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<span>Function</span> </div> </a> <ul id="toc-Function-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Toxicity</span> </div> </a> <button aria-controls="toc-Toxicity-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 Toxicity subsection</span> </button> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> <li id="toc-Hyperbilirubinemia" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Hyperbilirubinemia"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Hyperbilirubinemia</span> </div> </a> <ul id="toc-Hyperbilirubinemia-sublist" class="vector-toc-list"> <li id="toc-Jaundice" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Jaundice"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1.1</span> <span>Jaundice</span> </div> </a> <ul id="toc-Jaundice-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Kernicterus" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Kernicterus"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1.2</span> <span>Kernicterus</span> </div> </a> <ul id="toc-Kernicterus-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Health_benefits" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Health_benefits"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Health benefits</span> </div> </a> <ul id="toc-Health_benefits-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Blood_tests" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Blood_tests"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Blood tests</span> </div> </a> <button aria-controls="toc-Blood_tests-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 Blood tests subsection</span> </button> <ul id="toc-Blood_tests-sublist" class="vector-toc-list"> <li id="toc-Total_bilirubin" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Total_bilirubin"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.1</span> <span>Total bilirubin</span> </div> </a> <ul id="toc-Total_bilirubin-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Indirect_(unconjugated)" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Indirect_(unconjugated)"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Indirect (unconjugated)</span> </div> </a> <ul id="toc-Indirect_(unconjugated)-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Direct" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Direct"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3</span> <span>Direct</span> </div> </a> <ul id="toc-Direct-sublist" class="vector-toc-list"> <li id="toc-Conjugated" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Conjugated"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3.1</span> <span>Conjugated</span> </div> </a> <ul id="toc-Conjugated-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Delta_bilirubin" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Delta_bilirubin"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3.2</span> <span>Delta bilirubin</span> </div> </a> <ul id="toc-Delta_bilirubin-sublist" class="vector-toc-list"> <li id="toc-Half-life" class="vector-toc-list-item vector-toc-level-4"> <a class="vector-toc-link" href="#Half-life"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.3.2.1</span> <span>Half-life</span> </div> </a> <ul id="toc-Half-life-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Measurement_methods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Measurement_methods"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.4</span> <span>Measurement methods</span> </div> </a> <ul id="toc-Measurement_methods-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Blood_levels" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Blood_levels"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Blood levels</span> </div> </a> <ul id="toc-Blood_levels-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Urine_tests" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Urine_tests"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Urine tests</span> </div> </a> <ul id="toc-Urine_tests-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notable_people" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notable_people"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Notable people</span> </div> </a> <ul id="toc-Notable_people-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Notes" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Notes"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>Notes</span> </div> </a> <ul id="toc-Notes-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">13</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">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">Bilirubin</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 63 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-63" 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">63 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/Bilirubien" title="Bilirubien – Afrikaans" lang="af" hreflang="af" data-title="Bilirubien" 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/%D8%A8%D9%8A%D9%84%D9%8A%D8%B1%D9%88%D8%A8%D9%8A%D9%86" title="بيليروبين – Arabic" lang="ar" hreflang="ar" data-title="بيليروبين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A8%DB%8C%D9%84%DB%8C%E2%80%8C%D8%B1%D9%88%D8%A8%DB%8C%D9%86" title="بیلی‌روبین – South Azerbaijani" lang="azb" hreflang="azb" data-title="بیلی‌روبین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%AC%E0%A6%BF%E0%A6%B2%E0%A6%BF%E0%A6%B0%E0%A7%81%E0%A6%AC%E0%A6%BF%E0%A6%A8" title="বিলিরুবিন – Bangla" lang="bn" hreflang="bn" data-title="বিলিরুবিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%91%D1%96%D0%BB%D1%96%D1%80%D1%83%D0%B1%D1%96%D0%BD" title="Білірубін – Belarusian" lang="be" hreflang="be" data-title="Білірубін" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%91%D0%B8%D0%BB%D0%B8%D1%80%D1%83%D0%B1%D0%B8%D0%BD" title="Билирубин – Bulgarian" lang="bg" hreflang="bg" data-title="Билирубин" 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/Bilirubin" title="Bilirubin – Bosnian" lang="bs" hreflang="bs" data-title="Bilirubin" 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/Bilirubina" title="Bilirubina – Catalan" lang="ca" hreflang="ca" data-title="Bilirubina" 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/Bilirubin" title="Bilirubin – Czech" lang="cs" hreflang="cs" data-title="Bilirubin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-ary mw-list-item"><a href="https://ary.wikipedia.org/wiki/%D8%A8%D9%8A%D9%84%D9%8A%D8%B1%D9%88%D8%A8%D9%8A%D9%86" title="بيليروبين – Moroccan Arabic" lang="ary" hreflang="ary" data-title="بيليروبين" data-language-autonym="الدارجة" data-language-local-name="Moroccan Arabic" class="interlanguage-link-target"><span>الدارجة</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Bilirubin" title="Bilirubin – German" lang="de" hreflang="de" data-title="Bilirubin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A7%CE%BF%CE%BB%CE%B5%CF%81%CF%85%CE%B8%CF%81%CE%AF%CE%BD%CE%B7" title="Χολερυθρίνη – Greek" lang="el" hreflang="el" data-title="Χολερυθρίνη" 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/Bilirrubina" title="Bilirrubina – Spanish" lang="es" hreflang="es" data-title="Bilirrubina" 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/Bilirubino" title="Bilirubino – Esperanto" lang="eo" hreflang="eo" data-title="Bilirubino" 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/Bilirrubina" title="Bilirrubina – Basque" lang="eu" hreflang="eu" data-title="Bilirrubina" 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/%D8%A8%DB%8C%D9%84%DB%8C%E2%80%8C%D8%B1%D9%88%D8%A8%DB%8C%D9%86" title="بیلی‌روبین – Persian" lang="fa" hreflang="fa" data-title="بیلی‌روبین" 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/Bilirubine" title="Bilirubine – French" lang="fr" hreflang="fr" data-title="Bilirubine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Bilear%C3%BAibin" title="Bilearúibin – Irish" lang="ga" hreflang="ga" data-title="Bilearúibin" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Bilirrubina" title="Bilirrubina – Galician" lang="gl" hreflang="gl" data-title="Bilirrubina" 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%8C%EB%A6%AC%EB%A3%A8%EB%B9%88" title="빌리루빈 – Korean" lang="ko" hreflang="ko" data-title="빌리루빈" 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/%D4%B2%D5%AB%D5%AC%D5%AB%D5%BC%D5%B8%D6%82%D5%A2%D5%AB%D5%B6" title="Բիլիռուբին – Armenian" lang="hy" hreflang="hy" data-title="Բիլիռուբին" 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%AC%E0%A4%BF%E0%A4%B2%E0%A5%80%E0%A4%B0%E0%A5%81%E0%A4%AC%E0%A4%BF%E0%A4%A8" title="बिलीरुबिन – Hindi" lang="hi" hreflang="hi" data-title="बिलीरुबिन" 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/Bilirubin" title="Bilirubin – Croatian" lang="hr" hreflang="hr" data-title="Bilirubin" 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/Bilirubin" title="Bilirubin – Indonesian" lang="id" hreflang="id" data-title="Bilirubin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Bilirubina" title="Bilirubina – Italian" lang="it" hreflang="it" data-title="Bilirubina" 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%91%D7%99%D7%9C%D7%99%D7%A8%D7%95%D7%91%D7%99%D7%9F" title="בילירובין – Hebrew" lang="he" hreflang="he" data-title="בילירובין" 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/Bilirubin" title="Bilirubin – Javanese" lang="jv" hreflang="jv" data-title="Bilirubin" 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%91%E1%83%98%E1%83%9A%E1%83%98%E1%83%A0%E1%83%A3%E1%83%91%E1%83%98%E1%83%9C%E1%83%98" title="ბილირუბინი – Georgian" lang="ka" hreflang="ka" data-title="ბილირუბინი" data-language-autonym="ქართული" data-language-local-name="Georgian" class="interlanguage-link-target"><span>ქართული</span></a></li><li class="interlanguage-link interwiki-sw mw-list-item"><a href="https://sw.wikipedia.org/wiki/Bilirubini" title="Bilirubini – Swahili" lang="sw" hreflang="sw" data-title="Bilirubini" data-language-autonym="Kiswahili" data-language-local-name="Swahili" class="interlanguage-link-target"><span>Kiswahili</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Bilirub%C4%ABns" title="Bilirubīns – Latvian" lang="lv" hreflang="lv" data-title="Bilirubīns" 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/Bilirubinas" title="Bilirubinas – Lithuanian" lang="lt" hreflang="lt" data-title="Bilirubinas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Bilirubin" title="Bilirubin – Hungarian" lang="hu" hreflang="hu" data-title="Bilirubin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%91%D0%B8%D0%BB%D0%B8%D1%80%D1%83%D0%B1%D0%B8%D0%BD" title="Билирубин – Macedonian" lang="mk" hreflang="mk" data-title="Билирубин" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%AC%E0%B4%BF%E0%B4%B2%E0%B4%BF%E0%B4%B1%E0%B5%82%E0%B4%AC%E0%B4%BF%E0%B5%BB" title="ബിലിറൂബിൻ – Malayalam" lang="ml" hreflang="ml" data-title="ബിലിറൂബിൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Bilirubine" title="Bilirubine – Dutch" lang="nl" hreflang="nl" data-title="Bilirubine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%93%E3%83%AA%E3%83%AB%E3%83%93%E3%83%B3" title="ビリルビン – Japanese" lang="ja" hreflang="ja" data-title="ビリルビン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Bilirubin" title="Bilirubin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Bilirubin" 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-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Bilirubin" title="Bilirubin – Uzbek" lang="uz" hreflang="uz" data-title="Bilirubin" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pnb mw-list-item"><a href="https://pnb.wikipedia.org/wiki/%D8%A8%DB%8C%D9%84%DB%8C%D8%B1%D9%88%D8%A8%D9%86" title="بیلیروبن – Western Punjabi" lang="pnb" hreflang="pnb" data-title="بیلیروبن" data-language-autonym="پنجابی" data-language-local-name="Western Punjabi" class="interlanguage-link-target"><span>پنجابی</span></a></li><li class="interlanguage-link interwiki-nds mw-list-item"><a href="https://nds.wikipedia.org/wiki/Bilirubin" title="Bilirubin – Low German" lang="nds" hreflang="nds" data-title="Bilirubin" data-language-autonym="Plattdüütsch" data-language-local-name="Low German" class="interlanguage-link-target"><span>Plattdüütsch</span></a></li><li class="interlanguage-link interwiki-pl badge-Q17437798 badge-goodarticle mw-list-item" title="good article badge"><a href="https://pl.wikipedia.org/wiki/Bilirubina" title="Bilirubina – Polish" lang="pl" hreflang="pl" data-title="Bilirubina" 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/Bilirrubina" title="Bilirrubina – Portuguese" lang="pt" hreflang="pt" data-title="Bilirrubina" 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/Bilirubin%C4%83" title="Bilirubină – Romanian" lang="ro" hreflang="ro" data-title="Bilirubină" 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%91%D0%B8%D0%BB%D0%B8%D1%80%D1%83%D0%B1%D0%B8%D0%BD" title="Билирубин – Russian" lang="ru" hreflang="ru" data-title="Билирубин" 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/Bilirubina" title="Bilirubina – Albanian" lang="sq" hreflang="sq" data-title="Bilirubina" 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/Bilirubin" title="Bilirubin – Simple English" lang="en-simple" hreflang="en-simple" data-title="Bilirubin" 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-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Bilirub%C3%ADn" title="Bilirubín – Slovak" lang="sk" hreflang="sk" data-title="Bilirubín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Bilirubin" title="Bilirubin – Slovenian" lang="sl" hreflang="sl" data-title="Bilirubin" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%A8%DB%8C%D9%84%DB%8C%DA%95%D9%88%D9%88%D8%A8%DB%8C%D9%86" title="بیلیڕووبین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="بیلیڕووبین" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%91%D0%B8%D0%BB%D0%B8%D1%80%D1%83%D0%B1%D0%B8%D0%BD" title="Билирубин – Serbian" lang="sr" hreflang="sr" data-title="Билирубин" 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/Bilirubin" title="Bilirubin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Bilirubin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Bilirubiini" title="Bilirubiini – Finnish" lang="fi" hreflang="fi" data-title="Bilirubiini" 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/Bilirubin" title="Bilirubin – Swedish" lang="sv" hreflang="sv" data-title="Bilirubin" 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%AA%E0%AE%BF%E0%AE%B2%E0%AE%BF%E0%AE%B0%E0%AF%81%E0%AE%AA%E0%AE%BF%E0%AE%A9%E0%AF%8D" title="பிலிருபின் – Tamil" lang="ta" hreflang="ta" data-title="பிலிருபின்" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target"><span>தமிழ்</span></a></li><li class="interlanguage-link interwiki-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%91%D0%B8%D0%BB%D0%B8%D1%80%D1%83%D0%B1%D0%B8%D0%BD" title="Билирубин – Tatar" lang="tt" hreflang="tt" data-title="Билирубин" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9A%E0%B8%B4%E0%B8%A5%E0%B8%B4%E0%B8%A3%E0%B8%B9%E0%B8%9A%E0%B8%B4%E0%B8%99" title="บิลิรูบิน – Thai" lang="th" hreflang="th" data-title="บิลิรูบิน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tg mw-list-item"><a href="https://tg.wikipedia.org/wiki/%D0%91%D0%B8%D0%BB%D0%B8%D1%80%D1%83%D0%B1%D0%B8%D0%BD" title="Билирубин – Tajik" lang="tg" hreflang="tg" data-title="Билирубин" data-language-autonym="Тоҷикӣ" data-language-local-name="Tajik" class="interlanguage-link-target"><span>Тоҷикӣ</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Bilir%C3%BCbin" title="Bilirübin – Turkish" lang="tr" hreflang="tr" data-title="Bilirübin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%91%D1%96%D0%BB%D1%96%D1%80%D1%83%D0%B1%D1%96%D0%BD" title="Білірубін – Ukrainian" lang="uk" hreflang="uk" data-title="Білірубін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%A8%DB%8C%D9%84%DB%8C%D8%B1%D9%88%D8%A8%D9%86" title="بیلیروبن – Urdu" lang="ur" hreflang="ur" data-title="بیلیروبن" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Bilirubin" title="Bilirubin – Vietnamese" lang="vi" hreflang="vi" data-title="Bilirubin" 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-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E8%83%86%E7%BA%A2%E7%B4%A0" title="胆红素 – Wu" lang="wuu" hreflang="wuu" data-title="胆红素" 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 mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E8%83%86%E7%BA%A2%E7%B4%A0" title="胆红素 – Chinese" lang="zh" hreflang="zh" data-title="胆红素" 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/Q104219#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div 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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">"Billy Rubin" redirects here. For the American art scholar, see <a href="/wiki/William_Rubin" title="William Rubin">William Rubin</a>.</div> <p> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>Bilirubin </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Bilirubin_(CAS_635-65-4).svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Bilirubin_%28CAS_635-65-4%29.svg/220px-Bilirubin_%28CAS_635-65-4%29.svg.png" decoding="async" width="220" height="148" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Bilirubin_%28CAS_635-65-4%29.svg/330px-Bilirubin_%28CAS_635-65-4%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f8/Bilirubin_%28CAS_635-65-4%29.svg/440px-Bilirubin_%28CAS_635-65-4%29.svg.png 2x" data-file-width="327" data-file-height="220" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Bilirubin-from-xtal-1978-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Bilirubin-from-xtal-1978-3D-balls.png/220px-Bilirubin-from-xtal-1978-3D-balls.png" decoding="async" width="220" height="179" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Bilirubin-from-xtal-1978-3D-balls.png/330px-Bilirubin-from-xtal-1978-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Bilirubin-from-xtal-1978-3D-balls.png/440px-Bilirubin-from-xtal-1978-3D-balls.png 2x" data-file-width="2000" data-file-height="1624" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">3,3′-(2,17-Diethenyl-3,7,13,18-tetramethyl-1,19-dioxo-10,19,21,22,23,24-hexahydro-1<i>H</i>-biline-8,12-diyl)dipropanoic acid</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">3,3′-([1<sup>2</sup>(2)<i>Z</i>,6(7<sup>2</sup>)<i>Z</i>]-1<sup>3</sup>,7<sup>4</sup>-Diethenyl-1<sup>4</sup>,3<sup>3</sup>,5<sup>4</sup>,7<sup>3</sup>-tetramethyl-1<sup>5</sup>,7<sup>5</sup>-dioxo-1<sup>1</sup>,1<sup>5</sup>,7<sup>1</sup>,7<sup>5</sup>-tetrahydro-3<sup>1</sup><i>H</i>,5<sup>1</sup><i>H</i>-1,7(2),3,5(2,5)-tetrapyrrolaheptaphane-1<sup>2</sup>(2),6(7<sup>2</sup>)-diene-3<sup>4</sup>,5<sup>3</sup>-diyl)dipropanoic acid</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Bilirubin IXα</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=635-65-4">635-65-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CC1%3DC%28%2FC%3DC2C%28C%29%3DC%28C%3DC%29C%28N%2F2%29%3DO%29NC%28CC3%3DC%28CCC%28O%29%3DO%29C%28C%29%3DC%28%2FC%3DC4C%28C%3DC%29%3DC%28C%29C%28N%2F4%29%3DO%29N3%29%3DC1CCC%28O%29%3DO">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Cc1c%28c%28%5BnH%5Dc1%2FC%3DC%5C2%2FC%28%3DC%28C%28%3DO%29N2%29C%3DC%29C%29Cc3c%28c%28c%28%5BnH%5D3%29%2FC%3DC%5C4%2FC%28%3DC%28C%28%3DO%29N4%29C%29C%3DC%29C%29CCC%28%3DO%29O%29CCC%28%3DO%29O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16990">CHEBI:16990</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL501680">ChEMBL501680</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4444055.html">4444055</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.010.218">100.010.218</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q104219#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=4577">4577</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5280352">5280352</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/RFM9X3LJ49">RFM9X3LJ49</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID90239827,">DTXSID8060905 DTXSID90239827, DTXSID8060905</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q104219#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C33H36N4O6/c1-7-20-19(6)32(42)37-27(20)14-25-18(5)23(10-12-31(40)41)29(35-25)15-28-22(9-11-30(38)39)17(4)24(34-28)13-26-16(3)21(8-2)33(43)36-26/h7-8,13-14,34-35H,1-2,9-12,15H2,3-6H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b26-13-,27-14-<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: BPYKTIZUTYGOLE-IFADSCNNSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: BPYKTIZUTYGOLE-IFADSCNNBS</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CC1=C(/C=C2C(C)=C(C=C)C(N/2)=O)NC(CC3=C(CCC(O)=O)C(C)=C(/C=C4C(C=C)=C(C)C(N/4)=O)N3)=C1CCC(O)=O</div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">Cc1c(c([nH]c1/C=C\2/C(=C(C(=O)N2)C=C)C)Cc3c(c(c([nH]3)/C=C\4/C(=C(C(=O)N4)C)C=C)C)CCC(=O)O)CCC(=O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>33</sub><span title="Hydrogen">H</span><sub>36</sub><span title="Nitrogen">N</span><sub>4</sub><span title="Oxygen">O</span><sub>6</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002584673000000000♠"></span>584.673</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.31 g·cm-3<sup id="cite_ref-Reaxys_1-0" class="reference"><a href="#cite_note-Reaxys-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>235°C<sup id="cite_ref-Reaxysb_2-0" class="reference"><a href="#cite_note-Reaxysb-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443422624&page2=Bilirubin">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Bilirubin</b> (<b>BR</b>) (from the <a href="/wiki/Latin" title="Latin">Latin</a> for "red bile") is a red-orange compound that occurs in the normal <a href="/wiki/Catabolism" title="Catabolism">catabolic</a> pathway that breaks down <a href="/wiki/Heme" title="Heme">heme</a> in <a href="/wiki/Vertebrate" title="Vertebrate">vertebrates</a>. This catabolism is a necessary process in the body's clearance of waste products that arise from the destruction of aged or abnormal <a href="/wiki/Red_blood_cell" title="Red blood cell">red blood cells</a>.<sup id="cite_ref-BRAUNSTEIN.EVAN_2019_3-0" class="reference"><a href="#cite_note-BRAUNSTEIN.EVAN_2019-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> In the first step of bilirubin synthesis, the <a href="/wiki/Heme" title="Heme">heme</a> molecule is stripped from the <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a> molecule. Heme then passes through various processes of <a href="/wiki/Porphyrin" title="Porphyrin">porphyrin</a> catabolism, which varies according to the region of the body in which the breakdown occurs. For example, the molecules excreted in the <a href="/wiki/Urine" title="Urine">urine</a> differ from those in the <a href="/wiki/Feces" title="Feces">feces</a>.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The production of <a href="/wiki/Biliverdin" title="Biliverdin">biliverdin</a> from heme is the first major step in the catabolic pathway, after which the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Biliverdin_reductase" title="Biliverdin reductase">biliverdin reductase</a> performs the second step, producing bilirubin from biliverdin.<sup id="cite_ref-boron_5-0" class="reference"><a href="#cite_note-boron-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-mos_6-0" class="reference"><a href="#cite_note-mos-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Ultimately, bilirubin is broken down within the body, and its <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> excreted through <a href="/wiki/Bile" title="Bile">bile</a> and urine; elevated levels may indicate certain diseases.<sup id="cite_ref-Smith_Morton_2010_pp._85–105_7-0" class="reference"><a href="#cite_note-Smith_Morton_2010_pp._85–105-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> It is responsible for the yellow color of healing <a href="/wiki/Bruise" title="Bruise">bruises</a> and the yellow discoloration in <a href="/wiki/Jaundice" title="Jaundice">jaundice</a>. The bacterial enzyme bilirubin reductase is responsible for the breakdown of bilirubin in the gut.<sup id="cite_ref-:6_8-0" class="reference"><a href="#cite_note-:6-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> One breakdown product, <a href="/wiki/Urobilin" title="Urobilin">urobilin</a>, is the main component of the straw-yellow color in urine.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Another breakdown product, <a href="/wiki/Stercobilin" title="Stercobilin">stercobilin</a>, causes the brown color of feces. </p><p>Although bilirubin is usually found in animals rather than plants, at least one plant species, <i><a href="/wiki/Strelitzia_nicolai" title="Strelitzia nicolai">Strelitzia nicolai</a></i>, is known to contain the pigment.<sup id="cite_ref-pmid19206232_10-0" class="reference"><a href="#cite_note-pmid19206232-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=1" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bilirubin consists of an open-chain <a href="/wiki/Tetrapyrrole" title="Tetrapyrrole">tetrapyrrole</a>. It is formed by oxidative cleavage of a <a href="/wiki/Porphyrin" title="Porphyrin">porphyrin</a> in heme, which affords biliverdin. Biliverdin is reduced to bilirubin. After conjugation with <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a>, bilirubin is water-soluble and can be excreted.<sup id="cite_ref-:3_11-0" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Bilirubin is structurally similar to the <a href="/wiki/Pigment" title="Pigment">pigment</a> <a href="/wiki/Phycobilin" title="Phycobilin">phycobilin</a> used by certain algae to capture light energy, and to the pigment <a href="/wiki/Phytochrome" title="Phytochrome">phytochrome</a> used by plants to sense light. All of these contain an open chain of four pyrrolic rings.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Like these other pigments, some of the double-bonds in bilirubin <a href="/wiki/Cis-trans_isomerism" class="mw-redirect" title="Cis-trans isomerism">isomerize</a> when exposed to light. This isomerization is relevant to the <a href="/wiki/Phototherapy" class="mw-redirect" title="Phototherapy">phototherapy</a> of jaundiced newborns: the E,Z-isomers of bilirubin formed upon light exposure are more soluble than the unilluminated Z,Z-isomer, as the possibility of intramolecular hydrogen bonding is removed.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Increased solubility allows the excretion of unconjugated bilirubin in bile.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2024)">citation needed</span></a></i>]</sup> </p><p>Some textbooks and research articles show the incorrect geometric isomer of bilirubin.<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> The naturally occurring isomer is the Z,Z-isomer. </p> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=2" title="Edit section: Function"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bilirubin is created by the activity of <a href="/wiki/Biliverdin_reductase" title="Biliverdin reductase">biliverdin reductase</a> on <a href="/wiki/Biliverdin" title="Biliverdin">biliverdin</a>, a green tetrapyrrolic bile pigment that is also a product of heme <a href="/wiki/Catabolism" title="Catabolism">catabolism</a>. Bilirubin, when oxidized, reverts to become biliverdin once again. This cycle, in addition to the demonstration of the potent antioxidant activity of bilirubin,<sup id="cite_ref-PMID_3029864_15-0" class="reference"><a href="#cite_note-PMID_3029864-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> has led to the hypothesis that bilirubin's main physiologic role is as a cellular antioxidant.<sup id="cite_ref-pmid12456881_16-0" class="reference"><a href="#cite_note-pmid12456881-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Consistent with this, animal studies suggest that eliminating bilirubin results in endogenous oxidative stress.<sup id="cite_ref-PMID_29195835_18-0" class="reference"><a href="#cite_note-PMID_29195835-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Bilirubin's antioxidant activity may be particularly important in the brain, where it prevents excitotoxicity and neuronal death by scavenging superoxide during N-methyl-D-aspartic acid neurotransmission.<sup id="cite_ref-PMID_31353321_19-0" class="reference"><a href="#cite_note-PMID_31353321-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=3" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Heme_Breakdown.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Heme_Breakdown.png/250px-Heme_Breakdown.png" decoding="async" width="250" height="306" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Heme_Breakdown.png/375px-Heme_Breakdown.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d9/Heme_Breakdown.png/500px-Heme_Breakdown.png 2x" data-file-width="812" data-file-height="993" /></a><figcaption>Heme metabolism</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Bilirubin_metabolism_diagram.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Bilirubin_metabolism_diagram.png/396px-Bilirubin_metabolism_diagram.png" decoding="async" width="396" height="502" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b4/Bilirubin_metabolism_diagram.png/593px-Bilirubin_metabolism_diagram.png 1.5x, //upload.wikimedia.org/wikipedia/commons/b/b4/Bilirubin_metabolism_diagram.png 2x" data-file-width="781" data-file-height="991" /></a><figcaption>Heme and bilirubin metabolism</figcaption></figure> <p>Bilirubin in plasma is mostly produced by the destruction of erythrocytes. Heme is metabolized into <a href="/wiki/Biliverdin" title="Biliverdin">biliverdin</a> (via heme oxygenase) and then into bilirubin (via <a href="/wiki/Biliverdin_reductase" title="Biliverdin reductase">biliverdin reductase</a>) inside the macrophages. <sup id="cite_ref-:3_11-1" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Bilirubin is then released into the plasma and transported to the liver bound by <a href="/wiki/Albumin" title="Albumin">albumin</a>, since it is insoluble in water in this state. In this state, bilirubin is called unconjugated (despite being bound by albumin). <sup id="cite_ref-:3_11-2" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>In the liver, unconjugated bilirubin is up-taken by the hepatocytes and subsequently conjugated with glucuronic acid (via the enzyme <a href="/wiki/Uridine_diphosphate_glucuronyltransferase" class="mw-redirect" title="Uridine diphosphate glucuronyltransferase">uridine diphosphate–glucuronyl transferase</a>). In this state, bilirubin is soluble in water and it is called conjugated bilirubin. <sup id="cite_ref-:3_11-3" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Conjugated bilirubin is excreted into the bile ducts and enters the duodenum. During its transport to the colon, it is converted into <a href="/wiki/Urobilinogen" title="Urobilinogen">urobilinogen</a> by the bacterial enzyme bilirubin reductase.<sup id="cite_ref-:6_8-1" class="reference"><a href="#cite_note-:6-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Most of the urobilinogen is further reduced into <a href="/wiki/Stercobilinogen" title="Stercobilinogen">stercobilinogen</a> and is excreted through feces (air oxidizes stercobilinogen to <a href="/wiki/Stercobilin" title="Stercobilin">stercobilin</a>, which gives feces their characteristic brown color). <sup id="cite_ref-:3_11-4" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>A lesser amount of urobilinogen is re-absorbed into portal circulation and transferred to the liver. For the most part, this urobilinogen is recycled to conjugated bilirubin and this process closes the enterohepatic circle. There is also an amount of urobilinogen which is not recycled, but rather enters the systemic circulation and subsequently the kidneys, where it is excreted. Air oxidizes urobilinogen into <a href="/wiki/Urobilin" title="Urobilin">urobilin</a>, which gives urine its characteristic color.<sup id="cite_ref-:3_11-5" class="reference"><a href="#cite_note-:3-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:4_20-0" class="reference"><a href="#cite_note-:4-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>In parallel, a small amount of conjugated billirubin can also enter the systemic circulation and get excreted through urine. This is exaggerated in various pathological situations.<sup id="cite_ref-:4_20-1" class="reference"><a href="#cite_note-:4-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=4" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Hyperbilirubinemia">Hyperbilirubinemia</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=5" title="Edit section: Hyperbilirubinemia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Jaundice" title="Jaundice">Hyperbilirubinemia</a> is a higher-than-normal level of bilirubin in the blood. Hyperbilirubinemia may refer to increased levels of conjugated, unconjugated or both conjugated and unconjugated bilirubin. The causes of hyperbilirubinemia can also be classified into prehepatic, intrahepatic, and posthepatic. <sup id="cite_ref-:5_21-0" class="reference"><a href="#cite_note-:5-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Prehepatic causes are associated mostly with an increase of unconjugated (indirect) bilirubin.<sup id="cite_ref-:5_21-1" class="reference"><a href="#cite_note-:5-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> They include: </p> <ul><li><a href="/wiki/Hemolysis" title="Hemolysis">Hemolysis</a> or increased breakdown of red blood cells (for example hematoma resorption)</li></ul> <p>Intrahepatic causes can be associated with elevated levels of conjugated bilirubin, unconjugated bilirubin or both.<sup id="cite_ref-:5_21-2" class="reference"><a href="#cite_note-:5-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> They include:<sup id="cite_ref-:5_21-3" class="reference"><a href="#cite_note-:5-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Neonatal_jaundice" title="Neonatal jaundice">Neonatal hyperbilirubinemia</a>, where the newborn's liver is not able to properly process the bilirubin causing <a href="/wiki/Jaundice" title="Jaundice">jaundice</a></li> <li>Hepatocellular disease <ul><li>Viral infections (hepatitis A, B, and C)</li> <li>Chronic alcohol use</li> <li>Autoimmune disorders</li></ul></li> <li>Genetic syndromes: <ul><li><a href="/wiki/Gilbert%27s_syndrome" title="Gilbert's syndrome">Gilbert's syndrome</a> – a genetic disorder of bilirubin metabolism that can result in mild jaundice, found in about 5% of the population</li> <li><a href="/wiki/Rotor_syndrome" title="Rotor syndrome">Rotor syndrome</a>: non-itching jaundice, with rise of bilirubin in the patient's serum, mainly of the conjugated type</li> <li><a href="/wiki/Dubin%E2%80%93Johnson_syndrome" title="Dubin–Johnson syndrome">Dubin–Johnson syndrome</a></li> <li><a href="/wiki/Crigler%E2%80%93Najjar_syndrome" title="Crigler–Najjar syndrome">Crigler–Najjar syndrome</a></li></ul></li> <li><a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">Pharmaceutical drugs</a> (especially <a href="/wiki/Antipsychotic" title="Antipsychotic">antipsychotic</a>, some <a href="/wiki/Sex_hormone" title="Sex hormone">sex hormones</a>, and a wide range of other drugs) <ul><li><a href="/wiki/Sulfonamide_(medicine)" title="Sulfonamide (medicine)">Sulfonamides</a> are contraindicated in infants less than 2 months old (exception when used with <a href="/wiki/Pyrimethamine" title="Pyrimethamine">pyrimethamine</a> in treating <a href="/wiki/Toxoplasmosis" title="Toxoplasmosis">toxoplasmosis</a>) as they increase unconjugated bilirubin leading to <a href="/wiki/Kernicterus" title="Kernicterus">kernicterus</a>.<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></li> <li>Drugs such as <a href="/wiki/Protease_inhibitor_(pharmacology)" title="Protease inhibitor (pharmacology)">protease inhibitors</a> like <a href="/wiki/Indinavir" title="Indinavir">Indinavir</a> can also cause disorders of bilirubin metabolism by competitively inhibiting the <a href="/wiki/UGT1A1" class="mw-redirect" title="UGT1A1">UGT1A1</a> enzyme.<sup id="cite_ref-Ramakrishnan_Jialal_2019_23-0" class="reference"><a href="#cite_note-Ramakrishnan_Jialal_2019-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup></li></ul></li></ul> <p>Post-hepatic causes are associated with elevated levels of conjugated bilirubin. <sup id="cite_ref-:5_21-4" class="reference"><a href="#cite_note-:5-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> These include:<sup id="cite_ref-:5_21-5" class="reference"><a href="#cite_note-:5-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <ul><li>Unusually large bile duct obstruction, e.g. gallstone in common bile duct (which is the most common post-hepatic cause)</li> <li>Biliary stricture (benign or malignant)</li> <li>Cholangitis</li> <li>Severe liver failure with <a href="/wiki/Cirrhosis" title="Cirrhosis">cirrhosis</a> (e.g. <a href="/wiki/Primary_biliary_cirrhosis" class="mw-redirect" title="Primary biliary cirrhosis">primary biliary cirrhosis</a>)</li> <li>Pancreatitis</li></ul> <p>Cirrhosis may cause normal, moderately high or high levels of bilirubin, depending on exact features of the cirrhosis. </p><p>To further elucidate the causes of jaundice or increased bilirubin, it is usually simpler to look at other <a href="/wiki/Liver_function_tests" title="Liver function tests">liver function tests</a> (especially the enzymes <a href="/wiki/Alanine_transaminase" title="Alanine transaminase">alanine transaminase</a>, <a href="/wiki/Aspartate_transaminase" title="Aspartate transaminase">aspartate transaminase</a>, <a href="/wiki/Gamma-glutamyl_transpeptidase" class="mw-redirect" title="Gamma-glutamyl transpeptidase">gamma-glutamyl transpeptidase</a>, <a href="/wiki/Alkaline_phosphatase" title="Alkaline phosphatase">alkaline phosphatase</a>), <a href="/wiki/Blood_film" class="mw-redirect" title="Blood film">blood film</a> examination (<a href="/wiki/Hemolysis" title="Hemolysis">hemolysis</a>, etc.) or evidence of infective hepatitis (e.g., hepatitis A, B, C, delta, E, etc.).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2024)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Jaundice">Jaundice</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=6" title="Edit section: Jaundice"><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/Jaundice" title="Jaundice">Jaundice</a></div> <p>Hemoglobin acts to transport oxygen which the body receives to all body tissue via blood vessels. Over time, when red blood cells need to be replenished, the hemoglobin is broken down in the spleen; it breaks down into two parts: heme group consisting of iron and bile and protein fraction. While protein and iron are utilized to renew red blood cells, pigments that make up the red color in blood are deposited into the bile to form bilirubin.<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> Jaundice leads to raised bilirubin levels<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup>> that in turn negatively remove <a href="/wiki/Elastin" title="Elastin">elastin</a>-rich tissues.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Jaundice" title="Jaundice">Jaundice</a> may be noticeable in the <a href="/wiki/Sclera" title="Sclera">sclera</a> of the eyes at levels of about 2 to 3 mg/dl (34 to 51 μmol/L),<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> and in the skin at higher levels.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>note 1<span class="cite-bracket">]</span></a></sup> </p><p>Jaundice is classified, depending upon whether the bilirubin is free or conjugated to <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a>, into conjugated jaundice or unconjugated jaundice.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2008)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading4"><h4 id="Kernicterus">Kernicterus</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=7" title="Edit section: Kernicterus"><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/Kernicterus" title="Kernicterus">Kernicterus</a></div> <p>Unbound bilirubin (Bf) levels can be used to predict the risk of neurodevelopmental handicaps within infants.<sup id="cite_ref-SciFinder_29-0" class="reference"><a href="#cite_note-SciFinder-29"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Unconjugated <a href="/wiki/Hyperbilirubinaemia" class="mw-redirect" title="Hyperbilirubinaemia">hyperbilirubinemia</a> in a newborn can lead to accumulation of bilirubin in certain brain regions (particularly the <a href="/wiki/Basal_nuclei" class="mw-redirect" title="Basal nuclei">basal nuclei</a>) with consequent irreversible damage to these areas manifesting as various neurological deficits, <a href="/wiki/Seizure" title="Seizure">seizures</a>, abnormal <a href="/wiki/Reflexes" class="mw-redirect" title="Reflexes">reflexes</a> and eye movements. This type of neurological injury is known as kernicterus. The spectrum of clinical effect is called <a href="/w/index.php?title=Bilirubin_encephalopathy&action=edit&redlink=1" class="new" title="Bilirubin encephalopathy (page does not exist)">bilirubin encephalopathy</a>. The neurotoxicity of neonatal hyperbilirubinemia manifests because the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> has yet to develop fully,<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Accuracy_dispute#Disputed_statement" title="Wikipedia:Accuracy dispute"><span title="The material near this tag is possibly inaccurate or nonfactual. (September 2014)">dubious</span></a> – <a href="/wiki/Talk:Bilirubin#Toxicity_.26_the_blood-brain_barrier" title="Talk:Bilirubin">discuss</a></i>]</sup> and bilirubin can freely pass into the brain interstitium, whereas more developed individuals with increased bilirubin in the blood are protected. Aside from specific chronic medical conditions that may lead to hyperbilirubinemia, neonates in general are at increased risk since they lack the intestinal bacteria that facilitate the breakdown and excretion of conjugated bilirubin in the feces (this is largely why the feces of a neonate are paler than those of an adult). Instead the conjugated bilirubin is converted back into the unconjugated form by the enzyme <a href="/wiki/Beta-glucuronidase" class="mw-redirect" title="Beta-glucuronidase">β-glucuronidase</a> (in the gut, this enzyme is located in the brush border of the lining intestinal cells) and a large proportion is reabsorbed through the <a href="/wiki/Enterohepatic_circulation" title="Enterohepatic circulation">enterohepatic circulation</a>. In addition, recent studies point towards high total bilirubin levels as a cause for gallstones regardless of gender or age.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Health_benefits">Health benefits</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=8" title="Edit section: Health benefits"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the absence of liver disease, high levels of total bilirubin confers various health benefits.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Studies have also revealed that levels of serum bilirubin (SBR)<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> are inversely related to risk of certain heart diseases.<sup id="cite_ref-Novotn_33-0" class="reference"><a href="#cite_note-Novotn-33"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> While the poor solubility and potential toxicity of bilirubin limit its potential medicinal applications, current research is being done on whether bilirubin encapsulated silk fibrin nanoparticles can alleviate symptoms of disorders such as acute pancreatitis.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> In addition to this, there have been recent discoveries linking bilirubin and its ε-polylysine-bilirubin conjugate (PLL-BR), to more efficient insulin medication. It seems that bilirubin exhibits protective properties during the islet transplantation process when drugs are delivered throughout the bloodstream.<sup id="cite_ref-SciFinderb_36-0" class="reference"><a href="#cite_note-SciFinderb-36"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Blood_tests">Blood tests</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=9" title="Edit section: Blood tests"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Bilirubin is degraded by light. Blood collection tubes containing blood or (especially) serum to be used in bilirubin assays should be protected from illumination.<sup id="cite_ref-Rehak_2007_37-0" class="reference"><a href="#cite_note-Rehak_2007-37"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> For adults, blood is typically collected by needle from a vein in the arm.<sup id="cite_ref-Mayo_Clinic_2022_c113_38-0" class="reference"><a href="#cite_note-Mayo_Clinic_2022_c113-38"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> In newborns, blood is often collected from a heel stick, a technique that uses a small, sharp blade to cut the skin on the infant's heel and collect a few drops of blood into a small tube. Non-invasive technology is available in some health care facilities that will measure bilirubin by using an bilirubinometer which shines light onto the skin and calculates the amount of bilirubin by analysing how the light is absorbed or reflects. <sup id="cite_ref-nhs.uk_2017_c967_39-0" class="reference"><a href="#cite_note-nhs.uk_2017_c967-39"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> This device is also known as a transcutaneous bilirubin meter.<sup id="cite_ref-Lucanova_2021_40-0" class="reference"><a href="#cite_note-Lucanova_2021-40"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p><p>Bilirubin (in blood) is found in two forms: </p> <table class="wikitable sortable"> <tbody><tr> <th>Abb.</th> <th>Name(s)</th> <th>Water-soluble</th> <th>Reaction </th></tr> <tr> <td>"BC"</td> <td>"Conjugated bilirubin"</td> <td>Yes (bound to glucuronic acid)</td> <td>Reacts quickly when dyes (diazo reagent) are added to the blood specimen to produce <a href="/wiki/Azobilirubin" title="Azobilirubin">azobilirubin</a> "Direct bilirubin" </td></tr> <tr> <td>"BU"</td> <td>"Unconjugated bilirubin"</td> <td>No</td> <td>Reacts more slowly, still produces azobilirubin, Ethanol makes all bilirubin react promptly, then: indirect bilirubin = total bilirubin – direct bilirubin </td></tr></tbody></table> <p>Note: Conjugated bilirubin is often incorrectly called "direct bilirubin" and unconjugated bilirubin is incorrectly called "indirect bilirubin". Direct and indirect refer solely to how compounds are measured or detected in solution. Direct bilirubin is any form of bilirubin which is water-soluble and is available in solution to react with assay reagents; direct bilirubin is often made up largely of conjugated bilirubin, but some unconjugated bilirubin (up to 25%) can still be part of the "direct" bilirubin fraction. Likewise, not all conjugated bilirubin is readily available in solution for reaction or detection (for example, if it is hydrogen bonding with itself) and therefore would not be included in the direct bilirubin fraction.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2021)">citation needed</span></a></i>]</sup> </p><p>Total bilirubin (TBIL) measures both BU and BC. Total bilirubin assays work by using surfactants and accelerators (like caffeine) to bring all of the different bilirubin forms into solution where they can react with assay reagents. Total and direct bilirubin levels can be measured from the blood, but indirect bilirubin is calculated from the total and direct bilirubin.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2024)">citation needed</span></a></i>]</sup> </p><p>Indirect bilirubin is fat-soluble and direct bilirubin is water-soluble.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Total_bilirubin">Total bilirubin</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=10" title="Edit section: Total bilirubin"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Total bilirubin = direct bilirubin + indirect bilirubin<sup id="cite_ref-Tietze_2012_pp._86–122_42-0" class="reference"><a href="#cite_note-Tietze_2012_pp._86–122-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p><p>Elevation of both <a href="/wiki/Alanine_aminotransferase" class="mw-redirect" title="Alanine aminotransferase">alanine aminotransferase</a> (ALT) and bilirubin is more indicative of serious liver injury than is elevation in ALT alone, as postulated in <a href="/wiki/Hy%27s_law" title="Hy's law">Hy's law</a> that elucidates the relation between the lab test results and <a href="/wiki/Drug-induced_liver_injury" class="mw-redirect" title="Drug-induced liver injury">drug-induced liver injury</a><sup id="cite_ref-Gwaltney-Brant_2016_pp._87–99_43-0" class="reference"><a href="#cite_note-Gwaltney-Brant_2016_pp._87–99-43"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Indirect_(unconjugated)"><span id="Indirect_.28unconjugated.29"></span>Indirect (unconjugated)</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=11" title="Edit section: Indirect (unconjugated)"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The measurement of unconjugated bilirubin (UCB) is underestimated by measurement of indirect bilirubin, as unconjugated bilirubin (without/yet glucuronidation) reacts with diazosulfanilic acid to create <a href="/wiki/Azobilirubin" title="Azobilirubin">azobilirubin</a> which is measured as direct bilirubin.<sup id="cite_ref-Medscape_Reference_2019_44-0" class="reference"><a href="#cite_note-Medscape_Reference_2019-44"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Medscape_Reference_2019_II_45-0" class="reference"><a href="#cite_note-Medscape_Reference_2019_II-45"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Direct">Direct</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=12" title="Edit section: Direct"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Direct bilirubin = Conjugated bilirubin + delta bilirubin<sup id="cite_ref-Tietze_2012_pp._86–122_42-1" class="reference"><a href="#cite_note-Tietze_2012_pp._86–122-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Conjugated">Conjugated</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=13" title="Edit section: Conjugated"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In the liver, bilirubin is conjugated with <a href="/wiki/Glucuronic_acid" title="Glucuronic acid">glucuronic acid</a> by the enzyme <a href="/wiki/Glucuronyltransferase" class="mw-redirect" title="Glucuronyltransferase">glucuronyltransferase</a>, first to <a href="/wiki/Bilirubin_glucuronide" title="Bilirubin glucuronide">bilirubin glucuronide</a> and then to <a href="/wiki/Bilirubin_diglucuronide" title="Bilirubin diglucuronide">bilirubin diglucuronide</a>, making it soluble in water: the conjugated version is the main form of bilirubin present in the "direct" bilirubin fraction. Much of it goes into the bile and thus out into the small intestine. Though most <a href="/wiki/Bile_acid" title="Bile acid">bile acid</a> is reabsorbed in the <a href="/wiki/Terminal_ileum" class="mw-redirect" title="Terminal ileum">terminal ileum</a> to participate in <a href="/wiki/Enterohepatic_circulation" title="Enterohepatic circulation">enterohepatic circulation</a>, conjugated bilirubin is not absorbed and instead passes into the <a href="/wiki/Large_intestine" title="Large intestine">colon</a>.<sup id="cite_ref-handbook_46-0" class="reference"><a href="#cite_note-handbook-46"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p><p>There, colonic bacteria deconjugate and metabolize the bilirubin into colorless <a href="/wiki/Urobilinogen" title="Urobilinogen">urobilinogen</a>, which can be oxidized to form <a href="/wiki/Urobilin" title="Urobilin">urobilin</a> and <a href="/wiki/Stercobilin" title="Stercobilin">stercobilin</a>. Urobilin is excreted by the kidneys to give urine its yellow color and stercobilin is excreted in the feces giving stool its characteristic brown color. A trace (~1%) of the urobilinogen is reabsorbed into the <a href="/wiki/Enterohepatic_circulation" title="Enterohepatic circulation">enterohepatic circulation</a> to be re-excreted in the bile.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> </p><p>Conjugated bilirubin's half-life is shorter than delta bilirubin.<sup id="cite_ref-Sullivan_Gourley_2011_pp._176–186.e3_48-0" class="reference"><a href="#cite_note-Sullivan_Gourley_2011_pp._176–186.e3-48"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Delta_bilirubin">Delta bilirubin</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=14" title="Edit section: Delta bilirubin"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Although the terms direct and indirect bilirubin are used equivalently with conjugated and unconjugated bilirubin, this is not quantitatively correct, because the direct fraction includes both conjugated bilirubin and δ bilirubin.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (November 2021)">citation needed</span></a></i>]</sup> </p><p>Delta bilirubin is albumin-bound conjugated bilirubin.<sup id="cite_ref-Tietze_2012_pp._86–122_42-2" class="reference"><a href="#cite_note-Tietze_2012_pp._86–122-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> In the other words, delta bilirubin is the kind of bilirubin covalently bound to <a href="/wiki/Albumin" title="Albumin">albumin</a>, which appears in the serum when hepatic excretion of conjugated bilirubin is impaired in patients with <a href="/wiki/Hepatobiliary_disease" class="mw-redirect" title="Hepatobiliary disease">hepatobiliary disease</a>.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> Furthermore, direct bilirubin tends to overestimate conjugated bilirubin levels due to unconjugated bilirubin that has reacted with diazosulfanilic acid, leading to increased azobilirubin levels (and increased direct bilirubin).<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2024)">citation needed</span></a></i>]</sup> </p><p>δ bilirubin = total bilirubin – (unconjugated bilirubin + conjugated bilirubin)<sup id="cite_ref-Tietze_2012_pp._86–122_42-3" class="reference"><a href="#cite_note-Tietze_2012_pp._86–122-42"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading5"><h5 id="Half-life">Half-life</h5><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=15" title="Edit section: Half-life"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The half-life of delta bilirubin is equivalent to that of <a href="/wiki/Human_serum_albumin" title="Human serum albumin">albumin</a> since the former is bound to the latter, yields 2–3 weeks.<sup id="cite_ref-Kalakonda_John_2019_p._50-0" class="reference"><a href="#cite_note-Kalakonda_John_2019_p.-50"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Medscape_Reference_2019_44-1" class="reference"><a href="#cite_note-Medscape_Reference_2019-44"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>A free-of-bound bilirubin has a half-life of 2 to 4 hours.<sup id="cite_ref-Kalakonda_John_2019_p._50-1" class="reference"><a href="#cite_note-Kalakonda_John_2019_p.-50"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Bilirubin_glucuronide" title="Bilirubin glucuronide">Bilirubin glucuronide</a></div> <div class="mw-heading mw-heading3"><h3 id="Measurement_methods">Measurement methods</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=16" title="Edit section: Measurement methods"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Originally, the <a href="/wiki/Van_den_Bergh_reaction" title="Van den Bergh reaction">Van den Bergh reaction</a> was used for a qualitative estimate of bilirubin.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2024)">citation needed</span></a></i>]</sup> </p><p>This test is performed routinely in most <a href="/wiki/Medical_laboratory" title="Medical laboratory">medical laboratories</a> and can be measured by a variety of methods.<sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p><p>Total bilirubin is now often measured by the 2,5-dichlorophenyldiazonium (DPD) method, and direct bilirubin is often measured by the method of Jendrassik and Grof.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Blood_levels">Blood levels</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=17" title="Edit section: Blood levels"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The bilirubin level found in the body reflects the balance between production and excretion. Blood test results are advised to always be interpreted using the reference range provided by the laboratory that performed the test. The <a href="/wiki/SI_units" class="mw-redirect" title="SI units">SI units</a> are μmol/L.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> Typical ranges for adults are:<sup id="cite_ref-MedlinePlusBilirubin_54-0" class="reference"><a href="#cite_note-MedlinePlusBilirubin-54"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p> <ul><li>0–0.3 mg/dl – Direct (conjugated) bilirubin level</li> <li>0.1–1.2 mg/dl – Total serum bilirubin level</li></ul> <table class="wikitable"> <tbody><tr> <th></th> <th>μmol/l = micromole/litre</th> <th>mg/dl = milligram/ decilitre </th></tr> <tr> <td>total bilirubin</td> <td><21<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup></td> <td><1.23 </td></tr> <tr> <td>direct bilirubin</td> <td>1.0–5.1<sup id="cite_ref-WebMD_56-0" class="reference"><a href="#cite_note-WebMD-56"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup></td> <td>0–0.3,<sup id="cite_ref-MedlinePlus_57-0" class="reference"><a href="#cite_note-MedlinePlus-57"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup><br /> 0.1–0.3,<sup id="cite_ref-WebMD_56-1" class="reference"><a href="#cite_note-WebMD-56"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup><br /> 0.1–0.4<sup id="cite_ref-LSUHSC_58-0" class="reference"><a href="#cite_note-LSUHSC-58"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <div class="thumb tnone" style="margin-left:auto;margin-right:auto;overflow:hidden;width:auto;max-width:3508px"><div class="thumbinner"><div class="noresize" style="overflow:auto"><span typeof="mw:File"><a href="/wiki/File:Blood_values_sorted_by_mass_and_molar_concentration.png" class="mw-file-description" title="Reference ranges for blood tests, comparing blood content of bilirubin (shown in blue near horizontal center at around 3 mg/L and 3 μmol/L, scroll to the right to view) with other constituents"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Blood_values_sorted_by_mass_and_molar_concentration.png/3500px-Blood_values_sorted_by_mass_and_molar_concentration.png" decoding="async" width="3500" height="503" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cb/Blood_values_sorted_by_mass_and_molar_concentration.png/5250px-Blood_values_sorted_by_mass_and_molar_concentration.png 1.5x, //upload.wikimedia.org/wikipedia/commons/c/cb/Blood_values_sorted_by_mass_and_molar_concentration.png 2x" data-file-width="6798" data-file-height="977" /></a></span></div><div class="thumbcaption"><div class="magnify"><a href="/wiki/File:Blood_values_sorted_by_mass_and_molar_concentration.png" title="File:Blood values sorted by mass and molar concentration.png"> </a></div><a href="/wiki/Reference_ranges_for_blood_tests" title="Reference ranges for blood tests">Reference ranges for blood tests</a>, comparing blood content of bilirubin (shown in blue near horizontal center at around 3 mg/L and 3 μmol/L, scroll to the right to view) with other constituents<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup></div></div></div> <div class="mw-heading mw-heading2"><h2 id="Urine_tests">Urine tests</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=18" title="Edit section: Urine tests"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Urine bilirubin may also be clinically significant.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> Bilirubin is not normally detectable in the urine of healthy people. If the blood level of conjugated bilirubin becomes elevated, e.g. due to liver disease, excess conjugated bilirubin is excreted in the urine, indicating a pathological process.<sup id="cite_ref-61" class="reference"><a href="#cite_note-61"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> Unconjugated bilirubin is not water-soluble and so is not excreted in the urine. Testing urine for both bilirubin and <a href="/wiki/Urobilinogen" title="Urobilinogen">urobilinogen</a> can help differentiate obstructive liver disease from other causes of jaundice.<sup id="cite_ref-NBK302_62-0" class="reference"><a href="#cite_note-NBK302-62"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>As with billirubin, under normal circumstances, only a very small amount of urobilinogen is excreted in the <a href="/wiki/Urine" title="Urine">urine</a>. If the liver's function is impaired or when biliary drainage is blocked, some of the conjugated bilirubin leaks out of the hepatocytes and appears in the urine, turning it dark amber. However, in disorders involving <a href="/wiki/Hemolytic_anemia" title="Hemolytic anemia">hemolytic anemia</a>, an increased number of red blood cells are broken down, causing an increase in the amount of unconjugated bilirubin in the blood. Because the unconjugated bilirubin is not water-soluble, one will not see an increase in bilirubin in the urine. Because there is no problem with the liver or bile systems, this excess unconjugated bilirubin will go through all of the normal processing mechanisms that occur (e.g., conjugation, excretion in bile, metabolism to urobilinogen, reabsorption) and will show up as an increase of urobilinogen in the urine. This difference between increased urine bilirubin and increased urine urobilinogen helps to distinguish between various disorders in those systems.<sup id="cite_ref-NBK302_62-1" class="reference"><a href="#cite_note-NBK302-62"><span class="cite-bracket">[</span>61<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=Bilirubin&action=edit&section=19" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In ancient history, <a href="/wiki/Hippocrates" title="Hippocrates">Hippocrates</a> discussed bile pigments in two of the four <a href="/wiki/Humorism" title="Humorism">humours</a> in the context of a relationship between yellow and black biles.<sup id="cite_ref-:0_63-0" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> Hippocrates visited <a href="/wiki/Democritus" title="Democritus">Democritus</a> in <a href="/wiki/Abdera,_Thrace" title="Abdera, Thrace">Abdera</a> who was regarded as the expert in melancholy "black bile".<sup id="cite_ref-:0_63-1" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p><p>Relevant documentation emerged in 1827 when <a href="/wiki/Monsieur" title="Monsieur">M.</a> <a href="/wiki/Louis_Jacques_Th%C3%A9nard" title="Louis Jacques Thénard">Louis Jacques Thénard</a> examined the <a href="/wiki/Biliary_tract" title="Biliary tract">biliary tract</a> of an elephant that had died at a Paris zoo. He observed dilated bile ducts were full of yellow magma, which he isolated and found to be insoluble in water. Treating the yellow pigment with <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> produced a strong green color. Thenard suspected the green pigment was caused by impurities derived from mucus of bile.<sup id="cite_ref-:0_63-2" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Leopold_Gmelin" title="Leopold Gmelin">Leopold Gmelin</a> experimented with nitric acid in 1826 to establish the redox behavior in change from bilirubin to biliverdin, although the nomenclature did not exist at the time.<sup id="cite_ref-:0_63-3" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> The term <a href="/wiki/Biliverdin" title="Biliverdin">biliverdin</a> was coined by <a href="/wiki/J%C3%B6ns_Jacob_Berzelius" title="Jöns Jacob Berzelius">Jöns Jacob Berzelius</a> in 1840, although he preferred "bilifulvin" (yellow/red) over "bilirubin" (red). The term "bilirubin" was thought to have become mainstream based on the works of Staedeler in 1864 who crystallized bilirubin from cattle gallstones.<sup id="cite_ref-:0_63-4" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Rudolf_Virchow" title="Rudolf Virchow">Rudolf Virchow</a> in 1847 recognized hematoidin to be identical to bilirubin.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> It is not always distinguished from hematoidin, which one modern dictionary defines as synonymous with it<sup id="cite_ref-MWU_66-0" class="reference"><a href="#cite_note-MWU-66"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> but another defines as "apparently chemically identical with bilirubin but with a different site of origin, formed locally in the tissues from hemoglobin, particularly under conditions of reduced oxygen tension."<sup id="cite_ref-Dorlands_67-0" class="reference"><a href="#cite_note-Dorlands-67"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_63-5" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> The synonymous identity of bilirubin and hematoidin was confirmed in 1923 by Fischer and Steinmetz using analytical <a href="/wiki/Crystallography" title="Crystallography">crystallography</a>.<sup id="cite_ref-:0_63-6" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p><p>In the 1930s, significant advances in bilirubin isolation and synthesis were described by <a href="/wiki/Hans_Fischer" title="Hans Fischer">Hans Fischer</a>, <a href="https://de.wikipedia.org/wiki/Hans_Plieninger" class="extiw" title="de:Hans Plieninger">Plieninger</a>, and others,<sup id="cite_ref-:0_63-7" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> and pioneering work pertaining to <a href="/wiki/Endogeny_(biology)" title="Endogeny (biology)">endogenous</a> formation of bilirubin from heme was likewise conducted in the same decade.<sup id="cite_ref-:1_68-0" class="reference"><a href="#cite_note-:1-68"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> The suffix IXα is partially based on a system developed Fischer, which means the <a href="/wiki/Bilin_(biochemistry)" title="Bilin (biochemistry)">bilin</a>'s parent compound was protoporphyrin IX cleaved at the alpha-<a href="/wiki/Methine_group" title="Methine group">methine</a> bridge (see <a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">protoporphyrin IX nomenclature</a>).<sup id="cite_ref-:2_69-0" class="reference"><a href="#cite_note-:2-69"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p><p>Origins pertaining to the physiological activity of bilirubin were described by <a href="/w/index.php?title=Ernst_Stadelmann&action=edit&redlink=1" class="new" title="Ernst Stadelmann (page does not exist)">Ernst Stadelmann</a> in 1891, who may have observed the biotransformation of infused hemoglobin into bilirubin possibly inspired by <a href="/wiki/Ivan_Tarkhanov_(physiologist)" title="Ivan Tarkhanov (physiologist)">Ivan Tarkhanov</a>'s 1874 works.<sup id="cite_ref-:0_63-8" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> <a href="https://de.wikipedia.org/wiki/Georg_Barkan" class="extiw" title="de:Georg Barkan">Georg Barkan</a> suggested the source of endogenous bilirubin to be from hemoglobin in 1932.<sup id="cite_ref-70" class="reference"><a href="#cite_note-70"><span class="cite-bracket">[</span>69<span class="cite-bracket">]</span></a></sup> Plieninger and Fischer demonstrated an enzymatic oxidative loss of the alpha-<a href="/wiki/Methine_group" title="Methine group">methine</a> bridge of heme resulting in a bis-lactam structure in 1942.<sup id="cite_ref-:0_63-9" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> It is widely accepted that <a href="/wiki/Irving_London" title="Irving London">Irving London</a> was the first to demonstrate endogenous formation of bilirubin from hemoglobin in 1950,<sup id="cite_ref-71" class="reference"><a href="#cite_note-71"><span class="cite-bracket">[</span>70<span class="cite-bracket">]</span></a></sup> and Sjostrand demonstrated hemoglobin catabolism produces <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> between 1949 and 1952.<sup id="cite_ref-:1_68-1" class="reference"><a href="#cite_note-:1-68"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> 14C labeled protoporphyrin biotransformation to bilirubin evidence emerged in 1966 by <a href="/wiki/Cecil_Watson" title="Cecil Watson">Cecil Watson</a>.<sup id="cite_ref-:0_63-10" class="reference"><a href="#cite_note-:0-63"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Rudi_Schmid" title="Rudi Schmid">Rudi Schmid</a> and Tenhunen discovered <a href="/wiki/Heme_oxygenase" title="Heme oxygenase">heme oxygenase</a>, the enzyme responsible, in 1968.<sup id="cite_ref-:1_68-2" class="reference"><a href="#cite_note-:1-68"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> Earlier in 1963, Nakajima described a soluble "heme alpha-methnyl oxygeanse" which what later determined to be a non-enzymatic pathway, such as formation of a <a href="/wiki/1,2-Dioxetane" title="1,2-Dioxetane">1,2-Dioxetane</a> intermediate at the methine bridge resulting in carbon monoxide release and biliverdin formation.<sup id="cite_ref-:2_69-1" class="reference"><a href="#cite_note-:2-69"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Notable_people">Notable people</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=20" title="Edit section: Notable people"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Claudio_Tiribelli" title="Claudio Tiribelli">Claudio Tiribelli</a>, Italian hepatologist, studies on bilirubin<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2024)">citation needed</span></a></i>]</sup></li></ul> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=21" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Babesiosis" title="Babesiosis">Babesiosis</a></li> <li><a href="/wiki/Biliary_atresia" title="Biliary atresia">Biliary atresia</a></li> <li><a href="/wiki/Bilirubin_diglucuronide" title="Bilirubin diglucuronide">Bilirubin diglucuronide</a></li> <li><a href="/wiki/Biliverdin" title="Biliverdin">Biliverdin</a></li> <li><a href="/wiki/Crigler%E2%80%93Najjar_syndrome" title="Crigler–Najjar syndrome">Crigler–Najjar syndrome</a></li> <li><a href="/wiki/Gilbert%27s_syndrome" title="Gilbert's syndrome">Gilbert's syndrome</a>, a genetic disorder of bilirubin metabolism that can result in mild jaundice, found in about 5% of the population.</li> <li><a href="/wiki/Hy%27s_Law" class="mw-redirect" title="Hy's Law">Hy's Law</a></li> <li><a href="/wiki/Lumirubin" title="Lumirubin">Lumirubin</a></li> <li><a href="/wiki/Primary_biliary_cholangitis" title="Primary biliary cholangitis">Primary biliary cholangitis</a></li> <li><a href="/wiki/Primary_sclerosing_cholangitis" title="Primary sclerosing cholangitis">Primary sclerosing cholangitis</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Notes">Notes</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=22" title="Edit section: Notes"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text">For conversion, 1 mg/dl = 17.1 μmol/L.</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=23" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239543626"><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Reaxys-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Reaxys_1-0">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFBonnettDaviesHursthouse1976" class="citation journal cs1">Bonnett, Raymond; Davies, John E.; Hursthouse, Michael B. 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Elsevier. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/clinicalskillsfo0000tiet/page/86">86</a>–122. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fb978-0-323-07738-5.10005-5">10.1016/b978-0-323-07738-5.10005-5</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-07738-5" title="Special:BookSources/978-0-323-07738-5"><bdi>978-0-323-07738-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Review+of+Laboratory+and+Diagnostic+Tests&rft.btitle=Clinical+Skills+for+Pharmacists&rft.pages=86-122&rft.pub=Elsevier&rft.date=2012&rft_id=info%3Adoi%2F10.1016%2Fb978-0-323-07738-5.10005-5&rft.isbn=978-0-323-07738-5&rft.aulast=Tietze&rft.aufirst=KJ&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fclinicalskillsfo0000tiet&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABilirubin" class="Z3988"></span></span> </li> <li id="cite_note-Gwaltney-Brant_2016_pp._87–99-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-Gwaltney-Brant_2016_pp._87–99_43-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFGwaltney-Brant2016" class="citation book cs1">Gwaltney-Brant SM (2016). 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U.S. Department of Health, Education, and Welfare, Public Health Service, National Institutes of Health. pp. 27, 50.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=International+Symposium+on+Chemistry+and+Physiology+of+Bile+Pigments&rft.pages=27%2C+50&rft.pub=U.S.+Department+of+Health%2C+Education%2C+and+Welfare%2C+Public+Health+Service%2C+National+Institutes+of+Health&rft.date=1977&rft.aulast=Berk&rft.aufirst=Paul+D.&rft.au=Berlin%2C+Nathaniel+I.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DPZfDTn6BTEAC%26q%3Dmonoxide%26pg%3DPA9&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABilirubin" class="Z3988"></span></span> </li> <li id="cite_note-70"><span class="mw-cite-backlink"><b><a href="#cite_ref-70">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBarkanSchales1938" class="citation journal cs1">Barkan, Georg; Schales, Otto (1938). <a rel="nofollow" class="external text" href="https://www.nature.com/articles/142836b0">"A Hæmoglobin from Bile Pigment"</a>. <i>Nature</i>. <b>142</b> (3601): 836–837. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1938Natur.142..836B">1938Natur.142..836B</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1038%2F142836b0">10.1038/142836b0</a>. <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/1476-4687">1476-4687</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:4073510">4073510</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Nature&rft.atitle=A+H%C3%A6moglobin+from+Bile+Pigment&rft.volume=142&rft.issue=3601&rft.pages=836-837&rft.date=1938&rft_id=info%3Adoi%2F10.1038%2F142836b0&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A4073510%23id-name%3DS2CID&rft.issn=1476-4687&rft_id=info%3Abibcode%2F1938Natur.142..836B&rft.aulast=Barkan&rft.aufirst=Georg&rft.au=Schales%2C+Otto&rft_id=https%3A%2F%2Fwww.nature.com%2Farticles%2F142836b0&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABilirubin" class="Z3988"></span></span> </li> <li id="cite_note-71"><span class="mw-cite-backlink"><b><a href="#cite_ref-71">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.acs.org/content/acs/en/molecule-of-the-week/archive/b/bilirubin.html">"Bilirubin"</a>. <i>American Chemical Society</i><span class="reference-accessdate">. Retrieved <span class="nowrap">28 May</span> 2021</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=American+Chemical+Society&rft.atitle=Bilirubin&rft_id=https%3A%2F%2Fwww.acs.org%2Fcontent%2Facs%2Fen%2Fmolecule-of-the-week%2Farchive%2Fb%2Fbilirubin.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ABilirubin" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Bilirubin&action=edit&section=24" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.acb.org.uk/Nat%20Lab%20Med%20Hbk/Bililrubin.pdf">Bilirubin: analyte monograph</a> from The Association for Clinical Biochemistry and Laboratory Medicine</li></ul> <div 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href="/wiki/Bilin_(biochemistry)" title="Bilin (biochemistry)">Bilanes</a><br />(Linear)</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Bilirubin</a></li> <li><a href="/wiki/Biliverdin" title="Biliverdin">Biliverdin</a></li> <li><a href="/wiki/Stercobilinogen" title="Stercobilinogen">Stercobilinogen</a></li> <li><a href="/wiki/Stercobilin" title="Stercobilin">Stercobilin</a></li> <li><a href="/wiki/Urobilinogen" title="Urobilinogen">Urobilinogen</a></li> <li><a href="/wiki/Urobilin" title="Urobilin">Urobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytobilin&action=edit&redlink=1" class="new" title="Phytobilin (page does not exist)">Phytobilins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phytochromobilin" class="mw-redirect" title="Phytochromobilin">Phytochromobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phycobilin" title="Phycobilin">Phycobilins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phycoerythrobilin" title="Phycoerythrobilin">Phycoerythrobilin</a></li> <li><a href="/wiki/Phycocyanobilin" title="Phycocyanobilin">Phycocyanobilin</a></li> <li><a href="/wiki/Phycourobilin" title="Phycourobilin">Phycourobilin</a></li> <li><a href="/w/index.php?title=Phycoviolobilin&action=edit&redlink=1" class="new" title="Phycoviolobilin (page does not exist)">Phycoviolobilin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Macrocycle" title="Macrocycle">Macrocycle</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Corrinoid" title="Corrinoid">Corrinoids</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Protoporphyrin" class="mw-redirect" title="Protoporphyrin">Protoporphyrins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Heme" title="Heme">Heme</a> (<a href="/wiki/Heme_b" class="mw-redirect" title="Heme b"><i>b</i></a>, <a href="/wiki/Heme_c" class="mw-redirect" title="Heme c"><i>c</i></a>, <a href="/wiki/Heme_a" class="mw-redirect" title="Heme a"><i>a</i></a>, <a href="/wiki/Heme_o" class="mw-redirect" title="Heme o"><i>o</i></a>)</li> <li><a href="/w/index.php?title=Magnesium_protoporphyrin&action=edit&redlink=1" class="new" title="Magnesium protoporphyrin (page does not exist)">Magnesium protoporphyrin</a></li> <li><a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">Protoporphyrin IX</a></li> <li><a href="/wiki/Pterobilin" title="Pterobilin">Pterobilin</a></li> <li><a href="/wiki/Zinc_protoporphyrin" title="Zinc protoporphyrin">Zinc protoporphyrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytoporphyrin&action=edit&redlink=1" class="new" title="Phytoporphyrin (page does not exist)">Phytoporphyrins</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chlorophyll_c" title="Chlorophyll c">Chlorophyll <i>c</i></a></li> <li><a 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tests"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Clinical_biochemistry_blood_tests" title="Special:EditPage/Template:Clinical biochemistry blood tests"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Clinical_biochemistry_blood_tests" style="font-size:114%;margin:0 4em">Clinical biochemistry <a href="/wiki/Blood_test" title="Blood test">blood tests</a></div></th></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Electrolyte" title="Electrolyte">Electrolytes</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Serum_sodium" class="mw-redirect" title="Serum sodium">Sodium</a></li> <li><a href="/wiki/Potassium_in_biology" title="Potassium in biology">Potassium</a></li> <li><a href="/wiki/Serum_chloride" title="Serum chloride">Chloride</a></li> <li><a href="/wiki/Calcium_in_biology" title="Calcium in biology">Calcium</a></li> <li><a href="/wiki/Renal_function" class="mw-redirect" title="Renal function">Renal function</a> <ul><li><a href="/wiki/Creatinine" title="Creatinine">Creatinine</a></li> <li><a href="/wiki/Blood_urea_nitrogen" title="Blood urea nitrogen">Urea</a></li> <li><a href="/wiki/BUN-to-creatinine_ratio" class="mw-redirect" title="BUN-to-creatinine ratio">BUN-to-creatinine ratio</a></li></ul></li> <li><a href="/wiki/Plasma_osmolality" title="Plasma osmolality">Plasma osmolality</a></li> <li><a href="/wiki/Serum_osmolal_gap" class="mw-redirect" title="Serum osmolal gap">Serum osmolal gap</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Acid%E2%80%93base_homeostasis" title="Acid–base homeostasis">Acid-base</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Anion_gap" title="Anion gap">Anion gap</a></li> <li><a href="/wiki/Arterial_blood_gas_test" title="Arterial blood gas test">Arterial blood gas</a></li> <li><a href="/wiki/Base_excess" title="Base excess">Base excess</a></li> <li><a href="/wiki/Bicarbonate" title="Bicarbonate">Bicarbonate</a></li> <li><a href="/wiki/CO2_content" title="CO2 content">CO<sub>2</sub> content</a></li> <li><a href="/wiki/Lactic_acid#Blood_testing" title="Lactic acid">Lactate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Iron_tests" title="Iron tests">Iron tests</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ferritin" title="Ferritin">Ferritin</a></li> <li><a href="/wiki/Serum_iron" title="Serum iron">Serum iron</a></li> <li><a href="/wiki/Transferrin_saturation" title="Transferrin saturation">Transferrin saturation</a></li> <li><a href="/wiki/Total_iron-binding_capacity" title="Total iron-binding capacity">Total iron-binding capacity</a></li> <li><a href="/wiki/Transferrin" title="Transferrin">Transferrin</a></li> <li><a href="/wiki/Transferrin_receptor" title="Transferrin receptor">Transferrin receptor</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Endocrine_system" title="Endocrine system">Hormones</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/ACTH_stimulation_test" title="ACTH stimulation test">ACTH stimulation test</a></li> <li><a href="/wiki/Thyroid_function_tests" title="Thyroid function tests">Thyroid function tests</a> <ul><li><a href="/wiki/Thyroid-stimulating_hormone" title="Thyroid-stimulating hormone">Thyroid-stimulating hormone</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Metabolism" title="Metabolism">Metabolism</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Blood_glucose" class="mw-redirect" title="Blood glucose">Blood glucose</a> <ul><li><a href="/wiki/Glycated_hemoglobin" title="Glycated hemoglobin">Hemoglobin A1c</a></li></ul></li> <li><a href="/wiki/Lipid_panel" class="mw-redirect" title="Lipid panel">Lipid panel</a> <ul><li><a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">LDL</a></li> <li><a href="/wiki/High-density_lipoprotein" title="High-density lipoprotein">HDL</a></li> <li><a href="/wiki/Triglyceride#Role_in_disease" title="Triglyceride">Triglycerides</a></li> <li><a href="/wiki/Cholesterol#Clinical_significance" title="Cholesterol">Total cholesterol</a></li></ul></li> <li><a href="/wiki/Basic_metabolic_panel" title="Basic metabolic panel">Basic metabolic panel</a></li> <li><a href="/wiki/Comprehensive_metabolic_panel" title="Comprehensive metabolic panel">Comprehensive metabolic panel</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Cardiovascular_system" class="mw-redirect" title="Cardiovascular system">Cardiovascular</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cardiac_marker" title="Cardiac marker">Cardiac marker</a></li> <li><a href="/wiki/Troponin_test" class="mw-redirect" title="Troponin test">Troponin test</a></li> <li><a href="/wiki/CPK-MB_test" title="CPK-MB test">CPK-MB test</a></li> <li><a href="/wiki/Lactate_dehydrogenase" title="Lactate dehydrogenase">Lactate dehydrogenase</a></li> <li><a href="/wiki/Myoglobin" title="Myoglobin">Myoglobin</a></li> <li><a href="/wiki/Glycogen_phosphorylase_isoenzyme_BB" title="Glycogen phosphorylase isoenzyme BB">Glycogen phosphorylase isoenzyme BB</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Liver_function_tests" title="Liver function tests">Liver function tests</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>Proteins <ul><li><a href="/wiki/Human_serum_albumin" title="Human serum albumin">Human serum albumin</a></li> <li><a href="/wiki/Serum_total_protein" title="Serum total protein">Serum total protein</a></li></ul></li> <li><a href="/wiki/Alkaline_phosphatase" title="Alkaline phosphatase">ALP</a></li> <li><i><a href="/wiki/Transaminase" title="Transaminase">transaminases</a></i> <ul><li><a href="/wiki/Alanine_transaminase" title="Alanine transaminase">ALT</a></li> <li><a href="/wiki/Aspartate_transaminase" title="Aspartate transaminase">AST</a></li> <li><a href="/wiki/AST/ALT_ratio" title="AST/ALT ratio">AST/ALT ratio</a></li></ul></li> <li><a href="/wiki/Gamma-glutamyltransferase#Medical_applications" title="Gamma-glutamyltransferase">GGT</a></li> <li><a class="mw-selflink selflink">Bilirubin</a> <ul><li><a class="mw-selflink-fragment" href="#Unconjugated">Unconjugated</a></li> <li><a class="mw-selflink-fragment" href="#Conjugated">Conjugated</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Pancreas" title="Pancreas">Pancreas</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amylase" title="Amylase">Amylase</a></li> <li><a href="/wiki/Lipase" title="Lipase">Lipase</a> <ul><li><a href="/wiki/Pancreatic_lipase" class="mw-redirect" title="Pancreatic lipase">Pancreatic lipase</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%"><a href="/wiki/Small_molecule" title="Small molecule">Small molecules</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Blood_sugar_level" title="Blood sugar level">Blood sugar level</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/Hypoglycemia" title="Hypoglycemia">Hypoglycemia</a></li> <li><a href="/wiki/Hyperglycemia" title="Hyperglycemia">Hyperglycemia</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nitrogenous</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/Azotemia" title="Azotemia">Azotemia</a></li> <li><a href="/wiki/Hyperuricemia" title="Hyperuricemia">Hyperuricemia</a></li> <li><a href="/wiki/Hypouricemia" title="Hypouricemia">Hypouricemia</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="text-align: center;;width:1%">Proteins</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/Liver_function_tests" title="Liver function tests">LFT</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/Elevated_transaminases" title="Elevated transaminases">Elevated transaminases</a></li> <li><a href="/wiki/Elevated_alkaline_phosphatase" title="Elevated alkaline phosphatase">Elevated ALP</a></li> <li><a href="/wiki/Hypoproteinemia" title="Hypoproteinemia">Hypoproteinemia</a> <ul><li><a href="/wiki/Hypoalbuminemia" title="Hypoalbuminemia">Hypoalbuminemia</a></li></ul></li> <li><a href="/wiki/Hyperproteinemia" title="Hyperproteinemia">Hyperproteinemia</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Elevated_alpha-fetoprotein" title="Elevated alpha-fetoprotein">Elevated alpha-fetoprotein</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Heme_metabolic_intermediates" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Heme_metabolism_intermediates" title="Template:Heme metabolism intermediates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Heme_metabolism_intermediates" title="Template talk:Heme metabolism intermediates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Heme_metabolism_intermediates" title="Special:EditPage/Template:Heme metabolism intermediates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Heme_metabolic_intermediates" style="font-size:114%;margin:0 4em"><a href="/wiki/Heme" title="Heme">Heme</a> <a href="/wiki/Metabolic_intermediate" title="Metabolic intermediate">metabolic intermediates</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Porphyrin#Biosynthesis" title="Porphyrin">Porphyrin biosynthesis</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>early mitochondrial:</i></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminolevulinic_acid" title="Aminolevulinic acid">D-Aminolevulinic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>cytosolic:</i></span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Porphobilinogen" title="Porphobilinogen">Porphobilinogen</a></li> <li><a href="/wiki/Hydroxymethylbilane" title="Hydroxymethylbilane">Hydroxymethylbilane</a></li> <li><a href="/wiki/Uroporphyrinogen_III" title="Uroporphyrinogen III">Uroporphyrinogen III</a></li> <li><a href="/wiki/Coproporphyrinogen_III" title="Coproporphyrinogen III">Coproporphyrinogen III</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>late mitochondrial:</i></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Protoporphyrinogen_IX" title="Protoporphyrinogen IX">Protoporphyrinogen IX</a></li> <li><a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">Protoporphyrin IX</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/Heme#Degradation" title="Heme">Heme degradation</a><br />and excretion</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Breakdown_of_heme" scope="row" class="navbox-group" style="width:1%">Breakdown of heme</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%"><span class="nobold"><i>spleen:</i></span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Heme" title="Heme">Heme</a> → <a href="/wiki/Biliverdin" title="Biliverdin">Biliverdin</a> → <a class="mw-selflink selflink">Bilirubin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>blood:</i></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Bilirubin</a>+<a href="/wiki/Albumin" title="Albumin">Albumin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><span class="nobold"><i>liver:</i></span></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bilirubin_glucuronide" title="Bilirubin glucuronide">Bilirubin glucuronide</a></li> <li><a href="/wiki/Bilirubin_diglucuronide" title="Bilirubin diglucuronide">Bilirubin diglucuronide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intestine, excretion in feces</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/Stercobilinogen" title="Stercobilinogen">Stercobilinogen</a></li> <li><a href="/wiki/Stercobilin" title="Stercobilin">Stercobilin</a></li> <li><a href="/wiki/Urobilinogen" title="Urobilinogen">Urobilinogen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Kidney, excretion in urine</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/Urobilin" title="Urobilin">Urobilin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Aryl_hydrocarbon_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Aryl_hydrocarbon_receptor_modulators" title="Template:Aryl hydrocarbon receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Aryl_hydrocarbon_receptor_modulators" title="Template talk:Aryl hydrocarbon receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Aryl_hydrocarbon_receptor_modulators" title="Special:EditPage/Template:Aryl hydrocarbon receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Aryl_hydrocarbon_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor">Aryl hydrocarbon receptor</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align: center;"><a href="/wiki/Aryl_hydrocarbon_receptor" title="Aryl hydrocarbon receptor"><abbr title="Aryl hydrocarbon receptor">AhR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Aryl hydrocarbon receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i>Agonists:</i> <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a> <a href="/wiki/Metabolite" title="Metabolite">metabolites</a> (e.g., <a href="/wiki/Lipoxin_A4" class="mw-redirect" title="Lipoxin A4">lipoxin A4</a>, <a href="/wiki/Prostaglandin_G2" title="Prostaglandin G2">prostaglandin G2</a>)</li> <li><a href="/wiki/Carotenoid" title="Carotenoid">Dietary carotenoids</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Halogen" title="Halogen">Halogenated</a> <a href="/wiki/Aromatic_hydrocarbon" class="mw-redirect" title="Aromatic hydrocarbon">aromatic hydrocarbons</a> (e.g., <a href="/wiki/Polychlorinated_dibenzodioxin" class="mw-redirect" title="Polychlorinated dibenzodioxin">polychlorinated dibenzodioxins</a> (e.g., <a href="/wiki/2,3,7,8-Tetrachlorodibenzodioxin" title="2,3,7,8-Tetrachlorodibenzodioxin">TCDD</a>), <a href="/wiki/Dibenzofuran" title="Dibenzofuran">dibenzofurans</a>, <a href="/wiki/Biphenyl" title="Biphenyl">biphenyls</a>)</li> <li><a href="/w/index.php?title=2-(1H-Indol-3-ylcarbonyl)-4-thiazolecarboxylic_acid_methyl_ester&action=edit&redlink=1" class="new" title="2-(1H-Indol-3-ylcarbonyl)-4-thiazolecarboxylic acid methyl ester (page does not exist)">ΙΤΕ</a></li> <li><a href="/wiki/Low-density_lipoprotein" title="Low-density lipoprotein">Modified low-density lipoproteins</a></li> <li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbons</a> (e.g., <a href="/wiki/3-methylcholanthrene" class="mw-redirect" title="3-methylcholanthrene">3-methylcholanthrene</a>, <a href="/wiki/Benzo(a)pyrene" title="Benzo(a)pyrene">benzo[a]pyrene</a>, <a href="/wiki/Benzanthracene" class="mw-redirect" title="Benzanthracene">benzanthracenes</a>, <a href="/wiki/Benzoflavone" class="mw-redirect" title="Benzoflavone">benzoflavones</a> (e.g., <a href="/wiki/%CE%92-naphthoflavone" class="mw-redirect" title="Β-naphthoflavone">β-naphthoflavone</a>))</li> <li><a href="/wiki/Tapinarof" title="Tapinarof">Tapinarof (benvitimod)</a></li> <li><a href="/wiki/Tetrapyrole" class="mw-redirect" title="Tetrapyrole">Tetrapyroles</a> (e.g., <a class="mw-selflink selflink">bilirubin</a>)</li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a> <a href="/wiki/Chemical_derivative" class="mw-redirect" title="Chemical derivative">derivatives</a> (e.g., <a href="/wiki/Indigo_dye" title="Indigo dye">indigo dye</a>, <a href="/wiki/Indirubin" title="Indirubin">indirubin</a>)</li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=7-Ketocholesterol&action=edit&redlink=1" class="new" title="7-Ketocholesterol (page does not exist)">7-Ketocholesterol</a></li> <li><a href="/w/index.php?title=CH-223191&action=edit&redlink=1" class="new" title="CH-223191 (page does not exist)">CH-223191</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd></dl> </div></td></tr></tbody></table></div> <div 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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" 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data-file-width="20" data-file-height="20" /></a></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4145513-7">Germany</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Bilirubin"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85014033">United States</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Bilirubine"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb12302199m">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Bilirubine"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb12302199m">BnF data</a></span></span></li><li><span class="uid"><span 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