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class="vector-toc-link" href="#Breast_enhancement"> <div class="vector-toc-text"> 1.4.4 Breast enhancement </div> </a> <ul id="toc-Breast_enhancement-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Schizophrenia" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Schizophrenia"> <div class="vector-toc-text"> 1.4.5 Schizophrenia </div> </a> <ul id="toc-Schizophrenia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sexual_deviance" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Sexual_deviance"> <div class="vector-toc-text"> 1.4.6 Sexual deviance </div> </a> <ul id="toc-Sexual_deviance-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Available_forms" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Available_forms"> <div class="vector-toc-text"> 1.5 Available forms </div> </a> <ul id="toc-Available_forms-sublist" class="vector-toc-list"> </ul> 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class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Long-term_effects"> <div class="vector-toc-text"> 3.2 Long-term effects </div> </a> <ul id="toc-Long-term_effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Overdose" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Overdose"> <div class="vector-toc-text"> 4 Overdose </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> 5 Interactions </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> 6 Pharmacology </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button 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.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">"Altrad" redirects here. For the French corporation "Groupe Altrad", see <a href="/wiki/Mohed_Altrad" title="Mohed Altrad">Mohed Altrad</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">This article is about estradiol as a medication. For its role as a hormone, see <a href="/wiki/Estradiol" title="Estradiol">Estradiol</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Estradiol</caption><tbody><tr><td colspan="2" class="infobox-image"><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></td></tr><tr><td colspan="2" class="infobox-image"><a href="/wiki/File:Estradiol_3D_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Estradiol_3D_ball.png/235px-Estradiol_3D_ball.png" decoding="async" width="235" height="159" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Estradiol_3D_ball.png/353px-Estradiol_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Estradiol_3D_ball.png/470px-Estradiol_3D_ball.png 2x" data-file-width="2000" data-file-height="1351" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/ˌɛstrəˈdaɪoʊl/</a> <a href="/wiki/Help:Pronunciation_respelling_key" title="Help:Pronunciation respelling key">ES-trə-DY-ohl</a><a href="#cite_note-FordRoach2013-1">[1]</a><a href="#cite_note-HochadelMosby2015-2">[2]</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"><a href="#Brand_names">Many</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Oestradiol; E2; 17β-Estradiol; Estra-1,3,5(10)-triene-3,17β-diol</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/estradiol.html">Monograph</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><abbr class="country-name" title="United States">US</abbr> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Estradiol">Estradiol</a></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: B1</li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a> (<a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablet</a>) • <a href="/wiki/Sublingual_administration" title="Sublingual administration">Sublingual</a> (tablet) • <a href="/wiki/Intranasal_administration" class="mw-redirect" title="Intranasal administration">Intranasal</a> (<a href="/wiki/Nasal_spray" title="Nasal spray">nasal spray</a>) • <a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">Transdermal</a> (<a href="/wiki/Transdermal_patch" title="Transdermal patch">patch</a>, <a href="/wiki/Gel" title="Gel">gel</a>, <a href="/wiki/Cream_(pharmaceutical)" class="mw-redirect" title="Cream (pharmaceutical)">cream</a>, <a href="/wiki/Emulsion" title="Emulsion">emulsion</a>, <a href="/wiki/Transdermal_spray" title="Transdermal spray">spray</a>) • <a href="/wiki/Intravaginal_administration" title="Intravaginal administration">Vaginal</a> (tablet, cream, <a href="/wiki/Vaginal_suppository" class="mw-redirect" title="Vaginal suppository">suppository</a>, <a href="/wiki/Vaginal_insert" class="mw-redirect" title="Vaginal insert">insert</a>, <a href="/wiki/Vaginal_ring" title="Vaginal ring">ring</a>) • <a href="/wiki/Intramuscular_injection" title="Intramuscular injection"><abbr title="Intramuscular">IM</abbr> injection</a> (<a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</a>) • <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection"><abbr title="Subcutaneous">SC</abbr> injection</a> (<a href="/wiki/Aqueous_solution" title="Aqueous solution"><abbr title="aqueous solution">aq. soln.</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 aqueous solution) • <a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant">Subcutaneous implant</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_G03" title="ATC code G03">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;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><abbr class="country-name" title="Australia">AU</abbr>: <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)</li> <li><abbr class="country-name" title="Canada">CA</abbr>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a><a href="#cite_note-3">[3]</a></li> <li><abbr class="country-name" title="United Kingdom">UK</abbr>: <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li> <li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a></li> <li><abbr class="country-name" title="European Union">EU</abbr>: Rx-only<a href="#cite_note-4">[4]</a></li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">Oral: <5%<a href="#cite_note-pmid23375353-5">[5]</a> IM: 100%<a href="#cite_note-pmid7169965-6">[6]</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">~98%:<a href="#cite_note-pmid23375353-5">[5]</a><a href="#cite_note-FalconeHurd2007-7">[7]</a> • <a href="/wiki/Human_serum_albumin" title="Human serum albumin">Albumin</a>: 60% • <abbr title="sex hormone-binding globulin">SHBG</abbr>: 38% • Free: 2%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a> (via <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a>, <a href="/wiki/Sulfation" title="Sulfation">sulfation</a>, <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</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">Major (90%):<a href="#cite_note-pmid23375353-5">[5]</a> • <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a> • <a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a> • <a href="/wiki/Estrone_glucuronide" title="Estrone glucuronide">Estrone glucuronide</a> • <a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</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: 13–20 hours<a href="#cite_note-pmid23375353-5">[5]</a> Sublingual: 8–18 hours<a href="#cite_note-PriceBlauer1997-8">[8]</a> Transdermal (gel): 37 hours<a href="#cite_note-NauntonAl_Hadithy2006-9">[9]</a> IM (as <a href="/wiki/Estradiol_valerate" title="Estradiol valerate"><abbr title="estradiol valerate">EV</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 estradiol valerate): 4–5 days<a href="#cite_note-pmid7169965-6">[6]</a> IM (as <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate"><abbr title="estradiol cypionate">EC</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 estradiol cypionate): 8–10 days<a href="#cite_note-pmid22078184-10">[10]</a> <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection"><abbr title="Intravenous injection">IV</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 Intravenous injection (as <abbr title="estradiol">E2</abbr>): 1–2 hours<a href="#cite_note-pmid7169965-6">[6]</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>: 54%<a href="#cite_note-pmid23375353-5">[5]</a> <a href="/wiki/Feces" title="Feces">Feces</a>: 6%<a href="#cite_note-pmid23375353-5">[5]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol</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=50-28-2">50-28-2</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5757">5757</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=1013">1013</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/DB00783">DB00783</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.5554.html">5554</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/4TI98Z838E">4TI98Z838E</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/D00105">D00105</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/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:16469">CHEBI:16469</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL135">ChEMBL135</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C18H24O2</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">272.388 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=C%5BC%40%5D12CC%5BC%40H%5D3%5BC%40H%5D%28%5BC%40%40H%5D1CC%5BC%40%40H%5D2O%29CCC4%3DC3C%3DCC%28%3DC4%29O">Interactive image</a></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4)O</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/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:VOXZDWNPVJITMN-ZBRFXRBCSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=488623959&page2=Estradiol+%28medication%29">(verify)</a></td></tr></tbody></table> Estradiol (E2) is a <a href="/wiki/Medication" title="Medication">medication</a> and naturally occurring <a href="/wiki/Steroid_hormone" title="Steroid hormone">steroid hormone</a>.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-OettelSchillinger2012a-12">[12]</a><a href="#cite_note-OettelSchillinger2012b-13">[13]</a> It is an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> and is used mainly in <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a> and to treat <a href="/wiki/Hypogonadism" title="Hypogonadism">low sex hormone levels</a> in women.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid28376481-14">[14]</a> It is also used in <a href="/wiki/Hormonal_contraception" title="Hormonal contraception">hormonal birth control</a> for women, 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> and some <a href="/wiki/Non-binary_gender" title="Non-binary gender">non-binary</a> individuals, and in the treatment of <a href="/wiki/Hormone-sensitive_cancer" title="Hormone-sensitive cancer">hormone-sensitive cancers</a> like <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> in men and <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in women, among other uses.<a href="#cite_note-pmid23241152-15">[15]</a><a href="#cite_note-pmid12290848-16">[16]</a><a href="#cite_note-pmid28159148-17">[17]</a><a href="#cite_note-pmid25992351-18">[18]</a><a href="#cite_note-pmid27889048-19">[19]</a> Estradiol can be taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>, <a href="/wiki/Sublingual_administration" title="Sublingual administration">held and dissolved under the tongue</a>, as a <a href="/wiki/Gel" title="Gel">gel</a> or <a href="/wiki/Transdermal_patch" title="Transdermal patch">patch</a> that is <a href="/wiki/Transdermal" title="Transdermal">applied to the skin</a>, <a href="/wiki/Intravaginal_administration" title="Intravaginal administration">in through the vagina</a>, 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>, or through the use of an <a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant">implant that is placed into fat</a>, among other <a href="/wiki/Route_of_administration" title="Route of administration">routes</a>.<a href="#cite_note-pmid16112947-11">[11]</a> <a href="/wiki/Side_effect" title="Side effect">Side effects</a> of estradiol in women include <a href="/wiki/Breast_pain" title="Breast pain">breast tenderness</a>, <a href="/wiki/Mammoplasia" title="Mammoplasia">breast enlargement</a>, <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a>, and <a href="/wiki/Nausea" title="Nausea">nausea</a> among others.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-Estrace_Label-20">[20]</a> Men and children who are exposed to estradiol may develop <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a> of <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a>, such as <a href="/wiki/Breast_development" title="Breast development">breast development</a> and a <a href="/wiki/Gynoid_fat_distribution" title="Gynoid fat distribution">feminine pattern of fat distribution</a>, and men may also experience <a href="/wiki/Hypogonadism" title="Hypogonadism">low testosterone levels</a> and <a href="/wiki/Infertility" title="Infertility">infertility</a>.<a href="#cite_note-Pohanish2011-21">[21]</a><a href="#cite_note-CecilBennett1996-22">[22]</a> Estradiol may increase the risk of <a href="/wiki/Endometrial_hyperplasia" title="Endometrial hyperplasia">endometrial hyperplasia</a> and <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> in women with intact <a href="/wiki/Uterus" title="Uterus">uteruses</a> if it is not taken together with a <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> such as <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>.<a href="#cite_note-pmid16112947-11">[11]</a> The combination of estradiol with a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a>, though not with <a href="/wiki/Oral_administration" title="Oral administration">oral</a> progesterone, may increase the risk of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>.<a href="#cite_note-pmid27898258-23">[23]</a><a href="#cite_note-pmid24485796-24">[24]</a> Estradiol should not be used in women who are <a href="/wiki/Pregnancy" title="Pregnancy">pregnant</a> or <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeeding</a> or who have breast cancer, among other <a href="/wiki/Contraindication" title="Contraindication">contraindications</a>.<a href="#cite_note-Estrace_Label-20">[20]</a> Estradiol is a <a href="/wiki/Natural_product" title="Natural product">naturally occurring</a> and <a href="/wiki/Bioidentical_hormone_therapy" class="mw-redirect" title="Bioidentical hormone therapy">bioidentical</a> estrogen, or 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 estrogens like <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>.<a href="#cite_note-pmid16112947-11">[11]</a> Due to its estrogenic activity, estradiol has <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> effects and can inhibit <a href="/wiki/Fertility" title="Fertility">fertility</a> and suppress <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormone</a> <a href="/wiki/Biosynthesis" title="Biosynthesis">production</a> in both women and men.<a href="#cite_note-pmid3242384-25">[25]</a><a href="#cite_note-Ockrim_2003-26">[26]</a> Estradiol differs from non-bioidentical estrogens like <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a> and <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> in various ways, with implications for <a href="/wiki/Tolerability" title="Tolerability">tolerability</a> and <a href="/wiki/Drug_safety" class="mw-redirect" title="Drug safety">safety</a>.<a href="#cite_note-pmid16112947-11">[11]</a> Estradiol was discovered in 1933.<a href="#cite_note-Parl2000-27">[27]</a><a href="#cite_note-LauritzenStudd2005-28">[28]</a> It became available as a medication that same year, in an <a href="/wiki/Injection_(medicine)" title="Injection (medicine)">injectable</a> form known as <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>.<a href="#cite_note-Kaufman1933-29">[29]</a><a href="#cite_note-Buschbeck1934-30">[30]</a><a href="#cite_note-Biskind1935-31">[31]</a> Forms that were more useful by mouth, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> and <a href="/wiki/Micronization" title="Micronization">micronized</a> estradiol, were introduced in the 1960s and 1970s and increased its popularity by this route.<a href="#cite_note-KlinWochenschr1966-32">[32]</a><a href="#cite_note-pmid5593020-33">[33]</a><a href="#cite_note-Estrace-FDA-34">[34]</a> Estradiol is also used as other <a href="/wiki/Prodrugs" class="mw-redirect" title="Prodrugs">prodrugs</a>, like <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>.<a href="#cite_note-pmid16112947-11">[11]</a> Related estrogens such as ethinylestradiol, which is the most common estrogen in <a href="/wiki/Birth_control_pill" class="mw-redirect" title="Birth control pill">birth control pills</a>, and conjugated estrogens (brand name Premarin), which is used in menopausal hormone therapy, are used as medications as well.<a href="#cite_note-pmid16112947-11">[11]</a> In 2022, it was the 50th most commonly prescribed medication in the United States, with more than 12 million prescriptions.<a href="#cite_note-35">[35]</a><a href="#cite_note-36">[36]</a> It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<a href="#cite_note-37">[37]</a><a href="#cite_note-38">[38]</a><a href="#cite_note-39">[39]</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_(medication)&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Hormone_therapy">Hormone therapy</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=2" title="Edit section: Hormone therapy">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Menopause">Menopause</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=3" title="Edit section: Menopause">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/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">Menopausal hormone therapy</a></div> <figure class="mw-halign-right skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Hot_flashes_with_placebo_and_different_doses_of_oral_estradiol_in_menopausal_women.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Hot_flashes_with_placebo_and_different_doses_of_oral_estradiol_in_menopausal_women.png/425px-Hot_flashes_with_placebo_and_different_doses_of_oral_estradiol_in_menopausal_women.png" decoding="async" width="425" height="259" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Hot_flashes_with_placebo_and_different_doses_of_oral_estradiol_in_menopausal_women.png/638px-Hot_flashes_with_placebo_and_different_doses_of_oral_estradiol_in_menopausal_women.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f4/Hot_flashes_with_placebo_and_different_doses_of_oral_estradiol_in_menopausal_women.png/850px-Hot_flashes_with_placebo_and_different_doses_of_oral_estradiol_in_menopausal_women.png 2x" data-file-width="2372" data-file-height="1446" /></a><figcaption>Average number of moderate-to-severe <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a> per week with <a href="/wiki/Placebo" title="Placebo">placebo</a> and different doses of <a href="/wiki/Oral_estradiol" class="mw-redirect" title="Oral estradiol">oral estradiol</a> in menopausal women<a href="#cite_note-pmid10775738-40">[40]</a><a href="#cite_note-WiegratzKuhl2007-41">[41]</a></figcaption></figure> Estradiol is used in <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a> to prevent and treat moderate to severe <a href="/wiki/Menopause" title="Menopause">menopausal</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptoms</a> such as <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>, <a href="/wiki/Vaginal_dryness" class="mw-redirect" title="Vaginal dryness">vaginal dryness</a> and <a href="/wiki/Atrophic_vaginitis" title="Atrophic vaginitis">atrophy</a>, and <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a> (bone loss).<a href="#cite_note-pmid16112947-11">[11]</a> As unopposed estrogen therapy (using estrogen alone without progesterone) increases the risk of <a href="/wiki/Endometrial_hyperplasia" title="Endometrial hyperplasia">endometrial hyperplasia</a> and <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> in women with intact <a href="/wiki/Uterus" title="Uterus">uteruses</a>, estradiol is usually combined with a <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> like <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> or <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a> to prevent the effects of estradiol on the <a href="/wiki/Endometrium" title="Endometrium">endometrium</a>.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-Mutschler-42">[42]</a> This is not necessary if the woman has undergone a <a href="/wiki/Hysterectomy" title="Hysterectomy">hysterectomy</a> (surgical removal of the uterus).<a href="#cite_note-pmid16112947-11">[11]</a> A 2017 <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analysis</a> found that estradiol had no effect on depressive symptoms in peri- and postmenopausal women.<a href="#cite_note-pmid27603786-43">[43]</a> <table class="wikitable mw-collapsible mw-collapsed" style="font-size: small; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap" style="font-size: 105%;"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output .hlist dd:last-child::after,.mw-parser-output .hlist dt:last-child::after,.mw-parser-output .hlist li:last-child::after{content:none}.mw-parser-output .hlist dd dd:first-child::before,.mw-parser-output .hlist dd dt:first-child::before,.mw-parser-output .hlist dd li:first-child::before,.mw-parser-output .hlist dt dd:first-child::before,.mw-parser-output .hlist dt dt:first-child::before,.mw-parser-output .hlist dt li:first-child::before,.mw-parser-output .hlist li dd:first-child::before,.mw-parser-output .hlist li dt:first-child::before,.mw-parser-output .hlist li li:first-child::before{content:" (";font-weight:normal}.mw-parser-output .hlist dd dd:last-child::after,.mw-parser-output .hlist dd dt:last-child::after,.mw-parser-output .hlist dd li:last-child::after,.mw-parser-output .hlist dt dd:last-child::after,.mw-parser-output .hlist dt dt:last-child::after,.mw-parser-output .hlist dt li:last-child::after,.mw-parser-output .hlist li dd:last-child::after,.mw-parser-output .hlist li dt:last-child::after,.mw-parser-output .hlist li li:last-child::after{content:")";font-weight:normal}.mw-parser-output .hlist ol{counter-reset:listitem}.mw-parser-output .hlist ol>li{counter-increment:listitem}.mw-parser-output .hlist ol>li::before{content:" "counter(listitem)"\a0 "}.mw-parser-output .hlist dd ol>li:first-child::before,.mw-parser-output .hlist dt ol>li:first-child::before,.mw-parser-output .hlist li ol>li:first-child::before{content:" ("counter(listitem)"\a0 "}</style><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_dosages_for_menopausal_hormone_therapy" title="Template:Estrogen dosages for menopausal hormone therapy"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_dosages_for_menopausal_hormone_therapy" title="Template talk:Estrogen dosages for menopausal hormone therapy"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_dosages_for_menopausal_hormone_therapy" title="Special:EditPage/Template:Estrogen dosages for menopausal hormone therapy"><abbr title="Edit this template">e</abbr></a></li></ul></div> Estrogen dosages for menopausal hormone therapy </caption> <tbody><tr> <th>Route/form</th> <th>Estrogen</th> <th>Low</th> <th>Standard</th> <th>High </th></tr> <tr> <td rowspan="8"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td>Estradiol</td> <td>0.5–1 mg/day</td> <td>1–2 mg/day</td> <td>2–4 mg/day </td></tr> <tr> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></td> <td>0.5–1 mg/day</td> <td>1–2 mg/day</td> <td>2–4 mg/day </td></tr> <tr> <td><a href="/wiki/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a></td> <td>0.45–0.9 mg/day</td> <td>0.9–1.8 mg/day</td> <td>1.8–3.6 mg/day </td></tr> <tr> <td><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>Estradiol</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>Estradiol</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>Estradiol</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>Estradiol</td> <td>25 μg/day</td> <td>–</td> <td>– </td></tr> <tr> <td><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></td> <td>30 μg/day</td> <td>0.5 mg 2x/week</td> <td>0.5 mg/day </td></tr> <tr> <td rowspan="3"><a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular"><abbr title="Intramuscular">IM</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Intramuscular or <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection"><abbr title="subcutaneous">SC</abbr> injection</a></td> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></td> <td>–</td> <td>–</td> <td>4 mg 1x/4 weeks </td></tr> <tr> <td><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></td> <td>1 mg 1x/3–4 weeks</td> <td>3 mg 1x/3–4 weeks</td> <td>5 mg 1x/3–4 weeks </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>0.5 mg 1x/week</td> <td>1 mg 1x/week</td> <td>1.5 mg 1x/week </td></tr> <tr> <td><a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant"><abbr title="Subcutaneous">SC</abbr> implant</a></td> <td>Estradiol</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-heading4"><h4 id="Hypogonadism">Hypogonadism</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=4" title="Edit section: Hypogonadism">edit</a>]</div> Estrogen is responsible for the mediation of <a href="/wiki/Puberty" title="Puberty">puberty</a> in females, and in girls with <a href="/wiki/Delayed_puberty" title="Delayed puberty">delayed puberty</a> due to <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a> (low-functioning <a href="/wiki/Gonad" title="Gonad">gonads</a>, which can result in low <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormone</a> levels) such as in <a href="/wiki/Turner_syndrome" title="Turner syndrome">Turner syndrome</a>, estradiol is used to induce the development of and maintain female <a href="/wiki/Secondary_sexual_characteristic" class="mw-redirect" title="Secondary sexual characteristic">secondary sexual characteristics</a> such as <a href="/wiki/Breast" title="Breast">breasts</a>, wide <a href="/wiki/Hip" title="Hip">hips</a>, and a <a href="/wiki/Gynoid_fat_distribution" title="Gynoid fat distribution">female fat distribution</a>.<a href="#cite_note-pmid28446424-44">[44]</a><a href="#cite_note-pmid28376481-14">[14]</a><a href="#cite_note-RosenthalBurchum2017-45">[45]</a> It is also used to restore estradiol levels in adult premenopausal women with hypogonadism, for instance those with <a href="/wiki/Premature_ovarian_failure" class="mw-redirect" title="Premature ovarian failure">premature ovarian failure</a> or who have undergone <a href="/wiki/Oophorectomy" title="Oophorectomy">oophorectomy</a>.<a href="#cite_note-pmid28376481-14">[14]</a><a href="#cite_note-RosenthalBurchum2017-45">[45]</a> It is used to treat women with hypogonadism due to <a href="/wiki/Hypopituitarism" title="Hypopituitarism">hypopituitarism</a> as well.<a href="#cite_note-RosenthalBurchum2017-45">[45]</a><a href="#cite_note-pmid28376481-14">[14]</a> <div class="mw-heading mw-heading4"><h4 id="Transgender_women">Transgender women</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=5" title="Edit section: Transgender women">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">Feminizing hormone therapy</a></div> Estradiol is used as part of <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> and some <a href="/wiki/Non-binary_gender" title="Non-binary gender">non-binary</a> individuals.<a href="#cite_note-WPATH2011-46">[46]</a><a href="#cite_note-pmid28159148-17">[17]</a> The drug is used in higher dosages prior to <a href="/wiki/Gender-affirming_surgery" title="Gender-affirming surgery">gender-affirming surgery</a> or <a href="/wiki/Orchiectomy" title="Orchiectomy">orchiectomy</a> to help suppress <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> levels; after this procedure, estradiol continues to be used at lower dosages to maintain estradiol levels in the normal premenopausal female range.<a href="#cite_note-WPATH2011-46">[46]</a><a href="#cite_note-pmid28159148-17">[17]</a> <div class="mw-heading mw-heading3"><h3 id="Birth_control">Birth control</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=6" title="Edit section: Birth control">edit</a>]</div> Although almost all <a href="/wiki/Combined_oral_contraceptive" class="mw-redirect" title="Combined oral contraceptive">combined oral contraceptives</a> contain the synthetic estrogen ethinylestradiol,<a href="#cite_note-pmid25841596-47">[47]</a> natural estradiol itself is also used in some <a href="/wiki/Hormonal_contraceptive" class="mw-redirect" title="Hormonal contraceptive">hormonal contraceptives</a>, including in <a href="/wiki/Estradiol-containing_oral_contraceptive" class="mw-redirect" title="Estradiol-containing oral contraceptive">estradiol-containing oral contraceptives</a> and <a href="/wiki/Combined_injectable_contraceptive" class="mw-redirect" title="Combined injectable contraceptive">combined injectable contraceptives</a>.<a href="#cite_note-pmid23241152-15">[15]</a><a href="#cite_note-pmid12290848-16">[16]</a> It is formulated in combination with a <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestin</a> such as <a href="/wiki/Dienogest" title="Dienogest">dienogest</a>, <a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">nomegestrol acetate</a>, or medroxyprogesterone acetate, and is often used in the form of an ester prodrug like estradiol valerate or estradiol cypionate.<a href="#cite_note-pmid23241152-15">[15]</a><a href="#cite_note-pmid12290848-16">[16]</a> Hormonal contraceptives contain a progestin and/or estrogen and prevent <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> and thus the possibility of <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> by suppressing the secretion of the <a href="/wiki/Gonadotropin" title="Gonadotropin">gonadotropins</a> <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> (FSH) and <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH), the peak of which around the middle of the <a href="/wiki/Menstrual_cycle" title="Menstrual cycle">menstrual cycle</a> causes ovulation to occur.<a href="#cite_note-Glasier2010-48">[48]</a> <div class="mw-heading mw-heading3"><h3 id="Hormonal_cancer">Hormonal cancer</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=7" title="Edit section: Hormonal cancer">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Prostate_cancer">Prostate cancer</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=8" title="Edit section: Prostate cancer">edit</a>]</div> Estradiol is used as a form of <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">high-dose estrogen</a> therapy to treat <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> and is similarly effective to other therapies such as <a href="/wiki/Androgen_deprivation_therapy" title="Androgen deprivation therapy">androgen deprivation therapy</a> with <a href="/wiki/Castration" title="Castration">castration</a> and <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogens</a>.<a href="#cite_note-pmid25992351-18">[18]</a><a href="#cite_note-OettelSchillinger2012b-13">[13]</a><a href="#cite_note-pmid17239273-49">[49]</a><a href="#cite_note-pmid7500443-50">[50]</a> It is used in the form of long-lasting injected estradiol prodrugs like <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, and <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>,<a href="#cite_note-OettelSchillinger2012b-13">[13]</a><a href="#cite_note-pmid17239273-49">[49]</a><a href="#cite_note-Altwein1983-51">[51]</a> and has also more recently been assessed in the form of transdermal estradiol patches.<a href="#cite_note-pmid17239273-49">[49]</a><a href="#cite_note-pmid16006886-52">[52]</a> Estrogens are effective in the treatment of prostate cancer by suppressing <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> levels into the castrate range, increasing levels of <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> (SHBG) and thereby decreasing the fraction of free testosterone, and possibly also via direct <a href="/wiki/Cytotoxic" class="mw-redirect" title="Cytotoxic">cytotoxic</a> effects on prostate cancer cells.<a href="#cite_note-HongHolland2010-53">[53]</a><a href="#cite_note-pmid14532759-54">[54]</a><a href="#cite_note-CossJones2012-55">[55]</a> <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">Parenteral</a> estradiol is largely free of the <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> <a href="/wiki/Side_effect" title="Side effect">side effects</a> of the high oral dosages of synthetic estrogens like <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a> ad ethinylestradiol that were used previously.<a href="#cite_note-pmid17239273-49">[49]</a><a href="#cite_note-pmid2664738-56">[56]</a><a href="#cite_note-pmid17019433-57">[57]</a> In addition, estrogens may have advantages relative to castration in terms of hot flashes, sexual interest and function, osteoporosis, cognitive function, and <a href="/wiki/Quality_of_life" title="Quality of life">quality of life</a>.<a href="#cite_note-pmid17239273-49">[49]</a><a href="#cite_note-pmid17019433-57">[57]</a><a href="#cite_note-pmid14532759-54">[54]</a><a href="#cite_note-pmid21074215-58">[58]</a> However, side effects such as gynecomastia and feminization in general may be difficult to tolerate and unacceptable for many men.<a href="#cite_note-pmid17239273-49">[49]</a> <div class="mw-heading mw-heading4"><h4 id="Breast_cancer">Breast cancer</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=9" title="Edit section: Breast cancer">edit</a>]</div> <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">High-dose estrogen</a> therapy is effective in the treatment of about 35% of cases of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> in women who are at least 5 years menopausal and has comparable effectiveness to <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogen</a> therapy with medications like the <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulator</a> (SERM) <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>.<a href="#cite_note-pmid27889048-19">[19]</a><a href="#cite_note-ThomasKeenan2012-59">[59]</a><a href="#cite_note-MillerIngle2002-60">[60]</a> Although estrogens are rarely used in the treatment of breast cancer today and synthetic estrogens like diethylstilbestrol and ethinylestradiol have most commonly been used, estradiol itself has been used in the treatment of breast cancer as well.<a href="#cite_note-pmid27889048-19">[19]</a><a href="#cite_note-Estrace_Label-20">[20]</a><a href="#cite_note-EllisDehdahti2014-61">[61]</a> It has been used orally at very high doses (30 mg/day) in the treatment of therapy-naive breast cancer and orally at low doses (2 to 6 mg/day) in the treatment of breast cancer 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>.<a href="#cite_note-pmid27889048-19">[19]</a><a href="#cite_note-pmid23933149a-62">[62]</a><a href="#cite_note-Estrace_Label-20">[20]</a> <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a> is also used to treat breast cancer.<a href="#cite_note-Pharmanovia-Estradurin-63">[63]</a><a href="#cite_note-pmid393380a-64">[64]</a> <div class="mw-heading mw-heading3"><h3 id="Other_uses">Other uses</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=10" title="Edit section: Other uses">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Infertility">Infertility</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=11" title="Edit section: Infertility">edit</a>]</div> Estrogens may be used in treatment of <a href="/wiki/Infertility" title="Infertility">infertility</a> in women when there is a need to develop <a href="/wiki/Sperm" title="Sperm">sperm</a>-friendly <a href="/wiki/Cervical_mucus" class="mw-redirect" title="Cervical mucus">cervical mucus</a> or an appropriate <a href="/wiki/Uterine_lining" class="mw-redirect" title="Uterine lining">uterine lining</a>.<a href="#cite_note-Aiman2012-65">[65]</a><a href="#cite_note-SchattmanEsteves2015-66">[66]</a> It is also commonly used during in vitro fertilization (IVF). Estrogen helps maintain the endometrial lining of the uterus and help prepare for pregnancy. Research shows higher pregnancy rate if the mother takes estrogen in addition to progesterone.<a href="#cite_note-:1-67">[67]</a> Estradiol is the predominant form of estrogen during reproductive years and is most commonly prescribed.<a href="#cite_note-:1-67">[67]</a> <div class="mw-heading mw-heading4"><h4 id="Lactation_suppression">Lactation suppression</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=12" title="Edit section: Lactation suppression">edit</a>]</div> Estrogens can be used to suppress and cease <a href="/wiki/Lactation" title="Lactation">lactation</a> and <a href="/wiki/Breast_engorgement" title="Breast engorgement">breast engorgement</a> in <a href="/wiki/Postpartum" class="mw-redirect" title="Postpartum">postpartum</a> women who do not wish to <a href="/wiki/Breastfeeding" title="Breastfeeding">breastfeed</a>.<a href="#cite_note-Labhart2012-68">[68]</a><a href="#cite_note-ThomasKeenan2012-59">[59]</a> They do this by directly decreasing the sensitivity of the <a href="/wiki/Mammary_alveolus" title="Mammary alveolus">alveoli</a> of the <a href="/wiki/Mammary_gland" title="Mammary gland">mammary glands</a> to the <a href="/wiki/Galactagogue" title="Galactagogue">lactogenic hormone</a> <a href="/wiki/Prolactin" title="Prolactin">prolactin</a>.<a href="#cite_note-ThomasKeenan2012-59">[59]</a> <div class="mw-heading mw-heading4"><h4 id="Tall_stature">Tall stature</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=13" title="Edit section: Tall stature">edit</a>]</div> Estrogens have been used to limit final <a href="/wiki/Human_height" title="Human height">height</a> in adolescent girls with <a href="/wiki/Tall_stature" class="mw-redirect" title="Tall stature">tall stature</a>.<a href="#cite_note-pmid11392377-69">[69]</a> They do this by inducing <a href="/wiki/Epiphyseal_closure" class="mw-redirect" title="Epiphyseal closure">epiphyseal closure</a> and suppressing <a href="/wiki/Growth_hormone" title="Growth hormone">growth hormone</a>-induced hepatic production and by extension circulating levels of <a href="/wiki/Insulin-like_growth_factor-1" class="mw-redirect" title="Insulin-like growth factor-1">insulin-like growth factor-1</a> (IGF-1), a hormone that causes the body to grow and increase in size.<a href="#cite_note-pmid11392377-69">[69]</a> Although <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> and <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a> have mainly been used for this purpose, estradiol can also be employed.<a href="#cite_note-pmid28274950-70">[70]</a><a href="#cite_note-pmid27410906-71">[71]</a> <div class="mw-heading mw-heading4"><h4 id="Breast_enhancement">Breast enhancement</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=14" title="Edit section: Breast enhancement">edit</a>]</div> Estrogens are involved in <a href="/wiki/Breast_development" title="Breast development">breast development</a> and estradiol may be used as a form of hormonal breast enhancement to increase the <a href="/wiki/Breast_size" class="mw-redirect" title="Breast size">size of the breasts</a>.<a href="#cite_note-GöretzlehnerLauritzen2012-72">[72]</a><a href="#cite_note-ManselFodstad2007-73">[73]</a><a href="#cite_note-pmid9610425-74">[74]</a><a href="#cite_note-Lauritzen1980-75">[75]</a><a href="#cite_note-KaiserLeidenberger1991-76">[76]</a> Both polyestradiol phosphate monotherapy and <a href="/wiki/Pseudopregnancy" title="Pseudopregnancy">pseudopregnancy</a> with a combination of high-dosage intramuscular estradiol valerate and <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a> have been assessed for this purpose in clinical studies.<a href="#cite_note-GöretzlehnerLauritzen2012-72">[72]</a><a href="#cite_note-ManselFodstad2007-73">[73]</a><a href="#cite_note-pmid9610425-74">[74]</a><a href="#cite_note-Lauritzen1980-75">[75]</a> However, acute or temporary <a href="/wiki/Breast_enlargement" title="Breast enlargement">breast enlargement</a> is a well-known side effect of estrogens, and increases in breast size tend to regress following discontinuation of treatment.<a href="#cite_note-GöretzlehnerLauritzen2012-72">[72]</a><a href="#cite_note-pmid9610425-74">[74]</a><a href="#cite_note-Lauritzen1980-75">[75]</a> Aside from those without prior established breast development, evidence is lacking for a sustained increases in breast size with estrogens.<a href="#cite_note-GöretzlehnerLauritzen2012-72">[72]</a><a href="#cite_note-pmid9610425-74">[74]</a><a href="#cite_note-Lauritzen1980-75">[75]</a> <div class="mw-heading mw-heading4"><h4 id="Schizophrenia">Schizophrenia</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=15" title="Edit section: Schizophrenia">edit</a>]</div> Estradiol has been found to be effective in the <a href="/wiki/Adjunct_therapy" class="mw-redirect" title="Adjunct therapy">adjunctive</a> treatment of <a href="/wiki/Schizophrenia" title="Schizophrenia">schizophrenia</a> in women.<a href="#cite_note-pmid22998932-77">[77]</a><a href="#cite_note-pmid24732671-78">[78]</a><a href="#cite_note-pmid27824682-79">[79]</a> It has been found to significantly reduce <a href="/wiki/Positive_symptoms" class="mw-redirect" title="Positive symptoms">positive</a>, <a href="/wiki/Negative_symptoms" class="mw-redirect" title="Negative symptoms">negative</a>, and <a href="/wiki/Schizophrenia#Cognitive_dysfunction" title="Schizophrenia">cognitive symptoms</a>, with particular benefits on positive symptoms.<a href="#cite_note-pmid22998932-77">[77]</a><a href="#cite_note-pmid24732671-78">[78]</a><a href="#cite_note-pmid27824682-79">[79]</a><a href="#cite_note-pmid28673758-80">[80]</a> Other estrogens, as well as <a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">selective estrogen receptor modulators</a> (SERMs) like <a href="/wiki/Raloxifene" title="Raloxifene">raloxifene</a>, have been found to be effective in the adjunctive treatment of schizophrenia in women similarly.<a href="#cite_note-pmid22998932-77">[77]</a><a href="#cite_note-pmid29321530-81">[81]</a><a href="#cite_note-pmid27193386-82">[82]</a> Estrogens may be useful in the treatment of schizophrenia in men as well, but their use in this population is limited by <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminizing</a> <a href="/wiki/Side_effect" title="Side effect">side effects</a>.<a href="#cite_note-pmid28941299-83">[83]</a> SERMs, which have few or no feminizing side effects, have been found to be effective in the adjunctive treatment of schizophrenia in men similarly to in women and may be more useful than estrogens in this sex.<a href="#cite_note-pmid29321530-81">[81]</a><a href="#cite_note-pmid27193386-82">[82]</a> <div class="mw-heading mw-heading4"><h4 id="Sexual_deviance">Sexual deviance</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=16" title="Edit section: Sexual deviance">edit</a>]</div> Estradiol has been used at high doses to suppress <a href="/wiki/Sex_drive" class="mw-redirect" title="Sex drive">sex drive</a> in men with <a href="/wiki/Sexual_deviance" class="mw-redirect" title="Sexual deviance">sexual deviance</a> such as <a href="/wiki/Paraphilia" title="Paraphilia">paraphilias</a> and in <a href="/wiki/Sex_offender" title="Sex offender">sex offenders</a>.<a href="#cite_note-Guay2009-84">[84]</a><a href="#cite_note-MorganMorgan1984-85">[85]</a><a href="#cite_note-Chatz1972-86">[86]</a> It has specifically been used for this indication in the forms of <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injections</a> of <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> and <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a> and of <a href="/wiki/Subcutaneous_pellet_implant" class="mw-redirect" title="Subcutaneous pellet implant">subcutaneous pellet implants</a> of estradiol.<a href="#cite_note-Guay2009-84">[84]</a><a href="#cite_note-MorganMorgan1984-85">[85]</a><a href="#cite_note-Chatz1972-86">[86]</a> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=17" title="Edit section: Available forms">edit</a>]</div> <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 class="mw-selflink selflink">estradiol</a><a href="#cite_note-87">[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-88">[b]</a> </th> <th scope="col">Brand names<a href="#cite_note-89">[c]</a> </th></tr> <tr> <th scope="row" rowspan="2"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a> </th> <td>Estradiol</td> <td>Tablet</td> <td>0.1, 0.2, 0.5, 1, 2, 4 mg</td> <td>Estrace, Ovocyclin </td></tr> <tr> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></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">Estradiol </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">Estradiol </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-90">[d]</a> </th> <td>Estradiol</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><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></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>Estradiol</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-87"><a href="#cite_ref-87">^</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-88"><a href="#cite_ref-88">^</a> Doses are given per unit (ex: per tablet, per mL). </li> <li id="cite_note-89"><a href="#cite_ref-89">^</a> Other brand names may be manufactured or previously manufactured. </li> <li id="cite_note-90"><a href="#cite_ref-90">^</a> By intramuscular or subcutaneous injection. </li> </ol></div></div> Sources: <a href="#cite_note-Drugs@FDA-estdose-91">[87]</a><a href="#cite_note-Lobo_2007-92">[88]</a><a href="#cite_note-FalconeHurd2017-93">[89]</a><a href="#cite_note-Becker_2001-94">[90]</a><a href="#cite_note-KleemannEngel2014-95">[91]</a><a href="#cite_note-Muller1998-96">[92]</a><a href="#cite_note-KrishnaShah1996-97">[93]</a><a href="#cite_note-NNR1949-98">[94]</a><a href="#cite_note-AerodiolLabel-99">[95]</a><a href="#cite_note-Drugs.com-100">[96]</a><a href="#cite_note-pmid18382901-101">[97]</a><a href="#cite_note-PlouffeRavnikar2012-102">[98]</a><a href="#cite_note-UC1952-103">[99]</a><a href="#cite_note-Leidenberger2013-104">[100]</a></div></div> </td></tr></tbody></table> Estradiol is available in a variety of different formulations, including oral, intranasal, transdermal/topical, vaginal, injectable, and implantable preparations.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-LemkeWilliams2012-105">[101]</a> An <a href="/wiki/Ester" title="Ester">ester</a> may be attached to one or both of the <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl groups</a> of estradiol to improve its oral bioavailability and/or duration of action with injection.<a href="#cite_note-pmid16112947-11">[11]</a> Such modifications give rise to forms such as <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a> (oral and vaginal), <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> (oral and injectable), <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a> (injectable), <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a> (injectable), <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a> (injectable), and <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a> (injectable; a <a href="/wiki/Polymer" title="Polymer">polymerized</a> ester of estradiol), which are all <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a> of estradiol.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-LemkeWilliams2012-105">[101]</a><a href="#cite_note-pmid10230677-106">[102]</a> <style data-mw-deduplicate="TemplateStyles:r1275594942">@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-center .gallery{justify-content:center}.mw-parser-output .mod-gallery-left .gallery{justify-content:left}.mw-parser-output .mod-gallery-right .gallery{justify-content:right}.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.gallery.gallery{line-height:1.35em;display:flex;flex-wrap:wrap;column-gap:4px}.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{outline:solid var(--background-color-neutral,#eaecf0)1px}.mw-parser-output .mod-gallery .whitebg .thumb{background:var(--background-color-base,#fff)!important}@media screen{html.skin-theme-clientpref-night .mw-parser-output .mod-gallery .bordered-images .thumb img[alt*="\200b \200b \200b "],html.skin-theme-clientpref-night .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{outline:solid #d7d7d7 1px}html.skin-theme-clientpref-night .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{background:none!important}html.skin-theme-clientpref-night .mw-parser-output .mod-gallery .whitebg .thumb img:not([alt*="\200b \200b \200b "]):not([alt*="\200b \200b \200c "]){background:white!important}html.skin-theme-clientpref-night .mw-parser-output .mod-gallery img[alt*="\200b \200b \200b "]{filter:invert(1)hue-rotate(180deg)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .mod-gallery .bordered-images .thumb img[alt*="\200b \200b \200b "],html.skin-theme-clientpref-os .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{outline:solid #d7d7d7 1px}html.skin-theme-clientpref-os .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{background:none!important}html.skin-theme-clientpref-os .mw-parser-output .mod-gallery .whitebg .thumb img:not([alt*="\200b \200b \200b "]):not([alt*="\200b \200b \200c "]){background:white!important}html.skin-theme-clientpref-os .mw-parser-output .mod-gallery img[alt*="\200b \200b \200b "]{filter:invert(1)hue-rotate(180deg)}}</style><div class="mod-gallery mod-gallery-center" style=""font-size:small;""><div class="title"><div>Gallery of available forms of estradiol</div></div><div class="main"><div><ul class="gallery mw-gallery-traditional nochecker bordered-images whitebg"> <li class="gallerybox" style="width: 200px"> <div class="thumb" style="width: 195px; height: 185px;"><a href="/wiki/File:Progynova_(estradiol_valerate)_tablets_in_the_United_Kingdom.jpg" class="mw-file-description" title="Progynova (estradiol valerate) 2 mg oral tablets."><img alt="Progynova (estradiol valerate) 2 mg oral tablets." src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Progynova_%28estradiol_valerate%29_tablets_in_the_United_Kingdom.jpg/165px-Progynova_%28estradiol_valerate%29_tablets_in_the_United_Kingdom.jpg" decoding="async" width="165" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Progynova_%28estradiol_valerate%29_tablets_in_the_United_Kingdom.jpg/248px-Progynova_%28estradiol_valerate%29_tablets_in_the_United_Kingdom.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Progynova_%28estradiol_valerate%29_tablets_in_the_United_Kingdom.jpg/330px-Progynova_%28estradiol_valerate%29_tablets_in_the_United_Kingdom.jpg 2x" data-file-width="4813" data-file-height="3398" /></a></div> <div class="gallerytext">Progynova (<a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>) 2 mg <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a>.</div> </li> <li class="gallerybox" style="width: 200px"> <div class="thumb" style="width: 195px; height: 185px;"><a href="/wiki/File:Generic_estradiol_(Mylan)_0.1_mg_per_day_once-weekly_transdermal_systems.jpg" class="mw-file-description" title="Generic estradiol (Mylan) 100 μg/day once-weekly transdermal patches."><img alt="Generic estradiol (Mylan) 100 μg/day once-weekly transdermal patches." src="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Generic_estradiol_%28Mylan%29_0.1_mg_per_day_once-weekly_transdermal_systems.jpg/152px-Generic_estradiol_%28Mylan%29_0.1_mg_per_day_once-weekly_transdermal_systems.jpg" decoding="async" width="152" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/45/Generic_estradiol_%28Mylan%29_0.1_mg_per_day_once-weekly_transdermal_systems.jpg/228px-Generic_estradiol_%28Mylan%29_0.1_mg_per_day_once-weekly_transdermal_systems.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/45/Generic_estradiol_%28Mylan%29_0.1_mg_per_day_once-weekly_transdermal_systems.jpg/303px-Generic_estradiol_%28Mylan%29_0.1_mg_per_day_once-weekly_transdermal_systems.jpg 2x" data-file-width="2958" data-file-height="3024" /></a></div> <div class="gallerytext"><a href="/wiki/Generic_drug" title="Generic drug">Generic</a> estradiol (Mylan) 100 μg/day once-weekly <a href="/wiki/Transdermal_patch" title="Transdermal patch">transdermal patches</a>.</div> </li> <li class="gallerybox" style="width: 200px"> <div class="thumb" style="width: 195px; height: 185px;"><a href="/wiki/File:Estrogen_patch.jpg" class="mw-file-description" title="Vivelle-Dot (estradiol) 100 μg/day twice-weekly transdermal patches."><img alt="Vivelle-Dot (estradiol) 100 μg/day twice-weekly transdermal patches." src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Estrogen_patch.jpg/155px-Estrogen_patch.jpg" decoding="async" width="155" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Estrogen_patch.jpg/233px-Estrogen_patch.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/20/Estrogen_patch.jpg/310px-Estrogen_patch.jpg 2x" data-file-width="1408" data-file-height="1409" /></a></div> <div class="gallerytext">Vivelle-Dot (estradiol) 100 μg/day twice-weekly <a href="/wiki/Transdermal_patch" title="Transdermal patch">transdermal patches</a>.</div> </li> <li class="gallerybox" style="width: 200px"> <div class="thumb" style="width: 195px; height: 185px;"><a href="/wiki/File:EstroGel_0.06%25_(estradiol_transdermal_gel)_pumps.jpg" class="mw-file-description" title="EstroGel 0.06% (estradiol) once-daily hydroalcoholic transdermal gel. Delivers 0.75 mg estradiol per pump."><img alt="EstroGel 0.06% (estradiol) once-daily hydroalcoholic transdermal gel. Delivers 0.75 mg estradiol per pump." src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/EstroGel_0.06%25_%28estradiol_transdermal_gel%29_pumps.jpg/153px-EstroGel_0.06%25_%28estradiol_transdermal_gel%29_pumps.jpg" decoding="async" width="153" height="155" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3b/EstroGel_0.06%25_%28estradiol_transdermal_gel%29_pumps.jpg/230px-EstroGel_0.06%25_%28estradiol_transdermal_gel%29_pumps.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3b/EstroGel_0.06%25_%28estradiol_transdermal_gel%29_pumps.jpg/306px-EstroGel_0.06%25_%28estradiol_transdermal_gel%29_pumps.jpg 2x" data-file-width="2870" data-file-height="2910" /></a></div> <div class="gallerytext">EstroGel 0.06% (estradiol) once-daily <a href="/wiki/Hydroalcoholic" title="Hydroalcoholic">hydroalcoholic</a> <a href="/wiki/Transdermal_gel" class="mw-redirect" title="Transdermal gel">transdermal gel</a>. Delivers 0.75 mg estradiol per pump.</div> </li> <li class="gallerybox" style="width: 200px"> <div class="thumb" style="width: 195px; height: 185px;"><a href="/wiki/File:Depo-Estradiol_(estradiol_cypionate)_vials.jpg" class="mw-file-description" title="Depo-Estradiol 5 mg/mL (estradiol cypionate in oil solution) vials. Used by depot intramuscular injection."><img alt="Depo-Estradiol 5 mg/mL (estradiol cypionate in oil solution) vials. Used by depot intramuscular injection." src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Depo-Estradiol_%28estradiol_cypionate%29_vials.jpg/250px-Depo-Estradiol_%28estradiol_cypionate%29_vials.jpg" decoding="async" width="165" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3f/Depo-Estradiol_%28estradiol_cypionate%29_vials.jpg/330px-Depo-Estradiol_%28estradiol_cypionate%29_vials.jpg 2x" data-file-width="3395" data-file-height="2463" /></a></div> <div class="gallerytext">Depo-Estradiol 5 mg/mL (<a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a> in <a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</a>) <a href="/wiki/Vial" title="Vial">vials</a>. Used by <a href="/wiki/Depot_injection" title="Depot injection">depot</a> <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>.</div> </li> </ul></div></div></div> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=18" title="Edit section: Contraindications">edit</a>]</div> Estrogens like estradiol have a number of <a href="/wiki/Contraindication" title="Contraindication">contraindications</a>.<a href="#cite_note-pmid2215269-107">[103]</a><a href="#cite_note-LauritzenStudd2005-28">[28]</a><a href="#cite_note-Lauritzen2001-108">[104]</a><a href="#cite_note-Midwinter1976-109">[105]</a> Estradiol should be avoided when there is undiagnosed abnormal <a href="/wiki/Vaginal_bleeding" title="Vaginal bleeding">vaginal bleeding</a>, known, suspected or a history of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, current treatment for metastatic disease, known or suspected estrogen-dependent <a href="/wiki/Neoplasia" class="mw-redirect" title="Neoplasia">neoplasia</a>, <a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">deep vein thrombosis</a>, <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a> or history of these conditions, active or recent arterial <a href="/wiki/Thromboembolic_disease" class="mw-redirect" title="Thromboembolic disease">thromboembolic disease</a> such as <a href="/wiki/Stroke" title="Stroke">stroke</a>, <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>, <a href="/wiki/Liver_dysfunction" class="mw-redirect" title="Liver dysfunction">liver dysfunction</a> or <a href="/wiki/Liver_disease" title="Liver disease">disease</a>. Estradiol should not be taken by people with a <a href="/wiki/Hypersensitivity" title="Hypersensitivity">hypersensitivity</a>/<a href="/wiki/Allergy" title="Allergy">allergy</a> or those who are pregnant or are suspected pregnant.<a href="#cite_note-Estrace_Label-20">[20]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=19" 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/Estrogen_(medication)#Side_effects" title="Estrogen (medication)">Estrogen (medication) § Side effects</a>, and <a href="/wiki/List_of_side_effects_of_estradiol" title="List of side effects of estradiol">List of side effects of estradiol</a></div> Common <a href="/wiki/Side_effect" title="Side effect">side effects</a> of estradiol in women include <a href="/wiki/Headache" title="Headache">headache</a>, <a href="/wiki/Breast_pain" title="Breast pain">breast pain or tenderness</a>, <a href="/wiki/Breast_enlargement" title="Breast enlargement">breast enlargement</a>, <a href="/wiki/Irregular_menstruation" title="Irregular menstruation">irregular</a> <a href="/wiki/Vaginal_bleeding" title="Vaginal bleeding">vaginal bleeding or spotting</a>, <a href="/wiki/Abdominal_cramp" class="mw-redirect" title="Abdominal cramp">abdominal cramps</a>, <a href="/wiki/Bloating" title="Bloating">bloating</a>, <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a>, and <a href="/wiki/Nausea" title="Nausea">nausea</a>.<a href="#cite_note-Estrace_Label-20">[20]</a><a href="#cite_note-Estring_Label-110">[106]</a><a href="#cite_note-111">[107]</a><a href="#cite_note-pmid23375353-5">[5]</a> Other possible side effects of estrogens may include <a href="/wiki/High_blood_pressure" class="mw-redirect" title="High blood pressure">high blood pressure</a>, <a href="/wiki/High_blood_sugar" class="mw-redirect" title="High blood sugar">high blood sugar</a>, enlargement of <a href="/wiki/Uterine_fibroid" title="Uterine fibroid">uterine fibroids</a>, <a href="/wiki/Melasma" title="Melasma">melasma</a>, <a href="/wiki/Vaginal_yeast_infection" title="Vaginal yeast infection">vaginal yeast infections</a>, and <a href="/wiki/Liver_problems" class="mw-redirect" title="Liver problems">liver problems</a>.<a href="#cite_note-Estrace_Label-20">[20]</a> In men, estrogens can cause breast pain or tenderness, <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> (male <a href="/wiki/Breast_development" title="Breast development">breast development</a>), <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a>, <a href="/wiki/Demasculinization" class="mw-redirect" title="Demasculinization">demasculinization</a>, <a href="/wiki/Sexual_dysfunction" title="Sexual dysfunction">sexual dysfunction</a> (<a href="/wiki/Decreased_libido" class="mw-redirect" title="Decreased libido">decreased libido</a> and <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a>), <a href="/wiki/Hypogonadism" title="Hypogonadism">hypogonadism</a>, <a href="/wiki/Testicular_atrophy" title="Testicular atrophy">testicular atrophy</a>, and <a href="/wiki/Infertility" title="Infertility">infertility</a>.<a href="#cite_note-Pohanish2011-21">[21]</a><a href="#cite_note-CecilBennett1996-22">[22]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" width="610px" style="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:Side_effects_of_lower_versus_higher_dose_oral_estradiol" title="Template:Side effects of lower versus higher dose oral estradiol"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Side_effects_of_lower_versus_higher_dose_oral_estradiol" title="Template talk:Side effects of lower versus higher dose oral estradiol"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Side_effects_of_lower_versus_higher_dose_oral_estradiol" title="Special:EditPage/Template:Side effects of lower versus higher dose oral estradiol"><abbr title="Edit this template">e</abbr></a></li></ul></div> Side effects of lower versus higher dose oral estradiol </caption> <tbody><tr> <th rowspan="2">Serious adverse event </th> <th colspan="2"><a class="mw-selflink selflink"><abbr title="Estradiol_(medication)">Estradiol</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 Estradiol_(medication) 6 mg/day (n = 34) </th> <th colspan="2"><a class="mw-selflink selflink"><abbr title="Estradiol_(medication)">Estradiol</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 Estradiol_(medication) 30 mg/day (n = 32) </th></tr> <tr> <th width="75px">n </th> <th width="75px">% </th> <th width="75px">n </th> <th width="75px">% </th></tr> <tr> <td><a href="/wiki/Nausea" title="Nausea">Nausea</a>/<a href="/wiki/Vomiting" title="Vomiting">vomiting</a></td> <td>0</td> <td>0.0</td> <td>5</td> <td>15.6 </td></tr> <tr> <td><a href="/wiki/Hyponatremia" title="Hyponatremia">Hyponatremia</a></td> <td>1</td> <td>2.9</td> <td>5</td> <td>15.6 </td></tr> <tr> <td><a href="/wiki/Pleural_effusion" title="Pleural effusion">Pleural effusion</a></td> <td>0</td> <td>0.0</td> <td>4</td> <td>12.5 </td></tr> <tr> <td><a href="/wiki/Pain" title="Pain">Pain</a></td> <td>6</td> <td>17.6</td> <td>4</td> <td>12.5 </td></tr> <tr> <td><a href="/wiki/Thrombosis" title="Thrombosis">Thrombosis</a>/<a href="/wiki/Embolism" title="Embolism">embolism</a></td> <td>1</td> <td>2.9</td> <td>1</td> <td>3.1 </td></tr> <tr> <td><a href="/wiki/Brain_ischemia" title="Brain ischemia">Brain ischemia</a></td> <td>1</td> <td>2.9</td> <td>0</td> <td>0.0 </td></tr> <tr> <td><a href="/wiki/Infection" title="Infection">Infection</a></td> <td>2</td> <td>5.9</td> <td>3</td> <td>9.4 </td></tr> <tr> <td><a href="/wiki/Hypercalcemia" class="mw-redirect" title="Hypercalcemia">Hypercalcemia</a></td> <td>0</td> <td>0.0</td> <td>2</td> <td>6.3 </td></tr> <tr> <td>Other</td> <td>6</td> <td>17.6</td> <td>10</td> <td>31.3 </td></tr> <tr class="sortbottom"> <td colspan="5" style="width: 1px; font-size: small; background-color:#eaecf0; text-align: center;">Summary: <a href="/wiki/Side_effects" class="mw-redirect" title="Side effects">Side effects</a> in a small phase 2 study of women with <a href="/wiki/Metastatic_breast_cancer" title="Metastatic breast cancer">metastatic breast cancer</a> randomized to receive either 6 or 30 mg/day of <a href="/wiki/Pharmacokinetics_of_estradiol#Oral_administration" title="Pharmacokinetics of estradiol"><abbr title="Pharmacokinetics_of_estradiol#Oral_administration">oral estradiol</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 Pharmacokinetics_of_estradiol#Oral_administration as therapy. "The adverse event rate (≥grade 3) in the 30-mg group (11/32 [34%]; 95% confidence interval [CI], 23%-47%) was higher than in the 6-mg group (4/34 [18%]; 95% CI, 5%-22%; p=0.03). Clinical benefit rates were 9 of 32 (28%; 95% CI, 18%-41%) in the 30-mg group and 10 of 34 (29%; 95% CI, 19%-42%) in the 6-mg group." Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Blood_clots">Blood clots</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=20" title="Edit section: Blood clots">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estrogen_(medication)#Cardiovascular_events" title="Estrogen (medication)">Estrogen (medication) § Cardiovascular events</a></div> <a href="/wiki/Oral_administration" title="Oral administration">Oral</a> estradiol and <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, for instance in <a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">menopausal hormone therapy</a> or <a href="/wiki/Birth_control_pill" class="mw-redirect" title="Birth control pill">birth control pills</a>, are associated with a significantly higher risk of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a> (VTE) than non-use.<a href="#cite_note-pmid29936403-112">[108]</a><a href="#cite_note-pmid29570359-113">[109]</a><a href="#cite_note-pmid30626577-114">[110]</a><a href="#cite_note-pmid30519125-115">[111]</a> Higher doses of oral estrogens are associated with higher risks of VTE.<a href="#cite_note-pmid30626577-114">[110]</a><a href="#cite_note-pmid23136837-116">[112]</a><a href="#cite_note-pmid28049361-117">[113]</a> In contrast to oral estradiol, <a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">transdermal</a> and <a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">vaginal</a> estradiol at menopausal replacement dosages are not associated with a higher incidence of VTE.<a href="#cite_note-pmid29936403-112">[108]</a><a href="#cite_note-pmid29570359-113">[109]</a><a href="#cite_note-pmid25223916-118">[114]</a><a href="#cite_note-pmid30626577-114">[110]</a> Low doses (e.g., 50 μg/day) and high doses (e.g., 100 μg/day) of transdermal estradiol for menopausal replacement do not differ in terms of VTE risk.<a href="#cite_note-pmid21262434-119">[115]</a><a href="#cite_note-pmid25223916-118">[114]</a><a href="#cite_note-pmid26327865-120">[116]</a><a href="#cite_note-pmid30626577-114">[110]</a> The higher risk of VTE with oral estradiol can be attributed to the <a href="/wiki/First-pass_effect" class="mw-redirect" title="First-pass effect">first pass</a> and a disproportionate effect on <a href="/wiki/Liver_protein_synthesis" class="mw-redirect" title="Liver protein synthesis">liver synthesis</a> of <a href="/wiki/Coagulation_factor" class="mw-redirect" title="Coagulation factor">coagulation factors</a>.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid30008249-121">[117]</a> Even high doses of <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenteral</a> estradiol, such as high-dose <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, have minimal influence on coagulation factors, in contrast to oral estrogen therapy.<a href="#cite_note-pmid17019433-57">[57]</a><a href="#cite_note-pmid17239273-49">[49]</a><a href="#cite_note-pmid24932461-122">[118]</a> However, sufficient doses of parenteral estradiol, for instance very high doses of estradiol valerate by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>, can nonetheless activate coagulation, presumably increasing VTE risk.<a href="#cite_note-pmid16284988-123">[119]</a><a href="#cite_note-HorskyPresl1981-124">[120]</a> In addition to the <a href="/wiki/Route_of_administration" title="Route of administration">route of administration</a>, the type of estrogen influences VTE risk.<a href="#cite_note-pmid31465627-125">[121]</a><a href="#cite_note-pmid30008249-121">[117]</a> Oral <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a> are associated with a higher risk of VTE than oral estradiol.<a href="#cite_note-pmid26444994-126">[122]</a><a href="#cite_note-pmid26327865-120">[116]</a><a href="#cite_note-pmid24081194-127">[123]</a> <a href="/wiki/Estradiol-containing_birth_control_pill" title="Estradiol-containing birth control pill">Estradiol- and estradiol valerate-containing birth control pills</a> are associated with a lower risk of VTE than birth control pills containing <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>.<a href="#cite_note-pmid30519125-115">[111]</a><a href="#cite_note-pmid30008249-121">[117]</a> The relative risk of VTE is thought to be highest with oral ethinylestradiol, intermediate with oral conjugated estrogens, low with oral estradiol and parenteral estradiol valerate, and very low with transdermal estradiol.<a href="#cite_note-pmid31465627-125">[121]</a> Conjugated estrogens and ethinylestradiol are thought to have a higher risk of VTE than estradiol because they are resistant to <a href="/wiki/Liver" title="Liver">hepatic</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and have a disproportionate influence on liver production of coagulation factors.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid31465627-125">[121]</a><a href="#cite_note-pmid30008249-121">[117]</a> The combination of oral or transdermal estradiol and a progestin is associated with a higher risk of VTE than estradiol alone.<a href="#cite_note-pmid29570359-113">[109]</a><a href="#cite_note-pmid31372078-128">[124]</a> <a href="/wiki/Dydrogesterone" title="Dydrogesterone">Dydrogesterone</a> is associated with a lower risk than other progestins such as <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a> and <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, while oral <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> is associated with no increase in risk of VTE.<a href="#cite_note-pmid29570359-113">[109]</a><a href="#cite_note-pmid30626577-114">[110]</a> Older <a href="/wiki/Ageing" title="Ageing">age</a>, higher <a href="/wiki/Body_weight" class="mw-redirect" title="Body weight">body weight</a>, lower <a href="/wiki/Physical_activity" title="Physical activity">physical activity</a>, and <a href="/wiki/Smoking" title="Smoking">smoking</a> are all associated with a higher risk of VTE with oral estrogen therapy.<a href="#cite_note-pmid30008249-121">[117]</a><a href="#cite_note-pmid29526116-129">[125]</a><a href="#cite_note-pmid31372078-128">[124]</a><a href="#cite_note-pmid23136837-116">[112]</a> Risk of VTE with estrogen therapy is highest at the start of treatment, particularly during the first year, and decreases over time.<a href="#cite_note-pmid30008249-121">[117]</a><a href="#cite_note-pmid31372078-128">[124]</a> The <a href="/wiki/Absolute_risk" title="Absolute risk">absolute risk</a> of VTE with estrogen and/or progestin therapy is small.<a href="#cite_note-pmid27051991-130">[126]</a><a href="#cite_note-FDA2018-131">[127]</a><a href="#cite_note-pmid31372078-128">[124]</a> Women who are not on a birth control pill or hormone therapy have a risk of VTE of about 1 to 5 out of 10,000 women per year.<a href="#cite_note-pmid27051991-130">[126]</a><a href="#cite_note-FDA2018-131">[127]</a><a href="#cite_note-pmid26327865-120">[116]</a><a href="#cite_note-pmid31372078-128">[124]</a> In women taking a birth control pill containing ethinylestradiol and a progestin, the risk of VTE is in the range of 3 to 10 out of 10,000 women per year.<a href="#cite_note-pmid27051991-130">[126]</a><a href="#cite_note-FDA2018-131">[127]</a><a href="#cite_note-pmid31372078-128">[124]</a> Birth control pills containing estradiol valerate and a progestin are associated with about half the risk of VTE of ethinylestradiol/progestin-containing birth control pills.<a href="#cite_note-pmid30519125-115">[111]</a><a href="#cite_note-pmid28902531-132">[128]</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_women" class="mw-redirect" title="Transgender women">transgender women</a> likewise is associated with a lower risk of VTE than birth control pills containing ethinylestradiol and a progestin.<a href="#cite_note-pmid30602475-133">[129]</a><a href="#cite_note-pmid31465627-125">[121]</a> The risk of VTE during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>, when estrogens and progesterone increase to very high levels, is 5 to 20 in 10,000 women per year, while the risk is 40 to 65 per 10,000 women per year during the <a href="/wiki/Postpartum_period" title="Postpartum period">postpartum period</a>.<a href="#cite_note-FDA2018-131">[127]</a><a href="#cite_note-pmid31372078-128">[124]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="margin: 1em auto;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)" title="Template:Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)" title="Template talk:Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Risk_of_venous_thromboembolism_with_hormone_therapy_and_birth_control_pills_(QResearch/CPRD)" title="Special:EditPage/Template:Risk of venous thromboembolism with hormone therapy and birth control pills (QResearch/CPRD)"><abbr title="Edit this template">e</abbr></a></li></ul></div> Risk of venous thromboembolism (VTE) with hormone therapy and birth control (QResearch/CPRD) </caption> <tbody><tr> <th class="unsortable">Type</th> <th class="unsortable">Route</th> <th class="unsortable">Medications</th> <th><a href="/wiki/Odds_ratio" title="Odds ratio">Odds ratio</a> (95% <a href="/wiki/Confidence_interval" title="Confidence interval"><abbr title="confidence interval">CI</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip confidence interval) </th></tr> <tr> <td rowspan="14"><a href="/wiki/Menopausal_hormone_therapy" class="mw-redirect" title="Menopausal hormone therapy">Menopausal hormone therapy</a></td> <td rowspan="10"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td>Estradiol alone     ≤1 mg/day     >1 mg/day</td> <td>1.27 (1.16–1.39)* 1.22 (1.09–1.37)* 1.35 (1.18–1.55)* </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a> alone     ≤0.625 mg/day     >0.625 mg/day</td> <td>1.49 (1.39–1.60)* 1.40 (1.28–1.53)* 1.71 (1.51–1.93)* </td></tr> <tr> <td><a href="/wiki/Estradiol/medroxyprogesterone_acetate" title="Estradiol/medroxyprogesterone acetate">Estradiol/medroxyprogesterone acetate</a></td> <td>1.44 (1.09–1.89)* </td></tr> <tr> <td><a href="/wiki/Estradiol/dydrogesterone" title="Estradiol/dydrogesterone">Estradiol/dydrogesterone</a>     ≤1 mg/day <abbr title="estradiol">E2</abbr>     >1 mg/day <abbr title="estradiol">E2</abbr></td> <td>1.18 (0.98–1.42) 1.12 (0.90–1.40) 1.34 (0.94–1.90) </td></tr> <tr> <td><a href="/wiki/Estradiol/norethisterone" title="Estradiol/norethisterone">Estradiol/norethisterone</a>     ≤1 mg/day <abbr title="estradiol">E2</abbr>     >1 mg/day <abbr title="estradiol">E2</abbr></td> <td>1.68 (1.57–1.80)* 1.38 (1.23–1.56)* 1.84 (1.69–2.00)* </td></tr> <tr> <td><a href="/wiki/Estradiol/norgestrel" class="mw-redirect" title="Estradiol/norgestrel">Estradiol/norgestrel</a> or <a href="/wiki/Estradiol/drospirenone" title="Estradiol/drospirenone">estradiol/drospirenone</a></td> <td>1.42 (1.00–2.03) </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens/medroxyprogesterone_acetate" title="Conjugated estrogens/medroxyprogesterone acetate">Conjugated estrogens/medroxyprogesterone acetate</a></td> <td>2.10 (1.92–2.31)* </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens/norgestrel" title="Conjugated estrogens/norgestrel">Conjugated estrogens/norgestrel</a>     ≤0.625 mg/day <abbr title="conjugated estrogens">CEEs</abbr>     >0.625 mg/day <abbr title="conjugated estrogens">CEEs</abbr></td> <td>1.73 (1.57–1.91)* 1.53 (1.36–1.72)* 2.38 (1.99–2.85)* </td></tr> <tr> <td><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a> alone</td> <td>1.02 (0.90–1.15) </td></tr> <tr> <td><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a> alone</td> <td>1.49 (1.24–1.79)* </td></tr> <tr> <td rowspan="2"><a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">Transdermal</a></td> <td>Estradiol alone    ≤50 μg/day    >50 μg/day</td> <td>0.96 (0.88–1.04) 0.94 (0.85–1.03) 1.05 (0.88–1.24) </td></tr> <tr> <td>Estradiol/<a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a></td> <td>0.88 (0.73–1.01) </td></tr> <tr> <td rowspan="2"><a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">Vaginal</a></td> <td>Estradiol alone</td> <td>0.84 (0.73–0.97) </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a> alone</td> <td>1.04 (0.76–1.43) </td></tr> <tr> <td rowspan="7"><a href="/wiki/Combined_birth_control" class="mw-redirect" title="Combined birth control">Combined birth control</a></td> <td rowspan="7"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td><a href="/wiki/Ethinylestradiol/norethisterone" title="Ethinylestradiol/norethisterone">Ethinylestradiol/norethisterone</a></td> <td>2.56 (2.15–3.06)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/levonorgestrel" title="Ethinylestradiol/levonorgestrel">Ethinylestradiol/levonorgestrel</a></td> <td>2.38 (2.18–2.59)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/norgestimate" class="mw-redirect" title="Ethinylestradiol/norgestimate">Ethinylestradiol/norgestimate</a></td> <td>2.53 (2.17–2.96)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/desogestrel" title="Ethinylestradiol/desogestrel">Ethinylestradiol/desogestrel</a></td> <td>4.28 (3.66–5.01)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/gestodene" title="Ethinylestradiol/gestodene">Ethinylestradiol/gestodene</a></td> <td>3.64 (3.00–4.43)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/drospirenone" title="Ethinylestradiol/drospirenone">Ethinylestradiol/drospirenone</a></td> <td>4.12 (3.43–4.96)* </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol/cyproterone_acetate" title="Ethinylestradiol/cyproterone acetate">Ethinylestradiol/cyproterone acetate</a></td> <td>4.27 (3.57–5.11)* </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Notes: (1) <a href="/wiki/Nested_case%E2%80%93control_study" title="Nested case–control study">Nested case–control studies</a> (2015, 2019) based on data from the <a href="/wiki/QResearch" title="QResearch">QResearch</a> and <a href="/wiki/Clinical_Practice_Research_Datalink" title="Clinical Practice Research Datalink">Clinical Practice Research Datalink</a> (CPRD) databases. (2) <a href="/wiki/Bioidentical_hormone_therapy" class="mw-redirect" title="Bioidentical hormone therapy">Bioidentical</a> <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> was not included, but is known to be associated with no additional risk relative to estrogen alone. Footnotes: * = <a href="/wiki/Statistical_significance" title="Statistical significance">Statistically significant</a> (p < 0.01). Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Long-term_effects">Long-term effects</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=21" title="Edit section: Long-term effects">edit</a>]</div> Uncommon but serious possible side effects of estrogens associated with long-term therapy may include <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, <a href="/wiki/Uterine_cancer" title="Uterine cancer">uterine cancer</a>, <a href="/wiki/Stroke" title="Stroke">stroke</a>, <a href="/wiki/Heart_attack" class="mw-redirect" title="Heart attack">heart attack</a>, <a href="/wiki/Blood_clot" class="mw-redirect" title="Blood clot">blood clots</a>, <a href="/wiki/Dementia" title="Dementia">dementia</a>, <a href="/wiki/Gallbladder_disease" title="Gallbladder disease">gallbladder disease</a>, and <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</a>.<a href="#cite_note-Estrace-FDA-34">[34]</a> Warning signs of these serious side effects include <a href="/wiki/Breast_lump" class="mw-redirect" title="Breast lump">breast lumps</a>, unusual vaginal bleeding, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, <a href="/wiki/Faintness" class="mw-redirect" title="Faintness">faintness</a>, changes in <a href="/wiki/Speech" title="Speech">speech</a>, severe headaches, <a href="/wiki/Chest_pain" title="Chest pain">chest pain</a>, <a href="/wiki/Shortness_of_breath" title="Shortness of breath">shortness of breath</a>, <a href="/wiki/Pain" title="Pain">pain</a> in the legs, changes in <a href="/wiki/Visual_perception" title="Visual perception">vision</a>, and <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>.<a href="#cite_note-Estrace-FDA-34">[34]</a> Due to health risks observed with the combination of <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a> and <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a> in the <a href="/wiki/Women%27s_Health_Initiative" title="Women's Health Initiative">Women's Health Initiative</a> (WHI) studies (see below), the US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) label for Estrace (estradiol) advises that estrogens should be used in menopausal hormone therapy only for the shortest time possible and at the lowest effective dose.<a href="#cite_note-Estrace_Label-20">[20]</a> While the FDA states that is unknown if these risks generalize to estradiol (alone or in combination with progesterone or a progestin), it advises that in the absence of comparable data, the risks should be assumed to be similar.<a href="#cite_note-Estrace_Label-20">[20]</a> When used to treat menopausal symptoms, the FDA recommends that discontinuation of estradiol should be attempted every three to six months via a gradual dose taper.<a href="#cite_note-Estrace_Label-20">[20]</a> The combination of bioidentical <a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">transdermal</a> or <a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">vaginal</a> estradiol and <a href="/wiki/Oral_administration" title="Oral administration">oral</a> or vaginal <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> appears to be a safer form of hormone therapy than the combination of oral conjugated estrogens and medroxyprogesterone acetate and may not share the same health risks.<a href="#cite_note-pmid18775609-134">[130]</a><a href="#cite_note-pmid19179815-135">[131]</a><a href="#cite_note-pmid21464264-136">[132]</a><a href="#cite_note-pmid22432810-137">[133]</a><a href="#cite_note-pmid22432811-138">[134]</a><a href="#cite_note-pmid23848491-139">[135]</a><a href="#cite_note-pmid24398406-140">[136]</a><a href="#cite_note-pmid28301216-141">[137]</a><a href="#cite_note-pmid29526116-129">[125]</a> Advantages may include reduced or no risk of <a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">venous thromboembolism</a>, <a href="/wiki/Cardiovascular_disease" title="Cardiovascular disease">cardiovascular disease</a>, and <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, among others.<a href="#cite_note-pmid18775609-134">[130]</a><a href="#cite_note-pmid19179815-135">[131]</a><a href="#cite_note-pmid21464264-136">[132]</a><a href="#cite_note-pmid22432810-137">[133]</a><a href="#cite_note-pmid22432811-138">[134]</a><a href="#cite_note-pmid23848491-139">[135]</a><a href="#cite_note-pmid24398406-140">[136]</a><a href="#cite_note-pmid28301216-141">[137]</a><a href="#cite_note-pmid29526116-129">[125]</a> <table class="wikitable mw-collapsible mw-collapsed" style="font-size: small; margin-left: auto; margin-right: auto; border: none; text-align:center;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Results_of_the_Women%27s_Health_Initiative_menopausal_hormone_therapy_randomized_controlled_trials" title="Template:Results of the Women's Health Initiative menopausal hormone therapy randomized controlled trials"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Results_of_the_Women%27s_Health_Initiative_menopausal_hormone_therapy_randomized_controlled_trials" title="Template talk:Results of the Women's Health Initiative menopausal hormone therapy randomized controlled trials"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Results_of_the_Women%27s_Health_Initiative_menopausal_hormone_therapy_randomized_controlled_trials" title="Special:EditPage/Template:Results of the Women's Health Initiative menopausal hormone therapy randomized controlled trials"><abbr title="Edit this template">e</abbr></a></li></ul></div> Results of the Women's Health Initiative (WHI) menopausal hormone therapy randomized controlled trials </caption> <tbody><tr> <th rowspan="2">Clinical outcome </th> <th rowspan="2">Hypothesized effect on risk </th> <th colspan="3"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a> and <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a> (<a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens"><abbr title="conjugated estrogens">CEs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip conjugated estrogens 0.625 mg/day p.o. + <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate"><abbr title="medroxyprogesterone acetate">MPA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip medroxyprogesterone acetate 2.5 mg/day p.o.) (n = 16,608, with uterus, 5.2–5.6 years follow up) </th> <th colspan="3"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a> alone (<a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens"><abbr title="Conjugated estrogens">CEs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Conjugated estrogens 0.625 mg/day p.o.) (n = 10,739, no uterus, 6.8–7.1 years follow up) </th></tr> <tr> <th width="100px"><a href="/wiki/Hazard_ratio" title="Hazard ratio"><abbr title="Hazard ratio">HR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Hazard ratio </th> <th width="100px">95% <a href="/wiki/Confidence_interval" title="Confidence interval"><abbr title="Confidence interval">CI</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Confidence interval </th> <th width="100px"><a href="/wiki/Attributable_risk" class="mw-redirect" title="Attributable risk"><abbr title="Attributable risk">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Attributable risk </th> <th width="100px"><a href="/wiki/Hazard_ratio" title="Hazard ratio"><abbr title="Hazard ratio">HR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Hazard ratio </th> <th width="100px">95% <a href="/wiki/Confidence_interval" title="Confidence interval"><abbr title="Confidence interval">CI</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Confidence interval </th> <th width="100px"><a href="/wiki/Attributable_risk" class="mw-redirect" title="Attributable risk"><abbr title="Attributable risk">AR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Attributable risk </th></tr> <tr> <td style="text-align: left;"><a href="/wiki/Coronary_heart_disease" class="mw-redirect" title="Coronary heart disease">Coronary heart disease</a> </td> <td>Decreased </td> <td style="background: #ffcccb;">1.24 </td> <td>1.00–1.54 </td> <td style="background: #ffcccb;">+6 / 10,000 PYs </td> <td style="background: #cffbd4;">0.95 </td> <td>0.79–1.15 </td> <td style="background: #cffbd4;">−3 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Stroke" title="Stroke">Stroke</a> </td> <td>Decreased </td> <td style="background: #ffcccb;">1.31 </td> <td>1.02–1.68 </td> <td style="background: #ffcccb;">+8 / 10,000 PYs </td> <td style="background: #ffcccb;">1.37 </td> <td>1.09–1.73 </td> <td style="background: #ffcccb;">+12 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">Pulmonary embolism</a> </td> <td>Increased </td> <td style="background: #ffcccb;">2.13 </td> <td>1.45–3.11 </td> <td style="background: #ffcccb;">+10 / 10,000 PYs </td> <td style="background: #ffcccb;">1.37 </td> <td>0.90–2.07 </td> <td style="background: #ffcccb;">+4 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Venous_thromboembolism" class="mw-redirect" title="Venous thromboembolism">Venous thromboembolism</a> </td> <td>Increased </td> <td style="background: #ffcccb;">2.06 </td> <td>1.57–2.70 </td> <td style="background: #ffcccb;">+18 / 10,000 PYs </td> <td style="background: #ffcccb;">1.32 </td> <td>0.99–1.75 </td> <td style="background: #ffcccb;">+8 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Breast_cancer" title="Breast cancer">Breast cancer</a> </td> <td>Increased </td> <td style="background: #ffcccb;">1.24 </td> <td>1.02–1.50 </td> <td style="background: #ffcccb;">+8 / 10,000 PYs </td> <td style="background: #cffbd4;">0.80 </td> <td>0.62–1.04 </td> <td style="background: #cffbd4;">−6 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Colorectal_cancer" title="Colorectal cancer">Colorectal cancer</a> </td> <td>Decreased </td> <td style="background: #cffbd4;">0.56 </td> <td>0.38–0.81 </td> <td style="background: #cffbd4;">−7 / 10,000 PYs </td> <td style="background: #ffcccb;">1.08 </td> <td>0.75–1.55 </td> <td style="background: #ffcccb;">+1 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Endometrial_cancer" title="Endometrial cancer">Endometrial cancer</a> </td> <td>– </td> <td style="background: #cffbd4;">0.81 </td> <td>0.48–1.36 </td> <td style="background: #cffbd4;">−1 / 10,000 PYs </td> <td>– </td> <td>– </td> <td>– </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Hip_fracture" title="Hip fracture">Hip fractures</a> </td> <td>Decreased </td> <td style="background: #cffbd4;">0.67 </td> <td>0.47–0.96 </td> <td style="background: #cffbd4;">−5 / 10,000 PYs </td> <td style="background: #cffbd4;">0.65 </td> <td>0.45–0.94 </td> <td style="background: #cffbd4;">−7 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;">Total <a href="/wiki/Bone_fracture" title="Bone fracture">fractures</a> </td> <td>Decreased </td> <td style="background: #cffbd4;">0.76 </td> <td>0.69–0.83 </td> <td style="background: #cffbd4;">−47 / 10,000 PYs </td> <td style="background: #cffbd4;">0.71 </td> <td>0.64–0.80 </td> <td style="background: #cffbd4;">−53 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;">Total <a href="/wiki/Mortality_rate" title="Mortality rate">mortality</a> </td> <td>Decreased </td> <td style="background: #cffbd4;">0.98 </td> <td>0.82–1.18 </td> <td style="background: #cffbd4;">−1 / 10,000 PYs </td> <td style="background: #ffcccb;">1.04 </td> <td>0.91–1.12 </td> <td style="background: #ffcccb;">+3 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;">Global index </td> <td>– </td> <td style="background: #ffcccb;">1.15 </td> <td>1.03–1.28 </td> <td style="background: #ffcccb;">+19 / 10,000 PYs </td> <td style="background: #ffcccb;">1.01 </td> <td>1.09–1.12 </td> <td style="background: #ffcccb;">+2 / 10,000 PYs </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Diabetes" title="Diabetes">Diabetes</a> </td> <td>– </td> <td style="background: #cffbd4;">0.79 </td> <td>0.67–0.93 </td> <td> </td> <td style="background: #cffbd4;">0.88 </td> <td>0.77–1.01 </td> <td> </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Gallbladder_disease" title="Gallbladder disease">Gallbladder disease</a> </td> <td>Increased </td> <td style="background: #ffcccb;">1.59 </td> <td>1.28–1.97 </td> <td> </td> <td style="background: #ffcccb;">1.67 </td> <td>1.35–2.06 </td> <td> </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Stress_incontinence" title="Stress incontinence">Stress incontinence</a> </td> <td>– </td> <td style="background: #ffcccb;">1.87 </td> <td>1.61–2.18 </td> <td> </td> <td style="background: #ffcccb;">2.15 </td> <td>1.77–2.82 </td> <td> </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Urge_incontinence" class="mw-redirect" title="Urge incontinence">Urge incontinence</a> </td> <td>– </td> <td style="background: #ffcccb;">1.15 </td> <td>0.99–1.34 </td> <td> </td> <td style="background: #ffcccb;">1.32 </td> <td>1.10–1.58 </td> <td> </td></tr> <tr> <td style="text-align: left;"><a href="/wiki/Peripheral_artery_disease" title="Peripheral artery disease">Peripheral artery disease</a> </td> <td>– </td> <td style="background: #cffbd4;">0.89 </td> <td>0.63–1.25 </td> <td> </td> <td style="background: #ffcccb;">1.32 </td> <td>0.99–1.77 </td> <td> </td></tr> <tr> <td style="text-align: left;">Probable <a href="/wiki/Dementia" title="Dementia">dementia</a> </td> <td>Decreased </td> <td style="background: #ffcccb;">2.05 </td> <td>1.21–3.48 </td> <td> </td> <td style="background: #ffcccb;">1.49 </td> <td>0.83–2.66 </td> <td> </td></tr> <tr> <td colspan="8" style="width: 1px; background-color:#eaecf0; text-align: center;">Abbreviations: CEs = <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a>. MPA = <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>. p.o. = <a href="/wiki/Per_oral" class="mw-redirect" title="Per oral">per oral</a>. HR = <a href="/wiki/Hazard_ratio" title="Hazard ratio">hazard ratio</a>. AR = <a href="/wiki/Attributable_risk" class="mw-redirect" title="Attributable risk">attributable risk</a>. PYs = <a href="/wiki/Person%E2%80%93years" class="mw-redirect" title="Person–years">person–years</a>. CI = <a href="/wiki/Confidence_interval" title="Confidence interval">confidence interval</a>. Notes: <a href="/wiki/Sample_size" class="mw-redirect" title="Sample size">Sample sizes</a> (n) include <a href="/wiki/Placebo" title="Placebo">placebo</a> recipients, which were about half of patients. "Global index" is defined for each woman as the time to earliest diagnosis for <a href="/wiki/Coronary_heart_disease" class="mw-redirect" title="Coronary heart disease">coronary heart disease</a>, <a href="/wiki/Stroke" title="Stroke">stroke</a>, <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a>, <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, <a href="/wiki/Colorectal_cancer" title="Colorectal cancer">colorectal cancer</a>, <a href="/wiki/Endometrial_cancer" title="Endometrial cancer">endometrial cancer</a> (estrogen plus progestogen group only), <a href="/wiki/Hip_fracture" title="Hip fracture">hip fractures</a>, and <a href="/wiki/Death" title="Death">death</a> from other causes. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=22" title="Edit section: Overdose">edit</a>]</div> Estrogens are relatively safe in <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a>.<a href="#cite_note-pmid10230677-106">[102]</a> During <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>, levels of estradiol increase to very high concentrations that are as much as 100-fold normal levels.<a href="#cite_note-Becker2001-142">[138]</a><a href="#cite_note-Abbott2009-143">[139]</a><a href="#cite_note-Smith2001-144">[140]</a> In late pregnancy, the body produces and secretes approximately 100 mg of estrogens, including estradiol, <a href="/wiki/Estrone" title="Estrone">estrone</a>, and <a href="/wiki/Estriol" title="Estriol">estriol</a>, per day.<a href="#cite_note-Becker2001-142">[138]</a> Doses of estradiol of as high as 200 mg per day by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> for several weeks have been administered to humans in studies.<a href="#cite_note-pmid4890101-145">[141]</a><a href="#cite_note-pmid14236214-146">[142]</a> Serious <a href="/wiki/Adverse_effect" title="Adverse effect">adverse effects</a> have not been described following acute overdose of large doses of estrogen- and <a href="/wiki/Progestogen_(medication)" title="Progestogen (medication)">progestogen</a>-containing <a href="/wiki/Birth_control_pill" class="mw-redirect" title="Birth control pill">birth control pills</a> by small children.<a href="#cite_note-pmid10230677-106">[102]</a> <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">Symptoms</a> of estrogen overdosage 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/Vaginal_bleeding" title="Vaginal bleeding">vaginal bleeding</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-pmid2215269-107">[103]</a><a href="#cite_note-pmid10230677-106">[102]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=23" title="Edit section: Interactions">edit</a>]</div> <a href="/wiki/Enzyme_inducer" title="Enzyme inducer">Inducers</a> of <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> like <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> such as <a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">St. John's wort</a>, <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a>, <a href="/wiki/Carbamazepine" title="Carbamazepine">carbamazepine</a> and <a href="/wiki/Rifampicin" title="Rifampicin">rifampicin</a> decrease the circulating levels of estradiol by accelerating its <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>, whereas <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a> of cytochrome P450 enzymes like CYP3A4 such as <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a>, <a href="/wiki/Cimetidine" title="Cimetidine">cimetidine</a>,<a href="#cite_note-pmid11741520-147">[143]</a> <a href="/wiki/Clarithromycin" title="Clarithromycin">clarithromycin</a>, <a href="/wiki/Ketoconazole" title="Ketoconazole">ketoconazole</a>, <a href="/wiki/Itraconazole" title="Itraconazole">itraconazole</a>, <a href="/wiki/Ritonavir" title="Ritonavir">ritonavir</a> and <a href="/wiki/Grapefruit_juice" title="Grapefruit juice">grapefruit juice</a><a href="#cite_note-pmid7715468-148">[144]</a> may slow its metabolism resulting in increased levels of estradiol in the circulation.<a href="#cite_note-Estrace_Label-20">[20]</a> There is an interaction between estradiol and <a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">alcohol</a> such that alcohol considerably increases circulating levels of estradiol during oral estradiol therapy and also increases estradiol levels in normal premenopausal women and with parenteral estradiol therapy.<a href="#cite_note-Elsevier2002-149">[145]</a><a href="#cite_note-OettelSchillinger2012b-13">[13]</a><a href="#cite_note-pmid8940324-150">[146]</a><a href="#cite_note-pmid10397281-151">[147]</a> This appears to be due to a decrease in <a href="/wiki/Liver" title="Liver">hepatic</a> <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenase</a> <a href="/wiki/HSD17B2" title="HSD17B2">type 2</a> (17β-HSD2) activity and hence estradiol inactivation into estrone due to an alcohol-mediated increase in the ratio of <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NADH</a> to <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD</a> in the liver.<a href="#cite_note-pmid8940324-150">[146]</a><a href="#cite_note-pmid10397281-151">[147]</a> <a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a> may reduce the <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of high doses of oral estradiol.<a href="#cite_note-pmid29756046-152">[148]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=24" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=25" 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">Main article: <a href="/wiki/Pharmacodynamics_of_estradiol" title="Pharmacodynamics of estradiol">Pharmacodynamics of estradiol</a></div> Estradiol 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> (ERs), the <a href="/wiki/Estrogen_receptor_alpha" title="Estrogen receptor alpha"><abbr title="estrogen receptor alpha">ERα</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 alpha and <a href="/wiki/Estrogen_receptor_beta" title="Estrogen receptor beta"><abbr title="estrogen receptor beta">ERβ</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 beta.<a href="#cite_note-pmid16112947-11">[11]</a> It is also an agonist of <a href="/wiki/Membrane_estrogen_receptor" title="Membrane estrogen receptor">membrane estrogen receptors</a> (mERs), including the <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, <a href="/wiki/Gq-coupled_membrane_estrogen_receptor" class="mw-redirect" title="Gq-coupled membrane estrogen receptor"><abbr title="Gq-coupled membrane estrogen receptor">Gq-mER</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 Gq-coupled membrane estrogen receptor, <a href="/wiki/ER-X" title="ER-X">ER-X</a>, and <a href="/wiki/ERx" title="ERx">ERx</a>.<a href="#cite_note-pmid23756388-153">[149]</a><a href="#cite_note-pmid24530924-154">[150]</a> Estradiol is highly <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> for these ERs and mERs, and does not interact importantly with other <a href="/wiki/Steroid_hormone_receptor" title="Steroid hormone receptor">steroid hormone receptors</a>.<a href="#cite_note-pmid359134-155">[151]</a><a href="#cite_note-pmid3695484-156">[152]</a><a href="#cite_note-pmid7421203-157">[153]</a> It is far more <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potent</a> as an estrogen than are other <a href="/wiki/Bioidentical" class="mw-redirect" title="Bioidentical">bioidentical</a> estrogens like <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a> and <a href="/wiki/Estriol_(medication)" title="Estriol (medication)">estriol</a>.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-Labhart2012p548-158">[154]</a> Given by <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous injection</a> in mice, estradiol is about 10-fold more potent than estrone and about 100-fold more potent than estriol.<a href="#cite_note-Labhart2012p548-158">[154]</a> The ERs are expressed widely throughout the body, including in the <a href="/wiki/Breast" title="Breast">breasts</a>, <a href="/wiki/Uterus" title="Uterus">uterus</a>, <a href="/wiki/Vagina" title="Vagina">vagina</a>, <a href="/wiki/Adipose_tissue" title="Adipose tissue">fat</a>, <a href="/wiki/Skin" title="Skin">skin</a>, <a href="/wiki/Bone" title="Bone">bone</a>, <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Pituitary_gland" title="Pituitary gland">pituitary gland</a>, <a href="/wiki/Hypothalamus" title="Hypothalamus">hypothalamus</a>, and other parts of the <a href="/wiki/Brain" title="Brain">brain</a>.<a href="#cite_note-Parl2000-27">[27]</a> In accordance, estradiol has numerous effects throughout the body.<a href="#cite_note-Parl2000-27">[27]</a><a href="#cite_note-Dietrich2014-159">[155]</a><a href="#cite_note-ThornhillGangestad2008-160">[156]</a><a href="#cite_note-pmid12762829-161">[157]</a><a href="#cite_note-Hayward2003-162">[158]</a><a href="#cite_note-MelmedPolonsky2015-163">[159]</a><a href="#cite_note-JonesLopez2013-164">[160]</a><a href="#cite_note-OettelSchillinger2012b-13">[13]</a><a href="#cite_note-HongHolland2010-53">[53]</a><a href="#cite_note-Sloane2002-165">[161]</a><a href="#cite_note-KingBrucker2010-166">[162]</a><a href="#cite_note-Lobo2007-167">[163]</a><a href="#cite_note-WarshawskyJr.2005-168">[164]</a> Among other effects, estradiol produces <a href="/wiki/Breast_development" title="Breast development">breast development</a>, <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a>, changes in the <a href="/wiki/Female_reproductive_system" title="Female reproductive system">female reproductive system</a>, changes in <a href="/wiki/Liver_protein_synthesis" class="mw-redirect" title="Liver protein synthesis">liver protein synthesis</a>, and changes in <a href="/wiki/Brain" title="Brain">brain</a> function.<a href="#cite_note-MelmedPolonsky2015-163">[159]</a><a href="#cite_note-JonesLopez2013-164">[160]</a><a href="#cite_note-OettelSchillinger2012b-13">[13]</a><a href="#cite_note-HongHolland2010-53">[53]</a><a href="#cite_note-Sloane2002-165">[161]</a><a href="#cite_note-KingBrucker2010-166">[162]</a><a href="#cite_note-Lobo2007-167">[163]</a><a href="#cite_note-WarshawskyJr.2005-168">[164]</a> The effects of estradiol can influence health in both positive and negative ways.<a href="#cite_note-pmid16112947-11">[11]</a> In addition to the aforementioned effects, estradiol has <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> effects due to its estrogenic activity, and can inhibit <a href="/wiki/Ovulation" title="Ovulation">ovulation</a> and suppress <a href="/wiki/Gonad" title="Gonad">gonadal</a> <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormone</a> production.<a href="#cite_note-JonesLopez2013-164">[160]</a><a href="#cite_note-OettelSchillinger2012b-13">[13]</a><a href="#cite_note-HongHolland2010-53">[53]</a><a href="#cite_note-pmid14532759-54">[54]</a><a href="#cite_note-CossJones2012-55">[55]</a><a href="#cite_note-pmid3242384-25">[25]</a><a href="#cite_note-Ockrim_2003-26">[26]</a> At sufficiently high dosages, estradiol is a powerful antigonadotropin, capable of suppressing testosterone levels into the castrate/female range in men.<a href="#cite_note-HongHolland2010-53">[53]</a><a href="#cite_note-pmid14532759-54">[54]</a><a href="#cite_note-CossJones2012-55">[55]</a><a href="#cite_note-pmid3242384-25">[25]</a><a href="#cite_note-Ockrim_2003-26">[26]</a> There are differences between estradiol and other estrogens, such as non-bioidentical estrogens like natural <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a> and synthetic estrogens like <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> and <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>, with implications for <a href="/wiki/Pharmacodynamics" title="Pharmacodynamics">pharmacodynamics</a> and <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> as well as <a href="/wiki/Efficacy" title="Efficacy">efficacy</a>, <a href="/wiki/Tolerability" title="Tolerability">tolerability</a>, and <a href="/wiki/Drug_safety" class="mw-redirect" title="Drug safety">safety</a>.<a href="#cite_note-pmid16112947-11">[11]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=26" 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">Main article: <a href="/wiki/Pharmacokinetics_of_estradiol" title="Pharmacokinetics of estradiol">Pharmacokinetics of estradiol</a></div> Estradiol can be taken by a variety of different <a href="/wiki/Routes_of_administration" class="mw-redirect" title="Routes of administration">routes of administration</a>.<a href="#cite_note-pmid16112947-11">[11]</a> These include <a href="/wiki/Oral_administration" title="Oral administration">oral</a>, <a href="/wiki/Buccal_administration" title="Buccal administration">buccal</a>, <a href="/wiki/Sublingual_administration" title="Sublingual administration">sublingual</a>, <a href="/wiki/Intranasal_administration" class="mw-redirect" title="Intranasal administration">intranasal</a>, <a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">transdermal</a> (<a href="/wiki/Gel" title="Gel">gels</a>, <a href="/wiki/Cream_(pharmacy)" title="Cream (pharmacy)">creams</a>, <a href="/wiki/Transdermal_patch" title="Transdermal patch">patches</a>), <a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">vaginal</a> (<a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a>, creams, <a href="/wiki/Vaginal_ring" title="Vaginal ring">rings</a>, <a href="/wiki/Vaginal_suppository" class="mw-redirect" title="Vaginal suppository">suppositories</a>), <a href="/wiki/Rectal_administration" title="Rectal administration">rectal</a>, by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular</a> or <a href="/wiki/Subcutaneous_injection" class="mw-redirect" title="Subcutaneous injection">subcutaneous</a> <a href="/wiki/Injection_(medicine)" title="Injection (medicine)">injection</a> (in <a href="/wiki/Oil" title="Oil">oil</a> or <a href="/wiki/Aqueous" class="mw-redirect" title="Aqueous">aqueous</a>), and as a <a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant">subcutaneous implant</a>.<a href="#cite_note-pmid16112947-11">[11]</a> The <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of estradiol, including its <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a>, <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>, <a href="/wiki/Biological_half-life" title="Biological half-life">biological half-life</a>, and other parameters, differ by route of administration.<a href="#cite_note-pmid16112947-11">[11]</a> Likewise, the <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> of estradiol, and its local effects in certain <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>, most importantly the <a href="/wiki/Liver" title="Liver">liver</a>, differ by route of administration as well.<a href="#cite_note-pmid16112947-11">[11]</a> In particular, the oral route is subject to a high <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first-pass effect</a>, which results in high levels of estradiol and consequent estrogenic effects in the liver and low potency due to first-pass hepatic and <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestinal</a> metabolism into <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> like <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a> and <a href="/wiki/Estrogen_conjugate" title="Estrogen conjugate">estrogen conjugates</a>.<a href="#cite_note-pmid16112947-11">[11]</a> Conversely, this is not the case for <a href="/wiki/Parenteral" class="mw-redirect" title="Parenteral">parenteral</a> (non-oral) routes, which bypass the intestines and liver.<a href="#cite_note-pmid16112947-11">[11]</a> Different estradiol routes and dosages can achieve widely varying circulating estradiol levels.<a href="#cite_note-pmid16112947-11">[11]</a> For purposes of comparison with normal physiological circumstances, menstrual cycle circulating levels of estradiol in premenopausal women are 40 pg/mL in the early follicular phase, 250 pg/mL at the middle of the cycle, and 100 pg/mL during the mid-luteal phase.<a href="#cite_note-Lobo2007-167">[163]</a> Mean integrated levels of circulating estradiol in premenopausal women across the whole menstrual cycle have been reported to be in the range of 80 and 150 pg/mL, according to some sources.<a href="#cite_note-NotelovitzKeep2012-169">[165]</a><a href="#cite_note-ChristianSchoultz1994-170">[166]</a><a href="#cite_note-MüllerMacLeod2012-171">[167]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=27" title="Edit section: Chemistry">edit</a>]</div> <table role="presentation" cellpadding="0" style="border-spacing:0; clear:right; float:right;"> <tbody><tr> <td><div class="thumb tright"> <div class="thumbinner" style="width:396px;"> <div style="clear: both; font-weight: bold; font-size: 106.4%; text-align: center; background-color: light-dark(aliceblue,var(--background-color-neutral)); color:var(--color-base,light-dark(#202122,#eaecf0)); margin-bottom:3px;"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Chemical_structures_of_major_endogenous_estrogens_medication_version" title="Template:Chemical structures of major endogenous estrogens medication version"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemical_structures_of_major_endogenous_estrogens_medication_version" title="Template talk:Chemical structures of major endogenous estrogens medication version"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemical_structures_of_major_endogenous_estrogens_medication_version" title="Special:EditPage/Template:Chemical structures of major endogenous estrogens medication version"><abbr title="Edit this template">e</abbr></a></li></ul></div> Structures of major endogenous estrogens</div> <div class="skin-invert" style="position:relative; width:394px; height:260px; overflow:hidden; border:solid #ccc 1px; background-color:white;"> <div style="left:0px; top:0px; width:394px; position:absolute"> <img alt="Chemical structures of major endogenous estrogens" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Chemical_structures_of_major_endogenous_estrogens_no_labels.png/394px-Chemical_structures_of_major_endogenous_estrogens_no_labels.png" decoding="async" width="394" height="262" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Chemical_structures_of_major_endogenous_estrogens_no_labels.png/591px-Chemical_structures_of_major_endogenous_estrogens_no_labels.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Chemical_structures_of_major_endogenous_estrogens_no_labels.png/788px-Chemical_structures_of_major_endogenous_estrogens_no_labels.png 2x" data-file-width="2560" data-file-height="1700" /> </div> <div style="text-align:center; font-size:14px; line-height:110%"> <div style="background-color:transparent; color:black"><div id="annotation_53x107" style="position:absolute; left:53px; top:107px; line-height:110%;"><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a> (E1)</div> <div id="annotation_251x107" style="position:absolute; left:251px; top:107px; line-height:110%;">Estradiol (E2)</div> <div id="annotation_55x235" style="position:absolute; left:55px; top:235px; line-height:110%;"><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a> (E3)</div> <div id="annotation_253x235" style="position:absolute; left:253px; top:235px; line-height:110%;"><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a> (E4)</div></div> </div> </div> <div class="thumbcaption" style="clear:left"><div style="float:left;margin-right:0.5em"><img alt="The image above contains clickable links" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/20px-Interactive_icon.svg.png" decoding="async" width="18" height="27" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Interactive_icon.svg/40px-Interactive_icon.svg.png 1.5x" data-file-width="133" data-file-height="200" /></div>Note the <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl</a> (–OH) <a href="/wiki/Functional_group" title="Functional group">groups</a>: estrone (E1) has one, estradiol (E2) has two, estriol (E3) has three, and estetrol (E4) has four.</div> </div> </div> </td></tr></tbody></table> Estradiol is a <a href="/wiki/Natural_product" title="Natural product">naturally occurring</a> <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a>.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-RizkSallam2012-172">[168]</a> It is also known as 17β-estradiol (to distinguish it from <a href="/wiki/17%CE%B1-estradiol" class="mw-redirect" title="17α-estradiol">17α-estradiol</a>) or as estra-1,3,5(10)-triene-3,17β-diol.<a href="#cite_note-Elks2014-173">[169]</a><a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-pmid16112947-11">[11]</a> It has two <a href="/wiki/Hydroxyl_group" class="mw-redirect" title="Hydroxyl group">hydroxyl groups</a>, one at the C3 position and the other at the C17β position, as well as three <a href="/wiki/Double_bond" title="Double bond">double bonds</a> in the A <a href="/wiki/Ring_(chemistry)" title="Ring (chemistry)">ring</a> (the <a href="/wiki/Estra-1,3,5(10)-triene" class="mw-redirect" title="Estra-1,3,5(10)-triene">estra-1,3,5(10)-triene</a> core).<a href="#cite_note-RizkSallam2012-172">[168]</a><a href="#cite_note-pmid18744783-175">[171]</a> Due to its two hydroxyl groups, estradiol is often abbreviated as E2.<a href="#cite_note-RizkSallam2012-172">[168]</a> The structurally related estrogens, estrone (E1), estriol (E3), and <a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">estetrol</a> (E4) have one, three, and four hydroxyl groups, respectively.<a href="#cite_note-RizkSallam2012-172">[168]</a><a href="#cite_note-GivensAnderson1981-176">[172]</a> <div class="mw-heading mw-heading3"><h3 id="Hemihydrate">Hemihydrate</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=28" title="Edit section: Hemihydrate">edit</a>]</div> A <a href="/wiki/Hemihydrate" title="Hemihydrate">hemihydrate</a> form of estradiol, estradiol hemihydrate, is widely used medically under a large number of brand names similarly to estradiol.<a href="#cite_note-IndexNominum2000-174">[170]</a> In terms of <a href="/wiki/Biological_activity" title="Biological activity">activity</a> and <a href="/wiki/Bioequivalence" title="Bioequivalence">bioequivalence</a>, estradiol and its hemihydrate are identical, with the only disparities being an approximate 3% difference in <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> by weight (due to the presence of <a href="/wiki/Water" title="Water">water</a> molecules in the hemihydrate form of the substance) and a slower rate of <a href="/wiki/Drug_delivery" title="Drug delivery">release</a> with certain <a href="/wiki/Pharmaceutical_formulation" title="Pharmaceutical formulation">formulations</a> of the hemihydrate.<a href="#cite_note-HumansOrganization2007-177">[173]</a><a href="#cite_note-DesaiLee2007-178">[174]</a> This is because estradiol hemihydrate is more <a href="/wiki/Hydrate" title="Hydrate">hydrated</a> than <a href="/wiki/Anhydrous" title="Anhydrous">anhydrous</a> estradiol, and for this reason, is more <a href="/wiki/Solubility" title="Solubility">insoluble</a> in water in comparison, which results in slower <a href="/wiki/Absorption_(chemistry)" title="Absorption (chemistry)">absorption</a> rates with specific formulations of the drug such as vaginal tablets.<a href="#cite_note-DesaiLee2007-178">[174]</a> Estradiol hemihydrate has also been shown to result in less <a href="/wiki/Bioavailability" title="Bioavailability">systemic absorption</a> as a vaginal tablet formulation relative to other topical estradiol formulations such as vaginal creams.<a href="#cite_note-Wang-ChengNeuner2007-179">[175]</a> Estradiol hemihydrate is used in place of estradiol in some estradiol products.<a href="#cite_note-Drugs@FDA1-180">[176]</a><a href="#cite_note-LeeDesai2007-181">[177]</a><a href="#cite_note-Nursing2013-182">[178]</a> <div class="mw-heading mw-heading3"><h3 id="Derivatives">Derivatives</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=29" title="Edit section: Derivatives">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#Estradiol_derivatives" title="List of estrogens">List of estrogens § Estradiol derivatives</a>, <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> A variety of C17β and/or C3 <a href="/wiki/Ester" title="Ester">ester</a> <a href="/wiki/Prodrug" title="Prodrug">prodrugs</a> of estradiol, such as <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_dipropionate" title="Estradiol dipropionate">estradiol dipropionate</a>, <a href="/wiki/Estradiol_enantate" title="Estradiol enantate">estradiol enantate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, and <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a> (an estradiol ester in <a href="/wiki/Polymer" title="Polymer">polymeric</a> form), among many others, have been developed and introduced for medical use as estrogens.<a href="#cite_note-Elks2014-173">[169]</a><a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid1231448-183">[179]</a> <a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a> is also an estradiol ester, but with a <a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">nitrogen mustard</a> <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> attached, and is used as a <a href="/wiki/Cytostatic_antineoplastic_agent" class="mw-redirect" title="Cytostatic antineoplastic agent">cytostatic antineoplastic agent</a> in the treatment of prostate cancer.<a href="#cite_note-Elks2014-173">[169]</a><a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-pmid21756277-184">[180]</a> <a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a> and <a href="/wiki/Promestriene" title="Promestriene">promestriene</a> are <a href="/wiki/Ether" title="Ether">ether</a> prodrugs of estradiol that have been introduced for medical use as estrogens as well, although they are little known and rarely used.<a href="#cite_note-Elks2014-173">[169]</a><a href="#cite_note-IndexNominum2000-174">[170]</a> <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">Synthetic</a> derivatives of estradiol used as estrogens include <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>, <a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">ethinylestradiol sulfonate</a>, <a href="/wiki/Mestranol" title="Mestranol">mestranol</a>, <a href="/wiki/Methylestradiol" title="Methylestradiol">methylestradiol</a>, <a href="/wiki/Moxestrol" title="Moxestrol">moxestrol</a>, and <a href="/wiki/Quinestrol" title="Quinestrol">quinestrol</a>, all of which are 17α-<a href="/wiki/Substituent" title="Substituent">substituted</a> estradiol derivatives.<a href="#cite_note-Elks2014-173">[169]</a><a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-pmid16112947-11">[11]</a> Synthetic derivatives of estradiol used in <a href="/wiki/Scientific_research" class="mw-redirect" title="Scientific research">scientific research</a> include <a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a> and <a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a>.<a href="#cite_note-VaudryKah2018-185">[181]</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>Estradiol</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/40px-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/60px-Estradiol_3-acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_3-acetate.svg/120px-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/40px-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/60px-Estradiol_benzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_benzoate.svg/120px-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><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></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/40px-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/60px-Estradiol_butyrate_benzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_butyrate_benzoate.svg/120px-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/40px-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/60px-Estradiol_dienanthate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Estradiol_dienanthate.svg/120px-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/40px-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/60px-Estradiol_stearate_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/Estradiol_stearate_structure.svg/120px-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/40px-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/60px-Estramustine_phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/120px-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_(medication)&action=edit&section=30" title="Edit section: History">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#History" title="Estradiol">Estradiol § History</a></div> Estradiol was first discovered and <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> in 1933 via <a href="/wiki/Redox" title="Redox">reduction</a> of <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a>.<a href="#cite_note-LauritzenStudd2005-28">[28]</a> Subsequently, estradiol was isolated for the first time in 1935.<a href="#cite_note-Parl2000-27">[27]</a><a href="#cite_note-ShoupeHaseltine2012-186">[182]</a> It was also originally known as dihydroxyestrin, dihydrofolliculin, or alpha-estradiol.<a href="#cite_note-pmid18744783-175">[171]</a><a href="#cite_note-pmid18746057-187">[183]</a> Estradiol was first introduced for medical use, in the form of <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, a short-acting <a href="/wiki/Ester" title="Ester">ester</a> <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of estradiol administered by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a> in <a href="/wiki/Oil_solution" class="mw-redirect" title="Oil solution">oil solution</a>, under the brand name Progynon B in 1933.<a href="#cite_note-Kaufman1933-29">[29]</a><a href="#cite_note-Buschbeck1934-30">[30]</a><a href="#cite_note-Biskind1935-31">[31]</a><a href="#cite_note-Novak1935-188">[184]</a> Estradiol itself was also marketed in the 1930s and 1940s in the form of <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a> and <a href="/wiki/Solution_(chemistry)" title="Solution (chemistry)">solutions</a>, <a href="/wiki/Vaginal_administration" class="mw-redirect" title="Vaginal administration">vaginal</a> <a href="/wiki/Suppository" title="Suppository">suppositories</a>, and <a href="/wiki/Topical_administration" class="mw-redirect" title="Topical administration">topical</a> <a href="/wiki/Ointment" class="mw-redirect" title="Ointment">ointments</a> under a variety of brand names including Dimenformon, Gynoestryl, Ovocyclin, Progynon, and Progynon DH.<a href="#cite_note-Greene1941-189">[185]</a><a href="#cite_note-pmid18744783-175">[171]</a><a href="#cite_note-pmid29648134-190">[186]</a><a href="#cite_note-pmid18746057-187">[183]</a><a href="#cite_note-Fluhmann1944-191">[187]</a><a href="#cite_note-pmid29646930-192">[188]</a><a href="#cite_note-JAMA1943-193">[189]</a> Marketed vaginal estradiol suppositories were also used <a href="/wiki/Rectal_administration" title="Rectal administration">rectally</a>.<a href="#cite_note-Freed1941-194">[190]</a> <a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">Estradiol dipropionate</a>, another short-acting ester of estradiol in oil solution for use by intramuscular injection, was marketed under the brand name Di-Ovocylin by 1939.<a href="#cite_note-DorrGreene1939-195">[191]</a><a href="#cite_note-Greene1941-189">[185]</a> In contrast to estrone, estradiol was never marketed in oil solution for intramuscular injection.<a href="#cite_note-pmid13359169-196">[192]</a><a href="#cite_note-JAMA1943-193">[189]</a><a href="#cite_note-pmid15390574-197">[193]</a><a href="#cite_note-NNR1949a-198">[194]</a><a href="#cite_note-Greene1941-189">[185]</a><a href="#cite_note-pmid18744783-175">[171]</a><a href="#cite_note-pmid29648134-190">[186]</a><a href="#cite_note-pmid18746057-187">[183]</a><a href="#cite_note-Fluhmann1944-191">[187]</a><a href="#cite_note-pmid29646930-192">[188]</a> This is attributable to its short duration of action and the availability of longer-acting estradiol esters like estradiol benzoate and estradiol dipropionate.<a href="#cite_note-pmid13359169-196">[192]</a><a href="#cite_note-Reifenstein1944-199">[195]</a> Delivery of estrogens by <a href="/wiki/Nasal_spray" title="Nasal spray">nasal spray</a> was studied in 1929,<a href="#cite_note-Novak1935-188">[184]</a><a href="#cite_note-Paul_Pratt1932-200">[196]</a> and an estradiol nasal spray for local use was marketed by Schering under the brand name Progynon DH Nasal Spray by 1941.<a href="#cite_note-Schering1941-201">[197]</a><a href="#cite_note-Howard1949-202">[198]</a> <a href="/wiki/Sublingual_administration" title="Sublingual administration">Sublingual administration</a> of estradiol was first described in the early 1940s.<a href="#cite_note-Walton1944-203">[199]</a><a href="#cite_note-Corner1944-204">[200]</a><a href="#cite_note-LisserGordan1950-205">[201]</a> <a href="/wiki/Buccal_administration" title="Buccal administration">Buccal</a> estradiol tablets were marketed by <a href="/wiki/Schering_AG" title="Schering AG">Schering</a> under the brand name Progynon Buccal Tablets by 1949.<a href="#cite_note-JAPA1949-206">[202]</a> Estradiol tablets for use by the sublingual route were marketed under the brand name Estradiol Membrettes in 1950,<a href="#cite_note-DrugReporter1950-207">[203]</a><a href="#cite_note-APP1950-208">[204]</a><a href="#cite_note-Romaine1950-209">[205]</a><a href="#cite_note-Welsh1951-210">[206]</a> as well as under the brand name Diogynets by 1952.<a href="#cite_note-Society1952-211">[207]</a><a href="#cite_note-AAGP1954-212">[208]</a><a href="#cite_note-Spence1953-213">[209]</a> Longer-acting esters of estradiol in oil solution like <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a> (Delestrogen, Progynon Depot), <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a> (Depo-Estradiol), and <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a> (Delestrec, Progynon Depot 100), as well as the <a href="/wiki/Polymeric" class="mw-redirect" title="Polymeric">polymeric</a> estradiol ester <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a> in <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous solution</a> (Estradurin), were developed and introduced for use by intramuscular injection in the 1950s.<a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-Elks2014-173">[169]</a><a href="#cite_note-Publishing2013-214">[210]</a><a href="#cite_note-pmid7389356-215">[211]</a> Due to poor <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> and low <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a> relative to other estrogens, oral estradiol was not widely used as late as the early 1970s.<a href="#cite_note-pmid5023261-216">[212]</a> Instead, <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> and <a href="/wiki/Animal_product" title="Animal product">animal</a>-derived estrogens like <a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">conjugated estrogens</a>, <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>, and <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a> were typically used by the oral route.<a href="#cite_note-pmid5023261-216">[212]</a> In 1966, oral estradiol valerate was introduced by Schering for medical use under the brand name Progynova.<a href="#cite_note-KlinWochenschr1966-32">[32]</a><a href="#cite_note-pmid5593020-33">[33]</a><a href="#cite_note-pmid5728263-217">[213]</a><a href="#cite_note-pmid5045321-218">[214]</a> <a href="/wiki/Esterification" class="mw-redirect" title="Esterification">Esterification</a> of estradiol, as in estradiol valerate, was believed to improve its <a href="/wiki/Metabolic_stability" class="mw-redirect" title="Metabolic stability">metabolic stability</a> with oral administration.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid7169965-6">[6]</a> Studies in the 1960s showed that <a href="/wiki/Micronization" title="Micronization">micronization</a> of <a href="/wiki/Steroid" title="Steroid">steroids</a> such as <a href="/wiki/Spironolactone" title="Spironolactone">spironolactone</a> and <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a> improved their absorption and oral potency by several-fold.<a href="#cite_note-Dorfman2016-219">[215]</a><a href="#cite_note-HorskyPresl2012-220">[216]</a><a href="#cite_note-Brotherton1976-221">[217]</a><a href="#cite_note-pmid5753386-222">[218]</a><a href="#cite_note-pmid2112080-223">[219]</a> In 1972, micronization of estradiol was studied in women and was likewise found to improve the absorption and potency of estradiol by the oral route.<a href="#cite_note-pmid5023261-216">[212]</a> Subsequently, oral micronized estradiol was introduced for medical use in the United States under the brand name Estrace in 1975.<a href="#cite_note-Estrace-FDA-34">[34]</a><a href="#cite_note-224">[220]</a> However, oral micronized estradiol valerate had been introduced by Schering in 1968.<a href="#cite_note-KuhlWiegratz2008-225">[221]</a> Oral micronized estradiol and oral estradiol valerate have similar <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> and are both now widely used throughout the world.<a href="#cite_note-pmid16112947-11">[11]</a><a href="#cite_note-pmid7169965-6">[6]</a> After the introduction of oral micronized estradiol, vaginal and intranasal micronized estradiol were evaluated in 1977 and both subsequently introduced.<a href="#cite_note-pmid591620-226">[222]</a><a href="#cite_note-pmid16112947-11">[11]</a> The first transdermal estradiol gel, a hydroalcoholic gel known as EstroGel, was initially described in 1980 and was introduced in Europe around 1981.<a href="#cite_note-pmid16530874-227">[223]</a> Transdermal estradiol gel did not become available in the United States until 2004, when EstroGel was introduced in this country as well.<a href="#cite_note-pmid16530874-227">[223]</a> A transdermal estradiol emulsion, Estrasorb, was marketed in the United States in 2003 as well.<a href="#cite_note-pmid16530874-227">[223]</a> One of the earliest reports of transdermal estradiol patches was published in 1983.<a href="#cite_note-pmid16530874-227">[223]</a><a href="#cite_note-pmid15845914-228">[224]</a> Estraderm, a reservoir patch and the first transdermal estradiol patch to be marketed, was introduced in Europe in 1985 and in the United States in 1986.<a href="#cite_note-BensonWatkinson2011-229">[225]</a><a href="#cite_note-pmid15040576-230">[226]</a> The first transdermal matrix estradiol patches to be introduced were Climara and Vivelle between 1994 and 1996, and were followed by many others.<a href="#cite_note-pmid16530874-227">[223]</a><a href="#cite_note-pmid25560046-231">[227]</a> <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a>, a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of estradiol, was synthesized from estradiol by Inhoffen and Hohlweg in 1938 and was introduced for oral use by Schering in the United States under the brand name Estinyl in 1943.<a href="#cite_note-OettelSchillinger2012-232">[228]</a><a href="#cite_note-MosbyGenRx2001-233">[229]</a> Starting in the 1950s, ethinylestradiol became widely used in <a href="/wiki/Birth_control_pill" class="mw-redirect" title="Birth control pill">birth control pills</a>.<a href="#cite_note-OettelSchillinger2012-232">[228]</a> <a href="/wiki/Estradiol-containing_birth_control_pill" title="Estradiol-containing birth control pill">Estradiol-containing birth control pills</a> were initially studied in the 1970s, with the first report published in 1977.<a href="#cite_note-pmid319864-234">[230]</a><a href="#cite_note-pmid23384741-235">[231]</a> Development of birth control pills containing estradiol was motivated by the thrombotic risks of ethinylestradiol that were uncovered in the 1960s and 1970s.<a href="#cite_note-pmid28712325-236">[232]</a><a href="#cite_note-pmid20136565-237">[233]</a><a href="#cite_note-pmid23931030-238">[234]</a><a href="#cite_note-pmid23384741-235">[231]</a> More than 15 attempts were made at development of an estradiol-containing birth control pill starting in the 1970s, but were unsuccessful due to unacceptable <a href="/wiki/Menstrual_bleeding" class="mw-redirect" title="Menstrual bleeding">menstrual bleeding</a> patterns.<a href="#cite_note-pmid23384741-235">[231]</a> <a href="/wiki/Estradiol_valerate/cyproterone_acetate" title="Estradiol valerate/cyproterone acetate">Estradiol valerate/cyproterone acetate</a> (Femilar) was introduced for use as a birth control pill in <a href="/wiki/Finland" title="Finland">Finland</a> in 1993, but was never marketed elsewhere.<a href="#cite_note-pmid20004267-239">[235]</a> Subsequently, <a href="/wiki/Estradiol_valerate/dienogest" title="Estradiol valerate/dienogest">estradiol valerate/dienogest</a> (Natazia, Qlaira) was marketed as a birth control pill in 2008<a href="#cite_note-pmid22468839-240">[236]</a> and <a href="/wiki/Estradiol/nomegestrol_acetate" class="mw-redirect" title="Estradiol/nomegestrol acetate">estradiol/nomegestrol acetate</a> (Naemis, Zoely) was introduced in 2012.<a href="#cite_note-pmid28902531-132">[128]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=31" 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_(medication)&action=edit&section=32" title="Edit section: Generic names">edit</a>]</div> Estradiol is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of estradiol in American English 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 INN, <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/United_States_Pharmacopeia" title="United States Pharmacopeia"><abbr title="United States Pharmacopeia">USP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Pharmacopeia, <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name, <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dénomination Commune Française, and <a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name"><abbr title="Japanese Accepted Name">JAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Japanese Accepted Name.<a href="#cite_note-Drugs.com1-241">[237]</a><a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-Elks2014-173">[169]</a><a href="#cite_note-MortonHall2012-242">[238]</a><a href="#cite_note-KEGG-243">[239]</a> Estradiolo is the name of estradiol in Italian and the <a href="/wiki/Denominazione_Comune_Italiana" title="Denominazione Comune Italiana"><abbr title="Denominazione Comune Italiana">DCIT</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 Denominazione Comune Italiana<a href="#cite_note-Drugs.com1-241">[237]</a> and estradiolum is its name in Latin, whereas its name remains unchanged as estradiol in Spanish, Portuguese, French, and German.<a href="#cite_note-Drugs.com1-241">[237]</a><a href="#cite_note-IndexNominum2000-174">[170]</a> Oestradiol was the former <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name of estradiol and its name in British English,<a href="#cite_note-MortonHall2012-242">[238]</a> but the spelling was eventually changed to estradiol.<a href="#cite_note-Drugs.com1-241">[237]</a> When estradiol is provided in its hemihydrate form, 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 INN is estradiol hemihydrate.<a href="#cite_note-IndexNominum2000-174">[170]</a> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=33" title="Edit section: Brand names">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_estrogen_esters#Estradiol_esters" title="List of estrogen esters">List of estrogen esters § Estradiol esters</a>, <a href="/wiki/Combined_injectable_contraceptive#Available_forms" class="mw-redirect" title="Combined injectable contraceptive">Combined injectable contraceptive § Available forms</a>, and <a href="/wiki/Estradiol-containing_oral_contraceptive" class="mw-redirect" title="Estradiol-containing oral contraceptive">Estradiol-containing oral contraceptive</a></div> Estradiol is marketed under a large number of <a href="/wiki/Brand_name" class="mw-redirect" title="Brand name">brand names</a> throughout the world.<a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-Drugs.com1-241">[237]</a> Examples of major brand names in which estradiol has been marketed in include Climara, Climen, Dermestril, Divigel, Estrace, Natifa, Estraderm, Estraderm TTS, Estradot, Estreva, Estrimax, Estring, Estrofem, EstroGel, Evorel, Fem7 (or FemSeven), Imvexxy, Menorest, Oesclim, OestroGel, Sandrena, Systen, and Vagifem.<a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-Drugs.com1-241">[237]</a> <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a> is marketed mainly as Progynova and Progynon-Depot, while it is marketed as Delestrogen in the US.<a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-Drugs@FDA1-180">[176]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a> is used mainly in the US and is marketed under the brand name Depo-Estradiol.<a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-Drugs@FDA1-180">[176]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a> is available as Femtrace, Femring, and Menoring.<a href="#cite_note-Drugs@FDA1-180">[176]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] Estradiol is also widely available in combination with progestogens.<a href="#cite_note-Drugs.com1-241">[237]</a> It is available in combination with <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a> under the major brand names Activelle, Cliane, Estalis, Eviana, Evorel Conti, Evorel Sequi, Kliogest, Novofem, Sequidot, and Trisequens; with <a href="/wiki/Drospirenone" title="Drospirenone">drospirenone</a> as Angeliq; with <a href="/wiki/Dydrogesterone" title="Dydrogesterone">dydrogesterone</a> as Femoston, Femoston Conti; and with <a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">nomegestrol acetate</a> as Zoely.<a href="#cite_note-Drugs.com1-241">[237]</a> Estradiol valerate is available with <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a> as Climen; with <a href="/wiki/Dienogest" title="Dienogest">dienogest</a> as Climodien and Qlaira; with <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a> as Cyclo-Progynova and Progyluton; with <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a> as Klimonorm; with <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a> as Divina and Indivina; and with <a href="/wiki/Norethisterone_enantate" class="mw-redirect" title="Norethisterone enantate">norethisterone enantate</a> as Mesigyna and Mesygest.<a href="#cite_note-Drugs.com1-241">[237]</a> <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a> is available with medroxyprogesterone acetate as Cyclo-Provera, Cyclofem, Feminena, Lunelle, and Novafem;<a href="#cite_note-pmid12290848-16">[16]</a> <a href="/wiki/Estradiol_enantate" title="Estradiol enantate">estradiol enantate</a> with <a href="/wiki/Algestone_acetophenide" title="Algestone acetophenide">algestone acetophenide</a> as Deladroxate and Topasel;<a href="#cite_note-Drugs.com1-241">[237]</a><a href="#cite_note-Rowlands2009-244">[240]</a> and <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a> is marketed with <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> as Mestrolar and Nomestrol.<a href="#cite_note-Drugs.com1-241">[237]</a> Estradiol valerate is also widely available in combination with <a href="/wiki/Prasterone_enantate" class="mw-redirect" title="Prasterone enantate">prasterone enantate</a> (DHEA enantate) under the brand name Gynodian Depot.<a href="#cite_note-Drugs.com1-241">[237]</a> <div class="mw-heading mw-heading3"><h3 id="Slang_Names">Slang Names</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=34" title="Edit section: Slang Names">edit</a>]</div> Estradiol has a number of humorous nicknames among the transgender community. Among them are <a href="/wiki/Skittles_(confectionery)" title="Skittles (confectionery)">titty skittles</a>, <a href="/wiki/Mint_(candy)" title="Mint (candy)">breast mints</a>, <a href="/wiki/M%26M%27s" title="M&M's">femme&m's</a>, <a href="/wiki/Antibiotic" title="Antibiotic">antiboyotics</a>, <a href="/wiki/Antihistamine" title="Antihistamine">anticistamines</a>, <a href="/wiki/Hydraulic_fluid" title="Hydraulic fluid">trans-mission fluid</a>, and <a href="/wiki/The_Notorious_B.I.G." title="The Notorious B.I.G.">the Notorious H.R.T.</a><a href="#cite_note-245">[241]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=35" title="Edit section: Availability">edit</a>]</div> Estradiol and/or its esters are widely available in countries throughout the world in a variety of formulations.<a href="#cite_note-Drugs.com1-241">[237]</a><a href="#cite_note-Martindale-246">[242]</a><a href="#cite_note-Micromedex-247">[243]</a><a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-Drugs@FDA1-180">[176]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] Shortages of estradiol began around 2022, caused partly by the <a href="/wiki/COVID-19_pandemic" title="COVID-19 pandemic">COVID-19 pandemic</a> disrupting supply and due to increasing demand. In Britain, for example, prescriptions for all hormone replacement therapy drugs more than doubled between 2018 and 2022. The shortage remains as of March 2024.<a href="#cite_note-248">[244]</a><a href="#cite_note-249">[245]</a><a href="#cite_note-250">[246]</a> <div class="mw-heading mw-heading4"><h4 id="United_States">United States</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=36" title="Edit section: United States">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> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Estrogen_patch.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Estrogen_patch.jpg/225px-Estrogen_patch.jpg" decoding="async" width="225" height="225" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/20/Estrogen_patch.jpg/338px-Estrogen_patch.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/20/Estrogen_patch.jpg/450px-Estrogen_patch.jpg 2x" data-file-width="1408" data-file-height="1409" /></a><figcaption>Vivelle-Dot, an estradiol patch</figcaption></figure> As of November 2016<a class="external text" href="https://en.wikipedia.org/w/index.php?title=Estradiol_(medication)&action=edit">[update]</a>, estradiol is available in the United States in the following forms:<a href="#cite_note-Drugs@FDA1-180">[176]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] <ul><li>Oral tablets (Femtrace (as <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>), Gynodiol, Innofem, <a href="/wiki/Generic_drug" title="Generic drug">generics</a>)</li> <li>Transdermal patches (Alora, Climara, Esclim, Estraderm, FemPatch, Menostar, Minivelle, Vivelle, Vivelle-Dot, generics)</li> <li><a href="/wiki/Topical_gels" title="Topical gels">Topical gels</a> (Divigel, Elestrin, EstroGel, Sandrena), emulsions (Estrasorb), and sprays (Evamist)</li> <li>Vaginal tablets (Vagifem, generics), creams (Estrace), inserts (Imvexxy), and rings (Estring, Femring (as estradiol acetate))</li> <li>Oil solution for intramuscular injection (Delestrogen (as <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>), Depo-Estradiol (as <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>))</li></ul> Oral estradiol valerate (Progynova) and other esters of estradiol that are used by injection like <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_enantate" title="Estradiol enantate">estradiol enantate</a>, and <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a> all are not marketed in the US.<a href="#cite_note-Drugs@FDA1-180">[176]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a> (Estradurin) was marketed in the US previously but is no longer available.<a href="#cite_note-251">[247]</a> Estradiol is also available in the US in combination with progestogens for the treatment of menopausal symptoms and as a combined hormonal contraceptive:<a href="#cite_note-Drugs@FDA1-180">[176]</a>[<a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">failed verification</a>] <ul><li>Oral <a href="/wiki/Oil" title="Oil">oil</a>-filled <a href="/wiki/Capsule_(pharmacy)" title="Capsule (pharmacy)">capsules</a> with <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a> (<a href="/wiki/Estradiol/progesterone" title="Estradiol/progesterone">Bijuva</a>)<a href="#cite_note-AdisInsight-TX-001-HR-252">[248]</a><a href="#cite_note-pmid25944519-253">[249]</a></li> <li>Oral tablets with <a href="/wiki/Drospirenone" title="Drospirenone">drospirenone</a> (<a href="/wiki/Angeliq" class="mw-redirect" title="Angeliq">Angeliq</a>) and <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a> (<a href="/wiki/Activella" class="mw-redirect" title="Activella">Activella</a>, <a href="/wiki/Amabelz" class="mw-redirect" title="Amabelz">Amabelz</a>) and as estradiol valerate with <a href="/wiki/Dienogest" title="Dienogest">dienogest</a> (<a href="/wiki/Natazia" class="mw-redirect" title="Natazia">Natazia</a>)</li> <li>Transdermal patches with <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a> (<a href="/wiki/Climara_Pro" class="mw-redirect" title="Climara Pro">Climara Pro</a>) and norethisterone acetate (<a href="/wiki/Combipatch" class="mw-redirect" title="Combipatch">Combipatch</a>)</li></ul> Estradiol and estradiol esters are also available in custom preparations from <a href="/wiki/Compounding_pharmacy" class="mw-redirect" title="Compounding pharmacy">compounding pharmacies</a> in the US.<a href="#cite_note-pmid26035149-254">[250]</a> This includes subcutaneous pellet implants, which are not available in the United States as FDA-approved pharmaceutical drugs.<a href="#cite_note-pmid26418479-255">[251]</a> In addition, topical creams that contain estradiol are generally regulated as <a href="/wiki/Cosmetics" title="Cosmetics">cosmetics</a> rather than as drugs in the US and hence are also sold <a href="/wiki/Over-the-counter" class="mw-redirect" title="Over-the-counter">over-the-counter</a> and may be purchased without a <a href="/wiki/Medical_prescription" title="Medical prescription">prescription</a> on the <a href="/wiki/Internet" title="Internet">Internet</a>.<a href="#cite_note-pmid17549577-256">[252]</a> <div class="mw-heading mw-heading4"><h4 id="Other_countries">Other countries</h4>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=37" title="Edit section: Other countries">edit</a>]</div> Pharmaceutical estradiol <a href="/wiki/Subcutaneous_implant" title="Subcutaneous implant">subcutaneous pellet implants</a> were formerly available in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> and <a href="/wiki/Australia" title="Australia">Australia</a> under the brand name Estradiol Implants or Oestradiol Implants (<a href="/wiki/Organon_International" class="mw-redirect" title="Organon International">Organon</a>; 25, 50, or 100 mg), but have been discontinued.<a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-Melville2015-257">[253]</a><a href="#cite_note-Dollery1991-258">[254]</a><a href="#cite_note-Kar2005-259">[255]</a><a href="#cite_note-Walters1986-260">[256]</a> However, an estradiol subcutaneous implant with the brand name Meno-Implant (Organon; 20 mg) continues to be available in the <a href="/wiki/Netherlands" title="Netherlands">Netherlands</a>.<a href="#cite_note-Drugs.com1-241">[237]</a><a href="#cite_note-IndexNominum2000-174">[170]</a><a href="#cite_note-Braam2006-261">[257]</a><a href="#cite_note-Gezondheids-262">[258]</a> Previously, for instance in the 1970s and 1980s, other subcutaneous estradiol implant products such as Progynon Pellets (Schering; 25 mg) and Estropel Pellets (25 mg; Bartor Pharmacol) were marketed.<a href="#cite_note-Eskin1988-263">[259]</a><a href="#cite_note-AMA1977-264">[260]</a><a href="#cite_note-Jones1979-265">[261]</a> It has been said that pharmaceutical estradiol implants have been almost exclusively used in the United Kingdom.<a href="#cite_note-BirkhauserBarlow2005-266">[262]</a> Subcutaneous estradiol implants are also available as custom <a href="/wiki/Compounding_pharmacy" class="mw-redirect" title="Compounding pharmacy">compounded</a> products in some countries.<a href="#cite_note-pmid25387347-267">[263]</a><a href="#cite_note-pmid26418479-255">[251]</a><a href="#cite_note-pmid27032319-268">[264]</a> <div class="mw-heading mw-heading3"><h3 id="Economics">Economics</h3>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=38" title="Edit section: Economics">edit</a>]</div> <a href="/wiki/Generic_drug" title="Generic drug">Generic</a> oral estradiol tablets are much less expensive than other forms of estradiol such as <a href="/wiki/Transdermal_administration" class="mw-redirect" title="Transdermal administration">transdermal</a> <a href="/wiki/Transdermal_gel" class="mw-redirect" title="Transdermal gel">gel</a> and <a href="/wiki/Transdermal_patch" title="Transdermal patch">patches</a> and <a href="/wiki/Vaginal_ring" title="Vaginal ring">vaginal rings</a>.<a href="#cite_note-JAMA2019-269">[265]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=39" title="Edit section: Research">edit</a>]</div> A variety of <a href="/wiki/Estradiol-containing_combined_birth_control_pill" class="mw-redirect" title="Estradiol-containing combined birth control pill">estradiol-containing combined birth control pills</a> were studied but never marketed.<a href="#cite_note-pmid20004267-239">[235]</a> In addition, a variety of estradiol-containing <a href="/wiki/Combined_injectable_contraceptive" class="mw-redirect" title="Combined injectable contraceptive">combined injectable contraceptives</a> were studied but never marketed.<a href="#cite_note-pmid12290848-16">[16]</a><a href="#cite_note-pmid8013219-270">[266]</a><a href="#cite_note-pmid8013221-271">[267]</a><a href="#cite_note-pmid8013216-272">[268]</a><a href="#cite_note-Toppozada1983-273">[269]</a> Estradiol has been studied in the treatment of <a href="/wiki/Postpartum_depression" title="Postpartum depression">postpartum depression</a> and <a href="/wiki/Postpartum_psychosis" title="Postpartum psychosis">postpartum psychosis</a>.<a href="#cite_note-pmid16344831-274">[270]</a><a href="#cite_note-pmid20795848-275">[271]</a><a href="#cite_note-pmid19874247-276">[272]</a><a href="#cite_note-pmid19661765-277">[273]</a><a href="#cite_note-pmid14521476-278">[274]</a> Estrogens such as estradiol appear to improve <a href="/wiki/Sexual_desire" title="Sexual desire">sexual desire</a> and <a href="/wiki/Sexual_function" title="Sexual function">function</a> in women.<a href="#cite_note-pmid26589379-279">[275]</a><a href="#cite_note-pmid26944462-280">[276]</a> However, the available evidence overall does not support the use of estradiol and other estrogens for improving sexual desire and function in women as of 2016.<a href="#cite_note-pmid26944462-280">[276]</a> An exception is the use of estrogens to treat <a href="/wiki/Vaginal_atrophy" class="mw-redirect" title="Vaginal atrophy">vaginal atrophy</a>.<a href="#cite_note-pmid26944462-280">[276]</a> Estrogen therapy has been proposed as a potential treatment for <a href="/wiki/Autism" title="Autism">autism</a> but clinical studies are needed.<a href="#cite_note-pmid27789681-281">[277]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=40" 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-FordRoach2013-1"><a href="#cite_ref-FordRoach2013_1-0">^</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 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Deutsche Medizinische Wochenschrift. 60 (11): 389–393. <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-0028-1129842">10.1055/s-0028-1129842</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/0012-0472">0012-0472</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:72668930">72668930</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=Neue+Wege+der+Hormontherapie+in+der+Gyn%C3%A4kologie&rft.volume=60&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E389-%3C%2Fspan%3E393&rft.date=2009&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A72668930%23id-name%3DS2CID&rft.issn=0012-0472&rft_id=info%3Adoi%2F10.1055%2Fs-0028-1129842&rft.aulast=Buschbeck&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Biskind1935-31">^ <a href="#cite_ref-Biskind1935_31-0">a</a> <a href="#cite_ref-Biskind1935_31-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBiskind1935" class="citation journal cs1">Biskind MS (1935). "Commercial Glandular Products". Journal of the American Medical Association. 105 (9): 667. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1001%2Fjama.1935.92760350007009a">10.1001/jama.1935.92760350007009a</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/0002-9955">0002-9955</a>. <q>Progynon-B, Schering Corporation: This is crystalline hydroxyestrin benzoate obtained by hydrogenation of theelin and subsequent conversion to the benzoate. [...] Progynon-B is marketed in ampules containing 1 cc. of a sesame oil solution of hydroxyestrin benzoate of either 2,500, 5,000, 10,000 or 50,000 international units.</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+the+American+Medical+Association&rft.atitle=Commercial+Glandular+Products&rft.volume=105&rft.issue=9&rft.pages=667&rft.date=1935&rft_id=info%3Adoi%2F10.1001%2Fjama.1935.92760350007009a&rft.issn=0002-9955&rft.aulast=Biskind&rft.aufirst=MS&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-KlinWochenschr1966-32">^ <a href="#cite_ref-KlinWochenschr1966_32-0">a</a> <a href="#cite_ref-KlinWochenschr1966_32-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1">"Neue Spezialitäten". Klinische Wochenschrift. 44 (23): 1381. 1966. <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%2FBF01747900">10.1007/BF01747900</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0023-2173">0023-2173</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:20357182">20357182</a>. <q>NEUE SPEZIALITATEN [...] Progynova. 1 Dragee enthält 2 mg Oestradiolvalerinat (Klimakterium). Hersteller: Schering AG, Berlin 65.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Klinische+Wochenschrift&rft.atitle=Neue+Spezialit%C3%A4ten&rft.volume=44&rft.issue=23&rft.pages=1381&rft.date=1966&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20357182%23id-name%3DS2CID&rft.issn=0023-2173&rft_id=info%3Adoi%2F10.1007%2FBF01747900&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid5593020-33">^ <a href="#cite_ref-pmid5593020_33-0">a</a> <a href="#cite_ref-pmid5593020_33-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDapunt1967" class="citation journal cs1 cs1-prop-foreign-lang-source">Dapunt O (September 1967). "[The management of climacteric disorders using estradiol valerate (Progynova)]" [The management of climacteric disorders using estradiol valerate (Progynova)]. 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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=%3Cspan+class%3D%22nowrap%22%3E1167-%3C%2Fspan%3E1174&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+%28medication%29" class="Z3988"> </li> <li id="cite_note-Muller1998-96"><a href="#cite_ref-Muller1998_96-0">^</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+%3Cspan+class%3D%22nowrap%22%3E454-%3C%2Fspan%3E455%2C+%3Cspan+class%3D%22nowrap%22%3E566-%3C%2Fspan%3E567&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+%28medication%29" class="Z3988"> </li> <li id="cite_note-KrishnaShah1996-97"><a href="#cite_ref-KrishnaShah1996_97-0">^</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+%28medication%29" class="Z3988"> </li> <li id="cite_note-NNR1949-98"><a href="#cite_ref-NNR1949_98-0">^</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=%3Cspan+class%3D%22nowrap%22%3E692-%3C%2Fspan%3E694&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+%28medication%29" class="Z3988"> </li> <li id="cite_note-AerodiolLabel-99"><a href="#cite_ref-AerodiolLabel_99-0">^</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+%28medication%29" class="Z3988"> </li> <li id="cite_note-Drugs.com-100"><a href="#cite_ref-Drugs.com_100-0">^</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+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid18382901-101"><a href="#cite_ref-pmid18382901_101-0">^</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, et al. (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=%3Cspan+class%3D%22nowrap%22%3E173-%3C%2Fspan%3E7&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+%28medication%29" class="Z3988"> </li> <li id="cite_note-PlouffeRavnikar2012-102"><a href="#cite_ref-PlouffeRavnikar2012_102-0">^</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+%28medication%29" class="Z3988"> </li> <li id="cite_note-UC1952-103"><a href="#cite_ref-UC1952_103-0">^</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+%28medication%29" class="Z3988"> </li> <li id="cite_note-Leidenberger2013-104"><a href="#cite_ref-Leidenberger2013_104-0">^</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+%28medication%29" class="Z3988"> </li> <li id="cite_note-LemkeWilliams2012-105">^ <a href="#cite_ref-LemkeWilliams2012_105-0">a</a> <a href="#cite_ref-LemkeWilliams2012_105-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLemkeWilliams2012" class="citation book cs1">Lemke TL, Williams DA (24 January 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1419">Foye's Principles of Medicinal Chemistry</a>. Lippincott Williams & Wilkins. pp. 1419–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60913-345-0" title="Special:BookSources/978-1-60913-345-0"><bdi>978-1-60913-345-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034548/https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1419">Archived</a> from the original on 10 June 2022. 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Journal of Steroid Biochemistry. 12: 143–157. <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%2F0022-4731%2880%2990264-2">10.1016/0022-4731(80)90264-2</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/7421203">7421203</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+Steroid+Biochemistry&rft.atitle=Steroid+hormone+receptors+and+pharmacology&rft.volume=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E143-%3C%2Fspan%3E157&rft.date=1980-01&rft_id=info%3Adoi%2F10.1016%2F0022-4731%2880%2990264-2&rft_id=info%3Apmid%2F7421203&rft.aulast=Raynaud&rft.aufirst=JP&rft.au=Bouton%2C+MM&rft.au=Moguilewsky%2C+M&rft.au=Ojasoo%2C+T&rft.au=Philibert%2C+D&rft.au=Beck%2C+G&rft.au=Labrie%2C+F&rft.au=Mornon%2C+JP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Labhart2012p548-158">^ <a href="#cite_ref-Labhart2012p548_158-0">a</a> <a href="#cite_ref-Labhart2012p548_158-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLabhart2012" class="citation book cs1">Labhart A (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA548">Clinical Endocrinology: Theory and Practice</a>. Springer Science & Business Media. pp. 548–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-96158-8" title="Special:BookSources/978-3-642-96158-8"><bdi>978-3-642-96158-8</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200103073131/https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA548">Archived</a> from the original on 3 January 2020. Retrieved 11 November 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Endocrinology%3A+Theory+and+Practice&rft.pages=548-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-96158-8&rft.aulast=Labhart&rft.aufirst=A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DDAgJCAAAQBAJ%26pg%3DPA548&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Dietrich2014-159"><a href="#cite_ref-Dietrich2014_159-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDietrich2014" class="citation book cs1">Dietrich JE (18 June 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ipEpBAAAQBAJ&pg=PA53">Female Puberty: A Comprehensive Guide for Clinicians</a>. Springer. pp. 53–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4939-0912-4" title="Special:BookSources/978-1-4939-0912-4"><bdi>978-1-4939-0912-4</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200504210732/https://books.google.com/books?id=ipEpBAAAQBAJ&pg=PA53">Archived</a> from the original on 4 May 2020. Retrieved 9 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Female+Puberty%3A+A+Comprehensive+Guide+for+Clinicians&rft.pages=53-&rft.pub=Springer&rft.date=2014-06-18&rft.isbn=978-1-4939-0912-4&rft.aulast=Dietrich&rft.aufirst=JE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DipEpBAAAQBAJ%26pg%3DPA53&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-ThornhillGangestad2008-160"><a href="#cite_ref-ThornhillGangestad2008_160-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFThornhillGangestad2008" class="citation book cs1">Thornhill R, Gangestad SW (25 September 2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=joX0BgAAQBAJ&pg=PT145">The Evolutionary Biology of Human Female Sexuality</a>. Oxford University Press. pp. 145–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-988770-5" title="Special:BookSources/978-0-19-988770-5"><bdi>978-0-19-988770-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200504210809/https://books.google.com/books?id=joX0BgAAQBAJ&pg=PT145">Archived</a> from the original on 4 May 2020. Retrieved 9 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Evolutionary+Biology+of+Human+Female+Sexuality&rft.pages=145-&rft.pub=Oxford+University+Press&rft.date=2008-09-25&rft.isbn=978-0-19-988770-5&rft.aulast=Thornhill&rft.aufirst=R&rft.au=Gangestad%2C+SW&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DjoX0BgAAQBAJ%26pg%3DPT145&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid12762829-161"><a href="#cite_ref-pmid12762829_161-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRaine-FenningBrincatMuscat-Baron2003" class="citation journal cs1">Raine-Fenning NJ, Brincat MP, Muscat-Baron Y (2003). "Skin aging and menopause : implications for treatment". American Journal of Clinical Dermatology. 4 (6): 371–378. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2165%2F00128071-200304060-00001">10.2165/00128071-200304060-00001</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12762829">12762829</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:20392538">20392538</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Clinical+Dermatology&rft.atitle=Skin+aging+and+menopause+%3A+implications+for+treatment&rft.volume=4&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E371-%3C%2Fspan%3E378&rft.date=2003&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20392538%23id-name%3DS2CID&rft_id=info%3Apmid%2F12762829&rft_id=info%3Adoi%2F10.2165%2F00128071-200304060-00001&rft.aulast=Raine-Fenning&rft.aufirst=NJ&rft.au=Brincat%2C+MP&rft.au=Muscat-Baron%2C+Y&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Hayward2003-162"><a href="#cite_ref-Hayward2003_162-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHayward2003" class="citation book cs1">Hayward C (31 July 2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=JnO_VCuH7scC&pg=PA22">Gender Differences at Puberty</a>. Cambridge University Press. pp. 22–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-521-00165-6" title="Special:BookSources/978-0-521-00165-6"><bdi>978-0-521-00165-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200504210736/https://books.google.com/books?id=JnO_VCuH7scC&pg=PA22">Archived</a> from the original on 4 May 2020. Retrieved 9 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Gender+Differences+at+Puberty&rft.pages=22-&rft.pub=Cambridge+University+Press&rft.date=2003-07-31&rft.isbn=978-0-521-00165-6&rft.aulast=Hayward&rft.aufirst=C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DJnO_VCuH7scC%26pg%3DPA22&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-MelmedPolonsky2015-163">^ <a href="#cite_ref-MelmedPolonsky2015_163-0">a</a> <a href="#cite_ref-MelmedPolonsky2015_163-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMelmedPolonskyLarsenKronenberg2015" class="citation book cs1">Melmed S, Polonsky KS, Larsen PR, Kronenberg HM (11 November 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=iPIACwAAQBAJ&pg=PA1105">Williams Textbook of Endocrinology</a>. Elsevier Health Sciences. pp. 1105–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-34157-8" title="Special:BookSources/978-0-323-34157-8"><bdi>978-0-323-34157-8</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200504210750/https://books.google.com/books?id=iPIACwAAQBAJ&pg=PA1105">Archived</a> from the original on 4 May 2020. Retrieved 9 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Williams+Textbook+of+Endocrinology&rft.pages=1105-&rft.pub=Elsevier+Health+Sciences&rft.date=2015-11-11&rft.isbn=978-0-323-34157-8&rft.aulast=Melmed&rft.aufirst=S&rft.au=Polonsky%2C+KS&rft.au=Larsen%2C+PR&rft.au=Kronenberg%2C+HM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DiPIACwAAQBAJ%26pg%3DPA1105&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-JonesLopez2013-164">^ <a href="#cite_ref-JonesLopez2013_164-0">a</a> <a href="#cite_ref-JonesLopez2013_164-1">b</a> <a href="#cite_ref-JonesLopez2013_164-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJonesLopez2013" class="citation book cs1">Jones RE, Lopez KH (28 September 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=M4kEdSnS-pkC&pg=PA19">Human Reproductive Biology</a>. Academic Press. pp. 19–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-382185-0" title="Special:BookSources/978-0-12-382185-0"><bdi>978-0-12-382185-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Human+Reproductive+Biology&rft.pages=19-&rft.pub=Academic+Press&rft.date=2013-09-28&rft.isbn=978-0-12-382185-0&rft.aulast=Jones&rft.aufirst=RE&rft.au=Lopez%2C+KH&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DM4kEdSnS-pkC%26pg%3DPA19&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Sloane2002-165">^ <a href="#cite_ref-Sloane2002_165-0">a</a> <a href="#cite_ref-Sloane2002_165-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSloane2002" class="citation book cs1">Sloane E (2002). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=kqcYyk7zlHYC&pg=PA496">Biology of Women</a>. Cengage Learning. pp. 496–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7668-1142-3" title="Special:BookSources/978-0-7668-1142-3"><bdi>978-0-7668-1142-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200504210805/https://books.google.com/books?id=kqcYyk7zlHYC&pg=PA496">Archived</a> from the original on 4 May 2020. Retrieved 9 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Biology+of+Women&rft.pages=496-&rft.pub=Cengage+Learning&rft.date=2002&rft.isbn=978-0-7668-1142-3&rft.aulast=Sloane&rft.aufirst=E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DkqcYyk7zlHYC%26pg%3DPA496&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-KingBrucker2010-166">^ <a href="#cite_ref-KingBrucker2010_166-0">a</a> <a href="#cite_ref-KingBrucker2010_166-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKingBrucker2010" class="citation book cs1">King TL, Brucker MC (25 October 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=u1wq63x4VsYC&pg=PA1022">Pharmacology for Women's Health</a>. Jones & Bartlett Learning. pp. 1022–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7637-5329-0" title="Special:BookSources/978-0-7637-5329-0"><bdi>978-0-7637-5329-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pharmacology+for+Women%27s+Health&rft.pages=1022-&rft.pub=Jones+%26+Bartlett+Learning&rft.date=2010-10-25&rft.isbn=978-0-7637-5329-0&rft.aulast=King&rft.aufirst=TL&rft.au=Brucker%2C+MC&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Du1wq63x4VsYC%26pg%3DPA1022&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Lobo2007-167">^ <a href="#cite_ref-Lobo2007_167-0">a</a> <a href="#cite_ref-Lobo2007_167-1">b</a> <a href="#cite_ref-Lobo2007_167-2">c</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>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200504210745/https://books.google.com/books?id=gywV9hkcyOMC&pg=PA217">Archived</a> from the original on 4 May 2020. Retrieved 9 December 2016.</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+%3Cspan+class%3D%22nowrap%22%3E217-%3C%2Fspan%3E226%2C+%3Cspan+class%3D%22nowrap%22%3E770-%3C%2Fspan%3E771&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+%28medication%29" class="Z3988"> </li> <li id="cite_note-WarshawskyJr.2005-168">^ <a href="#cite_ref-WarshawskyJr.2005_168-0">a</a> <a href="#cite_ref-WarshawskyJr.2005_168-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWarshawskyLandolph_Jr2005" class="citation book cs1">Warshawsky D, Landolph Jr JR (31 October 2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zSvMBQAAQBAJ&pg=PA457">Molecular Carcinogenesis and the Molecular Biology of Human Cancer</a>. CRC Press. pp. 457–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-203-50343-0" title="Special:BookSources/978-0-203-50343-0"><bdi>978-0-203-50343-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200504210813/https://books.google.com/books?id=zSvMBQAAQBAJ&pg=PA457">Archived</a> from the original on 4 May 2020. Retrieved 9 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Molecular+Carcinogenesis+and+the+Molecular+Biology+of+Human+Cancer&rft.pages=457-&rft.pub=CRC+Press&rft.date=2005-10-31&rft.isbn=978-0-203-50343-0&rft.aulast=Warshawsky&rft.aufirst=D&rft.au=Landolph+Jr%2C+JR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzSvMBQAAQBAJ%26pg%3DPA457&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-NotelovitzKeep2012-169"><a href="#cite_ref-NotelovitzKeep2012_169-0">^</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>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201215185214/https://books.google.com/books?id=VM0hBQAAQBAJ&pg=PA397">Archived</a> from the original on 15 December 2020. Retrieved 27 November 2016. <q>[...] following the menopause, circulating estradiol levels decrease from a premenopausal mean of 120 pg/ml to only 13 pg/ml.</q></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+%28medication%29" class="Z3988"> </li> <li id="cite_note-ChristianSchoultz1994-170"><a href="#cite_ref-ChristianSchoultz1994_170-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChristianvon_Schoultz1994" class="citation book cs1">Christian C, von Schoultz B (15 March 1994). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=apU4AfUqSGwC&pg=PA9">Hormone Replacement Therapy: Standardized or Individually Adapted Doses?</a>. CRC Press. pp. 9–16, 60. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-85070-545-1" title="Special:BookSources/978-1-85070-545-1"><bdi>978-1-85070-545-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201215184621/https://books.google.com/books?id=apU4AfUqSGwC&pg=PA9">Archived</a> from the original on 15 December 2020. Retrieved 23 July 2018. <q>The mean integrated estradiol level during a full 28-day normal cycle is around 80 pg/ml.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormone+Replacement+Therapy%3A+Standardized+or+Individually+Adapted+Doses%3F&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9-%3C%2Fspan%3E16%2C+60&rft.pub=CRC+Press&rft.date=1994-03-15&rft.isbn=978-1-85070-545-1&rft.aulast=Christian&rft.aufirst=C&rft.au=von+Schoultz%2C+B&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DapU4AfUqSGwC%26pg%3DPA9&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-MüllerMacLeod2012-171"><a href="#cite_ref-MüllerMacLeod2012_171-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMüllerMacLeod2012" class="citation book cs1">Müller EE, MacLeod RM (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=TUXtBwAAQBAJ&pg=PA121">Neuroendocrine Perspectives</a>. Springer Science & Business Media. pp. 121–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4612-3554-5" title="Special:BookSources/978-1-4612-3554-5"><bdi>978-1-4612-3554-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201215185053/https://books.google.com/books?id=TUXtBwAAQBAJ&pg=PA121">Archived</a> from the original on 15 December 2020. Retrieved 27 November 2016. <q>[...] [premenopausal] mean [estradiol] concentration of 150 pg/ml [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Neuroendocrine+Perspectives&rft.pages=121-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4612-3554-5&rft.aulast=M%C3%BCller&rft.aufirst=EE&rft.au=MacLeod%2C+RM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DTUXtBwAAQBAJ%26pg%3DPA121&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-RizkSallam2012-172">^ <a href="#cite_ref-RizkSallam2012_172-0">a</a> <a href="#cite_ref-RizkSallam2012_172-1">b</a> <a href="#cite_ref-RizkSallam2012_172-2">c</a> <a href="#cite_ref-RizkSallam2012_172-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRizkSallam2012" class="citation book cs1">Rizk BR, Sallam HN (15 June 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=GdLBOMzvfBwC&pg=PA11">Clinical Infertility and In Vitro Fertilization</a>. JP Medical Ltd. pp. 11–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-93-5025-095-2" title="Special:BookSources/978-93-5025-095-2"><bdi>978-93-5025-095-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034549/https://books.google.com/books?id=GdLBOMzvfBwC&pg=PA11">Archived</a> from the original on 10 June 2022. Retrieved 3 July 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Infertility+and+In+Vitro+Fertilization&rft.pages=11-&rft.pub=JP+Medical+Ltd&rft.date=2012-06-15&rft.isbn=978-93-5025-095-2&rft.aulast=Rizk&rft.aufirst=BR&rft.au=Sallam%2C+HN&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DGdLBOMzvfBwC%26pg%3DPA11&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Elks2014-173">^ <a href="#cite_ref-Elks2014_173-0">a</a> <a href="#cite_ref-Elks2014_173-1">b</a> <a href="#cite_ref-Elks2014_173-2">c</a> <a href="#cite_ref-Elks2014_173-3">d</a> <a href="#cite_ref-Elks2014_173-4">e</a> <a href="#cite_ref-Elks2014_173-5">f</a> <a href="#cite_ref-Elks2014_173-6">g</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFElks2014" class="citation book cs1">Elks J (14 November 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA897">The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</a>. Springer. pp. 897–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4757-2085-3" title="Special:BookSources/978-1-4757-2085-3"><bdi>978-1-4757-2085-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Dictionary+of+Drugs%3A+Chemical+Data%3A+Chemical+Data%2C+Structures+and+Bibliographies&rft.pages=897-&rft.pub=Springer&rft.date=2014-11-14&rft.isbn=978-1-4757-2085-3&rft.aulast=Elks&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0vXTBwAAQBAJ%26pg%3DPA897&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-IndexNominum2000-174">^ <a href="#cite_ref-IndexNominum2000_174-0">a</a> <a href="#cite_ref-IndexNominum2000_174-1">b</a> <a href="#cite_ref-IndexNominum2000_174-2">c</a> <a href="#cite_ref-IndexNominum2000_174-3">d</a> <a href="#cite_ref-IndexNominum2000_174-4">e</a> <a href="#cite_ref-IndexNominum2000_174-5">f</a> <a href="#cite_ref-IndexNominum2000_174-6">g</a> <a href="#cite_ref-IndexNominum2000_174-7">h</a> <a href="#cite_ref-IndexNominum2000_174-8">i</a> <a href="#cite_ref-IndexNominum2000_174-9">j</a> <a href="#cite_ref-IndexNominum2000_174-10">k</a> <a href="#cite_ref-IndexNominum2000_174-11">l</a> <a href="#cite_ref-IndexNominum2000_174-12">m</a> <a href="#cite_ref-IndexNominum2000_174-13">n</a> <a href="#cite_ref-IndexNominum2000_174-14">o</a> <a href="#cite_ref-IndexNominum2000_174-15">p</a> <a href="#cite_ref-IndexNominum2000_174-16">q</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=5GpcTQD_L2oC&pg=PA406">Index Nominum 2000: International Drug Directory</a>. Taylor & Francis US. 2000. pp. 404–406. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-88763-075-1" title="Special:BookSources/978-3-88763-075-1"><bdi>978-3-88763-075-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210607193711/https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA406">Archived</a> from the original on 7 June 2021. Retrieved 13 September 2012.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Index+Nominum+2000%3A+International+Drug+Directory&rft.pages=%3Cspan+class%3D%22nowrap%22%3E404-%3C%2Fspan%3E406&rft.pub=Taylor+%26+Francis+US&rft.date=2000&rft.isbn=978-3-88763-075-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5GpcTQD_L2oC%26pg%3DPA406&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid18744783-175">^ <a href="#cite_ref-pmid18744783_175-0">a</a> <a href="#cite_ref-pmid18744783_175-1">b</a> <a href="#cite_ref-pmid18744783_175-2">c</a> <a href="#cite_ref-pmid18744783_175-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFluhmann1938" class="citation journal cs1">Fluhmann CF (November 1938). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1659459">"Estrogenic Hormones: Their Clinical Usage"</a>. California and Western Medicine. 49 (5): 362–366. <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/PMC1659459">1659459</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/18744783">18744783</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=California+and+Western+Medicine&rft.atitle=Estrogenic+Hormones%3A+Their+Clinical+Usage&rft.volume=49&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E362-%3C%2Fspan%3E366&rft.date=1938-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1659459%23id-name%3DPMC&rft_id=info%3Apmid%2F18744783&rft.aulast=Fluhmann&rft.aufirst=CF&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1659459&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-GivensAnderson1981-176"><a href="#cite_ref-GivensAnderson1981_176-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGivensAnderson1981" class="citation book cs1">Givens JR, Anderson GD (1981). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=kE44AQAAIAAJ">Endocrinology of Pregnancy: Based on the Proceedings of the Fifth Annual Symposium on Gynecologic Endocrinology, Held March 3-5, 1980 at the University of Tennessee, Memphis, Tennessee</a>. Year Book Medical Publishers. p. 158. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8151-3529-6" title="Special:BookSources/978-0-8151-3529-6"><bdi>978-0-8151-3529-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034550/https://books.google.com/books?id=kE44AQAAIAAJ">Archived</a> from the original on 10 June 2022. Retrieved 3 July 2018. <q>Estetrol (E4) is an estrogen with four hydroxyl groups. More specifically, E4, is 15α-hydroxyestriol.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Endocrinology+of+Pregnancy%3A+Based+on+the+Proceedings+of+the+Fifth+Annual+Symposium+on+Gynecologic+Endocrinology%2C+Held+March+3-5%2C+1980+at+the+University+of+Tennessee%2C+Memphis%2C+Tennessee&rft.pages=158&rft.pub=Year+Book+Medical+Publishers&rft.date=1981&rft.isbn=978-0-8151-3529-6&rft.aulast=Givens&rft.aufirst=JR&rft.au=Anderson%2C+GD&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DkE44AQAAIAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-HumansOrganization2007-177"><a href="#cite_ref-HumansOrganization2007_177-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFIARC_Working_Group_on_the_Evaluation_of_Carcinogenic_Risks_to_HumansWorld_Health_OrganizationInternational_Agency_for_Research_On_Cancer2007" class="citation book cs1">IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, World Health Organization, International Agency for Research On Cancer (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=aGDU5xibtNgC&pg=PA384">Combined Estrogen-Progestogen Contraceptives and Combined Estrogen-Progestogen Menopausal Therapy</a>. World Health Organization. p. 384. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-92-832-1291-1" title="Special:BookSources/978-92-832-1291-1"><bdi>978-92-832-1291-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20130606230031/http://books.google.com/books?id=aGDU5xibtNgC&pg=PA384">Archived</a> from the original on 6 June 2013. Retrieved 13 September 2012.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Combined+Estrogen-Progestogen+Contraceptives+and+Combined+Estrogen-Progestogen+Menopausal+Therapy&rft.pages=384&rft.pub=World+Health+Organization&rft.date=2007&rft.isbn=978-92-832-1291-1&rft.au=IARC+Working+Group+on+the+Evaluation+of+Carcinogenic+Risks+to+Humans&rft.au=World+Health+Organization&rft.au=International+Agency+for+Research+On+Cancer&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DaGDU5xibtNgC%26pg%3DPA384&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-DesaiLee2007-178">^ <a href="#cite_ref-DesaiLee2007_178-0">a</a> <a href="#cite_ref-DesaiLee2007_178-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDesaiLee2007" class="citation book cs1">Desai A, Lee M (7 May 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=v0rLyVSc8EYC&pg=PA337">Gibaldi's Drug Delivery Systems in Pharmaceutical Care</a>. ASHP. p. 337. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-58528-136-7" title="Special:BookSources/978-1-58528-136-7"><bdi>978-1-58528-136-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20130608042333/http://books.google.com/books?id=v0rLyVSc8EYC&pg=PA337">Archived</a> from the original on 8 June 2013. Retrieved 13 September 2012.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Gibaldi%27s+Drug+Delivery+Systems+in+Pharmaceutical+Care&rft.pages=337&rft.pub=ASHP&rft.date=2007-05-07&rft.isbn=978-1-58528-136-7&rft.aulast=Desai&rft.aufirst=A&rft.au=Lee%2C+M&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dv0rLyVSc8EYC%26pg%3DPA337&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Wang-ChengNeuner2007-179"><a href="#cite_ref-Wang-ChengNeuner2007_179-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWang-ChengNeunerBarnabei2007" class="citation book cs1">Wang-Cheng R, Neuner JM, Barnabei VM (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=mPs5Ly71OCQC&pg=PA91">Menopause</a>. ACP Press. pp. 91–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-930513-83-9" title="Special:BookSources/978-1-930513-83-9"><bdi>978-1-930513-83-9</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160610230533/https://books.google.com/books?id=mPs5Ly71OCQC&pg=PA91">Archived</a> from the original on 10 June 2016. 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ASHP. pp. 336–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-58528-136-7" title="Special:BookSources/978-1-58528-136-7"><bdi>978-1-58528-136-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034551/https://books.google.com/books?id=v0rLyVSc8EYC&pg=PA336">Archived</a> from the original on 10 June 2022. 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Postgraduate Medicine. 8 (5): 393–400. <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%2F00325481.1950.11694030">10.1080/00325481.1950.11694030</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/14780947">14780947</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Postgraduate+Medicine&rft.atitle=Sublingual+or+buccal+administration+of+steroidal+hormones&rft.volume=8&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E393-%3C%2Fspan%3E400&rft.date=1950-11&rft_id=info%3Adoi%2F10.1080%2F00325481.1950.11694030&rft_id=info%3Apmid%2F14780947&rft.aulast=Lisser&rft.aufirst=H&rft.au=Gordan%2C+GS&rft.au=Aird%2C+RB&rft.au=Arrick%2C+MS&rft.au=Craig%2C+LS&rft.au=Escamilla%2C+RF&rft.au=Goldberg%2C+MB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-JAPA1949-206"><a href="#cite_ref-JAPA1949_206-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation journal cs1">"New Prescription Products". Journal of the American Pharmaceutical Association (Practical Pharmacy Ed.). 10 (4): 198–206. 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%2931795-9">10.1016/S0095-9561(16)31795-9</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=New+Prescription+Products&rft.volume=10&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E198-%3C%2Fspan%3E206&rft.date=1949&rft_id=info%3Adoi%2F10.1016%2FS0095-9561%2816%2931795-9&rft.issn=0095-9561&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-DrugReporter1950-207"><a href="#cite_ref-DrugReporter1950_207-0">^</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=Y9YhAQAAMAAJ">Oil, Paint and Drug Reporter</a>. April 1950. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034552/https://books.google.com/books?id=Y9YhAQAAMAAJ">Archived</a> from the original on 10 June 2022. Retrieved 12 December 2019. <q>Trade Briefs Wyeth, Inc., Philadelphia, has commenced marketing "Estradiol Membrettes, 0.25 mg." as an addition to its hormone line.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Oil%2C+Paint+and+Drug+Reporter&rft.date=1950-04&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DY9YhAQAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-APP1950-208"><a href="#cite_ref-APP1950_208-0">^</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=gfcrAQAAMAAJ">American Professional Pharmacist</a>. American Professional Pharmacist, Incorporated. 1950. p. 647. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034553/https://books.google.com/books?id=gfcrAQAAMAAJ">Archived</a> from the original on 10 June 2022. Retrieved 12 December 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=American+Professional+Pharmacist&rft.pages=647&rft.pub=American+Professional+Pharmacist%2C+Incorporated&rft.date=1950&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DgfcrAQAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Romaine1950-209"><a href="#cite_ref-Romaine1950_209-0">^</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=4e2rAAAAIAAJ">Medical Times</a>. 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Educational Publishers. p. 155. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210829012048/https://books.google.com/books?id=1m-C5uGARQEC">Archived</a> from the original on 29 August 2021. 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Estradiol, U.S.P., Transmucosal Tablets 0.125 mg., 0.25 mg. and 1.0 mg.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Journal&rft.date=1952&rft.au=Omaha+Midwest+Clinical+Society&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D-e0vAQAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-AAGP1954-212"><a href="#cite_ref-AAGP1954_212-0">^</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=MxogAQAAMAAJ">General Practitioner</a>. American Academy of General Practice. April 1954. pp. 168–170. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034737/https://books.google.com/books?id=MxogAQAAMAAJ">Archived</a> from the original on 10 June 2022. Retrieved 12 December 2019. <q>Diogynets* [...] * brand of estradiol transmucosal tablets, scored: 0.125 mg., 0.25 mg. and 1.0 mg., bottles of 50 and 100.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=General+Practitioner&rft.pages=%3Cspan+class%3D%22nowrap%22%3E168-%3C%2Fspan%3E170&rft.pub=American+Academy+of+General+Practice&rft.date=1954-04&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DMxogAQAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Spence1953-213"><a href="#cite_ref-Spence1953_213-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAllan_William_Spence1953" class="citation book cs1">Allan William Spence (1953). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=-mdsAAAAMAAJ">Clinical Endocrinology</a>. 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A preliminary study of effectiveness, tolerance and patient preference"</a>. Obstetrics and Gynecology. 39 (5): 771–774. <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/5023261">5023261</a>. 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Die Medizinische Welt (in German). 23 (22): 834–836. <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/5045321">5045321</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Die+Medizinische+Welt&rft.atitle=%5BTherapy+of+climacteric+deficiency+symptoms+using+progynova%5D&rft.volume=23&rft.issue=22&rft.pages=%3Cspan+class%3D%22nowrap%22%3E834-%3C%2Fspan%3E836&rft.date=1972-05&rft_id=info%3Apmid%2F5045321&rft.aulast=Koed&rft.aufirst=J&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Dorfman2016-219"><a href="#cite_ref-Dorfman2016_219-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDorfman2016" class="citation book cs1">Dorfman RI (5 December 2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=BbLfBAAAQBAJ&pg=PA392">Steroidal Activity in Experimental Animals and Man</a>. Elsevier Science. pp. 392–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4832-7299-3" title="Special:BookSources/978-1-4832-7299-3"><bdi>978-1-4832-7299-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200818231558/https://books.google.com/books?id=BbLfBAAAQBAJ&pg=PA392">Archived</a> from the original on 18 August 2020. Retrieved 15 December 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Steroidal+Activity+in+Experimental+Animals+and+Man&rft.pages=392-&rft.pub=Elsevier+Science&rft.date=2016-12-05&rft.isbn=978-1-4832-7299-3&rft.aulast=Dorfman&rft.aufirst=RI&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBbLfBAAAQBAJ%26pg%3DPA392&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-HorskyPresl2012-220"><a href="#cite_ref-HorskyPresl2012_220-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHorskyPresl2012" class="citation book cs1">Horsky J, Presl J (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7IrpCAAAQBAJ&pg=PA313">Ovarian Function and its Disorders: Diagnosis and Therapy</a>. Springer Science & Business Media. pp. 313–. <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>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20211021002528/https://books.google.com/books?id=7IrpCAAAQBAJ&pg=PA313">Archived</a> from the original on 21 October 2021. Retrieved 8 December 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Ovarian+Function+and+its+Disorders%3A+Diagnosis+and+Therapy&rft.pages=313-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-009-8195-9&rft.aulast=Horsky&rft.aufirst=J&rft.au=Presl%2C+J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7IrpCAAAQBAJ%26pg%3DPA313&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Brotherton1976-221"><a href="#cite_ref-Brotherton1976_221-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrotherton1976" class="citation book cs1">Brotherton J (1976). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zt5sAAAAMAAJ">Sex Hormone Pharmacology</a>. Academic Press. p. 34. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-137250-7" title="Special:BookSources/978-0-12-137250-7"><bdi>978-0-12-137250-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sex+Hormone+Pharmacology&rft.pages=34&rft.pub=Academic+Press&rft.date=1976&rft.isbn=978-0-12-137250-7&rft.aulast=Brotherton&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dzt5sAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid5753386-222"><a href="#cite_ref-pmid5753386_222-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGibianKoppKramerNeumann1968" class="citation journal cs1">Gibian H, Kopp R, Kramer M, Neumann F, Richter H (1968). "Effect of particle size on biological activity of norethisterone acetate". Acta Physiologica Latino Americana. 18 (4): 323–326. <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/5753386">5753386</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Physiologica+Latino+Americana&rft.atitle=Effect+of+particle+size+on+biological+activity+of+norethisterone+acetate&rft.volume=18&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E323-%3C%2Fspan%3E326&rft.date=1968&rft_id=info%3Apmid%2F5753386&rft.aulast=Gibian&rft.aufirst=H&rft.au=Kopp%2C+R&rft.au=Kramer%2C+M&rft.au=Neumann%2C+F&rft.au=Richter%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid2112080-223"><a href="#cite_ref-pmid2112080_223-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHeShiLiaoZhu1990" class="citation journal cs1">He CH, Shi YE, Liao DL, Zhu YH, Xu JQ, Matlin SA, et al. (May 1990). "Comparative cross-over pharmacokinetic study on two types of postcoital contraceptive tablets containing levonorgestrel". Contraception. 41 (5): 557–567. <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%2890%2990064-3">10.1016/0010-7824(90)90064-3</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/2112080">2112080</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=Comparative+cross-over+pharmacokinetic+study+on+two+types+of+postcoital+contraceptive+tablets+containing+levonorgestrel&rft.volume=41&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E557-%3C%2Fspan%3E567&rft.date=1990-05&rft_id=info%3Adoi%2F10.1016%2F0010-7824%2890%2990064-3&rft_id=info%3Apmid%2F2112080&rft.aulast=He&rft.aufirst=CH&rft.au=Shi%2C+YE&rft.au=Liao%2C+DL&rft.au=Zhu%2C+YH&rft.au=Xu%2C+JQ&rft.au=Matlin%2C+SA&rft.au=Vince%2C+PM&rft.au=Fotherby%2C+K&rft.au=Van+Look%2C+PF&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-224"><a href="#cite_ref-224">^</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.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=084500">"Estrace: FDA-Approved Drugs"</a>. U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA). Retrieved 6 September 2024.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=U.S.+Food+and+Drug+Administration+%28FDA%29&rft.atitle=Estrace%3A+FDA-Approved+Drugs&rft_id=https%3A%2F%2Fwww.accessdata.fda.gov%2Fscripts%2Fcder%2Fdaf%2Findex.cfm%3Fevent%3Doverview.process%26ApplNo%3D084500&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-KuhlWiegratz2008-225"><a href="#cite_ref-KuhlWiegratz2008_225-0">^</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). Klimakterium, Postmenopause und Hormonsubstitution [Climacteric, Postmenopause and Hormone Replacement] (in German) (4 ed.). UNI-MED-Verlag. p. 18. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-83742-043-2" title="Special:BookSources/978-3-83742-043-2"><bdi>978-3-83742-043-2</bdi></a>. <q>With Progynon Depot-10, an oily solution of 10 mg estradiol valerate, an injection preparation had been available since 1953 and since 1966 coated tablets with estradiol valerate for oral therapy. 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+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid591620-226"><a href="#cite_ref-pmid591620_226-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRiggMilanesVillanuevaYen1977" class="citation journal cs1">Rigg LA, Milanes B, Villanueva B, Yen SS (December 1977). <a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjcem-45-6-1261">"Efficacy of intravaginal and intranasal administration of micronized estradiol-17beta"</a>. The Journal of Clinical Endocrinology and Metabolism. 45 (6): 1261–1264. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjcem-45-6-1261">10.1210/jcem-45-6-1261</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/591620">591620</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Clinical+Endocrinology+and+Metabolism&rft.atitle=Efficacy+of+intravaginal+and+intranasal+administration+of+micronized+estradiol-17beta&rft.volume=45&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1261-%3C%2Fspan%3E1264&rft.date=1977-12&rft_id=info%3Adoi%2F10.1210%2Fjcem-45-6-1261&rft_id=info%3Apmid%2F591620&rft.aulast=Rigg&rft.aufirst=LA&rft.au=Milanes%2C+B&rft.au=Villanueva%2C+B&rft.au=Yen%2C+SS&rft_id=https%3A%2F%2Fdoi.org%2F10.1210%252Fjcem-45-6-1261&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid16530874-227">^ <a href="#cite_ref-pmid16530874_227-0">a</a> <a href="#cite_ref-pmid16530874_227-1">b</a> <a href="#cite_ref-pmid16530874_227-2">c</a> <a href="#cite_ref-pmid16530874_227-3">d</a> <a href="#cite_ref-pmid16530874_227-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFYooLee2006" class="citation journal cs1">Yoo JW, Lee CH (May 2006). "Drug delivery systems for hormone therapy". Journal of Controlled Release. 112 (1): 1–14. <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.jconrel.2006.01.021">10.1016/j.jconrel.2006.01.021</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/16530874">16530874</a>. <q>Transdermal gels. The first system used for estrogen delivery through skin was the application of estrogen dissolved into a water–alcohol solvent in a form of gel for the treatment of postmenopausal symptoms [80] [...] EstroGel (Solvay) has been in the Europe market for more than 25 years, but approved in the US only in 2004. EstroGel contains 17β-estradiol in a hydro-alcoholic gel base which renders a controlled release profile. [...] Estrasorb (Novavax, Malvern, PA) is launched in 2003 as the first topical, lotion-like nanoemulsion for the treatment of vasomotor symptoms. [...] Conventional reservoir patches. The first transdermal patch for HT was Estraderm (Novartis, Switzerland) which was launched in Europe in 1985 and has been widely used ever since. [...] Transdermal matrix patches. [...] Climara (Berlex, Montville, NJ) was first introduced as the matrix patch in 1995. A year later, Vivelle (Novogyne, Miami, FL) was introduced in the market [...]</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+Controlled+Release&rft.atitle=Drug+delivery+systems+for+hormone+therapy&rft.volume=112&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E14&rft.date=2006-05&rft_id=info%3Adoi%2F10.1016%2Fj.jconrel.2006.01.021&rft_id=info%3Apmid%2F16530874&rft.aulast=Yoo&rft.aufirst=JW&rft.au=Lee%2C+CH&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid15845914-228"><a href="#cite_ref-pmid15845914_228-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDavisDinataleRivera-WollDavison2005" class="citation journal cs1">Davis SR, Dinatale I, Rivera-Woll L, Davison S (May 2005). <a rel="nofollow" class="external text" href="https://doi.org/10.1677%2Fjoe.1.05847">"Postmenopausal hormone therapy: from monkey glands to transdermal patches"</a>. The Journal of Endocrinology. 185 (2): 207–222. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1677%2Fjoe.1.05847">10.1677/joe.1.05847</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15845914">15845914</a>. <q>One of the earliest reports of the novel transdermal patch delivery system for oestradiol was published in 1983 (Laufer et al. 1983).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Endocrinology&rft.atitle=Postmenopausal+hormone+therapy%3A+from+monkey+glands+to+transdermal+patches&rft.volume=185&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E207-%3C%2Fspan%3E222&rft.date=2005-05&rft_id=info%3Adoi%2F10.1677%2Fjoe.1.05847&rft_id=info%3Apmid%2F15845914&rft.aulast=Davis&rft.aufirst=SR&rft.au=Dinatale%2C+I&rft.au=Rivera-Woll%2C+L&rft.au=Davison%2C+S&rft_id=https%3A%2F%2Fdoi.org%2F10.1677%252Fjoe.1.05847&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-BensonWatkinson2011-229"><a href="#cite_ref-BensonWatkinson2011_229-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBensonWatkinson2011" class="citation book cs1">Benson HA, Watkinson AC (2011). Benson HA, Watkinson AC (eds.). Transdermal and Topical Drug Delivery Today. Wiley. <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%2F9781118140505">10.1002/9781118140505</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781118140505" title="Special:BookSources/9781118140505"><bdi>9781118140505</bdi></a>. <q>Table 18.1 Passive Transdermal Drugs for Systemic Drug Delivery Launched in the United States and Europe [...] Drug: Estradiol. Indication: Female HRT. U.S. approval: 1986. Marketed in the EU: Yes.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Transdermal+and+Topical+Drug+Delivery+Today&rft.pub=Wiley&rft.date=2011&rft_id=info%3Adoi%2F10.1002%2F9781118140505&rft.isbn=9781118140505&rft.aulast=Benson&rft.aufirst=HA&rft.au=Watkinson%2C+AC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid15040576-230"><a href="#cite_ref-pmid15040576_230-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPrausnitzMitragotriLanger2004" class="citation journal cs1"><a href="/wiki/Mark_Prausnitz" title="Mark Prausnitz">Prausnitz MR</a>, Mitragotri S, Langer R (February 2004). "Current status and future potential of transdermal drug delivery". Nature Reviews. Drug Discovery. 3 (2): 115–124. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnrd1304">10.1038/nrd1304</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/15040576">15040576</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:28888964">28888964</a>. <q>Timeline: Important events in transdermal drug delivery: [...] 1986: Estraderm (17β-oestradiol) patch, FDA approval for hormone replacement.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Reviews.+Drug+Discovery&rft.atitle=Current+status+and+future+potential+of+transdermal+drug+delivery&rft.volume=3&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E115-%3C%2Fspan%3E124&rft.date=2004-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A28888964%23id-name%3DS2CID&rft_id=info%3Apmid%2F15040576&rft_id=info%3Adoi%2F10.1038%2Fnrd1304&rft.aulast=Prausnitz&rft.aufirst=MR&rft.au=Mitragotri%2C+S&rft.au=Langer%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid25560046-231"><a href="#cite_ref-pmid25560046_231-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPastoreKaliaHorstmannRoberts2015" class="citation journal cs1">Pastore MN, Kalia YN, Horstmann M, Roberts MS (May 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4403087">"Transdermal patches: history, development and pharmacology"</a>. 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Menopause. 22 (12): 1308–1316. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2FGME.0000000000000467">10.1097/GME.0000000000000467</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/PMC4666011">4666011</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/25944519">25944519</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Menopause&rft.atitle=Pharmacokinetics+of+the+first+combination+17%CE%B2-estradiol%2Fprogesterone+capsule+in+clinical+development+for+menopausal+hormone+therapy&rft.volume=22&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1308-%3C%2Fspan%3E1316&rft.date=2015-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4666011%23id-name%3DPMC&rft_id=info%3Apmid%2F25944519&rft_id=info%3Adoi%2F10.1097%2FGME.0000000000000467&rft.aulast=Pickar&rft.aufirst=JH&rft.au=Bon%2C+C&rft.au=Amadio%2C+JM&rft.au=Mirkin%2C+S&rft.au=Bernick%2C+B&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4666011&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid26035149-254"><a href="#cite_ref-pmid26035149_254-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKaunitzKaunitz2015" class="citation journal cs1">Kaunitz AM, Kaunitz JD (September 2015). "Compounded bioidentical hormone therapy: time for a reality check?". Menopause. 22 (9): 919–920. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2FGME.0000000000000484">10.1097/GME.0000000000000484</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/26035149">26035149</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Menopause&rft.atitle=Compounded+bioidentical+hormone+therapy%3A+time+for+a+reality+check%3F&rft.volume=22&rft.issue=9&rft.pages=%3Cspan+class%3D%22nowrap%22%3E919-%3C%2Fspan%3E920&rft.date=2015-09&rft_id=info%3Adoi%2F10.1097%2FGME.0000000000000484&rft_id=info%3Apmid%2F26035149&rft.aulast=Kaunitz&rft.aufirst=AM&rft.au=Kaunitz%2C+JD&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid26418479-255">^ <a href="#cite_ref-pmid26418479_255-0">a</a> <a href="#cite_ref-pmid26418479_255-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPinkertonPickar2016" class="citation journal cs1">Pinkerton JV, Pickar JH (February 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4927324">"Update on medical and regulatory issues pertaining to compounded and FDA-approved drugs, including hormone therapy"</a>. Menopause. 23 (2): 215–223. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2FGME.0000000000000523">10.1097/GME.0000000000000523</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/PMC4927324">4927324</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/26418479">26418479</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Menopause&rft.atitle=Update+on+medical+and+regulatory+issues+pertaining+to+compounded+and+FDA-approved+drugs%2C+including+hormone+therapy&rft.volume=23&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E215-%3C%2Fspan%3E223&rft.date=2016-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4927324%23id-name%3DPMC&rft_id=info%3Apmid%2F26418479&rft_id=info%3Adoi%2F10.1097%2FGME.0000000000000523&rft.aulast=Pinkerton&rft.aufirst=JV&rft.au=Pickar%2C+JH&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4927324&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid17549577-256"><a href="#cite_ref-pmid17549577_256-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFugh-BermanBythrow2007" class="citation journal cs1">Fugh-Berman A, Bythrow J (July 2007). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2219716">"Bioidentical hormones for menopausal hormone therapy: variation on a theme"</a>. Journal of General Internal Medicine. 22 (7): 1030–1034. <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%2Fs11606-007-0141-4">10.1007/s11606-007-0141-4</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/PMC2219716">2219716</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/17549577">17549577</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+General+Internal+Medicine&rft.atitle=Bioidentical+hormones+for+menopausal+hormone+therapy%3A+variation+on+a+theme&rft.volume=22&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1030-%3C%2Fspan%3E1034&rft.date=2007-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2219716%23id-name%3DPMC&rft_id=info%3Apmid%2F17549577&rft_id=info%3Adoi%2F10.1007%2Fs11606-007-0141-4&rft.aulast=Fugh-Berman&rft.aufirst=A&rft.au=Bythrow%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2219716&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Melville2015-257"><a href="#cite_ref-Melville2015_257-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMelville2015" class="citation book cs1">Melville C (22 September 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=UiadCgAAQBAJ&pg=PA108">Sexual and Reproductive Health at a Glance</a>. Wiley. pp. 108–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-119-23516-3" title="Special:BookSources/978-1-119-23516-3"><bdi>978-1-119-23516-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034739/https://books.google.com/books?id=UiadCgAAQBAJ&pg=PA108">Archived</a> from the original on 10 June 2022. Retrieved 17 February 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Sexual+and+Reproductive+Health+at+a+Glance&rft.pages=108-&rft.pub=Wiley&rft.date=2015-09-22&rft.isbn=978-1-119-23516-3&rft.aulast=Melville&rft.aufirst=C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DUiadCgAAQBAJ%26pg%3DPA108&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Dollery1991-258"><a href="#cite_ref-Dollery1991_258-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDollery1991" class="citation book cs1">Dollery CT (1991). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=fjBtAAAAMAAJ">Therapeutic Drugs</a>. Churchill Livingstone. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780443028465" title="Special:BookSources/9780443028465"><bdi>9780443028465</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220411035527/https://books.google.com/books?id=fJbtAAAAMAAJ">Archived</a> from the original on 11 April 2022. Retrieved 17 February 2019. <q>Parenteral preparations 1. Oestradiol implants (Organon, UK) are sterilized pellets containing 25, 50 or 100 mg. They are supplied individually in glass tubes.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Therapeutic+Drugs&rft.pub=Churchill+Livingstone&rft.date=1991&rft.isbn=9780443028465&rft.aulast=Dollery&rft.aufirst=CT&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DfjBtAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Kar2005-259"><a href="#cite_ref-Kar2005_259-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKar2005" class="citation book cs1">Kar A (2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=07g30rxCA0EC&pg=PA614">Medicinal Chemistry</a>. New Age International. pp. 614–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-81-224-1565-0" title="Special:BookSources/978-81-224-1565-0"><bdi>978-81-224-1565-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034745/https://books.google.com/books?id=07g30rxCA0EC&pg=PA614">Archived</a> from the original on 10 June 2022. Retrieved 17 February 2019. <q>Oestradiol Implants(R) (Organon, U.K.). Dose. [...] implantation, 20 to 100 mg.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Medicinal+Chemistry&rft.pages=614-&rft.pub=New+Age+International&rft.date=2005&rft.isbn=978-81-224-1565-0&rft.aulast=Kar&rft.aufirst=A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D07g30rxCA0EC%26pg%3DPA614&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Walters1986-260"><a href="#cite_ref-Walters1986_260-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWalters1986" class="citation book cs1">Walters WA (10 July 1986). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ev5rAAAAMAAJ">Transsexualism and sex reassignment</a>. Oxford University Press. p. 159. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-554462-6" title="Special:BookSources/978-0-19-554462-6"><bdi>978-0-19-554462-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034740/https://books.google.com/books?id=ev5rAAAAMAAJ">Archived</a> from the original on 10 June 2022. Retrieved 17 February 2019. <q>2. Injections or implants [...] Oestradiol Implants (Organon) 20 mg pellets. 50 mg pellets. 100 mg pellets.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Transsexualism+and+sex+reassignment&rft.pages=159&rft.pub=Oxford+University+Press&rft.date=1986-07-10&rft.isbn=978-0-19-554462-6&rft.aulast=Walters&rft.aufirst=WA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dev5rAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Braam2006-261"><a href="#cite_ref-Braam2006_261-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBraam2006" class="citation book cs1">Braam WJ (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=NjNUbonqKMYC&pg=PA79">Broze botten</a>. Inmerc. pp. 79–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-90-6611-844-7" title="Special:BookSources/978-90-6611-844-7"><bdi>978-90-6611-844-7</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034741/https://books.google.com/books?id=NjNUbonqKMYC&pg=PA79">Archived</a> from the original on 10 June 2022. Retrieved 17 February 2019.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Broze+botten&rft.pages=79-&rft.pub=Inmerc&rft.date=2006&rft.isbn=978-90-6611-844-7&rft.aulast=Braam&rft.aufirst=WJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DNjNUbonqKMYC%26pg%3DPA79&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Gezondheids-262"><a href="#cite_ref-Gezondheids_262-0">^</a> <a rel="nofollow" class="external free" href="https://www.gezondheidsnet.nl/medicijnen/meno-implantr">https://www.gezondheidsnet.nl/medicijnen/meno-implantr</a>[<a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot">permanent dead link</a>‍] </li> <li id="cite_note-Eskin1988-263"><a href="#cite_ref-Eskin1988_263-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEskin1988" class="citation book cs1">Eskin BA (1988). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Q8ZsAAAAMAAJ">The Menopause: Comprehensive Management</a>. Macmillan. p. 278. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-02-334230-1" title="Special:BookSources/978-0-02-334230-1"><bdi>978-0-02-334230-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034741/https://books.google.com/books?id=Q8ZsAAAAMAAJ">Archived</a> from the original on 10 June 2022. Retrieved 17 February 2019. <q>Estradiol Pellets — (Progynon Pellets — Progynon Associates), 25 mg (Estropel Pellets — Bartor Pharmacal).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Menopause%3A+Comprehensive+Management&rft.pages=278&rft.pub=Macmillan&rft.date=1988&rft.isbn=978-0-02-334230-1&rft.aulast=Eskin&rft.aufirst=BA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DQ8ZsAAAAMAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-AMA1977-264"><a href="#cite_ref-AMA1977_264-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAmerican_Medical_Association._Dept._of_DrugsCouncil_on_Drugs_(American_Medical_Association)American_Society_for_Clinical_Pharmacology_and_Therapeutics1977" class="citation book cs1">American Medical Association. Dept. of Drugs, Council on Drugs (American Medical Association), American Society for Clinical Pharmacology and Therapeutics (1 February 1977). "Estrogens, Progestagens, Oral Contraceptives, and Ovulatory Agents". <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0h7s_rfEZgkC">AMA drug evaluations</a>. Publishing Sciences Group. pp. 540–572. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-88416-175-2" title="Special:BookSources/978-0-88416-175-2"><bdi>978-0-88416-175-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200801102046/https://books.google.com/books?id=0h7s_rfEZgkC">Archived</a> from the original on 1 August 2020. Retrieved 17 February 2019. <q>Subcutaneous implantation: (Estradiol) One 25 mg pellet every three to four months or two 25 mg pellets every four to six months. Preparations. Progynon (Schering). Implantation: Pellets 25 mg.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Estrogens%2C+Progestagens%2C+Oral+Contraceptives%2C+and+Ovulatory+Agents&rft.btitle=AMA+drug+evaluations&rft.pages=%3Cspan+class%3D%22nowrap%22%3E540-%3C%2Fspan%3E572&rft.pub=Publishing+Sciences+Group&rft.date=1977-02-01&rft.isbn=978-0-88416-175-2&rft.au=American+Medical+Association.+Dept.+of+Drugs&rft.au=Council+on+Drugs+%28American+Medical+Association%29&rft.au=American+Society+for+Clinical+Pharmacology+and+Therapeutics&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0h7s_rfEZgkC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-Jones1979-265"><a href="#cite_ref-Jones1979_265-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJones1979" class="citation book cs1">Jones JM (1979). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=hKZKAQAAIAAJ">Physicians' Desk Reference</a>. Medical Economics Company. p. 1508. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8478-9982-1" title="Special:BookSources/978-0-8478-9982-1"><bdi>978-0-8478-9982-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220610034742/https://books.google.com/books?id=hKZKAQAAIAAJ">Archived</a> from the original on 10 June 2022. Retrieved 17 February 2019. <q>PROGYNON Pellets for subcutaneous implantation are cylindrical in shape with an approximate diameter of 3.2 mm. and length of 3.5 mm. Each PROGYNON Pellet contains 25 mg. estradiol.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Physicians%27+Desk+Reference&rft.pages=1508&rft.pub=Medical+Economics+Company&rft.date=1979&rft.isbn=978-0-8478-9982-1&rft.aulast=Jones&rft.aufirst=JM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DhKZKAQAAIAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-BirkhauserBarlow2005-266"><a href="#cite_ref-BirkhauserBarlow2005_266-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBirkhauserBarlowNotelovitzRees2005" class="citation book cs1">Birkhauser M, Barlow D, Notelovitz M, Rees M (12 August 2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=5ZuuGI556GEC&pg=PA27">Health Plan for the Adult Woman: Management Handbook</a>. 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Clinical Obstetrics and Gynecology. 52 (3): 516–529. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2FGRF.0b013e3181b5a395">10.1097/GRF.0b013e3181b5a395</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/PMC2782667">2782667</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/19661765">19661765</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Obstetrics+and+Gynecology&rft.atitle=Transdermal+estradiol+for+postpartum+depression%3A+a+promising+treatment+option&rft.volume=52&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E516-%3C%2Fspan%3E529&rft.date=2009-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2782667%23id-name%3DPMC&rft_id=info%3Apmid%2F19661765&rft_id=info%3Adoi%2F10.1097%2FGRF.0b013e3181b5a395&rft.aulast=Moses-Kolko&rft.aufirst=EL&rft.au=Berga%2C+SL&rft.au=Kalro%2C+B&rft.au=Sit%2C+DK&rft.au=Wisner%2C+KL&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2782667&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid14521476-278"><a href="#cite_ref-pmid14521476_278-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSharma2003" class="citation journal cs1">Sharma V (October 2003). 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Expert Opinion on Pharmacotherapy. 4 (10): 1651–1658. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1517%2F14656566.4.10.1651">10.1517/14656566.4.10.1651</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/14521476">14521476</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:23193276">23193276</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opinion+on+Pharmacotherapy&rft.atitle=Pharmacotherapy+of+postpartum+psychosis&rft.volume=4&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1651-%3C%2Fspan%3E1658&rft.date=2003-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23193276%23id-name%3DS2CID&rft_id=info%3Apmid%2F14521476&rft_id=info%3Adoi%2F10.1517%2F14656566.4.10.1651&rft.aulast=Sharma&rft.aufirst=V&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid26589379-279"><a href="#cite_ref-pmid26589379_279-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCappellettiWallen2016" class="citation journal cs1">Cappelletti M, Wallen K (February 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4720522">"Increasing women's sexual desire: The comparative effectiveness of estrogens and androgens"</a>. Hormones and Behavior. 78: 178–193. <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.yhbeh.2015.11.003">10.1016/j.yhbeh.2015.11.003</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/PMC4720522">4720522</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/26589379">26589379</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Hormones+and+Behavior&rft.atitle=Increasing+women%27s+sexual+desire%3A+The+comparative+effectiveness+of+estrogens+and+androgens&rft.volume=78&rft.pages=%3Cspan+class%3D%22nowrap%22%3E178-%3C%2Fspan%3E193&rft.date=2016-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4720522%23id-name%3DPMC&rft_id=info%3Apmid%2F26589379&rft_id=info%3Adoi%2F10.1016%2Fj.yhbeh.2015.11.003&rft.aulast=Cappelletti&rft.aufirst=M&rft.au=Wallen%2C+K&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4720522&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid26944462-280">^ <a href="#cite_ref-pmid26944462_280-0">a</a> <a href="#cite_ref-pmid26944462_280-1">b</a> <a href="#cite_ref-pmid26944462_280-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSantoroWorsleyMillerParish2016" class="citation journal cs1">Santoro N, Worsley R, Miller KK, Parish SJ, Davis SR (March 2016). "Role of Estrogens and Estrogen-Like Compounds in Female Sexual Function and Dysfunction". The Journal of Sexual Medicine. 13 (3): 305–316. <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.jsxm.2015.11.015">10.1016/j.jsxm.2015.11.015</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/26944462">26944462</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+Sexual+Medicine&rft.atitle=Role+of+Estrogens+and+Estrogen-Like+Compounds+in+Female+Sexual+Function+and+Dysfunction&rft.volume=13&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E305-%3C%2Fspan%3E316&rft.date=2016-03&rft_id=info%3Adoi%2F10.1016%2Fj.jsxm.2015.11.015&rft_id=info%3Apmid%2F26944462&rft.aulast=Santoro&rft.aufirst=N&rft.au=Worsley%2C+R&rft.au=Miller%2C+KK&rft.au=Parish%2C+SJ&rft.au=Davis%2C+SR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"> </li> <li id="cite_note-pmid27789681-281"><a href="#cite_ref-pmid27789681_281-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCriderPillai2017" class="citation journal cs1">Crider A, Pillai A (January 2017). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5193073">"Estrogen Signaling as a Therapeutic Target in Neurodevelopmental Disorders"</a>. The Journal of Pharmacology and Experimental Therapeutics. 360 (1): 48–58. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1124%2Fjpet.116.237412">10.1124/jpet.116.237412</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/PMC5193073">5193073</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/27789681">27789681</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+Pharmacology+and+Experimental+Therapeutics&rft.atitle=Estrogen+Signaling+as+a+Therapeutic+Target+in+Neurodevelopmental+Disorders&rft.volume=360&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E48-%3C%2Fspan%3E58&rft.date=2017-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5193073%23id-name%3DPMC&rft_id=info%3Apmid%2F27789681&rft_id=info%3Adoi%2F10.1124%2Fjpet.116.237412&rft.aulast=Crider&rft.aufirst=A&rft.au=Pillai%2C+A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5193073&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" 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_(medication)&action=edit&section=41" 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="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=%3Cspan+class%3D%22nowrap%22%3E3-%3C%2Fspan%3E63&rft.date=2005-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24616324%23id-name%3DS2CID&rft_id=info%3Apmid%2F16112947&rft_id=info%3Adoi%2F10.1080%2F13697130500148875&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOettelSchillinger2012" class="citation book cs1">Oettel M, Schillinger E (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=0BfrCAAAQBAJ">Estrogens and Antiestrogens I: Physiology and Mechanisms of Action of Estrogens and Antiestrogens</a>. Springer Science & Business Media. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-58616-3" title="Special:BookSources/978-3-642-58616-3"><bdi>978-3-642-58616-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Estrogens+and+Antiestrogens+I%3A+Physiology+and+Mechanisms+of+Action+of+Estrogens+and+Antiestrogens&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-58616-3&rft.aulast=Oettel&rft.aufirst=M&rft.au=Schillinger%2C+E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D0BfrCAAAQBAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOettelSchillinger2012" class="citation book cs1">Oettel M, Schillinger E (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=wBvyCAAAQBAJ">Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen</a>. Springer Science & Business Media. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-60107-1" title="Special:BookSources/978-3-642-60107-1"><bdi>978-3-642-60107-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Estrogens+and+Antiestrogens+II%3A+Pharmacology+and+Clinical+Application+of+Estrogens+and+Antiestrogen&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-3-642-60107-1&rft.aulast=Oettel&rft.aufirst=M&rft.au=Schillinger%2C+E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DwBvyCAAAQBAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFruzzettiTrémollieresBitzer2012" class="citation journal cs1">Fruzzetti F, Trémollieres F, Bitzer J (May 2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3399636">"An overview of the development of combined oral contraceptives containing estradiol: focus on estradiol valerate/dienogest"</a>. Gynecological Endocrinology. 28 (5): 400–408. <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%2F09513590.2012.662547">10.3109/09513590.2012.662547</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/PMC3399636">3399636</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/22468839">22468839</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gynecological+Endocrinology&rft.atitle=An+overview+of+the+development+of+combined+oral+contraceptives+containing+estradiol%3A+focus+on+estradiol+valerate%2Fdienogest&rft.volume=28&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E400-%3C%2Fspan%3E408&rft.date=2012-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3399636%23id-name%3DPMC&rft_id=info%3Apmid%2F22468839&rft_id=info%3Adoi%2F10.3109%2F09513590.2012.662547&rft.aulast=Fruzzetti&rft.aufirst=F&rft.au=Tr%C3%A9mollieres%2C+F&rft.au=Bitzer%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3399636&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" 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 title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Contraception&rft.atitle=Ethinyl+estradiol+and+17%CE%B2-estradiol+in+combined+oral+contraceptives%3A+pharmacokinetics%2C+pharmacodynamics+and+risk+assessment&rft.volume=87&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E706-%3C%2Fspan%3E727&rft.date=2013-06&rft_id=info%3Adoi%2F10.1016%2Fj.contraception.2012.12.011&rft_id=info%3Apmid%2F23375353&rft.aulast=Stanczyk&rft.aufirst=FZ&rft.au=Archer%2C+DF&rft.au=Bhavnani%2C+BR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=Estradiol_(medication)&action=edit&section=42" title="Edit section: External links">edit</a>]</div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a605041.html">"Estradiol Topical: MedlinePlus Drug Information"</a>. MedlinePlus.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=MedlinePlus&rft.atitle=Estradiol+Topical%3A+MedlinePlus+Drug+Information&rft_id=https%3A%2F%2Fmedlineplus.gov%2Fdruginfo%2Fmeds%2Fa605041.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a605042.html">"Estradiol Transdermal Patch: MedlinePlus Drug Information"</a>. MedlinePlus.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=MedlinePlus&rft.atitle=Estradiol+Transdermal+Patch%3A+MedlinePlus+Drug+Information&rft_id=https%3A%2F%2Fmedlineplus.gov%2Fdruginfo%2Fmeds%2Fa605042.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstradiol+%28medication%29" class="Z3988"></li></ul> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output 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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="Estradiol51" 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 class="mw-selflink selflink">Estradiol (as a medication)</a></li> <li><a href="/wiki/Pharmacodynamics_of_estradiol" title="Pharmacodynamics of estradiol">Pharmacodynamics of estradiol</a></li> <li><a href="/wiki/Pharmacokinetics_of_estradiol" title="Pharmacokinetics of estradiol">Pharmacokinetics of estradiol</a></li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogen (as a hormone)</a></li> <li><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen (as a medication)</a></li> <li><a href="/wiki/Hormone_replacement_therapy" title="Hormone replacement therapy">Menopausal hormone therapy</a></li> <li><a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">Feminizing hormone therapy</a></li> <li><a href="/wiki/Estradiol-containing_birth_control_pill" title="Estradiol-containing birth control pill">Estradiol-containing birth control pill</a></li> <li><a href="/wiki/Combined_injectable_birth_control" title="Combined injectable birth control">Combined injectable birth control</a></li> <li><a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">High-dose estrogen</a></li> <li><a href="/wiki/Hydroxylation_of_estradiol" title="Hydroxylation of estradiol">Hydroxylation of estradiol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_ester" title="Estrogen ester">Esters</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a></li> <li><a href="/wiki/Estradiol_acetylsalicylate" title="Estradiol acetylsalicylate">Estradiol acetylsalicylate</a></li> <li><a href="/wiki/Estradiol_anthranilate" title="Estradiol anthranilate">Estradiol anthranilate</a></li> <li><a href="/wiki/Estradiol_benzoate_butyrate" title="Estradiol benzoate butyrate">Estradiol benzoate butyrate</a></li> <li><a href="/wiki/Estradiol_benzoate_cyclooctenyl_ether" title="Estradiol benzoate cyclooctenyl ether">Estradiol benzoate cyclooctenyl ether</a></li> <li><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></li> <li><a href="/wiki/Estradiol_butyrylacetate" title="Estradiol butyrylacetate">Estradiol butyrylacetate</a></li> <li><a href="/wiki/Estradiol_cyclooctyl_acetate" title="Estradiol cyclooctyl acetate">Estradiol cyclooctyl acetate</a></li> <li><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></li> <li><a href="/wiki/Estradiol_decanoate" title="Estradiol decanoate">Estradiol decanoate</a></li> <li><a href="/wiki/Estradiol_diacetate" title="Estradiol diacetate">Estradiol diacetate</a></li> <li><a href="/wiki/Estradiol_dibutyrate" title="Estradiol dibutyrate">Estradiol dibutyrate</a></li> <li><a href="/wiki/Estradiol_dienantate" title="Estradiol dienantate">Estradiol dienantate</a></li> <li><a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">Estradiol dipropionate</a></li> <li><a href="/wiki/Estradiol_distearate" title="Estradiol distearate">Estradiol distearate</a></li> <li><a href="/wiki/Estradiol_disulfate" title="Estradiol disulfate">Estradiol disulfate</a></li> <li><a href="/wiki/Estradiol_diundecylate" title="Estradiol diundecylate">Estradiol diundecylate</a></li> <li><a href="/wiki/Estradiol_diundecylenate" title="Estradiol diundecylenate">Estradiol diundecylenate</a></li> <li><a href="/wiki/Estradiol_enantate" title="Estradiol enantate">Estradiol enantate</a></li> <li><a href="/wiki/Estradiol_furoate" title="Estradiol furoate">Estradiol furoate</a></li> <li><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></li> <li><a href="/wiki/Estradiol_hemisuccinate" title="Estradiol hemisuccinate">Estradiol hemisuccinate</a></li> <li><a href="/wiki/Estradiol_hexahydrobenzoate" title="Estradiol hexahydrobenzoate">Estradiol hexahydrobenzoate</a></li> <li><a href="/wiki/Estradiol_monopropionate" title="Estradiol monopropionate">Estradiol monopropionate</a></li> <li><a href="/wiki/Estradiol_mustard" title="Estradiol mustard">Estradiol mustard</a></li> <li><a href="/wiki/Estradiol_palmitate" title="Estradiol palmitate">Estradiol palmitate</a></li> <li><a href="/wiki/Estradiol_phenylpropionate" title="Estradiol phenylpropionate">Estradiol phenylpropionate</a></li> <li><a href="/wiki/Estradiol_phosphate" title="Estradiol phosphate">Estradiol phosphate</a></li> <li><a href="/wiki/Estradiol_pivalate" title="Estradiol pivalate">Estradiol pivalate</a></li> <li><a href="/wiki/Estradiol_propoxyphenylpropionate" title="Estradiol propoxyphenylpropionate">Estradiol propoxyphenylpropionate</a></li> <li><a href="/wiki/Estradiol_salicylate" title="Estradiol salicylate">Estradiol salicylate</a></li> <li><a href="/wiki/Estradiol_stearate" title="Estradiol stearate">Estradiol stearate</a></li> <li><a href="/wiki/Estradiol_sulfamate" title="Estradiol sulfamate">Estradiol sulfamate</a></li> <li><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></li> <li><a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">Estradiol undecylate</a></li> <li><a href="/wiki/Estradiol_undecylenate" title="Estradiol undecylenate">Estradiol undecylenate</a></li> <li><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate (estradiol normustine phosphate)</a></li> <li><a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Related</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a 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_antiestrogens109" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogens_and_antiestrogens" title="Template talk:Estrogens and antiestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogens_and_antiestrogens" title="Special:EditPage/Template:Estrogens and antiestrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogens_and_antiestrogens109" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a>†</li> <li><a class="mw-selflink selflink">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a>, <a href="/wiki/Estradiol_ester_mixture" class="mw-redirect" title="Estradiol ester mixture">estradiol ester mixtures</a> (<a href="/wiki/Climacteron" class="mw-redirect" title="Climacteron">Climacteron</a>))</li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a> (e.g., <a href="/wiki/Estriol_succinate" title="Estriol succinate">estriol succinate</a>, <a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">polyestriol phosphate</a>)</li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a> <ul><li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a># <ul><li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone; DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate</a></li></ul></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol (stilbestrol)</a></li> <li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters/ethers</a> <ul><li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (diethylstilbestrol dimethyl ether)</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol (diethylstilbestrol monomethyl ether)</a></li></ul></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol (promethestrol)</a> <ul><li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate (promethestrol dipropionate)</a></li></ul></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> (e.g., <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip follicle-stimulating hormone, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip luteinizing hormone)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor antagonists (incl. <a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor modulators/<a href="/wiki/Selective_estrogen_receptor_downregulators" class="mw-redirect" title="Selective estrogen receptor downregulators"><abbr title="selective estrogen receptor downregulators">SERDs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor downregulators)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a>†</li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a>#</li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a>†</li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a 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"><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_modulators1222" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators1222" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol">ent-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol">meso-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol">meso-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li>Unknown/unsorted: <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li>Xenoestrogens: <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (cis-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a 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="/wiki/G-1_(drug)" class="mw-redirect" title="G-1 (drug)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Nicotinic_acid" title="Nicotinic acid">Nicotinic acid</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Nicotinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a 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" 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modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output .portal-bar-content-related{margin:0;list-style:none}.mw-parser-output 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