121 lines
45 KiB
Text
121 lines
45 KiB
Text
<!DOCTYPE html>
|
|
<html xmlns="http://www.w3.org/1999/xhtml" xml:lang="en" class="no-js no-jr">
|
|
<head>
|
|
<!-- For pinger, set start time and add meta elements. -->
|
|
<script type="text/javascript">var ncbi_startTime = new Date();</script>
|
|
|
|
<!-- Logger begin -->
|
|
<meta name="ncbi_db" content="books">
|
|
<meta name="ncbi_pdid" content="book-part">
|
|
<meta name="ncbi_acc" content="NBK548491">
|
|
<meta name="ncbi_domain" content="livertox">
|
|
<meta name="ncbi_report" content="reader">
|
|
<meta name="ncbi_type" content="fulltext">
|
|
<meta name="ncbi_objectid" content="">
|
|
<meta name="ncbi_pcid" content="/NBK548491/?report=reader">
|
|
<meta name="ncbi_pagename" content="Antiandrogens - LiverTox - NCBI Bookshelf">
|
|
<meta name="ncbi_bookparttype" content="chapter">
|
|
<meta name="ncbi_app" content="bookshelf">
|
|
<!-- Logger end -->
|
|
|
|
<!--component id="Page" label="meta"/-->
|
|
<script type="text/javascript" src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.boots.min.js"> </script><title>Antiandrogens - LiverTox - NCBI Bookshelf</title>
|
|
<meta charset="utf-8">
|
|
<meta name="apple-mobile-web-app-capable" content="no">
|
|
<meta name="viewport" content="initial-scale=1,minimum-scale=1,maximum-scale=1,user-scalable=no">
|
|
<meta name="jr-col-layout" content="auto">
|
|
<meta name="jr-prev-unit" content="/books/n/livertox/AnthraxAntitoxins/?report=reader">
|
|
<meta name="jr-next-unit" content="/books/n/livertox/AntiarrhythmicAgents/?report=reader">
|
|
<meta name="bk-toc-url" content="/books/n/livertox/?report=toc">
|
|
<meta name="robots" content="INDEX,FOLLOW,NOARCHIVE">
|
|
<meta name="citation_inbook_title" content="LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]">
|
|
<meta name="citation_title" content="Antiandrogens">
|
|
<meta name="citation_publisher" content="National Institute of Diabetes and Digestive and Kidney Diseases">
|
|
<meta name="citation_date" content="2014/06/10">
|
|
<meta name="citation_pmid" content="31643810">
|
|
<meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK548491/">
|
|
<link rel="schema.DC" href="http://purl.org/DC/elements/1.0/">
|
|
<meta name="DC.Title" content="Antiandrogens">
|
|
<meta name="DC.Type" content="Text">
|
|
<meta name="DC.Publisher" content="National Institute of Diabetes and Digestive and Kidney Diseases">
|
|
<meta name="DC.Date" content="2014/06/10">
|
|
<meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK548491/">
|
|
<meta name="description" content="The antiandrogens are medications that act by binding to intracellular androgen receptors, preventing the effects of endogenous androgens on target tissues such as testes, hair follicles, hypothalamus, pituitary, ovaries and prostate gland. The antiandrogens are used for a variety of hyperandrogenic states such as acne, hirsutism, and paraphilias, but their major use is in therapy of prostate cancer. Chemically, antiandrogens are classified into steroidal (such as cyproterone acetate) and nonsteroidal (including flutamide, nilutamide and bicalutamide). Cyproterone, despite evaluation in many clinical trials, has yet to receive FDA approval for use the United States, largely because of its potential for hepatotoxicity. In contrast, flutamide, nilutamide and bicalutamide are now approved and in general clinical use for therapy of prostate cancer. The largest and longest clinical experience has been with flutamide which has been shown to produce clinical remission in patients with prostate cancer, and is also used in hyperandrogenic states including acne and hirsutism. Nilutamide has been extensively studied and is indicated for use in combination with surgical castration for the treatment of metastatic prostate cancer and is recommended to be started at the time of orchiectomy. Unlike flutamide, nilutamide has not been evaluated in detail as therapy of hirsutism or acne. Bicalutamide, the most recent antiandrogen to be approved for use in the United States, is also used in therapy of prostate cancer, but has not been approved for use in nonmalignant hyperandrogenic states.">
|
|
<meta name="og:title" content="Antiandrogens">
|
|
<meta name="og:type" content="book">
|
|
<meta name="og:description" content="The antiandrogens are medications that act by binding to intracellular androgen receptors, preventing the effects of endogenous androgens on target tissues such as testes, hair follicles, hypothalamus, pituitary, ovaries and prostate gland. The antiandrogens are used for a variety of hyperandrogenic states such as acne, hirsutism, and paraphilias, but their major use is in therapy of prostate cancer. Chemically, antiandrogens are classified into steroidal (such as cyproterone acetate) and nonsteroidal (including flutamide, nilutamide and bicalutamide). Cyproterone, despite evaluation in many clinical trials, has yet to receive FDA approval for use the United States, largely because of its potential for hepatotoxicity. In contrast, flutamide, nilutamide and bicalutamide are now approved and in general clinical use for therapy of prostate cancer. The largest and longest clinical experience has been with flutamide which has been shown to produce clinical remission in patients with prostate cancer, and is also used in hyperandrogenic states including acne and hirsutism. Nilutamide has been extensively studied and is indicated for use in combination with surgical castration for the treatment of metastatic prostate cancer and is recommended to be started at the time of orchiectomy. Unlike flutamide, nilutamide has not been evaluated in detail as therapy of hirsutism or acne. Bicalutamide, the most recent antiandrogen to be approved for use in the United States, is also used in therapy of prostate cancer, but has not been approved for use in nonmalignant hyperandrogenic states.">
|
|
<meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK548491/">
|
|
<meta name="og:site_name" content="NCBI Bookshelf">
|
|
<meta name="og:image" content="https://www.ncbi.nlm.nih.gov/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-livertox-lrg.png">
|
|
<meta name="twitter:card" content="summary">
|
|
<meta name="twitter:site" content="@ncbibooks">
|
|
<meta name="bk-non-canon-loc" content="/books/n/livertox/Anti-androgens/?report=reader">
|
|
<link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK548491/">
|
|
<link href="https://fonts.googleapis.com/css?family=Archivo+Narrow:400,700,400italic,700italic&subset=latin" rel="stylesheet" type="text/css">
|
|
<link rel="stylesheet" href="/corehtml/pmc/jatsreader/ptpmc_3.22/css/libs.min.css">
|
|
<link rel="stylesheet" href="/corehtml/pmc/jatsreader/ptpmc_3.22/css/jr.min.css">
|
|
<meta name="format-detection" content="telephone=no">
|
|
<link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books.min.css" type="text/css">
|
|
<link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css//books_print.min.css" type="text/css" media="print">
|
|
<link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books_reader.min.css" type="text/css">
|
|
<style type="text/css">p a.figpopup{display:inline !important} .bk_tt {font-family: monospace} .first-line-outdent .bk_ref {display: inline} .body-content h2, .body-content .h2 {border-bottom: 1px solid #97B0C8} .body-content h2.inline {border-bottom: none} a.page-toc-label , .jig-ncbismoothscroll a {text-decoration:none;border:0 !important} .temp-labeled-list .graphic {display:inline-block !important} .temp-labeled-list img{width:100%}</style>
|
|
|
|
<link rel="shortcut icon" href="//www.ncbi.nlm.nih.gov/favicon.ico">
|
|
<meta name="ncbi_phid" content="CE8C536F7D7AE1A100000000011200E5.m_5">
|
|
<meta name='referrer' content='origin-when-cross-origin'/><link type="text/css" rel="stylesheet" href="//static.pubmed.gov/portal/portal3rc.fcgi/4216699/css/3852956/3849091.css"></head>
|
|
<body>
|
|
<!-- Book content! -->
|
|
|
|
|
|
<div id="jr" data-jr-path="/corehtml/pmc/jatsreader/ptpmc_3.22/"><div class="jr-unsupported"><table class="modal"><tr><td><span class="attn inline-block"></span><br />Your browser does not support the NLM PubReader view.<br />Go to <a href="/pmc/about/pr-browsers/">this page</a> to see a list of supported browsers<br />or return to the <br /><a href="/books/NBK548491/?report=classic">regular view</a>.</td></tr></table></div><div id="jr-ui" class="hidden"><nav id="jr-head"><div class="flexh tb"><div id="jr-tb1"><a id="jr-links-sw" class="hidden" title="Links"><svg xmlns="http://www.w3.org/2000/svg" version="1.1" x="0px" y="0px" viewBox="0 0 70.6 85.3" style="enable-background:new 0 0 70.6 85.3;vertical-align:middle" xml:space="preserve" width="24" height="24">
|
|
<style type="text/css">.st0{fill:#939598;}</style>
|
|
<g>
|
|
<path class="st0" d="M36,0C12.8,2.2-22.4,14.6,19.6,32.5C40.7,41.4-30.6,14,35.9,9.8"></path>
|
|
<path class="st0" d="M34.5,85.3c23.2-2.2,58.4-14.6,16.4-32.5c-21.1-8.9,50.2,18.5-16.3,22.7"></path>
|
|
<path class="st0" d="M34.7,37.1c66.5-4.2-4.8-31.6,16.3-22.7c42.1,17.9,6.9,30.3-16.4,32.5h1.7c-66.2,4.4,4.8,31.6-16.3,22.7 c-42.1-17.9-6.9-30.3,16.4-32.5"></path>
|
|
</g>
|
|
</svg> Books</a></div><div class="jr-rhead f1 flexh"><div class="head"><a href="/books/n/livertox/AnthraxAntitoxins/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M75,30 c-80,60 -80,0 0,60 c-30,-60 -30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Prev</text></svg></a></div><div class="body"><div class="t">Antiandrogens</div><div class="j">LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]</div></div><div class="tail"><a href="/books/n/livertox/AntiarrhythmicAgents/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M25,30c80,60 80,0 0,60 c30,-60 30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Next</text></svg></a></div></div><div id="jr-tb2"><a id="jr-bkhelp-sw" class="btn wsprkl hidden" title="Help with NLM PubReader">?</a><a id="jr-help-sw" class="btn wsprkl hidden" title="Settings and typography in NLM PubReader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 512 512" preserveAspectRatio="none"><path d="M462,283.742v-55.485l-29.981-10.662c-11.431-4.065-20.628-12.794-25.274-24.001 c-0.002-0.004-0.004-0.009-0.006-0.013c-4.659-11.235-4.333-23.918,0.889-34.903l13.653-28.724l-39.234-39.234l-28.72,13.652 c-10.979,5.219-23.68,5.546-34.908,0.889c-0.005-0.002-0.01-0.003-0.014-0.005c-11.215-4.65-19.933-13.834-24-25.273L283.741,50 h-55.484l-10.662,29.981c-4.065,11.431-12.794,20.627-24.001,25.274c-0.005,0.002-0.009,0.004-0.014,0.005 c-11.235,4.66-23.919,4.333-34.905-0.889l-28.723-13.653l-39.234,39.234l13.653,28.721c5.219,10.979,5.545,23.681,0.889,34.91 c-0.002,0.004-0.004,0.009-0.006,0.013c-4.649,11.214-13.834,19.931-25.271,23.998L50,228.257v55.485l29.98,10.661 c11.431,4.065,20.627,12.794,25.274,24c0.002,0.005,0.003,0.01,0.005,0.014c4.66,11.236,4.334,23.921-0.888,34.906l-13.654,28.723 l39.234,39.234l28.721-13.652c10.979-5.219,23.681-5.546,34.909-0.889c0.005,0.002,0.01,0.004,0.014,0.006 c11.214,4.649,19.93,13.833,23.998,25.271L228.257,462h55.484l10.595-29.79c4.103-11.538,12.908-20.824,24.216-25.525 c0.005-0.002,0.009-0.004,0.014-0.006c11.127-4.628,23.694-4.311,34.578,0.863l28.902,13.738l39.234-39.234l-13.66-28.737 c-5.214-10.969-5.539-23.659-0.886-34.877c0.002-0.005,0.004-0.009,0.006-0.014c4.654-11.225,13.848-19.949,25.297-24.021 L462,283.742z M256,331.546c-41.724,0-75.548-33.823-75.548-75.546s33.824-75.547,75.548-75.547 c41.723,0,75.546,33.824,75.546,75.547S297.723,331.546,256,331.546z"></path></svg></a><a id="jr-fip-sw" class="btn wsprkl hidden" title="Find"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 550 600" preserveAspectRatio="none"><path fill="none" stroke="#000" stroke-width="36" stroke-linecap="round" style="fill:#FFF" d="m320,350a153,153 0 1,0-2,2l170,170m-91-117 110,110-26,26-110-110"></path></svg></a><a id="jr-rtoc-sw" class="btn wsprkl hidden" title="Table of Contents"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M20,20h10v8H20V20zM36,20h44v8H36V20zM20,37.33h10v8H20V37.33zM36,37.33h44v8H36V37.33zM20,54.66h10v8H20V54.66zM36,54.66h44v8H36V54.66zM20,72h10v8 H20V72zM36,72h44v8H36V72z"></path></svg></a></div></div></nav><nav id="jr-dash" class="noselect"><nav id="jr-dash" class="noselect"><div id="jr-pi" class="hidden"><a id="jr-pi-prev" class="hidden" title="Previous page"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M75,30 c-80,60 -80,0 0,60 c-30,-60 -30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Prev</text></svg></a><div class="pginfo">Page <i class="jr-pg-pn">0</i> of <i class="jr-pg-lp">0</i></div><a id="jr-pi-next" class="hidden" title="Next page"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M25,30c80,60 80,0 0,60 c30,-60 30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Next</text></svg></a></div><div id="jr-is-tb"><a id="jr-is-sw" class="btn wsprkl hidden" title="Switch between Figures/Tables strip and Progress bar"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><rect x="10" y="40" width="20" height="20"></rect><rect x="40" y="40" width="20" height="20"></rect><rect x="70" y="40" width="20" height="20"></rect></svg></a></div><nav id="jr-istrip" class="istrip hidden"><a id="jr-is-prev" href="#" class="hidden" title="Previous"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M80,40 60,65 80,90 70,90 50,65 70,40z M50,40 30,65 50,90 40,90 20,65 40,40z"></path><text x="35" y="25" textLength="60" style="font-size:25px">Prev</text></svg></a><a id="jr-is-next" href="#" class="hidden" title="Next"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M20,40 40,65 20,90 30,90 50,65 30,40z M50,40 70,65 50,90 60,90 80,65 60,40z"></path><text x="15" y="25" textLength="60" style="font-size:25px">Next</text></svg></a></nav><nav id="jr-progress"></nav></nav></nav><aside id="jr-links-p" class="hidden flexv"><div class="tb sk-htbar flexh"><div><a class="jr-p-close btn wsprkl">Done</a></div><div class="title-text f1">NCBI Bookshelf</div></div><div class="cnt lol f1"><a href="/books/">Home</a><a href="/books/browse/">Browse All Titles</a><a class="btn share" target="_blank" rel="noopener noreferrer" href="https://www.facebook.com/sharer/sharer.php?u=https://www.ncbi.nlm.nih.gov/books/NBK548491/"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 33 33" style="vertical-align:middle" width="24" height="24" preserveAspectRatio="none"><g><path d="M 17.996,32L 12,32 L 12,16 l-4,0 l0-5.514 l 4-0.002l-0.006-3.248C 11.993,2.737, 13.213,0, 18.512,0l 4.412,0 l0,5.515 l-2.757,0 c-2.063,0-2.163,0.77-2.163,2.209l-0.008,2.76l 4.959,0 l-0.585,5.514L 18,16L 17.996,32z"></path></g></svg> Share on Facebook</a><a class="btn share" target="_blank" rel="noopener noreferrer" href="https://twitter.com/intent/tweet?url=https://www.ncbi.nlm.nih.gov/books/NBK548491/&text=Antiandrogens"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 33 33" style="vertical-align:middle" width="24" height="24"><g><path d="M 32,6.076c-1.177,0.522-2.443,0.875-3.771,1.034c 1.355-0.813, 2.396-2.099, 2.887-3.632 c-1.269,0.752-2.674,1.299-4.169,1.593c-1.198-1.276-2.904-2.073-4.792-2.073c-3.626,0-6.565,2.939-6.565,6.565 c0,0.515, 0.058,1.016, 0.17,1.496c-5.456-0.274-10.294-2.888-13.532-6.86c-0.565,0.97-0.889,2.097-0.889,3.301 c0,2.278, 1.159,4.287, 2.921,5.465c-1.076-0.034-2.088-0.329-2.974-0.821c-0.001,0.027-0.001,0.055-0.001,0.083 c0,3.181, 2.263,5.834, 5.266,6.438c-0.551,0.15-1.131,0.23-1.73,0.23c-0.423,0-0.834-0.041-1.235-0.118 c 0.836,2.608, 3.26,4.506, 6.133,4.559c-2.247,1.761-5.078,2.81-8.154,2.81c-0.53,0-1.052-0.031-1.566-0.092 c 2.905,1.863, 6.356,2.95, 10.064,2.95c 12.076,0, 18.679-10.004, 18.679-18.68c0-0.285-0.006-0.568-0.019-0.849 C 30.007,8.548, 31.12,7.392, 32,6.076z"></path></g></svg> Share on Twitter</a></div></aside><aside id="jr-rtoc-p" class="hidden flexv"><div class="tb sk-htbar flexh"><div><a class="jr-p-close btn wsprkl">Done</a></div><div class="title-text f1">Table of Content</div></div><div class="cnt lol f1"><a href="/books/n/livertox/?report=reader">Title Information</a><a href="/books/n/livertox/toc/?report=reader">Table of Contents Page</a></div></aside><aside id="jr-help-p" class="hidden flexv"><div class="tb sk-htbar flexh"><div><a class="jr-p-close btn wsprkl">Done</a></div><div class="title-text f1">Settings</div></div><div class="cnt f1"><div id="jr-typo-p" class="typo"><div><a class="sf btn wsprkl">A-</a><a class="lf btn wsprkl">A+</a></div><div><a class="bcol-auto btn wsprkl"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 200 100" preserveAspectRatio="none"><text x="10" y="70" style="font-size:60px;font-family: Trebuchet MS, ArialMT, Arial, sans-serif" textLength="180">AUTO</text></svg></a><a class="bcol-1 btn wsprkl"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M15,25 85,25zM15,40 85,40zM15,55 85,55zM15,70 85,70z"></path></svg></a><a class="bcol-2 btn wsprkl"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M5,25 45,25z M55,25 95,25zM5,40 45,40z M55,40 95,40zM5,55 45,55z M55,55 95,55zM5,70 45,70z M55,70 95,70z"></path></svg></a></div></div><div class="lol"><a class="" href="/books/NBK548491/?report=classic">Switch to classic view</a><a href="/books/NBK548491/pdf/Bookshelf_NBK548491.pdf">PDF (146K)</a><a href="/books/NBK548491/?report=printable">Print View</a></div></div></aside><aside id="jr-bkhelp-p" class="hidden flexv"><div class="tb sk-htbar flexh"><div><a class="jr-p-close btn wsprkl">Done</a></div><div class="title-text f1">Help</div></div><div class="cnt f1 lol"><a id="jr-helpobj-sw" data-path="/corehtml/pmc/jatsreader/ptpmc_3.22/" data-href="/corehtml/pmc/jatsreader/ptpmc_3.22/img/bookshelf/help.xml" href="">Help</a><a href="mailto:info@ncbi.nlm.nih.gov?subject=PubReader%20feedback%20%2F%20NBK548491%20%2F%20sid%3ACE8B5AF87C7FFCB1_0191SID%20%2F%20phid%3ACE8C536F7D7AE1A100000000011200E5.4">Send us feedback</a><a id="jr-about-sw" data-path="/corehtml/pmc/jatsreader/ptpmc_3.22/" data-href="/corehtml/pmc/jatsreader/ptpmc_3.22/img/bookshelf/about.xml" href="">About PubReader</a></div></aside><aside id="jr-objectbox" class="thidden hidden"><div class="jr-objectbox-close wsprkl">✘</div><div class="jr-objectbox-inner cnt"><div class="jr-objectbox-drawer"></div></div></aside><nav id="jr-pm-left" class="hidden"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 40 800" preserveAspectRatio="none"><text font-stretch="ultra-condensed" x="800" y="-15" text-anchor="end" transform="rotate(90)" font-size="18" letter-spacing=".1em">Previous Page</text></svg></nav><nav id="jr-pm-right" class="hidden"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 40 800" preserveAspectRatio="none"><text font-stretch="ultra-condensed" x="800" y="-15" text-anchor="end" transform="rotate(90)" font-size="18" letter-spacing=".1em">Next Page</text></svg></nav><nav id="jr-fip" class="hidden"><nav id="jr-fip-term-p"><input type="search" placeholder="search this page" id="jr-fip-term" autocorrect="off" autocomplete="off" /><a id="jr-fip-mg" class="wsprkl btn" title="Find"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 550 600" preserveAspectRatio="none"><path fill="none" stroke="#000" stroke-width="36" stroke-linecap="round" style="fill:#FFF" d="m320,350a153,153 0 1,0-2,2l170,170m-91-117 110,110-26,26-110-110"></path></svg></a><a id="jr-fip-done" class="wsprkl btn" title="Dismiss find">✘</a></nav><nav id="jr-fip-info-p"><a id="jr-fip-prev" class="wsprkl btn" title="Jump to previuos match">◀</a><button id="jr-fip-matches">no matches yet</button><a id="jr-fip-next" class="wsprkl btn" title="Jump to next match">▶</a></nav></nav></div><div id="jr-epub-interstitial" class="hidden"></div><div id="jr-content"><article data-type="main"><div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><div class="fm-sec"><h1 id="_NBK548491_"><span class="title" itemprop="name">Antiandrogens</span></h1><p class="fm-aai"><a href="#_NBK548491_pubdet_">Publication Details</a></p></div></div><div class="body-content whole_rhythm" itemprop="text"><div id="Anti-androgens.OVERVIEW"><h2 id="_Anti-androgens_OVERVIEW_">OVERVIEW</h2><p>The antiandrogens are medications that act by binding to intracellular androgen receptors, preventing the effects of endogenous androgens on target tissues such as testes, hair follicles, hypothalamus, pituitary, ovaries and prostate gland. The antiandrogens are used for a variety of hyperandrogenic states such as acne, hirsutism, and paraphilias, but their major use is in therapy of prostate cancer. Chemically, antiandrogens are classified into steroidal (such as cyproterone acetate) and nonsteroidal (including flutamide, nilutamide and bicalutamide). Cyproterone, despite evaluation in many clinical trials, has yet to receive FDA approval for use the United States, largely because of its potential for hepatotoxicity. In contrast, flutamide, nilutamide and bicalutamide are now approved and in general clinical use for therapy of prostate cancer. The largest and longest clinical experience has been with flutamide which has been shown to produce clinical remission in patients with prostate cancer, and is also used in hyperandrogenic states including acne and hirsutism. Nilutamide has been extensively studied and is indicated for use in combination with surgical castration for the treatment of metastatic prostate cancer and is recommended to be started at the time of orchiectomy. Unlike flutamide, nilutamide has not been evaluated in detail as therapy of hirsutism or acne. Bicalutamide, the most recent antiandrogen to be approved for use in the United States, is also used in therapy of prostate cancer, but has not been approved for use in nonmalignant hyperandrogenic states.</p><p>All three nonsteroidal antiandrogens have been linked to instances of liver injury. Minor asymptomatic elevations in serum aminotransferase levels occur in 10% to 62% of patients on long term antiandrogen therapy, and prominent elevations (3 to 5 times the ULN) in 1% to 10%, the rates being somewhat higher for flutamide than nilutamide or bicalutamide. Instances of acute hepatitis with jaundice and even acute liver failure have been reported with all three antiandrogens. While most reports have related to flutamide, this may be due to its more extensive use. The rate of clinically apparent acute liver injury during prolonged antiandrogen therapy is reported to be as high as 9%, but is probably in the range of 0.1% to 1%. Screening for serum aminotransferase levels during the first few months of therapy is often recommended, but the effectiveness of this approach in preventing serious liver injury and death has not been shown.</p><p>Abiraterone is a more recently developed antiandrogen used to treat prostate cancer. Abiraterone is a steroid inhibitor of CYP17, an enzyme in the pathway of androgen production which has been shown to be effective in prolonging relapse free and overall survival in men with metastatic, castration-resistant prostate cancer. Abiraterone has been linked to a moderate rate of serum aminotransferasae elevations during therapy, but the abnormalities are usually mild and transient, and instances of clinically apparent liver injury have not been linked to use of this agent, although its general use has been limited.</p><p>Each of the antiandrogens is discussed separately with individual clinical cases and references. The following are links to each drug record.</p><ul><li class="half_rhythm"><div>
|
|
<a href="/books/n/livertox/Abiraterone/?report=reader">Abiraterone</a>
|
|
</div></li><li class="half_rhythm"><div>
|
|
<a href="/books/n/livertox/Apalutamide/?report=reader">Apalutamide</a>
|
|
</div></li><li class="half_rhythm"><div>
|
|
<a href="/books/n/livertox/Bicalutamide/?report=reader">Bicalutamide</a>
|
|
</div></li><li class="half_rhythm"><div>
|
|
<a href="/books/n/livertox/Cyproterone/?report=reader">Cyproterone</a>
|
|
</div></li><li class="half_rhythm"><div>
|
|
<a href="/books/n/livertox/Enzalutamide/?report=reader">Enzalutamide</a>
|
|
</div></li><li class="half_rhythm"><div>
|
|
<a href="/books/n/livertox/Flutamide/?report=reader">Flutamide</a>
|
|
</div></li><li class="half_rhythm"><div>
|
|
<a href="/books/n/livertox/Nilutamide/?report=reader">Nilutamide</a>
|
|
</div></li></ul></div><div id="Anti-androgens.CHEMICAL_FORMULAS_AND_STR"><h2 id="_Anti-androgens_CHEMICAL_FORMULAS_AND_STR_">CHEMICAL FORMULAS AND STRUCTURES</h2><div class="iconblock whole_rhythm clearfix ten_col table-wrap" id="figAntiandrogensT1"><a href="/books/NBK548491/table/Anti-androgens.T1/?report=objectonly" target="object" title="Table" class="img_link icnblk_img figpopup" rid-figpopup="figAntiandrogensT1" rid-ob="figobAntiandrogensT1"><img class="small-thumb" src="/books/NBK548491/table/Anti-androgens.T1/?report=thumb" src-large="/books/NBK548491/table/Anti-androgens.T1/?report=previmg" alt="Image " /></a><div class="icnblk_cntnt"><h4 id="Anti-androgens.T1"><a href="/books/NBK548491/table/Anti-androgens.T1/?report=objectonly" target="object" rid-ob="figobAntiandrogensT1">Table</a></h4></div></div></div><div id="Anti-androgens.ANNOTATED_BIBLIOGRAPHY"><h2 id="_Anti-androgens_ANNOTATED_BIBLIOGRAPHY_">ANNOTATED BIBLIOGRAPHY</h2><p>References updated: 10 June 2014</p><ul class="first-line-outdent"><li><div class="bk_ref" id="Anti-androgens.R1">Zimmerman HJ. Hepatotoxic effects of oncotherapeutic and immunosuppressive agents. In, Zimmerman HJ. Hepatotoxicity: the adverse effects of drugs and other chemicals on the liver. 2nd ed. Philadelphia: Lippincott, 1999, p. 699.<div><i>(Expert review of hepatotoxicity published in 1999, mentions that flutamide has led to instances of severe hepatic necrosis and fulminant hepatic failure).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R2">DeLeve LD. Flutamide. Cancer chemotherapy. In, Kaplowitz N, DeLeve LD, eds. Drug-induced liver disease. 3rd Edition. Amsterdam: Elsevier. 2013. pp. 559.<div><i>(Textbook on drug induced liver injury mentions that flutamide has been implicated in at least 46 cases of severe liver injury with 20 fatalities).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R3">Moy B, Lee RJ, Smith M. Hormone therapy in prostate cancer. Natural products in cancer chemotherapy: hormones and related agents. In, Brunton LL, Chabner BA, Knollman BC, eds. Goodman & Gilman's the pharmacological basis of therapeutics. 12th ed. New York: McGraw-Hill, 2011, pp. 1763-9.<div><i>(Textbook of pharmacology and therapeutics; discusses the role of androgen receptor blockers in prostate cancer including bicalutamide, flutamide and nilutamide).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R4">Meijers WH, Willemse PH, Sleijfer DT, Mulder NH, Grond J. Hepatocellular damage by cyproterone acetate. Eur J Cancer Clin Oncol 1986; 22: 1121-2. [<a href="https://pubmed.ncbi.nlm.nih.gov/2946585" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2946585</span></a>]<div><i> (In a study of 20 women with breast cancer, cyproterone was given in dose of 200-400 mg/day for 6 to 52 weeks; 5 developed ALT elevations, and two had acute hepatitis after 11 and 21 weeks, with ALT >10 times ULN and liver biopsies showing confluent necrosis).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R5">Lévesque H, Trivalle C, Manchon ND, Vinel JP, Moore N, Hémet J, Courtois H, et al. Fulminant hepatitis due to cyproterone acetate. Lancet 1989; 1: 215-6. [<a href="https://pubmed.ncbi.nlm.nih.gov/2563116" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 2563116</span></a>]<div><i>(78 year old man with prostate cancer developed jaundice 5 months after starting cyproterone [bilirubin 10.4 mg/dL, ALT 1015 U/L, Alk P 153 U/L], progressing to hepatic failure and death within 2 weeks of initial presentation).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R6">Parys BT, Hamid S, Thomson RG. Severe hepatocellular dysfunction following cyproterone acetate therapy. Br J Urol 1991; 67: 312-3. [<a href="https://pubmed.ncbi.nlm.nih.gov/1827039" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 1827039</span></a>]<div><i>(3 case reports of jaundice developing in men [ages 65 to 83 years] with prostate cancer given cyproterone for 9-12 months [bilirubin 19, 10.4, and 16.4 mg/dL; AST 254, 377 and 155 U/L; Alk P 218, 252 and 79 U/L], resolving within 12 weeks of stopping in 1 but progression to liver failure and death in the other 2 patients).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R7">McLeod DG. Tolerability of nonsteroidal antiandrogens in the treatment of advanced prostate cancer. Oncologist 1997; 2: 18-27. [<a href="https://pubmed.ncbi.nlm.nih.gov/10388026" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10388026</span></a>]<div><i>(Overview of the safety and side effects of the nonsteroidal antiandrogens; ALT elevations occur in 5-10% receiving drug vs 1-3% with placebo; clinically apparent hepatitis can occur and can be fatal; estimated rates being 3/10,000 treated).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R8">Friedman G, Lamoureux E, Sherker AH. Fatal fulminant hepatic failure due to cyproterone acetate. Dig Dis Sci 1999; 44: 1362-3. [<a href="https://pubmed.ncbi.nlm.nih.gov/10489919" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10489919</span></a>]<div><i>(81 and 66 year old men with prostate cancer developed jaundice 7 and 8 months after starting cyproterone [bilirubin 30 and 12.2 mg/dL, ALT 395 and 702 U/L, Alk P 376 and 144 U/L], with progression and fatal outcome in both. Review of 7 published cases; onset 2-15 [mean=8] months, bilirubin 9-30 times ULN, all hepatocellular).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R9">Pu YS, Liu CM, Kao JH, Chen J, Lai MK. Antiandrogen hepatotoxicity in patients with chronic viral hepatitis. Eur Urol 1999; 36: 293-7. [<a href="https://pubmed.ncbi.nlm.nih.gov/10473987" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 10473987</span></a>]<div><i>(Retrospective study of 121 men receiving antiandrogen therapy with flutamide or cyproterone found abnormal ALT levels in most or all who were HBsAg or anti-HCV positive; but many were not tested and frequency of ALT monitoring was unclear. Authors propose that antiandrogen hepatotoxicity is more frequent among men with preexisting hepatitis B or C, but no attempt was made to separate hepatotoxicity from exacerbation of underlying disease).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R10">Lin AD, Chen KK, Lin AT, Chang YH, Wu HH, Kuo JY, Huang WJ, et al. Antiandrogen-associated hepatotoxicity in the management of advanced prostate cancer. J Chin Med Assoc 2003; 66: 735-40. [<a href="https://pubmed.ncbi.nlm.nih.gov/15015823" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15015823</span></a>]<div><i>(Retrospective review of 229 patients with prostate cancer treated with flutamide or cyproterone combined with a luteinizing hormone-releasing hormone agonist, orchiectomy or radiotherapy with regular monitoring of ALT: ALT >2 times ULN occurred in 15% of flutamide and 9.5% CPA recipients; ALT >6 times ULN in 5% vs 4%; no deaths, a few had jaundice).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R11">Russo MW, Galanko JA, Shrestha R, Fried MW, Watkins P. Liver transplantation for acute liver failure from drug-induced liver injury in the United States. Liver Transpl 2004; 10: 1018-23. [<a href="https://pubmed.ncbi.nlm.nih.gov/15390328" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15390328</span></a>]<div><i>(Among ~50,000 liver transplants done in the United States between 1990 and 2002, 270 [0.5%] were done for drug induced acute liver failure, but no case was attributed to an antiandrogen, perhaps because patients with prostate cancer would not be eligible for liver transplantation).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R12">Thole Z, Manso G, Salgueiro E, Revuelta P, Hidalgo A. Hepatotoxicity induced by antiandrogens: a review of the literature. Urol Int 2004; 73: 289-95. Review. [<a href="https://pubmed.ncbi.nlm.nih.gov/15604569" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 15604569</span></a>]<div><i>(Systematic review of the literature from the Spanish pharmacovigilance group; 21 reports of hepatotoxicity from cyproterone, 46 flutamide, 4 nilumidine, only 1 bicalutamide; 6 cases of hepatocellular carcinoma linked to cyproterone therapy).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R13">Manso G, Thole Z, Salgueiro E, Revuelta P, Hidalgo A. Spontaneous reporting of hepatotoxicity associated with antiandrogens: data from the Spanish pharmacovigilance system. Pharmacoepidemiol Drug Saf 2006; 15: 253-9. [<a href="https://pubmed.ncbi.nlm.nih.gov/16294367" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16294367</span></a>]<div><i>(Analysis of spontaneous reporting to Spanish Pharmacovigilance system found 88 cases of flutamide, 11 bicalutamide and 15 cyproterone hepatotoxicity, latency 3-6 months; 2 fatalities, both from flutamide).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R14">Björnsson E, Olsson R. Suspected drug-induced liver fatalities reported to the WHO database. Dig Liver Dis 2006; 38: 33-8. (Survey of drug induced liver fatalities reported to WHO database between 1968-2003 revealed 4690 reports; flutamide ranked 11th with a total of 59 cases) [<a href="https://pubmed.ncbi.nlm.nih.gov/16054882" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 16054882</span></a>]<div><i>.</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R15">Chalasani N, Fontana RJ, Bonkovsky HL, Watkins PB, Davern T, Serrano J, Yang H, Rochon J; Drug Induced Liver Injury Network (DILIN). Causes, clinical features, and outcomes from a prospective study of drug-induced liver injury in the United States. Gastroenterology 2008; 135: 1924-34. [<a href="/pmc/articles/PMC3654244/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3654244</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/18955056" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18955056</span></a>]<div><i>(Among 300 cases of drug induced liver disease in the US collected between 2004 and 2008, none were attributed to an antiandrogen).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R16">Merwat SN, Kabbani W, Adler DG. Fulminant hepatic failure due to nilutamide hepatotoxicity. Dig Dis Sci 2009; 54: 910-3. [<a href="https://pubmed.ncbi.nlm.nih.gov/18688719" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18688719</span></a>]<div><i>(76 year old man with prostate cancer developed abdominal pain followed by jaundice 6 weeks after starting nilutamide [bilirubin 25.8 mg/dL, ALT 1793 U/L, Alk P 231 U/L, INR 1.7], followed by progressive hepatic and multiorgan failure and death).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R17">Reuben A, Koch DG, Lee WM; Acute Liver Failure Study Group. Drug-induced acute liver failure: results of a U.S. multicenter, prospective study. Hepatology 2010; 52: 2065-76. [<a href="/pmc/articles/PMC3992250/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3992250</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/20949552" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 20949552</span></a>]<div><i>(Among 1198 patients with acute liver failure enrolled in a US prospective study between 1998 and 2007, 133 were attributed to drug induced liver injury including 25 from antituberculosis drugs, 9 from sulfonamides, 12 from nitrofurantoin, 6 from antifungal agents, 11 from antiepileptic drugs, and 12 from herbals, but none were attributed to antiandrogen therapies).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R18">Brahm J, Brahm M, Segovia R, Latorre R, Zapata R, Poniachik J, Buckel E, Contreras L. Acute and fulminant hepatitis induced by flutamide: case series report and review of the literature. Ann Hepatol 2011; 10: 93-8. [<a href="https://pubmed.ncbi.nlm.nih.gov/21301018" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 21301018</span></a>]<div><i>(Analysis of 10 patients with flutamide hepatotoxicity seen at a single institution in Chile included 3 men [ages 67-80 with prostate cancer] and 7 women [ages 20-44 with hirsutism], onset after 40 to 180 days, 9 with jaundice [bilirubin 2.4 to 44 mg/dL, ALT 159 to 3360 U/L], 5 progressed to acute liver failure requiring liver transplantation [all women]).</i></div></div></li><li><div class="bk_ref" id="Anti-androgens.R19">Hernández N, Bessone F, Sánchez A, di Pace M, Brahm J, Zapata R, A Chirino R, et al. Profile of idiosyncratic drug induced liver injury in Latin America. An analysis of published reports. Ann Hepatol 2014; 13: 231-9. (Systematic review of literature of drug induced liver injury in Latin American countries published from 1996 to 2012 identified 176 cases, including 18 due to cyproterone and 12 to flutamide, 11 from Chile [10 in Brahm 2011] and 1 from Colombia). [<a href="https://pubmed.ncbi.nlm.nih.gov/24552865" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 24552865</span></a>]</div></li><li><div class="bk_ref" id="Anti-androgens.R20">Ryan CJ, Smith MR, Fizazi K, Saad F, Mulders PF, Sternberg CN, Miller K, et al.; COU-AA-302 Investigators. Abiraterone acetate plus prednisone versus placebo plus prednisone in chemotherapy-naive men with metastatic castration-resistant prostate cancer (COU-AA-302): final overall survival analysis of a randomised, double-blind, placebo-controlled phase 3 study. Lancet Oncol 2015; 16: 152-60. [<a href="https://pubmed.ncbi.nlm.nih.gov/25601341" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 25601341</span></a>]<div><i> (Among 1088 patients with metastatic, castration-resistant prostate cancer treated with abiraterone and prednisone vs prednisone alone, side effects included mild ALT elevations [13% vs 5%] that were rarely greater than 5 times ULN [0.7% vs 0%] and there were no instances of clinically apparent liver injury or liver related deaths).</i></div></div></li></ul></div><div id="bk_toc_contnr"></div></div></div><div class="fm-sec"><h2 id="_NBK548491_pubdet_">Publication Details</h2><h3>Publication History</h3><p class="small">Last Update: <span itemprop="dateModified">June 10, 2014</span>.</p><h3>Copyright</h3><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div></div><h3>Publisher</h3><p><a href="https://www.niddk.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Institute of Diabetes and Digestive and Kidney Diseases</a>, Bethesda (MD)</p><h3>NLM Citation</h3><p>LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Antiandrogens. [Updated 2014 Jun 10].<span class="bk_cite_avail"></span></p></div><div class="small-screen-prev"><a href="/books/n/livertox/AnthraxAntitoxins/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M75,30 c-80,60 -80,0 0,60 c-30,-60 -30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Prev</text></svg></a></div><div class="small-screen-next"><a href="/books/n/livertox/AntiarrhythmicAgents/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M25,30c80,60 80,0 0,60 c30,-60 30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Next</text></svg></a></div></article><article data-type="table-wrap" id="figobAntiandrogensT1"><div id="Anti-androgens.T1" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK548491/table/Anti-androgens.T1/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__Anti-androgens.T1_lrgtbl__"><table><tbody><tr><th id="hd_b_Anti-androgens.T1_1_1_1_1" rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">DRUG</th><th id="hd_b_Anti-androgens.T1_1_1_1_2" rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">CAS REGISTRY NO</th><th id="hd_b_Anti-androgens.T1_1_1_1_3" rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">MOLECULAR FORMULA</th><th id="hd_b_Anti-androgens.T1_1_1_1_4" rowspan="1" colspan="1" style="text-align:center;vertical-align:top;">STRUCTURE</th></tr><tr><td headers="hd_b_Anti-androgens.T1_1_1_1_1" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">Abiraterone</td><td headers="hd_b_Anti-androgens.T1_1_1_1_2" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
|
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/135089190" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">154229-19-3</a>
|
|
</td><td headers="hd_b_Anti-androgens.T1_1_1_1_3" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">C24-H31-N-O</td><td headers="hd_b_Anti-androgens.T1_1_1_1_4" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
|
<div class="graphic"><img src="/books/NBK548491/bin/Abiraterone_structure.jpg" alt="Abiraterone chemical structure" /></div>
|
|
</td></tr><tr><td headers="hd_b_Anti-androgens.T1_1_1_1_1" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">Bicalutamide</td><td headers="hd_b_Anti-androgens.T1_1_1_1_2" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
|
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/135014383" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">90357-06-5</a>
|
|
</td><td headers="hd_b_Anti-androgens.T1_1_1_1_3" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">C18-H14-F4-N2-O4-S</td><td headers="hd_b_Anti-androgens.T1_1_1_1_4" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
|
<div class="graphic"><img src="/books/NBK548491/bin/Bicalutamide_Structure_000.jpg" alt="Bicalutamide chemical structure" /></div>
|
|
</td></tr><tr><td headers="hd_b_Anti-androgens.T1_1_1_1_1" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">Flutamide</td><td headers="hd_b_Anti-androgens.T1_1_1_1_2" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
|
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134990691" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">13311-84-7</a>
|
|
</td><td headers="hd_b_Anti-androgens.T1_1_1_1_3" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">C11-H11-F3-N2-O3</td><td headers="hd_b_Anti-androgens.T1_1_1_1_4" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
|
<div class="graphic"><img src="/books/NBK548491/bin/Flutamide_Structure_000.jpg" alt="Flutamide chemical structure" /></div>
|
|
</td></tr><tr><td headers="hd_b_Anti-androgens.T1_1_1_1_1" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">Nilutamide</td><td headers="hd_b_Anti-androgens.T1_1_1_1_2" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
|
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/135006493" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">63612-50-0</a>
|
|
</td><td headers="hd_b_Anti-androgens.T1_1_1_1_3" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">C12-H10-F3-N3-O4</td><td headers="hd_b_Anti-androgens.T1_1_1_1_4" rowspan="1" colspan="1" style="text-align:center;vertical-align:middle;">
|
|
<div class="graphic"><img src="/books/NBK548491/bin/Nilutamide_Structure2.jpg" alt="Nilutamide chemical structure" /></div>
|
|
</td></tr></tbody></table></div></div></article></div><div id="jr-scripts"><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/libs.min.js"> </script><script src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.min.js"> </script></div></div>
|
|
|
|
|
|
|
|
|
|
<!-- Book content -->
|
|
|
|
<script type="text/javascript" src="/portal/portal3rc.fcgi/rlib/js/InstrumentNCBIBaseJS/InstrumentPageStarterJS.js"> </script>
|
|
|
|
|
|
<!-- CE8B5AF87C7FFCB1_0191SID /projects/books/PBooks@9.11 portal105 v4.1.r689238 Tue, Oct 22 2024 16:10:51 -->
|
|
<span id="portal-csrf-token" style="display:none" data-token="CE8B5AF87C7FFCB1_0191SID"></span>
|
|
|
|
<script type="text/javascript" src="//static.pubmed.gov/portal/portal3rc.fcgi/4216699/js/3968615.js" snapshot="books"></script></body>
|
|
</html>
|