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vector-toc-level-2"> <a class="vector-toc-link" href="#In_the_cytosol"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>In the cytosol</span> </div> </a> <ul id="toc-In_the_cytosol-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-In_mitochondria" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#In_mitochondria"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>In mitochondria</span> </div> </a> <ul id="toc-In_mitochondria-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Absorption_and_transport" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Absorption_and_transport"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Absorption and transport</span> </div> </a> <ul id="toc-Absorption_and_transport-sublist" class="vector-toc-list"> </ul> </li> </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">6</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">7</span> <span>References</span> </div> </a> <ul id="toc-References-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" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" 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Available in 28 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-28" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">28 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D9%8A%D8%A7%D9%86%D9%88%D9%83%D9%88%D8%A8%D8%A7%D9%84%D8%A7%D9%85%D9%8A%D9%86" title="سيانوكوبالامين – Arabic" lang="ar" hreflang="ar" data-title="سيانوكوبالامين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D9%88%DA%A9%D8%A8%D8%A7%D9%84%D8%A7%D9%85%DB%8C%D9%86" title="سیانوکبالامین – South Azerbaijani" lang="azb" hreflang="azb" data-title="سیانوکبالامین" 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/Cianocobalamina" title="Cianocobalamina – Catalan" lang="ca" hreflang="ca" data-title="Cianocobalamina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Cyanocobalamin" title="Cyanocobalamin – Welsh" lang="cy" hreflang="cy" data-title="Cyanocobalamin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Cianocobalamina" title="Cianocobalamina – Spanish" lang="es" hreflang="es" data-title="Cianocobalamina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Cianokobalamino" title="Cianokobalamino – Esperanto" lang="eo" hreflang="eo" data-title="Cianokobalamino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%DB%8C%D8%A7%D9%86%D9%88%DA%A9%D8%A8%D8%A7%D9%84%D8%A7%D9%85%DB%8C%D9%86" title="سیانوکبالامین – Persian" lang="fa" hreflang="fa" data-title="سیانوکبالامین" 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/Cyanocobalamine" title="Cyanocobalamine – French" lang="fr" hreflang="fr" data-title="Cyanocobalamine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Cianac%C3%B3balaim%C3%ADn" title="Cianacóbalaimín – Irish" lang="ga" hreflang="ga" data-title="Cianacóbalaimín" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Cianocobalamina" title="Cianocobalamina – Galician" lang="gl" hreflang="gl" data-title="Cianocobalamina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Sianokobalamin" title="Sianokobalamin – Indonesian" lang="id" hreflang="id" data-title="Sianokobalamin" 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-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%A6%D7%99%D7%90%D7%A0%D7%95%D7%A7%D7%95%D7%91%D7%9C%D7%9E%D7%99%D7%9F" title="ציאנוקובלמין – Hebrew" lang="he" hreflang="he" data-title="ציאנוקובלמין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%A6%D0%B8%D0%B0%D0%BD%D0%BA%D0%BE%D0%B1%D0%B0%D0%BB%D0%B0%D0%BC%D0%B8%D0%BD" title="Цианкобаламин – Kazakh" lang="kk" hreflang="kk" data-title="Цианкобаламин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%A6%D0%B8%D0%B0%D0%BD%D0%BA%D0%BE%D0%B1%D0%B0%D0%BB%D0%B0%D0%BC%D0%B8%D0%BD" title="Цианкобаламин – Kyrgyz" lang="ky" hreflang="ky" data-title="Цианкобаламин" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B8%E0%B5%88%E0%B4%A8%E0%B4%BE%E0%B4%95%E0%B5%8D%E0%B4%95%E0%B5%8B%E0%B4%AC%E0%B4%BE%E0%B4%B2%E0%B4%AE%E0%B5%88%E0%B5%BB" title="സൈനാക്കോബാലമൈൻ – Malayalam" lang="ml" hreflang="ml" data-title="സൈനാക്കോബാലമൈൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cyanocobalamine" title="Cyanocobalamine – Dutch" lang="nl" hreflang="nl" data-title="Cyanocobalamine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B7%E3%82%A2%E3%83%8E%E3%82%B3%E3%83%90%E3%83%A9%E3%83%9F%E3%83%B3" title="シアノコバラミン – Japanese" lang="ja" hreflang="ja" data-title="シアノコバラミン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%B8%E0%AD%8D%E0%AD%9F%E0%AC%BE%E0%AC%A8%E0%AD%8B%E0%AC%95%E0%AD%8B%E0%AC%AC%E0%AC%BE%E0%AC%B2%E0%AC%BE%E0%AC%AE%E0%AC%BF%E0%AC%A8" title="ସ୍ୟାନୋକୋବାଲାମିନ – Odia" lang="or" hreflang="or" data-title="ସ୍ୟାନୋକୋବାଲାମିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cyjanokobalamina" title="Cyjanokobalamina – Polish" lang="pl" hreflang="pl" data-title="Cyjanokobalamina" 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/Cianocobalamina" title="Cianocobalamina – Portuguese" lang="pt" hreflang="pt" data-title="Cianocobalamina" 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/Cianocobalamin%C4%83" title="Cianocobalamină – Romanian" lang="ro" hreflang="ro" data-title="Cianocobalamină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru badge-Q70894304 mw-list-item" title=""><a href="https://ru.wikipedia.org/wiki/%D0%A6%D0%B8%D0%B0%D0%BD%D0%BA%D0%BE%D0%B1%D0%B0%D0%BB%D0%B0%D0%BC%D0%B8%D0%BD" title="Цианкобаламин – Russian" lang="ru" hreflang="ru" data-title="Цианкобаламин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Cijanokobalamin" title="Cijanokobalamin – Serbian" lang="sr" hreflang="sr" data-title="Cijanokobalamin" 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/Cijanokobalamin" title="Cijanokobalamin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cijanokobalamin" 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/Syanokobalamiini" title="Syanokobalamiini – Finnish" lang="fi" hreflang="fi" data-title="Syanokobalamiini" 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/Cyanokobalamin" title="Cyanokobalamin – Swedish" lang="sv" hreflang="sv" data-title="Cyanokobalamin" 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%A6%D1%96%D0%B0%D0%BD%D0%BE%D0%BA%D0%BE%D0%B1%D0%B0%D0%BB%D0%B0%D0%BC%D1%96%D0%BD" title="Ціанокобаламін – Ukrainian" lang="uk" hreflang="uk" data-title="Ціанокобаламін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Cyanocobalamin" title="Cyanocobalamin – Vietnamese" lang="vi" hreflang="vi" data-title="Cyanocobalamin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</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/Q252251#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/Cyanocobalamin" title="View the content page [c]" accesskey="c"><span>Article</span></a></li><li id="ca-talk" class="vector-tab-noicon mw-list-item"><a href="/wiki/Talk:Cyanocobalamin" rel="discussion" title="Discuss improvements to the content page [t]" 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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Form of vitamin B-12</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Cyanocobalamin">Cyanocobalamin</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Cyanocobalamin-b12.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Cyanocobalamin-b12.png/220px-Cyanocobalamin-b12.png" decoding="async" width="220" height="254" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/79/Cyanocobalamin-b12.png/330px-Cyanocobalamin-b12.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/79/Cyanocobalamin-b12.png/440px-Cyanocobalamin-b12.png 2x" data-file-width="1356" data-file-height="1568" /></a></span><div class="infobox-caption"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a></div></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Cyanocobalamin-from-xtal-3D-st-noH.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/Cyanocobalamin-from-xtal-3D-st-noH.png/220px-Cyanocobalamin-from-xtal-3D-st-noH.png" decoding="async" width="220" height="174" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/Cyanocobalamin-from-xtal-3D-st-noH.png/330px-Cyanocobalamin-from-xtal-3D-st-noH.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/Cyanocobalamin-from-xtal-3D-st-noH.png/440px-Cyanocobalamin-from-xtal-3D-st-noH.png 2x" data-file-width="2524" data-file-height="2000" /></a></span><div class="infobox-caption"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Stick model</a> of cyanocobalamin based on the crystal structure<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Pronunciation</th><td class="infobox-data">sye AN oh koe BAL a min<sup id="cite_ref-Over2019_2-0" class="reference"><a href="#cite_note-Over2019-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Cobolin-M,<sup id="cite_ref-Over2019_2-1" class="reference"><a href="#cite_note-Over2019-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Depo-Cobolin,<sup id="cite_ref-Over2019_2-2" class="reference"><a href="#cite_note-Over2019-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> others<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/ppa/cyanocobalamin.html">Professional Drug Facts</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a604029.html">a604029</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Cyanocobalamin">Cyanocobalamin</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> Exempt<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/By_mouth" class="mw-redirect" title="By mouth">By mouth</a>, <a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular">intramuscular</a>, <a href="/wiki/Nasal_spray" title="Nasal spray">nasal spray</a><sup id="cite_ref-BNF76_5-0" class="reference"><a href="#cite_note-BNF76-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nose2019_6-0" class="reference"><a href="#cite_note-Nose2019-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_B03" title="ATC code B03">B03BA01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=B03BA01">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">OTC</a> / Rx-only</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=68-19-9">68-19-9</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/16212801">16212801</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00115">DB00115</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.24921423.html">24921423</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/P6YC3EG204">P6YC3EG204</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00166">D00166</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL2110563">ChEMBL2110563</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.618">100.000.618</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q252251#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>63</sub><span title="Hydrogen">H</span><sub>88</sub><span title="Cobalt">Co</span><span title="Nitrogen">N</span><sub>14</sub><span title="Oxygen">O</span><sub>14</sub><span title="Phosphorus">P</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7003135538799999999♠"></span>1<span style="margin-left:.25em;">355</span>.388</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC1%3DCC2%3DC%28C%3DC1C%29N%28C%3DN2%29C3C%28C%28C%28O3%29CO%29OP%28%3DO%29%28%5BO-%5D%29OC%28C%29CNC%28%3DO%29CCC4%28C%28C5C6%28C%28C%28C%28%3DC%28C7%3DNC%28%3DCC8%3DNC%28%3DC%28C4%3DN5%29C%29C%28C8%28C%29C%29CCC%28%3DO%29N%29C%28C7%28C%29CC%28%3DO%29N%29CCC%28%3DO%29N%29C%29%5BN-%5D6%29CCC%28%3DO%29N%29%28C%29CC%28%3DO%29N%29C%29CC%28%3DO%29N%29C%29O.%5BC-%5D%23N.%5BCo%2B3%5D">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">300 °C (572 °F) +</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a></th><td class="infobox-data">300 °C (572 °F) +</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></th><td class="infobox-data">1/80g/ml</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CC1=CC2=C(C=C1C)N(C=N2)C3C(C(C(O3)CO)OP(=O)([O-])OC(C)CNC(=O)CCC4(C(C5C6(C(C(C(=C(C7=NC(=CC8=NC(=C(C4=N5)C)C(C8(C)C)CCC(=O)N)C(C7(C)CC(=O)N)CCC(=O)N)C)[N-]6)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[C-]#N.[Co+3]</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;1-2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;-1;+3/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57?,59-,60+,61+,62+;;/m1../s1</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:FDJOLVPMNUYSCM-QJRSUKKJSA-L</div></li></ul> </div></td></tr></tbody></table> <p><b>Cyanocobalamin</b> is a form of <a href="/wiki/Vitamin_B12" title="Vitamin B12">vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span></a> used to treat and prevent <a href="/wiki/Vitamin_B12_deficiency" title="Vitamin B12 deficiency">vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> deficiency</a> except in the presence of <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> toxicity.<sup id="cite_ref-pmid82069_7-0" class="reference"><a href="#cite_note-pmid82069-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid3046314_8-0" class="reference"><a href="#cite_note-pmid3046314-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Over2019_2-3" class="reference"><a href="#cite_note-Over2019-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The deficiency may occur in <a href="/wiki/Pernicious_anemia" title="Pernicious anemia">pernicious anemia</a>, following <a href="/wiki/Gastrectomy" title="Gastrectomy">surgical removal of the stomach</a>, with <a href="/wiki/Fish_tapeworm" class="mw-redirect" title="Fish tapeworm">fish tapeworm</a>, or due to <a href="/wiki/Bowel_cancer" class="mw-redirect" title="Bowel cancer">bowel cancer</a>.<sup id="cite_ref-Daily2019_9-0" class="reference"><a href="#cite_note-Daily2019-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> <sup id="cite_ref-BNF76_5-1" class="reference"><a href="#cite_note-BNF76-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is used by mouth, by <a href="/wiki/Injection_into_a_muscle" class="mw-redirect" title="Injection into a muscle">injection into a muscle</a>, or as a <a href="/wiki/Nasal_spray" title="Nasal spray">nasal spray</a>.<sup id="cite_ref-BNF76_5-2" class="reference"><a href="#cite_note-BNF76-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nose2019_6-1" class="reference"><a href="#cite_note-Nose2019-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Cyanocobalamin is generally well tolerated.<sup id="cite_ref-Lil2019_10-0" class="reference"><a href="#cite_note-Lil2019-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Minor side effects may include diarrhea, nausea, upset stomach, and itchiness.<sup id="cite_ref-Pro2019_11-0" class="reference"><a href="#cite_note-Pro2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Serious side effects may include <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylaxis</a>, and <a href="/wiki/Low_blood_potassium" class="mw-redirect" title="Low blood potassium">low blood potassium</a> resulting in <a href="/wiki/Heart_failure" title="Heart failure">heart failure</a>.<sup id="cite_ref-Pro2019_11-1" class="reference"><a href="#cite_note-Pro2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Use is not recommended in those who are allergic to <a href="/wiki/Cobalt" title="Cobalt">cobalt</a> or have <a href="/wiki/Leber%27s_disease" class="mw-redirect" title="Leber's disease">Leber's disease</a>.<sup id="cite_ref-Daily2019_9-1" class="reference"><a href="#cite_note-Daily2019-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> No overdosage or toxicity has been reported.<sup id="cite_ref-Pro2019_11-2" class="reference"><a href="#cite_note-Pro2019-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> It is less preferred than <a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">hydroxocobalamin</a> for treating vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> deficiency because it has a slightly lower bioavailability. Some studies have shown it to possess an antihypotensive effect.<sup id="cite_ref-BNF76_5-3" class="reference"><a href="#cite_note-BNF76-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> is an <a href="/wiki/Essential_nutrient" class="mw-redirect" title="Essential nutrient">essential nutrient</a> meaning that it cannot be made by the body but is required for life.<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-Lil2019_10-1" class="reference"><a href="#cite_note-Lil2019-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Cyanocobalamin was first manufactured in the 1940s.<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> It is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a> and <a href="/wiki/Over_the_counter" class="mw-redirect" title="Over the counter">over the counter</a>.<sup id="cite_ref-BNF76_5-4" class="reference"><a href="#cite_note-BNF76-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Lil2019_10-2" class="reference"><a href="#cite_note-Lil2019-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> In 2022, it was the 131st most commonly prescribed medication in the United States, with more than 4<span class="nowrap"> </span>million prescriptions.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_use">Medical use</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanocobalamin&action=edit&section=1" title="Edit section: Medical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanocobalamin is usually prescribed after surgical removal of part or all of the <a href="/wiki/Stomach" title="Stomach">stomach</a> or <a href="/wiki/Intestine" class="mw-redirect" title="Intestine">intestine</a> to ensure adequate serum levels of vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span>. It is also used to treat <a href="/wiki/Pernicious_anemia" title="Pernicious anemia">pernicious anemia</a>, <a href="/wiki/Vitamin_B12_deficiency" title="Vitamin B12 deficiency">vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> deficiency</a> (due to low intake from food or inability to absorb due to genetic or other factors), <a href="/wiki/Thyrotoxicosis" class="mw-redirect" title="Thyrotoxicosis">thyrotoxicosis</a>, <a href="/wiki/Hemorrhage" class="mw-redirect" title="Hemorrhage">hemorrhage</a>, <a href="/wiki/Malignancy" title="Malignancy">malignancy</a>, liver disease and kidney disease. Cyanocobalamin injections are often prescribed to <a href="/wiki/Gastric_bypass" class="mw-redirect" title="Gastric bypass">gastric bypass</a> patients who have had part of their <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a> bypassed, making it difficult for <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> to be acquired via food or vitamins. Cyanocobalamin is also used to perform the <a href="/wiki/Schilling_test" title="Schilling test">Schilling test</a> to check ability to absorb vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span>.<sup id="cite_ref-umm_16-0" class="reference"><a href="#cite_note-umm-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Cyanocobalamin is also produced in the body (and then excreted via urine) after intravenous <a href="/wiki/Hydroxycobalamin" class="mw-redirect" title="Hydroxycobalamin">hydroxycobalamin</a> is used to treat <a href="/wiki/Cyanide_poisoning" title="Cyanide poisoning">cyanide poisoning</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanocobalamin&action=edit&section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Possible side effects of cyanocobalamin injection include allergic reactions such as <a href="/wiki/Hives" title="Hives">hives</a>, difficult breathing; redness of the face; swelling of the arms, hands, feet, ankles or lower legs; extreme thirst; and <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>. Less-serious side effects may include headache, dizziness, leg pain, <a href="/wiki/Itching" class="mw-redirect" title="Itching">itching</a>, or <a href="/wiki/Rash" title="Rash">rash</a>.<sup id="cite_ref-Sides2_18-0" class="reference"><a href="#cite_note-Sides2-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>Treatment of <a href="/wiki/Megaloblastic_anemia" title="Megaloblastic anemia">megaloblastic anemia</a> with concurrent vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> deficiency using <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> vitamers (including cyanocobalamin), creates the possibility of <a href="/wiki/Hypokalemia" title="Hypokalemia">hypokalemia</a> due to increased <a href="/wiki/Erythropoiesis" title="Erythropoiesis">erythropoiesis</a> (red blood cell production) and consequent cellular uptake of <a href="/wiki/Potassium" title="Potassium">potassium</a> upon anemia resolution.<sup id="cite_ref-Anemia_19-0" class="reference"><a href="#cite_note-Anemia-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> When treated with cyanocobalamin, patients with <a href="/wiki/Leber%27s_disease" class="mw-redirect" title="Leber's disease">Leber's disease</a> may develop serious <a href="/wiki/Optic_atrophy" class="mw-redirect" title="Optic atrophy">optic atrophy</a>, possibly leading to blindness.<sup id="cite_ref-blind_20-0" class="reference"><a href="#cite_note-blind-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanocobalamin&action=edit&section=3" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> is the "generic descriptor" name for any <a href="/wiki/Vitamer" title="Vitamer">vitamers</a> of vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span>. Animals, including humans, can convert cyanocobalamin to any one of the active vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> compounds.<sup id="cite_ref-PMC2809139_21-0" class="reference"><a href="#cite_note-PMC2809139-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Cyanocobalamin is one of the most widely manufactured <a href="/wiki/Vitamer" title="Vitamer">vitamers</a> in the vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> family (the family of chemicals that function as <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> when put into the body), because cyanocobalamin is the most air-stable of the <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> forms.<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> It is the easiest<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> to crystallize and therefore easiest<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> to purify after it is produced by <a href="/wiki/Bacterial_fermentation" class="mw-redirect" title="Bacterial fermentation">bacterial fermentation</a>. It can be obtained as dark red crystals or as an amorphous red powder. Cyanocobalamin is <a href="/wiki/Hygroscopic" class="mw-redirect" title="Hygroscopic">hygroscopic</a> in the <a href="/wiki/Anhydrous" title="Anhydrous">anhydrous</a> form, and sparingly soluble in water (1:80).<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> It is stable to <a href="/wiki/Autoclaving" class="mw-redirect" title="Autoclaving">autoclaving</a> for short periods at 121 °C (250 °F). The vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> <a href="/wiki/Coenzymes" class="mw-redirect" title="Coenzymes">coenzymes</a> are unstable in light. After consumption the cyanide <a href="/wiki/Ligand" title="Ligand">ligand</a> is replaced by other groups (<a href="/wiki/Adenosyl" class="mw-redirect" title="Adenosyl">adenosyl</a>, <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a>) to produce the biologically active forms. The <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> is converted to <a href="/wiki/Thiocyanate" title="Thiocyanate">thiocyanate</a> and excreted by the kidney.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Chemical_reactions">Chemical reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanocobalamin&action=edit&section=4" title="Edit section: Chemical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Various_reduced_forms_of_Cyanocobalamin.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Various_reduced_forms_of_Cyanocobalamin.jpg/220px-Various_reduced_forms_of_Cyanocobalamin.jpg" decoding="async" width="220" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Various_reduced_forms_of_Cyanocobalamin.jpg/330px-Various_reduced_forms_of_Cyanocobalamin.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d7/Various_reduced_forms_of_Cyanocobalamin.jpg/440px-Various_reduced_forms_of_Cyanocobalamin.jpg 2x" data-file-width="5193" data-file-height="3044" /></a><figcaption>Reduced forms of Cyanocobalamin, with a Co(I) (top), Co(II) (middle), and Co(III) (bottom)</figcaption></figure> <p>In the cobalamins, <a href="/wiki/Cobalt" title="Cobalt">cobalt</a> normally exists in the trivalent state, Co(III). However, under reducing conditions, the cobalt center is reduced to Co(II) or even Co(I), which are usually denoted as <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12r</sub></span></span></span> and <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12s</sub></span></span></span>, for reduced and super reduced respectively. </p><p><span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12r</sub></span></span></span> and <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12s</sub></span></span></span> can be prepared from cyanocobalamin by controlled potential reduction, or chemical reduction using <a href="/wiki/Sodium_borohydride" title="Sodium borohydride">sodium borohydride</a> in alkaline solution, <a href="/wiki/Zinc" title="Zinc">zinc</a> in <a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a>, or by the action of <a href="/wiki/Thiols" class="mw-redirect" title="Thiols">thiols</a>. Both <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12r</sub></span></span></span> and <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12s</sub></span></span></span> are stable indefinitely under oxygen-free conditions. <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12r</sub></span></span></span> appears orange-brown in solution, while <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12s</sub></span></span></span> appears bluish-green under natural daylight, and purple under artificial light.<sup id="cite_ref-MechB12_27-0" class="reference"><a href="#cite_note-MechB12-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p><span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12s</sub></span></span></span> is one of the most nucleophilic species known in aqueous solution.<sup id="cite_ref-MechB12_27-1" class="reference"><a href="#cite_note-MechB12-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> This property allows the convenient preparation of cobalamin analogs with different <a href="/wiki/Substituents" class="mw-redirect" title="Substituents">substituents</a>, via <a href="/wiki/Nucleophilic" class="mw-redirect" title="Nucleophilic">nucleophilic</a> attack on <a href="/wiki/Alkyl_halide" class="mw-redirect" title="Alkyl halide">alkyl halides</a> and vinyl halides.<sup id="cite_ref-MechB12_27-2" class="reference"><a href="#cite_note-MechB12-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>For example, cyanocobalamin can be converted to its analog cobalamins via reduction to <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12s</sub></span></span></span>, followed by the addition of the corresponding <a href="/wiki/Alkyl_halides" class="mw-redirect" title="Alkyl halides">alkyl halides</a>, <a href="/wiki/Acyl_halides" class="mw-redirect" title="Acyl halides">acyl halides</a>, <a href="/wiki/Alkene" title="Alkene">alkene</a> or <a href="/wiki/Alkyne" title="Alkyne">alkyne</a>. <a href="/wiki/Steric_hindrance" class="mw-redirect" title="Steric hindrance">Steric hindrance</a> is the major limiting factor in the synthesis of the <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> coenzyme analogs. For example, no reaction occurs between <a href="/wiki/Neopentyl" class="mw-redirect" title="Neopentyl">neopentyl</a> chloride and <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12s</sub></span></span></span>, whereas the secondary alkyl halide analogs are too unstable to be isolated.<sup id="cite_ref-MechB12_27-3" class="reference"><a href="#cite_note-MechB12-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> This effect may be due to the strong coordination between <a href="/wiki/Benzimidazole" title="Benzimidazole">benzimidazole</a> and the central cobalt atom, pulling it down into the plane of the <a href="/wiki/Corrin" title="Corrin">corrin</a> ring. The <a href="/wiki/Trans_effect" title="Trans effect">trans effect</a> determines the polarizability of the Co–C bond so formed. However, once the <a href="/wiki/Benzimidazole" title="Benzimidazole">benzimidazole</a> is detached from cobalt by quaternization with <a href="/wiki/Methyl_iodide" class="mw-redirect" title="Methyl iodide">methyl iodide</a>, it is replaced by <span class="chemf nowrap">H<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>O</span> or <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> ions. Various secondary alkyl halides are then readily attacked by the modified <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12s</sub></span></span></span> to give the corresponding stable cobalamin analogs.<sup id="cite_ref-InnoCatalyst_28-0" class="reference"><a href="#cite_note-InnoCatalyst-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> The products are usually extracted and purified by phenol-methylene chloride extraction or by column chromatography.<sup id="cite_ref-MechB12_27-4" class="reference"><a href="#cite_note-MechB12-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Cobalamin analogs prepared by this method include the naturally occurring coenzymes <a href="/wiki/Methylcobalamin" title="Methylcobalamin">methylcobalamin</a> and <a href="/wiki/Cobamamide" class="mw-redirect" title="Cobamamide">cobamamide</a>, and other cobalamins that do not occur naturally, such as vinylcobalamin, carboxymethylcobalamin and cyclohexylcobalamin.<sup id="cite_ref-MechB12_27-5" class="reference"><a href="#cite_note-MechB12-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> This reaction is under review for use as a catalyst for <a href="/wiki/Chemical_dehalogenation" class="mw-redirect" title="Chemical dehalogenation">chemical dehalogenation</a>, organic reagent and photosensitized catalyst systems.<sup id="cite_ref-Catalysis_29-0" class="reference"><a href="#cite_note-Catalysis-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanocobalamin&action=edit&section=5" title="Edit section: Production"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cyanocobalamin is commercially prepared by <a href="/wiki/Bacterial_fermentation" class="mw-redirect" title="Bacterial fermentation">bacterial fermentation</a>. Fermentation by a variety of <a href="/wiki/Microorganism" title="Microorganism">microorganisms</a> yields a mixture of <a href="/wiki/Methylcobalamin" title="Methylcobalamin">methylcobalamin</a>, <a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">hydroxocobalamin</a> and <a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">adenosylcobalamin</a>. These compounds are converted to cyanocobalamin by addition of <a href="/wiki/Potassium_cyanide" title="Potassium cyanide">potassium cyanide</a> in the presence of <a href="/wiki/Sodium_nitrite" title="Sodium nitrite">sodium nitrite</a> and heat. Since multiple species of <i><a href="/wiki/Propionibacterium" title="Propionibacterium">Propionibacterium</a></i> produce no <a href="/wiki/Exotoxin" title="Exotoxin">exotoxins</a> or <a href="/wiki/Endotoxin" class="mw-redirect" title="Endotoxin">endotoxins</a> and have been granted <a href="/wiki/GRAS" class="mw-redirect" title="GRAS">GRAS</a> status (generally regarded as safe) by the <a href="/wiki/United_States_Food_and_Drug_Administration" class="mw-redirect" title="United States Food and Drug Administration">United States Food and Drug Administration</a>, they are the preferred bacterial fermentation organisms for vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> production.<sup id="cite_ref-Riaz_30-0" class="reference"><a href="#cite_note-Riaz-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>Historically, the physiological form was initially thought to be cyanocobalamin. This was because <a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">hydroxocobalamin</a> produced by bacteria was changed to cyanocobalamin during purification in <a href="/wiki/Activated_charcoal" class="mw-redirect" title="Activated charcoal">activated charcoal</a> columns after separation from the bacterial cultures (because <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> is naturally present in activated charcoal).<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Cyanocobalamin is the form in most pharmaceutical preparations because adding cyanide stabilizes the molecule.<sup id="cite_ref-herbert_32-0" class="reference"><a href="#cite_note-herbert-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>The total world production of vitamin B<sub>12</sub>, by four companies (the French Sanofi-Aventis and three Chinese companies) in 2008 was 35 tonnes.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanocobalamin&action=edit&section=6" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The two bioactive forms of vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> are <a href="/wiki/Methylcobalamin" title="Methylcobalamin">methylcobalamin</a> in <a href="/wiki/Cytosol" title="Cytosol">cytosol</a> and <a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">adenosylcobalamin</a> in <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>. Multivitamins often contain cyanocobalamin, which is presumably converted to bioactive forms in the body. Both methylcobalamin and adenosylcobalamin are commercially available as supplement pills. The <a href="/wiki/MMACHC" title="MMACHC">MMACHC</a> gene product catalyzes the decyanation of cyanocobalamin as well as the dealkylation of alkylcobalamins including methylcobalamin and adenosylcobalamin.<sup id="cite_ref-Hannibal_34-0" class="reference"><a href="#cite_note-Hannibal-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> This function has also been attributed to <a href="/wiki/Cyanocobalamin_reductase_(cyanide-eliminating)" title="Cyanocobalamin reductase (cyanide-eliminating)">cobalamin reductases</a>.<sup id="cite_ref-Watanabe_35-0" class="reference"><a href="#cite_note-Watanabe-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> The MMACHC gene product and cobalamin reductases enable the interconversion of cyano- and alkylcobalamins.<sup id="cite_ref-Quadros_36-0" class="reference"><a href="#cite_note-Quadros-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>Cyanocobalamin is added as an ingredient to fortify<sup id="cite_ref-DSM-fortify_37-0" class="reference"><a href="#cite_note-DSM-fortify-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> nutrition in products such as baby formula, breakfast cereals and <a href="/wiki/Energy_drinks" class="mw-redirect" title="Energy drinks">energy drinks</a> as well as livestock feed. Vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> becomes inactive when exposed to <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> and <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a> in cigarette smoke. Vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> deficiency can develop with heavy regular use of <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">nitrous oxide</a> <span class="chemf nowrap">N<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span>O</span>, also known as "laughing gas", used for <a href="/wiki/Anaesthesia" class="mw-redirect" title="Anaesthesia">anaesthesia</a> in a clinical setting or as a propellant gas, it's commonly abused as a recreational drug.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> Vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> additionally becomes inactive when exposed to intense heat or electromagnetic radiation.<sup id="cite_ref-Watanabe2_39-0" class="reference"><a href="#cite_note-Watanabe2-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="In_the_cytosol">In the cytosol</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanocobalamin&action=edit&section=7" title="Edit section: In the cytosol"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a> and <a href="/wiki/5-methyltetrahydrofolate" class="mw-redirect" title="5-methyltetrahydrofolate">5-methyltetrahydrofolate</a> are needed by <a href="/wiki/Methionine_synthase" title="Methionine synthase">methionine synthase</a> in the <a href="/wiki/Methionine" title="Methionine">methionine</a> cycle to transfer a methyl group from <a href="/wiki/5-methyltetrahydrofolate" class="mw-redirect" title="5-methyltetrahydrofolate">5-methyltetrahydrofolate</a> to <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a>, thereby generating <a href="/wiki/Tetrahydrofolate" class="mw-redirect" title="Tetrahydrofolate">tetrahydrofolate</a> (THF) and <a href="/wiki/Methionine" title="Methionine">methionine</a>, which is used to make <a href="/wiki/SAMe" class="mw-redirect" title="SAMe">SAMe</a>. <a href="/wiki/SAMe" class="mw-redirect" title="SAMe">SAMe</a> is the universal methyl donor and is used for <a href="/wiki/DNA_methylation" title="DNA methylation">DNA methylation</a> and to make <a href="/wiki/Lipid_bilayer" title="Lipid bilayer">phospholipid</a> <a href="/wiki/Cell_membrane" title="Cell membrane">membranes</a>, <a href="/wiki/Choline" title="Choline">choline</a>, <a href="/wiki/Sphingomyelin" title="Sphingomyelin">sphingomyelin</a>, <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a>, and other <a href="/wiki/Neurotransmitters" class="mw-redirect" title="Neurotransmitters">neurotransmitters</a>. </p> <div class="mw-heading mw-heading3"><h3 id="In_mitochondria">In mitochondria</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanocobalamin&action=edit&section=8" title="Edit section: In mitochondria"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Odd-chain_FA_oxydation.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/88/Odd-chain_FA_oxydation.png/170px-Odd-chain_FA_oxydation.png" decoding="async" width="170" height="361" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/8/88/Odd-chain_FA_oxydation.png 1.5x" data-file-width="246" data-file-height="523" /></a><figcaption>Vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> <a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">adenosylcobalamin</a> in <a href="/wiki/Mitochondrion" title="Mitochondrion">mitochondrion</a>—cholesterol and protein metabolism</figcaption></figure> <p>The enzymes that use <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> as a built-in cofactor are <a href="/wiki/Methylmalonyl-CoA_mutase" title="Methylmalonyl-CoA mutase">methylmalonyl-CoA mutase</a> (<a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a> 4REQ<sup id="cite_ref-4REQ_40-0" class="reference"><a href="#cite_note-4REQ-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup>) and <a href="/wiki/Methionine_synthase" title="Methionine synthase">methionine synthase</a> (<a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a> 1Q8J).<sup id="cite_ref-1Q8J_41-0" class="reference"><a href="#cite_note-1Q8J-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>The metabolism of <a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a> occurs in the mitochondria and requires Vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> (as <a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">adenosylcobalamin</a>) to make <a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a>. When the conversion of propionyl-CoA to succinyl-CoA in the mitochondria fails due to Vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> deficiency, elevated blood levels of <a href="/wiki/Methylmalonic_acid" title="Methylmalonic acid">methylmalonic acid</a> (MMA) occur. Thus, elevated blood levels of <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a> and MMA may both be indicators of <a href="/wiki/Vitamin_B12_deficiency" title="Vitamin B12 deficiency">vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> deficiency</a>. </p><p><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a> is needed as <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> in <a href="/wiki/Methylmalonyl-CoA_mutase" title="Methylmalonyl-CoA mutase">methylmalonyl-CoA mutase</a>—MUT enzyme. Processing of cholesterol and protein gives <a href="/wiki/Propionyl-CoA" title="Propionyl-CoA">propionyl-CoA</a> that is converted to <a href="/wiki/Methylmalonyl-CoA" title="Methylmalonyl-CoA">methylmalonyl-CoA</a>, which is used by <a href="/wiki/Methylmalonyl-CoA_mutase" title="Methylmalonyl-CoA mutase">MUT enzyme</a> to make <a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a>. Vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> is needed to prevent anemia, since making <a href="/wiki/Porphyrin" title="Porphyrin">porphyrin</a> and <a href="/wiki/Heme" title="Heme">heme</a> in <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> for producing hemoglobin in red blood cells depends on <a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a> made by vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span>. </p> <div class="mw-heading mw-heading3"><h3 id="Absorption_and_transport">Absorption and transport</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cyanocobalamin&action=edit&section=9" title="Edit section: Absorption and transport"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Inadequate absorption of vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> may be related to <a href="/wiki/Coeliac_disease" title="Coeliac disease">coeliac disease</a>. Intestinal absorption of vitamin <span class="chemf nowrap">B<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline"></sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">12</sub></span></span></span> requires successively three different protein molecules: <a href="/wiki/Haptocorrin" title="Haptocorrin">haptocorrin</a>, <a href="/wiki/Intrinsic_factor" title="Intrinsic factor">intrinsic factor</a> and <a href="/wiki/Transcobalamin_II" class="mw-redirect" title="Transcobalamin II">transcobalamin II</a>. </p> <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=Cyanocobalamin&action=edit&section=10" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a></li> <li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cobalamin_biosynthesis" title="Cobalamin biosynthesis">Cobalamin biosynthesis</a></li></ul> <div style="clear:both;" class=""></div> <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=Cyanocobalamin&action=edit&section=11" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style 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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 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Proceedings+of+the+National+Academy+of+Sciences+of+the+United+States+of+America&rft.atitle=Structures+of+the+N-terminal+modules+imply+large+domain+motions+during+catalysis+by+methionine+synthase&rft.volume=101&rft.issue=11&rft.pages=3729-3736&rft.date=2004-03&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC374312%23id-name%3DPMC&rft_id=info%3Apmid%2F14752199&rft_id=info%3Adoi%2F10.1073%2Fpnas.0308082100&rft_id=info%3Abibcode%2F2004PNAS..101.3729E&rft.aulast=Evans&rft.aufirst=JC&rft.au=Huddler%2C+DP&rft.au=Hilgers%2C+MT&rft.au=Romanchuk%2C+G&rft.au=Matthews%2C+RG&rft.au=Ludwig%2C+ML&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC374312&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanocobalamin" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1236075235">.mw-parser-output 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Vitamins" title="Template:Vitamins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Vitamins" title="Template talk:Vitamins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Vitamins" title="Special:EditPage/Template:Vitamins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Vitamins_(A11)" style="font-size:114%;margin:0 4em"><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a> (<a href="/wiki/ATC_code_A11" title="ATC code A11">A11</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fat <br />soluble</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_A" title="Vitamin A">A</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/%CE%91-Carotene" title="Α-Carotene">α-Carotene</a></li> <li><a href="/wiki/%CE%92-Carotene" title="Β-Carotene">β-Carotene</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a><sup>#</sup></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_D" title="Vitamin D">D</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>D<sub>2</sub> <ul><li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a><sup>#</sup></li></ul></li> <li>D<sub>3</sub> <ul><li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Previtamin_D3" title="Previtamin D3">Previtamin D<sub>3</sub></a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a><sup>#</sup></li> <li><a href="/wiki/Calcifediol" title="Calcifediol">25-hydroxycholecalciferol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol (1,25-dihydroxycholecalciferol)</a></li> <li><a href="/wiki/Calcitroic_acid" title="Calcitroic acid">Calcitroic acid</a></li></ul></li> <li>D<sub>4</sub> <ul><li><a href="/wiki/22-Dihydroergocalciferol" title="22-Dihydroergocalciferol">Dihydroergocalciferol</a></li></ul></li> <li><a href="/wiki/Vitamin_D5" title="Vitamin D5">D<sub>5</sub></a></li> <li>D analogues <ul><li><a href="/wiki/Alfacalcidol" title="Alfacalcidol">Alfacalcidol</a></li> <li><a href="/wiki/Dihydrotachysterol" title="Dihydrotachysterol">Dihydrotachysterol</a></li> <li><a href="/wiki/Calcipotriol" title="Calcipotriol">Calcipotriol</a></li> <li><a href="/wiki/Tacalcitol" title="Tacalcitol">Tacalcitol</a></li> <li><a href="/wiki/Paricalcitol" title="Paricalcitol">Paricalcitol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_E" title="Vitamin E">E</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/Tocopherol" title="Tocopherol">Tocopherol</a> <ul><li><a href="/wiki/%CE%91-Tocopherol" title="Α-Tocopherol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocopherol" title="Β-Tocopherol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocopherol" title="Γ-Tocopherol">Gamma</a></li> <li><a href="/wiki/%CE%94-Tocopherol" title="Δ-Tocopherol">Delta</a></li></ul></li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienol</a> <ul><li><a href="/wiki/%CE%91-Tocotrienol" title="Α-Tocotrienol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocotrienol" title="Β-Tocotrienol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocotrienol" title="Γ-Tocotrienol">Gamma</a></li> <li>Delta</li></ul></li> <li><a href="/wiki/Tocofersolan" title="Tocofersolan">Tocofersolan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_K" title="Vitamin K">K</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/1,4-Naphthoquinone" title="1,4-Naphthoquinone">Naphthoquinone</a></li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone (K<sub>1</sub>)</a><sup>#</sup></li> <li><a href="/wiki/Vitamin_K2" title="Vitamin K2">Menaquinones (K<sub>2</sub>)</a></li> <li><a href="/wiki/Menadione" title="Menadione">Menadione (K<sub>3</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/Vitamin_K4" class="mw-redirect" title="Vitamin K4">Various (K<sub>4</sub>)</a></li> <li><a href="/wiki/4-Amino-2-methyl-1-naphthol" title="4-Amino-2-methyl-1-naphthol">4-Amino-2-methyl-1-naphthol (K<sub>5</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/2-Methylnaphthalene-1,4-diamine" title="2-Methylnaphthalene-1,4-diamine">2-Methylnaphthalene-1,4-diamine (K<sub>6</sub>)</a></li> <li><a href="/wiki/4-Amino-3-methyl-1-naphthol" title="4-Amino-3-methyl-1-naphthol">4-Amino-3-methyl-1-naphthol (K<sub>7</sub>)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Water <br />soluble</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/B_vitamins" title="B vitamins">B</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>B<sub>1</sub> <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B1_analogues" title="Vitamin B1 analogues">B<sub>1</sub> analogues</a> <ul><li><a href="/wiki/Acefurtiamine" title="Acefurtiamine">Acefurtiamine</a></li> <li><a href="/wiki/Allithiamine" title="Allithiamine">Allithiamine</a></li> <li><a href="/wiki/Benfotiamine" title="Benfotiamine">Benfotiamine</a></li> <li><a href="/wiki/Fursultiamine" title="Fursultiamine">Fursultiamine</a></li> <li><a href="/wiki/Octotiamine" title="Octotiamine">Octotiamine</a></li> <li><a href="/wiki/Prosultiamine" title="Prosultiamine">Prosultiamine</a></li> <li><a href="/wiki/Sulbutiamine" title="Sulbutiamine">Sulbutiamine</a></li></ul></li> <li>B<sub>2</sub> <ul><li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B3" title="Vitamin B3">B<sub>3</sub></a> <ul><li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Niacinamide</a><sup>#</sup></li></ul></li> <li>B<sub>5</sub> <ul><li><a href="/wiki/Pantothenic_acid" title="Pantothenic acid">Pantothenic acid</a></li> <li><a href="/wiki/Panthenol" title="Panthenol">Dexpanthenol</a></li> <li><a href="/wiki/Pantethine" title="Pantethine">Pantethine</a></li></ul></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">B<sub>6</sub></a> <ul><li><a href="/wiki/Pyridoxine" title="Pyridoxine">Pyridoxine</a><sup>#</sup>, <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">Pyridoxal phosphate</a></li> <li><a href="/wiki/Pyridoxamine" title="Pyridoxamine">Pyridoxamine</a></li> <li><a href="/wiki/Pyritinol" title="Pyritinol">Pyritinol</a></li></ul></li> <li>B<sub>7</sub> <ul><li><a href="/wiki/Biotin" title="Biotin">Biotin</a></li></ul></li> <li>B<sub>9</sub> <ul><li><a href="/wiki/Folate" title="Folate">Folic acid</a><sup>#</sup></li> <li><a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">Dihydrofolic acid</a></li> <li><a href="/wiki/Folinic_acid" title="Folinic acid">Folinic acid</a></li> <li><a href="/wiki/Levomefolic_acid" title="Levomefolic acid">Levomefolic acid</a></li></ul></li> <li><a href="/wiki/Vitamin_B12" title="Vitamin B12">B<sub>12</sub></a> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a class="mw-selflink selflink">Cyanocobalamin</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a><sup>#</sup></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_C" title="Vitamin C">C</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/Vitamin_C" title="Vitamin C">Ascorbic acid</a><sup>#</sup></li> <li><a href="/wiki/Dehydroascorbic_acid" title="Dehydroascorbic acid">Dehydroascorbic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</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/Multivitamin" title="Multivitamin">Multivitamins</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><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="Antianemic_preparations_(B03)" 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:Antianemic_preparations" title="Template:Antianemic preparations"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antianemic_preparations" title="Template talk:Antianemic preparations"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antianemic_preparations" title="Special:EditPage/Template:Antianemic preparations"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antianemic_preparations_(B03)" style="font-size:114%;margin:0 4em"><a href="/wiki/Anemia" title="Anemia">Antianemic preparations</a> (<a href="/wiki/ATC_code_B03" title="ATC code B03">B03</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Erythropoietin" title="Erythropoietin">Erythropoietins</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Erythropoietin" title="Erythropoietin">Erythropoietin</a></li> <li><a href="/wiki/Darbepoetin_alfa" title="Darbepoetin alfa">Darbepoetin alfa</a></li> <li><a href="/wiki/Methoxy_polyethylene_glycol-epoetin_beta" title="Methoxy polyethylene glycol-epoetin beta">Methoxy polyethylene glycol-epoetin beta</a></li> <li><a href="/wiki/Peginesatide" title="Peginesatide">Peginesatide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Iron_supplement" title="Iron supplement">Iron supplements</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/Iron(III)_oxide-hydroxide" title="Iron(III) oxide-hydroxide">Ferric hydroxide</a></li> <li><a href="/wiki/Ferric_maltol" title="Ferric maltol">Ferric maltol</a></li> <li><a href="/w/index.php?title=Ferrous_ascorbate&action=edit&redlink=1" class="new" title="Ferrous ascorbate (page does not exist)">Ferrous ascorbate</a></li> <li><a href="/w/index.php?title=Ferrous_aspartate&action=edit&redlink=1" class="new" title="Ferrous aspartate (page does not exist)">Ferrous aspartate</a></li> <li><a href="/wiki/Iron(II)_carbonate" title="Iron(II) carbonate">Ferrous carbonate</a></li> <li><a href="/wiki/Iron(II)_chloride" title="Iron(II) chloride">Ferrous chloride</a></li> <li><a href="/wiki/Ferric_derisomaltose" title="Ferric derisomaltose">Ferric derisomaltose</a></li> <li><a href="/wiki/Iron(II)_fumarate" title="Iron(II) fumarate">Ferrous fumarate</a></li> <li><a href="/wiki/Iron(II)_gluconate" title="Iron(II) gluconate">Ferrous gluconate</a></li> <li><a href="/w/index.php?title=Ferrous_glycine_sulfate&action=edit&redlink=1" class="new" title="Ferrous glycine sulfate (page does not exist)">Ferrous glycine sulfate</a></li> <li><a href="/w/index.php?title=Ferrous_iodine&action=edit&redlink=1" class="new" title="Ferrous iodine (page does not exist)">Ferrous iodine</a></li> <li><a href="/wiki/Ferrous_succinate" class="mw-redirect" title="Ferrous succinate">Ferrous succinate</a></li> <li><a href="/wiki/Iron(II)_sulfate" title="Iron(II) sulfate">Ferrous sulfate</a></li> <li><a href="/wiki/Ferrous_tartrate" title="Ferrous tartrate">Ferrous tartrate</a></li> <li><a href="/wiki/Iron_sucrose" title="Iron sucrose">Iron sucrose</a></li> <li><a href="/wiki/Sodium_ferric_gluconate_complex" title="Sodium ferric gluconate complex">Sodium ferric gluconate complex</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_B12" title="Vitamin B12">Vitamin B12</a> and<br /><a href="/wiki/Folic_acid" class="mw-redirect" title="Folic acid">folic acid</a> supplements</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 class="mw-selflink selflink">Cyanocobalamin</a></li> <li><a href="/w/index.php?title=Cyanocobalamin_tannin_complex&action=edit&redlink=1" class="new" title="Cyanocobalamin tannin complex (page does not exist)">Cyanocobalamin tannin complex</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a></li> <li><a href="/wiki/Cobamamide" class="mw-redirect" title="Cobamamide">Cobamamide</a></li> <li><a href="/wiki/Mecobalamin" class="mw-redirect" title="Mecobalamin">Mecobalamin</a></li> <li><a href="/wiki/Folic_acid" class="mw-redirect" title="Folic acid">Folic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/HIF_prolyl-hydroxylase_inhibitor" title="HIF prolyl-hydroxylase inhibitor">HIF prolyl-hydroxylase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Daprodustat" title="Daprodustat">Daprodustat</a></li> <li><a href="/wiki/Desidustat" title="Desidustat">Desidustat</a></li> <li><a href="/wiki/Enarodustat" title="Enarodustat">Enarodustat</a></li> <li><a href="/wiki/Molidustat" title="Molidustat">Molidustat</a></li> <li><a href="/wiki/Roxadustat" title="Roxadustat">Roxadustat</a></li> <li><a href="/wiki/Vadadustat" title="Vadadustat">Vadadustat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Luspatercept" title="Luspatercept">Luspatercept</a></li></ul> </div></td></tr></tbody></table></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="Types_of_tetrapyrroles" 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:Tetrapyrroles" title="Template:Tetrapyrroles"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tetrapyrroles" title="Template talk:Tetrapyrroles"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tetrapyrroles" title="Special:EditPage/Template:Tetrapyrroles"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_tetrapyrroles" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Tetrapyrrole" title="Tetrapyrrole">tetrapyrroles</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bilin_(biochemistry)" title="Bilin (biochemistry)">Bilanes</a><br />(Linear)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bilirubin" title="Bilirubin">Bilirubin</a></li> <li><a href="/wiki/Biliverdin" title="Biliverdin">Biliverdin</a></li> <li><a href="/wiki/Stercobilinogen" title="Stercobilinogen">Stercobilinogen</a></li> <li><a href="/wiki/Stercobilin" title="Stercobilin">Stercobilin</a></li> <li><a href="/wiki/Urobilinogen" title="Urobilinogen">Urobilinogen</a></li> <li><a href="/wiki/Urobilin" title="Urobilin">Urobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytobilin&action=edit&redlink=1" class="new" title="Phytobilin (page does not exist)">Phytobilins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phytochromobilin" class="mw-redirect" title="Phytochromobilin">Phytochromobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phycobilin" title="Phycobilin">Phycobilins</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/Phycoerythrobilin" title="Phycoerythrobilin">Phycoerythrobilin</a></li> <li><a href="/wiki/Phycocyanobilin" title="Phycocyanobilin">Phycocyanobilin</a></li> <li><a href="/wiki/Phycourobilin" title="Phycourobilin">Phycourobilin</a></li> <li><a href="/w/index.php?title=Phycoviolobilin&action=edit&redlink=1" class="new" title="Phycoviolobilin (page does not exist)">Phycoviolobilin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Macrocycle" title="Macrocycle">Macrocycle</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corrinoid" title="Corrinoid">Corrinoids</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/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a class="mw-selflink selflink">Cyanocobalamin</a></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Protoporphyrin" class="mw-redirect" title="Protoporphyrin">Protoporphyrins</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/Heme" title="Heme">Heme</a> (<a href="/wiki/Heme_b" class="mw-redirect" title="Heme b"><i>b</i></a>, <a href="/wiki/Heme_c" class="mw-redirect" title="Heme c"><i>c</i></a>, <a href="/wiki/Heme_a" class="mw-redirect" title="Heme a"><i>a</i></a>, <a href="/wiki/Heme_o" class="mw-redirect" title="Heme o"><i>o</i></a>)</li> <li><a href="/w/index.php?title=Magnesium_protoporphyrin&action=edit&redlink=1" class="new" title="Magnesium protoporphyrin (page does not exist)">Magnesium protoporphyrin</a></li> <li><a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">Protoporphyrin IX</a></li> <li><a href="/wiki/Pterobilin" title="Pterobilin">Pterobilin</a></li> <li><a href="/wiki/Zinc_protoporphyrin" title="Zinc protoporphyrin">Zinc protoporphyrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytoporphyrin&action=edit&redlink=1" class="new" title="Phytoporphyrin (page does not exist)">Phytoporphyrins</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/Chlorophyll_c" title="Chlorophyll c">Chlorophyll <i>c</i></a></li> <li><a href="/wiki/Protochlorophyllide" title="Protochlorophyllide">Protochlorophyllide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reduced<br />porphyrins</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Porphyrinogens" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Porphyrinogen" title="Porphyrinogen">Porphyrinogens</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/Uroporphyrinogen" title="Uroporphyrinogen">Uroporphyrinogen</a> (<a href="/wiki/Uroporphyrinogen_I" title="Uroporphyrinogen I">I</a>, <a href="/wiki/Uroporphyrinogen_III" title="Uroporphyrinogen III">III</a>)</li> <li><a href="/wiki/Coproporphyrinogens" title="Coproporphyrinogens">Coproporphyrinogen</a> (<a href="/wiki/Coproporphyrinogen_I" title="Coproporphyrinogen I">I</a>, <a href="/wiki/Coproporphyrinogen_III" title="Coproporphyrinogen III">III</a>)</li> <li><a href="/wiki/Protoporphyrinogen_IX" title="Protoporphyrinogen IX">Protoporphyrinogen IX</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chlorin" title="Chlorin">Chlorins</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/Chlorophyllide" title="Chlorophyllide">Chlorophyllide</a> (<a href="/wiki/Chlorophyllide_a" class="mw-redirect" title="Chlorophyllide a"><i>a</i></a>, <a href="/wiki/Chlorophyllide_b" class="mw-redirect" title="Chlorophyllide b"><i>b</i></a>)</li> <li><a href="/wiki/Chlorophyll" title="Chlorophyll">Chlorophyll</a> (<a href="/wiki/Chlorophyll_a" title="Chlorophyll a"><i>a</i></a>, <a href="/wiki/Chlorophyll_b" title="Chlorophyll b"><i>b</i></a>)</li> <li><a href="/wiki/Pheophytin" title="Pheophytin">Pheophytin</a> (<a href="/wiki/Pheophytin_a" class="mw-redirect" title="Pheophytin a"><i>a</i></a>, <a href="/w/index.php?title=Pheophytin_b&action=edit&redlink=1" class="new" title="Pheophytin b (page does not exist)"><i>b</i></a>)</li> <li><a href="/wiki/Bacteriochlorophyll_c" class="mw-redirect" title="Bacteriochlorophyll c">Bacteriochlorophyll <i>c</i></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bacteriochlorin" class="mw-redirect" title="Bacteriochlorin">Bacteriochlorins</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/Bacteriochlorophyll_a" class="mw-redirect" title="Bacteriochlorophyll a">Bacteriochlorophyll <i>a</i></a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isobacteriochlorin" class="mw-redirect" title="Isobacteriochlorin">Isobacteriochlorins</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/Siroheme" title="Siroheme">Siroheme</a></li> <li><a href="/wiki/Sirohydrochlorin" title="Sirohydrochlorin">Sirohydrochlorin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Corphin&action=edit&redlink=1" class="new" title="Corphin (page does not exist)">Corphins</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/Cofactor_F430" title="Cofactor F430">Cofactor F430</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><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="Dietary_supplements" 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_supplements" 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 class="mw-selflink selflink">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 href="/wiki/Lipoic_acid" title="Lipoic acid">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> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 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