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id="toc-Medical_uses-sublist" class="vector-toc-list"> <li id="toc-Organ_transplantation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Organ_transplantation"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.1</span> <span>Organ transplantation</span> </div> </a> <ul id="toc-Organ_transplantation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Skin" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Skin"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.2</span> <span>Skin</span> </div> </a> <ul id="toc-Skin-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Eyes" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Eyes"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.3</span> <span>Eyes</span> </div> </a> <ul id="toc-Eyes-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Contraindications_and_precautions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Contraindications_and_precautions"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Contraindications and precautions</span> </div> </a> <button aria-controls="toc-Contraindications_and_precautions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Contraindications and precautions subsection</span> </button> <ul id="toc-Contraindications_and_precautions-sublist" class="vector-toc-list"> <li id="toc-Topical_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Topical_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Topical use</span> </div> </a> <ul id="toc-Topical_use-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Side effects</span> </div> </a> <button aria-controls="toc-Side_effects-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Side effects subsection</span> </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-By_mouth_or_intravenous_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#By_mouth_or_intravenous_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>By mouth or intravenous use</span> </div> </a> <ul id="toc-By_mouth_or_intravenous_use-sublist" class="vector-toc-list"> <li id="toc-Carcinogenesis_and_mutagenesis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Carcinogenesis_and_mutagenesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1.1</span> <span>Carcinogenesis and mutagenesis</span> </div> </a> <ul id="toc-Carcinogenesis_and_mutagenesis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Topical_use_2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Topical_use_2"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Topical use</span> </div> </a> <ul id="toc-Topical_use_2-sublist" class="vector-toc-list"> <li id="toc-Cancer_risks" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Cancer_risks"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2.1</span> <span>Cancer risks</span> </div> </a> <ul id="toc-Cancer_risks-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Interactions</span> </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacogenetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacogenetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Pharmacogenetics</span> </div> </a> <ul id="toc-Pharmacogenetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Available_forms" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Available_forms"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Available forms</span> </div> </a> <ul id="toc-Available_forms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Research</span> </div> </a> <button aria-controls="toc-Research-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Research subsection</span> </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Lupus_nephritis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lupus_nephritis"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Lupus nephritis</span> </div> </a> <ul id="toc-Lupus_nephritis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ulcerative_colitis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ulcerative_colitis"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Ulcerative colitis</span> </div> </a> <ul id="toc-Ulcerative_colitis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</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 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Available in 28 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-28" 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">28 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%AA%D8%A7%D9%83%D8%B1%D9%88%D9%84%D9%8A%D9%85%D8%B3" title="تاكروليمس – Arabic" lang="ar" hreflang="ar" data-title="تاكروليمس" 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%AA%D8%A7%DA%A9%D8%B1%D9%88%D9%84%DB%8C%D9%85%D9%88%D8%B3" title="تاکرولیموس – South Azerbaijani" lang="azb" hreflang="azb" data-title="تاکرولیموس" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Tacrolim%C3%BAs" title="Tacrolimús – Catalan" lang="ca" hreflang="ca" data-title="Tacrolimús" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Takrolimus" title="Takrolimus – Czech" lang="cs" hreflang="cs" data-title="Takrolimus" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Tacrolimws" title="Tacrolimws – Welsh" lang="cy" hreflang="cy" data-title="Tacrolimws" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Tacrolimus" title="Tacrolimus – German" lang="de" hreflang="de" data-title="Tacrolimus" 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/Tacr%C3%B3limus" title="Tacrólimus – Spanish" lang="es" hreflang="es" data-title="Tacrólimus" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%AA%D8%A7%DA%A9%D8%B1%D9%88%D9%84%DB%8C%D9%85%D9%88%D8%B3" title="تاکرولیموس – Persian" lang="fa" hreflang="fa" data-title="تاکرولیموس" 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/Tacrolimus" title="Tacrolimus – French" lang="fr" hreflang="fr" data-title="Tacrolimus" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Takrolimus" title="Takrolimus – Indonesian" lang="id" hreflang="id" data-title="Takrolimus" 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/Tacrolimus" title="Tacrolimus – Italian" lang="it" hreflang="it" data-title="Tacrolimus" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%98%D7%A7%D7%A8%D7%95%D7%9C%D7%99%D7%9E%D7%95%D7%A1" title="טקרולימוס – Hebrew" lang="he" hreflang="he" data-title="טקרולימוס" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Takrolimusz" title="Takrolimusz – Hungarian" lang="hu" hreflang="hu" data-title="Takrolimusz" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A2%D0%B0%D0%BA%D1%80%D0%BE%D0%BB%D0%B8%D0%BC%D1%83%D1%81" title="Такролимус – Macedonian" lang="mk" hreflang="mk" data-title="Такролимус" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Tacrolimus" title="Tacrolimus – Dutch" lang="nl" hreflang="nl" data-title="Tacrolimus" 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%BF%E3%82%AF%E3%83%AD%E3%83%AA%E3%83%A0%E3%82%B9" title="タクロリムス – Japanese" lang="ja" hreflang="ja" data-title="タクロリムス" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%9F%E0%AC%BE%E0%AC%95%E0%AD%8D%E0%AC%B0%E0%AD%8B%E0%AC%B2%E0%AC%BF%E0%AC%AE%E0%AC%B8" title="ଟାକ୍ରୋଲିମସ – Odia" lang="or" hreflang="or" data-title="ଟାକ୍ରୋଲିମସ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Takrolimus" title="Takrolimus – Polish" lang="pl" hreflang="pl" data-title="Takrolimus" 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/Tacrolimo" title="Tacrolimo – Portuguese" lang="pt" hreflang="pt" data-title="Tacrolimo" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A2%D0%B0%D0%BA%D1%80%D0%BE%D0%BB%D0%B8%D0%BC%D1%83%D1%81" title="Такролимус – Russian" lang="ru" hreflang="ru" data-title="Такролимус" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Takrolimus" title="Takrolimus – Serbian" lang="sr" hreflang="sr" data-title="Takrolimus" 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/Takrolimus" title="Takrolimus – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Takrolimus" 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/Takrolimuusi" title="Takrolimuusi – Finnish" lang="fi" hreflang="fi" data-title="Takrolimuusi" 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/Takrolimus" title="Takrolimus – Swedish" lang="sv" hreflang="sv" data-title="Takrolimus" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Takrolimus" title="Takrolimus – Turkish" lang="tr" hreflang="tr" data-title="Takrolimus" 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%A2%D0%B0%D0%BA%D1%80%D0%BE%D0%BB%D1%96%D0%BC%D1%83%D1%81" title="Такролімус – Ukrainian" lang="uk" hreflang="uk" data-title="Такролімус" 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/Tacrolimus" title="Tacrolimus – Vietnamese" lang="vi" hreflang="vi" data-title="Tacrolimus" 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/%E4%BB%96%E5%85%8B%E8%8E%AB%E5%8F%B8" title="他克莫司 – Chinese" lang="zh" hreflang="zh" data-title="他克莫司" 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class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Immunosuppressive drug</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): Tacrolimus">Tacrolimus</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Tacrolimus2DCSD.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Tacrolimus2DCSD.svg/250px-Tacrolimus2DCSD.svg.png" decoding="async" width="250" height="225" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/68/Tacrolimus2DCSD.svg/375px-Tacrolimus2DCSD.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/68/Tacrolimus2DCSD.svg/500px-Tacrolimus2DCSD.svg.png 2x" data-file-width="1496" data-file-height="1344" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Tacrolimus-1YAT-ball-and-stick-model.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Tacrolimus-1YAT-ball-and-stick-model.png/250px-Tacrolimus-1YAT-ball-and-stick-model.png" decoding="async" width="250" height="200" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/40/Tacrolimus-1YAT-ball-and-stick-model.png/375px-Tacrolimus-1YAT-ball-and-stick-model.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/40/Tacrolimus-1YAT-ball-and-stick-model.png/500px-Tacrolimus-1YAT-ball-and-stick-model.png 2x" data-file-width="1819" data-file-height="1457" /></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">Prograf, Advagraf, Protopic, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">FK-506, fujimycin</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/tacrolimus.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/a601117.html">a601117</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Tacrolimus">Tacrolimus</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> C<sup id="cite_ref-Drugs.com_pregnancy_1-0" class="reference"><a href="#cite_note-Drugs.com_pregnancy-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li> <li 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/Topical_administration" class="mw-redirect" title="Topical administration">Topical</a>, <a href="/wiki/Oral_administration" title="Oral administration">by mouth</a>, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_D11" title="ATC code D11">D11AH01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D11AH01">WHO</a></span>) <br /><a href="/wiki/ATC_code_L04" title="ATC code L04">L04AD02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L04AD02">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="Canada">CA</abbr></small>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a><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="United States">US</abbr>:</small> <a href="/wiki/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_2-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>Rx-only<sup id="cite_ref-Prograf_FDA_label_4-0" class="reference"><a href="#cite_note-Prograf_FDA_label-4"><span class="cite-bracket">[</span>4<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-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></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">24% (5–67%), less after eating food rich in fat</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">≥98.8%</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> <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>, <a href="/wiki/CYP3A5" title="CYP3A5">CYP3A5</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">11.3 h for transplant patients (range 3.5–40.6 h)</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">Mostly fecal</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<i>S</i>,4<i>R</i>,5<i>S</i>,8<i>R</i>,9<i>E</i>,12<i>S</i>,14<i>S</i>,15<i>R</i>,16<i>S</i>,18<i>R</i>,26a<i>S</i>)-8-allyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-{(<i>E</i>)-2-[(1<i>R</i>,3<i>R</i>,4<i>R</i>)-4-hydroxy-3-methylcyclohexyl]-1-methylvinyl}-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3<i>H</i>-pyrido[2,1-<i>c</i>] [1,4]oxaazacyclotricosane-1,7,20,21(4<i>H</i>,23<i>H</i>)-tetrone</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=104987-11-3">104987-11-3</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/445643">445643</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/DB00864">DB00864</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.393220.html">393220</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/Y5L2157C4J">Y5L2157C4J</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/D08556">D08556</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00107">D00107</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:61049">CHEBI:61049</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL269732">ChEMBL269732</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/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>FK5 (<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=FK5">PDBe</a></span>, <span title="www.rcsb.org"><a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/FK5">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/DTXSID5046354">DTXSID5046354</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q411648#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/100.155.367">100.155.367</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q411648#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>44</sub><span title="Hydrogen">H</span><sub>69</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>12</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="7002804031000000000♠"></span>804.031</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%28C%29%5BC%40%40H%5D1%5BC%40%40%5D2%28O%5BC%40%5D%28O%29%28%5BC%40H%5D%28C%29C1%29C%28%3DO%29C%28%3DO%29N3%5BC%40%5D%28C%28%3DO%29O%5BC%40H%5D%28%5CC%28%3DC%5C%5BC%40H%5D4C%5BC%40%40H%5D%28OC%29%5BC%40H%5D%28O%29CC4%29%5CC%29%5BC%40H%5D%28C%29%5BC%40%40H%5D%28O%29CC%28%3DO%29%5BC%40H%5D%28CC%3DC%29%2FC%3DC%28%5CC%29%2FC%5BC%40H%5D%28C%29C%5BC%40%40H%5D2OC%29%28CCCC3%29%5BH%5D%29%5BH%5D">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O(C)[C@@H]1[C@@]2(O[C@](O)([C@H](C)C1)C(=O)C(=O)N3[C@](C(=O)O[C@H](\C(=C\[C@H]4C[C@@H](OC)[C@H](O)CC4)\C)[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(\C)/C[C@H](C)C[C@@H]2OC)(CCCC3)[H])[H]</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/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/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:QJJXYPPXXYFBGM-LFZNUXCKSA-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=461746192&page2=Tacrolimus">(verify)</a></span></span></td></tr></tbody></table> <p><b>Tacrolimus</b>, sold under the brand name <b>Prograf</b> among others, is an <a href="/wiki/Immunosuppressive_drug" title="Immunosuppressive drug">immunosuppressive drug</a>. After <a href="/wiki/Allotransplantation" title="Allotransplantation">allogenic</a> <a href="/wiki/Organ_transplant" class="mw-redirect" title="Organ transplant">organ transplant</a>, the risk of organ <a href="/wiki/Transplant_rejection" title="Transplant rejection">rejection</a> is moderate. To lower the risk of organ rejection, tacrolimus is given. The drug can also be sold as a <a href="/wiki/Topical_medication" title="Topical medication">topical medication</a> in the treatment of T cell-mediated diseases such as <a href="/wiki/Atopic_dermatitis" title="Atopic dermatitis">eczema</a> and <a href="/wiki/Psoriasis" title="Psoriasis">psoriasis</a>. For example, it is prescribed for severe refractory <a href="/wiki/Uveitis" title="Uveitis">uveitis</a> after a <a href="/wiki/Bone_marrow" title="Bone marrow">bone marrow</a> transplant, exacerbations of <a href="/wiki/Minimal_change_disease" title="Minimal change disease">minimal change disease</a>, <a href="/wiki/Kimura%27s_disease" title="Kimura's disease">Kimura's disease</a>, and <a href="/wiki/Vitiligo" title="Vitiligo">vitiligo</a>. It can be used to treat <a href="/wiki/Dry_eye_syndrome#Other" title="Dry eye syndrome">dry eye syndrome</a> in cats and dogs.<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><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Tacrolimus inhibits <a href="/wiki/Calcineurin" title="Calcineurin">calcineurin</a>, which is involved in the production of <a href="/wiki/Interleukin-2" class="mw-redirect" title="Interleukin-2">interleukin-2</a>, a <a href="/wiki/Molecule" title="Molecule">molecule</a> that promotes the development and <a href="/wiki/Cell_proliferation" title="Cell proliferation">proliferation</a> of <a href="/wiki/T_cell" title="T cell">T cells</a>, as part of the body's learned (or <a href="/wiki/Adaptive_immune_response" class="mw-redirect" title="Adaptive immune response">adaptive</a>) immune response. </p><p>Chemically, it is a <a href="/wiki/Macrolide" title="Macrolide">macrolide</a> <a href="/wiki/Lactone" title="Lactone">lactone</a><sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> that was first discovered in 1987, from the fermentation broth of a <a href="/wiki/Japan" title="Japan">Japanese</a> <a href="/wiki/Soil" title="Soil">soil</a> sample that contained the <a href="/wiki/Bacterium" class="mw-redirect" title="Bacterium">bacterium</a> <i><a href="/wiki/Streptomyces_tsukubensis" title="Streptomyces tsukubensis">Streptomyces tsukubensis</a></i>. 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> In 2021, it was the 296th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.<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> </p> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <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=Tacrolimus&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="Organ_transplantation">Organ transplantation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=2" title="Edit section: Organ transplantation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It has similar immunosuppressive properties to <a href="/wiki/Ciclosporin" title="Ciclosporin">ciclosporin</a>, but is much more potent. Immunosuppression with tacrolimus was associated with a significantly lower rate of acute rejection compared with ciclosporin-based immunosuppression (30.7% vs 46.4%) in one study.<sup id="cite_ref-Medscape2004-McCauley_13-0" class="reference"><a href="#cite_note-Medscape2004-McCauley-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Clinical outcome is better with tacrolimus than with ciclosporin during the first year of liver transplantation.<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><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> Long-term outcome has not been improved to the same extent. Tacrolimus is normally prescribed as part of a post-transplant cocktail including <a href="/wiki/Corticosteroids" class="mw-redirect" title="Corticosteroids">steroids</a>, <a href="/wiki/Mycophenolate" class="mw-redirect" title="Mycophenolate">mycophenolate</a>, and <a href="/wiki/IL-2_receptor" title="IL-2 receptor">IL-2 receptor</a> inhibitors such as <a href="/wiki/Basiliximab" title="Basiliximab">basiliximab</a>. Dosages are titrated to target blood levels at specific times after medication administration.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Skin">Skin</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=3" title="Edit section: Skin"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Eczema#Medications" class="mw-redirect" title="Eczema">Medications used in treatment of eczema</a></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Protopic.JPG" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Protopic.JPG/250px-Protopic.JPG" decoding="async" width="220" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Protopic.JPG/330px-Protopic.JPG 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Protopic.JPG/500px-Protopic.JPG 2x" data-file-width="3648" data-file-height="2432" /></a><figcaption>Tacrolimus 0.1% Ointment</figcaption></figure> <p>As an <a href="/wiki/Ointment" class="mw-redirect" title="Ointment">ointment</a>, tacrolimus is used in the treatment of <a href="/wiki/Dermatitis" title="Dermatitis">dermatitis</a> (eczema), in particular <a href="/wiki/Atopic_dermatitis" title="Atopic dermatitis">atopic dermatitis</a>, if topical corticosteroids and moisturisers fail in helping.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cancer_risk_with_topical_calcineuri_18-0" class="reference"><a href="#cite_note-Cancer_risk_with_topical_calcineuri-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> It suppresses inflammation in a similar way to <a href="/wiki/Steroid" title="Steroid">steroids</a>, and is equally as effective as a mid-potency steroid. An important advantage of tacrolimus is that, unlike steroids, it does not cause skin thinning (<a href="/wiki/Atrophy" title="Atrophy">atrophy</a>), or other steroid related side effects.<sup id="cite_ref-AC-Protopic_19-0" class="reference"><a href="#cite_note-AC-Protopic-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Cancer_risk_with_topical_calcineuri_18-1" class="reference"><a href="#cite_note-Cancer_risk_with_topical_calcineuri-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>It is applied on the active lesions until they heal off, but may also be used continuously in low doses (twice a week), and applied to the thinner skin over the face and eyelids.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2008)">citation needed</span></a></i>]</sup> Clinical trials of up to one year have been conducted. Recently it has also been used to treat segmental <a href="/wiki/Vitiligo" title="Vitiligo">vitiligo</a> in children, especially in areas on the face.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Eyes">Eyes</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=4" title="Edit section: Eyes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tacrolimus solution, as drops, is sometimes prescribed by veterinarians for <a href="/wiki/Keratoconjunctivitis" title="Keratoconjunctivitis">keratoconjunctivitis</a>, and other <a href="/wiki/Dry_eye" class="mw-redirect" title="Dry eye">dry eye</a> maladies, in the eyes of domestic <a href="/wiki/Cat" title="Cat">cats</a>, <a href="/wiki/Dog" title="Dog">dogs</a>, and <a href="/wiki/Horse" title="Horse">horses</a>.<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> It has been studied for use in human eyes.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Contraindications_and_precautions">Contraindications and precautions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=5" title="Edit section: Contraindications and precautions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Contraindications and precautions include:<sup id="cite_ref-AC_24-0" class="reference"><a href="#cite_note-AC-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Hepatic" class="mw-redirect" title="Hepatic">Hepatic</a> disease</li> <li>Immunosuppression</li> <li><a href="/wiki/Infant" title="Infant">Infants</a></li> <li><a href="/wiki/Infection" title="Infection">Infection</a></li> <li><a href="/wiki/Neoplastic" class="mw-redirect" title="Neoplastic">Neoplastic</a> disease, such as: <ul><li><a href="/wiki/Skin_cancer" title="Skin cancer">Skin cancer</a></li> <li><a href="/wiki/Lung_cancer" title="Lung cancer">Lung cancer</a></li></ul></li> <li><a href="/wiki/Oliguria" title="Oliguria">Oliguria</a></li> <li><a href="/wiki/Pregnancy" title="Pregnancy">Pregnancy</a></li> <li><a href="/wiki/QT_interval" title="QT interval">QT interval</a> prolongation</li> <li><a href="/wiki/Sunlight" title="Sunlight">Sunlight</a> (<a href="/wiki/UV" class="mw-redirect" title="UV">UV</a>) exposure</li> <li><a href="/wiki/Grapefruit" title="Grapefruit">Grapefruit</a> juice<sup id="cite_ref-DrugMetab-Fukatsu_25-0" class="reference"><a href="#cite_note-DrugMetab-Fukatsu-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Topical_use">Topical use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=6" title="Edit section: Topical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>Occlusive dressing</li> <li>Known or suspected malignant lesions</li> <li><a href="/wiki/Netherton%27s_syndrome" class="mw-redirect" title="Netherton's syndrome">Netherton's syndrome</a> or similar skin diseases</li> <li>Certain skin infections<sup id="cite_ref-AC-Protopic_19-1" class="reference"><a href="#cite_note-AC-Protopic-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup></li></ul> <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=Tacrolimus&action=edit&section=7" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="By_mouth_or_intravenous_use">By mouth or intravenous use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=8" title="Edit section: By mouth or intravenous use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Side effects can be severe and include <a href="/wiki/Infection" title="Infection">infection</a>, cardiac damage, <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Blurred_vision" title="Blurred vision">blurred vision</a>, liver and <a href="/wiki/Kidney" title="Kidney">kidney</a> problems (tacrolimus <a href="/wiki/Nephrotoxicity" title="Nephrotoxicity">nephrotoxicity</a>),<sup id="cite_ref-pmid19218475_26-0" class="reference"><a href="#cite_note-pmid19218475-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Hyperkalemia" title="Hyperkalemia">hyperkalemia</a>, <a href="/wiki/Hypomagnesemia" class="mw-redirect" title="Hypomagnesemia">hypomagnesemia</a>, <a href="/wiki/Hyperglycemia" title="Hyperglycemia">hyperglycemia</a>, <a href="/wiki/Diabetes_mellitus" class="mw-redirect" title="Diabetes mellitus">diabetes mellitus</a>, <a href="/wiki/Itch" title="Itch">itching</a>, lung damage (<a href="/wiki/Sirolimus" title="Sirolimus">sirolimus</a> also causes lung damage),<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> and various neuropsychiatric problems such as loss of appetite, <a href="/wiki/Insomnia" title="Insomnia">insomnia</a>, <a href="/wiki/Posterior_reversible_encephalopathy_syndrome" title="Posterior reversible encephalopathy syndrome">posterior reversible encephalopathy syndrome</a>, confusion, weakness, <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>, vivid nightmares, <a href="/wiki/Cramp" title="Cramp">cramps</a>, <a href="/wiki/Neuropathy" class="mw-redirect" title="Neuropathy">neuropathy</a>, <a href="/wiki/Seizure" title="Seizure">seizures</a>, <a href="/wiki/Tremor" title="Tremor">tremors</a>, and <a href="/wiki/Catatonia" title="Catatonia">catatonia</a>.<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>In addition, it may potentially increase the severity of existing fungal or infectious conditions such as <a href="/wiki/Varicella-zoster_virus" class="mw-redirect" title="Varicella-zoster virus">herpes zoster</a> or <a href="/wiki/Polyomavirus" class="mw-redirect" title="Polyomavirus">polyoma</a> viral infections.<sup id="cite_ref-AC_24-1" class="reference"><a href="#cite_note-AC-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Carcinogenesis_and_mutagenesis">Carcinogenesis and mutagenesis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=9" title="Edit section: Carcinogenesis and mutagenesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In people receiving immunosuppressants to reduce transplant graft rejection, an increased risk of malignancy (cancer) is a recognised complication.<sup id="cite_ref-AC_24-2" class="reference"><a href="#cite_note-AC-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The most common cancers are <a href="/wiki/Non-Hodgkin%27s_lymphoma" class="mw-redirect" title="Non-Hodgkin's lymphoma">non-Hodgkin's lymphoma</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> and <a href="/wiki/Skin_cancer" title="Skin cancer">skin cancers</a>. The risk appears to be related to the intensity and duration of treatment. </p> <div class="mw-heading mw-heading3"><h3 id="Topical_use_2">Topical use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=10" title="Edit section: Topical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The most common adverse events associated with the use of topical tacrolimus ointments, especially if used over a wide area, include a burning or itching sensation on the initial applications, with increased sensitivity to sunlight and heat on the affected areas.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2022)">citation needed</span></a></i>]</sup> Less common are <a href="/wiki/Flu-like_symptoms" class="mw-redirect" title="Flu-like symptoms">flu-like symptoms</a>, headache, cough, and burning eyes.<sup id="cite_ref-JAcadDerm-Hanifin_30-0" class="reference"><a href="#cite_note-JAcadDerm-Hanifin-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Cancer_risks">Cancer risks</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=11" title="Edit section: Cancer risks"><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">Further information: <a href="/wiki/Eczema#Medications" class="mw-redirect" title="Eczema">Eczema § Medications</a></div> <p>Tacrolimus and a related drug for eczema (<a href="/wiki/Pimecrolimus" title="Pimecrolimus">pimecrolimus</a>) were suspected of carrying a cancer risk, though the matter is still a subject of controversy. The FDA issued a health warning in March 2005 for the drug, based on animal models and a small number of patients. Until further human studies yield more conclusive results, the FDA recommends that users be advised of the potential risks. However, current practice by <a href="/wiki/United_Kingdom" title="United Kingdom">UK</a> dermatologists is not to consider this a significant real concern and they are increasingly recommending the use of these new drugs.<sup id="cite_ref-BAD2002_31-0" class="reference"><a href="#cite_note-BAD2002-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> A 2023 systematic review and meta-analysis published in <a href="/wiki/The_Lancet_Child_%26_Adolescent_Health" class="mw-redirect" title="The Lancet Child & Adolescent Health">The Lancet Child & Adolescent Health</a> concluded with moderate-certainty evidence that the two drugs were not associated with any increased risk of cancer.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=12" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Also like cyclosporin, it has a wide range of interactions. Tacrolimus is primarily metabolised by the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> system of liver enzymes, and there are many substances that interact with this system and induce or inhibit the system's metabolic activity.<sup id="cite_ref-AC_24-3" class="reference"><a href="#cite_note-AC-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Interactions include that with <a href="/wiki/Grapefruit" title="Grapefruit">grapefruit</a> which increases tacrolimus plasma concentrations. As infections are a major cause of morbidity and mortality in the post-transplant patient, the most commonly<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (October 2016)">citation needed</span></a></i>]</sup> reported interactions include interactions with anti-microbial drugs. Macrolide antibiotics including <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a> and <a href="/wiki/Clarithromycin" title="Clarithromycin">clarithromycin</a>, as well as several of the newer classes of antifungals, especially of the azole class (<a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a>, <a href="/wiki/Voriconazole" title="Voriconazole">voriconazole</a>), increase tacrolimus levels by competing for cytochrome enzymes.<sup id="cite_ref-AC_24-4" class="reference"><a href="#cite_note-AC-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=13" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=14" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:PDB_1fkk_EBI.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/PDB_1fkk_EBI.jpg/220px-PDB_1fkk_EBI.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/87/PDB_1fkk_EBI.jpg/330px-PDB_1fkk_EBI.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/87/PDB_1fkk_EBI.jpg/440px-PDB_1fkk_EBI.jpg 2x" data-file-width="800" data-file-height="600" /></a><figcaption><a href="/wiki/FKBP12" class="mw-redirect" title="FKBP12">FKBP12</a>, the target protein of tacrolimus</figcaption></figure> <p>Tacrolimus is a <a href="/wiki/Macrolide" title="Macrolide">macrolide</a> <a href="/wiki/Calcineurin_inhibitor" class="mw-redirect" title="Calcineurin inhibitor">calcineurin inhibitor</a>. In <a href="/wiki/T_cells" class="mw-redirect" title="T cells">T cells</a>, activation of the T cell receptor normally increases intracellular calcium, which acts via <a href="/wiki/Calmodulin" title="Calmodulin">calmodulin</a> to activate <a href="/wiki/Calcineurin" title="Calcineurin">calcineurin</a>. Calcineurin then dephosphorylates the transcription factor <a href="/wiki/NFAT" title="NFAT">nuclear factor of activated T cells</a> (NF-AT), which moves to the nucleus of the T cell and increases the activity of genes coding for IL-2 and related cytokines. Tacrolimus prevents the dephosphorylation of NF-AT.<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> </p><p>In detail, tacrolimus reduces <a href="/wiki/Peptidylprolyl_isomerase_A" title="Peptidylprolyl isomerase A">peptidylprolyl isomerase</a> activity by binding to the immunophilin <a href="/wiki/FKBP12" class="mw-redirect" title="FKBP12">FKBP12</a> (FK506 binding protein), creating a new complex. This FKBP12–FK506 complex interacts with and inhibits calcineurin, thus inhibiting both T <a href="/wiki/Lymphocyte" title="Lymphocyte">lymphocyte</a> signal transduction and IL-2 transcription.<sup id="cite_ref-Cell1991-Liu_34-0" class="reference"><a href="#cite_note-Cell1991-Liu-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> Although this activity is similar to that of cyclosporin, the incidence of acute rejection is reduced by tacrolimus use over cyclosporin use.<sup id="cite_ref-Medscape2004-McCauley_13-1" class="reference"><a href="#cite_note-Medscape2004-McCauley-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Although short-term immunosuppression concerning patient and graft survival is found to be similar between the two drugs, tacrolimus results in a more favorable lipid profile, and this may have important long-term implications given the prognostic influence of rejection on graft survival.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=15" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oral tacrolimus is slowly absorbed in the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a>, with a total <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> of 20 to 25% (but with variations from 5 to 67%) and <a href="/wiki/Cmax_(pharmacology)" title="Cmax (pharmacology)">highest blood plasma concentrations</a> (C<sub>max</sub>) reached after one to three hours. Taking the drug together with a meal, especially one rich in fat, slows down resorption and reduces bioavailability. In the blood, tacrolimus is mainly bound to <a href="/wiki/Erythrocyte" class="mw-redirect" title="Erythrocyte">erythrocytes</a>; only 5% are found in the <a href="/wiki/Blood_plasma" title="Blood plasma">plasma</a>, of which more than 98.8% are bound to <a href="/wiki/Plasma_protein" title="Plasma protein">plasma proteins</a>.<sup id="cite_ref-AC_24-5" class="reference"><a href="#cite_note-AC-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dinnendahl_36-0" class="reference"><a href="#cite_note-Dinnendahl-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>The substance is metabolized in the liver, mainly via <a href="/wiki/CYP3A" title="CYP3A">CYP3A</a>, and in the intestinal wall. All <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> found in the circulation are inactive. <a href="/wiki/Biological_half-life" title="Biological half-life">Biological half-life</a> varies widely and seems to be higher for healthy persons (43 hours on average) than for patients with liver transplants (12 hours) or kidney transplants (16 hours), due to differences in <a href="/wiki/Clearance_(pharmacology)" title="Clearance (pharmacology)">clearance</a>. Tacrolimus is predominantly eliminated via the faeces in form of its metabolites.<sup id="cite_ref-AC_24-6" class="reference"><a href="#cite_note-AC-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Dinnendahl_36-1" class="reference"><a href="#cite_note-Dinnendahl-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>When applied locally on eczema, tacrolimus has little to no bioavailability.<sup id="cite_ref-AC_24-7" class="reference"><a href="#cite_note-AC-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacogenetics">Pharmacogenetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=16" title="Edit section: Pharmacogenetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The predominant enzyme responsible for metabolism of tacrolimus is <a href="/wiki/CYP3A5" title="CYP3A5">CYP3A5</a>. <a href="/wiki/Genetic_variation" title="Genetic variation">Genetic variations</a> within <i>CYP3A5</i> that result in changes to the activity of the CYP3A5 protein can affect concentrations of tacrolimus within the body. In particular, individuals who are <a href="/wiki/Homozygous" class="mw-redirect" title="Homozygous">homozygous</a> for the G <a href="/wiki/Allele" title="Allele">allele</a> at the <a href="/wiki/Single_nucleotide_polymorphism" class="mw-redirect" title="Single nucleotide polymorphism">single nucleotide polymorphism</a> (SNP) rs776746 (also known as CYP3A5 *3/*3) have a non-functional CYP3A5 protein. The frequency of the G allele varies worldwide, from 4% in some African populations to 80–90% in Caucasian populations.<sup id="cite_ref-Bains2012_37-0" class="reference"><a href="#cite_note-Bains2012-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Across a large number of studies, individuals homozygous for the G allele have been shown to have higher concentrations of tacrolimus and require lower doses of the drug, as compared to individuals who are not homozygous for the G allele. Achieving target concentrations of tacrolimus is important – if levels are too low, then there is a risk of <a href="/wiki/Transplant_rejection" title="Transplant rejection">transplant rejection</a>, if levels are too high, there is a risk of drug toxicities. There is evidence to suggest that dosing patients based on rs776746 <a href="/wiki/Genotype" title="Genotype">genotype</a> can result in faster and more frequent achievement of target tacrolimus levels. However, there is a lack of consistent evidence as to whether dosing based on rs776746 genotype results in improved clinical outcomes (such as a decreased risk for transplant rejection or drug toxicities), likely because patients taking tacrolimus are subject to <a href="/wiki/Therapeutic_drug_monitoring" title="Therapeutic drug monitoring">therapeutic drug monitoring</a>.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><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>Studies have shown that genetic polymorphisms of genes other than CYP3A5, such as NR1I2<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> (encoding <a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor">PXR</a>), also significantly influence the pharmacokinetics of tacrolimus. </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=Tacrolimus&action=edit&section=17" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tacrolimus was discovered in 1987; it was among the first macrolide immunosuppressants discovered, preceded by the discovery of <a href="/wiki/Rapamycin" class="mw-redirect" title="Rapamycin">rapamycin</a> (sirolimus) on <a href="/wiki/Rapa_Nui" class="mw-redirect" title="Rapa Nui">Rapa Nui</a> (Easter Island) in 1975.<sup id="cite_ref-JAntibiot1987-Kino_44-0" class="reference"><a href="#cite_note-JAntibiot1987-Kino-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> It is produced by a soil bacterium, <i>Streptomyces tsukubensis</i>.<sup id="cite_ref-DrugDiscovToday2005-Pritchard_45-0" class="reference"><a href="#cite_note-DrugDiscovToday2005-Pritchard-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> The name tacrolimus is derived from "<a href="/wiki/Mount_Tsukuba" title="Mount Tsukuba">Tsukuba</a> macrolide immunosuppressant".<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> </p><p>The early development (investigational new drug phase) of tacrolimus, called at the time by the development code FK-506, happened in the next several years. A firsthand account of that process is given in <a href="/wiki/Thomas_Starzl" title="Thomas Starzl">Thomas Starzl</a>'s 1992 memoir.<sup id="cite_ref-Starzl-1992-chap-25_47-0" class="reference"><a href="#cite_note-Starzl-1992-chap-25-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>Tacrolimus was first <a href="/wiki/FDA_approval" class="mw-redirect" title="FDA approval">approved</a> by the US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) in 1994,<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> for use in <a href="/wiki/Liver_transplantation" title="Liver transplantation">liver transplantation</a>; the indications were extended to include kidney transplants.<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> Generic versions of tacrolimus were approved in the US in 2017.<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><p>Tacrolimus was approved for medical use in the European Union in 2002, for the treatment of moderate to severe atopic dermatitis.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> In 2007, the indications were expanded to include the prophylaxis of transplant rejection in adult kidney or liver allograft recipients and the treatment of allograft rejection resistant to treatment with other immunosuppressive medicinal products in adults.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> In 2009, the indications were expanded to include the prophylaxis of transplant rejection in adult and paediatric, kidney, liver or heart allograft recipients and the treatment of allograft rejection resistant to treatment with other immunosuppressive medicinal products in adults and children.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Available_forms">Available forms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=18" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A branded version of the drug is owned by <a href="/wiki/Astellas_Pharma" title="Astellas Pharma">Astellas Pharma</a>, and is sold under the brand name Prograf, given twice daily. A number of other manufacturers hold marketing authorisation for alternative brands of the twice-daily formulation.<sup id="cite_ref-BNFonline_55-0" class="reference"><a href="#cite_note-BNFonline-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>Once-daily formulations with marketing authorisation include Advagraf (Astellas Pharma) and Envarsus (marketed as Envarsus XR in US by <a href="/wiki/Veloxis_Pharmaceuticals" title="Veloxis Pharmaceuticals">Veloxis Pharmaceuticals</a> and marketed in Europe by <a href="/wiki/Chiesi_Farmaceutici_S.p.A." class="mw-redirect" title="Chiesi Farmaceutici S.p.A.">Chiesi</a>).<sup id="cite_ref-BNFonline_55-1" class="reference"><a href="#cite_note-BNFonline-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> These formulations are intended to reduce pharmacokinetic variation in blood levels and facilitate compliance with dosing.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (April 2020)">citation needed</span></a></i>]</sup> </p><p>The topical formulation is marketed by <a href="/wiki/LEO_Pharma" class="mw-redirect" title="LEO Pharma">LEO Pharma</a> under the name <b>Protopic</b>.<sup id="cite_ref-BNFonline_55-2" class="reference"><a href="#cite_note-BNFonline-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=19" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Tacrolimus_biosynthesis_part_1.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Tacrolimus_biosynthesis_part_1.tif/lossy-page1-300px-Tacrolimus_biosynthesis_part_1.tif.jpg" decoding="async" width="300" height="438" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Tacrolimus_biosynthesis_part_1.tif/lossy-page1-450px-Tacrolimus_biosynthesis_part_1.tif.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ec/Tacrolimus_biosynthesis_part_1.tif/lossy-page1-600px-Tacrolimus_biosynthesis_part_1.tif.jpg 2x" data-file-width="2143" data-file-height="3131" /></a></span> <span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Tacrolimus_biosynthesis_part_2.tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Tacrolimus_biosynthesis_part_2.tif/lossy-page1-300px-Tacrolimus_biosynthesis_part_2.tif.jpg" decoding="async" width="300" height="422" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/30/Tacrolimus_biosynthesis_part_2.tif/lossy-page1-450px-Tacrolimus_biosynthesis_part_2.tif.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/30/Tacrolimus_biosynthesis_part_2.tif/lossy-page1-600px-Tacrolimus_biosynthesis_part_2.tif.jpg 2x" data-file-width="2118" data-file-height="2976" /></a></span> <span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Tacrolimus_biosynthesis_part_3..tif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Tacrolimus_biosynthesis_part_3..tif/lossy-page1-300px-Tacrolimus_biosynthesis_part_3..tif.jpg" decoding="async" width="300" height="497" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Tacrolimus_biosynthesis_part_3..tif/lossy-page1-450px-Tacrolimus_biosynthesis_part_3..tif.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f1/Tacrolimus_biosynthesis_part_3..tif/lossy-page1-600px-Tacrolimus_biosynthesis_part_3..tif.jpg 2x" data-file-width="1866" data-file-height="3093" /></a></span> </p><p>The biosynthesis of tacrolimus is hybrid synthesis of both type 1 <a href="/wiki/Polyketide_synthases" class="mw-redirect" title="Polyketide synthases">polyketide synthases</a> (PKS 1) and <a href="/wiki/Nonribosomal_peptide" title="Nonribosomal peptide">nonribosomal peptide</a> syntheses (NRPS). The research shows the hybrid synthesis consists of ten modules of type 1 polyketide synthase and one module of nonribosomal peptide synthase. The synthetic enzymes for tacrolimus are found in 19 gene clusters named fkb. The 19 genes are fkbQ, fkbN, fkbM, fkbD, fkbA, fkbP, fkbO, fkbB, fkbC, fkbL, fkbK, fkbJ, fkbI, fkbH, fkbG, allD, allR, allK and allA.<sup id="cite_ref-Ordóñez-Robles_2018_56-0" class="reference"><a href="#cite_note-Ordóñez-Robles_2018-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>There are several possible ways of biosynthesis of tacrolimus. The fundamental units for biosynthesis are following: one molecule of 4,5-dihydroxycyclohex-1-enecarboxylic acid (DHCHC) as a starter unit, four molecules of malonyl-CoA, five molecules of methylmalonyl-CoA, one molecule of allylmalonyl-CoA as elongation units. However, two molecules of malonyl-CoA are able to be replaced by two molecules of methoxymalonyl CoA. Once two malonyl-CoA molecules are replaced, post-synthase tailoring steps are no longer required where two methoxymalonyl CoA molecules are substituted. The biosynthesis of methoxymalonyl CoA to Acyl Carrier protein is proceeded by five enzymes (fkbG, fkbH, fkbI, fkbJ, and fkbK). Allylmalonyl-CoA is also able to be replaced by propionylmalonyl-CoA.<sup id="cite_ref-Ordóñez-Robles_2018_56-1" class="reference"><a href="#cite_note-Ordóñez-Robles_2018-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>The starter unit, DHCHC from the <a href="/wiki/Chorismic_acid" title="Chorismic acid">chorismic acid</a> is formed by fkbO enzyme and loaded onto CoA-ligase domain (CoL). Then, it proceeds to NADPH dependent reduction(ER). Three enzymes, fkbA,B,C enforce processes from the loading module to the module 10, the last step of PKS 1. fkbB enzyme is responsible of allylmalonyl-CoA synthesis or possibly propionylmalonyl-CoA at C21, which it is an unusual step of general PKS 1. As mentioned, if two methoxymalonyl CoA molecules are substituted for two malonyl-CoA molecules, they will take place in module 7 and 8 (C13 and C15), and fkbA enzyme will enforce this process. After the last step (module 10) of PKS 1, one molecule of <small>L</small>-<a href="/wiki/Pipecolic_acid" title="Pipecolic acid">pipecolic acid</a> formed from <small>L</small>-<a href="/wiki/Lysine" title="Lysine">lysine</a> and catalyzed through fkbL enzyme synthesizes with the molecule from the module 10. The process of <small>L</small>-pipecolic acid synthesis is NRPS enforced by fkbP enzyme. After synthesizing the entire subunits, the molecule is cyclized. After the cyclization, the pre-tacrolimus molecule goes through the post-synthase tailoring steps such as oxidation and <a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine"><i>S</i>-adenosyl methionine</a>. Particularly fkbM enzyme is responsible of alcohol methylation targeting the alcohol of DHCHC starter unit (Carbon number 31 depicted in brown), and fkbD enzyme is responsible of C9 (depicted in green). After these tailoring steps, the tacrolimus molecule becomes biologically active.<sup id="cite_ref-Ordóñez-Robles_2018_56-2" class="reference"><a href="#cite_note-Ordóñez-Robles_2018-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Chen_2013_57-0" class="reference"><a href="#cite_note-Chen_2013-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Mo_2009_58-0" class="reference"><a href="#cite_note-Mo_2009-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=20" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Lupus_nephritis">Lupus nephritis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=21" title="Edit section: Lupus nephritis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tacrolimus has been shown to reduce the risk of serious infections while also increasing <a href="/wiki/Remission_(medicine)" title="Remission (medicine)">remission</a> of kidney function in <a href="/wiki/Lupus_nephritis" title="Lupus nephritis">lupus nephritis</a>.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Ulcerative_colitis">Ulcerative colitis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=22" title="Edit section: Ulcerative colitis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Tacrolimus has been used to suppress the inflammation associated with <a href="/wiki/Ulcerative_colitis" title="Ulcerative colitis">ulcerative colitis</a> (UC), a form of <a href="/wiki/Inflammatory_bowel_disease" title="Inflammatory bowel disease">inflammatory bowel disease</a>. Although almost exclusively used in trial cases only, tacrolimus has shown to be significantly effective in the suppression of flares of UC.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> A 2022 updated Cochrane systematic review found that tacrolimus may be superior to placebo in achieving remission and improvement in UC.<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> </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=Tacrolimus&action=edit&section=23" 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-Drugs.com_pregnancy-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Drugs.com_pregnancy_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://www.drugs.com/pregnancy/tacrolimus.html">"Tacrolimus Use During Pregnancy"</a>. <i>Drugs.com</i>. 3 October 2019<span class="reference-accessdate">. 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(identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/35388476">35388476</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Cochrane+Database+of+Systematic+Reviews&rft.atitle=Tacrolimus+%28FK506%29+for+induction+of+remission+in+corticosteroid-refractory+ulcerative+colitis&rft.volume=2022&rft.issue=4&rft.pages=CD007216&rft.date=2022-04&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8987360%23id-name%3DPMC&rft_id=info%3Apmid%2F35388476&rft_id=info%3Adoi%2F10.1002%2F14651858.CD007216.pub2&rft.aulast=Gordon&rft.aufirst=M&rft.au=Sinopoulou%2C+V&rft.au=Akobeng%2C+AK&rft.au=Pana%2C+M&rft.au=Gasiea%2C+R&rft.au=Moran%2C+GW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC8987360&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATacrolimus" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=24" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLvQiZhouShi2020" class="citation journal cs1">Lv X, Qi J, Zhou M, Shi B, Cai C, Tang Y, et al. (June 2020). "Comparative efficacy of 20 graft-versus-host disease prophylaxis therapies for patients after hematopoietic stem-cell transplantation: A multiple-treatments network meta-analysis". <i>Critical Reviews in Oncology/Hematology</i>. <b>150</b>: 102944. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.critrevonc.2020.102944">10.1016/j.critrevonc.2020.102944</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32247246">32247246</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:214794350">214794350</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Critical+Reviews+in+Oncology%2FHematology&rft.atitle=Comparative+efficacy+of+20+graft-versus-host+disease+prophylaxis+therapies+for+patients+after+hematopoietic+stem-cell+transplantation%3A+A+multiple-treatments+network+meta-analysis&rft.volume=150&rft.pages=102944&rft.date=2020-06&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A214794350%23id-name%3DS2CID&rft_id=info%3Apmid%2F32247246&rft_id=info%3Adoi%2F10.1016%2Fj.critrevonc.2020.102944&rft.aulast=Lv&rft.aufirst=X&rft.au=Qi%2C+J&rft.au=Zhou%2C+M&rft.au=Shi%2C+B&rft.au=Cai%2C+C&rft.au=Tang%2C+Y&rft.au=Pan%2C+T&rft.au=Han%2C+Y&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATacrolimus" class="Z3988"></span></li></ul> </div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Tacrolimus&action=edit&section=25" 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://medlineplus.gov/druginfo/meds/a608037.html">"Tacrolimus Injection"</a>. <i>MedlinePlus</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=MedlinePlus&rft.atitle=Tacrolimus+Injection&rft_id=https%3A%2F%2Fmedlineplus.gov%2Fdruginfo%2Fmeds%2Fa608037.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATacrolimus" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a602020.html">"Tacrolimus Topical"</a>. <i>MedlinePlus</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=MedlinePlus&rft.atitle=Tacrolimus+Topical&rft_id=https%3A%2F%2Fmedlineplus.gov%2Fdruginfo%2Fmeds%2Fa602020.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATacrolimus" class="Z3988"></span></li> <li><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?name=Tacrolimus">Tacrolimus</a> at the U.S. National Library of Medicine <a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">Medical Subject Headings</a> (MeSH)</li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.fda.gov/drugs/drug-safety-and-availability/fda-approves-new-use-transplant-drug-based-real-world-evidence">"FDA Approves New Use of Transplant Drug Based on Real-World Evidence"</a>. <i>U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA)</i>. 30 September 2021.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=U.S.+Food+and+Drug+Administration+%28FDA%29&rft.atitle=FDA+Approves+New+Use+of+Transplant+Drug+Based+on+Real-World+Evidence&rft.date=2021-09-30&rft_id=https%3A%2F%2Fwww.fda.gov%2Fdrugs%2Fdrug-safety-and-availability%2Ffda-approves-new-use-transplant-drug-based-real-world-evidence&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATacrolimus" 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 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href="/wiki/Lithium_succinate" title="Lithium succinate">Lithium succinate</a></li></ul></li> <li><i><a href="/wiki/Topical_steroid" title="Topical steroid">Topical corticosteroids</a></i> (e.g., <a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Skin_whitening" title="Skin whitening">Skin lightening</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/Hydroquinone" title="Hydroquinone">Hydroquinone</a></li> <li><a href="/wiki/Mequinol" title="Mequinol">Mequinol</a></li> <li><a href="/wiki/Monobenzone" title="Monobenzone">Monobenzone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sun_tanning" title="Sun tanning">Skin darkening</a></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/Afamelanotide" title="Afamelanotide">Afamelanotide</a></li> <li><a href="/wiki/Melanotan_II" title="Melanotan II">Melanotan II</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anti-inflammatories" class="mw-redirect" title="Anti-inflammatories">Anti-inflammatories</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/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/%CE%93-Linolenic_acid" title="Γ-Linolenic acid">Gamolenic acid</a></li> <li><a href="/wiki/Oxaceprol" title="Oxaceprol">Oxaceprol</a></li> <li><a href="/wiki/Pimecrolimus" title="Pimecrolimus">Pimecrolimus</a></li> <li><a class="mw-selflink selflink">Tacrolimus</a></li></ul> <ul><li><i><a href="/wiki/Topical_steroid" title="Topical steroid">Topical corticosteroids</a></i> (e.g., <a href="/wiki/Hydrocortisone" title="Hydrocortisone">hydrocortisone</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Management_of_hair_loss" title="Management of hair loss">Alopecia treatments</a></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><i><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase inhibitors</a></i> <ul><li><a href="/wiki/Alfatradiol" title="Alfatradiol">Alfatradiol</a></li> <li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto extract</a></li></ul></li> <li><i><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a></i> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Topilutamide" title="Topilutamide">Topilutamide (fluridil)</a></li></ul></li> <li><i><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium channel openers</a></i> <ul><li><a href="/wiki/Minoxidil" title="Minoxidil">Minoxidil</a></li></ul></li> <li><i>Others</i> <ul><li><a href="/wiki/Nepidermin" title="Nepidermin">Nepidermin</a></li> <li><a href="/wiki/Ritlecitinib" title="Ritlecitinib">Ritlecitinib</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hair_growth_inhibitor" class="mw-redirect" title="Hair growth inhibitor">Hair growth 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><i><a href="/wiki/5%CE%B1-Reductase_inhibitor" title="5α-Reductase inhibitor">5α-Reductase inhibitors</a></i> <ul><li><a href="/wiki/Dutasteride" title="Dutasteride">Dutasteride</a></li> <li><a href="/wiki/Finasteride" title="Finasteride">Finasteride</a></li></ul></li> <li><i><a href="/wiki/Antiandrogen" title="Antiandrogen">Antiandrogens</a></i> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li></ul></li> <li><a href="/wiki/Eflornithine" title="Eflornithine">Eflornithine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</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/Abrocitinib" title="Abrocitinib">Abrocitinib</a></li> <li><a href="/wiki/Aminobenzoate" class="mw-redirect" title="Aminobenzoate">Aminobenzoate potassium</a></li> <li><a href="/wiki/Androgen" title="Androgen">Androgens</a> (e.g., <a href="/wiki/Testosterone_(medication)" title="Testosterone (medication)">testosterone</a>)</li> <li><a href="/wiki/Benzoylperoxide" class="mw-redirect" title="Benzoylperoxide">Benzoylperoxide</a></li> <li><a href="/wiki/Brimonidine" title="Brimonidine">Brimonidine</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Calcium_gluconate" title="Calcium gluconate">Calcium gluconate</a></li> <li><a href="/wiki/Collagen" title="Collagen">Collagen</a></li> <li><a href="/wiki/Crisaborole" title="Crisaborole">Crisaborole</a></li> <li><a href="/wiki/Cromoglicic_acid" title="Cromoglicic acid">Cromoglicic acid</a></li> <li><a href="/wiki/Delgocitinib" title="Delgocitinib">Delgocitinib</a></li> <li><a href="/wiki/Deoxycholic_acid" title="Deoxycholic acid">Deoxycholic acid</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></li> <li><a href="/wiki/Dupilumab" title="Dupilumab">Dupilumab</a></li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a> (e.g., <a href="/wiki/Estradiol" title="Estradiol">estradiol</a>)</li> <li><a href="/wiki/Glycopyrronium_bromide" title="Glycopyrronium bromide">Glycopyrronium bromide</a></li> <li><a href="/wiki/Glycopyrronium_tosylate" title="Glycopyrronium tosylate">Glycopyrronium tosylate</a></li> <li><a href="/wiki/Hyaluronic_acid" title="Hyaluronic acid">Hyaluronic acid</a></li> <li><a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">Hydrogen peroxide</a></li> <li><a href="/wiki/Ivermectin" title="Ivermectin">Ivermectin</a></li> <li><a href="/wiki/Lebrikizumab" title="Lebrikizumab">Lebrikizumab</a></li> <li><a href="/wiki/Lokivetmab" title="Lokivetmab">Lokivetmab</a></li> <li><a href="/wiki/Medical_uses_of_magnesium_sulfate" title="Medical uses of magnesium sulfate">Magnesium sulfate</a></li> <li><a href="/wiki/Metandienone" title="Metandienone">Metandienone</a></li> <li><a href="/wiki/Nemolizumab" title="Nemolizumab">Nemolizumab</a></li> <li><a href="/wiki/Oclacitinib" title="Oclacitinib">Oclacitinib</a></li> <li><a href="/wiki/Oxymetazoline" title="Oxymetazoline">Oxymetazoline</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a></li> <li><a href="/wiki/Pregnenolone_acetate" title="Pregnenolone acetate">Pregnenolone acetate</a></li> <li><a href="/wiki/Progestogen" title="Progestogen">Progestogens</a> (e.g., <a href="/wiki/Progesterone_(medication)" title="Progesterone (medication)">progesterone</a>)</li> <li><a href="/wiki/Ruxolitinib" title="Ruxolitinib">Ruxolitinib</a></li> <li><a href="/wiki/Sofpironium_bromide" title="Sofpironium bromide">Sofpironium bromide</a></li> <li><a href="/wiki/Tiratricol" title="Tiratricol">Tiratricol</a></li> <li><a href="/wiki/Tralokinumab" title="Tralokinumab">Tralokinumab</a></li></ul> </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="Immunosuppressive_drugs_/_Immunosuppressants_(L04)180" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse 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:Immunosuppressants" title="Template:Immunosuppressants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Immunosuppressants" title="Template talk:Immunosuppressants"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Immunosuppressants" title="Special:EditPage/Template:Immunosuppressants"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Immunosuppressive_drugs_/_Immunosuppressants_(L04)180" style="font-size:114%;margin:0 4em"><a href="/wiki/Immunosuppressive_drug" title="Immunosuppressive drug">Immunosuppressive drugs</a> / <a href="/wiki/Immunosuppression" title="Immunosuppression">Immunosuppressants</a> (<a href="/wiki/ATC_code_L04" title="ATC code L04">L04</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intracellular<br />(initiation)</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/Antimetabolite" title="Antimetabolite">Antimetabolites</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/Purine_synthesis_inhibitor" class="mw-redirect" title="Purine synthesis inhibitor">purine synthesis inhibitors</a></i> <ul><li><a href="/wiki/Azathioprine" title="Azathioprine">Azathioprine</a></li> <li><a href="/wiki/Mycophenolic_acid" title="Mycophenolic acid">Mycophenolic acid</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Dihydroorotate_dehydrogenase" title="Dihydroorotate dehydrogenase">dihydroorotate dehydrogenase</a></i> inhibitors <ul><li><a href="/wiki/Leflunomide" title="Leflunomide">Leflunomide</a></li> <li><a href="/wiki/Teriflunomide" title="Teriflunomide">Teriflunomide</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Antifolate" title="Antifolate">antifolate</a></i> <ul><li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Macrolide" title="Macrolide">Macrolides</a>/<br />other <a href="/wiki/Interleukin_2" title="Interleukin 2">IL-2</a> inhibitors</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/FKBP" title="FKBP">FKBP</a>/<a href="/wiki/Cyclophilin" title="Cyclophilin">Cyclophilin</a>/<a href="/wiki/Calcineurin" title="Calcineurin">Calcineurin</a></i> <ul><li><a href="/wiki/Ciclosporin" title="Ciclosporin">Ciclosporin</a></li> <li><a href="/wiki/Pimecrolimus" title="Pimecrolimus">Pimecrolimus</a></li> <li><a class="mw-selflink selflink">Tacrolimus</a></li> <li><a href="/wiki/Voclosporin" title="Voclosporin">Voclosporin</a></li></ul></li></ul> <ul><li><a href="/wiki/Abetimus" title="Abetimus">Abetimus</a></li> <li><a href="/wiki/Gusperimus" title="Gusperimus">Gusperimus</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Immunomodulatory_imide_drug" class="mw-redirect" title="Immunomodulatory imide drug">IMiDs</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/Lenalidomide" title="Lenalidomide">Lenalidomide</a></li> <li><a href="/wiki/Pomalidomide" title="Pomalidomide">Pomalidomide</a></li> <li><a href="/wiki/Thalidomide" title="Thalidomide">Thalidomide</a></li> <li><i><a href="/wiki/PDE4_inhibitor" title="PDE4 inhibitor">PDE4 inhibitor</a></i> <ul><li><a href="/wiki/Apremilast" title="Apremilast">Apremilast</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intracellular<br />(reception)</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/Interleukin_1_receptor_antagonist" class="mw-redirect" title="Interleukin 1 receptor antagonist">IL-1 receptor antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anakinra" title="Anakinra">Anakinra</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/MTOR" title="MTOR">mTOR</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/Everolimus" title="Everolimus">Everolimus</a></li> <li><a href="/wiki/Ridaforolimus" title="Ridaforolimus">Ridaforolimus</a></li> <li><a href="/wiki/Sirolimus" title="Sirolimus">Sirolimus</a></li> <li><a href="/wiki/Temsirolimus" title="Temsirolimus">Temsirolimus</a></li> <li><a href="/wiki/Umirolimus" title="Umirolimus">Umirolimus</a></li> <li><a href="/wiki/Zotarolimus" title="Zotarolimus">Zotarolimus</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Extracellular</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/Antibody" title="Antibody">Antibodies</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monoclonal_antibody" title="Monoclonal antibody">Monoclonal</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Serum target<br />(noncellular)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Complement_component_5" title="Complement component 5">Complement component 5</a></i> <ul><li><a href="/wiki/Eculizumab" title="Eculizumab">Eculizumab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/TNF_inhibitor" title="TNF inhibitor">TNF</a></i> <ul><li><a href="/wiki/Adalimumab" title="Adalimumab">Adalimumab</a></li> <li><a href="/wiki/Afelimomab" title="Afelimomab">Afelimomab</a></li> <li><a href="/wiki/Certolizumab_pegol" title="Certolizumab pegol">Certolizumab pegol</a></li> <li><a href="/wiki/Golimumab" title="Golimumab">Golimumab</a></li> <li><a href="/wiki/Infliximab" title="Infliximab">Infliximab</a></li> <li><a href="/wiki/Nerelimomab" title="Nerelimomab">Nerelimomab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Interleukin" title="Interleukin">Interleukin</a></i> <ul><li><a href="/wiki/Anakinra" title="Anakinra">Anakinra</a></li> <li><a href="/wiki/Basiliximab" title="Basiliximab">Basiliximab</a></li> <li><a href="/wiki/Bimekizumab" title="Bimekizumab">Bimekizumab</a></li> <li><a href="/wiki/Briakinumab" title="Briakinumab">Briakinumab</a></li> <li><a href="/wiki/Brodalumab" title="Brodalumab">Brodalumab</a></li> <li><a href="/wiki/Canakinumab" title="Canakinumab">Canakinumab</a></li> <li><a href="/wiki/Daclizumab" title="Daclizumab">Daclizumab</a></li> <li><a href="/wiki/Guselkumab" title="Guselkumab">Guselkumab</a></li> <li><a href="/wiki/Ixekizumab" title="Ixekizumab">Ixekizumab</a></li> <li><a href="/w/index.php?title=Netakimab&action=edit&redlink=1" class="new" title="Netakimab (page does not exist)">Netakimab</a></li> <li><a href="/wiki/Olokizumab" title="Olokizumab">Olokizumab</a></li> <li><a href="/wiki/Rilonacept" title="Rilonacept">Rilonacept</a></li> <li><a href="/wiki/Risankizumab" title="Risankizumab">Risankizumab</a></li> <li><a href="/wiki/Sarilumab" title="Sarilumab">Sarilumab</a></li> <li><a href="/wiki/Satralizumab" title="Satralizumab">Satralizumab</a></li> <li><a href="/wiki/Secukinumab" title="Secukinumab">Secukinumab</a></li> <li><a href="/wiki/Siltuximab" title="Siltuximab">Siltuximab</a></li> <li><a href="/wiki/Sirukumab" title="Sirukumab">Sirukumab</a></li> <li><a href="/wiki/Spesolimab" title="Spesolimab">Spesolimab</a></li> <li><a href="/wiki/Tildrakizumab" title="Tildrakizumab">Tildrakizumab</a></li> <li><a href="/wiki/Tocilizumab" title="Tocilizumab">Tocilizumab</a></li> <li><a href="/wiki/Ustekinumab" title="Ustekinumab">Ustekinumab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Interleukin_5" title="Interleukin 5">Interleukin 5</a></i> <ul><li><a href="/wiki/Mepolizumab" title="Mepolizumab">Mepolizumab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Immunoglobulin_E" title="Immunoglobulin E">Immunoglobulin E</a></i> <ul><li><a href="/wiki/Omalizumab" title="Omalizumab">Omalizumab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Interferon" title="Interferon">Interferon</a></i> <ul><li><a href="/wiki/Faralimomab" title="Faralimomab">Faralimomab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Interleukin_6" title="Interleukin 6">IL-6</a></i> <ul><li><a href="/wiki/Elsilimomab" title="Elsilimomab">Elsilimomab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Interleukin_12" title="Interleukin 12">IL-12</a>, <a href="/wiki/Interleukin_13" title="Interleukin 13">IL-13</a>, and <a href="/wiki/Interleukin_23" title="Interleukin 23">IL-23</a></i> <ul><li><a href="/wiki/Lebrikizumab" title="Lebrikizumab">Lebrikizumab</a></li> <li><a href="/wiki/Ustekinumab" title="Ustekinumab">Ustekinumab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/Interleukin_17" title="Interleukin 17">IL-17A</a></i> <ul><li><a href="/wiki/Secukinumab" title="Secukinumab">Secukinumab</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Cellular<br />target</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/CD3_(immunology)" title="CD3 (immunology)">CD3</a></i> <ul><li><a href="/wiki/Muromonab-CD3" title="Muromonab-CD3">Muromonab-CD3</a></li> <li><a href="/wiki/Otelixizumab" title="Otelixizumab">Otelixizumab</a></li> <li><a href="/wiki/Teplizumab" title="Teplizumab">Teplizumab</a></li> <li><a href="/wiki/Visilizumab" title="Visilizumab">Visilizumab</a></li></ul></li> <li><i><a href="/wiki/CD4" title="CD4">CD4</a></i> <ul><li><a href="/wiki/Clenoliximab" title="Clenoliximab">Clenoliximab</a></li> <li><a href="/wiki/Keliximab" title="Keliximab">Keliximab</a></li> <li><a href="/wiki/Zanolimumab" title="Zanolimumab">Zanolimumab</a></li></ul></li> <li><i><a href="/wiki/CD11a" class="mw-redirect" title="CD11a">CD11a</a></i> <ul><li><a href="/wiki/Efalizumab" title="Efalizumab">Efalizumab</a></li></ul></li> <li><i><a href="/wiki/CD18" class="mw-redirect" title="CD18">CD18</a></i> <ul><li><a href="/wiki/Erlizumab" title="Erlizumab">Erlizumab</a></li></ul></li> <li><i><a href="/wiki/CD20" title="CD20">CD20</a></i> <ul><li><a href="/wiki/Obinutuzumab" title="Obinutuzumab">Obinutuzumab</a></li> <li><a href="/wiki/Ocrelizumab" title="Ocrelizumab">Ocrelizumab</a> (<a href="/wiki/Ocrelizumab/hyaluronidase" title="Ocrelizumab/hyaluronidase">+hyaluronidase</a>)</li> <li><a href="/wiki/Pascolizumab" title="Pascolizumab">Pascolizumab</a></li> <li><a href="/wiki/Rituximab" title="Rituximab">Rituximab</a></li> <li><a href="/wiki/Ublituximab" title="Ublituximab">Ublituximab</a></li></ul></li> <li><i><a href="/wiki/CD23" title="CD23">CD23</a></i> <ul><li><a href="/wiki/Gomiliximab" class="mw-redirect" title="Gomiliximab">Gomiliximab</a></li> <li><a href="/wiki/Lumiliximab" title="Lumiliximab">Lumiliximab</a></li></ul></li> <li><i><a href="/wiki/CD40_(protein)" title="CD40 (protein)">CD40</a></i> <ul><li><a href="/wiki/Teneliximab" title="Teneliximab">Teneliximab</a></li> <li><a href="/wiki/Toralizumab" title="Toralizumab">Toralizumab</a></li></ul></li> <li><i><a href="/wiki/L-selectin" title="L-selectin">CD62L/L-selectin</a></i> <ul><li><a href="/wiki/Aselizumab" title="Aselizumab">Aselizumab</a></li></ul></li> <li><i><a href="/wiki/CD80" title="CD80">CD80</a></i> <ul><li><a href="/wiki/Galiximab" title="Galiximab">Galiximab</a></li></ul></li> <li><i><a href="/wiki/Basigin" title="Basigin">CD147/Basigin</a></i> <ul><li><a href="/wiki/Gavilimomab" title="Gavilimomab">Gavilimomab</a></li></ul></li> <li><i><a href="/wiki/CD154" title="CD154">CD154</a></i> <ul><li><a href="/wiki/Frexalimab" title="Frexalimab">Frexalimab</a></li> <li><a href="/wiki/Ruplizumab" title="Ruplizumab">Ruplizumab</a></li></ul></li></ul> <ul><li><i>BLyS</i> <ul><li><a href="/wiki/Belimumab" title="Belimumab">Belimumab</a></li></ul></li> <li><i><a href="/wiki/Chloramphenicol_acetyltransferase" title="Chloramphenicol acetyltransferase">CAT</a></i> <ul><li><a href="/wiki/Bertilimumab" title="Bertilimumab">Bertilimumab</a></li> <li><a href="/wiki/Lerdelimumab" title="Lerdelimumab">Lerdelimumab</a></li> <li><a href="/wiki/Metelimumab" title="Metelimumab">Metelimumab</a></li></ul></li> <li><i><a href="/wiki/Integrin" title="Integrin">Integrin</a></i> <ul><li><a href="/wiki/Natalizumab" title="Natalizumab">Natalizumab</a></li> <li><a href="/wiki/Vedolizumab" title="Vedolizumab">Vedolizumab</a></li></ul></li> <li><i><a href="/wiki/Interleukin-6_receptor" title="Interleukin-6 receptor">Interleukin-6 receptor</a></i> <ul><li><a href="/wiki/Tocilizumab" title="Tocilizumab">Tocilizumab</a></li></ul></li> <li><i><a href="/wiki/Lymphocyte_function-associated_antigen_1" title="Lymphocyte function-associated antigen 1">LFA-1</a></i> <ul><li><a href="/wiki/Odulimomab" title="Odulimomab">Odulimomab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/IL-2_receptor" title="IL-2 receptor">IL-2 receptor/CD25</a></i> <ul><li><a href="/wiki/Basiliximab" title="Basiliximab">Basiliximab</a></li> <li><a href="/wiki/Daclizumab" title="Daclizumab">Daclizumab</a></li> <li><a href="/wiki/Inolimomab" title="Inolimomab">Inolimomab</a></li></ul></li></ul> <ul><li><i><a href="/wiki/T_cell" title="T cell">T-lymphocyte</a></i> (<a href="/wiki/Zolimomab_aritox" title="Zolimomab aritox">Zolimomab aritox</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Unsorted</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/Alemtuzumab" title="Alemtuzumab">Alemtuzumab</a></li> <li><a href="/wiki/Anifrolumab" title="Anifrolumab">Anifrolumab</a></li> <li><a href="/wiki/Atorolimumab" title="Atorolimumab">Atorolimumab</a></li> <li><a href="/w/index.php?title=Begelomab&action=edit&redlink=1" class="new" title="Begelomab (page does not exist)">Begelomab</a></li> <li><a href="/wiki/Cedelizumab" title="Cedelizumab">Cedelizumab</a></li> <li><a href="/wiki/Emapalumab" title="Emapalumab">Emapalumab</a></li> <li><a href="/wiki/Fontolizumab" title="Fontolizumab">Fontolizumab</a></li> <li><a href="/wiki/Inebilizumab" title="Inebilizumab">Inebilizumab</a></li> <li><a href="/wiki/Maslimomab" title="Maslimomab">Maslimomab</a></li> <li><a href="/wiki/Morolimumab" title="Morolimumab">Morolimumab</a></li> <li><a href="/wiki/Ofatumumab" title="Ofatumumab">Ofatumumab</a></li> <li><a href="/wiki/Pexelizumab" title="Pexelizumab">Pexelizumab</a></li> <li><a href="/wiki/Reslizumab" title="Reslizumab">Reslizumab</a></li> <li><a href="/wiki/Rovelizumab" title="Rovelizumab">Rovelizumab</a></li> <li><a href="/wiki/Siplizumab" title="Siplizumab">Siplizumab</a></li> <li><a href="/wiki/Talizumab" title="Talizumab">Talizumab</a></li> <li><a href="/wiki/Telimomab_aritox" title="Telimomab aritox">Telimomab aritox</a></li> <li><a href="/wiki/Teprotumumab" title="Teprotumumab">Teprotumumab</a></li> <li><a href="/wiki/Vapaliximab" title="Vapaliximab">Vapaliximab</a></li> <li><a href="/wiki/Vepalimomab" title="Vepalimomab">Vepalimomab</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polyclonal_antibodies" title="Polyclonal antibodies">Polyclonal</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/Anti-thymocyte_globulin" title="Anti-thymocyte globulin">Anti-thymocyte globulin</a></li> <li><a href="/wiki/Anti-lymphocyte_globulin" title="Anti-lymphocyte globulin">Anti-lymphocyte globulin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">-cept (<a href="/wiki/Fusion_protein" title="Fusion protein">Fusion</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/CTLA-4" class="mw-redirect" title="CTLA-4">CTLA-4</a></i> <ul><li><a href="/wiki/Abatacept" title="Abatacept">Abatacept</a></li> <li><a href="/wiki/Belatacept" title="Belatacept">Belatacept</a></li></ul></li> <li><i><a href="/wiki/TNF_inhibitor" title="TNF inhibitor">TNF inhibitor</a></i> <ul><li><a href="/wiki/Etanercept" title="Etanercept">Etanercept</a></li> <li><a href="/w/index.php?title=Opinercept&action=edit&redlink=1" class="new" title="Opinercept (page does not exist)">Opinercept</a></li></ul></li> <li><a href="/wiki/Aflibercept" title="Aflibercept">Aflibercept</a></li> <li><a href="/wiki/Alefacept" title="Alefacept">Alefacept</a></li> <li><a href="/wiki/Rilonacept" title="Rilonacept">Rilonacept</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Unsorted</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/Avacopan" title="Avacopan">Avacopan</a></li> <li><a href="/wiki/Baricitinib" title="Baricitinib">Baricitinib</a></li> <li><a href="/wiki/Bimekizumab" title="Bimekizumab">Bimekizumab</a></li> <li><a href="/wiki/Blisibimod" title="Blisibimod">Blisibimod</a></li> <li><a href="/wiki/Briakinumab" title="Briakinumab">Briakinumab</a></li> <li><a href="/wiki/Brodalumab" title="Brodalumab">Brodalumab</a></li> <li><a href="/wiki/Canakinumab" title="Canakinumab">Canakinumab</a></li> <li><a href="/wiki/Crovalimab" title="Crovalimab">Crovalimab</a></li> <li><a href="/wiki/Danicopan" title="Danicopan">Danicopan</a></li> <li><a href="/wiki/Darvadstrocel" title="Darvadstrocel">Darvadstrocel</a></li> <li><a href="/wiki/Deucravacitinib" title="Deucravacitinib">Deucravacitinib</a></li> <li><a href="/wiki/Deuruxolitinib" title="Deuruxolitinib">Deuruxolitinib</a></li> <li><a href="/wiki/Dimethyl_fumarate" title="Dimethyl fumarate">Dimethyl fumarate</a></li> <li><a href="/wiki/Diroximel_fumarate" title="Diroximel fumarate">Diroximel fumarate</a></li> <li><a href="/wiki/Efgartigimod_alfa" title="Efgartigimod alfa">Efgartigimod alfa</a> (<a href="/wiki/Efgartigimod_alfa/hyaluronidase" title="Efgartigimod alfa/hyaluronidase">+hyaluronidase</a>)</li> <li><a href="/wiki/Etrasimod" title="Etrasimod">Etrasimod</a></li> <li><a href="/wiki/Filgotinib" title="Filgotinib">Filgotinib</a></li> <li><a href="/wiki/Fingolimod" title="Fingolimod">Fingolimod</a></li> <li><a href="/wiki/Guselkumab" title="Guselkumab">Guselkumab</a></li> <li><a href="/wiki/Iptacopan" title="Iptacopan">Iptacopan</a></li> <li><a href="/w/index.php?title=Itacitinib&action=edit&redlink=1" class="new" title="Itacitinib (page does not exist)">Itacitinib</a></li> <li><a href="/wiki/Ixekizumab" title="Ixekizumab">Ixekizumab</a></li> <li><a href="/w/index.php?title=Netakimab&action=edit&redlink=1" class="new" title="Netakimab (page does not exist)">Netakimab</a></li> <li><a href="/wiki/Olokizumab" title="Olokizumab">Olokizumab</a></li> <li><a href="/wiki/Ozanimod" title="Ozanimod">Ozanimod</a></li> <li><a href="/wiki/Peficitinib" title="Peficitinib">Peficitinib</a></li> <li><a href="/wiki/Pegcetacoplan" title="Pegcetacoplan">Pegcetacoplan</a></li> <li><a href="/wiki/Pirfenidone" title="Pirfenidone">Pirfenidone</a></li> <li><a href="/wiki/Ponesimod" title="Ponesimod">Ponesimod</a></li> <li><a href="/wiki/Ravulizumab" title="Ravulizumab">Ravulizumab</a></li> <li><a href="/wiki/Risankizumab" title="Risankizumab">Risankizumab</a></li> <li><a href="/wiki/Ritlecitinib" title="Ritlecitinib">Ritlecitinib</a></li> <li><a href="/wiki/Rozanolixizumab" title="Rozanolixizumab">Rozanolixizumab</a></li> <li><a href="/wiki/Sarilumab" title="Sarilumab">Sarilumab</a></li> <li><a href="/wiki/Satralizumab" title="Satralizumab">Satralizumab</a></li> <li><a href="/wiki/Siltuximab" title="Siltuximab">Siltuximab</a></li> <li><a href="/wiki/Siponimod" title="Siponimod">Siponimod</a></li> <li><a href="/wiki/Sirukumab" title="Sirukumab">Sirukumab</a></li> <li><a href="/wiki/Spesolimab" title="Spesolimab">Spesolimab</a></li> <li><a href="/wiki/Sutimlimab" title="Sutimlimab">Sutimlimab</a></li> <li><a href="/wiki/Telitacicept" title="Telitacicept">Telitacicept</a></li> <li><a href="/wiki/Tildrakizumab" title="Tildrakizumab">Tildrakizumab</a></li> <li><a href="/wiki/Tofacitinib" title="Tofacitinib">Tofacitinib</a></li> <li><a href="/wiki/Upadacitinib" title="Upadacitinib">Upadacitinib</a></li></ul> </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="Xenobiotic-sensing_receptor_modulators953" 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:Xenobiotic-sensing_receptor_modulators" title="Template:Xenobiotic-sensing receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Xenobiotic-sensing_receptor_modulators" title="Template talk:Xenobiotic-sensing receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Xenobiotic-sensing_receptor_modulators" title="Special:EditPage/Template:Xenobiotic-sensing receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Xenobiotic-sensing_receptor_modulators953" style="font-size:114%;margin:0 4em"><a href="/wiki/Xenobiotic-sensing_receptor" title="Xenobiotic-sensing receptor">Xenobiotic-sensing receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Constitutive_androstane_receptor" title="Constitutive androstane receptor"><abbr title="Constitutive androstane receptor">CAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Constitutive androstane receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/w/index.php?title=6,7-Dimethylesculetin&action=edit&redlink=1" class="new" title="6,7-Dimethylesculetin (page does not exist)">6,7-Dimethylesculetin</a></li> <li><a href="/wiki/Amiodarone" title="Amiodarone">Amiodarone</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/w/index.php?title=Benfuracarb&action=edit&redlink=1" class="new" title="Benfuracarb (page does not exist)">Benfuracarb</a></li> <li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Carvedilol" title="Carvedilol">Carvedilol</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Chrysin" title="Chrysin">Chrysin</a></li> <li><a href="/w/index.php?title=CITCO_(drug)&action=edit&redlink=1" class="new" title="CITCO (drug) (page does not exist)">CITCO</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cypermethrin" title="Cypermethrin">Cypermethrin</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Efavirenz" title="Efavirenz">Efavirenz</a></li> <li><a href="/wiki/Ellagic_acid" title="Ellagic acid">Ellagic acid</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Methoxychlor" title="Methoxychlor">Methoxychlor</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nefazodone" title="Nefazodone">Nefazodone</a></li> <li><a href="/wiki/Nevirapine" title="Nevirapine">Nevirapine</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/w/index.php?title=Octicizer&action=edit&redlink=1" class="new" title="Octicizer (page does not exist)">Octicizer</a></li> <li><a href="/wiki/Permethrin" title="Permethrin">Permethrin</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">Phenytoin</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/w/index.php?title=TCPOBOP&action=edit&redlink=1" class="new" title="TCPOBOP (page does not exist)">TCPOBOP</a></li> <li><a href="/wiki/Telmisartan" title="Telmisartan">Telmisartan</a></li> <li><a href="/wiki/Tolnaftate" title="Tolnaftate">Tolnaftate</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=3,17%CE%B2-Estradiol&action=edit&redlink=1" class="new" title="3,17β-Estradiol (page does not exist)">3,17β-Estradiol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B1-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3α-ol (page does not exist)">3α-Androstanol</a></li> <li><a href="/wiki/5%CE%B1-Androst-16-en-3%CE%B1-ol" class="mw-redirect" title="5α-Androst-16-en-3α-ol">3α-Androstenol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-3%CE%B2-ol&action=edit&redlink=1" class="new" title="5α-Androstan-3β-ol (page does not exist)">3β-Androstanol</a></li> <li><a href="/w/index.php?title=5%CE%B1-Androstan-17-ol&action=edit&redlink=1" class="new" title="5α-Androstan-17-ol (page does not exist)">17-Androstanol</a></li> <li><a href="/wiki/Allyl_isothiocyanate" title="Allyl isothiocyanate">AITC</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/w/index.php?title=Nigramide_J&action=edit&redlink=1" class="new" title="Nigramide J (page does not exist)">Nigramide J</a></li> <li><a href="/wiki/Okadaic_acid" title="Okadaic acid">Okadaic acid</a></li> <li><a href="/wiki/PK-11195" class="mw-redirect" title="PK-11195">PK-11195</a></li> <li><a href="/w/index.php?title=S-07662&action=edit&redlink=1" class="new" title="S-07662 (page does not exist)">S-07662</a></li> <li><a href="/w/index.php?title=T-0901317&action=edit&redlink=1" class="new" title="T-0901317 (page does not exist)">T-0901317</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Pregnane_X_receptor" title="Pregnane X receptor"><abbr title="Pregnane X receptor">PXR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Pregnane X receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/17%CE%B1-Hydroxypregnenolone" title="17α-Hydroxypregnenolone">17α-Hydroxypregnenolone</a></li> <li><a href="/wiki/17%CE%B1-Hydroxyprogesterone" title="17α-Hydroxyprogesterone">17α-Hydroxyprogesterone</a></li> <li><a href="/wiki/%CE%944-Androstenedione" class="mw-redirect" title="Δ4-Androstenedione">Δ<sup>4</sup>-Androstenedione</a></li> <li><a href="/wiki/%CE%945-Androstenediol" class="mw-redirect" title="Δ5-Androstenediol">Δ<sup>5</sup>-Androstenediol</a></li> <li><a href="/wiki/%CE%945-Androstenedione" class="mw-redirect" title="Δ5-Androstenedione">Δ<sup>5</sup>-Androstenedione</a></li> <li><a href="/w/index.php?title=AA-861&action=edit&redlink=1" class="new" title="AA-861 (page does not exist)">AA-861</a></li> <li><a href="/wiki/Allopregnanediol" title="Allopregnanediol">Allopregnanediol</a></li> <li><a href="/wiki/5%CE%B1-Dihydroprogesterone" title="5α-Dihydroprogesterone">Allopregnanedione (5α-dihydroprogesterone)</a></li> <li><a href="/wiki/Allopregnanolone" title="Allopregnanolone">Allopregnanolone (brexanolone)</a></li> <li><a href="/wiki/Alpha-Lipoic_acid" class="mw-redirect" title="Alpha-Lipoic acid">Alpha-Lipoic acid</a></li> <li><a href="/wiki/Ambrisentan" title="Ambrisentan">Ambrisentan</a></li> <li><a href="/wiki/AMI-193" class="mw-redirect" title="AMI-193">AMI-193</a></li> <li><a href="/wiki/Amlodipine_besylate" class="mw-redirect" title="Amlodipine besylate">Amlodipine besylate</a></li> <li><a href="/wiki/Antimycotic" class="mw-redirect" title="Antimycotic">Antimycotics</a></li> <li><a href="/wiki/Artemisinin" title="Artemisinin">Artemisinin</a></li> <li><a href="/wiki/Aurothioglucose" title="Aurothioglucose">Aurothioglucose</a></li> <li><a href="/wiki/Bile_acid" title="Bile acid">Bile acids</a></li> <li><a href="/wiki/Bithionol" title="Bithionol">Bithionol</a></li> <li><a href="/wiki/Bosentan" title="Bosentan">Bosentan</a></li> <li><a href="/w/index.php?title=Bumecaine&action=edit&redlink=1" class="new" title="Bumecaine (page does not exist)">Bumecaine</a></li> <li><a href="/wiki/Cafestol" title="Cafestol">Cafestol</a></li> <li><a href="/wiki/Cephaloridine" title="Cephaloridine">Cephaloridine</a></li> <li><a href="/wiki/Cephradine" class="mw-redirect" title="Cephradine">Cephradine</a></li> <li><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></li> <li><a href="/wiki/Ciglitazone" title="Ciglitazone">Ciglitazone</a></li> <li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Clofenvinfos" class="mw-redirect" title="Clofenvinfos">Clofenvinfos</a></li> <li><a href="/wiki/Chloroxine" title="Chloroxine">Chloroxine</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Colforsin" class="mw-redirect" title="Colforsin">Colforsin</a></li> <li><a href="/wiki/Corticosterone" title="Corticosterone">Corticosterone</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Dexamethasone" title="Dexamethasone">Dexamethasone</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>)</li> <li><a href="/wiki/Dehydroepiandrosterone_sulfate" title="Dehydroepiandrosterone sulfate">DHEA-S</a> (<a href="/wiki/Prasterone_sulfate" title="Prasterone sulfate">prasterone sulfate</a>)</li> <li><a href="/wiki/Dibunate_sodium" class="mw-redirect" title="Dibunate sodium">Dibunate sodium</a></li> <li><a href="/wiki/Diclazuril" title="Diclazuril">Diclazuril</a></li> <li><a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Dimercaprol" title="Dimercaprol">Dimercaprol</a></li> <li><a href="/w/index.php?title=Dinaline&action=edit&redlink=1" class="new" title="Dinaline (page does not exist)">Dinaline</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a></li> <li><a href="/wiki/Docusate_calcium" class="mw-redirect" title="Docusate calcium">Docusate calcium</a></li> <li><a href="/wiki/Dodecylbenzenesulfonic_acid" class="mw-redirect" title="Dodecylbenzenesulfonic acid">Dodecylbenzenesulfonic acid</a></li> <li><a href="/wiki/Dronabinol" title="Dronabinol">Dronabinol</a></li> <li><a href="/wiki/Droxidopa" title="Droxidopa">Droxidopa</a></li> <li><a href="/wiki/Eburnamonine" class="mw-redirect" title="Eburnamonine">Eburnamonine</a></li> <li><a href="/wiki/Ecopipam" title="Ecopipam">Ecopipam</a></li> <li><a href="/wiki/Enzacamene" title="Enzacamene">Enzacamene</a></li> <li><a href="/wiki/Epothilone_B" class="mw-redirect" title="Epothilone B">Epothilone B</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/w/index.php?title=Febantel&action=edit&redlink=1" class="new" title="Febantel (page does not exist)">Febantel</a></li> <li><a href="/wiki/Felodipine" title="Felodipine">Felodipine</a></li> <li><a href="/wiki/Fenbendazole" title="Fenbendazole">Fenbendazole</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a></li> <li><a href="/wiki/Flucloxacillin" title="Flucloxacillin">Flucloxacillin</a></li> <li><a href="/wiki/Fluorometholone" title="Fluorometholone">Fluorometholone</a></li> <li><a href="/wiki/Griseofulvin" title="Griseofulvin">Griseofulvin</a></li> <li><a href="/wiki/Guggulsterone" title="Guggulsterone">Guggulsterone</a></li> <li><a href="/wiki/Haloprogin" title="Haloprogin">Haloprogin</a></li> <li><a href="/wiki/Hetacillin_potassium" class="mw-redirect" title="Hetacillin potassium">Hetacillin potassium</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum"><i>Hypericum perforatum</i> (St John's wort)</a></li> <li><a href="/wiki/Indinavir_sulfate" class="mw-redirect" title="Indinavir sulfate">Indinavir sulfate</a></li> <li><a href="/wiki/Lasalocid_sodium" class="mw-redirect" title="Lasalocid sodium">Lasalocid sodium</a></li> <li><a href="/wiki/Levothyroxine" title="Levothyroxine">Levothyroxine</a></li> <li>Linolenic acid: <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">α-Linolenic acid</a> and <a href="/wiki/%CE%93-Linolenic_acid" title="Γ-Linolenic acid">γ-Linolenic acid</a></li> <li><a href="/w/index.php?title=LOE-908&action=edit&redlink=1" class="new" title="LOE-908 (page does not exist)">LOE-908</a></li> <li><a href="/wiki/Loratadine" title="Loratadine">Loratadine</a></li> <li><a href="/wiki/Lovastatin" title="Lovastatin">Lovastatin</a></li> <li><a href="/wiki/Meclizine" title="Meclizine">Meclizine</a></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Methylprednisolone" title="Methylprednisolone">Methylprednisolone</a></li> <li><a href="/wiki/Metyrapone" title="Metyrapone">Metyrapone</a></li> <li><a href="/wiki/Mevastatin" title="Mevastatin">Mevastatin</a></li> <li><a href="/wiki/Mifepristone" title="Mifepristone">Mifepristone</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Nicardipine" title="Nicardipine">Nicardipine</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Nifedipine" title="Nifedipine">Nifedipine</a></li> <li><a href="/wiki/Nilvadipine" title="Nilvadipine">Nilvadipine</a></li> <li><a href="/wiki/Nisoldipine" title="Nisoldipine">Nisoldipine</a></li> <li><a href="/wiki/Norelgestromin" title="Norelgestromin">Norelgestromin</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a></li> <li><a href="/wiki/Orlistat" title="Orlistat">Orlistat</a></li> <li><a href="/wiki/Oxatomide" title="Oxatomide">Oxatomide</a></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">Phenobarbital</a></li> <li><a href="/wiki/Piperine" title="Piperine">Piperine</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a></li> <li><a href="/wiki/Prednisolone" title="Prednisolone">Prednisolone</a></li> <li><a href="/wiki/Pregnanediol" title="Pregnanediol">Pregnanediol</a></li> <li><a href="/wiki/5%CE%B2-Dihydroprogesterone" title="5β-Dihydroprogesterone">Pregnanedione (5β-dihydroprogesterone)</a></li> <li><a href="/wiki/Pregnanolone" title="Pregnanolone">Pregnanolone</a></li> <li><a href="/wiki/Pregnenolone" title="Pregnenolone">Pregnenolone</a></li> <li><a href="/wiki/Pregnenolone_16%CE%B1-carbonitrile" title="Pregnenolone 16α-carbonitrile">Pregnenolone 16α-carbonitrile</a></li> <li><a href="/wiki/Proadifen" title="Proadifen">Proadifen</a></li> <li><a href="/wiki/Progesterone" title="Progesterone">Progesterone</a></li> <li><a href="/wiki/Quingestrone" title="Quingestrone">Quingestrone</a></li> <li><a href="/wiki/Reserpine" title="Reserpine">Reserpine</a></li> <li><a href="/wiki/Reverse_triiodothyronine" title="Reverse triiodothyronine">Reverse triiodothyronine</a></li> <li><a href="/wiki/Rifampicin" title="Rifampicin">Rifampicin</a></li> <li><a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li> <li><a href="/wiki/Rimexolone" title="Rimexolone">Rimexolone</a></li> <li><a href="/wiki/Riodipine" title="Riodipine">Riodipine</a></li> <li><a href="/wiki/Ritonavir" title="Ritonavir">Ritonavir</a></li> <li><a href="/wiki/Simvastatin" title="Simvastatin">Simvastatin</a></li> <li><a href="/wiki/Sirolimus" title="Sirolimus">Sirolimus</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a></li> <li><a href="/wiki/Spiroxatrine" title="Spiroxatrine">Spiroxatrine</a></li> <li><a href="/w/index.php?title=SR-12813&action=edit&redlink=1" class="new" title="SR-12813 (page does not exist)">SR-12813</a></li> <li><a href="/w/index.php?title=Suberoylanilide&action=edit&redlink=1" class="new" title="Suberoylanilide (page does not exist)">Suberoylanilide</a></li> <li><a href="/wiki/Sulfisoxazole" class="mw-redirect" title="Sulfisoxazole">Sulfisoxazole</a></li> <li><a href="/wiki/Suramin" title="Suramin">Suramin</a></li> <li><a class="mw-selflink selflink">Tacrolimus</a></li> <li><a href="/w/index.php?title=Tenylidone&action=edit&redlink=1" class="new" title="Tenylidone (page does not exist)">Tenylidone</a></li> <li><a href="/wiki/Terconazole" title="Terconazole">Terconazole</a></li> <li><a href="/wiki/Testosterone_isocaproate" title="Testosterone isocaproate">Testosterone isocaproate</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li> <li><a href="/wiki/Thiamylal_sodium" class="mw-redirect" title="Thiamylal sodium">Thiamylal sodium</a></li> <li><a href="/wiki/Thiothixene" class="mw-redirect" title="Thiothixene">Thiothixene</a></li> <li><a href="/wiki/Thonzonium_bromide" title="Thonzonium bromide">Thonzonium bromide</a></li> <li><a href="/wiki/Tianeptine" title="Tianeptine">Tianeptine</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/w/index.php?title=Tropanyl_3,5-dimethulbenzoate&action=edit&redlink=1" class="new" title="Tropanyl 3,5-dimethulbenzoate (page does not exist)">Tropanyl 3,5-dimethulbenzoate</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/wiki/Zeranol" title="Zeranol">Zeranol</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Sesamin" title="Sesamin">Sesamin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd></dl> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output .portal-bar-content-related{margin:0;list-style:none}.mw-parser-output .portal-bar-item{display:inline-block;margin:0.15em 0.2em;min-height:24px;line-height:24px}@media screen and (max-width:768px){.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;flex-flow:column wrap;align-items:baseline}.mw-parser-output .portal-bar-header{text-align:center;flex:0;padding-left:0.5em;margin:0 auto}.mw-parser-output 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