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class="vector-toc-numb">2</span> <span>Side effects</span> </div> </a> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-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 Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Cisplatin_resistance" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cisplatin_resistance"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Cisplatin resistance</span> </div> </a> <ul id="toc-Cisplatin_resistance-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Transplatin" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Transplatin"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Transplatin</span> </div> </a> <ul id="toc-Transplatin-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Molecular_structure" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Molecular_structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Molecular structure</span> </div> </a> <ul id="toc-Molecular_structure-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-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </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> <ul id="toc-Research-sublist" class="vector-toc-list"> </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-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-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">10</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">Cisplatin</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 36 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-36" 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">36 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%B3%D9%8A%D8%B3%D8%A8%D9%84%D8%A7%D8%AA%D9%8A%D9%86" title="سيسبلاتين – Arabic" lang="ar" hreflang="ar" data-title="سيسبلاتين" 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%B3%DB%8C%D8%B3%E2%80%8C%D9%BE%D9%84%D8%A7%D8%AA%DB%8C%D9%86" title="سیس‌پلاتین – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیس‌پلاتین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A6%D0%B8%D1%81%D0%BF%D0%BB%D0%B0%D1%82%D0%B8%D0%BD" title="Цисплатин – Bulgarian" lang="bg" hreflang="bg" data-title="Цисплатин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Cisplatin" title="Cisplatin – Bosnian" lang="bs" hreflang="bs" data-title="Cisplatin" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cisplat%C3%AD" title="Cisplatí – Catalan" lang="ca" hreflang="ca" data-title="Cisplatí" 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/Cisplatin" title="Cisplatin – Welsh" lang="cy" hreflang="cy" data-title="Cisplatin" 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/Cisplatin" title="Cisplatin – German" lang="de" hreflang="de" data-title="Cisplatin" 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%A3%CE%B9%CF%83%CF%80%CE%BB%CE%B1%CF%84%CE%AF%CE%BD%CE%B7" title="Σισπλατίνη – Greek" lang="el" hreflang="el" data-title="Σισπλατίνη" 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/Cisplatino" title="Cisplatino – Spanish" lang="es" hreflang="es" data-title="Cisplatino" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Zisplatino" title="Zisplatino – Basque" lang="eu" hreflang="eu" data-title="Zisplatino" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%D8%B3%E2%80%8C%D9%BE%D9%84%D8%A7%D8%AA%DB%8C%D9%86" title="سیس‌پلاتین – Persian" lang="fa" hreflang="fa" data-title="سیس‌پلاتین" 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/Cisplatine" title="Cisplatine – French" lang="fr" hreflang="fr" data-title="Cisplatine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%8B%9C%EC%8A%A4%ED%94%8C%EB%9D%BC%ED%8B%B4" title="시스플라틴 – Korean" lang="ko" hreflang="ko" data-title="시스플라틴" 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/%D5%91%D5%AB%D5%BD%D5%BA%D5%AC%D5%A1%D5%BF%D5%AB%D5%B6" title="Ցիսպլատին – Armenian" lang="hy" hreflang="hy" data-title="Ցիսպլատին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A4%BF%E0%A4%B8%E0%A4%AA%E0%A5%8D%E0%A4%B2%E0%A5%87%E0%A4%9F%E0%A4%BF%E0%A4%A8" title="सिसप्लेटिन – Hindi" lang="hi" hreflang="hi" data-title="सिसप्लेटिन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Sisplatin" title="Sisplatin – Indonesian" lang="id" hreflang="id" data-title="Sisplatin" 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/Cisplatino" title="Cisplatino – Italian" lang="it" hreflang="it" data-title="Cisplatino" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A6%D7%99%D7%A1%D7%A4%D7%9C%D7%90%D7%98%D7%99%D7%9F" title="ציספלאטין – Hebrew" lang="he" hreflang="he" data-title="ציספלאטין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Ciszplatin" title="Ciszplatin – Hungarian" lang="hu" hreflang="hu" data-title="Ciszplatin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A6%D0%B8%D1%81%D0%BF%D0%BB%D0%B0%D1%82%D0%B8%D0%BD" title="Цисплатин – Macedonian" lang="mk" hreflang="mk" data-title="Цисплатин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cisplatine" title="Cisplatine – Dutch" lang="nl" hreflang="nl" data-title="Cisplatine" 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%82%B7%E3%82%B9%E3%83%97%E3%83%A9%E3%83%81%E3%83%B3" title="シスプラチン – Japanese" lang="ja" hreflang="ja" data-title="シスプラチン" 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%B8%E0%AC%BF%E0%AC%B8%E0%AC%AA%E0%AD%8D%E0%AC%B2%E0%AC%BE%E0%AC%9F%E0%AC%BF%E0%AC%A8" title="ସିସପ୍ଲାଟିନ – Odia" lang="or" hreflang="or" data-title="ସିସପ୍ଲାଟିନ" 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/Cisplatyna" title="Cisplatyna – Polish" lang="pl" hreflang="pl" data-title="Cisplatyna" 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/Cisplatina" title="Cisplatina – Portuguese" lang="pt" hreflang="pt" data-title="Cisplatina" 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/Cisplatin%C4%83" title="Cisplatină – Romanian" lang="ro" hreflang="ro" data-title="Cisplatină" 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%A6%D0%B8%D1%81%D0%BF%D0%BB%D0%B0%D1%82%D0%B8%D0%BD" title="Цисплатин – Russian" lang="ru" hreflang="ru" data-title="Цисплатин" 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/Cisplatin" title="Cisplatin – Slovenian" lang="sl" hreflang="sl" data-title="Cisplatin" 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/Cisplatin" title="Cisplatin – Serbian" lang="sr" hreflang="sr" data-title="Cisplatin" 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/Cisplatin" title="Cisplatin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cisplatin" 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/Sisplatiini" title="Sisplatiini – Finnish" lang="fi" hreflang="fi" data-title="Sisplatiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%8B%E0%B8%B4%E0%B8%AA%E0%B8%9E%E0%B8%A5%E0%B8%B2%E0%B8%95%E0%B8%B4%E0%B8%99" title="ซิสพลาติน – Thai" lang="th" hreflang="th" data-title="ซิสพลาติน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Sisplatin" title="Sisplatin – Turkish" lang="tr" hreflang="tr" data-title="Sisplatin" 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%A6%D0%B8%D1%81%D0%BF%D0%BB%D0%B0%D1%82%D0%B8%D0%BD" title="Цисплатин – Ukrainian" lang="uk" hreflang="uk" data-title="Цисплатин" 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/Cisplatin" title="Cisplatin – Vietnamese" lang="vi" hreflang="vi" data-title="Cisplatin" 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%A1%BA%E9%93%82" title="顺铂 – Chinese" lang="zh" hreflang="zh" data-title="顺铂" 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 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drug</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">"Cisplatine" redirects here. For the Brazilian province that existed from 1821 to 1828, see <a href="/wiki/Cisplatina" title="Cisplatina">Cisplatina</a>. For the conflict in that province, see <a href="/wiki/Cisplatine_War" title="Cisplatine War">Cisplatine War</a>.</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): Cisplatin">Cisplatin</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:CisplatinTR.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/CisplatinTR.svg/220px-CisplatinTR.svg.png" decoding="async" width="220" height="131" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1c/CisplatinTR.svg/330px-CisplatinTR.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1c/CisplatinTR.svg/440px-CisplatinTR.svg.png 2x" data-file-width="128" data-file-height="76" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><table style="width:100%; margin:0;"><tbody><tr> <td style="vertical-align:top; text-align:center; width:50%;"><span class="bg-transparent" typeof="mw:File"><a href="/wiki/File:Cisplatin-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Cisplatin-3D-balls.png/140px-Cisplatin-3D-balls.png" decoding="async" width="140" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/96/Cisplatin-3D-balls.png/210px-Cisplatin-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/96/Cisplatin-3D-balls.png/280px-Cisplatin-3D-balls.png 2x" data-file-width="1100" data-file-height="914" /></a></span></td> <td style="vertical-align:top; text-align:center; width:50%;"><span class="mw-default-size bg-transparent" typeof="mw:File/Frameless"><a href="/wiki/File:Cisplatin-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Cisplatin-3D-vdW.png/110px-Cisplatin-3D-vdW.png" decoding="async" width="110" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Cisplatin-3D-vdW.png/165px-Cisplatin-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Cisplatin-3D-vdW.png/220px-Cisplatin-3D-vdW.png 2x" data-file-width="1100" data-file-height="949" /></a></span></td> </tr></tbody></table></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;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Platinol, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Cisplatinum, platamin, neoplatin, cismaplat, <i>cis</i>-diamminedichloroplatinum(II) (CDDP)</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/cisplatin.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/a684036.html">a684036</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="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=Cisplatin">Cisplatin</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<sup id="cite_ref-Drugs.com_pregnancy_1-0" class="reference"><a href="#cite_note-Drugs.com_pregnancy-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li> <li>Contraindicated<sup id="cite_ref-Drugs.com_pregnancy_1-1" class="reference"><a href="#cite_note-Drugs.com_pregnancy-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></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></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">L01XA01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L01XA01">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></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/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_2-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>Rx-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">100% (IV)</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">> 95%</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">30–100 hours</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">Renal</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%;"><a href="/wiki/Polyhedral_symbol" title="Polyhedral symbol">(<i>SP</i>-4-2)</a>-diamminedichloridoplatinum(II)</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=15663-27-1">15663-27-1</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></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/2767">2767</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/DB00515">DB00515</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></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.76401.html">76401</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></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/Q20Q21Q62J">Q20Q21Q62J</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/D00275">D00275</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></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:27899">CHEBI:27899</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></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/ChEMBL2068237">ChEMBL2068237</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></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB ligand</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>CPT (<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=CPT">PDBe</a></span>, <span title="www.rcsb.org"><a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/CPT">RCSB PDB</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/DTXSID50275807">DTXSID50275807</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q412415#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/100.036.106">100.036.106</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q412415#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">[Pt(NH<sub>3</sub>)<sub>2</sub>Cl<sub>2</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="7002300050000000000♠"></span>300.05</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=%5BNH3%2B%5D%5BPt%2B2%5D%28Cl%29%28Cl%29%5BNH3%2B%5D">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%;">[NH3+][Pt+2](Cl)(Cl)[NH3+]</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/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+2/p-2<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><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:LXZZYRPGZAFOLE-UHFFFAOYSA-L<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=457790642&page2=Cisplatin">(verify)</a></span></span></td></tr></tbody></table> <p><b>Cisplatin</b> is a chemical compound with <a href="/wiki/Chemical_formula" title="Chemical formula">formula</a> <i>cis</i>-<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">[Pt(NH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>Cl<sub class="template-chem2-sub">2</sub>]</span>. It is a <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complex</a> of <a href="/wiki/Platinum" title="Platinum">platinum</a> that is used as a <a href="/wiki/Chemotherapy_medication" class="mw-redirect" title="Chemotherapy medication">chemotherapy medication</a> used to treat a number of <a href="/wiki/Cancers" class="mw-redirect" title="Cancers">cancers</a>.<sup id="cite_ref-AHFS2016_3-0" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> These include <a href="/wiki/Testicular_cancer" title="Testicular cancer">testicular cancer</a>, <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</a>, <a href="/wiki/Cervical_cancer" title="Cervical cancer">cervical cancer</a>, <a href="/wiki/Bladder_cancer" title="Bladder cancer">bladder cancer</a>, <a href="/wiki/Head_and_neck_cancer" title="Head and neck cancer">head and neck cancer</a>, <a href="/wiki/Esophageal_cancer" title="Esophageal cancer">esophageal cancer</a>, <a href="/wiki/Lung_cancer" title="Lung cancer">lung cancer</a>, <a href="/wiki/Mesothelioma" title="Mesothelioma">mesothelioma</a>, <a href="/wiki/Brain_tumors" class="mw-redirect" title="Brain tumors">brain tumors</a> and <a href="/wiki/Neuroblastoma" title="Neuroblastoma">neuroblastoma</a>.<sup id="cite_ref-AHFS2016_3-1" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is given by <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">injection into a vein</a>.<sup id="cite_ref-AHFS2016_3-2" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Common side effects include <a href="/wiki/Bone_marrow_suppression" title="Bone marrow suppression">bone marrow suppression</a>, <a href="/wiki/Hearing_problems" class="mw-redirect" title="Hearing problems">hearing problems</a> including severe hearing loss, <a href="/wiki/Nephrotoxicity" title="Nephrotoxicity">kidney damage</a>, and <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>.<sup id="cite_ref-AHFS2016_3-3" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid29051464_5-0" class="reference"><a href="#cite_note-pmid29051464-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Other serious side effects include numbness, trouble walking, <a href="/wiki/Allergic_reactions" class="mw-redirect" title="Allergic reactions">allergic reactions</a>, <a href="/wiki/Electrolyte_problems" class="mw-redirect" title="Electrolyte problems">electrolyte problems</a>, and <a href="/wiki/Heart_disease" class="mw-redirect" title="Heart disease">heart disease</a>.<sup id="cite_ref-AHFS2016_3-4" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Use during pregnancy can cause harm to the developing fetus.<sup id="cite_ref-Drugs.com_pregnancy_1-3" class="reference"><a href="#cite_note-Drugs.com_pregnancy-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AHFS2016_3-5" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Cisplatin is in the <a href="/wiki/Platinum-based_antineoplastic" title="Platinum-based antineoplastic">platinum-based antineoplastic</a> family of medications.<sup id="cite_ref-AHFS2016_3-6" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It works in part by binding to DNA and inhibiting <a href="/wiki/DNA_replication" title="DNA replication">its replication</a>.<sup id="cite_ref-AHFS2016_3-7" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Cisplatin was first reported in 1845 and licensed for medical use in 1978 and 1979.<sup id="cite_ref-Fis2006_6-0" class="reference"><a href="#cite_note-Fis2006-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-AHFS2016_3-8" class="reference"><a href="#cite_note-AHFS2016-3"><span class="cite-bracket">[</span>3<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_7-0" class="reference"><a href="#cite_note-WHO21st-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WHO22nd_8-0" class="reference"><a href="#cite_note-WHO22nd-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cisplatin&action=edit&section=1" title="Edit section: Medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cisplatin is administered <a href="/wiki/Intravenously" class="mw-redirect" title="Intravenously">intravenously</a> as short-term infusion in normal saline for treatment of solid and haematological malignancies. It is used to treat various types of cancers, including <a href="/wiki/Sarcoma" title="Sarcoma">sarcomas</a>, some <a href="/wiki/Carcinoma" title="Carcinoma">carcinomas</a> (e.g., <a href="/wiki/Lung_cancer" title="Lung cancer">small cell lung cancer</a>, <a href="/wiki/Squamous_cell_carcinoma_of_the_head_and_neck" class="mw-redirect" title="Squamous cell carcinoma of the head and neck">squamous cell carcinoma of the head and neck</a> and <a href="/wiki/Ovarian_cancer" title="Ovarian cancer">ovarian cancer</a>), <a href="/wiki/Lymphoma" title="Lymphoma">lymphomas</a>, <a href="/wiki/Bladder_cancer" title="Bladder cancer">bladder cancer</a>, <a href="/wiki/Cervical_cancer" title="Cervical cancer">cervical cancer</a>,<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Germ_cell_tumor" title="Germ cell tumor">germ cell tumors</a>. </p><p>The introduction of cisplatin as a standard treatment for testicular cancer improved remission rates from 5–10% before 1974 to 75–85% by 1984.<sup id="cite_ref-Treatment_of_testicular_cancer:_a_n_10-0" class="reference"><a href="#cite_note-Treatment_of_testicular_cancer:_a_n-10"><span class="cite-bracket">[</span>10<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=Cisplatin&action=edit&section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cisplatin has a number of side effects that can limit its use: </p> <ul><li><a href="/wiki/Nephrotoxicity" title="Nephrotoxicity">Nephrotoxicity</a> (kidney damage) is the primary dose-limiting side effect and is of major clinical concern. Cisplatin selectively accumulates into the <a href="/wiki/Proximal_tubule" title="Proximal tubule">proximal tubule</a> via basolateral-to-apical transport, where it disrupts mitochondrial energetics and <a href="/wiki/Endoplasmic_reticulum" title="Endoplasmic reticulum">endoplasmic reticulum</a> Ca<sup>2+</sup> homeostasis and stimulates <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> and pro-inflammatory <a href="/wiki/Cytokines" class="mw-redirect" title="Cytokines">cytokines</a>.<sup id="cite_ref-Miller_11-0" class="reference"><a href="#cite_note-Miller-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Multiple mitigation strategies are being explored clinically and pre-clinically, including hydration regimens, <a href="/wiki/Amifostine" title="Amifostine">amifostine</a>, transporter inhibitors, antioxidants, anti-inflammatories, and <a href="/wiki/Epoxyeicosatrienoic_acids" class="mw-redirect" title="Epoxyeicosatrienoic acids">epoxyeicosatrienoic acids</a> and their analogues.<sup id="cite_ref-Miller_11-1" class="reference"><a href="#cite_note-Miller-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Singh_12-0" class="reference"><a href="#cite_note-Singh-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Neurotoxicity" title="Neurotoxicity">Neurotoxicity</a> (nerve damage) can be anticipated by performing <a href="/wiki/Nerve_conduction_studies" class="mw-redirect" title="Nerve conduction studies">nerve conduction studies</a> before and after treatment. Common neurological side effects of cisplatin include visual perception and hearing disorder, which can occur soon after treatment begins.<sup id="cite_ref-Milosavljevic_2010_13-0" class="reference"><a href="#cite_note-Milosavljevic_2010-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> While triggering apoptosis through interfering with DNA replication remains the primary mechanism of cisplatin, this has not been found to contribute to neurological side effects. Cisplatin noncompetitively inhibits an archetypal, membrane-bound mechanosensitive sodium-hydrogen ion transporter known as <a href="/wiki/SLC9A1" class="mw-redirect" title="SLC9A1">NHE-1</a>.<sup id="cite_ref-Milosavljevic_2010_13-1" class="reference"><a href="#cite_note-Milosavljevic_2010-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It is primarily found on cells of the peripheral nervous system, which are aggregated in large numbers near the ocular and aural stimuli-receiving centers. This noncompetitive interaction has been linked to hydroelectrolytic imbalances and cytoskeleton alterations, both of which have been confirmed in vitro and in vivo. However, NHE-1 inhibition has been found to be both dose-dependent (half-inhibition = 30 μg/mL) and reversible.<sup id="cite_ref-Milosavljevic_2010_13-2" class="reference"><a href="#cite_note-Milosavljevic_2010-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Cisplatin can increase levels of <a href="/wiki/Sphingosine-1-phosphate" title="Sphingosine-1-phosphate">sphingosine-1-phosphate</a> in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>, contributing to the development of <a href="/wiki/Post-chemotherapy_cognitive_impairment" title="Post-chemotherapy cognitive impairment">post-chemotherapy cognitive impairment</a>.<sup id="cite_ref-pmid36047496_14-0" class="reference"><a href="#cite_note-pmid36047496-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Nausea" title="Nausea">Nausea</a> and <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>: cisplatin is one of the most emetogenic chemotherapy agents, but this symptom is managed with prophylactic antiemetics (<a href="/wiki/Ondansetron" title="Ondansetron">ondansetron</a>, <a href="/wiki/Granisetron" title="Granisetron">granisetron</a>, etc.) in combination with <a href="/wiki/Corticosteroids" class="mw-redirect" title="Corticosteroids">corticosteroids</a>. <a href="/wiki/Aprepitant" title="Aprepitant">Aprepitant</a> combined with <a href="/wiki/Ondansetron" title="Ondansetron">ondansetron</a> and <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a> has been shown to be better for highly emetogenic chemotherapy than just <a href="/wiki/Ondansetron" title="Ondansetron">ondansetron</a> and <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a>.</li> <li><a href="/wiki/Ototoxicity" title="Ototoxicity">Ototoxicity</a> and hearing loss associated with cisplatin can be severe and is considered to be a dose-limiting side effect.<sup id="cite_ref-pmid29051464_5-1" class="reference"><a href="#cite_note-pmid29051464-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Audiometric analysis may be necessary to assess the severity of ototoxicity. Other drugs (such as the <a href="/wiki/Aminoglycoside" title="Aminoglycoside">aminoglycoside</a> antibiotic class) may also cause ototoxicity, and the administration of this class of antibiotics in patients receiving cisplatin is generally avoided. The ototoxicity of both the aminoglycosides and cisplatin may be related to their ability to bind to <a href="/wiki/Melanin" title="Melanin">melanin</a> in the <a href="/wiki/Stria_vascularis" class="mw-redirect" title="Stria vascularis">stria vascularis</a> of the inner ear or the generation of <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a>. In September 2022, the U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) approved <a href="/wiki/Sodium_thiosulfate_(medical_use)" title="Sodium thiosulfate (medical use)">sodium thiosulfate</a> under the brand name Pedmark to lessen the risk of ototoxicity and hearing loss in people receiving cisplatin.<sup id="cite_ref-pmid35489339_16-0" class="reference"><a href="#cite_note-pmid35489339-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Winstead_2022_17-0" class="reference"><a href="#cite_note-Winstead_2022-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-FDA_2022_18-0" class="reference"><a href="#cite_note-FDA_2022-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> There is ongoing investigation of <a href="/wiki/Acetylcysteine" title="Acetylcysteine">acetylcysteine</a> injections as a preventative measure.<sup id="cite_ref-pmid29051464_5-2" class="reference"><a href="#cite_note-pmid29051464-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Electrolyte_disturbance" class="mw-redirect" title="Electrolyte disturbance">Electrolyte disturbance</a>: Cisplatin can cause hypomagnesaemia, hypokalaemia and hypocalcaemia. The hypocalcaemia seems to occur in those with low serum magnesium secondary to cisplatin, so it is not primarily due to the cisplatin.</li> <li><a href="/wiki/Hemolytic_anemia" title="Hemolytic anemia">Hemolytic anemia</a> can be developed after several courses of cisplatin. It is suggested that an antibody reacting with a cisplatin-red-cell membrane is responsible for <a href="/wiki/Hemolysis" title="Hemolysis">hemolysis</a>.<sup id="cite_ref-pmid6788166_20-0" class="reference"><a href="#cite_note-pmid6788166-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cisplatin&action=edit&section=3" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cisplatin interferes with DNA replication, which kills the fastest proliferating cells, which in theory are cancerous. Following administration, one chloride ion is slowly displaced by water to give the <a href="/wiki/Aquo_complex" class="mw-redirect" title="Aquo complex">aquo complex</a> <i>cis</i>-[PtCl(NH<sub>3</sub>)<sub>2</sub>(H<sub>2</sub>O)]<sup>+</sup>, in a process termed <a href="/wiki/Aquation" title="Aquation">aquation</a>. Dissociation of the chloride is favored inside the cell because the intracellular chloride concentration is only 3–20% of the approximately 100 mM chloride concentration in the extracellular fluid.<sup id="cite_ref-WangLippard2005_21-0" class="reference"><a href="#cite_note-WangLippard2005-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><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>The water molecule in <i>cis</i>-[PtCl(NH<sub>3</sub>)<sub>2</sub>(H<sub>2</sub>O)]<sup>+</sup> is itself easily displaced by the <i>N</i>-<a href="/wiki/Heterocyclic_amine" title="Heterocyclic amine">heterocyclic bases</a> on <a href="/wiki/DNA" title="DNA">DNA</a>. <a href="/wiki/Guanine" title="Guanine">Guanine</a> preferentially binds. A model compound has been prepared and crystals were examined by <a href="/wiki/X-ray" title="X-ray">X-ray</a> crystallography<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> </p><p>Subsequent to formation of [PtCl(guanine-DNA)(NH<sub>3</sub>)<sub>2</sub>]<sup>+</sup>, crosslinking can occur via displacement of the other chloride, typically by another guanine.<sup id="cite_ref-trzaska_24-0" class="reference"><a href="#cite_note-trzaska-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Cisplatin crosslinks DNA in several ways, interfering with cell division by <a href="/wiki/Mitosis" title="Mitosis">mitosis</a>. The damaged DNA elicits <a href="/wiki/DNA_repair" title="DNA repair">DNA repair</a> mechanisms, which in turn activate <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a> when repair proves impossible. In 2008, apoptosis induced by cisplatin on human colon cancer cells was shown to depend on the mitochondrial serine-protease <a href="/wiki/HTRA2" class="mw-redirect" title="HTRA2">Omi/Htra2</a>.<sup id="cite_ref-pmid18606591_25-0" class="reference"><a href="#cite_note-pmid18606591-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Since this was only demonstrated for colon carcinoma cells, it remains an open question whether the Omi/Htra2 protein participates in the cisplatin-induced apoptosis in carcinomas from other tissues.<sup id="cite_ref-pmid18606591_25-1" class="reference"><a href="#cite_note-pmid18606591-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>Most notable among the changes in DNA are the 1,2-intrastrand cross-links with <a href="/wiki/Purine" title="Purine">purine</a> bases. These include 1,2-intrastrand d(<a href="/wiki/Guanine" title="Guanine">Gp</a>G) adducts, which form nearly 90% of the adducts, and the less common 1,2-intrastrand d(<a href="/wiki/Adenosine" title="Adenosine">Ap</a>G) adducts. Coordination chemists have obtained crystals of the products of reacting cisplain with small models of DNA. Here is a <a href="/wiki/POVray" class="mw-redirect" title="POVray">POVray</a> plot of the platinum binding to a small model of DNA.<sup id="cite_ref-pmid4048939_26-0" class="reference"><a href="#cite_note-pmid4048939-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Cisplain_adduct_with_two_Gs_bonded_to_ribose_and_linked_by_phosphate.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Cisplain_adduct_with_two_Gs_bonded_to_ribose_and_linked_by_phosphate.png/220px-Cisplain_adduct_with_two_Gs_bonded_to_ribose_and_linked_by_phosphate.png" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Cisplain_adduct_with_two_Gs_bonded_to_ribose_and_linked_by_phosphate.png/330px-Cisplain_adduct_with_two_Gs_bonded_to_ribose_and_linked_by_phosphate.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d4/Cisplain_adduct_with_two_Gs_bonded_to_ribose_and_linked_by_phosphate.png/440px-Cisplain_adduct_with_two_Gs_bonded_to_ribose_and_linked_by_phosphate.png 2x" data-file-width="640" data-file-height="480" /></a><figcaption>A POVray plot of the atomic coordinates for the cis Pt(NH3)2 and short fragment of DNA which was reported by Stephen J. Lippard in Science 1985</figcaption></figure> <p>1,3-intrastrand d(GpXpG) adducts occur but are readily excised by the <a href="/wiki/Nucleotide" title="Nucleotide">nucleotide</a> excision repair (<a href="/wiki/Nucleotide_excision_repair" title="Nucleotide excision repair">NER</a>). Other adducts include inter-strand crosslinks and nonfunctional adducts that have been postulated to contribute to cisplatin's activity. Interaction with cellular proteins, particularly <a href="/wiki/High_mobility_group" class="mw-redirect" title="High mobility group">HMG</a> domain proteins, has also been advanced as a mechanism of interfering with mitosis, although this is probably not its primary method of action.<sup id="cite_ref-pmid27688757_27-0" class="reference"><a href="#cite_note-pmid27688757-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cisplatin_resistance">Cisplatin resistance</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cisplatin&action=edit&section=4" title="Edit section: Cisplatin resistance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cisplatin combination chemotherapy is the cornerstone of treatment of many cancers. Initial platinum responsiveness is high, but the majority of cancer patients will eventually relapse with cisplatin-resistant disease. Many mechanisms of cisplatin resistance have been proposed, including changes in cellular uptake and efflux of the drug, increased detoxification of the drug, inhibition of <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>, increased <a href="/wiki/DNA_repair" title="DNA repair">DNA repair</a> or changes in metabolism.<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><sup id="cite_ref-Stordal_2007_29-0" class="reference"><a href="#cite_note-Stordal_2007-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Oxaliplatin" title="Oxaliplatin">Oxaliplatin</a> is active in highly cisplatin-resistant cancer cells in the laboratory; however, there is little evidence for its activity in the clinical treatment of patients with cisplatin-resistant cancer.<sup id="cite_ref-Stordal_2007_29-1" class="reference"><a href="#cite_note-Stordal_2007-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> The drug <a href="/wiki/Paclitaxel" title="Paclitaxel">paclitaxel</a> may be useful in the treatment of cisplatin-resistant cancer; the mechanism for this activity is as yet unknown.<sup id="cite_ref-pmid17881133_30-0" class="reference"><a href="#cite_note-pmid17881133-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Transplatin">Transplatin</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cisplatin&action=edit&section=5" title="Edit section: Transplatin"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Trans-Dichlorodiammineplatinum(II)" class="mw-redirect" title="Trans-Dichlorodiammineplatinum(II)">Transplatin</a>, the <a href="/wiki/Cis%E2%80%93trans_isomerism#Coordination_complexes" title="Cis–trans isomerism"><i>trans</i>-stereoisomer</a> of cisplatin, has formula <a href="/wiki/Trans-Dichlorodiammineplatinum(II)" class="mw-redirect" title="Trans-Dichlorodiammineplatinum(II)"><i>trans</i>-[PtCl<sub>2</sub>(NH<sub>3</sub>)<sub>2</sub>]</a> and does not exhibit a comparably useful pharmacological effect. Two mechanisms have been suggested to explain the reduced anticancer effect of transplatin. Firstly, the <i>trans</i> arrangement of the chloro ligands is thought to confer transplatin with greater chemical reactivity, causing transplatin to become deactivated before it reaches the DNA, where cisplatin exerts its pharmacological action. Secondly, the stereo-conformation of transplatin is such that it is unable to form the characteristic 1,2-intrastrand d(GpG) adducts formed by cisplatin in abundance.<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> <div class="mw-heading mw-heading2"><h2 id="Molecular_structure">Molecular structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cisplatin&action=edit&section=6" title="Edit section: Molecular structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cisplatin is the <a href="/wiki/Square_planar_molecular_geometry" title="Square planar molecular geometry">square planar</a> <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complex</a> cis-[Pt(NH<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>].<sup id="cite_ref-Miessler_1999_32-0" class="reference"><a href="#cite_note-Miessler_1999-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 286–8">: 286–8 </span></sup><sup id="cite_ref-Housecroft_2005_33-0" class="reference"><a href="#cite_note-Housecroft_2005-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 689">: 689 </span></sup> The prefix <i>cis</i> indicates the <a href="/wiki/Cis%E2%80%93trans_isomerism#Coordination_complexes" title="Cis–trans isomerism"><i>cis</i> isomer</a> in which two similar ligands are in adjacent positions.<sup id="cite_ref-Miessler_1999_32-1" class="reference"><a href="#cite_note-Miessler_1999-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Housecroft_2005_33-1" class="reference"><a href="#cite_note-Housecroft_2005-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 550">: 550 </span></sup> The systematic chemical name of this molecule is <i>cis</i>–diamminedichloroplatinum,<sup id="cite_ref-Miessler_1999_32-2" class="reference"><a href="#cite_note-Miessler_1999-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 286">: 286 </span></sup> where <i>ammine</i> with two m's indicates an <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> (NH<sub>3</sub>) <a href="/wiki/Ligand" title="Ligand">ligand</a>, as opposed to an organic <a href="/wiki/Amine" title="Amine">amine</a> with one m.<sup id="cite_ref-Miessler_1999_32-3" class="reference"><a href="#cite_note-Miessler_1999-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 284">: 284 </span></sup> </p> <style 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.mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{background:none!important}html.skin-theme-clientpref-night .mw-parser-output .mod-gallery .whitebg .thumb img:not([alt*="\200b \200b \200b "]):not([alt*="\200b \200b \200c "]){background:white!important}html.skin-theme-clientpref-night .mw-parser-output .mod-gallery img[alt*="\200b \200b \200b "]{filter:invert(1)hue-rotate(180deg)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .mod-gallery .bordered-images .thumb img[alt*="\200b \200b \200b "],html.skin-theme-clientpref-os .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{outline:solid #d7d7d7 1px}html.skin-theme-clientpref-os .mw-parser-output .skin-invert-image .mod-gallery .whitebg .thumb.thumb.thumb img{background:none!important}html.skin-theme-clientpref-os .mw-parser-output .mod-gallery .whitebg .thumb img:not([alt*="\200b \200b \200b "]):not([alt*="\200b \200b \200c "]){background:white!important}html.skin-theme-clientpref-os .mw-parser-output .mod-gallery img[alt*="\200b \200b \200b "]{filter:invert(1)hue-rotate(180deg)}}</style><div class="mod-gallery mod-gallery-default mod-gallery-center"><div class="main"><div><ul class="gallery mw-gallery-traditional nochecker bordered-images"> <li class="gallerybox" style="width: 195px"> <div class="thumb" style="width: 190px; height: 190px;"><span typeof="mw:File"><a href="/wiki/File:Solution_structure_of_Cisplatin-induced_Interstrand_GG_cross-link.png" class="mw-file-description" title="Solution structure of cisplatin (highlighted) interstrand GG adducts with double-stranded DNA. (PDB: 1DDP)"><img alt="Solution structure of cisplatin (highlighted) interstrand GG adducts with double-stranded DNA. (PDB: 1DDP)" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Solution_structure_of_Cisplatin-induced_Interstrand_GG_cross-link.png/160px-Solution_structure_of_Cisplatin-induced_Interstrand_GG_cross-link.png" decoding="async" width="160" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/Solution_structure_of_Cisplatin-induced_Interstrand_GG_cross-link.png/240px-Solution_structure_of_Cisplatin-induced_Interstrand_GG_cross-link.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/Solution_structure_of_Cisplatin-induced_Interstrand_GG_cross-link.png/320px-Solution_structure_of_Cisplatin-induced_Interstrand_GG_cross-link.png 2x" data-file-width="1259" data-file-height="1049" /></a></span></div> <div class="gallerytext">Solution structure of cisplatin (highlighted) interstrand GG adducts with double-stranded DNA. (<a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a>: <a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/1ddp">1DDP</a>)</div> </li> <li class="gallerybox" style="width: 195px"> <div class="thumb" style="width: 190px; height: 190px;"><span typeof="mw:File"><a href="/wiki/File:X-Ray_diffraction_structure_of_Cisplatin_intra-strand_GG_adducts.png" class="mw-file-description" title="2.60Å resolution crystal structure of cisplatin (highlighted) intrastrand GG adducts with double-stranded DNA. Note: the hydrogens on amine ligands are not shown. (PDB: 1AIO)"><img alt="2.60Å resolution crystal structure of cisplatin (highlighted) intrastrand GG adducts with double-stranded DNA. Note: the hydrogens on amine ligands are not shown. (PDB: 1AIO)" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/X-Ray_diffraction_structure_of_Cisplatin_intra-strand_GG_adducts.png/160px-X-Ray_diffraction_structure_of_Cisplatin_intra-strand_GG_adducts.png" decoding="async" width="160" height="133" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/23/X-Ray_diffraction_structure_of_Cisplatin_intra-strand_GG_adducts.png/240px-X-Ray_diffraction_structure_of_Cisplatin_intra-strand_GG_adducts.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/23/X-Ray_diffraction_structure_of_Cisplatin_intra-strand_GG_adducts.png/320px-X-Ray_diffraction_structure_of_Cisplatin_intra-strand_GG_adducts.png 2x" data-file-width="1259" data-file-height="1049" /></a></span></div> <div class="gallerytext">2.60Å resolution crystal structure of cisplatin (highlighted) intrastrand GG adducts with double-stranded DNA. Note: the hydrogens on amine ligands are not shown. (<a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a>: <a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/1AIO">1AIO</a>)</div> </li> </ul></div></div></div> <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=Cisplatin&action=edit&section=7" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The compound <i>cis</i>-[Pt(NH<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub>] was first described by Italian chemist <a href="/w/index.php?title=Michele_Peyrone&action=edit&redlink=1" class="new" title="Michele Peyrone (page does not exist)">Michele Peyrone</a> in 1845, and known for a long time as Peyrone's salt.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> The structure was deduced by <a href="/wiki/Alfred_Werner" title="Alfred Werner">Alfred Werner</a> in 1893.<sup id="cite_ref-trzaska_24-1" class="reference"><a href="#cite_note-trzaska-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> In 1965, <a href="/wiki/Barnett_Rosenberg" title="Barnett Rosenberg">Barnett Rosenberg</a>, Van Camp et al. of <a href="/wiki/Michigan_State_University" title="Michigan State University">Michigan State University</a> discovered that <a href="/wiki/Electrolysis" title="Electrolysis">electrolysis</a> of platinum electrodes generated a soluble platinum complex which inhibited binary fission in <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a></i> (<i>E. coli</i>) bacteria. Although bacterial cell growth continued, cell division was arrested, the bacteria growing as filaments up to 300 times their normal length.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> The octahedral Pt(IV) complex <i>cis</i>-[PtCl<sub>4</sub>(NH<sub>3</sub>)<sub>2</sub>], but not the <i>trans</i> isomer, was found to be effective at forcing filamentous growth of <i>E. coli</i> cells. The square planar Pt(II) complex, <i>cis</i>-[PtCl<sub>2</sub>(NH<sub>3</sub>)<sub>2</sub>] turned out to be even more effective at forcing filamentous growth.<sup id="cite_ref-pmid5337590_37-0" class="reference"><a href="#cite_note-pmid5337590-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> This finding led to the observation that <i>cis</i>-[PtCl<sub>2</sub>(NH<sub>3</sub>)<sub>2</sub>] was indeed highly effective at regressing the mass of <a href="/wiki/Sarcoma" title="Sarcoma">sarcomas</a> in <a href="/wiki/Rat" title="Rat">rats</a>.<sup id="cite_ref-pmid5782119_39-0" class="reference"><a href="#cite_note-pmid5782119-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Confirmation of this discovery, and extension of testing to other tumour cell lines launched the medicinal applications of cisplatin. Cisplatin was approved for use in testicular and ovarian cancers by the U.S. Food and Drug Administration on 19 December 1978.<sup id="cite_ref-trzaska_24-2" class="reference"><a href="#cite_note-trzaska-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-isbn0-691-14180-0_40-0" class="reference"><a href="#cite_note-isbn0-691-14180-0-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> and in the UK (and in several other European countries) in 1979.<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> Cisplatin was the first to be developed.<sup id="cite_ref-Kelland_43-0" class="reference"><a href="#cite_note-Kelland-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> In 1983 pediatric oncologist Roger Packer began incorporating cisplatin into adjuvant chemotherapy for the treatment of childhood <a href="/wiki/Medulloblastoma" title="Medulloblastoma">medulloblastoma</a>.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> The new protocol that he developed led to a marked increase in disease-free survival rates for patients with medulloblastoma, up to around 85%.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> The Packer Protocol has since become a standard treatment for medulloblastoma. Likewise, cisplatin has been found to be particularly effective against <a href="/wiki/Testicular_cancer" title="Testicular cancer">testicular cancer</a>, where its use improved the cure rate from 10% to 85%.<sup id="cite_ref-Treatment_of_testicular_cancer:_a_n_10-1" class="reference"><a href="#cite_note-Treatment_of_testicular_cancer:_a_n-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cisplatin&action=edit&section=8" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Syntheses of cisplatin start from <a href="/wiki/Potassium_tetrachloroplatinate" title="Potassium tetrachloroplatinate">potassium tetrachloroplatinate</a>. Several procedures are available. One obstacle is the facile formation of <a href="/wiki/Magnus%27s_green_salt" title="Magnus's green salt">Magnus's green salt</a> (MGS), which has the same empirical formula as cisplatin. The traditional way to avoid MGS involves the conversion of K<sub>2</sub>PtCl<sub>4</sub> to <a href="/wiki/Potassium_tetraiodoplatinate" title="Potassium tetraiodoplatinate">K<sub>2</sub>PtI<sub>4</sub></a>, as originally described by Dhara.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Alderden_47-0" class="reference"><a href="#cite_note-Alderden-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> Reaction with <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> forms PtI<sub>2</sub>(NH<sub>3</sub>)<sub>2</sub> which is isolated as a yellow compound. When <a href="/wiki/Silver_nitrate" title="Silver nitrate">silver nitrate</a> in water is added insoluble <a href="/wiki/Silver_iodide" title="Silver iodide">silver iodide</a> precipitates and [Pt(OH<sub>2</sub>)<sub>2</sub>(NH<sub>3</sub>)<sub>2</sub>](NO<sub>3</sub>)<sub>2</sub> remains in solution. Addition of <a href="/wiki/Potassium_chloride" title="Potassium chloride">potassium chloride</a> will form the final product which precipitates<sup id="cite_ref-Alderden_47-1" class="reference"><a href="#cite_note-Alderden-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> In the triiodo intermediate the addition of the second ammonia ligand is governed by the <a href="/wiki/Trans_effect" title="Trans effect">trans effect</a>.<sup id="cite_ref-Alderden_47-2" class="reference"><a href="#cite_note-Alderden-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Cisplatin_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Cisplatin_synthesis.svg/600px-Cisplatin_synthesis.svg.png" decoding="async" width="600" height="270" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/31/Cisplatin_synthesis.svg/900px-Cisplatin_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/31/Cisplatin_synthesis.svg/1200px-Cisplatin_synthesis.svg.png 2x" data-file-width="785" data-file-height="353" /></a></span></dd></dl> <p>A <a href="/wiki/One-pot_synthesis" title="One-pot synthesis">one-pot synthesis</a> of cisplatin from K<sub>2</sub>PtCl<sub>4</sub> has been developed. It relies on the slow release of ammonia from ammonium acetate.<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> </p> <div style="clear:both;" class=""></div> <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=Cisplatin&action=edit&section=9" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cisplatin has been studied with <a href="/wiki/Auger_therapy" title="Auger therapy">Auger therapy</a> to increase the therapeutic effects of cisplatin, without increasing normal tissue toxicities.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> However, due to significant side effects, the search for structurally novel Pt(II) and Pd(II) compounds exhibiting antineoplastic activity is extremely important and aims to develop more effective and less toxic drugs.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> Cisplatin-like molecules ([PtCl(NH<sub>3</sub>)<sub>2</sub>] and [Pt(NH<sub>3</sub>)Cl<sub>2</sub>]) linked by variable length alkandiamine chains have attracted some interest in cancer chemotherapy.<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><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<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> <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=Cisplatin&action=edit&section=10" 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 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.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 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"Cytotoxic activity of metal complexes of biogenic polyamines: polynuclear platinum(II) chelates". <i>Journal of Medicinal Chemistry</i>. <b>47</b> (11): <span class="nowrap">2917–</span>2925. <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%2Fjm0311238">10.1021/jm0311238</a>. <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/10316%2F10605">10316/10605</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/15139770">15139770</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+Medicinal+Chemistry&rft.atitle=Cytotoxic+activity+of+metal+complexes+of+biogenic+polyamines%3A+polynuclear+platinum%28II%29+chelates&rft.volume=47&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2917-%3C%2Fspan%3E2925&rft.date=2004-05&rft_id=info%3Ahdl%2F10316%2F10605&rft_id=info%3Apmid%2F15139770&rft_id=info%3Adoi%2F10.1021%2Fjm0311238&rft.aulast=Teixeira&rft.aufirst=LJ&rft.au=Seabra%2C+M&rft.au=Reis%2C+E&rft.au=da+Cruz%2C+MT&rft.au=de+Lima%2C+MC&rft.au=Pereira%2C+E&rft.au=Miranda%2C+MA&rft.au=Marques%2C+MP&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACisplatin" class="Z3988"></span></span> </li> <li id="cite_note-52"><span class="mw-cite-backlink"><b><a href="#cite_ref-52">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVinciChateigner2022" class="citation journal cs1">Vinci D, Chateigner D (1 December 2022). <a rel="nofollow" class="external text" href="https://scripts.iucr.org/cgi-bin/paper?S2052520622009660">"Synthesis and structural characterization of a new dinuclear platinum(III) complex, [Pt 2 Cl 4 (NH 3 ) 2 {μ-HN=C(O)Bu t } 2 ]"</a>. <i>Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials</i>. <b>78</b> (6): <span class="nowrap">835–</span>841. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1107%2FS2052520622009660">10.1107/S2052520622009660</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2052-5206">2052-5206</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/PMC9728019">9728019</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Acta+Crystallographica+Section+B+Structural+Science%2C+Crystal+Engineering+and+Materials&rft.atitle=Synthesis+and+structural+characterization+of+a+new+dinuclear+platinum%28III%29+complex%2C+%5BPt+2+Cl+4+%28NH+3+%29+2+%7B%CE%BC-HN%3DC%28O%29Bu+t+%7D+2+%5D&rft.volume=78&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E835-%3C%2Fspan%3E841&rft.date=2022-12-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC9728019%23id-name%3DPMC&rft.issn=2052-5206&rft_id=info%3Adoi%2F10.1107%2FS2052520622009660&rft.aulast=Vinci&rft.aufirst=D&rft.au=Chateigner%2C+D&rft_id=https%3A%2F%2Fscripts.iucr.org%2Fcgi-bin%2Fpaper%3FS2052520622009660&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACisplatin" class="Z3988"></span></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 id="CITEREFOmondiOjwachJaganyi2020" class="citation journal cs1">Omondi RO, Ojwach SO, Jaganyi D (November 2020). "Review of comparative studies of cytotoxic activities of Pt(II), Pd(II), Ru(II)/(III) and Au(III) complexes, their kinetics of ligand substitution reactions and DNA/BSA interactions". <i>Inorganica Chimica Acta</i>. <b>512</b>: 119883. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.ica.2020.119883">10.1016/j.ica.2020.119883</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:225575546">225575546</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Inorganica+Chimica+Acta&rft.atitle=Review+of+comparative+studies+of+cytotoxic+activities+of+Pt%28II%29%2C+Pd%28II%29%2C+Ru%28II%29%2F%28III%29+and+Au%28III%29+complexes%2C+their+kinetics+of+ligand+substitution+reactions+and+DNA%2FBSA+interactions&rft.volume=512&rft.pages=119883&rft.date=2020-11&rft_id=info%3Adoi%2F10.1016%2Fj.ica.2020.119883&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A225575546%23id-name%3DS2CID&rft.aulast=Omondi&rft.aufirst=RO&rft.au=Ojwach%2C+SO&rft.au=Jaganyi%2C+D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACisplatin" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cisplatin&action=edit&section=11" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDabrowiak2009" class="citation book cs1">Dabrowiak JC (2009). "Cisplatin". <i>Metals in Medicine</i> (1 ed.). John Wiley & Sons. pp. <span class="nowrap">73–</span>107. <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%2F9780470684986.ch3">10.1002/9780470684986.ch3</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-68196-1" title="Special:BookSources/978-0-470-68196-1"><bdi>978-0-470-68196-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cisplatin&rft.btitle=Metals+in+Medicine&rft.pages=%3Cspan+class%3D%22nowrap%22%3E73-%3C%2Fspan%3E107&rft.edition=1&rft.pub=John+Wiley+%26+Sons&rft.date=2009&rft_id=info%3Adoi%2F10.1002%2F9780470684986.ch3&rft.isbn=978-0-470-68196-1&rft.aulast=Dabrowiak&rft.aufirst=James+C.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACisplatin" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFRiddellLippard2018" class="citation book cs1">Riddell IA, Lippard SJ (2018). "Cisplatin and Oxaliplatin: Our Current Understanding of Their Actions". In Sigel A, Sigel H, Freisinger E, Sigel RK (eds.). <i>Metallo-Drugs: Development and Action of Anticancer Agents</i>. Metal Ions in Life Sciences. Vol. 18. Berlin: de Gruyter GmbH. pp. <span class="nowrap">1–</span>42. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1515%2F9783110470734-007">10.1515/9783110470734-007</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-11-046984-4" title="Special:BookSources/978-3-11-046984-4"><bdi>978-3-11-046984-4</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/29394020">29394020</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cisplatin+and+Oxaliplatin%3A+Our+Current+Understanding+of+Their+Actions&rft.btitle=Metallo-Drugs%3A+Development+and+Action+of+Anticancer+Agents&rft.place=Berlin&rft.series=Metal+Ions+in+Life+Sciences&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1-%3C%2Fspan%3E42&rft.pub=de+Gruyter+GmbH&rft.date=2018&rft_id=info%3Apmid%2F29394020&rft_id=info%3Adoi%2F10.1515%2F9783110470734-007&rft.isbn=978-3-11-046984-4&rft.aulast=Riddell&rft.aufirst=IA&rft.au=Lippard%2C+SJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACisplatin" class="Z3988"></span></li></ul> </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=Cisplatin&action=edit&section=12" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://druginfo.nlm.nih.gov/drugportal/name/cisplatin">"Cisplatin"</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=Cisplatin&rft_id=https%3A%2F%2Fdruginfo.nlm.nih.gov%2Fdrugportal%2Fname%2Fcisplatin&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACisplatin" class="Z3988"></span></li> <li><a rel="nofollow" class="external text" href="https://publications.iarc.fr/_publications/media/download/3339/e9c601280dccaa5a877bbc1ef1bd8e4a683ec189.pdf">IARC Monograph: "Cisplatin"</a></li> <li>Wikiversity page for the International Ototoxicity Management Group: <a class="external free" href="https://en.wikiversity.org/wiki/International_Ototoxicity_Management_Group_(IOMG)">https://en.wikiversity.org/wiki/International_Ototoxicity_Management_Group_(IOMG)</a></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 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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 href="/wiki/Doxorubicin" title="Doxorubicin">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 class="mw-selflink selflink">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> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"></div><div role="navigation" class="navbox" aria-labelledby="Platinum_compounds59" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Platinum_compounds" title="Template:Platinum compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Platinum_compounds" title="Template talk:Platinum compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Platinum_compounds" title="Special:EditPage/Template:Platinum compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Platinum_compounds59" style="font-size:114%;margin:0 4em"><a href="/wiki/Platinum_compounds" class="mw-redirect" title="Platinum compounds">Platinum compounds</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pt(−II)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Caesium_platinide&action=edit&redlink=1" class="new" title="Caesium platinide (page does not exist)">Cs<sub>2</sub>Pt</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pt(0)</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/Tetrakis(triphenylphosphine)platinum(0)" title="Tetrakis(triphenylphosphine)platinum(0)">Pt(PPh<sub>3</sub>)<sub>4</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pt(II)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carboplatin" title="Carboplatin">Pt(NH<sub>3</sub>)<sub>2</sub>(CO<sub>2</sub>)<sub>2</sub>C<sub>4</sub>H<sub>6</sub></a></li> <li><a class="mw-selflink selflink"><i>cis</i>-Pt(NH<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub></a></li> <li><a href="/wiki/Transplatin" title="Transplatin"><i>trans</i>-Pt(NH<sub>3</sub>)<sub>2</sub>Cl<sub>2</sub></a></li> <li><a href="/wiki/Krogmann%27s_salt" title="Krogmann's salt">K<sub>2</sub>Pt(CN)<sub>4</sub></a></li> <li><a href="/wiki/Magnus%27s_green_salt" title="Magnus's green salt">Pt(NH<sub>3</sub>)<sub>4</sub>PtCl<sub>4</sub></a></li> <li><a href="/wiki/Nedaplatin" title="Nedaplatin">Pt(NH<sub>3</sub>)<sub>2</sub>CO<sub>2</sub>CH<sub>2</sub>O</a></li> <li><a href="/wiki/Oxaliplatin" title="Oxaliplatin">(Cy(NH<sub>2</sub>)<sub>2</sub>)PtC<sub>2</sub>O<sub>4</sub></a></li> <li><a href="/wiki/Picoplatin" title="Picoplatin">NH<sub>3</sub>PtCl<sub>2</sub>(PyrMe)</a></li> <li><a href="/wiki/Platinum(II)_acetate" title="Platinum(II) acetate">Pt(OAc)<sub>2</sub></a></li> <li><a href="/wiki/Platinum(II)_bromide" title="Platinum(II) bromide">PtBr<sub>2</sub></a></li> <li><a href="/wiki/Platinum(II)_chloride" title="Platinum(II) chloride">PtCl<sub>2</sub></a></li> <li><a href="/wiki/Platinum(II)_fluoride" title="Platinum(II) fluoride">PtF<sub>2</sub></a></li> <li><a href="/wiki/Platinum(II)_iodide" title="Platinum(II) iodide"><span class="chemf nowrap">PtI<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></span></a></li> <li><a href="/wiki/Platinum_diphosphide" title="Platinum diphosphide"><span class="chemf nowrap">PtP<sub class="template-chem2-sub">2</sub></span></a></li> <li><a href="/wiki/Potassium_tetrachloroplatinate" title="Potassium tetrachloroplatinate">K<sub>2</sub>PtCl<sub>4</sub></a></li> <li><a href="/wiki/Triplatin_tetranitrate" title="Triplatin tetranitrate">[(PtCl(NH<sub>3</sub>)<sub>2</sub>(C<sub>6</sub>H<sub>12</sub>(NH<sub>2</sub>)<sub>2</sub>))Pt(NH<sub>3</sub>)<sub>2</sub>](NO<sub>3</sub>)<sub>4</sub></a></li> <li><a href="/w/index.php?title=Platinum(II)_hydroxide&action=edit&redlink=1" class="new" title="Platinum(II) hydroxide (page does not exist)">Pt(OH)<sub>2</sub></a></li> <li><a href="/wiki/Platinum-samarium" class="mw-redirect" title="Platinum-samarium">PtSm</a></li> <li><a href="/wiki/Platinum(II)_bis(acetylacetonate)" title="Platinum(II) bis(acetylacetonate)">Pt(C<sub>5</sub>H<sub>7</sub>O<sub>2</sub>)<sub>2</sub></a></li> <li><a href="/wiki/Platinum(II)_sulfide" title="Platinum(II) sulfide">PtS</a></li></ul></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Organoplatinum(II)_compounds32" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organoplatinum" class="mw-redirect" title="Organoplatinum">Organoplatinum</a>(II) compounds</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <li><a href="/wiki/Dichloro(cycloocta-1,5-diene)platinum(II)" title="Dichloro(cycloocta-1,5-diene)platinum(II)">PtCl<sub>2</sub>(Cod)</a></li> <li><a href="/wiki/Platinum_fulminate" title="Platinum fulminate">Pt(CNO)<sub>2</sub></a></li> <li><a href="/wiki/Zeise%27s_salt" title="Zeise's salt">KPtCl<sub>3</sub>C<sub>2</sub>H<sub>4</sub></a></li> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pt(IV)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adams%27_catalyst" title="Adams' catalyst">PtO<sub>2</sub></a></li> <li><a href="/wiki/Ammonium_hexachloroplatinate" title="Ammonium hexachloroplatinate">(NH<sub>4</sub>)<sub>2</sub>PtCl<sub>6</sub></a></li> <li><a href="/wiki/Chloroplatinic_acid" title="Chloroplatinic acid">H<sub>2</sub>PtCl<sub>6</sub></a></li> <li><a href="/wiki/Platinum(IV)_bromide" title="Platinum(IV) bromide">PtBr<sub>4</sub></a></li> <li><a href="/wiki/Platinum(IV)_chloride" title="Platinum(IV) chloride">PtCl<sub>4</sub></a></li> <li><a href="/wiki/Platinum_tetrafluoride" title="Platinum tetrafluoride">PtF<sub>4</sub></a></li> <li><a href="/wiki/Potassium_hexachloroplatinate" title="Potassium hexachloroplatinate">K<sub>2</sub>PtCl<sub>6</sub></a></li> <li><a href="/wiki/Satraplatin" title="Satraplatin">Pt(OAc)<sub>2</sub>Cl<sub>2</sub>(NH<sub>3</sub>)(NH<sub>2</sub>Cy)</a></li> <li><a href="/wiki/Sodium_hexachloroplatinate" title="Sodium hexachloroplatinate">Na<sub>2</sub>PtCl<sub>6</sub></a></li> <li><a href="/w/index.php?title=Platinum(IV)_hydroxide&action=edit&redlink=1" class="new" title="Platinum(IV) hydroxide (page does not exist)">Pt(OH)<sub>4</sub></a></li> <li><a href="/wiki/Platinum(IV)_iodide" title="Platinum(IV) iodide"><span class="chemf nowrap">PtI<sub class="template-chem2-sub">4</sub></span></a></li> <li><a href="/wiki/Platinum(IV)_sulfide" class="mw-redirect" title="Platinum(IV) sulfide">PtS<sub>2</sub></a></li> <li><a href="/wiki/Platinum_diselenide" title="Platinum diselenide">PtSe<sub>2</sub></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pt(V)</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/Platinum_pentafluoride" title="Platinum pentafluoride">PtF<sub>5</sub></a></li> <li><a href="/wiki/Dioxygenyl_hexafluoroplatinate" title="Dioxygenyl hexafluoroplatinate">O<sub>2</sub>PtF<sub>6</sub></a></li> <li><a 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