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recommendations</span> </div> </a> <button aria-controls="toc-Dietary_recommendations-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 Dietary recommendations subsection</span> </button> <ul id="toc-Dietary_recommendations-sublist" class="vector-toc-list"> <li id="toc-Fortification" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fortification"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Fortification</span> </div> </a> <ul id="toc-Fortification-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Sources" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Sources</span> </div> </a> <button aria-controls="toc-Sources-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 Sources subsection</span> </button> <ul id="toc-Sources-sublist" class="vector-toc-list"> <li id="toc-Vitamin_K1" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vitamin_K1"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Vitamin K<sub>1</sub></span> </div> </a> <ul id="toc-Vitamin_K1-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Vitamin_K2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Vitamin_K2"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Vitamin K<sub>2</sub></span> </div> </a> <ul id="toc-Vitamin_K2-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Vitamin_K_deficiency" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Vitamin_K_deficiency"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Vitamin K deficiency</span> </div> </a> <ul id="toc-Vitamin_K_deficiency-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Medical_uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Medical_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Medical uses</span> </div> </a> <button aria-controls="toc-Medical_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 Medical uses subsection</span> </button> <ul id="toc-Medical_uses-sublist" class="vector-toc-list"> <li id="toc-Treating_vitamin_deficiency_in_newborns" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Treating_vitamin_deficiency_in_newborns"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Treating vitamin deficiency in newborns</span> </div> </a> <ul id="toc-Treating_vitamin_deficiency_in_newborns-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Managing_warfarin_therapy" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Managing_warfarin_therapy"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Managing warfarin therapy</span> </div> </a> <ul id="toc-Managing_warfarin_therapy-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Treating_rodenticide_poisoning" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Treating_rodenticide_poisoning"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Treating rodenticide poisoning</span> </div> </a> <ul id="toc-Treating_rodenticide_poisoning-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Methods_of_assessment" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Methods_of_assessment"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Methods of assessment</span> </div> </a> <ul id="toc-Methods_of_assessment-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Side effects</span> </div> </a> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Non-human_uses" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Non-human_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Non-human uses</span> </div> </a> <ul id="toc-Non-human_uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Chemistry</span> </div> </a> <button aria-controls="toc-Chemistry-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 Chemistry subsection</span> </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Conversion_of_vitamin_K1_to_vitamin_K2" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Conversion_of_vitamin_K1_to_vitamin_K2"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Conversion of vitamin K<sub>1</sub> to vitamin K<sub>2</sub></span> </div> </a> <ul id="toc-Conversion_of_vitamin_K1_to_vitamin_K2-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Physiology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Physiology"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Physiology</span> </div> </a> <button aria-controls="toc-Physiology-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 Physiology subsection</span> </button> <ul id="toc-Physiology-sublist" class="vector-toc-list"> <li id="toc-Absorption" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Absorption"> <div class="vector-toc-text"> <span class="vector-toc-numb">8.1</span> <span>Absorption</span> </div> </a> <ul id="toc-Absorption-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Biochemistry</span> </div> </a> <button aria-controls="toc-Biochemistry-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 Biochemistry subsection</span> </button> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> <li id="toc-Function_in_animals" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Function_in_animals"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Function in animals</span> </div> </a> <ul id="toc-Function_in_animals-sublist" class="vector-toc-list"> <li id="toc-Gamma-carboxyglutamate_proteins" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Gamma-carboxyglutamate_proteins"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1.1</span> <span>Gamma-carboxyglutamate proteins</span> </div> </a> <ul id="toc-Gamma-carboxyglutamate_proteins-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Function_in_plants_and_cyanobacteria" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Function_in_plants_and_cyanobacteria"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Function in plants and cyanobacteria</span> </div> </a> <ul id="toc-Function_in_plants_and_cyanobacteria-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Function_in_other_bacteria" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Function_in_other_bacteria"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.3</span> <span>Function in other bacteria</span> </div> </a> <ul id="toc-Function_in_other_bacteria-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Research" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Research"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Research</span> </div> </a> <button aria-controls="toc-Research-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Research subsection</span> </button> <ul id="toc-Research-sublist" class="vector-toc-list"> <li id="toc-Osteoporosis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Osteoporosis"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.1</span> <span>Osteoporosis</span> </div> </a> <ul id="toc-Osteoporosis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cardiovascular_health" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cardiovascular_health"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.2</span> <span>Cardiovascular health</span> </div> </a> <ul id="toc-Cardiovascular_health-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">11.3</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">14</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 cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Vitamin K</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 72 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-72" 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">72 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Vitamien_K" title="Vitamien K – Afrikaans" lang="af" hreflang="af" data-title="Vitamien K" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D8%AA%D8%A7%D9%85%D9%8A%D9%86_%D9%83" title="فيتامين ك – Arabic" lang="ar" hreflang="ar" data-title="فيتامين ك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-hyw mw-list-item"><a href="https://hyw.wikipedia.org/wiki/%C2%AB%D5%94%D5%A7%D5%B5%C2%BB_%D5%AF%D5%A5%D5%B6%D5%BD%D5%A1%D5%B6%D5%AB%D6%82%D5%A9" title="«Քէյ» կենսանիւթ – Western Armenian" lang="hyw" hreflang="hyw" data-title="«Քէյ» կենսանիւթ" data-language-autonym="Արեւմտահայերէն" data-language-local-name="Western Armenian" class="interlanguage-link-target"><span>Արեւմտահայերէն</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Vitamina_K" title="Vitamina K – Asturian" lang="ast" hreflang="ast" data-title="Vitamina K" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/K_vitamini" title="K vitamini – Azerbaijani" lang="az" hreflang="az" data-title="K vitamini" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%88%DB%8C%D8%AA%D8%A7%D9%85%DB%8C%D9%86_%DA%A9%D8%A7" title="ویتامین کا – South Azerbaijani" lang="azb" hreflang="azb" data-title="ویتامین کا" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ban mw-list-item"><a href="https://ban.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Balinese" lang="ban" hreflang="ban" data-title="Vitamin K" data-language-autonym="Basa Bali" data-language-local-name="Balinese" class="interlanguage-link-target"><span>Basa Bali</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AD%E0%A6%BF%E0%A6%9F%E0%A6%BE%E0%A6%AE%E0%A6%BF%E0%A6%A8_%E0%A6%95%E0%A7%87" title="ভিটামিন কে – Bangla" lang="bn" hreflang="bn" data-title="ভিটামিন কে" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-zh-min-nan mw-list-item"><a href="https://zh-min-nan.wikipedia.org/wiki/B%C3%AE-t%C3%A1-m%C3%ADn_K" title="Bî-tá-mín K – Minnan" lang="nan" hreflang="nan" data-title="Bî-tá-mín K" data-language-autonym="閩南語 / Bân-lâm-gú" data-language-local-name="Minnan" class="interlanguage-link-target"><span>閩南語 / Bân-lâm-gú</span></a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Bitamina_K" title="Bitamina K – Central Bikol" lang="bcl" hreflang="bcl" data-title="Bitamina K" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target"><span>Bikol Central</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%92%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD_K" title="Витамин K – Bulgarian" lang="bg" hreflang="bg" data-title="Витамин K" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Bosnian" lang="bs" hreflang="bs" data-title="Vitamin K" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Vitamina_K" title="Vitamina K – Catalan" lang="ca" hreflang="ca" data-title="Vitamina K" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Vitam%C3%ADn_K" title="Vitamín K – Czech" lang="cs" hreflang="cs" data-title="Vitamín K" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Danish" lang="da" hreflang="da" data-title="Vitamin K" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – German" lang="de" hreflang="de" data-title="Vitamin K" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-dv mw-list-item"><a href="https://dv.wikipedia.org/wiki/%DE%88%DE%A8%DE%93%DE%A6%DE%89%DE%A8%DE%82%DE%B0_%DE%86%DE%AD" title="ވިޓަމިން ކޭ – Divehi" lang="dv" hreflang="dv" data-title="ވިޓަމިން ކޭ" data-language-autonym="ދިވެހިބަސް" data-language-local-name="Divehi" class="interlanguage-link-target"><span>ދިވެހިބަސް</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Naftokinoonid" title="Naftokinoonid – Estonian" lang="et" hreflang="et" data-title="Naftokinoonid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%92%CE%B9%CF%84%CE%B1%CE%BC%CE%AF%CE%BD%CE%B7_%CE%9A" title="Βιταμίνη Κ – Greek" lang="el" hreflang="el" data-title="Βιταμίνη Κ" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Vitamina_K" title="Vitamina K – Spanish" lang="es" hreflang="es" data-title="Vitamina K" 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/Vitamino_K" title="Vitamino K – Esperanto" lang="eo" hreflang="eo" data-title="Vitamino K" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/K_bitamina" title="K bitamina – Basque" lang="eu" hreflang="eu" data-title="K bitamina" 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%88%DB%8C%D8%AA%D8%A7%D9%85%DB%8C%D9%86_%DA%A9%D8%A7" title="ویتامین کا – Persian" lang="fa" hreflang="fa" data-title="ویتامین کا" 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/Vitamine_K" title="Vitamine K – French" lang="fr" hreflang="fr" data-title="Vitamine K" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Vitamina_K" title="Vitamina K – Galician" lang="gl" hreflang="gl" data-title="Vitamina K" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B9%84%ED%83%80%EB%AF%BC_K" title="비타민 K – Korean" lang="ko" hreflang="ko" data-title="비타민 K" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8E%D5%AB%D5%BF%D5%A1%D5%B4%D5%AB%D5%B6_K" title="Վիտամին K – Armenian" lang="hy" hreflang="hy" data-title="Վիտամին K" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B5%E0%A4%BF%E0%A4%9F%E0%A4%BE%E0%A4%AE%E0%A4%BF%E0%A4%A8_%E0%A4%95%E0%A5%87" title="विटामिन के – Hindi" lang="hi" hreflang="hi" data-title="विटामिन के" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Croatian" lang="hr" hreflang="hr" data-title="Vitamin K" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Indonesian" lang="id" hreflang="id" data-title="Vitamin K" 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-is mw-list-item"><a href="https://is.wikipedia.org/wiki/K-v%C3%ADtam%C3%ADn" title="K-vítamín – Icelandic" lang="is" hreflang="is" data-title="K-vítamín" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Vitamina_K" title="Vitamina K – Italian" lang="it" hreflang="it" data-title="Vitamina K" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%95%D7%99%D7%98%D7%9E%D7%99%D7%9F_K" title="ויטמין K – Hebrew" lang="he" hreflang="he" data-title="ויטמין K" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Javanese" lang="jv" hreflang="jv" data-title="Vitamin K" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-ka mw-list-item"><a href="https://ka.wikipedia.org/wiki/%E1%83%95%E1%83%98%E1%83%A2%E1%83%90%E1%83%9B%E1%83%98%E1%83%9C%E1%83%98_K" title="ვიტამინი K – Georgian" lang="ka" hreflang="ka" data-title="ვიტამინი K" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%9A_%D0%B2%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD%D0%B8" title="К витамини – Kyrgyz" lang="ky" hreflang="ky" data-title="К витамини" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target"><span>Кыргызча</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Vitaminum_K" title="Vitaminum K – Latin" lang="la" hreflang="la" data-title="Vitaminum K" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/K_vitam%C4%ABns" title="K vitamīns – Latvian" lang="lv" hreflang="lv" data-title="K vitamīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Vitaminas_K" title="Vitaminas K – Lithuanian" lang="lt" hreflang="lt" data-title="Vitaminas K" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%9C%E0%B5%80%E0%B4%B5%E0%B4%95%E0%B4%82_%E0%B4%95%E0%B5%86" title="ജീവകം കെ – Malayalam" lang="ml" hreflang="ml" data-title="ജീവകം കെ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-mr mw-list-item"><a href="https://mr.wikipedia.org/wiki/%E0%A4%95%E0%A5%87-%E0%A4%9C%E0%A5%80%E0%A4%B5%E0%A4%A8%E0%A4%B8%E0%A4%A4%E0%A5%8D%E0%A4%A4%E0%A5%8D%E0%A4%B5" title="के-जीवनसत्त्व – Marathi" lang="mr" hreflang="mr" data-title="के-जीवनसत्त्व" data-language-autonym="मराठी" data-language-local-name="Marathi" class="interlanguage-link-target"><span>मराठी</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Malay" lang="ms" hreflang="ms" data-title="Vitamin K" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-my mw-list-item"><a href="https://my.wikipedia.org/wiki/%E1%80%97%E1%80%AE%E1%80%90%E1%80%AC%E1%80%99%E1%80%84%E1%80%BA%E1%80%80%E1%80%B1" title="ဗီတာမင်ကေ – Burmese" lang="my" hreflang="my" data-title="ဗီတာမင်ကေ" data-language-autonym="မြန်မာဘာသာ" data-language-local-name="Burmese" class="interlanguage-link-target"><span>မြန်မာဘာသာ</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Vitamine_K" title="Vitamine K – Dutch" lang="nl" hreflang="nl" data-title="Vitamine K" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ne mw-list-item"><a href="https://ne.wikipedia.org/wiki/%E0%A4%AD%E0%A4%BF%E0%A4%9F%E0%A4%BE%E0%A4%AE%E0%A4%BF%E0%A4%A8_%E0%A4%95%E0%A5%87" title="भिटामिन के – Nepali" lang="ne" hreflang="ne" data-title="भिटामिन के" data-language-autonym="नेपाली" data-language-local-name="Nepali" class="interlanguage-link-target"><span>नेपाली</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%93%E3%82%BF%E3%83%9F%E3%83%B3K" title="ビタミンK – Japanese" lang="ja" hreflang="ja" data-title="ビタミンK" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Vitamin K" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Vitamin K" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Vitamina_K" title="Vitamina K – Occitan" lang="oc" hreflang="oc" data-title="Vitamina K" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target"><span>Occitan</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Witamina_K" title="Witamina K – Polish" lang="pl" hreflang="pl" data-title="Witamina K" 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/Vitamina_K" title="Vitamina K – Portuguese" lang="pt" hreflang="pt" data-title="Vitamina K" 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/Vitamina_K" title="Vitamina K – Romanian" lang="ro" hreflang="ro" data-title="Vitamina K" 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%92%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD_K" title="Витамин K – Russian" lang="ru" hreflang="ru" data-title="Витамин K" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Vitamina_K" title="Vitamina K – Albanian" lang="sq" hreflang="sq" data-title="Vitamina K" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Simple English" lang="en-simple" hreflang="en-simple" data-title="Vitamin K" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Slovenian" lang="sl" hreflang="sl" data-title="Vitamin K" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%92%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD_%D0%9A" title="Витамин К – Serbian" lang="sr" hreflang="sr" data-title="Витамин К" 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/Vitamin_K" title="Vitamin K – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Vitamin K" 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-su mw-list-item"><a href="https://su.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Sundanese" lang="su" hreflang="su" data-title="Vitamin K" data-language-autonym="Sunda" data-language-local-name="Sundanese" class="interlanguage-link-target"><span>Sunda</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/K-vitamiinit" title="K-vitamiinit – Finnish" lang="fi" hreflang="fi" data-title="K-vitamiinit" 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/K-vitamin" title="K-vitamin – Swedish" lang="sv" hreflang="sv" data-title="K-vitamin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%89%E0%AE%AF%E0%AE%BF%E0%AE%B0%E0%AF%8D%E0%AE%9A%E0%AF%8D%E0%AE%9A%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AF%81_%E0%AE%95%E0%AF%87" title="உயிர்ச்சத்து கே – Tamil" lang="ta" hreflang="ta" data-title="உயிர்ச்சத்து கே" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%A7%E0%B8%B4%E0%B8%95%E0%B8%B2%E0%B8%A1%E0%B8%B4%E0%B8%99%E0%B9%80%E0%B8%84" title="วิตามินเค – Thai" lang="th" hreflang="th" data-title="วิตามินเค" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/K_vitamini" title="K vitamini – Turkish" lang="tr" hreflang="tr" data-title="K vitamini" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-tyv mw-list-item"><a href="https://tyv.wikipedia.org/wiki/%D0%92%D0%98%D0%A2%D0%90%D0%9C%D0%98%D0%9D_%D0%9A" title="ВИТАМИН К – Tuvinian" lang="tyv" hreflang="tyv" data-title="ВИТАМИН К" data-language-autonym="Тыва дыл" data-language-local-name="Tuvinian" class="interlanguage-link-target"><span>Тыва дыл</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%92%D1%96%D1%82%D0%B0%D0%BC%D1%96%D0%BD_K" title="Вітамін K – Ukrainian" lang="uk" hreflang="uk" data-title="Вітамін K" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ug mw-list-item"><a href="https://ug.wikipedia.org/wiki/%DB%8B%D9%89%D8%AA%D8%A7%D9%85%D9%89%D9%86_K" title="ۋىتامىن K – Uyghur" lang="ug" hreflang="ug" data-title="ۋىتامىن K" data-language-autonym="ئۇيغۇرچە / Uyghurche" data-language-local-name="Uyghur" class="interlanguage-link-target"><span>ئۇيغۇرچە / Uyghurche</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Vitamin_K" title="Vitamin K – Vietnamese" lang="vi" hreflang="vi" data-title="Vitamin K" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-war mw-list-item"><a href="https://war.wikipedia.org/wiki/Bitamina_K" title="Bitamina K – Waray" lang="war" hreflang="war" data-title="Bitamina K" data-language-autonym="Winaray" data-language-local-name="Waray" class="interlanguage-link-target"><span>Winaray</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%BB%B4%E7%94%9F%E7%B4%A0K" title="维生素K – Wu" lang="wuu" hreflang="wuu" data-title="维生素K" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%B6%AD%E4%BB%96%E5%91%BDK" title="維他命K – Cantonese" lang="yue" hreflang="yue" data-title="維他命K" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%BB%B4%E7%94%9F%E7%B4%A0K" title="维生素K – Chinese" lang="zh" hreflang="zh" data-title="维生素K" 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/Q182338#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 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Click here for more information."><img alt="This is a good article. Click here for more information." src="//upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/19px-Symbol_support_vote.svg.png" decoding="async" width="19" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/29px-Symbol_support_vote.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/39px-Symbol_support_vote.svg.png 2x" data-file-width="180" data-file-height="185" /></a></span></div></div> </div> <div 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">Fat-soluble vitamers</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the family of vitamers. For vitamin K<sub>1</sub>, the form most commonly used as a dietary supplement or in a multi-vitamin, see <a href="/wiki/Phytomenadione" title="Phytomenadione">Phytomenadione</a>.</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"><tbody><tr><th colspan="2" class="infobox-above" style="background-color: #ddbbee">Vitamin K</th></tr><tr><td colspan="2" class="infobox-subheader"><i><a href="/wiki/Drug_class" title="Drug class">Drug class</a></i></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size skin-invert-image" typeof="mw:File/Frameless"><a href="/wiki/File:K-Vitamine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/K-Vitamine.svg/280px-K-Vitamine.svg.png" decoding="async" width="280" height="345" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/K-Vitamine.svg/420px-K-Vitamine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/K-Vitamine.svg/560px-K-Vitamine.svg.png 2x" data-file-width="447" data-file-height="550" /></a></span><div class="infobox-caption">Vitamin K structures.</div></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Class identifiers</th></tr><tr><th scope="row" class="infobox-label">Use</th><td class="infobox-data"><a href="/wiki/Vitamin_K_deficiency" title="Vitamin K deficiency">Vitamin K deficiency</a>, <a href="/wiki/Warfarin#Overdose" title="Warfarin">Warfarin overdose</a></td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><a href="/wiki/ATC_code_B02BA" class="mw-redirect" title="ATC code B02BA">B02BA</a></td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Biological_target" title="Biological target">Biological target</a></th><td class="infobox-data"><a href="/wiki/Gamma-glutamyl_carboxylase" title="Gamma-glutamyl carboxylase">Gamma-glutamyl carboxylase</a></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Clinical data</th></tr><tr><th scope="row" class="infobox-label"><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/enc/vitamin-k.html">Medical Encyclopedia</a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">External links</th></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a></th><td class="infobox-data"><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?ui=D014812">D014812</a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Legal status</th></tr><tr><td colspan="2" class="infobox-below" style="background: #e8e8e8; text-align: center"><a href="https://www.wikidata.org/wiki/Q182338" class="extiw" title="d:Q182338">In Wikidata</a></td></tr></tbody></table> <p><b>Vitamin K</b> is a family of structurally similar, <a href="/wiki/Fat-soluble" class="mw-redirect" title="Fat-soluble">fat-soluble</a> <a href="/wiki/Vitamer" title="Vitamer">vitamers</a> found in foods and marketed as <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplements</a>.<sup id="cite_ref-ods_1-0" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/Human_body" title="Human body">human body</a> requires vitamin K for <a href="/wiki/Post-translational_modification" title="Post-translational modification">post-synthesis modification</a> of certain <a href="/wiki/Protein" title="Protein">proteins</a> that are required for blood <a href="/wiki/Coagulation" title="Coagulation">coagulation</a> ("K" from Danish <i>koagulation</i>, for "coagulation") or for controlling <a href="/wiki/Molecular_binding" title="Molecular binding">binding</a> of <a href="/wiki/Calcium" title="Calcium">calcium</a> in <a href="/wiki/Bone" title="Bone">bones</a> and other <a href="/wiki/Tissue_(biology)" title="Tissue (biology)">tissues</a>.<sup id="cite_ref-Higdon_2-0" class="reference"><a href="#cite_note-Higdon-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The complete synthesis involves final modification of these <span class="nowrap">so-called</span> "<a href="/wiki/Gla_protein" class="mw-redirect" title="Gla protein">Gla proteins</a>" by the enzyme <a href="/wiki/Gamma-glutamyl_carboxylase" title="Gamma-glutamyl carboxylase">gamma-glutamyl carboxylase</a> that uses vitamin K as a <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a>. </p><p>Vitamin K is used in the liver as the intermediate VKH<sub>2</sub> to deprotonate a <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> residue and then is reprocessed into vitamin K through a vitamin K oxide intermediate.<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> The presence of uncarboxylated proteins indicates a <a href="/wiki/Vitamin_K_deficiency" title="Vitamin K deficiency">vitamin K deficiency</a>. Carboxylation allows them to bind (<a href="/wiki/Chelate" class="mw-redirect" title="Chelate">chelate</a>) <a href="/wiki/Calcium" title="Calcium">calcium</a> ions, which they cannot do otherwise.<sup id="cite_ref-PKIN2020VitK_4-0" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Without vitamin K, blood coagulation is seriously impaired, and uncontrolled bleeding occurs. Research suggests that deficiency of vitamin K may also weaken bones, potentially contributing to <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>, and may promote <a href="/wiki/Calcification" title="Calcification">calcification</a> of arteries and other soft tissues.<sup id="cite_ref-Higdon_2-1" class="reference"><a href="#cite_note-Higdon-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PKIN2020VitK_4-1" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DRItext_5-0" class="reference"><a href="#cite_note-DRItext-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Chemically, the vitamin K family comprises 2-<a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a>-<a href="/wiki/1,4-naphthoquinone" class="mw-redirect" title="1,4-naphthoquinone">1,4-naphthoquinone</a> (3-) <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivatives</a>. Vitamin K includes two natural vitamers: <a href="/wiki/Phylloquinone" class="mw-redirect" title="Phylloquinone">vitamin K<sub>1</sub></a> (<a href="/wiki/Phylloquinone" class="mw-redirect" title="Phylloquinone">phylloquinone</a>) and <a href="/wiki/Vitamin_K2" title="Vitamin K2">vitamin K<sub>2</sub></a> (<a href="/wiki/Menaquinone" class="mw-redirect" title="Menaquinone">menaquinone</a>).<sup id="cite_ref-PKIN2020VitK_4-2" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Vitamin K<sub>2</sub>, in turn, consists of a number of related chemical subtypes, with differing lengths of carbon side chains made of <a href="/wiki/Isoprene#isoprenoids" title="Isoprene">isoprenoid</a> groups of atoms. The two most studied are menaquinone-4 (MK-4) and menaquinone-7 (MK-7). </p><p>Vitamin K<sub>1</sub> is made by plants, and is found in highest amounts in <a href="/wiki/Leaf_vegetable" title="Leaf vegetable">green leafy vegetables</a>, being directly involved in <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>. It is active as a vitamin in animals and performs the classic functions of vitamin K, including its activity in the production of blood-clotting proteins. Animals may also convert it to vitamin K<sub>2</sub>, variant MK-4. <a href="/wiki/Bacteria" title="Bacteria">Bacteria</a> in the <a href="/wiki/Gut_flora" class="mw-redirect" title="Gut flora">gut flora</a> can also convert K<sub>1</sub> into K<sub>2</sub>. All forms of K<sub>2</sub> other than MK-4 can only be produced by bacteria, which use these during <a href="/wiki/Anaerobic_respiration" title="Anaerobic respiration">anaerobic respiration</a>. Vitamin K<sub>3</sub> (<a href="/wiki/Menadione" title="Menadione">menadione</a>), a synthetic form of vitamin K, was used to treat vitamin K deficiency, but because it interferes with the function of <a href="/wiki/Glutathione" title="Glutathione">glutathione</a>, it is no longer used in this manner in human nutrition.<sup id="cite_ref-Higdon_2-2" class="reference"><a href="#cite_note-Higdon-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Definition">Definition</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=1" title="Edit section: Definition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vitamin K refers to structurally similar, fat-soluble vitamers found in foods and marketed as dietary supplements. "Vitamin K" include several chemical compounds. These are similar in structure in that they share a quinone ring, but differ in the length and degree of saturation of the carbon tail and the number of repeating isoprene units in the side chain (see figures in Chemistry section). Plant-sourced forms are primarily vitamin K<sub>1</sub>. Animal-sourced foods are primarily vitamin K<sub>2</sub>.<sup id="cite_ref-ods_1-1" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-USDA-VitK_7-0" class="reference"><a href="#cite_note-USDA-VitK-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Vitamin K has several roles: an essential nutrient absorbed from food, a product synthesized and marketed as part of a multi-vitamin or as a single-vitamin dietary supplement, and a prescription medication for specific purposes.<sup id="cite_ref-ods_1-2" class="reference"><a href="#cite_note-ods-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Dietary_recommendations">Dietary recommendations</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=2" title="Edit section: Dietary recommendations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The US <a href="/wiki/National_Academy_of_Medicine" title="National Academy of Medicine">National Academy of Medicine</a> does not distinguish between K<sub>1</sub> and K<sub>2</sub> – both are counted as vitamin K. When recommendations were last updated in 1998, sufficient information was not available to establish an <a href="/wiki/Estimated_Average_Requirement" class="mw-redirect" title="Estimated Average Requirement">estimated average requirement</a> or <a href="/wiki/Recommended_Dietary_Allowance" class="mw-redirect" title="Recommended Dietary Allowance">recommended dietary allowance</a>, terms that exist for most vitamins. In instances such as these, the academy defines <a href="/wiki/Adequate_intake" class="mw-redirect" title="Adequate intake">adequate intakes</a> (AIs) as amounts that appear to be sufficient to maintain good health, with the understanding that at some later date, AIs will be replaced by more exact information. The current AIs for adult women and men ages 19 and older are 90 and 120 μg/day, respectively, for pregnancy is 90 μg/day, and for lactation is 90 μg/day. For infants up to 12 months, the AI is 2.0–2.5 μg/day; for children ages 1–18 years the AI increases with age from 30 to 75 μg/day. As for safety, the academy sets <a href="/wiki/Tolerable_upper_intake_level" class="mw-redirect" title="Tolerable upper intake level">tolerable upper intake levels</a> (known as "upper limits") for vitamins and minerals when evidence is sufficient. Vitamin K has no upper limit, as human data for adverse effects from high doses are not sufficient.<sup id="cite_ref-DRItext_5-1" class="reference"><a href="#cite_note-DRItext-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>In the European Union, adequate intake is defined the same way as in the US. For women and men over age 18 the adequate intake is set at 70 μg/day, for pregnancy 70 μg/day, and for lactation 70 μg/day. For children ages 1–17 years, adequate intake values increase with age from 12 to 65 μg/day.<sup id="cite_ref-EFSAAIs_8-0" class="reference"><a href="#cite_note-EFSAAIs-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Japan set adequate intakes for adult women at 65 μg/day and for men at 75 μg/day.<sup id="cite_ref-JapanDRI_9-0" class="reference"><a href="#cite_note-JapanDRI-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> The European Union and Japan also reviewed safety and concluded – as had the United States – that there was insufficient evidence to set an upper limit for vitamin K.<sup id="cite_ref-JapanDRI_9-1" class="reference"><a href="#cite_note-JapanDRI-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EFSA_10-0" class="reference"><a href="#cite_note-EFSA-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>For US food and dietary supplement labeling purposes, the amount in a serving is expressed as a percentage of daily value. For vitamin K labeling purposes, 100% of the daily value was 80 μg, but on 27 May 2016 it was revised upwards to 120 μg, to bring it into agreement with the highest value for adequate intake.<sup id="cite_ref-FedReg_11-0" class="reference"><a href="#cite_note-FedReg-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Compliance with the updated labeling regulations was required by 1 January 2020 for manufacturers with <a href="/wiki/US$" class="mw-redirect" title="US$">US$</a>10 million or more in annual food sales, and by 1 January 2021 for manufacturers with lower volume food sales.<sup id="cite_ref-FDAdelay_13-0" class="reference"><a href="#cite_note-FDAdelay-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> A table of the old and new adult daily values is provided at <a href="/wiki/Reference_Daily_Intake" title="Reference Daily Intake">Reference Daily Intake</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Fortification">Fortification</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=3" title="Edit section: Fortification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>According to the Global Fortification Data Exchange, vitamin K deficiency is so rare that no countries require that foods be fortified.<sup id="cite_ref-Map_15-0" class="reference"><a href="#cite_note-Map-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> does not have recommendations on vitamin K fortification.<sup id="cite_ref-WHOfortif_16-0" class="reference"><a href="#cite_note-WHOfortif-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=4" title="Edit section: Sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vitamin K<sub>1</sub> is primarily from plants, especially leafy green vegetables. Small amounts are provided by animal-sourced foods. Vitamin K<sub>2</sub> is primarily from animal-sourced foods, with poultry and eggs much better sources than beef, pork or fish.<sup id="cite_ref-USDA-VitK_7-1" class="reference"><a href="#cite_note-USDA-VitK-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> One exception to the latter is <i><a href="/wiki/Natt%C5%8D" title="Nattō">nattō</a></i>, which is made from bacteria-fermented soybeans. It is a rich food source of vitamin K<sub>2</sub> variant MK-7, made by the bacteria.<sup id="cite_ref-Tarvainen2019_17-0" class="reference"><a href="#cite_note-Tarvainen2019-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Vitamin_K1">Vitamin K<sub>1</sub></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=5" title="Edit section: Vitamin K1"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1088965794">@media(min-width:720px){.mw-parser-output .columns-start .column{float:left;min-width:20em}.mw-parser-output .columns-2 .column{width:50%}.mw-parser-output .columns-3 .column{width:33.3%}.mw-parser-output .columns-4 .column{width:25%}.mw-parser-output .columns-5 .column{width:20%}}</style><div class="columns-start columns-3"><div class="column"> <table class="wikitable"> <tbody><tr> <th>Plant-sourced<sup id="cite_ref-USDA-VitK_7-2" class="reference"><a href="#cite_note-USDA-VitK-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </th> <th>Amount K<sub>1</sub><br /> (μg / measure) </th></tr> <tr> <td><a href="/wiki/Collard_(plant)" title="Collard (plant)">Collard greens</a> boiled, drained, <style data-mw-deduplicate="TemplateStyles:r1154941027">.mw-parser-output .frac{white-space:nowrap}.mw-parser-output .frac .num,.mw-parser-output .frac .den{font-size:80%;line-height:0;vertical-align:super}.mw-parser-output .frac .den{vertical-align:sub}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>530 </td></tr> <tr> <td><a href="/wiki/Spinach" title="Spinach">Spinach</a> boiled, drained, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>445 </td></tr> <tr> <td><a href="/wiki/Turnip_greens" class="mw-redirect" title="Turnip greens">Turnip greens</a> boiled, drained, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>425 </td></tr> <tr> <td><a href="/wiki/Spinach" title="Spinach">Spinach</a> raw, 1 cup</td> <td>145 </td></tr> <tr> <td><a href="/wiki/Brussels_sprout" title="Brussels sprout">Brussels sprouts</a> boiled, drained, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>110 </td></tr> <tr> <td><a href="/wiki/Kale" title="Kale">Kale</a> raw, 1 cup</td> <td>82 </td></tr> <tr> <td><a href="/wiki/Broccoli" title="Broccoli">Broccoli</a> boiled, drained, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>81 </td></tr> <tr> <td><a href="/wiki/Asparagus" title="Asparagus">Asparagus</a> boiled, drained, 4 spears</td> <td>48 </td></tr> <tr> <td><a href="/wiki/Kiwifruit" title="Kiwifruit">Kiwifruit</a> peeled, sliced, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>36 </td></tr> <tr> <td><a href="/wiki/Chinese_cabbage" title="Chinese cabbage">Chinese cabbage</a> cooked, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>29 </td></tr> <tr> <td><a href="/wiki/Blueberries" class="mw-redirect" title="Blueberries">Blueberries</a> frozen, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>21 </td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1088965794"></div><div class="column"> <table class="wikitable"> <tbody><tr> <th>Plant-sourced<sup id="cite_ref-USDA-VitK_7-3" class="reference"><a href="#cite_note-USDA-VitK-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </th> <th>Amount K<sub>1</sub><br /> (μg / measure) </th></tr> <tr> <td><a href="/wiki/Hazelnuts" class="mw-redirect" title="Hazelnuts">Hazelnuts</a> chopped, 1 cup</td> <td>16 </td></tr> <tr> <td><a href="/wiki/Grapes" class="mw-redirect" title="Grapes">Grapes</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>11 </td></tr> <tr> <td><a href="/wiki/Tomato" title="Tomato">Tomato</a> products, 1 cup</td> <td>9.2 </td></tr> <tr> <td><a href="/wiki/Olive_oil" title="Olive oil">Olive oil</a>, 1 tablespoon</td> <td>8.1 </td></tr> <tr> <td><a href="/wiki/Zucchini" title="Zucchini">Zucchini</a> boiled, drained, 1.0 cup</td> <td>7.6 </td></tr> <tr> <td><a href="/wiki/Mango" title="Mango">Mango</a> pieces, 1 cup</td> <td>6.9 </td></tr> <tr> <td><a href="/wiki/Pear" title="Pear">Pears</a>, pieces, 1 cup</td> <td>6.2 </td></tr> <tr> <td><a href="/wiki/Potato" title="Potato">Potato</a> baked, including skin, one</td> <td>6.0 </td></tr> <tr> <td><a href="/wiki/Sweet_potato" title="Sweet potato">Sweet potato</a> baked, one</td> <td>2.6 </td></tr> <tr> <td><a href="/wiki/Bread" title="Bread">Bread</a> whole wheat, 1 slice</td> <td>2.5 </td></tr> <tr> <td><a href="/wiki/Bread" title="Bread">Bread</a> white, 1 slice</td> <td>2.2 </td></tr> <tr> <td><i><a href="/wiki/Natt%C5%8D" title="Nattō">Nattō</a></i>, 100 g<sup id="cite_ref-Schurgers2000_18-0" class="reference"><a href="#cite_note-Schurgers2000-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup></td> <td>34.7 </td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1088965794"></div><div class="column"> <table class="wikitable"> <tbody><tr> <th>Animal-sourced<sup id="cite_ref-USDA-VitK_7-4" class="reference"><a href="#cite_note-USDA-VitK-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </th> <th>Amount K<sub>1</sub><br /> (μg / measure) </th></tr> <tr> <td><a href="/wiki/Chicken_as_food" title="Chicken as food">Chicken</a>, 113g (4 oz)</td> <td>2.7–3.3 </td></tr> <tr> <td><a href="/wiki/Mollusk" class="mw-redirect" title="Mollusk">Mollusks</a>, 113g (4 oz)</td> <td>2.2 </td></tr> <tr> <td><a href="/wiki/Cheese" title="Cheese">Cheese</a> diced, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1154941027"><span class="frac"><span class="num">1</span>⁄<span class="den">2</span></span> cup</td> <td>1.4–1.7 </td></tr> <tr> <td><a href="/wiki/Beef" title="Beef">Beef</a>, 113g (4 oz)</td> <td>0.9 </td></tr> <tr> <td><a href="/wiki/Pork" title="Pork">Pork</a> sausage, 113g (4 oz)</td> <td>0.9 </td></tr> <tr> <td><a href="/wiki/Yogurt" title="Yogurt">Yogurt</a> whole milk, 1 cup</td> <td>0.4 </td></tr> <tr> <td><a href="/wiki/Milk" title="Milk">Milk</a> whole or low fat, 1 cup</td> <td>0.2 </td></tr> <tr> <td><a href="/wiki/Fish" title="Fish">Fish</a>, 113g (4 oz)</td> <td>0.1 </td></tr> <tr> <td><a href="/wiki/Egg_as_food" class="mw-redirect" title="Egg as food">Eggs</a>, one</td> <td>0.1 </td></tr> <tr> <td><a href="/wiki/Human_milk" class="mw-redirect" title="Human milk">Human milk</a>, 1 liter</td> <td>0.85–9.2 (median 2.5)<sup id="cite_ref-Mihatsch2016_19-0" class="reference"><a href="#cite_note-Mihatsch2016-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> </div><div style="clear: both"></div></div> <div class="mw-heading mw-heading3"><h3 id="Vitamin_K2">Vitamin K<sub>2</sub></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=6" title="Edit section: Vitamin K2"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Vitamin_K2#Dietary_sources" title="Vitamin K2">Vitamin K2 § Dietary sources</a></div> <p>Animal-sourced foods are a source of vitamin K<sub>2</sub>.<sup id="cite_ref-Schurgers2000_18-1" class="reference"><a href="#cite_note-Schurgers2000-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Elder2006_20-0" class="reference"><a href="#cite_note-Elder2006-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The MK-4 form is from conversion of plant-sourced vitamin K<sub>1</sub> in various tissues in the body.<sup id="cite_ref-Shearer2008_21-0" class="reference"><a href="#cite_note-Shearer2008-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1088965794"><div class="columns-start columns-3"><div class="column"> <table class="wikitable"> <tbody><tr> <th>Animal Source<sup id="cite_ref-Schurgers2000_18-2" class="reference"><a href="#cite_note-Schurgers2000-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </th> <th>Amount K<sub>2</sub><br /> MK-4 to MK-7<br /> (μg / 100 g) </th></tr> <tr> <td><a href="/wiki/Domestic_goose" title="Domestic goose">Goose</a></td> <td>31 </td></tr> <tr> <td><a href="/wiki/Chicken_as_food" title="Chicken as food">Chicken</a></td> <td>8.9 </td></tr> <tr> <td><a href="/wiki/Pork" title="Pork">Pork</a></td> <td>2.1 </td></tr> <tr> <td><a href="/wiki/Beef" title="Beef">Beef</a></td> <td>1.1 </td></tr> <tr> <td><a href="/wiki/Salmon" title="Salmon">Salmon</a></td> <td>0.5 </td></tr> <tr> <td><a href="/wiki/Egg_yolk" class="mw-redirect" title="Egg yolk">Egg yolk</a></td> <td>32 </td></tr> <tr> <td><a href="/wiki/Egg_white" title="Egg white">Egg white</a></td> <td>0.9 </td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1088965794"></div><div class="column"> <table class="wikitable"> <tbody><tr> <th>Animal Source<sup id="cite_ref-Schurgers2000_18-3" class="reference"><a href="#cite_note-Schurgers2000-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Elder2006_20-1" class="reference"><a href="#cite_note-Elder2006-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </th> <th>Amount K<sub>2</sub><br /> MK-4 to MK-7<br /> (μg / 100 g) </th></tr> <tr> <td><a href="/wiki/Milk" title="Milk">Milk</a>, whole</td> <td>0.9 </td></tr> <tr> <td><a href="/wiki/Milk" title="Milk">Milk</a>, skim</td> <td>0.0 </td></tr> <tr> <td><a href="/wiki/Yogurt" title="Yogurt">Yogurt</a>, whole milk</td> <td>0.9 </td></tr> <tr> <td><a href="/wiki/Butter" title="Butter">Butter</a></td> <td>15 </td></tr> <tr> <td><a href="/wiki/Cheese" title="Cheese">Cheese</a>, hard</td> <td>8–10 </td></tr> <tr> <td><a href="/wiki/Cheese" title="Cheese">Cheese</a>, soft</td> <td>3.6 </td></tr></tbody></table> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1088965794"></div><div class="column"> <table class="wikitable"> <tbody><tr> <th>Fermented Source<sup id="cite_ref-Tarvainen2019_17-1" class="reference"><a href="#cite_note-Tarvainen2019-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </th> <th>Amount K<sub>2</sub><br /> MK-4 to MK-7<br /> (μg / 100 g) </th></tr> <tr> <td><i><a href="/wiki/Natt%C5%8D" title="Nattō">Nattō</a></i></td> <td>1103 (90% MK-7) </td></tr></tbody></table> </div><div style="clear: both"></div></div> <div class="mw-heading mw-heading2"><h2 id="Vitamin_K_deficiency">Vitamin K deficiency</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=7" title="Edit section: Vitamin K deficiency"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Vitamin_K_deficiency" title="Vitamin K deficiency">Vitamin K deficiency</a></div> <p>Because vitamin K aids mechanisms for blood clotting, its deficiency may lead to reduced blood clotting, and in severe cases, can result in reduced clotting, increased bleeding, and increased <a href="/wiki/Prothrombin_time" title="Prothrombin time">prothrombin time</a>.<sup id="cite_ref-Higdon_2-3" class="reference"><a href="#cite_note-Higdon-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DRItext_5-2" class="reference"><a href="#cite_note-DRItext-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Normal diets are usually not deficient in vitamin K, indicating that deficiency is uncommon in healthy children and adults.<sup id="cite_ref-PKIN2020VitK_4-3" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> An exception may be infants who are at an increased risk of deficiency regardless of the vitamin status of the mother during pregnancy and breast feeding due to poor transfer of the vitamin to the placenta and low amounts of the vitamin in breast milk.<sup id="cite_ref-Mihatsch2016_19-1" class="reference"><a href="#cite_note-Mihatsch2016-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Secondary deficiencies can occur in people who consume adequate amounts, but have malabsorption conditions, such as <a href="/wiki/Cystic_fibrosis" title="Cystic fibrosis">cystic fibrosis</a> or chronic pancreatitis, and in people who have <a href="/wiki/Liver_disease" title="Liver disease">liver damage or disease</a>.<sup id="cite_ref-Higdon_2-4" class="reference"><a href="#cite_note-Higdon-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Secondary vitamin K deficiency can also occur in people who have a prescription for a vitamin K antagonist drug, such as warfarin.<sup id="cite_ref-Higdon_2-5" class="reference"><a href="#cite_note-Higdon-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PKIN2020VitK_4-4" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> A drug associated with increased risk of vitamin K deficiency is <a href="/wiki/Cefamandole" title="Cefamandole">cefamandole</a>, although the mechanism is unknown.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=8" title="Edit section: Medical uses"><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:Vitamina_K_20220202_122653.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Vitamina_K_20220202_122653.jpg/220px-Vitamina_K_20220202_122653.jpg" decoding="async" width="220" height="245" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Vitamina_K_20220202_122653.jpg/330px-Vitamina_K_20220202_122653.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b7/Vitamina_K_20220202_122653.jpg/440px-Vitamina_K_20220202_122653.jpg 2x" data-file-width="763" data-file-height="850" /></a><figcaption>Injectable solutions of vitamin K</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Treating_vitamin_deficiency_in_newborns">Treating vitamin deficiency in newborns</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=9" title="Edit section: Treating vitamin deficiency in newborns"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vitamin K is given as an injection to newborns to prevent <a href="/wiki/Vitamin_K_deficiency_bleeding" title="Vitamin K deficiency bleeding">vitamin K deficiency bleeding</a>.<sup id="cite_ref-Mihatsch2016_19-2" class="reference"><a href="#cite_note-Mihatsch2016-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> The blood clotting factors of newborn babies are roughly 30–60% that of adult values; this appears to be a consequence of poor transfer of the vitamin across the placenta, and thus low fetal plasma vitamin K.<sup id="cite_ref-Mihatsch2016_19-3" class="reference"><a href="#cite_note-Mihatsch2016-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Occurrence of vitamin K deficiency bleeding in the first week of the infant's life is estimated at between 1 in 60 and 1 in 250.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Human_milk" class="mw-redirect" title="Human milk">Human milk</a> contains 0.85–9.2 μg/L (median 2.5 μg/L) of vitamin K<sub>1</sub>, while infant formula is formulated in range of 24–175 μg/L.<sup id="cite_ref-Mihatsch2016_19-4" class="reference"><a href="#cite_note-Mihatsch2016-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Late onset bleeding, with onset 2 to 12 weeks after birth, can be a consequence of exclusive breastfeeding, especially if there was no preventive treatment.<sup id="cite_ref-Mihatsch2016_19-5" class="reference"><a href="#cite_note-Mihatsch2016-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Late onset prevalence reported at 35 cases per 100,000 live births in infants who had not received prophylaxis at or shortly after birth.<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> Vitamin K deficiency bleeding occurs more frequently in the Asian population compared to the Caucasian population.<sup id="cite_ref-Mihatsch2016_19-6" class="reference"><a href="#cite_note-Mihatsch2016-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Bleeding in infants due to vitamin K deficiency can be severe, leading to hospitalization, <a href="/wiki/Brain_damage" class="mw-redirect" title="Brain damage">brain damage</a>, and death. Intramuscular injection, typically given shortly after birth, is more effective in preventing vitamin K deficiency bleeding than oral administration, which calls for weekly dosing up to three months of age.<sup id="cite_ref-Mihatsch2016_19-7" class="reference"><a href="#cite_note-Mihatsch2016-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Managing_warfarin_therapy">Managing warfarin therapy</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=10" title="Edit section: Managing warfarin therapy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a> is an <a href="/wiki/Anticoagulant" title="Anticoagulant">anticoagulant</a> drug. It functions by inhibiting an enzyme that is responsible for recycling vitamin K to a functional state. As a consequence, proteins that should be modified by vitamin K are not, including proteins essential to blood clotting, and are thus not functional.<sup id="cite_ref-Whitlon_25-0" class="reference"><a href="#cite_note-Whitlon-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> The purpose of the drug is to reduce risk of inappropriate blood clotting, which can have serious, potentially fatal consequences.<sup id="cite_ref-Higdon_2-6" class="reference"><a href="#cite_note-Higdon-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The proper anticoagulant action of warfarin is a function of vitamin K intake and drug dose. Due to differing absorption of the drug and amounts of vitamin K in the diet, dosing must be monitored and customized for each patient.<sup id="cite_ref-Gong2011_26-0" class="reference"><a href="#cite_note-Gong2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Some foods are so high in vitamin K<sub>1</sub> that medical advice is to avoid those (examples: collard greens, spinach, turnip greens) entirely, and for foods with a modestly high vitamin content, keep consumption as consistent as possible, so that the combination of vitamin intake and warfarin keep the anti-clotting activity in the therapeutic range.<sup id="cite_ref-auto1_27-0" class="reference"><a href="#cite_note-auto1-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Vitamin K is a treatment for bleeding events caused by overdose of the drug.<sup id="cite_ref-Tomaselli2017_28-0" class="reference"><a href="#cite_note-Tomaselli2017-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> The vitamin can be administered by mouth, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenously</a> or <a href="/wiki/Subcutaneous_tissue" title="Subcutaneous tissue">subcutaneously</a>.<sup id="cite_ref-Tomaselli2017_28-1" class="reference"><a href="#cite_note-Tomaselli2017-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Oral vitamin K is used in situations when a person's <a href="/wiki/International_normalised_ratio" class="mw-redirect" title="International normalised ratio">International normalized ratio</a> is greater than 10 but there is no active bleeding.<sup id="cite_ref-auto1_27-1" class="reference"><a href="#cite_note-auto1-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> The newer anticoagulants <a href="/wiki/Apixaban" title="Apixaban">apixaban</a>, <a href="/wiki/Dabigatran" title="Dabigatran">dabigatran</a> and <a href="/wiki/Rivaroxaban" title="Rivaroxaban">rivaroxaban</a> are not vitamin K antagonists.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Treating_rodenticide_poisoning">Treating rodenticide poisoning</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=11" title="Edit section: Treating rodenticide poisoning"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Coumarin" title="Coumarin">Coumarin</a> is used in the pharmaceutical industry as a precursor reagent in the synthesis of a number of synthetic anticoagulant pharmaceuticals.<sup id="cite_ref-pubchem19_31-0" class="reference"><a href="#cite_note-pubchem19-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> One subset, <a href="/wiki/4-hydroxycoumarins" class="mw-redirect" title="4-hydroxycoumarins">4-hydroxycoumarins</a>, act as <a href="/wiki/Vitamin_K_antagonist" title="Vitamin K antagonist">vitamin K antagonists</a>. They block the regeneration and recycling of vitamin K. Some of the 4-hydroxycoumarin anticoagulant class of chemicals are designed to have high potency and long residence times in the body, and these are used specifically as second generation <a href="/wiki/Rodenticide" title="Rodenticide">rodenticides</a> ("rat poison"). Death occurs after a period of several days to two weeks, usually from internal hemorrhaging.<sup id="cite_ref-pubchem19_31-1" class="reference"><a href="#cite_note-pubchem19-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> For humans, and for animals that have consumed either the rodenticide or rats poisoned by the rodenticide, treatment is prolonged administration of large amounts of vitamin K.<sup id="cite_ref-Bateman2016_32-0" class="reference"><a href="#cite_note-Bateman2016-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> This dosing must sometimes be continued for up to nine months in cases of poisoning by "<a href="/wiki/Superwarfarin" title="Superwarfarin">superwarfarin</a>" rodenticides such as <a href="/wiki/Brodifacoum" title="Brodifacoum">brodifacoum</a>. Oral vitamin K<sub>1</sub> is preferred over other vitamin K<sub>1</sub> routes of administration because it has fewer side effects.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Methods_of_assessment">Methods of assessment</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=12" title="Edit section: Methods of assessment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>An increase in <a href="/wiki/Prothrombin_time" title="Prothrombin time">prothrombin time</a>, a coagulation assay, has been used as an indicator of vitamin K status, but it lacks sufficient sensitivity and specificity for this application.<sup id="cite_ref-Card2020_35-0" class="reference"><a href="#cite_note-Card2020-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Serum phylloquinone is the most commonly used marker of vitamin K status. Concentrations <0.15 μg/L are indicative of deficiency. Disadvantages include exclusion of the other vitamin K vitamers and interference from recent dietary intake.<sup id="cite_ref-Card2020_35-1" class="reference"><a href="#cite_note-Card2020-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Vitamin K is required for the gamma-carboxylation of specific glutamic acid residues within the Gla domain of the 17 vitamin K–dependent proteins. Thus, a rise in uncarboxylated versions of these proteins is an indirect but sensitive and specific marker for vitamin K deficiency. If uncarboxylated prothrombin is being measured, this "Protein induced by Vitamin K Absence/antagonism (PIVKA-II)" is elevated in vitamin K deficiency. </p><p>The test is used to assess risk of vitamin K–deficient bleeding in newborn infants.<sup id="cite_ref-Card2020_35-2" class="reference"><a href="#cite_note-Card2020-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Osteocalcin" title="Osteocalcin">Osteocalcin</a> is involved in calcification of bone tissue. The ratio of uncarboxylated osteocalcin to carboxylated osteocalcin increases with vitamin K deficiency. Vitamin K2 has been shown to lower this ratio and improve <a href="/wiki/Lumbar" title="Lumbar">lumbar</a> vertebrae <a href="/wiki/Bone_mineral_density" class="mw-redirect" title="Bone mineral density">bone mineral density</a>.<sup id="cite_ref-Su2019_36-0" class="reference"><a href="#cite_note-Su2019-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Matrix Gla protein must undergo vitamin K dependent phosphorylation and carboxylation. Elevated plasma concentration of dephosphorylated, uncarboxylated MGP is indicative of vitamin K deficiency.<sup id="cite_ref-Chen2019_37-0" class="reference"><a href="#cite_note-Chen2019-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Side_effects">Side effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=13" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>No known toxicity is associated with high oral doses of the vitamin K<sub>1</sub> or vitamin K<sub>2</sub> forms of vitamin K, so regulatory agencies from US, Japan and European Union concur that no <a href="/wiki/Tolerable_upper_intake_level#Current_recommendations" class="mw-redirect" title="Tolerable upper intake level">tolerable upper intake levels</a> needs to be set.<sup id="cite_ref-DRItext_5-3" class="reference"><a href="#cite_note-DRItext-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-JapanDRI_9-2" class="reference"><a href="#cite_note-JapanDRI-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EFSA_10-1" class="reference"><a href="#cite_note-EFSA-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> However, vitamin K<sub>1</sub> has been associated with severe adverse reactions such as <a href="/wiki/Bronchospasm" title="Bronchospasm">bronchospasm</a> and <a href="/wiki/Cardiac_arrest" title="Cardiac arrest">cardiac arrest</a> when given intravenously. The reaction is described as a nonimmune-mediated <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylactoid reaction</a>, with incidence of 3 per 10,000 treatments. The majority of reactions occurred when polyoxyethylated <a href="/wiki/Castor_oil" title="Castor oil">castor oil</a> was used as the solubilizing agent.<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> </p> <div class="mw-heading mw-heading2"><h2 id="Non-human_uses">Non-human uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=14" title="Edit section: Non-human uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Menadione, a natural<sup id="cite_ref-nat_39-0" class="reference"><a href="#cite_note-nat-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> compound sometimes referred to as vitamin K<sub>3</sub>, is used in the <a href="/wiki/Pet_food" title="Pet food">pet food</a> industry because once consumed it is converted to vitamin K<sub>2</sub>.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> The US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> has banned this form from sale as a human <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> because overdoses have been shown to cause <a href="/wiki/Allergic_reaction" class="mw-redirect" title="Allergic reaction">allergic reactions</a>, <a href="/wiki/Hemolytic_anemia" title="Hemolytic anemia">hemolytic anemia</a>, and <a href="/wiki/Cytotoxicity" title="Cytotoxicity">cytotoxicity</a> in liver cells.<sup id="cite_ref-Higdon_2-7" class="reference"><a href="#cite_note-Higdon-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/4-Amino-2-methyl-1-naphthol" title="4-Amino-2-methyl-1-naphthol">4-amino-2-methyl-1-naphthol</a> ("K<sub>5</sub>") is not natural and hence not a "vitamin". Research with "K<sub>5</sub>" suggests it may inhibit <a href="/wiki/Fungal" class="mw-redirect" title="Fungal">fungal</a> growth in fruit juices.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=15" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size 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>Vitamin K<sub>1</sub> (phylloquinone) – both forms of the vitamin contain a functional <a href="/wiki/Naphthoquinone" title="Naphthoquinone">naphthoquinone</a> ring and an <a href="/wiki/Aliphatic" class="mw-redirect" title="Aliphatic">aliphatic</a> side chain. Phylloquinone has a <a href="/wiki/Phytane" title="Phytane">phytyl</a> side chain.</figcaption></figure> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Menaquinone.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Menaquinone.svg/220px-Menaquinone.svg.png" decoding="async" width="220" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Menaquinone.svg/330px-Menaquinone.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Menaquinone.svg/440px-Menaquinone.svg.png 2x" data-file-width="1809" data-file-height="755" /></a><figcaption>Vitamin K<sub>2</sub> (menaquinone). In menaquinone, the side chain is composed of a varying number of <a href="/wiki/Isoprene#isoprenoids" title="Isoprene">isoprenoid</a> residues. The most common number of these residues is four, since animal <a href="/wiki/Enzyme" title="Enzyme">enzymes</a> normally produce menaquinone-4 from plant phylloquinone.</figcaption></figure> <p>The structure of phylloquinone, Vitamin K<sub>1</sub>, is marked by the presence of a <a href="/wiki/Phytyl" class="mw-redirect" title="Phytyl">phytyl</a> sidechain.<sup id="cite_ref-DRItext_5-4" class="reference"><a href="#cite_note-DRItext-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Vitamin K<sub>1</sub> has an (E) trans double bond responsible for its biological activity, and two chiral centers on the phytyl sidechain.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Vitamin K<sub>1</sub> appears as a yellow viscous liquid at room temperature due to its absorption of violet light in the UV-visible spectra obtained by <a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">ultraviolet–visible spectroscopy</a>.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> The structures of menaquinones, vitamin K<sub>2</sub>, are marked by the polyisoprenyl side chain present in the molecule that can contain four to 13 isoprenyl units. MK-4 is the most common form.<sup id="cite_ref-DRItext_5-5" class="reference"><a href="#cite_note-DRItext-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> The large size of Vitamin K<sub>1</sub> gives many different peaks in mass spectroscopy, most of which involve derivatives of the naphthoquinone ring base and the alkyl side chain.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Phytomenadione_(vitamin_K1).jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Phytomenadione_%28vitamin_K1%29.jpg/220px-Phytomenadione_%28vitamin_K1%29.jpg" decoding="async" width="220" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Phytomenadione_%28vitamin_K1%29.jpg/330px-Phytomenadione_%28vitamin_K1%29.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6d/Phytomenadione_%28vitamin_K1%29.jpg/440px-Phytomenadione_%28vitamin_K1%29.jpg 2x" data-file-width="3501" data-file-height="1940" /></a><figcaption>A sample of phytomenadione for injection, also called phylloquinone</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Conversion_of_vitamin_K1_to_vitamin_K2">Conversion of vitamin K<sub>1</sub> to vitamin K<sub>2</sub></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=16" title="Edit section: Conversion of vitamin K1 to vitamin K2"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Vitamin_K2" title="Vitamin K2">Vitamin K<sub>2</sub></a></div> <p>In animals, the MK-4 form of vitamin K<sub>2</sub> is produced by conversion of vitamin K<sub>1</sub> in the <a href="/wiki/Testes" class="mw-redirect" title="Testes">testes</a>, <a href="/wiki/Pancreas" title="Pancreas">pancreas</a>, and <a href="/wiki/Artery" title="Artery">arterial</a> walls.<sup id="cite_ref-Shearer2008_21-1" class="reference"><a href="#cite_note-Shearer2008-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> While major questions still surround the biochemical pathway for this transformation, the conversion is not dependent on <a href="/wiki/Gut_bacteria" class="mw-redirect" title="Gut bacteria">gut bacteria</a>, as it occurs in germ-free rats<sup id="cite_ref-ReferenceB_45-0" class="reference"><a href="#cite_note-ReferenceB-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> and in parenterally administered K<sub>1</sub> in rats.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> There is evidence that the conversion proceeds by removal of the phytyl tail of K<sub>1</sub> to produce menadione (also referred to as vitamin K<sub>3</sub>) as an intermediate, which is then <a href="/wiki/Prenylation" title="Prenylation">prenylated</a> to produce MK-4.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Physiology">Physiology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=17" title="Edit section: Physiology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In animals, vitamin K is involved in the <a href="/wiki/Carboxylation" title="Carboxylation">carboxylation</a> of certain <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> residues in proteins to form <a href="/wiki/Gamma-carboxyglutamate" class="mw-redirect" title="Gamma-carboxyglutamate">gamma-carboxyglutamate</a> (Gla) residues. The modified residues are often (but not always) situated within specific <a href="/wiki/Protein_domains" class="mw-redirect" title="Protein domains">protein domains</a> called <a href="/wiki/Gla_domain" title="Gla domain">Gla domains</a>. Gla residues are usually involved in binding <a href="/wiki/Calcium_in_biology" title="Calcium in biology">calcium</a>, and are essential for the biological activity of all known Gla proteins.<sup id="cite_ref-Furie_49-0" class="reference"><a href="#cite_note-Furie-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Gla_domain#Human_proteins_containing_this_domain" title="Gla domain">17 human proteins with Gla domains</a> have been discovered; they play key roles in the regulation of three physiological processes: </p> <ul><li><a href="/wiki/Blood_coagulation" class="mw-redirect" title="Blood coagulation">Blood coagulation</a>: <a href="/wiki/Prothrombin" class="mw-redirect" title="Prothrombin">prothrombin</a> (factor II), <a href="/wiki/Factor_VII" title="Factor VII">factors VII</a>, <a href="/wiki/Factor_IX" title="Factor IX">IX</a>, and <a href="/wiki/Factor_X" title="Factor X">X</a>, and <a href="/wiki/Protein_C" title="Protein C">proteins C</a>, <a href="/wiki/Protein_S" title="Protein S">S</a>, and <a href="/wiki/Protein_Z" title="Protein Z">Z</a><sup id="cite_ref-Mann_50-0" class="reference"><a href="#cite_note-Mann-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Bone_metabolism" class="mw-redirect" title="Bone metabolism">Bone metabolism</a>: <a href="/wiki/Osteocalcin" title="Osteocalcin">osteocalcin</a>, <a href="/wiki/Matrix_Gla_protein" title="Matrix Gla protein">matrix Gla protein</a> (MGP),<sup id="cite_ref-Price_51-0" class="reference"><a href="#cite_note-Price-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Periostin" title="Periostin">periostin</a>,<sup id="cite_ref-Coutu_52-0" class="reference"><a href="#cite_note-Coutu-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> and Gla-rich protein.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup></li> <li>Vascular biology: Matrix Gla protein, <a href="/wiki/GAS6" title="GAS6">growth arrest – specific protein 6</a> (Gas6)<sup id="cite_ref-Hafizi_55-0" class="reference"><a href="#cite_note-Hafizi-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup></li> <li>Unknown functions: proline-rich γ-carboxyglutamyl proteins 1 and 2, and transmembrane γ-carboxy glutamyl proteins 3 and 4.<sup id="cite_ref-Kulman_56-0" class="reference"><a href="#cite_note-Kulman-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Absorption">Absorption</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=18" title="Edit section: Absorption"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vitamin K is absorbed through the <a href="/wiki/Jejunum" title="Jejunum">jejunum</a> and <a href="/wiki/Ileum" title="Ileum">ileum</a> in the <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a>. The process requires <a href="/wiki/Bile" title="Bile">bile</a> and <a href="/wiki/Pancreatic_juice" title="Pancreatic juice">pancreatic juices</a>. Estimates for absorption are on the order of 80% for vitamin K<sub>1</sub> in its free form (as a dietary supplement) but much lower when present in foods. For example, the absorption of vitamin K from kale and spinach – foods identified as having a high vitamin K content – are on the order of 4% to 17% regardless of whether raw or cooked.<sup id="cite_ref-PKIN2020VitK_4-5" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Less information is available for absorption of vitamin K<sub>2</sub> from foods.<sup id="cite_ref-PKIN2020VitK_4-6" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-DRItext_5-6" class="reference"><a href="#cite_note-DRItext-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>The intestinal membrane protein <a href="/wiki/NPC1L1" title="NPC1L1">Niemann–Pick C1-like 1</a> (NPC1L1) mediates cholesterol absorption. Animal studies show that it also factors into absorption of vitamins E and K<sub>1</sub>.<sup id="cite_ref-Yamanashi2017_57-0" class="reference"><a href="#cite_note-Yamanashi2017-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> The same study predicts potential interaction between SR-BI and CD36 proteins as well.<sup id="cite_ref-Yamanashi2017_57-1" class="reference"><a href="#cite_note-Yamanashi2017-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> The drug <a href="/wiki/Ezetimibe" title="Ezetimibe">ezetimibe</a> inhibits NPC1L1 causing a reduction in cholesterol absorption in humans, and in animal studies, also reduces vitamin E and vitamin K<sub>1</sub> absorption. An expected consequence would be that administration of ezetimibe to people who take warfarin (a vitamin K antagonist) would potentiate the warfarin effect. This has been confirmed in humans.<sup id="cite_ref-Yamanashi2017_57-2" class="reference"><a href="#cite_note-Yamanashi2017-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p> <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=Vitamin_K&action=edit&section=19" title="Edit section: Biochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Function_in_animals">Function in animals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=20" title="Edit section: Function in animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></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 section <b>is missing information</b> about invertebrates.<span class="hide-when-compact"> Please expand the section to include this information. Further details may exist on the <a href="/wiki/Talk:Vitamin_K" title="Talk:Vitamin K">talk page</a>.</span> <span class="date-container"><i>(<span class="date">January 2021</span>)</i></span></div></td></tr></tbody></table> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:K1_vitamin_Mechanism_of_Action.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/K1_vitamin_Mechanism_of_Action.svg/350px-K1_vitamin_Mechanism_of_Action.svg.png" decoding="async" width="350" height="147" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/K1_vitamin_Mechanism_of_Action.svg/525px-K1_vitamin_Mechanism_of_Action.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/K1_vitamin_Mechanism_of_Action.svg/700px-K1_vitamin_Mechanism_of_Action.svg.png 2x" data-file-width="471" data-file-height="198" /></a><figcaption>Cyclic mechanism of action of vitamin K</figcaption></figure> <div class="skin-invert-image"> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:308px;max-width:308px"><div class="trow"><div class="tsingle" style="width:152px;max-width:152px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Vitamin_K_reduziert.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Vitamin_K_reduziert.svg/150px-Vitamin_K_reduziert.svg.png" decoding="async" width="150" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Vitamin_K_reduziert.svg/225px-Vitamin_K_reduziert.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/59/Vitamin_K_reduziert.svg/300px-Vitamin_K_reduziert.svg.png 2x" data-file-width="217" data-file-height="186" /></a></span></div><div class="thumbcaption">Vitamin K <a href="/wiki/Hydroquinone" title="Hydroquinone">hydroquinone</a></div></div><div class="tsingle" style="width:152px;max-width:152px"><div class="thumbimage"><span typeof="mw:File"><a href="/wiki/File:Vitamin-K-Epoxid.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Vitamin-K-Epoxid.svg/150px-Vitamin-K-Epoxid.svg.png" decoding="async" width="150" height="129" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/18/Vitamin-K-Epoxid.svg/225px-Vitamin-K-Epoxid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/18/Vitamin-K-Epoxid.svg/300px-Vitamin-K-Epoxid.svg.png 2x" data-file-width="217" data-file-height="186" /></a></span></div><div class="thumbcaption">Vitamin K <a href="/wiki/Epoxide" title="Epoxide">epoxide</a></div></div></div><div class="trow" style="display:flex"><div class="thumbcaption">In both cases R represents the isoprenoid side chain.</div></div></div></div> </div> <p>Vitamin K is distributed differently within animals depending on its specific homologue. Vitamin K<sub>1</sub> is mainly present in the liver, heart and pancreas, while MK-4 is better represented in the kidneys, brain and pancreas. The liver also contains longer chain homologues MK-7 to MK-13.<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p><p>The function of vitamin K<sub>2</sub> in the animal cell is to add a <a href="/wiki/Carboxylic_acid" title="Carboxylic acid">carboxylic acid</a> <a href="/wiki/Functional_group" title="Functional group">functional group</a> to a <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a> (Glu) <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> residue in a <a href="/wiki/Protein" title="Protein">protein</a>, to form a <a href="/wiki/Gamma-carboxyglutamate" class="mw-redirect" title="Gamma-carboxyglutamate">gamma-carboxyglutamate</a> (Gla) residue. This is a somewhat uncommon <a href="/wiki/Posttranslational_modification" class="mw-redirect" title="Posttranslational modification">posttranslational modification</a> of the protein, which is then known as a <a href="/wiki/Gla_domain" title="Gla domain">"Gla protein"</a>. The presence of two −COOH (carboxylic acid) groups on the same carbon in the gamma-carboxyglutamate residue allows it to <a href="/wiki/Chelation" title="Chelation">chelate</a> <a href="/wiki/Calcium_ion" class="mw-redirect" title="Calcium ion">calcium ions</a>. The binding of calcium ions in this way very often triggers the function or binding of Gla-protein enzymes, such as the so-called vitamin K–dependent clotting factors discussed below.<sup id="cite_ref-InterPro_59-0" class="reference"><a href="#cite_note-InterPro-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p><p>Within the cell, vitamin K participates in a cyclic process. The vitamin undergoes electron <a href="/wiki/Redox" title="Redox">reduction</a> to a reduced form called vitamin K hydroquinone (quinol), catalyzed by the enzyme <a href="/wiki/Vitamin_K_epoxide_reductase" title="Vitamin K epoxide reductase">vitamin K epoxide reductase</a> (VKOR).<sup id="cite_ref-Oldenburg_60-0" class="reference"><a href="#cite_note-Oldenburg-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> Another enzyme then <a href="/wiki/Redox" title="Redox">oxidizes</a> vitamin K hydroquinone to allow carboxylation of Glu to Gla; this enzyme is called <a href="/wiki/Gamma-glutamyl_carboxylase" title="Gamma-glutamyl carboxylase">gamma-glutamyl carboxylase</a><sup id="cite_ref-Presnell_61-0" class="reference"><a href="#cite_note-Presnell-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> or the vitamin K–dependent carboxylase. The carboxylation reaction only proceeds if the carboxylase enzyme is able to oxidize vitamin K hydroquinone to vitamin K epoxide at the same time. The carboxylation and epoxidation reactions are said to be coupled. Vitamin K epoxide is then restored to vitamin K by VKOR. The reduction and subsequent reoxidation of vitamin K coupled with carboxylation of Glu is called the vitamin K cycle.<sup id="cite_ref-Stafford_62-0" class="reference"><a href="#cite_note-Stafford-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> Humans are rarely deficient in vitamin K because, in part, vitamin K<sub>2</sub> is continuously recycled in cells.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a> and other <a href="/wiki/4-hydroxycoumarins" class="mw-redirect" title="4-hydroxycoumarins">4-hydroxycoumarins</a> block the action of VKOR.<sup id="cite_ref-Whitlon_25-1" class="reference"><a href="#cite_note-Whitlon-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> This results in decreased concentrations of vitamin K and vitamin K hydroquinone in tissues, such that the carboxylation reaction catalyzed by the glutamyl carboxylase is inefficient. This results in the production of clotting factors with inadequate Gla. Without Gla on the <a href="/wiki/N-terminus" title="N-terminus">amino termini</a> of these factors, they no longer bind stably to the blood vessel <a href="/wiki/Endothelium" title="Endothelium">endothelium</a> and cannot activate <a href="/wiki/Clotting" class="mw-redirect" title="Clotting">clotting</a> to allow formation of a clot during tissue injury. As it is impossible to predict what dose of warfarin will give the desired degree of clotting suppression, warfarin treatment must be carefully monitored to avoid underdose and overdose.<sup id="cite_ref-Gong2011_26-1" class="reference"><a href="#cite_note-Gong2011-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Gamma-carboxyglutamate_proteins">Gamma-carboxyglutamate proteins</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=21" title="Edit section: Gamma-carboxyglutamate proteins"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Gla_domain" title="Gla domain">Gla domain</a></div> <p>The following human Gla-containing proteins ("Gla proteins") have been characterized to the level of primary structure: blood coagulation factors II (<a href="/wiki/Prothrombin" class="mw-redirect" title="Prothrombin">prothrombin</a>), VII, IX, and X, anticoagulant <a href="/wiki/Protein_C" title="Protein C">protein C</a> and <a href="/wiki/Protein_S" title="Protein S">protein S</a>, and the factor X-targeting <a href="/wiki/Protein_Z" title="Protein Z">protein Z</a>. The bone Gla protein <a href="/wiki/Osteocalcin" title="Osteocalcin">osteocalcin</a>, the calcification-inhibiting <a href="/wiki/Matrix_Gla_protein" title="Matrix Gla protein">matrix Gla protein</a> (MGP), the <a href="/wiki/Cell_growth" title="Cell growth">cell growth</a> regulating growth arrest specific gene 6 protein, and the four transmembrane Gla proteins, the function of which is at present unknown. The Gla domain is responsible for high-affinity binding of <a href="/wiki/Calcium_ions" class="mw-redirect" title="Calcium ions">calcium ions</a> (Ca<sup>2+</sup>) to Gla proteins, which is often necessary for their conformation, and always necessary for their function.<sup id="cite_ref-InterPro_59-1" class="reference"><a href="#cite_note-InterPro-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p><p>Gla proteins are known to occur in a wide variety of vertebrates: mammals, birds, reptiles, and fish. The <a href="/wiki/Venom" title="Venom">venom</a> of a number of <a href="/wiki/Snakes_of_Australia" title="Snakes of Australia">Australian snakes</a> acts by activating the human blood-clotting system. In some cases, activation is accomplished by snake Gla-containing enzymes that bind to the <a href="/wiki/Endothelium" title="Endothelium">endothelium</a> of human blood vessels and catalyze the conversion of procoagulant clotting factors into activated ones, leading to unwanted and potentially deadly clotting.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p><p>Another interesting class of invertebrate Gla-containing proteins is synthesized by the fish-hunting snail <i><a href="/wiki/Conus_geographus" title="Conus geographus">Conus geographus</a></i>.<sup id="cite_ref-Terlau_65-0" class="reference"><a href="#cite_note-Terlau-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> These snails produce a venom containing hundreds of neuroactive <a href="/wiki/Peptides" class="mw-redirect" title="Peptides">peptides</a>, or <a href="/wiki/Conotoxin" title="Conotoxin">conotoxins</a>, which is sufficiently toxic to kill an adult human. Several of the conotoxins contain two to five Gla residues.<sup id="cite_ref-Buczek_66-0" class="reference"><a href="#cite_note-Buczek-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Function_in_plants_and_cyanobacteria">Function in plants and cyanobacteria</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=22" title="Edit section: Function in plants and cyanobacteria"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vitamin K<sub>1</sub> is an important chemical in green plants (including land plants and green algae) and some species of <a href="/wiki/Cyanobacteria" title="Cyanobacteria">cyanobacteria</a>, where it functions as an <a href="/wiki/Electron_acceptor" title="Electron acceptor">electron acceptor</a> transferring one electron in <a href="/wiki/Photosystem_I" title="Photosystem I">photosystem I</a> during <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>.<sup id="cite_ref-Basset2017_67-0" class="reference"><a href="#cite_note-Basset2017-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> For this reason, vitamin K<sub>1</sub> is found in large quantities in the photosynthetic tissues of plants (green <a href="/wiki/Leaf" title="Leaf">leaves</a>, and dark green leafy vegetables such as <a href="/wiki/Romaine_lettuce" title="Romaine lettuce">romaine lettuce</a>, <a href="/wiki/Kale" title="Kale">kale</a>, and <a href="/wiki/Spinach" title="Spinach">spinach</a>), but it occurs in far smaller quantities in other plant tissues.<sup id="cite_ref-USDA-VitK_7-5" class="reference"><a href="#cite_note-USDA-VitK-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Basset2017_67-1" class="reference"><a href="#cite_note-Basset2017-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p><p>Detection of VKORC1 homologues active on the K<sub>1</sub>-epioxide suggest that K<sub>1</sub> may have a non-redox function in these organisms. In plants but not cyanobacteria, knockout of this gene show growth restriction similar to mutants lacking the ability to produce K<sub>1</sub>.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Function_in_other_bacteria">Function in other bacteria</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=23" title="Edit section: Function in other bacteria"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Many bacteria, including <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a></i> found in the <a href="/wiki/Large_intestine" title="Large intestine">large intestine</a>, can synthesize vitamin K<sub>2</sub> (MK-7 up to MK-11),<sup id="cite_ref-Bentley_69-0" class="reference"><a href="#cite_note-Bentley-69"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> but not vitamin K<sub>1</sub>. In the vitamin K<sub>2</sub> synthesizing bacteria, menaquinone transfers two <a href="/wiki/Electron" title="Electron">electrons</a> between two different small molecules, during oxygen-independent metabolic energy production processes (<a href="/wiki/Anaerobic_respiration" title="Anaerobic respiration">anaerobic respiration</a>).<sup id="cite_ref-Haddock_70-0" class="reference"><a href="#cite_note-Haddock-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> For example, a small molecule with an excess of electrons (also called an electron donor) such as <a href="/wiki/Lactic_acid" title="Lactic acid">lactate</a>, <a href="/wiki/Formate" title="Formate">formate</a>, or <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a>, with the help of an enzyme, passes two electrons to menaquinone. The menaquinone, with the help of another enzyme, then transfers these two electrons to a suitable oxidant, such as <a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a> or <a href="/wiki/Nitrate" title="Nitrate">nitrate</a> (also called an electron acceptor). Adding two electrons to <a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a> or <a href="/wiki/Nitrate" title="Nitrate">nitrate</a> converts the molecule to <a href="/wiki/Succinate" class="mw-redirect" title="Succinate">succinate</a> or <a href="/wiki/Nitrite" title="Nitrite">nitrite</a> plus <a href="/wiki/Water" title="Water">water</a>, respectively.<sup id="cite_ref-Haddock_70-1" class="reference"><a href="#cite_note-Haddock-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p><p>Some of these reactions generate a cellular energy source, <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a>, in a manner similar to <a href="/wiki/Eukaryotic" class="mw-redirect" title="Eukaryotic">eukaryotic</a> cell <a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a>, except the final electron acceptor is not <a href="/wiki/Molecular_oxygen" class="mw-redirect" title="Molecular oxygen">molecular oxygen</a>, but <a href="/wiki/Fumarate" class="mw-redirect" title="Fumarate">fumarate</a> or <a href="/wiki/Nitrate" title="Nitrate">nitrate</a>. In <a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a>, the final oxidant is <a href="/wiki/Molecular_oxygen" class="mw-redirect" title="Molecular oxygen">molecular oxygen</a>, which accepts four electrons from an electron donor such as <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a> to be converted to <a href="/wiki/Water" title="Water">water</a>. <i>E. coli</i>, as <a href="/wiki/Facultative_anaerobe" class="mw-redirect" title="Facultative anaerobe">facultative anaerobes</a>, can carry out both <a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a> and menaquinone-mediated anaerobic respiration.<sup id="cite_ref-Haddock_70-2" class="reference"><a href="#cite_note-Haddock-70"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=24" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In 1929, Danish scientist <a href="/wiki/Carl_Peter_Henrik_Dam" class="mw-redirect" title="Carl Peter Henrik Dam">Henrik Dam</a> investigated the role of <a href="/wiki/Cholesterol" title="Cholesterol">cholesterol</a> by feeding chickens a cholesterol-depleted diet.<sup id="cite_ref-Dam_71-0" class="reference"><a href="#cite_note-Dam-71"><span class="cite-bracket">[</span>71<span class="cite-bracket">]</span></a></sup> He initially replicated experiments reported by scientists at the <a href="/wiki/Ontario_Agricultural_College" title="Ontario Agricultural College">Ontario Agricultural College</a>.<sup id="cite_ref-Dam_2_72-0" class="reference"><a href="#cite_note-Dam_2-72"><span class="cite-bracket">[</span>72<span class="cite-bracket">]</span></a></sup> McFarlane, Graham and Richardson, working on the chick feed program at OAC, used <a href="/wiki/Chloroform" title="Chloroform">chloroform</a> to remove all fat from chick chow. They noticed that chicks fed only fat-depleted chow developed hemorrhages and started bleeding from tag sites.<sup id="cite_ref-OAC_73-0" class="reference"><a href="#cite_note-OAC-73"><span class="cite-bracket">[</span>73<span class="cite-bracket">]</span></a></sup> Dam found that these defects could not be restored by adding purified cholesterol to the diet. It appeared that – together with the cholesterol – a second compound was extracted from the food, and this compound was called the coagulation vitamin. The new vitamin received the letter K because the initial discoveries were reported in a German journal, in which it was designated as <i>Koagulationsvitamin</i>. <a href="/wiki/Edward_Adelbert_Doisy" title="Edward Adelbert Doisy">Edward Adelbert Doisy</a> of <a href="/wiki/Saint_Louis_University" title="Saint Louis University">Saint Louis University</a> did much of the research that led to the discovery of the structure and chemical nature of vitamin K.<sup id="cite_ref-MacCorquodale_74-0" class="reference"><a href="#cite_note-MacCorquodale-74"><span class="cite-bracket">[</span>74<span class="cite-bracket">]</span></a></sup> Dam and Doisy shared the 1943 <a href="/wiki/Nobel_Prize" title="Nobel Prize">Nobel Prize</a> for medicine for their work on vitamin K<sub>1</sub> and K<sub>2</sub> published in 1939. Several laboratories synthesized the compound(s) in 1939.<sup id="cite_ref-Fieser_75-0" class="reference"><a href="#cite_note-Fieser-75"><span class="cite-bracket">[</span>75<span class="cite-bracket">]</span></a></sup> </p><p>For several decades, the vitamin K–deficient chick model was the only method of quantifying vitamin K in various foods: the chicks were made vitamin K–deficient and subsequently fed with known amounts of vitamin K–containing food. The extent to which blood coagulation was restored by the diet was taken as a measure for its vitamin K content. Three groups of physicians independently found this: Biochemical Institute, University of Copenhagen (Dam and Johannes Glavind), <a href="/wiki/University_of_Iowa" title="University of Iowa">University of Iowa</a> Department of Pathology (Emory Warner, <a href="/wiki/Kenneth_Brinkhous" title="Kenneth Brinkhous">Kenneth Brinkhous</a>, and Harry Pratt Smith), and the <a href="/wiki/Mayo_Clinic" title="Mayo Clinic">Mayo Clinic</a> (<a href="/wiki/Hugh_Butt" title="Hugh Butt">Hugh Butt</a>, <a href="/wiki/Albert_Snell" title="Albert Snell">Albert Snell</a>, and Arnold Osterberg).<sup id="cite_ref-dam-nobel_76-0" class="reference"><a href="#cite_note-dam-nobel-76"><span class="cite-bracket">[</span>76<span class="cite-bracket">]</span></a></sup> </p><p>The first published report of successful treatment with vitamin K of life-threatening hemorrhage in a jaundiced patient with prothrombin deficiency was made in 1938 by Smith, Warner, and Brinkhous.<sup id="cite_ref-Warner_77-0" class="reference"><a href="#cite_note-Warner-77"><span class="cite-bracket">[</span>77<span class="cite-bracket">]</span></a></sup> </p><p>The precise function of vitamin K was not discovered until 1974, when <a href="/wiki/Prothrombin" class="mw-redirect" title="Prothrombin">prothrombin</a>, a blood coagulation protein, was confirmed to be vitamin K dependent. When the vitamin is present, prothrombin has amino acids near the amino terminus of the protein as <a href="/wiki/%CE%93-carboxyglutamate" class="mw-redirect" title="Γ-carboxyglutamate">γ-carboxyglutamate</a> instead of <a href="/wiki/Glutamate" class="mw-redirect" title="Glutamate">glutamate</a>, and is able to bind calcium, part of the clotting process.<sup id="cite_ref-78" class="reference"><a href="#cite_note-78"><span class="cite-bracket">[</span>78<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=25" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Osteoporosis">Osteoporosis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=26" title="Edit section: Osteoporosis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Vitamin K is required for the gamma-carboxylation of <a href="/wiki/Osteocalcin" title="Osteocalcin">osteocalcin</a> in bone.<sup id="cite_ref-Hamidi2013_79-0" class="reference"><a href="#cite_note-Hamidi2013-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup> The risk of <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>, assessed via <a href="/wiki/Bone_mineral_density" class="mw-redirect" title="Bone mineral density">bone mineral density</a> and fractures, was not affected for people on warfarin therapy – a vitamin K antagonist.<sup id="cite_ref-Fiordellisi2019_80-0" class="reference"><a href="#cite_note-Fiordellisi2019-80"><span class="cite-bracket">[</span>80<span class="cite-bracket">]</span></a></sup> Studies investigating whether vitamin K supplementation reduces risk of bone fractures have shown mixed results.<sup id="cite_ref-PKIN2020VitK_4-7" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hamidi2013_79-1" class="reference"><a href="#cite_note-Hamidi2013-79"><span class="cite-bracket">[</span>79<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Mott2019_81-0" class="reference"><a href="#cite_note-Mott2019-81"><span class="cite-bracket">[</span>81<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Hao2017_82-0" class="reference"><a href="#cite_note-Hao2017-82"><span class="cite-bracket">[</span>82<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Cardiovascular_health">Cardiovascular health</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=27" title="Edit section: Cardiovascular health"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Matrix Gla protein is a vitamin K-dependent protein found in bone, but also in soft tissues such as arteries, where it appears to function as an anti-calcification protein. In animal studies, animals that lack the gene for MGP exhibit calcification of arteries and other soft tissues.<sup id="cite_ref-PKIN2020VitK_4-8" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> In humans, <a href="/wiki/Keutel_syndrome" title="Keutel syndrome">Keutel syndrome</a> is a rare <a href="/wiki/Recessive_gene" class="mw-redirect" title="Recessive gene">recessive genetic</a> disorder associated with abnormalities in the gene coding for MGP and characterized by abnormal <a href="/wiki/Diffuse" class="mw-redirect" title="Diffuse">diffuse</a> <a href="/wiki/Cartilage" title="Cartilage">cartilage</a> <a href="/wiki/Calcification" title="Calcification">calcification</a>.<sup id="cite_ref-Munroe1999_83-0" class="reference"><a href="#cite_note-Munroe1999-83"><span class="cite-bracket">[</span>83<span class="cite-bracket">]</span></a></sup> These observations led to a theory that in humans, inadequately carboxylated MGP, due to low dietary intake of the vitamin, could result in increased risk of arterial calcification and coronary heart disease.<sup id="cite_ref-PKIN2020VitK_4-9" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>In <a href="/wiki/Meta-analysis" title="Meta-analysis">meta-analyses</a> of population studies, low intake of vitamin K was associated with inactive MGP, <a href="/wiki/Artery" title="Artery">arterial</a> <a href="/wiki/Calcification" title="Calcification">calcification</a><sup id="cite_ref-ReferenceA_84-0" class="reference"><a href="#cite_note-ReferenceA-84"><span class="cite-bracket">[</span>84<span class="cite-bracket">]</span></a></sup> and arterial stiffness.<sup id="cite_ref-Roumeliotis2019_85-0" class="reference"><a href="#cite_note-Roumeliotis2019-85"><span class="cite-bracket">[</span>85<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Maresz2015_86-0" class="reference"><a href="#cite_note-Maresz2015-86"><span class="cite-bracket">[</span>86<span class="cite-bracket">]</span></a></sup> Lower dietary intakes of vitamin K<sub>1</sub> and vitamin K<sub>2</sub> were also associated with higher <a href="/wiki/Coronary_heart_disease" class="mw-redirect" title="Coronary heart disease">coronary heart disease</a>.<sup id="cite_ref-Chen2019_37-1" class="reference"><a href="#cite_note-Chen2019-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-autogenerated1_87-0" class="reference"><a href="#cite_note-autogenerated1-87"><span class="cite-bracket">[</span>87<span class="cite-bracket">]</span></a></sup> When blood concentration of circulating vitamin K<sub>1</sub> was assessed there was an increased risk in all cause mortality linked to low concentration.<sup id="cite_ref-88" class="reference"><a href="#cite_note-88"><span class="cite-bracket">[</span>88<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Shea2020_89-0" class="reference"><a href="#cite_note-Shea2020-89"><span class="cite-bracket">[</span>89<span class="cite-bracket">]</span></a></sup> In contrast to these population studies, a review of randomized trials using supplementation with either vitamin K<sub>1</sub> or vitamin K<sub>2</sub> reported no role in mitigating vascular calcification or reducing arterial stiffness. The trials were too short to assess any impact on coronary heart disease or mortality.<sup id="cite_ref-Vlasschaert2020_90-0" class="reference"><a href="#cite_note-Vlasschaert2020-90"><span class="cite-bracket">[</span>90<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=28" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Population studies suggest that vitamin K status may have roles in inflammation, brain function, endocrine function and an anti-cancer effect. For all of these, there is not sufficient evidence from intervention trials to draw any conclusions.<sup id="cite_ref-PKIN2020VitK_4-10" class="reference"><a href="#cite_note-PKIN2020VitK-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> From a review of observational trials, long-term use of vitamin K antagonists as anticoagulation therapy is associated with lower cancer incidence in general.<sup id="cite_ref-91" class="reference"><a href="#cite_note-91"><span class="cite-bracket">[</span>91<span class="cite-bracket">]</span></a></sup> There are conflicting reviews as to whether agonists reduce the risk of prostate cancer.<sup id="cite_ref-92" class="reference"><a href="#cite_note-92"><span class="cite-bracket">[</span>92<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-93" class="reference"><a href="#cite_note-93"><span class="cite-bracket">[</span>93<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=Vitamin_K&action=edit&section=29" 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 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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" 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(2020). "Vitamin K". <i>Present Knowledge in Nutrition, Eleventh Edition</i>. 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Oncol</i>. <b>42</b> (9): 717–724. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2FCOC.0000000000000571">10.1097/COC.0000000000000571</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/31313676">31313676</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:197421591">197421591</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Am.+J.+Clin.+Oncol.&rft.atitle=Long-Term+Vitamin+K+Antagonists+and+Cancer+Risk%3A+A+Systematic+Review+and+Meta-Analysis&rft.volume=42&rft.issue=9&rft.pages=717-724&rft.date=2019-09&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A197421591%23id-name%3DS2CID&rft_id=info%3Apmid%2F31313676&rft_id=info%3Adoi%2F10.1097%2FCOC.0000000000000571&rft.aulast=Shurrab&rft.aufirst=M&rft.au=Quinn%2C+KL&rft.au=Kitchlu%2C+A&rft.au=Jackevicius%2C+CA&rft.au=Ko%2C+DT&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVitamin+K" class="Z3988"></span></span> </li> <li id="cite_note-92"><span class="mw-cite-backlink"><b><a href="#cite_ref-92">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLuoLuoLaiChen2018" class="citation journal cs1">Luo JD, Luo J, Lai C, Chen J, Meng HZ (December 2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6310569">"Is use of vitamin K antagonists associated with the risk of prostate cancer?: A meta-analysis"</a>. <i>Medicine (Baltimore)</i>. <b>97</b> (49): e13489. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2FMD.0000000000013489">10.1097/MD.0000000000013489</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6310569">6310569</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/30544443">30544443</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Medicine+%28Baltimore%29&rft.atitle=Is+use+of+vitamin+K+antagonists+associated+with+the+risk+of+prostate+cancer%3F%3A+A+meta-analysis&rft.volume=97&rft.issue=49&rft.pages=e13489&rft.date=2018-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6310569%23id-name%3DPMC&rft_id=info%3Apmid%2F30544443&rft_id=info%3Adoi%2F10.1097%2FMD.0000000000013489&rft.aulast=Luo&rft.aufirst=JD&rft.au=Luo%2C+J&rft.au=Lai%2C+C&rft.au=Chen%2C+J&rft.au=Meng%2C+HZ&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6310569&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVitamin+K" class="Z3988"></span></span> </li> <li id="cite_note-93"><span class="mw-cite-backlink"><b><a href="#cite_ref-93">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFKristensenJensenSkriverFriis2019" class="citation journal cs1">Kristensen KB, Jensen PH, Skriver C, Friis S, Pottegård A (April 2019). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210417215749/https://findresearcher.sdu.dk:8443/ws/files/154496758/SDU_kopi_kristensenetal.pdf">"Use of vitamin K antagonists and risk of prostate cancer: Meta-analysis and nationwide case-control study"</a> <span class="cs1-format">(PDF)</span>. <i>Int. J. Cancer</i>. <b>144</b> (7): 1522–1529. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fijc.31886">10.1002/ijc.31886</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/30246248">30246248</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:52339455">52339455</a>. Archived from <a rel="nofollow" class="external text" href="https://findresearcher.sdu.dk:8443/ws/files/154496758/SDU_kopi_kristensenetal.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 17 April 2021<span class="reference-accessdate">. Retrieved <span class="nowrap">13 October</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Int.+J.+Cancer&rft.atitle=Use+of+vitamin+K+antagonists+and+risk+of+prostate+cancer%3A+Meta-analysis+and+nationwide+case-control+study&rft.volume=144&rft.issue=7&rft.pages=1522-1529&rft.date=2019-04&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A52339455%23id-name%3DS2CID&rft_id=info%3Apmid%2F30246248&rft_id=info%3Adoi%2F10.1002%2Fijc.31886&rft.aulast=Kristensen&rft.aufirst=KB&rft.au=Jensen%2C+PH&rft.au=Skriver%2C+C&rft.au=Friis%2C+S&rft.au=Potteg%C3%A5rd%2C+A&rft_id=https%3A%2F%2Ffindresearcher.sdu.dk%3A8443%2Fws%2Ffiles%2F154496758%2FSDU_kopi_kristensenetal.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVitamin+K" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Vitamin_K&action=edit&section=30" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://agresearchmag.ars.usda.gov/AR/archive/2000/Jan/green0100.pdf">"Vitamin K: Another Reason to Eat Your Greens"</a> <span class="cs1-format">(PDF)</span>. <i>Agricultural Research</i>. <b>48</b> (1). January 2000. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/2169-8244">2169-8244</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Agricultural+Research&rft.atitle=Vitamin+K%3A+Another+Reason+to+Eat+Your+Greens&rft.volume=48&rft.issue=1&rft.date=2000-01&rft.issn=2169-8244&rft_id=https%3A%2F%2Fagresearchmag.ars.usda.gov%2FAR%2Farchive%2F2000%2FJan%2Fgreen0100.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVitamin+K" class="Z3988"></span></li></ul> <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=Vitamin_K&action=edit&section=31" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1235681985">.mw-parser-output .side-box{margin:4px 0;box-sizing:border-box;border:1px solid #aaa;font-size:88%;line-height:1.25em;background-color:var(--background-color-interactive-subtle,#f8f9fa);display:flow-root}.mw-parser-output .side-box-abovebelow,.mw-parser-output .side-box-text{padding:0.25em 0.9em}.mw-parser-output .side-box-image{padding:2px 0 2px 0.9em;text-align:center}.mw-parser-output .side-box-imageright{padding:2px 0.9em 2px 0;text-align:center}@media(min-width:500px){.mw-parser-output .side-box-flex{display:flex;align-items:center}.mw-parser-output .side-box-text{flex:1;min-width:0}}@media(min-width:720px){.mw-parser-output .side-box{width:238px}.mw-parser-output .side-box-right{clear:right;float:right;margin-left:1em}.mw-parser-output .side-box-left{margin-right:1em}}</style><style data-mw-deduplicate="TemplateStyles:r1237033735">@media print{body.ns-0 .mw-parser-output .sistersitebox{display:none!important}}@media 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src="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/40px-Wiktionary-logo-en-v2.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/60px-Wiktionary-logo-en-v2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/99/Wiktionary-logo-en-v2.svg/80px-Wiktionary-logo-en-v2.svg.png 2x" data-file-width="512" data-file-height="512" /></span></span></div> <div class="side-box-text plainlist">Look up <i><b><a href="https://en.wiktionary.org/wiki/Special:Search/vitamin_k" class="extiw" title="wiktionary:Special:Search/vitamin k">vitamin k</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <ul><li>Vitamin K: <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5280483">CID 5280483</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a></li> <li>Vitamin K1 (phylloquinone, phytomenadione): <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5284607">CID 5284607</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a></li> <li>Vitamin K2 (menaquinone 6): <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5283547">CID 5283547</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a></li> <li>Vitamin K3 (menadione): <a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/4055">CID 4055</a> from <a href="/wiki/PubChem" title="PubChem">PubChem</a></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 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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 class="mw-selflink selflink">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 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="Enzyme_cofactors" 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:Enzyme_cofactors" title="Template:Enzyme cofactors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Enzyme_cofactors" title="Template talk:Enzyme cofactors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Enzyme_cofactors" title="Special:EditPage/Template:Enzyme cofactors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Enzyme_cofactors" style="font-size:114%;margin:0 4em"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a> <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactors</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Active forms</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" title="Vitamin">vitamins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thiamine_pyrophosphate" title="Thiamine pyrophosphate">TPP / ThDP</a> (B<sub>1</sub>)</li> <li><a href="/wiki/Flavin_mononucleotide" title="Flavin mononucleotide">FMN</a>, <a href="/wiki/Flavin_adenine_dinucleotide" title="Flavin adenine dinucleotide">FAD</a> (B<sub>2</sub>)</li> <li><a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NAD<sup>+</sup></a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NADH</a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADP<sup>+</sup></a>, <a href="/wiki/Nicotinamide_adenine_dinucleotide_phosphate" title="Nicotinamide adenine dinucleotide phosphate">NADPH</a> (B<sub>3</sub>)</li> <li><a href="/wiki/Coenzyme_A" title="Coenzyme A">Coenzyme A</a> (B<sub>5</sub>)</li> <li><a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">PLP / P5P</a> (B<sub>6</sub>)</li> <li><a href="/wiki/Biotin" title="Biotin">Biotin</a> (B<sub>7</sub>)</li> <li><a href="/wiki/Tetrahydrofolic_acid" title="Tetrahydrofolic acid">THFA / H<sub>4</sub>FA</a>, <a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">DHFA / H<sub>2</sub>FA</a>, <a href="/wiki/5,10-Methylenetetrahydrofolate" title="5,10-Methylenetetrahydrofolate">MTHF</a> (B<sub>9</sub>)</li> <li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">AdoCbl</a>, <a href="/wiki/Methylcobalamin" title="Methylcobalamin">MeCbl</a> (B<sub>12</sub>)</li> <li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a> (C)</li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone</a> (K<sub>1</sub>), <a class="mw-selflink selflink">Menaquinone</a> (K<sub>2</sub>)</li> <li><a href="/wiki/Coenzyme_F420" title="Coenzyme F420">Coenzyme F420</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cofactor_(biochemistry)#Non-vitamins" title="Cofactor (biochemistry)">non-vitamins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a></li> <li><a href="/wiki/Cytidine_triphosphate" title="Cytidine triphosphate">CTP</a></li> <li><a href="/wiki/S-Adenosyl_methionine" title="S-Adenosyl methionine">SAMe</a></li> <li><a href="/wiki/3%27-Phosphoadenosine-5%27-phosphosulfate" title="3'-Phosphoadenosine-5'-phosphosulfate">PAPS</a></li> <li><a href="/wiki/Glutathione" title="Glutathione">GSH</a></li> <li><a href="/wiki/Coenzyme_B" title="Coenzyme B">Coenzyme B</a></li> <li><a href="/wiki/Cofactor_F430" title="Cofactor F430">Cofactor F430</a></li> <li><a href="/wiki/Coenzyme_M" title="Coenzyme M">Coenzyme M</a></li> <li><a href="/wiki/Coenzyme_Q10" title="Coenzyme Q10">Coenzyme Q</a></li> <li><a href="/wiki/Heme" title="Heme">Heme / Haem</a> (<a href="/wiki/Heme_A" title="Heme A">A</a>, <a href="/wiki/Heme_B" title="Heme B">B</a>, <a href="/wiki/Heme_C" title="Heme C">C</a>, <a href="/wiki/Heme_O" title="Heme O">O</a>)</li> <li><a href="/wiki/Lipoic_acid" title="Lipoic acid">Lipoic Acid</a></li> <li><a href="/wiki/Methanofuran" title="Methanofuran">Methanofuran</a></li> <li><a href="/wiki/Molybdopterin" title="Molybdopterin">Molybdopterin</a></li> <li><a href="/wiki/Mycofactocin" title="Mycofactocin">Mycofactocin</a></li> <li><a href="/wiki/Pyrroloquinoline_quinone" title="Pyrroloquinoline quinone">PQQ</a></li> <li><a href="/wiki/Tetrahydrobiopterin" title="Tetrahydrobiopterin">THB / BH<sub>4</sub></a></li> <li><a href="/wiki/Tetrahydromethanopterin" title="Tetrahydromethanopterin">THMPT / H<sub>4</sub>MPT</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mineral_(nutrient)" title="Mineral (nutrient)">metal ions</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Calcium" title="Calcium">Ca<sup>2+</sup></a></li> <li><a href="/wiki/Copper" title="Copper">Cu<sup>2+</sup></a></li> <li><a href="/wiki/Iron" title="Iron">Fe<sup>2+</sup>, Fe<sup>3+</sup></a></li> <li><a href="/wiki/Magnesium" title="Magnesium">Mg<sup>2+</sup></a></li> <li><a href="/wiki/Manganese" title="Manganese">Mn<sup>2+</sup></a></li> <li><a href="/wiki/Molybdenum" title="Molybdenum">Mo</a></li> <li><a href="/wiki/Nickel" title="Nickel">Ni<sup>2+</sup></a></li> <li><a href="/wiki/Zinc" title="Zinc">Zn<sup>2+</sup></a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Base forms</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Vitamin" title="Vitamin">vitamins</a></i>: <i>see <a href="/wiki/Template:Vitamins" title="Template:Vitamins">vitamins</a></i></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></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 class="mw-selflink selflink">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 href="/wiki/Menadione" title="Menadione">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> <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 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