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screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title">Nilutamide</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Nilutamide.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Nilutamide.svg/225px-Nilutamide.svg.png" decoding="async" width="225" height="167" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Nilutamide.svg/338px-Nilutamide.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ea/Nilutamide.svg/450px-Nilutamide.svg.png 2x" data-file-width="512" data-file-height="379" /></a></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Nilutamide_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Nilutamide_molecule_ball.png/225px-Nilutamide_molecule_ball.png" decoding="async" width="225" height="188" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Nilutamide_molecule_ball.png/338px-Nilutamide_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Nilutamide_molecule_ball.png/450px-Nilutamide_molecule_ball.png 2x" data-file-width="2000" data-file-height="1668" /></a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data">nye-LOO-tah-mide<a href="#cite_note-LiverTox-1">[1]</a> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Nilandron, Anandron</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">RU-23908</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/nilutamide.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/a697044.html">a697044</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a><a href="#cite_note-PerryDoll2012-2">[2]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Nonsteroidal_antiandrogen" title="Nonsteroidal antiandrogen">Nonsteroidal antiandrogen</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a href="/wiki/ATC_code_L02" title="ATC code L02">L02BB02</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L02BB02">WHO</a>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Boxed_warning" title="Boxed warning">WARNING</a><a href="#cite_note-FDA-AllBoxedWarnings-3">[3]</a></li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">Good<a href="#cite_note-PerryDoll2012-2">[2]</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">80–84%<a href="#cite_note-LemkeWilliams2012-4">[4]</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/CYP2C19" title="CYP2C19">CYP2C19</a>, <a href="/wiki/Flavin-containing_monooxygenase" title="Flavin-containing monooxygenase"><abbr title="flavin-containing monooxygenase">FMO</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 flavin-containing monooxygenase)<a href="#cite_note-PerryDoll2012-2">[2]</a><a href="#cite_note-LemkeWilliams2012-4">[4]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">At least 5, some active<a href="#cite_note-LemkeWilliams2012-4">[4]</a><a href="#cite_note-ChabnerLongo2010-5">[5]</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">Mean: 56 hours (~2 days)<a href="#cite_note-KolvenbagFurr2009-6">[6]</a> Range: 23–87 hours<a href="#cite_note-KolvenbagFurr2009-6">[6]</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Urine" title="Urine">Urine</a>: 62%<a href="#cite_note-PerryDoll2012-2">[2]</a><a href="#cite_note-LemkeWilliams2012-4">[4]</a> <a href="/wiki/Feces" title="Feces">Feces</a>: <10%<a href="#cite_note-PerryDoll2012-2">[2]</a><a href="#cite_note-LemkeWilliams2012-4">[4]</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione</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=63612-50-0">63612-50-0</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/4493">4493</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=2864">2864</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/DB00665">DB00665</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4337.html">4337</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/51G6I8B902">51G6I8B902</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/D00965">D00965</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:7573">CHEBI:7573</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1274">ChEMBL1274</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/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/DTXSID3034165">DTXSID3034165</a> <a href="https://www.wikidata.org/wiki/Q3877030#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/100.153.268">100.153.268</a> <a href="https://www.wikidata.org/wiki/Q3877030#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">C12H10F3N3O4</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">317.224 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=CC1%28C%28%3DO%29N%28C%28%3DO%29N1%29C2%3DCC%28%3DC%28C%3DC2%29%5BN%2B%5D%28%3DO%29%5BO-%5D%29C%28F%29%28F%29F%29C">Interactive image</a></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">149 °C (300 °F)</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CC1(C(=O)N(C(=O)N1)C2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20) <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:XWXYUMMDTVBTOU-UHFFFAOYSA-N <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style>  <a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=462261036&page2=Nilutamide">(verify)</a></td></tr></tbody></table> Nilutamide, sold under the brand names Nilandron and Anandron, is a <a href="/wiki/Nonsteroidal_antiandrogen" title="Nonsteroidal antiandrogen">nonsteroidal antiandrogen</a> (NSAA) which is used in the treatment of <a href="/wiki/Prostate_cancer" title="Prostate cancer">prostate cancer</a>.<a href="#cite_note-8">[8]</a><a href="#cite_note-Elks2014-9">[9]</a><a href="#cite_note-IndexNominum2000-10">[10]</a><a href="#cite_note-MortonHall2012-11">[11]</a><a href="#cite_note-Drugs.com-12">[12]</a><a href="#cite_note-DenisGriffiths1999-13">[13]</a> It has also been studied as a component of <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">feminizing hormone therapy</a> for <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a> and to treat <a href="/wiki/Acne" title="Acne">acne</a> and <a href="/wiki/Seborrhea" class="mw-redirect" title="Seborrhea">seborrhea</a> in women.<a href="#cite_note-Denis2012a-14">[14]</a><a href="#cite_note-KreukelsSteensma2013-15">[15]</a><a href="#cite_note-pmid2744186-16">[16]</a><a href="#cite_note-pmid2462132-17">[17]</a> It is taken <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>.<a href="#cite_note-LemkeWilliams2012-4">[4]</a> <a href="/wiki/Side_effect" title="Side effect">Side effects</a> in men include <a href="/wiki/Breast_tenderness" class="mw-redirect" title="Breast tenderness">breast tenderness</a> and <a href="/wiki/Gynecomastia" title="Gynecomastia">enlargement</a>, <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a>, <a href="/wiki/Sexual_dysfunction" title="Sexual dysfunction">sexual dysfunction</a>, and <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a>.<a href="#cite_note-pmid8997470-18">[18]</a><a href="#cite_note-Dart2004-19">[19]</a><a href="#cite_note-MDMD2008-20">[20]</a><a href="#cite_note-Lehne2013-21">[21]</a> <a href="/wiki/Nausea" title="Nausea">Nausea</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, <a href="/wiki/Visual_disturbance" class="mw-redirect" title="Visual disturbance">visual disturbances</a>, <a href="/wiki/Alcohol_intolerance" title="Alcohol intolerance">alcohol intolerance</a>, <a href="/wiki/Elevated_liver_enzymes" class="mw-redirect" title="Elevated liver enzymes">elevated liver enzymes</a>, and <a href="/wiki/Interstitial_pneumonitis" class="mw-redirect" title="Interstitial pneumonitis">lung disease</a> can occur in both sexes.<a href="#cite_note-Lehne2013-21">[21]</a><a href="#cite_note-Becker2001-22">[22]</a><a href="#cite_note-Dart2004-19">[19]</a><a href="#cite_note-WeinKavoussi2011-23">[23]</a><a href="#cite_note-Jafri2014-24">[24]</a><a href="#cite_note-BoarderNewby2010-25">[25]</a> Rarely, nilutamide can cause <a href="/wiki/Respiratory_failure" title="Respiratory failure">respiratory failure</a> and <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">liver damage</a>.<a href="#cite_note-pmid8997470-18">[18]</a><a href="#cite_note-Lehne2013-21">[21]</a> These unfavorable side effects, along with a number of associated cases of death, have limited the use of nilutamide.<a href="#cite_note-DenisGriffiths1999-13">[13]</a><a href="#cite_note-DeVitaLawrence2016-26">[26]</a><a href="#cite_note-Chang2005-27">[27]</a> Nilutamide acts as a <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> of the <a href="/wiki/Androgen_receptor" title="Androgen receptor">androgen receptor</a> (AR), preventing the effects of <a href="/wiki/Androgen" title="Androgen">androgens</a> like <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> and <a href="/wiki/Dihydrotestosterone" title="Dihydrotestosterone">dihydrotestosterone</a> (DHT) in the body.<a href="#cite_note-SinghGauthier2000-28">[28]</a><a href="#cite_note-Denis2012a-14">[14]</a> Because most prostate cancer <a href="/wiki/Cell_(biology)" title="Cell (biology)">cells</a> rely on these <a href="/wiki/Hormone" title="Hormone">hormones</a> for <a href="/wiki/Cell_growth" title="Cell growth">growth</a> and <a href="/wiki/Cell_survival" class="mw-redirect" title="Cell survival">survival</a>, nilutamide can slow the progression of prostate cancer and extend life in men with the disease.<a href="#cite_note-Denis2012a-14">[14]</a> Nilutamide was discovered in 1977 and was first introduced for medical use in 1987.<a href="#cite_note-Elks2014-9">[9]</a><a href="#cite_note-LabrieLagacé1978-29">[29]</a><a href="#cite_note-pmid385986-30">[30]</a><a href="#cite_note-KolvenbagFurr2009-6">[6]</a> It became available in the United States in 1996.<a href="#cite_note-Pavlik2012-31">[31]</a><a href="#cite_note-BohlGao2005-32">[32]</a><a href="#cite_note-AdisInsight-33">[33]</a> The drug has largely been replaced by newer and improved NSAAs, namely <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a> and <a href="/wiki/Enzalutamide" title="Enzalutamide">enzalutamide</a>, due to their better <a href="/wiki/Efficacy" title="Efficacy">efficacy</a>, <a href="/wiki/Drug_tolerability" class="mw-redirect" title="Drug tolerability">tolerability</a>, and <a href="/wiki/Drug_safety" class="mw-redirect" title="Drug safety">safety</a>, and is now rarely used.<a href="#cite_note-Gulley2011-34">[34]</a> It is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<a href="#cite_note-WHO22nd-35">[35]</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=Nilutamide&action=edit&section=1" title="Edit section: Medical uses">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Prostate_cancer">Prostate cancer</h3>[<a href="/w/index.php?title=Nilutamide&action=edit&section=2" title="Edit section: Prostate cancer">edit</a>]</div> Nilutamide is used in prostate cancer in combination with a <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone">gonadotropin-releasing hormone</a> (GnRH) <a href="/wiki/Gonadotropin-releasing_hormone_analogue" class="mw-redirect" title="Gonadotropin-releasing hormone analogue">analogue</a> at a dosage of 300 mg/day (150 mg twice daily) for the first 4 weeks of treatment, and 150 mg/day thereafter.<a href="#cite_note-Chang2005-27">[27]</a><a href="#cite_note-Upfal2006-36">[36]</a> It is not indicated as a <a href="/wiki/Monotherapy" class="mw-redirect" title="Monotherapy">monotherapy</a> in prostate cancer.<a href="#cite_note-Chang2005-27">[27]</a> Only one small non-comparative study has assessed nilutamide as a monotherapy in prostate cancer.<a href="#cite_note-pmid12603397-37">[37]</a> Nilutamide has been used to prevent the effects of the <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> flare at the start of GnRH agonist therapy in men with prostate cancer.<a href="#cite_note-pmid16986003-38">[38]</a><a href="#cite_note-pmid8481213-39">[39]</a><a href="#cite_note-pmid2503723-40">[40]</a> <div class="mw-heading mw-heading3"><h3 id="Transgender_hormone_therapy">Transgender hormone therapy</h3>[<a href="/w/index.php?title=Nilutamide&action=edit&section=3" title="Edit section: Transgender hormone therapy">edit</a>]</div> Nilutamide has been studied for use as a component of <a href="/wiki/Feminizing_hormone_therapy" title="Feminizing hormone therapy">feminizing hormone therapy</a> for <a href="/wiki/Transgender_women" class="mw-redirect" title="Transgender women">transgender women</a>.<a href="#cite_note-Denis2012a-14">[14]</a><a href="#cite_note-KreukelsSteensma2013-15">[15]</a> It has been assessed in at least five small <a href="/wiki/Clinical_trial" title="Clinical trial">clinical studies</a> for this purpose in treatment-naive subjects.<a href="#cite_note-KreukelsSteensma2013-15">[15]</a><a href="#cite_note-AsschemanGooren1989-41">[41]</a><a href="#cite_note-Raode_Voogt1988-42">[42]</a><a href="#cite_note-van_KemenadeCohen-Kettenis1989-43">[43]</a><a href="#cite_note-GoorenSpinder1987-44">[44]</a><a href="#cite_note-De_VoogtRao1987-45">[45]</a> In these studies, nilutamide monotherapy at a dosage of 300 mg/day, induced observable signs of clinical <a href="/wiki/Feminization_(biology)" title="Feminization (biology)">feminization</a> in young transgender women (age range 19–33 years) within 8 weeks,<a href="#cite_note-Raode_Voogt1988-42">[42]</a> including <a href="/wiki/Breast_development" title="Breast development">breast development</a>, decreased <a href="/wiki/Body_hair" title="Body hair">body hair</a> (though not <a href="/wiki/Facial_hair" title="Facial hair">facial hair</a>),<a href="#cite_note-AsschemanGooren1989-41">[41]</a> decreased <a href="/wiki/Morning_erection" class="mw-redirect" title="Morning erection">morning erections</a> and <a href="/wiki/Sex_drive" class="mw-redirect" title="Sex drive">sex drive</a>,<a href="#cite_note-van_KemenadeCohen-Kettenis1989-43">[43]</a> and positive psychological and emotional changes.<a href="#cite_note-van_KemenadeCohen-Kettenis1989-43">[43]</a><a href="#cite_note-Cohen-KettenisGooren1993-46">[46]</a> Signs of breast development occurred in all subjects within 6 weeks and were associated with increased <a href="/wiki/Nipple_sensitivity" class="mw-redirect" title="Nipple sensitivity">nipple sensitivity</a>,<a href="#cite_note-De_VoogtRao1987-45">[45]</a><a href="#cite_note-Raode_Voogt1988-42">[42]</a><a href="#cite_note-van_KemenadeCohen-Kettenis1989-43">[43]</a> and along with decreased hair growth, were the earliest sign of feminization.<a href="#cite_note-Raode_Voogt1988-42">[42]</a> Nilutamide did not change the size of the <a href="/wiki/Prostate_gland" class="mw-redirect" title="Prostate gland">prostate gland</a> (which is the same as with high-dosage <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a> and <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a> treatment for as long as 18 months), but was found to alter its <a href="/wiki/Histology" title="Histology">histology</a>, including increased <a href="/wiki/Stromal_tissue" class="mw-redirect" title="Stromal tissue">stromal tissue</a> with a significant reduction in <a href="/wiki/Acinus" title="Acinus">acini</a> and atrophic <a href="/wiki/Epithelial_cell" class="mw-redirect" title="Epithelial cell">epithelial cells</a>, indicating glandular <a href="/wiki/Atrophy" title="Atrophy">atrophy</a>.<a href="#cite_note-GoorenSpinder1987-44">[44]</a><a href="#cite_note-De_VoogtRao1987-45">[45]</a><a href="#cite_note-AdisInternational1993-47">[47]</a> In addition, readily apparent histological changes were observed in the <a href="/wiki/Testicle" title="Testicle">testes</a>, including a reduction in <a href="/wiki/Seminiferous_tubule" title="Seminiferous tubule">tubular</a> and <a href="/wiki/Interstitial_cell" class="mw-redirect" title="Interstitial cell">interstitial cells</a>.<a href="#cite_note-GoorenSpinder1987-44">[44]</a> Nilutamide was found to more than double <a href="/wiki/Luteinizing_hormone" title="Luteinizing hormone">luteinizing hormone</a> (LH) and <a href="/wiki/Testosterone" title="Testosterone">testosterone</a> levels and to triple <a href="/wiki/Estradiol" title="Estradiol">estradiol</a> levels.<a href="#cite_note-AsschemanGooren1989-41">[41]</a><a href="#cite_note-Raode_Voogt1988-42">[42]</a><a href="#cite_note-GoorenSpinder1987-44">[44]</a> In contrast, <a href="/wiki/Follicle-stimulating_hormone" title="Follicle-stimulating hormone">follicle-stimulating hormone</a> levels remained unchanged.<a href="#cite_note-Raode_Voogt1988-42">[42]</a><a href="#cite_note-GoorenSpinder1987-44">[44]</a> A slight but significant increase in <a href="/wiki/Prolactin" title="Prolactin">prolactin</a> levels was observed, and levels of <a href="/wiki/Sex_hormone-binding_globulin" title="Sex hormone-binding globulin">sex hormone-binding globulin</a> increased as well.<a href="#cite_note-Raode_Voogt1988-42">[42]</a><a href="#cite_note-GoorenSpinder1987-44">[44]</a> The addition of ethinylestradiol to nilutamide therapy after 8 weeks abolished the increase in LH, testosterone, and estradiol levels and dramatically suppressed testosterone levels, into the <a href="/wiki/Castration" title="Castration">castrate</a> range.<a href="#cite_note-AsschemanGooren1989-41">[41]</a><a href="#cite_note-Raode_Voogt1988-42">[42]</a> Both nilutamide alone and the combination of nilutamide and <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> were regarded as resulting in effective and favorable antiandrogen action and feminization in transgender women.<a href="#cite_note-AsschemanGooren1989-41">[41]</a><a href="#cite_note-Raode_Voogt1988-42">[42]</a> <div class="mw-heading mw-heading3"><h3 id="Skin_conditions">Skin conditions</h3>[<a href="/w/index.php?title=Nilutamide&action=edit&section=4" title="Edit section: Skin conditions">edit</a>]</div> Nilutamide has been assessed in the treatment of <a href="/wiki/Acne" title="Acne">acne</a> and <a href="/wiki/Seborrhea" class="mw-redirect" title="Seborrhea">seborrhea</a> in women in at least one small clinical study.<a href="#cite_note-pmid2744186-16">[16]</a><a href="#cite_note-pmid2462132-17">[17]</a> The dosage used was 200 mg/day, and in the study, "seborrhea and acne decreased markedly within the first month and practically disappeared after 2 months of [nilutamide] treatment."<a href="#cite_note-pmid2744186-16">[16]</a><a href="#cite_note-pmid2462132-17">[17]</a> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3>[<a href="/w/index.php?title=Nilutamide&action=edit&section=5" title="Edit section: Available forms">edit</a>]</div> Nilutamide is available in the form of 50 and 150 mg <a href="/wiki/Oral_administration" title="Oral administration">oral</a> <a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</a>.<a href="#cite_note-Meyers2018-48">[48]</a> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2>[<a href="/w/index.php?title=Nilutamide&action=edit&section=6" title="Edit section: Side effects">edit</a>]</div> General <a href="/wiki/Side_effect" title="Side effect">side effects</a> of NSAAs, including nilutamide, include <a href="/wiki/Gynecomastia" title="Gynecomastia">gynecomastia</a>, <a href="/wiki/Mastodynia" class="mw-redirect" title="Mastodynia">breast pain/tenderness</a>, <a href="/wiki/Hot_flash" title="Hot flash">hot flashes</a> (67%), <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>, <a href="/wiki/Fatigue_(medical)" class="mw-redirect" title="Fatigue (medical)">fatigue</a>, <a href="/wiki/Sexual_dysfunction" title="Sexual dysfunction">sexual dysfunction</a> (including loss of <a href="/wiki/Libido" title="Libido">libido</a> and <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a>), decreased <a href="/wiki/Muscle" title="Muscle">muscle</a> mass, and decreased <a href="/wiki/Bone" title="Bone">bone</a> mass with an associated increase in <a href="/wiki/Bone_fracture" title="Bone fracture">fractures</a>.<a href="#cite_note-Dart2004-19">[19]</a><a href="#cite_note-MDMD2008-20">[20]</a><a href="#cite_note-Lehne2013-21">[21]</a> Also, <a href="/wiki/Nausea" title="Nausea">nausea</a> (24–27%), <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, <a href="/wiki/Constipation" title="Constipation">constipation</a> (20%), and <a href="/wiki/Insomnia" title="Insomnia">insomnia</a> (16%) may occur with nilutamide.<a href="#cite_note-Lehne2013-21">[21]</a> Nilutamide monotherapy is known to eventually induce gynecomastia in 40 to 80% of men treated with it for prostate cancer, usually within 6 to 9 months of treatment initiation.<a href="#cite_note-Bautista-VidalBarnoiu2014-49">[49]</a><a href="#cite_note-DeepinderBraunstein2012-50">[50]</a><a href="#cite_note-MichalopoulosKeshtgar2012-51">[51]</a><a href="#cite_note-pmid16321765-52">[52]</a> Relative to other NSAAs, nilutamide has been uniquely associated with mild and reversible <a href="/wiki/Visual_disturbance" class="mw-redirect" title="Visual disturbance">visual disturbances</a> (31–58%) including <a href="/wiki/Delayed_ocular_adaptation_to_darkness" class="mw-redirect" title="Delayed ocular adaptation to darkness">delayed ocular adaptation to darkness</a> and impaired <a href="/wiki/Color_vision" title="Color vision">color vision</a>,<a href="#cite_note-Becker2001-22">[22]</a> a <a href="/wiki/Disulfiram" title="Disulfiram">disulfiram</a>-like<a href="#cite_note-Dart2004-19">[19]</a> <a href="/wiki/Drinking_alcohol" class="mw-redirect" title="Drinking alcohol">alcohol</a> <a href="/wiki/Drug_intolerance" title="Drug intolerance">intolerance</a> (19%), <a href="/wiki/Interstitial_pneumonitis" class="mw-redirect" title="Interstitial pneumonitis">interstitial pneumonitis</a> (0.77–2.4%)<a href="#cite_note-Gulley2011-34">[34]</a><a href="#cite_note-CamusIII2010-53">[53]</a><a href="#cite_note-Held-Warmkessel2006-54">[54]</a> (which can result in <a href="/wiki/Dyspnea" class="mw-redirect" title="Dyspnea">dyspnea</a> (1%) as a secondary effect and can progress to <a href="/wiki/Pulmonary_fibrosis" title="Pulmonary fibrosis">pulmonary fibrosis</a>),<a href="#cite_note-WeinKavoussi2011-23">[23]</a> and <a href="/wiki/Hepatitis" title="Hepatitis">hepatitis</a> (1%), and has a higher incidence of nausea and vomiting compared to other NSAAs.<a href="#cite_note-DenisGriffiths1999-13">[13]</a><a href="#cite_note-Chang2005-27">[27]</a><a href="#cite_note-Lehne2013-21">[21]</a><a href="#cite_note-RamonDenis2007-55">[55]</a> The incidence of interstitial pneumonitis with nilutamide has been found to be much higher in <a href="/wiki/Japanese_people" title="Japanese people">Japanese</a> patients (12.6%), warranting particular caution in <a href="/wiki/Asian_people" title="Asian people">Asian</a> individuals.<a href="#cite_note-Mahler1996-56">[56]</a><a href="#cite_note-Micromedex2003-57">[57]</a> There is a case report of simultaneous liver and lung toxicity in a nilutamide-treated patient.<a href="#cite_note-pmid1580304-58">[58]</a> There is also a risk of <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a> with nilutamide, though occurrence is very rare and the risk is significantly less than with flutamide.<a href="#cite_note-KolvenbagFurr2009-6">[6]</a><a href="#cite_note-Aronson2009-59">[59]</a> The incidence of abnormal <a href="/wiki/Liver_function_tests" title="Liver function tests">liver function tests</a> (e.g., <a href="/wiki/Elevated_transaminases" title="Elevated transaminases">elevated liver enzymes</a>) has been variously reported as 2 to 33% with nilutamide.<a href="#cite_note-pmid10388026-60">[60]</a><a href="#cite_note-LiverTox-1">[1]</a> For comparison, the risk of elevated liver enzymes has been reported as 4 to 62% in the case of <a href="/wiki/Flutamide" title="Flutamide">flutamide</a>.<a href="#cite_note-pmid10388026-60">[60]</a><a href="#cite_note-Jafri2014-24">[24]</a><a href="#cite_note-KolvenbagFurr2009-6">[6]</a> The risk of hepatotoxicity with nilutamide has been described as far less than with flutamide.<a href="#cite_note-LiverTox-1">[1]</a> <a href="/wiki/Fulminant_hepatic_failure" class="mw-redirect" title="Fulminant hepatic failure">Fulminant hepatic failure</a> has been reported for nilutamide, with fatal outcome.<a href="#cite_note-KolvenbagFurr2009-6">[6]</a><a href="#cite_note-Aronson2011-61">[61]</a><a href="#cite_note-pmid8977826-62">[62]</a><a href="#cite_note-MerwatKabbani2008-63">[63]</a> Between 1986 and 2003, the numbers of published cases of hepatotoxicity for antiandrogens totaled 46 for flutamide, 21 for <a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">cyproterone acetate</a>, 4 for nilutamide, and 1 for <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a>.<a href="#cite_note-ChitturiFarrell2013-64">[64]</a> Similarly to flutamide, nilutamide exhibits <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondrial</a> <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> in <a href="/wiki/Hepatocyte" title="Hepatocyte">hepatocytes</a> by inhibiting <a href="/wiki/Electron_transport_chain#Complex_I" title="Electron transport chain">respiratory complex I</a> (<a href="/wiki/NADH:ubiquinone_reductase_(H%2B-translocating)" class="mw-redirect" title="NADH:ubiquinone reductase (H+-translocating)">NADH ubiquinone oxidoreductase</a>) (though not <a href="/wiki/Electron_transport_chain#Mitochondrial_redox_carriers" title="Electron transport chain">respiratory complexes II, III, or IV</a>) in the <a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a>, resulting in reduced <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> and <a href="/wiki/Glutathione" title="Glutathione">glutathione</a> production and thus decreased hepatocyte survival.<a href="#cite_note-MerwatKabbani2008-63">[63]</a><a href="#cite_note-pmid8035313-65">[65]</a><a href="#cite_note-CoeJia2007-66">[66]</a> The <a href="/wiki/Nitro_compound" title="Nitro compound">nitro</a> <a href="/wiki/Functional_group" title="Functional group">group</a> of nilutamide has been theorized to be involved in both its hepatotoxicity and its <a href="/wiki/Pulmonary_toxicity" title="Pulmonary toxicity">pulmonary toxicity</a>.<a href="#cite_note-CoeJia2007-66">[66]</a><a href="#cite_note-BoelsterliHo2006-67">[67]</a> <table class="wikitable sortable 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:Side_effects_of_combined_androgen_blockade_with_nilutamide_and_surgical_castration" title="Template:Side effects of combined androgen blockade with nilutamide and surgical castration"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Side_effects_of_combined_androgen_blockade_with_nilutamide_and_surgical_castration" title="Template talk:Side effects of combined androgen blockade with nilutamide and surgical castration"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Side_effects_of_combined_androgen_blockade_with_nilutamide_and_surgical_castration" title="Special:EditPage/Template:Side effects of combined androgen blockade with nilutamide and surgical castration"><abbr title="Edit this template">e</abbr></a></li></ul></div> Side effects of combined androgen blockade with nilutamide and surgical castration </caption> <tbody><tr> <th>Class</th> <th><a href="/wiki/Side_effect" title="Side effect">Side effect</a></th> <th>Nilutamide 150 mg/day + <a href="/wiki/Orchiectomy" title="Orchiectomy">orchiectomy</a> (n = 225) (%)a,b</th> <th><a href="/wiki/Placebo" title="Placebo">Placebo</a> + <a href="/wiki/Orchiectomy" title="Orchiectomy">orchi- ectomy</a> (n = 232) (%)a,b </th></tr> <tr> <td><a href="/wiki/Cardiovascular_system" class="mw-redirect" title="Cardiovascular system">Cardiovascular system</a></td> <td><a href="/wiki/Hypertension" title="Hypertension">Hypertension</a></td> <td>5.3</td> <td>2.6 </td></tr> <tr> <td rowspan="2"><a href="/wiki/Human_digestive_system" title="Human digestive system">Digestive system</a></td> <td><a href="/wiki/Nausea" title="Nausea">Nausea</a></td> <td>9.8</td> <td>6.0 </td></tr> <tr> <td><a href="/wiki/Constipation" title="Constipation">Constipation</a></td> <td>7.1</td> <td>3.9 </td></tr> <tr> <td><a href="/wiki/Endocrine_system" title="Endocrine system">Endocrine system</a></td> <td><a href="/wiki/Hot_flash" title="Hot flash">Hot flashes</a></td> <td>28.4</td> <td>22.4 </td></tr> <tr> <td rowspan="2"><a href="/wiki/Metabolic_system" class="mw-redirect" title="Metabolic system">Metabolic</a> and <a href="/wiki/Nutritional_system" class="mw-redirect" title="Nutritional system">nutritional system</a></td> <td><a href="/wiki/Increased_aspartate_transaminase" class="mw-redirect" title="Increased aspartate transaminase">Increased aspartate transaminase</a></td> <td>8.0</td> <td>3.9 </td></tr> <tr> <td><a href="/wiki/Increased_alanine_transaminase" class="mw-redirect" title="Increased alanine transaminase">Increased alanine transaminase</a></td> <td>7.6</td> <td>4.3 </td></tr> <tr> <td><a href="/wiki/Nervous_system" title="Nervous system">Nervous system</a></td> <td><a href="/wiki/Dizziness" title="Dizziness">Dizziness</a></td> <td>7.1</td> <td>3.4 </td></tr> <tr> <td><a href="/wiki/Respiratory_system" title="Respiratory system">Respiratory system</a></td> <td><a href="/wiki/Dyspnea" class="mw-redirect" title="Dyspnea">Dyspnea</a></td> <td>6.2</td> <td>7.3 </td></tr> <tr> <td rowspan="2"><a href="/wiki/Special_senses" title="Special senses">Special senses</a></td> <td><a href="/wiki/Impaired_adaptation_to_darkness" class="mw-redirect" title="Impaired adaptation to darkness">Impaired adaptation to darkness</a></td> <td>12.9</td> <td>1.3 </td></tr> <tr> <td><a href="/wiki/Abnormal_vision" class="mw-redirect" title="Abnormal vision">Abnormal vision</a></td> <td>6.7</td> <td>1.7 </td></tr> <tr> <td><a href="/wiki/Urogenital_system" class="mw-redirect" title="Urogenital system">Urogenital system</a></td> <td><a href="/wiki/Urinary_tract_infection" title="Urinary tract infection">Urinary tract infection</a></td> <td>8.0</td> <td>9.1 </td></tr> <tr> <td colspan="2">Overall</td> <td>86</td> <td>81 </td></tr> <tr> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = <a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a> studies of <a href="/wiki/Combined_androgen_blockade" class="mw-redirect" title="Combined androgen blockade">combined androgen blockade</a> (nilutamide + <a href="/wiki/Orchiectomy" title="Orchiectomy">orchiectomy</a>) in men with <a href="/wiki/Advanced_prostate_cancer" class="mw-redirect" title="Advanced prostate cancer">advanced prostate cancer</a>. b = Incidence ≥5% regardless of <a href="/wiki/Causality" title="Causality">causality</a>. Sources: See template. </td></tr></tbody></table> <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:Side_effects_of_combined_androgen_blockade_with_nilutamide_and_a_GnRH_agonist" title="Template:Side effects of combined androgen blockade with nilutamide and a GnRH agonist"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Side_effects_of_combined_androgen_blockade_with_nilutamide_and_a_GnRH_agonist" title="Template talk:Side effects of combined androgen blockade with nilutamide and a GnRH agonist"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Side_effects_of_combined_androgen_blockade_with_nilutamide_and_a_GnRH_agonist" title="Special:EditPage/Template:Side effects of combined androgen blockade with nilutamide and a GnRH agonist"><abbr title="Edit this template">e</abbr></a></li></ul></div> Side effects of combined androgen blockade with nilutamide and a GnRH agonist </caption> <tbody><tr> <th>Class</th> <th><a href="/wiki/Side_effect" title="Side effect">Side effect</a></th> <th>Nilutamide 150 mg/day + <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a> (n = 209) (%)a,b</th> <th><a href="/wiki/Placebo" title="Placebo">Placebo</a> + <a href="/wiki/Leuprorelin" title="Leuprorelin">leupro- relin</a> (n = 202) (%)a,b </th></tr> <tr> <td rowspan="8"><a href="/wiki/Body_as_a_whole" class="mw-redirect" title="Body as a whole">Body as a whole</a></td> <td><a href="/wiki/Pain" title="Pain">Pain</a></td> <td>26.8</td> <td>27.7 </td></tr> <tr> <td><a href="/wiki/Headache" title="Headache">Headache</a></td> <td>13.9</td> <td>10.4 </td></tr> <tr> <td><a href="/wiki/Asthenia" class="mw-redirect" title="Asthenia">Asthenia</a></td> <td>19.1</td> <td>20.8 </td></tr> <tr> <td><a href="/wiki/Back_pain" title="Back pain">Back pain</a></td> <td>11.5</td> <td>16.8 </td></tr> <tr> <td><a href="/wiki/Abdominal_pain" title="Abdominal pain">Abdominal pain</a></td> <td>10.0</td> <td>5.4 </td></tr> <tr> <td><a href="/wiki/Chest_pain" title="Chest pain">Chest pain</a></td> <td>7.2</td> <td>4.5 </td></tr> <tr> <td><a href="/wiki/Flu_syndrome" class="mw-redirect" title="Flu syndrome">Flu syndrome</a></td> <td>7.2</td> <td>3.0 </td></tr> <tr> <td><a href="/wiki/Fever" title="Fever">Fever</a></td> <td>5.3</td> <td>6.4 </td></tr> <tr> <td><a href="/wiki/Cardiovascular_system" class="mw-redirect" title="Cardiovascular system">Cardiovascular system</a></td> <td><a href="/wiki/Hypertension" title="Hypertension">Hypertension</a></td> <td>9.1</td> <td>9.9 </td></tr> <tr> <td rowspan="5"><a href="/wiki/Human_digestive_system" title="Human digestive system">Digestive system</a></td> <td><a href="/wiki/Nausea" title="Nausea">Nausea</a></td> <td>23.9</td> <td>8.4 </td></tr> <tr> <td><a href="/wiki/Constipation" title="Constipation">Constipation</a></td> <td>19.6</td> <td>16.8 </td></tr> <tr> <td><a href="/wiki/Anorexia_(symptom)" title="Anorexia (symptom)">Anorexia</a></td> <td>11.0</td> <td>6.4 </td></tr> <tr> <td><a href="/wiki/Dyspepsia" class="mw-redirect" title="Dyspepsia">Dyspepsia</a></td> <td>6.7</td> <td>4.5 </td></tr> <tr> <td><a href="/wiki/Vomiting" title="Vomiting">Vomiting</a></td> <td>5.7</td> <td>4.0 </td></tr> <tr> <td rowspan="3"><a href="/wiki/Endocrine_system" title="Endocrine system">Endocrine system</a></td> <td><a href="/wiki/Hot_flash" title="Hot flash">Hot flashes</a></td> <td>66.5</td> <td>59.4 </td></tr> <tr> <td><a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">Erectile dysfunction</a></td> <td>11.0</td> <td>12.9 </td></tr> <tr> <td><a href="/wiki/Decreased_libido" class="mw-redirect" title="Decreased libido">Decreased libido</a></td> <td>11.0</td> <td>4.5 </td></tr> <tr> <td><a href="/wiki/Hemic_system" class="mw-redirect" title="Hemic system">Hemic</a> and <a href="/wiki/Lymphatic_system" title="Lymphatic system">lymphatic system</a></td> <td><a href="/wiki/Anemia" title="Anemia">Anemia</a></td> <td>7.2</td> <td>6.4 </td></tr> <tr> <td rowspan="3"><a href="/wiki/Metabolic_system" class="mw-redirect" title="Metabolic system">Metabolic</a> and <a href="/wiki/Nutritional_system" class="mw-redirect" title="Nutritional system">nutritional system</a></td> <td><a href="/wiki/Increased_aspartate_transaminase" class="mw-redirect" title="Increased aspartate transaminase">Increased aspartate transaminase</a></td> <td>12.9</td> <td>13.9 </td></tr> <tr> <td><a href="/wiki/Peripheral_edema" title="Peripheral edema">Peripheral edema</a></td> <td>12.4</td> <td>17.3 </td></tr> <tr> <td><a href="/wiki/Increased_alanine_transaminase" class="mw-redirect" title="Increased alanine transaminase">Increased alanine transaminase</a></td> <td>9.1</td> <td>8.9 </td></tr> <tr> <td><a href="/wiki/Musculoskeletal_system" class="mw-redirect" title="Musculoskeletal system">Musculoskeletal system</a></td> <td><a href="/wiki/Bone_pain" title="Bone pain">Bone pain</a></td> <td>6.2</td> <td>5.0 </td></tr> <tr> <td rowspan="4"><a href="/wiki/Nervous_system" title="Nervous system">Nervous system</a></td> <td><a href="/wiki/Insomnia" title="Insomnia">Insomnia</a></td> <td>16.3</td> <td>15.8 </td></tr> <tr> <td><a href="/wiki/Dizziness" title="Dizziness">Dizziness</a></td> <td>10.0</td> <td>11.4 </td></tr> <tr> <td><a href="/wiki/Depression_(mood)" title="Depression (mood)">Depression</a></td> <td>8.6</td> <td>7.4 </td></tr> <tr> <td><a href="/wiki/Hypesthesia" class="mw-redirect" title="Hypesthesia">Hypesthesia</a></td> <td>5.3</td> <td>2.0 </td></tr> <tr> <td rowspan="3"><a href="/wiki/Respiratory_system" title="Respiratory system">Respiratory system</a></td> <td><a href="/wiki/Dyspnea" class="mw-redirect" title="Dyspnea">Dyspnea</a></td> <td>10.5</td> <td>7.4 </td></tr> <tr> <td><a href="/wiki/Upper_respiratory_infection" class="mw-redirect" title="Upper respiratory infection">Upper respiratory infection</a></td> <td>8.1</td> <td>10.9 </td></tr> <tr> <td><a href="/wiki/Pneumonia" title="Pneumonia">Pneumonia</a></td> <td>5.3</td> <td>3.5 </td></tr> <tr> <td rowspan="4"><a href="/wiki/Skin" title="Skin">Skin</a> and <a href="/wiki/Appendage" title="Appendage">appendages</a></td> <td><a href="/wiki/Sweating" class="mw-redirect" title="Sweating">Sweating</a></td> <td>6.2</td> <td>3.0 </td></tr> <tr> <td><a href="/wiki/Decreased_body_hair" class="mw-redirect" title="Decreased body hair">Decreased body hair</a></td> <td>5.7</td> <td>0.5 </td></tr> <tr> <td><a href="/wiki/Dry_skin" class="mw-redirect" title="Dry skin">Dry skin</a></td> <td>5.3</td> <td>2.5 </td></tr> <tr> <td><a href="/wiki/Rash" title="Rash">Rash</a></td> <td>5.3</td> <td>4.0 </td></tr> <tr> <td rowspan="4"><a href="/wiki/Special_senses" title="Special senses">Special senses</a></td> <td><a href="/wiki/Impaired_adaptation_to_darkness" class="mw-redirect" title="Impaired adaptation to darkness">Impaired adaptation to darkness</a></td> <td>56.9</td> <td>5.4 </td></tr> <tr> <td><a href="/wiki/Chromatopsia" class="mw-redirect" title="Chromatopsia">Chromatopsia</a></td> <td>8.6</td> <td>0.0 </td></tr> <tr> <td><a href="/wiki/Impaired_adaptation_to_light" class="mw-redirect" title="Impaired adaptation to light">Impaired adaptation to light</a></td> <td>7.7</td> <td>1.0 </td></tr> <tr> <td><a href="/wiki/Abnormal_vision" class="mw-redirect" title="Abnormal vision">Abnormal vision</a></td> <td>6.2</td> <td>4.5 </td></tr> <tr> <td rowspan="6"><a href="/wiki/Urogenital_system" class="mw-redirect" title="Urogenital system">Urogenital system</a></td> <td><a href="/wiki/Testicular_atrophy" title="Testicular atrophy">Testicular atrophy</a></td> <td>16.3</td> <td>12.4 </td></tr> <tr> <td><a href="/wiki/Gynecomastia" title="Gynecomastia">Gynecomastia</a></td> <td>10.5</td> <td>11.9 </td></tr> <tr> <td><a href="/wiki/Urinary_tract_infection" title="Urinary tract infection">Urinary tract infection</a></td> <td>8.6</td> <td>21.3 </td></tr> <tr> <td><a href="/wiki/Hematuria" title="Hematuria">Hematuria</a></td> <td>8.1</td> <td>7.9 </td></tr> <tr> <td><a href="/wiki/Urinary_tract_disorder" class="mw-redirect" title="Urinary tract disorder">Urinary tract disorder</a></td> <td>7.2</td> <td>10.4 </td></tr> <tr> <td><a href="/wiki/Nocturia" title="Nocturia">Nocturia</a></td> <td>6.7</td> <td>6.4 </td></tr> <tr> <td colspan="2">Overall</td> <td>99.5</td> <td>98.5 </td></tr> <tr> <td colspan="4" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = <a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a> studies of <a href="/wiki/Combined_androgen_blockade" class="mw-redirect" title="Combined androgen blockade">combined androgen blockade</a> (nilutamide + <a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonist</a>) in men with <a href="/wiki/Advanced_prostate_cancer" class="mw-redirect" title="Advanced prostate cancer">advanced prostate cancer</a>. b = Incidence ≥5% regardless of <a href="/wiki/Causality" title="Causality">causality</a>. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2>[<a href="/w/index.php?title=Nilutamide&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=Nilutamide&action=edit&section=8" title="Edit section: Pharmacodynamics">edit</a>]</div> <div class="mw-heading mw-heading4"><h4 id="Antiandrogenic_activity">Antiandrogenic activity</h4>[<a href="/w/index.php?title=Nilutamide&action=edit&section=9" title="Edit section: Antiandrogenic activity">edit</a>]</div> <table class="wikitable floatright" style="width:100px; text-align:left; margin-left:auto; margin-right:auto; border:none;"> <caption><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Affinities_of_selected_androgen_receptor_ligands" title="Template:Affinities of selected androgen receptor ligands"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Affinities_of_selected_androgen_receptor_ligands" title="Template talk:Affinities of selected androgen receptor ligands"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Affinities_of_selected_androgen_receptor_ligands" title="Special:EditPage/Template:Affinities of selected androgen receptor ligands"><abbr title="Edit this template">e</abbr></a></li></ul></div> Affinities<a href="#cite_note-68">[a]</a><a href="#cite_note-pmid2788775-69">[68]</a> </caption> <tbody><tr> <th scope="col">Compound </th> <th scope="col"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="Relative binding affinity">RBA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Relative binding affinity<a href="#cite_note-70">[b]</a> </th></tr> <tr> <th scope="row"><a href="/wiki/Metribolone" title="Metribolone">Metribolone</a> </th> <td>100 </td></tr> <tr> <th scope="row"><a href="/wiki/Androstanolone" title="Androstanolone">Dihydrotestosterone</a> </th> <td>85 </td></tr> <tr> <th scope="row"><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a> </th> <td>7.8 </td></tr> <tr> <th scope="row"><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a> </th> <td>1.4 </td></tr> <tr> <th scope="row">Nilutamide </th> <td>0.9 </td></tr> <tr> <th scope="row"><a href="/wiki/Hydroxyflutamide" title="Hydroxyflutamide">Hydroxyflutamide</a> </th> <td>0.57 </td></tr> <tr> <th scope="row"><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a> </th> <td><0.0057 </td></tr> <tr class="sortbottom"> <td colspan="2" style="background-color:#FFFFFF; text-align: left; border:none;">Notes: <div style="font-size:85%;"><style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-lower-alpha"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-68"><a href="#cite_ref-68">^</a> At androgen receptors; measured in human prostate tissue. </li> <li id="cite_note-70"><a href="#cite_ref-70">^</a> Relative to <a href="/wiki/Metribolone" title="Metribolone">Metribolone</a>, which is by definition 100% </li> </ol></div></div></div> </td></tr></tbody></table> Nilutamide acts as a <a href="/wiki/Binding_selectivity" title="Binding selectivity">selective</a> <a href="/wiki/Competitive_antagonist" class="mw-redirect" title="Competitive antagonist">competitive</a> <a href="/wiki/Silent_antagonist" class="mw-redirect" title="Silent antagonist">silent antagonist</a> of the AR (<a href="/wiki/IC50" title="IC50">IC50</a> = 412 nM),<a href="#cite_note-SinghGauthier2000-28">[28]</a> which prevents androgens like testosterone and DHT from activating the receptor.<a href="#cite_note-Denis2012a-14">[14]</a> The affinity of nilutamide for the AR is about 1 to 4% of that of testosterone and is similar to that of <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a> and <a href="/wiki/2-hydroxyflutamide" class="mw-redirect" title="2-hydroxyflutamide">2-hydroxyflutamide</a>.<a href="#cite_note-Gaillard1996-71">[69]</a><a href="#cite_note-FiggChau2010-72">[70]</a><a href="#cite_note-BenniVemer1990-73">[71]</a> Similarly to 2-hydroxyflutamide, but unlike bicalutamide, nilutamide is able to weakly activate the AR at high concentrations.<a href="#cite_note-FiggChau2010-72">[70]</a> It does not inhibit <a href="/wiki/5%CE%B1-reductase" class="mw-redirect" title="5α-reductase">5α-reductase</a>.<a href="#cite_note-pmid3331376-74">[72]</a> Like other NSAAs such as flutamide and bicalutamide, nilutamide, without concomitant GnRH analogue therapy, increases serum androgen (by two-fold in the case of testosterone), <a href="/wiki/Estrogen" title="Estrogen">estrogen</a>, and <a href="/wiki/Prolactin" title="Prolactin">prolactin</a> levels due to inhibition of AR-mediated suppression of <a href="/wiki/Steroidogenesis" class="mw-redirect" title="Steroidogenesis">steroidogenesis</a> via <a href="/wiki/Negative_feedback" title="Negative feedback">negative feedback</a> on the <a href="/wiki/Hypothalamic%E2%80%93pituitary%E2%80%93gonadal_axis" title="Hypothalamic–pituitary–gonadal axis">hypothalamic–pituitary–gonadal axis</a>.<a href="#cite_note-Denis2012a-14">[14]</a> As such, though nilutamide is still effective as an antiandrogen as a monotherapy, it is given in combination with a GnRH analogue such as <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a> in prostate cancer to suppress androgen concentrations to castrate levels in order to attain <a href="/wiki/Maximum_androgen_blockade" title="Maximum androgen blockade">maximal androgen blockade</a> (MAB).<a href="#cite_note-Denis2012a-14">[14]</a> Like flutamide and bicalutamide, nilutamide is able to cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> and has <a href="/wiki/Central_nervous_system" title="Central nervous system">central</a> antiandrogen actions.<a href="#cite_note-pmid385986-30">[30]</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:Relative_affinities_of_first-generation_nonsteroidal_antiandrogens_for_the_androgen_receptor" title="Template:Relative affinities of first-generation nonsteroidal antiandrogens for the androgen receptor"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Relative_affinities_of_first-generation_nonsteroidal_antiandrogens_for_the_androgen_receptor" title="Template talk:Relative affinities of first-generation nonsteroidal antiandrogens for the androgen receptor"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Relative_affinities_of_first-generation_nonsteroidal_antiandrogens_for_the_androgen_receptor" title="Special:EditPage/Template:Relative affinities of first-generation nonsteroidal antiandrogens for the androgen receptor"><abbr title="Edit this template">e</abbr></a></li></ul></div> Relative affinities of first-generation nonsteroidal antiandrogens for the androgen receptor </caption> <tbody><tr> <th rowspan="2">Species</th> <th colspan="3"><a href="/wiki/Half_maximal_inhibitory_concentration" class="mw-redirect" title="Half maximal inhibitory concentration"><abbr title="Half maximal inhibitory concentration">IC50</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 inhibitory concentration (nM)</th> <th colspan="3"><a href="/wiki/Relative_binding_affinity" class="mw-redirect" title="Relative binding affinity"><abbr title="Relative binding affinity">RBA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Relative binding affinity (ratio) </th></tr> <tr> <th><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></th> <th><a href="/wiki/2-Hydroxyflutamide" class="mw-redirect" title="2-Hydroxyflutamide">2-Hydroxyflutamide</a></th> <th><a class="mw-selflink selflink">Nilutamide</a></th> <th><abbr title="Bicalutamide">Bica</abbr> / <abbr title="2-hydroxyflutamide">2-OH-flu</abbr></th> <th><abbr title="Bicalutamide">Bica</abbr> / <abbr title="nilutamide">nilu</abbr></th> <th>Ref </th></tr> <tr> <td>Rat</td> <td>190</td> <td>700</td> <td><abbr title="No data">ND</abbr></td> <td>4.0</td> <td><abbr title="No data">ND</abbr></td> <td><a href="#cite_note-pmid3625091-75">[73]</a> </td></tr> <tr> <td>Rat</td> <td>~400</td> <td>~900</td> <td>~900</td> <td>2.3</td> <td>2.3</td> <td><a href="#cite_note-pmid8136296Receptor-76">[74]</a> </td></tr> <tr> <td>Rat</td> <td><abbr title="No data">ND</abbr></td> <td><abbr title="No data">ND</abbr></td> <td><abbr title="No data">ND</abbr></td> <td>3.3</td> <td><abbr title="No data">ND</abbr></td> <td><a href="#cite_note-pmid2615358-77">[75]</a> </td></tr> <tr> <td>Rata</td> <td>3595</td> <td>4565</td> <td>18620</td> <td>1.3</td> <td>5.2</td> <td><a href="#cite_note-LuoMartel1996-78">[76]</a> </td></tr> <tr> <td>Human</td> <td>~300</td> <td>~700</td> <td>~500</td> <td>2.5</td> <td>1.6</td> <td><a href="#cite_note-Ayub_1989-79">[77]</a> </td></tr> <tr> <td>Human</td> <td>~100</td> <td>~300</td> <td><abbr title="No data">ND</abbr></td> <td>~3.0</td> <td><abbr title="No data">ND</abbr></td> <td><a href="#cite_note-pmid8693644-80">[78]</a> </td></tr> <tr> <td>Humana</td> <td>2490</td> <td>2345</td> <td>5300</td> <td>1.0</td> <td>2.1</td> <td><a href="#cite_note-LuoMartel1996-78">[76]</a> </td></tr> <tr class="sortbottom"> <td colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;">Footnotes: a = Controversial data. Sources: See template. </td></tr></tbody></table> <div class="mw-heading mw-heading4"><h4 id="Cytochrome_P450_inhibition">Cytochrome P450 inhibition</h4>[<a href="/w/index.php?title=Nilutamide&action=edit&section=10" title="Edit section: Cytochrome P450 inhibition">edit</a>]</div> Nilutamide is known to inhibit several <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> enzymes, including <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a>, <a href="/wiki/CYP2C9" title="CYP2C9">CYP2C9</a>, and <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>, and can result in increased levels of medications that are <a href="/wiki/Metabolism" title="Metabolism">metabolized</a> by these <a href="/wiki/Enzyme" title="Enzyme">enzymes</a>.<a href="#cite_note-FerrandoLevenson2010-81">[79]</a> It has also been found to inhibit the enzyme <a href="/wiki/CYP17A1" title="CYP17A1">CYP17A1</a> (17α-hydroxylase/17,20-lyase) in vitro and thus the <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a> of androgens.<a href="#cite_note-HarrisColeman1993-82">[80]</a><a href="#cite_note-pmid2956461-83">[81]</a> However, nilutamide monotherapy significantly increases testosterone levels in vivo, so the clinical significance of this finding is uncertain.<a href="#cite_note-HarrisColeman1993-82">[80]</a><a href="#cite_note-pmid2956461-83">[81]</a> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3>[<a href="/w/index.php?title=Nilutamide&action=edit&section=11" title="Edit section: Pharmacokinetics">edit</a>]</div> Nilutamide has an <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of 23 to 87 hours, with a mean of 56 hours,<a href="#cite_note-KolvenbagFurr2009-6">[6]</a> or about two days; this allows for once-daily administration.<a href="#cite_note-DenisGriffiths1999-13">[13]</a> <a href="/wiki/Steady_state" title="Steady state">Steady state</a> (plateau) levels of the drug are attained after two weeks of administration with a dosage of 150 mg twice daily (300 mg/day total).<a href="#cite_note-Denis2012b-84">[82]</a> It is <a href="/wiki/Metabolized" class="mw-redirect" title="Metabolized">metabolized</a> by <a href="/wiki/CYP2C19" title="CYP2C19">CYP2C19</a>, with at least five <a href="/wiki/Metabolite" title="Metabolite">metabolites</a>.<a href="#cite_note-ChabnerLongo2010-5">[5]</a> Virtually all of the antiandrogenic activity of nilutamide comes from the parent drug (as opposed to metabolites).<a href="#cite_note-MahlerVerhelst1998-85">[83]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Nilutamide&action=edit&section=12" title="Edit section: Chemistry">edit</a>]</div> Nilutamide is structurally related to the <a href="/wiki/Nonsteroidal_antiandrogen#First-generation" title="Nonsteroidal antiandrogen">first-generation</a> NSAAs <a href="/wiki/Flutamide" title="Flutamide">flutamide</a> and <a href="/wiki/Bicalutamide" title="Bicalutamide">bicalutamide</a> as well as to the <a href="/wiki/Nonsteroidal_antiandrogen#Second-generation" title="Nonsteroidal antiandrogen">second-generation</a> NSAAs <a href="/wiki/Enzalutamide" title="Enzalutamide">enzalutamide</a> and <a href="/wiki/Apalutamide" title="Apalutamide">apalutamide</a>. <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Nilutamide&action=edit&section=13" title="Edit section: History">edit</a>]</div> Nilutamide was developed by <a href="/wiki/Roussel_Uclaf" title="Roussel Uclaf">Roussel</a> and was first described in 1977.<a href="#cite_note-Elks2014-9">[9]</a><a href="#cite_note-LabrieLagacé1978-29">[29]</a><a href="#cite_note-pmid385986-30">[30]</a> It was first introduced for medical use in 1987 in <a href="/wiki/France" title="France">France</a><a href="#cite_note-KolvenbagFurr2009-6">[6]</a><a href="#cite_note-FischerKlein2018-86">[84]</a> and was the second NSAA to be marketed, with flutamide preceding it and bicalutamide following it in 1995.<a href="#cite_note-DenisGriffiths1999-13">[13]</a><a href="#cite_note-87">[85]</a> It was not introduced until 1996 in the <a href="/wiki/United_States" title="United States">United States</a>.<a href="#cite_note-Pavlik2012-31">[31]</a><a href="#cite_note-BohlGao2005-32">[32]</a><a href="#cite_note-AdisInsight-33">[33]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Nilutamide&action=edit&section=14" 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=Nilutamide&action=edit&section=15" title="Edit section: Generic names">edit</a>]</div> Nilutamide is the <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> of the drug and its <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name"><abbr title="International Nonproprietary Name">INN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip International Nonproprietary Name, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name"><abbr title="United States Adopted Name">USAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip United States Adopted Name, <a href="/wiki/British_Approved_Name" title="British Approved Name"><abbr title="British Approved Name">BAN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip British Approved Name, and <a href="/wiki/D%C3%A9nomination_Commune_Fran%C3%A7aise" title="Dénomination Commune Française"><abbr title="Dénomination Commune Française">DCF</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dénomination Commune Française.<a href="#cite_note-Elks2014-9">[9]</a><a href="#cite_note-IndexNominum2000-10">[10]</a><a href="#cite_note-MortonHall2012-11">[11]</a><a href="#cite_note-Drugs.com-12">[12]</a> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3>[<a href="/w/index.php?title=Nilutamide&action=edit&section=16" title="Edit section: Brand names">edit</a>]</div> Nilutamide is marketed under the brand name Nilandron in the <a href="/wiki/United_States" title="United States">United States</a> and under the brand name Anandron elsewhere in the world such as in <a href="/wiki/Australia" title="Australia">Australia</a>, <a href="/wiki/Canada" title="Canada">Canada</a>, <a href="/wiki/Europe" title="Europe">Europe</a>, and <a href="/wiki/Latin_America" title="Latin America">Latin America</a>.<a href="#cite_note-IndexNominum2000-10">[10]</a><a href="#cite_note-Drugs.com-12">[12]</a> <div class="mw-heading mw-heading3"><h3 id="Availability">Availability</h3>[<a href="/w/index.php?title=Nilutamide&action=edit&section=17" title="Edit section: Availability">edit</a>]</div> Nilutamide is or has been available in the United States, Canada, Australia, Europe, Latin America, <a href="/wiki/Egypt" title="Egypt">Egypt</a>, and <a href="/wiki/Lebanon" title="Lebanon">Lebanon</a>.<a href="#cite_note-IndexNominum2000-10">[10]</a><a href="#cite_note-Drugs.com-12">[12]</a> In Europe, it is or has been available in <a href="/wiki/Belgium" title="Belgium">Belgium</a>, <a href="/wiki/Croatia" title="Croatia">Croatia</a>, the <a href="/wiki/Czech_Republic" title="Czech Republic">Czech Republic</a>, <a href="/wiki/Finland" title="Finland">Finland</a>, <a href="/wiki/France" title="France">France</a>, the <a href="/wiki/Netherlands" title="Netherlands">Netherlands</a>, <a href="/wiki/Norway" title="Norway">Norway</a>, <a href="/wiki/Poland" title="Poland">Poland</a>, <a href="/wiki/Portugal" title="Portugal">Portugal</a>, <a href="/wiki/Serbia" title="Serbia">Serbia</a>, <a href="/wiki/Sweden" title="Sweden">Sweden</a>, <a href="/wiki/Switzerland" title="Switzerland">Switzerland</a>, and <a href="/wiki/Yugoslavia" title="Yugoslavia">Yugoslavia</a>.<a href="#cite_note-IndexNominum2000-10">[10]</a><a href="#cite_note-Drugs.com-12">[12]</a> in Latin America, it is or has been available in <a href="/wiki/Argentina" title="Argentina">Argentina</a>, <a href="/wiki/Brazil" title="Brazil">Brazil</a>, and <a href="/wiki/Mexico" title="Mexico">Mexico</a>.<a href="#cite_note-IndexNominum2000-10">[10]</a><a href="#cite_note-Drugs.com-12">[12]</a> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2>[<a href="/w/index.php?title=Nilutamide&action=edit&section=18" title="Edit section: Research">edit</a>]</div> The combination of an <a href="/wiki/Estrogen_(medication)" title="Estrogen (medication)">estrogen</a> and nilutamide as a form of <a href="/wiki/Combined_androgen_blockade" class="mw-redirect" title="Combined androgen blockade">combined androgen blockade</a> for the treatment of prostate cancer has been studied in animals.<a href="#cite_note-pmid3420036-88">[86]</a> Nilutamide has been studied in the treatment of advanced breast cancer.<a href="#cite_note-pmid25665553-89">[87]</a><a href="#cite_note-pmid1903951-90">[88]</a> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Nilutamide&action=edit&section=19" title="Edit section: References">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-LiverTox-1">^ <a href="#cite_ref-LiverTox_1-0">a</a> <a href="#cite_ref-LiverTox_1-1">b</a> <a href="#cite_ref-LiverTox_1-2">c</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://livertox.nih.gov/Nilutamide.htm">"Nilutamide - LiverTox"</a>. <a href="/wiki/National_Institutes_of_Health" title="National Institutes of Health">National Institutes of Health</a>. 2012. <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/31643176">31643176</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180924224717/https://livertox.nih.gov/Nilutamide.htm">Archived</a> from the original on 24 September 2018. Retrieved 24 September 2018. <q>In large registration clinical trials, ALT elevations occurred in 2% to 33% of patients during nilutamide therapy. The elevations were usually mild, asymptomatic and transient, rarely requiring drug discontinuation. In rare instances, clinically apparent acute liver injury has occurred during nilutamide therapy, but the number of published cases are few, and the agent appears to be far less hepatotoxic than flutamide.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=National+Institutes+of+Health&rft.atitle=Nilutamide+-+LiverTox&rft.date=2012&rft_id=info%3Apmid%2F31643176&rft_id=https%3A%2F%2Flivertox.nih.gov%2FNilutamide.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-PerryDoll2012-2">^ <a href="#cite_ref-PerryDoll2012_2-0">a</a> <a href="#cite_ref-PerryDoll2012_2-1">b</a> <a href="#cite_ref-PerryDoll2012_2-2">c</a> <a href="#cite_ref-PerryDoll2012_2-3">d</a> <a href="#cite_ref-PerryDoll2012_2-4">e</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPerryDollFreter2012" class="citation book cs1">Perry MC, Doll DC, Freter CE (30 July 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=My3SjQTguyYC&pg=PA711">Perry's The Chemotherapy Source Book</a>. Lippincott Williams & Wilkins. pp. 711–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4698-0343-2" title="Special:BookSources/978-1-4698-0343-2"><bdi>978-1-4698-0343-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Perry%27s+The+Chemotherapy+Source+Book&rft.pages=711-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2012-07-30&rft.isbn=978-1-4698-0343-2&rft.aulast=Perry&rft.aufirst=MC&rft.au=Doll%2C+DC&rft.au=Freter%2C+CE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DMy3SjQTguyYC%26pg%3DPA711&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-FDA-AllBoxedWarnings-3"><a href="#cite_ref-FDA-AllBoxedWarnings_3-0">^</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://nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802">"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"</a>. nctr-crs.fda.gov. <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a>. Retrieved 22 October 2023.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=nctr-crs.fda.gov&rft.atitle=FDA-sourced+list+of+all+drugs+with+black+box+warnings+%28Use+Download+Full+Results+and+View+Query+links.%29&rft_id=https%3A%2F%2Fnctr-crs.fda.gov%2Ffdalabel%2Fui%2Fspl-summaries%2Fcriteria%2F343802&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-LemkeWilliams2012-4">^ <a href="#cite_ref-LemkeWilliams2012_4-0">a</a> <a href="#cite_ref-LemkeWilliams2012_4-1">b</a> <a href="#cite_ref-LemkeWilliams2012_4-2">c</a> <a href="#cite_ref-LemkeWilliams2012_4-3">d</a> <a href="#cite_ref-LemkeWilliams2012_4-4">e</a> <a href="#cite_ref-LemkeWilliams2012_4-5">f</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLemkeWilliams2012" class="citation book cs1">Lemke TL, Williams DA (24 January 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA1373">Foye's Principles of Medicinal Chemistry</a>. Lippincott Williams & Wilkins. pp. 1373–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60913-345-0" title="Special:BookSources/978-1-60913-345-0"><bdi>978-1-60913-345-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Foye%27s+Principles+of+Medicinal+Chemistry&rft.pages=1373-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2012-01-24&rft.isbn=978-1-60913-345-0&rft.aulast=Lemke&rft.aufirst=TL&rft.au=Williams%2C+DA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DSd6ot9ul-bUC%26pg%3DPA1373&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-ChabnerLongo2010-5">^ <a href="#cite_ref-ChabnerLongo2010_5-0">a</a> <a href="#cite_ref-ChabnerLongo2010_5-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChabnerLongo2010" class="citation book cs1">Chabner BA, Longo DL (8 November 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=WL4arNFsQa8C&pg=PA680">Cancer Chemotherapy and Biotherapy: Principles and Practice</a>. Lippincott Williams & Wilkins. pp. 680–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60547-431-1" title="Special:BookSources/978-1-60547-431-1"><bdi>978-1-60547-431-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110224032/https://books.google.com/books?id=WL4arNFsQa8C&pg=PA680">Archived</a> from the original on 10 January 2023. Retrieved 12 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Cancer+Chemotherapy+and+Biotherapy%3A+Principles+and+Practice&rft.pages=680-&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2010-11-08&rft.isbn=978-1-60547-431-1&rft.aulast=Chabner&rft.aufirst=BA&rft.au=Longo%2C+DL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DWL4arNFsQa8C%26pg%3DPA680&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-KolvenbagFurr2009-6">^ <a href="#cite_ref-KolvenbagFurr2009_6-0">a</a> <a href="#cite_ref-KolvenbagFurr2009_6-1">b</a> <a href="#cite_ref-KolvenbagFurr2009_6-2">c</a> <a href="#cite_ref-KolvenbagFurr2009_6-3">d</a> <a href="#cite_ref-KolvenbagFurr2009_6-4">e</a> <a href="#cite_ref-KolvenbagFurr2009_6-5">f</a> <a href="#cite_ref-KolvenbagFurr2009_6-6">g</a> <a href="#cite_ref-KolvenbagFurr2009_6-7">h</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKolvenbagFurr2009" class="citation book cs1">Kolvenbag GJ, Furr BJ (2009). "Nonsteroidal Antiandrogens". In Jordan VC, Furr HJ (eds.). Hormone Therapy in Breast and Prostate Cancer. Humana Press. pp. 347–368. <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%2F978-1-59259-152-7_16">10.1007/978-1-59259-152-7_16</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-60761-471-5" title="Special:BookSources/978-1-60761-471-5"><bdi>978-1-60761-471-5</bdi></a>. <q>Although the t1/2 of nilutamide is h (mean 56 h) (39), suggesting that once-daily dosing would be appropriate, a three times per day regimen has been employed in most clinical trials.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Nonsteroidal+Antiandrogens&rft.btitle=Hormone+Therapy+in+Breast+and+Prostate+Cancer&rft.pages=347-368&rft.pub=Humana+Press&rft.date=2009&rft_id=info%3Adoi%2F10.1007%2F978-1-59259-152-7_16&rft.isbn=978-1-60761-471-5&rft.aulast=Kolvenbag&rft.aufirst=GJ&rft.au=Furr%2C+BJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-7"><a href="#cite_ref-7">^</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/pregnancy/nilutamide.html">"Nilutamide (Nilandron) Use During Pregnancy"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201028022327/https://www.drugs.com/pregnancy/nilutamide.html">Archived</a> from the original on 28 October 2020. Retrieved 20 July 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Nilutamide+%28Nilandron%29+Use+During+Pregnancy&rft_id=https%3A%2F%2Fwww.drugs.com%2Fpregnancy%2Fnilutamide.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-8"><a href="#cite_ref-8">^</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/2017/020169s008lbl.pdf">"NILANDRON® (nilutamide)"</a> (PDF). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210330022054/https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020169s008lbl.pdf">Archived</a> (PDF) from the original on 30 March 2021. 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Springer. pp. 873–. <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=873-&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%3DPA873&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-IndexNominum2000-10">^ <a href="#cite_ref-IndexNominum2000_10-0">a</a> <a href="#cite_ref-IndexNominum2000_10-1">b</a> <a href="#cite_ref-IndexNominum2000_10-2">c</a> <a href="#cite_ref-IndexNominum2000_10-3">d</a> <a href="#cite_ref-IndexNominum2000_10-4">e</a> <a href="#cite_ref-IndexNominum2000_10-5">f</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=PA737">Index Nominum 2000: International Drug Directory</a>. Taylor & Francis. 2000. pp. 737–. <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=737-&rft.pub=Taylor+%26+Francis&rft.date=2000&rft.isbn=978-3-88763-075-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5GpcTQD_L2oC%26pg%3DPA737&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-MortonHall2012-11">^ <a href="#cite_ref-MortonHall2012_11-0">a</a> <a href="#cite_ref-MortonHall2012_11-1">b</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=PA199">Concise Dictionary of Pharmacological Agents: Properties and Synonyms</a>. Springer Science & Business Media. pp. 199–. <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=199-&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%3DPA199&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Drugs.com-12">^ <a href="#cite_ref-Drugs.com_12-0">a</a> <a href="#cite_ref-Drugs.com_12-1">b</a> <a href="#cite_ref-Drugs.com_12-2">c</a> <a href="#cite_ref-Drugs.com_12-3">d</a> <a href="#cite_ref-Drugs.com_12-4">e</a> <a href="#cite_ref-Drugs.com_12-5">f</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/nilutamide.html">"Nilutamide"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201202070855/https://www.drugs.com/international/nilutamide.html">Archived</a> from the original on 2 December 2020. 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Springer Science & Business Media. pp. 280–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4614-7441-8" title="Special:BookSources/978-1-4614-7441-8"><bdi>978-1-4614-7441-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Gender+Dysphoria+and+Disorders+of+Sex+Development%3A+Progress+in+Care+and+Knowledge&rft.pages=280-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2013-07-01&rft.isbn=978-1-4614-7441-8&rft.aulast=Kreukels&rft.aufirst=BP&rft.au=Steensma%2C+TD&rft.au=De+Vries%2C+AL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DYQ5GAAAAQBAJ%26pg%3DPA280&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid2744186-16">^ <a href="#cite_ref-pmid2744186_16-0">a</a> <a href="#cite_ref-pmid2744186_16-1">b</a> <a href="#cite_ref-pmid2744186_16-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCouzinetThomasThalabardBrailly1989" class="citation journal cs1">Couzinet B, Thomas G, Thalabard JC, Brailly S, Schaison G (July 1989). 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Oxford University Press, USA. pp. 479–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-971055-3" title="Special:BookSources/978-0-19-971055-3"><bdi>978-0-19-971055-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110224047/https://books.google.com/books?id=mpZ8Dp2KdHMC&pg=PA479">Archived</a> from the original on 10 January 2023. 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Wolters Kluwer Health. pp. 1006–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4963-5421-1" title="Special:BookSources/978-1-4963-5421-1"><bdi>978-1-4963-5421-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Prostate+and+Other+Genitourinary+Cancers%3A+Cancer%3A+Principles+%26+Practice+of+Oncology&rft.pages=1006-&rft.pub=Wolters+Kluwer+Health&rft.date=2016-03-18&rft.isbn=978-1-4963-5421-1&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBf3DCwAAQBAJ%26pg%3DPT1006&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Chang2005-27">^ <a href="#cite_ref-Chang2005_27-0">a</a> <a href="#cite_ref-Chang2005_27-1">b</a> <a href="#cite_ref-Chang2005_27-2">c</a> <a href="#cite_ref-Chang2005_27-3">d</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChang2005" class="citation book cs1">Chang C (1 January 2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4xQAr3Uh8EUC&pg=PA11">Prostate Cancer: Basic Mechanisms and Therapeutic Approaches</a>. World Scientific. pp. 11–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-981-256-920-2" title="Special:BookSources/978-981-256-920-2"><bdi>978-981-256-920-2</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Prostate+Cancer%3A+Basic+Mechanisms+and+Therapeutic+Approaches&rft.pages=11-&rft.pub=World+Scientific&rft.date=2005-01-01&rft.isbn=978-981-256-920-2&rft.aulast=Chang&rft.aufirst=C&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4xQAr3Uh8EUC%26pg%3DPA11&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-SinghGauthier2000-28">^ <a href="#cite_ref-SinghGauthier2000_28-0">a</a> <a href="#cite_ref-SinghGauthier2000_28-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSinghGauthierLabrie2000" class="citation journal cs1">Singh SM, Gauthier S, Labrie F (February 2000). 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(1978). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1365-2605.1978.tb00008.x">"Interactions Between LHRH, Sex Steroids and "Inhibin" in the Control of LH and FSH Secretion"</a>. International Journal of Andrology. 1 (s2a): 81–101. <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.1365-2605.1978.tb00008.x">10.1111/j.1365-2605.1978.tb00008.x</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0105-6263">0105-6263</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+Andrology&rft.atitle=Interactions+Between+LHRH%2C+Sex+Steroids+and+%22Inhibin%22+in+the+Control+of+LH+and+FSH+Secretion&rft.volume=1&rft.issue=s2a&rft.pages=81-101&rft.date=1978&rft_id=info%3Adoi%2F10.1111%2Fj.1365-2605.1978.tb00008.x&rft.issn=0105-6263&rft.aulast=Labrie&rft.aufirst=F&rft.au=Lagac%C3%A9%2C+L&rft.au=Ferland%2C+L&rft.au=Kelly%2C+PA&rft.au=Drouin%2C+J&rft.au=Massicotte%2C+J&rft.au=Bonne%2C+C&rft.au=Raynaud%2C+JP&rft.au=Dorrington%2C+JH&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.1365-2605.1978.tb00008.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid385986-30">^ <a href="#cite_ref-pmid385986_30-0">a</a> <a href="#cite_ref-pmid385986_30-1">b</a> <a href="#cite_ref-pmid385986_30-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRaynaudBonneBoutonLagace1979" class="citation journal cs1">Raynaud JP, Bonne C, Bouton MM, Lagace L, Labrie F (July 1979). "Action of a non-steroid anti-androgen, RU 23908, in peripheral and central tissues". Journal of Steroid Biochemistry. 11 (1A): 93–99. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-4731%2879%2990281-4">10.1016/0022-4731(79)90281-4</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/385986">385986</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Steroid+Biochemistry&rft.atitle=Action+of+a+non-steroid+anti-androgen%2C+RU+23908%2C+in+peripheral+and+central+tissues&rft.volume=11&rft.issue=1A&rft.pages=93-99&rft.date=1979-07&rft_id=info%3Adoi%2F10.1016%2F0022-4731%2879%2990281-4&rft_id=info%3Apmid%2F385986&rft.aulast=Raynaud&rft.aufirst=JP&rft.au=Bonne%2C+C&rft.au=Bouton%2C+MM&rft.au=Lagace%2C+L&rft.au=Labrie%2C+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Pavlik2012-31">^ <a href="#cite_ref-Pavlik2012_31-0">a</a> <a href="#cite_ref-Pavlik2012_31-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPavlik2012" class="citation book cs1">Pavlik EJ (6 December 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=LAnpBwAAQBAJ&pg=PA167">Estrogens, Progestins, and Their Antagonists: Health Issues</a>. Springer Science & Business Media. pp. 167–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4612-4096-9" title="Special:BookSources/978-1-4612-4096-9"><bdi>978-1-4612-4096-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Estrogens%2C+Progestins%2C+and+Their+Antagonists%3A+Health+Issues&rft.pages=167-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2012-12-06&rft.isbn=978-1-4612-4096-9&rft.aulast=Pavlik&rft.aufirst=EJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DLAnpBwAAQBAJ%26pg%3DPA167&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-BohlGao2005-32">^ <a href="#cite_ref-BohlGao2005_32-0">a</a> <a href="#cite_ref-BohlGao2005_32-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBohlGaoMillerBell2005" class="citation journal cs1">Bohl CE, Gao W, Miller DD, Bell CE, Dalton JT (April 2005). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1087923">"Structural basis for antagonism and resistance of bicalutamide in prostate cancer"</a>. Proceedings of the National Academy of Sciences of the United States of America. 102 (17): 6201–6206. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2005PNAS..102.6201B">2005PNAS..102.6201B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.0500381102">10.1073/pnas.0500381102</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/PMC1087923">1087923</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/15833816">15833816</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&rft.atitle=Structural+basis+for+antagonism+and+resistance+of+bicalutamide+in+prostate+cancer&rft.volume=102&rft.issue=17&rft.pages=6201-6206&rft.date=2005-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1087923%23id-name%3DPMC&rft_id=info%3Apmid%2F15833816&rft_id=info%3Adoi%2F10.1073%2Fpnas.0500381102&rft_id=info%3Abibcode%2F2005PNAS..102.6201B&rft.aulast=Bohl&rft.aufirst=CE&rft.au=Gao%2C+W&rft.au=Miller%2C+DD&rft.au=Bell%2C+CE&rft.au=Dalton%2C+JT&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1087923&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-AdisInsight-33">^ <a href="#cite_ref-AdisInsight_33-0">a</a> <a href="#cite_ref-AdisInsight_33-1">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="http://adisinsight.springer.com/drugs/800004379">"Nilutamide - AdisInsight"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210505173834/https://adisinsight.springer.com/drugs/800004379">Archived</a> from the original on 5 May 2021. Retrieved 26 June 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Nilutamide+-+AdisInsight&rft_id=http%3A%2F%2Fadisinsight.springer.com%2Fdrugs%2F800004379&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Gulley2011-34">^ <a href="#cite_ref-Gulley2011_34-0">a</a> <a href="#cite_ref-Gulley2011_34-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGulley2011" class="citation book cs1">Gulley JL (2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=WJkjgbRJe3EC&pg=PT81">Prostate Cancer</a>. Demos Medical Publishing. pp. 81–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-935281-91-7" title="Special:BookSources/978-1-935281-91-7"><bdi>978-1-935281-91-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Prostate+Cancer&rft.pages=81-&rft.pub=Demos+Medical+Publishing&rft.date=2011&rft.isbn=978-1-935281-91-7&rft.aulast=Gulley&rft.aufirst=JL&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DWJkjgbRJe3EC%26pg%3DPT81&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-WHO22nd-35"><a href="#cite_ref-WHO22nd_35-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWorld_Health_Organization2021" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<a rel="nofollow" class="external text" href="https://hdl.handle.net/10665%2F345533">10665/345533</a>. WHO/MHP/HPS/EML/2021.02.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=World+Health+Organization+model+list+of+essential+medicines%3A+22nd+list+%282021%29&rft.place=Geneva&rft.pub=World+Health+Organization&rft.date=2021&rft_id=info%3Ahdl%2F10665%2F345533&rft.au=World+Health+Organization&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Upfal2006-36"><a href="#cite_ref-Upfal2006_36-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFUpfal2006" class="citation book cs1">Upfal J (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=7O9kiqN2q2YC&pg=PA283">The Australian Drug Guide: Every Person's Guide to Prescription and Over-the-counter Medicines, Street Drugs, Vaccines, Vitamins and Minerals...</a> Black Inc. pp. 283–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-86395-174-6" title="Special:BookSources/978-1-86395-174-6"><bdi>978-1-86395-174-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Australian+Drug+Guide%3A+Every+Person%27s+Guide+to+Prescription+and+Over-the-counter+Medicines%2C+Street+Drugs%2C+Vaccines%2C+Vitamins+and+Minerals...&rft.pages=283-&rft.pub=Black+Inc.&rft.date=2006&rft.isbn=978-1-86395-174-6&rft.aulast=Upfal&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D7O9kiqN2q2YC%26pg%3DPA283&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid12603397-37"><a href="#cite_ref-pmid12603397_37-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAnderson2003" class="citation journal cs1">Anderson J (March 2003). "The role of antiandrogen monotherapy in the treatment of prostate cancer". BJU International. 91 (5): 455–461. <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.1464-410X.2003.04026.x">10.1046/j.1464-410X.2003.04026.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/12603397">12603397</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:8639102">8639102</a>. <q>Trial experience with nilutamide monotherapy is limited to one small non-comparative study involving 26 patients with metastatic disease given nilutamide 100 mg three times daily (the dose used when nilutamide is administered as a component of MAB) [14]. The median progression-free survival in these patients was 9 months, with a median overall survival of 23 months. There have been no comparative trials of nilutamide with other antiandrogens or with castration [15]. The limited available data on nilutamide monotherapy means that no meaningful conclusions about the role of nilutamide in this setting can be determined. Nilutamide is not licensed as monotherapy.</q></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+role+of+antiandrogen+monotherapy+in+the+treatment+of+prostate+cancer&rft.volume=91&rft.issue=5&rft.pages=455-461&rft.date=2003-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A8639102%23id-name%3DS2CID&rft_id=info%3Apmid%2F12603397&rft_id=info%3Adoi%2F10.1046%2Fj.1464-410X.2003.04026.x&rft.aulast=Anderson&rft.aufirst=J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid16986003-38"><a href="#cite_ref-pmid16986003_38-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFThompson2001" class="citation journal cs1">Thompson IM (2001). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1476081">"Flare Associated with LHRH-Agonist Therapy"</a>. 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"Sex steroids and pulsatile luteinizing hormone release in men. Studies in estrogen-treated agonadal subjects and eugonadal subjects treated with a novel nonsteroidal antiandrogen". The Journal of Clinical Endocrinology and Metabolism. 64 (4): 763–770. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1210%2Fjcem-64-4-763">10.1210/jcem-64-4-763</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/3102546">3102546</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Clinical+Endocrinology+and+Metabolism&rft.atitle=Sex+steroids+and+pulsatile+luteinizing+hormone+release+in+men.+Studies+in+estrogen-treated+agonadal+subjects+and+eugonadal+subjects+treated+with+a+novel+nonsteroidal+antiandrogen&rft.volume=64&rft.issue=4&rft.pages=763-770&rft.date=1987-04&rft_id=info%3Adoi%2F10.1210%2Fjcem-64-4-763&rft_id=info%3Apmid%2F3102546&rft.aulast=Gooren&rft.aufirst=L&rft.au=Spinder%2C+T&rft.au=Spijkstra%2C+JJ&rft.au=van+Kessel%2C+H&rft.au=Smals%2C+A&rft.au=Rao%2C+BR&rft.au=Hoogslag%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-De_VoogtRao1987-45">^ <a href="#cite_ref-De_VoogtRao1987_45-0">a</a> <a href="#cite_ref-De_VoogtRao1987_45-1">b</a> <a href="#cite_ref-De_VoogtRao1987_45-2">c</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFde_VoogtRaoGeldofGooren1987" class="citation journal cs1">de Voogt HJ, Rao BR, Geldof AA, Gooren LJ, Bouman FG (1987). "Androgen action blockade does not result in reduction in size but changes histology of the normal human prostate". The Prostate. 11 (4): 305–311. <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.2990110403">10.1002/pros.2990110403</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/2960959">2960959</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:84632739">84632739</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&rft.atitle=Androgen+action+blockade+does+not+result+in+reduction+in+size+but+changes+histology+of+the+normal+human+prostate&rft.volume=11&rft.issue=4&rft.pages=305-311&rft.date=1987&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A84632739%23id-name%3DS2CID&rft_id=info%3Apmid%2F2960959&rft_id=info%3Adoi%2F10.1002%2Fpros.2990110403&rft.aulast=de+Voogt&rft.aufirst=HJ&rft.au=Rao%2C+BR&rft.au=Geldof%2C+AA&rft.au=Gooren%2C+LJ&rft.au=Bouman%2C+FG&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Cohen-KettenisGooren1993-46"><a href="#cite_ref-Cohen-KettenisGooren1993_46-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCohen-KettenisGooren1993" class="citation journal cs1">Cohen-Kettenis PT, Gooren LJ (1993). 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Adis International. 1993. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110224014/https://books.google.com/books?id=roFNAQAAIAAJ">Archived</a> from the original on 10 January 2023. Retrieved 2 April 2018. <q>In 16 male subjects undergoing androgen blockade with nilutamide 100 to 300 mg/day for 8 weeks for male to female gender reassignment, prostate volume was not changed (de Voogt et al. 1987).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drugs+%26+Aging&rft.pub=Adis+International&rft.date=1993&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DroFNAQAAIAAJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Meyers2018-48"><a href="#cite_ref-Meyers2018_48-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMeyers2018" class="citation book cs1">Meyers RA (2 March 2018). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=kuhPDwAAQBAJ&pg=PA46">Translational Medicine: Molecular Pharmacology and Drug Discovery</a>. Wiley. pp. 46–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-68719-0" title="Special:BookSources/978-3-527-68719-0"><bdi>978-3-527-68719-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110224026/https://books.google.com/books?id=kuhPDwAAQBAJ&pg=PA46">Archived</a> from the original on 10 January 2023. Retrieved 2 August 2018.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Translational+Medicine%3A+Molecular+Pharmacology+and+Drug+Discovery&rft.pages=46-&rft.pub=Wiley&rft.date=2018-03-02&rft.isbn=978-3-527-68719-0&rft.aulast=Meyers&rft.aufirst=RA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DkuhPDwAAQBAJ%26pg%3DPA46&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Bautista-VidalBarnoiu2014-49"><a href="#cite_ref-Bautista-VidalBarnoiu2014_49-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBautista-VidalBarnoiuGarcía-GalisteoGómez-Lechuga2014" class="citation journal cs1">Bautista-Vidal C, Barnoiu O, García-Galisteo E, Gómez-Lechuga P, Baena-González V (2014). "Treatment of gynecomastia in patients with prostate cancer and androgen deprivation". Actas Urologicas Espanolas. 38 (1): 34–40. <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.acuroe.2013.10.002">10.1016/j.acuroe.2013.10.002</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/23850393">23850393</a>. <q>[...] the frequency of gynecomastia with antiandrogens in monotherapy is [...] around [...] 79% with nilutamide [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Actas+Urologicas+Espanolas&rft.atitle=Treatment+of+gynecomastia+in+patients+with+prostate+cancer+and+androgen+deprivation&rft.volume=38&rft.issue=1&rft.pages=34-40&rft.date=2014&rft_id=info%3Adoi%2F10.1016%2Fj.acuroe.2013.10.002&rft_id=info%3Apmid%2F23850393&rft.aulast=Bautista-Vidal&rft.aufirst=C&rft.au=Barnoiu%2C+O&rft.au=Garc%C3%ADa-Galisteo%2C+E&rft.au=G%C3%B3mez-Lechuga%2C+P&rft.au=Baena-Gonz%C3%A1lez%2C+V&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-DeepinderBraunstein2012-50"><a href="#cite_ref-DeepinderBraunstein2012_50-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDeepinderBraunstein2012" class="citation journal cs1">Deepinder F, Braunstein GD (September 2012). "Drug-induced gynecomastia: an evidence-based review". Expert Opinion on Drug Safety. 11 (5): 779–795. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1517%2F14740338.2012.712109">10.1517/14740338.2012.712109</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/22862307">22862307</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:22938364">22938364</a>. <q>Treatment with estrogen has the highest incidence of gynecomastia, at 40 – 80%, anti-androgens, including flutamide, bicalutamide and nilutamide, are next, with a 40 – 70% incidence, followed by GnRH analogs (goserelin, leuprorelin) and combined androgen deprivation [...]</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opinion+on+Drug+Safety&rft.atitle=Drug-induced+gynecomastia%3A+an+evidence-based+review&rft.volume=11&rft.issue=5&rft.pages=779-795&rft.date=2012-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A22938364%23id-name%3DS2CID&rft_id=info%3Apmid%2F22862307&rft_id=info%3Adoi%2F10.1517%2F14740338.2012.712109&rft.aulast=Deepinder&rft.aufirst=F&rft.au=Braunstein%2C+GD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-MichalopoulosKeshtgar2012-51"><a href="#cite_ref-MichalopoulosKeshtgar2012_51-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMichalopoulosKeshtgar2012" class="citation journal cs1">Michalopoulos NV, Keshtgar MR (October 2012). "Images in clinical medicine. Gynecomastia induced by prostate-cancer treatment". The New England Journal of Medicine. 367 (15): 1449. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1056%2FNEJMicm1209166">10.1056/NEJMicm1209166</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/23050528">23050528</a>. <q>Gynecomastia occurs in up to 80% of patients who receive nonsteroidal antiandrogens (eg, bicalutamide, flutamide, or nilutamide), usually within the first 6 to 9 months after the initiation of treatment.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+New+England+Journal+of+Medicine&rft.atitle=Images+in+clinical+medicine.+Gynecomastia+induced+by+prostate-cancer+treatment&rft.volume=367&rft.issue=15&rft.pages=1449&rft.date=2012-10&rft_id=info%3Adoi%2F10.1056%2FNEJMicm1209166&rft_id=info%3Apmid%2F23050528&rft.aulast=Michalopoulos&rft.aufirst=NV&rft.au=Keshtgar%2C+MR&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid16321765-52"><a href="#cite_ref-pmid16321765_52-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDi_LorenzoAutorinoPerdonàDe_Placido2005" class="citation journal cs1">Di Lorenzo G, Autorino R, Perdonà S, De Placido S (December 2005). "Management of gynaecomastia in patients with prostate cancer: a systematic review". The Lancet. Oncology. 6 (12): 972–979. <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%2805%2970464-2">10.1016/S1470-2045(05)70464-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16321765">16321765</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=Management+of+gynaecomastia+in+patients+with+prostate+cancer%3A+a+systematic+review&rft.volume=6&rft.issue=12&rft.pages=972-979&rft.date=2005-12&rft_id=info%3Adoi%2F10.1016%2FS1470-2045%2805%2970464-2&rft_id=info%3Apmid%2F16321765&rft.aulast=Di+Lorenzo&rft.aufirst=G&rft.au=Autorino%2C+R&rft.au=Perdon%C3%A0%2C+S&rft.au=De+Placido%2C+S&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-CamusIII2010-53"><a href="#cite_ref-CamusIII2010_53-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCamusRosenow_III2010" class="citation book cs1">Camus P, Rosenow III EC (29 October 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=QlJsBgAAQBAJ&pg=PA235">Drug-induced and Iatrogenic Respiratory Disease</a>. CRC Press. pp. 235–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4441-2869-7" title="Special:BookSources/978-1-4441-2869-7"><bdi>978-1-4441-2869-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drug-induced+and+Iatrogenic+Respiratory+Disease&rft.pages=235-&rft.pub=CRC+Press&rft.date=2010-10-29&rft.isbn=978-1-4441-2869-7&rft.aulast=Camus&rft.aufirst=P&rft.au=Rosenow+III%2C+EC&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DQlJsBgAAQBAJ%26pg%3DPA235&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Held-Warmkessel2006-54"><a href="#cite_ref-Held-Warmkessel2006_54-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHeld-Warmkessel2006" class="citation book cs1">Held-Warmkessel J (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dZe4ZSVDdBsC&pg=PA257">Contemporary Issues in Prostate Cancer: A Nursing Perspective</a>. Jones & Bartlett Learning. pp. 257–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7637-3075-8" title="Special:BookSources/978-0-7637-3075-8"><bdi>978-0-7637-3075-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Contemporary+Issues+in+Prostate+Cancer%3A+A+Nursing+Perspective&rft.pages=257-&rft.pub=Jones+%26+Bartlett+Learning&rft.date=2006&rft.isbn=978-0-7637-3075-8&rft.aulast=Held-Warmkessel&rft.aufirst=J&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DdZe4ZSVDdBsC%26pg%3DPA257&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-RamonDenis2007-55"><a href="#cite_ref-RamonDenis2007_55-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRamonDenis2007" class="citation book cs1">Ramon J, Denis LJ (5 June 2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=Bg6ZbqhhboUC&pg=PA229">Prostate Cancer</a>. Springer Science & Business Media. pp. 229–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-540-40901-4" title="Special:BookSources/978-3-540-40901-4"><bdi>978-3-540-40901-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Prostate+Cancer&rft.pages=229-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2007-06-05&rft.isbn=978-3-540-40901-4&rft.aulast=Ramon&rft.aufirst=J&rft.au=Denis%2C+LJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBg6ZbqhhboUC%26pg%3DPA229&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Mahler1996-56"><a href="#cite_ref-Mahler1996_56-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMahler1996" class="citation book cs1">Mahler C (1996). "A Review of the Clinical Studies with Nilutamide". Antiandrogens in Prostate Cancer. pp. 105–111. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-45745-6_10">10.1007/978-3-642-45745-6_10</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-45747-0" title="Special:BookSources/978-3-642-45747-0"><bdi>978-3-642-45747-0</bdi></a>. <q>Akaza had to prematurely terminate a nilutamide study in Japan as 12.6% of his patients developed interstitial lung disease [4]. This complication has been mainly observed in Japan and much less in other trials worldwide.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=A+Review+of+the+Clinical+Studies+with+Nilutamide&rft.btitle=Antiandrogens+in+Prostate+Cancer&rft.pages=105-111&rft.date=1996&rft_id=info%3Adoi%2F10.1007%2F978-3-642-45745-6_10&rft.isbn=978-3-642-45747-0&rft.aulast=Mahler&rft.aufirst=C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Micromedex2003-57"><a href="#cite_ref-Micromedex2003_57-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMicromedex2003" class="citation book cs1">Micromedex (1 January 2003). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zEzWtsVl-KgC">USP DI 2003: Drug Information for Healthcare Professionals</a>. Thomson Micromedex. pp. 220–224. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-56363-429-1" title="Special:BookSources/978-1-56363-429-1"><bdi>978-1-56363-429-1</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110224310/https://books.google.com/books?id=zEzWtsVl-KgC">Archived</a> from the original on 10 January 2023. Retrieved 12 October 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=USP+DI+2003%3A+Drug+Information+for+Healthcare+Professionals&rft.pages=220-224&rft.pub=Thomson+Micromedex&rft.date=2003-01-01&rft.isbn=978-1-56363-429-1&rft.au=Micromedex&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzEzWtsVl-KgC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid1580304-58"><a href="#cite_ref-pmid1580304_58-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGomezDupontCusanTremblay1992" class="citation journal cs1">Gomez JL, Dupont A, Cusan L, Tremblay M, Tremblay M, Labrie F (May 1992). "Simultaneous liver and lung toxicity related to the nonsteroidal antiandrogen nilutamide (Anandron): a case report". The American Journal of Medicine. 92 (5): 563–566. <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%2F0002-9343%2892%2990756-2">10.1016/0002-9343(92)90756-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/1580304">1580304</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+American+Journal+of+Medicine&rft.atitle=Simultaneous+liver+and+lung+toxicity+related+to+the+nonsteroidal+antiandrogen+nilutamide+%28Anandron%29%3A+a+case+report&rft.volume=92&rft.issue=5&rft.pages=563-566&rft.date=1992-05&rft_id=info%3Adoi%2F10.1016%2F0002-9343%2892%2990756-2&rft_id=info%3Apmid%2F1580304&rft.aulast=Gomez&rft.aufirst=JL&rft.au=Dupont%2C+A&rft.au=Cusan%2C+L&rft.au=Tremblay%2C+M&rft.au=Tremblay%2C+M&rft.au=Labrie%2C+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Aronson2009-59"><a href="#cite_ref-Aronson2009_59-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAronson2009" class="citation book cs1">Aronson JK (21 February 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=BWMeSwVwfTkC&pg=PA150">Meyler's Side Effects of Endocrine and Metabolic Drugs</a>. Elsevier. pp. 150–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-08-093292-7" title="Special:BookSources/978-0-08-093292-7"><bdi>978-0-08-093292-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Meyler%27s+Side+Effects+of+Endocrine+and+Metabolic+Drugs&rft.pages=150-&rft.pub=Elsevier&rft.date=2009-02-21&rft.isbn=978-0-08-093292-7&rft.aulast=Aronson&rft.aufirst=JK&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DBWMeSwVwfTkC%26pg%3DPA150&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid10388026-60">^ <a href="#cite_ref-pmid10388026_60-0">a</a> <a href="#cite_ref-pmid10388026_60-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMcLeod1997" class="citation journal cs1">McLeod DG (1997). <a rel="nofollow" class="external text" href="https://doi.org/10.1634%2Ftheoncologist.2-1-18">"Tolerability of Nonsteroidal Antiandrogens in the Treatment of Advanced Prostate Cancer"</a>. The Oncologist. 2 (1): 18–27. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1634%2Ftheoncologist.2-1-18">10.1634/theoncologist.2-1-18</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/10388026">10388026</a>. <q>Incidences of abnormal liver function test results have been variously reported from 2%-33% in nilutamide groups [13, 32, 33, 45] and from 4%-62% in flutamide groups [5, 7, 9, 11, 34, 38-40, 48] in trials of monotherapy and CAB.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Oncologist&rft.atitle=Tolerability+of+Nonsteroidal+Antiandrogens+in+the+Treatment+of+Advanced+Prostate+Cancer&rft.volume=2&rft.issue=1&rft.pages=18-27&rft.date=1997&rft_id=info%3Adoi%2F10.1634%2Ftheoncologist.2-1-18&rft_id=info%3Apmid%2F10388026&rft.aulast=McLeod&rft.aufirst=DG&rft_id=https%3A%2F%2Fdoi.org%2F10.1634%252Ftheoncologist.2-1-18&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Aronson2011-61"><a href="#cite_ref-Aronson2011_61-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAronson2011" class="citation book cs1">Aronson JK (2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=zegpAgEt3CcC&pg=PA874">Side Effects of Drugs Annual: A Worldwide Yearly Survey of New Data in Adverse Drug Reactions</a>. Elsevier. pp. 874–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-53741-6" title="Special:BookSources/978-0-444-53741-6"><bdi>978-0-444-53741-6</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Side+Effects+of+Drugs+Annual%3A+A+Worldwide+Yearly+Survey+of+New+Data+in+Adverse+Drug+Reactions&rft.pages=874-&rft.pub=Elsevier&rft.date=2011&rft.isbn=978-0-444-53741-6&rft.aulast=Aronson&rft.aufirst=JK&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DzegpAgEt3CcC%26pg%3DPA874&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid8977826-62"><a href="#cite_ref-pmid8977826_62-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMartyGodartDoermannMérillon1996" class="citation journal cs1 cs1-prop-foreign-lang-source">Marty F, Godart D, Doermann F, Mérillon H (1996). "[Fatal fulminating hepatitis caused by nilutamide. A new case]". Gastroenterologie Clinique et Biologique (in French). 20 (8–9): 710–711. <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/8977826">8977826</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gastroenterologie+Clinique+et+Biologique&rft.atitle=%5BFatal+fulminating+hepatitis+caused+by+nilutamide.+A+new+case%5D&rft.volume=20&rft.issue=8%E2%80%939&rft.pages=710-711&rft.date=1996&rft_id=info%3Apmid%2F8977826&rft.aulast=Marty&rft.aufirst=F&rft.au=Godart%2C+D&rft.au=Doermann%2C+F&rft.au=M%C3%A9rillon%2C+H&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-MerwatKabbani2008-63">^ <a href="#cite_ref-MerwatKabbani2008_63-0">a</a> <a href="#cite_ref-MerwatKabbani2008_63-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMerwatKabbaniAdler2009" class="citation journal cs1">Merwat SN, Kabbani W, Adler DG (April 2009). "Fulminant hepatic failure due to nilutamide hepatotoxicity". Digestive Diseases and Sciences. 54 (4): 910–913. <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%2Fs10620-008-0406-8">10.1007/s10620-008-0406-8</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/18688719">18688719</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:27421870">27421870</a>. <q>In addition, nilutamide is noted to exhibit mitochondrial toxicity by inhibiting complex I activity of the mitochondrial respiratory chain leading to the impairment of ATP formation and the biosynthesis of glutathione, thereby possibly predisposing the liver to toxicity [13].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Digestive+Diseases+and+Sciences&rft.atitle=Fulminant+hepatic+failure+due+to+nilutamide+hepatotoxicity&rft.volume=54&rft.issue=4&rft.pages=910-913&rft.date=2009-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A27421870%23id-name%3DS2CID&rft_id=info%3Apmid%2F18688719&rft_id=info%3Adoi%2F10.1007%2Fs10620-008-0406-8&rft.aulast=Merwat&rft.aufirst=SN&rft.au=Kabbani%2C+W&rft.au=Adler%2C+DG&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-ChitturiFarrell2013-64"><a href="#cite_ref-ChitturiFarrell2013_64-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChitturiFarrell2013" class="citation book cs1">Chitturi S, Farrell GC (2013). "Adverse Effects of Hormones and Hormone Antagonists on the Liver". Drug-Induced Liver Disease. Vol. 3. Academic Press. pp. 605–619. <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%2FB978-0-12-387817-5.00033-9">10.1016/B978-0-12-387817-5.00033-9</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780123878175" title="Special:BookSources/9780123878175"><bdi>9780123878175</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/11096606">11096606</a>. <q>Liver injury is well recognized with all antiandrogens (Table 33-3). Thus, among all published cases identified between 1986 and 2003, flutamide (46), cyproterone (21), nilutamide (4), and bicalutamide (1) were implicated [107,108].</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Adverse+Effects+of+Hormones+and+Hormone+Antagonists+on+the+Liver&rft.btitle=Drug-Induced+Liver+Disease&rft.pages=605-619&rft.pub=Academic+Press&rft.date=2013&rft_id=info%3Apmid%2F11096606&rft_id=info%3Adoi%2F10.1016%2FB978-0-12-387817-5.00033-9&rft.isbn=9780123878175&rft.aulast=Chitturi&rft.aufirst=S&rft.au=Farrell%2C+GC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> <code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: <code class="cs1-code">|journal=</code> ignored (<a href="/wiki/Help:CS1_errors#periodical_ignored" title="Help:CS1 errors">help</a>) </li> <li id="cite_note-pmid8035313-65"><a href="#cite_ref-pmid8035313_65-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBersonSchmetsFischFau1994" class="citation journal cs1">Berson A, Schmets L, Fisch C, Fau D, Wolf C, Fromenty B, et al. (July 1994). "Inhibition by nilutamide of the mitochondrial respiratory chain and ATP formation. Possible contribution to the adverse effects of this antiandrogen". The Journal of Pharmacology and Experimental Therapeutics. 270 (1): 167–176. <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/8035313">8035313</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Pharmacology+and+Experimental+Therapeutics&rft.atitle=Inhibition+by+nilutamide+of+the+mitochondrial+respiratory+chain+and+ATP+formation.+Possible+contribution+to+the+adverse+effects+of+this+antiandrogen&rft.volume=270&rft.issue=1&rft.pages=167-176&rft.date=1994-07&rft_id=info%3Apmid%2F8035313&rft.aulast=Berson&rft.aufirst=A&rft.au=Schmets%2C+L&rft.au=Fisch%2C+C&rft.au=Fau%2C+D&rft.au=Wolf%2C+C&rft.au=Fromenty%2C+B&rft.au=Deschamps%2C+D&rft.au=Pessayre%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-CoeJia2007-66">^ <a href="#cite_ref-CoeJia2007_66-0">a</a> <a href="#cite_ref-CoeJia2007_66-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFCoeJiaHoRademacher2007" class="citation journal cs1">Coe KJ, Jia Y, Ho HK, Rademacher P, Bammler TK, Beyer RP, et al. (September 2007). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2802183">"Comparison of the cytotoxicity of the nitroaromatic drug flutamide to its cyano analogue in the hepatocyte cell line TAMH: evidence for complex I inhibition and mitochondrial dysfunction using toxicogenomic screening"</a>. Chemical Research in Toxicology. 20 (9): 1277–1290. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Ftx7001349">10.1021/tx7001349</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/PMC2802183">2802183</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/17702527">17702527</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Research+in+Toxicology&rft.atitle=Comparison+of+the+cytotoxicity+of+the+nitroaromatic+drug+flutamide+to+its+cyano+analogue+in+the+hepatocyte+cell+line+TAMH%3A+evidence+for+complex+I+inhibition+and+mitochondrial+dysfunction+using+toxicogenomic+screening&rft.volume=20&rft.issue=9&rft.pages=1277-1290&rft.date=2007-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2802183%23id-name%3DPMC&rft_id=info%3Apmid%2F17702527&rft_id=info%3Adoi%2F10.1021%2Ftx7001349&rft.aulast=Coe&rft.aufirst=KJ&rft.au=Jia%2C+Y&rft.au=Ho%2C+HK&rft.au=Rademacher%2C+P&rft.au=Bammler%2C+TK&rft.au=Beyer%2C+RP&rft.au=Farin%2C+FM&rft.au=Woodke%2C+L&rft.au=Plymate%2C+SR&rft.au=Fausto%2C+N&rft.au=Nelson%2C+SD&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2802183&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-BoelsterliHo2006-67"><a href="#cite_ref-BoelsterliHo2006_67-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoelsterliHoZhouLeow2006" class="citation journal cs1">Boelsterli UA, Ho HK, Zhou S, Leow KY (October 2006). "Bioactivation and hepatotoxicity of nitroaromatic drugs". Current Drug Metabolism. 7 (7): 715–727. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F138920006778520606">10.2174/138920006778520606</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/17073576">17073576</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Drug+Metabolism&rft.atitle=Bioactivation+and+hepatotoxicity+of+nitroaromatic+drugs&rft.volume=7&rft.issue=7&rft.pages=715-727&rft.date=2006-10&rft_id=info%3Adoi%2F10.2174%2F138920006778520606&rft_id=info%3Apmid%2F17073576&rft.aulast=Boelsterli&rft.aufirst=UA&rft.au=Ho%2C+HK&rft.au=Zhou%2C+S&rft.au=Leow%2C+KY&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid2788775-69"><a href="#cite_ref-pmid2788775_69-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAyubLevell1989" class="citation journal cs1">Ayub M, Levell MJ (August 1989). "The effect of ketoconazole related imidazole drugs and antiandrogens on [3H] R 1881 binding to the prostatic androgen receptor and [3H]5 alpha-dihydrotestosterone and [3H]cortisol binding to plasma proteins". J. Steroid Biochem. 33 (2): 251–5. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0022-4731%2889%2990301-4">10.1016/0022-4731(89)90301-4</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/2788775">2788775</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Steroid+Biochem.&rft.atitle=The+effect+of+ketoconazole+related+imidazole+drugs+and+antiandrogens+on+%5B3H%5D+R+1881+binding+to+the+prostatic+androgen+receptor+and+%5B3H%5D5+alpha-dihydrotestosterone+and+%5B3H%5Dcortisol+binding+to+plasma+proteins&rft.volume=33&rft.issue=2&rft.pages=251-5&rft.date=1989-08&rft_id=info%3Adoi%2F10.1016%2F0022-4731%2889%2990301-4&rft_id=info%3Apmid%2F2788775&rft.aulast=Ayub&rft.aufirst=M&rft.au=Levell%2C+MJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-Gaillard1996-71"><a href="#cite_ref-Gaillard1996_71-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGaillard1996" class="citation book cs1">Gaillard M (1996). "Pharmacodynamics and Pharmacokinetics of Nilutamide in Animal and Man". Antiandrogens in Prostate Cancer. pp. 95–103. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-45745-6_9">10.1007/978-3-642-45745-6_9</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-45747-0" title="Special:BookSources/978-3-642-45747-0"><bdi>978-3-642-45747-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Pharmacodynamics+and+Pharmacokinetics+of+Nilutamide+in+Animal+and+Man&rft.btitle=Antiandrogens+in+Prostate+Cancer&rft.pages=95-103&rft.date=1996&rft_id=info%3Adoi%2F10.1007%2F978-3-642-45745-6_9&rft.isbn=978-3-642-45747-0&rft.aulast=Gaillard&rft.aufirst=M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-FiggChau2010-72">^ <a href="#cite_ref-FiggChau2010_72-0">a</a> <a href="#cite_ref-FiggChau2010_72-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFFiggChauSmall2010" class="citation book cs1">Figg W, Chau CH, Small EJ (14 September 2010). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4KDrjeWA5-UC&pg=PA71">Drug Management of Prostate Cancer</a>. Springer Science & Business Media. pp. 71–. <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>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230110224030/https://books.google.com/books?id=4KDrjeWA5-UC&pg=PA71">Archived</a> from the original on 10 January 2023. Retrieved 12 October 2016.</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=71-&rft.pub=Springer+Science+%26+Business+Media&rft.date=2010-09-14&rft.isbn=978-1-60327-829-4&rft.aulast=Figg&rft.aufirst=W&rft.au=Chau%2C+CH&rft.au=Small%2C+EJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4KDrjeWA5-UC%26pg%3DPA71&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-BenniVemer1990-73"><a href="#cite_ref-BenniVemer1990_73-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBenniVemer1990" class="citation book cs1">Benni HJ, Vemer HM (15 December 1990). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=q6zqFrCLUoIC&pg=PA153">Chronic Hyperandrogenic Anovulation</a>. CRC Press. pp. 153–. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-85070-322-8" title="Special:BookSources/978-1-85070-322-8"><bdi>978-1-85070-322-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Chronic+Hyperandrogenic+Anovulation&rft.pages=153-&rft.pub=CRC+Press&rft.date=1990-12-15&rft.isbn=978-1-85070-322-8&rft.aulast=Benni&rft.aufirst=HJ&rft.au=Vemer%2C+HM&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dq6zqFrCLUoIC%26pg%3DPA153&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid3331376-74"><a href="#cite_ref-pmid3331376_74-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRaynaudFietLe_GoffMartin1987" class="citation journal cs1">Raynaud JP, Fiet J, Le Goff JM, Martin PM, Moguilewsky M, Ojasoo T (1987). 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The Prostate. 13 (1): 69–78. <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.2990130108">10.1002/pros.2990130108</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/3420036">3420036</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:23553575">23553575</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&rft.atitle=Efficacy+and+advantages+in+the+use+of+low+doses+of+Anandron+and+estrogen+combination+in+the+treatment+of+prostate+cancer&rft.volume=13&rft.issue=1&rft.pages=69-78&rft.date=1988&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A23553575%23id-name%3DS2CID&rft_id=info%3Apmid%2F3420036&rft_id=info%3Adoi%2F10.1002%2Fpros.2990130108&rft.aulast=Rao&rft.aufirst=BR&rft.au=Geldof%2C+AA&rft.au=van+der+Wilt%2C+CL&rft.au=de+Voogt%2C+HJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid25665553-89"><a href="#cite_ref-pmid25665553_89-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChiaO'BrienBrownLim2015" class="citation journal cs1">Chia K, O'Brien M, Brown M, Lim E (February 2015). <a rel="nofollow" class="external text" href="http://handle.unsw.edu.au/1959.4/61991">"Targeting the androgen receptor in breast cancer"</a>. Current Oncology Reports. 17 (2): 4. <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%2Fs11912-014-0427-8">10.1007/s11912-014-0427-8</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/25665553">25665553</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:5174768">5174768</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Oncology+Reports&rft.atitle=Targeting+the+androgen+receptor+in+breast+cancer&rft.volume=17&rft.issue=2&rft.pages=4&rft.date=2015-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A5174768%23id-name%3DS2CID&rft_id=info%3Apmid%2F25665553&rft_id=info%3Adoi%2F10.1007%2Fs11912-014-0427-8&rft.aulast=Chia&rft.aufirst=K&rft.au=O%27Brien%2C+M&rft.au=Brown%2C+M&rft.au=Lim%2C+E&rft_id=http%3A%2F%2Fhandle.unsw.edu.au%2F1959.4%2F61991&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"> </li> <li id="cite_note-pmid1903951-90"><a href="#cite_ref-pmid1903951_90-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMillwardCantwellDowsettCarmichael1991" class="citation journal cs1">Millward MJ, Cantwell BM, Dowsett M, Carmichael J, Harris AL (May 1991). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1972372">"Phase II clinical and endocrine study of Anandron (RU-23908) in advanced post-menopausal breast cancer"</a>. British Journal of Cancer. 63 (5): 763–764. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fbjc.1991.170">10.1038/bjc.1991.170</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/PMC1972372">1972372</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/1903951">1903951</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+Cancer&rft.atitle=Phase+II+clinical+and+endocrine+study+of+Anandron+%28RU-23908%29+in+advanced+post-menopausal+breast+cancer&rft.volume=63&rft.issue=5&rft.pages=763-764&rft.date=1991-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1972372%23id-name%3DPMC&rft_id=info%3Apmid%2F1903951&rft_id=info%3Adoi%2F10.1038%2Fbjc.1991.170&rft.aulast=Millward&rft.aufirst=MJ&rft.au=Cantwell%2C+BM&rft.au=Dowsett%2C+M&rft.au=Carmichael%2C+J&rft.au=Harris%2C+AL&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1972372&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" 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=Nilutamide&action=edit&section=20" 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="CITEREFRaynaudBonneMoguilewskyLefebvre1984" class="citation journal cs1">Raynaud JP, Bonne C, Moguilewsky M, Lefebvre FA, Bélanger A, Labrie F (1984). "The pure antiandrogen RU 23908 (Anandron), a candidate of choice for the combined antihormonal treatment of prostatic cancer: a review". The Prostate. 5 (3): 299–311. <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.2990050307">10.1002/pros.2990050307</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/6374639">6374639</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:85417869">85417869</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&rft.atitle=The+pure+antiandrogen+RU+23908+%28Anandron%29%2C+a+candidate+of+choice+for+the+combined+antihormonal+treatment+of+prostatic+cancer%3A+a+review&rft.volume=5&rft.issue=3&rft.pages=299-311&rft.date=1984&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A85417869%23id-name%3DS2CID&rft_id=info%3Apmid%2F6374639&rft_id=info%3Adoi%2F10.1002%2Fpros.2990050307&rft.aulast=Raynaud&rft.aufirst=JP&rft.au=Bonne%2C+C&rft.au=Moguilewsky%2C+M&rft.au=Lefebvre%2C+FA&rft.au=B%C3%A9langer%2C+A&rft.au=Labrie%2C+F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMoguilewskyBertagnaHucher1987" class="citation journal cs1">Moguilewsky M, Bertagna C, Hucher M (1987). 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"Nilutamide: an antiandrogen for the treatment of prostate cancer". The Annals of Pharmacotherapy. 31 (1): 65–75. <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%2F106002809703100112">10.1177/106002809703100112</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/8997470">8997470</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:20347526">20347526</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Annals+of+Pharmacotherapy&rft.atitle=Nilutamide%3A+an+antiandrogen+for+the+treatment+of+prostate+cancer&rft.volume=31&rft.issue=1&rft.pages=65-75&rft.date=1997-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20347526%23id-name%3DS2CID&rft_id=info%3Apmid%2F8997470&rft_id=info%3Adoi%2F10.1177%2F106002809703100112&rft.aulast=Dole&rft.aufirst=EJ&rft.au=Holdsworth%2C+MT&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFIversenMelezinekSchmidt2001" class="citation journal cs1">Iversen P, Melezinek I, Schmidt A (January 2001). <a rel="nofollow" class="external text" href="https://doi.org/10.1046%2Fj.1464-410x.2001.00988.x">"Nonsteroidal antiandrogens: a therapeutic option for patients with advanced prostate cancer who wish to retain sexual interest and function"</a>. BJU International. 87 (1): 47–56. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1046%2Fj.1464-410x.2001.00988.x">10.1046/j.1464-410x.2001.00988.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/11121992">11121992</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:28215804">28215804</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=Nonsteroidal+antiandrogens%3A+a+therapeutic+option+for+patients+with+advanced+prostate+cancer+who+wish+to+retain+sexual+interest+and+function&rft.volume=87&rft.issue=1&rft.pages=47-56&rft.date=2001-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A28215804%23id-name%3DS2CID&rft_id=info%3Apmid%2F11121992&rft_id=info%3Adoi%2F10.1046%2Fj.1464-410x.2001.00988.x&rft.aulast=Iversen&rft.aufirst=P&rft.au=Melezinek%2C+I&rft.au=Schmidt%2C+A&rft_id=https%3A%2F%2Fdoi.org%2F10.1046%252Fj.1464-410x.2001.00988.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANilutamide" class="Z3988"></li></ul> </div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid 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#fdfdfd}.mw-parser-output .navbox-title{background-color:#ccf}.mw-parser-output .navbox-abovebelow,.mw-parser-output .navbox-group,.mw-parser-output .navbox-subgroup .navbox-title{background-color:#ddf}.mw-parser-output .navbox-subgroup .navbox-group,.mw-parser-output .navbox-subgroup .navbox-abovebelow{background-color:#e6e6ff}.mw-parser-output .navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Androgens_and_antiandrogens" 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:Androgens_and_antiandrogens" title="Template:Androgens and antiandrogens"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Androgens_and_antiandrogens" title="Template talk:Androgens and antiandrogens"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Androgens_and_antiandrogens" title="Special:EditPage/Template:Androgens and antiandrogens"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Androgens_and_antiandrogens" style="font-size:114%;margin:0 4em"><a href="/wiki/Androgen" title="Androgen">Androgens</a> and <a href="/wiki/Antiandrogen" title="Antiandrogen">antiandrogens</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Androgen" title="Androgen">Androgens</a> (incl. <a href="/wiki/Anabolic%E2%80%93androgenic_steroid" class="mw-redirect" title="Anabolic–androgenic steroid"><abbr title="anabolic–androgenic steroid">AAS</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 anabolic–androgenic steroid)</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:9em;;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 <a href="/wiki/Agonist" title="Agonist">agonists</a></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/Androstenediol_dipropionate" title="Androstenediol dipropionate">Androstenediol dipropionate</a></li> <li><a href="/wiki/Boldenone_undecylenate" title="Boldenone undecylenate">Boldenone undecylenate</a></li> <li><a href="/wiki/Clostebol" title="Clostebol">Clostebol</a></li> <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> <li><a href="/wiki/Cloxotestosterone_acetate" title="Cloxotestosterone acetate">Cloxotestosterone acetate</a></li> <li><a href="/wiki/Prasterone" title="Prasterone">Prasterone (dehydroepiandrosterone, DHEA)</a></li> <li><a href="/wiki/Prasterone_enanthate" title="Prasterone enanthate">Prasterone enanthate (DHEA enanthate)</a></li> <li><a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">Prasterone sulfate (DHEA sulfate)</a></li> <li><a href="/wiki/Quinbolone" title="Quinbolone">Quinbolone</a></li> <li><a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">Testosterone</a>#</li> <li><a href="/wiki/List_of_androgen_esters#Testosterone_esters" title="List of androgen esters">Testosterone esters</a> (e.g., <a href="/wiki/Testosterone_cypionate" title="Testosterone cypionate">testosterone cypionate</a>, <a href="/wiki/Testosterone_enanthate" title="Testosterone enanthate">testosterone enanthate</a>, <a href="/wiki/Testosterone_propionate" title="Testosterone propionate">testosterone propionate</a>, <a href="/wiki/Testosterone_undecanoate" title="Testosterone undecanoate">testosterone undecanoate</a>, <a href="/wiki/Testosterone_ester_mixture" class="mw-redirect" title="Testosterone ester mixture">testosterone ester mixtures</a> (<a href="/wiki/Deposterona" class="mw-redirect" title="Deposterona">Deposterona</a>, <a href="/wiki/Omnadren" class="mw-redirect" title="Omnadren">Omnadren</a>, <a href="/wiki/Testosterone_propionate/testosterone_phenylpropionate/testosterone_isocaproate/testosterone_decanoate" title="Testosterone propionate/testosterone phenylpropionate/testosterone isocaproate/testosterone decanoate">Sustanon</a>, <a href="/wiki/Testoviron_depot" class="mw-redirect" title="Testoviron depot">Testoviron Depot</a>))</li></ul> <ul><li>Dihydrotestosterone derivatives: <a href="/wiki/Androstanolone" title="Androstanolone">Androstanolone (stanolone, dihydrotestosterone, DHT)</a></li> <li><a href="/wiki/List_of_androgen_esters#Dihydrotestosterone_esters" title="List of androgen esters">Androstanolone esters</a></li> <li><a href="/wiki/Bolazine_capronate" title="Bolazine capronate">Bolazine capronate</a></li> <li><a href="/wiki/Drostanolone_propionate" title="Drostanolone propionate">Drostanolone propionate (dromostanolone propionate)</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/Mesterolone" title="Mesterolone">Mesterolone</a></li> <li><a href="/wiki/Metenolone_acetate" title="Metenolone acetate">Metenolone acetate (methenolone acetate)</a></li> <li><a href="/wiki/Metenolone_enanthate" title="Metenolone enanthate">Metenolone enanthate (methenolone enanthate)</a></li> <li><a href="/wiki/Stenbolone_acetate" title="Stenbolone acetate">Stenbolone acetate</a></li></ul> <ul><li>19-Nortestosterone derivatives: <a href="/wiki/Bolandiol_dipropionate" title="Bolandiol dipropionate">Bolandiol dipropionate</a></li> <li><a href="/wiki/List_of_androgen_esters#Nandrolone_esters" title="List of androgen esters">Nandrolone esters</a> (e.g., <a href="/wiki/Nandrolone_decanoate" title="Nandrolone decanoate">nandrolone decanoate</a>, <a href="/wiki/Nandrolone_phenylpropionate" title="Nandrolone phenylpropionate">nandrolone phenylpropionate</a>)</li> <li><a href="/wiki/Norclostebol" title="Norclostebol">Norclostebol</a></li> <li><a href="/wiki/Norclostebol_acetate" title="Norclostebol acetate">Norclostebol acetate</a></li> <li><a href="/wiki/Oxabolone_cipionate" title="Oxabolone cipionate">Oxabolone cipionate (oxabolone cypionate)</a></li> <li><a href="/wiki/Trenbolone_acetate" title="Trenbolone acetate">Trenbolone acetate</a></li> <li><a href="/wiki/Trenbolone_hexahydrobenzylcarbonate" title="Trenbolone hexahydrobenzylcarbonate">Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)</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/Chlorodehydromethyltestosterone" title="Chlorodehydromethyltestosterone">Chlorodehydromethyltestosterone (CDMT)</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/Metandienone" title="Metandienone">Metandienone (methandienone, methandrostenolone)</a></li> <li><a href="/wiki/Methandriol" title="Methandriol">Methandriol (methylandrostenediol)</a></li> <li><a href="/wiki/Methandriol_bisenanthoyl_acetate" title="Methandriol bisenanthoyl acetate">Methandriol bisenanthoyl acetate</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> <li><a href="/wiki/Methyltestosterone" title="Methyltestosterone">Methyltestosterone</a></li> <li><a href="/wiki/Methyltestosterone_3-hexyl_ether" title="Methyltestosterone 3-hexyl ether">Methyltestosterone 3-hexyl ether</a></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 (thiomesterone)</a></li></ul> <ul><li>17α-Alkylated dihydrotestosterone derivatives: <a href="/wiki/Androisoxazole" title="Androisoxazole">Androisoxazole</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/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/Ethylestrenol" title="Ethylestrenol">Ethylestrenol</a></li> <li><a href="/wiki/Mibolerone" title="Mibolerone">Mibolerone</a></li> <li><a href="/wiki/Norethandrolone" title="Norethandrolone">Norethandrolone</a></li> <li><a href="/wiki/Normethandrone" title="Normethandrone">Normethandrone (methylestrenolone, normethisterone)</a></li> <li><a href="/wiki/Propetandrol" title="Propetandrol">Propetandrol (propethandrol)</a></li></ul> <ul><li>17α-Vinyltestosterone derivatives: <a href="/wiki/Norvinisterone" title="Norvinisterone">Norvinisterone (vinylnortestosterone)</a></li></ul> <ul><li>17α-Ethynyltestosterone derivatives: <a href="/wiki/Danazol" title="Danazol">Danazol</a></li> <li><a href="/wiki/Gestrinone" title="Gestrinone">Gestrinone</a></li> <li><a href="/wiki/Progestin" class="mw-redirect" title="Progestin">Progestins</a> (e.g., <a href="/wiki/Ethisterone" title="Ethisterone">ethisterone (ethynyltestosterone)</a>, <a href="/wiki/Levonorgestrel" title="Levonorgestrel">levonorgestrel</a>, <a href="/wiki/Norgestrel" title="Norgestrel">norgestrel</a>, <a href="/wiki/Norethisterone" title="Norethisterone">norethisterone (norethindrone)</a>, <a href="/wiki/Lynestrenol" title="Lynestrenol">lynestrenol</a>, <a href="/wiki/Norgestrienone" title="Norgestrienone">norgestrienone</a>)</li> <li><a href="/wiki/Tibolone" title="Tibolone">Tibolone</a></li></ul> <ul><li>Progesterone derivatives: <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">Medroxyprogesterone acetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;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/Antiestrogen" title="Antiestrogen">Antiestrogens</a> (e.g., <a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a>, <a href="/wiki/Clomifene" title="Clomifene">clomifene</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonists</a> (e.g., <a href="/wiki/Gonadotropin-releasing_hormone" title="Gonadotropin-releasing hormone">GnRH (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/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, <a href="/wiki/Human_chorionic_gonadotropin" title="Human chorionic gonadotropin"><abbr title="human chorionic gonadotropin">hCG</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 human chorionic gonadotropin)</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/Antiandrogen" title="Antiandrogen">Antiandrogens</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:9em;;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 <a href="/wiki/Receptor_antagonist" title="Receptor antagonist">antagonists</a></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/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+niraparib</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/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Delmadinone_acetate" title="Delmadinone acetate">Delmadinone acetate</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/Medrogestone" title="Medrogestone">Medrogestone</a></li> <li><a href="/wiki/Megestrol_acetate" title="Megestrol acetate">Megestrol acetate</a></li> <li><a href="/wiki/Nomegestrol_acetate" title="Nomegestrol acetate">Nomegestrol acetate</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/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul> <ul><li>Nonsteroidal: <a href="/wiki/Apalutamide" title="Apalutamide">Apalutamide</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Cimetidine</a></li> <li><a href="/wiki/Darolutamide" title="Darolutamide">Darolutamide</a></li> <li><a href="/wiki/Enzalutamide" title="Enzalutamide">Enzalutamide</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a class="mw-selflink selflink">Nilutamide</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a>†</li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Steroidogenesis_inhibitor" title="Steroidogenesis inhibitor">Steroidogenesis inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="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%;text-align:center;"><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase</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/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Epristeride" title="Epristeride">Epristeride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</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/Abiraterone_acetate" title="Abiraterone acetate">Abiraterone acetate</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+niraparib</a></li> <li><a href="/wiki/Aminoglutethimide" title="Aminoglutethimide">Aminoglutethimide</a></li> <li><a href="/wiki/Bifluranol" title="Bifluranol">Bifluranol</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a class="mw-selflink selflink">Nilutamide</a></li> <li><a href="/wiki/Seviteronel" title="Seviteronel">Seviteronel</a>†</li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:9em;;text-align:center;"><a href="/wiki/Antigonadotropin" title="Antigonadotropin">Antigonadotropins</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/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_releaser" class="mw-redirect" title="Prolactin releaser">prolactin releasers</a>) (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/Estrogen" title="Estrogen">Estrogens</a> (e.g., <a href="/wiki/Bifluranol" title="Bifluranol">bifluranol</a>, <a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">diethylstilbestrol</a>, <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>, <a href="/wiki/List_of_estrogen_esters#Estradiol_esters" title="List of estrogen esters">estradiol esters</a>, <a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">ethinylestradiol</a>, <a href="/wiki/Ethinylestradiol_sulfonate" title="Ethinylestradiol sulfonate">ethinylestradiol sulfonate</a>, <a href="/wiki/Paroxypropione" title="Paroxypropione">paroxypropione</a>)</li> <li><a href="/wiki/GnRH_agonist" class="mw-redirect" title="GnRH agonist">GnRH agonists</a> (e.g., <a href="/wiki/Leuprorelin" title="Leuprorelin">leuprorelin</a>)</li> <li><a href="/wiki/GnRH_antagonist" class="mw-redirect" title="GnRH antagonist">GnRH antagonists</a> (e.g., <a href="/wiki/Cetrorelix" title="Cetrorelix">cetrorelix</a>)</li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (incl., <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/Hydroxyprogesterone_caproate" title="Hydroxyprogesterone caproate">hydroxyprogesterone caproate</a>, <a href="/wiki/Gestonorone_caproate" title="Gestonorone caproate">gestonorone 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:9em;;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <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-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Androgen_receptor_modulators" title="Template:Androgen receptor modulators">Androgen receptor 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:Progestogens_and_antiprogestogens" title="Template:Progestogens and antiprogestogens">Progestogens and antiprogestogens</a></dd> <dd><a href="/wiki/List_of_androgens/anabolic_steroids" class="mw-redirect" title="List of androgens/anabolic steroids">List of androgens/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="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 class="mw-selflink selflink">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><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" 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=Nilutamide&oldid=1260920724">https://en.wikipedia.org/w/index.php?title=Nilutamide&oldid=1260920724</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:CYP17A1_inhibitors" title="Category:CYP17A1 inhibitors">CYP17A1 inhibitors</a></li><li><a href="/wiki/Category:Disulfiram-like_drugs" 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