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cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle History subsection</span> </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Initial_cancer_research" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Initial_cancer_research"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Initial cancer research</span> </div> </a> <ul id="toc-Initial_cancer_research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-HIV/AIDS_research" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#HIV/AIDS_research"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>HIV/AIDS research</span> </div> </a> <ul id="toc-HIV/AIDS_research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Patent_filed_and_FDA_approval" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Patent_filed_and_FDA_approval"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Patent filed and FDA approval</span> </div> </a> <ul id="toc-Patent_filed_and_FDA_approval-sublist" class="vector-toc-list"> </ul> </li> </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> <ul id="toc-Society_and_culture-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">7</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">8</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Zidovudine</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 42 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-42" 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">42 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Sidovudien" title="Sidovudien – Afrikaans" lang="af" hreflang="af" data-title="Sidovudien" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B2%D9%8A%D8%AF%D9%88%D9%81%D9%88%D8%AF%D9%8A%D9%86" title="زيدوفودين – Arabic" lang="ar" hreflang="ar" data-title="زيدوفودين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B2%DB%8C%D8%AF%D9%88%D9%88%D8%AF%DB%8C%D9%86" title="زیدوودین – South Azerbaijani" lang="azb" hreflang="azb" data-title="زیدوودین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%9C%E0%A6%BF%E0%A6%A1%E0%A7%8B%E0%A6%AD%E0%A7%81%E0%A6%A1%E0%A6%BF%E0%A6%A8" title="জিডোভুডিন – Bangla" lang="bn" hreflang="bn" data-title="জিডোভুডিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Zidovudina" title="Zidovudina – Catalan" lang="ca" hreflang="ca" data-title="Zidovudina" 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/Sidofwdin" title="Sidofwdin – Welsh" lang="cy" hreflang="cy" data-title="Sidofwdin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Zidovudin" title="Zidovudin – Danish" lang="da" hreflang="da" data-title="Zidovudin" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Zidovudin" title="Zidovudin – German" lang="de" hreflang="de" data-title="Zidovudin" 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/Zidovudina" title="Zidovudina – Spanish" lang="es" hreflang="es" data-title="Zidovudina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Zidovudino" title="Zidovudino – Esperanto" lang="eo" hreflang="eo" data-title="Zidovudino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Zidobudina" title="Zidobudina – Basque" lang="eu" hreflang="eu" data-title="Zidobudina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B2%DB%8C%D8%AF%D9%88%D9%88%D8%AF%DB%8C%D9%86" title="زیدوودین – Persian" lang="fa" hreflang="fa" data-title="زیدوودین" 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/Zidovudine" title="Zidovudine – French" lang="fr" hreflang="fr" data-title="Zidovudine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Ais%C3%ADdit%C3%ADmid%C3%ADn" title="Aisíditímidín – Irish" lang="ga" hreflang="ga" data-title="Aisíditímidín" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%A7%80%EB%8F%84%EB%B6%80%EB%94%98" title="지도부딘 – Korean" lang="ko" hreflang="ko" data-title="지도부딘" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B6%D5%AB%D5%A4%D5%B8%D5%BE%D5%B8%D6%82%D5%A4%D5%AB%D5%B6" title="Զիդովուդին – Armenian" lang="hy" hreflang="hy" data-title="Զիդովուդին" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Zidovudino" title="Zidovudino – Ido" lang="io" hreflang="io" data-title="Zidovudino" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Zidovudin" title="Zidovudin – Indonesian" lang="id" hreflang="id" data-title="Zidovudin" 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/Azidotimidina" title="Azidotimidina – Italian" lang="it" hreflang="it" data-title="Azidotimidina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Zidovudin" title="Zidovudin – Hungarian" lang="hu" hreflang="hu" data-title="Zidovudin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Zidovudina" title="Zidovudina – Malay" lang="ms" hreflang="ms" data-title="Zidovudina" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%97%D0%B8%D0%B4%D0%BE%D0%B2%D1%83%D0%B4%D0%B8%D0%BD" title="Зидовудин – Mongolian" lang="mn" hreflang="mn" data-title="Зидовудин" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target"><span>Монгол</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Zidovudine" title="Zidovudine – Dutch" lang="nl" hreflang="nl" data-title="Zidovudine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B8%E3%83%89%E3%83%96%E3%82%B8%E3%83%B3" title="ジドブジン – Japanese" lang="ja" hreflang="ja" data-title="ジドブジン" 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-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Zidovudin" title="Zidovudin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Zidovudin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%9C%E0%AC%BF%E0%AC%A1%E0%AD%8B%E0%AC%AD%E0%AD%81%E0%AC%A1%E0%AC%BF%E0%AC%A8" title="ଜିଡୋଭୁଡିନ – Odia" lang="or" hreflang="or" data-title="ଜିଡୋଭୁଡିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-ps mw-list-item"><a href="https://ps.wikipedia.org/wiki/%D8%B2%D9%8A%DA%89%D9%88%D9%88%DA%89%D9%8A%D9%86" title="زيډووډين – Pashto" lang="ps" hreflang="ps" data-title="زيډووډين" data-language-autonym="پښتو" data-language-local-name="Pashto" class="interlanguage-link-target"><span>پښتو</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Azydotymidyna" title="Azydotymidyna – Polish" lang="pl" hreflang="pl" data-title="Azydotymidyna" 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/Zidovudina" title="Zidovudina – Portuguese" lang="pt" hreflang="pt" data-title="Zidovudina" 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/Zidovudin%C4%83" title="Zidovudină – Romanian" lang="ro" hreflang="ro" data-title="Zidovudină" 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%97%D0%B8%D0%B4%D0%BE%D0%B2%D1%83%D0%B4%D0%B8%D0%BD" title="Зидовудин – Russian" lang="ru" hreflang="ru" data-title="Зидовудин" 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/Zidovudin" title="Zidovudin – Slovenian" lang="sl" hreflang="sl" data-title="Zidovudin" 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/Zidovudin" title="Zidovudin – Serbian" lang="sr" hreflang="sr" data-title="Zidovudin" 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/Zidovudin" title="Zidovudin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Zidovudin" 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/Atsidotymidiini" title="Atsidotymidiini – Finnish" lang="fi" hreflang="fi" data-title="Atsidotymidiini" 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/AZT" title="AZT – Swedish" lang="sv" hreflang="sv" data-title="AZT" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%9C%E0%B0%BF%E0%B0%A1%E0%B1%8B%E0%B0%B5%E0%B1%81%E0%B0%A1%E0%B0%BF%E0%B0%A8%E0%B1%8D" title="జిడోవుడిన్ – Telugu" lang="te" hreflang="te" data-title="జిడోవుడిన్" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%8B%E0%B8%B4%E0%B9%82%E0%B8%94%E0%B8%A7%E0%B8%B9%E0%B8%94%E0%B8%B5%E0%B8%99" title="ซิโดวูดีน – Thai" lang="th" hreflang="th" data-title="ซิโดวูดีน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Zidovudin" title="Zidovudin – Turkish" lang="tr" hreflang="tr" data-title="Zidovudin" 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%90%D0%97%D0%A2" title="АЗТ – Ukrainian" lang="uk" hreflang="uk" data-title="АЗТ" 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/Zidovudine" title="Zidovudine – Vietnamese" lang="vi" hreflang="vi" data-title="Zidovudine" 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%BD%90%E5%A4%9A%E5%A4%AB%E5%AE%9A" title="齐多夫定 – Chinese" lang="zh" hreflang="zh" data-title="齐多夫定" 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/Q198504#sitelinks-wikipedia" 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.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">"AZT" redirects here. For other uses, see <a href="/wiki/AZT_(disambiguation)" class="mw-disambig" title="AZT (disambiguation)">AZT (disambiguation)</a>.</div> <p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Zidovudine">Zidovudine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Zidovudine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Zidovudine.svg/155px-Zidovudine.svg.png" decoding="async" width="155" height="168" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/32/Zidovudine.svg/233px-Zidovudine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/32/Zidovudine.svg/310px-Zidovudine.svg.png 2x" data-file-width="512" data-file-height="555" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="bg-transparent" typeof="mw:File"><a href="/wiki/File:Zidovudine-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Zidovudine-from-xtal-3D-bs-17.png/155px-Zidovudine-from-xtal-3D-bs-17.png" decoding="async" width="155" height="189" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Zidovudine-from-xtal-3D-bs-17.png/233px-Zidovudine-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d1/Zidovudine-from-xtal-3D-bs-17.png/310px-Zidovudine-from-xtal-3D-bs-17.png 2x" data-file-width="1801" data-file-height="2191" /></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;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Retrovir, others</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/zidovudine.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/a687007.html">a687007</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="European Union">EU</abbr></small> <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">EMA</a>: <span title="www.ema.europa.eu: 'Zidovudine'"><a rel="nofollow" class="external text" href="https://www.ema.europa.eu/en/medicines/search_api_aggregation_ema_active_substance_and_inn_common_name/Zidovudine">by INN</a></span></li> <li><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Zidovudine">Zidovudine</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> B3</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/Oral_administration" title="Oral administration">By mouth</a>, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a>, <a href="/wiki/Suppository" title="Suppository">rectal suppository</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_J05" title="ATC code J05">J05AF01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J05AF01">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="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)<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></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_1-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>Rx-only<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Rx-only<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li> <li>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">Complete absorption, following first-pass metabolism systemic availability 75% (range 52 to 75%)</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">30 to 38%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a></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">0.5 to 3 hours</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a> and <a href="/wiki/Bile_duct" title="Bile duct">Bile duct</a></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%;">3'-deoxy-3'-azido-thymidine <br /> 1-[(2<i>R</i>,4<i>S</i>,5<i>S</i>)-4-Azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></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=30516-87-1">30516-87-1</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/35370">35370</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=4825">4825</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/DB00495">DB00495</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.32555.html">32555</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/4B9XT59T7S">4B9XT59T7S</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/D00413">D00413</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:10110">CHEBI:10110</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/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/ChEMBL129">ChEMBL129</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/NIAID_ChemDB" title="NIAID ChemDB">NIAID ChemDB</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemdb.niaid.nih.gov"><a rel="nofollow" class="external text" href="https://chemdb.niaid.nih.gov/CompoundDetails.aspx?AIDSNO=000001">000001</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB ligand</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>AZZ (<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=AZZ">PDBe</a></span>, <span title="www.rcsb.org"><a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/AZZ">RCSB PDB</a></span>)</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID8020127">DTXSID8020127</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q198504#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/100.152.492">100.152.492</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q198504#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>10</sub><span title="Hydrogen">H</span><sub>13</sub><span title="Nitrogen">N</span><sub>5</sub><span title="Oxygen">O</span><sub>4</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="7002267245000000000♠"></span>267.245</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=O%3DC1NC%28C%28C%29%3DCN1%5BC%40%40H%5D2O%5BC%40H%5D%28CO%29%5BC%40%40H%5D%28N%3D%5BN%2B%5D%3D%5BN-%5D%29C2%29%3DO">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%;">O=C1NC(C(C)=CN1[C@@H]2O[C@H](CO)[C@@H](N=[N+]=[N-])C2)=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/C10H13N5O4/c1-5-3-15(10(18)12-9(5)17)8-2-6(13-14-11)7(4-16)19-8/h3,6-8,16H,2,4H2,1H3,(H,12,17,18)/t6-,7+,8+/m0/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:HBOMLICNUCNMMY-XLPZGREQSA-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=441946513&page2=Zidovudine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Zidovudine</b> (<b>ZDV</b>), also known as <b>azidothymidine</b> (<b>AZT</b>), was the first <a href="/wiki/Antiretroviral_medication" class="mw-redirect" title="Antiretroviral medication">antiretroviral medication</a> used to prevent and treat <a href="/wiki/HIV/AIDS" title="HIV/AIDS">HIV/AIDS</a>. It is generally recommended for use in combination with other antiretrovirals.<sup id="cite_ref-AHFS2016_6-0" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It may be used to prevent <a href="/wiki/Vertical_transmission" title="Vertical transmission">mother-to-child spread during birth</a> or after a <a href="/wiki/Needlestick_injury" title="Needlestick injury">needlestick injury</a> or other potential exposure.<sup id="cite_ref-AHFS2016_6-1" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is sold both by itself and together as <a href="/wiki/Lamivudine/zidovudine" title="Lamivudine/zidovudine">lamivudine/zidovudine</a> and <a href="/wiki/Abacavir/lamivudine/zidovudine" title="Abacavir/lamivudine/zidovudine">abacavir/lamivudine/zidovudine</a>.<sup id="cite_ref-AHFS2016_6-2" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It can be used by mouth or by slow <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">injection into a vein</a>.<sup id="cite_ref-AHFS2016_6-3" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Common side effects include headaches, fever, and nausea.<sup id="cite_ref-AHFS2016_6-4" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Serious side effects include <a href="/wiki/Liver_problems" class="mw-redirect" title="Liver problems">liver problems</a>, <a href="/wiki/Myopathy" title="Myopathy">muscle damage</a>, and <a href="/wiki/Lactic_acidosis" title="Lactic acidosis">high blood lactate levels</a>.<sup id="cite_ref-AHFS2016_6-5" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It is commonly used in <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> and appears to be safe for the fetus.<sup id="cite_ref-AHFS2016_6-6" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> ZDV is of the <a href="/wiki/Nucleoside_analog_reverse-transcriptase_inhibitor" class="mw-redirect" title="Nucleoside analog reverse-transcriptase inhibitor">nucleoside analog reverse-transcriptase inhibitor</a> (NRTI) class.<sup id="cite_ref-AHFS2016_6-7" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> It works by inhibiting the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Reverse_transcriptase" title="Reverse transcriptase">reverse transcriptase</a> that HIV uses to make DNA and therefore decreases replication of the virus.<sup id="cite_ref-AHFS2016_6-8" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Zidovudine was first described in 1964.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> It was resynthesized from a public-domain formula by <a href="/wiki/Burroughs_Wellcome" class="mw-redirect" title="Burroughs Wellcome">Burroughs Wellcome</a>.<sup id="cite_ref-latimes.com_8-0" class="reference"><a href="#cite_note-latimes.com-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It was approved in the United States in 1987 and was the first treatment for HIV.<sup id="cite_ref-AHFS2016_6-9" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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> 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_10-0" class="reference"><a href="#cite_note-WHO23rd-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<sup id="cite_ref-AHFS2016_6-10" class="reference"><a href="#cite_note-AHFS2016-6"><span class="cite-bracket">[</span>6<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=Zidovudine&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="HIV_treatment">HIV treatment</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Zidovudine&action=edit&section=2" title="Edit section: HIV treatment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>AZT was usually dosed twice a day in combination with other antiretroviral therapies. This approach is referred to as Highly Active Antiretroviral Therapy (<a href="/wiki/HAART" class="mw-redirect" title="HAART">HAART</a>) and is used to prevent the likelihood of HIV resistance.<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><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> As of 2019, the standard is a three-drug once-daily oral treatment that can include AZT.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="HIV_prevention">HIV prevention</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Zidovudine&action=edit&section=3" title="Edit section: HIV prevention"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>AZT has been used for <a href="/wiki/Post-exposure_prophylaxis" title="Post-exposure prophylaxis">post-exposure prophylaxis</a> (PEP) in combination with another antiretroviral drug called <a href="/wiki/Lamivudine" title="Lamivudine">lamivudine</a>. Together they work to substantially reduce the risk of HIV infection following the first single exposure to the virus.<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> More recently, AZT has been replaced by other antiretrovirals such as <a href="/wiki/Tenofovir_disoproxil" title="Tenofovir disoproxil">tenofovir</a> to provide PEP.<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> Before tenofovir, a principal part of the <a href="/wiki/Clinical_pathway" title="Clinical pathway">clinical pathway</a> for both pre-exposure prophylaxis and post-exposure treatment of <a href="/wiki/Vertical_transmission" title="Vertical transmission">mother-to-child transmission</a> of HIV during pregnancy, labor, and delivery and has been proven to be integral to uninfected siblings' <a href="/wiki/Perinatal" class="mw-redirect" title="Perinatal">perinatal</a> and <a href="/wiki/Neonatal" class="mw-redirect" title="Neonatal">neonatal</a> development.<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><sup id="cite_ref-pmid17476315_17-0" class="reference"><a href="#cite_note-pmid17476315-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Without AZT, 10–15% of fetuses with HIV-infected mothers will themselves become infected.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> AZT has been shown to reduce this risk to 8% when given in a three-part regimen post-conception, delivery, and six weeks post-delivery. Consistent and proactive precautionary measures, such as the rigorous use of antiretroviral medications, <a href="/wiki/Cesarean_section" class="mw-redirect" title="Cesarean section">cesarean section</a>, face masks, heavy-duty rubber gloves, clinically segregated disposable diapers, and avoidance of mouth contact will further reduce child-attendant transmission of HIV to as little as 1–2%.<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><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><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><p>During 1994 to 1999, AZT was the primary form of prevention of mother-to-child HIV transmission. AZT prophylaxis prevented more than 1000 parental and infant deaths from AIDS in the United States.<sup id="cite_ref-pmid16741877_22-0" class="reference"><a href="#cite_note-pmid16741877-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> In the U.S. at that time, the accepted standard of care for HIV-positive mothers was known as the 076 regimen and involved five daily doses of AZT from the second trimester onwards, as well as AZT intravenously administered during labour.<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> As this treatment was lengthy and expensive, it was deemed unfeasible in the <a href="/wiki/Global_South" class="mw-redirect" title="Global South">Global South</a>, where mother-to-child transmission was a significant problem. A number of studies were initiated in the late 1990s that sought to test the efficacy of a shorter, simpler regimen for use in 'resource-poor' countries.<sup id="cite_ref-Crane,_Johanna_2010_24-0" class="reference"><a href="#cite_note-Crane,_Johanna_2010-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> This AZT short course was an inferior standard of care and would have been considered malpractice if trialed in the US; however, it was nonetheless a treatment that would improve the care and survival of impoverished subjects.<sup id="cite_ref-Crane,_Johanna_2010_24-1" class="reference"><a href="#cite_note-Crane,_Johanna_2010-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Antibacterial_properties">Antibacterial properties</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Zidovudine&action=edit&section=4" title="Edit section: Antibacterial properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Zidovudine also has antibacterial properties,<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> though not routinely used in clinical settings. It acts on bacteria with a mechanism of action still not fully explained. Promising results from <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i> and <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i> studies showed the efficacy of AZT also against multidrug-resistant <a href="/wiki/Gram-negative_bacteria" title="Gram-negative bacteria">gram-negative bacteria</a> (including <a href="/wiki/Mcr-1" class="mw-redirect" title="Mcr-1">mcr-1</a> carrying and metallo-<a href="/wiki/%CE%92-lactamase" class="mw-redirect" title="Β-lactamase">β-lactamase</a> producing isolates), especially in combination with other active agents (e.g., <a href="/wiki/Fosfomycin" title="Fosfomycin">fosfomycin</a>, <a href="/wiki/Colistin" title="Colistin">colistin</a>, <a href="/wiki/Tigecycline" title="Tigecycline">tigecycline</a>).<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><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> <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=Zidovudine&action=edit&section=5" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most common side effects include nausea, vomiting, <a href="/wiki/Acid_reflux" class="mw-redirect" title="Acid reflux">acid reflux</a> (heartburn), headache, cosmetic reduction in abdominal body fat, trouble sleeping, and loss of appetite. Less common side effects include faint discoloration of fingernails and toenails, mood elevation, occasional tingling or transient numbness of the hands or feet, and minor skin discoloration. Allergic reactions are rare.<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>Early long-term higher-dose therapy with AZT was initially associated with side effects that sometimes limited therapy, including <a href="/wiki/Anemia" title="Anemia">anemia</a>, <a href="/wiki/Neutropenia" title="Neutropenia">neutropenia</a>, <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a>, <a href="/wiki/Cardiomyopathy" title="Cardiomyopathy">cardiomyopathy</a>, and <a href="/wiki/Myopathy" title="Myopathy">myopathy</a>. All of these conditions were generally found to be reversible upon reduction of AZT dosages. They have been attributed to several possible causes, including transient depletion of <a href="/wiki/Mitochondrial_DNA" title="Mitochondrial DNA">mitochondrial DNA</a>, sensitivity of the γ-DNA polymerase in some cell <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>,<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> the depletion of <a href="/wiki/Thymidine_triphosphate" title="Thymidine triphosphate">thymidine triphosphate</a>, <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>, reduction of intracellular <small>L</small>-<a href="/wiki/Carnitine" title="Carnitine">carnitine</a> or <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a> of the muscle cells.<sup id="cite_ref-Scruggs_30-0" class="reference"><a href="#cite_note-Scruggs-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Anemia due to AZT was successfully treated using <a href="/wiki/Erythropoietin" title="Erythropoietin">erythropoetin</a> to stimulate <a href="/wiki/Red_blood_cell" title="Red blood cell">red blood cell</a> production.<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><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> Drugs that inhibit <a href="/wiki/Liver" title="Liver">hepatic</a> <a href="/wiki/Glucuronidation" title="Glucuronidation">glucuronidation</a>, such as <a href="/wiki/Indomethacin" class="mw-redirect" title="Indomethacin">indomethacin</a>, <a href="/wiki/Nordazepam" title="Nordazepam">nordazepam</a>, <a href="/wiki/Acetylsalicylic_acid" class="mw-redirect" title="Acetylsalicylic acid">acetylsalicylic acid</a> (aspirin) and <a href="/wiki/Trimethoprim" title="Trimethoprim">trimethoprim</a> decreased the elimination rate and increased the therapeutic strength of the medication.<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> Today, side effects are much less common with the use of lower doses of AZT.<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> According to IARC, there is sufficient evidence in experimental animals for the <a href="/wiki/Carcinogen" title="Carcinogen">carcinogenicity</a> of zidovudine; it is possibly carcinogenic to humans (<a href="/wiki/Group_2B_carcinogen" class="mw-redirect" title="Group 2B carcinogen">Group 2B</a>).<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> In 2009, the State of California added zidovudine to its list of chemicals "known to the state of California to cause cancer and other reproductive harm."<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-heading3"><h3 id="Viral_resistance">Viral resistance</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Zidovudine&action=edit&section=6" title="Edit section: Viral resistance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Even at the highest doses that can be tolerated in patients, AZT is not potent enough to prevent all HIV replication and may only slow the replication of the virus and progression of the disease. Prolonged AZT treatment can lead to HIV developing resistance to AZT by <a href="/wiki/Mutation" title="Mutation">mutation</a> of its <a href="/wiki/Reverse_transcriptase" title="Reverse transcriptase">reverse transcriptase</a>.<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> To slow the development of resistance, physicians generally recommend that AZT be given in combination with another <a href="/wiki/Reverse-transcriptase_inhibitor#Nucleoside_analog_reverse-transcriptase_inhibitors_(NARTIs_or_NRTIs)" title="Reverse-transcriptase inhibitor">reverse-transcriptase inhibitor</a> and an antiretroviral from another group, such as a <a href="/wiki/Protease_inhibitor_(pharmacology)" title="Protease inhibitor (pharmacology)">protease inhibitor</a>, <a href="/wiki/Reverse-transcriptase_inhibitor#Non-nucleoside_reverse-transcriptase_inhibitors_(NNRTIs)" title="Reverse-transcriptase inhibitor">non-nucleoside reverse-transcriptase inhibitor</a>, or <a href="/wiki/Integrase_inhibitor" title="Integrase inhibitor">integrase inhibitor</a>; this type of therapy is known as <a href="/wiki/HAART" class="mw-redirect" title="HAART">HAART</a> (Highly Active Anti Retroviral Therapy). </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=Zidovudine&action=edit&section=7" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Azt_pills.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/66/Azt_pills.JPG/250px-Azt_pills.JPG" decoding="async" width="250" height="166" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/6/66/Azt_pills.JPG 1.5x" data-file-width="350" data-file-height="232" /></a><figcaption>AZT in oral, injectable, and suppository form</figcaption></figure> <p>AZT is a <a href="/wiki/Thymidine" title="Thymidine">thymidine</a> analogue. AZT works by selectively inhibiting HIV's <a href="/wiki/Reverse_transcriptase" title="Reverse transcriptase">reverse transcriptase</a>, the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> that the virus uses to make a <a href="/wiki/DNA" title="DNA">DNA</a> copy of its <a href="/wiki/RNA" title="RNA">RNA</a>. Reverse transcription is necessary for production of HIV's double-stranded DNA, which would be subsequently integrated into the genetic material of the infected <a href="/wiki/Cell_(biology)" title="Cell (biology)">cell</a> (where it is called a <a href="/wiki/Provirus" title="Provirus">provirus</a>).<sup id="cite_ref-MitsuyaPNAS_39-0" class="reference"><a href="#cite_note-MitsuyaPNAS-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Yarchoan_R,_Klecker_R,_Weinhold_K,_Markham_P,_Lyerly_H,_Durack_D,_Gelmann_E,_Lehrman_S,_Blum_R,_Barry_D_1986_575–80_40-0" class="reference"><a href="#cite_note-Yarchoan_R,_Klecker_R,_Weinhold_K,_Markham_P,_Lyerly_H,_Durack_D,_Gelmann_E,_Lehrman_S,_Blum_R,_Barry_D_1986_575–80-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Cellular enzymes convert AZT into the effective 5'-triphosphate form. Some studies have shown that terminating synthesis of HIV's DNA chains is the specific inhibitory mechanism.<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> </p><p>At very high doses, AZT's triphosphate form may also inhibit <a href="/wiki/DNA_polymerase" title="DNA polymerase">DNA polymerase</a> used by human cells to undergo <a href="/wiki/Cell_division" title="Cell division">cell division</a>, but regardless of dosage AZT has an approximately 100-fold greater affinity for HIV's reverse transcriptase.<sup id="cite_ref-FurmanPNAS_43-0" class="reference"><a href="#cite_note-FurmanPNAS-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> The selectivity has been suggested to be due to the cell's ability to quickly repair its own DNA chain if it is disrupted by AZT during its formation, whereas the HIV virus lacks that ability.<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> Thus AZT inhibits HIV replication without affecting the function of uninfected cells.<sup id="cite_ref-MitsuyaPNAS_39-1" class="reference"><a href="#cite_note-MitsuyaPNAS-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> At sufficiently high dosages, AZT begins to inhibit the cellular DNA polymerase used by <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> to replicate, accounting for its potentially toxic but reversible effects on <a href="/wiki/Cardiac_muscle" title="Cardiac muscle">cardiac</a> and <a href="/wiki/Skeletal_muscle" title="Skeletal muscle">skeletal muscles</a>, causing <a href="/wiki/Myositis" title="Myositis">myositis</a>.<sup id="cite_ref-Yarchoan_R,_Mitsuya_H,_Myers_C,_Broder_S_1989_726–38_45-0" class="reference"><a href="#cite_note-Yarchoan_R,_Mitsuya_H,_Myers_C,_Broder_S_1989_726–38-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </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=Zidovudine&action=edit&section=8" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Azt_crystal.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Azt_crystal.JPG/250px-Azt_crystal.JPG" decoding="async" width="250" height="178" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/0/01/Azt_crystal.JPG 1.5x" data-file-width="350" data-file-height="249" /></a><figcaption>A crystal of AZT, viewed under polarized light</figcaption></figure> <p>Enantiopure AZT crystallizes in the <a href="/wiki/Monoclinic_crystal_system" title="Monoclinic crystal system">monoclinic</a> space group P2<sub>1</sub>. The primary intermolecular bonding motif is a hydrogen bonded dimeric ring formed from two N-H<sup>...</sup>O interactions.<sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Zidovudine&action=edit&section=9" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Initial_cancer_research">Initial cancer research</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Zidovudine&action=edit&section=10" title="Edit section: Initial cancer research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the 1960s, the theory that most <a href="/wiki/Cancer" title="Cancer">cancers</a> were caused by environmental <a href="/wiki/Retrovirus" title="Retrovirus">retroviruses</a> gained clinical support and funding. It had recently become known, due to the work of Nobel laureates <a href="/wiki/Howard_Temin" class="mw-redirect" title="Howard Temin">Howard Temin</a> and <a href="/wiki/David_Baltimore" title="David Baltimore">David Baltimore</a>,<sup id="cite_ref-test75_52-0" class="reference"><a href="#cite_note-test75-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> that nearly all avian cancers were caused by bird retroviruses, but corresponding human retroviruses had not yet been found. </p><p>In parallel work, other compounds that successfully blocked the synthesis of nucleic acids had been proven to be both antibacterial, antiviral, and anticancer agents, the leading work being done at the laboratory of Nobel laureates <a href="/wiki/George_H._Hitchings" title="George H. Hitchings">George H. Hitchings</a> and <a href="/wiki/Gertrude_Elion" class="mw-redirect" title="Gertrude Elion">Gertrude Elion</a>, leading to the development of the antitumor agent <a href="/wiki/6-mercaptopurine" class="mw-redirect" title="6-mercaptopurine">6-mercaptopurine</a>.<sup id="cite_ref-test88_53-0" class="reference"><a href="#cite_note-test88-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>Richard E. Beltz first synthesized AZT in 1961, but did not publish his research.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup><a href="/wiki/Jerome_Horwitz" title="Jerome Horwitz">Jerome Horwitz</a> of the Barbara Ann Karmanos Cancer Institute and <a href="/wiki/Wayne_State_University_School_of_Medicine" title="Wayne State University School of Medicine">Wayne State University School of Medicine</a> synthesized AZT in 1964 under a <a href="/wiki/United_States" title="United States">US</a> <a href="/wiki/National_Institutes_of_Health" title="National Institutes of Health">National Institutes of Health</a> (NIH) <a href="/wiki/Federal_grant" class="mw-redirect" title="Federal grant">grant</a>.<sup id="cite_ref-pmid20018391_56-0" class="reference"><a href="#cite_note-pmid20018391-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-horwitz64_57-0" class="reference"><a href="#cite_note-horwitz64-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-filmazt2002_58-0" class="reference"><a href="#cite_note-filmazt2002-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> Development was shelved after it proved biologically inert in mice.<sup id="cite_ref-pmid20018391_56-1" class="reference"><a href="#cite_note-pmid20018391-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-nytimes_59-0" class="reference"><a href="#cite_note-nytimes-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> In 1974, Wolfram Ostertag of the <a href="/wiki/Max_Planck_Institute_for_Experimental_Medicine" title="Max Planck Institute for Experimental Medicine">Max Planck Institute for Experimental Medicine</a> in <a href="/wiki/G%C3%B6ttingen" title="Göttingen">Göttingen</a>, Germany, reported that AZT specifically targeted <a href="/wiki/Friend_virus" title="Friend virus">Friend virus</a> (strain of <a href="/wiki/Murine_leukemia_virus" title="Murine leukemia virus">murine leukemia virus</a>).<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p><p>This report attracted little interest from other researchers as the Friend leukemia virus is a retrovirus, and at the time, there were no known human diseases caused by retroviruses.<sup id="cite_ref-Sneader_2006_260–261_61-0" class="reference"><a href="#cite_note-Sneader_2006_260–261-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="HIV/AIDS_research"><span id="HIV.2FAIDS_research"></span>HIV/AIDS research</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Zidovudine&action=edit&section=11" title="Edit section: HIV/AIDS research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1983, researchers at the Institut Pasteur in Paris identified the retrovirus now known as the Human Immunodeficiency Virus (HIV) as the cause of acquired immunodeficiency syndrome (AIDS) in humans.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> Shortly thereafter, <a href="/wiki/Samuel_Broder" title="Samuel Broder">Samuel Broder</a>, <a href="/wiki/Hiroaki_Mitsuya" title="Hiroaki Mitsuya">Hiroaki Mitsuya</a>, and <a href="/wiki/Robert_Yarchoan" title="Robert Yarchoan">Robert Yarchoan</a> of the United States <a href="/wiki/National_Cancer_Institute" title="National Cancer Institute">National Cancer Institute</a> (NCI) initiated a program to develop therapies for HIV/AIDS.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> Using a line of <a href="/wiki/T_helper_cell" title="T helper cell">CD4<sup>+</sup> T cells</a> that they had made, they developed an assay to screen drugs for their ability to protect CD4<sup>+</sup> T cells from being killed by HIV. In order to expedite the process of discovering a drug, the NCI researchers actively sought collaborations with pharmaceutical companies having access to libraries of compounds with potential antiviral activity.<sup id="cite_ref-MitsuyaPNAS_39-2" class="reference"><a href="#cite_note-MitsuyaPNAS-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> This assay could simultaneously test both the anti-HIV effect of the compounds and their toxicity against infected T cells. </p><p>In June 1984, Burroughs-Wellcome virologist Marty St. Clair set up a program to discover drugs with the potential to inhibit HIV replication. Burroughs-Wellcome had expertise in nucleoside analogs and viral diseases, led by researchers including <a href="/wiki/George_Hitchings" class="mw-redirect" title="George Hitchings">George Hitchings</a>, <a href="/wiki/Gertrude_B._Elion" title="Gertrude B. Elion">Gertrude Elion</a>, David Barry, Paul (Chip) McGuirt Jr., Philip Furman, Martha St. Clair, <a href="/wiki/Janet_Rideout" title="Janet Rideout">Janet Rideout</a>, Sandra Lehrman and others. Their research efforts were focused in part on the viral enzyme <a href="/wiki/Reverse_transcriptase" title="Reverse transcriptase">reverse transcriptase</a>. Reverse transcriptase is an enzyme that retroviruses, including HIV, utilize to replicate themselves. Secondary testing was performed in mouse cells infected with the retroviruses Friend virus or Harvey sarcoma virus, as the Wellcome group did not have a viable in-house HIV antiviral assay in place at that time, and these other retroviruses were believed to represent reasonable surrogates. AZT proved to be a remarkably potent inhibitor of both Friend virus and Harvey sarcoma virus, and a search of the company's records showed that it had demonstrated low toxicity when tested for its antibacterial activity in rats many years earlier. Based in part on these results, AZT was selected by nucleoside chemist Janet Rideout as one of 11 compounds to send to the NCI for testing in that organization's HIV antiviral assay.<sup id="cite_ref-Sneader_2006_260–261_61-1" class="reference"><a href="#cite_note-Sneader_2006_260–261-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>In February 1985, the NCI scientists found that AZT had potent efficacy in vitro.<sup id="cite_ref-MitsuyaPNAS_39-3" class="reference"><a href="#cite_note-MitsuyaPNAS-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid20018391_56-2" class="reference"><a href="#cite_note-pmid20018391-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> Several months later, a phase 1 <a href="/wiki/Clinical_trial" title="Clinical trial">clinical trial</a> of AZT at the NCI was initiated at the NCI and Duke University.<sup id="cite_ref-Yarchoan_R,_Klecker_R,_Weinhold_K,_Markham_P,_Lyerly_H,_Durack_D,_Gelmann_E,_Lehrman_S,_Blum_R,_Barry_D_1986_575–80_40-1" class="reference"><a href="#cite_note-Yarchoan_R,_Klecker_R,_Weinhold_K,_Markham_P,_Lyerly_H,_Durack_D,_Gelmann_E,_Lehrman_S,_Blum_R,_Barry_D_1986_575–80-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Yarchoan_R,_Mitsuya_H,_Myers_C,_Broder_S_1989_726–38_45-1" class="reference"><a href="#cite_note-Yarchoan_R,_Mitsuya_H,_Myers_C,_Broder_S_1989_726–38-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> In doing this Phase I trial, they built on their experience in doing an earlier trial, with suramin, another drug that had shown effective anti-HIV activity in the laboratory. This initial trial of AZT proved that the drug could be safely administered to patients with HIV, that it increased their <a href="/wiki/CD4" title="CD4">CD4</a> counts, restored T cell immunity as measured by skin testing, and that it showed strong evidence of clinical effectiveness, such as inducing weight gain in AIDS patients. It also showed that levels of AZT that worked in vitro could be injected into patients in serum and suppository form, and that the drug penetrated deeply only into infected brains. </p> <div class="mw-heading mw-heading3"><h3 id="Patent_filed_and_FDA_approval">Patent filed and FDA approval</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Zidovudine&action=edit&section=12" title="Edit section: Patent filed and FDA approval"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A flawed <a href="/wiki/Double-blind" class="mw-redirect" title="Double-blind">double-blind</a>, <a href="/wiki/Placebo" title="Placebo">placebo</a>-controlled <a href="/wiki/Randomized_trial" class="mw-redirect" title="Randomized trial">randomized trial</a> of AZT was subsequently conducted by Burroughs-Wellcome and suggested that AZT safely prolongs the lives of people with HIV. However, it was quickly unblinded and several more in the drug receiving group later perished.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Burroughs-Wellcome filed for a patent for AZT in 1985. The Anti-Infective Advisory Committee to United States <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) voted ten to one to recommend the approval of AZT.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> The FDA approved the drug (via the then-new <a href="/wiki/FDA_Fast_Track_Development_Program" class="mw-redirect" title="FDA Fast Track Development Program">FDA accelerated approval system</a>) for use against HIV, AIDS, and AIDS Related Complex (ARC, a now-obsolete medical term for pre-AIDS illness) on March 20, 1987.<sup id="cite_ref-Cimons_69-0" class="reference"><a href="#cite_note-Cimons-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> The time between the first demonstration that AZT was active against HIV in the laboratory and its approval was 25 months. </p><p>AZT was subsequently approved unanimously for infants and children in 1990.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> AZT was initially administered in significantly higher dosages than today, typically 400 mg every four hours, day and night, compared to modern dosage of 300 mg twice daily.<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> The paucity of alternatives for treating HIV/AIDS at that time unambiguously affirmed the health risk/benefit ratio, with inevitable slow, disfiguring, and painful death from HIV outweighing the drug's side effect of transient <a href="/wiki/Anemia" title="Anemia">anemia</a> and malaise. </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=Zidovudine&action=edit&section=13" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951" /><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Cost_of_HIV_treatment" title="Cost of HIV treatment">Cost of HIV treatment</a></div> <p>Until 1991, 80% of the $420 million allocated to the National Institute of Health's AIDS Clinical Trials Group, went toward studies of AZT. Aside from two similarly designed chemotherapies, ddI and ddC, from approval of AZT in 1987 until 1993, no other drugs against AIDS were approved, leading to criticism that research preoccupation with AZT and its close relatives, and the massive diverting of funds to such, had delayed the development of more efficacious drugs.<sup id="cite_ref-latimes.com_8-1" class="reference"><a href="#cite_note-latimes.com-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>In 1991, the advocacy group <a href="/wiki/Public_Citizen" title="Public Citizen">Public Citizen</a> filed a lawsuit claiming that the patents were invalid. Subsequently, Barr Laboratories and Novopharm Ltd. also challenged the patent, in part based on the assertion that NCI scientists Samuel Broder, Hiroaki Mitsuya, and Robert Yarchoan should have been named as inventors, and those two companies applied to the FDA to sell AZT as a generic drug. In response, <a href="/wiki/Burroughs_Wellcome" class="mw-redirect" title="Burroughs Wellcome">Burroughs Wellcome</a> Co. filed a lawsuit against the two companies. The <a href="/wiki/United_States_Court_of_Appeals_for_the_Federal_Circuit" title="United States Court of Appeals for the Federal Circuit">United States Court of Appeals for the Federal Circuit</a> ruled in 1992 in favor of Burroughs Wellcome, ruling that even though they had never tested it against HIV, they had conceived of it working before they sent it to the NCI scientists. This suit was appealed up to the Supreme Court of the US, but in 1996 the Court declined to formally review it.<sup id="cite_ref-72" class="reference"><a href="#cite_note-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> The case, <i><a rel="nofollow" class="external text" href="https://openjurist.org/40/f3d/1223">Burroughs Wellcome Co. v. Barr Laboratories</a></i>, was a landmark in US law of inventorship.<sup id="cite_ref-73" class="reference"><a href="#cite_note-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> </p><p>In 2002, another lawsuit was filed challenging the patent by the <a href="/wiki/AIDS_Healthcare_Foundation" title="AIDS Healthcare Foundation">AIDS Healthcare Foundation</a>, which also filed an antitrust case against <a href="/wiki/GSK_Plc" class="mw-redirect" title="GSK Plc">GSK</a>.<sup id="cite_ref-Law3602004_74-0" class="reference"><a href="#cite_note-Law3602004-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> The patent case was dismissed in 2003 and AHF filed a new case challenging the patent.<sup id="cite_ref-Law3602004_74-1" class="reference"><a href="#cite_note-Law3602004-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> </p><p>GSK's patents on AZT expired in 2005, and in September 2005, the FDA approved three <a href="/wiki/Generic_drug" title="Generic drug">generic</a> versions.<sup id="cite_ref-75" class="reference"><a href="#cite_note-75"><span class="cite-bracket">[</span>75<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=Zidovudine&action=edit&section=14" 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-FDA-AllBoxedWarnings-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-FDA-AllBoxedWarnings_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="https://nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802">"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"</a>. <i>nctr-crs.fda.gov</i>. <a href="/wiki/FDA" class="mw-redirect" title="FDA">FDA</a><span class="reference-accessdate">. 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cs1">Armstrong M, Murphy Jr GM (April 26, 2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4025834">"Inventorship and ownership considerations and pitfalls with collaborative research: patent highlight"</a>. <i>ACS Medicinal Chemistry Letters</i>. <b>3</b> (5): <span class="nowrap">349–</span>51. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fml300084e">10.1021/ml300084e</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4025834">4025834</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/24900477">24900477</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=ACS+Medicinal+Chemistry+Letters&rft.atitle=Inventorship+and+ownership+considerations+and+pitfalls+with+collaborative+research%3A+patent+highlight.&rft.volume=3&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E349-%3C%2Fspan%3E51&rft.date=2012-04-26&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4025834%23id-name%3DPMC&rft_id=info%3Apmid%2F24900477&rft_id=info%3Adoi%2F10.1021%2Fml300084e&rft.aulast=Armstrong&rft.aufirst=M&rft.au=Murphy+Jr%2C+GM&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4025834&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZidovudine" class="Z3988"></span></span> </li> <li id="cite_note-Law3602004-74"><span class="mw-cite-backlink">^ <a href="#cite_ref-Law3602004_74-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Law3602004_74-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMeland2004" class="citation news cs1">Meland M (May 3, 2004). <a rel="nofollow" class="external text" href="http://www.law360.com/articles/1396/judge-denies-request-to-dismiss-patent-challenge-vs-glaxo-s-azt">"Judge Denies Request To Dismiss Patent Challenge Vs. Glaxo's AZT – Law360"</a>. <i>Law360</i>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161117212239/http://www.law360.com/articles/1396/judge-denies-request-to-dismiss-patent-challenge-vs-glaxo-s-azt">Archived</a> from the original on November 17, 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Law360&rft.atitle=Judge+Denies+Request+To+Dismiss+Patent+Challenge+Vs.+Glaxo%27s+AZT+%E2%80%93+Law360&rft.date=2004-05-03&rft.aulast=Meland&rft.aufirst=M&rft_id=http%3A%2F%2Fwww.law360.com%2Farticles%2F1396%2Fjudge-denies-request-to-dismiss-patent-challenge-vs-glaxo-s-azt&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZidovudine" class="Z3988"></span></span> </li> <li id="cite_note-75"><span class="mw-cite-backlink"><b><a href="#cite_ref-75">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.fda.gov/ForPatients/Illness/HIVAIDS/History/ucm151081.htm">"HIV/AIDS History of Approvals – HIV/AIDS Historical Time Line 2000 – 2010"</a>. U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA). August 8, 2014. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161023204558/https://www.fda.gov/ForPatients/Illness/HIVAIDS/History/ucm151081.htm">Archived</a> from the original on October 23, 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=HIV%2FAIDS+History+of+Approvals+%E2%80%93+HIV%2FAIDS+Historical+Time+Line+2000+%E2%80%93+2010&rft.pub=U.S.+Food+and+Drug+Administration+%28FDA%29&rft.date=2014-08-08&rft_id=https%3A%2F%2Fwww.fda.gov%2FForPatients%2FIllness%2FHIVAIDS%2FHistory%2Fucm151081.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZidovudine" 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=Zidovudine&action=edit&section=15" 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/zidovudine">"Zidovudine"</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=Zidovudine&rft_id=https%3A%2F%2Fdruginfo.nlm.nih.gov%2Fdrugportal%2Fname%2Fzidovudine&rfr_id=info%3Asid%2Fen.wikipedia.org%3AZidovudine" class="Z3988"></span></li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist 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title="Lenacapavir">Lenacapavir (LEN)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Entry_inhibitor" title="Entry inhibitor">Entry/fusion inhibitors</a> <br /> <i>(<a href="/wiki/Discovery_and_development_of_CCR5_receptor_antagonists" class="mw-redirect" title="Discovery and development of CCR5 receptor antagonists">Discovery and development</a>)</i></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><i><a href="/wiki/Gp41" title="Gp41">gp41</a></i> (<a href="/wiki/Enfuvirtide" title="Enfuvirtide">Enfuvirtide (ENF, T-20)</a>)<sup>◊</sup></li> <li><i><a href="/wiki/CCR5" title="CCR5">CCR5</a></i> (<a href="/wiki/Maraviroc" title="Maraviroc">Maraviroc (MVC)</a></li> <li><a href="/wiki/Vicriviroc" title="Vicriviroc">Vicriviroc</a><sup>†</sup>, <a href="/wiki/Cenicriviroc" title="Cenicriviroc">Cenicriviroc</a><sup>†</sup>, <a href="/wiki/Leronlimab" title="Leronlimab">Leronlimab</a><sup>†</sup>)</li> <li><i><a href="/wiki/CD4" title="CD4">CD4</a></i> (<a href="/wiki/Ibalizumab" title="Ibalizumab">Ibalizumab (IBA)</a>, <a href="/wiki/Semzuvolimab" title="Semzuvolimab">Semzuvolimab</a><sup>§</sup>)</li> <li><i><a href="/wiki/Gp120" class="mw-redirect" title="Gp120">gp120</a></i> (<a href="/wiki/Fostemsavir" title="Fostemsavir">Fostemsavir (FTR)</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Integrase_inhibitor" title="Integrase inhibitor">Integrase inhibitors</a><br />(Integrase strand transfer inhibitors (INSTI))</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bictegravir" title="Bictegravir">Bictegravir (BIC)</a></li> <li><a href="/wiki/Cabotegravir" title="Cabotegravir">Cabotegravir (CAB)</a></li> <li><a href="/wiki/Dolutegravir" title="Dolutegravir">Dolutegravir (DTG)</a><sup>#</sup></li> <li><a href="/wiki/Elvitegravir" title="Elvitegravir">Elvitegravir (EVG)</a></li> <li><a href="/wiki/Raltegravir" title="Raltegravir">Raltegravir (RAL)</a><sup>#</sup></li> <li><a href="/wiki/BI_224436" title="BI 224436">BI 224436</a><sup>†</sup></li> <li><a href="/wiki/MK-2048" title="MK-2048">MK-2048</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Maturation_inhibitor" title="Maturation inhibitor">Maturation inhibitors</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/Bevirimat" title="Bevirimat">Bevirimat</a><sup>†</sup></li> <li><a href="/wiki/BMS-955176" title="BMS-955176">BMS-955176</a><sup>§</sup></li> <li><a href="/wiki/Fipravirimat" title="Fipravirimat">Fipravirimat</a><sup>§</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Protease_inhibitor_(pharmacology)" title="Protease inhibitor (pharmacology)">Protease Inhibitors (PI)</a><br /><i>(<a href="/wiki/Discovery_and_development_of_HIV_protease_inhibitors" class="mw-redirect" title="Discovery and development of HIV protease inhibitors">Discovery and development</a>)</i></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%">1<sup>st</sup> generation</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/Amprenavir" title="Amprenavir">Amprenavir (APV)</a><sup>‡</sup></li> <li><a href="/wiki/Fosamprenavir" title="Fosamprenavir">Fosamprenavir (FPV)</a></li> <li><a href="/wiki/Indinavir" title="Indinavir">Indinavir (IDV)</a><sup>◊</sup></li> <li><a href="/wiki/Lopinavir" title="Lopinavir">Lopinavir (LPV)</a></li> <li><a href="/wiki/Nelfinavir" title="Nelfinavir">Nelfinavir (NFV)</a><sup>◊</sup></li> <li><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir (RTV)</a><sup>#</sup></li> <li><a href="/wiki/Saquinavir" title="Saquinavir">Saquinavir (SQV)</a><sup>◊</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">2<sup>nd</sup> generation</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/Atazanavir" title="Atazanavir">Atazanavir (ATV)</a>°<sup>#</sup></li> <li><a href="/wiki/Darunavir" title="Darunavir">Darunavir (DRV)</a>°<sup>#</sup></li> <li><a href="/wiki/Tipranavir" title="Tipranavir">Tipranavir (TPV)</a><sup>◊</sup></li> <li><a href="/wiki/TMC-310911" title="TMC-310911">TMC-310911</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/Reverse-transcriptase_inhibitor" title="Reverse-transcriptase inhibitor">Reverse-transcriptase<br /> inhibitors</a> (RTIs)</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/Reverse-transcriptase_inhibitor" title="Reverse-transcriptase inhibitor">Nucleoside and<br /> nucleotide (NRTI)</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/Nucleoside_analogue" title="Nucleoside analogue">Nucleoside analogues</a>/<a href="/wiki/Reverse-transcriptase_inhibitor#Nucleoside_analog_reverse-transcriptase_inhibitors_.28NARTIs_or_NRTIs.29" title="Reverse-transcriptase inhibitor">NRTIs</a>:</i> <a href="/wiki/Abacavir" title="Abacavir">Abacavir (ABC)</a><sup>#</sup></li> <li><a href="/wiki/Didanosine" title="Didanosine">Didanosine (ddI)</a><sup>◊</sup></li> <li><a href="/wiki/Emtricitabine" title="Emtricitabine">Emtricitabine (FTC)</a></li> <li><a href="/wiki/Lamivudine" title="Lamivudine">Lamivudine (3TC)</a><sup>#</sup></li> <li><a href="/wiki/Stavudine" title="Stavudine">Stavudine (d4T)</a><sup>◊</sup></li> <li><a href="/wiki/Zalcitabine" title="Zalcitabine">Zalcitabine (ddC)</a><sup>‡</sup></li> <li><a class="mw-selflink selflink">Zidovudine (AZT, ZDV)</a><sup>#</sup></li> <li><a href="/wiki/Amdoxovir" title="Amdoxovir">Amdoxovir</a><sup>†</sup></li> <li><a href="/wiki/Apricitabine" title="Apricitabine">Apricitabine</a><sup>†</sup></li> <li><a href="/wiki/Censavudine" title="Censavudine">Censavudine</a><sup>†</sup></li> <li><a href="/wiki/Elvucitabine" title="Elvucitabine">Elvucitabine</a><sup>†</sup></li> <li><a href="/wiki/Islatravir" title="Islatravir">Islatravir (EFdA, ISL)</a><sup>§</sup></li> <li><a href="/wiki/Racivir" title="Racivir">Racivir</a><sup>†</sup></li> <li><a href="/wiki/Stampidine" title="Stampidine">Stampidine</a><sup>†</sup></li></ul> <ul><li><i><a href="/wiki/Nucleotide_analogue" class="mw-redirect" title="Nucleotide analogue">Nucleotide analogues</a>/<a href="/wiki/Reverse-transcriptase_inhibitor#Nucleotide_analog_reverse-transcriptase_inhibitors_.28NtARTIs_or_NtRTIs.29" title="Reverse-transcriptase inhibitor">NtRTIs</a>:</i> <a href="/wiki/Tenofovir_disoproxil" title="Tenofovir disoproxil">Tenofovir disoproxil (TDF)</a><sup>#</sup></li> <li><a href="/wiki/Tenofovir_alafenamide" title="Tenofovir alafenamide">Tenofovir alafenamide (TAF)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Reverse-transcriptase_inhibitor#Non-nucleoside_reverse-transcriptase_inhibitors_(NNRTIs)" title="Reverse-transcriptase inhibitor">Non-nucleoside (NNRTI)</a><br /><i>(<a href="/wiki/Discovery_and_development_of_non-nucleoside_reverse-transcriptase_inhibitors" title="Discovery and development of non-nucleoside reverse-transcriptase inhibitors">Discovery and development</a>)</i></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%">1<sup>st</sup> generation</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/Efavirenz" title="Efavirenz">Efavirenz (EFV)</a><sup>#</sup></li> <li><a href="/wiki/Nevirapine" title="Nevirapine">Nevirapine (NVP)</a><sup>#</sup></li> <li><a href="/wiki/Delavirdine" title="Delavirdine">Delavirdine (DLV)</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">2<sup>nd</sup> generation</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/Diarylpyrimidines" title="Diarylpyrimidines">diarylpyrimidines</a></i> <ul><li><a href="/wiki/Dapivirine" title="Dapivirine">Dapivirine (DPV)</a></li> <li><a href="/wiki/Etravirine" title="Etravirine">Etravirine (ETR)</a></li> <li><a href="/wiki/Rilpivirine" title="Rilpivirine">Rilpivirine (RPV)</a></li></ul></li> <li><a href="/wiki/Doravirine" title="Doravirine">Doravirine (DOR)</a></li> <li><a href="/wiki/Elsulfavirine" title="Elsulfavirine">Elsulfavirine (ESV)</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/Fixed-dose_combination_(antiretroviral)" class="mw-redirect" title="Fixed-dose combination (antiretroviral)">Combined formulations</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/Abacavir/lamivudine" title="Abacavir/lamivudine">Abacavir/lamivudine</a><sup>#</sup></li> <li><a href="/wiki/Abacavir/dolutegravir/lamivudine" title="Abacavir/dolutegravir/lamivudine">Abacavir/dolutegravir/lamivudine</a>°</li> <li><a href="/wiki/Abacavir/lamivudine/zidovudine" title="Abacavir/lamivudine/zidovudine">Abacavir/lamivudine/zidovudine</a></li> <li><a href="/wiki/Atazanavir/cobicistat" title="Atazanavir/cobicistat">Atazanavir/cobicistat</a></li> <li><a href="/wiki/Bictegravir/emtricitabine/tenofovir_alafenamide" title="Bictegravir/emtricitabine/tenofovir alafenamide">Bictegravir/emtricitabine/tenofovir alafenamide</a>°</li> <li><a href="/wiki/Cabotegravir/rilpivirine" title="Cabotegravir/rilpivirine">Cabotegravir/rilpivirine</a></li> <li><a href="/wiki/Darunavir/cobicistat" title="Darunavir/cobicistat">Darunavir/cobicistat</a></li> <li><a href="/wiki/Darunavir/cobicistat/emtricitabine/tenofovir_alafenamide" class="mw-redirect" title="Darunavir/cobicistat/emtricitabine/tenofovir alafenamide">Darunavir/cobicistat/emtricitabine/tenofovir alafenamide</a>°</li> <li><a href="/wiki/Dolutegravir/emtricitabine/tenofovir_alafenamide" class="mw-redirect" title="Dolutegravir/emtricitabine/tenofovir alafenamide">Dolutegravir/emtricitabine/tenofovir alafenamide</a></li> <li><a href="/wiki/Dolutegravir/lamivudine" title="Dolutegravir/lamivudine">Dolutegravir/lamivudine</a>°</li> <li><a href="/wiki/Dolutegravir/lamivudine/tenofovir_alafenamide" class="mw-redirect" title="Dolutegravir/lamivudine/tenofovir alafenamide">Dolutegravir/lamivudine/tenofovir alafenamide</a>°</li> <li><a href="/wiki/Dolutegravir/lamivudine/tenofovir_disoproxil" class="mw-redirect" title="Dolutegravir/lamivudine/tenofovir disoproxil">Dolutegravir/lamivudine/tenofovir disoproxil</a>°<sup>#</sup></li> <li><a href="/wiki/Dolutegravir/rilpivirine" title="Dolutegravir/rilpivirine">Dolutegravir/rilpivirine</a></li> <li><a href="/wiki/Doravirine/lamivudine/tenofovir_disoproxil" class="mw-redirect" title="Doravirine/lamivudine/tenofovir disoproxil">Doravirine/lamivudine/tenofovir disoproxil</a></li> <li><a href="/wiki/Efavirenz/emtricitabine/tenofovir_disoproxil" class="mw-redirect" title="Efavirenz/emtricitabine/tenofovir disoproxil">Efavirenz/emtricitabine/tenofovir disoproxil</a><sup>#</sup></li> <li><a href="/wiki/Efavirenz/lamivudine/tenofovir_disoproxil" class="mw-redirect" title="Efavirenz/lamivudine/tenofovir disoproxil">Efavirenz/lamivudine/tenofovir disoproxil</a><sup>#</sup></li> <li><a href="/wiki/Elvitegravir/cobicistat/emtricitabine/tenofovir_alafenamide" class="mw-redirect" title="Elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide">Elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide</a></li> <li><a href="/wiki/Elvitegravir/cobicistat/emtricitabine/tenofovir_disoproxil" class="mw-redirect" title="Elvitegravir/cobicistat/emtricitabine/tenofovir disoproxil">Elvitegravir/cobicistat/emtricitabine/tenofovir disoproxil</a></li> <li><a href="/wiki/Emtricitabine/tenofovir_alafenamide" class="mw-redirect" title="Emtricitabine/tenofovir alafenamide">Emtricitabine/tenofovir alafenamide</a></li> <li><a href="/wiki/Emtricitabine/rilpivirine/tenofovir_alafenamide" class="mw-redirect" title="Emtricitabine/rilpivirine/tenofovir alafenamide">Emtricitabine/rilpivirine/tenofovir alafenamide</a></li> <li><a href="/wiki/Emtricitabine/rilpivirine/tenofovir_disoproxil" class="mw-redirect" title="Emtricitabine/rilpivirine/tenofovir disoproxil">Emtricitabine/rilpivirine/tenofovir disoproxil</a></li> <li><a href="/wiki/Emtricitabine/tenofovir_disoproxil" class="mw-redirect" title="Emtricitabine/tenofovir disoproxil">Emtricitabine/tenofovir disoproxil</a><sup>#</sup></li> <li><a href="/wiki/Lamivudine/nevirapine/stavudine" title="Lamivudine/nevirapine/stavudine">Lamivudine/nevirapine/stavudine</a></li> <li><a href="/wiki/Lamivudine/nevirapine/zidovudine" title="Lamivudine/nevirapine/zidovudine">Lamivudine/nevirapine/zidovudine</a></li> <li><a href="/wiki/Lamivudine/raltegravir" title="Lamivudine/raltegravir">Lamivudine/raltegravir</a></li> <li><a href="/wiki/Lamivudine/tenofovir_disoproxil" class="mw-redirect" title="Lamivudine/tenofovir disoproxil">Lamivudine/tenofovir disoproxil</a><sup>#</sup></li> <li><a href="/wiki/Lamivudine/zidovudine" title="Lamivudine/zidovudine">Lamivudine/zidovudine</a><sup>#</sup></li> <li><a href="/wiki/Lopinavir/ritonavir" title="Lopinavir/ritonavir">Lopinavir/ritonavir</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Pharmacokinetic boosters</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cobicistat" title="Cobicistat">Cobicistat (c)</a></li> <li><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir (r)</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Experimental agents</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/Antiviral_drug#Uncoating_inhibitor" title="Antiviral drug">Uncoating inhibitors</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/TRIM5alpha" title="TRIM5alpha">TRIM5alpha</a> (gene)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Transcription_(genetics)" class="mw-redirect" title="Transcription (genetics)">Transcription 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><a href="/wiki/Tat_(HIV)#Clinical_significance" title="Tat (HIV)">Tat antagonists</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiviral_drug#Translation_.2F_ribozymes" title="Antiviral drug">Translation inhibitors</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/Trichosanthin" title="Trichosanthin">Trichosanthin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiviral_drug#BNAbs.2F_BNAbs" title="Antiviral drug"> BNAbs</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/Elipovimab" title="Elipovimab">Elipovimab</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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abzyme" title="Abzyme">Abzyme</a></li> <li><a href="/wiki/BIT225" title="BIT225">BIT225</a><sup>†</sup></li> <li><a href="/wiki/Calanolide_A" title="Calanolide A">Calanolide A</a></li> <li><a href="/wiki/Ceragenin" title="Ceragenin">Ceragenin</a></li> <li><a href="/wiki/Cyanovirin-N" title="Cyanovirin-N">Cyanovirin-N</a></li> <li><a href="/wiki/Diarylpyrimidines" title="Diarylpyrimidines">Diarylpyrimidines</a></li> <li><a href="/wiki/Epigallocatechin_gallate" title="Epigallocatechin gallate">Epigallocatechin gallate (EGCG)</a></li> <li><a href="/wiki/Foscarnet" title="Foscarnet">Foscarnet</a></li> <li><a href="/wiki/Fosdevirine" title="Fosdevirine">Fosdevirine</a><sup>†</sup></li> <li><a href="/wiki/Griffithsin" title="Griffithsin">Griffithsin</a></li> <li><a href="/wiki/Hydroxycarbamide" title="Hydroxycarbamide">Hydroxycarbamide</a></li> <li><a href="/wiki/KP-1461" title="KP-1461">KP-1461</a><sup>†</sup></li> <li><a href="/wiki/Miltefosine" title="Miltefosine">Miltefosine</a></li> <li><a href="/wiki/Portmanteau_inhibitor" title="Portmanteau inhibitor">Portmanteau inhibitors</a></li> <li><a href="/wiki/Scytovirin" title="Scytovirin">Scytovirin</a></li> <li><a href="/wiki/Seliciclib" title="Seliciclib">Seliciclib</a><sup>†</sup></li> <li><a href="/wiki/Synergistic_enhancer_(antiretroviral)" title="Synergistic enhancer (antiretroviral)">Synergistic enhancers</a></li> <li><a href="/wiki/Tre_recombinase" title="Tre recombinase">Tre recombinase</a></li> <li><a href="/wiki/Zinc_finger_protein_transcription_factor" class="mw-redirect" title="Zinc finger protein transcription factor">Zinc finger protein transcription factor</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Failed agents</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/Aplaviroc" title="Aplaviroc">Aplaviroc</a></li> <li><a href="/wiki/Atevirdine" title="Atevirdine">Atevirdine</a></li> <li><a href="/wiki/Brecanavir" title="Brecanavir">Brecanavir</a></li> <li><a href="/wiki/Capravirine" title="Capravirine">Capravirine</a></li> <li><a href="/wiki/Dexelvucitabine" title="Dexelvucitabine">Dexelvucitabine</a></li> <li><a href="/wiki/Droxinavir" title="Droxinavir">Droxinavir</a></li> <li><a href="/wiki/Lasinavir" title="Lasinavir">Lasinavir</a></li> <li><a href="/wiki/Emivirine" title="Emivirine">Emivirine</a></li> <li><a href="/wiki/Lersivirine" class="mw-redirect" title="Lersivirine">Lersivirine</a></li> <li><a href="/wiki/Lodenosine" title="Lodenosine">Lodenosine</a></li> <li><a href="/wiki/Loviride" title="Loviride">Loviride</a></li> <li><a href="/wiki/Mozenavir" title="Mozenavir">Mozenavir</a></li> <li><a href="/w/index.php?title=Palinavir&action=edit&redlink=1" class="new" title="Palinavir (page does not exist)">Palinavir</a></li> <li><a href="/w/index.php?title=Telinavir&action=edit&redlink=1" class="new" title="Telinavir (page does not exist)">Telinavir</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div> °<a href="/wiki/United_States_Department_of_Health_and_Human_Services" title="United States Department of Health and Human Services">DHHS</a> <i>recommended</i> <a href="/wiki/Therapy#Lines_of_therapy" title="Therapy">initial regimen options</a>. <sup>◊</sup>Formerly or rarely used agent.<br /></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="GSK201" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:GSK" title="Template:GSK"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GSK" title="Template talk:GSK"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GSK" title="Special:EditPage/Template:GSK"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GSK201" style="font-size:114%;margin:0 4em"><a href="/wiki/GSK_plc" title="GSK plc">GSK</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Subsidiaries</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%">Current</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/GlaxoSmithKline_Pakistan" class="mw-redirect" title="GlaxoSmithKline Pakistan">GlaxoSmithKline Pakistan</a></li> <li><a href="/wiki/GlaxoSmithKline_Pharmaceuticals_Ltd" class="mw-redirect" title="GlaxoSmithKline Pharmaceuticals Ltd">GlaxoSmithKline Pharmaceuticals Ltd</a></li> <li><a href="/wiki/Stiefel_Laboratories" title="Stiefel Laboratories">Stiefel Laboratories</a></li> <li><a href="/wiki/Tesaro" title="Tesaro">Tesaro</a></li> <li><a href="/wiki/ViiV_Healthcare" title="ViiV Healthcare">ViiV Healthcare</a> (85%)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Former</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"><a href="/wiki/Haleon" title="Haleon">Haleon</a></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Predecessors,<br />acquisitions</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/Allen_%26_Hanburys" title="Allen & Hanburys">Allen & Hanburys</a></li> <li><a href="/wiki/Beecham_Group" title="Beecham Group">Beecham Group</a></li> <li><a href="/wiki/Block_Drug" title="Block Drug">Block Drug</a></li> <li><a href="/wiki/GSK_plc#Glaxo_Wellcome" title="GSK plc">Burroughs Wellcome</a></li> <li><a href="/wiki/GSK_plc#Glaxo_Wellcome" title="GSK plc">Glaxo</a></li> <li><a href="/wiki/GSK_plc#Glaxo_Wellcome" title="GSK plc">Glaxo Wellcome</a></li> <li><a href="/wiki/Human_Genome_Sciences" title="Human Genome Sciences">Human Genome Sciences</a></li> <li><a href="/wiki/Recherche_et_Industrie_Th%C3%A9rapeutiques" title="Recherche et Industrie Thérapeutiques">Recherche et Industrie Thérapeutiques</a></li> <li><a href="/wiki/Reliant_Pharmaceuticals" title="Reliant Pharmaceuticals">Reliant Pharmaceuticals</a></li> <li><a href="/wiki/S._E._Massengill_Company" title="S. E. Massengill Company">S. E. Massengill Company</a></li> <li><a href="/wiki/GSK_plc#SmithKline_Beecham" title="GSK plc">SmithKline Beecham</a></li> <li><a href="/wiki/Smith,_Kline_%26_French" title="Smith, Kline & French">Smith, Kline & French</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</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%">Current</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%">Pharma</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/Fluticasone/salmeterol" title="Fluticasone/salmeterol">Advair</a></li> <li><a href="/wiki/Orlistat" title="Orlistat">Alli</a></li> <li><a href="/wiki/Amoxicillin/clavulanic_acid" title="Amoxicillin/clavulanic acid">Augmentin</a></li> <li><a href="/wiki/Rosiglitazone" title="Rosiglitazone">Avandia</a></li> <li><a href="/wiki/Beclometasone" title="Beclometasone">Beconase</a></li> <li><a href="/wiki/Ibandronic_acid" title="Ibandronic acid">Boniva</a></li> <li><a href="/wiki/Fluticasone_propionate" title="Fluticasone propionate">Flixonase</a></li> <li><a href="/wiki/Topotecan" title="Topotecan">Hycamtin</a></li> <li><a href="/wiki/Lamotrigine" title="Lamotrigine">Lamictal</a></li> <li><a href="/wiki/Paroxetine" title="Paroxetine">Paxil/Seroxat</a></li> <li><a href="/wiki/Piboserod" title="Piboserod">Serlipet</a></li> <li><a href="/wiki/Cimetidine" title="Cimetidine">Tagamet</a></li> <li><a href="/wiki/Salbutamol" title="Salbutamol">Ventolin</a></li> <li><a href="/wiki/Bupropion" title="Bupropion">Wellbutrin/Zyban</a></li> <li><a href="/wiki/Ranitidine" title="Ranitidine">Zantac</a> … <a href="/wiki/List_of_GSK_plc_products" title="List of GSK plc products"><b>more</b></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Vaccines</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/Respiratory_syncytial_virus_vaccine" title="Respiratory syncytial virus vaccine">Arexvy</a></li> <li><a href="/wiki/Bexsero" class="mw-redirect" title="Bexsero">Bexsero</a></li> <li><a href="/wiki/Boostrix" class="mw-redirect" title="Boostrix">Boostrix</a></li> <li><a href="/wiki/Cervarix" title="Cervarix">Cervarix</a></li> <li><a href="/wiki/Engerix-B" class="mw-redirect" title="Engerix-B">Engerix-B </a></li> <li><a href="/wiki/Fluarix" class="mw-redirect" title="Fluarix">Fluarix</a></li> <li><a href="/wiki/FluLaval" class="mw-redirect" title="FluLaval">FluLaval</a></li> <li><a href="/wiki/Havrix" class="mw-redirect" title="Havrix">Havrix</a></li> <li><a href="/wiki/Hepatyrix" class="mw-redirect" title="Hepatyrix">Hepatyrix</a></li> <li><a href="/wiki/Hiberix" class="mw-redirect" title="Hiberix">Hiberix</a></li> <li><a href="/wiki/Infanrix" class="mw-redirect" title="Infanrix">Infanrix</a></li> <li><a href="/wiki/H5N1_vaccine" title="H5N1 vaccine">H5N1 vaccine</a></li> <li><a href="/wiki/Kinrix" class="mw-redirect" title="Kinrix">Kinrix</a></li> <li><a href="/wiki/Menveo" class="mw-redirect" title="Menveo">Menveo</a></li> <li><a href="/wiki/Pandemrix" title="Pandemrix">Pandemrix</a></li> <li><a href="/wiki/Pediarix" class="mw-redirect" title="Pediarix">Pediarix</a></li> <li><a href="/wiki/Rabavert" class="mw-redirect" title="Rabavert">Rabavert</a></li> <li><a href="/wiki/Rotarix" class="mw-redirect" title="Rotarix">Rotarix</a></li> <li><a href="/wiki/Zoster_vaccine#Shingrix" title="Zoster vaccine">Shingrix</a></li> <li><a href="/wiki/Hepatitis_A_and_B_vaccine" title="Hepatitis A and B vaccine">Twinrix</a> … <a href="/wiki/List_of_GSK_plc_products" title="List of GSK plc products"><b>more</b></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Former</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/Actifed" title="Actifed">Actifed</a></li> <li>Advil</li> <li><a href="/wiki/Aquafresh" class="mw-redirect" title="Aquafresh">Aquafresh</a></li> <li><a href="/wiki/BC_Powder" title="BC Powder">BC Powder</a></li> <li><a href="/wiki/Biotene" title="Biotene">Biotene</a></li> <li><a href="/wiki/Caltrate" title="Caltrate">Caltrate</a></li> <li><a href="/wiki/Centrum_(multivitamin)" title="Centrum (multivitamin)">Centrum</a></li> <li><a href="/wiki/ChapStick" title="ChapStick">ChapStick</a></li> <li><a href="/wiki/Emergen-C" title="Emergen-C">Emergen-C</a></li> <li><a href="/wiki/Eno_(drug)" title="Eno (drug)">Eno</a></li> <li><a href="/wiki/Excedrin_(brand)" title="Excedrin (brand)">Excedrin</a></li> <li>Flonase</li> <li><a href="/wiki/Geritol" title="Geritol">Geritol</a></li> <li><a href="/wiki/Goody%27s_Powder" title="Goody's Powder">Goody's Powder</a></li> <li><a href="/wiki/Horlicks" title="Horlicks">Horlicks</a></li> <li><a href="/wiki/Lucozade" title="Lucozade">Lucozade</a></li> <li><a href="/wiki/Nicoderm" class="mw-redirect" title="Nicoderm">Nicoderm</a></li> <li><a href="/wiki/Nicorette" title="Nicorette">Nicorette</a></li> <li><a href="/wiki/Niquitin" title="Niquitin">NiQuitin</a></li> <li><a href="/wiki/Parodontax" title="Parodontax">Parodontax</a></li> <li><a href="/wiki/Ribena" title="Ribena">Ribena</a></li> <li><a href="/wiki/Sensodyne" title="Sensodyne">Sensodyne</a></li> <li><a href="/wiki/Tums" title="Tums">Tums</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">People</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%">Board of <br />Directors</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/Philip_Hampton" title="Philip Hampton">Philip Hampton</a></li> <li><a href="/wiki/Emma_Walmsley" title="Emma Walmsley">Emma Walmsley</a></li> <li><a href="/wiki/Simon_Dingemans" title="Simon Dingemans">Simon Dingemans</a></li> <li><a href="/wiki/Roy_M._Anderson" title="Roy M. Anderson">Roy M. Anderson</a></li> <li><a href="/wiki/M._S._Banga" title="M. S. Banga">Manvinder Banga</a></li> <li><a href="/wiki/Patrick_Vallance" title="Patrick Vallance">Patrick Vallance</a></li> <li><a href="/wiki/Vivienne_Cox" title="Vivienne Cox">Vivienne Cox</a></li> <li><a href="/wiki/Lynn_Elsenhans" title="Lynn Elsenhans">Lynn Elsenhans</a></li> <li>Jesse Goodman</li> <li><a href="/wiki/Judy_Lewent" title="Judy Lewent">Judy Lewent</a></li> <li><a href="/wiki/Urs_Rohner" title="Urs Rohner">Urs Rohner</a></li> <li><a href="/wiki/Laurie_Glimcher" title="Laurie Glimcher">Laurie Glimcher</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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thomas_Beecham_(chemist)" title="Thomas Beecham (chemist)">Thomas Beecham</a></li> <li><a href="/wiki/Silas_M._Burroughs_(pharmacist)" title="Silas M. Burroughs (pharmacist)">Silas M. Burroughs</a></li> <li><a href="/wiki/Mahlon_Kline" title="Mahlon Kline">Mahlon Kline</a></li> <li><a href="/wiki/John_K._Smith" title="John K. Smith">John K. Smith</a></li> <li><a href="/wiki/Henry_Wellcome" title="Henry Wellcome">Henry Wellcome</a></li> <li><a href="/wiki/Andrew_Witty" title="Andrew Witty">Andrew Witty</a></li> <li><a href="/wiki/Chris_Gent" title="Chris Gent">Chris Gent</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Litigation</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/Canada_v._GlaxoSmithKline_Inc." class="mw-redirect" title="Canada v. GlaxoSmithKline Inc.">Canada v. GlaxoSmithKline Inc.</a></i></li> <li><i><a href="/wiki/Christopher_v._SmithKline_Beecham_Corp." title="Christopher v. SmithKline Beecham Corp.">Christopher v. SmithKline Beecham Corp.</a></i></li> <li><i><a href="/wiki/GlaxoSmithKline_Services_Unlimited_v_Commission" title="GlaxoSmithKline Services Unlimited v Commission">GlaxoSmithKline Services Unlimited v Commission</a></i></li> <li><i><a href="/wiki/United_States_v._Glaxo_Group_Ltd." title="United States v. Glaxo Group Ltd.">United States v. Glaxo Group Ltd.</a></i></li> <li><i><a href="/wiki/United_States_v._GlaxoSmithKline" title="United States v. GlaxoSmithKline">United States v. GlaxoSmithKline</a></i></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-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Drug_Industry_Documents_Archive" title="Drug Industry Documents Archive">Drug Industry Documents Archive</a></li> <li><a href="/wiki/GlaxoSmithKline_Prize" title="GlaxoSmithKline Prize">GlaxoSmithKline Prize</a></li> <li><i><a href="/wiki/Side_Effects_(Bass_book)" title="Side Effects (Bass book)">Side Effects</a></i></li> <li><a href="/wiki/Study_329" title="Study 329">Study 329</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" 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