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.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">Estramustine phosphate</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Estramustine_phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/250px-Estramustine_phosphate.svg.png" decoding="async" width="250" height="161" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/375px-Estramustine_phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/500px-Estramustine_phosphate.svg.png 2x" data-file-width="1995" data-file-height="1285" /></a></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Estramustine_phosphate_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Estramustine_phosphate_molecule_ball.png/250px-Estramustine_phosphate_molecule_ball.png" decoding="async" width="250" height="183" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Estramustine_phosphate_molecule_ball.png/375px-Estramustine_phosphate_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Estramustine_phosphate_molecule_ball.png/500px-Estramustine_phosphate_molecule_ball.png 2x" data-file-width="2560" data-file-height="1878" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Emcyt, Estracyt</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">EMP; Leo 299; NSC-89199; Ro 21-8837/001; Estradiol normustine phosphate; Estradiol 3-normustine 17β-phosphate; Estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(dihydrogen phosphate)</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/emcyt.html">Monograph</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a608046.html">a608046</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/U.S._Food_and_Drug_Administration" class="mw-redirect" title="U.S. Food and Drug Administration">FDA</a>: <a rel="nofollow" class="external text" href="https://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.SearchAction&SearchTerm=Estramustine&SearchType=BasicSearch">Estramustine</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>: D</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/Intravenous_therapy" title="Intravenous therapy">IV</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/Chemotherapeutic_agent" class="mw-redirect" title="Chemotherapeutic agent">Chemotherapeutic agent</a>; <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogen</a>; <a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_L01" title="ATC code L01">L01XX11</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L01XX11">WHO</a>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><abbr class="country-name" title="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></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></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">44–75% (as estramustine and estromustine)<a href="#cite_note-pmid9515186-1">[1]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">• Estradiol: 98%<a href="#cite_note-pmid16112947-2">[2]</a> • Estrone: 96%<a href="#cite_note-pmid16112947-2">[2]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a>, <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestines</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-MSR-6">[6]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">• <a href="/wiki/Estramustine" title="Estramustine">Estramustine</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a> • <a href="/wiki/Estromustine" title="Estromustine">Estromustine</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a> • <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a> • <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a> • <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">Phosphoric acid</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a> • <a href="/wiki/Normustine" title="Normustine">Normustine</a><a href="#cite_note-Inoue2018-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination half-life</a></th><td class="infobox-data">• EMP: 1.27 hours<a href="#cite_note-pmid7579781-5">[5]</a> • Estromustine: 10–14 hrs<a href="#cite_note-pmid9515186-1">[1]</a> • Estrone: 15–17 hours<a href="#cite_note-pmid9515186-1">[1]</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/Bile" title="Bile">Bile</a>, <a href="/wiki/Fece" class="mw-redirect" title="Fece">feces</a> (2.9–4.8%)<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-MSR-6">[6]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">[(8R,9S,13S,14S,17S)-13-methyl-17-phosphonooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] N,N-bis(2-chloroethyl)carbamate</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=4891-15-0">4891-15-0</a> 52205-73-9 (<a href="/wiki/Sodium" title="Sodium">sodium</a>) 325726-21-4 (<a href="/wiki/Meglumine" title="Meglumine">meglumine</a>)</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/259329">259329</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=9076">9076</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/DB01196">DB01196</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.227633.html">227633</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/MUZ9585Y7B">MUZ9585Y7B</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/D02398+D06397">D02398+D06397</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68643">CHEBI:68643</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1756">ChEMBL1756</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> (<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID7048667">DTXSID7048667</a> <a href="https://www.wikidata.org/wiki/Q27137070#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.023.193">100.023.193</a> <a href="https://www.wikidata.org/wiki/Q27137070#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data">C23H32Cl2NO6P</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">520.38 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%5D2OP%28%3DO%29%28O%29O%29CCC4%3DC3C%3DCC%28%3DC4%29OC%28%3DO%29N%28CCCl%29CCCl">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]2OP(=O)(O)O)CCC4=C3C=CC(=C4)OC(=O)N(CCCl)CCCl</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/C23H32Cl2NO6P/c1-23-9-8-18-17-5-3-16(31-22(27)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)32-33(28,29)30/h3,5,14,18-21H,2,4,6-13H2,1H3,(H2,28,29,30)/t18-,19-,20+,21+,23+/m1/s1</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:ADFOJJHRTBFFOF-RBRWEJTLSA-N</div></li></ul> </div></td></tr></tbody></table> Estramustine phosphate (EMP), also known as estradiol normustine phosphate and sold under the brand names Emcyt and Estracyt, is a dual <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> and <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a> medication which is used in the treatment of <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> in men.<a href="#cite_note-EmcytLabel-7">[7]</a><a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid27684806-8">[8]</a><a href="#cite_note-pmid21756277-9">[9]</a><a href="#cite_note-SimpsonWagstaff2003-10">[10]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid9050135-11">[11]</a><a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-pmid8595142-12">[12]</a> It is taken multiple times a day <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a> or by <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">injection into a vein</a>.<a href="#cite_note-EmcytLabel-7">[7]</a><a href="#cite_note-pmid27684806-8">[8]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-pmid8595142-12">[12]</a> <a href="/wiki/Side_effect" title="Side effect">Side effects</a> of EMP include <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</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/Thromboembolism" title="Thromboembolism">blood clots</a>, and <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> complications.<a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid21756277-9">[9]</a><a href="#cite_note-pmid9274433-13">[13]</a> EMP is a dual <a href="/wiki/Cytostatic" class="mw-redirect" title="Cytostatic">cytostatic</a> and hence <a href="/wiki/Chemotherapeutic_agent" class="mw-redirect" title="Chemotherapeutic agent">chemotherapeutic agent</a> and a <a href="/wiki/Hormonal_therapy_(oncology)" title="Hormonal therapy (oncology)">hormonal anticancer agent</a> of the <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> type.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-OettelSchillinger2012-14">[14]</a><a href="#cite_note-pmid7579781-5">[5]</a> It is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Estramustine" title="Estramustine">estramustine</a> and <a href="/wiki/Estromustine" title="Estromustine">estromustine</a> in terms of its cytostatic effects and a prodrug of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> in relation to its <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> effects.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a> EMP has strong estrogenic effects at typical clinical dosages, and consequently has marked <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> and functional <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogenic</a> effects.<a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-OettelSchillinger2012-14">[14]</a> EMP was introduced for medical use in the early 1970s.<a href="#cite_note-pmid11240822-3">[3]</a> It is available in the <a href="/wiki/United_States" title="United States">United States</a>, <a href="/wiki/Canada" title="Canada">Canada</a>, the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a>, other <a href="/wiki/Europe" title="Europe">European</a> countries, and elsewhere in the world.<a href="#cite_note-IndexNominum2000-15">[15]</a><a href="#cite_note-Drugs.com-16">[16]</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=Estramustine_phosphate&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> EMP is indicated, in the <a href="/wiki/United_States" title="United States">United States</a>, for the <a href="/wiki/Palliative_care" title="Palliative care">palliative treatment</a> of <a href="/wiki/Metastatic" class="mw-redirect" title="Metastatic">metastatic</a> and/or progressive prostate cancer,<a href="#cite_note-MSR-6">[6]</a> whereas in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> it is indicated for the treatment of unresponsive or <a href="/wiki/Relapse" title="Relapse">relapsing</a> prostate cancer.<a href="#cite_note-EMP-EMC-17">[17]</a><a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-SimpsonWagstaff2003-10">[10]</a> The medication is usually reserved for use in hormone-refractory cases of prostate cancer, although it has been used as a first-line monotherapy as well.<a href="#cite_note-pmid11240822-3">[3]</a> <a href="/wiki/Response_rate_(medicine)" class="mw-redirect" title="Response rate (medicine)">Response rates</a> with EMP in prostate cancer are said to be equivalent to conventional <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">high-dose estrogen</a> therapy.<a href="#cite_note-Lupulescu1990-18">[18]</a> Due to its relatively severe side effects and toxicity, EMP has rarely been used in the treatment of prostate cancer.<a href="#cite_note-Inoue2018-4">[4]</a> This is especially true in <a href="/wiki/Western_world" title="Western world">Western countries</a> today.<a href="#cite_note-Inoue2018-4">[4]</a> As a result, and also due to the scarce side effects of <a href="/wiki/Gonadotropin-releasing_hormone_modulator" title="Gonadotropin-releasing hormone modulator">gonadotropin-releasing hormone modulators</a> (GnRH modulators) like <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>, EMP was almost abandoned.<a href="#cite_note-pmid11240822-3">[3]</a> However, encouraging clinical research findings resulted in renewed interest of EMP for the treatment of prostate cancer.<a href="#cite_note-pmid11240822-3">[3]</a> EMP has been used at doses of 140 to 1,400 mg/day orally in the treatment of prostate cancer.<a href="#cite_note-StellaBorchardt2007-19">[19]</a> However, oral EMP is most commonly used at a dose of 560 to 640 mg/day (280–320 mg twice daily).<a href="#cite_note-pmid9515186-1">[1]</a> The recommended dosage of oral EMP in the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) label for Emcyt is 14 mg per kg of body weight (i.e., one 140 mg oral capsule for each 10 kg or 22 lbs of body weight) given in 3 or 4 divided doses per day.<a href="#cite_note-EmcytLabel-7">[7]</a> The label states that most patients in studies of oral EMP in the United States have received 10 to 16 mg per kg per day.<a href="#cite_note-EmcytLabel-7">[7]</a> This would be about 900 to 1,440 mg/day for a 90-kg or 200-lb man.<a href="#cite_note-EmcytLabel-7">[7]</a> Lower doses of oral EMP, such as 280 mg/day, have been found to have comparable effectiveness as higher doses but with improved <a href="/wiki/Tolerability" title="Tolerability">tolerability</a> and reduced toxicity.<a href="#cite_note-Inoue2018-4">[4]</a> Doses of 140 mg/day have been described as a very low dosage.<a href="#cite_note-pmid20094950-20">[20]</a> EMP has been used at doses of 240 to 450 mg/day intravenously.<a href="#cite_note-pmid9515186-1">[1]</a> EMP and other estrogens such as <a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">polyestradiol phosphate</a> and <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> are far less costly than newer therapies such as GnRH modulators, <a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">abiraterone acetate</a>, and <a href="/wiki/Enzalutamide" title="Enzalutamide">enzalutamide</a>.<a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid14644018-21">[21]</a><a href="#cite_note-pmid10699602-22">[22]</a> In addition, estrogens may offer significant benefits over other means of <a href="/wiki/Androgen_deprivation_therapy" title="Androgen deprivation therapy">androgen deprivation therapy</a>, for instance in terms of <a href="/wiki/Osteoporosis" title="Osteoporosis">bone loss</a> and <a href="/wiki/Bone_fracture" title="Bone fracture">fractures</a>, <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>, <a href="/wiki/Cognition" title="Cognition">cognition</a>, and <a href="/wiki/Metabolism" title="Metabolism">metabolic status</a>.<a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid10699602-22">[22]</a> EMP has been used to prevent the <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> flare at the start of <a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonist</a> therapy in men with prostate cancer.<a href="#cite_note-pmid7541359-23">[23]</a> <table class="wikitable mw-collapsible mw-collapsed" style="text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><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_prostate_cancer" title="Template:Estrogen dosages for prostate cancer"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_dosages_for_prostate_cancer" title="Template talk:Estrogen dosages for prostate cancer"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_dosages_for_prostate_cancer" title="Special:EditPage/Template:Estrogen dosages for prostate cancer"><abbr title="Edit this template">e</abbr></a></li></ul></div> Estrogen dosages for prostate cancer </caption> <tbody><tr> <th>Route/form</th> <th>Estrogen</th> <th>Dosage </th></tr> <tr> <td rowspan="11"><a href="/wiki/Oral_administration" title="Oral administration">Oral</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>1–2 mg 3x/day </td></tr> <tr> <td><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></td> <td>1.25–2.5 mg 3x/day </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></td> <td>0.15–3 mg/day </td></tr> <tr> <td><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></td> <td>1–2 mg 1x/week </td></tr> <tr> <td><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></td> <td>1–3 mg/day </td></tr> <tr> <td><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a></td> <td>5 mg/day </td></tr> <tr> <td><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a></td> <td>5 mg/day </td></tr> <tr> <td><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol</a></td> <td>100–480 mg 1–3x/day </td></tr> <tr> <td><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></td> <td>12–48 mg/day </td></tr> <tr> <td><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></td> <td>900 mg/day </td></tr> <tr> <td>Estramustine phosphate</td> <td>140–1400 mg/day </td></tr> <tr> <td><a href="/wiki/Transdermal_patch" title="Transdermal patch">Transdermal patch</a></td> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>2–6x 100 μg/day Scrotal: 1x 100 μg/day </td></tr> <tr> <td rowspan="6"><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_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td>1.66 mg 3x/week </td></tr> <tr> <td><a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">Estradiol dipropionate</a></td> <td>5 mg 1x/week </td></tr> <tr> <td><a href="/wiki/Estradiol_valerate" title="Estradiol valerate">Estradiol valerate</a></td> <td>10–40 mg 1x/1–2 weeks </td></tr> <tr> <td><a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">Estradiol undecylate</a></td> <td>100 mg 1x/4 weeks </td></tr> <tr> <td><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></td> <td>Alone: 160–320 mg 1x/4 weeks With oral <abbr title="ethinylestradiol">EE</abbr>: 40–80 mg 1x/4 weeks </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>2–4 mg 2–3x/week </td></tr> <tr> <td rowspan="2"><a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection"><abbr title="Intravenous">IV</abbr> injection</a></td> <td><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol</a></td> <td>300–1200 mg 1–7x/week </td></tr> <tr> <td>Estramustine phosphate</td> <td>240–450 mg/day </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Note: Dosages are not necessarily equivalent. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=2" title="Edit section: Available forms">edit</a>]</div> EMP is or has been available in the form of both <a href="/wiki/Capsule_(pharmacy)" title="Capsule (pharmacy)">capsules</a> (140 mg, 280 mg) for <a href="/wiki/Oral_administration" title="Oral administration">oral administration</a> and <a href="/wiki/Aqueous_solution" title="Aqueous solution">aqueous solutions</a> (300 mg) for <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous injection</a>.<a href="#cite_note-StellaBorchardt2007-19">[19]</a><a href="#cite_note-Muller1998-24">[24]</a><a href="#cite_note-Becker2001-25">[25]</a><a href="#cite_note-EmcytLabel-7">[7]</a> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=3" title="Edit section: Contraindications">edit</a>]</div> EMP is <a href="/wiki/Contraindication" title="Contraindication">contraindicated</a> when used in children, patients <a href="/wiki/Hypersensitivity" title="Hypersensitivity">hypersensitive</a> to estrogens or <a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">nitrogen mustards</a>, those with <a href="/wiki/Peptic_ulcer" class="mw-redirect" title="Peptic ulcer">peptic ulcer</a> (an <a href="/wiki/Ulcer" title="Ulcer">ulcer</a> in the <a href="/wiki/Digestive_tract" class="mw-redirect" title="Digestive tract">digestive tract</a>), those with severely <a href="/wiki/Liver_impairment" class="mw-redirect" title="Liver impairment">compromised liver function</a>, those with weak <a href="/wiki/Heart" title="Heart">heart</a> <a href="/wiki/Muscle" title="Muscle">muscle</a> (also known as <a href="/wiki/Cardiac_insufficiency" class="mw-redirect" title="Cardiac insufficiency">myocardial insufficiency</a>) and those with <a href="/wiki/Thromboembolism" title="Thromboembolism">thromboembolic disorders</a> or complications related to <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a>.<a href="#cite_note-EMP-EMC-17">[17]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=4" title="Edit section: Side effects">edit</a>]</div> The <a href="/wiki/Side_effect" title="Side effect">side effects</a> of EMP overall have been described as relatively severe.<a href="#cite_note-pmid11240822-3">[3]</a> The most common side effects of EMP have been reported to be <a href="/wiki/Gastrointestinal" class="mw-redirect" title="Gastrointestinal">gastrointestinal</a> side effects like <a href="/wiki/Nausea" title="Nausea">nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, and <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, with nausea and vomiting occurring in 40% of men.<a href="#cite_note-pmid21756277-9">[9]</a><a href="#cite_note-pmid9515186-1">[1]</a> They are usually mild or moderate in severity, and the nausea and vomiting can be managed with <a href="/wiki/Prophylactic" class="mw-redirect" title="Prophylactic">prophylactic</a> <a href="/wiki/Antiemetic" title="Antiemetic">antiemetic</a> medications.<a href="#cite_note-pmid21756277-9">[9]</a> Nonetheless, severe cases of gastrointestinal side effects with EMP may require dose reduction or <a href="/wiki/Medication_discontinuation" title="Medication discontinuation">discontinuation</a> of therapy.<a href="#cite_note-pmid9515186-1">[1]</a> Although nausea and vomiting have been reported to be the most common side effects of EMP, <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> (male breast development) has been found to occur in as many as 83% of men treated with EMP, and the incidence of <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a> is possibly similar to or slightly less than the risk of gynecomastia.<a href="#cite_note-pmid11240822-3">[3]</a> As a rule, <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a>, a <a href="/wiki/Gynoid_fat_distribution" title="Gynoid fat distribution">gynoid fat distribution</a>, <a href="/wiki/Demasculinization" class="mw-redirect" title="Demasculinization">demasculinization</a>, and impotence are said to occur in virtually or nearly 100% of men treated with <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">high-dose estrogen</a> therapy.<a href="#cite_note-pmid9274433-13">[13]</a><a href="#cite_note-pmid15663992-26">[26]</a> Decreased <a href="/wiki/Human_sexual_activity" title="Human sexual activity">sexual activity</a> has also been reported in men treated with EMP.<a href="#cite_note-pmid9515186-1">[1]</a> These side effects are due to high <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> levels and low <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> levels.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a> Prophylactic <a href="/wiki/Radiotherapy" class="mw-redirect" title="Radiotherapy">irradiation</a> of the <a href="/wiki/Breast" title="Breast">breasts</a> can be used to decrease the incidence and severity of gynecomastia with estrogens.<a href="#cite_note-pmid9274433-13">[13]</a> Severe adverse effects of EMP are <a href="/wiki/Thromboembolic" class="mw-redirect" title="Thromboembolic">thromboembolic</a> and <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> complications including <a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">pulmonary embolism</a>, <a href="/wiki/Deep_vein_thrombosis" title="Deep vein thrombosis">deep vein thrombosis</a>, <a href="/wiki/Stroke" title="Stroke">stroke</a>, <a href="/wiki/Thrombophlebitis" title="Thrombophlebitis">thrombophlebitis</a>, <a href="/wiki/Coronary_artery_disease" title="Coronary artery disease">coronary artery disease</a> (ischemic heart disease; e.g., <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a>), <a href="/wiki/Thrombophlebitis" title="Thrombophlebitis">thrombophlebitis</a>, and <a href="/wiki/Congestive_heart_failure" class="mw-redirect" title="Congestive heart failure">congestive heart failure</a> with <a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">fluid retention</a>.<a href="#cite_note-pmid21756277-9">[9]</a><a href="#cite_note-pmid9515186-1">[1]</a> EMP produces cardiovascular toxicity similarly to <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>, but to a lesser extent in comparison at low doses (e.g., 280 mg/day oral EMP vs. 1 mg/day oral diethylstilbestrol).<a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid7500443-27">[27]</a> The prostate cancer disease state also increases the risk of thromboembolism, and combination with <a href="/wiki/Docetaxel" title="Docetaxel">docetaxel</a> may exacerbate the risk of thromboembolism as well.<a href="#cite_note-pmid21756277-9">[9]</a> <a href="/wiki/Meta-analysis" title="Meta-analysis">Meta-analyses</a> of <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trials</a> have found that the overall risk of thromboembolism with EMP is 4 to 7%, relative to 0.4% for chemotherapy regimens without EMP.<a href="#cite_note-pmid21756277-9">[9]</a><a href="#cite_note-pmid15536625-28">[28]</a> Thromboembolism is the major <a href="/wiki/Toxicity" title="Toxicity">toxicity</a>-related cause of <a href="/wiki/Medication_discontinuation" title="Medication discontinuation">discontinuation</a> of EMP.<a href="#cite_note-pmid17942366-29">[29]</a> <a href="/wiki/Anticoagulant" title="Anticoagulant">Anticoagulant</a> therapy with medications such as <a href="/wiki/Aspirin" title="Aspirin">aspirin</a>, <a href="/wiki/Warfarin" title="Warfarin">warfarin</a>, unfractionated and low-<a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular-weight</a> <a href="/wiki/Heparin" title="Heparin">heparin</a>, and <a href="/wiki/Vitamin_K_antagonist" title="Vitamin K antagonist">vitamin K antagonists</a> can be useful for decreasing the risk of thromboembolism with EMP and other estrogens like <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a> and <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>.<a href="#cite_note-pmid21756277-9">[9]</a><a href="#cite_note-pmid25920994-30">[30]</a><a href="#cite_note-Inoue2018-4">[4]</a> Adverse <a href="/wiki/Liver_function_tests" title="Liver function tests">liver function tests</a> are commonly seen with EMP, but severe <a href="/wiki/Liver_dysfunction" class="mw-redirect" title="Liver dysfunction">liver dysfunction</a> is rare with the medication.<a href="#cite_note-pmid9515186-1">[1]</a> <a href="/wiki/Central_nervous_system" title="Central nervous system">Central nervous system</a> side effects are rarely seen with EMP, although <a href="/wiki/Ventricular_system#Clinical_significance" title="Ventricular system">enlarged ventricles</a> and <a href="/wiki/Neuron" title="Neuron">neuronal</a> <a href="/wiki/Pigmentation" class="mw-redirect" title="Pigmentation">pigmentation</a> have been reported in monkeys treated with very high doses of EMP (20–140 mg/kg/day) for 3 to 6 months.<a href="#cite_note-pmid9515186-1">[1]</a> EMP does not appear to have cytostatic effects in normal <a href="/wiki/Brain" title="Brain">brain</a> tissue.<a href="#cite_note-pmid9515186-1">[1]</a> In women treated with EMP in clinical studies, a few instances of minor <a href="/wiki/Gynecological" class="mw-redirect" title="Gynecological">gynecological</a> <a href="/wiki/Hemorrhage" class="mw-redirect" title="Hemorrhage">hemorrhages</a> have been observed.<a href="#cite_note-pmid9515186-1">[1]</a> EMP is described as relatively well tolerated among cytostatic antineoplastic and nitrogen-mustard agents, rarely or not at all being associated with significant <a href="/wiki/Hematology" title="Hematology">hematologic</a> <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> such as <a href="/wiki/Myelosuppression" class="mw-redirect" title="Myelosuppression">myelosuppression</a> (bone marrow suppression), gastrointestinal toxicity, or other more marked toxicity associated with such agents.<a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid6375076-31">[31]</a> In contrast to most other cytostatic agents, which often cause myelosuppression, <a href="/wiki/Leukopenia" title="Leukopenia">leukopenia</a> (decreased <a href="/wiki/White_blood_cell" title="White blood cell">white blood cell</a> count), and <a href="/wiki/Neutropenia" title="Neutropenia">neutropenia</a> (decreased <a href="/wiki/Neutrophil" title="Neutrophil">neutrophil</a> count), EMP actually produces <a href="/wiki/Leukocytosis" title="Leukocytosis">leukocytosis</a> (increased white blood cell count) as a side effect.<a href="#cite_note-pmid86404-32">[32]</a><a href="#cite_note-pmid6349745-33">[33]</a> In a small low-dose study using 280 mg/day oral EMP for 150 days, tolerability was significantly improved, with gastrointestinal <a href="/wiki/Irritation" title="Irritation">irritation</a> occurring in only 15% of men, and there was no incidence of severe cardiovascular toxicity or deep vein thrombosis.<a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-Inoue2018-4">[4]</a> In addition, no other side effects besides slight transient <a href="/wiki/Elevated_liver_enzymes" class="mw-redirect" title="Elevated liver enzymes">elevated liver enzymes</a> were observed.<a href="#cite_note-pmid11240822-3">[3]</a> These findings suggest that lower doses of oral EMP may be a safer option than higher doses for the treatment of prostate cancer.<a href="#cite_note-Inoue2018-4">[4]</a> However, a subsequent 2004 <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analysis</a> of 23 studies of thromboembolic events with EMP found substantial incidence of thromboembolic events regardless of dosage and no association of EMP dose with risk of these complications.<a href="#cite_note-pmid15536625-28">[28]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" 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_estramustine_phosphate_(EMC)" title="Template:Side effects of estramustine phosphate (EMC)"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Side_effects_of_estramustine_phosphate_(EMC)" title="Template talk:Side effects of estramustine phosphate (EMC)"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Side_effects_of_estramustine_phosphate_(EMC)" title="Special:EditPage/Template:Side effects of estramustine phosphate (EMC)"><abbr title="Edit this template">e</abbr></a></li></ul></div> Side effects of estramustine phosphate (EMC) </caption> <tbody><tr> <th style="font-weight:bold;"><a href="/wiki/System_organ_class" class="mw-redirect" title="System organ class">System organ class</a> </th> <th style="font-weight:bold;">Very common (≥10%) </th> <th style="font-weight:bold;">Common (1–10%) </th> <th style="font-weight:bold;">Frequency unknownc </th></tr> <tr> <td><a href="/wiki/Blood_disorder" class="mw-redirect" title="Blood disorder">Blood</a> and <a href="/wiki/Lymphatic_disorder" class="mw-redirect" title="Lymphatic disorder">lymphatic system disorders</a> </td> <td><a href="/wiki/Anemia" title="Anemia">Anemia</a>; <a href="/wiki/Leukopenia" title="Leukopenia">Leukopenia</a> </td> <td><a href="/wiki/Thrombocytopenia" title="Thrombocytopenia">Thrombocytopenia</a> </td> <td> </td></tr> <tr> <td><a href="/wiki/Immune_system_disorder" class="mw-redirect" title="Immune system disorder">Immune system disorders</a> </td> <td> </td> <td> </td> <td><a href="/wiki/Hypersensitivity" title="Hypersensitivity">Hypersensitivity</a> </td></tr> <tr> <td><a href="/wiki/Metabolic_disorder" title="Metabolic disorder">Metabolism</a> and <a href="/wiki/Nutrition_disorder" class="mw-redirect" title="Nutrition disorder">nutrition disorders</a> </td> <td><a href="/wiki/Water_retention_(medicine)" class="mw-redirect" title="Water retention (medicine)">Fluid retention</a> </td> <td> </td> <td> </td></tr> <tr> <td><a href="/wiki/Psychiatric_disorder" class="mw-redirect" title="Psychiatric disorder">Psychiatric disorders</a> </td> <td> </td> <td> </td> <td><a href="/wiki/Confusion" title="Confusion">Confusional state</a>; <a href="/wiki/Depression_(mood)" title="Depression (mood)">Depression</a> </td></tr> <tr> <td><a href="/wiki/Nervous_system_disorder" class="mw-redirect" title="Nervous system disorder">Nervous system disorders</a> </td> <td> </td> <td><a href="/wiki/Lethargy" title="Lethargy">Lethargy</a>; <a href="/wiki/Headache" title="Headache">Headache</a> </td> <td> </td></tr> <tr> <td><a href="/wiki/Cardiac_disorder" class="mw-redirect" title="Cardiac disorder">Cardiac disorders</a> </td> <td><a href="/wiki/Congestive_heart_failure" class="mw-redirect" title="Congestive heart failure">Congestive heart failure</a> </td> <td><a href="/wiki/Myocardial_infarction" title="Myocardial infarction">Myocardial infarction</a> </td> <td><a href="/wiki/Myocardial_ischemia" class="mw-redirect" title="Myocardial ischemia">Myocardial ischemia</a> </td></tr> <tr> <td><a href="/wiki/Vascular_disorder" class="mw-redirect" title="Vascular disorder">Vascular disorders</a> </td> <td> </td> <td><a href="/wiki/Embolism" title="Embolism">Embolism</a> </td> <td><a href="/wiki/Hypertension" title="Hypertension">Hypertension</a> </td></tr> <tr> <td><a href="/wiki/Gastrointestinal_disorder" class="mw-redirect" title="Gastrointestinal disorder">Gastrointestinal disorders</a> </td> <td><a href="/wiki/Nausea" title="Nausea">Nausea</a>b; <a href="/wiki/Vomiting" title="Vomiting">Vomiting</a>b; <a href="/wiki/Diarrhea" title="Diarrhea">Diarrhea</a>b </td> <td> </td> <td> </td></tr> <tr> <td><a href="/wiki/Hepatobiliary_disorder" class="mw-redirect" title="Hepatobiliary disorder">Hepatobiliary disorders</a> </td> <td><a href="/wiki/Abnormal_hepatic_function" class="mw-redirect" title="Abnormal hepatic function">Abnormal hepatic function</a> </td> <td> </td> <td> </td></tr> <tr> <td><a href="/wiki/Integumentary_disorder" class="mw-redirect" title="Integumentary disorder">Skin and subcutaneous tissue disorders</a> </td> <td> </td> <td> </td> <td><a href="/wiki/Angioedema" title="Angioedema">Angioedema</a>c; <a href="/wiki/Allergic_dermatitis" class="mw-redirect" title="Allergic dermatitis">Allergic dermatitis</a> </td></tr> <tr> <td><a href="/wiki/Musculoskeletal_disorder" title="Musculoskeletal disorder">Musculoskeletal</a> and <a href="/wiki/Connective_tissue_disorder" class="mw-redirect" title="Connective tissue disorder">connective tissue disorders</a> </td> <td> </td> <td> </td> <td><a href="/wiki/Muscle_weakness" title="Muscle weakness">Muscle weakness</a> </td></tr> <tr> <td><a href="/wiki/Reproductive_disorder" class="mw-redirect" title="Reproductive disorder">Reproductive system</a> and <a href="/wiki/Breast_disorder" class="mw-redirect" title="Breast disorder">breast disorders</a> </td> <td><a href="/wiki/Gynecomastia" title="Gynecomastia">Gynecomastia</a> </td> <td> </td> <td><a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">Erectile dysfunction</a> </td></tr> <tr> <td>General disorders and administration site conditions </td> <td> </td> <td> </td> <td><a href="/wiki/Injection_site_reaction" title="Injection site reaction">Injection site</a> <a href="/wiki/Thrombosis" title="Thrombosis">thrombosis</a> (<a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous"><abbr title="intravenous">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 <a href="/wiki/Solution_(chemistry)" title="Solution (chemistry)">solution</a>) </td></tr> <tr class="sortbottom"> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = Could not be estimated from available data. b = Especially during the first 2 weeks of therapy. c = Angioedema (<a href="/wiki/Quincke_edema" class="mw-redirect" title="Quincke edema">Quincke edema</a>, <a href="/wiki/Larynx_edema" class="mw-redirect" title="Larynx edema">larynx edema</a>) can occur. Often occurs in combination with <a href="/wiki/ACE_inhibitor" title="ACE inhibitor">ACE inhibitors</a>. EMP should be immediately discontinued if angioedema occurs. Sources: See template. </td></tr></tbody></table> <table class="wikitable sortable mw-collapsible mw-collapsed" 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_estramustine_phosphate_(FDA)" title="Template:Side effects of estramustine phosphate (FDA)"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Side_effects_of_estramustine_phosphate_(FDA)" title="Template talk:Side effects of estramustine phosphate (FDA)"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Side_effects_of_estramustine_phosphate_(FDA)" title="Special:EditPage/Template:Side effects of estramustine phosphate (FDA)"><abbr title="Edit this template">e</abbr></a></li></ul></div> Side effects of estramustine phosphate (FDA) </caption> <tbody><tr> <th><a href="/wiki/Side_effect" title="Side effect">Side effect</a></th> <th>Estramustine phosphate (oral 11.5–15.9 mg/kg/day) (n = 93) (%)</th> <th><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> (oral 3.0 mg/day) (n = 93) (%) </th></tr> <tr> <th colspan="3"><a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">Cardiovascular</a> and <a href="/wiki/Respiratory" class="mw-redirect" title="Respiratory">respiratory</a> </th></tr> <tr> <td><a href="/wiki/Cardiac_arrest" title="Cardiac arrest">Cardiac arrest</a></td> <td>0</td> <td>2 </td></tr> <tr> <td><a href="/wiki/Cerebrovascular_accident" class="mw-redirect" title="Cerebrovascular accident">Cerebrovascular accident</a> (stroke)</td> <td>2</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Myocardial_infarction" title="Myocardial infarction">Myocardial infarction</a> (heart attack)</td> <td>3</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Thrombophlebitis" title="Thrombophlebitis">Thrombophlebitis</a></td> <td>3</td> <td>7 </td></tr> <tr> <td><a href="/wiki/Pulmonary_embolism" title="Pulmonary embolism">Pulmonary embolism</a></td> <td>2</td> <td>5 </td></tr> <tr> <td><a href="/wiki/Congestive_heart_failure" class="mw-redirect" title="Congestive heart failure">Congestive heart failure</a></td> <td>3</td> <td>2 </td></tr> <tr> <td><a href="/wiki/Edema" title="Edema">Edema</a> (<a href="/wiki/Swelling_(medical)" class="mw-redirect" title="Swelling (medical)">swelling</a>)</td> <td>19</td> <td>17 </td></tr> <tr> <td><a href="/wiki/Dyspnea" class="mw-redirect" title="Dyspnea">Dyspnea</a> (shortness of breath)</td> <td>11</td> <td>3 </td></tr> <tr> <td><a href="/wiki/Leg_cramps" class="mw-redirect" title="Leg cramps">Leg cramps</a></td> <td>8</td> <td>11 </td></tr> <tr> <td><a href="/wiki/Upper_respiratory_discharge" class="mw-redirect" title="Upper respiratory discharge">Upper respiratory discharge</a></td> <td>1</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Hoarseness" class="mw-redirect" title="Hoarseness">Hoarseness</a></td> <td>1</td> <td>0 </td></tr> <tr> <th colspan="3"><a href="/wiki/Gastrointestinal" class="mw-redirect" title="Gastrointestinal">Gastrointestinal</a> </th></tr> <tr> <td><a href="/wiki/Nausea" title="Nausea">Nausea</a></td> <td>15</td> <td>8 </td></tr> <tr> <td><a href="/wiki/Diarrhea" title="Diarrhea">Diarrhea</a></td> <td>12</td> <td>11 </td></tr> <tr> <td>Minor <a href="/wiki/Gastrointestinal_upset" class="mw-redirect" title="Gastrointestinal upset">gastrointestinal upset</a></td> <td>11</td> <td>6 </td></tr> <tr> <td><a href="/wiki/Anorexia_(symptom)" title="Anorexia (symptom)">Anorexia</a> (appetite loss)</td> <td>4</td> <td>3 </td></tr> <tr> <td><a href="/wiki/Flatulence" title="Flatulence">Flatulence</a></td> <td>2</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Vomiting" title="Vomiting">Vomiting</a></td> <td>1</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Gastrointestinal_bleeding" title="Gastrointestinal bleeding">Gastrointestinal bleeding</a></td> <td>1</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Burning_throat" class="mw-redirect" title="Burning throat">Burning throat</a></td> <td>1</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Thirst" title="Thirst">Thirst</a></td> <td>1</td> <td>0 </td></tr> <tr> <th colspan="3"><a href="/wiki/Integumentary" class="mw-redirect" title="Integumentary">Integumentary</a> </th></tr> <tr> <td><a href="/wiki/Rash" title="Rash">Rash</a></td> <td>1</td> <td>4 </td></tr> <tr> <td><a href="/wiki/Pruritus" class="mw-redirect" title="Pruritus">Pruritus</a> (itching)</td> <td>2</td> <td>2 </td></tr> <tr> <td><a href="/wiki/Dry_skin" class="mw-redirect" title="Dry skin">Dry skin</a></td> <td>2</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Pigmentation" class="mw-redirect" title="Pigmentation">Pigment changes</a></td> <td>0</td> <td>3 </td></tr> <tr> <td><a href="/wiki/Easy_bruising" class="mw-redirect" title="Easy bruising">Easy bruising</a></td> <td>3</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Flushing_(physiology)" title="Flushing (physiology)">Flushing</a></td> <td>1</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Night_sweat" class="mw-redirect" title="Night sweat">Night sweats</a></td> <td>0</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Skin_peeling" class="mw-redirect" title="Skin peeling">Peeling of fingertip skin</a></td> <td>1</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Scalp_hair_loss" class="mw-redirect" title="Scalp hair loss">Thinning hair</a></td> <td>1</td> <td>1 </td></tr> <tr> <th colspan="3"><a href="/wiki/Breast" title="Breast">Breast</a> changes </th></tr> <tr> <td><a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">Breast tenderness</a></td> <td>66</td> <td>64 </td></tr> <tr> <td colspan="3"><a href="/wiki/Mammoplasia" title="Mammoplasia">Breast enlargement</a> (<a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a> or male <a href="/wiki/Breast_development" title="Breast development">breast development</a>) </td></tr> <tr> <td>  Mild</td> <td>60</td> <td>54 </td></tr> <tr> <td>  Moderate</td> <td>10</td> <td>16 </td></tr> <tr> <td>  Marked</td> <td>0</td> <td>5 </td></tr> <tr> <th colspan="3">Miscellaneous </th></tr> <tr> <td><a href="/wiki/Lethargy" title="Lethargy">Lethargy</a> alone</td> <td>4</td> <td>3 </td></tr> <tr> <td><a href="/wiki/Depression_(mood)" title="Depression (mood)">Depression</a></td> <td>0</td> <td>2 </td></tr> <tr> <td><a href="/wiki/Emotional_lability" title="Emotional lability">Emotional lability</a></td> <td>2</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Insomnia" title="Insomnia">Insomnia</a></td> <td>3</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Headache" title="Headache">Headache</a></td> <td>1</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Anxiety" title="Anxiety">Anxiety</a></td> <td>1</td> <td>0 </td></tr> <tr> <td><a href="/wiki/Chest_pain" title="Chest pain">Chest pain</a></td> <td>1</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Hot_flash" title="Hot flash">Hot flashes</a></td> <td>0</td> <td>1 </td></tr> <tr> <td><a href="/w/index.php?title=Eye_pain&action=edit&redlink=1" class="new" title="Eye pain (page does not exist)">Eye pain</a></td> <td>0</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Lacrimation" class="mw-redirect" title="Lacrimation">Lacrimation</a> (eye tears)</td> <td>1</td> <td>1 </td></tr> <tr> <td><a href="/wiki/Tinnitus" title="Tinnitus">Tinnitus</a></td> <td>0</td> <td>1 </td></tr> <tr> <th colspan="3">Laboratory abnormalities </th></tr> <tr> <td colspan="3"><a href="/wiki/Hematologic" class="mw-redirect" title="Hematologic">Hematologic</a> (<a href="/wiki/Blood" title="Blood">blood</a>) </td></tr> <tr> <td><a href="/wiki/Leukopenia" title="Leukopenia">Leukopenia</a> (low <a href="/wiki/White_blood_cell" title="White blood cell">white blood cells</a>)</td> <td>4</td> <td>2 </td></tr> <tr> <td><a href="/wiki/Thrombopenia" class="mw-redirect" title="Thrombopenia">Thrombopenia</a> (low <a href="/wiki/Platelet" title="Platelet">platelets</a>)</td> <td>1</td> <td>2 </td></tr> <tr> <td colspan="3"><a href="/wiki/Hepatic" class="mw-redirect" title="Hepatic">Hepatic</a> (liver) </td></tr> <tr> <td><a href="/wiki/Bilirubin" title="Bilirubin">Bilirubin</a> alone</td> <td>1</td> <td>5 </td></tr> <tr> <td>Bilirubin and <a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase"><abbr title="lactate dehydrogenase">LDH</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 lactate dehydrogenase</td> <td>0</td> <td>1 </td></tr> <tr> <td>Bilirubin and <a href="/wiki/Aspartate_transaminase" title="Aspartate transaminase"><abbr title="aspartate transaminase">AST</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 aspartate transaminase</td> <td>2</td> <td>1 </td></tr> <tr> <td>Bilirubin, LDH, and SGOT</td> <td>2</td> <td>0 </td></tr> <tr> <td>LDH and/or SGOT</td> <td>31</td> <td>28 </td></tr> <tr> <td colspan="3">Miscellaneous </td></tr> <tr> <td>Transient <a href="/wiki/Hypercalcemia" class="mw-redirect" title="Hypercalcemia">hypercalcemia</a> (high <a href="/wiki/Calcium" title="Calcium">calcium</a>)</td> <td>0</td> <td>1 </td></tr> <tr class="sortbottom"> <td colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;">Sources: <a href="#cite_note-Emcyt-Label-34">[34]</a> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=5" title="Edit section: Overdose">edit</a>]</div> There has been no clinical experience with <a href="/wiki/Overdose" class="mw-redirect" title="Overdose">overdose</a> of EMP.<a href="#cite_note-EmcytLabel-7">[7]</a> Overdose of EMP may result in pronounced manifestations of the known adverse effects of the medication.<a href="#cite_note-EmcytLabel-7">[7]</a> There is no specific <a href="/wiki/Antidote" title="Antidote">antidote</a> for overdose of EMP.<a href="#cite_note-EMP-EMC-17">[17]</a> In the event of overdose, <a href="/wiki/Gastric_lavage" title="Gastric lavage">gastric lavage</a> should be used to evacuate gastric contents as necessary and treatment should be <a href="/wiki/Symptom" class="mw-redirect" title="Symptom">symptom</a>-based and supportive.<a href="#cite_note-EmcytLabel-7">[7]</a><a href="#cite_note-EMP-EMC-17">[17]</a> In the case of dangerously low counts of <a href="/wiki/Red_blood_cell" title="Red blood cell">red blood cells</a>, <a href="/wiki/White_blood_cell" title="White blood cell">white blood cells</a>, or <a href="/wiki/Platelet" title="Platelet">platelets</a>, <a href="/wiki/Whole_blood" title="Whole blood">whole blood</a> may be given as needed.<a href="#cite_note-EMP-EMC-17">[17]</a> <a href="/wiki/Liver" title="Liver">Liver</a> function should be monitored with EMP overdose.<a href="#cite_note-EMP-EMC-17">[17]</a> After an overdose of EMP, <a href="/wiki/Hematological" class="mw-redirect" title="Hematological">hematological</a> and <a href="/wiki/Liver" title="Liver">hepatic</a> parameters should continue to be monitored for at least 6 weeks.<a href="#cite_note-EmcytLabel-7">[7]</a> EMP has been used at high doses of as much as 1,260 mg/day by the <a href="/wiki/Oral_administration" title="Oral administration">oral</a> route and 240 to 450 mg/day by <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">intravenous injection</a>.<a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=6" title="Edit section: Interactions">edit</a>]</div> EMP has been reported to increase the <a href="/wiki/Efficacy" title="Efficacy">efficacy</a> and <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> of <a href="/wiki/Tricyclic_antidepressants" class="mw-redirect" title="Tricyclic antidepressants">tricyclic antidepressants</a> like <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a> and <a href="/wiki/Imipramine" title="Imipramine">imipramine</a>.<a href="#cite_note-EMP-EMC-17">[17]</a> When products containing <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, and/or <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, such as <a href="/wiki/Dairy_product" title="Dairy product">dairy products</a> like <a href="/wiki/Milk" title="Milk">milk</a>, various <a href="/wiki/Food" title="Food">foods</a> <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplements</a>, and <a href="/wiki/Antacid" title="Antacid">antacids</a>, are consumed concomitantly with EMP, an <a href="/wiki/Water_solubility" class="mw-redirect" title="Water solubility">insoluble</a> <a href="/wiki/Chelate_complex" class="mw-redirect" title="Chelate complex">chelate complex</a>/<a href="/wiki/Phosphate" title="Phosphate">phosphate</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> between EMP and these <a href="/wiki/Metal" title="Metal">metals</a> can be formed, and this can markedly impair the <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> and hence <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of EMP.<a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-EMP-EMC-17">[17]</a> There may be an increased risk of <a href="/wiki/Angioedema" title="Angioedema">angioedema</a> in those concurrently taking <a href="/wiki/ACE_inhibitor" title="ACE inhibitor">ACE inhibitors</a>.<a href="#cite_note-EMP-EMC-17">[17]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=7" title="Edit section: Pharmacology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=8" title="Edit section: Pharmacodynamics">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Pharmacodynamics_of_estradiol" title="Pharmacodynamics of estradiol">Pharmacodynamics of estradiol</a></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Estramustine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Estramustine.svg/250px-Estramustine.svg.png" decoding="async" width="250" height="159" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Estramustine.svg/375px-Estramustine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Estramustine.svg/500px-Estramustine.svg.png 2x" data-file-width="512" data-file-height="325" /></a><figcaption><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a>, the major active cytostatic form of estramustine phosphate.</figcaption></figure> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Estradiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/250px-Estradiol.svg.png" decoding="async" width="250" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/375px-Estradiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/500px-Estradiol.svg.png 2x" data-file-width="512" data-file-height="324" /></a><figcaption><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a>, the major active estrogenic form of estramustine phosphate.</figcaption></figure> EMP, also known as estradiol normustine phosphate, is a combined <a href="/wiki/Estrogen_ester" title="Estrogen ester">estrogen ester</a> and <a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">nitrogen mustard</a> <a href="/wiki/Ester" title="Ester">ester</a>.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-OettelSchillinger2012-14">[14]</a> It consists of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>, an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a>, linked with a <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> ester as well as an ester of <a href="/wiki/Normustine" title="Normustine">normustine</a>, a nitrogen mustard.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-OettelSchillinger2012-14">[14]</a> In terms of its <a href="/wiki/Pharmacodynamic" class="mw-redirect" title="Pharmacodynamic">pharmacodynamic</a> effects, EMP is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> of <a href="/wiki/Estramustine" title="Estramustine">estramustine</a>, <a href="/wiki/Estromustine" title="Estromustine">estromustine</a>, and <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a> As a prodrug of estradiol, EMP is an estrogen and hence an <a href="/wiki/Agonist" title="Agonist">agonist</a> of the <a href="/wiki/Estrogen_receptor" title="Estrogen receptor">estrogen receptors</a>.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid16112947-2">[2]</a> EMP itself has only very weak <a href="/wiki/Affinity_(pharmacology)" class="mw-redirect" title="Affinity (pharmacology)">affinity</a> for the estrogen receptors.<a href="#cite_note-pmid9515186-1">[1]</a> The medication is of about 91% higher <a href="/wiki/Molecular_weight" class="mw-redirect" title="Molecular weight">molecular weight</a> than estradiol due to the presence of its C3 normustine and C17β phosphate esters.<a href="#cite_note-Elks2014-35">[35]</a><a href="#cite_note-IndexNominum2000-15">[15]</a> Because EMP is a prodrug of estradiol, it may be considered to be a <a href="/wiki/Natural_product" title="Natural product">natural</a> and <a href="/wiki/Bioidentical_hormone_replacement_therapy" title="Bioidentical hormone replacement therapy">bioidentical</a> form of estrogen,<a href="#cite_note-OettelSchillinger2012-14">[14]</a> although it does have additional cytostatic activity via estramustine and estromustine.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a> EMP acts by a dual <a href="/wiki/Mechanism_of_action" title="Mechanism of action">mechanism of action</a>: 1) direct cytostatic activity via a number of actions; and 2) as a form of <a href="/wiki/High-dose_estrogen" class="mw-redirect" title="High-dose estrogen">high-dose estrogen</a> therapy via estrogen receptor-mediated <a href="/wiki/Antigonadotropic" class="mw-redirect" title="Antigonadotropic">antigonadotropic</a> and functional <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogenic</a> effects.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-OettelSchillinger2012-14">[14]</a> The antigonadotropic and functional antiandrogenic effects of EMP consist of strong suppression of <a href="/wiki/Gonad" title="Gonad">gonadal</a> <a href="/wiki/Androgen" title="Androgen">androgen</a> <a href="/wiki/Biosynthesis" title="Biosynthesis">production</a> and hence circulating levels of androgens such as <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>; greatly increased levels of <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> and hence a decreased fraction of free androgens in the <a href="/wiki/Circulatory_system" title="Circulatory system">circulation</a>; and direct antiandrogenic actions in prostate cells.<a href="#cite_note-pmid6375076-31">[31]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid10076535-36">[36]</a><a href="#cite_note-pmid2093302-37">[37]</a><a href="#cite_note-pmid7190620-38">[38]</a> The free androgen index with oral EMP has been found to be on average 4.6-fold lower than with <a href="/wiki/Orchiectomy" title="Orchiectomy">orchiectomy</a>.<a href="#cite_note-pmid2093302-37">[37]</a> As such, EMP therapy results in considerably stronger <a href="/wiki/Androgen_deprivation_therapy" title="Androgen deprivation therapy">androgen deprivation</a> than orchiectomy.<a href="#cite_note-pmid7190620-38">[38]</a> Metabolites of EMP, including estramustine, estromustine, estradiol, and <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a>, have been found to act as weak <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a> of the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (<a href="/wiki/Half-maximal_effective_concentration" class="mw-redirect" title="Half-maximal effective concentration"><abbr title="half-maximal effective concentration">EC50</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 half-maximal effective concentration = 0.5–3.1 μM), although the clinical significance of this is unknown.<a href="#cite_note-pmid12084341-39">[39]</a><a href="#cite_note-pmid10076535-36">[36]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid9515186-1">[1]</a> Extremely high levels of estradiol and estrone occur during EMP therapy.<a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-Inoue2018-4">[4]</a> The estrogenic <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> of EMP are responsible for its most common adverse effects and its <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a> <a href="/wiki/Toxicity" title="Toxicity">toxicity</a>.<a href="#cite_note-pmid9515186-1">[1]</a> EMP has been described as having relatively weak estrogenic effects in some publications.<a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-pmid6375076-31">[31]</a> However, it has shown essentially the same rates and degrees of estrogenic effects, such as <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a>, <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a>, cardiovascular toxicity, changes in <a href="/wiki/Liver_protein_synthesis" class="mw-redirect" title="Liver protein synthesis">liver protein synthesis</a>, and testosterone suppression, as high-dose <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a> and <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> in clinical studies.<a href="#cite_note-EmcytLabel-7">[7]</a><a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid6375076-31">[31]</a><a href="#cite_note-pmid7190620-38">[38]</a><a href="#cite_note-pmid3092893-40">[40]</a> The notion that EMP has relatively weak estrogen activity may have been based on <a href="/wiki/Animal_research" class="mw-redirect" title="Animal research">animal research</a>, which found that EMP had 100-fold lower <a href="/wiki/Uterotrophic" class="mw-redirect" title="Uterotrophic">uterotrophic</a> effects than estradiol in rats, and may also not have taken into account the very high doses of EMP used clinically in humans.<a href="#cite_note-pmid3092893-40">[40]</a><a href="#cite_note-Fredholm1974-41">[41]</a> The mechanism of action of the <a href="/wiki/Cytostatic" class="mw-redirect" title="Cytostatic">cytostatic</a> effects of EMP is complex and only partially understood.<a href="#cite_note-pmid9515186-1">[1]</a> EMP is considered to mainly be a <a href="/wiki/Mitotic_inhibitor" title="Mitotic inhibitor">mitotic inhibitor</a>, inhibiting mechanisms involved in the <a href="/wiki/Mitosis" title="Mitosis">mitosis</a> phase of the <a href="/wiki/Cell_cycle" title="Cell cycle">cell cycle</a>.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-Inoue2018-4">[4]</a> Specifically, it binds to <a href="/wiki/Microtubule-associated_protein" title="Microtubule-associated protein">microtubule-associated proteins</a> and/or to <a href="/wiki/Tubulin" title="Tubulin">tubulin</a> and produces <a href="/wiki/Depolymerization" title="Depolymerization">depolymerization</a> of <a href="/wiki/Microtubule" title="Microtubule">microtubules</a> (Kd = 10–20 μM for estramustine), resulting in the arrest of <a href="/wiki/Cell_division" title="Cell division">cell division</a> in the <a href="/wiki/G2_phase#G2/M_Checkpoint" title="G2 phase">G2/M phase</a> (specifically <a href="/wiki/Metaphase" title="Metaphase">metaphase</a>).<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid1545778-42">[42]</a> EMP was originally thought to mediate its cytostatic effects as a prodrug of <a href="/wiki/Normustine" title="Normustine">normustine</a>, a <a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">nitrogen mustard</a>, and hence was thought to be an <a href="/wiki/Alkylating_antineoplastic_agent" title="Alkylating antineoplastic agent">alkylating antineoplastic agent</a>.<a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-SimpsonWagstaff2003-10">[10]</a><a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-OettelSchillinger2012-14">[14]</a> However, subsequent research has found that EMP is devoid of alkylating actions, and that the influence of EMP on microtubules is mediated by intact estramustine and estromustine, with normustine or estradiol alone having only minor or negligible effects.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid6373212-43">[43]</a> As such, the unique properties of the estramustine and estromustine <a href="/wiki/Chemical_structure" title="Chemical structure">structures</a>, containing a <a href="/wiki/Carbamate" title="Carbamate">carbamate</a>-<a href="/wiki/Ester" title="Ester">ester</a> <a href="/wiki/Chemical_bond" title="Chemical bond">bond</a>, appear to be responsible for the cytostatic effects of EMP.<a href="#cite_note-pmid9515186-1">[1]</a> In addition to its antimitotic actions, EMP has also been found to produce other cytostatic effects, including induction of <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>, interference with <a href="/wiki/DNA_synthesis" title="DNA synthesis">DNA synthesis</a>, <a href="/wiki/Nuclear_matrix" title="Nuclear matrix">nuclear matrix</a> interaction, <a href="/wiki/Cell_membrane" title="Cell membrane">cell membrane</a> alterations, induction of <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> (free oxygen radicals), and possibly additional mechanisms.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-Inoue2018-4">[4]</a> EMP has been found to have a <a href="/wiki/Radiosensitizer" title="Radiosensitizer">radiosensitizing</a> effect in prostate cancer and <a href="/wiki/Glioma" title="Glioma">glioma</a> cells, improving sensitivity to <a href="/wiki/Radiation_therapy" title="Radiation therapy">radiation therapy</a> as well.<a href="#cite_note-pmid9515186-1">[1]</a> The cytostatic metabolites of EMP are accumulated in <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a> in a <a href="/wiki/Tissue_selectivity" title="Tissue selectivity">selective</a> manner, for instance in <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a>.<a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-Inoue2018-4">[4]</a> This may be due to the presence of a specific estramustine-binding protein (EMBP) (Kd = 10–35 nM for estramustine), also known as prostatin or prostatic secretion protein (PSP), which has been detected in prostate cancer, <a href="/wiki/Glioma" title="Glioma">glioma</a>, <a href="/wiki/Melanoma" title="Melanoma">melanoma</a>, and <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a> cells.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid2682681-44">[44]</a> Because of its tissue selectivity, EMP is said to produce minimal cytostatic effects in healthy tissues, and its tissue selectivity may be responsible for its therapeutic cytostatic efficacy against prostate cancer cells.<a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid9515186-1">[1]</a> EMP was originally developed as a dual ester prodrug of an estrogen and normustine as a nitrogen mustard alkylating antineoplastic agent which, due to the affinity of the estrogen <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a> for estrogen receptors, would be selectively accumulated in estrogen target tissues and hence estrogen receptor-positive <a href="/wiki/Tumor" class="mw-redirect" title="Tumor">tumor</a> cells.<a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-OettelSchillinger2012-14">[14]</a><a href="#cite_note-pmid16112947-2">[2]</a> Consequentially, it was thought that EMP would preferentially deliver the alkylating normustine moiety to these tissues, allowing for reduced cytostatic effects in healthy tissues and hence improved <a href="/wiki/Efficacy" title="Efficacy">efficacy</a> and <a href="/wiki/Tolerability" title="Tolerability">tolerability</a>.<a href="#cite_note-Inoue2018-4">[4]</a> However, subsequent research found that there is very limited and slow <a href="/wiki/Bond_cleavage" title="Bond cleavage">cleavage</a> of the normustine ester and that EMP is devoid of alkylating activity.<a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-pmid6375076-31">[31]</a> In addition, it appears that estramustine and estromustine may be preferentially accumulated in estrogen target tissues not due to affinity for the estrogen receptors, but instead due to affinity for the distinct EMBP.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a> Extremely high, <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>-like levels of estradiol may be responsible for the <a href="/wiki/Leukocytosis" title="Leukocytosis">leukocytosis</a> (increased <a href="/wiki/White_blood_cell" title="White blood cell">white blood cell</a> count) that is observed in individuals treated with EMP.<a href="#cite_note-pmid86404-32">[32]</a><a href="#cite_note-pmid6349745-33">[33]</a> This side effect is in contrast to most other cytotoxic agents, which instead cause <a href="/wiki/Myelosuppression" class="mw-redirect" title="Myelosuppression">myelosuppression</a> (<a href="/wiki/Bone_marrow" title="Bone marrow">bone marrow</a> suppression), <a href="/wiki/Leukopenia" title="Leukopenia">leukopenia</a> (decreased white blood cell count), and <a href="/wiki/Neutropenia" title="Neutropenia">neutropenia</a> (decreased <a href="/wiki/Neutrophil" title="Neutrophil">neutrophil</a> count).[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] <div class="mw-heading mw-heading4"><h4 id="Antigonadotropic_effects">Antigonadotropic effects</h4>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=9" title="Edit section: Antigonadotropic effects">edit</a>]</div> EMP at a dosage 280 mg/day has been found to suppress testosterone levels in men into the <a href="/wiki/Castration" title="Castration">castrate</a> range (to 30 ng/dL) within 20 days and to the low castrate range (to 10 ng/dL) within 30 days.<a href="#cite_note-pmid11240822-3">[3]</a> Similarly, a dosage of 70 mg/day EMP suppressed testosterone levels into the castrate range within 4 weeks.<a href="#cite_note-pmid11240822-3">[3]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=10" title="Edit section: Pharmacokinetics">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Pharmacokinetics_of_estradiol" title="Pharmacokinetics of estradiol">Pharmacokinetics of estradiol</a></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Estradiol_and_testosterone_levels_with_280_mg_per_day_oral_estramustine_phosphate_in_men_with_prostate_cancer.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/Estradiol_and_testosterone_levels_with_280_mg_per_day_oral_estramustine_phosphate_in_men_with_prostate_cancer.png/450px-Estradiol_and_testosterone_levels_with_280_mg_per_day_oral_estramustine_phosphate_in_men_with_prostate_cancer.png" decoding="async" width="450" height="267" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/98/Estradiol_and_testosterone_levels_with_280_mg_per_day_oral_estramustine_phosphate_in_men_with_prostate_cancer.png/675px-Estradiol_and_testosterone_levels_with_280_mg_per_day_oral_estramustine_phosphate_in_men_with_prostate_cancer.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/98/Estradiol_and_testosterone_levels_with_280_mg_per_day_oral_estramustine_phosphate_in_men_with_prostate_cancer.png/900px-Estradiol_and_testosterone_levels_with_280_mg_per_day_oral_estramustine_phosphate_in_men_with_prostate_cancer.png 2x" data-file-width="1869" data-file-height="1107" /></a><figcaption>Estradiol and testosterone levels during therapy with 280 mg/day oral EMP in men with prostate cancer (n = 11).<a href="#cite_note-pmid11240822-3">[3]</a></figcaption></figure> <table class="wikitable floatright"> <caption>Pharmacokinetics of estromustine after a single dose of EMP in men with prostate cancer (n = 5) </caption> <tbody><tr> <th>Parameter</th> <th><abbr title="intravenous injection">IV</abbr> 300 mg</th> <th>Oral 420 mg </th></tr> <tr> <td><a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)"><abbr title="Peak levels">Cmax</abbr></a></td> <td>506 ± 61 ng/mL</td> <td>362 ± 38 ng/mL </td></tr> <tr> <td><a href="/wiki/Tmax_(pharmacology)" class="mw-redirect" title="Tmax (pharmacology)">Tmax</a></td> <td>2.6 ± 0.4 hours</td> <td>2.2 ± 0.2 hours </td></tr> <tr> <td><a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life"><abbr title="Elimination half-life">t1/2</abbr></a></td> <td>10.3 ± 0.95 hours</td> <td>13.6 ± 3.09 hours </td></tr> <tr> <td><a href="/wiki/Area_under_the_curve_(pharmacokinetics)" title="Area under the curve (pharmacokinetics)"><abbr title="Area-under-the-curve levels (total exposure)">AUC0–32</abbr></a></td> <td>4.82 ± 0.62</td> <td>2.88 ± 0.34 </td></tr> <tr> <td><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></td> <td>100.0%</td> <td>43.7% ± 4.6% </td></tr> <tr class="sortbottom"> <td colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;">Sources: <a href="#cite_note-pmid6375076-31">[31]</a> </td></tr></tbody></table> <table class="wikitable floatright"> <caption> Levels of EMP metabolites during continuous therapy with 560 mg/day oral EMP in men </caption> <tbody><tr> <th>Metabolite</th> <th>Plasma</th> <th>Ratio </th></tr> <tr> <td><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></td> <td>20,000–23,000 pg/mL</td> <td rowspan="2">1:9.6–9.8 </td></tr> <tr> <td><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></td> <td>191,000–267,000 pg/mL </td></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td>4,900–9,000 pg/mL</td> <td rowspan="2">1:9.4–11.8 </td></tr> <tr> <td><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></td> <td>71,000–85,000 pg/mL </td></tr> <tr class="sortbottom"> <td colspan="3" style="width: 1px; background-color:#eaecf0; text-align: center;">Sources: <a href="#cite_note-pmid6375076-31">[31]</a> </td></tr></tbody></table> Upon <a href="/wiki/Oral_administration" title="Oral administration">oral ingestion</a>, EMP is rapidly and completely <a href="/wiki/Dephosphorylation" title="Dephosphorylation">dephosphorylated</a> by <a href="/wiki/Phosphatase" title="Phosphatase">phosphatases</a> into <a href="/wiki/Estramustine" title="Estramustine">estramustine</a> during the <a href="/wiki/First-pass_metabolism" class="mw-redirect" title="First-pass metabolism">first pass</a> in the <a href="/wiki/Gastrointestinal" class="mw-redirect" title="Gastrointestinal">gastrointestinal</a> tract.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-CavalliKaye2009-45">[45]</a> Estramustine is also partially but considerably <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a> into <a href="/wiki/Estromustine" title="Estromustine">estromustine</a> by <a href="/wiki/17%CE%B2-hydroxysteroid_dehydrogenase" class="mw-redirect" title="17β-hydroxysteroid dehydrogenase">17β-hydroxysteroid dehydrogenases</a> during the first pass.<a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid8595142-12">[12]</a><a href="#cite_note-pmid6673977-46">[46]</a> As such, EMP reaches the <a href="/wiki/Circulatory_system" title="Circulatory system">circulation</a> as estramustine and estromustine, and the major <a href="/wiki/Metabolite" title="Metabolite">metabolite</a> of EMP is estromustine.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid8595142-12">[12]</a> A limited quantity of approximately 10 to 15% of estramustine and estromustine is further slowly <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> via <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of the <a href="/wiki/Normustine" title="Normustine">normustine</a> <a href="/wiki/Ester" title="Ester">ester</a> into <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a> and <a href="/wiki/Estrone_(medication)" title="Estrone (medication)">estrone</a>, respectively.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid6375076-31">[31]</a> This <a href="/wiki/Chemical_reaction" title="Chemical reaction">reaction</a> is believed to be <a href="/wiki/Catalysis" title="Catalysis">catalyzed</a> by <a href="/wiki/Carbamidase" class="mw-redirect" title="Carbamidase">carbamidases</a>, although the <a href="/wiki/Gene" title="Gene">genes</a> encoding the responsible enzymes have not been characterized.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid19735314-47">[47]</a><a href="#cite_note-pmid15733111-48">[48]</a> The circulating levels of normustine formed from EMP are insignificant.<a href="#cite_note-pmid6373212-43">[43]</a><a href="#cite_note-GateTew2011-49">[49]</a> Release of <a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">nitrogen mustard</a> <a href="/wiki/Gas" title="Gas">gas</a> from normustine via cleavage of the <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> <a href="/wiki/Functional_group" title="Functional group">group</a> has not been demonstrated and does not seem to occur.<a href="#cite_note-pmid1545778-42">[42]</a><a href="#cite_note-pmid6375076-31">[31]</a> The oral <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of EMP is low, which is due to profound first-pass metabolism; specifically, dephosphorylation of EMP.<a href="#cite_note-pmid9515186-1">[1]</a> The oral bioavailability of EMP specifically as estramustine and estromustine is 44 to 75%, suggesting that <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> may be incomplete.<a href="#cite_note-pmid9515186-1">[1]</a> In any case, there is a linear relationship between the oral dose of EMP and circulating levels of estramustine and estromustine.<a href="#cite_note-pmid9515186-1">[1]</a> Consumption of <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, or <a href="/wiki/Magnesium" title="Magnesium">magnesium</a> with oral EMP can markedly impair its bioavailability due to diminished <a href="/wiki/Absorption_(pharmacokinetics)" class="mw-redirect" title="Absorption (pharmacokinetics)">absorption</a> from the intestines, and this may interfere with its therapeutic effectiveness at low doses.<a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-EMP-EMC-17">[17]</a> Following a single oral dose of 420 mg EMP in men with prostate cancer, <a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">maximal</a> levels of estromustine were 310 to 475 ng/mL (475,000 pg/mL) and occurred after 2 to 3 hours.<a href="#cite_note-pmid9515186-1">[1]</a> Estradiol levels with 280 mg/day oral EMP have been found to increase to very high concentrations within one week of therapy.<a href="#cite_note-pmid11240822-3">[3]</a> In one study, levels of estradiol were over 20,000 pg/mL after 10 days, were about 30,000 pg/mL after 30 days, and peaked at about 40,000 pg/mL at 50 days.<a href="#cite_note-pmid11240822-3">[3]</a> Another study found lower estradiol levels of 4,900 to 9,000 pg/mL during chronic therapy with 560 mg/day oral EMP.<a href="#cite_note-pmid6375076-31">[31]</a> An additional study found estradiol levels of about 17,000 pg/mL with 140 mg/day oral EMP and 38,000 pg/mL with 280 mg/day oral EMP.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] The circulating levels of estradiol and estrone during EMP therapy have been reported to exceed normal levels in men by more than 100- and 1,000-fold, respectively.<a href="#cite_note-Inoue2018-4">[4]</a><a href="#cite_note-pmid6375076-31">[31]</a> Levels of estramustine and estradiol in the circulation are markedly lower than those of estromustine and estrone, respectively, with a ratio of about 1:10 in both cases.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid6375076-31">[31]</a> Nonetheless, estradiol levels during EMP therapy appear to be similar to those that occur in mid-to-late <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a>, which range from 5,000 to 40,000 pg/mL.<a href="#cite_note-Abbott2009-50">[50]</a> No unchanged EMP is seen in the circulation with oral administration.<a href="#cite_note-pmid9515186-1">[1]</a> The <a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">pharmacokinetics</a> of EMP are different with <a href="/wiki/Intravenous_injection" class="mw-redirect" title="Intravenous injection">intravenous injection</a>.<a href="#cite_note-pmid9515186-1">[1]</a> Following a single intravenous injection of 300 mg EMP, levels of EMP were higher than those of its metabolites for the first 8 hours.<a href="#cite_note-pmid9515186-1">[1]</a> This is likely due to the bypassing of first-pass metabolism.<a href="#cite_note-pmid9515186-1">[1]</a> However, by 24 hours after the dose, unchanged EMP could no longer be detected in the circulation.<a href="#cite_note-pmid9515186-1">[1]</a> The <a href="/wiki/Clearance_(pharmacology)" title="Clearance (pharmacology)">clearance</a> of EMP from <a href="/wiki/Blood_plasma" title="Blood plasma">blood plasma</a> is 4.85 ± 0.684 L/h.<a href="#cite_note-pmid9515186-1">[1]</a> The <a href="/wiki/Volume_of_distribution" title="Volume of distribution">volumes of distribution</a> of EMP with intravenous injection were small; under a two-compartment model, the volume of distribution for the central compartment was 0.043 L/kg and for the peripheral compartment was 0.11 L/kg.<a href="#cite_note-pmid9515186-1">[1]</a> The <a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">plasma protein binding</a> of EMP is high.<a href="#cite_note-pmid9515186-1">[1]</a> Estramustine is accumulated in <a href="/wiki/Tumor" class="mw-redirect" title="Tumor">tumor</a> tissue, for instance <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a> and <a href="/wiki/Glioma" title="Glioma">glioma</a> tissue, with estramustine levels much higher in these tissues than in plasma (e.g., 6.3- and 15.9-fold, respectively).<a href="#cite_note-pmid9515186-1">[1]</a> Conversely, levels of estromustine in tumor versus plasma are similar (1.0- and 0.5-fold, respectively).<a href="#cite_note-pmid9515186-1">[1]</a> Estramustine and estromustine appear to accumulate in <a href="/wiki/Adipose_tissue" title="Adipose tissue">adipose tissue</a>.<a href="#cite_note-pmid9515186-1">[1]</a> The <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of estromustine with oral EMP was 13.6 hours on average, with a range of 8.8 to 22.7 hours.<a href="#cite_note-pmid9515186-1">[1]</a> Conversely, the elimination half-life of estromustine with intravenous injection was 10.3 hours, with a range of 7.36 to 12.3 hours.<a href="#cite_note-pmid9515186-1">[1]</a> For comparison, the corresponding elimination half-lives of estrone were 16.5 and 14.7 hours for oral and intravenous administration, respectively.<a href="#cite_note-pmid9515186-1">[1]</a> Estramustine and estromustine are mainly <a href="/wiki/Excretion" title="Excretion">excreted</a> in <a href="/wiki/Bile" title="Bile">bile</a> and hence in <a href="/wiki/Feces" title="Feces">feces</a>.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid6375076-31">[31]</a> They are not believed to be excreted in <a href="/wiki/Urine" title="Urine">urine</a>.<a href="#cite_note-pmid9515186-1">[1]</a> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Estramustine_phosphate_metabolism.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Estramustine_phosphate_metabolism.png/900px-Estramustine_phosphate_metabolism.png" decoding="async" width="900" height="350" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/56/Estramustine_phosphate_metabolism.png/1350px-Estramustine_phosphate_metabolism.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/56/Estramustine_phosphate_metabolism.png/1800px-Estramustine_phosphate_metabolism.png 2x" data-file-width="2550" data-file-height="991" /></a><figcaption><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a> of oral estramustine phosphate in humans.<a href="#cite_note-pmid7579781-5">[5]</a><a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid6375076-31">[31]</a><a href="#cite_note-pmid19735314-47">[47]</a><a href="#cite_note-pmid15733111-48">[48]</a></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=11" title="Edit section: Chemistry">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Estrogen_ester" title="Estrogen ester">Estrogen ester</a>, <a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">List of estrogen esters § Estradiol esters</a>, and <a href="/wiki/List_of_hormonal_cytostatic_antineoplastic_agents" title="List of hormonal cytostatic antineoplastic agents">List of hormonal cytostatic antineoplastic agents</a></div> EMP, also known as estradiol 3-normustine 17β-phosphate or as estradiol 3-(bis(2-chloroethyl)carbamate) 17β-(dihydrogen phosphate), is a <a href="/wiki/Synthetic_compound" class="mw-redirect" title="Synthetic compound">synthetic</a> <a href="/wiki/Estrane" title="Estrane">estrane</a> <a href="/wiki/Steroid" title="Steroid">steroid</a> and a <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivative</a> of <a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">estradiol</a>.<a href="#cite_note-Elks2014-35">[35]</a><a href="#cite_note-IndexNominum2000-15">[15]</a> It is an <a href="/wiki/Estrogen_ester" title="Estrogen ester">estrogen ester</a>; specifically, EMP is a <a href="/wiki/Ester" title="Ester">diester</a> of estradiol with a C3 <a href="/wiki/Normustine" title="Normustine">normustine</a> (<a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">nitrogen mustard</a>–<a href="/wiki/Carbamate" title="Carbamate">carbamate</a> <a href="/wiki/Moiety_(chemistry)" title="Moiety (chemistry)">moiety</a>) ester and a C17β <a href="/wiki/Phosphate" title="Phosphate">phosphate</a> ester.<a href="#cite_note-Elks2014-35">[35]</a><a href="#cite_note-IndexNominum2000-15">[15]</a> EMP is provided as the <a href="/wiki/Sodium" title="Sodium">sodium</a> or <a href="/wiki/Meglumine" title="Meglumine">meglumine</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a>.<a href="#cite_note-Elks2014-35">[35]</a><a href="#cite_note-IndexNominum2000-15">[15]</a><a href="#cite_note-Muller1998-24">[24]</a> EMP is similar as a compound to other <a href="/wiki/Estradiol_ester" class="mw-redirect" title="Estradiol ester">estradiol esters</a> such as <a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">estradiol sulfate</a> and <a href="/wiki/Estradiol_valerate" title="Estradiol valerate">estradiol valerate</a>, but differs in the presence of its nitrogen mustard ester moiety.<a href="#cite_note-Elks2014-35">[35]</a><a href="#cite_note-IndexNominum2000-15">[15]</a> <a href="/wiki/Antineoplastic_agent" class="mw-redirect" title="Antineoplastic agent">Antineoplastic agents</a> related to EMP, although none of them were marketed, include <a href="/wiki/Alestramustine" title="Alestramustine">alestramustine</a>, <a href="/wiki/Atrimustine" title="Atrimustine">atrimustine</a>, <a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">cytestrol acetate</a>, <a href="/wiki/Estradiol_mustard" title="Estradiol mustard">estradiol mustard</a>, <a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966</a>, and <a href="/wiki/Phenestrol" title="Phenestrol">phenestrol</a>.<a href="#cite_note-Elks2014-35">[35]</a><a href="#cite_note-IndexNominum2000-15">[15]</a> Due to its <a href="/wiki/Hydrophilic" class="mw-redirect" title="Hydrophilic">hydrophilic</a> phosphate ester moiety, EMP is a readily <a href="/wiki/Water_solubility" class="mw-redirect" title="Water solubility">water-soluble</a> compound.<a href="#cite_note-Loftsson2014-51">[51]</a><a href="#cite_note-Bernal1997-52">[52]</a><a href="#cite_note-Murff2012-53">[53]</a> This is in contrast to most other estradiol esters, which are <a href="/wiki/Fatty_acid" title="Fatty acid">fatty acid</a> esters and <a href="/wiki/Lipophilic" class="mw-redirect" title="Lipophilic">lipophilic</a> compounds that are not particularly <a href="/wiki/Water_solubility" class="mw-redirect" title="Water solubility">soluble</a> in <a href="/wiki/Water" title="Water">water</a>.<a href="#cite_note-pmid16112947-2">[2]</a> Unlike EMP, estramustine is highly lipophilic, practically insoluble in water, and non-<a href="/wiki/Ionization" title="Ionization">ionizable</a>.<a href="#cite_note-StellaBorchardt2007-19">[19]</a> The phosphate ester of EMP was incorporated into the molecule in order to increase its water solubility and allow for <a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration">intravenous administration</a>.<a href="#cite_note-EmcytLabel-7">[7]</a> The molecular weight of EMP sodium is 564.3 g/mol, of EMP meglumine is 715.6 g/mol, of EMP is 520.4 g/mol, of estramustine is 440.4 g/mol, and of estradiol is 272.4 g/mol.<a href="#cite_note-PubChem-54">[54]</a> As a result of these differences in molecular weights, EMP contains about 52%, EMP sodium about 48%, and EMP meglumine about 38% of the amount of estradiol within their structures as does an equal-mass quantity of estradiol.<a href="#cite_note-PubChem-54">[54]</a> <table class="wikitable sortable mw-collapsible mw-collapsed" style="font-size:small; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption class="nowrap"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Structural_properties_of_selected_estradiol_esters" title="Template:Structural properties of selected estradiol esters"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Structural_properties_of_selected_estradiol_esters" title="Template talk:Structural properties of selected estradiol esters"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Structural_properties_of_selected_estradiol_esters" title="Special:EditPage/Template:Structural properties of selected estradiol esters"><abbr title="Edit this template">e</abbr></a></li></ul></div> Structural properties of selected estradiol esters </caption> <tbody><tr> <th rowspan="2">Estrogen</th> <th rowspan="2" class="unsortable">Structure</th> <th colspan="4">Ester(s)</th> <th rowspan="2">Relative <abbr title="molecular weight">mol. weight</abbr></th> <th rowspan="2">Relative <abbr title="estradiol">E2</abbr> contentb</th> <th rowspan="2">log Pc </th></tr> <tr> <th>Position(s)</th> <th class="unsortable">Moiet(ies)</th> <th>Type</th> <th>Lengtha </th></tr> <tr> <td><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/35px-Estradiol.svg.png" decoding="async" width="35" height="22" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/53px-Estradiol.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/00/Estradiol.svg/70px-Estradiol.svg.png 2x" data-file-width="512" data-file-height="324" /></a><figcaption></figcaption></figure></td> <td>–</td> <td>–</td> <td>–</td> <td>–</td> <td>1.00</td> <td>1.00</td> <td>4.0 </td></tr> <tr> <td><a href="/wiki/Estradiol_acetate" title="Estradiol acetate">Estradiol acetate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_3-acetate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_3-acetate.svg/35px-Estradiol_3-acetate.svg.png" decoding="async" width="35" height="21" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_3-acetate.svg/53px-Estradiol_3-acetate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_3-acetate.svg/70px-Estradiol_3-acetate.svg.png 2x" data-file-width="1350" data-file-height="810" /></a><figcaption></figcaption></figure></td> <td>C3</td> <td><a href="/wiki/Ethanoic_acid" class="mw-redirect" title="Ethanoic acid">Ethanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>2</td> <td>1.15</td> <td>0.87</td> <td>4.2 </td></tr> <tr> <td><a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">Estradiol benzoate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_benzoate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_benzoate.svg/35px-Estradiol_benzoate.svg.png" decoding="async" width="35" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_benzoate.svg/53px-Estradiol_benzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0d/Estradiol_benzoate.svg/70px-Estradiol_benzoate.svg.png 2x" data-file-width="512" data-file-height="292" /></a><figcaption></figcaption></figure></td> <td>C3</td> <td><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a></td> <td>Aromatic fatty acid</td> <td>– (~4–5)</td> <td>1.38</td> <td>0.72</td> <td>4.7 </td></tr> <tr> <td><a href="/wiki/Estradiol_dipropionate" title="Estradiol dipropionate">Estradiol dipropionate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_dipropionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Estradiol_dipropionate.svg/35px-Estradiol_dipropionate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Estradiol_dipropionate.svg/53px-Estradiol_dipropionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/16/Estradiol_dipropionate.svg/70px-Estradiol_dipropionate.svg.png 2x" data-file-width="512" data-file-height="263" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Propanoic_acid" class="mw-redirect" title="Propanoic acid">Propanoic acid</a> (×2)</td> <td>Straight-chain fatty acid</td> <td>3 (×2)</td> <td>1.41</td> <td>0.71</td> <td>4.9 </td></tr> <tr> <td><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/35px-Estradiol_butyrate_benzoate.svg.png" decoding="async" width="35" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_butyrate_benzoate.svg/53px-Estradiol_butyrate_benzoate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c6/Estradiol_butyrate_benzoate.svg/70px-Estradiol_butyrate_benzoate.svg.png 2x" data-file-width="965" data-file-height="540" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a>, <a href="/wiki/Butyric_acid" title="Butyric acid">butyric acid</a></td> <td>Mixed fatty acid</td> <td>– (~6, 2)</td> <td>1.64</td> <td>0.61</td> <td>6.3 </td></tr> <tr> <td><a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">Estradiol cypionate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_17_beta-cypionate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Estradiol_17_beta-cypionate.svg/35px-Estradiol_17_beta-cypionate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Estradiol_17_beta-cypionate.svg/53px-Estradiol_17_beta-cypionate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8d/Estradiol_17_beta-cypionate.svg/70px-Estradiol_17_beta-cypionate.svg.png 2x" data-file-width="512" data-file-height="269" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Cyclopentylpropanoic_acid" class="mw-redirect" title="Cyclopentylpropanoic acid">Cyclopentylpropanoic acid</a></td> <td>Cyclic fatty acid</td> <td>– (~6)</td> <td>1.46</td> <td>0.69</td> <td>6.9 </td></tr> <tr> <td><a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">Estradiol enanthate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_enanthate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Estradiol_enanthate.png/35px-Estradiol_enanthate.png" decoding="async" width="35" height="17" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Estradiol_enanthate.png/53px-Estradiol_enanthate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b2/Estradiol_enanthate.png/70px-Estradiol_enanthate.png 2x" data-file-width="2407" data-file-height="1144" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Heptanoic_acid" class="mw-redirect" title="Heptanoic acid">Heptanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>7</td> <td>1.41</td> <td>0.71</td> <td>6.7–7.3 </td></tr> <tr> <td><a href="/wiki/Estradiol_dienanthate" class="mw-redirect" title="Estradiol dienanthate">Estradiol dienanthate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_dienanthate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Estradiol_dienanthate.svg/35px-Estradiol_dienanthate.svg.png" decoding="async" width="35" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Estradiol_dienanthate.svg/53px-Estradiol_dienanthate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Estradiol_dienanthate.svg/70px-Estradiol_dienanthate.svg.png 2x" data-file-width="2605" data-file-height="900" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Heptanoic_acid" class="mw-redirect" title="Heptanoic acid">Heptanoic acid</a> (×2)</td> <td>Straight-chain fatty acid</td> <td>7 (×2)</td> <td>1.82</td> <td>0.55</td> <td>8.1–10.4 </td></tr> <tr> <td><a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">Estradiol undecylate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_undecylate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Estradiol_undecylate.svg/35px-Estradiol_undecylate.svg.png" decoding="async" width="35" height="13" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Estradiol_undecylate.svg/53px-Estradiol_undecylate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Estradiol_undecylate.svg/70px-Estradiol_undecylate.svg.png 2x" data-file-width="512" data-file-height="186" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Undecanoic_acid" class="mw-redirect" title="Undecanoic acid">Undecanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>11</td> <td>1.62</td> <td>0.62</td> <td>9.2–9.8 </td></tr> <tr> <td><a href="/wiki/Estradiol_stearate" title="Estradiol stearate">Estradiol stearate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_stearate_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Estradiol_stearate_structure.svg/35px-Estradiol_stearate_structure.svg.png" decoding="async" width="35" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Estradiol_stearate_structure.svg/53px-Estradiol_stearate_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/Estradiol_stearate_structure.svg/70px-Estradiol_stearate_structure.svg.png 2x" data-file-width="3160" data-file-height="900" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Octadecanoic_acid" class="mw-redirect" title="Octadecanoic acid">Octadecanoic acid</a></td> <td>Straight-chain fatty acid</td> <td>18</td> <td>1.98</td> <td>0.51</td> <td>12.2–12.4 </td></tr> <tr> <td><a href="/wiki/Estradiol_distearate" title="Estradiol distearate">Estradiol distearate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_distearate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Estradiol_distearate.svg/35px-Estradiol_distearate.svg.png" decoding="async" width="35" height="15" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Estradiol_distearate.svg/53px-Estradiol_distearate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f9/Estradiol_distearate.svg/70px-Estradiol_distearate.svg.png 2x" data-file-width="1615" data-file-height="705" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Octadecanoic_acid" class="mw-redirect" title="Octadecanoic acid">Octadecanoic acid</a> (×2)</td> <td>Straight-chain fatty acid</td> <td>18 (×2)</td> <td>2.96</td> <td>0.34</td> <td>20.2 </td></tr> <tr> <td><a href="/wiki/Estradiol_sulfate" title="Estradiol sulfate">Estradiol sulfate</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_sulfate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/35px-Estradiol_sulfate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/53px-Estradiol_sulfate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/70px-Estradiol_sulfate.svg.png 2x" data-file-width="690" data-file-height="360" /></a><figcaption></figcaption></figure></td> <td>C3</td> <td><a href="/wiki/Sulfuric_acid" title="Sulfuric acid">Sulfuric acid</a></td> <td>Water-soluble conjugate</td> <td>–</td> <td>1.29</td> <td>0.77</td> <td>0.3–3.8 </td></tr> <tr> <td><a href="/wiki/Estradiol_glucuronide" title="Estradiol glucuronide">Estradiol glucuronide</a></td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estradiol_sulfate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/35px-Estradiol_sulfate.svg.png" decoding="async" width="35" height="18" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/53px-Estradiol_sulfate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/64/Estradiol_sulfate.svg/70px-Estradiol_sulfate.svg.png 2x" data-file-width="690" data-file-height="360" /></a><figcaption></figcaption></figure></td> <td>C17β</td> <td><a href="/wiki/Glucuronic_acid" title="Glucuronic acid">Glucuronic acid</a></td> <td>Water-soluble conjugate</td> <td>–</td> <td>1.65</td> <td>0.61</td> <td>2.1–2.7 </td></tr> <tr> <td>Estramustine phosphated</td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Estramustine_phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/35px-Estramustine_phosphate.svg.png" decoding="async" width="35" height="23" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/53px-Estramustine_phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Estramustine_phosphate.svg/70px-Estramustine_phosphate.svg.png 2x" data-file-width="1995" data-file-height="1285" /></a><figcaption></figcaption></figure></td> <td>C3, C17β</td> <td><a href="/wiki/Normustine" title="Normustine">Normustine</a>, <a href="/wiki/Phosphoric_acid" title="Phosphoric acid">phosphoric acid</a></td> <td>Water-soluble conjugate</td> <td>–</td> <td>1.91</td> <td>0.52</td> <td>2.9–5.0 </td></tr> <tr> <td><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a>e</td> <td><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Polyestradiol_phosphate.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Polyestradiol_phosphate.svg/35px-Polyestradiol_phosphate.svg.png" decoding="async" width="35" height="24" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Polyestradiol_phosphate.svg/53px-Polyestradiol_phosphate.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Polyestradiol_phosphate.svg/70px-Polyestradiol_phosphate.svg.png 2x" data-file-width="1550" data-file-height="1050" /></a><figcaption></figcaption></figure></td> <td>C3–C17β</td> <td><a href="/wiki/Phosphoric_acid" title="Phosphoric acid">Phosphoric acid</a></td> <td>Water-soluble conjugate</td> <td>–</td> <td>1.23f</td> <td>0.81f</td> <td>2.9g </td></tr> <tr class="sortbottom"> <td colspan="10" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = Length of <a href="/wiki/Ester" title="Ester">ester</a> in <a href="/wiki/Carbon" title="Carbon">carbon</a> <a href="/wiki/Atom" title="Atom">atoms</a> for <a href="/wiki/Straight-chain_fatty_acid" class="mw-redirect" title="Straight-chain fatty acid">straight-chain fatty acids</a> or approximate length of ester in carbon atoms for <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> or <a href="/wiki/Cyclic_compound" title="Cyclic compound">cyclic</a> fatty acids. b = Relative estradiol content by weight (i.e., relative <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogenic</a> exposure). c = Experimental or predicted <a href="/wiki/Partition_coefficient" title="Partition coefficient">octanol/water partition coefficient</a> (i.e., <a href="/wiki/Lipophilicity" title="Lipophilicity">lipophilicity</a>/<a href="/wiki/Hydrophobicity" class="mw-redirect" title="Hydrophobicity">hydrophobicity</a>). Retrieved from <a href="/wiki/PubChem" title="PubChem">PubChem</a>, <a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a>, and <a href="/wiki/DrugBank" title="DrugBank">DrugBank</a>. d = Also known as estradiol normustine phosphate. e = <a href="/wiki/Polymer" title="Polymer">Polymer</a> of <a href="/wiki/Estradiol_phosphate" title="Estradiol phosphate">estradiol phosphate</a> (~13 <a href="/wiki/Repeat_unit" title="Repeat unit">repeat units</a>). f = Relative molecular weight or estradiol content per repeat unit. g = log P of repeat unit (i.e., estradiol phosphate). Sources: See individual articles. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=12" title="Edit section: History">edit</a>]</div> EMP was first <a href="/wiki/Chemical_synthesis" title="Chemical synthesis">synthesized</a> in the mid-1960s and was <a href="/wiki/Patent" title="Patent">patented</a> in 1967.<a href="#cite_note-pmid1545778-42">[42]</a> It was initially developed for the treatment of <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>.<a href="#cite_note-pmid9515186-1">[1]</a> The idea for EMP was inspired by the uptake and accumulation of <a href="/wiki/Radiolabel" class="mw-redirect" title="Radiolabel">radiolabeled</a> estrogens into breast cancer tissue.<a href="#cite_note-pmid9515186-1">[1]</a> However, initial clinical findings of EMP in women with breast cancer were disappointing.<a href="#cite_note-pmid9515186-1">[1]</a> Subsequently, radiolabeled EMP was found to be taken up into and accumulated rat <a href="/wiki/Prostate_gland" class="mw-redirect" title="Prostate gland">prostate gland</a>, and this finding culminated in the medication being repurposed for the treatment of <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a> EMP was introduced for medical use in the treatment of this condition in the early 1970s, and was approved in the <a href="/wiki/United_States" title="United States">United States</a> for this indication in 1981.<a href="#cite_note-pmid9515186-1">[1]</a><a href="#cite_note-pmid11240822-3">[3]</a><a href="#cite_note-FiggChau2010-55">[55]</a> EMP was originally introduced for use by intravenous injection.<a href="#cite_note-pmid6375076-31">[31]</a> Subsequently, an oral formulation was introduced, and the intravenous preparation was almost abandoned in favor of the oral version.<a href="#cite_note-pmid6375076-31">[31]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=13" 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=Estramustine_phosphate&action=edit&section=14" title="Edit section: Generic names">edit</a>]</div> EMP is provided as the <a href="/wiki/Sodium" title="Sodium">sodium</a> <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> for <a href="/wiki/Oral_administration" title="Oral administration">oral administration</a>, which has the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic names</a> estramustine phosphate sodium (<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) and estramustine sodium phosphate (<a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BANM</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name, <a href="/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), and as the <a href="/wiki/Meglumine" title="Meglumine">meglumine</a> salt for <a href="/wiki/Intravenous_administration" class="mw-redirect" title="Intravenous administration">intravenous administration</a>, which has the generic name estramustine phosphate meglumine.<a href="#cite_note-Muller1998-24">[24]</a><a href="#cite_note-Elks2014-35">[35]</a><a href="#cite_note-IndexNominum2000-15">[15]</a><a href="#cite_note-MortonHall2012-56">[56]</a><a href="#cite_note-Drugs.com-16">[16]</a> The <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INNM</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name is estramustine phosphate.<a href="#cite_note-Elks2014-35">[35]</a> The name estramustine phosphate is a contraction of estradiol normustine phosphate.<a href="#cite_note-Elks2014-35">[35]</a><a href="#cite_note-Drugs.com-16">[16]</a> EMP is also known by its former developmental code names Leo 299, Ro 21-8837, and Ro 21-8837/001.<a href="#cite_note-Elks2014-35">[35]</a><a href="#cite_note-IndexNominum2000-15">[15]</a><a href="#cite_note-Drugs.com-16">[16]</a> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=15" title="Edit section: Brand names">edit</a>]</div> EMP is most commonly marketed under the brand names Estracyt and Emcyt, but has also been sold under a number of other brand names, including Amsupros, Biasetyl, Cellmustin, Estramustin HEXAL, Estramustina Filaxis, Estranovag, Multosin, Multosin Injekt, Proesta, Prostamustin, and Suloprost.<a href="#cite_note-IndexNominum2000-15">[15]</a><a href="#cite_note-Drugs.com-16">[16]</a><a href="#cite_note-Muller1998-24">[24]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=16" title="Edit section: Availability">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/List_of_estrogens_available_in_the_United_States" title="List of estrogens available in the United States">List of estrogens available in the United States</a></div> EMP is marketed in the <a href="/wiki/United_States" title="United States">United States</a>,<a href="#cite_note-Drugs@FDA-57">[57]</a> <a href="/wiki/Canada" title="Canada">Canada</a>, and <a href="/wiki/Mexico" title="Mexico">Mexico</a> under the brand name Emcyt, whereas the medication is marketed under the brand name Estracyt in the <a href="/wiki/United_Kingdom" title="United Kingdom">United Kingdom</a> and elsewhere throughout <a href="/wiki/Europe" title="Europe">Europe</a> as well as in <a href="/wiki/Argentina" title="Argentina">Argentina</a>, <a href="/wiki/Chile" title="Chile">Chile</a>, and <a href="/wiki/Hong_Kong" title="Hong Kong">Hong Kong</a>.<a href="#cite_note-IndexNominum2000-15">[15]</a> It has been discontinued in a number of countries, including <a href="/wiki/Australia" title="Australia">Australia</a>, <a href="/wiki/Brazil" title="Brazil">Brazil</a>, <a href="/wiki/Ireland" title="Ireland">Ireland</a>, and <a href="/wiki/Norway" title="Norway">Norway</a>.<a href="#cite_note-Martindale-58">[58]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=17" title="Edit section: Research">edit</a>]</div> EMP has been studied in the treatment of other <a href="/wiki/Cancer" title="Cancer">cancers</a> such as <a href="/wiki/Glioma" title="Glioma">glioma</a> and <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>.<a href="#cite_note-pmid9515186-1">[1]</a> It has been found to slightly improve <a href="/wiki/Quality_of_life" title="Quality of life">quality of life</a> in people with glioma during the first 3 months of therapy.<a href="#cite_note-pmid9515186-1">[1]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Estramustine_phosphate&action=edit&section=18" title="Edit section: References">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-pmid9515186-1">^ <a href="#cite_ref-pmid9515186_1-0">a</a> <a href="#cite_ref-pmid9515186_1-1">b</a> <a href="#cite_ref-pmid9515186_1-2">c</a> <a href="#cite_ref-pmid9515186_1-3">d</a> <a href="#cite_ref-pmid9515186_1-4">e</a> <a href="#cite_ref-pmid9515186_1-5">f</a> <a href="#cite_ref-pmid9515186_1-6">g</a> <a href="#cite_ref-pmid9515186_1-7">h</a> <a href="#cite_ref-pmid9515186_1-8">i</a> <a href="#cite_ref-pmid9515186_1-9">j</a> <a href="#cite_ref-pmid9515186_1-10">k</a> <a href="#cite_ref-pmid9515186_1-11">l</a> <a href="#cite_ref-pmid9515186_1-12">m</a> <a href="#cite_ref-pmid9515186_1-13">n</a> <a href="#cite_ref-pmid9515186_1-14">o</a> <a href="#cite_ref-pmid9515186_1-15">p</a> <a href="#cite_ref-pmid9515186_1-16">q</a> <a href="#cite_ref-pmid9515186_1-17">r</a> <a href="#cite_ref-pmid9515186_1-18">s</a> <a href="#cite_ref-pmid9515186_1-19">t</a> <a href="#cite_ref-pmid9515186_1-20">u</a> <a href="#cite_ref-pmid9515186_1-21">v</a> <a href="#cite_ref-pmid9515186_1-22">w</a> <a href="#cite_ref-pmid9515186_1-23">x</a> <a href="#cite_ref-pmid9515186_1-24">y</a> <a href="#cite_ref-pmid9515186_1-25">z</a> <a href="#cite_ref-pmid9515186_1-26">aa</a> <a href="#cite_ref-pmid9515186_1-27">ab</a> <a href="#cite_ref-pmid9515186_1-28">ac</a> <a href="#cite_ref-pmid9515186_1-29">ad</a> <a href="#cite_ref-pmid9515186_1-30">ae</a> <a href="#cite_ref-pmid9515186_1-31">af</a> <a href="#cite_ref-pmid9515186_1-32">ag</a> <a href="#cite_ref-pmid9515186_1-33">ah</a> <a href="#cite_ref-pmid9515186_1-34">ai</a> <a href="#cite_ref-pmid9515186_1-35">aj</a> <a href="#cite_ref-pmid9515186_1-36">ak</a> <a href="#cite_ref-pmid9515186_1-37">al</a> <a href="#cite_ref-pmid9515186_1-38">am</a> <a href="#cite_ref-pmid9515186_1-39">an</a> <a href="#cite_ref-pmid9515186_1-40">ao</a> <a href="#cite_ref-pmid9515186_1-41">ap</a> <a href="#cite_ref-pmid9515186_1-42">aq</a> <a href="#cite_ref-pmid9515186_1-43">ar</a> <a href="#cite_ref-pmid9515186_1-44">as</a> <a href="#cite_ref-pmid9515186_1-45">at</a> <a href="#cite_ref-pmid9515186_1-46">au</a> <a href="#cite_ref-pmid9515186_1-47">av</a> <a href="#cite_ref-pmid9515186_1-48">aw</a> <a href="#cite_ref-pmid9515186_1-49">ax</a> <a href="#cite_ref-pmid9515186_1-50">ay</a> <a href="#cite_ref-pmid9515186_1-51">az</a> <a href="#cite_ref-pmid9515186_1-52">ba</a> <a href="#cite_ref-pmid9515186_1-53">bb</a> <a href="#cite_ref-pmid9515186_1-54">bc</a> <a href="#cite_ref-pmid9515186_1-55">bd</a> <a href="#cite_ref-pmid9515186_1-56">be</a> <a href="#cite_ref-pmid9515186_1-57">bf</a> <a href="#cite_ref-pmid9515186_1-58">bg</a> <a href="#cite_ref-pmid9515186_1-59">bh</a> <a href="#cite_ref-pmid9515186_1-60">bi</a> <a href="#cite_ref-pmid9515186_1-61">bj</a> <a href="#cite_ref-pmid9515186_1-62">bk</a> <a href="#cite_ref-pmid9515186_1-63">bl</a> <a href="#cite_ref-pmid9515186_1-64">bm</a> <a href="#cite_ref-pmid9515186_1-65">bn</a> <a href="#cite_ref-pmid9515186_1-66">bo</a> <a href="#cite_ref-pmid9515186_1-67">bp</a> <a href="#cite_ref-pmid9515186_1-68">bq</a> <a href="#cite_ref-pmid9515186_1-69">br</a> <a href="#cite_ref-pmid9515186_1-70">bs</a> <a href="#cite_ref-pmid9515186_1-71">bt</a> <a href="#cite_ref-pmid9515186_1-72">bu</a> <a href="#cite_ref-pmid9515186_1-73">bv</a> <a href="#cite_ref-pmid9515186_1-74">bw</a> <a href="#cite_ref-pmid9515186_1-75">bx</a> <a href="#cite_ref-pmid9515186_1-76">by</a> <a href="#cite_ref-pmid9515186_1-77">bz</a> <a href="#cite_ref-pmid9515186_1-78">ca</a> <a href="#cite_ref-pmid9515186_1-79">cb</a> <a href="#cite_ref-pmid9515186_1-80">cc</a> <a href="#cite_ref-pmid9515186_1-81">cd</a> <a href="#cite_ref-pmid9515186_1-82">ce</a> <a href="#cite_ref-pmid9515186_1-83">cf</a> <a href="#cite_ref-pmid9515186_1-84">cg</a> <a href="#cite_ref-pmid9515186_1-85">ch</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFBergenheimHenriksson1998" class="citation journal cs1">Bergenheim AT, Henriksson R (February 1998). "Pharmacokinetics and pharmacodynamics of estramustine phosphate". Clinical Pharmacokinetics. 34 (2): 163–172. <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%2F00003088-199834020-00004">10.2165/00003088-199834020-00004</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/9515186">9515186</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:1943973">1943973</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Pharmacokinetics&rft.atitle=Pharmacokinetics+and+pharmacodynamics+of+estramustine+phosphate&rft.volume=34&rft.issue=2&rft.pages=163-172&rft.date=1998-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A1943973%23id-name%3DS2CID&rft_id=info%3Apmid%2F9515186&rft_id=info%3Adoi%2F10.2165%2F00003088-199834020-00004&rft.aulast=Bergenheim&rft.aufirst=AT&rft.au=Henriksson%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid16112947-2">^ <a href="#cite_ref-pmid16112947_2-0">a</a> <a href="#cite_ref-pmid16112947_2-1">b</a> <a href="#cite_ref-pmid16112947_2-2">c</a> <a href="#cite_ref-pmid16112947_2-3">d</a> <a href="#cite_ref-pmid16112947_2-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKuhl2005" class="citation journal cs1">Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F13697130500148875">10.1080/13697130500148875</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16112947">16112947</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:24616324">24616324</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Climacteric&rft.atitle=Pharmacology+of+estrogens+and+progestogens%3A+influence+of+different+routes+of+administration&rft.volume=8&rft.issue=Suppl+1&rft.pages=3-63&rft.date=2005-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A24616324%23id-name%3DS2CID&rft_id=info%3Apmid%2F16112947&rft_id=info%3Adoi%2F10.1080%2F13697130500148875&rft.aulast=Kuhl&rft.aufirst=H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid11240822-3">^ <a href="#cite_ref-pmid11240822_3-0">a</a> <a href="#cite_ref-pmid11240822_3-1">b</a> <a href="#cite_ref-pmid11240822_3-2">c</a> <a href="#cite_ref-pmid11240822_3-3">d</a> <a href="#cite_ref-pmid11240822_3-4">e</a> <a href="#cite_ref-pmid11240822_3-5">f</a> <a href="#cite_ref-pmid11240822_3-6">g</a> <a href="#cite_ref-pmid11240822_3-7">h</a> <a href="#cite_ref-pmid11240822_3-8">i</a> <a href="#cite_ref-pmid11240822_3-9">j</a> <a href="#cite_ref-pmid11240822_3-10">k</a> <a href="#cite_ref-pmid11240822_3-11">l</a> <a href="#cite_ref-pmid11240822_3-12">m</a> <a href="#cite_ref-pmid11240822_3-13">n</a> <a href="#cite_ref-pmid11240822_3-14">o</a> <a href="#cite_ref-pmid11240822_3-15">p</a> <a href="#cite_ref-pmid11240822_3-16">q</a> <a href="#cite_ref-pmid11240822_3-17">r</a> <a href="#cite_ref-pmid11240822_3-18">s</a> <a href="#cite_ref-pmid11240822_3-19">t</a> <a href="#cite_ref-pmid11240822_3-20">u</a> <a href="#cite_ref-pmid11240822_3-21">v</a> <a href="#cite_ref-pmid11240822_3-22">w</a> <a href="#cite_ref-pmid11240822_3-23">x</a> <a href="#cite_ref-pmid11240822_3-24">y</a> <a href="#cite_ref-pmid11240822_3-25">z</a> <a href="#cite_ref-pmid11240822_3-26">aa</a> <a href="#cite_ref-pmid11240822_3-27">ab</a> <a href="#cite_ref-pmid11240822_3-28">ac</a> <a href="#cite_ref-pmid11240822_3-29">ad</a> <a href="#cite_ref-pmid11240822_3-30">ae</a> <a href="#cite_ref-pmid11240822_3-31">af</a> <a href="#cite_ref-pmid11240822_3-32">ag</a> <a href="#cite_ref-pmid11240822_3-33">ah</a> <a href="#cite_ref-pmid11240822_3-34">ai</a> <a href="#cite_ref-pmid11240822_3-35">aj</a> <a href="#cite_ref-pmid11240822_3-36">ak</a> <a href="#cite_ref-pmid11240822_3-37">al</a> <a href="#cite_ref-pmid11240822_3-38">am</a> <a href="#cite_ref-pmid11240822_3-39">an</a> <a href="#cite_ref-pmid11240822_3-40">ao</a> <a href="#cite_ref-pmid11240822_3-41">ap</a> <a href="#cite_ref-pmid11240822_3-42">aq</a> <a href="#cite_ref-pmid11240822_3-43">ar</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKitamura2001" class="citation journal cs1">Kitamura T (February 2001). "Necessity of re-evaluation of estramustine phosphate sodium (EMP) as a treatment option for first-line monotherapy in advanced prostate cancer". International Journal of Urology. 8 (2): 33–36. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1046%2Fj.1442-2042.2001.00254.x">10.1046/j.1442-2042.2001.00254.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11240822">11240822</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:43384150">43384150</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Urology&rft.atitle=Necessity+of+re-evaluation+of+estramustine+phosphate+sodium+%28EMP%29+as+a+treatment+option+for+first-line+monotherapy+in+advanced+prostate+cancer&rft.volume=8&rft.issue=2&rft.pages=33-36&rft.date=2001-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A43384150%23id-name%3DS2CID&rft_id=info%3Apmid%2F11240822&rft_id=info%3Adoi%2F10.1046%2Fj.1442-2042.2001.00254.x&rft.aulast=Kitamura&rft.aufirst=T&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Inoue2018-4">^ <a href="#cite_ref-Inoue2018_4-0">a</a> <a href="#cite_ref-Inoue2018_4-1">b</a> <a href="#cite_ref-Inoue2018_4-2">c</a> <a href="#cite_ref-Inoue2018_4-3">d</a> <a href="#cite_ref-Inoue2018_4-4">e</a> <a href="#cite_ref-Inoue2018_4-5">f</a> <a href="#cite_ref-Inoue2018_4-6">g</a> <a href="#cite_ref-Inoue2018_4-7">h</a> <a href="#cite_ref-Inoue2018_4-8">i</a> <a href="#cite_ref-Inoue2018_4-9">j</a> <a href="#cite_ref-Inoue2018_4-10">k</a> <a href="#cite_ref-Inoue2018_4-11">l</a> <a href="#cite_ref-Inoue2018_4-12">m</a> <a href="#cite_ref-Inoue2018_4-13">n</a> <a href="#cite_ref-Inoue2018_4-14">o</a> <a href="#cite_ref-Inoue2018_4-15">p</a> <a href="#cite_ref-Inoue2018_4-16">q</a> <a href="#cite_ref-Inoue2018_4-17">r</a> <a href="#cite_ref-Inoue2018_4-18">s</a> <a href="#cite_ref-Inoue2018_4-19">t</a> <a href="#cite_ref-Inoue2018_4-20">u</a> <a href="#cite_ref-Inoue2018_4-21">v</a> <a href="#cite_ref-Inoue2018_4-22">w</a> <a href="#cite_ref-Inoue2018_4-23">x</a> <a href="#cite_ref-Inoue2018_4-24">y</a> <a href="#cite_ref-Inoue2018_4-25">z</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFInoue2018" class="citation book cs1">Inoue T (2018). "Role of Estramustine Phosphate and Other Estrogens for Castration-Resistant Prostate Cancer". Hormone Therapy and Castration Resistance of Prostate Cancer. Springer. pp. 249–256. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-981-10-7013-6_26">10.1007/978-981-10-7013-6_26</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-981-10-7012-9" title="Special:BookSources/978-981-10-7012-9"><bdi>978-981-10-7012-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Role+of+Estramustine+Phosphate+and+Other+Estrogens+for+Castration-Resistant+Prostate+Cancer&rft.btitle=Hormone+Therapy+and+Castration+Resistance+of+Prostate+Cancer&rft.pages=249-256&rft.pub=Springer&rft.date=2018&rft_id=info%3Adoi%2F10.1007%2F978-981-10-7013-6_26&rft.isbn=978-981-10-7012-9&rft.aulast=Inoue&rft.aufirst=T&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid7579781-5">^ <a href="#cite_ref-pmid7579781_5-0">a</a> <a href="#cite_ref-pmid7579781_5-1">b</a> <a href="#cite_ref-pmid7579781_5-2">c</a> <a href="#cite_ref-pmid7579781_5-3">d</a> <a href="#cite_ref-pmid7579781_5-4">e</a> <a href="#cite_ref-pmid7579781_5-5">f</a> <a href="#cite_ref-pmid7579781_5-6">g</a> <a href="#cite_ref-pmid7579781_5-7">h</a> <a href="#cite_ref-pmid7579781_5-8">i</a> <a href="#cite_ref-pmid7579781_5-9">j</a> <a href="#cite_ref-pmid7579781_5-10">k</a> <a href="#cite_ref-pmid7579781_5-11">l</a> <a href="#cite_ref-pmid7579781_5-12">m</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPerryMcTavish1995" class="citation journal cs1">Perry CM, McTavish D (July 1995). "Estramustine phosphate sodium. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in prostate cancer". Drugs & Aging. 7 (1): 49–74. <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%2F00002512-199507010-00006">10.2165/00002512-199507010-00006</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/7579781">7579781</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:36725810">36725810</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drugs+%26+Aging&rft.atitle=Estramustine+phosphate+sodium.+A+review+of+its+pharmacodynamic+and+pharmacokinetic+properties%2C+and+therapeutic+efficacy+in+prostate+cancer&rft.volume=7&rft.issue=1&rft.pages=49-74&rft.date=1995-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A36725810%23id-name%3DS2CID&rft_id=info%3Apmid%2F7579781&rft_id=info%3Adoi%2F10.2165%2F00002512-199507010-00006&rft.aulast=Perry&rft.aufirst=CM&rft.au=McTavish%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-MSR-6">^ <a href="#cite_ref-MSR_6-0">a</a> <a href="#cite_ref-MSR_6-1">b</a> <a href="#cite_ref-MSR_6-2">c</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://reference.medscape.com/drug/emcyt-estramustine-342085#showall">"Emcyt (estramustine) dosing, indications, interactions, adverse effects, and more"</a>. Medscape Reference. WebMD. Retrieved 8 February 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Medscape+Reference&rft.atitle=Emcyt+%28estramustine%29+dosing%2C+indications%2C+interactions%2C+adverse+effects%2C+and+more&rft_id=http%3A%2F%2Freference.medscape.com%2Fdrug%2Femcyt-estramustine-342085%23showall&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-EmcytLabel-7">^ <a href="#cite_ref-EmcytLabel_7-0">a</a> <a href="#cite_ref-EmcytLabel_7-1">b</a> <a href="#cite_ref-EmcytLabel_7-2">c</a> <a href="#cite_ref-EmcytLabel_7-3">d</a> <a href="#cite_ref-EmcytLabel_7-4">e</a> <a href="#cite_ref-EmcytLabel_7-5">f</a> <a href="#cite_ref-EmcytLabel_7-6">g</a> <a href="#cite_ref-EmcytLabel_7-7">h</a> <a href="#cite_ref-EmcytLabel_7-8">i</a> <a href="#cite_ref-EmcytLabel_7-9">j</a> <a href="#cite_ref-EmcytLabel_7-10">k</a> <a href="#cite_ref-EmcytLabel_7-11">l</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/drugsatfda_docs/label/2008/018045s023lbl.pdf">"Emcyt estramustine phosphate sodium capsules"</a> (PDF). FDA. Retrieved 14 March 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=FDA&rft.atitle=Emcyt+estramustine+phosphate+sodium+capsules&rft_id=https%3A%2F%2Fwww.accessdata.fda.gov%2Fdrugsatfda_docs%2Flabel%2F2008%2F018045s023lbl.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid27684806-8">^ <a href="#cite_ref-pmid27684806_8-0">a</a> <a href="#cite_ref-pmid27684806_8-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFQinLiZhangTang2016" class="citation journal cs1">Qin Z, Li X, Zhang J, Tang J, Han P, Xu Z, et al. (September 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5265899">"Chemotherapy with or without estramustine for treatment of castration-resistant prostate cancer: A systematic review and meta-analysis"</a>. Medicine. 95 (39): e4801. <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%2FMD.0000000000004801">10.1097/MD.0000000000004801</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/PMC5265899">5265899</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/27684806">27684806</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Medicine&rft.atitle=Chemotherapy+with+or+without+estramustine+for+treatment+of+castration-resistant+prostate+cancer%3A+A+systematic+review+and+meta-analysis&rft.volume=95&rft.issue=39&rft.pages=e4801&rft.date=2016-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5265899%23id-name%3DPMC&rft_id=info%3Apmid%2F27684806&rft_id=info%3Adoi%2F10.1097%2FMD.0000000000004801&rft.aulast=Qin&rft.aufirst=Z&rft.au=Li%2C+X&rft.au=Zhang%2C+J&rft.au=Tang%2C+J&rft.au=Han%2C+P&rft.au=Xu%2C+Z&rft.au=Yu%2C+Y&rft.au=Yang%2C+C&rft.au=Wang%2C+C&rft.au=Xu%2C+T&rft.au=Xu%2C+Z&rft.au=Zou%2C+Q&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5265899&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid21756277-9">^ <a href="#cite_ref-pmid21756277_9-0">a</a> <a href="#cite_ref-pmid21756277_9-1">b</a> <a href="#cite_ref-pmid21756277_9-2">c</a> <a href="#cite_ref-pmid21756277_9-3">d</a> <a href="#cite_ref-pmid21756277_9-4">e</a> <a href="#cite_ref-pmid21756277_9-5">f</a> <a href="#cite_ref-pmid21756277_9-6">g</a> <a href="#cite_ref-pmid21756277_9-7">h</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRaveryFizaziOudardDrouet2011" class="citation journal cs1">Ravery V, Fizazi K, Oudard S, Drouet L, Eymard JC, Culine S, et al. (December 2011). "The use of estramustine phosphate in the modern management of advanced prostate cancer". BJU International. 108 (11): 1782–1786. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1464-410X.2011.10201.x">10.1111/j.1464-410X.2011.10201.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21756277">21756277</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:33456591">33456591</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BJU+International&rft.atitle=The+use+of+estramustine+phosphate+in+the+modern+management+of+advanced+prostate+cancer&rft.volume=108&rft.issue=11&rft.pages=1782-1786&rft.date=2011-12&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A33456591%23id-name%3DS2CID&rft_id=info%3Apmid%2F21756277&rft_id=info%3Adoi%2F10.1111%2Fj.1464-410X.2011.10201.x&rft.aulast=Ravery&rft.aufirst=V&rft.au=Fizazi%2C+K&rft.au=Oudard%2C+S&rft.au=Drouet%2C+L&rft.au=Eymard%2C+JC&rft.au=Culine%2C+S&rft.au=Gravis%2C+G&rft.au=Hennequin%2C+C&rft.au=Zerbib%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-SimpsonWagstaff2003-10">^ <a href="#cite_ref-SimpsonWagstaff2003_10-0">a</a> <a href="#cite_ref-SimpsonWagstaff2003_10-1">b</a> <a href="#cite_ref-SimpsonWagstaff2003_10-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSimpsonWagstaff2003" class="citation journal cs1">Simpson D, Wagstaff AJ (2003). "Estramustine Phosphate Sodium". American Journal of Cancer. 2 (5): 373–390. <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%2F00024669-200302050-00013">10.2165/00024669-200302050-00013</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:70507026">70507026</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+Cancer&rft.atitle=Estramustine+Phosphate+Sodium&rft.volume=2&rft.issue=5&rft.pages=373-390&rft.date=2003&rft_id=info%3Adoi%2F10.2165%2F00024669-200302050-00013&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A70507026%23id-name%3DS2CID&rft.aulast=Simpson&rft.aufirst=D&rft.au=Wagstaff%2C+AJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid9050135-11"><a href="#cite_ref-pmid9050135_11-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHudes1997" class="citation journal cs1">Hudes G (February 1997). "Estramustine-based chemotherapy". Seminars in Urologic Oncology. 15 (1): 13–19. <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/9050135">9050135</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Seminars+in+Urologic+Oncology&rft.atitle=Estramustine-based+chemotherapy&rft.volume=15&rft.issue=1&rft.pages=13-19&rft.date=1997-02&rft_id=info%3Apmid%2F9050135&rft.aulast=Hudes&rft.aufirst=G&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid8595142-12">^ <a href="#cite_ref-pmid8595142_12-0">a</a> <a href="#cite_ref-pmid8595142_12-1">b</a> <a href="#cite_ref-pmid8595142_12-2">c</a> <a href="#cite_ref-pmid8595142_12-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKreis1995" class="citation book cs1">Kreis W (1995). "Estramustine revisited". Concepts, Mechanisms, and New Targets for Chemotherapy. Cancer Treatment and Research. Vol. 78. Springer. pp. 163–184. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-4615-2007-8_8">10.1007/978-1-4615-2007-8_8</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4613-5829-9" title="Special:BookSources/978-1-4613-5829-9"><bdi>978-1-4613-5829-9</bdi></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/8595142">8595142</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Estramustine+revisited&rft.btitle=Concepts%2C+Mechanisms%2C+and+New+Targets+for+Chemotherapy&rft.series=Cancer+Treatment+and+Research&rft.pages=163-184&rft.pub=Springer&rft.date=1995&rft_id=info%3Apmid%2F8595142&rft_id=info%3Adoi%2F10.1007%2F978-1-4615-2007-8_8&rft.isbn=978-1-4613-5829-9&rft.aulast=Kreis&rft.aufirst=W&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid9274433-13">^ <a href="#cite_ref-pmid9274433_13-0">a</a> <a href="#cite_ref-pmid9274433_13-1">b</a> <a href="#cite_ref-pmid9274433_13-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGalbraithDuchesne1997" class="citation journal cs1">Galbraith SM, Duchesne GM (April 1997). "Androgens and prostate cancer: biology, pathology and hormonal therapy". European Journal of Cancer. 33 (4): 545–554. <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%2FS0959-8049%2896%2900444-3">10.1016/S0959-8049(96)00444-3</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/9274433">9274433</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Cancer&rft.atitle=Androgens+and+prostate+cancer%3A+biology%2C+pathology+and+hormonal+therapy&rft.volume=33&rft.issue=4&rft.pages=545-554&rft.date=1997-04&rft_id=info%3Adoi%2F10.1016%2FS0959-8049%2896%2900444-3&rft_id=info%3Apmid%2F9274433&rft.aulast=Galbraith&rft.aufirst=SM&rft.au=Duchesne%2C+GM&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-OettelSchillinger2012-14">^ <a href="#cite_ref-OettelSchillinger2012_14-0">a</a> <a href="#cite_ref-OettelSchillinger2012_14-1">b</a> <a href="#cite_ref-OettelSchillinger2012_14-2">c</a> <a href="#cite_ref-OettelSchillinger2012_14-3">d</a> <a href="#cite_ref-OettelSchillinger2012_14-4">e</a> <a href="#cite_ref-OettelSchillinger2012_14-5">f</a> <a href="#cite_ref-OettelSchillinger2012_14-6">g</a> <a href="#cite_ref-OettelSchillinger2012_14-7">h</a> <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&pg=PA540">Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen</a>. Springer Science & Business Media. pp. 540–. <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.pages=540-&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%26pg%3DPA540&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-IndexNominum2000-15">^ <a href="#cite_ref-IndexNominum2000_15-0">a</a> <a href="#cite_ref-IndexNominum2000_15-1">b</a> <a href="#cite_ref-IndexNominum2000_15-2">c</a> <a href="#cite_ref-IndexNominum2000_15-3">d</a> <a href="#cite_ref-IndexNominum2000_15-4">e</a> <a href="#cite_ref-IndexNominum2000_15-5">f</a> <a href="#cite_ref-IndexNominum2000_15-6">g</a> <a href="#cite_ref-IndexNominum2000_15-7">h</a> <a href="#cite_ref-IndexNominum2000_15-8">i</a> <a href="#cite_ref-IndexNominum2000_15-9">j</a> <a href="#cite_ref-IndexNominum2000_15-10">k</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. January 2000. pp. 406–407. <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>.</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=406-407&rft.pub=Taylor+%26+Francis&rft.date=2000-01&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%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Drugs.com-16">^ <a href="#cite_ref-Drugs.com_16-0">a</a> <a href="#cite_ref-Drugs.com_16-1">b</a> <a href="#cite_ref-Drugs.com_16-2">c</a> <a href="#cite_ref-Drugs.com_16-3">d</a> <a href="#cite_ref-Drugs.com_16-4">e</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/estramustine.html">"Estramustine Uses, Side Effects & Warnings"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Estramustine+Uses%2C+Side+Effects+%26+Warnings&rft_id=https%3A%2F%2Fwww.drugs.com%2Finternational%2Festramustine.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-EMP-EMC-17">^ <a href="#cite_ref-EMP-EMC_17-0">a</a> <a href="#cite_ref-EMP-EMC_17-1">b</a> <a href="#cite_ref-EMP-EMC_17-2">c</a> <a href="#cite_ref-EMP-EMC_17-3">d</a> <a href="#cite_ref-EMP-EMC_17-4">e</a> <a href="#cite_ref-EMP-EMC_17-5">f</a> <a href="#cite_ref-EMP-EMC_17-6">g</a> <a href="#cite_ref-EMP-EMC_17-7">h</a> <a href="#cite_ref-EMP-EMC_17-8">i</a> <a href="#cite_ref-EMP-EMC_17-9">j</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://web.archive.org/web/20140222203824/http://www.medicines.org.uk/emc/medicine/1511/SPC/Estracyt+Capsules/">"Estracyt Capsules - Summary of Product Characteristics (SPC)"</a>. electronic Medicines Compendium. Pfizer Limited. 12 August 2013. Archived from <a rel="nofollow" class="external text" href="http://www.medicines.org.uk/emc/medicine/1511/SPC/Estracyt+Capsules/">the original</a> on 22 February 2014. Retrieved 8 February 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=electronic+Medicines+Compendium&rft.atitle=Estracyt+Capsules+-+Summary+of+Product+Characteristics+%28SPC%29&rft.date=2013-08-12&rft_id=http%3A%2F%2Fwww.medicines.org.uk%2Femc%2Fmedicine%2F1511%2FSPC%2FEstracyt%2BCapsules%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Lupulescu1990-18"><a href="#cite_ref-Lupulescu1990_18-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLupulescu1990" class="citation book cs1">Lupulescu A (24 October 1990). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=VddUa-2cp-YC&pg=PA40">Hormones and Vitamins in Cancer Treatment</a>. CRC Press. pp. 40–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-8493-5973-6" title="Special:BookSources/978-0-8493-5973-6"><bdi>978-0-8493-5973-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Hormones+and+Vitamins+in+Cancer+Treatment&rft.pages=40-&rft.pub=CRC+Press&rft.date=1990-10-24&rft.isbn=978-0-8493-5973-6&rft.aulast=Lupulescu&rft.aufirst=A&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DVddUa-2cp-YC%26pg%3DPA40&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-StellaBorchardt2007-19">^ <a href="#cite_ref-StellaBorchardt2007_19-0">a</a> <a href="#cite_ref-StellaBorchardt2007_19-1">b</a> <a href="#cite_ref-StellaBorchardt2007_19-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStellaBorchardtHagemanOliyai2007" class="citation book cs1">Stella V, Borchardt R, Hageman M, Oliyai R, Maag H, Tilley J, eds. (12 March 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=qkjHxX5TgHEC&pg=PA174">Prodrugs: Challenges and Rewards</a>. Springer Science & Business Media. pp. 174–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-387-49782-2" title="Special:BookSources/978-0-387-49782-2"><bdi>978-0-387-49782-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Prodrugs%3A+Challenges+and+Rewards&rft.pages=174-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2007-03-12&rft.isbn=978-0-387-49782-2&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DqkjHxX5TgHEC%26pg%3DPA174&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid20094950-20"><a href="#cite_ref-pmid20094950_20-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKitamuraSuzukiNishimatsuKurosaki2010" class="citation journal cs1">Kitamura T, Suzuki M, Nishimatsu H, Kurosaki T, Enomoto Y, Fukuhara H, et al. (January 2010). "Final report on low-dose estramustine phosphate (EMP) monotherapy and very low-dose EMP therapy combined with LH-RH agonist for previously untreated advanced prostate cancer". Aktuelle Urologie. 41 (Suppl 1): S34–S40. <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-0029-1224657">10.1055/s-0029-1224657</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/20094950">20094950</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:7710924">7710924</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Aktuelle+Urologie&rft.atitle=Final+report+on+low-dose+estramustine+phosphate+%28EMP%29+monotherapy+and+very+low-dose+EMP+therapy+combined+with+LH-RH+agonist+for+previously+untreated+advanced+prostate+cancer&rft.volume=41&rft.issue=Suppl+1&rft.pages=S34-S40&rft.date=2010-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A7710924%23id-name%3DS2CID&rft_id=info%3Apmid%2F20094950&rft_id=info%3Adoi%2F10.1055%2Fs-0029-1224657&rft.aulast=Kitamura&rft.aufirst=T&rft.au=Suzuki%2C+M&rft.au=Nishimatsu%2C+H&rft.au=Kurosaki%2C+T&rft.au=Enomoto%2C+Y&rft.au=Fukuhara%2C+H&rft.au=Kume%2C+H&rft.au=Takeuchi%2C+T&rft.au=Miao%2C+L&rft.au=Jiangang%2C+H&rft.au=Xiaoqiang%2C+L&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid14644018-21"><a href="#cite_ref-pmid14644018_21-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSayedTaxel2003" class="citation journal cs1">Sayed Y, Taxel P (December 2003). "The use of estrogen therapy in men". Current Opinion in Pharmacology. 3 (6): 650–654. <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.coph.2003.07.004">10.1016/j.coph.2003.07.004</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/14644018">14644018</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Opinion+in+Pharmacology&rft.atitle=The+use+of+estrogen+therapy+in+men&rft.volume=3&rft.issue=6&rft.pages=650-654&rft.date=2003-12&rft_id=info%3Adoi%2F10.1016%2Fj.coph.2003.07.004&rft_id=info%3Apmid%2F14644018&rft.aulast=Sayed&rft.aufirst=Y&rft.au=Taxel%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid10699602-22">^ <a href="#cite_ref-pmid10699602_22-0">a</a> <a href="#cite_ref-pmid10699602_22-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHedlundHenriksson2000" class="citation journal cs1">Hedlund PO, Henriksson P (March 2000). "Parenteral estrogen versus total androgen ablation in the treatment of advanced prostate carcinoma: effects on overall survival and cardiovascular mortality. The Scandinavian Prostatic Cancer Group (SPCG)-5 Trial Study". Urology. 55 (3): 328–333. <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%2Fs0090-4295%2899%2900580-4">10.1016/s0090-4295(99)00580-4</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/10699602">10699602</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Parenteral+estrogen+versus+total+androgen+ablation+in+the+treatment+of+advanced+prostate+carcinoma%3A+effects+on+overall+survival+and+cardiovascular+mortality.+The+Scandinavian+Prostatic+Cancer+Group+%28SPCG%29-5+Trial+Study&rft.volume=55&rft.issue=3&rft.pages=328-333&rft.date=2000-03&rft_id=info%3Adoi%2F10.1016%2Fs0090-4295%2899%2900580-4&rft_id=info%3Apmid%2F10699602&rft.aulast=Hedlund&rft.aufirst=PO&rft.au=Henriksson%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid7541359-23"><a href="#cite_ref-pmid7541359_23-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFShimizuShibataJinboSatoh1995" class="citation journal cs1">Shimizu TS, Shibata Y, Jinbo H, Satoh J, Yamanaka H (1995). "Estramustine phosphate for preventing flare-up in luteinizing hormone-releasing hormone analogue depot therapy". European Urology. 27 (3): 192–195. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000475159">10.1159/000475159</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/7541359">7541359</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Urology&rft.atitle=Estramustine+phosphate+for+preventing+flare-up+in+luteinizing+hormone-releasing+hormone+analogue+depot+therapy&rft.volume=27&rft.issue=3&rft.pages=192-195&rft.date=1995&rft_id=info%3Adoi%2F10.1159%2F000475159&rft_id=info%3Apmid%2F7541359&rft.aulast=Shimizu&rft.aufirst=TS&rft.au=Shibata%2C+Y&rft.au=Jinbo%2C+H&rft.au=Satoh%2C+J&rft.au=Yamanaka%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Muller1998-24">^ <a href="#cite_ref-Muller1998_24-0">a</a> <a href="#cite_ref-Muller1998_24-1">b</a> <a href="#cite_ref-Muller1998_24-2">c</a> <a href="#cite_ref-Muller1998_24-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMullerDessing1998" class="citation book cs1">Muller NF, Dessing RP, eds. (19 June 1998). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=2HBPHmclMWIC&pg=PA245">European Drug Index: European Drug Registrations</a> (Fourth ed.). CRC Press. pp. 245, 454. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-7692-2114-5" title="Special:BookSources/978-3-7692-2114-5"><bdi>978-3-7692-2114-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=European+Drug+Index%3A+European+Drug+Registrations&rft.pages=245%2C+454&rft.edition=Fourth&rft.pub=CRC+Press&rft.date=1998-06-19&rft.isbn=978-3-7692-2114-5&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2HBPHmclMWIC%26pg%3DPA245&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Becker2001-25"><a href="#cite_ref-Becker2001_25-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBecker2001" class="citation book cs1">Becker KL (2001). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FVfzRvaucq8C&pg=PA2153">Principles and Practice of Endocrinology and Metabolism</a>. Lippincott Williams & Wilkins. pp. 2153–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-1750-2" title="Special:BookSources/978-0-7817-1750-2"><bdi>978-0-7817-1750-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Principles+and+Practice+of+Endocrinology+and+Metabolism&rft.pages=2153-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2001&rft.isbn=978-0-7817-1750-2&rft.aulast=Becker&rft.aufirst=KL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFVfzRvaucq8C%26pg%3DPA2153&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid15663992-26"><a href="#cite_ref-pmid15663992_26-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTammela2004" class="citation journal cs1">Tammela T (November 2004). "Endocrine treatment of prostate cancer". The Journal of Steroid Biochemistry and Molecular Biology. 92 (4): 287–295. <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.jsbmb.2004.10.005">10.1016/j.jsbmb.2004.10.005</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/15663992">15663992</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:25425351">25425351</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+Steroid+Biochemistry+and+Molecular+Biology&rft.atitle=Endocrine+treatment+of+prostate+cancer&rft.volume=92&rft.issue=4&rft.pages=287-295&rft.date=2004-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A25425351%23id-name%3DS2CID&rft_id=info%3Apmid%2F15663992&rft_id=info%3Adoi%2F10.1016%2Fj.jsbmb.2004.10.005&rft.aulast=Tammela&rft.aufirst=T&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid7500443-27"><a href="#cite_ref-pmid7500443_27-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCoxCrawford1995" class="citation journal cs1">Cox RL, Crawford ED (December 1995). "Estrogens in the treatment of prostate cancer". The Journal of Urology. 154 (6): 1991–1998. <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%2FS0022-5347%2801%2966670-9">10.1016/S0022-5347(01)66670-9</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7500443">7500443</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+Urology&rft.atitle=Estrogens+in+the+treatment+of+prostate+cancer&rft.volume=154&rft.issue=6&rft.pages=1991-1998&rft.date=1995-12&rft_id=info%3Adoi%2F10.1016%2FS0022-5347%2801%2966670-9&rft_id=info%3Apmid%2F7500443&rft.aulast=Cox&rft.aufirst=RL&rft.au=Crawford%2C+ED&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid15536625-28">^ <a href="#cite_ref-pmid15536625_28-0">a</a> <a href="#cite_ref-pmid15536625_28-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLubinieckiBerlinWeinsteinVaughn2004" class="citation journal cs1">Lubiniecki GM, Berlin JA, Weinstein RB, Vaughn DJ (December 2004). "Thromboembolic events with estramustine phosphate-based chemotherapy in patients with hormone-refractory prostate carcinoma: results of a meta-analysis". Cancer. 101 (12): 2755–2759. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcncr.20673">10.1002/cncr.20673</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/15536625">15536625</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:21465413">21465413</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer&rft.atitle=Thromboembolic+events+with+estramustine+phosphate-based+chemotherapy+in+patients+with+hormone-refractory+prostate+carcinoma%3A+results+of+a+meta-analysis&rft.volume=101&rft.issue=12&rft.pages=2755-2759&rft.date=2004-12&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A21465413%23id-name%3DS2CID&rft_id=info%3Apmid%2F15536625&rft_id=info%3Adoi%2F10.1002%2Fcncr.20673&rft.aulast=Lubiniecki&rft.aufirst=GM&rft.au=Berlin%2C+JA&rft.au=Weinstein%2C+RB&rft.au=Vaughn%2C+DJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid17942366-29"><a href="#cite_ref-pmid17942366_29-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFizaziLe_MaitreHudesBerry2007" class="citation journal cs1">Fizazi K, Le Maitre A, Hudes G, Berry WR, Kelly WK, Eymard JC, et al. (November 2007). "Addition of estramustine to chemotherapy and survival of patients with castration-refractory prostate cancer: a meta-analysis of individual patient data". The Lancet. Oncology. 8 (11): 994–1000. <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%2FS1470-2045%2807%2970284-X">10.1016/S1470-2045(07)70284-X</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17942366">17942366</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Lancet.+Oncology&rft.atitle=Addition+of+estramustine+to+chemotherapy+and+survival+of+patients+with+castration-refractory+prostate+cancer%3A+a+meta-analysis+of+individual+patient+data&rft.volume=8&rft.issue=11&rft.pages=994-1000&rft.date=2007-11&rft_id=info%3Adoi%2F10.1016%2FS1470-2045%2807%2970284-X&rft_id=info%3Apmid%2F17942366&rft.aulast=Fizazi&rft.aufirst=K&rft.au=Le+Maitre%2C+A&rft.au=Hudes%2C+G&rft.au=Berry%2C+WR&rft.au=Kelly%2C+WK&rft.au=Eymard%2C+JC&rft.au=Logothetis%2C+CJ&rft.au=Pignon%2C+JP&rft.au=Michiels%2C+S&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid25920994-30"><a href="#cite_ref-pmid25920994_30-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPetrioliRovielloFiaschiLaera2015" class="citation journal cs1">Petrioli R, Roviello G, Fiaschi AI, Laera L, Bianco V, Ponchietti R, et al. (October 2015). "Low-Dose Estramustine Phosphate and Concomitant Low-Dose Acetylsalicylic Acid in Heavily Pretreated Patients With Advanced Castration-Resistant Prostate Cancer". Clinical Genitourinary Cancer. 13 (5): 441–446. <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.clgc.2015.03.004">10.1016/j.clgc.2015.03.004</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/25920994">25920994</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Genitourinary+Cancer&rft.atitle=Low-Dose+Estramustine+Phosphate+and+Concomitant+Low-Dose+Acetylsalicylic+Acid+in+Heavily+Pretreated+Patients+With+Advanced+Castration-Resistant+Prostate+Cancer&rft.volume=13&rft.issue=5&rft.pages=441-446&rft.date=2015-10&rft_id=info%3Adoi%2F10.1016%2Fj.clgc.2015.03.004&rft_id=info%3Apmid%2F25920994&rft.aulast=Petrioli&rft.aufirst=R&rft.au=Roviello%2C+G&rft.au=Fiaschi%2C+AI&rft.au=Laera%2C+L&rft.au=Bianco%2C+V&rft.au=Ponchietti%2C+R&rft.au=Barbanti%2C+G&rft.au=Francini%2C+E&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid6375076-31">^ <a href="#cite_ref-pmid6375076_31-0">a</a> <a href="#cite_ref-pmid6375076_31-1">b</a> <a href="#cite_ref-pmid6375076_31-2">c</a> <a href="#cite_ref-pmid6375076_31-3">d</a> <a href="#cite_ref-pmid6375076_31-4">e</a> <a href="#cite_ref-pmid6375076_31-5">f</a> <a href="#cite_ref-pmid6375076_31-6">g</a> <a href="#cite_ref-pmid6375076_31-7">h</a> <a href="#cite_ref-pmid6375076_31-8">i</a> <a href="#cite_ref-pmid6375076_31-9">j</a> <a href="#cite_ref-pmid6375076_31-10">k</a> <a href="#cite_ref-pmid6375076_31-11">l</a> <a href="#cite_ref-pmid6375076_31-12">m</a> <a href="#cite_ref-pmid6375076_31-13">n</a> <a href="#cite_ref-pmid6375076_31-14">o</a> <a href="#cite_ref-pmid6375076_31-15">p</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGunnarssonForshell1984" class="citation journal cs1">Gunnarsson PO, Forshell GP (June 1984). "Clinical pharmacokinetics of estramustine phosphate". Urology. 23 (6 Suppl): 22–27. <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%2FS0090-4295%2884%2980093-X">10.1016/S0090-4295(84)80093-X</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6375076">6375076</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Clinical+pharmacokinetics+of+estramustine+phosphate&rft.volume=23&rft.issue=6+Suppl&rft.pages=22-27&rft.date=1984-06&rft_id=info%3Adoi%2F10.1016%2FS0090-4295%2884%2980093-X&rft_id=info%3Apmid%2F6375076&rft.aulast=Gunnarsson&rft.aufirst=PO&rft.au=Forshell%2C+GP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid86404-32">^ <a href="#cite_ref-pmid86404_32-0">a</a> <a href="#cite_ref-pmid86404_32-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAlexanderHancockMasoodPeet1979" class="citation journal cs1">Alexander NC, Hancock AK, Masood MB, Peet BG, Price JJ, Turner RL, et al. (March 1979). "Estracyt in advanced carcinoma of the breast: a phase II study". Clinical Radiology. 30 (2): 139–147. <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%2FS0009-9260%2879%2980133-6">10.1016/S0009-9260(79)80133-6</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/86404">86404</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Radiology&rft.atitle=Estracyt+in+advanced+carcinoma+of+the+breast%3A+a+phase+II+study&rft.volume=30&rft.issue=2&rft.pages=139-147&rft.date=1979-03&rft_id=info%3Adoi%2F10.1016%2FS0009-9260%2879%2980133-6&rft_id=info%3Apmid%2F86404&rft.aulast=Alexander&rft.aufirst=NC&rft.au=Hancock%2C+AK&rft.au=Masood%2C+MB&rft.au=Peet%2C+BG&rft.au=Price%2C+JJ&rft.au=Turner%2C+RL&rft.au=Stone%2C+J&rft.au=Ward%2C+AJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid6349745-33">^ <a href="#cite_ref-pmid6349745_33-0">a</a> <a href="#cite_ref-pmid6349745_33-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDaponteSylvesterDe_PauwFryszman1983" class="citation journal cs1">Daponte D, Sylvester R, De Pauw M, Fryszman A, Smith RM, Smith PH (August 1983). "Change in white cell count during treatment of advanced cancer of the prostate with estramustine phosphate and with stilboestrol". British Journal of Urology. 55 (4): 408–412. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1464-410X.1983.tb03333.x">10.1111/j.1464-410X.1983.tb03333.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6349745">6349745</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Urology&rft.atitle=Change+in+white+cell+count+during+treatment+of+advanced+cancer+of+the+prostate+with+estramustine+phosphate+and+with+stilboestrol&rft.volume=55&rft.issue=4&rft.pages=408-412&rft.date=1983-08&rft_id=info%3Adoi%2F10.1111%2Fj.1464-410X.1983.tb03333.x&rft_id=info%3Apmid%2F6349745&rft.aulast=Daponte&rft.aufirst=D&rft.au=Sylvester%2C+R&rft.au=De+Pauw%2C+M&rft.au=Fryszman%2C+A&rft.au=Smith%2C+RM&rft.au=Smith%2C+PH&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Emcyt-Label-34"><a href="#cite_ref-Emcyt-Label_34-0">^</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.accessdata.fda.gov/drugsatfda_docs/label/2008/018045s023lbl.pdf">"Emcyt estramustine phosphate sodium capsules"</a> (PDF). FDA. Retrieved 14 March 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=FDA&rft.atitle=Emcyt+estramustine+phosphate+sodium+capsules&rft_id=https%3A%2F%2Fwww.accessdata.fda.gov%2Fdrugsatfda_docs%2Flabel%2F2008%2F018045s023lbl.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Elks2014-35">^ <a href="#cite_ref-Elks2014_35-0">a</a> <a href="#cite_ref-Elks2014_35-1">b</a> <a href="#cite_ref-Elks2014_35-2">c</a> <a href="#cite_ref-Elks2014_35-3">d</a> <a href="#cite_ref-Elks2014_35-4">e</a> <a href="#cite_ref-Elks2014_35-5">f</a> <a href="#cite_ref-Elks2014_35-6">g</a> <a href="#cite_ref-Elks2014_35-7">h</a> <a href="#cite_ref-Elks2014_35-8">i</a> <a href="#cite_ref-Elks2014_35-9">j</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=PA502">The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies</a>. Springer. pp. 502–503. <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=502-503&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%3DPA502&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid10076535-36">^ <a href="#cite_ref-pmid10076535_36-0">a</a> <a href="#cite_ref-pmid10076535_36-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWangLiuKreisBudman1998" class="citation journal cs1">Wang LG, Liu XM, Kreis W, Budman DR (May 1998). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0006-2952%2897%2900657-6">"Androgen antagonistic effect of estramustine phosphate (EMP) metabolites on wild-type and mutated androgen receptor"</a>. Biochemical Pharmacology. 55 (9): 1427–1433. <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%2FS0006-2952%2897%2900657-6">10.1016/S0006-2952(97)00657-6</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/10076535">10076535</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemical+Pharmacology&rft.atitle=Androgen+antagonistic+effect+of+estramustine+phosphate+%28EMP%29+metabolites+on+wild-type+and+mutated+androgen+receptor&rft.volume=55&rft.issue=9&rft.pages=1427-1433&rft.date=1998-05&rft_id=info%3Adoi%2F10.1016%2FS0006-2952%2897%2900657-6&rft_id=info%3Apmid%2F10076535&rft.aulast=Wang&rft.aufirst=LG&rft.au=Liu%2C+XM&rft.au=Kreis%2C+W&rft.au=Budman%2C+DR&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252FS0006-2952%252897%252900657-6&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid2093302-37">^ <a href="#cite_ref-pmid2093302_37-0">a</a> <a href="#cite_ref-pmid2093302_37-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVan_PoppelWerbrouckBaert1990" class="citation journal cs1">Van Poppel H, Werbrouck PW, Baert L (1990). "Effect of estramustine phosphate on free androgens. A comparative study of the effect of orchiectomy and estramustine phosphate on free androgens in patients with prostatic cancer". Acta Urologica Belgica. 58 (4): 89–95. <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/2093302">2093302</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Urologica+Belgica&rft.atitle=Effect+of+estramustine+phosphate+on+free+androgens.+A+comparative+study+of+the+effect+of+orchiectomy+and+estramustine+phosphate+on+free+androgens+in+patients+with+prostatic+cancer&rft.volume=58&rft.issue=4&rft.pages=89-95&rft.date=1990&rft_id=info%3Apmid%2F2093302&rft.aulast=Van+Poppel&rft.aufirst=H&rft.au=Werbrouck%2C+PW&rft.au=Baert%2C+L&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid7190620-38">^ <a href="#cite_ref-pmid7190620_38-0">a</a> <a href="#cite_ref-pmid7190620_38-1">b</a> <a href="#cite_ref-pmid7190620_38-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKarrWajsmanKirdaniMurphy1980" class="citation journal cs1">Karr JP, Wajsman Z, Kirdani RY, Murphy GP, Sandberg AA (August 1980). "Effects of diethylstilbestrol and estramustine phosphate on serum sex hormone binding globulin and testosterone levels in prostate cancer patients". The Journal of Urology. 124 (2): 232–236. <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%2FS0022-5347%2817%2955383-5">10.1016/S0022-5347(17)55383-5</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/7190620">7190620</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+Urology&rft.atitle=Effects+of+diethylstilbestrol+and+estramustine+phosphate+on+serum+sex+hormone+binding+globulin+and+testosterone+levels+in+prostate+cancer+patients&rft.volume=124&rft.issue=2&rft.pages=232-236&rft.date=1980-08&rft_id=info%3Adoi%2F10.1016%2FS0022-5347%2817%2955383-5&rft_id=info%3Apmid%2F7190620&rft.aulast=Karr&rft.aufirst=JP&rft.au=Wajsman%2C+Z&rft.au=Kirdani%2C+RY&rft.au=Murphy%2C+GP&rft.au=Sandberg%2C+AA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid12084341-39"><a href="#cite_ref-pmid12084341_39-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOlsonPienta2000" class="citation journal cs1">Olson KB, Pienta KJ (May 2000). "Recent advances in chemotherapy for advanced prostate cancer". Current Urology Reports. 1 (1): 48–56. <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%2Fs11934-000-0035-z">10.1007/s11934-000-0035-z</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/12084341">12084341</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:31084737">31084737</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Urology+Reports&rft.atitle=Recent+advances+in+chemotherapy+for+advanced+prostate+cancer&rft.volume=1&rft.issue=1&rft.pages=48-56&rft.date=2000-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A31084737%23id-name%3DS2CID&rft_id=info%3Apmid%2F12084341&rft_id=info%3Adoi%2F10.1007%2Fs11934-000-0035-z&rft.aulast=Olson&rft.aufirst=KB&rft.au=Pienta%2C+KJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid3092893-40">^ <a href="#cite_ref-pmid3092893_40-0">a</a> <a href="#cite_ref-pmid3092893_40-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDaehlinDambervon_SchoultzBergman1986" class="citation journal cs1">Daehlin L, Damber JE, von Schoultz B, Bergman B (August 1986). "The oestrogenic effects of ethinyl oestradiol/polyoestradiol phosphate and estramustine phosphate in patients with prostatic carcinoma. A comparative study of oestrogen sensitive liver proteins, gonadotrophins and prolactin". British Journal of Urology. 58 (4): 412–416. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1464-410X.1986.tb09095.x">10.1111/j.1464-410X.1986.tb09095.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3092893">3092893</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=British+Journal+of+Urology&rft.atitle=The+oestrogenic+effects+of+ethinyl+oestradiol%2Fpolyoestradiol+phosphate+and+estramustine+phosphate+in+patients+with+prostatic+carcinoma.+A+comparative+study+of+oestrogen+sensitive+liver+proteins%2C+gonadotrophins+and+prolactin&rft.volume=58&rft.issue=4&rft.pages=412-416&rft.date=1986-08&rft_id=info%3Adoi%2F10.1111%2Fj.1464-410X.1986.tb09095.x&rft_id=info%3Apmid%2F3092893&rft.aulast=Daehlin&rft.aufirst=L&rft.au=Damber%2C+JE&rft.au=von+Schoultz%2C+B&rft.au=Bergman%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Fredholm1974-41"><a href="#cite_ref-Fredholm1974_41-0">^</a> Fredholm, B., Jensen, G., Lindskog, M., & Muntzing, J. (1974, January). Effects of estramustine phosphate (Estracyt) on growth of DMBA-induced mammary tumors in rats. In Acta Pharmacologica et Toxicologica (Vol. 35, pp. 28-28). 35 Norre Sogade, PO Box 2148, DK-1016 Copenhagen, Denmark: Munksgaard Int Publ Ltd. </li> <li id="cite_note-pmid1545778-42">^ <a href="#cite_ref-pmid1545778_42-0">a</a> <a href="#cite_ref-pmid1545778_42-1">b</a> <a href="#cite_ref-pmid1545778_42-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPunziDuaxStrongGriffin1992" class="citation journal cs1">Punzi JS, Duax WL, Strong P, Griffin JF, Flocco MM, Zacharias DE, et al. (March 1992). <a rel="nofollow" class="external text" href="http://molpharm.aspetjournals.org/content/41/3/569">"Molecular conformation of estramustine and two analogues"</a>. Molecular Pharmacology. 41 (3): 569–576. <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/1545778">1545778</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Pharmacology&rft.atitle=Molecular+conformation+of+estramustine+and+two+analogues&rft.volume=41&rft.issue=3&rft.pages=569-576&rft.date=1992-03&rft_id=info%3Apmid%2F1545778&rft.aulast=Punzi&rft.aufirst=JS&rft.au=Duax%2C+WL&rft.au=Strong%2C+P&rft.au=Griffin%2C+JF&rft.au=Flocco%2C+MM&rft.au=Zacharias%2C+DE&rft.au=Carrell%2C+HL&rft.au=Tew%2C+KD&rft.au=Glusker%2C+JP&rft_id=http%3A%2F%2Fmolpharm.aspetjournals.org%2Fcontent%2F41%2F3%2F569&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid6373212-43">^ <a href="#cite_ref-pmid6373212_43-0">a</a> <a href="#cite_ref-pmid6373212_43-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHauserMerryman1984" class="citation journal cs1">Hauser AR, Merryman R (May 1984). "Estramustine phosphate sodium". Drug Intelligence & Clinical Pharmacy. 18 (5): 368–374. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F106002808401800502">10.1177/106002808401800502</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/6373212">6373212</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:25303747">25303747</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Intelligence+%26+Clinical+Pharmacy&rft.atitle=Estramustine+phosphate+sodium&rft.volume=18&rft.issue=5&rft.pages=368-374&rft.date=1984-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A25303747%23id-name%3DS2CID&rft_id=info%3Apmid%2F6373212&rft_id=info%3Adoi%2F10.1177%2F106002808401800502&rft.aulast=Hauser&rft.aufirst=AR&rft.au=Merryman%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid2682681-44"><a href="#cite_ref-pmid2682681_44-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTewStearns1989" class="citation journal cs1">Tew KD, Stearns ME (1989). "Estramustine--a nitrogen mustard/steroid with antimicrotubule activity". Pharmacology & Therapeutics. 43 (3): 299–319. <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%2F0163-7258%2889%2990012-0">10.1016/0163-7258(89)90012-0</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/2682681">2682681</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology+%26+Therapeutics&rft.atitle=Estramustine--a+nitrogen+mustard%2Fsteroid+with+antimicrotubule+activity&rft.volume=43&rft.issue=3&rft.pages=299-319&rft.date=1989&rft_id=info%3Adoi%2F10.1016%2F0163-7258%2889%2990012-0&rft_id=info%3Apmid%2F2682681&rft.aulast=Tew&rft.aufirst=KD&rft.au=Stearns%2C+ME&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-CavalliKaye2009-45"><a href="#cite_ref-CavalliKaye2009_45-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCavalliKayeHansenArmitage2009" class="citation book cs1">Cavalli F, Kaye SB, Hansen HH, Armitage JO, Piccart-Gebhart M, eds. (12 September 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=WdDKBQAAQBAJ&pg=PA442">Textbook of Medical Oncology</a> (Fourth ed.). CRC Press. pp. 442–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-203-09289-7" title="Special:BookSources/978-0-203-09289-7"><bdi>978-0-203-09289-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Textbook+of+Medical+Oncology&rft.pages=442-&rft.edition=Fourth&rft.pub=CRC+Press&rft.date=2009-09-12&rft.isbn=978-0-203-09289-7&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DWdDKBQAAQBAJ%26pg%3DPA442&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid6673977-46"><a href="#cite_ref-pmid6673977_46-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGunnarssonAnderssonJohansson1983" class="citation journal cs1">Gunnarsson O, Andersson SB, Johansson SA (1983). "The hydrolysis of estramustine phosphate; in vitro studies". European Journal of Drug Metabolism and Pharmacokinetics. 8 (4): 395–402. <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%2FBF03188772">10.1007/BF03188772</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/6673977">6673977</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:22105700">22105700</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Drug+Metabolism+and+Pharmacokinetics&rft.atitle=The+hydrolysis+of+estramustine+phosphate%3B+in+vitro+studies&rft.volume=8&rft.issue=4&rft.pages=395-402&rft.date=1983&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A22105700%23id-name%3DS2CID&rft_id=info%3Apmid%2F6673977&rft_id=info%3Adoi%2F10.1007%2FBF03188772&rft.aulast=Gunnarsson&rft.aufirst=O&rft.au=Andersson%2C+SB&rft.au=Johansson%2C+SA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid19735314-47">^ <a href="#cite_ref-pmid19735314_47-0">a</a> <a href="#cite_ref-pmid19735314_47-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFOzekiTakeuchiSuzukiKitamura2009" class="citation journal cs1">Ozeki T, Takeuchi M, Suzuki M, Kitamura T, Takayanagi R, Yokoyama H, Yamada Y (October 2009). "Single nucleotide polymorphisms of 17beta-hydroxysteroid dehydrogenase type 7 gene: mechanism of estramustine-related adverse reactions?". International Journal of Urology. 16 (10): 836–841. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1442-2042.2009.02374.x">10.1111/j.1442-2042.2009.02374.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19735314">19735314</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:38350076">38350076</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Urology&rft.atitle=Single+nucleotide+polymorphisms+of+17beta-hydroxysteroid+dehydrogenase+type+7+gene%3A+mechanism+of+estramustine-related+adverse+reactions%3F&rft.volume=16&rft.issue=10&rft.pages=836-841&rft.date=2009-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A38350076%23id-name%3DS2CID&rft_id=info%3Apmid%2F19735314&rft_id=info%3Adoi%2F10.1111%2Fj.1442-2042.2009.02374.x&rft.aulast=Ozeki&rft.aufirst=T&rft.au=Takeuchi%2C+M&rft.au=Suzuki%2C+M&rft.au=Kitamura%2C+T&rft.au=Takayanagi%2C+R&rft.au=Yokoyama%2C+H&rft.au=Yamada%2C+Y&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-pmid15733111-48">^ <a href="#cite_ref-pmid15733111_48-0">a</a> <a href="#cite_ref-pmid15733111_48-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSuzukiMutoHaraOzeki2005" class="citation journal cs1">Suzuki M, Muto S, Hara K, Ozeki T, Yamada Y, Kadowaki T, et al. (February 2005). "Single-nucleotide polymorphisms in the 17beta-hydroxysteroid dehydrogenase genes might predict the risk of side-effects of estramustine phosphate sodium in prostate cancer patients". International Journal of Urology. 12 (2): 166–172. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1442-2042.2005.01004.x">10.1111/j.1442-2042.2005.01004.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15733111">15733111</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:71166897">71166897</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Urology&rft.atitle=Single-nucleotide+polymorphisms+in+the+17beta-hydroxysteroid+dehydrogenase+genes+might+predict+the+risk+of+side-effects+of+estramustine+phosphate+sodium+in+prostate+cancer+patients&rft.volume=12&rft.issue=2&rft.pages=166-172&rft.date=2005-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A71166897%23id-name%3DS2CID&rft_id=info%3Apmid%2F15733111&rft_id=info%3Adoi%2F10.1111%2Fj.1442-2042.2005.01004.x&rft.aulast=Suzuki&rft.aufirst=M&rft.au=Muto%2C+S&rft.au=Hara%2C+K&rft.au=Ozeki%2C+T&rft.au=Yamada%2C+Y&rft.au=Kadowaki%2C+T&rft.au=Tomita%2C+K&rft.au=Kameyama%2C+S&rft.au=Kitamura%2C+T&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-GateTew2011-49"><a href="#cite_ref-GateTew2011_49-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGateTew2011" class="citation book cs1">Gate L, Tew KD (2011). "Alkylating Agents". Cancer Management in Man: Chemotherapy, Biological Therapy, Hyperthermia and Supporting Measures. Cancer Growth and Progression. Springer. pp. 61–85. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-90-481-9704-0_4">10.1007/978-90-481-9704-0_4</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-90-481-9703-3" title="Special:BookSources/978-90-481-9703-3"><bdi>978-90-481-9703-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Alkylating+Agents&rft.btitle=Cancer+Management+in+Man%3A+Chemotherapy%2C+Biological+Therapy%2C+Hyperthermia+and+Supporting+Measures&rft.series=Cancer+Growth+and+Progression&rft.pages=61-85&rft.pub=Springer&rft.date=2011&rft_id=info%3Adoi%2F10.1007%2F978-90-481-9704-0_4&rft.isbn=978-90-481-9703-3&rft.aulast=Gate&rft.aufirst=L&rft.au=Tew%2C+KD&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Abbott2009-50"><a href="#cite_ref-Abbott2009_50-0">^</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://web.archive.org/web/20211127070253/https://www.ilexmedical.com/files/PDF/Estradiol_ARC.pdf">"Estradiol"</a> (PDF). Abbott Laboratories. November 2009. Archived from <a rel="nofollow" class="external text" href="http://www.ilexmedical.com/files/PDF/Estradiol_ARC.pdf">the original</a> (PDF) on 2021-11-27. Retrieved 2018-09-20.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Abbott+Laboratories&rft.atitle=Estradiol&rft.date=2009-11&rft_id=http%3A%2F%2Fwww.ilexmedical.com%2Ffiles%2FPDF%2FEstradiol_ARC.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Loftsson2014-51"><a href="#cite_ref-Loftsson2014_51-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLoftsson2014" class="citation book cs1">Loftsson T (25 January 2014). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dUzyAQAAQBAJ&pg=PA77">Drug Stability for Pharmaceutical Scientists</a>. Academic Press. pp. 77–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-411562-0" title="Special:BookSources/978-0-12-411562-0"><bdi>978-0-12-411562-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drug+Stability+for+Pharmaceutical+Scientists&rft.pages=77-&rft.pub=Academic+Press&rft.date=2014-01-25&rft.isbn=978-0-12-411562-0&rft.aulast=Loftsson&rft.aufirst=T&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdUzyAQAAQBAJ%26pg%3DPA77&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Bernal1997-52"><a href="#cite_ref-Bernal1997_52-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBernal1997" class="citation book cs1">Bernal S (21 August 1997). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=x9rL5HiTFTUC&pg=PA287">Drug Resistance in Oncology</a>. CRC Press. pp. 287–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4200-0209-6" title="Special:BookSources/978-1-4200-0209-6"><bdi>978-1-4200-0209-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drug+Resistance+in+Oncology&rft.pages=287-&rft.pub=CRC+Press&rft.date=1997-08-21&rft.isbn=978-1-4200-0209-6&rft.aulast=Bernal&rft.aufirst=S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dx9rL5HiTFTUC%26pg%3DPA287&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Murff2012-53"><a href="#cite_ref-Murff2012_53-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMurff2012" class="citation book cs1">Murff SJ (20 February 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=CqIPtcoUiMMC&pg=PA89">Safety and Health Handbook for Cytotoxic Drugs</a>. Government Institutes. pp. 89–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60590-705-5" title="Special:BookSources/978-1-60590-705-5"><bdi>978-1-60590-705-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Safety+and+Health+Handbook+for+Cytotoxic+Drugs&rft.pages=89-&rft.pub=Government+Institutes&rft.date=2012-02-20&rft.isbn=978-1-60590-705-5&rft.aulast=Murff&rft.aufirst=SJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DCqIPtcoUiMMC%26pg%3DPA89&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-PubChem-54">^ <a href="#cite_ref-PubChem_54-0">a</a> <a href="#cite_ref-PubChem_54-1">b</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://pubchem.ncbi.nlm.nih.gov/compound/259329">"Estramustine phosphate"</a>. PubChem. U.S. National Library of Medicine.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem&rft.atitle=Estramustine+phosphate&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2F259329&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-FiggChau2010-55"><a href="#cite_ref-FiggChau2010_55-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFiggChauSmall2010" class="citation book cs1">Figg WD, Chau CH, Small EJ (14 September 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4KDrjeWA5-UC&pg=PA402">Drug Management of Prostate Cancer</a>. Springer Science & Business Media. pp. 402–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60327-829-4" title="Special:BookSources/978-1-60327-829-4"><bdi>978-1-60327-829-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drug+Management+of+Prostate+Cancer&rft.pages=402-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2010-09-14&rft.isbn=978-1-60327-829-4&rft.aulast=Figg&rft.aufirst=WD&rft.au=Chau%2C+CH&rft.au=Small%2C+EJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4KDrjeWA5-UC%26pg%3DPA402&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-MortonHall2012-56"><a href="#cite_ref-MortonHall2012_56-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMortonHall2012" class="citation book cs1">Morton IK, Hall JM (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA114">Concise Dictionary of Pharmacological Agents: Properties and Synonyms</a>. Springer Science & Business Media. pp. 114–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-94-011-4439-1" title="Special:BookSources/978-94-011-4439-1"><bdi>978-94-011-4439-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Concise+Dictionary+of+Pharmacological+Agents%3A+Properties+and+Synonyms&rft.pages=114-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-94-011-4439-1&rft.aulast=Morton&rft.aufirst=IK&rft.au=Hall%2C+JM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DtsjrCAAAQBAJ%26pg%3DPA114&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Drugs@FDA-57"><a href="#cite_ref-Drugs@FDA_57-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.accessdata.fda.gov/scripts/cder/daf/">"Drugs@FDA: FDA Approved Drug Products"</a>. United States Food and Drug Administration. Retrieved 29 January 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Drugs%40FDA%3A+FDA+Approved+Drug+Products&rft.pub=United+States+Food+and+Drug+Administration&rft_id=http%3A%2F%2Fwww.accessdata.fda.gov%2Fscripts%2Fcder%2Fdaf%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"> </li> <li id="cite_note-Martindale-58"><a href="#cite_ref-Martindale_58-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSweetman,_S2013" class="citation book cs1">Sweetman, S, ed. (12 February 2013). "Estramustine Sodium Phosphate". <a rel="nofollow" class="external text" href="http://www.medicinescomplete.com/mc/martindale/current/1832-c.htm">Martindale: The Complete Drug Reference</a>. London, UK: Pharmaceutical Press. Retrieved 8 February 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Estramustine+Sodium+Phosphate&rft.btitle=Martindale%3A+The+Complete+Drug+Reference&rft.place=London%2C+UK&rft.pub=Pharmaceutical+Press&rft.date=2013-02-12&rft_id=http%3A%2F%2Fwww.medicinescomplete.com%2Fmc%2Fmartindale%2Fcurrent%2F1832-c.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" 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=Estramustine_phosphate&action=edit&section=19" 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 refbegin-columns references-column-width" style="column-width: 30em"> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTew1983" class="citation journal cs1">Tew KD (September 1983). "The mechanism of action of estramustine". Seminars in Oncology. 10 (3 Suppl 3): 21–26. <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/6364362">6364362</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Seminars+in+Oncology&rft.atitle=The+mechanism+of+action+of+estramustine&rft.volume=10&rft.issue=3+Suppl+3&rft.pages=21-26&rft.date=1983-09&rft_id=info%3Apmid%2F6364362&rft.aulast=Tew&rft.aufirst=KD&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHoisaeterBakke1983" class="citation journal cs1">Hoisaeter PA, Bakke A (September 1983). "Estramustine phosphate (Estracyt): experimental and clinical studies in Europe". Seminars in Oncology. 10 (3 Suppl 3): 27–33. <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/6364363">6364363</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Seminars+in+Oncology&rft.atitle=Estramustine+phosphate+%28Estracyt%29%3A+experimental+and+clinical+studies+in+Europe&rft.volume=10&rft.issue=3+Suppl+3&rft.pages=27-33&rft.date=1983-09&rft_id=info%3Apmid%2F6364363&rft.aulast=Hoisaeter&rft.aufirst=PA&rft.au=Bakke%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSandberg1983" class="citation journal cs1">Sandberg AA (September 1983). "Metabolic aspects and actions unique to Estracyt". Seminars in Oncology. 10 (3 Suppl 3): 3–15. <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/6364364">6364364</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Seminars+in+Oncology&rft.atitle=Metabolic+aspects+and+actions+unique+to+Estracyt&rft.volume=10&rft.issue=3+Suppl+3&rft.pages=3-15&rft.date=1983-09&rft_id=info%3Apmid%2F6364364&rft.aulast=Sandberg&rft.aufirst=AA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaukaas1984" class="citation journal cs1">Haukaas SA (1984). "Immunological effects of diethylstilbestrol and estramustine phosphate". Scandinavian Journal of Urology and Nephrology. Supplementum. 83: 1–32. <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/6387896">6387896</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Scandinavian+Journal+of+Urology+and+Nephrology.+Supplementum&rft.atitle=Immunological+effects+of+diethylstilbestrol+and+estramustine+phosphate&rft.volume=83&rft.pages=1-32&rft.date=1984&rft_id=info%3Apmid%2F6387896&rft.aulast=Haukaas&rft.aufirst=SA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHauserMerryman1984" class="citation journal cs1">Hauser AR, Merryman R (May 1984). "Estramustine phosphate sodium". Drug Intelligence & Clinical Pharmacy. 18 (5): 368–374. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1177%2F106002808401800502">10.1177/106002808401800502</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/6373212">6373212</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:25303747">25303747</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drug+Intelligence+%26+Clinical+Pharmacy&rft.atitle=Estramustine+phosphate+sodium&rft.volume=18&rft.issue=5&rft.pages=368-374&rft.date=1984-05&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A25303747%23id-name%3DS2CID&rft_id=info%3Apmid%2F6373212&rft_id=info%3Adoi%2F10.1177%2F106002808401800502&rft.aulast=Hauser&rft.aufirst=AR&rft.au=Merryman%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSandberg1984" class="citation journal cs1">Sandberg AA (June 1984). "Metabolic parameters of Estracyt pertinent to its effects in prostatic cancer". Urology. 23 (6 Suppl): 11–21. <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%2FS0090-4295%2884%2980092-8">10.1016/S0090-4295(84)80092-8</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/6375075">6375075</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Metabolic+parameters+of+Estracyt+pertinent+to+its+effects+in+prostatic+cancer&rft.volume=23&rft.issue=6+Suppl&rft.pages=11-21&rft.date=1984-06&rft_id=info%3Adoi%2F10.1016%2FS0090-4295%2884%2980092-8&rft_id=info%3Apmid%2F6375075&rft.aulast=Sandberg&rft.aufirst=AA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGunnarssonForshell1984" class="citation journal cs1">Gunnarsson PO, Forshell GP (June 1984). "Clinical pharmacokinetics of estramustine phosphate". Urology. 23 (6 Suppl): 22–27. <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%2FS0090-4295%2884%2980093-X">10.1016/S0090-4295(84)80093-X</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6375076">6375076</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Clinical+pharmacokinetics+of+estramustine+phosphate&rft.volume=23&rft.issue=6+Suppl&rft.pages=22-27&rft.date=1984-06&rft_id=info%3Adoi%2F10.1016%2FS0090-4295%2884%2980093-X&rft_id=info%3Apmid%2F6375076&rft.aulast=Gunnarsson&rft.aufirst=PO&rft.au=Forshell%2C+GP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFForsgrenBjörk1984" class="citation journal cs1">Forsgren B, Björk P (June 1984). "Specific binding of estramustine to prostatic proteins". Urology. 23 (6 Suppl): 34–38. <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%2FS0090-4295%2884%2980095-3">10.1016/S0090-4295(84)80095-3</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/6375077">6375077</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Specific+binding+of+estramustine+to+prostatic+proteins&rft.volume=23&rft.issue=6+Suppl&rft.pages=34-38&rft.date=1984-06&rft_id=info%3Adoi%2F10.1016%2FS0090-4295%2884%2980095-3&rft_id=info%3Apmid%2F6375077&rft.aulast=Forsgren&rft.aufirst=B&rft.au=Bj%C3%B6rk%2C+P&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKallandHaukaas1984" class="citation journal cs1">Kalland T, Haukaas SA (June 1984). "Immunologic effects of estramustine phosphate". Urology. 23 (6 Suppl): 39–45. <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%2FS0090-4295%2884%2980096-5">10.1016/S0090-4295(84)80096-5</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/6375078">6375078</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Immunologic+effects+of+estramustine+phosphate&rft.volume=23&rft.issue=6+Suppl&rft.pages=39-45&rft.date=1984-06&rft_id=info%3Adoi%2F10.1016%2FS0090-4295%2884%2980096-5&rft_id=info%3Apmid%2F6375078&rft.aulast=Kalland&rft.aufirst=T&rft.au=Haukaas%2C+SA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHøisaeter1984" class="citation journal cs1">Høisaeter PA (June 1984). "Mode of action of Emcyt". Urology. 23 (6 Suppl): 46–48. <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%2FS0090-4295%2884%2980097-7">10.1016/S0090-4295(84)80097-7</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6375079">6375079</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Mode+of+action+of+Emcyt&rft.volume=23&rft.issue=6+Suppl&rft.pages=46-48&rft.date=1984-06&rft_id=info%3Adoi%2F10.1016%2FS0090-4295%2884%2980097-7&rft_id=info%3Apmid%2F6375079&rft.aulast=H%C3%B8isaeter&rft.aufirst=PA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMüntzingGunnarsson1984" class="citation journal cs1">Müntzing J, Gunnarsson K (June 1984). "Preclinical pharmacology and toxicology of estramustine phosphate". Urology. 23 (6 Suppl): 6–10. <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%2FS0090-4295%2884%2980091-6">10.1016/S0090-4295(84)80091-6</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/6375082">6375082</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Preclinical+pharmacology+and+toxicology+of+estramustine+phosphate&rft.volume=23&rft.issue=6+Suppl&rft.pages=6-10&rft.date=1984-06&rft_id=info%3Adoi%2F10.1016%2FS0090-4295%2884%2980091-6&rft_id=info%3Apmid%2F6375082&rft.aulast=M%C3%BCntzing&rft.aufirst=J&rft.au=Gunnarsson%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSlackMurphy1984" class="citation journal cs1">Slack NH, Murphy GP (June 1984). "Clinical toxicity and long-term results of Emcyt therapy for prostate cancer". Urology. 23 (6 Suppl): 73–77. <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%2FS0090-4295%2884%2980103-X">10.1016/S0090-4295(84)80103-X</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6375085">6375085</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Urology&rft.atitle=Clinical+toxicity+and+long-term+results+of+Emcyt+therapy+for+prostate+cancer&rft.volume=23&rft.issue=6+Suppl&rft.pages=73-77&rft.date=1984-06&rft_id=info%3Adoi%2F10.1016%2FS0090-4295%2884%2980103-X&rft_id=info%3Apmid%2F6375085&rft.aulast=Slack&rft.aufirst=NH&rft.au=Murphy%2C+GP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHedlund1985" class="citation journal cs1">Hedlund PO (1985). "Mode of action of estramustine phosphate in hormone dependent and hormone non-dependent prostate cancer". Progress in Clinical and Biological Research. 185A: 197–202. <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/3898129">3898129</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Progress+in+Clinical+and+Biological+Research&rft.atitle=Mode+of+action+of+estramustine+phosphate+in+hormone+dependent+and+hormone+non-dependent+prostate+cancer&rft.volume=185A&rft.pages=197-202&rft.date=1985&rft_id=info%3Apmid%2F3898129&rft.aulast=Hedlund&rft.aufirst=PO&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHedlund1987" class="citation journal cs1">Hedlund PO (1987). "Estracyt--mode of action and clinical experience". Progress in Clinical and Biological Research. 243B: 215–219. <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/3309981">3309981</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Progress+in+Clinical+and+Biological+Research&rft.atitle=Estracyt--mode+of+action+and+clinical+experience&rft.volume=243B&rft.pages=215-219&rft.date=1987&rft_id=info%3Apmid%2F3309981&rft.aulast=Hedlund&rft.aufirst=PO&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMurphy1987" class="citation journal cs1">Murphy GP (1987). "A current review of the clinical experience with Estracyt". Progress in Clinical and Biological Research. 243B: 221–225. <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/3309982">3309982</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Progress+in+Clinical+and+Biological+Research&rft.atitle=A+current+review+of+the+clinical+experience+with+Estracyt&rft.volume=243B&rft.pages=221-225&rft.date=1987&rft_id=info%3Apmid%2F3309982&rft.aulast=Murphy&rft.aufirst=GP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFForsgren1988" class="citation journal cs1">Forsgren B (1988). "Estramustine-binding protein in rat and human prostate". Scandinavian Journal of Urology and Nephrology. Supplementum. 107: 56–58. <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/3287598">3287598</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Scandinavian+Journal+of+Urology+and+Nephrology.+Supplementum&rft.atitle=Estramustine-binding+protein+in+rat+and+human+prostate&rft.volume=107&rft.pages=56-58&rft.date=1988&rft_id=info%3Apmid%2F3287598&rft.aulast=Forsgren&rft.aufirst=B&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTewStearns1989" class="citation journal cs1">Tew KD, Stearns ME (1989). "Intracellular effects of estramustine (Estracyt/Emcyt)". Progress in Clinical and Biological Research. 303: 169–175. <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/2674983">2674983</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Progress+in+Clinical+and+Biological+Research&rft.atitle=Intracellular+effects+of+estramustine+%28Estracyt%2FEmcyt%29&rft.volume=303&rft.pages=169-175&rft.date=1989&rft_id=info%3Apmid%2F2674983&rft.aulast=Tew&rft.aufirst=KD&rft.au=Stearns%2C+ME&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTewStearns1989" class="citation journal cs1">Tew KD, Stearns ME (1989). "Estramustine--a nitrogen mustard/steroid with antimicrotubule activity". Pharmacology & Therapeutics. 43 (3): 299–319. <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%2F0163-7258%2889%2990012-0">10.1016/0163-7258(89)90012-0</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/2682681">2682681</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology+%26+Therapeutics&rft.atitle=Estramustine--a+nitrogen+mustard%2Fsteroid+with+antimicrotubule+activity&rft.volume=43&rft.issue=3&rft.pages=299-319&rft.date=1989&rft_id=info%3Adoi%2F10.1016%2F0163-7258%2889%2990012-0&rft_id=info%3Apmid%2F2682681&rft.aulast=Tew&rft.aufirst=KD&rft.au=Stearns%2C+ME&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKönyves1989" class="citation journal cs1">Könyves I (1989). "Estramustine phosphate (Estracyt) in the treatment of prostatic carcinoma". International Urology and Nephrology. 21 (4): 393–397. <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%2FBF02559635">10.1007/BF02559635</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/2693392">2693392</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:9727646">9727646</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Urology+and+Nephrology&rft.atitle=Estramustine+phosphate+%28Estracyt%29+in+the+treatment+of+prostatic+carcinoma&rft.volume=21&rft.issue=4&rft.pages=393-397&rft.date=1989&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A9727646%23id-name%3DS2CID&rft_id=info%3Apmid%2F2693392&rft_id=info%3Adoi%2F10.1007%2FBF02559635&rft.aulast=K%C3%B6nyves&rft.aufirst=I&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBensonHartley-Asp1990" class="citation journal cs1">Benson R, Hartley-Asp B (1990). "Mechanisms of action and clinical uses of estramustine". Cancer Investigation. 8 (3–4): 375–380. <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%2F07357909009012056">10.3109/07357909009012056</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/2207764">2207764</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer+Investigation&rft.atitle=Mechanisms+of+action+and+clinical+uses+of+estramustine&rft.volume=8&rft.issue=3%E2%80%934&rft.pages=375-380&rft.date=1990&rft_id=info%3Adoi%2F10.3109%2F07357909009012056&rft_id=info%3Apmid%2F2207764&rft.aulast=Benson&rft.aufirst=R&rft.au=Hartley-Asp%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVan_PoppelBaert1991" class="citation journal cs1">Van Poppel H, Baert L (1991). "The present role of estramustine phosphate in advanced prostate cancer". Progress in Clinical and Biological Research. 370: 323–341. <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/1924466">1924466</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Progress+in+Clinical+and+Biological+Research&rft.atitle=The+present+role+of+estramustine+phosphate+in+advanced+prostate+cancer&rft.volume=370&rft.pages=323-341&rft.date=1991&rft_id=info%3Apmid%2F1924466&rft.aulast=Van+Poppel&rft.aufirst=H&rft.au=Baert%2C+L&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJanknegt1992" class="citation journal cs1">Janknegt RA (1992). "Estramustine phosphate and other cytotoxic drugs in the treatment of poor prognostic advanced prostate cancer". The Prostate. Supplement. 4: 105–110. <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%2Fpros.2990210516">10.1002/pros.2990210516</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/1574449">1574449</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:40562112">40562112</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Prostate.+Supplement&rft.atitle=Estramustine+phosphate+and+other+cytotoxic+drugs+in+the+treatment+of+poor+prognostic+advanced+prostate+cancer&rft.volume=4&rft.pages=105-110&rft.date=1992&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A40562112%23id-name%3DS2CID&rft_id=info%3Apmid%2F1574449&rft_id=info%3Adoi%2F10.1002%2Fpros.2990210516&rft.aulast=Janknegt&rft.aufirst=RA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTewGluskerHartley-AspHudes1992" class="citation journal cs1">Tew KD, Glusker JP, Hartley-Asp B, Hudes G, Speicher LA (December 1992). "Preclinical and clinical perspectives on the use of estramustine as an antimitotic drug". Pharmacology & Therapeutics. 56 (3): 323–339. <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%2F0163-7258%2892%2990023-S">10.1016/0163-7258(92)90023-S</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/1301594">1301594</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology+%26+Therapeutics&rft.atitle=Preclinical+and+clinical+perspectives+on+the+use+of+estramustine+as+an+antimitotic+drug&rft.volume=56&rft.issue=3&rft.pages=323-339&rft.date=1992-12&rft_id=info%3Adoi%2F10.1016%2F0163-7258%2892%2990023-S&rft_id=info%3Apmid%2F1301594&rft.aulast=Tew&rft.aufirst=KD&rft.au=Glusker%2C+JP&rft.au=Hartley-Asp%2C+B&rft.au=Hudes%2C+G&rft.au=Speicher%2C+LA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKreis1995" class="citation book cs1">Kreis W (1995). "Estramustine revisited". Concepts, Mechanisms, and New Targets for Chemotherapy. Cancer Treatment and Research. Vol. 78. Springer. pp. 163–184. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-1-4615-2007-8_8">10.1007/978-1-4615-2007-8_8</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4613-5829-9" title="Special:BookSources/978-1-4613-5829-9"><bdi>978-1-4613-5829-9</bdi></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/8595142">8595142</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Estramustine+revisited&rft.btitle=Concepts%2C+Mechanisms%2C+and+New+Targets+for+Chemotherapy&rft.series=Cancer+Treatment+and+Research&rft.pages=163-184&rft.pub=Springer&rft.date=1995&rft_id=info%3Apmid%2F8595142&rft_id=info%3Adoi%2F10.1007%2F978-1-4615-2007-8_8&rft.isbn=978-1-4613-5829-9&rft.aulast=Kreis&rft.aufirst=W&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPerryMcTavish1995" class="citation journal cs1">Perry CM, McTavish D (July 1995). "Estramustine phosphate sodium. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in prostate cancer". Drugs & Aging. 7 (1): 49–74. <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%2F00002512-199507010-00006">10.2165/00002512-199507010-00006</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/7579781">7579781</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:36725810">36725810</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Drugs+%26+Aging&rft.atitle=Estramustine+phosphate+sodium.+A+review+of+its+pharmacodynamic+and+pharmacokinetic+properties%2C+and+therapeutic+efficacy+in+prostate+cancer&rft.volume=7&rft.issue=1&rft.pages=49-74&rft.date=1995-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A36725810%23id-name%3DS2CID&rft_id=info%3Apmid%2F7579781&rft_id=info%3Adoi%2F10.2165%2F00002512-199507010-00006&rft.aulast=Perry&rft.aufirst=CM&rft.au=McTavish%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHudes1997" class="citation journal cs1">Hudes G (February 1997). "Estramustine-based chemotherapy". Seminars in Urologic Oncology. 15 (1): 13–19. <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/9050135">9050135</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Seminars+in+Urologic+Oncology&rft.atitle=Estramustine-based+chemotherapy&rft.volume=15&rft.issue=1&rft.pages=13-19&rft.date=1997-02&rft_id=info%3Apmid%2F9050135&rft.aulast=Hudes&rft.aufirst=G&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBergenheimHenriksson1998" class="citation journal cs1">Bergenheim AT, Henriksson R (February 1998). "Pharmacokinetics and pharmacodynamics of estramustine phosphate". Clinical Pharmacokinetics. 34 (2): 163–172. <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%2F00003088-199834020-00004">10.2165/00003088-199834020-00004</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/9515186">9515186</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:1943973">1943973</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Pharmacokinetics&rft.atitle=Pharmacokinetics+and+pharmacodynamics+of+estramustine+phosphate&rft.volume=34&rft.issue=2&rft.pages=163-172&rft.date=1998-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A1943973%23id-name%3DS2CID&rft_id=info%3Apmid%2F9515186&rft_id=info%3Adoi%2F10.2165%2F00003088-199834020-00004&rft.aulast=Bergenheim&rft.aufirst=AT&rft.au=Henriksson%2C+R&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKitamura2001" class="citation journal cs1">Kitamura T (February 2001). "Necessity of re-evaluation of estramustine phosphate sodium (EMP) as a treatment option for first-line monotherapy in advanced prostate cancer". International Journal of Urology. 8 (2): 33–36. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1046%2Fj.1442-2042.2001.00254.x">10.1046/j.1442-2042.2001.00254.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11240822">11240822</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:43384150">43384150</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=International+Journal+of+Urology&rft.atitle=Necessity+of+re-evaluation+of+estramustine+phosphate+sodium+%28EMP%29+as+a+treatment+option+for+first-line+monotherapy+in+advanced+prostate+cancer&rft.volume=8&rft.issue=2&rft.pages=33-36&rft.date=2001-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A43384150%23id-name%3DS2CID&rft_id=info%3Apmid%2F11240822&rft_id=info%3Adoi%2F10.1046%2Fj.1442-2042.2001.00254.x&rft.aulast=Kitamura&rft.aufirst=T&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRaveryFizaziOudardDrouet2011" class="citation journal cs1">Ravery V, Fizazi K, Oudard S, Drouet L, Eymard JC, Culine S, et al. (December 2011). "The use of estramustine phosphate in the modern management of advanced prostate cancer". BJU International. 108 (11): 1782–1786. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1464-410X.2011.10201.x">10.1111/j.1464-410X.2011.10201.x</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/21756277">21756277</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:33456591">33456591</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BJU+International&rft.atitle=The+use+of+estramustine+phosphate+in+the+modern+management+of+advanced+prostate+cancer&rft.volume=108&rft.issue=11&rft.pages=1782-1786&rft.date=2011-12&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A33456591%23id-name%3DS2CID&rft_id=info%3Apmid%2F21756277&rft_id=info%3Adoi%2F10.1111%2Fj.1464-410X.2011.10201.x&rft.aulast=Ravery&rft.aufirst=V&rft.au=Fizazi%2C+K&rft.au=Oudard%2C+S&rft.au=Drouet%2C+L&rft.au=Eymard%2C+JC&rft.au=Culine%2C+S&rft.au=Gravis%2C+G&rft.au=Hennequin%2C+C&rft.au=Zerbib%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFQinLiZhangTang2016" class="citation journal cs1">Qin Z, Li X, Zhang J, Tang J, Han P, Xu Z, et al. (September 2016). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5265899">"Chemotherapy with or without estramustine for treatment of castration-resistant prostate cancer: A systematic review and meta-analysis"</a>. Medicine. 95 (39): e4801. <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%2FMD.0000000000004801">10.1097/MD.0000000000004801</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/PMC5265899">5265899</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/27684806">27684806</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Medicine&rft.atitle=Chemotherapy+with+or+without+estramustine+for+treatment+of+castration-resistant+prostate+cancer%3A+A+systematic+review+and+meta-analysis&rft.volume=95&rft.issue=39&rft.pages=e4801&rft.date=2016-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5265899%23id-name%3DPMC&rft_id=info%3Apmid%2F27684806&rft_id=info%3Adoi%2F10.1097%2FMD.0000000000004801&rft.aulast=Qin&rft.aufirst=Z&rft.au=Li%2C+X&rft.au=Zhang%2C+J&rft.au=Tang%2C+J&rft.au=Han%2C+P&rft.au=Xu%2C+Z&rft.au=Yu%2C+Y&rft.au=Yang%2C+C&rft.au=Wang%2C+C&rft.au=Xu%2C+T&rft.au=Xu%2C+Z&rft.au=Zou%2C+Q&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC5265899&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEstramustine+phosphate" class="Z3988"></li></ul> </div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style 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.navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style></div><div role="navigation" class="navbox" aria-labelledby="Estradiol" style="padding:3px"><table class="nowraplinks mw-collapsible expanded navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estradiol" title="Template:Estradiol"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estradiol" title="Template talk:Estradiol"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estradiol" 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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 class="mw-selflink selflink">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="Intracellular_chemotherapeutic_agents_/_antineoplastic_agents_(L01)" 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:Chemotherapeutic_agents" title="Template:Chemotherapeutic agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemotherapeutic_agents" class="mw-redirect" title="Template talk:Chemotherapeutic agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemotherapeutic_agents" title="Special:EditPage/Template:Chemotherapeutic agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Intracellular_chemotherapeutic_agents_/_antineoplastic_agents_(L01)" style="font-size:114%;margin:0 4em">Intracellular <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapeutic agents</a> / <a href="/wiki/Antineoplastic" class="mw-redirect" title="Antineoplastic">antineoplastic agents</a> (<a href="/wiki/ATC_code_L01" title="ATC code L01">L01</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Spindle_poison" title="Spindle poison">SPs</a>/<a href="/wiki/Mitotic_inhibitor" title="Mitotic inhibitor">MIs</a> (<a href="/wiki/M_phase" class="mw-redirect" title="M phase">M phase</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:1%">Block <a href="/wiki/Microtubule" title="Microtubule">microtubule</a> assembly</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Vinca_alkaloid" title="Vinca alkaloid">Vinca alkaloids</a> (<a href="/wiki/Vinblastine" title="Vinblastine">Vinblastine</a>#</li> <li><a href="/wiki/Vincristine" title="Vincristine">Vincristine</a>#</li> <li><a href="/wiki/Vindesine" title="Vindesine">Vindesine</a></li> <li><a href="/wiki/Vinflunine" title="Vinflunine">Vinflunine</a>§</li> <li><a href="/wiki/Vinorelbine" title="Vinorelbine">Vinorelbine</a>#)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Block microtubule disassembly</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Taxane" title="Taxane">Taxanes</a> (<a href="/wiki/Cabazitaxel" title="Cabazitaxel">Cabazitaxel</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a>#</li> <li><a href="/wiki/Larotaxel" title="Larotaxel">Larotaxel</a></li> <li><a href="/wiki/Ortataxel" title="Ortataxel">Ortataxel</a>†</li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a>#</li> <li><a href="/wiki/Tesetaxel" title="Tesetaxel">Tesetaxel</a>)</li> <li><a href="/wiki/Epothilone" title="Epothilone">Epothilones</a> (<a href="/wiki/Ixabepilone" title="Ixabepilone">Ixabepilone</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/DNA_replication" title="DNA replication">DNA replication</a> inhibitor</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:1%">DNA precursors/ <a href="/wiki/Antimetabolite" title="Antimetabolite">antimetabolites</a> (<a href="/wiki/S_phase" title="S phase">S phase</a>)</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:1%"><a href="/wiki/Antifolate" title="Antifolate">Folic acid</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Dihydrofolate_reductase_inhibitor" title="Dihydrofolate reductase inhibitor">Dihydrofolate reductase inhibitor</a> (<a href="/wiki/Aminopterin" title="Aminopterin">Aminopterin</a></li> <li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a>#</li> <li><a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Pralatrexate" title="Pralatrexate">Pralatrexate</a>)</li> <li><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">Thymidylate synthase inhibitor</a> (<a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Raltitrexed" title="Raltitrexed">Raltitrexed</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Purine_analogue" title="Purine analogue">Purine</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_deaminase_inhibitor" class="mw-redirect" title="Adenosine deaminase inhibitor">Adenosine deaminase inhibitor</a> (<a href="/wiki/Pentostatin" title="Pentostatin">Pentostatin</a>)</li></ul> <ul><li><a href="/wiki/Halogenation" title="Halogenation">Halogenated</a>/<a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">ribonucleotide reductase inhibitors</a> (<a href="/wiki/Cladribine" title="Cladribine">Cladribine</a></li> <li><a href="/wiki/Clofarabine" title="Clofarabine">Clofarabine</a></li> <li><a href="/wiki/Fludarabine" title="Fludarabine">Fludarabine</a>)</li> <li><a href="/wiki/Nelarabine" title="Nelarabine">Nelarabine</a></li> <li><a href="/wiki/Rabacfosadine" title="Rabacfosadine">Rabacfosadine</a></li> <li><a href="/wiki/Thiopurine" title="Thiopurine">Thiopurine</a> (<a href="/wiki/Mercaptopurine" title="Mercaptopurine">Mercaptopurine</a>#</li> <li><a href="/wiki/Tioguanine" title="Tioguanine">Tioguanine</a>#)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrimidine_analogue" title="Pyrimidine analogue">Pyrimidine</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">Thymidylate synthase inhibitor</a> (<a href="/wiki/Capecitabine" title="Capecitabine">Capecitabine</a>#</li> <li><a href="/wiki/Carmofur" title="Carmofur">Carmofur</a></li> <li><a href="/wiki/Doxifluridine" title="Doxifluridine">Doxifluridine</a></li> <li><a href="/wiki/Floxuridine" title="Floxuridine">Floxuridine</a></li> <li><a href="/wiki/Fluorouracil" title="Fluorouracil">Fluorouracil</a>#</li> <li><a href="/wiki/Tegafur" title="Tegafur">Tegafur</a> (<a href="/wiki/Tegafur/gimeracil/oteracil" title="Tegafur/gimeracil/oteracil">+gimeracil/oteracil</a>))</li></ul> <ul><li><a href="/wiki/DNA_polymerase_inhibitor" class="mw-redirect" title="DNA polymerase inhibitor">DNA polymerase inhibitor</a> (<a href="/wiki/Cytarabine" title="Cytarabine">Cytarabine</a># <a href="/wiki/Daunorubicin/cytarabine" title="Daunorubicin/cytarabine">+daunorubicin</a>)</li></ul> <ul><li><a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">Ribonucleotide reductase inhibitor</a> (<a href="/wiki/Gemcitabine" title="Gemcitabine">Gemcitabine</a>#)</li></ul> <ul><li><a href="/wiki/Hypomethylating_agent" title="Hypomethylating agent">Hypomethylating agent</a> (<a href="/wiki/Azacitidine" title="Azacitidine">Azacitidine</a></li> <li><a href="/wiki/Decitabine" title="Decitabine">Decitabine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleotide" title="Deoxyribonucleotide">Deoxyribonucleotide</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">Ribonucleotide reductase inhibitor</a> (<a href="/wiki/Hydroxycarbamide" title="Hydroxycarbamide">Hydroxycarbamide</a>#)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Topoisomerase_inhibitor" title="Topoisomerase inhibitor">Topoisomerase inhibitors</a> (<a href="/wiki/S_phase" title="S phase">S phase</a>)</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:1%"><a href="/wiki/Type_I_topoisomerase#Inhibition" title="Type I topoisomerase">I</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Camptotheca" title="Camptotheca">Camptotheca</a> (<a href="/wiki/Belotecan" title="Belotecan">Belotecan</a></li> <li><a href="/wiki/Camptothecin" title="Camptothecin">Camptothecin</a></li> <li><a href="/w/index.php?title=Cositecan&action=edit&redlink=1" class="new" title="Cositecan (page does not exist)">Cositecan</a>†</li> <li><a href="/wiki/Etirinotecan_pegol" title="Etirinotecan pegol">Etirinotecan pegol</a>†</li> <li><a href="/wiki/Exatecan" title="Exatecan">Exatecan</a></li> <li><a href="/w/index.php?title=Gimatecan&action=edit&redlink=1" class="new" title="Gimatecan (page does not exist)">Gimatecan</a></li> <li><a href="/wiki/Irinotecan" title="Irinotecan">Irinotecan</a>#</li> <li><a href="/wiki/Lurtotecan" title="Lurtotecan">Lurtotecan</a>‡</li> <li><a href="/wiki/Rubitecan" title="Rubitecan">Rubitecan</a>‡</li> <li><a href="/w/index.php?title=Silatecan&action=edit&redlink=1" class="new" title="Silatecan (page does not exist)">Silatecan</a>§</li> <li><a href="/wiki/Topotecan" title="Topotecan">Topotecan</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_II_topoisomerase#Inhibition" title="Type II topoisomerase">II</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Podophyllum_peltatum" title="Podophyllum peltatum">Podophyllum</a> (<a href="/wiki/Etoposide" title="Etoposide">Etoposide</a>#</li> <li><a href="/wiki/Teniposide" title="Teniposide">Teniposide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_II_topoisomerase#Inhibition" title="Type II topoisomerase">II</a>+<a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">Intercalation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anthracycline" title="Anthracycline">Anthracyclines</a> (<a href="/wiki/Aclarubicin" title="Aclarubicin">Aclarubicin</a></li> <li><a href="/wiki/Amrubicin" title="Amrubicin">Amrubicin</a>†</li> <li><a href="/wiki/Daunorubicin" title="Daunorubicin">Daunorubicin</a># (<a href="/wiki/Daunorubicin/cytarabine" title="Daunorubicin/cytarabine">+cytarabine</a>)</li> <li><a href="/wiki/Doxorubicin" title="Doxorubicin">Doxorubicin</a>#</li> <li><a href="/wiki/Epirubicin" title="Epirubicin">Epirubicin</a></li> <li><a href="/wiki/Idarubicin" title="Idarubicin">Idarubicin</a></li> <li><a href="/wiki/Pirarubicin" title="Pirarubicin">Pirarubicin</a></li> <li><a href="/wiki/Valrubicin" title="Valrubicin">Valrubicin</a></li> <li><a href="/wiki/Zorubicin" title="Zorubicin">Zorubicin</a>)</li> <li><a href="/wiki/Anthraquinone" title="Anthraquinone">Anthracenediones</a> (<a href="/wiki/Losoxantrone" title="Losoxantrone">Losoxantrone</a></li> <li><a href="/wiki/Mitoxantrone" title="Mitoxantrone">Mitoxantrone</a></li> <li><a href="/wiki/Pixantrone" title="Pixantrone">Pixantrone</a>)</li> <li><a href="/wiki/Amsacrine" title="Amsacrine">Amsacrine</a></li> <li><a href="/wiki/Bisantrene" title="Bisantrene">Bisantrene</a></li> <li><a href="/wiki/Crisnatol" title="Crisnatol">Crisnatol</a></li> <li><a href="/wiki/Menogaril" title="Menogaril">Menogaril</a>§</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Crosslinking_of_DNA" title="Crosslinking of DNA">Crosslinking of DNA</a> (<a href="/wiki/Cell-cycle_nonspecific_antineoplastic_agents" title="Cell-cycle nonspecific antineoplastic agents">CCNS</a>)</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:1%"><a href="/wiki/Alkylating_antineoplastic_agent" title="Alkylating antineoplastic agent">Alkylating</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">Nitrogen mustards</a>: <a href="/wiki/Bendamustine" title="Bendamustine">Bendamustine</a>#</li> <li><a href="/wiki/Chlormethine" title="Chlormethine">Chlormethine</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a># (<a href="/wiki/Ifosfamide" title="Ifosfamide">Ifosfamide</a>#</li> <li><a href="/wiki/Trofosfamide" title="Trofosfamide">Trofosfamide</a>)</li> <li><a href="/wiki/Chlorambucil" title="Chlorambucil">Chlorambucil</a>#</li> <li><a href="/wiki/Melphalan" title="Melphalan">Melphalan</a> (<a href="/wiki/Melphalan_flufenamide" title="Melphalan flufenamide">Melphalan flufenamide</a>)</li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Uramustine" title="Uramustine">Uramustine</a></li></ul> <ul><li><a href="/wiki/Nitrosourea" title="Nitrosourea">Nitrosoureas</a>: <a href="/wiki/Carmustine" title="Carmustine">Carmustine</a></li> <li><a href="/wiki/Fotemustine" title="Fotemustine">Fotemustine</a></li> <li><a href="/wiki/Lomustine" title="Lomustine">Lomustine</a> (<a href="/wiki/Semustine" title="Semustine">Semustine</a>)</li> <li><a href="/wiki/Nimustine" title="Nimustine">Nimustine</a></li> <li><a href="/wiki/Ranimustine" title="Ranimustine">Ranimustine</a></li> <li><a href="/wiki/Streptozotocin" title="Streptozotocin">Streptozocin</a></li></ul> <ul><li><a href="/wiki/Alkyl_sulfonate" title="Alkyl sulfonate">Alkyl sulfonates</a>: <a href="/wiki/Busulfan" title="Busulfan">Busulfan</a> (<a href="/wiki/Mannosulfan" title="Mannosulfan">Mannosulfan</a></li> <li><a href="/wiki/Treosulfan" title="Treosulfan">Treosulfan</a>)</li></ul> <ul><li><a href="/wiki/Aziridine" title="Aziridine">Aziridines</a>: <a href="/wiki/Carboquone" title="Carboquone">Carboquone</a></li> <li><a href="/wiki/Thiotepa" title="Thiotepa">Thiotepa</a></li> <li><a href="/wiki/Triaziquone" title="Triaziquone">Triaziquone</a></li> <li><a href="/wiki/Triethylenemelamine" title="Triethylenemelamine">Triethylenemelamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Platinum-based_antineoplastic" title="Platinum-based antineoplastic">Platinum-based</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboplatin" title="Carboplatin">Carboplatin</a>#</li> <li><a href="/wiki/Cisplatin" title="Cisplatin">Cisplatin</a>#</li> <li><a href="/wiki/Dicycloplatin" title="Dicycloplatin">Dicycloplatin</a></li> <li><a href="/wiki/Nedaplatin" title="Nedaplatin">Nedaplatin</a></li> <li><a href="/wiki/Oxaliplatin" title="Oxaliplatin">Oxaliplatin</a>#</li> <li><a href="/wiki/Satraplatin" title="Satraplatin">Satraplatin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkylating_antineoplastic_agent#Nonclassical" title="Alkylating antineoplastic agent">Nonclassical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Altretamine" title="Altretamine">Altretamine</a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">Hydrazines</a> (<a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a>#)</li> <li><a href="/wiki/Etoglucid" title="Etoglucid">Etoglucid</a></li> <li><a href="/wiki/Mitobronitol" title="Mitobronitol">Mitobronitol</a></li> <li><a href="/wiki/Pipobroman" title="Pipobroman">Pipobroman</a></li> <li><a href="/wiki/Triazene" title="Triazene">Triazenes</a> (<a href="/wiki/Dacarbazine" title="Dacarbazine">Dacarbazine</a>#</li> <li><a href="/wiki/Mitozolomide" title="Mitozolomide">Mitozolomide</a>§</li> <li><a href="/wiki/Temozolomide" title="Temozolomide">Temozolomide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">Intercalation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a> (<a href="/wiki/Dactinomycin" title="Dactinomycin">Dactinomycin</a>#</li> <li><a href="/wiki/Bleomycin" title="Bleomycin">Bleomycin</a>#</li> <li><a href="/wiki/Mitomycins" title="Mitomycins">Mitomycins</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Photosensitizer" title="Photosensitizer">Photosensitizers</a>/<a href="/wiki/Photodynamic_therapy" title="Photodynamic therapy">PDT</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/Aminolevulinic_acid" title="Aminolevulinic acid">Aminolevulinic acid</a></li> <li><a href="/wiki/Efaproxiral" title="Efaproxiral">Efaproxiral</a></li> <li><a href="/wiki/Methyl_aminolevulinate" title="Methyl aminolevulinate">Methyl aminolevulinate</a></li> <li><a href="/wiki/Padeliporfin" title="Padeliporfin">Padeliporfin</a></li> <li><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrin derivatives</a> (<a href="/wiki/Porfimer_sodium" title="Porfimer sodium">Porfimer sodium</a></li> <li><a href="/wiki/Talaporfin" title="Talaporfin">Talaporfin</a></li> <li><a href="/wiki/Temoporfin" title="Temoporfin">Temoporfin</a></li> <li><a href="/wiki/Verteporfin" title="Verteporfin">Verteporfin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</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:1%"><a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">Enzyme inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Farnesyltransferase_inhibitor" title="Farnesyltransferase inhibitor">FI</a> (<a href="/wiki/Tipifarnib" title="Tipifarnib">Tipifarnib</a>§)</li> <li><a href="/wiki/Cyclin-dependent_kinase" title="Cyclin-dependent kinase">CDK</a> <a href="/wiki/Protein_kinase_inhibitor" title="Protein kinase inhibitor">inhibitors</a> (<a href="/wiki/Abemaciclib" title="Abemaciclib">Abemaciclib</a></li> <li><a href="/wiki/Alvocidib" title="Alvocidib">Alvocidib</a>†</li> <li><a href="/wiki/Palbociclib" title="Palbociclib">Palbociclib</a></li> <li><a href="/wiki/Ribociclib" title="Ribociclib">Ribociclib</a></li> <li><a href="/wiki/Seliciclib" title="Seliciclib">Seliciclib</a>†)</li> <li><a href="/wiki/Proteasome_inhibitor" title="Proteasome inhibitor">PrI</a> <ul><li><a href="/wiki/Bortezomib" title="Bortezomib">Bortezomib</a></li> <li><a href="/wiki/Carfilzomib" title="Carfilzomib">Carfilzomib</a></li> <li><a href="/wiki/Oprozomib" title="Oprozomib">Oprozomib</a></li> <li><a href="/wiki/Ixazomib" title="Ixazomib">Ixazomib</a></li></ul></li> <li><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">PhI</a> (<a href="/wiki/Anagrelide" title="Anagrelide">Anagrelide</a>)</li> <li><a href="/wiki/IMP_dehydrogenase" class="mw-redirect" title="IMP dehydrogenase">IMPDI</a> (<a href="/wiki/Tiazofurin" title="Tiazofurin">Tiazofurin</a>§)</li> <li><a href="/wiki/Lipoxygenase_inhibitor" class="mw-redirect" title="Lipoxygenase inhibitor">LI</a> (<a href="/wiki/Masoprocol" title="Masoprocol">Masoprocol</a>)</li> <li><a href="/wiki/PARP_inhibitor" title="PARP inhibitor">PARP inhibitor</a> (<a href="/wiki/Fuzuloparib" title="Fuzuloparib">Fuzuloparib</a></li> <li><a href="/wiki/Niraparib" title="Niraparib">Niraparib</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+abiraterone acetate</a></li> <li><a href="/wiki/Olaparib" title="Olaparib">Olaparib</a></li> <li><a href="/wiki/Rucaparib" title="Rucaparib">Rucaparib</a>)</li> <li><a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">HDAC</a> (<a href="/wiki/Belinostat" title="Belinostat">Belinostat</a></li> <li><a href="/wiki/Entinostat" title="Entinostat">Entinostat</a></li> <li><a href="/wiki/Panobinostat" title="Panobinostat">Panobinostat</a></li> <li><a href="/wiki/Romidepsin" title="Romidepsin">Romidepsin</a></li> <li><a href="/wiki/Vorinostat" title="Vorinostat">Vorinostat</a>)</li> <li><a href="/wiki/Phosphoinositide_3-kinase_inhibitor" title="Phosphoinositide 3-kinase inhibitor">PIKI</a> (Pi3K) (<a href="/wiki/Alpelisib" title="Alpelisib">Alpelisib</a></li> <li><a href="/wiki/Copanlisib" title="Copanlisib">Copanlisib</a>‡</li> <li><a href="/wiki/Duvelisib" title="Duvelisib">Duvelisib</a></li> <li><a href="/wiki/Idelalisib" title="Idelalisib">Idelalisib</a></li> <li><a href="/wiki/Inavolisib" title="Inavolisib">Inavolisib</a></li> <li><a href="/wiki/Umbralisib" title="Umbralisib">Umbralisib</a>‡)</li> <li><a href="/wiki/Isocitrate_dehydrogenase" title="Isocitrate dehydrogenase">IDH</a> (<a href="/wiki/Enasidenib" title="Enasidenib">Enasidenib</a></li> <li><a href="/wiki/Ivosidenib" title="Ivosidenib">Ivosidenib</a></li> <li><a href="/wiki/Olutasidenib" title="Olutasidenib">Olutasidenib</a></li> <li><a href="/wiki/Vorasidenib" title="Vorasidenib">Vorasidenib</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Receptor antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Endothelin_receptor_antagonist" title="Endothelin receptor antagonist">ERA</a> (<a href="/wiki/Atrasentan" title="Atrasentan">Atrasentan</a>)</li> <li><a href="/wiki/Retinoid_X_receptor" title="Retinoid X receptor">Retinoid X receptor</a> (<a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a>)</li> <li><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroid</a> (<a href="/wiki/Testolactone" title="Testolactone">Testolactone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/ungrouped</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adagrasib" title="Adagrasib">Adagrasib</a></li> <li><a href="/wiki/Aflibercept" title="Aflibercept">Aflibercept</a></li> <li><a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">Arsenic trioxide</a></li> <li><a href="/wiki/Asparagine" title="Asparagine">Asparagine depleters</a> (<a href="/wiki/Asparaginase" title="Asparaginase">Asparaginase</a>#/<a href="/wiki/Pegaspargase" title="Pegaspargase">Pegaspargase</a>)</li> <li><a href="/wiki/Axicabtagene_ciloleucel" title="Axicabtagene ciloleucel">Axicabtagene ciloleucel</a></li> <li><a href="/wiki/Belzutifan" title="Belzutifan">Belzutifan</a></li> <li><a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a></li> <li><a href="/wiki/Brexucabtagene_autoleucel" title="Brexucabtagene autoleucel">Brexucabtagene autoleucel</a></li> <li><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a></li> <li><a href="/wiki/Ciltacabtagene_autoleucel" title="Ciltacabtagene autoleucel">Ciltacabtagene autoleucel</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Denileukin_diftitox" title="Denileukin diftitox">Denileukin diftitox</a></li> <li><a href="/wiki/Eflornithine" title="Eflornithine">Eflornithine</a></li> <li><a href="/wiki/Elesclomol" title="Elesclomol">Elesclomol</a>§</li> <li><a href="/wiki/Elsamitrucin" title="Elsamitrucin">Elsamitrucin</a></li> <li><a href="/wiki/Epacadostat" title="Epacadostat">Epacadostat</a></li> <li><a href="/wiki/Eribulin" title="Eribulin">Eribulin</a></li> <li><a class="mw-selflink selflink">Estramustine</a></li> <li><a href="/wiki/Glasdegib" title="Glasdegib">Glasdegib</a></li> <li><a href="/wiki/Idecabtagene_vicleucel" title="Idecabtagene vicleucel">Idecabtagene vicleucel</a></li> <li><a href="/wiki/Imetelstat" title="Imetelstat">Imetelstat</a></li> <li><a href="/wiki/Lifileucel" title="Lifileucel">Lifileucel</a></li> <li><a href="/wiki/Lisocabtagene_maraleucel" title="Lisocabtagene maraleucel">Lisocabtagene maraleucel</a></li> <li><a href="/wiki/Lonidamine" title="Lonidamine">Lonidamine</a></li> <li><a href="/wiki/Lucanthone" title="Lucanthone">Lucanthone</a></li> <li><a href="/wiki/Lurbinectedin" title="Lurbinectedin">Lurbinectedin</a></li> <li><a href="/wiki/Mitoguazone" title="Mitoguazone">Mitoguazone</a></li> <li><a href="/wiki/Mitotane" title="Mitotane">Mitotane</a></li> <li><a href="/wiki/Nadofaragene_firadenovec" title="Nadofaragene firadenovec">Nadofaragene firadenovec</a></li> <li><a href="/wiki/Navitoclax" title="Navitoclax">Navitoclax</a></li> <li><a href="/wiki/Obecabtagene_autoleucel" title="Obecabtagene autoleucel">Obecabtagene autoleucel</a></li> <li><a href="/wiki/Oblimersen" title="Oblimersen">Oblimersen</a>†</li> <li><a href="/wiki/Omacetaxine_mepesuccinate" title="Omacetaxine mepesuccinate">Omacetaxine mepesuccinate</a></li> <li><a href="/wiki/Plitidepsin" title="Plitidepsin">Plitidepsin</a></li> <li><a href="/wiki/Tabelecleucel" title="Tabelecleucel">Tabelecleucel</a></li> <li><a href="/wiki/Retinoid" title="Retinoid">Retinoids</a> (<a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a>#)</li> <li><a href="/wiki/Selinexor" title="Selinexor">Selinexor</a></li> <li><a href="/w/index.php?title=Sitimagene_ceradenovec&action=edit&redlink=1" class="new" title="Sitimagene ceradenovec (page does not exist)">Sitimagene ceradenovec</a></li> <li><a href="/wiki/Sotorasib" title="Sotorasib">Sotorasib</a></li> <li><a href="/wiki/Tagraxofusp" title="Tagraxofusp">Tagraxofusp</a></li> <li><a href="/wiki/Talimogene_laherparepvec" title="Talimogene laherparepvec">Talimogene laherparepvec</a></li> <li><a href="/wiki/Tazemetostat" title="Tazemetostat">Tazemetostat</a></li> <li><a href="/wiki/Tebentafusp" title="Tebentafusp">Tebentafusp</a></li> <li><a href="/wiki/Tiazofurine" class="mw-redirect" title="Tiazofurine">Tiazofurine</a></li> <li><a href="/wiki/Tigilanol_tiglate" title="Tigilanol tiglate">Tigilanol tiglate</a></li> <li><a href="/wiki/Tisagenlecleucel" title="Tisagenlecleucel">Tisagenlecleucel</a></li> <li><a href="/wiki/Trabectedin" title="Trabectedin">Trabectedin</a></li> <li><a href="/wiki/Veliparib" title="Veliparib">Veliparib</a></li> <li><a href="/wiki/Venetoclax" title="Venetoclax">Venetoclax</a></li> <li><a href="/w/index.php?title=Verdinexor&action=edit&redlink=1" class="new" title="Verdinexor (page does not exist)">Verdinexor</a></li> <li><a href="/wiki/Vosaroxin" title="Vosaroxin">Vosaroxin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><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></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Estrogens_and_antiestrogens" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogens_and_antiestrogens" title="Template talk:Estrogens and antiestrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogens_and_antiestrogens" title="Special:EditPage/Template:Estrogens and antiestrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogens_and_antiestrogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a> and <a href="/wiki/Antiestrogen" title="Antiestrogen">antiestrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">Estrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li>Certain <a href="/wiki/Androgen" title="Androgen">androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>) (via estrogenic metabolites)</li> <li>Certain <a href="/wiki/Progestin" class="mw-redirect" title="Progestin">progestins</a> (e.g., <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone</a>, <a href="/wiki/Noretynodrel" title="Noretynodrel">noretynodrel</a>, <a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">etynodiol diacetate</a>, <a href="/wiki/Tibolone" title="Tibolone">tibolone</a>)</li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol_(medication)" title="Estetrol (medication)">Estetrol</a>†</li> <li><a href="/wiki/Estradiol_(medication)" title="Estradiol (medication)">Estradiol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a> (e.g., <a href="/wiki/Estradiol_acetate" title="Estradiol acetate">estradiol acetate</a>, <a href="/wiki/Estradiol_benzoate" title="Estradiol benzoate">estradiol benzoate</a>, <a href="/wiki/Estradiol_cypionate" title="Estradiol cypionate">estradiol cypionate</a>, <a href="/wiki/Estradiol_enanthate" class="mw-redirect" title="Estradiol enanthate">estradiol enanthate</a>, <a href="/wiki/Estradiol_undecylate" title="Estradiol undecylate">estradiol undecylate</a>, <a 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 class="mw-selflink selflink">Estramustine phosphate</a></li> <li><a href="/wiki/Estriol_(medication)" title="Estriol (medication)">Estriol</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a> (e.g., <a href="/wiki/Estriol_succinate" title="Estriol succinate">estriol succinate</a>, <a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">polyestriol phosphate</a>)</li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estrone_(medication)" title="Estrone (medication)">Estrone</a></li> <li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a> <ul><li><a href="/wiki/Estrone_sulfate_(medication)" title="Estrone sulfate (medication)">Estrone sulfate</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate (piperazine estrone sulfate)</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a># <ul><li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone; DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate</a></li></ul></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol (stilbestrol)</a></li> <li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters/ethers</a> <ul><li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (diethylstilbestrol dimethyl ether)</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol (diethylstilbestrol monomethyl ether)</a></li></ul></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol (promethestrol)</a> <ul><li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate (promethestrol dipropionate)</a></li></ul></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Progonadotropin" title="Progonadotropin">Progonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a> (e.g., <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> (gonadorelin)</a>, <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/Gonadotropin" title="Gonadotropin">Gonadotropins</a> (e.g., <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone"><abbr title="follicle-stimulating hormone">FSH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip follicle-stimulating hormone, <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone"><abbr title="luteinizing hormone">LH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip luteinizing hormone)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Antiestrogen" title="Antiestrogen">Antiestrogens</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor antagonists (incl. <a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor modulators/<a href="/wiki/Selective_estrogen_receptor_downregulators" class="mw-redirect" title="Selective estrogen receptor downregulators"><abbr title="selective estrogen receptor downregulators">SERDs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip selective estrogen receptor downregulators)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a>†</li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a>#</li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a>†</li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a>#</li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li></ul> <ul><li>Exclusively antagonistic: <a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li></ul> <ul><li>Noncompetitive inhibitors: <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Aromatase_inhibitor" title="Aromatase inhibitor">Aromatase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>First-generation: <a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Testolactone" title="Testolactone">Testolactone</a></li></ul> <ul><li>Second-generation: <a href="/wiki/Fadrozole" title="Fadrozole">Fadrozole</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li></ul> <ul><li>Third-generation: <a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Letrozole" title="Letrozole">Letrozole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Androgen" title="Androgen">Androgens</a>/<a href="/wiki/Anabolic_steroid" title="Anabolic steroid">anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a>, <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">testosterone esters</a>, <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">nandrolone esters</a>, <a href="/wiki/Oxandrolone" title="Oxandrolone">oxandrolone</a>, <a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">fluoxymesterone</a>)</li> <li><a href="/wiki/D2_receptor" class="mw-redirect" title="D2 receptor">D2 receptor</a> <a href="/wiki/Dopamine_antagonist" title="Dopamine antagonist">antagonists</a> (<a href="/wiki/Prolactin" title="Prolactin">prolactin</a> releasers) (e.g., <a href="/wiki/Domperidone" title="Domperidone">domperidone</a>, <a href="/wiki/Metoclopramide" title="Metoclopramide">metoclopramide</a>, <a href="/wiki/Risperidone" title="Risperidone">risperidone</a>, <a href="/wiki/Haloperidol" title="Haloperidol">haloperidol</a>, <a href="/wiki/Chlorpromazine" title="Chlorpromazine">chlorpromazine</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sulpiride</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>, <a href="/wiki/Goserelin" title="Goserelin">goserelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist"><abbr title="gonadotropin-releasing hormone">GnRH</abbr> antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>, <a href="/wiki/Elagolix" title="Elagolix">elagolix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">chlormadinone acetate</a>, <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone caproate</a>, <a href="/wiki/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a>, <a href="/wiki/Megestrol_acetate" title="Megestrol acetate">megestrol acetate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:10em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Mixed mechanism of action: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li></ul> <ul><li>Androstenedione immunogens: <a href="/wiki/Androvax" title="Androvax">Androvax (androstenedione albumin)</a></li> <li><a href="/wiki/Ovandrotone_albumin" title="Ovandrotone albumin">Ovandrotone albumin (Fecundin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0;background:#DDDDFF;"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Androgen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgen_receptor_modulators" title="Template talk:Androgen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgen_receptor_modulators" title="Special:EditPage/Template:Androgen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen_receptor" title="Androgen receptor">Androgen 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/Androgen_receptor" title="Androgen receptor"><abbr title="Androgen receptor">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 Androgen 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>Testosterone derivatives: <a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Dehydroepiandrosterone" title="4-Dehydroepiandrosterone">4-Dehydroepiandrosterone (4-DHEA)</a></li> <li><a href="/wiki/4-Hydroxytestosterone" title="4-Hydroxytestosterone">4-Hydroxytestosterone</a></li> <li><a href="/w/index.php?title=4,17%CE%B1-Dimethyltestosterone&action=edit&redlink=1" class="new" title="4,17α-Dimethyltestosterone (page does not exist)">4,17α-Dimethyltestosterone</a></li> <li><a href="/wiki/5-Androstenedione" title="5-Androstenedione">5-Androstenedione</a></li> <li><a href="/wiki/11-Ketotestosterone" title="11-Ketotestosterone">11-Ketotestosterone</a></li> <li><a href="/wiki/11%CE%B2-Hydroxyandrostenedione" title="11β-Hydroxyandrostenedione">11β-Hydroxyandrostenedione</a></li> <li><a href="/wiki/Adrenosterone" title="Adrenosterone">Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">Androstenediol (5-androstenediol)</a> <ul><li><a href="/wiki/Androstenediol_3%CE%B2-acetate" title="Androstenediol 3β-acetate">Androstenediol 3β-acetate</a></li> <li><a href="/wiki/Androstenediol_17%CE%B2-acetate" title="Androstenediol 17β-acetate">Androstenediol 17β-acetate</a></li> <li><a href="/wiki/Androstenediol_diacetate" title="Androstenediol diacetate">Androstenediol diacetate</a></li> <li><a href="/wiki/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li></ul></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">Androstenedione (4-androstenedione)</a></li> <li><a href="/wiki/Atamestane" title="Atamestane">Atamestane</a></li> <li><a href="/wiki/Boldenone" title="Boldenone">Boldenone</a> <ul><li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li></ul></li> <li><a href="/wiki/Boldione" title="Boldione">Boldione (1,4-androstadienedione)</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a> <ul><li><a href="/wiki/Clostebol_acetate" title="Clostebol acetate">Clostebol acetate</a></li> <li><a href="/wiki/Clostebol_caproate" title="Clostebol caproate">Clostebol caproate</a></li> <li><a href="/wiki/Clostebol_propionate" title="Clostebol propionate">Clostebol propionate</a></li></ul></li> <li><a href="/wiki/Cloxotestosterone" title="Cloxotestosterone">Cloxotestosterone</a> <ul><li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li></ul></li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA (androstenolone, prasterone; 5-DHEA)</a> <ul><li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">DHEA enanthate (prasterone enanthate)</a></li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA sulfate</a></li></ul></li> <li><a href="/wiki/Exemestane" title="Exemestane">Exemestane</a></li> <li><a href="/wiki/Formestane" title="Formestane">Formestane</a></li> <li><a href="/wiki/Plomestane" title="Plomestane">Plomestane</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Silandrone" title="Silandrone">Silandrone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a># (<a href="/wiki/Testosterone/dutasteride" title="Testosterone/dutasteride">+dutasteride</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a></li> <li><a href="/wiki/Polytestosterone_phloretin_phosphate" title="Polytestosterone phloretin phosphate">Polytestosterone phloretin phosphate</a></li></ul></li></ul> <ul><li>5α-Dihydrotestosterone derivatives: <a href="/wiki/1-Androstenediol" title="1-Androstenediol">1-Androstenediol</a></li> <li><a href="/wiki/1-Androstenedione" title="1-Androstenedione">1-Androstenedione</a></li> <li><a href="/wiki/1-Androsterone" title="1-Androsterone">1-Androsterone (1-andro, 1-DHEA)</a></li> <li><a href="/wiki/1-Testosterone" title="1-Testosterone">1-Testosterone</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/wiki/5%CE%B1-Androst-2-en-17-one" class="mw-redirect" title="5α-Androst-2-en-17-one">5α-Androst-2-en-17-one</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/11-Ketodihydrotestosterone" title="11-Ketodihydrotestosterone">11-Ketodihydrotestosterone</a></li> <li><a href="/wiki/Androsterone" title="Androsterone">Androsterone</a></li> <li><a href="/wiki/Bolazine" title="Bolazine">Bolazine</a> <ul><li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li></ul></li> <li><a href="/w/index.php?title=Dihydroethyltestosterone&action=edit&redlink=1" class="new" title="Dihydroethyltestosterone (page does not exist)">Dihydroethyltestosterone</a></li> <li><a href="/wiki/Dihydrofluoxymesterone" title="Dihydrofluoxymesterone">Dihydrofluoxymesterone</a></li> <li><a href="/w/index.php?title=Dihydromethylandrostenediol&action=edit&redlink=1" class="new" title="Dihydromethylandrostenediol (page does not exist)">Dihydromethylandrostenediol</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone (DHT)</a> (<a href="/wiki/Androstanolone" title="Androstanolone">androstanolone, stanolone</a>) <ul><li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Dihydrotestosterone esters</a></li></ul></li> <li><a href="/wiki/Drostanolone" title="Drostanolone">Drostanolone</a> <ul><li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate</a></li></ul></li> <li><a href="/wiki/Epiandrosterone" title="Epiandrosterone">Epiandrosterone</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Mesabolone" title="Mesabolone">Mesabolone</a></li> <li><a href="/wiki/Mesterolone" title="Mesterolone">Mesterolone</a> <ul><li><a href="/wiki/Mesterolone_cipionate" title="Mesterolone cipionate">Mesterolone cipionate</a></li></ul></li> <li><a href="/wiki/Methyldiazinol" title="Methyldiazinol">Methyldiazinol</a></li> <li><a href="/wiki/Nisterime" title="Nisterime">Nisterime</a> <ul><li><a href="/wiki/Nisterime_acetate" title="Nisterime acetate">Nisterime acetate</a></li></ul></li> <li><a href="/wiki/Prostanozol" title="Prostanozol">Prostanozol</a></li> <li><a href="/wiki/Stenbolone" title="Stenbolone">Stenbolone</a> <ul><li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul></li> <li><a href="/wiki/Testifenon" title="Testifenon">Testifenon (testiphenon, testiphenone)</a></li></ul> <ul><li>19-Nortestosterone derivatives: <a href="/wiki/7%CE%B1-Methyl-19-norandrostenedione" title="7α-Methyl-19-norandrostenedione">7α-Methyl-19-norandrostenedione (MENT dione, trestione)</a></li> <li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone" title="11β-Methyl-19-nortestosterone">11β-Methyl-19-nortestosterone</a> <ul><li><a href="/wiki/11%CE%B2-Methyl-19-nortestosterone_dodecylcarbonate" title="11β-Methyl-19-nortestosterone dodecylcarbonate">11β-Methyl-19-nortestosterone dodecylcarbonate</a></li></ul></li> <li><a href="/wiki/19-Nor-5-androstenediol" title="19-Nor-5-androstenediol">19-Nor-5-androstenediol</a></li> <li><a href="/wiki/19-Nor-5-androstenedione" title="19-Nor-5-androstenedione">19-Nor-5-androstenedione</a></li> <li><a href="/wiki/19-Nordehydroepiandrosterone" title="19-Nordehydroepiandrosterone">19-Nordehydroepiandrosterone</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a> <ul><li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li></ul></li> <li><a href="/wiki/Bolandione" title="Bolandione">Bolandione (19-nor-4-androstenedione)</a></li> <li><a href="/wiki/Bolmantalate" title="Bolmantalate">Bolmantalate (nandrolone adamantoate)</a></li> <li><a href="/wiki/Dienedione" title="Dienedione">Dienedione</a></li> <li><a href="/wiki/Dienolone" title="Dienolone">Dienolone</a></li> <li><a href="/wiki/Dimethandrolone" title="Dimethandrolone">Dimethandrolone</a> <ul><li><a href="/wiki/Dimethandrolone_buciclate" title="Dimethandrolone buciclate">Dimethandrolone buciclate</a></li> <li><a href="/wiki/Dimethandrolone_dodecylcarbonate" title="Dimethandrolone dodecylcarbonate">Dimethandrolone dodecylcarbonate</a></li> <li><a href="/wiki/Dimethandrolone_undecanoate" title="Dimethandrolone undecanoate">Dimethandrolone undecanoate</a></li></ul></li> <li><a href="/wiki/LS-1727" title="LS-1727">LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)</a></li> <li><a href="/wiki/Methoxydienone" title="Methoxydienone">Methoxydienone (methoxygonadiene)</a></li> <li><a href="/wiki/Nandrolone" title="Nandrolone">Nandrolone</a> <ul><li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">Nandrolone esters</a></li></ul></li> <li><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a> <ul><li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li></ul></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Oxabolone" title="Oxabolone">Oxabolone</a> <ul><li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li></ul></li> <li><a href="/wiki/Trenbolone" title="Trenbolone">Trenbolone</a> <ul><li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_enanthate" title="Trenbolone enanthate">Trenbolone enanthate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate</a></li> <li><a href="/wiki/Trenbolone_undecanoate" title="Trenbolone undecanoate">Trenbolone undecanoate</a></li></ul></li> <li><a href="/wiki/Trendione" title="Trendione">Trendione</a></li> <li><a href="/wiki/Trestolone" title="Trestolone">Trestolone (MENT)</a> <ul><li><a href="/wiki/Trestolone_acetate" title="Trestolone acetate">Trestolone acetate</a></li> <li><a href="/wiki/Trestolone_enanthate" title="Trestolone enanthate">Trestolone enanthate</a></li></ul></li></ul> <ul><li>5α-Dihydro-19-nortestosterone derivatives: <a href="/wiki/5%CE%B1-Dihydronandrolone" title="5α-Dihydronandrolone">5α-Dihydronandrolone</a></li> <li><a href="/w/index.php?title=5%CE%B1-Dihydrotrestolone&action=edit&redlink=1" class="new" title="5α-Dihydrotrestolone (page does not exist)">5α-Dihydrotrestolone</a></li> <li><a href="/wiki/19-Norandrosterone" title="19-Norandrosterone">19-Norandrosterone</a></li></ul> <ul><li>17α-Alkylated testosterone derivatives: <a href="/wiki/Bolasterone" title="Bolasterone">Bolasterone</a></li> <li><a href="/wiki/Calusterone" title="Calusterone">Calusterone</a></li> <li><a href="/wiki/Chlorodehydromethylandrostenediol" title="Chlorodehydromethylandrostenediol">Chlorodehydromethylandrostenediol (CDMA)</a></li> <li><a href="/wiki/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</a></li> <li><a href="/wiki/Chloromethylandrostenediol" title="Chloromethylandrostenediol">Chloromethylandrostenediol (CMA)</a></li> <li><a href="/wiki/Enestebol" title="Enestebol">Enestebol</a></li> <li><a href="/wiki/Ethyltestosterone" title="Ethyltestosterone">Ethyltestosterone</a></li> <li><a href="/wiki/Fluoxymesterone" title="Fluoxymesterone">Fluoxymesterone</a></li> <li><a href="/wiki/Formebolone" title="Formebolone">Formebolone</a></li> <li><a href="/wiki/Hydroxystenozole" title="Hydroxystenozole">Hydroxystenozole</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone (methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a> <ul><li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</a></li> <li><a href="/wiki/Methandriol_diacetate" title="Methandriol diacetate">Methandriol diacetate</a></li> <li><a href="/wiki/Methandriol_dipropionate" title="Methandriol dipropionate">Methandriol dipropionate</a></li> <li><a href="/wiki/Methandriol_propionate" title="Methandriol propionate">Methandriol propionate</a></li></ul></li> <li><a href="/wiki/Methylclostebol" title="Methylclostebol">Methylclostebol (chloromethyltestosterone)</a></li> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a> (<a href="/wiki/Esterified_estrogens/methyltestosterone" title="Esterified estrogens/methyltestosterone">+esterified estrogens</a>) <ul><li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></li></ul></li> <li><a href="/wiki/Oxymesterone" title="Oxymesterone">Oxymesterone</a></li> <li><a href="/wiki/Penmesterol" title="Penmesterol">Penmesterol</a></li> <li><a href="/wiki/Tiomesterone" title="Tiomesterone">Tiomesterone</a></li></ul> <ul><li>17α-Alkylated 5α-dihydrotestosterone derivatives: <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</a></li> <li><a href="/wiki/Desoxymethyltestosterone" title="Desoxymethyltestosterone">Desoxymethyltestosterone</a></li> <li><a href="/wiki/Furazabol" title="Furazabol">Furazabol</a></li> <li><a href="/wiki/Mebolazine" title="Mebolazine">Mebolazine (dimethazine)</a></li> <li><a href="/wiki/Mestanolone" title="Mestanolone">Mestanolone</a></li> <li><a href="/wiki/Metenolone" title="Metenolone">Metenolone</a> <ul><li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate</a></li></ul></li> <li><a href="/wiki/Methasterone" title="Methasterone">Methasterone</a></li> <li><a href="/wiki/Methyl-1-testosterone" title="Methyl-1-testosterone">Methyl-1-testosterone</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylstenbolone" title="Methylstenbolone">Methylstenbolone</a></li> <li><a href="/wiki/Oxandrolone" title="Oxandrolone">Oxandrolone</a></li> <li><a href="/wiki/Oxymetholone" title="Oxymetholone">Oxymetholone</a></li> <li><a href="/wiki/Stanozolol" title="Stanozolol">Stanozolol</a></li></ul> <ul><li>17α-Alkylated 19-nortestosterone derivatives: <a href="/wiki/Bolenol" title="Bolenol">Bolenol</a></li> <li><a href="/wiki/Dimethyldienolone" title="Dimethyldienolone">Dimethyldienolone</a></li> <li><a href="/wiki/Dimethyltrienolone" title="Dimethyltrienolone">Dimethyltrienolone</a></li> <li><a href="/wiki/Ethyldienolone" title="Ethyldienolone">Ethyldienolone</a></li> <li><a href="/wiki/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></li> <li><a href="/wiki/Methyldienolone" title="Methyldienolone">Methyldienolone</a></li> <li><a href="/wiki/Methylhydroxynandrolone" title="Methylhydroxynandrolone">Methylhydroxynandrolone (MOHN, MHN)</a></li> <li><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norboletone" title="Norboletone">Norboletone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol</a></li> <li><a href="/wiki/RU-2309" title="RU-2309">RU-2309</a></li> <li><a href="/wiki/Tetrahydrogestrinone" title="Tetrahydrogestrinone">Tetrahydrogestrinone</a></li></ul> <ul><li>17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: <a href="/wiki/5%CE%B1-Dihydronorethandrolone" title="5α-Dihydronorethandrolone">5α-Dihydronorethandrolone</a></li> <li><a href="/wiki/5%CE%B1-Dihydronormethandrone" title="5α-Dihydronormethandrone">5α-Dihydronormethandrone</a></li></ul> <ul><li>17α-Vinyltestosterone derivatives: <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li>17α-Vinyl-19-nortestosterone derivatives: <a href="/wiki/Vinyltestosterone" title="Vinyltestosterone">Vinyltestosterone</a></li></ul> <ul><li>17α-Ethynyltestosterone derivatives: <a href="/wiki/Danazol" title="Danazol">Danazol</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/Ethisterone" title="Ethisterone">Ethisterone (ethynyltestosterone)</a></li></ul> <ul><li>5α-Dihydro-17α-ethynyltestosterone derivatives: <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/Dihydroethisterone" class="mw-redirect" title="Dihydroethisterone">Dihydroethisterone</a></li></ul> <ul><li>17α-Ethynyl-19-nortestosterone derivatives: <a href="/wiki/%CE%944-Tibolone" title="Δ4-Tibolone">Δ4-Tibolone</a></li> <li><a href="/wiki/Desogestrel" title="Desogestrel">Desogestrel</a></li> <li><a href="/wiki/Etonogestrel" title="Etonogestrel">Etonogestrel</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a> <ul><li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li></ul></li> <li><a href="/wiki/Gestodene" title="Gestodene">Gestodene</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Levonorgestrel" title="Levonorgestrel">Levonorgestrel</a></li> <li><a href="/wiki/Levonorgestrel_ester" class="mw-redirect" title="Levonorgestrel ester">Levonorgestrel esters</a> (e.g., <a href="/wiki/Levonorgestrel_butanoate" title="Levonorgestrel butanoate">levonorgestrel butanoate</a>)</li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a> <ul><li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li></ul></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Norethisterone_ester" class="mw-redirect" title="Norethisterone ester">Norethisterone esters</a> (e.g., <a href="/wiki/Norethisterone_acetate" title="Norethisterone acetate">norethisterone acetate</a>, <a href="/wiki/Norethisterone_enanthate" title="Norethisterone enanthate">norethisterone enanthate</a>)</li> <li><a href="/wiki/Norgestrel" title="Norgestrel">Norgestrel</a></li> <li><a href="/wiki/Norgestrienone" title="Norgestrienone">Norgestrienone</a></li> <li><a href="/wiki/Quingestanol" title="Quingestanol">Quingestanol</a> <ul><li><a href="/wiki/Quingestanol_acetate" title="Quingestanol acetate">Quingestanol acetate</a></li></ul></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: <a href="/wiki/5%CE%B1-Dihydrolevonorgestrel" title="5α-Dihydrolevonorgestrel">5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/5%CE%B1-Dihydronorethisterone" title="5α-Dihydronorethisterone">5α-Dihydronorethisterone</a></li></ul> <ul><li>Progesterone derivatives: <a href="/wiki/6%CE%B1-Methylprogesterone" title="6α-Methylprogesterone">6α-Methylprogesterone</a></li> <li><a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li></ul> <ul><li>Others/unsorted: <a href="/wiki/3-Keto-5%CE%B1-abiraterone" title="3-Keto-5α-abiraterone">3-Keto-5α-abiraterone</a></li> <li><a href="/wiki/5%CE%B1-Androstane" class="mw-redirect" title="5α-Androstane">5α-Androstane</a></li> <li><a href="/wiki/Alternariol" title="Alternariol">Alternariol</a></li> <li><a href="/wiki/Cl-4AS-1" title="Cl-4AS-1">Cl-4AS-1</a></li> <li><a href="/wiki/Drupanol" title="Drupanol">Drupanol</a></li> <li><a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li> <li><a href="/wiki/ZM-182345" title="ZM-182345">ZM-182345</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center"><a href="/wiki/Selective_androgen_receptor_modulator" title="Selective androgen receptor modulator"><abbr title="Selective androgen receptor modulator">SARMs</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 androgen receptor modulator</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Nonsteroidal: <a href="/w/index.php?title=198RL26&action=edit&redlink=1" class="new" title="198RL26 (page does not exist)">198RL26</a></li> <li><a href="/wiki/ACP-105" title="ACP-105">ACP-105</a></li> <li><a href="/wiki/AC-262,536" title="AC-262,536">AC-262,536</a></li> <li><a href="/wiki/Acetothiolutamide" title="Acetothiolutamide">Acetothiolutamide</a></li> <li><a href="/wiki/Acetoxolutamide" title="Acetoxolutamide">Acetoxolutamide</a></li> <li><a href="/wiki/Andarine" title="Andarine">Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)</a></li> <li><a href="/wiki/BMS-564,929" title="BMS-564,929">BMS-564,929</a></li> <li><a href="/w/index.php?title=DTIB&action=edit&redlink=1" class="new" title="DTIB (page does not exist)">DTIB</a></li> <li><a href="/wiki/Enobosarm" title="Enobosarm">Enobosarm (ostarine, MK-2866, GTx-024, S-22)</a></li> <li><a href="/w/index.php?title=FTBU-1&action=edit&redlink=1" class="new" title="FTBU-1 (page does not exist)">FTBU-1</a></li> <li><a href="/wiki/GLPG-0492" title="GLPG-0492">GLPG-0492</a></li> <li><a href="/wiki/GSK2881078" title="GSK2881078">GSK2881078</a></li> <li><a href="/wiki/GSK-4336A" title="GSK-4336A">GSK-4336A</a></li> <li><a href="/w/index.php?title=GSK-8698&action=edit&redlink=1" class="new" title="GSK-8698 (page does not exist)">GSK-8698</a></li> <li><a href="/wiki/LG121071" title="LG121071">LG121071 (LGD-121071)</a></li> <li><a href="/wiki/LGD-2226" title="LGD-2226">LGD-2226</a></li> <li><a href="/wiki/LGD-2941" title="LGD-2941">LGD-2941 (LGD-122941)</a></li> <li><a href="/wiki/LGD-3303" title="LGD-3303">LGD-3303</a></li> <li><a href="/wiki/LGD-4033" class="mw-redirect" title="LGD-4033">LGD-4033</a></li> <li><a href="/wiki/LY305" title="LY305">LY305</a></li> <li><a href="/wiki/JNJ-26146900" title="JNJ-26146900">JNJ-26146900</a></li> <li><a href="/wiki/JNJ-28330835" title="JNJ-28330835">JNJ-28330835</a></li> <li><a href="/wiki/JNJ-37654032" title="JNJ-37654032">JNJ-37654032</a></li> <li><a href="/wiki/OPK-88004" title="OPK-88004">OPK-88004 (LY-2452473, TT-701)</a></li> <li><a href="/w/index.php?title=ORM-11984&action=edit&redlink=1" class="new" title="ORM-11984 (page does not exist)">ORM-11984</a></li> <li><a href="/wiki/PF-06260414" title="PF-06260414">PF-06260414</a></li> <li><a href="/w/index.php?title=R-1_(drug)&action=edit&redlink=1" class="new" title="R-1 (drug) (page does not exist)">R-1</a></li> <li><a href="/wiki/RU-59063" title="RU-59063">RU-59063</a></li> <li><a href="/w/index.php?title=S-1_(drug)&action=edit&redlink=1" class="new" title="S-1 (drug) (page does not exist)">S-1</a></li> <li><a href="/wiki/S-23_(drug)" title="S-23 (drug)">S-23</a></li> <li><a href="/wiki/S-40503" title="S-40503">S-40503</a></li> <li><a href="/w/index.php?title=S-101479&action=edit&redlink=1" class="new" title="S-101479 (page does not exist)">S-101479</a></li> <li><a href="/wiki/Vosilasarm" title="Vosilasarm">Vosilasarm</a></li></ul> <ul><li>Steroidal: <a href="/w/index.php?title=EM-9017&action=edit&redlink=1" class="new" title="EM-9017 (page does not exist)">EM-9017</a></li> <li><a href="/wiki/MK-0773" title="MK-0773">MK-0773</a></li> <li><a href="/wiki/TFM-4AS-1" title="TFM-4AS-1">TFM-4AS-1</a></li> <li><a href="/wiki/YK-11" title="YK-11">YK-11</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>Steroidal: <a href="/wiki/7%CE%B1-Thioprogesterone" title="7α-Thioprogesterone">7α-Thioprogesterone</a></li> <li><a href="/wiki/7%CE%B1-Thiospironolactone" title="7α-Thiospironolactone">7α-Thiospironolactone</a></li> <li><a href="/wiki/7%CE%B1-Thiomethylspironolactone" title="7α-Thiomethylspironolactone">7α-Thiomethylspironolactone</a></li> <li><a href="/wiki/11%CE%B1-Hydroxyprogesterone" title="11α-Hydroxyprogesterone">11α-Hydroxyprogesterone</a></li> <li><a href="/wiki/15%CE%B2-Hydroxycyproterone_acetate" title="15β-Hydroxycyproterone acetate">15β-Hydroxycyproterone acetate</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/Allyltestosterone" title="Allyltestosterone">Allyltestosterone</a></li> <li><a href="/wiki/Benorterone" title="Benorterone">Benorterone</a></li> <li><a href="/wiki/BOMT" title="BOMT">BOMT</a></li> <li><a href="/wiki/Canrenoic_acid" title="Canrenoic acid">Canrenoic acid</a></li> <li><a href="/wiki/Canrenone" title="Canrenone">Canrenone</a></li> <li><a href="/wiki/Chlormadinone_acetate" title="Chlormadinone acetate">Chlormadinone acetate</a></li> <li><a href="/wiki/Clascoterone" title="Clascoterone">Clascoterone</a></li> <li><a href="/wiki/Clometerone" title="Clometerone">Clometerone</a></li> <li><a href="/wiki/Cyproheptadine" title="Cyproheptadine">Cyproheptadine</a></li> <li><a href="/wiki/Cyproterone" title="Cyproterone">Cyproterone</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delanterone" title="Delanterone">Delanterone</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</a></li> <li><a href="/wiki/Dicirenone" title="Dicirenone">Dicirenone</a></li> <li><a href="/wiki/Dienogest" title="Dienogest">Dienogest</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/DU-41165" title="DU-41165">DU-41165</a></li> <li><a href="/wiki/Edogestrone" title="Edogestrone">Edogestrone</a></li> <li><a href="/w/index.php?title=EM-4350&action=edit&redlink=1" class="new" title="EM-4350 (page does not exist)">EM-4350</a></li> <li><a href="/wiki/EM-5854" title="EM-5854">EM-5854</a></li> <li><a href="/w/index.php?title=EM-5855&action=edit&redlink=1" class="new" title="EM-5855 (page does not exist)">EM-5855</a></li> <li><a href="/w/index.php?title=EM-6537&action=edit&redlink=1" class="new" title="EM-6537 (page does not exist)">EM-6537</a></li> <li><a href="/wiki/Epitestosterone" title="Epitestosterone">Epitestosterone</a></li> <li><a href="/wiki/Galeterone" title="Galeterone">Galeterone</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/w/index.php?title=Ludaterone&action=edit&redlink=1" class="new" title="Ludaterone (page does not exist)">Ludaterone</a></li> <li><a href="/wiki/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Mespirenone" title="Mespirenone">Mespirenone</a></li> <li><a href="/wiki/Metogest" title="Metogest">Metogest</a></li> <li><a href="/wiki/Mexrenone" title="Mexrenone">Mexrenone</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</a></li> <li><a href="/wiki/Nordinone" title="Nordinone">Nordinone</a></li> <li><a href="/wiki/Osaterone" title="Osaterone">Osaterone</a></li> <li><a href="/wiki/Osaterone_acetate" title="Osaterone acetate">Osaterone acetate</a></li> <li><a href="/wiki/Oxendolone" title="Oxendolone">Oxendolone</a></li> <li><a href="/wiki/Potassium_canrenoate" title="Potassium canrenoate">Potassium canrenoate</a></li> <li><a href="/wiki/Promegestone" title="Promegestone">Promegestone</a></li> <li><a href="/wiki/Prorenone" title="Prorenone">Prorenone</a></li> <li><a href="/wiki/Rosterolone" title="Rosterolone">Rosterolone</a></li> <li><a href="/w/index.php?title=RU-15328&action=edit&redlink=1" class="new" title="RU-15328 (page does not exist)">RU-15328</a></li> <li><a href="/wiki/SC-5233" title="SC-5233">SC-5233 (spirolactone)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spirorenone" title="Spirorenone">Spirorenone</a></li> <li><a href="/wiki/Spiroxasone" title="Spiroxasone">Spiroxasone</a></li> <li><a href="/wiki/Topterone" title="Topterone">Topterone</a></li> <li><a href="/wiki/Trimegestone" title="Trimegestone">Trimegestone</a></li> <li><a href="/wiki/Trimethyltrienolone" title="Trimethyltrienolone">Trimethyltrienolone (R-2956)</a></li> <li><a href="/wiki/Zanoterone" title="Zanoterone">Zanoterone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/5N-Bicalutamide" title="5N-Bicalutamide">5N-Bicalutamide</a></li> <li><a href="/wiki/AA560" title="AA560">AA560</a></li> <li><a href="/w/index.php?title=Antarlide&action=edit&redlink=1" class="new" title="Antarlide (page does not exist)">Antarlides</a></li> <li><a href="/w/index.php?title=Arabilin&action=edit&redlink=1" class="new" title="Arabilin (page does not exist)">Arabilin</a></li> <li><a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Atraric_acid" title="Atraric acid">Atraric acid</a></li> <li><a href="/w/index.php?title=AZD-3514&action=edit&redlink=1" class="new" title="AZD-3514 (page does not exist)">AZD-3514</a></li> <li><a href="/wiki/Bakuchiol" title="Bakuchiol">Bakuchiol</a></li> <li><a href="/wiki/Bavdegalutamide" title="Bavdegalutamide">Bavdegalutamide</a></li> <li><a href="/w/index.php?title=BAY-1024767&action=edit&redlink=1" class="new" title="BAY-1024767 (page does not exist)">BAY-1024767</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Bisphenol" title="Bisphenol">Bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A_diglycidyl_ether" title="Bisphenol A diglycidyl ether">BADGE</a>, <a href="/w/index.php?title=Bisphenol_F_diglycidyl_ether&action=edit&redlink=1" class="new" title="Bisphenol F diglycidyl ether (page does not exist)">BFDGE</a>, <a href="/wiki/Bisphenol_A" title="Bisphenol A">bisphenol A</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">bisphenol F</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">bisphenol S</a>)</li> <li><a href="/w/index.php?title=BMS-501949&action=edit&redlink=1" class="new" title="BMS-501949 (page does not exist)">BMS-501949</a></li> <li><a href="/w/index.php?title=BMS-570511&action=edit&redlink=1" class="new" title="BMS-570511 (page does not exist)">BMS-570511</a></li> <li><a href="/wiki/BMS-641988" title="BMS-641988">BMS-641988</a></li> <li><a href="/w/index.php?title=CH5137291&action=edit&redlink=1" class="new" title="CH5137291 (page does not exist)">CH5137291</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/wiki/Cioteronel" title="Cioteronel">Cioteronel</a></li> <li><a href="/wiki/Cyanonilutamide" title="Cyanonilutamide">Cyanonilutamide</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (via metabolite <a href="/wiki/Dichlorodiphenyldichloroethylene" title="Dichlorodiphenyldichloroethylene">p,p’-DDE</a>)</li> <li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li> <li><a href="/wiki/DIMP_(antiandrogen)" title="DIMP (antiandrogen)">DIMP</a></li> <li><a href="/wiki/Endosulfan" title="Endosulfan">Endosulfan</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/EPI-001" title="EPI-001">EPI-001</a></li> <li><a href="/wiki/Fenarimol" title="Fenarimol">Fenarimol</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Hydroxyflutamide" title="Hydroxyflutamide">Hydroxyflutamide</a></li> <li><a href="/wiki/Inocoterone" title="Inocoterone">Inocoterone</a></li> <li><a href="/wiki/Inocoterone_acetate" title="Inocoterone acetate">Inocoterone acetate</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Ketodarolutamide" title="Ketodarolutamide">Ketodarolutamide</a></li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/w/index.php?title=LG-105&action=edit&redlink=1" class="new" title="LG-105 (page does not exist)">LG-105</a></li> <li><a href="/wiki/LG-120907" title="LG-120907">LG-120907</a></li> <li><a href="/w/index.php?title=LGD-1331&action=edit&redlink=1" class="new" title="LGD-1331 (page does not exist)">LGD-1331</a></li> <li><a href="/wiki/Linuron" title="Linuron">Linuron</a></li> <li><a href="/wiki/Masofaniten" title="Masofaniten">Masofaniten</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/w/index.php?title=N-Butylbenzenesulfonamide&action=edit&redlink=1" class="new" title="N-Butylbenzenesulfonamide (page does not exist)">N-Butylbenzenesulfonamide</a></li> <li><a href="/wiki/N-Desmethylapalutamide" title="N-Desmethylapalutamide">N-Desmethylapalutamide</a></li> <li><a href="/wiki/N-Desmethylenzalutamide" title="N-Desmethylenzalutamide">N-Desmethylenzalutamide</a></li> <li><a href="/wiki/Nilutamide" title="Nilutamide">Nilutamide</a></li> <li><a href="/w/index.php?title=ONC1-13B&action=edit&redlink=1" class="new" title="ONC1-13B (page does not exist)">ONC1-13B</a></li> <li><a href="/wiki/Pentomone" title="Pentomone">Pentomone</a></li> <li><a href="/w/index.php?title=PF-998425&action=edit&redlink=1" class="new" title="PF-998425 (page does not exist)">PF-998425</a></li> <li><a href="/wiki/Phenothrin" title="Phenothrin">Phenothrin</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/wiki/Procymidone" title="Procymidone">Procymidone</a></li> <li><a href="/wiki/Proxalutamide" title="Proxalutamide">Proxalutamide</a></li> <li><a href="/wiki/Pyrilutamide" title="Pyrilutamide">Pyrilutamide</a></li> <li><a href="/wiki/Ralaniten" title="Ralaniten">Ralaniten (EPI-002)</a></li> <li><a href="/wiki/Ralaniten_acetate" title="Ralaniten acetate">Ralaniten acetate (EPI-506)</a></li> <li><a href="/wiki/RD-162" title="RD-162">RD-162</a></li> <li><a href="/wiki/Rezvilutamide" title="Rezvilutamide">Rezvilutamide</a></li> <li><a href="/w/index.php?title=Ro_2-7239&action=edit&redlink=1" class="new" title="Ro 2-7239 (page does not exist)">Ro 2-7239</a></li> <li><a href="/w/index.php?title=Ro_5-2537&action=edit&redlink=1" class="new" title="Ro 5-2537 (page does not exist)">Ro 5-2537</a></li> <li><a href="/wiki/RU-22930" title="RU-22930">RU-22930</a></li> <li><a href="/wiki/RU-56187" title="RU-56187">RU-56187</a></li> <li><a href="/wiki/RU-57073" title="RU-57073">RU-57073</a></li> <li><a href="/wiki/RU-58642" title="RU-58642">RU-58642</a></li> <li><a href="/wiki/RU-58841" title="RU-58841">RU-58841</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a></li> <li><a href="/wiki/Thalidomide" title="Thalidomide">Thalidomide</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/wiki/Vinclozolin" title="Vinclozolin">Vinclozolin</a></li> <li><a href="/w/index.php?title=YM-580&action=edit&redlink=1" class="new" title="YM-580 (page does not exist)">YM-580</a></li> <li><a href="/w/index.php?title=YM-92088&action=edit&redlink=1" class="new" title="YM-92088 (page does not exist)">YM-92088</a></li> <li><a href="/w/index.php?title=YM-175735&action=edit&redlink=1" class="new" title="YM-175735 (page does not exist)">YM-175735</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/GPRC6A" title="GPRC6A">GPRC6A</a></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/Cation" class="mw-redirect" title="Cation">Cations</a> (incl. <a href="/wiki/Aluminium" title="Aluminium">aluminium</a>, <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Gadolinium" title="Gadolinium">gadolinium</a>, <a href="/wiki/Magnesium" title="Magnesium">magnesium</a>, <a href="/wiki/Strontium" title="Strontium">strontium</a>, <a href="/wiki/Zinc" title="Zinc">zinc</a>)</li> <li><a href="/wiki/Dehydroandrosterone" title="Dehydroandrosterone">Dehydroandrosterone</a></li> <li><a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">Dihydrotestosterone</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Amino_acid" title="Amino acid">L-α-Amino acids</a> (incl. <a href="/wiki/Arginine" title="Arginine">L-arginine</a>, <a href="/wiki/Lysine" title="Lysine">L-lysine</a>, <a href="/wiki/Ornithine" title="Ornithine">L-ornithine</a>)</li> <li><a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a></li> <li><a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin"><abbr title="Sex hormone-binding globulin">SHBG</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Sex hormone-binding globulin</li> <li><a href="/wiki/Testosterone" title="Testosterone">Testosterone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens">Androgens and antiandrogens</a></dd> <dd><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators">Estrogen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_androgens_and_anabolic_steroids" title="List of androgens and anabolic steroids">List of androgens and anabolic steroids</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Estrogen_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Estrogen_receptor_modulators" title="Template:Estrogen receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Estrogen_receptor_modulators" title="Template talk:Estrogen receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Estrogen_receptor_modulators" title="Special:EditPage/Template:Estrogen receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Estrogen_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor">Estrogen receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Estrogen_receptor" title="Estrogen receptor"><abbr title="Estrogen receptor">ER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Estrogen receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Steroidal: <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Methyl-19-methyleneandrosta-3,5-dien-17%CE%B2-ol" title="3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol">3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol</a></li> <li><a href="/wiki/3%CE%B1-Androstanediol" title="3α-Androstanediol">3α-Androstanediol</a></li> <li><a href="/w/index.php?title=3%CE%B1,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3α,5α-Dihydrolevonorgestrel (page does not exist)">3α,5α-Dihydrolevonorgestrel</a></li> <li><a href="/w/index.php?title=3%CE%B2,5%CE%B1-Dihydrolevonorgestrel&action=edit&redlink=1" class="new" title="3β,5α-Dihydrolevonorgestrel (page does not exist)">3β,5α-Dihydrolevonorgestrel</a></li> <li><a href="/wiki/3%CE%B1-Hydroxytibolone" title="3α-Hydroxytibolone">3α-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Hydroxytibolone" title="3β-Hydroxytibolone">3β-Hydroxytibolone</a></li> <li><a href="/wiki/3%CE%B2-Androstanediol" title="3β-Androstanediol">3β-Androstanediol</a></li> <li><a href="/wiki/4-Androstenediol" title="4-Androstenediol">4-Androstenediol</a></li> <li><a href="/wiki/4-Androstenedione" class="mw-redirect" title="4-Androstenedione">4-Androstenedione</a></li> <li><a href="/wiki/4-Fluoroestradiol" title="4-Fluoroestradiol">4-Fluoroestradiol</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a></li> <li><a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li> <li><a href="/wiki/5-Androstenediol" class="mw-redirect" title="5-Androstenediol">5-Androstenediol</a></li> <li><a href="/wiki/7-Keto-DHEA" title="7-Keto-DHEA">7-Oxo-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Hydroxy-DHEA" title="7α-Hydroxy-DHEA">7α-Hydroxy-DHEA</a></li> <li><a href="/wiki/7%CE%B1-Methylestradiol" title="7α-Methylestradiol">7α-Methylestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/8,9-Dehydroestradiol" title="8,9-Dehydroestradiol">8,9-Dehydroestradiol</a></li> <li><a href="/wiki/8,9-Dehydroestrone" title="8,9-Dehydroestrone">8,9-Dehydroestrone</a></li> <li><a href="/wiki/8%CE%B2-VE2" title="8β-VE2">8β-VE2</a></li> <li><a href="/wiki/10%CE%B2,17%CE%B2-Dihydroxyestra-1,4-dien-3-one" title="10β,17β-Dihydroxyestra-1,4-dien-3-one">10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)</a></li> <li><a href="/wiki/11%CE%B2-Chloromethylestradiol" title="11β-Chloromethylestradiol">11β-Chloromethylestradiol</a></li> <li><a href="/wiki/11%CE%B2-Methoxyestradiol" title="11β-Methoxyestradiol">11β-Methoxyestradiol</a></li> <li><a href="/wiki/15%CE%B1-Hydroxyestradiol" title="15α-Hydroxyestradiol">15α-Hydroxyestradiol</a></li> <li><a href="/wiki/16-Ketoestradiol" title="16-Ketoestradiol">16-Ketoestradiol</a></li> <li><a href="/wiki/16-Ketoestrone" title="16-Ketoestrone">16-Ketoestrone</a></li> <li><a href="/wiki/16%CE%B1-Fluoroestradiol" class="mw-redirect" title="16α-Fluoroestradiol">16α-Fluoroestradiol</a></li> <li><a href="/wiki/16%CE%B1-Hydroxy-DHEA" title="16α-Hydroxy-DHEA">16α-Hydroxy-DHEA</a></li> <li><a href="/wiki/16%CE%B1-Hydroxyestrone" title="16α-Hydroxyestrone">16α-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B1-Iodoestradiol" class="mw-redirect" title="16α-Iodoestradiol">16α-Iodoestradiol</a></li> <li><a href="/wiki/16%CE%B1-LE2" title="16α-LE2">16α-LE2</a></li> <li><a href="/wiki/16%CE%B2-Hydroxyestrone" title="16β-Hydroxyestrone">16β-Hydroxyestrone</a></li> <li><a href="/wiki/16%CE%B2,17%CE%B1-Epiestriol" title="16β,17α-Epiestriol">16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Estradiol" title="17α-Estradiol">17α-Estradiol</a> (<a href="/wiki/Alfatradiol" title="Alfatradiol">alfatradiol</a>)</li> <li><a href="/wiki/17%CE%B1-Dihydroequilenin" title="17α-Dihydroequilenin">17α-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B1-Dihydroequilin" title="17α-Dihydroequilin">17α-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B1-Epiestriol" title="17α-Epiestriol">17α-Epiestriol (16α-hydroxy-17α-estradiol)</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B1-androstanediol" title="17α-Ethynyl-3α-androstanediol">17α-Ethynyl-3α-androstanediol</a></li> <li><a href="/wiki/17%CE%B1-Ethynyl-3%CE%B2-androstanediol" title="17α-Ethynyl-3β-androstanediol">17α-Ethynyl-3β-androstanediol</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilenin" title="17β-Dihydroequilenin">17β-Dihydroequilenin</a></li> <li><a href="/wiki/17%CE%B2-Dihydroequilin" title="17β-Dihydroequilin">17β-Dihydroequilin</a></li> <li><a href="/wiki/17%CE%B2-Methyl-17%CE%B1-dihydroequilenin" title="17β-Methyl-17α-dihydroequilenin">17β-Methyl-17α-dihydroequilenin</a></li> <li><a href="/wiki/Abiraterone" class="mw-redirect" title="Abiraterone">Abiraterone</a></li> <li><a href="/wiki/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a></li> <li><a href="/wiki/Alestramustine" title="Alestramustine">Alestramustine</a></li> <li><a href="/wiki/Almestrone" title="Almestrone">Almestrone</a></li> <li><a href="/wiki/Anabolic_steroid" title="Anabolic steroid">Anabolic steroids</a> (e.g., <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">esters</a>, <a href="/wiki/Methyltestosterone" title="Methyltestosterone">methyltestosterone</a>, <a href="/wiki/Metandienone" title="Metandienone">metandienone (methandrostenolone)</a>, <a href="/wiki/Nandrolone" title="Nandrolone">nandrolone</a> and <a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">esters</a>, many others; via estrogenic metabolites)</li> <li><a href="/wiki/Atrimustine" title="Atrimustine">Atrimustine</a></li> <li><a href="/wiki/Bolandiol" title="Bolandiol">Bolandiol</a></li> <li><a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/Butolame" title="Butolame">Butolame</a></li> <li><a href="/wiki/Clomestrone" title="Clomestrone">Clomestrone</a></li> <li><a href="/wiki/Cloxestradiol" title="Cloxestradiol">Cloxestradiol</a> <ul><li><a href="/wiki/Cloxestradiol_acetate" title="Cloxestradiol acetate">Cloxestradiol acetate</a></li></ul></li> <li><a href="/wiki/Conjugated_estriol" title="Conjugated estriol">Conjugated estriol</a></li> <li><a href="/wiki/Conjugated_estrogens" title="Conjugated estrogens">Conjugated estrogens</a></li> <li><a href="/wiki/Cyclodiol" title="Cyclodiol">Cyclodiol</a></li> <li><a href="/wiki/Cyclotriol" title="Cyclotriol">Cyclotriol</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA-S</a></li> <li><a href="/wiki/Ent-Estradiol" title="Ent-Estradiol">ent-Estradiol</a></li> <li><a href="/wiki/Epiestriol" title="Epiestriol">Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)</a></li> <li><a href="/wiki/Epimestrol" title="Epimestrol">Epimestrol</a></li> <li><a href="/wiki/Equilenin" title="Equilenin">Equilenin</a></li> <li><a href="/wiki/Equilin" title="Equilin">Equilin</a></li> <li><a href="/wiki/ERA-63" title="ERA-63">ERA-63 (ORG-37663)</a></li> <li><a href="/wiki/Esterified_estrogens" title="Esterified estrogens">Esterified estrogens</a></li> <li><a href="/wiki/Estetrol" title="Estetrol">Estetrol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">Estradiol esters</a></li> <li><a href="/wiki/Lipoidal_estradiol" title="Lipoidal estradiol">Lipoidal estradiol</a></li> <li><a href="/wiki/Polyestradiol_phosphate" title="Polyestradiol phosphate">Polyestradiol phosphate</a></li></ul></li> <li><a href="/wiki/Estramustine" title="Estramustine">Estramustine</a></li> <li><a class="mw-selflink selflink">Estramustine phosphate</a></li> <li><a href="/wiki/Estrapronicate" title="Estrapronicate">Estrapronicate</a></li> <li><a href="/wiki/Estrazinol" title="Estrazinol">Estrazinol</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estriol_esters" title="List of estrogen esters">Estriol esters</a></li> <li><a href="/wiki/Polyestriol_phosphate" title="Polyestriol phosphate">Polyestriol phosphate</a></li></ul></li> <li><a href="/wiki/Estrofurate" title="Estrofurate">Estrofurate</a></li> <li><a href="/wiki/Estrogenic_substances" title="Estrogenic substances">Estrogenic substances</a></li> <li><a href="/wiki/Estromustine" title="Estromustine">Estromustine</a></li> <li><a href="/wiki/Estrone" title="Estrone">Estrone</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Estrone_esters" title="List of estrogen esters">Estrone esters</a></li> <li><a href="/wiki/Estrone_methyl_ether" title="Estrone methyl ether">Estrone methyl ether</a></li> <li><a href="/wiki/Estropipate" title="Estropipate">Estropipate</a></li></ul></li> <li><a href="/wiki/Etamestrol" title="Etamestrol">Etamestrol (eptamestrol)</a></li> <li><a href="/wiki/Ethinylandrostenediol" title="Ethinylandrostenediol">Ethinylandrostenediol</a> <ul><li><a href="/wiki/Ethandrostate" title="Ethandrostate">Ethandrostate</a></li></ul></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a> <ul><li><a href="/wiki/Ethinylestradiol_3-benzoate" class="mw-redirect" title="Ethinylestradiol 3-benzoate">Ethinylestradiol 3-benzoate</a></li> <li><a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">Ethinylestradiol sulfonate</a></li></ul></li> <li><a href="/wiki/Ethinylestriol" title="Ethinylestriol">Ethinylestriol</a></li> <li><a href="/wiki/Ethylestradiol" title="Ethylestradiol">Ethylestradiol</a></li> <li><a href="/wiki/Etynodiol" title="Etynodiol">Etynodiol</a></li> <li><a href="/wiki/Etynodiol_diacetate" title="Etynodiol diacetate">Etynodiol diacetate</a></li> <li><a href="/wiki/Hexolame" title="Hexolame">Hexolame</a></li> <li><a href="/wiki/Hippulin" title="Hippulin">Hippulin</a></li> <li><a href="/wiki/Hydroxyestrone_diacetate" title="Hydroxyestrone diacetate">Hydroxyestrone diacetate</a></li> <li><a href="/wiki/Lynestrenol" title="Lynestrenol">Lynestrenol</a></li> <li><a href="/wiki/Lynestrenol_phenylpropionate" title="Lynestrenol phenylpropionate">Lynestrenol phenylpropionate</a></li> <li><a href="/wiki/Mestranol" title="Mestranol">Mestranol</a></li> <li><a href="/wiki/Methylestradiol" title="Methylestradiol">Methylestradiol</a></li> <li><a href="/wiki/Moxestrol" title="Moxestrol">Moxestrol</a></li> <li><a href="/wiki/Mytatrienediol" title="Mytatrienediol">Mytatrienediol</a></li> <li><a href="/wiki/Nilestriol" title="Nilestriol">Nilestriol</a></li> <li><a href="/wiki/Norethisterone" title="Norethisterone">Norethisterone</a></li> <li><a href="/wiki/Noretynodrel" title="Noretynodrel">Noretynodrel</a></li> <li><a href="/wiki/Orestrate" title="Orestrate">Orestrate</a></li> <li><a href="/wiki/Pentolame" title="Pentolame">Pentolame</a></li> <li><a href="/wiki/Prodiame" title="Prodiame">Prodiame</a></li> <li><a href="/wiki/Prolame" title="Prolame">Prolame</a></li> <li><a href="/wiki/Promestriene" title="Promestriene">Promestriene</a></li> <li><a href="/wiki/RU-16117" title="RU-16117">RU-16117</a></li> <li><a href="/wiki/Quinestradol" title="Quinestradol">Quinestradol</a></li> <li><a href="/wiki/Quinestrol" title="Quinestrol">Quinestrol</a></li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/(S,S)-Tetrahydrochrysene" title="(S,S)-Tetrahydrochrysene">(S,S)-THC</a></li> <li><a href="/wiki/2,8-Dihydroxyhexahydrochrysene" title="2,8-Dihydroxyhexahydrochrysene">2,8-DHHHC</a></li> <li><a href="/w/index.php?title=%CE%92-LGND1&action=edit&redlink=1" class="new" title="Β-LGND1 (page does not exist)">β-LGND1</a></li> <li><a href="/wiki/%CE%92-LGND2" title="Β-LGND2">β-LGND2 (GTx-878)</a></li> <li><a href="/w/index.php?title=AC-186&action=edit&redlink=1" class="new" title="AC-186 (page does not exist)">AC-186</a></li> <li><a href="/wiki/Allenestrol" title="Allenestrol">Allenestrol</a></li> <li><a href="/wiki/Allenolic_acid" title="Allenolic acid">Allenolic acid</a></li> <li><a href="/wiki/Benzestrol" title="Benzestrol">Benzestrol</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Bisdehydrodoisynolic_acid" title="Bisdehydrodoisynolic acid">Bisdehydrodoisynolic acid</a></li> <li><a href="/wiki/Butestrol" title="Butestrol">Butestrol</a></li> <li><a href="/wiki/Carbestrol" title="Carbestrol">Carbestrol</a></li> <li><a href="/wiki/D-15414" title="D-15414">D-15414</a></li> <li><a href="/wiki/DCW234" title="DCW234">DCW234</a></li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Dienestrol" title="Dienestrol">Dienestrol</a> <ul><li><a href="/wiki/Dienestrol_diacetate" title="Dienestrol diacetate">Dienestrol diacetate</a></li></ul></li> <li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Diethylstilbestrol_esters" title="List of estrogen esters">Diethylstilbestrol esters</a></li></ul></li> <li><a href="/wiki/Dimestrol" title="Dimestrol">Dimestrol (dianisylhexene)</a></li> <li><a href="/wiki/Dimethylstilbestrol" title="Dimethylstilbestrol">Dimethylstilbestrol</a></li> <li><a href="/wiki/Doisynoestrol" title="Doisynoestrol">Doisynoestrol (fenocycline)</a></li> <li><a href="/wiki/Doisynolic_acid" title="Doisynolic acid">Doisynolic acid</a></li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Elacestrant" title="Elacestrant">Elacestrant</a></li> <li><a href="/wiki/ERB-196" title="ERB-196">ERB-196 (WAY-202196)</a></li> <li><a href="/wiki/Erteberel" title="Erteberel">Erteberel (SERBA-1, LY-500307)</a></li> <li><a href="/wiki/Estrobin" title="Estrobin">Estrobin (DBE)</a></li> <li><a href="/wiki/Fenestrel" title="Fenestrel">Fenestrel</a></li> <li><a href="/wiki/FERb_033" title="FERb 033">FERb 033</a></li> <li><a href="/wiki/Fosfestrol" title="Fosfestrol">Fosfestrol (diethylstilbestrol diphosphate)</a></li> <li><a href="/wiki/Furostilbestrol" title="Furostilbestrol">Furostilbestrol (diethylstilbestrol difuroate)</a></li> <li><a href="/wiki/GTx-758" title="GTx-758">GTx-758</a></li> <li><a href="/wiki/Hexestrol" title="Hexestrol">Hexestrol</a> <ul><li><a href="/wiki/List_of_estrogen_esters#Hexestrol_esters" title="List of estrogen esters">Hexestrol esters</a></li></ul></li> <li><a href="/wiki/ICI-85966" title="ICI-85966">ICI-85966 (Stilbostat)</a></li> <li><a href="/wiki/M2613" title="M2613">M2613</a></li> <li><a href="/wiki/Meso-Butestrol" title="Meso-Butestrol">meso-Butestrol</a></li> <li><a href="/wiki/Meso-Hexestrol" class="mw-redirect" title="Meso-Hexestrol">meso-Hexestrol</a></li> <li><a href="/wiki/Mestilbol" title="Mestilbol">Mestilbol</a></li> <li><a href="/wiki/Methallenestril" title="Methallenestril">Methallenestril</a></li> <li><a href="/wiki/Methestrol" title="Methestrol">Methestrol</a></li> <li><a href="/wiki/Methestrol_dipropionate" title="Methestrol dipropionate">Methestrol dipropionate</a></li> <li><a href="/wiki/Paroxypropione" title="Paroxypropione">Paroxypropione</a></li> <li><a href="/wiki/Pentafluranol" title="Pentafluranol">Pentafluranol</a></li> <li><a href="/wiki/Phenestrol" title="Phenestrol">Phenestrol</a></li> <li><a href="/wiki/Prinaberel" title="Prinaberel">Prinaberel (ERB-041, WAY-202041)</a></li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quadrosilan" title="Quadrosilan">Quadrosilan</a></li> <li><a href="/w/index.php?title=SC-3296&action=edit&redlink=1" class="new" title="SC-3296 (page does not exist)">SC-3296</a></li> <li><a href="/wiki/SC-4289" title="SC-4289">SC-4289</a></li> <li><a href="/wiki/SERBA-2" title="SERBA-2">SERBA-2</a></li> <li><a href="/wiki/SKF-82,958" title="SKF-82,958">SKF-82,958</a></li> <li><a href="/wiki/Terfluranol" title="Terfluranol">Terfluranol</a></li> <li><a href="/wiki/Triphenylbromoethylene" title="Triphenylbromoethylene">Triphenylbromoethylene</a></li> <li><a href="/wiki/Triphenylchloroethylene" title="Triphenylchloroethylene">Triphenylchloroethylene</a></li> <li><a href="/wiki/Triphenyliodoethylene" title="Triphenyliodoethylene">Triphenyliodoethylene</a></li> <li><a href="/wiki/Triphenylmethylethylene" title="Triphenylmethylethylene">Triphenylmethylethylene (triphenylpropene)</a></li> <li><a href="/wiki/WAY-166818" title="WAY-166818">WAY-166818</a></li> <li><a href="/w/index.php?title=WAY-169916&action=edit&redlink=1" class="new" title="WAY-169916 (page does not exist)">WAY-169916</a></li> <li><a href="/wiki/WAY-200070" title="WAY-200070">WAY-200070</a></li> <li><a href="/wiki/WAY-204688" title="WAY-204688">WAY-204688 (SIM-688)</a></li> <li><a href="/wiki/WAY-214156" title="WAY-214156">WAY-214156</a></li></ul> <ul><li>Unknown/unsorted: <a href="/wiki/ERB-26" title="ERB-26">ERB-26</a></li> <li><a href="/wiki/ERA-45" title="ERA-45">ERA-45</a></li> <li><a href="/wiki/ERB-79" title="ERB-79">ERB-79</a></li> <li><a href="/wiki/ZK-283197" title="ZK-283197">ZK-283197</a></li></ul> <ul><li>Xenoestrogens: <a href="/wiki/Anise" title="Anise">Anise</a>-related (e.g., <a href="/wiki/Anethole" title="Anethole">anethole</a>, <a href="/wiki/Anol" title="Anol">anol</a>, <a href="/wiki/Dianethole" title="Dianethole">dianethole</a>, <a href="/wiki/Dianol" title="Dianol">dianol</a>, <a href="/wiki/Photoanethole" title="Photoanethole">photoanethole</a>)</li> <li><a href="/wiki/Chalconoid" title="Chalconoid">Chalconoids</a> (e.g., <a href="/wiki/Isoliquiritigenin" title="Isoliquiritigenin">isoliquiritigenin</a>, <a href="/wiki/Phloretin" title="Phloretin">phloretin</a>, <a href="/wiki/Phlorizin" title="Phlorizin">phlorizin (phloridzin)</a>, <a href="/wiki/Wedelolactone" title="Wedelolactone">wedelolactone</a>)</li> <li><a href="/wiki/Coumestan" title="Coumestan">Coumestans</a> (e.g., <a href="/wiki/Coumestrol" title="Coumestrol">coumestrol</a>, <a href="/wiki/Psoralidin" title="Psoralidin">psoralidin</a>)</li> <li><a href="/wiki/Flavonoid" title="Flavonoid">Flavonoids</a> (incl. <a href="/wiki/7,8-Dihydroxyflavone" class="mw-redirect" title="7,8-Dihydroxyflavone">7,8-DHF</a>, <a href="/wiki/8-Prenylnaringenin" title="8-Prenylnaringenin">8-prenylnaringenin</a>, <a href="/wiki/Apigenin" title="Apigenin">apigenin</a>, <a href="/wiki/Baicalein" title="Baicalein">baicalein</a>, <a href="/wiki/Baicalin" title="Baicalin">baicalin</a>, <a href="/wiki/Biochanin_A" title="Biochanin A">biochanin A</a>, <a href="/wiki/Calycosin" title="Calycosin">calycosin</a>, <a href="/wiki/Catechin" title="Catechin">catechin</a>, <a href="/wiki/Daidzein" title="Daidzein">daidzein</a>, <a href="/wiki/Daidzin" title="Daidzin">daidzin</a>, <a href="/wiki/Epicatechin_gallate" title="Epicatechin gallate">ECG</a>, <a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">EGCG</a>, <a href="/wiki/Epicatechin" class="mw-redirect" title="Epicatechin">epicatechin</a>, <a href="/wiki/Equol" title="Equol">equol</a>, <a href="/wiki/Formononetin" title="Formononetin">formononetin</a>, <a href="/wiki/Glabrene" title="Glabrene">glabrene</a>, <a href="/wiki/Glabridin" title="Glabridin">glabridin</a>, <a href="/wiki/Genistein" title="Genistein">genistein</a>, <a href="/wiki/Genistin" title="Genistin">genistin</a>, <a href="/wiki/Glycitein" title="Glycitein">glycitein</a>, <a href="/wiki/Kaempferol" title="Kaempferol">kaempferol</a>, <a href="/wiki/Liquiritigenin" title="Liquiritigenin">liquiritigenin</a>, <a href="/wiki/Mirificin" title="Mirificin">mirificin</a>, <a href="/wiki/Myricetin" title="Myricetin">myricetin</a>, <a href="/wiki/Naringenin" title="Naringenin">naringenin</a>, <a href="/w/index.php?title=Penduletin&action=edit&redlink=1" class="new" title="Penduletin (page does not exist)">penduletin</a>, <a href="/wiki/Pinocembrin" title="Pinocembrin">pinocembrin</a>, <a href="/wiki/Prunetin" title="Prunetin">prunetin</a>, <a href="/wiki/Puerarin" title="Puerarin">puerarin</a>, <a href="/wiki/Quercetin" title="Quercetin">quercetin</a>, <a href="/wiki/Tectoridin" title="Tectoridin">tectoridin</a>, <a href="/wiki/Tectorigenin" title="Tectorigenin">tectorigenin</a>)</li> <li><a href="/wiki/Lavender_oil" title="Lavender oil">Lavender oil</a></li> <li><a href="/wiki/Lignan" title="Lignan">Lignans</a> (e.g., <a href="/wiki/Enterodiol" title="Enterodiol">enterodiol</a>, <a href="/wiki/Enterolactone" title="Enterolactone">enterolactone</a>, <a href="/wiki/Nyasol" title="Nyasol">nyasol (cis-hinokiresinol)</a>)</li> <li><a href="/wiki/Metalloestrogen" title="Metalloestrogen">Metalloestrogens</a> (e.g., <a href="/wiki/Cadmium" title="Cadmium">cadmium</a>)</li> <li><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a> (e.g., <a href="/wiki/Alternariol" title="Alternariol">alternariol</a>, <a href="/wiki/Dieldrin" title="Dieldrin">dieldrin</a>, <a href="/wiki/Endosulfan" title="Endosulfan">endosulfan</a>, <a href="/wiki/Fenarimol" title="Fenarimol">fenarimol</a>, <a href="/wiki/HPTE" title="HPTE">HPTE</a>, <a href="/wiki/Methiocarb" title="Methiocarb">methiocarb</a>, <a href="/wiki/Methoxychlor" title="Methoxychlor">methoxychlor</a>, <a href="/wiki/Triclocarban" title="Triclocarban">triclocarban</a>, <a href="/wiki/Triclosan" title="Triclosan">triclosan</a>)</li> <li><a href="/wiki/Phytosteroid" title="Phytosteroid">Phytosteroids</a> (e.g., <a href="/wiki/Digitoxin" title="Digitoxin">digitoxin</a> (<a href="/wiki/Digitalis" title="Digitalis">digitalis</a>), <a href="/wiki/Diosgenin" title="Diosgenin">diosgenin</a>, <a href="/wiki/Guggulsterone" title="Guggulsterone">guggulsterone</a>)</li> <li><a href="/wiki/Phytosterol" title="Phytosterol">Phytosterols</a> (e.g., <a href="/wiki/%CE%92-sitosterol" class="mw-redirect" title="Β-sitosterol">β-sitosterol</a>, <a href="/wiki/Campesterol" title="Campesterol">campesterol</a>, <a href="/wiki/Stigmasterol" title="Stigmasterol">stigmasterol</a>)</li> <li><a href="/wiki/Resorcylic_acid_lactone" title="Resorcylic acid lactone">Resorcylic acid lactones</a> (e.g., <a href="/wiki/Zearalanone" title="Zearalanone">zearalanone</a>, <a href="/wiki/%CE%91-zearalenol" class="mw-redirect" title="Α-zearalenol">α-zearalenol</a>, <a href="/wiki/%CE%92-zearalenol" class="mw-redirect" title="Β-zearalenol">β-zearalenol</a>, <a href="/wiki/Zearalenone" title="Zearalenone">zearalenone</a>, <a href="/wiki/Zeranol" title="Zeranol">zeranol (α-zearalanol)</a>, <a href="/wiki/Taleranol" title="Taleranol">taleranol (teranol, β-zearalanol)</a>)</li> <li><a href="/wiki/Steroid" title="Steroid">Steroid</a>-like (e.g., <a href="/wiki/Deoxymiroestrol" class="mw-redirect" title="Deoxymiroestrol">deoxymiroestrol</a>, <a href="/wiki/Miroestrol" title="Miroestrol">miroestrol</a>)</li> <li><a href="/wiki/Stilbenoid" title="Stilbenoid">Stilbenoids</a> (e.g., <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, <a href="/wiki/Rhaponticin" title="Rhaponticin">rhaponticin</a>)</li> <li><a href="/wiki/Synthetic_xenoestrogen" class="mw-redirect" title="Synthetic xenoestrogen">Synthetic xenoestrogens</a> (e.g., <a href="/wiki/Alkylphenol" title="Alkylphenol">alkylphenols</a>, <a href="/wiki/Bisphenol" title="Bisphenol">bisphenols</a> (e.g., <a href="/wiki/Bisphenol_A" title="Bisphenol A">BPA</a>, <a href="/wiki/Bisphenol_F" title="Bisphenol F">BPF</a>, <a href="/wiki/Bisphenol_S" title="Bisphenol S">BPS</a>), <a href="/wiki/Dichlorodiphenyltrichloroethane" class="mw-redirect" title="Dichlorodiphenyltrichloroethane">DDT</a>, <a href="/wiki/Paraben" title="Paraben">parabens</a>, <a href="/wiki/Polybrominated_biphenyl" title="Polybrominated biphenyl">PBBs</a>, <a href="/wiki/4-hydroxybenzoic_acid" class="mw-redirect" title="4-hydroxybenzoic acid">PHBA</a>, <a href="/wiki/Phthalate" class="mw-redirect" title="Phthalate">phthalates</a>, <a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a>)</li> <li>Others (e.g., <a href="/wiki/Agnuside" title="Agnuside">agnuside</a>, <a href="/w/index.php?title=Rotundifuran&action=edit&redlink=1" class="new" title="Rotundifuran (page does not exist)">rotundifuran</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Mixed (<a href="/wiki/Selective_estrogen_receptor_modulators" class="mw-redirect" title="Selective estrogen receptor modulators"><abbr title="Selective estrogen receptor modulators">SERMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective estrogen receptor modulators)</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Phenylbenzofuran" title="2-Phenylbenzofuran">2-Phenylbenzofuran</a></li> <li><a href="/w/index.php?title=2-Phenylbenzothiophene&action=edit&redlink=1" class="new" title="2-Phenylbenzothiophene (page does not exist)">2-Phenylbenzothiophene</a></li> <li><a href="/wiki/4%27-Hydroxynorendoxifen" title="4'-Hydroxynorendoxifen">4'-Hydroxynorendoxifen</a></li> <li><a href="/wiki/27-Hydroxycholesterol" title="27-Hydroxycholesterol">27-Hydroxycholesterol</a></li> <li><a href="/wiki/Acefluranol" title="Acefluranol">Acefluranol</a></li> <li><a href="/wiki/Acolbifene" title="Acolbifene">Acolbifene</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene</a></li> <li><a href="/wiki/Anordiol" title="Anordiol">Anordiol</a></li> <li><a href="/wiki/Anordrin" title="Anordrin">Anordrin</a></li> <li><a href="/wiki/Arzoxifene" title="Arzoxifene">Arzoxifene</a></li> <li><a href="/wiki/Bazedoxifene" title="Bazedoxifene">Bazedoxifene</a></li> <li><a href="/wiki/Brilanestrant" title="Brilanestrant">Brilanestrant</a></li> <li><a href="/wiki/Broparestrol" title="Broparestrol">Broparestrol</a></li> <li><a href="/wiki/Camizestrant" title="Camizestrant">Camizestrant</a></li> <li><a href="/wiki/Chlorotrianisene" title="Chlorotrianisene">Chlorotrianisene</a></li> <li><a href="/wiki/Clomifene" title="Clomifene">Clomifene</a></li> <li><a href="/wiki/Clomifenoxide" title="Clomifenoxide">Clomifenoxide</a></li> <li><a href="/w/index.php?title=CN-55945-27&action=edit&redlink=1" class="new" title="CN-55945-27 (page does not exist)">CN-55945-27</a></li> <li><a href="/wiki/Cyclofenil" title="Cyclofenil">Cyclofenil</a></li> <li><a href="/w/index.php?title=D-15413&action=edit&redlink=1" class="new" title="D-15413 (page does not exist)">D-15413</a></li> <li><a href="/wiki/Desmethylchlorotrianisene" title="Desmethylchlorotrianisene">Desmethylchlorotrianisene</a></li> <li><a href="/wiki/Droloxifene" title="Droloxifene">Droloxifene</a></li> <li><a href="/wiki/Enclomifene" title="Enclomifene">Enclomifene</a></li> <li><a href="/wiki/Endoxifen" title="Endoxifen">Endoxifen</a></li> <li><a href="/wiki/Etacstil" title="Etacstil">Etacstil (GW-5638, DPC-974)</a></li> <li><a href="/wiki/Ethamoxytriphetol" title="Ethamoxytriphetol">Ethamoxytriphetol (MER-25)</a></li> <li><a href="/wiki/Femarelle" title="Femarelle">Femarelle</a></li> <li><a href="/wiki/Fispemifene" title="Fispemifene">Fispemifene</a></li> <li><a href="/w/index.php?title=GW-7604&action=edit&redlink=1" class="new" title="GW-7604 (page does not exist)">GW-7604</a></li> <li><a href="/wiki/ICI-55548" class="mw-redirect" title="ICI-55548">ICI-55548</a></li> <li><a href="/wiki/Idoxifene" title="Idoxifene">Idoxifene</a></li> <li><a href="/wiki/Lasofoxifene" title="Lasofoxifene">Lasofoxifene</a></li> <li><a href="/wiki/Levormeloxifene" title="Levormeloxifene">Levormeloxifene</a></li> <li><a href="/wiki/LN-1643" class="mw-redirect" title="LN-1643">LN-1643</a></li> <li><a href="/wiki/LN-2299" class="mw-redirect" title="LN-2299">LN-2299</a></li> <li><a href="/w/index.php?title=LY-117018&action=edit&redlink=1" class="new" title="LY-117018 (page does not exist)">LY-117018</a></li> <li><a href="/wiki/Menerba" title="Menerba">Menerba</a></li> <li><a href="/wiki/Miproxifene" title="Miproxifene">Miproxifene</a></li> <li><a href="/wiki/Miproxifene_phosphate" title="Miproxifene phosphate">Miproxifene phosphate</a></li> <li><a href="/w/index.php?title=MRL-37&action=edit&redlink=1" class="new" title="MRL-37 (page does not exist)">MRL-37</a></li> <li><a href="/wiki/Nafoxidine" title="Nafoxidine">Nafoxidine</a></li> <li><a href="/wiki/Nitromifene" title="Nitromifene">Nitromifene</a></li> <li><a href="/wiki/NNC_45-0095" title="NNC 45-0095">NNC 45-0095</a></li> <li><a href="/w/index.php?title=NNC_45-0320&action=edit&redlink=1" class="new" title="NNC 45-0320 (page does not exist)">NNC 45-0320</a></li> <li><a href="/w/index.php?title=NNC_45-0781&action=edit&redlink=1" class="new" title="NNC 45-0781 (page does not exist)">NNC 45-0781</a></li> <li><a href="/w/index.php?title=NNC_45-1506&action=edit&redlink=1" class="new" title="NNC 45-1506 (page does not exist)">NNC 45-1506</a></li> <li><a href="/wiki/Ormeloxifene" title="Ormeloxifene">Ormeloxifene</a></li> <li><a href="/wiki/Ospemifene" title="Ospemifene">Ospemifene</a></li> <li><a href="/wiki/Panomifene" title="Panomifene">Panomifene</a></li> <li><a href="/wiki/Pipendoxifene" title="Pipendoxifene">Pipendoxifene</a></li> <li><a href="/w/index.php?title=Promensil&action=edit&redlink=1" class="new" title="Promensil (page does not exist)">Promensil</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Rimostil" title="Rimostil">Rimostil (P-081)</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/w/index.php?title=SS1010&action=edit&redlink=1" class="new" title="SS1010 (page does not exist)">SS1010</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/Toremifene" title="Toremifene">Toremifene</a></li> <li><a href="/wiki/Trioxifene" title="Trioxifene">Trioxifene</a></li> <li><a href="/w/index.php?title=TZE-5323&action=edit&redlink=1" class="new" title="TZE-5323 (page does not exist)">TZE-5323</a></li> <li><a href="/w/index.php?title=U-11555A&action=edit&redlink=1" class="new" title="U-11555A (page does not exist)">U-11555A</a></li> <li><a href="/w/index.php?title=U-11634&action=edit&redlink=1" class="new" title="U-11634 (page does not exist)">U-11634</a></li> <li><a href="/w/index.php?title=Y-134&action=edit&redlink=1" class="new" title="Y-134 (page does not exist)">Y-134</a></li> <li><a href="/wiki/Zindoxifene" title="Zindoxifene">Zindoxifene</a></li> <li><a href="/wiki/Zuclomifene" title="Zuclomifene">Zuclomifene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/(R,R)-Tetrahydrochrysene" title="(R,R)-Tetrahydrochrysene">(R,R)-THC</a></li> <li><a href="/wiki/7%CE%B2-Hydroxy-DHEA" title="7β-Hydroxy-DHEA">7β-Hydroxy-DHEA</a></li> <li><a href="/w/index.php?title=Chloroindazole&action=edit&redlink=1" class="new" title="Chloroindazole (page does not exist)">Chloroindazole</a></li> <li><a href="/wiki/Cytestrol_acetate" title="Cytestrol acetate">Cytestrol acetate</a></li> <li><a href="/w/index.php?title=EM-800&action=edit&redlink=1" class="new" title="EM-800 (page does not exist)">EM-800 (SCH-57050)</a></li> <li><a href="/wiki/Epitiostanol" title="Epitiostanol">Epitiostanol</a></li> <li><a href="/w/index.php?title=ERA-90&action=edit&redlink=1" class="new" title="ERA-90 (page does not exist)">ERA-90</a></li> <li><a href="/w/index.php?title=ERB-88&action=edit&redlink=1" class="new" title="ERB-88 (page does not exist)">ERB-88</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/wiki/Glyceollin" title="Glyceollin">Glyceollins</a> (<a href="/wiki/Glyceollin_I" title="Glyceollin I">I</a>, <a href="/w/index.php?title=Glyceollin_II&action=edit&redlink=1" class="new" title="Glyceollin II (page does not exist)">II</a>, <a href="/wiki/Glyceollin_III" title="Glyceollin III">III</a>, <a href="/w/index.php?title=Glyceollin_IV&action=edit&redlink=1" class="new" title="Glyceollin IV (page does not exist)">IV</a>)</li> <li><a href="/wiki/ICI-164384" title="ICI-164384">ICI-164384</a></li> <li><a href="/w/index.php?title=MDL-101906&action=edit&redlink=1" class="new" title="MDL-101906 (page does not exist)">MDL-101906</a></li> <li><a href="/wiki/Mepitiostane" title="Mepitiostane">Mepitiostane</a></li> <li><a href="/wiki/Methylepitiostanol" title="Methylepitiostanol">Methylepitiostanol</a></li> <li><a href="/wiki/Methylpiperidinopyrazole" title="Methylpiperidinopyrazole">Methylpiperidinopyrazole</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li> <li><a href="/w/index.php?title=Oxabicycloheptene_sulfonate&action=edit&redlink=1" class="new" title="Oxabicycloheptene sulfonate (page does not exist)">Oxabicycloheptene sulfonate</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/PHTPP" title="PHTPP">PHTPP</a></li> <li><a href="/wiki/Prochloraz" title="Prochloraz">Prochloraz</a></li> <li><a href="/w/index.php?title=RU-39411&action=edit&redlink=1" class="new" title="RU-39411 (page does not exist)">RU-39411</a></li> <li><a href="/w/index.php?title=RU-58668&action=edit&redlink=1" class="new" title="RU-58668 (page does not exist)">RU-58668</a></li> <li><a href="/w/index.php?title=SS1020&action=edit&redlink=1" class="new" title="SS1020 (page does not exist)">SS1020</a></li> <li><a href="/wiki/TAS-108" title="TAS-108">TAS-108 (SR-16234)</a></li> <li><a href="/wiki/ZB716" title="ZB716">ZB716</a></li> <li><a href="/w/index.php?title=ZK-164015&action=edit&redlink=1" class="new" title="ZK-164015 (page does not exist)">ZK-164015</a></li> <li><a href="/w/index.php?title=ZK-191703&action=edit&redlink=1" class="new" title="ZK-191703 (page does not exist)">ZK-191703</a></li></ul> <ul><li>Coregulator-binding modulators: <a href="/wiki/ERX-11" title="ERX-11">ERX-11</a></li></ul> <ul><li>Noncompetitive inhibitors: <a href="/wiki/Trilostane" title="Trilostane">Trilostane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/G_protein-coupled_estrogen_receptor" class="mw-redirect" title="G protein-coupled estrogen receptor"><abbr title="G protein-coupled estrogen receptor">GPER</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip G protein-coupled estrogen receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Agonists</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/7%CE%B2-Hydroxyepiandrosterone" title="7β-Hydroxyepiandrosterone">7β-Hydroxyepiandrosterone</a></li> <li><a href="/wiki/Afimoxifene" title="Afimoxifene">Afimoxifene (4-hydroxytamoxifen)</a></li> <li><a href="/wiki/Aldosterone" title="Aldosterone">Aldosterone</a></li> <li><a href="/wiki/Atrazine" title="Atrazine">Atrazine</a></li> <li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/DDT" title="DDT">DDT</a> (<a href="/wiki/P,p%27-DDT" class="mw-redirect" title="P,p'-DDT">p,p'-DDT</a>, <a href="/w/index.php?title=O%27,p%27-DDE&action=edit&redlink=1" class="new" title="O',p'-DDE (page does not exist)">o',p'-DDE</a>)</li> <li><a href="/wiki/Diarylpropionitrile" title="Diarylpropionitrile">Diarylpropionitrile</a></li> <li><a href="/wiki/Equol" title="Equol">Equol</a></li> <li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant (ICI-182780)</a></li> <li><a href="/w/index.php?title=G-1_(drug)&action=edit&redlink=1" class="new" title="G-1 (drug) (page does not exist)">G-1</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GPER-L1&action=edit&redlink=1" class="new" title="GPER-L1 (page does not exist)">GPER-L1</a></li> <li><a href="/w/index.php?title=GPER-L2&action=edit&redlink=1" class="new" title="GPER-L2 (page does not exist)">GPER-L2</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Kepone" class="mw-redirect" title="Kepone">Kepone</a></li> <li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Polychlorinated_biphenyl" title="Polychlorinated biphenyl">PCBs</a> (<a href="/w/index.php?title=2,2%27,5%27-PCB-4-OH&action=edit&redlink=1" class="new" title="2,2',5'-PCB-4-OH (page does not exist)">2,2',5'-PCB-4-OH</a>)</li> <li><a href="/wiki/Propylpyrazoletriol" title="Propylpyrazoletriol">Propylpyrazoletriol</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">Quercetin</a></li> <li><a href="/wiki/Raloxifene" title="Raloxifene">Raloxifene</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=STX_(drug)&action=edit&redlink=1" class="new" title="STX (drug) (page does not exist)">STX</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Tectoridin" title="Tectoridin">Tectoridin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Antagonists</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/CCL18" title="CCL18">CCL18</a></li> <li><a href="/wiki/Estriol" title="Estriol">Estriol</a></li> <li><a href="/w/index.php?title=G-15_(drug)&action=edit&redlink=1" class="new" title="G-15 (drug) (page does not exist)">G-15</a></li> <li><a href="/w/index.php?title=G-36_(drug)&action=edit&redlink=1" class="new" title="G-36 (drug) (page does not exist)">G-36</a></li> <li><a href="/wiki/MIBE" title="MIBE">MIBE</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center">Unknown</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li> <li><a href="/wiki/Zearalenone" title="Zearalenone">Zearalenone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Estrogens_and_antiestrogens" title="Template:Estrogens and antiestrogens">Estrogens and antiestrogens</a></dd> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor modulators</a></dd> <dd><a href="/wiki/Template:Progesterone_receptor_modulators" title="Template:Progesterone receptor modulators">Progesterone receptor modulators</a></dd> <dd><a href="/wiki/List_of_steroidal_estrogens" class="mw-redirect" title="List of steroidal estrogens">List of estrogens</a></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&useformat=desktop" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Estramustine_phosphate&oldid=1243345320">https://en.wikipedia.org/w/index.php?title=Estramustine_phosphate&oldid=1243345320</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div 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