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<div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Cellular transport</span> </div> </a> <ul id="toc-Cellular_transport-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Enzymatic_activity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Enzymatic_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Enzymatic activity</span> </div> </a> <ul id="toc-Enzymatic_activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biological_sources_and_degradation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biological_sources_and_degradation"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.4</span> <span>Biological sources and degradation</span> </div> </a> <ul id="toc-Biological_sources_and_degradation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Diseases" class="vector-toc-list-item vector-toc-level-1 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class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemical_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Chemical synthesis</span> </div> </a> <ul id="toc-Chemical_synthesis-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-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">5.1</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacodynamics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacodynamics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Pharmacodynamics</span> </div> </a> <ul id="toc-Pharmacodynamics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Clinical_research" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Clinical_research"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Clinical research</span> </div> </a> <ul id="toc-Clinical_research-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_lipoic_acids" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Other_lipoic_acids"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Other lipoic acids</span> </div> </a> <ul id="toc-Other_lipoic_acids-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav 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" 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Available in 30 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-30" 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">30 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%AD%D9%85%D8%B6_%D8%A7%D9%84%D9%84%D9%8A%D8%A8%D9%88%D9%8A%D9%83" title="حمض الليبويك – Arabic" lang="ar" hreflang="ar" data-title="حمض الليبويك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Lipoik_tur%C5%9Fu" title="Lipoik turşu – Azerbaijani" lang="az" hreflang="az" data-title="Lipoik turşu" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%84%DB%8C%D9%BE%D9%88%D8%A6%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="لیپوئیک اسید – South Azerbaijani" lang="azb" hreflang="azb" data-title="لیپوئیک اسید" 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/%C3%80cid_lipoic" title="Àcid lipoic – Catalan" lang="ca" hreflang="ca" data-title="Àcid lipoic" 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/Kyselina_lipoov%C3%A1" title="Kyselina lipoová – Czech" lang="cs" hreflang="cs" data-title="Kyselina lipoová" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Lipons%C3%A4ure" title="Liponsäure – German" lang="de" hreflang="de" data-title="Liponsäure" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Lipoehape" title="Lipoehape – Estonian" lang="et" hreflang="et" data-title="Lipoehape" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_lipoico" title="Ácido lipoico – Spanish" lang="es" hreflang="es" data-title="Ácido lipoico" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%84%DB%8C%D9%BE%D9%88%D8%A6%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="لیپوئیک اسید – Persian" lang="fa" hreflang="fa" data-title="لیپوئیک اسید" 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/Acide_lipo%C3%AFque" title="Acide lipoïque – French" lang="fr" hreflang="fr" data-title="Acide lipoïque" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/%C3%81cido_lipoico" title="Ácido lipoico – Galician" lang="gl" hreflang="gl" data-title="Ácido lipoico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A6%AC%ED%8F%AC%EC%82%B0" title="리포산 – Korean" lang="ko" hreflang="ko" data-title="리포산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_lipoat" title="Asam lipoat – Indonesian" lang="id" hreflang="id" data-title="Asam lipoat" 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/Acido_lipoico" title="Acido lipoico – Italian" lang="it" hreflang="it" data-title="Acido lipoico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/%CE%91-liponsav" title="Α-liponsav – Hungarian" lang="hu" hreflang="hu" data-title="Α-liponsav" 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%9B%D0%B8%D0%BF%D0%BE%D0%B8%D0%BD%D1%81%D0%BA%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Липоинска киселина – Macedonian" lang="mk" hreflang="mk" data-title="Липоинска киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%CE%91-%E3%83%AA%E3%83%9D%E9%85%B8" title="Α-リポ酸 – Japanese" lang="ja" hreflang="ja" data-title="Α-リポ酸" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Tioktat_kislota" title="Tioktat kislota – Uzbek" lang="uz" hreflang="uz" data-title="Tioktat kislota" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_liponowy" title="Kwas liponowy – Polish" lang="pl" hreflang="pl" data-title="Kwas liponowy" 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/%C3%81cido_lipoico" title="Ácido lipoico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido lipoico" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Acid_lipoic" title="Acid lipoic – Romanian" lang="ro" hreflang="ro" data-title="Acid lipoic" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9B%D0%B8%D0%BF%D0%BE%D0%B5%D0%B2%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Липоевая кислота – Russian" lang="ru" hreflang="ru" data-title="Липоевая кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_lipoov%C3%A1" title="Kyselina lipoová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina lipoová" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Lipoinska_kiselina" title="Lipoinska kiselina – Serbian" lang="sr" hreflang="sr" data-title="Lipoinska kiselina" 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/Lipoinska_kiselina" title="Lipoinska kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Lipoinska kiselina" 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/Lipoiinihappo" title="Lipoiinihappo – Finnish" lang="fi" hreflang="fi" data-title="Lipoiinihappo" 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/Liponsyra" title="Liponsyra – Swedish" lang="sv" hreflang="sv" data-title="Liponsyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9B%D1%96%D0%BF%D0%BE%D1%94%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Ліпоєва кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Ліпоєва кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%84%D9%BE%D9%88%D8%A6%DA%A9_%D8%AA%DB%8C%D8%B2%D8%A7%D8%A8" title="لپوئک تیزاب – Urdu" lang="ur" hreflang="ur" data-title="لپوئک تیزاب" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A1%AB%E8%BE%9B%E9%85%B8" title="硫辛酸 – Chinese" lang="zh" hreflang="zh" data-title="硫辛酸" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q312229#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div class="vector-page-toolbar-container"> <div id="left-navigation"> <nav aria-label="Namespaces"> <div id="p-associated-pages" class="vector-menu vector-menu-tabs mw-portlet mw-portlet-associated-pages" > <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li id="ca-nstab-main" class="selected vector-tab-noicon mw-list-item"><a href="/wiki/Lipoic_acid" title="View the content page [c]" 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Alpha_lipoic_acid&redirect=no" class="mw-redirect" title="Alpha lipoic acid">Alpha lipoic acid</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to be confused with <a href="/wiki/Linolenic_acid" title="Linolenic acid">linolenic acid</a>, <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a>, or <a href="/wiki/%CE%91-Linolenic_acid" title="Α-Linolenic acid">alpha-Linolenic acid</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Lipoic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Lipoic_acid.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Lipoic_acid.svg/220px-Lipoic_acid.svg.png" decoding="async" width="220" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Lipoic_acid.svg/330px-Lipoic_acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9f/Lipoic_acid.svg/440px-Lipoic_acid.svg.png 2x" data-file-width="512" data-file-height="221" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Lipoic-acid-3D-vdW.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Lipoic-acid-3D-vdW.png/250px-Lipoic-acid-3D-vdW.png" decoding="async" width="220" height="110" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Lipoic-acid-3D-vdW.png/330px-Lipoic-acid-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/dc/Lipoic-acid-3D-vdW.png/500px-Lipoic-acid-3D-vdW.png 2x" data-file-width="1100" data-file-height="552" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Lipoic-acid-from-xtal-3D-bs-17.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Lipoic-acid-from-xtal-3D-bs-17.png/220px-Lipoic-acid-from-xtal-3D-bs-17.png" decoding="async" width="220" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Lipoic-acid-from-xtal-3D-bs-17.png/330px-Lipoic-acid-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Lipoic-acid-from-xtal-3D-bs-17.png/440px-Lipoic-acid-from-xtal-3D-bs-17.png 2x" data-file-width="3000" data-file-height="1214" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Lipoov%C3%A1_kyselina.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Lipoov%C3%A1_kyselina.jpg/250px-Lipoov%C3%A1_kyselina.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Lipoov%C3%A1_kyselina.jpg/330px-Lipoov%C3%A1_kyselina.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/33/Lipoov%C3%A1_kyselina.jpg/500px-Lipoov%C3%A1_kyselina.jpg 2x" data-file-width="9280" data-file-height="6944" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(<i>R</i>)-5-(1,2-Dithiolan-3-yl)pentanoic acid</div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">α-Lipoic acid; Alpha lipoic acid; Thioctic acid; 6,8-Dithiooctanoic acid</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1077-28-7">1077-28-7</a></span> (racemate)<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="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=1200-22-2">1200-22-2</a></span> (<i>R</i>)<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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><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%3DC%28O%29CCCC%5BC%40H%5D1SSCC1">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Beilstein_database" title="Beilstein database">Beilstein Reference</a></div> </td> <td>81851 </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><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=30314">CHEBI:30314</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> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><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/ChEMBL134342">ChEMBL134342</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> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><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.5886.html">5886</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> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><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/DB00166">DB00166</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> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.012.793">100.012.793</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q312229#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> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>214-071-2</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=4822">4822</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><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/C16241">C16241</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> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Lipoic+acid">Lipoic+acid</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><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/6112">6112</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><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/73Y7P0K73Y">73Y7P0K73Y</a></span> (racemate)<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="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/VLL71EBS9Z">VLL71EBS9Z</a></span> (<i>R</i>)<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> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><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></div> </td> <td><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/DTXSID7025508">DTXSID7025508</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q312229#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> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/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><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: AGBQKNBQESQNJD-SSDOTTSWSA-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></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: AGBQKNBQESQNJD-SSDOTTSWBZ</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)CCCC[C@H]1SSCC1</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>8</sub><span title="Hydrogen">H</span><sub>14</sub><span title="Oxygen">O</span><sub>2</sub><span title="Sulfur">S</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002206320000000000♠"></span>206.32</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Yellow needle-like crystals </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>60–62 °C (140–144 °F; 333–335 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Very Slightly Soluble(0.24 g/L)<sup id="cite_ref-pubmed_1-0" class="reference"><a href="#cite_note-pubmed-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in ethanol 50 mg/mL </td> <td>Soluble </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_A16" title="ATC code A16">A16AX01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=A16AX01">WHO</a></span>)  </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetics</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></div> </td> <td>30% (oral)<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Lipoamide" title="Lipoamide">Lipoamide</a><br /><a href="/wiki/Asparagusic_acid" title="Asparagusic acid">Asparagusic acid</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477002603&page2=Lipoic+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <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><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Lipoic acid</b> (<b>LA</b>), also known as <b>α-lipoic acid</b>, <b>alpha-lipoic acid</b> (<b>ALA</b>) and <b>thioctic acid</b>, is an <a href="/wiki/Organosulfur_compound" class="mw-redirect" title="Organosulfur compound">organosulfur compound</a> derived from <a href="/wiki/Caprylic_acid" title="Caprylic acid">caprylic acid</a> (octanoic acid).<sup id="cite_ref-lpi_3-0" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> ALA, which is made in animals normally, is essential for <a href="/wiki/Aerobic_metabolism" class="mw-redirect" title="Aerobic metabolism">aerobic metabolism</a>. It is also available as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> or <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical drug</a> in some countries. <b>Lipoate</b> is the <a href="/wiki/Conjugate_base" class="mw-redirect" title="Conjugate base">conjugate base</a> of lipoic acid, and the most prevalent form of LA under physiological conditions.<sup id="cite_ref-lpi_3-1" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Only the (<i>R</i>)-(+)-<a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> (RLA) exists in nature. RLA is an essential <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> of many processes.<sup id="cite_ref-lpi_3-2" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Physical_and_chemical_properties">Physical and chemical properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=1" title="Edit section: Physical and chemical properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lipoic acid contains two sulfur atoms connected by a <a href="/wiki/Disulfide_bond" class="mw-redirect" title="Disulfide bond">disulfide bond</a> in the <a href="/wiki/1,2-dithiolane" class="mw-redirect" title="1,2-dithiolane">1,2-dithiolane</a> ring. It also carries a carboxylic acid group. It is considered to be oxidized relative to its acyclic relative dihydrolipoic acid, in which each sulfur exists as a thiol.<sup id="cite_ref-lpi_3-3" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is a yellow solid. </p><p>(<i>R</i>)-(+)-lipoic acid (RLA) occurs naturally, but (<i>S</i>)-(-)-lipoic acid (SLA) has been synthesized. </p><p>For use in <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> materials and <a href="/wiki/Compounding" title="Compounding">compounding</a> pharmacies, the <a href="/wiki/United_States_Pharmacopeia" title="United States Pharmacopeia">USP</a> established an official monograph for R/S-LA.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biological_function">Biological function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=2" title="Edit section: Biological function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lipoic acid is a cofactor for five enzymes or classes of enzymes: <a href="/wiki/Pyruvate_dehydrogenase" title="Pyruvate dehydrogenase">pyruvate dehydrogenase</a>, <a href="/wiki/Oxoglutarate_dehydrogenase_complex" title="Oxoglutarate dehydrogenase complex">α-ketoglutarate dehydrogenase</a>, the <a href="/wiki/Glycine_cleavage_system" title="Glycine cleavage system">glycine cleavage system</a>, <a href="/wiki/Branched-chain_alpha-keto_acid_dehydrogenase_complex" title="Branched-chain alpha-keto acid dehydrogenase complex">branched-chain alpha-keto acid dehydrogenase</a>, and the α-oxo(keto)adipate dehydrogenase. The first two are critical to the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>. The GCS regulates <a href="/wiki/Glycine" title="Glycine">glycine</a> concentrations.<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> </p><p>HDAC1, HDAC2, HDAC3, HDAC6, HDAC8, and HDAC10 are targets of the reduced form (open dithiol) of (<i>R</i>)-lipoic acid. <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> </p> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis_and_attachment">Biosynthesis and attachment</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=3" title="Edit section: Biosynthesis and attachment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most endogenously produced RLA are not "free" because octanoic acid, the precursor to RLA, is bound to the enzyme complexes prior to enzymatic insertion of the sulfur atoms. As a cofactor, RLA is covalently attached by an amide bond to a terminal lysine residue of the enzyme's lipoyl domains. The precursor to lipoic acid, <a href="/wiki/Octanoic_acid" class="mw-redirect" title="Octanoic acid">octanoic acid</a>, is made via <a href="/wiki/Fatty_acid_biosynthesis" class="mw-redirect" title="Fatty acid biosynthesis">fatty acid biosynthesis</a> in the form of octanoyl-<a href="/wiki/Acyl_carrier_protein" title="Acyl carrier protein">acyl carrier protein</a>.<sup id="cite_ref-lpi_3-4" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In <a href="/wiki/Eukaryotes" class="mw-redirect" title="Eukaryotes">eukaryotes</a>, a second fatty acid biosynthetic pathway in <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> is used for this purpose.<sup id="cite_ref-lpi_3-5" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The octanoate is transferred as a thioester of <a href="/wiki/Acyl_carrier_protein" title="Acyl carrier protein">acyl carrier protein</a> from <a href="/wiki/Fatty_acid_biosynthesis" class="mw-redirect" title="Fatty acid biosynthesis">fatty acid biosynthesis</a> to an <a href="/wiki/Amide" title="Amide">amide</a> of the lipoyl domain protein by an <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> called an octanoyltransferase.<sup id="cite_ref-lpi_3-6" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Two hydrogens of octanoate are replaced with sulfur groups via a <a href="/wiki/Radical_SAM" class="mw-redirect" title="Radical SAM">radical SAM</a> mechanism, by <a href="/wiki/Lipoyl_synthase" title="Lipoyl synthase">lipoyl synthase</a>.<sup id="cite_ref-lpi_3-7" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> As a result, lipoic acid is synthesized attached to proteins and no free lipoic acid is produced. Lipoic acid can be removed whenever proteins are degraded and by action of the enzyme lipoamidase.<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> Free lipoate can be used by some organisms as an enzyme called <a href="/wiki/Lipoate_protein_ligase" class="mw-redirect" title="Lipoate protein ligase">lipoate protein ligase</a> that attaches it covalently to the correct protein. The <a href="/wiki/Ligase" title="Ligase">ligase</a> activity of this <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> requires <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</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> </p> <div class="mw-heading mw-heading3"><h3 id="Cellular_transport">Cellular transport</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=4" title="Edit section: Cellular transport"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Along with <a href="/wiki/Sodium" title="Sodium">sodium</a> and the vitamins <a href="/wiki/Biotin" title="Biotin">biotin</a> (B7) and <a href="/wiki/Pantothenic_acid" title="Pantothenic acid">pantothenic acid</a> (B5), lipoic acid enters cells through the <a href="/wiki/Sodium-dependent_multivitamin_transporter" title="Sodium-dependent multivitamin transporter">SMVT</a> (sodium-dependent multivitamin transporter). Each of the compounds transported by the SMVT is competitive with the others. For example research has shown that increasing intake of lipoic acid<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> or pantothenic acid<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> reduces the uptake of biotin and/or the activities of biotin-dependent enzymes. </p> <div class="mw-heading mw-heading3"><h3 id="Enzymatic_activity">Enzymatic activity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=5" title="Edit section: Enzymatic activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lipoic acid is a <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> for at least five <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> systems.<sup id="cite_ref-lpi_3-8" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Two of these are in the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a> through which many organisms turn nutrients into energy. Lipoylated <a href="/wiki/Enzymes" class="mw-redirect" title="Enzymes">enzymes</a> have lipoic acid attached to them covalently. The lipoyl group transfers <a href="/wiki/Acyl" class="mw-redirect" title="Acyl">acyl</a> groups in <a href="/w/index.php?title=2-oxoacid_dehydrogenase&action=edit&redlink=1" class="new" title="2-oxoacid dehydrogenase (page does not exist)">2-oxoacid dehydrogenase</a> complexes, and <a href="/wiki/Methylamine" title="Methylamine">methylamine</a> group in the <a href="/wiki/Glycine_cleavage_complex" class="mw-redirect" title="Glycine cleavage complex">glycine cleavage complex</a> or <a href="/wiki/Glycine_dehydrogenase" title="Glycine dehydrogenase">glycine dehydrogenase</a>.<sup id="cite_ref-lpi_3-9" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Lipoic acid is the cofactor of the following enzymes in humans:<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><sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption> </caption> <tbody><tr> <th>EC-number </th> <th>Enzyme </th> <th>Gene </th> <th>Multienzyme complex </th> <th>Type of metabolism </th></tr> <tr> <td><a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> <a rel="nofollow" class="external text" href="https://enzyme.expasy.org/EC/2.3.1.12">2.3.1.12</a> </td> <td><a href="/wiki/Dihydrolipoyl_transacetylase" title="Dihydrolipoyl transacetylase">dihydrolipoyl transacetylase</a> (E2) </td> <td><a href="/wiki/DLAT" class="mw-redirect" title="DLAT">DLAT</a> </td> <td><a href="/wiki/Pyruvate_dehydrogenase_complex" title="Pyruvate dehydrogenase complex">pyruvate dehydrogenase complex</a> (PDC) </td> <td rowspan="2"><a href="/wiki/Energy_metabolism" class="mw-redirect" title="Energy metabolism">energy metabolism</a> </td></tr> <tr> <td rowspan="2">EC <a rel="nofollow" class="external text" href="https://enzyme.expasy.org/EC/2.3.1.61">2.3.1.61</a> </td> <td rowspan="2"><a href="/wiki/Dihydrolipoyllysine-residue_succinyltransferase" title="Dihydrolipoyllysine-residue succinyltransferase">dihydrolipoyl succinyltransferase</a> (E2) </td> <td rowspan="2"><a href="/wiki/DLST" title="DLST">DLST</a> </td> <td><a href="/wiki/Oxoglutarate_dehydrogenase_complex" title="Oxoglutarate dehydrogenase complex">oxoglutarate dehydrogenase complex</a> (OGDC) </td></tr> <tr> <td><a href="/w/index.php?title=2-oxoadipate_dehydrogenase_complex&action=edit&redlink=1" class="new" title="2-oxoadipate dehydrogenase complex (page does not exist)">2-oxoadipate dehydrogenase complex</a> (OADHC) </td> <td rowspan="3"><a href="/wiki/Amino_acid_metabolism" class="mw-redirect" title="Amino acid metabolism">amino acid metabolism</a> </td></tr> <tr> <td>EC <a rel="nofollow" class="external text" href="https://enzyme.expasy.org/EC/2.3.1.168">2.3.1.168</a> </td> <td><a href="/w/index.php?title=Dihydrolipoyl_transacylase&action=edit&redlink=1" class="new" title="Dihydrolipoyl transacylase (page does not exist)">dihydrolipoyl transacylase</a> (E2) </td> <td><a href="/wiki/DBT_(gene)" title="DBT (gene)">DBT</a> </td> <td><a href="/wiki/Branched-chain_alpha-keto_acid_dehydrogenase_complex" title="Branched-chain alpha-keto acid dehydrogenase complex">branched-chain α-ketoacid dehydrogenase complex</a> (BCKDC) </td></tr> <tr> <td> </td> <td><a href="/wiki/GCSH" title="GCSH">H-protein</a> </td> <td><a href="/wiki/GCSH" title="GCSH">GCSH</a> </td> <td><a href="/wiki/Glycine_cleavage_system" title="Glycine cleavage system">glycine cleavage system</a> (GCS) </td></tr></tbody></table> <p>The most-studied of these is the pyruvate dehydrogenase complex.<sup id="cite_ref-lpi_3-10" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> These complexes have three central subunits: E1-3, which are the decarboxylase, lipoyl transferase, and <a href="/wiki/Dihydrolipoamide_dehydrogenase" title="Dihydrolipoamide dehydrogenase">dihydrolipoamide dehydrogenase</a>, respectively. These complexes have a central E2 core and the other subunits surround this core to form the complex. In the gap between these two subunits, the lipoyl domain ferries intermediates between the active sites.<sup id="cite_ref-lpi_3-11" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> The lipoyl domain itself is attached by a flexible linker to the E2 core and the number of lipoyl domains varies from one to three for a given organism. The number of domains has been experimentally varied and seems to have little effect on growth until over nine are added, although more than three decreased activity of the complex.<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> </p><p>Lipoic acid serves as co-factor to the <a href="/wiki/Acetoin_dehydrogenase" title="Acetoin dehydrogenase">acetoin dehydrogenase</a> complex catalyzing the conversion of <a href="/wiki/Acetoin" title="Acetoin">acetoin</a> (3-hydroxy-2-butanone) to acetaldehyde and <a href="/wiki/Acetyl_coenzyme_A" class="mw-redirect" title="Acetyl coenzyme A">acetyl coenzyme A</a>.<sup id="cite_ref-lpi_3-12" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Glycine_cleavage_system" title="Glycine cleavage system">glycine cleavage system</a> differs from the other complexes, and has a different nomenclature.<sup id="cite_ref-lpi_3-13" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In this system, the H protein is a free lipoyl domain with additional helices, the L protein is a dihydrolipoamide dehydrogenase, the P protein is the decarboxylase, and the T protein transfers the <a href="/wiki/Methylamine" title="Methylamine">methylamine</a> from lipoate to <a href="/wiki/Tetrahydrofolate" class="mw-redirect" title="Tetrahydrofolate">tetrahydrofolate</a> (THF) yielding methylene-THF and ammonia. Methylene-THF is then used by serine hydroxymethyltransferase to synthesize <a href="/wiki/Serine" title="Serine">serine</a> from <a href="/wiki/Glycine" title="Glycine">glycine</a>. This system is part of plant <a href="/wiki/Photorespiration" title="Photorespiration">photorespiration</a>.<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="Biological_sources_and_degradation">Biological sources and degradation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=6" title="Edit section: Biological sources and degradation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Lipoic acid is present in many foods in which it is bound to lysine in proteins,<sup id="cite_ref-lpi_3-14" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> but slightly more so in kidney, heart, liver, spinach, broccoli, and yeast extract.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Naturally occurring lipoic acid is always covalently bound and not readily available from dietary sources.<sup id="cite_ref-lpi_3-15" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In addition, the amount of lipoic acid present in dietary sources is low. For instance, the purification of lipoic acid to determine its structure used an estimated 10 tons of liver residue, which yielded 30 mg of lipoic acid.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> As a result, all lipoic acid available as a supplement is chemically synthesized.<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. (November 2024)">citation needed</span></a></i>]</sup> </p><p>Baseline levels (prior to supplementation) of RLA and R-DHLA have not been detected in human plasma.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> RLA has been detected at 12.3−43.1 ng/mL following acid hydrolysis, which releases protein-bound lipoic acid. Enzymatic hydrolysis of protein bound lipoic acid released 1.4−11.6 ng/mL and <1-38.2 ng/mL using <a href="/wiki/Subtilisin" title="Subtilisin">subtilisin</a> and <a href="/wiki/Alcalase" class="mw-redirect" title="Alcalase">alcalase</a>, respectively.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Digestive proteolytic enzymes cleave the R-lipoyllysine residue from the mitochondrial enzyme complexes derived from food but are unable to cleave the lipoic acid-<small>L</small>-<a href="/wiki/Lysine" title="Lysine">lysine</a> amide bond.<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> Both synthetic lipoamide and (<i>R</i>)-lipoyl-<small>L</small>-lysine are rapidly cleaved by serum lipoamidases, which release free (<i>R</i>)-lipoic acid and either <small>L</small>-lysine or ammonia.<sup id="cite_ref-lpi_3-16" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Little is known about the degradation and utilization of aliphatic sulfides such as lipoic acid, except for <a href="/wiki/Cysteine" title="Cysteine">cysteine</a>.<sup id="cite_ref-lpi_3-17" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Lipoic acid is metabolized in a variety of ways when given as a dietary supplement in mammals.<sup id="cite_ref-lpi_3-18" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ReferenceA_24-0" class="reference"><a href="#cite_note-ReferenceA-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Degradation to tetranorlipoic acid, oxidation of one or both of the sulfur atoms to the sulfoxide, and S-methylation of the sulfide were observed. Conjugation of unmodified lipoic acid to glycine was detected especially in mice.<sup id="cite_ref-ReferenceA_24-1" class="reference"><a href="#cite_note-ReferenceA-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Degradation of lipoic acid is similar in humans, although it is not clear if the sulfur atoms become significantly oxidized.<sup id="cite_ref-lpi_3-19" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Apparently mammals are not capable of utilizing lipoic acid as a sulfur source. </p> <div class="mw-heading mw-heading2"><h2 id="Diseases">Diseases</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=7" title="Edit section: Diseases"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Combined_malonic_and_methylmalonic_aciduria_(CMAMMA)"><span id="Combined_malonic_and_methylmalonic_aciduria_.28CMAMMA.29"></span>Combined malonic and methylmalonic aciduria (CMAMMA)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=8" title="Edit section: Combined malonic and methylmalonic aciduria (CMAMMA)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the metabolic disease <a href="/wiki/Combined_malonic_and_methylmalonic_aciduria" title="Combined malonic and methylmalonic aciduria">combined malonic and methylmalonic aciduria</a> (CMAMMA) due to <a href="/wiki/ACSF3" title="ACSF3">ACSF3</a> deficiency, mitochondrial fatty acid synthesis (mtFASII), which is the precursor reaction of lipoic acid biosynthesis, is impaired.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_27-0" class="reference"><a href="#cite_note-:0-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The result is a reduced <a href="/wiki/Post-translational_modification#PTMs_involving_addition_of_functional_groups" title="Post-translational modification">lipoylation</a> degree of important mitochondrial enzymes, such as <a href="/wiki/Pyruvate_dehydrogenase_complex" title="Pyruvate dehydrogenase complex">pyruvate dehydrogenase complex</a> (PDC) and <a href="/wiki/Oxoglutarate_dehydrogenase_complex" title="Oxoglutarate dehydrogenase complex">α-ketoglutarate dehydrogenase complex</a> (α-KGDHC).<sup id="cite_ref-:0_27-1" class="reference"><a href="#cite_note-:0-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Supplementation with lipoic acid does not restore mitochondrial function.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_27-2" class="reference"><a href="#cite_note-:0-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemical_synthesis">Chemical synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=9" title="Edit section: Chemical synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span typeof="mw:File"><a href="/wiki/File:(R)-Liponic_Acid_Structural_Formula_V.1.svg" class="mw-file-description" title="R-isomer"><img alt="R-isomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/%28R%29-Liponic_Acid_Structural_Formula_V.1.svg/200px-%28R%29-Liponic_Acid_Structural_Formula_V.1.svg.png" decoding="async" width="200" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9a/%28R%29-Liponic_Acid_Structural_Formula_V.1.svg/300px-%28R%29-Liponic_Acid_Structural_Formula_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9a/%28R%29-Liponic_Acid_Structural_Formula_V.1.svg/400px-%28R%29-Liponic_Acid_Structural_Formula_V.1.svg.png 2x" data-file-width="376" data-file-height="158" /></a></span> <span typeof="mw:File"><a href="/wiki/File:(S)-Liponic_Acid_Structural_Formula_V.1.svg" class="mw-file-description" title="S-isomer"><img alt="S-isomer" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/%28S%29-Liponic_Acid_Structural_Formula_V.1.svg/200px-%28S%29-Liponic_Acid_Structural_Formula_V.1.svg.png" decoding="async" width="200" height="84" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/97/%28S%29-Liponic_Acid_Structural_Formula_V.1.svg/300px-%28S%29-Liponic_Acid_Structural_Formula_V.1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/97/%28S%29-Liponic_Acid_Structural_Formula_V.1.svg/400px-%28S%29-Liponic_Acid_Structural_Formula_V.1.svg.png 2x" data-file-width="376" data-file-height="158" /></a></span> </p><p>SLA did not exist prior to chemical synthesis in 1952.<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><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> SLA is produced in equal amounts with RLA during achiral manufacturing processes. The racemic form was more widely used clinically in Europe and Japan in the 1950s to 1960s despite the early recognition that the various forms of LA are not bioequivalent.<sup id="cite_ref-Kleeman_31-0" class="reference"><a href="#cite_note-Kleeman-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> The first synthetic procedures appeared for RLA and SLA in the mid-1950s.<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><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><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Advances in chiral chemistry led to more efficient technologies for manufacturing the single enantiomers by both classical resolution and <a href="/wiki/Asymmetric_synthesis" class="mw-redirect" title="Asymmetric synthesis">asymmetric synthesis</a> and the demand for RLA also grew at this time. In the 21st century, R/S-LA, RLA and SLA with high chemical and/or optical purities are available in industrial quantities. At the current time, most of the world supply of R/S-LA and RLA is manufactured in China and smaller amounts in Italy, Germany, and Japan. RLA is produced by modifications of a process first described by Georg Lang in a Ph.D. thesis and later patented by DeGussa.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Although RLA is favored nutritionally due to its "vitamin-like" role in metabolism, both RLA and R/S-LA are widely available as dietary supplements. Both <a href="/wiki/Stereospecific" class="mw-redirect" title="Stereospecific">stereospecific</a> and non-stereospecific reactions are known to occur <i>in vivo</i> and contribute to the mechanisms of action, but evidence to date indicates RLA may be the <a href="/wiki/Eutomer" class="mw-redirect" title="Eutomer">eutomer</a> (the nutritionally and therapeutically preferred form).<sup id="cite_ref-Carlson08_38-0" class="reference"><a href="#cite_note-Carlson08-38"><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> </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=Lipoic_acid&action=edit&section=10" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <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=Lipoic_acid&action=edit&section=11" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 2007 human <a href="/wiki/Pharmacokinetic" class="mw-redirect" title="Pharmacokinetic">pharmacokinetic</a> study of sodium RLA demonstrated the maximum concentration in plasma and bioavailability are significantly greater than the free acid form, and rivals plasma levels achieved by intravenous administration of the free acid form.<sup id="cite_ref-ReferenceB_40-0" class="reference"><a href="#cite_note-ReferenceB-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> Additionally, high plasma levels comparable to those in animal models where Nrf2 was activated were achieved.<sup id="cite_ref-ReferenceB_40-1" class="reference"><a href="#cite_note-ReferenceB-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>The various forms of LA are not bioequivalent.<sup id="cite_ref-Kleeman_31-1" class="reference"><a href="#cite_note-Kleeman-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Very few studies compare individual enantiomers with racemic lipoic acid. It is unclear if twice as much racemic lipoic acid can replace RLA.<sup id="cite_ref-ReferenceB_40-2" class="reference"><a href="#cite_note-ReferenceB-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>The toxic dose of LA in cats is much lower than that in humans or dogs and produces hepatocellular toxicity.<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> <div class="mw-heading mw-heading3"><h3 id="Pharmacodynamics">Pharmacodynamics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=12" title="Edit section: Pharmacodynamics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The mechanism and action of lipoic acid when supplied externally to an organism is controversial. Lipoic acid in a cell seems primarily to induce the oxidative stress response rather than directly scavenge free radicals. This effect is specific for RLA.<sup id="cite_ref-Shay08_42-0" class="reference"><a href="#cite_note-Shay08-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Despite the strongly reducing milieu, LA has been detected intracellularly in both oxidized and reduced forms.<sup id="cite_ref-Packer1995_43-0" class="reference"><a href="#cite_note-Packer1995-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> LA is able to scavenge reactive oxygen and reactive nitrogen species in a biochemical assay due to long incubation times, but there is little evidence this occurs within a cell or that radical scavenging contributes to the primary mechanisms of action of LA.<sup id="cite_ref-Shay08_42-1" class="reference"><a href="#cite_note-Shay08-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ReferenceC_44-0" class="reference"><a href="#cite_note-ReferenceC-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> The relatively good scavenging activity of LA toward <a href="/wiki/Hypochlorous_acid" title="Hypochlorous acid">hypochlorous acid</a> (a bactericidal produced by neutrophils that may produce inflammation and tissue damage) is due to the strained conformation of the 5-membered dithiolane ring, which is lost upon reduction to DHLA. In cells, LA is reduced to dihydrolipoic acid, which is generally regarded as the more bioactive form of LA and the form responsible for most of the antioxidant effects and for lowering the redox activities of unbound iron and copper.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> This theory has been challenged due to the high level of reactivity of the two free sulfhydryls, low intracellular concentrations of DHLA as well as the rapid methylation of one or both sulfhydryls, rapid side-chain oxidation to shorter metabolites and rapid efflux from the cell. Although both DHLA and LA have been found inside cells after administration, most intracellular DHLA probably exists as mixed disulfides with various cysteine residues from cytosolic and mitochondrial proteins.<sup id="cite_ref-Carlson08_38-1" class="reference"><a href="#cite_note-Carlson08-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Recent findings suggest therapeutic and anti-aging effects are due to modulation of signal transduction and gene transcription, which improve the antioxidant status of the cell. However, this likely occurs via pro-oxidant mechanisms, not by radical scavenging or reducing effects.<sup id="cite_ref-Shay08_42-2" class="reference"><a href="#cite_note-Shay08-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ReferenceC_44-1" class="reference"><a href="#cite_note-ReferenceC-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shay_in_Packer_46-0" class="reference"><a href="#cite_note-Shay_in_Packer-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>All the <a href="/wiki/Disulfide" title="Disulfide">disulfide</a> forms of LA (R/S-LA, RLA and SLA) can be reduced to <a href="/wiki/DHLA" class="mw-redirect" title="DHLA">DHLA</a> although both tissue specific and stereoselective (preference for one enantiomer over the other) reductions have been reported in model systems. At least two cytosolic enzymes, <a href="/wiki/Glutathione_reductase" title="Glutathione reductase">glutathione reductase</a> (GR) and <a href="/wiki/Thioredoxin_reductase" title="Thioredoxin reductase">thioredoxin reductase</a> (Trx1), and two mitochondrial enzymes, <a href="/wiki/Lipoamide_dehydrogenase" class="mw-redirect" title="Lipoamide dehydrogenase">lipoamide dehydrogenase</a> and <a href="/wiki/Thioredoxin_reductase" title="Thioredoxin reductase">thioredoxin reductase</a> (Trx2), reduce LA. SLA is stereoselectively reduced by cytosolic GR whereas Trx1, Trx2 and lipoamide dehydrogenase stereoselectively reduce RLA. (<i>R</i>)-(+)-lipoic acid is enzymatically or chemically reduced to (<i>R</i>)-(-)-dihydrolipoic acid whereas (<i>S</i>)-(-)-lipoic acid is reduced to (<i>S</i>)-(+)-dihydrolipoic acid.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-50" class="reference"><a href="#cite_note-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Dihydrolipoic acid (DHLA) can also form intracellularly and extracellularly via non-enzymatic, <a href="/wiki/Thiol-disulfide_exchange" class="mw-redirect" title="Thiol-disulfide exchange">thiol-disulfide exchange reactions</a>.<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><p>RLA may function <i>in vivo</i> like a B-vitamin and at higher doses like plant-derived nutrients, such as <a href="/wiki/Curcumin" title="Curcumin">curcumin</a>, <a href="/wiki/Sulforaphane" title="Sulforaphane">sulforaphane</a>, <a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a>, and other nutritional substances that induce <a href="/wiki/Drug_metabolism#Phase_II_–_conjugation" title="Drug metabolism">phase II detoxification enzymes</a>, thus acting as cytoprotective agents.<sup id="cite_ref-Shay_in_Packer_46-1" class="reference"><a href="#cite_note-Shay_in_Packer-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> This stress response indirectly improves the antioxidant capacity of the cell.<sup id="cite_ref-Shay08_42-3" class="reference"><a href="#cite_note-Shay08-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p><p>The (<i>S</i>)-enantiomer of LA was shown to be toxic when administered to thiamine-deficient rats.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Gal1965_57-0" class="reference"><a href="#cite_note-Gal1965-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p><p>Several studies have demonstrated that SLA either has lower activity than RLA or interferes with the specific effects of RLA by <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitive inhibition</a>.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><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><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><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="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=13" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>R/S-LA and RLA are widely available as over-the-counter nutritional supplements in the United States in the form of capsules, tablets, and aqueous liquids, and have been marketed as <a href="/wiki/Antioxidants" class="mw-redirect" title="Antioxidants">antioxidants</a> and pertaining to cellular glucose utilization for metabolic disorders and type 2 diabetes.<sup id="cite_ref-lpi_3-20" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Although the body can synthesize LA, it can also be absorbed from the diet. Dietary supplementation in doses from 200–600 mg is likely to provide up to 1000 times the amount available from a regular diet. Gastrointestinal absorption is variable and decreases with the use of food. It is therefore recommended that dietary LA be taken 30–60 minutes before or at least 120 minutes after a meal. Maximum blood levels of LA are achieved 30–60 minutes after dietary supplementation, and it is thought to be largely metabolized in the liver.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p><p>In Germany, LA is approved as a drug for the treatment of <a href="/wiki/Diabetic_neuropathy" title="Diabetic neuropathy">diabetic neuropathy</a> since 1966 and is available as a non-prescription pharmaceutical.<sup id="cite_ref-Ziegle_64-0" class="reference"><a href="#cite_note-Ziegle-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Clinical_research">Clinical research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=14" title="Edit section: Clinical research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to the <a href="/wiki/American_Cancer_Society" title="American Cancer Society">American Cancer Society</a> as of 2013, "there is no reliable scientific evidence at this time that lipoic acid prevents the development or spread of cancer".<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> As of 2015, intravenously administered ALA is unapproved anywhere in the world except Germany for <a href="/wiki/Diabetic_neuropathy" title="Diabetic neuropathy">diabetic neuropathy</a>, but has been proven reasonably safe and effective.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> As of 2012, there was no good evidence alpha lipoic acid helps people with <a href="/wiki/Mitochondrial_disorders" class="mw-redirect" title="Mitochondrial disorders">mitochondrial disorders</a>.<sup id="cite_ref-pmid22513923_67-0" class="reference"><a href="#cite_note-pmid22513923-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> A 2018 review recommended ALA as an anti-obesity supplement with low dosage (< 600 mg/day) for a short period (<10 weeks).<sup id="cite_ref-Namazi_68-0" class="reference"><a href="#cite_note-Namazi-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Other_lipoic_acids">Other lipoic acids</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=15" title="Edit section: Other lipoic acids"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li>β-lipoic acid is a thiosulfinate of α-lipoic acid</li></ul> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Lipoic_acid&action=edit&section=16" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Aminolevulinic_acid" title="Aminolevulinic acid">Aminolevulinic acid</a></li></ul> <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=Lipoic_acid&action=edit&section=17" 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-pubmed-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-pubmed_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 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class="navbox-group" style="width:1%"><a href="/wiki/Vitamin" title="Vitamin">vitamins</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/Thiamine_pyrophosphate" title="Thiamine pyrophosphate">TPP / ThDP</a> (B<sub>1</sub>)</li> <li><a href="/wiki/Flavin_mononucleotide" title="Flavin mononucleotide">FMN</a>, <a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a> (B<sub>2</sub>)</li> <li><a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD<sup>+</sup></a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NADH</a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADP<sup>+</sup></a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADPH</a> (B<sub>3</sub>)</li> <li><a href="/wiki/Coenzyme_A" title="Coenzyme A">Coenzyme A</a> (B<sub>5</sub>)</li> <li><a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">PLP / P5P</a> (B<sub>6</sub>)</li> <li><a href="/wiki/Biotin" title="Biotin">Biotin</a> (B<sub>7</sub>)</li> <li><a href="/wiki/Tetrahydrofolic_acid" title="Tetrahydrofolic acid">THFA / H<sub>4</sub>FA</a>, <a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">DHFA / H<sub>2</sub>FA</a>, <a href="/wiki/5,10-Methylenetetrahydrofolate" title="5,10-Methylenetetrahydrofolate">MTHF</a> (B<sub>9</sub>)</li> <li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">AdoCbl</a>, <a href="/wiki/Methylcobalamin" title="Methylcobalamin">MeCbl</a> (B<sub>12</sub>)</li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a> (C)</li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone</a> (K<sub>1</sub>), <a href="/wiki/Vitamin_K" title="Vitamin K">Menaquinone</a> (K<sub>2</sub>)</li> <li><a href="/wiki/Coenzyme_F420" title="Coenzyme F420">Coenzyme F420</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cofactor_(biochemistry)#Non-vitamins" title="Cofactor (biochemistry)">non-vitamins</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/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine">SAMe</a></li> <li><a href="/wiki/3%27-Phosphoadenosine-5%27-phosphosulfate" title="3'-Phosphoadenosine-5'-phosphosulfate">PAPS</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">GSH</a></li> <li><a href="/wiki/Coenzyme_B" title="Coenzyme B">Coenzyme B</a></li> <li><a href="/wiki/Cofactor_F430" title="Cofactor F430">Cofactor F430</a></li> <li><a href="/wiki/Coenzyme_M" title="Coenzyme M">Coenzyme M</a></li> <li><a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">Coenzyme Q</a></li> <li><a href="/wiki/Heme" title="Heme">Heme / Haem</a> (<a href="/wiki/Heme_A" title="Heme A">A</a>, <a href="/wiki/Heme_B" title="Heme B">B</a>, <a href="/wiki/Heme_C" title="Heme C">C</a>, <a href="/wiki/Heme_O" title="Heme O">O</a>)</li> <li><a class="mw-selflink selflink">Lipoic Acid</a></li> <li><a href="/wiki/Methanofuran" title="Methanofuran">Methanofuran</a></li> <li><a href="/wiki/Molybdopterin" title="Molybdopterin">Molybdopterin</a></li> <li><a href="/wiki/Mycofactocin" title="Mycofactocin">Mycofactocin</a></li> <li><a href="/wiki/Pyrroloquinoline_quinone" title="Pyrroloquinoline quinone">PQQ</a></li> <li><a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">THB / BH<sub>4</sub></a></li> <li><a href="/wiki/Tetrahydromethanopterin" title="Tetrahydromethanopterin">THMPT / H<sub>4</sub>MPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">metal ions</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/Calcium" title="Calcium">Ca<sup>2+</sup></a></li> <li><a href="/wiki/Copper" title="Copper">Cu<sup>2+</sup></a></li> <li><a href="/wiki/Iron" title="Iron">Fe<sup>2+</sup>, Fe<sup>3+</sup></a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Mg<sup>2+</sup></a></li> <li><a href="/wiki/Manganese" title="Manganese">Mn<sup>2+</sup></a></li> <li><a href="/wiki/Molybdenum" title="Molybdenum">Mo</a></li> <li><a href="/wiki/Nickel" title="Nickel">Ni<sup>2+</sup></a></li> <li><a href="/wiki/Zinc" title="Zinc">Zn<sup>2+</sup></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Base forms</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/Vitamin" title="Vitamin">vitamins</a></i>: <i>see <a href="/wiki/Template:Vitamins" title="Template:Vitamins">vitamins</a></i></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" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Chelating_agents_/_chelation_therapy_(V03AC,_others)460" style="padding:3px"><table class="nowraplinks hlist 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:Chelating_agents" title="Template:Chelating agents"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Chelating_agents" title="Template talk:Chelating agents"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Chelating_agents" title="Special:EditPage/Template:Chelating agents"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Chelating_agents_/_chelation_therapy_(V03AC,_others)460" style="font-size:114%;margin:0 4em"><a href="/wiki/Chelation" title="Chelation">Chelating agents</a> / <a href="/wiki/Chelation_therapy" title="Chelation therapy">chelation therapy</a> (<a href="/wiki/ATC_code_V03#V03AC" title="ATC code V03">V03AC</a>, others)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Copper" title="Copper">Copper</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/Penicillamine" title="Penicillamine">Penicillamine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Iron" title="Iron">Iron</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/Deferasirox" title="Deferasirox">Deferasirox</a></li> <li><a href="/wiki/Deferiprone" title="Deferiprone">Deferiprone</a></li> <li><a href="/wiki/Deferoxamine" title="Deferoxamine">Deferoxamine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lead" title="Lead">Lead</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/Dimercaprol" title="Dimercaprol">BAL</a><sup>#</sup></li> <li><a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">EDTA</a><sup>#</sup> <ul><li><a href="/wiki/Dexrazoxane" title="Dexrazoxane">Dexrazoxane</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thallium" title="Thallium">Thallium</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/Prussian_blue" title="Prussian blue">Prussian blue</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">ALA</a></li> <li><a href="/wiki/BAPTA" title="BAPTA">BAPTA</a></li> <li><a href="/wiki/2,3-Dimercapto-1-propanesulfonic_acid" title="2,3-Dimercapto-1-propanesulfonic acid">DMPS</a></li> <li><a href="/wiki/Dimercaptosuccinic_acid" class="mw-redirect" title="Dimercaptosuccinic acid">DMSA</a><sup>#</sup></li> <li><a href="/wiki/Pentetic_acid" title="Pentetic acid">DTPA</a></li> <li><a href="/wiki/EGTA_(chemical)" class="mw-redirect" title="EGTA (chemical)">EGTA</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Antioxidants62" 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:Antioxidants" title="Template:Antioxidants"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a 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(vitamin C)</li> <li><a href="/wiki/Carotenoid" title="Carotenoid">Carotenoids</a> (<a href="/wiki/Vitamin_A" title="Vitamin A">vitamin A</a>)</li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/wiki/Edaravone" title="Edaravone">Edaravone</a></li> <li><a href="/wiki/Antioxidant_effect_of_polyphenols_and_natural_phenols" title="Antioxidant effect of polyphenols and natural phenols">Polyphenols</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">Glutathione</a></li> <li><a href="/wiki/Hydroxytyrosol" title="Hydroxytyrosol">Hydroxytyrosol</a></li> <li><a href="/wiki/Carnitine" title="Carnitine"><small>L</small>-carnitine</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li> <li><a href="/wiki/Mofegiline" title="Mofegiline">Mofegiline</a></li> <li><a href="/wiki/Acetylcysteine" title="Acetylcysteine"><i>N</i>-Acetylcysteine</a> (NAC)</li> <li><a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin"><i>N</i>-Acetylserotonin</a> (NAS)</li> <li><a href="/wiki/Oleocanthal" title="Oleocanthal">Oleocanthal</a></li> <li><a href="/wiki/Oleuropein" title="Oleuropein">Oleuropein</a></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a></li> <li><a href="/wiki/Tocopherol" title="Tocopherol">Tocopherols</a> (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>)</li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienols</a> (<a href="/wiki/Vitamin_E" title="Vitamin E">vitamin E</a>)</li> <li><a href="/wiki/Tyrosol" title="Tyrosol">Tyrosol</a></li> <li><a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">Ubiquinone</a> (coenzyme Q)</li> <li><a href="/wiki/Uric_acid" title="Uric acid">Uric acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fuel antioxidants</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/Butylated_hydroxyanisole" title="Butylated hydroxyanisole">Butylated hydroxyanisole</a></li> <li><a href="/wiki/Butylated_hydroxytoluene" title="Butylated hydroxytoluene">Butylated hydroxytoluene</a></li> <li><a href="/wiki/2,6-Di-tert-butylphenol" title="2,6-Di-tert-butylphenol">2,6-Di-<i>tert</i>-butylphenol</a></li> <li><a href="/wiki/1,2-Diaminopropane" title="1,2-Diaminopropane">1,2-Diaminopropane</a></li> <li><a href="/wiki/2,4-Dimethyl-6-tert-butylphenol" title="2,4-Dimethyl-6-tert-butylphenol">2,4-Dimethyl-6-<i>tert</i>-butylphenol</a></li> <li><a href="/wiki/Ethylenediamine" title="Ethylenediamine">Ethylenediamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Measurements</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/Folin%E2%80%93Ciocalteu_reagent" title="Folin–Ciocalteu reagent">Folin method</a></li> <li><a href="/wiki/Oxygen_radical_absorbance_capacity" title="Oxygen radical absorbance capacity">ORAC</a></li> <li><a href="/wiki/Trolox_equivalent_antioxidant_capacity" title="Trolox equivalent antioxidant capacity">TEAC</a></li> <li><a href="/wiki/Ferric_reducing_ability_of_plasma" title="Ferric reducing ability of plasma">FRAP</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="Dietary_supplements155" 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:Dietary_supplement" title="Template:Dietary supplement"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Dietary_supplement" title="Template talk:Dietary supplement"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Dietary_supplement" title="Special:EditPage/Template:Dietary supplement"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Dietary_supplements155" style="font-size:114%;margin:0 4em"><a href="/wiki/Dietary_supplement" title="Dietary supplement">Dietary supplements</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types</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/Bodybuilding_supplement" title="Bodybuilding supplement">Bodybuilding supplement</a></li> <li><a href="/wiki/Energy_drink" title="Energy drink">Energy drink</a></li> <li><a href="/wiki/Energy_bar" title="Energy bar">Energy bar</a></li> <li><a href="/wiki/Essential_fatty_acid" title="Essential fatty acid">Fatty acids</a></li> <li><a href="/wiki/Herbal_medicine" title="Herbal medicine">Herbal supplements</a></li> <li><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">Minerals</a></li> <li><a href="/wiki/Prebiotic_(nutrition)" title="Prebiotic (nutrition)">Prebiotics</a></li> <li><a href="/wiki/Probiotic" title="Probiotic">Probiotics</a> (<a href="/wiki/Lactobacillus" title="Lactobacillus">Lactobacillus</a></li> <li><a href="/wiki/Bifidobacterium" title="Bifidobacterium">Bifidobacterium</a>)</li> <li><a href="/wiki/Protein_supplement" title="Protein supplement">Protein supplements</a></li> <li><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a> and<br /><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">chemical elements<br /> ("minerals")</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/Vitamin_A" title="Vitamin A">Retinol (Vitamin A)</a></li> <li><a href="/wiki/B_vitamins" title="B vitamins">B vitamins</a> <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine (B<sub>1</sub>)</a></li> <li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin (B<sub>2</sub>)</a></li> <li><a href="/wiki/Niacin_(nutrient)" class="mw-redirect" title="Niacin (nutrient)">Niacin (B<sub>3</sub>)</a></li> <li><a href="/wiki/Pantothenic_acid" title="Pantothenic acid">Pantothenic acid (B<sub>5</sub>)</a></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">Pyridoxine (B<sub>6</sub>)</a></li> <li><a href="/wiki/Biotin" title="Biotin">Biotin (B<sub>7</sub>)</a></li> <li><a href="/wiki/Folate" title="Folate">Folic acid (B<sub>9</sub>)</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin (B<sub>12</sub>)</a></li></ul></li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid (Vitamin C)</a></li> <li><a href="/wiki/Vitamin_D" title="Vitamin D">Ergocalciferol and Cholecalciferol (Vitamin D)</a></li> <li><a href="/wiki/Vitamin_E" title="Vitamin E">Tocopherol (Vitamin E)</a></li> <li><a href="/wiki/Vitamin_K" title="Vitamin K">Naphthoquinone (Vitamin K)</a></li></ul> <ul><li><a href="/wiki/Calcium_supplement" title="Calcium supplement">Calcium</a></li> <li><a href="/wiki/Choline" title="Choline">Choline</a></li> <li><a href="/wiki/Chromium" title="Chromium">Chromium</a></li> <li><a href="/wiki/Cobalt" title="Cobalt">Cobalt</a></li> <li><a href="/wiki/Copper" title="Copper">Copper</a></li> <li><a href="/wiki/Fluorine" title="Fluorine">Fluorine</a></li> <li><a href="/wiki/Iodine" title="Iodine">Iodine</a></li> <li><a href="/wiki/Iron" title="Iron">Iron</a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Magnesium</a></li> <li><a href="/wiki/Manganese" title="Manganese">Manganese</a></li> <li><a href="/wiki/Molybdenum" title="Molybdenum">Molybdenum</a></li> <li><a href="/wiki/Phosphorus" title="Phosphorus">Phosphorus</a></li> <li><a href="/wiki/Potassium" title="Potassium">Potassium</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a></li> <li><a href="/wiki/Sodium" title="Sodium">Sodium</a></li> <li><a href="/wiki/Sulfur" title="Sulfur">Sulfur</a></li> <li><a href="/wiki/Zinc" title="Zinc">Zinc</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other common <br />ingredients</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/Arginine_alpha-ketoglutarate" title="Arginine alpha-ketoglutarate">AAKG</a></li> <li><a href="/wiki/Beta-Hydroxy_beta-methylbutyric_acid" class="mw-redirect" title="Beta-Hydroxy beta-methylbutyric acid">β-hydroxy β-methylbutyrate</a></li> <li><a href="/wiki/Carnitine" title="Carnitine">Carnitine</a></li> <li><a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">Chondroitin sulfate</a></li> <li><a href="/wiki/Cod_liver_oil" title="Cod liver oil">Cod liver oil</a></li> <li><a href="/wiki/Copper_gluconate" title="Copper gluconate">Copper gluconate</a></li> <li><a href="/wiki/Creatine" title="Creatine">Creatine</a></li> <li><a href="/wiki/Dietary_fiber" title="Dietary fiber">Dietary fiber</a></li> <li><a href="/wiki/Echinacea#Medicinal_effects" title="Echinacea">Echinacea</a></li> <li><a href="/wiki/Ephedra_(medicine)" title="Ephedra (medicine)">Ephedra</a></li> <li><a href="/wiki/Fish_oil" title="Fish oil">Fish oil</a></li> <li><a href="/wiki/Folate" title="Folate">Folic acid</a></li> <li><a href="/wiki/Ginseng" title="Ginseng">Ginseng</a></li> <li><a href="/wiki/Glucosamine" title="Glucosamine">Glucosamine</a></li> <li><a href="/wiki/Glutamine" title="Glutamine">Glutamine</a></li> <li><a href="/wiki/Grape_seed_extract" title="Grape seed extract">Grape seed extract</a></li> <li><a href="/wiki/Guarana" title="Guarana">Guarana</a></li> <li><a href="/wiki/Iron_supplement" title="Iron supplement">Iron supplements</a></li> <li><a href="/wiki/Lonicera_japonica" title="Lonicera japonica">Japanese honeysuckle</a></li> <li><a href="/wiki/Krill_oil" title="Krill oil">Krill oil</a></li> <li><a href="/wiki/Lingzhi_(mushroom)" title="Lingzhi (mushroom)">Lingzhi</a></li> <li><a href="/wiki/Linseed_oil" title="Linseed oil">Linseed oil</a></li> <li><a class="mw-selflink selflink">Lipoic acid</a></li> <li><a href="/wiki/Silybum_marianum#Health_benefits" title="Silybum marianum">Milk thistle</a></li> <li><a href="/wiki/Melatonin_(supplement)" class="mw-redirect" title="Melatonin (supplement)">Melatonin</a></li> <li><a href="/wiki/Red_yeast_rice" title="Red yeast rice">Red yeast rice</a></li> <li><a href="/wiki/Royal_jelly" title="Royal jelly">Royal jelly</a></li> <li><a href="/wiki/Saw_palmetto_extract" title="Saw palmetto extract">Saw palmetto</a></li> <li><a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">Spirulina</a></li> <li><a href="/wiki/Hypericum_perforatum#Medicinal_uses" title="Hypericum perforatum">St John's wort</a></li> <li><a href="/wiki/Taurine" title="Taurine">Taurine</a></li> <li><a href="/wiki/Wheatgrass" title="Wheatgrass">Wheatgrass</a></li> <li><a href="/wiki/Goji" title="Goji">Wolfberry</a></li> <li><a href="/wiki/Yohimbine" title="Yohimbine">Yohimbine</a></li> <li><a href="/wiki/Zinc_gluconate" title="Zinc gluconate">Zinc gluconate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related articles</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/Codex_Alimentarius" title="Codex Alimentarius">Codex Alimentarius</a></li> <li><a href="/wiki/Enzyte" title="Enzyte">Enzyte</a></li> <li><a href="/wiki/Hadacol" title="Hadacol">Hadacol</a></li> <li><a href="/wiki/Herbal_tea" title="Herbal tea">Herbal tea</a></li> <li><a href="/wiki/Nutraceutical" title="Nutraceutical">Nutraceutical</a></li> <li><a href="/wiki/Multivitamin" title="Multivitamin">Multivitamin</a></li> <li><a href="/wiki/Nutrition" title="Nutrition">Nutrition</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" 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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 href="/wiki/Tacrolimus" title="Tacrolimus">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>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Lipoic_acid&oldid=1279619858">https://en.wikipedia.org/w/index.php?title=Lipoic_acid&oldid=1279619858</a>"</div></div> <div id="catlinks" class="catlinks" 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