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class="vector-toc-numb">2</span> <span>Terminology</span> </div> </a> <ul id="toc-Terminology-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Uses</span> </div> </a> <button aria-controls="toc-Uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Uses subsection</span> </button> <ul id="toc-Uses-sublist" class="vector-toc-list"> <li id="toc-Animal_feed" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Animal_feed"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Animal feed</span> </div> </a> <ul id="toc-Animal_feed-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Human_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Human_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Human use</span> </div> </a> <ul id="toc-Human_use-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Toxicology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicology"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Toxicology</span> </div> </a> <ul id="toc-Toxicology-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">5</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button 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Available in 21 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-21" 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">21 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D9%8A%D9%86%D8%A7%D8%AF%D9%8A%D9%88%D9%86" title="ميناديون – Arabic" lang="ar" hreflang="ar" data-title="ميناديون" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%85%D9%86%D8%A7%D8%AF%DB%8C%D9%88%D9%86" title="منادیون – South Azerbaijani" lang="azb" hreflang="azb" data-title="منادیون" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Menadion" title="Menadion – Welsh" lang="cy" hreflang="cy" data-title="Menadion" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Menadion" title="Menadion – German" lang="de" hreflang="de" data-title="Menadion" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Menadiona" title="Menadiona – Spanish" lang="es" hreflang="es" data-title="Menadiona" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Menadiona" title="Menadiona – Basque" lang="eu" hreflang="eu" data-title="Menadiona" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%85%D9%86%D8%A7%D8%AF%DB%8C%D9%88%D9%86" title="منادیون – Persian" lang="fa" hreflang="fa" data-title="منادیون" 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/M%C3%A9nadione" title="Ménadione – French" lang="fr" hreflang="fr" data-title="Ménadione" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%92%D0%B8%D0%BA%D0%B0%D1%81%D0%BE%D0%BB" title="Викасол – Kazakh" lang="kk" hreflang="kk" data-title="Викасол" 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%92%D0%B8%D0%BA%D0%B0%D1%81%D0%BE%D0%BB" title="Викасол – Kyrgyz" lang="ky" hreflang="ky" data-title="Викасол" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Menadion" title="Menadion – Dutch" lang="nl" hreflang="nl" data-title="Menadion" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%A1%E3%83%8A%E3%82%B8%E3%82%AA%E3%83%B3" title="メナジオン – Japanese" lang="ja" hreflang="ja" data-title="メナジオン" 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-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Menadion" title="Menadion – Polish" lang="pl" hreflang="pl" data-title="Menadion" 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/Menadiona" title="Menadiona – Portuguese" lang="pt" hreflang="pt" data-title="Menadiona" 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/Menadion%C4%83" title="Menadionă – Romanian" lang="ro" hreflang="ro" data-title="Menadionă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9C%D0%B5%D0%BD%D0%B0%D0%B4%D0%B8%D0%BE%D0%BD" title="Менадион – Russian" lang="ru" hreflang="ru" data-title="Менадион" 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/Menadion" title="Menadion – Serbian" lang="sr" hreflang="sr" data-title="Menadion" 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/Menadion" title="Menadion – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Menadion" 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/Menadioni" title="Menadioni – Finnish" lang="fi" hreflang="fi" data-title="Menadioni" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9C%D0%B5%D0%BD%D0%B0%D0%B4%D1%96%D0%BE%D0%BD" title="Менадіон – Ukrainian" lang="uk" hreflang="uk" data-title="Менадіон" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%94%B2%E8%90%98%E9%86%8C" title="甲萘醌 – Chinese" lang="zh" hreflang="zh" data-title="甲萘醌" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q192471#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 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.hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Not to confuse with <a href="/wiki/Menaquinone" class="mw-redirect" title="Menaquinone">menaquinone</a>-3<i>, aka MK-3, a version of <a href="/wiki/Vitamin_K2" title="Vitamin K2">vitamin K2</a></i> series having 3 isoprene groups</div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Missing_information plainlinks metadata ambox ambox-content" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Wiki_letter_w.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/44px-Wiki_letter_w.svg.png" decoding="async" width="44" height="44" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/66px-Wiki_letter_w.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/6/6c/Wiki_letter_w.svg/88px-Wiki_letter_w.svg.png 2x" data-file-width="44" data-file-height="44" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This article <b>is missing information</b> about drugbox or more Chembox Pharmacology.<span class="hide-when-compact"> Please expand the article to include this information. Further details may exist on the <a href="/wiki/Talk:Menadione" title="Talk:Menadione">talk page</a>.</span> <span class="date-container"><i>(<span class="date">January 2021</span>)</i></span></div></td></tr></tbody></table><style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Menadione<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> </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Menadione.svg" class="mw-file-description" title="Skeletal formula"><img alt="Skeletal formula" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Menadione.svg/140px-Menadione.svg.png" decoding="async" width="140" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Menadione.svg/210px-Menadione.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/ed/Menadione.svg/280px-Menadione.svg.png 2x" data-file-width="291" data-file-height="305" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Menadione-from-xtal-3D-bs-17.png" class="mw-file-description" title="Ball-and-stick model"><img alt="Ball-and-stick model" src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Menadione-from-xtal-3D-bs-17.png/170px-Menadione-from-xtal-3D-bs-17.png" decoding="async" width="170" height="127" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Menadione-from-xtal-3D-bs-17.png/255px-Menadione-from-xtal-3D-bs-17.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/Menadione-from-xtal-3D-bs-17.png/340px-Menadione-from-xtal-3D-bs-17.png 2x" data-file-width="3087" data-file-height="2311" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2-Methylnaphthalene-1,4-dione</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Menaphthone; Vitamin K<sub>3</sub>; β-Methyl-1,4-naphthoquinone; 2-Methyl-1,4-naphthodione; 2-Methyl-1,4-naphthoquinone</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=58-27-5">58-27-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%5C2c1c%28cccc1%29C%28%3DO%29%2FC%28%3DC%2F2%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=28869">CHEBI:28869</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL590">ChEMBL590</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.3915.html">3915</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00170">DB00170</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.338">100.000.338</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q192471#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D02335">D02335</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/4055">4055</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/723JX6CXY5">723JX6CXY5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID4021715">DTXSID4021715</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q192471#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MJVAVZPDRWSRRC-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: MJVAVZPDRWSRRC-UHFFFAOYAY</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C\2c1c(cccc1)C(=O)/C(=C/2)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>11</sub><span title="Hydrogen">H</span><sub>8</sub><span title="Oxygen">O</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002172183000000000♠"></span>172.183</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Bright yellow crystals </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.225g/cm3 </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>105 to 107 °C (221 to 225 °F; 378 to 380 K) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Insoluble </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_B02" title="ATC code B02">B02BA02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=B02BA02">WHO</a></span>)  </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li>Contraindicated (India)<sup id="cite_ref-dui_2-0" class="reference"><a href="#cite_note-dui-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul> </div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>Oral</li><li>Intravenous</li><li><a href="/wiki/Intramuscular_injection" title="Intramuscular injection">Intramuscular</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li>Generally Rx or withdrawn for human use; approved in animal feed</li></ul></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>113.8 °C (236.8 °F; 386.9 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>0.5 g/kg (oral, mouse) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=411385075&page2=Menadione">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Menadione</b> is a synthetic<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><sup id="cite_ref-nat_4-0" class="reference"><a href="#cite_note-nat-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the formula C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>C<sub>2</sub>H(CH<sub>3</sub>). It is an <a href="/wiki/Structural_analog" title="Structural analog">analog</a> of <a href="/wiki/1,4-Naphthoquinone" title="1,4-Naphthoquinone">1,4-naphthoquinone</a> with a <a href="/wiki/Methyl_group" title="Methyl group">methyl group</a> in the 2-position.<sup id="cite_ref-pmid19098979_5-0" class="reference"><a href="#cite_note-pmid19098979-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It is sometimes called <b>vitamin K<sub>3</sub></b>. Use is allowed as a <a href="/wiki/Dietary_supplement" title="Dietary supplement">nutritional supplement</a> in <a href="/wiki/Animal_feed" title="Animal feed">animal feed</a> because of its <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a> activity. </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Menadione&action=edit&section=1" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Menadione is converted to <a href="/wiki/Vitamin_K2" title="Vitamin K2">vitamin K<sub>2</sub></a> (specifically, <a href="/wiki/MK-4" class="mw-redirect" title="MK-4">MK-4</a>) by the <a href="/wiki/Prenyltransferase" title="Prenyltransferase">prenyltransferase</a> action of <a href="/wiki/Vertebrate" title="Vertebrate">vertebrate</a> <a href="/wiki/UBIAD1" title="UBIAD1">UBIAD1</a>.<sup id="cite_ref-nat_4-1" class="reference"><a href="#cite_note-nat-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> This reaction requires the hydroquinone (reduced) form of K<sub>3</sub>, <a href="/wiki/Menadiol" title="Menadiol">menadiol</a>, produced by <a href="/wiki/NQO1" class="mw-redirect" title="NQO1">NQO1</a>.<sup id="cite_ref-:0_6-0" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Menadione is also a circulating form of vitamin K, produced in small amounts (1–5%) after intestinal absorption of K<sub>1</sub> and K<sub>2</sub>. This circulation explains the uneven tissue distribution of MK-4, especially since menadione can penetrate the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a>. The cleavage enzyme is yet to be identified. As K<sub>3</sub> is known to be toxic in large amounts, researchers speculate that the cleavage process is closely regulated.<sup id="cite_ref-:0_6-1" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Terminology">Terminology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Menadione&action=edit&section=2" title="Edit section: Terminology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The compound is variously known as vitamin K<sub>3</sub><sup id="cite_ref-pmid15939799_7-0" class="reference"><a href="#cite_note-pmid15939799-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> and <a href="/wiki/Provitamin" title="Provitamin">provitamin</a> K<sub>3</sub>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Proponents of the latter name generally argue that the compound is not a real <a href="/wiki/Vitamin" title="Vitamin">vitamin</a> due to its artificial status (prior to its identification as a circulating intermediate) and its lack of a 3-methyl side chain preventing it from exerting all the functions (specifically, it cannot act as a cofactor for <a href="/wiki/GGCX" class="mw-redirect" title="GGCX">GGCX</a> <i>in vitro</i>)<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> of the K vitamins. </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Menadione&action=edit&section=3" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Phylloquinone_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Phylloquinone_structure.svg/220px-Phylloquinone_structure.svg.png" decoding="async" width="220" height="104" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/93/Phylloquinone_structure.svg/330px-Phylloquinone_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/93/Phylloquinone_structure.svg/440px-Phylloquinone_structure.svg.png 2x" data-file-width="1600" data-file-height="755" /></a><figcaption>The menadione core is apparent in the structure of <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a>.</figcaption></figure> <p>It is an intermediate in the chemical synthesis of vitamin K by first reduction to the <a href="/wiki/Diol" title="Diol">diol</a> <a href="/wiki/Menadiol" title="Menadiol">menadiol</a>, which is susceptible to coupling to the <a href="/wiki/Phytol" title="Phytol">phytol</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is a useful intermediate for organic synthesis in general, as it can be made and modified in a number of ways.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Menadione can be used to generate <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a> to perform flow cytometry analysis on. It can also be used in microbiological evaluation to, for example, detect <a href="/wiki/Fastidious" class="mw-redirect" title="Fastidious">fastidious</a> microorganisms.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Animal_feed">Animal feed</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Menadione&action=edit&section=4" title="Edit section: Animal feed"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the United States, menadione is used in various types of animal feed and is described as having a history of safe use for this purpose, being used in poultry feed prior to 1958.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>Low-dose menadione is used as an inexpensive micronutrient for livestock in many countries. Forms of menadione are also included in some pet foods in developed countries as a source of vitamin K. These doses have yielded no reported cases of toxicity from menadione in livestock or pets. Although handling may be hazardous, the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> found in 2013 that it is an effective source of vitamin K in animal nutrition that does not pose a risk to the environment.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Human_use">Human use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Menadione&action=edit&section=5" title="Edit section: Human use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Despite the fact that it can serve as a precursor to various types of <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a>, menadione is generally not used as a nutritional supplement in economically developed countries. Menadione for human use at pharmaceutical strength is available in some countries with large lower income populations, such as India.<sup id="cite_ref-dui_2-1" class="reference"><a href="#cite_note-dui-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The typical daily dose is 10 mg oral or 2 mg parenteral.<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> It is used in the treatment of <a href="/wiki/Hypoprothrombinemia" title="Hypoprothrombinemia">hypoprothrombinemia</a> outside of the United States.<sup id="cite_ref-dui_2-2" class="reference"><a href="#cite_note-dui-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicology">Toxicology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Menadione&action=edit&section=6" title="Edit section: Toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Menadione is not believed to be carcinogenic.<sup id="cite_ref-Hassan_16-0" class="reference"><a href="#cite_note-Hassan-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> K3 can cause generation of reactive oxygen species (ROS) by <a href="/wiki/Redox_cycling" class="mw-redirect" title="Redox cycling">redox cycling</a> and arylation of thiols using its reactive 3-position.<sup id="cite_ref-:0_6-2" class="reference"><a href="#cite_note-:0-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> ROS generation explains various toxic effects of excessive menadione, including DNA damage and cell death,<sup id="cite_ref-Hassan_16-1" class="reference"><a href="#cite_note-Hassan-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> or on a whole-animal level, cardiac and renal toxicity in rats.<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="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Menadione&action=edit&section=7" 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"><i><a href="/wiki/The_Merck_Index" class="mw-redirect" title="The Merck Index">The Merck Index</a></i>, 11th Edition, <b>5714</b></span> </li> <li id="cite_note-dui-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-dui_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-dui_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-dui_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugsupdate.com/generic/view/1153/Menadione">"Menadione drug information"</a>. <i>DrugsUpdate India</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DrugsUpdate+India&rft.atitle=Menadione+drug+information&rft_id=https%3A%2F%2Fwww.drugsupdate.com%2Fgeneric%2Fview%2F1153%2FMenadione&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMenadione" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://go.drugbank.com/drugs/DB00170">"Menadione"</a>. <i>go.drugbank.com</i><span class="reference-accessdate">. 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Retrieved <span class="nowrap">2 February</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Sigma-Aldrich&rft.atitle=Menadione&rft_id=https%3A%2F%2Fwww.sigmaaldrich.com%2FUS%2Fen%2Fproduct%2Fsigma%2Fm5625&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMenadione" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://www.fda.gov/animal-veterinary/safe-feed/vitamin-k-substances-and-animal-feed">"Vitamin K Substances and Animal Feed"</a>. <i>FDA</i>. 2 April 2021.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=FDA&rft.atitle=Vitamin+K+Substances+and+Animal+Feed&rft.date=2021-04-02&rft_id=https%3A%2F%2Fwww.fda.gov%2Fanimal-veterinary%2Fsafe-feed%2Fvitamin-k-substances-and-animal-feed&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMenadione" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFEFSA_Panel_on_Additives_and_Products_or_Substances_used_in_Animal_Feed_(FEEDAP)2014" class="citation journal cs1">EFSA Panel on Additives and Products or Substances used in Animal Feed (FEEDAP) (January 2014). <a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2014.3532">"Scientific Opinion on the safety and efficacy of vitamin K3 (menadione sodium bisulphite and menadione nicotinamide bisulphite) as a feed additive for all animal species"</a>. <i>EFSA Journal</i>. <b>12</b> (1): 3532. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2014.3532">10.2903/j.efsa.2014.3532</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=EFSA+Journal&rft.atitle=Scientific+Opinion+on+the+safety+and+efficacy+of+vitamin+K3+%28menadione+sodium+bisulphite+and+menadione+nicotinamide+bisulphite%29+as+a+feed+additive+for+all+animal+species.&rft.volume=12&rft.issue=1&rft.pages=3532&rft.date=2014-01&rft_id=info%3Adoi%2F10.2903%2Fj.efsa.2014.3532&rft.au=EFSA+Panel+on+Additives+and+Products+or+Substances+used+in+Animal+Feed+%28FEEDAP%29&rft_id=https%3A%2F%2Fdoi.org%2F10.2903%252Fj.efsa.2014.3532&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMenadione" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=B02BA02">"Menadione (B02BA02)"</a>. <i>WHOCC - ATC/DDD Index</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=WHOCC+-+ATC%2FDDD+Index&rft.atitle=Menadione+%28B02BA02%29&rft_id=https%3A%2F%2Fwww.whocc.no%2Fatc_ddd_index%2F%3Fcode%3DB02BA02&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMenadione" class="Z3988"></span></span> </li> <li id="cite_note-Hassan-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-Hassan_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Hassan_16-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHassan2013" class="citation book cs1">Hassan, Ghada S. (2013). "Menadione". <i>Profiles of Drug Substances, Excipients and Related Methodology</i>. Vol. 38. pp. 227–313. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FB978-0-12-407691-4.00006-X">10.1016/B978-0-12-407691-4.00006-X</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780124076914" title="Special:BookSources/9780124076914"><bdi>9780124076914</bdi></a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23668406">23668406</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:242264898">242264898</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Menadione&rft.btitle=Profiles+of+Drug+Substances%2C+Excipients+and+Related+Methodology&rft.pages=227-313&rft.date=2013&rft_id=info%3Adoi%2F10.1016%2FB978-0-12-407691-4.00006-X&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A242264898%23id-name%3DS2CID&rft_id=info%3Apmid%2F23668406&rft.isbn=9780124076914&rft.aulast=Hassan&rft.aufirst=Ghada+S.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMenadione" class="Z3988"></span> <span class="cs1-visible-error citation-comment"><code class="cs1-code">{{<a href="/wiki/Template:Cite_book" title="Template:Cite book">cite book</a>}}</code>: </span><span class="cs1-visible-error citation-comment"><code class="cs1-code">|journal=</code> ignored (<a href="/wiki/Help:CS1_errors#periodical_ignored" title="Help:CS1 errors">help</a>)</span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChiouZhangFerransTzeng1997" class="citation journal cs1">Chiou, TJ; Zhang, J; Ferrans, VJ; Tzeng, WF (31 December 1997). "Cardiac and renal toxicity of menadione in rat". <i>Toxicology</i>. <b>124</b> (3): 193–202. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fs0300-483x%2897%2900162-5">10.1016/s0300-483x(97)00162-5</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9482121">9482121</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicology&rft.atitle=Cardiac+and+renal+toxicity+of+menadione+in+rat.&rft.volume=124&rft.issue=3&rft.pages=193-202&rft.date=1997-12-31&rft_id=info%3Adoi%2F10.1016%2Fs0300-483x%2897%2900162-5&rft_id=info%3Apmid%2F9482121&rft.aulast=Chiou&rft.aufirst=TJ&rft.au=Zhang%2C+J&rft.au=Ferrans%2C+VJ&rft.au=Tzeng%2C+WF&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMenadione" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Menadione&action=edit&section=8" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><i><a rel="nofollow" class="external text" href="http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1381.htm">Menadione</a></i> in the Pesticide Properties DataBase (PPDB)</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline 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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 class="mw-selflink selflink">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 href="/wiki/Cyanocobalamin" title="Cyanocobalamin">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="Antihemorrhagics_(B02)" 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:Antihemorrhagics" title="Template:Antihemorrhagics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antihemorrhagics" title="Template talk:Antihemorrhagics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antihemorrhagics" title="Special:EditPage/Template:Antihemorrhagics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antihemorrhagics_(B02)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antihemorrhagic" title="Antihemorrhagic">Antihemorrhagics</a> (<a href="/wiki/ATC_code_B02" title="ATC code B02">B02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antihemorrhagic" title="Antihemorrhagic">Antihemorrhagics</a><br />(<a href="/wiki/Coagulation" title="Coagulation">coagulation</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%">Systemic</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/Vitamin_K" title="Vitamin K">Vitamin K</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/Phylloquinone" class="mw-redirect" title="Phylloquinone">Phytomenadione (K<sub>1</sub>)</a></li> <li><a class="mw-selflink selflink">Menadione (K<sub>3</sub>)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Coagulation" title="Coagulation">Coagulation<br /> factors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>intrinsic:</i></li> <li><a href="/wiki/Factor_VIII" title="Factor VIII">VIII</a>/(<a href="/wiki/Damoctocog_alfa_pegol" title="Damoctocog alfa pegol">Damoctocog alfa pegol</a>, <a href="/wiki/Efanesoctocog_alfa" title="Efanesoctocog alfa">Efanesoctocog alfa</a>, <a href="/wiki/Efmoroctocog_alfa" title="Efmoroctocog alfa">Efmoroctocog alfa</a>, <a href="/wiki/Moroctocog_alfa" title="Moroctocog alfa">Moroctocog alfa</a>, <a href="/wiki/Susoctocog_alfa" title="Susoctocog alfa">Susoctocog alfa</a>, <a href="/wiki/Turoctocog_alfa" title="Turoctocog alfa">Turoctocog alfa</a>, <a href="/wiki/Valoctocogene_roxaparvovec" title="Valoctocogene roxaparvovec">Valoctocogene roxaparvovec</a>, <a href="/wiki/Factor_VIII_(medication)" title="Factor VIII (medication)">von Willebrand factor</a>)</li> <li><a href="/wiki/Factor_IX" title="Factor IX">IX</a>/(<a href="/wiki/Fidanacogene_elaparvovec" title="Fidanacogene elaparvovec">Fidanacogene elaparvovec</a>, <a href="/wiki/Nonacog_alfa" class="mw-redirect" title="Nonacog alfa">Nonacog alfa</a>)</li></ul> <ul><li><i>extrinsic:</i> <a href="/wiki/Factor_VII" title="Factor VII">VII</a>/<a href="/wiki/Recombinant_factor_VIIa" title="Recombinant factor VIIa">Eptacog alfa</a></li></ul> <ul><li><i>common:</i> <a href="/wiki/Factor_X" title="Factor X">X</a></li> <li><a href="/wiki/Thrombin" title="Thrombin">II/Thrombin</a></li> <li><a href="/wiki/Fibrinogen" title="Fibrinogen">I/Fibrinogen</a></li> <li><a href="/wiki/Factor_XIII" title="Factor XIII">XIII</a>/<a href="/wiki/Catridecacog" title="Catridecacog">Catridecacog</a></li></ul> <ul><li><i>combinations:</i> <a href="/wiki/Prothrombin_complex_concentrate" title="Prothrombin complex concentrate">Prothrombin complex concentrate</a> (II, VII, IX, X, protein C and S)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other<br /> systemic</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/Batroxobin" title="Batroxobin">Batroxobin</a></li> <li><a href="/wiki/Carbazochrome" title="Carbazochrome">Carbazochrome</a></li> <li><a href="/wiki/Concizumab" title="Concizumab">Concizumab</a></li> <li><a href="/wiki/Etamsylate" title="Etamsylate">Etamsylate</a></li> <li><a href="/wiki/Fostamatinib" title="Fostamatinib">Fostamatinib</a></li> <li><a href="/wiki/Marstacimab" title="Marstacimab">Marstacimab</a></li> <li><i><a href="/wiki/Thrombopoietin_receptor_agonist" class="mw-redirect" title="Thrombopoietin receptor agonist">thrombopoietin receptor agonist</a></i> <ul><li><a href="/wiki/Romiplostim" title="Romiplostim">Romiplostim</a></li> <li><a href="/wiki/Avatrombopag" title="Avatrombopag">Avatrombopag</a></li> <li><a href="/wiki/Eltrombopag" title="Eltrombopag">Eltrombopag</a></li> <li><a href="/wiki/Lusutrombopag" title="Lusutrombopag">Lusutrombopag</a></li> <li><a href="/wiki/Rafutrombopag" class="mw-redirect" title="Rafutrombopag">Rafutrombopag</a></li></ul></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Local</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/Absorbable_gelatin_sponge" title="Absorbable gelatin sponge">Absorbable gelatin sponge</a></li> <li><a href="/wiki/Calcium_alginate" title="Calcium alginate">Calcium alginate</a></li> <li><a href="/wiki/Collagen" title="Collagen">Collagen</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a>/<a href="/wiki/Adrenalone" title="Adrenalone">adrenalone</a></li> <li><a href="/wiki/Fibrin_glue" title="Fibrin glue">Fibrin glue</a></li> <li><a href="/wiki/Oxidized_cellulose" title="Oxidized cellulose">Oxidized cellulose</a></li> <li><a href="/wiki/Tetragalacturonic_acid_hydroxymethylester" title="Tetragalacturonic acid hydroxymethylester">Tetragalacturonic acid hydroxymethylester</a></li> <li><a href="/wiki/Thrombin" title="Thrombin">Thrombin</a></li> <li><a href="/wiki/Hemostatic_Powder_Spray_TC-325" title="Hemostatic Powder Spray TC-325">Hemostatic Powder Spray TC-325</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antifibrinolytic" title="Antifibrinolytic">Antifibrinolytics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Amino_acid" title="Amino acid">amino acids</a></i> <ul><li><a href="/wiki/Aminocaproic_acid" title="Aminocaproic acid">Aminocaproic acid</a></li> <li><a href="/wiki/Tranexamic_acid" title="Tranexamic acid">Tranexamic acid</a></li> <li><a href="/wiki/Aminomethylbenzoic_acid" title="Aminomethylbenzoic acid">Aminomethylbenzoic acid</a></li></ul></li> <li><i><a href="/wiki/Serpin" title="Serpin">serpins</a></i> <ul><li><a href="/wiki/Aprotinin" title="Aprotinin">Aprotinin</a></li> <li><a href="/wiki/Alpha_1-antitrypsin" class="mw-redirect" title="Alpha 1-antitrypsin">Alfa1 antitrypsin</a></li> <li><a href="/wiki/C1-inhibitor" title="C1-inhibitor">C1-inhibitor</a></li> <li><a href="/wiki/Camostat" title="Camostat">Camostat</a></li></ul></li> <li>unsorted <ul><li><a href="/wiki/Ulinastatin" title="Ulinastatin">Ulinastatin</a></li></ul></li></ul> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" 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