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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-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Chemistry</span> </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Society and culture</span> </div> </a> <button aria-controls="toc-Society_and_culture-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Society and culture subsection</span> </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Suppliers" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Suppliers"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Suppliers</span> </div> </a> <ul id="toc-Suppliers-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Shortage" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Shortage"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Shortage</span> </div> </a> <ul id="toc-Shortage-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Controversy" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Controversy"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Controversy</span> </div> </a> <button aria-controls="toc-Controversy-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 Controversy subsection</span> </button> <ul id="toc-Controversy-sublist" class="vector-toc-list"> <li id="toc-Pharmaceutical_bioprospecting" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmaceutical_bioprospecting"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Pharmaceutical bioprospecting</span> </div> </a> <ul id="toc-Pharmaceutical_bioprospecting-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Vincristine_and_confusion_with_other_drugs_in_administration" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Vincristine_and_confusion_with_other_drugs_in_administration"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Vincristine and confusion with other drugs in administration</span> </div> </a> <ul id="toc-Vincristine_and_confusion_with_other_drugs_in_administration-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">9</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">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</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 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id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Vincristine</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 33 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-33" 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">33 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/%D9%81%D9%8A%D9%86%D9%83%D8%B1%D9%8A%D8%B3%D8%AA%D9%8A%D9%86" title="فينكريستين – Arabic" lang="ar" hreflang="ar" data-title="فينكريستين" 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/%D9%88%DB%8C%D9%86%DA%A9%D8%B1%DB%8C%D8%B3%D8%AA%DB%8C%D9%86" title="وینکریستین – South Azerbaijani" lang="azb" hreflang="azb" data-title="وینکریستین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Vincristina" title="Vincristina – Catalan" lang="ca" hreflang="ca" data-title="Vincristina" 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/Fincristin" title="Fincristin – Welsh" lang="cy" hreflang="cy" data-title="Fincristin" 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/Vincristin" title="Vincristin – German" lang="de" hreflang="de" data-title="Vincristin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Vincristina" title="Vincristina – Spanish" lang="es" hreflang="es" data-title="Vincristina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%88%DB%8C%D9%86%DA%A9%D8%B1%DB%8C%D8%B3%D8%AA%DB%8C%D9%86" title="وینکریستین – Persian" lang="fa" hreflang="fa" data-title="وینکریستین" 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/Vincristine" title="Vincristine – French" lang="fr" hreflang="fr" data-title="Vincristine" 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/%EB%B9%88%ED%81%AC%EB%A6%AC%EC%8A%A4%ED%8B%B4" title="빈크리스틴 – Korean" lang="ko" hreflang="ko" data-title="빈크리스틴" 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%8E%D5%AB%D5%B6%D5%AF%D6%80%D5%AB%D5%BD%D5%BF%D5%AB%D5%B6" title="Վինկրիստին – Armenian" lang="hy" hreflang="hy" data-title="Վինկրիստին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Vinkristin" title="Vinkristin – Indonesian" lang="id" hreflang="id" data-title="Vinkristin" 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/Vincristina" title="Vincristina – Italian" lang="it" hreflang="it" data-title="Vincristina" 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%95%D7%99%D7%A0%D7%A7%D7%A8%D7%99%D7%A1%D7%98%D7%99%D7%9F" title="וינקריסטין – Hebrew" lang="he" hreflang="he" data-title="וינקריסטין" 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/Vinkrisztin" title="Vinkrisztin – Hungarian" lang="hu" hreflang="hu" data-title="Vinkrisztin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Vincristine" title="Vincristine – Dutch" lang="nl" hreflang="nl" data-title="Vincristine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%93%E3%83%B3%E3%82%AF%E3%83%AA%E3%82%B9%E3%83%81%E3%83%B3" title="ビンクリスチン – Japanese" lang="ja" hreflang="ja" data-title="ビンクリスチン" 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%AD%E0%AC%BF%E0%AC%A8%E2%80%8C%E0%AD%8D%E2%80%8C%E0%AC%95%E0%AD%8D%E0%AC%B0%E0%AC%BF%E0%AC%B8%E0%AD%8D%E0%AC%9F%E0%AC%BF%E0%AC%A8%E0%AD%8D" title="ଭିନ‌୍‌କ୍ରିସ୍ଟିନ୍ – Odia" lang="or" hreflang="or" data-title="ଭିନ‌୍‌କ୍ରିସ୍ଟିନ୍" 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/Winkrystyna" title="Winkrystyna – Polish" lang="pl" hreflang="pl" data-title="Winkrystyna" 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/Vincristina" title="Vincristina – Portuguese" lang="pt" hreflang="pt" data-title="Vincristina" 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/Vincristin%C4%83" title="Vincristină – Romanian" lang="ro" hreflang="ro" data-title="Vincristină" 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%92%D0%B8%D0%BD%D0%BA%D1%80%D0%B8%D1%81%D1%82%D0%B8%D0%BD" title="Винкристин – Russian" lang="ru" hreflang="ru" data-title="Винкристин" 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/Vinkristin" title="Vinkristin – Slovenian" lang="sl" hreflang="sl" data-title="Vinkristin" 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/Vinkristin" title="Vinkristin – Serbian" lang="sr" hreflang="sr" data-title="Vinkristin" 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/Vinkristin" title="Vinkristin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Vinkristin" 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/Vinkristiini" title="Vinkristiini – Finnish" lang="fi" hreflang="fi" data-title="Vinkristiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Vinkristin" title="Vinkristin – Swedish" lang="sv" hreflang="sv" data-title="Vinkristin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tl mw-list-item"><a href="https://tl.wikipedia.org/wiki/Vincristine" title="Vincristine – Tagalog" lang="tl" hreflang="tl" data-title="Vincristine" data-language-autonym="Tagalog" data-language-local-name="Tagalog" class="interlanguage-link-target"><span>Tagalog</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%B5%E0%AE%BF%E0%AE%A9%E0%AF%8D%E0%AE%95%E0%AF%8D%E0%AE%95%E0%AE%BF%E0%AE%B0%E0%AE%BF%E0%AE%9A%E0%AF%81%E0%AE%9F%E0%AF%8D%E0%AE%9F%E0%AF%80%E0%AE%A9%E0%AF%8D" title="வின்க்கிரிசுட்டீன் – Tamil" lang="ta" hreflang="ta" data-title="வின்க்கிரிசுட்டீன்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%B5%E0%B0%BF%E0%B0%A8%E0%B1%8D%E2%80%8C%E0%B0%95%E0%B1%8D%E0%B0%B0%E0%B0%BF%E0%B0%B8%E0%B1%8D%E0%B0%9F%E0%B1%80%E0%B0%A8%E0%B1%8D" title="విన్‌క్రిస్టీన్ – Telugu" lang="te" hreflang="te" data-title="విన్‌క్రిస్టీన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Vinkristin" title="Vinkristin – Turkish" lang="tr" hreflang="tr" data-title="Vinkristin" 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%92%D1%96%D0%BD%D0%BA%D1%80%D0%B8%D1%81%D1%82%D0%B8%D0%BD" title="Вінкристин – Ukrainian" lang="uk" hreflang="uk" data-title="Вінкристин" 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/Vincristine" title="Vincristine – Vietnamese" lang="vi" hreflang="vi" data-title="Vincristine" 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%95%BF%E6%98%A5%E6%96%B0%E7%A2%B1" title="长春新碱 – Chinese" lang="zh" hreflang="zh" data-title="长春新碱" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q408977#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Vincristine" title="View the content 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound; chemotherapy medication</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">Not to be confused with <a href="/wiki/Vinblastine" title="Vinblastine">vinblastine</a>.</div> <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): Vincristine">Vincristine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Vincristine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Vincristine.svg/240px-Vincristine.svg.png" decoding="async" width="240" height="181" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Vincristine.svg/360px-Vincristine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/bf/Vincristine.svg/480px-Vincristine.svg.png 2x" data-file-width="1712" data-file-height="1292" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="bg-transparent" typeof="mw:File"><a href="/wiki/File:Vincristine3DanBS.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Vincristine3DanBS.gif/200px-Vincristine3DanBS.gif" decoding="async" width="200" height="200" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/7/71/Vincristine3DanBS.gif 1.5x" data-file-width="256" data-file-height="256" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data"><span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˈ/: primary stress follows">ˈ</span><span title="'v' in 'vie'">v</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'k' in 'kind'">k</span><span title="'r' in 'rye'">r</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'s' in 'sigh'">s</span><span title="'t' in 'tie'">t</span><span title="/iː/: 'ee' in 'fleece'">iː</span><span title="'n' in 'nigh'">n</span></span>/</a></span> <span class="ext-phonos"><span data-nosnippet="" id="ooui-php-1" class="noexcerpt ext-phonos-PhonosButton ext-phonos-PhonosButton-emptylabel oo-ui-widget oo-ui-widget-enabled oo-ui-buttonElement oo-ui-buttonElement-frameless oo-ui-iconElement oo-ui-buttonWidget" data-ooui="{"_":"mw.Phonos.PhonosButton","href":"\/\/upload.wikimedia.org\/wikipedia\/commons\/transcoded\/3\/39\/En-us-Vincristine.ogg\/En-us-Vincristine.ogg.mp3","rel":["nofollow"],"framed":false,"icon":"volumeUp","data":{"ipa":"","text":"","lang":"en","wikibase":"","file":"En-us-Vincristine.ogg"},"classes":["noexcerpt","ext-phonos-PhonosButton","ext-phonos-PhonosButton-emptylabel"]}"><a role="button" tabindex="0" href="//upload.wikimedia.org/wikipedia/commons/transcoded/3/39/En-us-Vincristine.ogg/En-us-Vincristine.ogg.mp3" rel="nofollow" aria-label="Play audio" title="Play audio" class="oo-ui-buttonElement-button"><span class="oo-ui-iconElement-icon oo-ui-icon-volumeUp"></span><span class="oo-ui-labelElement-label"></span><span class="oo-ui-indicatorElement-indicator oo-ui-indicatorElement-noIndicator"></span></a></span><sup class="ext-phonos-attribution noexcerpt navigation-not-searchable"><a href="/wiki/File:En-us-Vincristine.ogg" title="File:En-us-Vincristine.ogg">ⓘ</a></sup></span></span><sup id="cite_ref-DictionaryVincristine_1-0" class="reference"><a href="#cite_note-DictionaryVincristine-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Oncovin, Vincasar, Marqibo, others<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">leurocristine ki</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/vincristine-sulfate.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/a682822.html">a682822</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=Vincristine">Vincristine</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> D</li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a></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">L01CA02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L01CA02">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/Prescription_drug" title="Prescription drug">℞-only</a></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">n/a (not reliably absorbed by the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">GI tract</a>)<sup id="cite_ref-MD_3-0" class="reference"><a href="#cite_note-MD-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></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">~44%<sup id="cite_ref-MSR_4-0" class="reference"><a href="#cite_note-MSR-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data">Liver, mostly via <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> and <a href="/wiki/CYP3A5" title="CYP3A5">CYP3A5</a><sup id="cite_ref-MD_3-3" class="reference"><a href="#cite_note-MD-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></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">19 to 155 hours (mean: 85 hours)<sup id="cite_ref-MD_3-1" class="reference"><a href="#cite_note-MD-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data">Faeces (70–80%), urine (10–20%)<sup id="cite_ref-MD_3-2" class="reference"><a href="#cite_note-MD-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(3a<i>R</i>,3a1<i>R</i>,4<i>R</i>,5<i>S</i>,5a<i>R</i>,10b<i>R</i>)-Methyl 4-acetoxy-3a-ethyl-9-((5<i>S</i>,7<i>S</i>,9<i>S</i>)-5-ethyl-5-hydroxy-9-(methoxycarbonyl)-2,4,5,6,7,8,9,10-octahydro-1<i>H</i>-3,7-methano[1]azacycloundecino[5,4-<i>b</i>]indol-9-yl)-6-formyl-5-hydroxy-8-methoxy-3a,3a1,4,5,5a,6,11,12-octahydro-1<i>H</i>-indolizino[8,1-cd]carbazole-5-carboxylate</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=57-22-7">57-22-7</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/5978">5978</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=6785">6785</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/DB00541">DB00541</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.5758.html">5758</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/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/5J49Q6B70F">5J49Q6B70F</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/D08679">D08679</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:28445">CHEBI:28445</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/ChEMBL303560">ChEMBL303560</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/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/DTXSID1032278">DTXSID1032278</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408977#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/100.000.289">100.000.289</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408977#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>46</sub><span title="Hydrogen">H</span><sub>56</sub><span title="Nitrogen">N</span><sub>4</sub><span title="Oxygen">O</span><sub>10</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="7002824972000000000♠"></span>824.972</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=CC%5BC%40%40%5D1%28C%5BC%40%40H%5D2C%5BC%40%40%5D%28C3%3DC%28CCN%28C2%29C1%29C4%3DCC%3DCC%3DC4N3%29%28C5%3DC%28C%3DC6C%28%3DC5%29%5BC%40%5D78CCN9%5BC%40H%5D7%5BC%40%40%5D%28C%3DCC9%29%28%5BC%40H%5D%28%5BC%40%40%5D%28%5BC%40%40H%5D8N6C%3DO%29%28C%28%3DO%29OC%29O%29OC%28%3DO%29C%29CC%29OC%29C%28%3DO%29OC%29O">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CC[C@@]1(C[C@@H]2C[C@@](C3=C(CCN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C=O)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC)O</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C46H56N4O10/c1-7-42(55)22-28-23-45(40(53)58-5,36-30(14-18-48(24-28)<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:OGWKCGZFUXNPDA-XQKSVPLYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=461759697&page2=Vincristine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Vincristine</b>, also known as <b>leurocristine</b> and marketed under the brand name <b>Oncovin</b> among others, is a <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a> medication used to treat a number of types of <a href="/wiki/Cancer" title="Cancer">cancer</a>.<sup id="cite_ref-AHFS2015_5-0" class="reference"><a href="#cite_note-AHFS2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> This includes <a href="/wiki/Acute_lymphocytic_leukemia" class="mw-redirect" title="Acute lymphocytic leukemia">acute lymphocytic leukemia</a>, <a href="/wiki/Acute_myeloid_leukemia" title="Acute myeloid leukemia">acute myeloid leukemia</a>, <a href="/wiki/Hodgkin%27s_disease" class="mw-redirect" title="Hodgkin's disease">Hodgkin's disease</a>, <a href="/wiki/Neuroblastoma" title="Neuroblastoma">neuroblastoma</a>, and <a href="/wiki/Small_cell_lung_cancer" class="mw-redirect" title="Small cell lung cancer">small cell lung cancer</a> among others.<sup id="cite_ref-AHFS2015_5-1" class="reference"><a href="#cite_note-AHFS2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is given intravenously.<sup id="cite_ref-AHFS2015_5-2" class="reference"><a href="#cite_note-AHFS2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Most people experience some side effects from vincristine treatment.<sup id="cite_ref-AHFS2015_5-3" class="reference"><a href="#cite_note-AHFS2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Commonly it causes a change in sensation, hair loss, constipation, difficulty walking, and headaches.<sup id="cite_ref-AHFS2015_5-4" class="reference"><a href="#cite_note-AHFS2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Serious side effects may include <a href="/wiki/Neuropathic_pain" title="Neuropathic pain">neuropathic pain</a>, lung damage, or <a href="/wiki/Leukopenia" title="Leukopenia">low white blood cells</a> which increases the risk of infection.<sup id="cite_ref-AHFS2015_5-5" class="reference"><a href="#cite_note-AHFS2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Use during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> may result in <a href="/wiki/Birth_defects" class="mw-redirect" title="Birth defects">birth defects</a>.<sup id="cite_ref-AHFS2015_5-6" class="reference"><a href="#cite_note-AHFS2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It works by <a href="/wiki/Mitotic_inhibitor" title="Mitotic inhibitor">stopping cells from dividing properly</a>.<sup id="cite_ref-AHFS2015_5-7" class="reference"><a href="#cite_note-AHFS2015-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is vital that it not be given <a href="/wiki/Intrathecal_administration" title="Intrathecal administration">intrathecally</a>, as this may kill.<sup id="cite_ref-ChotsampancharoenSripornsawanWongchanchailert2015_6-0" class="reference"><a href="#cite_note-ChotsampancharoenSripornsawanWongchanchailert2015-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Vincristine was first isolated in 1961.<sup id="cite_ref-Rav2011_7-0" class="reference"><a href="#cite_note-Rav2011-7"><span class="cite-bracket">[</span>7<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-WHO23rd_8-0" class="reference"><a href="#cite_note-WHO23rd-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Vinca_alkaloid" title="Vinca alkaloid">vinca alkaloid</a> that can be obtained from the Madagascar periwinkle <i><a href="/wiki/Catharanthus_roseus" title="Catharanthus roseus">Catharanthus roseus</a></i>.<sup id="cite_ref-Rav2011_7-1" class="reference"><a href="#cite_note-Rav2011-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vincristine is delivered via <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenous</a> <a href="/wiki/Route_of_administration" title="Route of administration">infusion</a> for use in various types of <a href="/wiki/Chemotherapy_regimens" class="mw-redirect" title="Chemotherapy regimens">chemotherapy regimens</a>.<sup id="cite_ref-MD_3-4" class="reference"><a href="#cite_note-MD-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Its main uses are in non-Hodgkin's <a href="/wiki/Lymphoma" title="Lymphoma">lymphoma</a> as part of the chemotherapy regimen <a href="/wiki/CHOP_(chemotherapy)" title="CHOP (chemotherapy)">CHOP</a> R-CVP, <a href="/wiki/Hodgkin%27s_lymphoma" class="mw-redirect" title="Hodgkin's lymphoma">Hodgkin's lymphoma</a> as part of MOPP, COPP, BEACOPP, or the less popular <a href="/wiki/Stanford_V" title="Stanford V">Stanford V</a> chemotherapy regimen in <a href="/wiki/Acute_lymphoblastic_leukemia" title="Acute lymphoblastic leukemia">acute lymphoblastic leukemia</a> (ALL), and in treatment for <a href="/wiki/Nephroblastoma" class="mw-redirect" title="Nephroblastoma">nephroblastoma</a> as well as the chemotherapy regimen VDC-IE for <a href="/wiki/Ewing%27s_Sarcoma" class="mw-redirect" title="Ewing's Sarcoma">Ewing's Sarcoma</a>. <sup id="cite_ref-MD_3-5" class="reference"><a href="#cite_note-MD-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is also used to induce remission in ALL with <a href="/wiki/Dexamethasone" title="Dexamethasone">dexamethasone</a> and L-<a href="/wiki/Asparaginase" title="Asparaginase">asparaginase</a>, and in combination with <a href="/wiki/Prednisone" title="Prednisone">prednisone</a> to treat childhood leukemia.<sup id="cite_ref-MD_3-6" class="reference"><a href="#cite_note-MD-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Vincristine is occasionally used as an <a href="/wiki/Immunosuppressant" class="mw-redirect" title="Immunosuppressant">immunosuppressant</a>, for example, in treating <a href="/wiki/Thrombotic_thrombocytopenic_purpura" title="Thrombotic thrombocytopenic purpura">thrombotic thrombocytopenic purpura</a> (TTP) or chronic <a href="/wiki/Idiopathic_thrombocytopenic_purpura" class="mw-redirect" title="Idiopathic thrombocytopenic purpura">idiopathic thrombocytopenic purpura</a> (ITP).<sup id="cite_ref-MD_3-7" class="reference"><a href="#cite_note-MD-3"><span class="cite-bracket">[</span>3<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=Vincristine&action=edit&section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The main side effects of vincristine are <a href="/wiki/Chemotherapy-induced_peripheral_neuropathy" title="Chemotherapy-induced peripheral neuropathy">chemotherapy-induced peripheral neuropathy</a>, <a href="/wiki/Hyponatremia" title="Hyponatremia">hyponatremia</a>, <a href="/wiki/Constipation" title="Constipation">constipation</a>, and <a href="/wiki/Alopecia" class="mw-redirect" title="Alopecia">hair loss</a>. </p><p>Vincristine-induced neuropathy is the main dose-limiting side effect.<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> Chemotherapy-induced peripheral neuropathy can be severe, and may be a reason to reduce or avoid using vincristine. The symptoms are progressive and enduring tingling numbness, pain and hypersensitivity to cold, beginning in the hands and feet and sometimes affecting the arms and legs.<sup id="cite_ref-NCI_10-0" class="reference"><a href="#cite_note-NCI-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> One of the first symptoms of peripheral neuropathy is <a href="/wiki/Foot_drop" title="Foot drop">foot drop</a>: A person with a family history of foot drop and/or <a href="/wiki/Charcot-Marie-Tooth_disease" class="mw-redirect" title="Charcot-Marie-Tooth disease">Charcot-Marie-Tooth disease</a> (CMT) should avoid vincristine.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> A 2021 study has suggested that <a href="/wiki/Anakinra" title="Anakinra">anakinra</a> can reduce the neuropathy.<sup id="cite_ref-starabova_12-0" class="reference"><a href="#cite_note-starabova-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-queensland_13-0" class="reference"><a href="#cite_note-queensland-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Accidental injection of vinca alkaloids into the spinal canal (<a href="/wiki/Intrathecal" class="mw-redirect" title="Intrathecal">intrathecal</a> administration) is highly dangerous, with a mortality rate approaching 100 percent. The medical literature documents cases of ascending <a href="/wiki/Paralysis" title="Paralysis">paralysis</a> due to massive <a href="/wiki/Encephalopathy" title="Encephalopathy">encephalopathy</a> and spinal nerve <a href="/wiki/Demyelination" class="mw-redirect" title="Demyelination">demyelination</a>, accompanied by intractable pain, almost uniformly leading to death. Several patients have survived after aggressive and immediate intervention. Rescue treatments consist of washout of the <a href="/wiki/Cerebrospinal_fluid" title="Cerebrospinal fluid">cerebrospinal fluid</a> and administration of protective medications.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Children may do better following this injury. One child, who was aggressively treated at the time of the injection, recovered almost completely with only mild neurological deficits.<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> A significant series of inadvertent intrathecal vincristine administration occurred in <a href="/wiki/China" title="China">China</a> in 2007 when batches of <a href="/wiki/Cytarabine" title="Cytarabine">cytarabine</a> and <a href="/wiki/Methotrexate" title="Methotrexate">methotrexate</a> (both often used intrathecally) manufactured by the company Shanghai Hualian were found to be contaminated with vincristine.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>The overuse of vincristine may also lead to <a href="/wiki/Drug_resistance" title="Drug resistance">drug resistance</a> by overexpression of the <a href="/wiki/P-glycoprotein" title="P-glycoprotein">p-glycoprotein</a> pump (Pgp). There is an attempt to overcome resistance by the addition of derivatives and substituents to the vincristine molecule.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=3" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vincristine works partly by binding to the <a href="/wiki/Tubulin" title="Tubulin">tubulin</a> protein, stopping the tubulin dimers from polymerizing to form microtubules, causing the cell to be unable to separate its <a href="/wiki/Chromosome" title="Chromosome">chromosomes</a> during the <a href="/wiki/Metaphase" title="Metaphase">metaphase</a>.<sup id="cite_ref-Elsevier_18-0" class="reference"><a href="#cite_note-Elsevier-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The cell then undergoes <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>.<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> The vincristine molecule inhibits <a href="/wiki/Leukocyte" class="mw-redirect" title="Leukocyte">leukocyte</a> production and maturation.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> A downside, however, to vincristine is that it does not only affect the division of cancer cells. It affects all rapidly dividing cell types, making it necessary for the very specific administration of the drug.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=4" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The natural extraction of vincristine from <i>Catharanthus roseus</i> is produced at a percent yield of less than 0.0003%. For this reason, alternate methods to produce synthetic vincristine are being used.<sup id="cite_ref-Stereocontrolled_total_synthesis_of_22-0" class="reference"><a href="#cite_note-Stereocontrolled_total_synthesis_of-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> Vincristine is created through the semi-synthesis coupling of indole alkaloids <a href="/wiki/Vindoline" title="Vindoline">vindoline</a> and <a href="/wiki/Catharanthine" title="Catharanthine">catharanthine</a> in the vinca plant.<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> It can also now be synthesized through a stereocontrolled total synthesis technique which retains the correct stereochemistry at C18' and C2'. The absolute stereochemistry at these carbons is responsible for vincristine's anticancer activity.<sup id="cite_ref-Stereocontrolled_total_synthesis_of_22-1" class="reference"><a href="#cite_note-Stereocontrolled_total_synthesis_of-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Liposome" title="Liposome">liposome</a> encapsulation of vincristine enhances the efficacy of the vincristine drug while simultaneously decreasing the <a href="/wiki/Neurotoxicity" title="Neurotoxicity">neurotoxicity</a> associated with it. Liposome encapsulation increases vincristine's plasma concentration and circulation lifetime in the body, and allows the drug to enter cells more easily.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=5" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Having been used as a folk remedy for centuries, studies in the 1950s revealed that the rosy periwinkle <i><a href="/wiki/Catharanthus_roseus" title="Catharanthus roseus">Catharanthus roseus</a></i> contained over 120 alkaloids, many of which are biologically active, the two most significant being vincristine and <a href="/wiki/Vinblastine" title="Vinblastine">vinblastine</a>. Its use as an anti-tumor, anti-mutagenic agent is well documented in the ancient <a href="/wiki/Ayurveda" title="Ayurveda">Ayurveda</a> system of medicine and in the folk culture of <a href="/wiki/Madagascar" title="Madagascar">Madagascar</a> and <a href="/wiki/Southern_Africa" title="Southern Africa">Southern Africa</a>.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> It was not found to be anti-diabetic in double blinded controlled studies.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> While initial studies for its use in <a href="/wiki/Diabetes_mellitus" class="mw-redirect" title="Diabetes mellitus">diabetes mellitus</a> were disappointing, the discovery that it caused <a href="/wiki/Myelosuppression" class="mw-redirect" title="Myelosuppression">myelosuppression</a> (decreased activity of the bone marrow) led to its study in mice with <a href="/wiki/Leukemia" title="Leukemia">leukemia</a>, whose lifespan was prolonged by the use of a vinca preparation. Treatment of the ground plant with <a href="/wiki/Hexane" title="Hexane">Skellysolve-B</a> (hexane), followed by dilute <a href="/wiki/Tartaric_acid" title="Tartaric acid">tartaric acid</a> and <a href="/wiki/Benzene" title="Benzene">benzene</a> extraction, provided an active fraction. This fraction was further <a href="/wiki/Chromatography" title="Chromatography">chromatographed</a> on deactivated <a href="/wiki/Aluminium_oxide" title="Aluminium oxide">aluminium oxide</a> using <a href="/wiki/Chloroform" title="Chloroform">trichloromethane</a> and benzene, and separation by pH using extraction with various buffers to yield vincristine.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Vincristine was approved by the US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) in July 1963 under the trade name Oncovin and was marketed by <a href="/wiki/Eli_Lilly_and_Company" title="Eli Lilly and Company">Eli Lilly and Company</a>. The drug was initially developed by a team at Lilly Research Laboratories in <a href="/wiki/Indianapolis" title="Indianapolis">Indianapolis</a> where it was demonstrated that vincristine cured artificially induced leukemia in mice and remission of acute leukemias of childhood.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>Production of vincristine required one ton of dried periwinkle leaves to produce one ounce of vincristine. The periwinkle was grown on a ranch in Texas.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=6" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Suppliers">Suppliers</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=7" title="Edit section: Suppliers"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Until recently, two <a href="/wiki/Generic_drug" title="Generic drug">generic drug</a> makers were suppliers of vincristine in the United States: <a href="/wiki/Teva_Pharmaceuticals" title="Teva Pharmaceuticals">Teva</a> and <a href="/wiki/Pfizer" title="Pfizer">Pfizer</a>. In 2019 Teva stopped producing vincristine, leaving Pfizer as the only company in production.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2019)">citation needed</span></a></i>]</sup> Teva has said that they will restart production, and expect it to be available in 2020.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Shortage">Shortage</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=8" title="Edit section: Shortage"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In October 2019 an impending shortage was reported; no adequate substitute is known for treating childhood-cancers.<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> By 2022, the shortage of vincristine continued.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Controversy">Controversy</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=9" title="Edit section: Controversy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Pharmaceutical_bioprospecting">Pharmaceutical bioprospecting</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=10" title="Edit section: Pharmaceutical bioprospecting"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vincristine's origins are debated as an example of <a href="/wiki/Bioprospecting" title="Bioprospecting">pharmaceutical bioprospecting</a> in the fields of <a href="/wiki/Ethnobotany" title="Ethnobotany">ethnobotany</a> and <a href="/wiki/Ethnomedicine" title="Ethnomedicine">ethnomedicine</a>. Some consider the <i><a href="/wiki/Catharanthus_roseus" title="Catharanthus roseus">Catharanthus roseus</a></i> plant from which vincristine is derived, and its <a href="/wiki/Folk_medicine" class="mw-redirect" title="Folk medicine">folk remedies</a> to be endemic to Madagascar, and that Madagascar was denied royalties from vincristine sales.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> However, <i>Catharanthus roseus</i> has a documented history in folk medicine treatments in other locations. In 1963, Lilly researchers acknowledged that the plant was used in Brazil to treat hemorrhage, scurvy, toothaches, and chronic wounds; in the British West Indies to treat diabetic ulcers; and in the Philippines and South Africa as an oral hypoglycemic agent – but not as a treatment for cancer.<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> </p><p><i>Catharanthus roseus</i> has been a cosmopolitan species since before the <a href="/wiki/Industrial_Revolution" title="Industrial Revolution">Industrial Revolution</a> and the plant's use in folk remedies suggested general bioactivity for diabetes treatment, not cancer. In the mid-eighteenth century, botanist Judith Sumner recorded the arrival of <i>Catharanthus roseus</i> at London's <a href="/wiki/Chelsea_Physic_Garden" title="Chelsea Physic Garden">Chelsea Physic Garden</a> from the <a href="/wiki/Jardin_des_plantes" title="Jardin des plantes">Jardin des plantes</a> in Paris. It's unclear how the plant first arrived in Paris and the details of its origins in Madagascar beyond reports of its transport from Madagascar by early European explorers. Vincristine was initially distributed at cost to increase accessibility, though later switched to a for-profit model to recover the costs of production and development. According to Michael Brown, vincristine may not be a tidy example of pharmaceutical bioprospecting, but it demonstrates how pharmaceuticals with a history of use in folk medicine have intellectual property claims which are difficult to untangle.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Vincristine_and_confusion_with_other_drugs_in_administration">Vincristine and confusion with other drugs in administration</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=11" title="Edit section: Vincristine and confusion with other drugs in administration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vincristine has been involved in a number of medical errors. Multiple instances of vincristine having been administered improperly, after having been confused with other drugs, have occurred. If delivered into the spine (intrathecal) it causes paralysis and usually death. </p><p>In 2003 two Australian oncology pharmacists recommended a solution. The suggested procedure is to prepare and administer vincristine in a small volume mini-bag rather than a syringe thus physically preventing the vincristine syringe being accidentally attached to a spinal needle. Acceptance of this safer procedure has been slow.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=12" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 2012, the FDA approved a liposomal formulation of vincristine branded as Marqibo.<sup id="cite_ref-37" class="reference"><a href="#cite_note-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><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> Marqibo was voluntarily withdrawn from the US market in November, 2021.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>A nano-particle bound version of vincristine was under development as of 2014.<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> </p><p>In 1995 and 2006 Malagasy <a href="/wiki/Agronomists" class="mw-redirect" title="Agronomists">agronomists</a> and American <a href="/wiki/Political_ecologists" class="mw-redirect" title="Political ecologists">political ecologists</a> studied the production of <i>Catharanthus roseus</i> around <a href="/wiki/Fort_Dauphin_(Madagascar)" class="mw-redirect" title="Fort Dauphin (Madagascar)">Fort Dauphin</a> and <a href="/wiki/Ambovombe-Androy" title="Ambovombe-Androy">Ambovombe</a> and its export as a natural source of the alkaloids used to make vincristine, vinblastine and other <a href="/wiki/Vinca_alkaloid" title="Vinca alkaloid">vinca alkaloid</a> cancer drugs. Their research focused on the wild collection of periwinkle roots and leaves from roadsides and fields and its industrial cultivation on large farms.<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><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><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> </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=Vincristine&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-DictionaryVincristine-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-DictionaryVincristine_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://dictionary.reference.com/browse/Vincristine">"Vincristine"</a>. <i>Dictionary.com</i>. 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Retrieved <span class="nowrap">19 June</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Federal+Register&rft.atitle=Acrotech+Biopharma+LLC%3B+Withdrawal+of+Approval+of+New+Drug+Application+for+MARQIBO+%28VinCRIStine+Sulfate+LIPOSOME+Injection%29%2C+5+milligrams%2F5+milliliters&rft.date=2022-05-02&rft_id=https%3A%2F%2Fwww.federalregister.gov%2Fdocuments%2F2022%2F05%2F02%2F2022-09235%2Facrotech-biopharma-llc-withdrawal-of-approval-of-new-drug-application-for-marqibo-vincristine&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVincristine" class="Z3988"></span></span> </li> <li id="cite_note-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-41">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://seekingalpha.com/article/2658685-bind-therapeutics-bind-ceo-scott-minick-on-q3-2014-results-earnings-call-transcript?part=single">Bind Therapeutics conference call of Nov 6, 2014</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160303230202/http://seekingalpha.com/article/2658685-bind-therapeutics-bind-ceo-scott-minick-on-q3-2014-results-earnings-call-transcript?part=single">Archived</a> 2016-03-03 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAndriamanalintsoa1995" class="citation book cs1 cs1-prop-foreign-lang-source">Andriamanalintsoa, Jean Joseph (1995). <a rel="nofollow" class="external text" href="http://madadoc.irenala.edu.mg/documents/v4312_MEM%2012099.pdf"><i>Contribution a l'etude de la producition de la pervenche de Madagascar ou Catharanthus roseus, Cas d' Ambovombe, d'Amboasary-sud, de Beloha et Tsihombe</i></a> <span class="cs1-format">(PhD Dissertation)</span> (in French). Antananarivo, Madagascar: Universityersité d'Antananarivo, Ecole Superieur des Sciences Agronomiques.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Contribution+a+l%27etude+de+la+producition+de+la+pervenche+de+Madagascar+ou+Catharanthus+roseus%2C+Cas+d%27+Ambovombe%2C+d%27Amboasary-sud%2C+de+Beloha+et+Tsihombe&rft.place=Antananarivo%2C+Madagascar&rft.pub=Universityersit%C3%A9+d%27Antananarivo%2C+Ecole+Superieur+des+Sciences+Agronomiques&rft.date=1995&rft.aulast=Andriamanalintsoa&rft.aufirst=Jean+Joseph&rft_id=http%3A%2F%2Fmadadoc.irenala.edu.mg%2Fdocuments%2Fv4312_MEM%252012099.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVincristine" class="Z3988"></span></span> </li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNeimark2009" class="citation book cs1">Neimark, Benjamin (2009). "At the "Pharm" gate: The case study of the rosy periwinkle (Catharanthus roseus)". <a rel="nofollow" class="external text" href="https://doi.org/doi:10.7282/T3WD40Q7"><i>Industrial Heartlands of Nature: The Political Economy of Biological Prospecting in Madagascar</i></a> <span class="cs1-format">(PhD Dissertation)</span>. New Brunswick: Rutgers, The State University of New Jersey. p. 70-112. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.7282%2FT3WD40Q7">10.7282/T3WD40Q7</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=At+the+%22Pharm%22+gate%3A+The+case+study+of+the+rosy+periwinkle+%28Catharanthus+roseus%29&rft.btitle=Industrial+Heartlands+of+Nature%3A+The+Political+Economy+of+Biological+Prospecting+in+Madagascar&rft.place=New+Brunswick&rft.pages=70-112&rft.pub=Rutgers%2C+The+State+University+of+New+Jersey&rft.date=2009&rft_id=info%3Adoi%2F10.7282%2FT3WD40Q7&rft.aulast=Neimark&rft.aufirst=Benjamin&rft_id=https%3A%2F%2Fdoi.org%2Fdoi%3A10.7282%2FT3WD40Q7&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVincristine" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFNeimark2012" class="citation journal cs1">Neimark, Ben (2012). <a rel="nofollow" class="external text" href="https://www.tandfonline.com/doi/citedby/10.1080/03066150.2012.666975?scroll=top&needAccess=true&role=tab">"Green grabbing at the 'pharm' gate: rosy periwinkle production in southern Madagascar"</a>. <i>The Journal of Peasant Studies</i>. <b>39</b> (2): 423-445. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F03066150.2012.666975">10.1080/03066150.2012.666975</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:153584071">153584071</a><span class="reference-accessdate">. Retrieved <span class="nowrap">14 July</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Peasant+Studies&rft.atitle=Green+grabbing+at+the+%27pharm%27+gate%3A+rosy+periwinkle+production+in+southern+Madagascar&rft.volume=39&rft.issue=2&rft.pages=423-445&rft.date=2012&rft_id=info%3Adoi%2F10.1080%2F03066150.2012.666975&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A153584071%23id-name%3DS2CID&rft.aulast=Neimark&rft.aufirst=Ben&rft_id=https%3A%2F%2Fwww.tandfonline.com%2Fdoi%2Fcitedby%2F10.1080%2F03066150.2012.666975%3Fscroll%3Dtop%26needAccess%3Dtrue%26role%3Dtab&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVincristine" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vincristine&action=edit&section=14" 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/vincristine">"Vincristine"</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=Vincristine&rft_id=https%3A%2F%2Fdruginfo.nlm.nih.gov%2Fdrugportal%2Fname%2Fvincristine&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVincristine" class="Z3988"></span></li> <li><a rel="nofollow" class="external text" href="http://www.chm.bris.ac.uk/webprojects2002/jjones/Content/vincristine.htm">Vincristine and vinblastine</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190328074038/http://www.chm.bris.ac.uk/webprojects2002/jjones/Content/vincristine.htm">Archived</a> 2019-03-28 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20070915032627/http://biotech.icmb.utexas.edu/botany/perihist.html">Description and Natural History of the Periwinkle</a></li> <li><a rel="nofollow" class="external text" href="https://www.organic-chemistry.org/Highlights/2006/05June.shtm">The Boger Route to (−)-Vindoline</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 ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output 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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 class="mw-selflink selflink">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 href="/wiki/Cisplatin" title="Cisplatin">Cisplatin</a><sup>#</sup></li> <li><a href="/wiki/Dicycloplatin" title="Dicycloplatin">Dicycloplatin</a></li> <li><a href="/wiki/Nedaplatin" title="Nedaplatin">Nedaplatin</a></li> <li><a href="/wiki/Oxaliplatin" title="Oxaliplatin">Oxaliplatin</a><sup>#</sup></li> <li><a href="/wiki/Satraplatin" title="Satraplatin">Satraplatin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkylating_antineoplastic_agent#Nonclassical" title="Alkylating antineoplastic agent">Nonclassical</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Altretamine" title="Altretamine">Altretamine</a></li> <li><i><a href="/wiki/Hydrazine" title="Hydrazine">Hydrazines</a></i> (<a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a><sup>#</sup>)</li> <li><a href="/wiki/Etoglucid" title="Etoglucid">Etoglucid</a></li> <li><a href="/wiki/Mitobronitol" title="Mitobronitol">Mitobronitol</a></li> <li><a href="/wiki/Pipobroman" title="Pipobroman">Pipobroman</a></li> <li><i><a href="/wiki/Triazene" title="Triazene">Triazenes</a></i> (<a href="/wiki/Dacarbazine" title="Dacarbazine">Dacarbazine</a><sup>#</sup></li> <li><a href="/wiki/Mitozolomide" title="Mitozolomide">Mitozolomide</a><sup>§</sup></li> <li><a href="/wiki/Temozolomide" title="Temozolomide">Temozolomide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">Intercalation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a> (<a href="/wiki/Dactinomycin" title="Dactinomycin">Dactinomycin</a><sup>#</sup></li> <li><a href="/wiki/Bleomycin" title="Bleomycin">Bleomycin</a><sup>#</sup></li> <li><a href="/wiki/Mitomycins" title="Mitomycins">Mitomycins</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Photosensitizer" title="Photosensitizer">Photosensitizers</a>/<a href="/wiki/Photodynamic_therapy" title="Photodynamic therapy">PDT</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminolevulinic_acid" title="Aminolevulinic acid">Aminolevulinic acid</a></li> <li><a href="/wiki/Efaproxiral" title="Efaproxiral">Efaproxiral</a></li> <li><a href="/wiki/Methyl_aminolevulinate" title="Methyl aminolevulinate">Methyl aminolevulinate</a></li> <li><a href="/wiki/Padeliporfin" title="Padeliporfin">Padeliporfin</a></li> <li><i><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrin derivatives</a></i> (<a href="/wiki/Porfimer_sodium" title="Porfimer sodium">Porfimer sodium</a></li> <li><a href="/wiki/Talaporfin" title="Talaporfin">Talaporfin</a></li> <li><a href="/wiki/Temoporfin" title="Temoporfin">Temoporfin</a></li> <li><a href="/wiki/Verteporfin" title="Verteporfin">Verteporfin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">Enzyme inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Farnesyltransferase_inhibitor" title="Farnesyltransferase inhibitor">FI</a></i> (<a href="/wiki/Tipifarnib" title="Tipifarnib">Tipifarnib</a><sup>§</sup>)</li> <li><i><a href="/wiki/Cyclin-dependent_kinase" title="Cyclin-dependent kinase">CDK</a> <a href="/wiki/Protein_kinase_inhibitor" title="Protein kinase inhibitor">inhibitors</a></i> (<a href="/wiki/Abemaciclib" title="Abemaciclib">Abemaciclib</a></li> <li><a href="/wiki/Alvocidib" title="Alvocidib">Alvocidib</a><sup>†</sup></li> <li><a href="/wiki/Palbociclib" title="Palbociclib">Palbociclib</a></li> <li><a href="/wiki/Ribociclib" title="Ribociclib">Ribociclib</a></li> <li><a href="/wiki/Seliciclib" title="Seliciclib">Seliciclib</a><sup>†</sup>)</li> <li><i><a href="/wiki/Proteasome_inhibitor" title="Proteasome inhibitor">PrI</a></i> <ul><li><a href="/wiki/Bortezomib" title="Bortezomib">Bortezomib</a></li> <li><a href="/wiki/Carfilzomib" title="Carfilzomib">Carfilzomib</a></li> <li><a href="/wiki/Oprozomib" title="Oprozomib">Oprozomib</a></li> <li><a href="/wiki/Ixazomib" title="Ixazomib">Ixazomib</a></li></ul></li> <li><i><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">PhI</a></i> (<a href="/wiki/Anagrelide" title="Anagrelide">Anagrelide</a>)</li> <li><i><a href="/wiki/IMP_dehydrogenase" class="mw-redirect" title="IMP dehydrogenase">IMPDI</a></i> (<a href="/wiki/Tiazofurin" title="Tiazofurin">Tiazofurin</a><sup>§</sup>)</li> <li><i><a href="/wiki/Lipoxygenase_inhibitor" class="mw-redirect" title="Lipoxygenase inhibitor">LI</a></i> (<a href="/wiki/Masoprocol" title="Masoprocol">Masoprocol</a>)</li> <li><i><a href="/wiki/PARP_inhibitor" title="PARP inhibitor">PARP inhibitor</a></i> (<a href="/wiki/Fuzuloparib" title="Fuzuloparib">Fuzuloparib</a></li> <li><a href="/wiki/Niraparib" title="Niraparib">Niraparib</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+abiraterone acetate</a></li> <li><a href="/wiki/Olaparib" title="Olaparib">Olaparib</a></li> <li><a href="/wiki/Rucaparib" title="Rucaparib">Rucaparib</a>)</li> <li><i><a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">HDAC</a></i> (<a href="/wiki/Belinostat" title="Belinostat">Belinostat</a></li> <li><a href="/wiki/Entinostat" title="Entinostat">Entinostat</a></li> <li><a href="/wiki/Panobinostat" title="Panobinostat">Panobinostat</a></li> <li><a href="/wiki/Romidepsin" title="Romidepsin">Romidepsin</a></li> <li><a href="/wiki/Vorinostat" title="Vorinostat">Vorinostat</a>)</li> <li><i><a href="/wiki/Phosphoinositide_3-kinase_inhibitor" title="Phosphoinositide 3-kinase inhibitor">PIKI</a> (Pi3K)</i> (<a href="/wiki/Alpelisib" title="Alpelisib">Alpelisib</a></li> <li><a href="/wiki/Copanlisib" title="Copanlisib">Copanlisib</a><sup>‡</sup></li> <li><a href="/wiki/Duvelisib" title="Duvelisib">Duvelisib</a></li> <li><a href="/wiki/Idelalisib" title="Idelalisib">Idelalisib</a></li> <li><a href="/wiki/Inavolisib" title="Inavolisib">Inavolisib</a></li> <li><a href="/wiki/Umbralisib" title="Umbralisib">Umbralisib</a><sup>‡</sup>)</li> <li><i><a href="/wiki/Isocitrate_dehydrogenase" title="Isocitrate dehydrogenase">IDH</a></i> (<a href="/wiki/Enasidenib" title="Enasidenib">Enasidenib</a></li> <li><a href="/wiki/Ivosidenib" title="Ivosidenib">Ivosidenib</a></li> <li><a href="/wiki/Olutasidenib" title="Olutasidenib">Olutasidenib</a></li> <li><a href="/wiki/Vorasidenib" title="Vorasidenib">Vorasidenib</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Receptor antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Endothelin_receptor_antagonist" title="Endothelin receptor antagonist">ERA</a></i> (<a href="/wiki/Atrasentan" title="Atrasentan">Atrasentan</a>)</li> <li><i><a href="/wiki/Retinoid_X_receptor" title="Retinoid X receptor">Retinoid X receptor</a></i> (<a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a>)</li> <li><i><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroid</a></i> (<a href="/wiki/Testolactone" title="Testolactone">Testolactone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/ungrouped</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adagrasib" title="Adagrasib">Adagrasib</a></li> <li><a href="/wiki/Aflibercept" title="Aflibercept">Aflibercept</a></li> <li><a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">Arsenic trioxide</a></li> <li><i><a href="/wiki/Asparagine" title="Asparagine">Asparagine depleters</a></i> (<a href="/wiki/Asparaginase" title="Asparaginase">Asparaginase</a><sup>#</sup>/<a href="/wiki/Pegaspargase" title="Pegaspargase">Pegaspargase</a>)</li> <li><a href="/wiki/Axicabtagene_ciloleucel" title="Axicabtagene ciloleucel">Axicabtagene ciloleucel</a></li> <li><a href="/wiki/Belzutifan" title="Belzutifan">Belzutifan</a></li> <li><a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a></li> <li><a href="/wiki/Brexucabtagene_autoleucel" title="Brexucabtagene autoleucel">Brexucabtagene autoleucel</a></li> <li><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a></li> <li><a href="/wiki/Ciltacabtagene_autoleucel" title="Ciltacabtagene autoleucel">Ciltacabtagene autoleucel</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Denileukin_diftitox" title="Denileukin diftitox">Denileukin diftitox</a></li> <li><a href="/wiki/Eflornithine" title="Eflornithine">Eflornithine</a></li> <li><a href="/wiki/Elesclomol" title="Elesclomol">Elesclomol</a><sup>§</sup></li> <li><a href="/wiki/Elsamitrucin" title="Elsamitrucin">Elsamitrucin</a></li> <li><a href="/wiki/Epacadostat" title="Epacadostat">Epacadostat</a></li> <li><a href="/wiki/Eribulin" title="Eribulin">Eribulin</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine</a></li> <li><a href="/wiki/Glasdegib" title="Glasdegib">Glasdegib</a></li> <li><a href="/wiki/Idecabtagene_vicleucel" title="Idecabtagene vicleucel">Idecabtagene vicleucel</a></li> <li><a href="/wiki/Imetelstat" title="Imetelstat">Imetelstat</a></li> <li><a href="/wiki/Lifileucel" title="Lifileucel">Lifileucel</a></li> <li><a href="/wiki/Lisocabtagene_maraleucel" title="Lisocabtagene maraleucel">Lisocabtagene maraleucel</a></li> <li><a href="/wiki/Lonidamine" title="Lonidamine">Lonidamine</a></li> <li><a href="/wiki/Lucanthone" title="Lucanthone">Lucanthone</a></li> <li><a href="/wiki/Lurbinectedin" title="Lurbinectedin">Lurbinectedin</a></li> <li><a href="/wiki/Mitoguazone" title="Mitoguazone">Mitoguazone</a></li> <li><a href="/wiki/Mitotane" title="Mitotane">Mitotane</a></li> <li><a href="/wiki/Nadofaragene_firadenovec" title="Nadofaragene firadenovec">Nadofaragene firadenovec</a></li> <li><a href="/wiki/Navitoclax" title="Navitoclax">Navitoclax</a></li> <li><a href="/wiki/Obecabtagene_autoleucel" title="Obecabtagene autoleucel">Obecabtagene autoleucel</a></li> <li><a href="/wiki/Oblimersen" title="Oblimersen">Oblimersen</a><sup>†</sup></li> <li><a href="/wiki/Omacetaxine_mepesuccinate" title="Omacetaxine mepesuccinate">Omacetaxine mepesuccinate</a></li> <li><a href="/wiki/Plitidepsin" title="Plitidepsin">Plitidepsin</a></li> <li><a href="/wiki/Tabelecleucel" title="Tabelecleucel">Tabelecleucel</a></li> <li><i><a href="/wiki/Retinoid" title="Retinoid">Retinoids</a></i> (<a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a><sup>#</sup>)</li> <li><a href="/wiki/Selinexor" title="Selinexor">Selinexor</a></li> <li><a href="/w/index.php?title=Sitimagene_ceradenovec&action=edit&redlink=1" class="new" title="Sitimagene ceradenovec (page does not exist)">Sitimagene ceradenovec</a></li> <li><a href="/wiki/Sotorasib" title="Sotorasib">Sotorasib</a></li> <li><a href="/wiki/Tagraxofusp" title="Tagraxofusp">Tagraxofusp</a></li> <li><a href="/wiki/Talimogene_laherparepvec" title="Talimogene laherparepvec">Talimogene laherparepvec</a></li> <li><a href="/wiki/Tazemetostat" title="Tazemetostat">Tazemetostat</a></li> <li><a href="/wiki/Tebentafusp" title="Tebentafusp">Tebentafusp</a></li> <li><a href="/wiki/Tiazofurine" class="mw-redirect" title="Tiazofurine">Tiazofurine</a></li> <li><a href="/wiki/Tigilanol_tiglate" title="Tigilanol tiglate">Tigilanol tiglate</a></li> <li><a href="/wiki/Tisagenlecleucel" title="Tisagenlecleucel">Tisagenlecleucel</a></li> <li><a href="/wiki/Trabectedin" title="Trabectedin">Trabectedin</a></li> <li><a href="/wiki/Veliparib" title="Veliparib">Veliparib</a></li> <li><a href="/wiki/Venetoclax" title="Venetoclax">Venetoclax</a></li> <li><a href="/w/index.php?title=Verdinexor&action=edit&redlink=1" class="new" title="Verdinexor (page does not exist)">Verdinexor</a></li> <li><a href="/wiki/Vosaroxin" title="Vosaroxin">Vosaroxin</a></li></ul> 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