.issue=Suppl+1&rft.pages=3-63&rft.date=2005-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24616324%23id-name%3DS2CID&rft_id=info%3Apmid%2F16112947&rft_id=info%3Adoi%2F10.1080%2F13697130500148875&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+valerate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStanczykArcherBhavnani2013" class="citation journal cs1">Stanczyk FZ, Archer DF, Bhavnani BR (June 2013). "Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment". Contraception. 87 (6): 706–727. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.contraception.2012.12.011">10.1016/j.contraception.2012.12.011</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/23375353">23375353</a>.</cite><span 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.navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Estradiol" style="padding:3px"><table class="nowraplinks mw-collapsible expanded 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: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 class="mw-selflink selflink">Estradiol valerate</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate (estradiol normustine phosphate)</a></li> <li><a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Estrogens_and_antiestrogens" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogens_and_antiestrogens" title="Template talk:Estrogens and antiestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogens_and_antiestrogens" title="Special:EditPage/Template:Estrogens and antiestrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogens_and_antiestrogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a>†</li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a class="mw-selflink selflink">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 href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol">ent-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol">meso-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol">meso-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li>Unknown/unsorted: <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li>Xenoestrogens: <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (cis-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a 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>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Estradiol_valerate&oldid=1254902551">https://en.wikipedia.org/w/index.php?title=Estradiol_valerate&oldid=1254902551</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" 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