CINXE.COM

<!DOCTYPE html> <html class="client-nojs vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-sticky-header-enabled vector-toc-available" lang="en" dir="ltr"> <head> <meta charset="UTF-8"> <title>Doxorubicin - Wikipedia</title> <script>(function(){var className="client-js vector-feature-language-in-header-enabled vector-feature-language-in-main-page-header-disabled vector-feature-page-tools-pinned-disabled vector-feature-toc-pinned-clientpref-1 vector-feature-main-menu-pinned-disabled vector-feature-limited-width-clientpref-1 vector-feature-limited-width-content-enabled vector-feature-custom-font-size-clientpref-1 vector-feature-appearance-pinned-clientpref-1 vector-feature-night-mode-enabled skin-theme-clientpref-day vector-sticky-header-enabled vector-toc-available";var cookie=document.cookie.match(/(?:^|; )enwikimwclientpreferences=([^;]+)/);if(cookie){cookie[1].split('%2C').forEach(function(pref){className=className.replace(new RegExp('(^| )'+pref.replace(/-clientpref-\w+$|[^\w-]+/g,'')+'-clientpref-\\w+( |$)'),'$1'+pref+'$2');});}document.documentElement.className=className;}());RLCONF={"wgBreakFrames":false,"wgSeparatorTransformTable":["",""],"wgDigitTransformTable":["",""],"wgDefaultDateFormat":"dmy","wgMonthNames":["","January","February","March","April","May","June","July","August","September","October","November","December"],"wgRequestId":"3e89eb90-e8da-4be2-b4a8-bc885fc31350","wgCanonicalNamespace":"","wgCanonicalSpecialPageName":false,"wgNamespaceNumber":0,"wgPageName":"Doxorubicin","wgTitle":"Doxorubicin","wgCurRevisionId":1280964764,"wgRevisionId":1280964764,"wgArticleId":1802881,"wgIsArticle":true,"wgIsRedirect":false,"wgAction":"view","wgUserName":null,"wgUserGroups":["*"],"wgCategories":["All articles with dead external links","Articles with dead external links from November 2021","Articles with permanently dead external links","Webarchive template wayback links","CS1 Italian-language sources (it)","Articles with short description","Short description is different from Wikidata","Use dmy dates from March 2023","Drugs with non-standard legal status","Articles with changed EBI identifier","ECHA InfoCard ID from Wikidata","Articles with changed InChI identifier","Multiple chemicals in Infobox drug","Chemicals using indexlabels","Chemical articles with multiple CAS registry numbers","Chemical articles with multiple PubChem CIDs","Chemical articles with multiple ChEBIs","Drug has EMA link","Drugboxes which contain changes to verified fields","Drugboxes which contain changes to watched fields","Commons category link from Wikidata","Good articles","Wikipedia medicine articles ready to translate","Anthracyclines","Anthraquinone glycosides","CYP2D6 inhibitors","DNA intercalaters","Embryotoxins","IARC Group 2A carcinogens","Italian inventions","Drugs developed by Johnson \u0026 Johnson","Orphan drugs","Drugs developed by Pfizer","Teratogens","Topoisomerase inhibitors","World Health Organization essential medicines"],"wgPageViewLanguage":"en","wgPageContentLanguage":"en","wgPageContentModel":"wikitext","wgRelevantPageName":"Doxorubicin","wgRelevantArticleId":1802881,"wgIsProbablyEditable":true,"wgRelevantPageIsProbablyEditable":true,"wgRestrictionEdit":[],"wgRestrictionMove":[],"wgNoticeProject":"wikipedia","wgCiteReferencePreviewsActive":false,"wgFlaggedRevsParams":{"tags":{"status":{"levels":1}}},"wgMediaViewerOnClick":true,"wgMediaViewerEnabledByDefault":true,"wgPopupsFlags":0,"wgVisualEditor":{"pageLanguageCode":"en","pageLanguageDir":"ltr","pageVariantFallbacks":"en"},"wgMFDisplayWikibaseDescriptions":{"search":true,"watchlist":true,"tagline":false,"nearby":true},"wgWMESchemaEditAttemptStepOversample":false,"wgWMEPageLength":50000,"wgEditSubmitButtonLabelPublish":true,"wgULSPosition":"interlanguage","wgULSisCompactLinksEnabled":false,"wgVector2022LanguageInHeader":true,"wgULSisLanguageSelectorEmpty":false,"wgWikibaseItemId":"Q18936","wgCheckUserClientHintsHeadersJsApi":["brands","architecture","bitness","fullVersionList","mobile","model","platform","platformVersion"],"GEHomepageSuggestedEditsEnableTopics":true,"wgGETopicsMatchModeEnabled":false,"wgGELevelingUpEnabledForUser":false}; RLSTATE={"ext.globalCssJs.user.styles":"ready","site.styles":"ready","user.styles":"ready","ext.globalCssJs.user":"ready","user":"ready","user.options":"loading","ext.cite.styles":"ready","skins.vector.search.codex.styles":"ready","skins.vector.styles":"ready","skins.vector.icons":"ready","jquery.makeCollapsible.styles":"ready","ext.wikimediamessages.styles":"ready","ext.visualEditor.desktopArticleTarget.noscript":"ready","ext.uls.interlanguage":"ready","wikibase.client.init":"ready"};RLPAGEMODULES=["ext.cite.ux-enhancements","mediawiki.page.media","site","mediawiki.page.ready","jquery.makeCollapsible","mediawiki.toc","skins.vector.js","ext.centralNotice.geoIP","ext.centralNotice.startUp","ext.gadget.ReferenceTooltips","ext.gadget.switcher","ext.urlShortener.toolbar","ext.centralauth.centralautologin","mmv.bootstrap","ext.popups","ext.visualEditor.desktopArticleTarget.init","ext.visualEditor.targetLoader","ext.echo.centralauth","ext.eventLogging","ext.wikimediaEvents","ext.navigationTiming","ext.uls.interface","ext.cx.eventlogging.campaigns","ext.cx.uls.quick.actions","wikibase.client.vector-2022","ext.checkUser.clientHints","ext.quicksurveys.init","ext.growthExperiments.SuggestedEditSession"];</script> <script>(RLQ=window.RLQ||[]).push(function(){mw.loader.impl(function(){return["user.options@12s5i",function($,jQuery,require,module){mw.user.tokens.set({"patrolToken":"+\\","watchToken":"+\\","csrfToken":"+\\"}); }];});});</script> <link rel="stylesheet" href="/w/load.php?lang=en&modules=ext.cite.styles%7Cext.uls.interlanguage%7Cext.visualEditor.desktopArticleTarget.noscript%7Cext.wikimediamessages.styles%7Cjquery.makeCollapsible.styles%7Cskins.vector.icons%2Cstyles%7Cskins.vector.search.codex.styles%7Cwikibase.client.init&only=styles&skin=vector-2022"> <script async="" src="/w/load.php?lang=en&modules=startup&only=scripts&raw=1&skin=vector-2022"></script> <meta name="ResourceLoaderDynamicStyles" content=""> <link rel="stylesheet" href="/w/load.php?lang=en&modules=site.styles&only=styles&skin=vector-2022"> <meta name="generator" content="MediaWiki 1.44.0-wmf.22"> <meta name="referrer" content="origin"> <meta name="referrer" content="origin-when-cross-origin"> <meta name="robots" content="max-image-preview:standard"> <meta name="format-detection" content="telephone=no"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Doxorubicin.svg/1200px-Doxorubicin.svg.png"> <meta property="og:image:width" content="1200"> <meta property="og:image:height" content="919"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Doxorubicin.svg/800px-Doxorubicin.svg.png"> <meta property="og:image:width" content="800"> <meta property="og:image:height" content="613"> <meta property="og:image" content="https://upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Doxorubicin.svg/640px-Doxorubicin.svg.png"> <meta property="og:image:width" content="640"> <meta property="og:image:height" content="490"> <meta name="viewport" content="width=1120"> <meta property="og:title" content="Doxorubicin - Wikipedia"> <meta property="og:type" content="website"> <link rel="preconnect" href="//upload.wikimedia.org"> <link rel="alternate" media="only screen and (max-width: 640px)" href="//en.m.wikipedia.org/wiki/Doxorubicin"> <link rel="alternate" type="application/x-wiki" title="Edit this page" href="/w/index.php?title=Doxorubicin&action=edit"> <link rel="apple-touch-icon" href="/static/apple-touch/wikipedia.png"> <link rel="icon" href="/static/favicon/wikipedia.ico"> <link rel="search" type="application/opensearchdescription+xml" href="/w/rest.php/v1/search" title="Wikipedia (en)"> <link rel="EditURI" type="application/rsd+xml" href="//en.wikipedia.org/w/api.php?action=rsd"> <link rel="canonical" href="https://en.wikipedia.org/wiki/Doxorubicin"> <link rel="license" href="https://creativecommons.org/licenses/by-sa/4.0/deed.en"> <link rel="alternate" type="application/atom+xml" title="Wikipedia Atom feed" href="/w/index.php?title=Special:RecentChanges&feed=atom"> <link rel="dns-prefetch" href="//meta.wikimedia.org" /> <link rel="dns-prefetch" href="login.wikimedia.org"> </head> <body class="skin--responsive skin-vector skin-vector-search-vue mediawiki ltr sitedir-ltr mw-hide-empty-elt ns-0 ns-subject mw-editable page-Doxorubicin rootpage-Doxorubicin skin-vector-2022 action-view"><a class="mw-jump-link" href="#bodyContent">Jump to content</a> <div class="vector-header-container"> <header class="vector-header mw-header"> <div class="vector-header-start"> <nav class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-dropdown" class="vector-dropdown vector-main-menu-dropdown vector-button-flush-left vector-button-flush-right" title="Main menu" > <input type="checkbox" id="vector-main-menu-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-main-menu-dropdown" class="vector-dropdown-checkbox " aria-label="Main menu" > <label id="vector-main-menu-dropdown-label" for="vector-main-menu-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-menu mw-ui-icon-wikimedia-menu"></span> <span class="vector-dropdown-label-text">Main menu</span> </label> <div class="vector-dropdown-content"> <div id="vector-main-menu-unpinned-container" class="vector-unpinned-container"> <div id="vector-main-menu" class="vector-main-menu vector-pinnable-element"> <div class="vector-pinnable-header vector-main-menu-pinnable-header vector-pinnable-header-unpinned" data-feature-name="main-menu-pinned" data-pinnable-element-id="vector-main-menu" data-pinned-container-id="vector-main-menu-pinned-container" data-unpinned-container-id="vector-main-menu-unpinned-container" > <div class="vector-pinnable-header-label">Main menu</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-main-menu.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-main-menu.unpin">hide</button> </div> <div id="p-navigation" class="vector-menu mw-portlet mw-portlet-navigation" > <div class="vector-menu-heading"> Navigation </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-mainpage-description" class="mw-list-item"><a href="/wiki/Main_Page" title="Visit the main page [z]" accesskey="z"><span>Main page</span></a></li><li id="n-contents" class="mw-list-item"><a href="/wiki/Wikipedia:Contents" title="Guides to browsing Wikipedia"><span>Contents</span></a></li><li id="n-currentevents" class="mw-list-item"><a href="/wiki/Portal:Current_events" title="Articles related to current events"><span>Current events</span></a></li><li id="n-randompage" class="mw-list-item"><a href="/wiki/Special:Random" title="Visit a randomly selected article [x]" accesskey="x"><span>Random article</span></a></li><li id="n-aboutsite" class="mw-list-item"><a href="/wiki/Wikipedia:About" title="Learn about Wikipedia and how it works"><span>About Wikipedia</span></a></li><li id="n-contactpage" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us" title="How to contact Wikipedia"><span>Contact us</span></a></li> </ul> </div> </div> <div id="p-interaction" class="vector-menu mw-portlet mw-portlet-interaction" > <div class="vector-menu-heading"> Contribute </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="n-help" class="mw-list-item"><a href="/wiki/Help:Contents" title="Guidance on how to use and edit Wikipedia"><span>Help</span></a></li><li id="n-introduction" class="mw-list-item"><a href="/wiki/Help:Introduction" title="Learn how to edit Wikipedia"><span>Learn to edit</span></a></li><li id="n-portal" class="mw-list-item"><a href="/wiki/Wikipedia:Community_portal" title="The hub for editors"><span>Community portal</span></a></li><li id="n-recentchanges" class="mw-list-item"><a href="/wiki/Special:RecentChanges" title="A list of recent changes to Wikipedia [r]" accesskey="r"><span>Recent changes</span></a></li><li id="n-upload" class="mw-list-item"><a href="/wiki/Wikipedia:File_upload_wizard" title="Add images or other media for use on Wikipedia"><span>Upload file</span></a></li><li id="n-specialpages" class="mw-list-item"><a href="/wiki/Special:SpecialPages"><span>Special pages</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> <a href="/wiki/Main_Page" class="mw-logo"> <img class="mw-logo-icon" src="/static/images/icons/wikipedia.png" alt="" aria-hidden="true" height="50" width="50"> <span class="mw-logo-container skin-invert"> <img class="mw-logo-wordmark" alt="Wikipedia" src="/static/images/mobile/copyright/wikipedia-wordmark-en.svg" style="width: 7.5em; height: 1.125em;"> <img class="mw-logo-tagline" alt="The Free Encyclopedia" src="/static/images/mobile/copyright/wikipedia-tagline-en.svg" width="117" height="13" style="width: 7.3125em; height: 0.8125em;"> </span> </a> </div> <div class="vector-header-end"> <div id="p-search" role="search" class="vector-search-box-vue vector-search-box-collapses vector-search-box-show-thumbnail vector-search-box-auto-expand-width vector-search-box"> <a href="/wiki/Special:Search" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only search-toggle" title="Search Wikipedia [f]" accesskey="f"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </a> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail cdx-typeahead-search--auto-expand-width"> <form action="/w/index.php" id="searchform" class="cdx-search-input cdx-search-input--has-end-button"> <div id="simpleSearch" class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia" aria-label="Search Wikipedia" autocapitalize="sentences" title="Search Wikipedia [f]" accesskey="f" id="searchInput" > <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <nav class="vector-user-links vector-user-links-wide" aria-label="Personal tools"> <div class="vector-user-links-main"> <div id="p-vector-user-menu-preferences" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-userpage" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-dropdown" class="vector-dropdown " title="Change the appearance of the page's font size, width, and color" > <input type="checkbox" id="vector-appearance-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-appearance-dropdown" class="vector-dropdown-checkbox " aria-label="Appearance" > <label id="vector-appearance-dropdown-label" for="vector-appearance-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-appearance mw-ui-icon-wikimedia-appearance"></span> <span class="vector-dropdown-label-text">Appearance</span> </label> <div class="vector-dropdown-content"> <div id="vector-appearance-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div id="p-vector-user-menu-notifications" class="vector-menu mw-portlet emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> <div id="p-vector-user-menu-overflow" class="vector-menu mw-portlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="https://donate.wikimedia.org/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=en.wikipedia.org&uselang=en" class=""><span>Donate</span></a> </li> <li id="pt-createaccount-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:CreateAccount&returnto=Doxorubicin" title="You are encouraged to create an account and log in; however, it is not mandatory" class=""><span>Create account</span></a> </li> <li id="pt-login-2" class="user-links-collapsible-item mw-list-item user-links-collapsible-item"><a data-mw="interface" href="/w/index.php?title=Special:UserLogin&returnto=Doxorubicin" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o" class=""><span>Log in</span></a> </li> </ul> </div> </div> </div> <div id="vector-user-links-dropdown" class="vector-dropdown vector-user-menu vector-button-flush-right vector-user-menu-logged-out" title="Log in and more options" > <input type="checkbox" id="vector-user-links-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-user-links-dropdown" class="vector-dropdown-checkbox " aria-label="Personal tools" > <label id="vector-user-links-dropdown-label" for="vector-user-links-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-ellipsis mw-ui-icon-wikimedia-ellipsis"></span> <span class="vector-dropdown-label-text">Personal tools</span> </label> <div class="vector-dropdown-content"> <div id="p-personal" class="vector-menu mw-portlet mw-portlet-personal user-links-collapsible-item" title="User menu" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-sitesupport" class="user-links-collapsible-item mw-list-item"><a href="https://donate.wikimedia.org/?wmf_source=donate&wmf_medium=sidebar&wmf_campaign=en.wikipedia.org&uselang=en"><span>Donate</span></a></li><li id="pt-createaccount" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:CreateAccount&returnto=Doxorubicin" title="You are encouraged to create an account and log in; however, it is not mandatory"><span class="vector-icon mw-ui-icon-userAdd mw-ui-icon-wikimedia-userAdd"></span> <span>Create account</span></a></li><li id="pt-login" class="user-links-collapsible-item mw-list-item"><a href="/w/index.php?title=Special:UserLogin&returnto=Doxorubicin" title="You're encouraged to log in; however, it's not mandatory. [o]" accesskey="o"><span class="vector-icon mw-ui-icon-logIn mw-ui-icon-wikimedia-logIn"></span> <span>Log in</span></a></li> </ul> </div> </div> <div id="p-user-menu-anon-editor" class="vector-menu mw-portlet mw-portlet-user-menu-anon-editor" > <div class="vector-menu-heading"> Pages for logged out editors <a href="/wiki/Help:Introduction" aria-label="Learn more about editing"><span>learn more</span></a> </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="pt-anoncontribs" class="mw-list-item"><a href="/wiki/Special:MyContributions" title="A list of edits made from this IP address [y]" accesskey="y"><span>Contributions</span></a></li><li id="pt-anontalk" class="mw-list-item"><a href="/wiki/Special:MyTalk" title="Discussion about edits from this IP address [n]" accesskey="n"><span>Talk</span></a></li> </ul> </div> </div> </div> </div> </nav> </div> </header> </div> <div class="mw-page-container"> <div class="mw-page-container-inner"> <div class="vector-sitenotice-container"> <div id="siteNotice"></div> </div> <div class="vector-column-start"> <div class="vector-main-menu-container"> <div id="mw-navigation"> <nav id="mw-panel" class="vector-main-menu-landmark" aria-label="Site"> <div id="vector-main-menu-pinned-container" class="vector-pinned-container"> </div> </nav> </div> </div> <div class="vector-sticky-pinned-container"> <nav id="mw-panel-toc" aria-label="Contents" data-event-name="ui.sidebar-toc" class="mw-table-of-contents-container vector-toc-landmark"> <div id="vector-toc-pinned-container" class="vector-pinned-container"> <div id="vector-toc" class="vector-toc vector-pinnable-element"> <div class="vector-pinnable-header vector-toc-pinnable-header vector-pinnable-header-pinned" data-feature-name="toc-pinned" data-pinnable-element-id="vector-toc" > <h2 class="vector-pinnable-header-label">Contents</h2> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-toc.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-toc.unpin">hide</button> </div> <ul class="vector-toc-contents" id="mw-panel-toc-list"> <li id="toc-mw-content-text" class="vector-toc-list-item vector-toc-level-1"> <a href="#" class="vector-toc-link"> <div class="vector-toc-text">(Top)</div> </a> </li> <li id="toc-Medical_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Medical_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">1</span> <span>Medical uses</span> </div> </a> <ul id="toc-Medical_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Side effects</span> </div> </a> <button aria-controls="toc-Side_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Side effects subsection</span> </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-Cardiotoxicity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiotoxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Cardiotoxicity</span> </div> </a> <ul id="toc-Cardiotoxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Liposomal_formulations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Liposomal_formulations"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Liposomal formulations</span> </div> </a> <ul id="toc-Liposomal_formulations-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Society and culture</span> </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Society and culture subsection</span> </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Legal status</span> </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Names"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Names</span> </div> </a> <ul id="toc-Names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Formulations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Formulations"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Formulations</span> </div> </a> <ul id="toc-Formulations-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Research</span> </div> </a> <button aria-controls="toc-Research-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Research subsection</span> </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Antimalarial_activity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antimalarial_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Antimalarial activity</span> </div> </a> <ul id="toc-Antimalarial_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fluorescence" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fluorescence"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Fluorescence</span> </div> </a> <ul id="toc-Fluorescence-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Doxorubicin</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 32 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-32" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">32 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AF%D9%88%D9%83%D8%B3%D9%88%D8%B1%D9%88%D8%A8%D9%8A%D8%B3%D9%8A%D9%86" title="دوكسوروبيسين – Arabic" lang="ar" hreflang="ar" data-title="دوكسوروبيسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%AF%D9%88%DA%A9%D8%B3%D9%88%D8%B1%D8%A7%D8%A8%DB%8C%D8%B3%DB%8C%D9%86" title="دوکسورابیسین – South Azerbaijani" lang="azb" hreflang="azb" data-title="دوکسورابیسین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Doxorubicina" title="Doxorubicina – Catalan" lang="ca" hreflang="ca" data-title="Doxorubicina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Docsorwbicin" title="Docsorwbicin – Welsh" lang="cy" hreflang="cy" data-title="Docsorwbicin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Doxorubicin" title="Doxorubicin – German" lang="de" hreflang="de" data-title="Doxorubicin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%94%CE%BF%CE%BE%CE%BF%CF%81%CE%BF%CF%85%CE%BC%CF%80%CE%B9%CE%BA%CE%AF%CE%BD%CE%B7" title="Δοξορουμπικίνη – Greek" lang="el" hreflang="el" data-title="Δοξορουμπικίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Doxorrubicina" title="Doxorrubicina – Spanish" lang="es" hreflang="es" data-title="Doxorrubicina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AF%D9%88%DA%A9%D8%B3%D9%88%D8%B1%D8%A7%D8%A8%DB%8C%D8%B3%DB%8C%D9%86" title="دوکسورابیسین – Persian" lang="fa" hreflang="fa" data-title="دوکسورابیسین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Doxorubicine" title="Doxorubicine – French" lang="fr" hreflang="fr" data-title="Doxorubicine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Doxorrubicina" title="Doxorrubicina – Galician" lang="gl" hreflang="gl" data-title="Doxorrubicina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%8F%85%EC%86%8C%EB%A3%A8%EB%B9%84%EC%8B%A0" title="독소루비신 – Korean" lang="ko" hreflang="ko" data-title="독소루비신" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B4%D5%B8%D6%84%D5%BD%D5%B8%D5%BC%D5%B8%D6%82%D5%A2%D5%AB%D6%81%D5%AB%D5%B6" title="Դոքսոռուբիցին – Armenian" lang="hy" hreflang="hy" data-title="Դոքսոռուբիցին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Doksorubisin" title="Doksorubisin – Indonesian" lang="id" hreflang="id" data-title="Doksorubisin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Doxorubicina" title="Doxorubicina – Italian" lang="it" hreflang="it" data-title="Doxorubicina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Doxorubicin" title="Doxorubicin – Hungarian" lang="hu" hreflang="hu" data-title="Doxorubicin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Doxorubicine" title="Doxorubicine – Dutch" lang="nl" hreflang="nl" data-title="Doxorubicine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%89%E3%82%AD%E3%82%BD%E3%83%AB%E3%83%93%E3%82%B7%E3%83%B3" title="ドキソルビシン – Japanese" lang="ja" hreflang="ja" data-title="ドキソルビシン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%A1%E0%AC%95%E0%AD%8D%E0%AC%B8%E0%AD%8B%E0%AC%B0%E0%AD%81%E0%AC%AC%E0%AC%BF%E0%AC%B8%E0%AC%BF%E0%AC%A8" title="ଡକ୍ସୋରୁବିସିନ – Odia" lang="or" hreflang="or" data-title="ଡକ୍ସୋରୁବିସିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Doksorubicyna" title="Doksorubicyna – Polish" lang="pl" hreflang="pl" data-title="Doksorubicyna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Doxorrubicina" title="Doxorrubicina – Portuguese" lang="pt" hreflang="pt" data-title="Doxorrubicina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Doxorubicin%C4%83" title="Doxorubicină – Romanian" lang="ro" hreflang="ro" data-title="Doxorubicină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%94%D0%BE%D0%BA%D1%81%D0%BE%D1%80%D1%83%D0%B1%D0%B8%D1%86%D0%B8%D0%BD" title="Доксорубицин – Russian" lang="ru" hreflang="ru" data-title="Доксорубицин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Doksorubicin" title="Doksorubicin – Slovenian" lang="sl" hreflang="sl" data-title="Doksorubicin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Doksorubicin" title="Doksorubicin – Serbian" lang="sr" hreflang="sr" data-title="Doksorubicin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Doksorubicin" title="Doksorubicin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Doksorubicin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Doksorubisiini" title="Doksorubisiini – Finnish" lang="fi" hreflang="fi" data-title="Doksorubisiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Doxorubicin" title="Doxorubicin – Swedish" lang="sv" hreflang="sv" data-title="Doxorubicin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Doxorubicin" title="Doxorubicin – Tagalog" lang="tl" hreflang="tl" data-title="Doxorubicin" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Doksorubisin" title="Doksorubisin – Turkish" lang="tr" hreflang="tr" data-title="Doksorubisin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%94%D0%BE%D0%BA%D1%81%D0%BE%D1%80%D1%83%D0%B1%D1%96%D1%86%D0%B8%D0%BD" title="Доксорубіцин – Ukrainian" lang="uk" hreflang="uk" data-title="Доксорубіцин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Doxorubicin" title="Doxorubicin – Vietnamese" lang="vi" hreflang="vi" data-title="Doxorubicin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%98%BF%E9%BB%B4%E7%B4%A0" title="阿黴素 – Chinese" lang="zh" hreflang="zh" data-title="阿黴素" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q18936#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Doxorubicin" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Doxorubicin" rel="discussion" title="Discuss improvements to the content page [t]" accesskey="t"><span>Talk</span></a></li> </ul> </div> </div> <div id="vector-variants-dropdown" class="vector-dropdown emptyPortlet" > <input type="checkbox" id="vector-variants-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-variants-dropdown" class="vector-dropdown-checkbox " aria-label="Change language variant" > <label id="vector-variants-dropdown-label" for="vector-variants-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">English</span> </label> <div class="vector-dropdown-content"> <div id="p-variants" class="vector-menu mw-portlet mw-portlet-variants emptyPortlet" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> </ul> </div> </div> </div> </div> </nav> </div> <div id="right-navigation" class="vector-collapsible"> <nav aria-label="Views"> <div id="p-views" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-views" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-view" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Doxorubicin"><span>Read</span></a></li><li id="ca-edit" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Doxorubicin&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-history" class="vector-tab-noicon mw-list-item"><a href="/w/index.php?title=Doxorubicin&action=history" title="Past revisions of this page [h]" accesskey="h"><span>View history</span></a></li> </ul> </div> </div> </nav> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-dropdown" class="vector-dropdown vector-page-tools-dropdown" > <input type="checkbox" id="vector-page-tools-dropdown-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-tools-dropdown" class="vector-dropdown-checkbox " aria-label="Tools" > <label id="vector-page-tools-dropdown-label" for="vector-page-tools-dropdown-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet" aria-hidden="true" ><span class="vector-dropdown-label-text">Tools</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-tools-unpinned-container" class="vector-unpinned-container"> <div id="vector-page-tools" class="vector-page-tools vector-pinnable-element"> <div class="vector-pinnable-header vector-page-tools-pinnable-header vector-pinnable-header-unpinned" data-feature-name="page-tools-pinned" data-pinnable-element-id="vector-page-tools" data-pinned-container-id="vector-page-tools-pinned-container" data-unpinned-container-id="vector-page-tools-unpinned-container" > <div class="vector-pinnable-header-label">Tools</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-page-tools.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-page-tools.unpin">hide</button> </div> <div id="p-cactions" class="vector-menu mw-portlet mw-portlet-cactions emptyPortlet vector-has-collapsible-items" title="More options" > <div class="vector-menu-heading"> Actions </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-more-view" class="selected vector-more-collapsible-item mw-list-item"><a href="/wiki/Doxorubicin"><span>Read</span></a></li><li id="ca-more-edit" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Doxorubicin&action=edit" title="Edit this page [e]" accesskey="e"><span>Edit</span></a></li><li id="ca-more-history" class="vector-more-collapsible-item mw-list-item"><a href="/w/index.php?title=Doxorubicin&action=history"><span>View history</span></a></li> </ul> </div> </div> <div id="p-tb" class="vector-menu mw-portlet mw-portlet-tb" > <div class="vector-menu-heading"> General </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="t-whatlinkshere" class="mw-list-item"><a href="/wiki/Special:WhatLinksHere/Doxorubicin" title="List of all English Wikipedia pages containing links to this page [j]" accesskey="j"><span>What links here</span></a></li><li id="t-recentchangeslinked" class="mw-list-item"><a href="/wiki/Special:RecentChangesLinked/Doxorubicin" rel="nofollow" title="Recent changes in pages linked from this page [k]" accesskey="k"><span>Related changes</span></a></li><li id="t-upload" class="mw-list-item"><a href="//en.wikipedia.org/wiki/Wikipedia:File_Upload_Wizard" title="Upload files [u]" accesskey="u"><span>Upload file</span></a></li><li id="t-permalink" class="mw-list-item"><a href="/w/index.php?title=Doxorubicin&oldid=1280964764" title="Permanent link to this revision of this page"><span>Permanent link</span></a></li><li id="t-info" class="mw-list-item"><a href="/w/index.php?title=Doxorubicin&action=info" title="More information about this page"><span>Page information</span></a></li><li id="t-cite" class="mw-list-item"><a href="/w/index.php?title=Special:CiteThisPage&page=Doxorubicin&id=1280964764&wpFormIdentifier=titleform" title="Information on how to cite this page"><span>Cite this page</span></a></li><li id="t-urlshortener" class="mw-list-item"><a href="/w/index.php?title=Special:UrlShortener&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FDoxorubicin"><span>Get shortened URL</span></a></li><li id="t-urlshortener-qrcode" class="mw-list-item"><a href="/w/index.php?title=Special:QrCode&url=https%3A%2F%2Fen.wikipedia.org%2Fwiki%2FDoxorubicin"><span>Download QR code</span></a></li> </ul> </div> </div> <div id="p-coll-print_export" class="vector-menu mw-portlet mw-portlet-coll-print_export" > <div class="vector-menu-heading"> Print/export </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="coll-download-as-rl" class="mw-list-item"><a href="/w/index.php?title=Special:DownloadAsPdf&page=Doxorubicin&action=show-download-screen" title="Download this page as a PDF file"><span>Download as PDF</span></a></li><li id="t-print" class="mw-list-item"><a href="/w/index.php?title=Doxorubicin&printable=yes" title="Printable version of this page [p]" accesskey="p"><span>Printable version</span></a></li> </ul> </div> </div> <div id="p-wikibase-otherprojects" class="vector-menu mw-portlet mw-portlet-wikibase-otherprojects" > <div class="vector-menu-heading"> In other projects </div> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="wb-otherproject-link wb-otherproject-commons mw-list-item"><a href="https://commons.wikimedia.org/wiki/Category:Doxorubicin" hreflang="en"><span>Wikimedia Commons</span></a></li><li id="t-wikibase" class="wb-otherproject-link wb-otherproject-wikibase-dataitem mw-list-item"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q18936" title="Structured data on this page hosted by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> <div id="mw-indicator-good-star" class="mw-indicator"><div class="mw-parser-output"><span typeof="mw:File"><a href="/wiki/Wikipedia:Good_articles*" title="This is a good article. Click here for more information."><img alt="This is a good article. Click here for more information." src="//upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/19px-Symbol_support_vote.svg.png" decoding="async" width="19" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/29px-Symbol_support_vote.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/39px-Symbol_support_vote.svg.png 2x" data-file-width="180" data-file-height="185" /></a></span></div></div> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemotherapy medication</div> <p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Doxorubicin">Doxorubicin</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size skin-invert-image" typeof="mw:File/Frameless"><a href="/wiki/File:Doxorubicin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Doxorubicin.svg/220px-Doxorubicin.svg.png" decoding="async" width="220" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Doxorubicin.svg/330px-Doxorubicin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Doxorubicin.svg/440px-Doxorubicin.svg.png 2x" data-file-width="1583" data-file-height="1212" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Doxorubicin_3D_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Doxorubicin_3D_ball.png/250px-Doxorubicin_3D_ball.png" decoding="async" width="220" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Doxorubicin_3D_ball.png/330px-Doxorubicin_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cd/Doxorubicin_3D_ball.png/500px-Doxorubicin_3D_ball.png 2x" data-file-width="2000" data-file-height="1490" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'d' in 'dye'">d</span><span title="/ɒ/: 'o' in 'body'">ɒ</span><span title="'k' in 'kind'">k</span><span title="'s' in 'sigh'">s</span><span title="/ə/: 'a' in 'about'">ə</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'r' in 'rye'">r</span><span title="/uː/: 'oo' in 'goose'">uː</span><span title="'b' in 'buy'">b</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'s' in 'sigh'">s</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span></span>/</a></span></span> </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">Adriamycin, Caelyx,<sup id="cite_ref-Caelyx_pegylated_liposomal_EPAR_1-0" class="reference"><a href="#cite_note-Caelyx_pegylated_liposomal_EPAR-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Myocet,<sup id="cite_ref-Myocet_liposomal_EPAR_2-0" class="reference"><a href="#cite_note-Myocet_liposomal_EPAR-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biosimilar" title="Biosimilar">Biosimilars</a></th><td class="infobox-data">Zolsketil pegylated liposomal,<sup id="cite_ref-Zolsketil_pegylated_liposomal_EPAR_3-0" class="reference"><a href="#cite_note-Zolsketil_pegylated_liposomal_EPAR-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Celdoxome pegylated liposomal<sup id="cite_ref-Celdoxome_pegylated_liposomal_EPAR_4-0" class="reference"><a href="#cite_note-Celdoxome_pegylated_liposomal_EPAR-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></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"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/doxorubicin-hydrochloride.html">Monograph</a></span></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"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a682221.html">a682221</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="European Union">EU</abbr></small> <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">EMA</a>: <span title="www.ema.europa.eu: 'Doxorubicin'"><a rel="nofollow" class="external text" href="https://www.ema.europa.eu/en/medicines/search_api_aggregation_ema_active_substance_and_inn_common_name/Doxorubicin">by INN</a></span></li> <li><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Doxorubicin">Doxorubicin</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> D</li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a>, <a href="/wiki/Intravesical" class="mw-redirect" title="Intravesical">intravesical</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_L01" title="ATC code L01">L01DB01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L01DB01">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)</li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)</li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Rx-only<sup id="cite_ref-Caelyx_pegylated_liposomal_EPAR_1-1" class="reference"><a href="#cite_note-Caelyx_pegylated_liposomal_EPAR-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Myocet_liposomal_EPAR_2-1" class="reference"><a href="#cite_note-Myocet_liposomal_EPAR-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Zolsketil_pegylated_liposomal_EPAR_3-1" class="reference"><a href="#cite_note-Zolsketil_pegylated_liposomal_EPAR-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Celdoxome_pegylated_liposomal_EPAR_4-1" class="reference"><a href="#cite_note-Celdoxome_pegylated_liposomal_EPAR-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">5% (by mouth)</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">75%<sup id="cite_ref-MSR_8-0" class="reference"><a href="#cite_note-MSR-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></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">Liver</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 <span class="nowrap">half-life</span></a></th><td class="infobox-data">Triphasic; 12 minutes, 3.3 hours, 30 hours. Mean: 1–3 hours<sup id="cite_ref-MSR_8-1" class="reference"><a href="#cite_note-MSR-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MD_9-0" class="reference"><a href="#cite_note-MD-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></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">Urine (5–12%), faeces (40–50%)<sup id="cite_ref-MSR_8-2" class="reference"><a href="#cite_note-MSR-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(7<i>S</i>,9<i>S</i>)-7-[(2<i>R</i>,4<i>S</i>,5<i>S</i>,6<i>S</i>)-4-Amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7<i>H</i>-tetracene-5,12-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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=23214-92-8">23214-92-8</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li><li>as HCl: <span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=25316-40-9">25316-40-9</a></span></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> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/31703">31703</a></span></li><li>as HCl: <span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/443939">443939</a></span></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><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7069">7069</a></span></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><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00997">DB00997</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li><li>as HCl: <span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DBSALT000060">DBSALT000060</a></span></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><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.29400.html">29400</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li><li>as HCl: <span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.391993.html">391993</a></span></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><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/80168379AG">80168379AG</a></span></li><li>as HCl: <span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/82F2G7BL4E">82F2G7BL4E</a></span></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><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D03899">D03899</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li><li>as HCl: <span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D01275">D01275</a></span></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><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28748">CHEBI:28748</a></span><sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></li><li>as HCl: <span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31522">CHEBI:31522</a></span></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><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL53463">ChEMBL53463</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li><li>as HCl: <span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL359744">ChEMBL359744</a></span></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> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID8021480">DTXSID8021480</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q18936#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></span></span></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"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.041.344">100.041.344</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q18936#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></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>27</sub><span title="Hydrogen">H</span><sub>29</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>11</sub></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"><span class="nowrap"><span data-sort-value="7002543525000000000♠"></span>543.525</span> g·mol<sup>−1</sup></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><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=C%5BC%40H%5D1%5BC%40H%5D%28%5BC%40H%5D%28C%5BC%40%40H%5D%28O1%29O%5BC%40H%5D2C%5BC%40%40%5D%28Cc3c2c%28c4c%28c3O%29C%28%3DO%29c5cccc%28c5C4%3DO%29OC%29O%29%28C%28%3DO%29CO%29O%29N%29O">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](Cc3c2c(c4c(c3O)C(=O)c5cccc(c5C4=O)OC)O)(C(=O)CO)O)N)O</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27 (36,16(30)9–29)7-12-19(15)26(35)21–20(24(12)33)23 (32)11-4-3-5-14(37–2)18(11)25(21)34/h3-5,10,13,15, 17,22,29,31,33,35-36H,6–9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></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:AOJJSUZBOXZQNB-TZSSRYMLSA-N<sup> <span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup></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><span class="nobold"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><span typeof="mw:File"><span><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" /></span></span><span style="display:none">Y</span></sup> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=458446335&page2=Doxorubicin">(verify)</a></span></span></td></tr></tbody></table> <p><b>Doxorubicin</b>, sold under the brand name <b>Adriamycin</b> among others, is a <a href="/wiki/Chemotherapy_medication" class="mw-redirect" title="Chemotherapy medication">chemotherapy medication</a> used to treat <a href="/wiki/Cancer" title="Cancer">cancer</a>.<sup id="cite_ref-AHFS2017_10-0" class="reference"><a href="#cite_note-AHFS2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> This includes <a href="/wiki/Breast_cancer" title="Breast cancer">breast cancer</a>, <a href="/wiki/Bladder_cancer" title="Bladder cancer">bladder cancer</a>, <a href="/wiki/Kaposi%27s_sarcoma" title="Kaposi's sarcoma">Kaposi's sarcoma</a>, <a href="/wiki/Lymphoma" title="Lymphoma">lymphoma</a>, and <a href="/wiki/Acute_lymphocytic_leukemia" class="mw-redirect" title="Acute lymphocytic leukemia">acute lymphocytic leukemia</a>.<sup id="cite_ref-AHFS2017_10-1" class="reference"><a href="#cite_note-AHFS2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is often used <a href="/wiki/Combination_chemotherapy" class="mw-redirect" title="Combination chemotherapy">together with other chemotherapy agents</a>.<sup id="cite_ref-AHFS2017_10-2" class="reference"><a href="#cite_note-AHFS2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Doxorubicin is given by <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">injection into a vein</a>.<sup id="cite_ref-AHFS2017_10-3" class="reference"><a href="#cite_note-AHFS2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Common side effects include <a href="/wiki/Hair_loss" title="Hair loss">hair loss</a>, <a href="/wiki/Bone_marrow_suppression" title="Bone marrow suppression">bone marrow suppression</a>, <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, rash, and <a href="/wiki/Stomatitis" title="Stomatitis">inflammation of the mouth</a>.<sup id="cite_ref-AHFS2017_10-4" class="reference"><a href="#cite_note-AHFS2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Other serious side effects may include <a href="/wiki/Allergic_reactions" class="mw-redirect" title="Allergic reactions">allergic reactions</a> such as <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylaxis</a>, <a href="/wiki/Cardiotoxicity" title="Cardiotoxicity">heart damage</a>, tissue damage at the site of injection, <a href="/wiki/Radiation_burn#Delayed_effects" title="Radiation burn">radiation recall</a>, and treatment-related <a href="/wiki/Leukemia" title="Leukemia">leukemia</a>.<sup id="cite_ref-AHFS2017_10-5" class="reference"><a href="#cite_note-AHFS2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> People often experience red discoloration of the urine for a few days.<sup id="cite_ref-AHFS2017_10-6" class="reference"><a href="#cite_note-AHFS2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Doxorubicin is in the <a href="/wiki/Anthracycline" title="Anthracycline">anthracycline</a> and <a href="/wiki/Chemotherapy#Cytotoxic_antibiotics" title="Chemotherapy">antitumor antibiotic</a> family of medications.<sup id="cite_ref-AHFS2017_10-7" class="reference"><a href="#cite_note-AHFS2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It works in part by interfering with the function of <a href="/wiki/DNA" title="DNA">DNA</a>.<sup id="cite_ref-Ta2013_11-0" class="reference"><a href="#cite_note-Ta2013-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Doxorubicin was approved for medical use in the United States in 1974.<sup id="cite_ref-AHFS2017_10-8" class="reference"><a href="#cite_note-AHFS2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> 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>.<sup id="cite_ref-WHO21st_12-0" class="reference"><a href="#cite_note-WHO21st-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BNF69_13-0" class="reference"><a href="#cite_note-BNF69-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Versions that are <a href="/wiki/Pegylated" class="mw-redirect" title="Pegylated">pegylated</a> and in <a href="/wiki/Liposomes" class="mw-redirect" title="Liposomes">liposomes</a> are also available; however, they are more expensive.<sup id="cite_ref-BNF69_13-1" class="reference"><a href="#cite_note-BNF69-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Doxorubicin was originally made from the bacterium <i><a href="/wiki/Streptomyces_peucetius" title="Streptomyces peucetius">Streptomyces peucetius</a></i>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the EU doxorubicin pegylated liposomal (as Caelyx) is <a href="/wiki/Indicated" class="mw-redirect" title="Indicated">indicated</a> to treat breast cancer, ovarian cancer, and AIDS-related Kaposi's sarcoma. It is indicated to treat <a href="/wiki/Multiple_myeloma" title="Multiple myeloma">multiple myeloma</a> in combination with <a href="/wiki/Bortezomib" title="Bortezomib">bortezomib</a>.<sup id="cite_ref-Caelyx_pegylated_liposomal_EPAR_1-2" class="reference"><a href="#cite_note-Caelyx_pegylated_liposomal_EPAR-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Doxorubicin hydrochloride (as Myocet liposomal) is indicated to treat breast cancer in combination with <a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">cyclophosphamide</a>.<sup id="cite_ref-Myocet_liposomal_EPAR_2-2" class="reference"><a href="#cite_note-Myocet_liposomal_EPAR-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Doxorubicin is commonly used to treat some <a href="/wiki/Leukemia" title="Leukemia">leukemias</a> and <a href="/wiki/Lymphomas" class="mw-redirect" title="Lymphomas">lymphomas</a>, as well as cancers of the <a href="/wiki/Bladder_cancer" title="Bladder cancer">bladder</a>, <a href="/wiki/Breast_cancer" title="Breast cancer">breast</a>, <a href="/wiki/Stomach_cancer" title="Stomach cancer">stomach</a>, <a href="/wiki/Lung_cancer" title="Lung cancer">lung</a>, <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovaries</a>, <a href="/wiki/Thyroid_cancer" title="Thyroid cancer">thyroid</a>, <a href="/wiki/Soft_tissue_sarcoma" class="mw-redirect" title="Soft tissue sarcoma">soft tissue sarcoma</a> as well as <a href="/wiki/Aggressive_fibromatosis" title="Aggressive fibromatosis">aggressive fibromatosis</a> (desmoid tumor), <a href="/wiki/Multiple_myeloma" title="Multiple myeloma">multiple myeloma</a>, and others.<sup id="cite_ref-MD_9-1" class="reference"><a href="#cite_note-MD-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AMH_15-0" class="reference"><a href="#cite_note-AMH-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Alman_2020_16-0" class="reference"><a href="#cite_note-Alman_2020-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Commonly used doxorubicin-containing <a href="/wiki/Chemotherapy_regimen" title="Chemotherapy regimen">regimens</a> are AC (Adriamycin, <a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">cyclophosphamide</a>), TAC (<a href="/wiki/Taxotere" class="mw-redirect" title="Taxotere">taxotere</a>, AC), <a href="/wiki/ABVD" title="ABVD">ABVD</a> (Adriamycin, <a href="/wiki/Bleomycin" title="Bleomycin">bleomycin</a>, <a href="/wiki/Vinblastine" title="Vinblastine">vinblastine</a>, <a href="/wiki/Dacarbazine" title="Dacarbazine">dacarbazine</a>), <a href="/wiki/BEACOPP" title="BEACOPP">BEACOPP</a>, <a href="/wiki/CHOP_(chemotherapy)" title="CHOP (chemotherapy)">CHOP</a> (cyclophosphamide, hydroxydaunorubicin, <a href="/wiki/Vincristine" title="Vincristine">vincristine</a>, <a href="/wiki/Prednisone" title="Prednisone">prednisone</a>) and FAC (<a href="/wiki/5-fluorouracil" class="mw-redirect" title="5-fluorouracil">5-fluorouracil</a>, adriamycin, cyclophosphamide).<sup id="cite_ref-MD_9-2" class="reference"><a href="#cite_note-MD-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Its activity is inhibited by certain antioxidant plant extracts, for example <i><a href="/wiki/Tragia_volubilis" title="Tragia volubilis">Tragia volubilis</a></i> aqueous extract.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Doxil (see below) is used primarily for the treatment of ovarian cancer where the disease has progressed or recurred after <a href="/wiki/Cisplatin" title="Cisplatin">platinum-based chemotherapy</a>, or for the treatment of <a href="/wiki/AIDS" class="mw-redirect" title="AIDS">AIDS</a>-related <a href="/wiki/Kaposi%27s_sarcoma" title="Kaposi's sarcoma">Kaposi's sarcoma</a>.<sup id="cite_ref-Doxil_info_18-0" class="reference"><a href="#cite_note-Doxil_info-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Cardiotoxicity">Cardiotoxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=3" title="Edit section: Cardiotoxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The most dangerous side effect of doxorubicin is <a href="/wiki/Dilated_cardiomyopathy" title="Dilated cardiomyopathy">dilated cardiomyopathy</a>, leading to <a href="/wiki/Congestive_heart_failure" class="mw-redirect" title="Congestive heart failure">congestive heart failure</a>. The rate of cardiomyopathy is dependent on its cumulative dose, with an incidence about 4% when the dose of doxorubicin is 500–550 mg/m<sup>2</sup>, 18% when the dose is 551–600 mg/m<sup>2</sup> and 36% when the dose exceeds 600 mg/m<sup>2</sup>.<sup id="cite_ref-Chaterjee_19-0" class="reference"><a href="#cite_note-Chaterjee-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> There are several ways in which doxorubicin is believed to cause cardiomyopathy, including <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a> due to iron accumulation, downregulation of genes for contractile proteins, and <a href="/wiki/P53" title="P53">p53</a>-mediated <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>.<sup id="cite_ref-Chaterjee_19-1" class="reference"><a href="#cite_note-Chaterjee-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Doxorubicin-induced cardiomyopathy typically results in dilated cardiomyopathy, with all four cardiac chambers being enlarged.<sup id="cite_ref-Chat2010_21-0" class="reference"><a href="#cite_note-Chat2010-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> This results in both systolic and diastolic dysfunction.<sup id="cite_ref-Chat2010_21-1" class="reference"><a href="#cite_note-Chat2010-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Eventually, heart failure can result, which carries a 50% mortality rate.<sup id="cite_ref-Chat2010_21-2" class="reference"><a href="#cite_note-Chat2010-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> There is no effective treatment against established cardiomyopathy caused by the drug as of 2010.<sup id="cite_ref-Chat2010_21-3" class="reference"><a href="#cite_note-Chat2010-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The drug <a href="/wiki/Dexrazoxane" title="Dexrazoxane">dexrazoxane</a>, which is an iron <a href="/wiki/Chelation" title="Chelation">chelator</a> may be used to decrease the risk of doxorubicin's cardiotoxicity in certain cases.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p><br /> </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=4" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Another common and potentially fatal complication of doxorubicin is <a href="/wiki/Typhlitis" class="mw-redirect" title="Typhlitis">typhlitis</a>, an acute life-threatening inflammation of the bowel.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Additionally, some people may develop <a href="/wiki/Palmar_plantar_erythrodysesthesia" class="mw-redirect" title="Palmar plantar erythrodysesthesia">palmar plantar erythrodysesthesia</a> (PPE), characterized by skin eruptions on the palms of the hand or soles of the feet, swelling, pain, and <a href="/wiki/Erythema" title="Erythema">erythema</a>.<sup id="cite_ref-Doxil_info_18-1" class="reference"><a href="#cite_note-Doxil_info-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Due to these side effects and its red color, doxorubicin has earned the nickname "red devil"<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-BlochCancerFaq_25-0" class="reference"><a href="#cite_note-BlochCancerFaq-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> or "red death."<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>Chemotherapy can cause reactivation of <a href="/wiki/Hepatitis_B" title="Hepatitis B">hepatitis B</a>, and doxorubicin-containing regimens are no exception.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>Doxorubicin and several chemotherapeutic drugs (including cyclophosphamide) can cause a loss of <a href="/wiki/Skin_pigmentation" class="mw-redirect" title="Skin pigmentation">skin pigmentation</a>.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Liposomal_formulations">Liposomal formulations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=5" title="Edit section: Liposomal formulations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span class="anchor" id="Liposomal_form"></span> </p><p>There is a <a href="/wiki/Pegylated" class="mw-redirect" title="Pegylated">pegylated</a> (polyethylene glycol coated) <a href="/wiki/Liposome" title="Liposome">liposome</a>-encapsulated form of doxorubicin, developed to treat <a href="/wiki/Kaposi%27s_sarcoma" title="Kaposi's sarcoma">Kaposi's sarcoma</a>. The <a href="/wiki/Polyethylene_glycol" title="Polyethylene glycol">polyethylene glycol</a> coating results in preferential concentration of doxorubicin in the skin. However, this also results in a side effect called palmar plantar erythrodysesthesia (PPE), more commonly known as hand-foot syndrome. </p><p>Following administration of this form of doxorubicin, small amounts of the drug can leak from capillaries in the palms of the hands and soles of the feet. The result of this leakage is redness, tenderness, and peeling of the skin that can be uncomfortable and even painful. In clinical testing at 50 mg/m<sup>2</sup> dosing every four weeks, half of people developed hand-foot syndrome. The rate of this side effect limits the dose of this formulation that can be given as compared with plain doxorubicin in the same treatment regimen, thereby limiting potential substitution. Substitution would be desirable because liposome-encapsulated doxorubicin is less cardiotoxic than unencapsulated doxorubicin. This liposome-encapsulated form is also approved by the FDA for treatment of ovarian cancer and multiple myeloma.<sup id="cite_ref-Macmillan_30-0" class="reference"><a href="#cite_note-Macmillan-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>A non-pegylated liposomal doxorubicin, called Myocet, is approved in the European Union and in Canada for the treatment of metastatic breast cancer in combination with <a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">cyclophosphamide</a>,<sup id="cite_ref-Myocet_liposomal_EPAR_2-3" class="reference"><a href="#cite_note-Myocet_liposomal_EPAR-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> but it has not been approved by the FDA for use in the United States. Unlike Doxil, the Myocet liposome does not have a polyethylene glycol coating, and therefore does not result in the same rate of PPE. The minimization of this side effect may allow for one-for-one (1:1) substitution with doxorubicin in the same treatment regimen, thereby improving safety with no loss of efficacy. Like Doxil, the liposomal encapsulation of the doxorubicin limits the cardiotoxicity. In theory, by limiting the cardiotoxicity of doxorubicin through liposomal encapsulation, it can be used safely in concurrent combination with other cardiotoxic chemotherapy drugs, such as <a href="/wiki/Trastuzumab" title="Trastuzumab">trastuzumab</a>. There is an FDA <a href="/wiki/Boxed_warning" title="Boxed warning">boxed warning</a> that trastuzumab cannot be used in concurrent combination with doxorubicin, only in sequential combination. Though concurrent combination of trastuzumab and doxorubicin in clinical studies found superior tumor response, the combination resulted in unacceptable cardiotoxicity, including risk of cardiac failure manifesting as <a href="/wiki/Congestive_heart_failure" class="mw-redirect" title="Congestive heart failure">congestive heart failure</a> (CHF). Published phase II study results have shown that Myocet, trastuzumab, and <a href="/wiki/Paclitaxel" title="Paclitaxel">paclitaxel</a> can safely be used concurrently without the cardiac risk, as measured by reduction in <a href="/wiki/LVEF" class="mw-redirect" title="LVEF">LVEF</a> function, while still achieving superior tumor response. This finding is the basis for the ongoing phase III trial for FDA approval.<sup id="cite_ref-Macmillan_30-1" class="reference"><a href="#cite_note-Macmillan-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=6" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Biosynthesis_of_doxorubicin" title="Biosynthesis of doxorubicin">Biosynthesis of doxorubicin</a></div> <p>Doxorubicin (DXR) is a 14-<a href="/wiki/Hydroxylated" class="mw-redirect" title="Hydroxylated">hydroxylated</a> version of <a href="/wiki/Daunorubicin" title="Daunorubicin">daunorubicin</a>, the immediate precursor of DXR in its <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthetic</a> pathway. </p><p><a href="/wiki/Daunorubicin" title="Daunorubicin">Daunorubicin</a> is more abundantly found as a <a href="/wiki/Natural_product" title="Natural product">natural product</a> because it is produced by a number of different <a href="/wiki/Wild_type" title="Wild type">wild type</a> <a href="/wiki/Strain_(biology)" title="Strain (biology)">strains</a> of <i><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a></i>. In contrast, only one known non-<a href="/wiki/Wild_type" title="Wild type">wild type</a> <a href="/wiki/Species" title="Species">species</a>, <i><a href="/wiki/Streptomyces_peucetius" title="Streptomyces peucetius">Streptomyces peucetius</a></i> <a href="/wiki/Subspecies" title="Subspecies">subspecies</a> <i>cesius</i> ATCC 27952, was initially found to be capable of producing the more widely used doxorubicin.<sup id="cite_ref-pmid9864344_32-0" class="reference"><a href="#cite_note-pmid9864344-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> This strain was created by Arcamone et al. in 1969 by <a href="/wiki/Mutation" title="Mutation">mutating</a> a strain producing daunorubicin, but not DXR, at least in detectable quantities.<sup id="cite_ref-pmid5365804_33-0" class="reference"><a href="#cite_note-pmid5365804-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Subsequently, Hutchinson's group showed that under special environmental conditions, or by the introduction of <a href="/wiki/Modifications_(genetics)" title="Modifications (genetics)">genetic modifications</a>, other strains of <i>Streptomyces</i> can produce doxorubicin.<sup id="cite_ref-pmid7828855_34-0" class="reference"><a href="#cite_note-pmid7828855-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> His group also <a href="/wiki/Cloned" class="mw-redirect" title="Cloned">cloned</a> many of the <a href="/wiki/Genes" class="mw-redirect" title="Genes">genes</a> required for DXR production, although not all of them have been fully characterized. In 1996, Strohl's group discovered, isolated and characterized dox A, the <a href="/wiki/Gene" title="Gene">gene</a> encoding the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> that converts daunorubicin into DXR.<sup id="cite_ref-pmid8655530_35-0" class="reference"><a href="#cite_note-pmid8655530-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>By 1999, they produced recombinant dox A, a <a href="/wiki/Cytochrome_P450_oxidase" class="mw-redirect" title="Cytochrome P450 oxidase">cytochrome P450 oxidase</a>, and found that it <a href="/wiki/Catalyzes" class="mw-redirect" title="Catalyzes">catalyzes</a> multiple steps in DXR <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a>, including steps leading to daunorubicin.<sup id="cite_ref-pmid9864343_36-0" class="reference"><a href="#cite_note-pmid9864343-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> This was significant because it became clear that all daunorubicin-producing strains have the necessary <a href="/wiki/Genes" class="mw-redirect" title="Genes">genes</a> to produce DXR, the much more therapeutically important of the two. Hutchinson's group went on to develop methods to improve the yield of DXR, from the <a href="/wiki/Industrial_fermentation" title="Industrial fermentation">fermentation</a> process used in its commercial production, not only by introducing dox A encoding <a href="/wiki/Plasmids" class="mw-redirect" title="Plasmids">plasmids</a>, but also by introducing mutations to deactivate <a href="/wiki/Enzymes" class="mw-redirect" title="Enzymes">enzymes</a> that shunt DXR precursors to less useful products, for example baumycin-like <a href="/wiki/Glycosides" class="mw-redirect" title="Glycosides">glycosides</a>.<sup id="cite_ref-pmid9864344_32-1" class="reference"><a href="#cite_note-pmid9864344-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Some triple mutants, that also <a href="/wiki/Gene_expression" title="Gene expression">over-expressed</a> dox A, were able to double the yield of DXR. This is of more than academic interest, because at that time DXR cost about $1.37 million per kg and current production in 1999 was 225 kg per annum.<sup id="cite_ref-pmid10455495_37-0" class="reference"><a href="#cite_note-pmid10455495-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>More efficient production techniques have brought the price down to $1.1 million per kg for the non<a href="/wiki/Liposomal" class="mw-redirect" title="Liposomal">liposomal</a> formulation. Although DXR can be produced <a href="/wiki/Semisynthesis" title="Semisynthesis">semi-synthetically</a> from daunorubicin, the process involves <a href="/wiki/Electrophilic" class="mw-redirect" title="Electrophilic">electrophilic</a> <a href="/wiki/Bromination" class="mw-redirect" title="Bromination">bromination</a> and multiple steps, and the yield is poor.<sup id="cite_ref-pmid8022857_38-0" class="reference"><a href="#cite_note-pmid8022857-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Since daunorubicin is produced by <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a>, it would be ideal if the <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> could complete DXR synthesis more effectively. </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=7" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Doxorubicin%E2%80%93DNA_complex_1D12.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Doxorubicin%E2%80%93DNA_complex_1D12.png/220px-Doxorubicin%E2%80%93DNA_complex_1D12.png" decoding="async" width="220" height="232" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Doxorubicin%E2%80%93DNA_complex_1D12.png/330px-Doxorubicin%E2%80%93DNA_complex_1D12.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ee/Doxorubicin%E2%80%93DNA_complex_1D12.png/440px-Doxorubicin%E2%80%93DNA_complex_1D12.png 2x" data-file-width="720" data-file-height="760" /></a><figcaption>Diagram of two doxorubicin molecules intercalating DNA, from <span class="plainlinks"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a>: <a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/1D12">1D12</a></span>.<sup id="cite_ref-frederick_39-0" class="reference"><a href="#cite_note-frederick-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>Doxorubicin interacts with DNA by <a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">intercalation</a> and inhibition of macromolecular <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesis</a>.<sup id="cite_ref-Ta2013_11-1" class="reference"><a href="#cite_note-Ta2013-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-fornari_40-0" class="reference"><a href="#cite_note-fornari-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-momparler_41-0" class="reference"><a href="#cite_note-momparler-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> This inhibits the progression of <a href="/wiki/Topoisomerase_II" class="mw-redirect" title="Topoisomerase II">topoisomerase II</a>, an enzyme which relaxes supercoils in DNA for <a href="/wiki/Transcription_(genetics)" class="mw-redirect" title="Transcription (genetics)">transcription</a>.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Doxorubicin stabilizes the topoisomerase II complex after it has broken the DNA chain for replication, preventing the DNA double helix from being released and thereby stopping the process of <a href="/wiki/DNA_replication" title="DNA replication">replication</a>.<sup id="cite_ref-Ta2013_11-2" class="reference"><a href="#cite_note-Ta2013-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It may also increase quinone type free radical production, hence contributing to its cytotoxicity.<sup id="cite_ref-AMH_15-1" class="reference"><a href="#cite_note-AMH-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>The planar aromatic chromophore portion of the molecule intercalates between two base pairs of the DNA, while the six-membered daunosamine sugar sits in the minor groove and interacts with flanking base pairs immediately adjacent to the intercalation site, as evidenced by several crystal structures.<sup id="cite_ref-frederick_39-1" class="reference"><a href="#cite_note-frederick-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pigram_43-0" class="reference"><a href="#cite_note-pigram-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>By <a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">intercalation</a>, doxorubicin can also induce <a href="/wiki/Histone" title="Histone">histone</a> eviction from transcriptionally active <a href="/wiki/Chromatin" title="Chromatin">chromatin</a>.<sup id="cite_ref-Pang_44-0" class="reference"><a href="#cite_note-Pang-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pang_45-0" class="reference"><a href="#cite_note-pang-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> As a result, the <a href="/wiki/DNA_repair" title="DNA repair">DNA damage response</a>, <a href="/wiki/Epigenome" title="Epigenome">epigenome</a> and <a href="/wiki/Transcriptome" title="Transcriptome">transcriptome</a> are deregulated in doxorubicin-exposed cells.<sup id="cite_ref-Pang_44-1" class="reference"><a href="#cite_note-Pang-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=8" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Andria_-_Castel_del_Monte_-_202209012324.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Andria_-_Castel_del_Monte_-_202209012324.jpg/220px-Andria_-_Castel_del_Monte_-_202209012324.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Andria_-_Castel_del_Monte_-_202209012324.jpg/330px-Andria_-_Castel_del_Monte_-_202209012324.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c9/Andria_-_Castel_del_Monte_-_202209012324.jpg/440px-Andria_-_Castel_del_Monte_-_202209012324.jpg 2x" data-file-width="4000" data-file-height="3000" /></a><figcaption>Bacteria producing doxorubicin were originally discovered in soil near <a href="/wiki/Castel_del_Monte,_Apulia" title="Castel del Monte, Apulia">Castel del Monte, Apulia</a>.</figcaption></figure> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Anthracycline#History" title="Anthracycline">Anthracycline § History</a>, <a href="/wiki/Daunorubicin#History" title="Daunorubicin">Daunorubicin § History</a>, and <a href="/wiki/History_of_cancer_chemotherapy" title="History of cancer chemotherapy">History of cancer chemotherapy</a></div> <p>In the 1950s, an Italian research company, <a href="/wiki/Farmitalia" title="Farmitalia">Farmitalia</a> Research Laboratories, began an organized effort to find anticancer compounds from soil-based microbes. A soil sample was isolated from the area surrounding the <a href="/wiki/Castel_del_Monte,_Apulia" title="Castel del Monte, Apulia">Castel del Monte</a>, a 13th-century castle. A new strain of <i><a href="/wiki/Streptomyces_peucetius" title="Streptomyces peucetius">Streptomyces peucetius</a></i>, which produced a red pigment, was isolated, and an antibiotic from this bacterium was effective against tumors in mice. Since a group of French researchers discovered the same compound at about the same time, the two teams named the compound <a href="/wiki/Daunorubicin" title="Daunorubicin">daunorubicin</a>, combining the name <i><a href="/wiki/Dauni" class="mw-redirect" title="Dauni">Dauni</a></i>, a pre-Roman tribe that occupied the area of Italy where the compound was isolated, with the French word for <a href="/wiki/Ruby" title="Ruby">ruby</a>, <i>rubis</i>, describing the color.<sup id="cite_ref-weiss_46-0" class="reference"><a href="#cite_note-weiss-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> Clinical trials began in the 1960s, and the drug was successful in treating acute leukemia and lymphoma. However, by 1967, it was recognized that daunorubicin could lead to fatal cardiac toxicity.<sup id="cite_ref-TanC_49-0" class="reference"><a href="#cite_note-TanC-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p><p>Researchers at Farmitalia soon discovered that changes in biological activity could be made by minor changes in the structure of the compound. A strain of <i>Streptomyces</i> was mutated using <i>N</i>-nitroso-<i>N</i>-methyl urethane, and this new strain produced a different, red-colored antibiotic. They named this new compound Adriamycin, after the <a href="/wiki/Adriatic_Sea" title="Adriatic Sea">Adriatic Sea</a>, and the name was later changed to doxorubicin to conform to the established naming convention.<sup id="cite_ref-pmid5365804_33-1" class="reference"><a href="#cite_note-pmid5365804-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> Doxorubicin showed better activity than daunorubicin against mouse tumors, and especially solid tumors. It also showed a higher <a href="/wiki/Therapeutic_index" title="Therapeutic index">therapeutic index</a>, yet the <a href="/wiki/Cardiotoxicity" title="Cardiotoxicity">cardiotoxicity</a> remained.<sup id="cite_ref-DiMarcoA_50-0" class="reference"><a href="#cite_note-DiMarcoA-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p><p>Doxorubicin and daunorubicin together can be thought of as prototype compounds for the <a href="/wiki/Anthracycline" title="Anthracycline">anthracyclines</a>. Subsequent research has led to many other anthracycline antibiotics, or analogs, and there are now over 2,000 known analogs of doxorubicin. By 1991, 553 of them had been evaluated in the screening program at the <a href="/wiki/National_Cancer_Institute" title="National Cancer Institute">National Cancer Institute</a> (NCI).<sup id="cite_ref-weiss_46-1" class="reference"><a href="#cite_note-weiss-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> In 2016 GPX-150 was granted <a href="/wiki/Orphan_drug" title="Orphan drug">orphan drug</a> designation by US FDA.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=9" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=10" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>On 24 March 2022, the <a href="/wiki/Committee_for_Medicinal_Products_for_Human_Use" title="Committee for Medicinal Products for Human Use">Committee for Medicinal Products for Human Use</a> (CHMP) of the <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA) adopted a positive opinion, recommending the granting of a marketing authorization for the medicinal product Zolsketil pegylated liposomal, intended for the treatment of metastatic breast cancer, advanced ovarian cancer, progressive multiple myeloma and AIDS-related Kaposi's sarcoma.<sup id="cite_ref-Zolsketil_pegylated_liposomal:_Pending_EC_decision_52-0" class="reference"><a href="#cite_note-Zolsketil_pegylated_liposomal:_Pending_EC_decision-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> The applicant for this medicinal product is Accord Healthcare S.L.U.<sup id="cite_ref-Zolsketil_pegylated_liposomal:_Pending_EC_decision_52-1" class="reference"><a href="#cite_note-Zolsketil_pegylated_liposomal:_Pending_EC_decision-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Zolsketil pegylated liposomal is a hybrid medicine of Adriamycin.<sup id="cite_ref-Zolsketil_pegylated_liposomal:_Pending_EC_decision_52-2" class="reference"><a href="#cite_note-Zolsketil_pegylated_liposomal:_Pending_EC_decision-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> It contains the same active substance as Adriamycin, but is available in a pegylated liposomal formulation.<sup id="cite_ref-Zolsketil_pegylated_liposomal:_Pending_EC_decision_52-3" class="reference"><a href="#cite_note-Zolsketil_pegylated_liposomal:_Pending_EC_decision-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Zolsketil pegylated liposomal was approved for medical use in the European Union in May 2022.<sup id="cite_ref-Zolsketil_pegylated_liposomal_EPAR_3-2" class="reference"><a href="#cite_note-Zolsketil_pegylated_liposomal_EPAR-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>On 21 July 2022, the CHMP adopted a positive opinion, recommending the granting of a marketing authorization for the medicinal product Celdoxome pegylated liposomal, intended for the treatment of metastatic breast cancer, advanced ovarian cancer, progressive multiple myeloma and AIDS-related Kaposi's sarcoma.<sup id="cite_ref-Celdoxome_pegylated_liposomal:_Pending_EC_decision_54-0" class="reference"><a href="#cite_note-Celdoxome_pegylated_liposomal:_Pending_EC_decision-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> The applicant for this medicinal product is YES Pharmaceutical Development Services GmbH.<sup id="cite_ref-Celdoxome_pegylated_liposomal:_Pending_EC_decision_54-1" class="reference"><a href="#cite_note-Celdoxome_pegylated_liposomal:_Pending_EC_decision-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> Celdoxome pegylated liposomal is a hybrid medicine of Adriamycin which has been authorized in the EU since 24 October 1979.<sup id="cite_ref-Celdoxome_pegylated_liposomal:_Pending_EC_decision_54-2" class="reference"><a href="#cite_note-Celdoxome_pegylated_liposomal:_Pending_EC_decision-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> Celdoxome pegylated liposomal contains the same active substance as Adriamycin, but is available in a pegylated liposomal formulation.<sup id="cite_ref-Celdoxome_pegylated_liposomal:_Pending_EC_decision_54-3" class="reference"><a href="#cite_note-Celdoxome_pegylated_liposomal:_Pending_EC_decision-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> Celdoxome pegylated liposomal was approved for medical use in the European Union in September 2022.<sup id="cite_ref-Celdoxome_pegylated_liposomal_EPAR_4-2" class="reference"><a href="#cite_note-Celdoxome_pegylated_liposomal_EPAR-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Names">Names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=11" title="Edit section: Names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is also known as hydroxydaunorubicin and hydroxydaunomycin.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>It is sold under a number of different brand names, including Adriamycin PFS, Adriamycin RDF, or Rubex.<sup id="cite_ref-MD_9-3" class="reference"><a href="#cite_note-MD-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Formulations">Formulations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=12" title="Edit section: Formulations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Doxorubicin is photosensitive, and containers are often covered by an aluminum bag and/or brown wax paper to prevent light from affecting it.<sup id="cite_ref-MD_9-4" class="reference"><a href="#cite_note-MD-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Doxorubicin is also available in <a href="/wiki/Liposome" title="Liposome">liposome</a>-encapsulated forms as Doxil (<a href="/wiki/PEGylation" title="PEGylation">pegylated</a> form), Myocet (nonpegylated form), and Caelyx,<sup id="cite_ref-Caelyx_pegylated_liposomal_EPAR_1-3" class="reference"><a href="#cite_note-Caelyx_pegylated_liposomal_EPAR-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> which are also given by intravenous injection.<sup id="cite_ref-MD_9-5" class="reference"><a href="#cite_note-MD-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The FDA approved the first generic version of Doxil, made by Sun, in February 2013.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=13" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Combination_therapy" title="Combination therapy">Combination therapy</a> experiments with <a href="/wiki/Sirolimus" title="Sirolimus">sirolimus</a> (rapamycin) and doxorubicin have shown promise in treating <a href="/wiki/Akt" class="mw-redirect" title="Akt">Akt</a>-positive <a href="/wiki/Lymphoma" title="Lymphoma">lymphomas</a> in mice.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p><p>Further, the release of photo-activated adriamycin with the aid of nanoporous optical antenna resulted in significant anti-cancer effect in MCF-7 breast cancer cells.<sup id="cite_ref-:1_58-0" class="reference"><a href="#cite_note-:1-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> In 2006, animal research coupling a <a href="/wiki/Murine" class="mw-redirect" title="Murine">murine</a> <a href="/wiki/Monoclonal_antibody" title="Monoclonal antibody">monoclonal antibody</a> with doxorubicin created an <a href="/wiki/Immunoconjugate" title="Immunoconjugate">immunoconjugate</a> that was able to eliminate <a href="/wiki/HIV" title="HIV">HIV-1</a> infection in mice.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Antimalarial_activity">Antimalarial activity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=14" title="Edit section: Antimalarial activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There is some evidence for antimalarial activity for doxorubicin and similar compounds. In 2009, a compound similar in structure to doxorubicin was found to inhibit <a href="/wiki/Plasmepsin" title="Plasmepsin">plasmepsin</a> II, an enzyme unique to the malarial parasite <i><a href="/wiki/Plasmodium_falciparum" title="Plasmodium falciparum">Plasmodium falciparum</a></i>.<sup id="cite_ref-friedman_61-0" class="reference"><a href="#cite_note-friedman-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> The pharmaceutical company <a href="/wiki/GlaxoSmithKline" class="mw-redirect" title="GlaxoSmithKline">GlaxoSmithKline</a> (GSK) later identified doxorubicin in a set of compounds that inhibit parasite growth.<sup id="cite_ref-Gamo_62-0" class="reference"><a href="#cite_note-Gamo-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Fluorescence">Fluorescence</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=15" title="Edit section: Fluorescence"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Doxorubicin is also known to be fluorescent. This has often been used to characterize doxorubicin concentrations, and has opened the possibility of using the molecule as a <a href="/wiki/Theranostic" class="mw-redirect" title="Theranostic">theranostic</a> agent. However, there are significant limitations, as doxorubicin's fluorescence spectrum is known to depend on a variety of factors, including the pH of the environment, solvent <a href="/wiki/Dielectric_constant" class="mw-redirect" title="Dielectric constant">dielectric constant</a> and others. Doxorubicin fluorescence is quenched by binding to DNA, and shielded by micelle encapsulation. It is also known to self-quench at high concentrations. In contrast, histone binding amplifies fluorescence.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=16" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Caelyx_pegylated_liposomal_EPAR-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Caelyx_pegylated_liposomal_EPAR_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Caelyx_pegylated_liposomal_EPAR_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Caelyx_pegylated_liposomal_EPAR_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Caelyx_pegylated_liposomal_EPAR_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.ema.europa.eu/en/medicines/human/EPAR/caelyx-pegylated-liposomal">"Caelyx pegylated liposomal EPAR"</a>. <i><a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EPAR)</i>. 17 September 2018. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220621052132/https://www.ema.europa.eu/en/medicines/human/EPAR/caelyx-pegylated-liposomal">Archived</a> from the original on 21 June 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">20 June</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=European+Medicines+Agency+%28EPAR%29&rft.atitle=Caelyx+pegylated+liposomal+EPAR&rft.date=2018-09-17&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fmedicines%2Fhuman%2FEPAR%2Fcaelyx-pegylated-liposomal&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Myocet_liposomal_EPAR-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-Myocet_liposomal_EPAR_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Myocet_liposomal_EPAR_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Myocet_liposomal_EPAR_2-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Myocet_liposomal_EPAR_2-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><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.ema.europa.eu/en/medicines/human/EPAR/myocet-liposomal-previously-myocet">"Myocet liposomal EPAR"</a>. <i>European Medicines Agency</i>. 17 September 2018. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220225004945/https://www.ema.europa.eu/en/medicines/human/EPAR/myocet-liposomal-previously-myocet">Archived</a> from the original on 25 February 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">20 June</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=European+Medicines+Agency&rft.atitle=Myocet+liposomal+EPAR&rft.date=2018-09-17&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fmedicines%2Fhuman%2FEPAR%2Fmyocet-liposomal-previously-myocet&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span> Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</span> </li> <li id="cite_note-Zolsketil_pegylated_liposomal_EPAR-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Zolsketil_pegylated_liposomal_EPAR_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Zolsketil_pegylated_liposomal_EPAR_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Zolsketil_pegylated_liposomal_EPAR_3-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><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.ema.europa.eu/en/medicines/human/EPAR/zolsketil-pegylated-liposomal">"Zolsketil pegylated liposomal EPAR"</a>. <i><a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA)</i>. 24 January 2022. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220621052452/https://www.ema.europa.eu/en/medicines/human/EPAR/zolsketil-pegylated-liposomal">Archived</a> from the original on 21 June 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">20 June</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=European+Medicines+Agency+%28EMA%29&rft.atitle=Zolsketil+pegylated+liposomal+EPAR&rft.date=2022-01-24&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fmedicines%2Fhuman%2FEPAR%2Fzolsketil-pegylated-liposomal&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span> Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</span> </li> <li id="cite_note-Celdoxome_pegylated_liposomal_EPAR-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-Celdoxome_pegylated_liposomal_EPAR_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Celdoxome_pegylated_liposomal_EPAR_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Celdoxome_pegylated_liposomal_EPAR_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><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.ema.europa.eu/en/medicines/human/EPAR/celdoxome-pegylated-liposomal">"Celdoxome pegylated liposomal EPAR"</a>. <i><a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA)</i>. 20 June 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">31 January</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=European+Medicines+Agency+%28EMA%29&rft.atitle=Celdoxome+pegylated+liposomal+EPAR&rft.date=2022-06-20&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fmedicines%2Fhuman%2FEPAR%2Fceldoxome-pegylated-liposomal&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span> Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=61804">"Caelyx product information"</a>. <i><a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a></i>. 25 April 2012. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220621054714/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=61804">Archived</a> from the original on 21 June 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">20 June</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Health+Canada&rft.atitle=Caelyx+product+information&rft.date=2012-04-25&rft_id=https%3A%2F%2Fhealth-products.canada.ca%2Fdpd-bdpp%2Finfo.do%3Flang%3Den%26code%3D61804&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=69014">"Myocet product information"</a>. <i><a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a></i>. 25 April 2012<span class="reference-accessdate">. Retrieved <span class="nowrap">20 June</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Health+Canada&rft.atitle=Myocet+product+information&rft.date=2012-04-25&rft_id=https%3A%2F%2Fhealth-products.canada.ca%2Fdpd-bdpp%2Finfo.do%3Flang%3Den%26code%3D69014&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=98300">"Taro-doxorubicin liposomal product information"</a>. <i><a href="/wiki/Health_Canada" title="Health Canada">Health Canada</a></i>. 25 April 2012. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210514034702/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=98300">Archived</a> from the original on 14 May 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">20 June</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Health+Canada&rft.atitle=Taro-doxorubicin+liposomal+product+information&rft.date=2012-04-25&rft_id=https%3A%2F%2Fhealth-products.canada.ca%2Fdpd-bdpp%2Finfo.do%3Flang%3Den%26code%3D98300&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-MSR-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-MSR_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MSR_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MSR_8-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://reference.medscape.com/drug/doxorubicin-342120#showall">"(doxorubicin) dosing, indications, interactions, adverse effects, and more"</a>. <i>Medscape Reference</i>. WebMD. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140416181339/http://reference.medscape.com/drug/doxorubicin-342120#showall">Archived</a> from the original on 16 April 2014<span class="reference-accessdate">. Retrieved <span class="nowrap">15 April</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Medscape+Reference&rft.atitle=%28doxorubicin%29+dosing%2C+indications%2C+interactions%2C+adverse+effects%2C+and+more&rft_id=http%3A%2F%2Freference.medscape.com%2Fdrug%2Fdoxorubicin-342120%23showall&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-MD-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-MD_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MD_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-MD_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-MD_9-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-MD_9-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-MD_9-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBrayfield2013" class="citation web cs1">Brayfield A, ed. (19 December 2013). <a rel="nofollow" class="external text" href="http://www.medicinescomplete.com/mc/martindale/current/ms-21514-e.htm">"Doxorubicin"</a>. <i>Martindale: The Complete Drug Reference</i>. Pharmaceutical Press. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210828065005/https://about.medicinescomplete.com/wp-content/themes/mc-marketing/assets/images/favicons-tiles/favicon.ico">Archived</a> from the original on 28 August 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">15 April</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Martindale%3A+The+Complete+Drug+Reference&rft.atitle=Doxorubicin&rft.date=2013-12-19&rft_id=http%3A%2F%2Fwww.medicinescomplete.com%2Fmc%2Fmartindale%2Fcurrent%2Fms-21514-e.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-AHFS2017-10"><span class="mw-cite-backlink">^ <a href="#cite_ref-AHFS2017_10-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AHFS2017_10-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-AHFS2017_10-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-AHFS2017_10-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-AHFS2017_10-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-AHFS2017_10-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-AHFS2017_10-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-AHFS2017_10-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-AHFS2017_10-8"><sup><i><b>i</b></i></sup></a></span> <span class="reference-text"><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/monograph/doxorubicin-hydrochloride.html">"Doxorubicin Hydrochloride"</a>. The American Society of Health-System Pharmacists. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161011065815/https://www.drugs.com/monograph/doxorubicin-hydrochloride.html">Archived</a> from the original on 11 October 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">12 January</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Doxorubicin+Hydrochloride&rft.pub=The+American+Society+of+Health-System+Pharmacists&rft_id=https%3A%2F%2Fwww.drugs.com%2Fmonograph%2Fdoxorubicin-hydrochloride.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Ta2013-11"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ta2013_11-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ta2013_11-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ta2013_11-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTacarSriamornsakDass2013" class="citation journal cs1">Tacar O, Sriamornsak P, Dass CR (February 2013). <a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.2042-7158.2012.01567.x">"Doxorubicin: an update on anticancer molecular action, toxicity and novel drug delivery systems"</a>. <i>The Journal of Pharmacy and Pharmacology</i>. <b>65</b> (2): <span class="nowrap">157–</span>170. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.2042-7158.2012.01567.x">10.1111/j.2042-7158.2012.01567.x</a></span>. <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/23278683">23278683</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:34737360">34737360</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+Pharmacy+and+Pharmacology&rft.atitle=Doxorubicin%3A+an+update+on+anticancer+molecular+action%2C+toxicity+and+novel+drug+delivery+systems&rft.volume=65&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E157-%3C%2Fspan%3E170&rft.date=2013-02&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A34737360%23id-name%3DS2CID&rft_id=info%3Apmid%2F23278683&rft_id=info%3Adoi%2F10.1111%2Fj.2042-7158.2012.01567.x&rft.aulast=Tacar&rft.aufirst=O&rft.au=Sriamornsak%2C+P&rft.au=Dass%2C+CR&rft_id=https%3A%2F%2Fdoi.org%2F10.1111%252Fj.2042-7158.2012.01567.x&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-WHO21st-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-WHO21st_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWorld_Health_Organization2019" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2019). <i>World Health Organization model list of essential medicines: 21st list 2019</i>. Geneva: World Health Organization. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10665%2F325771">10665/325771</a></span>. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.</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+21st+list+2019&rft.place=Geneva&rft.pub=World+Health+Organization&rft.date=2019&rft_id=info%3Ahdl%2F10665%2F325771&rft.au=World+Health+Organization&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-BNF69-13"><span class="mw-cite-backlink">^ <a href="#cite_ref-BNF69_13-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-BNF69_13-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><i>British national formulary : BNF 69</i> (69 ed.). British Medical Association. 2015. p. 583. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780857111562" title="Special:BookSources/9780857111562"><bdi>9780857111562</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=British+national+formulary+%3A+BNF+69&rft.pages=583&rft.edition=69&rft.pub=British+Medical+Association&rft.date=2015&rft.isbn=9780857111562&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRavina2011" class="citation book cs1">Ravina E (2011). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA291"><i>The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs</i></a>. John Wiley & Sons. p. 291. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527326693" title="Special:BookSources/9783527326693"><bdi>9783527326693</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170918185523/https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA291">Archived</a> from the original on 18 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Evolution+of+Drug+Discovery%3A+From+Traditional+Medicines+to+Modern+Drugs&rft.pages=291&rft.pub=John+Wiley+%26+Sons&rft.date=2011&rft.isbn=9783527326693&rft.aulast=Ravina&rft.aufirst=E&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DiDNy0XxGqT8C%26pg%3DPA291&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-AMH-15"><span class="mw-cite-backlink">^ <a href="#cite_ref-AMH_15-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AMH_15-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRossi2013" class="citation book cs1">Rossi S, ed. (2013). <i>Australian Medicines Handbook</i> (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-9805790-9-3" title="Special:BookSources/978-0-9805790-9-3"><bdi>978-0-9805790-9-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Australian+Medicines+Handbook&rft.place=Adelaide&rft.edition=2013&rft.pub=The+Australian+Medicines+Handbook+Unit+Trust&rft.date=2013&rft.isbn=978-0-9805790-9-3&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Alman_2020-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-Alman_2020_16-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAlmanAttiaBaumgartenBenson2020" class="citation journal cs1">Alman B, Attia S, Baumgarten C, Benson C, Blay JY, Bonvalot S, et al. (Desmoid Tumor Working Group) (March 2020). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ejca.2019.11.013">"The management of desmoid tumours: A joint global consensus-based guideline approach for adult and paediatric patients"</a>. <i>European Journal of Cancer</i>. <b>127</b>: <span class="nowrap">96–</span>107. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ejca.2019.11.013">10.1016/j.ejca.2019.11.013</a></span>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/2318%2F1793788">2318/1793788</a></span>. <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/32004793">32004793</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:210998595">210998595</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Journal+of+Cancer&rft.atitle=The+management+of+desmoid+tumours%3A+A+joint+global+consensus-based+guideline+approach+for+adult+and+paediatric+patients&rft.volume=127&rft.pages=%3Cspan+class%3D%22nowrap%22%3E96-%3C%2Fspan%3E107&rft.date=2020-03&rft_id=info%3Ahdl%2F2318%2F1793788&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A210998595%23id-name%3DS2CID&rft_id=info%3Apmid%2F32004793&rft_id=info%3Adoi%2F10.1016%2Fj.ejca.2019.11.013&rft.aulast=Alman&rft.aufirst=B&rft.au=Attia%2C+S&rft.au=Baumgarten%2C+C&rft.au=Benson%2C+C&rft.au=Blay%2C+JY&rft.au=Bonvalot%2C+S&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252Fj.ejca.2019.11.013&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBailon-MoscosoCoronel-HidalgoDuarte-CasarGuamán-Ortiz2023" class="citation journal cs1">Bailon-Moscoso N, Coronel-Hidalgo J, Duarte-Casar R, Guamán-Ortiz LM, Figueroa JG, Romero-Benavides JC (November 2023). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10669231">"Exploring the Antioxidant Potential of Tragia volubilis L.: Mitigating Chemotherapeutic Effects of Doxorubicin on Tumor Cells"</a>. <i>Antioxidants</i>. <b>12</b> (11): 2003. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3390%2Fantiox12112003">10.3390/antiox12112003</a></span>. <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/2076-3921">2076-3921</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10669231">10669231</a></span>. <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/38001856">38001856</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Antioxidants&rft.atitle=Exploring+the+Antioxidant+Potential+of+Tragia+volubilis+L.%3A+Mitigating+Chemotherapeutic+Effects+of+Doxorubicin+on+Tumor+Cells&rft.volume=12&rft.issue=11&rft.pages=2003&rft.date=2023-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10669231%23id-name%3DPMC&rft.issn=2076-3921&rft_id=info%3Apmid%2F38001856&rft_id=info%3Adoi%2F10.3390%2Fantiox12112003&rft.aulast=Bailon-Moscoso&rft.aufirst=N&rft.au=Coronel-Hidalgo%2C+J&rft.au=Duarte-Casar%2C+R&rft.au=Guam%C3%A1n-Ortiz%2C+LM&rft.au=Figueroa%2C+JG&rft.au=Romero-Benavides%2C+JC&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10669231&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Doxil_info-18"><span class="mw-cite-backlink">^ <a href="#cite_ref-Doxil_info_18-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Doxil_info_18-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text">"<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20070921075517/http://www.orthobiotech.com/common/prescribing_information/DOXIL/PDF/DOXIL_PI_Booklet.pdf">"DOXIL Product Information"</a> <span class="cs1-format">(PDF)</span>. Archived from <a rel="nofollow" class="external text" href="http://www.orthobiotech.com/common/prescribing_information/DOXIL/PDF/DOXIL_PI_Booklet.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 21 September 2007<span class="reference-accessdate">. Retrieved <span class="nowrap">19 April</span> 2007</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=DOXIL+Product+Information&rft_id=http%3A%2F%2Fwww.orthobiotech.com%2Fcommon%2Fprescribing_information%2FDOXIL%2FPDF%2FDOXIL_PI_Booklet.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Chaterjee-19"><span class="mw-cite-backlink">^ <a href="#cite_ref-Chaterjee_19-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Chaterjee_19-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChatterjeeZhangHonboKarliner2010" class="citation journal cs1">Chatterjee K, Zhang J, Honbo N, Karliner JS (January 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2848530">"Doxorubicin cardiomyopathy"</a>. <i>Cardiology</i>. <b>115</b> (2): <span class="nowrap">155–</span>162. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000265166">10.1159/000265166</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2848530">2848530</a></span>. <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/20016174">20016174</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cardiology&rft.atitle=Doxorubicin+cardiomyopathy&rft.volume=115&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E155-%3C%2Fspan%3E162&rft.date=2010-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2848530%23id-name%3DPMC&rft_id=info%3Apmid%2F20016174&rft_id=info%3Adoi%2F10.1159%2F000265166&rft.aulast=Chatterjee&rft.aufirst=K&rft.au=Zhang%2C+J&rft.au=Honbo%2C+N&rft.au=Karliner%2C+JS&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2848530&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFIchikawaGhanefarBayevaWu2014" class="citation journal cs1">Ichikawa Y, Ghanefar M, Bayeva M, Wu R, Khechaduri A, Naga Prasad SV, et al. (February 2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3904631">"Cardiotoxicity of doxorubicin is mediated through mitochondrial iron accumulation"</a>. <i>The Journal of Clinical Investigation</i>. <b>124</b> (2): <span class="nowrap">617–</span>630. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1172%2FJCI72931">10.1172/JCI72931</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3904631">3904631</a></span>. <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/24382354">24382354</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+Investigation&rft.atitle=Cardiotoxicity+of+doxorubicin+is+mediated+through+mitochondrial+iron+accumulation&rft.volume=124&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E617-%3C%2Fspan%3E630&rft.date=2014-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3904631%23id-name%3DPMC&rft_id=info%3Apmid%2F24382354&rft_id=info%3Adoi%2F10.1172%2FJCI72931&rft.aulast=Ichikawa&rft.aufirst=Y&rft.au=Ghanefar%2C+M&rft.au=Bayeva%2C+M&rft.au=Wu%2C+R&rft.au=Khechaduri%2C+A&rft.au=Naga+Prasad%2C+SV&rft.au=Mutharasan%2C+RK&rft.au=Naik%2C+TJ&rft.au=Ardehali%2C+H&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3904631&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Chat2010-21"><span class="mw-cite-backlink">^ <a href="#cite_ref-Chat2010_21-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Chat2010_21-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Chat2010_21-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Chat2010_21-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFChatterjeeZhangHonboKarliner2010" class="citation journal cs1">Chatterjee K, Zhang J, Honbo N, Karliner JS (2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2848530">"Doxorubicin cardiomyopathy"</a>. <i>Cardiology</i>. <b>115</b> (2): <span class="nowrap">155–</span>162. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000265166">10.1159/000265166</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2848530">2848530</a></span>. <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/20016174">20016174</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cardiology&rft.atitle=Doxorubicin+cardiomyopathy&rft.volume=115&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E155-%3C%2Fspan%3E162&rft.date=2010&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2848530%23id-name%3DPMC&rft_id=info%3Apmid%2F20016174&rft_id=info%3Adoi%2F10.1159%2F000265166&rft.aulast=Chatterjee&rft.aufirst=K&rft.au=Zhang%2C+J&rft.au=Honbo%2C+N&rft.au=Karliner%2C+JS&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2848530&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text"><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/monograph/dexrazoxane-hydrochloride.html">"Dexrazoxane Hydrochloride Monograph for Professionals - Drugs.com"</a>. <i>Drugs.com</i>. American Society of Health-System Pharmacists. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180801124706/https://www.drugs.com/monograph/dexrazoxane-hydrochloride.html">Archived</a> from the original on 1 August 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">1 August</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Drugs.com&rft.atitle=Dexrazoxane+Hydrochloride+Monograph+for+Professionals+-+Drugs.com&rft_id=https%3A%2F%2Fwww.drugs.com%2Fmonograph%2Fdexrazoxane-hydrochloride.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKaczmarekBrinkmanHeyndrickxVandenabeele2012" class="citation journal cs1">Kaczmarek A, Brinkman BM, Heyndrickx L, Vandenabeele P, Krysko DV (March 2012). "Severity of doxorubicin-induced small intestinal mucositis is regulated by the TLR-2 and TLR-9 pathways". <i>The Journal of Pathology</i>. <b>226</b> (4): <span class="nowrap">598–</span>608. <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%2Fpath.3009">10.1002/path.3009</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/21960132">21960132</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:206325412">206325412</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+Pathology&rft.atitle=Severity+of+doxorubicin-induced+small+intestinal+mucositis+is+regulated+by+the+TLR-2+and+TLR-9+pathways&rft.volume=226&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E598-%3C%2Fspan%3E608&rft.date=2012-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A206325412%23id-name%3DS2CID&rft_id=info%3Apmid%2F21960132&rft_id=info%3Adoi%2F10.1002%2Fpath.3009&rft.aulast=Kaczmarek&rft.aufirst=A&rft.au=Brinkman%2C+BM&rft.au=Heyndrickx%2C+L&rft.au=Vandenabeele%2C+P&rft.au=Krysko%2C+DV&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged November 2021">permanent dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://voice.ons.org/news-and-views/outpatient-oncology-drug-series-doxorubicin-is-the-infamous-red-devil">"Outpatient Oncology Drug Series: Doxorubicin is the Infamous Red Devil"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20180421163336/https://voice.ons.org/news-and-views/outpatient-oncology-drug-series-doxorubicin-is-the-infamous-red-devil">Archived</a> from the original on 21 April 2018<span class="reference-accessdate">. Retrieved <span class="nowrap">21 April</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Outpatient+Oncology+Drug+Series%3A+Doxorubicin+is+the+Infamous+Red+Devil&rft_id=https%3A%2F%2Fvoice.ons.org%2Fnews-and-views%2Foutpatient-oncology-drug-series-doxorubicin-is-the-infamous-red-devil&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-BlochCancerFaq-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-BlochCancerFaq_25-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBlochBloch" class="citation web cs1">Bloch R, Bloch A. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20070626082335/http://www.blochcancer.org/fighting/chap13.html">"25 Most Asked Questions"</a>. <i>Fighting Cancer</i>. R. A. Bloch Cancer Foundation. Archived from <a rel="nofollow" class="external text" href="http://www.blochcancer.org/fighting/chap13.html">the original</a> on 26 June 2007<span class="reference-accessdate">. Retrieved <span class="nowrap">28 June</span> 2007</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Fighting+Cancer&rft.atitle=25+Most+Asked+Questions&rft.aulast=Bloch&rft.aufirst=R&rft.au=Bloch%2C+A&rft_id=http%3A%2F%2Fwww.blochcancer.org%2Ffighting%2Fchap13.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGroopman2007" class="citation book cs1"><a href="/wiki/Jerome_Groopman" title="Jerome Groopman">Groopman JE</a> (2007). <a href="/wiki/How_Doctors_Think" title="How Doctors Think"><i>How Doctors Think</i></a>. Boston: Houghton Mifflin. p. <a rel="nofollow" class="external text" href="https://archive.org/details/howdoctorsthink00groo/page/49">49</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-618-61003-7" title="Special:BookSources/978-0-618-61003-7"><bdi>978-0-618-61003-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=How+Doctors+Think&rft.place=Boston&rft.pages=49&rft.pub=Houghton+Mifflin&rft.date=2007&rft.isbn=978-0-618-61003-7&rft.aulast=Groopman&rft.aufirst=JE&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFYeoLamZeeChan2004" class="citation journal cs1">Yeo W, Lam KC, Zee B, Chan PS, Mo FK, Ho WM, et al. (November 2004). <a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fannonc%2Fmdh430">"Hepatitis B reactivation in patients with hepatocellular carcinoma undergoing systemic chemotherapy"</a>. <i>Annals of Oncology</i>. <b>15</b> (11): <span class="nowrap">1661–</span>1666. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Fannonc%2Fmdh430">10.1093/annonc/mdh430</a></span>. <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/15520068">15520068</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annals+of+Oncology&rft.atitle=Hepatitis+B+reactivation+in+patients+with+hepatocellular+carcinoma+undergoing+systemic+chemotherapy&rft.volume=15&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1661-%3C%2Fspan%3E1666&rft.date=2004-11&rft_id=info%3Adoi%2F10.1093%2Fannonc%2Fmdh430&rft_id=info%3Apmid%2F15520068&rft.aulast=Yeo&rft.aufirst=W&rft.au=Lam%2C+KC&rft.au=Zee%2C+B&rft.au=Chan%2C+PS&rft.au=Mo%2C+FK&rft.au=Ho%2C+WM&rft.au=Wong%2C+WL&rft.au=Leung%2C+TW&rft.au=Chan%2C+AT&rft.au=Ma%2C+B&rft.au=Mok%2C+TS&rft.au=Johnson%2C+PJ&rft_id=https%3A%2F%2Fdoi.org%2F10.1093%252Fannonc%252Fmdh430&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDillonHirschfieldAllisonRege2008" class="citation journal cs1">Dillon R, Hirschfield GM, Allison ME, Rege KP (July 2008). "Fatal reactivation of hepatitis B after chemotherapy for lymphoma". <i>BMJ</i>. <b>337</b>: a423. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1136%2Fbmj.39490.680498.BE">10.1136/bmj.39490.680498.BE</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/18595895">18595895</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:11661945">11661945</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=BMJ&rft.atitle=Fatal+reactivation+of+hepatitis+B+after+chemotherapy+for+lymphoma&rft.volume=337&rft.pages=a423&rft.date=2008-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A11661945%23id-name%3DS2CID&rft_id=info%3Apmid%2F18595895&rft_id=info%3Adoi%2F10.1136%2Fbmj.39490.680498.BE&rft.aulast=Dillon&rft.aufirst=R&rft.au=Hirschfield%2C+GM&rft.au=Allison%2C+ME&rft.au=Rege%2C+KP&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.nejm.org/image-challenge?ci=09012011&query=TOC">"Image Challenge | NEJM"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20130316203047/http://www.nejm.org/image-challenge?ci=09012011&query=TOC">Archived</a> from the original on 16 March 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">1 September</span> 2011</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Image+Challenge+%26%23124%3B+NEJM&rft_id=http%3A%2F%2Fwww.nejm.org%2Fimage-challenge%3Fci%3D09012011%26query%3DTOC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Macmillan-30"><span class="mw-cite-backlink">^ <a href="#cite_ref-Macmillan_30-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Macmillan_30-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.macmillan.org.uk/Cancerinformation/Cancertreatment/Treatmenttypes/Chemotherapy/Individualdrugs/Liposomaldoxorubicin.aspx">"Liposomal doxorubicin (Caelyx, Myocet)"</a>. Macmillan Cancer Support. 1 April 2009. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20091129030936/http://www.macmillan.org.uk/Cancerinformation/Cancertreatment/Treatmenttypes/Chemotherapy/Individualdrugs/Liposomaldoxorubicin.aspx">Archived</a> from the original on 29 November 2009<span class="reference-accessdate">. Retrieved <span class="nowrap">27 November</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Liposomal+doxorubicin+%28Caelyx%2C+Myocet%29&rft.pub=Macmillan+Cancer+Support&rft.date=2009-04-01&rft_id=http%3A%2F%2Fwww.macmillan.org.uk%2FCancerinformation%2FCancertreatment%2FTreatmenttypes%2FChemotherapy%2FIndividualdrugs%2FLiposomaldoxorubicin.aspx&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.chemocare.com/bio/doxorubicin_liposomal.asp">"Doxorubicin liposomal"</a>. <i>Chemocare</i>. <a href="/wiki/Cleveland_Clinic" title="Cleveland Clinic">Cleveland Clinic</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20100102095755/http://chemocare.com/bio/doxorubicin_liposomal.asp">Archived</a> from the original on 2 January 2010<span class="reference-accessdate">. Retrieved <span class="nowrap">27 November</span> 2009</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Chemocare&rft.atitle=Doxorubicin+liposomal&rft_id=http%3A%2F%2Fwww.chemocare.com%2Fbio%2Fdoxorubicin_liposomal.asp&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-pmid9864344-32"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid9864344_32-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid9864344_32-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLomovskayaOttenDoi-KatayamaFonstein1999" class="citation journal cs1">Lomovskaya N, Otten SL, Doi-Katayama Y, Fonstein L, Liu XC, Takatsu T, et al. (January 1999). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC103563">"Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene"</a>. <i>Journal of Bacteriology</i>. <b>181</b> (1): <span class="nowrap">305–</span>318. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FJB.181.1.305-318.1999">10.1128/JB.181.1.305-318.1999</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC103563">103563</a></span>. <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/9864344">9864344</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+Bacteriology&rft.atitle=Doxorubicin+overproduction+in+Streptomyces+peucetius%3A+cloning+and+characterization+of+the+dnrU+ketoreductase+and+dnrV+genes+and+the+doxA+cytochrome+P-450+hydroxylase+gene&rft.volume=181&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E305-%3C%2Fspan%3E318&rft.date=1999-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC103563%23id-name%3DPMC&rft_id=info%3Apmid%2F9864344&rft_id=info%3Adoi%2F10.1128%2FJB.181.1.305-318.1999&rft.aulast=Lomovskaya&rft.aufirst=N&rft.au=Otten%2C+SL&rft.au=Doi-Katayama%2C+Y&rft.au=Fonstein%2C+L&rft.au=Liu%2C+XC&rft.au=Takatsu%2C+T&rft.au=Inventi-Solari%2C+A&rft.au=Filippini%2C+S&rft.au=Torti%2C+F&rft.au=Colombo%2C+AL&rft.au=Hutchinson%2C+CR&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC103563&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-pmid5365804-33"><span class="mw-cite-backlink">^ <a href="#cite_ref-pmid5365804_33-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pmid5365804_33-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFArcamoneCassinelliFantiniGrein1969" class="citation journal cs1">Arcamone F, Cassinelli G, Fantini G, Grein A, Orezzi P, Pol C, et al. (November 1969). "Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius". <i>Biotechnology and Bioengineering</i>. <b>11</b> (6): <span class="nowrap">1101–</span>1110. <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%2Fbit.260110607">10.1002/bit.260110607</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/5365804">5365804</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:21897153">21897153</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biotechnology+and+Bioengineering&rft.atitle=Adriamycin%2C+14-hydroxydaunomycin%2C+a+new+antitumor+antibiotic+from+S.+peucetius+var.+caesius&rft.volume=11&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1101-%3C%2Fspan%3E1110&rft.date=1969-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A21897153%23id-name%3DS2CID&rft_id=info%3Apmid%2F5365804&rft_id=info%3Adoi%2F10.1002%2Fbit.260110607&rft.aulast=Arcamone&rft.aufirst=F&rft.au=Cassinelli%2C+G&rft.au=Fantini%2C+G&rft.au=Grein%2C+A&rft.au=Orezzi%2C+P&rft.au=Pol%2C+C&rft.au=Spalla%2C+C&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-pmid7828855-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid7828855_34-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGrimmMadduriAliHutchinson1994" class="citation journal cs1">Grimm A, Madduri K, Ali A, Hutchinson CR (December 1994). <a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0378-1119%2894%2990625-4">"Characterization of the Streptomyces peucetius ATCC 29050 genes encoding doxorubicin polyketide synthase"</a>. <i>Gene</i>. <b>151</b> (<span class="nowrap">1–</span>2): <span class="nowrap">1–</span>10. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0378-1119%2894%2990625-4">10.1016/0378-1119(94)90625-4</a></span>. <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/7828855">7828855</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gene&rft.atitle=Characterization+of+the+Streptomyces+peucetius+ATCC+29050+genes+encoding+doxorubicin+polyketide+synthase&rft.volume=151&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E10&rft.date=1994-12&rft_id=info%3Adoi%2F10.1016%2F0378-1119%2894%2990625-4&rft_id=info%3Apmid%2F7828855&rft.aulast=Grimm&rft.aufirst=A&rft.au=Madduri%2C+K&rft.au=Ali%2C+A&rft.au=Hutchinson%2C+CR&rft_id=https%3A%2F%2Fdoi.org%2F10.1016%252F0378-1119%252894%252990625-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-pmid8655530-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid8655530_35-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDickensStrohl1996" class="citation journal cs1">Dickens ML, Strohl WR (June 1996). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC178102">"Isolation and characterization of a gene from Streptomyces sp. strain C5 that confers the ability to convert daunomycin to doxorubicin on Streptomyces lividans TK24"</a>. <i>Journal of Bacteriology</i>. <b>178</b> (11): <span class="nowrap">3389–</span>3395. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2Fjb.178.11.3389-3395.1996">10.1128/jb.178.11.3389-3395.1996</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC178102">178102</a></span>. <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/8655530">8655530</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+Bacteriology&rft.atitle=Isolation+and+characterization+of+a+gene+from+Streptomyces+sp.+strain+C5+that+confers+the+ability+to+convert+daunomycin+to+doxorubicin+on+Streptomyces+lividans+TK24&rft.volume=178&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3389-%3C%2Fspan%3E3395&rft.date=1996-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC178102%23id-name%3DPMC&rft_id=info%3Apmid%2F8655530&rft_id=info%3Adoi%2F10.1128%2Fjb.178.11.3389-3395.1996&rft.aulast=Dickens&rft.aufirst=ML&rft.au=Strohl%2C+WR&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC178102&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-pmid9864343-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid9864343_36-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWalczakDickensPriestleyStrohl1999" class="citation journal cs1">Walczak RJ, Dickens ML, Priestley ND, Strohl WR (January 1999). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC103562">"Purification, properties, and characterization of recombinant Streptomyces sp. strain C5 DoxA, a cytochrome P-450 catalyzing multiple steps in doxorubicin biosynthesis"</a>. <i>Journal of Bacteriology</i>. <b>181</b> (1): <span class="nowrap">298–</span>304. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FJB.181.1.298-304.1999">10.1128/JB.181.1.298-304.1999</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC103562">103562</a></span>. <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/9864343">9864343</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+Bacteriology&rft.atitle=Purification%2C+properties%2C+and+characterization+of+recombinant+Streptomyces+sp.+strain+C5+DoxA%2C+a+cytochrome+P-450+catalyzing+multiple+steps+in+doxorubicin+biosynthesis&rft.volume=181&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E298-%3C%2Fspan%3E304&rft.date=1999-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC103562%23id-name%3DPMC&rft_id=info%3Apmid%2F9864343&rft_id=info%3Adoi%2F10.1128%2FJB.181.1.298-304.1999&rft.aulast=Walczak&rft.aufirst=RJ&rft.au=Dickens%2C+ML&rft.au=Priestley%2C+ND&rft.au=Strohl%2C+WR&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC103562&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-pmid10455495-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid10455495_37-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHutchinsonColombo1999" class="citation journal cs1">Hutchinson CR, Colombo AL (July 1999). "Genetic engineering of doxorubicin production in Streptomyces peucetius: a review". <i>Journal of Industrial Microbiology & Biotechnology</i>. <b>23</b> (1): <span class="nowrap">647–</span>652. <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%2Fsj.jim.2900673">10.1038/sj.jim.2900673</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/10455495">10455495</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:27337697">27337697</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+Industrial+Microbiology+%26+Biotechnology&rft.atitle=Genetic+engineering+of+doxorubicin+production+in+Streptomyces+peucetius%3A+a+review&rft.volume=23&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E647-%3C%2Fspan%3E652&rft.date=1999-07&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A27337697%23id-name%3DS2CID&rft_id=info%3Apmid%2F10455495&rft_id=info%3Adoi%2F10.1038%2Fsj.jim.2900673&rft.aulast=Hutchinson&rft.aufirst=CR&rft.au=Colombo%2C+AL&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-pmid8022857-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid8022857_38-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLown1993" class="citation journal cs1">Lown JW (November 1993). "Anthracycline and anthraquinone anticancer agents: current status and recent developments". <i>Pharmacology & Therapeutics</i>. <b>60</b> (2): <span class="nowrap">185–</span>214. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0163-7258%2893%2990006-Y">10.1016/0163-7258(93)90006-Y</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/8022857">8022857</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacology+%26+Therapeutics&rft.atitle=Anthracycline+and+anthraquinone+anticancer+agents%3A+current+status+and+recent+developments&rft.volume=60&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E185-%3C%2Fspan%3E214&rft.date=1993-11&rft_id=info%3Adoi%2F10.1016%2F0163-7258%2893%2990006-Y&rft_id=info%3Apmid%2F8022857&rft.aulast=Lown&rft.aufirst=JW&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-frederick-39"><span class="mw-cite-backlink">^ <a href="#cite_ref-frederick_39-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-frederick_39-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFrederickWilliamsUghettovan_der_Marel1990" class="citation journal cs1">Frederick CA, Williams LD, Ughetto G, van der Marel GA, van Boom JH, Rich A, et al. (March 1990). "Structural comparison of anticancer drug-DNA complexes: adriamycin and daunomycin". <i>Biochemistry</i>. <b>29</b> (10): <span class="nowrap">2538–</span>2549. <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%2Fbi00462a016">10.1021/bi00462a016</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/2334681">2334681</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biochemistry&rft.atitle=Structural+comparison+of+anticancer+drug-DNA+complexes%3A+adriamycin+and+daunomycin&rft.volume=29&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2538-%3C%2Fspan%3E2549&rft.date=1990-03&rft_id=info%3Adoi%2F10.1021%2Fbi00462a016&rft_id=info%3Apmid%2F2334681&rft.aulast=Frederick&rft.aufirst=CA&rft.au=Williams%2C+LD&rft.au=Ughetto%2C+G&rft.au=van+der+Marel%2C+GA&rft.au=van+Boom%2C+JH&rft.au=Rich%2C+A&rft.au=Wang%2C+AH&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span> Crystal structure is available for download as a <a rel="nofollow" class="external text" href="http://www.rcsb.org/pdb/explore.do?structureId=1D12">PDB</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20080114013050/http://www.rcsb.org/pdb/explore.do?structureId=1D12">Archived</a> 14 January 2008 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a> file.</span> </li> <li id="cite_note-fornari-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-fornari_40-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFornariRandolphYalowichRitke1994" class="citation journal cs1">Fornari FA, Randolph JK, Yalowich JC, Ritke MK, Gewirtz DA (April 1994). "Interference by doxorubicin with DNA unwinding in MCF-7 breast tumor cells". <i>Molecular Pharmacology</i>. <b>45</b> (4): <span class="nowrap">649–</span>656. <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%2FS0026-895X%2825%2910149-1">10.1016/S0026-895X(25)10149-1</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/8183243">8183243</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Pharmacology&rft.atitle=Interference+by+doxorubicin+with+DNA+unwinding+in+MCF-7+breast+tumor+cells&rft.volume=45&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E649-%3C%2Fspan%3E656&rft.date=1994-04&rft_id=info%3Adoi%2F10.1016%2FS0026-895X%2825%2910149-1&rft_id=info%3Apmid%2F8183243&rft.aulast=Fornari&rft.aufirst=FA&rft.au=Randolph%2C+JK&rft.au=Yalowich%2C+JC&rft.au=Ritke%2C+MK&rft.au=Gewirtz%2C+DA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-momparler-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-momparler_41-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMomparlerKaronSiegelAvila1976" class="citation journal cs1">Momparler RL, Karon M, Siegel SE, Avila F (August 1976). <a rel="nofollow" class="external text" href="http://cancerres.aacrjournals.org/cgi/reprint/36/8/2891">"Effect of adriamycin on DNA, RNA, and protein synthesis in cell-free systems and intact cells"</a>. <i>Cancer Research</i>. <b>36</b> (8): <span class="nowrap">2891–</span>2895. <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/1277199">1277199</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20090205063327/http://cancerres.aacrjournals.org/cgi/reprint/36/8/2891">Archived</a> from the original on 5 February 2009.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer+Research&rft.atitle=Effect+of+adriamycin+on+DNA%2C+RNA%2C+and+protein+synthesis+in+cell-free+systems+and+intact+cells&rft.volume=36&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2891-%3C%2Fspan%3E2895&rft.date=1976-08&rft_id=info%3Apmid%2F1277199&rft.aulast=Momparler&rft.aufirst=RL&rft.au=Karon%2C+M&rft.au=Siegel%2C+SE&rft.au=Avila%2C+F&rft_id=http%3A%2F%2Fcancerres.aacrjournals.org%2Fcgi%2Freprint%2F36%2F8%2F2891&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPommierLeoZhangMarchand2010" class="citation journal cs1">Pommier Y, Leo E, Zhang H, Marchand C (May 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7316379">"DNA topoisomerases and their poisoning by anticancer and antibacterial drugs"</a>. <i>Chemistry & Biology</i>. <b>17</b> (5): <span class="nowrap">421–</span>433. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.chembiol.2010.04.012">10.1016/j.chembiol.2010.04.012</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7316379">7316379</a></span>. <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/20534341">20534341</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemistry+%26+Biology&rft.atitle=DNA+topoisomerases+and+their+poisoning+by+anticancer+and+antibacterial+drugs&rft.volume=17&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E421-%3C%2Fspan%3E433&rft.date=2010-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7316379%23id-name%3DPMC&rft_id=info%3Apmid%2F20534341&rft_id=info%3Adoi%2F10.1016%2Fj.chembiol.2010.04.012&rft.aulast=Pommier&rft.aufirst=Y&rft.au=Leo%2C+E&rft.au=Zhang%2C+H&rft.au=Marchand%2C+C&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7316379&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-pigram-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-pigram_43-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPigramFullerHamilton1972" class="citation journal cs1">Pigram WJ, Fuller W, Hamilton LD (January 1972). "Stereochemistry of intercalation: interaction of daunomycin with DNA". <i>Nature</i>. <b>235</b> (53): <span class="nowrap">17–</span>19. <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%2Fnewbio235017a0">10.1038/newbio235017a0</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/4502404">4502404</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Stereochemistry+of+intercalation%3A+interaction+of+daunomycin+with+DNA&rft.volume=235&rft.issue=53&rft.pages=%3Cspan+class%3D%22nowrap%22%3E17-%3C%2Fspan%3E19&rft.date=1972-01&rft_id=info%3Adoi%2F10.1038%2Fnewbio235017a0&rft_id=info%3Apmid%2F4502404&rft.aulast=Pigram&rft.aufirst=WJ&rft.au=Fuller%2C+W&rft.au=Hamilton%2C+LD&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Pang-44"><span class="mw-cite-backlink">^ <a href="#cite_ref-Pang_44-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Pang_44-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPangQiaoJanssenVelds2013" class="citation journal cs1">Pang B, Qiao X, Janssen L, Velds A, Groothuis T, Kerkhoven R, et al. (2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3674280">"Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin"</a>. <i>Nature Communications</i>. <b>4</b> (5): 1908. <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/2013NatCo...4.1908P">2013NatCo...4.1908P</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fncomms2921">10.1038/ncomms2921</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3674280">3674280</a></span>. <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/23715267">23715267</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Communications&rft.atitle=Drug-induced+histone+eviction+from+open+chromatin+contributes+to+the+chemotherapeutic+effects+of+doxorubicin&rft.volume=4&rft.issue=5&rft.pages=1908&rft.date=2013&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3674280%23id-name%3DPMC&rft_id=info%3Apmid%2F23715267&rft_id=info%3Adoi%2F10.1038%2Fncomms2921&rft_id=info%3Abibcode%2F2013NatCo...4.1908P&rft.aulast=Pang&rft.aufirst=B&rft.au=Qiao%2C+X&rft.au=Janssen%2C+L&rft.au=Velds%2C+A&rft.au=Groothuis%2C+T&rft.au=Kerkhoven%2C+R&rft.au=Nieuwland%2C+M&rft.au=Ovaa%2C+H&rft.au=Rottenberg%2C+S&rft.au=van+Tellingen%2C+O&rft.au=Janssen%2C+J&rft.au=Huijgens%2C+P&rft.au=Zwart%2C+W&rft.au=Neefjes%2C+J&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3674280&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-pang-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-pang_45-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPangde_JongQiaoWessels2015" class="citation journal cs1">Pang B, de Jong J, Qiao X, Wessels LF, Neefjes J (July 2015). "Chemical profiling of the genome with anti-cancer drugs defines target specificities". <i>Nature Chemical Biology</i>. <b>11</b> (7): <span class="nowrap">472–</span>480. <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%2Fnchembio.1811">10.1038/nchembio.1811</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/25961671">25961671</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature+Chemical+Biology&rft.atitle=Chemical+profiling+of+the+genome+with+anti-cancer+drugs+defines+target+specificities&rft.volume=11&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E472-%3C%2Fspan%3E480&rft.date=2015-07&rft_id=info%3Adoi%2F10.1038%2Fnchembio.1811&rft_id=info%3Apmid%2F25961671&rft.aulast=Pang&rft.aufirst=B&rft.au=de+Jong%2C+J&rft.au=Qiao%2C+X&rft.au=Wessels%2C+LF&rft.au=Neefjes%2C+J&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-weiss-46"><span class="mw-cite-backlink">^ <a href="#cite_ref-weiss_46-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-weiss_46-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWeiss1992" class="citation journal cs1">Weiss RB (December 1992). "The anthracyclines: will we ever find a better doxorubicin?". <i>Seminars in Oncology</i>. <b>19</b> (6): <span class="nowrap">670–</span>686. <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/1462166">1462166</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Seminars+in+Oncology&rft.atitle=The+anthracyclines%3A+will+we+ever+find+a+better+doxorubicin%3F&rft.volume=19&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E670-%3C%2Fspan%3E686&rft.date=1992-12&rft_id=info%3Apmid%2F1462166&rft.aulast=Weiss&rft.aufirst=RB&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-47">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBaruffa1966" class="citation journal cs1">Baruffa G (1966). "Clinical trials in Plasmodium falciparum malaria with a long-acting sulphonamide". <i>Transactions of the Royal Society of Tropical Medicine and Hygiene</i>. <b>60</b> (2): <span class="nowrap">222–</span>224. <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%2F0035-9203%2866%2990030-7">10.1016/0035-9203(66)90030-7</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/5332105">5332105</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Transactions+of+the+Royal+Society+of+Tropical+Medicine+and+Hygiene&rft.atitle=Clinical+trials+in+Plasmodium+falciparum+malaria+with+a+long-acting+sulphonamide&rft.volume=60&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E222-%3C%2Fspan%3E224&rft.date=1966&rft_id=info%3Adoi%2F10.1016%2F0035-9203%2866%2990030-7&rft_id=info%3Apmid%2F5332105&rft.aulast=Baruffa&rft.aufirst=G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-48"><span class="mw-cite-backlink"><b><a href="#cite_ref-48">^</a></b></span> <span class="reference-text">Per prior citation, the first publication: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCamerinoPalamidessi1960" class="citation journal cs1 cs1-prop-foreign-lang-source">Camerino B, Palamidessi G (1960). "Derivati della parazina II. Sulfonamdopir". <i>Gazz Chim Ital</i> (in Italian). <b>90</b>: <span class="nowrap">1802–</span>1815.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Gazz+Chim+Ital&rft.atitle=Derivati+della+parazina+II.+Sulfonamdopir&rft.volume=90&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1802-%3C%2Fspan%3E1815&rft.date=1960&rft.aulast=Camerino&rft.aufirst=B&rft.au=Palamidessi%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-TanC-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-TanC_49-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTanTasakaYuMurphy1967" class="citation journal cs1">Tan C, Tasaka H, Yu KP, Murphy ML, Karnofsky DA (March 1967). <a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F1097-0142%281967%2920%3A3%3C333%3A%3AAID-CNCR2820200302%3E3.0.CO%3B2-K">"Daunomycin, an antitumor antibiotic, in the treatment of neoplastic disease. Clinical evaluation with special reference to childhood leukemia"</a>. <i>Cancer</i>. <b>20</b> (3): <span class="nowrap">333–</span>353. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F1097-0142%281967%2920%3A3%3C333%3A%3AAID-CNCR2820200302%3E3.0.CO%3B2-K">10.1002/1097-0142(1967)20:3<333::AID-CNCR2820200302>3.0.CO;2-K</a></span>. <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/4290058">4290058</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:19272219">19272219</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer&rft.atitle=Daunomycin%2C+an+antitumor+antibiotic%2C+in+the+treatment+of+neoplastic+disease.+Clinical+evaluation+with+special+reference+to+childhood+leukemia&rft.volume=20&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E333-%3C%2Fspan%3E353&rft.date=1967-03&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A19272219%23id-name%3DS2CID&rft_id=info%3Apmid%2F4290058&rft_id=info%3Adoi%2F10.1002%2F1097-0142%281967%2920%3A3%3C333%3A%3AAID-CNCR2820200302%3E3.0.CO%3B2-K&rft.aulast=Tan&rft.aufirst=C&rft.au=Tasaka%2C+H&rft.au=Yu%2C+KP&rft.au=Murphy%2C+ML&rft.au=Karnofsky%2C+DA&rft_id=https%3A%2F%2Fdoi.org%2F10.1002%252F1097-0142%25281967%252920%253A3%253C333%253A%253AAID-CNCR2820200302%253E3.0.CO%253B2-K&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-DiMarcoA-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-DiMarcoA_50-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFDi_MarcoGaetaniScarpinato1969" class="citation journal cs1">Di Marco A, Gaetani M, Scarpinato B (February 1969). "Adriamycin (NSC-123,127): a new antibiotic with antitumor activity". <i>Cancer Chemotherapy Reports</i>. <b>53</b> (1): <span class="nowrap">33–</span>37. <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/5772652">5772652</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Cancer+Chemotherapy+Reports&rft.atitle=Adriamycin+%28NSC-123%2C127%29%3A+a+new+antibiotic+with+antitumor+activity&rft.volume=53&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E33-%3C%2Fspan%3E37&rft.date=1969-02&rft_id=info%3Apmid%2F5772652&rft.aulast=Di+Marco&rft.aufirst=A&rft.au=Gaetani%2C+M&rft.au=Scarpinato%2C+B&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-51"><span class="mw-cite-backlink"><b><a href="#cite_ref-51">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.cancernetwork.com/sarcoma/investigational-sarcoma-drug-gpx-150-gets-orphan-drug-designation">Investigational Sarcoma Drug GPX-150 Gets Orphan Drug Designation. 2016</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160124010110/http://www.cancernetwork.com/sarcoma/investigational-sarcoma-drug-gpx-150-gets-orphan-drug-designation">Archived</a> 24 January 2016 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span> </li> <li id="cite_note-Zolsketil_pegylated_liposomal:_Pending_EC_decision-52"><span class="mw-cite-backlink">^ <a href="#cite_ref-Zolsketil_pegylated_liposomal:_Pending_EC_decision_52-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Zolsketil_pegylated_liposomal:_Pending_EC_decision_52-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Zolsketil_pegylated_liposomal:_Pending_EC_decision_52-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Zolsketil_pegylated_liposomal:_Pending_EC_decision_52-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><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.ema.europa.eu/en/medicines/human/summaries-opinion/zolsketil-pegylated-liposomal">"Zolsketil pegylated liposomal: Pending EC decision"</a>. <i><a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA)</i>. 24 March 2022. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220329163755/https://www.ema.europa.eu/en/medicines/human/summaries-opinion/zolsketil-pegylated-liposomal">Archived</a> from the original on 29 March 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">29 March</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=European+Medicines+Agency+%28EMA%29&rft.atitle=Zolsketil+pegylated+liposomal%3A+Pending+EC+decision&rft.date=2022-03-24&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fmedicines%2Fhuman%2Fsummaries-opinion%2Fzolsketil-pegylated-liposomal&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span> Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</span> </li> <li id="cite_note-53"><span class="mw-cite-backlink"><b><a href="#cite_ref-53">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://ec.europa.eu/health/documents/community-register/html/h1629.htm">"Zolsketil Product information"</a>. <i>Union Register of medicinal products</i><span class="reference-accessdate">. Retrieved <span class="nowrap">3 March</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Union+Register+of+medicinal+products&rft.atitle=Zolsketil+Product+information&rft_id=https%3A%2F%2Fec.europa.eu%2Fhealth%2Fdocuments%2Fcommunity-register%2Fhtml%2Fh1629.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Celdoxome_pegylated_liposomal:_Pending_EC_decision-54"><span class="mw-cite-backlink">^ <a href="#cite_ref-Celdoxome_pegylated_liposomal:_Pending_EC_decision_54-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Celdoxome_pegylated_liposomal:_Pending_EC_decision_54-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Celdoxome_pegylated_liposomal:_Pending_EC_decision_54-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Celdoxome_pegylated_liposomal:_Pending_EC_decision_54-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><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.ema.europa.eu/en/medicines/human/summaries-opinion/celdoxome-pegylated-liposomal">"Celdoxome pegylated liposomal: Pending EC decision"</a>. <i><a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA)</i>. 22 July 2022. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20220728183716/https://www.ema.europa.eu/en/medicines/human/summaries-opinion/celdoxome-pegylated-liposomal">Archived</a> from the original on 28 July 2022<span class="reference-accessdate">. Retrieved <span class="nowrap">30 July</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=European+Medicines+Agency+%28EMA%29&rft.atitle=Celdoxome+pegylated+liposomal%3A+Pending+EC+decision&rft.date=2022-07-22&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fmedicines%2Fhuman%2Fsummaries-opinion%2Fceldoxome-pegylated-liposomal&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span> Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.</span> </li> <li id="cite_note-55"><span class="mw-cite-backlink"><b><a href="#cite_ref-55">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a682221.html">"Doxorubicin: MedlinePlus Drug Information"</a>. <i>medlineplus.gov</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200713131707/https://medlineplus.gov/druginfo/meds/a682221.html">Archived</a> from the original on 13 July 2020<span class="reference-accessdate">. Retrieved <span class="nowrap">12 July</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=medlineplus.gov&rft.atitle=Doxorubicin%3A+MedlinePlus+Drug+Information&rft_id=https%3A%2F%2Fmedlineplus.gov%2Fdruginfo%2Fmeds%2Fa682221.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-56"><span class="mw-cite-backlink"><b><a href="#cite_ref-56">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation pressrelease cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20140228161954/https://www.fda.gov/newsevents/newsroom/pressannouncements/ucm337872.htm">"FDA approval of generic version of cancer drug Doxil is expected to help resolve shortage"</a> (Press release). U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA). 4 February 2013. Archived from <a rel="nofollow" class="external text" href="https://www.fda.gov/newsevents/newsroom/pressannouncements/ucm337872.htm">the original</a> on 28 February 2014<span class="reference-accessdate">. Retrieved <span class="nowrap">22 February</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=FDA+approval+of+generic+version+of+cancer+drug+Doxil+is+expected+to+help+resolve+shortage&rft.pub=U.S.+Food+and+Drug+Administration+%28FDA%29&rft.date=2013-02-04&rft_id=https%3A%2F%2Fwww.fda.gov%2Fnewsevents%2Fnewsroom%2Fpressannouncements%2Fucm337872.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-57">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWendelDe_StanchinaFridmanMalina2004" class="citation journal cs1">Wendel HG, De Stanchina E, Fridman JS, Malina A, Ray S, Kogan S, et al. (March 2004). "Survival signalling by Akt and eIF4E in oncogenesis and cancer therapy". <i>Nature</i>. <b>428</b> (6980): <span class="nowrap">332–</span>337. <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/2004Natur.428..332W">2004Natur.428..332W</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnature02369">10.1038/nature02369</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/15029198">15029198</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:4426215">4426215</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Survival+signalling+by+Akt+and+eIF4E+in+oncogenesis+and+cancer+therapy&rft.volume=428&rft.issue=6980&rft.pages=%3Cspan+class%3D%22nowrap%22%3E332-%3C%2Fspan%3E337&rft.date=2004-03&rft_id=info%3Adoi%2F10.1038%2Fnature02369&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4426215%23id-name%3DS2CID&rft_id=info%3Apmid%2F15029198&rft_id=info%3Abibcode%2F2004Natur.428..332W&rft.aulast=Wendel&rft.aufirst=HG&rft.au=De+Stanchina%2C+E&rft.au=Fridman%2C+JS&rft.au=Malina%2C+A&rft.au=Ray%2C+S&rft.au=Kogan%2C+S&rft.au=Cordon-Cardo%2C+C&rft.au=Pelletier%2C+J&rft.au=Lowe%2C+SW&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-:1-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-:1_58-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSahaMondalKhisteLusic2021" class="citation journal cs1">Saha T, Mondal J, Khiste S, Lusic H, Hu ZW, Jayabalan R, et al. (September 2021). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8478290">"Nanotherapeutic approaches to overcome distinct drug resistance barriers in models of breast cancer"</a>. <i>Nanophotonics</i>. <b>10</b> (12): <span class="nowrap">3063–</span>3073. <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/2021Nanop..10..142S">2021Nanop..10..142S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1515%2Fnanoph-2021-0142">10.1515/nanoph-2021-0142</a></span>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8478290">8478290</a></span>. <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/34589378">34589378</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nanophotonics&rft.atitle=Nanotherapeutic+approaches+to+overcome+distinct+drug+resistance+barriers+in+models+of+breast+cancer&rft.volume=10&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3063-%3C%2Fspan%3E3073&rft.date=2021-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8478290%23id-name%3DPMC&rft_id=info%3Apmid%2F34589378&rft_id=info%3Adoi%2F10.1515%2Fnanoph-2021-0142&rft_id=info%3Abibcode%2F2021Nanop..10..142S&rft.aulast=Saha&rft.aufirst=T&rft.au=Mondal%2C+J&rft.au=Khiste%2C+S&rft.au=Lusic%2C+H&rft.au=Hu%2C+ZW&rft.au=Jayabalan%2C+R&rft.au=Hodgetts%2C+KJ&rft.au=Jang%2C+H&rft.au=Sengupta%2C+S&rft.au=Eunice+Lee%2C+S&rft.au=Park%2C+Y&rft.au=Lee%2C+LP&rft.au=Goldman%2C+A&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8478290&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-59"><span class="mw-cite-backlink"><b><a href="#cite_ref-59">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFJohanssonGoldenbergGriffithsWahren2006" class="citation journal cs1">Johansson S, Goldenberg DM, Griffiths GL, Wahren B, Hinkula J (October 2006). <a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F01.aids.0000247111.58961.60">"Elimination of HIV-1 infection by treatment with a doxorubicin-conjugated anti-envelope antibody"</a>. <i>AIDS</i>. <b>20</b> (15): <span class="nowrap">1911–</span>1915. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F01.aids.0000247111.58961.60">10.1097/01.aids.0000247111.58961.60</a></span>. <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/16988511">16988511</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:42286690">42286690</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=AIDS&rft.atitle=Elimination+of+HIV-1+infection+by+treatment+with+a+doxorubicin-conjugated+anti-envelope+antibody&rft.volume=20&rft.issue=15&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1911-%3C%2Fspan%3E1915&rft.date=2006-10&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A42286690%23id-name%3DS2CID&rft_id=info%3Apmid%2F16988511&rft_id=info%3Adoi%2F10.1097%2F01.aids.0000247111.58961.60&rft.aulast=Johansson&rft.aufirst=S&rft.au=Goldenberg%2C+DM&rft.au=Griffiths%2C+GL&rft.au=Wahren%2C+B&rft.au=Hinkula%2C+J&rft_id=https%3A%2F%2Fdoi.org%2F10.1097%252F01.aids.0000247111.58961.60&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-60"><span class="mw-cite-backlink"><b><a href="#cite_ref-60">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMitsuyasu2013" class="citation journal cs1">Mitsuyasu R (May 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3789644">"Curing HIV: lessons from cancer therapy"</a>. <i>Current Opinion in HIV and AIDS</i>. <b>8</b> (3): <span class="nowrap">224–</span>229. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2FCOH.0b013e32835ef0a1">10.1097/COH.0b013e32835ef0a1</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3789644">3789644</a></span>. <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/23454863">23454863</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Opinion+in+HIV+and+AIDS&rft.atitle=Curing+HIV%3A+lessons+from+cancer+therapy&rft.volume=8&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E224-%3C%2Fspan%3E229&rft.date=2013-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3789644%23id-name%3DPMC&rft_id=info%3Apmid%2F23454863&rft_id=info%3Adoi%2F10.1097%2FCOH.0b013e32835ef0a1&rft.aulast=Mitsuyasu&rft.aufirst=R&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3789644&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-friedman-61"><span class="mw-cite-backlink"><b><a href="#cite_ref-friedman_61-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFriedmanCaflisch2009" class="citation journal cs1">Friedman R, Caflisch A (August 2009). <a rel="nofollow" class="external text" href="https://archive.today/20130105091659/http://www3.interscience.wiley.com/journal/122407624/abstract?CRETRY=1&SRETRY=0">"Discovery of plasmepsin inhibitors by fragment-based docking and consensus scoring"</a>. <i>ChemMedChem</i>. <b>4</b> (8): <span class="nowrap">1317–</span>1326. <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%2Fcmdc.200900078">10.1002/cmdc.200900078</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/19472268">19472268</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:14642593">14642593</a>. Archived from <a rel="nofollow" class="external text" href="http://www3.interscience.wiley.com/journal/122407624/abstract?CRETRY=1&SRETRY=0">the original</a> on 5 January 2013<span class="reference-accessdate">. Retrieved <span class="nowrap">28 May</span> 2010</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ChemMedChem&rft.atitle=Discovery+of+plasmepsin+inhibitors+by+fragment-based+docking+and+consensus+scoring&rft.volume=4&rft.issue=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1317-%3C%2Fspan%3E1326&rft.date=2009-08&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A14642593%23id-name%3DS2CID&rft_id=info%3Apmid%2F19472268&rft_id=info%3Adoi%2F10.1002%2Fcmdc.200900078&rft.aulast=Friedman&rft.aufirst=R&rft.au=Caflisch%2C+A&rft_id=http%3A%2F%2Fwww3.interscience.wiley.com%2Fjournal%2F122407624%2Fabstract%3FCRETRY%3D1%26SRETRY%3D0&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-Gamo-62"><span class="mw-cite-backlink"><b><a href="#cite_ref-Gamo_62-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGamoSanzVidalde_Cozar2010" class="citation journal cs1">Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, et al. (May 2010). "Thousands of chemical starting points for antimalarial lead identification". <i>Nature</i>. <b>465</b> (7296): <span class="nowrap">305–</span>310. <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/2010Natur.465..305G">2010Natur.465..305G</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fnature09107">10.1038/nature09107</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/20485427">20485427</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:1143258">1143258</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=Thousands+of+chemical+starting+points+for+antimalarial+lead+identification&rft.volume=465&rft.issue=7296&rft.pages=%3Cspan+class%3D%22nowrap%22%3E305-%3C%2Fspan%3E310&rft.date=2010-05&rft_id=info%3Adoi%2F10.1038%2Fnature09107&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A1143258%23id-name%3DS2CID&rft_id=info%3Apmid%2F20485427&rft_id=info%3Abibcode%2F2010Natur.465..305G&rft.aulast=Gamo&rft.aufirst=FJ&rft.au=Sanz%2C+LM&rft.au=Vidal%2C+J&rft.au=de+Cozar%2C+C&rft.au=Alvarez%2C+E&rft.au=Lavandera%2C+JL&rft.au=Vanderwall%2C+DE&rft.au=Green%2C+DV&rft.au=Kumar%2C+V&rft.au=Hasan%2C+S&rft.au=Brown%2C+JR&rft.au=Peishoff%2C+CE&rft.au=Cardon%2C+LR&rft.au=Garcia-Bustos%2C+JF&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-63">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKarukstisThompsonWhilesRosenfeld1998" class="citation journal cs1">Karukstis KK, Thompson EH, Whiles JA, Rosenfeld RJ (July 1998). "Deciphering the fluorescence signature of daunomycin and doxorubicin". <i>Biophysical Chemistry</i>. <b>73</b> (3): <span class="nowrap">249–</span>263. <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%2Fs0301-4622%2898%2900150-1">10.1016/s0301-4622(98)00150-1</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/9700924">9700924</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Biophysical+Chemistry&rft.atitle=Deciphering+the+fluorescence+signature+of+daunomycin+and+doxorubicin&rft.volume=73&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E249-%3C%2Fspan%3E263&rft.date=1998-07&rft_id=info%3Adoi%2F10.1016%2Fs0301-4622%2898%2900150-1&rft_id=info%3Apmid%2F9700924&rft.aulast=Karukstis&rft.aufirst=KK&rft.au=Thompson%2C+EH&rft.au=Whiles%2C+JA&rft.au=Rosenfeld%2C+RJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> <li id="cite_note-64"><span class="mw-cite-backlink"><b><a href="#cite_ref-64">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMohanRapoport2010" class="citation journal cs1">Mohan P, Rapoport N (December 2010). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2997862">"Doxorubicin as a molecular nanotheranostic agent: effect of doxorubicin encapsulation in micelles or nanoemulsions on the ultrasound-mediated intracellular delivery and nuclear trafficking"</a>. <i>Molecular Pharmaceutics</i>. <b>7</b> (6): <span class="nowrap">1959–</span>1973. <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%2Fmp100269f">10.1021/mp100269f</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2997862">2997862</a></span>. <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/20957997">20957997</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Molecular+Pharmaceutics&rft.atitle=Doxorubicin+as+a+molecular+nanotheranostic+agent%3A+effect+of+doxorubicin+encapsulation+in+micelles+or+nanoemulsions+on+the+ultrasound-mediated+intracellular+delivery+and+nuclear+trafficking&rft.volume=7&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1959-%3C%2Fspan%3E1973&rft.date=2010-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2997862%23id-name%3DPMC&rft_id=info%3Apmid%2F20957997&rft_id=info%3Adoi%2F10.1021%2Fmp100269f&rft.aulast=Mohan&rft.aufirst=P&rft.au=Rapoport%2C+N&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2997862&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Doxorubicin&action=edit&section=17" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/20px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/40px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></a></span> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Doxorubicin" class="extiw" title="commons:Category:Doxorubicin">Doxorubicin</a> at Wikimedia Commons</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://druginfo.nlm.nih.gov/drugportal/name/doxorubicin">"Doxorubicin"</a>. <i>Drug Information Portal</i>. U.S. National Library of Medicine.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Drug+Information+Portal&rft.atitle=Doxorubicin&rft_id=https%3A%2F%2Fdruginfo.nlm.nih.gov%2Fdrugportal%2Fname%2Fdoxorubicin&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://druginfo.nlm.nih.gov/drugportal/name/doxorubicin%20hydrochloride">"Doxorubicin hydrochloride"</a>. <i>Drug Information Portal</i>. U.S. National Library of Medicine.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Drug+Information+Portal&rft.atitle=Doxorubicin+hydrochloride&rft_id=https%3A%2F%2Fdruginfo.nlm.nih.gov%2Fdrugportal%2Fname%2Fdoxorubicin%2520hydrochloride&rfr_id=info%3Asid%2Fen.wikipedia.org%3ADoxorubicin" class="Z3988"></span></li></ul> <div class="navbox-styles"><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:r1236075235">.mw-parser-output .navbox{box-sizing:border-box;border:1px solid #a2a9b1;width:100%;clear:both;font-size:88%;text-align:center;padding:1px;margin:1em auto 0}.mw-parser-output .navbox .navbox{margin-top:0}.mw-parser-output .navbox+.navbox,.mw-parser-output .navbox+.navbox-styles+.navbox{margin-top:-1px}.mw-parser-output .navbox-inner,.mw-parser-output .navbox-subgroup{width:100%}.mw-parser-output .navbox-group,.mw-parser-output .navbox-title,.mw-parser-output .navbox-abovebelow{padding:0.25em 1em;line-height:1.5em;text-align:center}.mw-parser-output .navbox-group{white-space:nowrap;text-align:right}.mw-parser-output .navbox,.mw-parser-output .navbox-subgroup{background-color:#fdfdfd}.mw-parser-output .navbox-list{line-height:1.5em;border-color:#fdfdfd}.mw-parser-output .navbox-list-with-group{text-align:left;border-left-width:2px;border-left-style:solid}.mw-parser-output tr+tr>.navbox-abovebelow,.mw-parser-output tr+tr>.navbox-group,.mw-parser-output tr+tr>.navbox-image,.mw-parser-output tr+tr>.navbox-list{border-top:2px solid #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="Intracellular_chemotherapeutic_agents_/_antineoplastic_agents_(L01)604" 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" /><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:Chemotherapeutic_agents" title="Template:Chemotherapeutic agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chemotherapeutic_agents" class="mw-redirect" title="Template talk:Chemotherapeutic agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chemotherapeutic_agents" title="Special:EditPage/Template:Chemotherapeutic agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Intracellular_chemotherapeutic_agents_/_antineoplastic_agents_(L01)604" style="font-size:114%;margin:0 4em">Intracellular <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapeutic agents</a> / <a href="/wiki/Antineoplastic" class="mw-redirect" title="Antineoplastic">antineoplastic agents</a> (<a href="/wiki/ATC_code_L01" title="ATC code L01">L01</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Spindle_poison" title="Spindle poison">SPs</a>/<a href="/wiki/Mitotic_inhibitor" title="Mitotic inhibitor">MIs</a><br />(<a href="/wiki/M_phase" class="mw-redirect" title="M phase">M phase</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Block <a href="/wiki/Microtubule" title="Microtubule">microtubule</a> assembly</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Vinca_alkaloid" title="Vinca alkaloid">Vinca alkaloids</a></i> (<a href="/wiki/Vinblastine" title="Vinblastine">Vinblastine</a><sup>#</sup></li> <li><a href="/wiki/Vincristine" title="Vincristine">Vincristine</a><sup>#</sup></li> <li><a href="/wiki/Vindesine" title="Vindesine">Vindesine</a></li> <li><a href="/wiki/Vinflunine" title="Vinflunine">Vinflunine</a><sup>§</sup></li> <li><a href="/wiki/Vinorelbine" title="Vinorelbine">Vinorelbine</a><sup>#</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Block microtubule disassembly</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Taxane" title="Taxane">Taxanes</a></i> (<a href="/wiki/Cabazitaxel" title="Cabazitaxel">Cabazitaxel</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a><sup>#</sup></li> <li><a href="/wiki/Larotaxel" title="Larotaxel">Larotaxel</a></li> <li><a href="/wiki/Ortataxel" title="Ortataxel">Ortataxel</a><sup>†</sup></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a><sup>#</sup></li> <li><a href="/wiki/Tesetaxel" title="Tesetaxel">Tesetaxel</a>)</li> <li><i><a href="/wiki/Epothilone" title="Epothilone">Epothilones</a></i> (<a href="/wiki/Ixabepilone" title="Ixabepilone">Ixabepilone</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/DNA_replication" title="DNA replication">DNA replication</a><br />inhibitor</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">DNA precursors/<br /><a href="/wiki/Antimetabolite" title="Antimetabolite">antimetabolites</a><br />(<a href="/wiki/S_phase" title="S phase">S phase</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antifolate" title="Antifolate">Folic acid</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Dihydrofolate_reductase_inhibitor" title="Dihydrofolate reductase inhibitor">Dihydrofolate reductase inhibitor</a></i> (<a href="/wiki/Aminopterin" title="Aminopterin">Aminopterin</a></li> <li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a><sup>#</sup></li> <li><a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Pralatrexate" title="Pralatrexate">Pralatrexate</a>)</li> <li><i><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">Thymidylate synthase inhibitor</a></i> (<a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Raltitrexed" title="Raltitrexed">Raltitrexed</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Purine_analogue" title="Purine analogue">Purine</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Adenosine_deaminase_inhibitor" class="mw-redirect" title="Adenosine deaminase inhibitor">Adenosine deaminase inhibitor</a></i> (<a href="/wiki/Pentostatin" title="Pentostatin">Pentostatin</a>)</li></ul> <ul><li><i><a href="/wiki/Halogenation" title="Halogenation">Halogenated</a>/<a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">ribonucleotide reductase inhibitors</a></i> (<a href="/wiki/Cladribine" title="Cladribine">Cladribine</a></li> <li><a href="/wiki/Clofarabine" title="Clofarabine">Clofarabine</a></li> <li><a href="/wiki/Fludarabine" title="Fludarabine">Fludarabine</a>)</li> <li><a href="/wiki/Nelarabine" title="Nelarabine">Nelarabine</a></li> <li><a href="/wiki/Rabacfosadine" title="Rabacfosadine">Rabacfosadine</a></li> <li><i><a href="/wiki/Thiopurine" title="Thiopurine">Thiopurine</a></i> (<a href="/wiki/Mercaptopurine" title="Mercaptopurine">Mercaptopurine</a><sup>#</sup></li> <li><a href="/wiki/Tioguanine" title="Tioguanine">Tioguanine</a><sup>#</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrimidine_analogue" title="Pyrimidine analogue">Pyrimidine</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">Thymidylate synthase inhibitor</a></i> (<a href="/wiki/Capecitabine" title="Capecitabine">Capecitabine</a><sup>#</sup></li> <li><a href="/wiki/Carmofur" title="Carmofur">Carmofur</a></li> <li><a href="/wiki/Doxifluridine" title="Doxifluridine">Doxifluridine</a></li> <li><a href="/wiki/Floxuridine" title="Floxuridine">Floxuridine</a></li> <li><a href="/wiki/Fluorouracil" title="Fluorouracil">Fluorouracil</a><sup>#</sup></li> <li><a href="/wiki/Tegafur" title="Tegafur">Tegafur</a> (<a href="/wiki/Tegafur/gimeracil/oteracil" title="Tegafur/gimeracil/oteracil">+gimeracil/oteracil</a>))</li></ul> <ul><li><i><a href="/wiki/DNA_polymerase_inhibitor" class="mw-redirect" title="DNA polymerase inhibitor">DNA polymerase inhibitor</a></i> (<a href="/wiki/Cytarabine" title="Cytarabine">Cytarabine</a><sup>#</sup> <a href="/wiki/Daunorubicin/cytarabine" title="Daunorubicin/cytarabine">+daunorubicin</a>)</li></ul> <ul><li><i><a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">Ribonucleotide reductase inhibitor</a></i> (<a href="/wiki/Gemcitabine" title="Gemcitabine">Gemcitabine</a><sup>#</sup>)</li></ul> <ul><li><i><a href="/wiki/Hypomethylating_agent" title="Hypomethylating agent">Hypomethylating agent</a></i> (<a href="/wiki/Azacitidine" title="Azacitidine">Azacitidine</a></li> <li><a href="/wiki/Decitabine" title="Decitabine">Decitabine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleotide" title="Deoxyribonucleotide">Deoxyribonucleotide</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">Ribonucleotide reductase inhibitor</a></i> (<a href="/wiki/Hydroxycarbamide" title="Hydroxycarbamide">Hydroxycarbamide</a><sup>#</sup>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Topoisomerase_inhibitor" title="Topoisomerase inhibitor">Topoisomerase inhibitors</a><br />(<a href="/wiki/S_phase" title="S phase">S phase</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_I_topoisomerase#Inhibition" title="Type I topoisomerase">I</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Camptotheca" title="Camptotheca">Camptotheca</a></i> (<a href="/wiki/Belotecan" title="Belotecan">Belotecan</a></li> <li><a href="/wiki/Camptothecin" title="Camptothecin">Camptothecin</a></li> <li><a href="/w/index.php?title=Cositecan&action=edit&redlink=1" class="new" title="Cositecan (page does not exist)">Cositecan</a><sup>†</sup></li> <li><a href="/wiki/Etirinotecan_pegol" title="Etirinotecan pegol">Etirinotecan pegol</a><sup>†</sup></li> <li><a href="/wiki/Exatecan" title="Exatecan">Exatecan</a></li> <li><a href="/w/index.php?title=Gimatecan&action=edit&redlink=1" class="new" title="Gimatecan (page does not exist)">Gimatecan</a></li> <li><a href="/wiki/Irinotecan" title="Irinotecan">Irinotecan</a><sup>#</sup></li> <li><a href="/wiki/Lurtotecan" title="Lurtotecan">Lurtotecan</a><sup>‡</sup></li> <li><a href="/wiki/Rubitecan" title="Rubitecan">Rubitecan</a><sup>‡</sup></li> <li><a href="/w/index.php?title=Silatecan&action=edit&redlink=1" class="new" title="Silatecan (page does not exist)">Silatecan</a><sup>§</sup></li> <li><a href="/wiki/Topotecan" title="Topotecan">Topotecan</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_II_topoisomerase#Inhibition" title="Type II topoisomerase">II</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Podophyllum_peltatum" title="Podophyllum peltatum">Podophyllum</a></i> (<a href="/wiki/Etoposide" title="Etoposide">Etoposide</a><sup>#</sup></li> <li><a href="/wiki/Teniposide" title="Teniposide">Teniposide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_II_topoisomerase#Inhibition" title="Type II topoisomerase">II</a>+<a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">Intercalation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Anthracycline" title="Anthracycline">Anthracyclines</a></i> (<a href="/wiki/Aclarubicin" title="Aclarubicin">Aclarubicin</a></li> <li><a href="/wiki/Amrubicin" title="Amrubicin">Amrubicin</a><sup>†</sup></li> <li><a href="/wiki/Daunorubicin" title="Daunorubicin">Daunorubicin</a><sup>#</sup> (<a href="/wiki/Daunorubicin/cytarabine" title="Daunorubicin/cytarabine">+cytarabine</a>)</li> <li><a class="mw-selflink selflink">Doxorubicin</a><sup>#</sup></li> <li><a href="/wiki/Epirubicin" title="Epirubicin">Epirubicin</a></li> <li><a href="/wiki/Idarubicin" title="Idarubicin">Idarubicin</a></li> <li><a href="/wiki/Pirarubicin" title="Pirarubicin">Pirarubicin</a></li> <li><a href="/wiki/Valrubicin" title="Valrubicin">Valrubicin</a></li> <li><a href="/wiki/Zorubicin" title="Zorubicin">Zorubicin</a>)</li> <li><i><a href="/wiki/Anthraquinone" title="Anthraquinone">Anthracenediones</a></i> (<a href="/wiki/Losoxantrone" title="Losoxantrone">Losoxantrone</a></li> <li><a href="/wiki/Mitoxantrone" title="Mitoxantrone">Mitoxantrone</a></li> <li><a href="/wiki/Pixantrone" title="Pixantrone">Pixantrone</a>)</li> <li><a href="/wiki/Amsacrine" title="Amsacrine">Amsacrine</a></li> <li><a href="/wiki/Bisantrene" title="Bisantrene">Bisantrene</a></li> <li><a href="/wiki/Crisnatol" title="Crisnatol">Crisnatol</a></li> <li><a href="/wiki/Menogaril" title="Menogaril">Menogaril</a><sup>§</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Crosslinking_of_DNA" title="Crosslinking of DNA">Crosslinking of DNA</a><br />(<a href="/wiki/Cell-cycle_nonspecific_antineoplastic_agents" title="Cell-cycle nonspecific antineoplastic agents">CCNS</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkylating_antineoplastic_agent" title="Alkylating antineoplastic agent">Alkylating</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">Nitrogen mustards</a>:</i> <a href="/wiki/Bendamustine" title="Bendamustine">Bendamustine</a><sup>#</sup></li> <li><a href="/wiki/Chlormethine" title="Chlormethine">Chlormethine</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a><sup>#</sup> (<a href="/wiki/Ifosfamide" title="Ifosfamide">Ifosfamide</a><sup>#</sup></li> <li><a href="/wiki/Trofosfamide" title="Trofosfamide">Trofosfamide</a>)</li> <li><a href="/wiki/Chlorambucil" title="Chlorambucil">Chlorambucil</a><sup>#</sup></li> <li><a href="/wiki/Melphalan" title="Melphalan">Melphalan</a> (<a href="/wiki/Melphalan_flufenamide" title="Melphalan flufenamide">Melphalan flufenamide</a>)</li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Uramustine" title="Uramustine">Uramustine</a></li></ul> <ul><li><i><a href="/wiki/Nitrosourea" title="Nitrosourea">Nitrosoureas</a>:</i> <a href="/wiki/Carmustine" title="Carmustine">Carmustine</a></li> <li><a href="/wiki/Fotemustine" title="Fotemustine">Fotemustine</a></li> <li><a href="/wiki/Lomustine" title="Lomustine">Lomustine</a> (<a href="/wiki/Semustine" title="Semustine">Semustine</a>)</li> <li><a href="/wiki/Nimustine" title="Nimustine">Nimustine</a></li> <li><a href="/wiki/Ranimustine" title="Ranimustine">Ranimustine</a></li> <li><a href="/wiki/Streptozotocin" title="Streptozotocin">Streptozocin</a></li></ul> <ul><li><i><a href="/wiki/Alkyl_sulfonate" title="Alkyl sulfonate">Alkyl sulfonates</a>:</i> <a href="/wiki/Busulfan" title="Busulfan">Busulfan</a> (<a href="/wiki/Mannosulfan" title="Mannosulfan">Mannosulfan</a></li> <li><a href="/wiki/Treosulfan" title="Treosulfan">Treosulfan</a>)</li></ul> <ul><li><i><a href="/wiki/Aziridine" title="Aziridine">Aziridines</a>:</i> <a href="/wiki/Carboquone" title="Carboquone">Carboquone</a></li> <li><a href="/wiki/Thiotepa" title="Thiotepa">Thiotepa</a></li> <li><a href="/wiki/Triaziquone" title="Triaziquone">Triaziquone</a></li> <li><a href="/wiki/Triethylenemelamine" title="Triethylenemelamine">Triethylenemelamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Platinum-based_antineoplastic" title="Platinum-based antineoplastic">Platinum-based</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboplatin" title="Carboplatin">Carboplatin</a><sup>#</sup></li> <li><a href="/wiki/Cisplatin" title="Cisplatin">Cisplatin</a><sup>#</sup></li> <li><a href="/wiki/Dicycloplatin" title="Dicycloplatin">Dicycloplatin</a></li> <li><a href="/wiki/Nedaplatin" title="Nedaplatin">Nedaplatin</a></li> <li><a href="/wiki/Oxaliplatin" title="Oxaliplatin">Oxaliplatin</a><sup>#</sup></li> <li><a href="/wiki/Satraplatin" title="Satraplatin">Satraplatin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkylating_antineoplastic_agent#Nonclassical" title="Alkylating antineoplastic agent">Nonclassical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Altretamine" title="Altretamine">Altretamine</a></li> <li><i><a href="/wiki/Hydrazine" title="Hydrazine">Hydrazines</a></i> (<a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a><sup>#</sup>)</li> <li><a href="/wiki/Etoglucid" title="Etoglucid">Etoglucid</a></li> <li><a href="/wiki/Mitobronitol" title="Mitobronitol">Mitobronitol</a></li> <li><a href="/wiki/Pipobroman" title="Pipobroman">Pipobroman</a></li> <li><i><a href="/wiki/Triazene" title="Triazene">Triazenes</a></i> (<a href="/wiki/Dacarbazine" title="Dacarbazine">Dacarbazine</a><sup>#</sup></li> <li><a href="/wiki/Mitozolomide" title="Mitozolomide">Mitozolomide</a><sup>§</sup></li> <li><a href="/wiki/Temozolomide" title="Temozolomide">Temozolomide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">Intercalation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a> (<a href="/wiki/Dactinomycin" title="Dactinomycin">Dactinomycin</a><sup>#</sup></li> <li><a href="/wiki/Bleomycin" title="Bleomycin">Bleomycin</a><sup>#</sup></li> <li><a href="/wiki/Mitomycins" title="Mitomycins">Mitomycins</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Photosensitizer" title="Photosensitizer">Photosensitizers</a>/<a href="/wiki/Photodynamic_therapy" title="Photodynamic therapy">PDT</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminolevulinic_acid" title="Aminolevulinic acid">Aminolevulinic acid</a></li> <li><a href="/wiki/Efaproxiral" title="Efaproxiral">Efaproxiral</a></li> <li><a href="/wiki/Methyl_aminolevulinate" title="Methyl aminolevulinate">Methyl aminolevulinate</a></li> <li><a href="/wiki/Padeliporfin" title="Padeliporfin">Padeliporfin</a></li> <li><i><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrin derivatives</a></i> (<a href="/wiki/Porfimer_sodium" title="Porfimer sodium">Porfimer sodium</a></li> <li><a href="/wiki/Talaporfin" title="Talaporfin">Talaporfin</a></li> <li><a href="/wiki/Temoporfin" title="Temoporfin">Temoporfin</a></li> <li><a href="/wiki/Verteporfin" title="Verteporfin">Verteporfin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">Enzyme inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Farnesyltransferase_inhibitor" title="Farnesyltransferase inhibitor">FI</a></i> (<a href="/wiki/Tipifarnib" title="Tipifarnib">Tipifarnib</a><sup>§</sup>)</li> <li><i><a href="/wiki/Cyclin-dependent_kinase" title="Cyclin-dependent kinase">CDK</a> <a href="/wiki/Protein_kinase_inhibitor" title="Protein kinase inhibitor">inhibitors</a></i> (<a href="/wiki/Abemaciclib" title="Abemaciclib">Abemaciclib</a></li> <li><a href="/wiki/Alvocidib" title="Alvocidib">Alvocidib</a><sup>†</sup></li> <li><a href="/wiki/Palbociclib" title="Palbociclib">Palbociclib</a></li> <li><a href="/wiki/Ribociclib" title="Ribociclib">Ribociclib</a></li> <li><a href="/wiki/Seliciclib" title="Seliciclib">Seliciclib</a><sup>†</sup>)</li> <li><i><a href="/wiki/Proteasome_inhibitor" title="Proteasome inhibitor">PrI</a></i> <ul><li><a href="/wiki/Bortezomib" title="Bortezomib">Bortezomib</a></li> <li><a href="/wiki/Carfilzomib" title="Carfilzomib">Carfilzomib</a></li> <li><a href="/wiki/Oprozomib" title="Oprozomib">Oprozomib</a></li> <li><a href="/wiki/Ixazomib" title="Ixazomib">Ixazomib</a></li></ul></li> <li><i><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">PhI</a></i> (<a href="/wiki/Anagrelide" title="Anagrelide">Anagrelide</a>)</li> <li><i><a href="/wiki/IMP_dehydrogenase" class="mw-redirect" title="IMP dehydrogenase">IMPDI</a></i> (<a href="/wiki/Tiazofurin" title="Tiazofurin">Tiazofurin</a><sup>§</sup>)</li> <li><i><a href="/wiki/Lipoxygenase_inhibitor" class="mw-redirect" title="Lipoxygenase inhibitor">LI</a></i> (<a href="/wiki/Masoprocol" title="Masoprocol">Masoprocol</a>)</li> <li><i><a href="/wiki/PARP_inhibitor" title="PARP inhibitor">PARP inhibitor</a></i> (<a href="/wiki/Fuzuloparib" title="Fuzuloparib">Fuzuloparib</a></li> <li><a href="/wiki/Niraparib" title="Niraparib">Niraparib</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+abiraterone acetate</a></li> <li><a href="/wiki/Olaparib" title="Olaparib">Olaparib</a></li> <li><a href="/wiki/Rucaparib" title="Rucaparib">Rucaparib</a>)</li> <li><i><a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">HDAC</a></i> (<a href="/wiki/Belinostat" title="Belinostat">Belinostat</a></li> <li><a href="/wiki/Entinostat" title="Entinostat">Entinostat</a></li> <li><a href="/wiki/Panobinostat" title="Panobinostat">Panobinostat</a></li> <li><a href="/wiki/Romidepsin" title="Romidepsin">Romidepsin</a></li> <li><a href="/wiki/Vorinostat" title="Vorinostat">Vorinostat</a>)</li> <li><i><a href="/wiki/Phosphoinositide_3-kinase_inhibitor" title="Phosphoinositide 3-kinase inhibitor">PIKI</a> (Pi3K)</i> (<a href="/wiki/Alpelisib" title="Alpelisib">Alpelisib</a></li> <li><a href="/wiki/Copanlisib" title="Copanlisib">Copanlisib</a><sup>‡</sup></li> <li><a href="/wiki/Duvelisib" title="Duvelisib">Duvelisib</a></li> <li><a href="/wiki/Idelalisib" title="Idelalisib">Idelalisib</a></li> <li><a href="/wiki/Inavolisib" title="Inavolisib">Inavolisib</a></li> <li><a href="/wiki/Umbralisib" title="Umbralisib">Umbralisib</a><sup>‡</sup>)</li> <li><i><a href="/wiki/Isocitrate_dehydrogenase" title="Isocitrate dehydrogenase">IDH</a></i> (<a href="/wiki/Enasidenib" title="Enasidenib">Enasidenib</a></li> <li><a href="/wiki/Ivosidenib" title="Ivosidenib">Ivosidenib</a></li> <li><a href="/wiki/Olutasidenib" title="Olutasidenib">Olutasidenib</a></li> <li><a href="/wiki/Vorasidenib" title="Vorasidenib">Vorasidenib</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Receptor antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Endothelin_receptor_antagonist" title="Endothelin receptor antagonist">ERA</a></i> (<a href="/wiki/Atrasentan" title="Atrasentan">Atrasentan</a>)</li> <li><i><a href="/wiki/Retinoid_X_receptor" title="Retinoid X receptor">Retinoid X receptor</a></i> (<a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a>)</li> <li><i><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroid</a></i> (<a href="/wiki/Testolactone" title="Testolactone">Testolactone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/ungrouped</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adagrasib" title="Adagrasib">Adagrasib</a></li> <li><a href="/wiki/Aflibercept" title="Aflibercept">Aflibercept</a></li> <li><a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">Arsenic trioxide</a></li> <li><i><a href="/wiki/Asparagine" title="Asparagine">Asparagine depleters</a></i> (<a href="/wiki/Asparaginase" title="Asparaginase">Asparaginase</a><sup>#</sup>/<a href="/wiki/Pegaspargase" title="Pegaspargase">Pegaspargase</a>)</li> <li><a href="/wiki/Axicabtagene_ciloleucel" title="Axicabtagene ciloleucel">Axicabtagene ciloleucel</a></li> <li><a href="/wiki/Belzutifan" title="Belzutifan">Belzutifan</a></li> <li><a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a></li> <li><a href="/wiki/Brexucabtagene_autoleucel" title="Brexucabtagene autoleucel">Brexucabtagene autoleucel</a></li> <li><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a></li> <li><a href="/wiki/Ciltacabtagene_autoleucel" title="Ciltacabtagene autoleucel">Ciltacabtagene autoleucel</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Denileukin_diftitox" title="Denileukin diftitox">Denileukin diftitox</a></li> <li><a href="/wiki/Eflornithine" title="Eflornithine">Eflornithine</a></li> <li><a href="/wiki/Elesclomol" title="Elesclomol">Elesclomol</a><sup>§</sup></li> <li><a href="/wiki/Elsamitrucin" title="Elsamitrucin">Elsamitrucin</a></li> <li><a href="/wiki/Epacadostat" title="Epacadostat">Epacadostat</a></li> <li><a href="/wiki/Eribulin" title="Eribulin">Eribulin</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine</a></li> <li><a href="/wiki/Glasdegib" title="Glasdegib">Glasdegib</a></li> <li><a href="/wiki/Idecabtagene_vicleucel" title="Idecabtagene vicleucel">Idecabtagene vicleucel</a></li> <li><a href="/wiki/Imetelstat" title="Imetelstat">Imetelstat</a></li> <li><a href="/wiki/Lifileucel" title="Lifileucel">Lifileucel</a></li> <li><a href="/wiki/Lisocabtagene_maraleucel" title="Lisocabtagene maraleucel">Lisocabtagene maraleucel</a></li> <li><a href="/wiki/Lonidamine" title="Lonidamine">Lonidamine</a></li> <li><a href="/wiki/Lucanthone" title="Lucanthone">Lucanthone</a></li> <li><a href="/wiki/Lurbinectedin" title="Lurbinectedin">Lurbinectedin</a></li> <li><a href="/wiki/Mitoguazone" title="Mitoguazone">Mitoguazone</a></li> <li><a href="/wiki/Mitotane" title="Mitotane">Mitotane</a></li> <li><a href="/wiki/Nadofaragene_firadenovec" title="Nadofaragene firadenovec">Nadofaragene firadenovec</a></li> <li><a href="/wiki/Navitoclax" title="Navitoclax">Navitoclax</a></li> <li><a href="/wiki/Obecabtagene_autoleucel" title="Obecabtagene autoleucel">Obecabtagene autoleucel</a></li> <li><a href="/wiki/Oblimersen" title="Oblimersen">Oblimersen</a><sup>†</sup></li> <li><a href="/wiki/Omacetaxine_mepesuccinate" title="Omacetaxine mepesuccinate">Omacetaxine mepesuccinate</a></li> <li><a href="/wiki/Plitidepsin" title="Plitidepsin">Plitidepsin</a></li> <li><a href="/wiki/Tabelecleucel" title="Tabelecleucel">Tabelecleucel</a></li> <li><i><a href="/wiki/Retinoid" title="Retinoid">Retinoids</a></i> (<a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a><sup>#</sup>)</li> <li><a href="/wiki/Selinexor" title="Selinexor">Selinexor</a></li> <li><a href="/w/index.php?title=Sitimagene_ceradenovec&action=edit&redlink=1" class="new" title="Sitimagene ceradenovec (page does not exist)">Sitimagene ceradenovec</a></li> <li><a href="/wiki/Sotorasib" title="Sotorasib">Sotorasib</a></li> <li><a href="/wiki/Tagraxofusp" title="Tagraxofusp">Tagraxofusp</a></li> <li><a href="/wiki/Talimogene_laherparepvec" title="Talimogene laherparepvec">Talimogene laherparepvec</a></li> <li><a href="/wiki/Tazemetostat" title="Tazemetostat">Tazemetostat</a></li> <li><a href="/wiki/Tebentafusp" title="Tebentafusp">Tebentafusp</a></li> <li><a href="/wiki/Tiazofurine" class="mw-redirect" title="Tiazofurine">Tiazofurine</a></li> <li><a href="/wiki/Tigilanol_tiglate" title="Tigilanol tiglate">Tigilanol tiglate</a></li> <li><a href="/wiki/Tisagenlecleucel" title="Tisagenlecleucel">Tisagenlecleucel</a></li> <li><a href="/wiki/Trabectedin" title="Trabectedin">Trabectedin</a></li> <li><a href="/wiki/Veliparib" title="Veliparib">Veliparib</a></li> <li><a href="/wiki/Venetoclax" title="Venetoclax">Venetoclax</a></li> <li><a href="/w/index.php?title=Verdinexor&action=edit&redlink=1" class="new" title="Verdinexor (page does not exist)">Verdinexor</a></li> <li><a href="/wiki/Vosaroxin" title="Vosaroxin">Vosaroxin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><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><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output .portal-bar-content-related{margin:0;list-style:none}.mw-parser-output .portal-bar-item{display:inline-block;margin:0.15em 0.2em;min-height:24px;line-height:24px}@media screen and (max-width:768px){.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;flex-flow:column wrap;align-items:baseline}.mw-parser-output .portal-bar-header{text-align:center;flex:0;padding-left:0.5em;margin:0 auto}.mw-parser-output .portal-bar-related{font-size:100%;align-items:flex-start}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;align-items:center;flex:0;column-gap:1em;border-top:1px solid #a2a9b1;margin:0 auto;list-style:none}.mw-parser-output .portal-bar-content-related{border-top:none;margin:0;list-style:none}}.mw-parser-output .navbox+link+.portal-bar,.mw-parser-output .navbox+style+.portal-bar,.mw-parser-output .navbox+link+.portal-bar-bordered,.mw-parser-output .navbox+style+.portal-bar-bordered,.mw-parser-output .sister-bar+link+.portal-bar,.mw-parser-output .sister-bar+style+.portal-bar,.mw-parser-output .portal-bar+.navbox-styles+.navbox,.mw-parser-output .portal-bar+.navbox-styles+.sister-bar{margin-top:-1px}</style><div class="portal-bar noprint metadata noviewer portal-bar-bordered" role="navigation" aria-label="Portals"><span class="portal-bar-header"><a href="/wiki/Wikipedia:Contents/Portals" title="Wikipedia:Contents/Portals">Portal</a>:</span><ul class="portal-bar-content"><li class="portal-bar-item"><span class="nowrap"><span typeof="mw:File"><span><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/20px-WHO_Rod.svg.png" decoding="async" width="8" height="19" class="mw-file-element" data-file-width="107" data-file-height="250" /></span></span> </span><a href="/wiki/Portal:Medicine" title="Portal:Medicine">Medicine</a></li></ul></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" /><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox728" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q18936#identifiers" 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></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4150505-0">Germany</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Doxorubicin"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85001015">United States</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://www.nli.org.il/en/authorities/987007292944205171">Israel</a></span></li></ul></div></td></tr></tbody></table></div> <p class="mw-empty-elt"> </p>    </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=Doxorubicin&oldid=1280964764">https://en.wikipedia.org/w/index.php?title=Doxorubicin&oldid=1280964764</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:Anthracyclines" title="Category:Anthracyclines">Anthracyclines</a></li><li><a href="/wiki/Category:Anthraquinone_glycosides" title="Category:Anthraquinone glycosides">Anthraquinone glycosides</a></li><li><a href="/wiki/Category:CYP2D6_inhibitors" title="Category:CYP2D6 inhibitors">CYP2D6 inhibitors</a></li><li><a href="/wiki/Category:DNA_intercalaters" title="Category:DNA intercalaters">DNA intercalaters</a></li><li><a href="/wiki/Category:Embryotoxins" title="Category:Embryotoxins">Embryotoxins</a></li><li><a href="/wiki/Category:IARC_Group_2A_carcinogens" title="Category:IARC Group 2A carcinogens">IARC Group 2A carcinogens</a></li><li><a href="/wiki/Category:Italian_inventions" title="Category:Italian inventions">Italian inventions</a></li><li><a href="/wiki/Category:Drugs_developed_by_Johnson_%26_Johnson" title="Category:Drugs developed by Johnson & Johnson">Drugs developed by Johnson & Johnson</a></li><li><a href="/wiki/Category:Orphan_drugs" title="Category:Orphan drugs">Orphan drugs</a></li><li><a href="/wiki/Category:Drugs_developed_by_Pfizer" title="Category:Drugs developed by Pfizer">Drugs developed by Pfizer</a></li><li><a href="/wiki/Category:Teratogens" title="Category:Teratogens">Teratogens</a></li><li><a href="/wiki/Category:Topoisomerase_inhibitors" title="Category:Topoisomerase inhibitors">Topoisomerase inhibitors</a></li><li><a href="/wiki/Category:World_Health_Organization_essential_medicines" title="Category:World Health Organization essential medicines">World Health Organization essential medicines</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:All_articles_with_dead_external_links" title="Category:All articles with dead external links">All articles with dead external links</a></li><li><a href="/wiki/Category:Articles_with_dead_external_links_from_November_2021" title="Category:Articles with dead external links from November 2021">Articles with dead external links from November 2021</a></li><li><a href="/wiki/Category:Articles_with_permanently_dead_external_links" title="Category:Articles with permanently dead external links">Articles with permanently dead external links</a></li><li><a href="/wiki/Category:Webarchive_template_wayback_links" title="Category:Webarchive template wayback links">Webarchive template wayback links</a></li><li><a href="/wiki/Category:CS1_Italian-language_sources_(it)" title="Category:CS1 Italian-language sources (it)">CS1 Italian-language sources (it)</a></li><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:Use_dmy_dates_from_March_2023" title="Category:Use dmy dates from March 2023">Use dmy dates from March 2023</a></li><li><a href="/wiki/Category:Drugs_with_non-standard_legal_status" title="Category:Drugs with non-standard legal status">Drugs with non-standard legal status</a></li><li><a href="/wiki/Category:Articles_with_changed_EBI_identifier" title="Category:Articles with changed EBI identifier">Articles with changed EBI identifier</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Articles_with_changed_InChI_identifier" title="Category:Articles with changed InChI identifier">Articles with changed InChI identifier</a></li><li><a href="/wiki/Category:Multiple_chemicals_in_Infobox_drug" title="Category:Multiple chemicals in Infobox drug">Multiple chemicals in Infobox drug</a></li><li><a href="/wiki/Category:Chemicals_using_indexlabels" title="Category:Chemicals using indexlabels">Chemicals using indexlabels</a></li><li><a href="/wiki/Category:Chemical_articles_with_multiple_CAS_registry_numbers" title="Category:Chemical articles with multiple CAS registry numbers">Chemical articles with multiple CAS registry numbers</a></li><li><a href="/wiki/Category:Chemical_articles_with_multiple_PubChem_CIDs" title="Category:Chemical articles with multiple PubChem CIDs">Chemical articles with multiple PubChem CIDs</a></li><li><a href="/wiki/Category:Chemical_articles_with_multiple_ChEBIs" title="Category:Chemical articles with multiple ChEBIs">Chemical articles with multiple ChEBIs</a></li><li><a href="/wiki/Category:Drug_has_EMA_link" title="Category:Drug has EMA link">Drug has EMA link</a></li><li><a href="/wiki/Category:Drugboxes_which_contain_changes_to_verified_fields" title="Category:Drugboxes which contain changes to verified fields">Drugboxes which contain changes to verified fields</a></li><li><a href="/wiki/Category:Drugboxes_which_contain_changes_to_watched_fields" title="Category:Drugboxes which contain changes to watched fields">Drugboxes which contain changes to watched fields</a></li><li><a href="/wiki/Category:Commons_category_link_from_Wikidata" title="Category:Commons category link from Wikidata">Commons category link from Wikidata</a></li><li><a href="/wiki/Category:Good_articles" title="Category:Good articles">Good articles</a></li><li><a href="/wiki/Category:Wikipedia_medicine_articles_ready_to_translate" title="Category:Wikipedia medicine articles ready to translate">Wikipedia medicine articles ready to translate</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 17 March 2025, at 13:40<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. By using this site, you agree to the <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Terms_of_Use" class="extiw" title="foundation:Special:MyLanguage/Policy:Terms of Use">Terms of Use</a> and <a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy" class="extiw" title="foundation:Special:MyLanguage/Policy:Privacy policy">Privacy Policy</a>. Wikipedia® is a registered trademark of the <a rel="nofollow" class="external text" href="https://wikimediafoundation.org/">Wikimedia Foundation, Inc.</a>, a non-profit organization.</li> </ul> <ul id="footer-places"> <li id="footer-places-privacy"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Privacy_policy">Privacy policy</a></li> <li id="footer-places-about"><a href="/wiki/Wikipedia:About">About Wikipedia</a></li> <li id="footer-places-disclaimers"><a href="/wiki/Wikipedia:General_disclaimer">Disclaimers</a></li> <li id="footer-places-contact"><a href="//en.wikipedia.org/wiki/Wikipedia:Contact_us">Contact Wikipedia</a></li> <li id="footer-places-wm-codeofconduct"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Universal_Code_of_Conduct">Code of Conduct</a></li> <li id="footer-places-developers"><a href="https://developer.wikimedia.org">Developers</a></li> <li id="footer-places-statslink"><a href="https://stats.wikimedia.org/#/en.wikipedia.org">Statistics</a></li> <li id="footer-places-cookiestatement"><a href="https://foundation.wikimedia.org/wiki/Special:MyLanguage/Policy:Cookie_statement">Cookie statement</a></li> <li id="footer-places-mobileview"><a href="//en.m.wikipedia.org/w/index.php?title=Doxorubicin&mobileaction=toggle_view_mobile" class="noprint stopMobileRedirectToggle">Mobile view</a></li> </ul> <ul id="footer-icons" class="noprint"> <li id="footer-copyrightico"><a href="https://www.wikimedia.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><picture><source media="(min-width: 500px)" srcset="/static/images/footer/wikimedia-button.svg" width="84" height="29"><img src="/static/images/footer/wikimedia.svg" width="25" height="25" alt="Wikimedia Foundation" lang="en" loading="lazy"></picture></a></li> <li id="footer-poweredbyico"><a href="https://www.mediawiki.org/" class="cdx-button cdx-button--fake-button cdx-button--size-large cdx-button--fake-button--enabled"><picture><source media="(min-width: 500px)" srcset="/w/resources/assets/poweredby_mediawiki.svg" width="88" height="31"><img src="/w/resources/assets/mediawiki_compact.svg" alt="Powered by MediaWiki" lang="en" width="25" height="25" loading="lazy"></picture></a></li> </ul> </footer> </div> </div> </div> <div class="vector-header-container vector-sticky-header-container"> <div id="vector-sticky-header" class="vector-sticky-header"> <div class="vector-sticky-header-start"> <div class="vector-sticky-header-icon-start vector-button-flush-left vector-button-flush-right" aria-hidden="true"> <button class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-sticky-header-search-toggle" tabindex="-1" data-event-name="ui.vector-sticky-search-form.icon"><span class="vector-icon mw-ui-icon-search mw-ui-icon-wikimedia-search"></span> <span>Search</span> </button> </div> <div role="search" class="vector-search-box-vue vector-search-box-show-thumbnail vector-search-box"> <div class="vector-typeahead-search-container"> <div class="cdx-typeahead-search cdx-typeahead-search--show-thumbnail"> <form action="/w/index.php" id="vector-sticky-search-form" class="cdx-search-input cdx-search-input--has-end-button"> <div class="cdx-search-input__input-wrapper" data-search-loc="header-moved"> <div class="cdx-text-input cdx-text-input--has-start-icon"> <input class="cdx-text-input__input" type="search" name="search" placeholder="Search Wikipedia"> <span class="cdx-text-input__icon cdx-text-input__start-icon"></span> </div> <input type="hidden" name="title" value="Special:Search"> </div> <button class="cdx-button cdx-search-input__end-button">Search</button> </form> </div> </div> </div> <div class="vector-sticky-header-context-bar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-sticky-header-toc" class="vector-dropdown mw-portlet mw-portlet-sticky-header-toc vector-sticky-header-toc vector-button-flush-left" > <input type="checkbox" id="vector-sticky-header-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-sticky-header-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-sticky-header-toc-label" for="vector-sticky-header-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-sticky-header-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <div class="vector-sticky-header-context-bar-primary" aria-hidden="true" ><span class="mw-page-title-main">Doxorubicin</span></div> </div> </div> <div class="vector-sticky-header-end" aria-hidden="true"> <div class="vector-sticky-header-icons"> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-talk-sticky-header" tabindex="-1" data-event-name="talk-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbles mw-ui-icon-wikimedia-speechBubbles"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-subject-sticky-header" tabindex="-1" data-event-name="subject-sticky-header"><span class="vector-icon mw-ui-icon-article mw-ui-icon-wikimedia-article"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-history-sticky-header" tabindex="-1" data-event-name="history-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-history mw-ui-icon-wikimedia-wikimedia-history"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only mw-watchlink" id="ca-watchstar-sticky-header" tabindex="-1" data-event-name="watch-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-star mw-ui-icon-wikimedia-wikimedia-star"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-edit-sticky-header" tabindex="-1" data-event-name="wikitext-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-wikiText mw-ui-icon-wikimedia-wikimedia-wikiText"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-ve-edit-sticky-header" tabindex="-1" data-event-name="ve-edit-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-edit mw-ui-icon-wikimedia-wikimedia-edit"></span> <span></span> </a> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only" id="ca-viewsource-sticky-header" tabindex="-1" data-event-name="ve-edit-protected-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-editLock mw-ui-icon-wikimedia-wikimedia-editLock"></span> <span></span> </a> </div> <div class="vector-sticky-header-buttons"> <button class="cdx-button cdx-button--weight-quiet mw-interlanguage-selector" id="p-lang-btn-sticky-header" tabindex="-1" data-event-name="ui.dropdown-p-lang-btn-sticky-header"><span class="vector-icon mw-ui-icon-wikimedia-language mw-ui-icon-wikimedia-wikimedia-language"></span> <span>32 languages</span> </button> <a href="#" class="cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive" id="ca-addsection-sticky-header" tabindex="-1" data-event-name="addsection-sticky-header"><span class="vector-icon mw-ui-icon-speechBubbleAdd-progressive mw-ui-icon-wikimedia-speechBubbleAdd-progressive"></span> <span>Add topic</span> </a> </div> <div class="vector-sticky-header-icon-end"> <div class="vector-user-links"> </div> </div> </div> </div> </div> <div class="mw-portlet mw-portlet-dock-bottom emptyPortlet" id="p-dock-bottom"> <ul> </ul> </div> <script>(RLQ=window.RLQ||[]).push(function(){mw.config.set({"wgHostname":"mw-web.codfw.main-5c6f46dcf-pz8dp","wgBackendResponseTime":182,"wgPageParseReport":{"limitreport":{"cputime":"0.964","walltime":"1.215","ppvisitednodes":{"value":10271,"limit":1000000},"postexpandincludesize":{"value":339534,"limit":2097152},"templateargumentsize":{"value":14278,"limit":2097152},"expansiondepth":{"value":19,"limit":100},"expensivefunctioncount":{"value":9,"limit":500},"unstrip-depth":{"value":1,"limit":20},"unstrip-size":{"value":288471,"limit":5000000},"entityaccesscount":{"value":1,"limit":400},"timingprofile":["100.00% 1023.860 1 -total"," 35.84% 366.939 1 Template:Reflist"," 33.79% 345.943 1 Template:Infobox_drug"," 27.70% 283.649 1 Template:Infobox"," 14.47% 148.130 36 Template:Cite_journal"," 12.78% 130.891 23 Template:Cite_web"," 10.70% 109.579 7 Template:Navbox"," 8.71% 89.215 1 Template:Chemotherapeutic_Agents"," 7.32% 74.927 2 Template:Short_description"," 6.63% 67.924 17 Template:Unbulleted_list"]},"scribunto":{"limitreport-timeusage":{"value":"0.491","limit":"10.000"},"limitreport-memusage":{"value":11024466,"limit":52428800}},"cachereport":{"origin":"mw-web.codfw.main-5c6f46dcf-5vbc9","timestamp":"20250331030128","ttl":2592000,"transientcontent":false}}});});</script> <script type="application/ld+json">{"@context":"https:\/\/schema.org","@type":"Article","name":"Doxorubicin","url":"https:\/\/en.wikipedia.org\/wiki\/Doxorubicin","sameAs":"http:\/\/www.wikidata.org\/entity\/Q18936","mainEntity":"http:\/\/www.wikidata.org\/entity\/Q18936","author":{"@type":"Organization","name":"Contributors to Wikimedia projects"},"publisher":{"@type":"Organization","name":"Wikimedia Foundation, Inc.","logo":{"@type":"ImageObject","url":"https:\/\/www.wikimedia.org\/static\/images\/wmf-hor-googpub.png"}},"datePublished":"2005-04-27T01:24:58Z","dateModified":"2025-03-17T13:40:23Z","image":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/d\/d3\/Doxorubicin.svg","headline":"chemical compound"}</script> </body> </html>