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mw-first-heading"><span class="mw-page-title-main">Calcifediol</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 19 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-19" 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">19 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D8%A7%D9%84%D8%B3%D9%8A%D9%81%D9%8A%D8%AF%D9%8A%D9%88%D9%84" title="كالسيفيديول – Arabic" lang="ar" hreflang="ar" data-title="كالسيفيديول" 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/%DA%A9%D9%84%D8%B3%DB%8C%D9%81%D8%AF%DB%8C%D9%88%D9%84" title="کلسیفدیول – South Azerbaijani" lang="azb" hreflang="azb" data-title="کلسیفدیول" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Calciffediol" title="Calciffediol – Welsh" lang="cy" hreflang="cy" data-title="Calciffediol" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Calcidiol" title="Calcidiol – German" lang="de" hreflang="de" data-title="Calcidiol" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Calcifediol" title="Calcifediol – Spanish" lang="es" hreflang="es" data-title="Calcifediol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Kaltzifediol" title="Kaltzifediol – Basque" lang="eu" hreflang="eu" data-title="Kaltzifediol" 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/%DA%A9%D9%84%D8%B3%DB%8C%D9%81%D8%AF%DB%8C%D9%88%D9%84" title="کلسیفدیول – Persian" lang="fa" hreflang="fa" data-title="کلسیفدیول" 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/Calcif%C3%A9diol" title="Calcifédiol – French" lang="fr" hreflang="fr" data-title="Calcifédiol" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Calcifediol" title="Calcifediol – Galician" lang="gl" hreflang="gl" data-title="Calcifediol" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Kalsifediol" title="Kalsifediol – Indonesian" lang="id" hreflang="id" data-title="Kalsifediol" 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/Calcidiolo" title="Calcidiolo – Italian" lang="it" hreflang="it" data-title="Calcidiolo" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Calcidiol" title="Calcidiol – Dutch" lang="nl" hreflang="nl" data-title="Calcidiol" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AB%E3%83%AB%E3%82%B7%E3%83%95%E3%82%A7%E3%82%B8%E3%82%AA%E3%83%BC%E3%83%AB" title="カルシフェジオール – Japanese" lang="ja" hreflang="ja" data-title="カルシフェジオール" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kalcyfediol" title="Kalcyfediol – Polish" lang="pl" hreflang="pl" data-title="Kalcyfediol" 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/Calcifediol" title="Calcifediol – Portuguese" lang="pt" hreflang="pt" data-title="Calcifediol" 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/Calcifediol" title="Calcifediol – Romanian" lang="ro" hreflang="ro" data-title="Calcifediol" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Kalcifediol" title="Kalcifediol – Serbian" lang="sr" hreflang="sr" data-title="Kalcifediol" 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/Kalcifediol" title="Kalcifediol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Kalcifediol" 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/Kalsidioli" title="Kalsidioli – Finnish" lang="fi" hreflang="fi" data-title="Kalsidioli" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li> </ul> <div class="after-portlet 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<div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">"Calcidiol" redirects here. For the drug marketed as "Calcidol", see <a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a>.</div> <style data-mw-deduplicate="TemplateStyles:r1084375498">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>Calcifediol </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Calcidiol2.svg" class="mw-file-description"><img alt="Skeletal formula of calcifediol" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Calcidiol2.svg/220px-Calcidiol2.svg.png" decoding="async" width="220" height="182" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Calcidiol2.svg/330px-Calcidiol2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3e/Calcidiol2.svg/440px-Calcidiol2.svg.png 2x" data-file-width="625" data-file-height="516" /></a></span> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Calcifediol_3D_ball.png" class="mw-file-description"><img alt="Ball-and-stick model of the calcifediol molecule" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Calcifediol_3D_ball.png/220px-Calcifediol_3D_ball.png" decoding="async" width="220" height="257" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/63/Calcifediol_3D_ball.png/330px-Calcifediol_3D_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/63/Calcifediol_3D_ball.png/440px-Calcifediol_3D_ball.png 2x" data-file-width="1715" data-file-height="2000" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(1<i>S</i>,3<i>Z</i>)-3-[(2<i>E</i>)-2-{(1<i>R</i>,3a<i>S</i>,7a<i>R</i>)-1-[(2<i>R</i>)-6-Hydroxy-6-methylheptan-2-yl]-7a-methyloctahydro-4<i>H</i>-inden-4-ylidene}ethylidene]-4-methylidenecyclohexan-1-ol</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;">25-Hydroxyvitamin D3<br />25-Hydroxycholecalciferol<br />Calcidiol<sup id="cite_ref-nomen-d_1-0" class="reference"><a href="#cite_note-nomen-d-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></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=19356-17-3">19356-17-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%5BC%40%40H%5D1CC%28%5CC%28%3DC%29CC1%29%3DC%5CC%3DC2%2FCCC%5BC%40%5D3%28%5BC%40H%5D2CC%5BC%40%40H%5D3%5BC%40H%5D%28C%29CCCC%28O%29%28C%29C%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17933">CHEBI:17933</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL1222">ChEMBL1222</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.4446820.html">4446820</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00146">DB00146</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/100.039.067">100.039.067</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q139307#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=6921">6921</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C01561">C01561</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a> </td> <td><span title="www.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://www.nlm.nih.gov/cgi/mesh/2014/MB_cgi?mode=&term=Calcifediol">Calcifediol</a></span> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5283731">5283731</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/T0WXW8F54E">T0WXW8F54E</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/DTXSID0022721">DTXSID0022721</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q139307#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/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: JWUBBDSIWDLEOM-DTOXIADCSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23+,24-,25+,27-/m1/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: JWUBBDSIWDLEOM-DTOXIADCBI</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CCCC(O)(C)C)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C<sub>27</sub>H<sub>44</sub>O<sub>2</sub>  </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>400.64 g/mol    </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_H05" title="ATC code H05">H05BX05</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=H05BX05">WHO</a></span>)  </td></tr> <tr> <td><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/12px-X_mark.svg.png" decoding="async" width="12" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/18px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/24px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=480474501&page2=Calcifediol">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>Calcifediol</b>, also known as <b>calcidiol</b>, <b>25-hydroxycholecalciferol</b>, or <b>25-hydroxyvitamin D<sub>3</sub></b> (abbreviated <b>25(OH)D<sub>3</sub></b>),<sup id="cite_ref-nomen-d_1-1" class="reference"><a href="#cite_note-nomen-d-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> is a form of <a href="/wiki/Vitamin_D" title="Vitamin D">vitamin D</a> produced in the <a href="/wiki/Liver" title="Liver">liver</a> by <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> of <a href="/wiki/Vitamin_D3" class="mw-redirect" title="Vitamin D3">vitamin D<sub>3</sub></a> (cholecalciferol) by the enzyme <a href="/wiki/Vitamin_D_25-hydroxylase" class="mw-redirect" title="Vitamin D 25-hydroxylase">vitamin D 25-hydroxylase</a>.<sup id="cite_ref-lpi_3-0" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NIH-ODS-2020_4-0" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bikle2014_5-0" class="reference"><a href="#cite_note-Bikle2014-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Calcifediol can be further hydroxylated by the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/25-Hydroxyvitamin_D3_1-alpha-hydroxylase" class="mw-redirect" title="25-Hydroxyvitamin D3 1-alpha-hydroxylase">25(OH)D-1α-hydroxylase</a>, primarily in the kidney, to form <a href="/wiki/Calcitriol" title="Calcitriol">calcitriol</a> (1,25-(OH)<sub>2</sub>D<sub>3</sub>), which is the active hormonal form of vitamin D.<sup id="cite_ref-lpi_3-1" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NIH-ODS-2020_4-1" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bikle2014_5-1" class="reference"><a href="#cite_note-Bikle2014-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Calcifediol is strongly bound in blood by the <a href="/wiki/Vitamin_D-binding_protein" title="Vitamin D-binding protein">vitamin D-binding protein</a>.<sup id="cite_ref-Bikle2014_5-2" class="reference"><a href="#cite_note-Bikle2014-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Measurement of serum calcifediol is the usual test performed to determine a person's vitamin D status, to show <a href="/wiki/Vitamin_D_deficiency" title="Vitamin D deficiency">vitamin D deficiency</a> or sufficiency.<sup id="cite_ref-NIH-ODS-2020_4-2" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bikle2014_5-3" class="reference"><a href="#cite_note-Bikle2014-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Calcifediol is available as an oral medication in some countries to supplement vitamin D status.<sup id="cite_ref-NIH-ODS-2020_4-3" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid29713796_6-0" class="reference"><a href="#cite_note-pmid29713796-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-RayaldeeFDA_7-0" class="reference"><a href="#cite_note-RayaldeeFDA-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Biology">Biology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Calcifediol&action=edit&section=1" title="Edit section: Biology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Calcifediol is the precursor for calcitriol, the active form of vitamin D.<sup id="cite_ref-lpi_3-2" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NIH-ODS-2020_4-4" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is synthesized in the liver, by hydroxylation of cholecalciferol (vitamin D<sub>3</sub>) at the 25-position.<sup id="cite_ref-lpi_3-3" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This enzymatic 25-hydroxylase reaction is mostly due to the actions of <a href="/wiki/CYP2R1" title="CYP2R1">CYP2R1</a>, present in <a href="/wiki/Microsomes" class="mw-redirect" title="Microsomes">microsomes</a>, although other enzymes such as <a href="/wiki/Mitochondrial" class="mw-redirect" title="Mitochondrial">mitochondrial</a> <a href="/wiki/CYP27A1" title="CYP27A1">CYP27A1</a> can contribute.<sup id="cite_ref-Bikle2014_5-4" class="reference"><a href="#cite_note-Bikle2014-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid31589774_8-0" class="reference"><a href="#cite_note-pmid31589774-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Variations in the expression and activity of CYP2R1, such as low levels in <a href="/wiki/Obesity" title="Obesity">obesity</a>, affect circulating calcifediol.<sup id="cite_ref-pmid31589774_8-1" class="reference"><a href="#cite_note-pmid31589774-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Similarly, vitamin D<sub>2</sub>, <a href="/wiki/Ergocalciferol" title="Ergocalciferol">ergocalciferol</a>, can also be 25-hydroxylated to form 25-hydroxyergocalciferol, (ercalcidiol, 25(OH)D<sub>2</sub>);<sup id="cite_ref-nomen-d_1-2" class="reference"><a href="#cite_note-nomen-d-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> both forms are measured together in blood as 25(OH)D.<sup id="cite_ref-lpi_3-4" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NIH-ODS-2020_4-5" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>At a typical intake of cholecalciferol (up to 2000 IU/day), conversion to calcifediol is rapid. When large doses are given (100,000 IU), it takes 7 days to reach peak calcifediol concentrations.<sup id="cite_ref-pmid18541563_9-0" class="reference"><a href="#cite_note-pmid18541563-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Calcifediol binds in the blood to vitamin D-binding protein (also known as gc-globulin) and is the main circulating vitamin D metabolite.<sup id="cite_ref-NIH-ODS-2020_4-6" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bikle2014_5-5" class="reference"><a href="#cite_note-Bikle2014-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Calcifediol has an <a href="/wiki/Elimination_half-life" class="mw-redirect" title="Elimination half-life">elimination half-life</a> of around 15 to 30 days.<sup id="cite_ref-NIH-ODS-2020_4-7" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid18541563_9-1" class="reference"><a href="#cite_note-pmid18541563-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Calcifediol is further hydroxylated at the 1-alpha-position in the kidneys to form 1,25-(OH)<sub>2</sub>D<sub>3</sub>, calcitriol.<sup id="cite_ref-lpi_3-5" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NIH-ODS-2020_4-8" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> This enzymatic <a href="/wiki/25-Hydroxyvitamin_D3_1-alpha-hydroxylase" class="mw-redirect" title="25-Hydroxyvitamin D3 1-alpha-hydroxylase">25(OH)D-1α-hydroxylase</a> reaction is performed exclusively by <a href="/wiki/CYP27B1" class="mw-redirect" title="CYP27B1">CYP27B1</a>, which is highly expressed in the kidneys where it is principally regulated by <a href="/wiki/Parathyroid_hormone" title="Parathyroid hormone">parathyroid hormone</a>, but also by <a href="/wiki/FGF23" class="mw-redirect" title="FGF23">FGF23</a> and calcitriol itself.<sup id="cite_ref-lpi_3-6" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Bikle2014_5-6" class="reference"><a href="#cite_note-Bikle2014-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid31589774_8-2" class="reference"><a href="#cite_note-pmid31589774-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> CYP27B1 is also expressed in a number of other tissues, including <a href="/wiki/Macrophages" class="mw-redirect" title="Macrophages">macrophages</a>, <a href="/wiki/Monocytes" class="mw-redirect" title="Monocytes">monocytes</a>, <a href="/wiki/Keratinocytes" class="mw-redirect" title="Keratinocytes">keratinocytes</a>, <a href="/wiki/Placenta" title="Placenta">placenta</a> and <a href="/wiki/Parathyroid_gland" title="Parathyroid gland">parathyroid gland</a> and extra-renal synthesis of calcitriol from calcifediol has been shown to have biological effects in these tissues.<sup id="cite_ref-pmid31589774_8-3" class="reference"><a href="#cite_note-pmid31589774-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid22446158_10-0" class="reference"><a href="#cite_note-pmid22446158-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>Calcifediol is also converted into <a href="/wiki/24,25-dihydroxycholecalciferol" class="mw-redirect" title="24,25-dihydroxycholecalciferol">24,25-dihydroxycholecalciferol</a> by 24-hydroxylation.<sup id="cite_ref-lpi_3-7" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> This enzymatic reaction is performed by <a href="/wiki/CYP24A1" title="CYP24A1">CYP24A1</a> which is expressed in many vitamin D target tissues including kidney, and is induced by calcitriol.<sup id="cite_ref-Bikle2014_5-7" class="reference"><a href="#cite_note-Bikle2014-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> This will inactivate calcitriol to <a href="/wiki/Calcitroic_acid" title="Calcitroic acid">calcitroic acid</a>, but 24,25-(OH)<sub>2</sub>D<sub>3</sub> may have some biological actions itself.<sup id="cite_ref-Bikle2014_5-8" class="reference"><a href="#cite_note-Bikle2014-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Blood_test_for_vitamin_D_deficiency">Blood test for vitamin D deficiency</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Calcifediol&action=edit&section=2" title="Edit section: Blood test for vitamin D deficiency"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Vitamin_D#Recommended_serum_levels" title="Vitamin D">Vitamin D § Recommended serum levels</a></div> <p>In medical practice, a blood test for 25-hydroxy-vitamin D, 25(OH)D, is used to determine an individual's vitamin D status.<sup id="cite_ref-MedlinePlus_11-0" class="reference"><a href="#cite_note-MedlinePlus-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The name 25(OH)D refers to any combination of calcifediol (25-hydroxy-cholecalciferol), derived from vitamin D<sub>3</sub>, and ercalcidiol (25-hydroxy-ergocalciferol),<sup id="cite_ref-nomen-d_1-3" class="reference"><a href="#cite_note-nomen-d-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> derived from vitamin D<sub>2</sub>. The first of these (also known as 25-hydroxy vitamin D3) is made by the body, or is sourced from certain animal foods or cholecalciferol supplements. The second (25-hydroxy vitamin D2) is from certain vegetable foods or ergocalciferol supplements.<sup id="cite_ref-MedlinePlus_11-1" class="reference"><a href="#cite_note-MedlinePlus-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Clinical tests for 25(OH)D often measure the total level of both of these two compounds together, generally without differentiating.<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>This measurement is considered the best indicator of overall vitamin D status.<sup id="cite_ref-MedlinePlus_11-2" class="reference"><a href="#cite_note-MedlinePlus-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-heaney_13-0" class="reference"><a href="#cite_note-heaney-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> US labs generally report 25(OH)D levels as ng/mL. Other countries use nmol/L. Multiply ng/mL by 2.5 to convert to nmol/L.<sup id="cite_ref-NIH-ODS-2020_4-9" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>This test can be used to diagnose <a href="/wiki/Vitamin_D_deficiency" title="Vitamin D deficiency">vitamin D deficiency</a>, and is performed in people with high risk for vitamin D deficiency, when the results of the test can be used to support beginning replacement therapy with vitamin D supplements.<sup id="cite_ref-NIH-ODS-2020_4-10" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ASCPfive_15-0" class="reference"><a href="#cite_note-ASCPfive-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Patients with <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>, <a href="/wiki/Chronic_kidney_disease" title="Chronic kidney disease">chronic kidney disease</a>, <a href="/wiki/Malabsorption" title="Malabsorption">malabsorption</a>, <a href="/wiki/Obesity" title="Obesity">obesity</a>, and some other infections may be at greater risk for being vitamin D-deficient and so are more likely to have this test.<sup id="cite_ref-ASCPfive_15-1" class="reference"><a href="#cite_note-ASCPfive-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Although vitamin D deficiency is common in some populations including those living at higher latitudes or with limited sun exposure, the 25(OH)D test is not usually requested for the entire population.<sup id="cite_ref-ASCPfive_15-2" class="reference"><a href="#cite_note-ASCPfive-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Physicians may advise low risk patients to take <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> vitamin D supplements in place of having screening.<sup id="cite_ref-ASCPfive_15-3" class="reference"><a href="#cite_note-ASCPfive-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>It is the most <a href="/wiki/Sensitivity_and_specificity" title="Sensitivity and specificity">sensitive</a> measure, though experts have called for improved standardization and reproducibility across different laboratories.<sup id="cite_ref-NIH-ODS-2020_4-11" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-heaney_13-1" class="reference"><a href="#cite_note-heaney-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> According to <a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a>, the recommended range of 25(OH)D is 20 to 40 ng/mL (50 to 100 nmol/L) though they recognize many experts recommend 30 to 50 ng/mL (75 to 125 nmol/L).<sup id="cite_ref-MedlinePlus_11-3" class="reference"><a href="#cite_note-MedlinePlus-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The normal range varies widely depending on several factors, including age and geographic location. A broad <a href="/wiki/Reference_ranges_for_blood_tests" title="Reference ranges for blood tests">reference range</a> of 20 to 150 nmol/L (8-60 ng/mL) has also been suggested,<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> while other studies have defined levels below 80 nmol/L (32 ng/mL) as indicative of vitamin D deficiency.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Increasing calcifediol levels up to levels of 80 nmol/L (32 ng/mL) are associated with increasing the fraction of calcium that is absorbed from the gut.<sup id="cite_ref-heaney_13-2" class="reference"><a href="#cite_note-heaney-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Urinary calcium excretion balances intestinal calcium absorption and does not increase with calcifediol levels up to ~400 nmol/L (160 ng/mL).<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Supplementation">Supplementation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Calcifediol&action=edit&section=3" title="Edit section: Supplementation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Calcifediol supplements have been used in some studies to improve vitamin D status.<sup id="cite_ref-NIH-ODS-2020_4-12" class="reference"><a href="#cite_note-NIH-ODS-2020-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Indications for their use include vitamin D deficiency or insufficiency, refractory rickets (<a href="/wiki/Vitamin_D_resistant_rickets" class="mw-redirect" title="Vitamin D resistant rickets">vitamin D resistant rickets</a>), <a href="/wiki/Familial_hypophosphatemia" class="mw-redirect" title="Familial hypophosphatemia">familial hypophosphatemia</a>, <a href="/wiki/Hypoparathyroidism" title="Hypoparathyroidism">hypoparathyroidism</a>, hypocalcemia and <a href="/wiki/Renal_osteodystrophy" title="Renal osteodystrophy">renal osteodystrophy</a> and, with calcium, in primary or corticosteroid-induced <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Calcifediol may have advantages over cholecalciferol for the correction of vitamin D deficiency states.<sup id="cite_ref-pmid29713796_6-1" class="reference"><a href="#cite_note-pmid29713796-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> A review of the results of nine <a href="/wiki/Randomized_control_trials" class="mw-redirect" title="Randomized control trials">randomized control trials</a> which compared oral doses of both, found that calcifediol was 3.2-fold more potent than cholecalciferol.<sup id="cite_ref-pmid29713796_6-2" class="reference"><a href="#cite_note-pmid29713796-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Calcifediol is better absorbed from the intestine and has greater affinity for the vitamin-D-binding protein, both of which increase its bioavailability.<sup id="cite_ref-pmid31064117_20-0" class="reference"><a href="#cite_note-pmid31064117-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Orally administered calcifediol has a much shorter half-life with faster elimination.<sup id="cite_ref-pmid31064117_20-1" class="reference"><a href="#cite_note-pmid31064117-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> These properties may be beneficial in people with intestinal <a href="/wiki/Malabsorption" title="Malabsorption">malabsorption</a>, obesity, or treated with certain other medications.<sup id="cite_ref-pmid31064117_20-2" class="reference"><a href="#cite_note-pmid31064117-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>In 2016, the FDA approved a formulation of calcifediol (Rayaldee) 60 microgram daily as a prescription medication to treat secondary <a href="/wiki/Hyperparathyroidism" title="Hyperparathyroidism">hyperparathyroidism</a> in patients with <a href="/wiki/Chronic_kidney_disease" title="Chronic kidney disease">chronic kidney disease</a>.<sup id="cite_ref-RayaldeeFDA_7-1" class="reference"><a href="#cite_note-RayaldeeFDA-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactive_pathway_map">Interactive pathway map</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Calcifediol&action=edit&section=4" title="Edit section: Interactive pathway map"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div style="overflow:auto;text-align: right"> <p><i>Click on genes, proteins and metabolites below to link to respective articles.</i> <sup id="cite_ref-WikiPathways_21-0" class="reference"><a href="#cite_note-WikiPathways-21"><span class="cite-bracket">[</span>§ 1<span class="cite-bracket">]</span></a></sup> </p> <div class="thumb tright"> <div class="thumbinner" style="width: 377px;"> <div class="thumbimage" style="width: 375px; height: 350px; overflow: hidden;"> <div style="position: relative; top: -335.917704536249px; left: -96.8837858324146px; width: {{{bSize}}}px"><div class="noresize">[[File:<div class="noresize thumb tnone" style=";"> <div class="thumbinner" style="overflow:hidden;width:1118px;"> <div class="thumbimage" style="overflow:hidden; position:relative; background-color:white;"> <div style=";left:0px; top:0px; width:1116px; position:absolute;"> <figure class="mw-default-size mw-halign-right noresize" typeof="mw:File"><a href="/wiki/Vitamin_D#Interactive_pathway_map" title="Go to pathway article"><img alt="VitaminDSynthesis_WP1531" src="//upload.wikimedia.org/wikipedia/commons/2/27/VitaminDSynthesis_WP1531.png" decoding="async" width="1116" height="1069" class="mw-file-element" data-file-width="1116" data-file-height="1069" usemap="#ImageMap_80523bcf44d6d157" /></a><map name="ImageMap_80523bcf44d6d157"><area href="/wiki/7-Dehydrocholesterol" shape="rect" coords="238,109,314,137" alt="Go to article" title="Go to article" /><area href="/wiki/Previtamin_D3" shape="rect" coords="233,227,318,252" alt="Go to article" title="Go to article" /><area href="/wiki/Cholecalciferol" shape="rect" coords="228,307,321,332" alt="Go to article" title="Go to article" /><area href="/wiki/Calcifediol" shape="rect" coords="243,471,306,501" alt="Go to article" title="Go to article" /><area href="/wiki/CYP2R1" shape="rect" coords="246,377,305,400" alt="go to article" title="go to article" /><area href="/wiki/Calcifediol" shape="rect" coords="593,471,655,501" alt="Go to article" title="Go to article" /><area href="/wiki/24,25-Dihydroxycholecalciferol" shape="rect" coords="1001,465,1087,505" alt="Go to article" title="Go to article" /><area href="/wiki/Calcitriol" shape="rect" coords="586,751,662,778" alt="Go to article" title="Go to article" /><area href="/wiki/25-Hydroxyvitamin_D3_1-alpha-hydroxylase" shape="rect" coords="581,680,664,707" alt="go to article" title="go to article" /><area href="/wiki/Parathyroid_hormone" shape="rect" coords="704,582,822,607" alt="go to article" title="go to article" /><area href="/wiki/CYP24A1" shape="rect" coords="857,474,933,499" alt="go to article" title="go to article" /><area href="/wiki/Vitamin_D-binding_protein" shape="rect" coords="656,814,797,843" alt="go to article" title="go to article" /><area href="/wiki/Calcium_in_biology" shape="rect" coords="762,709,789,729" alt="Go to article" title="Go to article" /><area href="/wiki/Phosphate" shape="rect" coords="789,709,816,729" alt="Go to article" title="Go to article" /><area href="/wiki/Calcitriol_receptor" shape="rect" coords="594,894,654,923" alt="go to article" title="go to article" /><area href="/wiki/Vitamin_D-binding_protein" shape="rect" coords="370,330,514,357" alt="Go to article" title="Go to article" /><area href="/wiki/CYP27A1" shape="rect" coords="246,400,305,422" alt="go to article" title="go to article" /><area href="/wiki/Retinoid_X_receptor_alpha" shape="rect" coords="676,911,732,934" alt="go to article" title="go to article" /><area href="/wiki/Retinoid_X_receptor_beta" shape="rect" coords="676,934,732,957" alt="go to article" title="go to article" /><area href="/wiki/Cholesterol" shape="rect" coords="235,29,315,49" alt="Go to article" title="Go to article" /><area href="/wiki/7-Dehydrocholesterol_reductase" shape="rect" coords="245,72,307,92" alt="go to article" title="go to article" /></map><figcaption></figcaption></figure></div> <div style="text-align:left; background-color:transparent; color:white; line-height:110%;"> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:76px; height:0px; overflow:hidden; position:relative; left:237.79492833517088px; top:121.919335370502px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:85px; height:0px; overflow:hidden; position:relative; left:233.0px; top:237px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span 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style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:27px; height:0px; overflow:hidden; position:relative; left:788.6957001102534px; top:714.059683236407px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:59.4692642691966px; height:0px; overflow:hidden; position:relative; left:594.077867865401px; top:908.021871202915px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:144.25px; height:0px; overflow:hidden; position:relative; left:369.9992649761124px; top:341.735767396645px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:59.3333333333332px; height:0px; overflow:hidden; position:relative; left:245.97243660418965px; top:407.25533740767px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:55.666666666667px; height:0px; overflow:hidden; position:relative; left:676.333333333333px; top:919.021871202916px; background:transparent; border-top:3px blue solid"></div>]]</span></div> <div id="annotation_0x0" style="position:absolute; left:0px; top:0px; line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; 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line-height:110%;"><span style="background-color:transparent; color:inherit;">[[<div style="display:block; width:55.5625px; height:22.2083333333355px; overflow:hidden; position:relative; left:243.10253583241456px; top:458.813537869581px; background:transparent; border:4px black solid"></div>]]</span></div> </div> <div style="visibility:hidden"><figure class="mw-default-size mw-halign-right noresize" typeof="mw:File"><a href="/wiki/Vitamin_D#Interactive_pathway_map" title="Go to pathway article"><img alt="VitaminDSynthesis_WP1531" src="//upload.wikimedia.org/wikipedia/commons/2/27/VitaminDSynthesis_WP1531.png" decoding="async" width="1116" height="1069" class="mw-file-element" data-file-width="1116" data-file-height="1069" usemap="#ImageMap_80523bcf44d6d157" /></a><map name="ImageMap_80523bcf44d6d157"><area href="/wiki/7-Dehydrocholesterol" shape="rect" coords="238,109,314,137" alt="Go to article" title="Go to article" /><area href="/wiki/Previtamin_D3" shape="rect" coords="233,227,318,252" alt="Go to article" title="Go to article" /><area href="/wiki/Cholecalciferol" shape="rect" coords="228,307,321,332" alt="Go to article" title="Go to article" /><area href="/wiki/Calcifediol" shape="rect" coords="243,471,306,501" alt="Go to article" title="Go to article" /><area href="/wiki/CYP2R1" shape="rect" coords="246,377,305,400" alt="go to article" title="go to article" /><area href="/wiki/Calcifediol" shape="rect" coords="593,471,655,501" alt="Go to article" title="Go to article" /><area href="/wiki/24,25-Dihydroxycholecalciferol" shape="rect" coords="1001,465,1087,505" alt="Go to article" title="Go to article" /><area href="/wiki/Calcitriol" shape="rect" coords="586,751,662,778" alt="Go to article" title="Go to article" /><area href="/wiki/25-Hydroxyvitamin_D3_1-alpha-hydroxylase" shape="rect" coords="581,680,664,707" alt="go to article" title="go to article" /><area href="/wiki/Parathyroid_hormone" shape="rect" coords="704,582,822,607" alt="go to article" title="go to article" /><area href="/wiki/CYP24A1" shape="rect" coords="857,474,933,499" alt="go to article" title="go to article" /><area href="/wiki/Vitamin_D-binding_protein" shape="rect" coords="656,814,797,843" alt="go to article" title="go to article" /><area href="/wiki/Calcium_in_biology" shape="rect" coords="762,709,789,729" alt="Go to article" title="Go to article" /><area href="/wiki/Phosphate" shape="rect" coords="789,709,816,729" alt="Go to article" title="Go to article" /><area href="/wiki/Calcitriol_receptor" shape="rect" coords="594,894,654,923" alt="go to article" title="go to article" /><area href="/wiki/Vitamin_D-binding_protein" shape="rect" coords="370,330,514,357" alt="Go to article" title="Go to article" /><area href="/wiki/CYP27A1" shape="rect" coords="246,400,305,422" alt="go to article" title="go to article" /><area href="/wiki/Retinoid_X_receptor_alpha" shape="rect" coords="676,911,732,934" alt="go to article" title="go to article" /><area href="/wiki/Retinoid_X_receptor_beta" shape="rect" coords="676,934,732,957" alt="go to article" title="go to article" /><area href="/wiki/Cholesterol" shape="rect" coords="235,29,315,49" alt="Go to article" title="Go to article" /><area href="/wiki/7-Dehydrocholesterol_reductase" shape="rect" coords="245,72,307,92" alt="go to article" title="go to article" /></map><figcaption></figcaption></figure></div> </div> <div class="thumbcaption"></div> </div></div>|alt=Vitamin D Synthesis Pathway (<a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP1531">view</a> / <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php?title=Pathway:WP1531&action=edit">edit</a>)]]</div></div> </div> <div class="thumbcaption"> <div class="magnify"><a href="/wiki/File:VitaminDSynthesis_WP1531.png" title="File:VitaminDSynthesis WP1531.png"> </a></div>Vitamin D Synthesis Pathway (<a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP1531">view</a> / <a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php?title=Pathway:WP1531&action=edit">edit</a>) </div> </div> </div> <div style="clear:both;" class=""></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-WikiPathways-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-WikiPathways_21-0">^</a></b></span> <span class="reference-text">The interactive pathway map can be edited at WikiPathways: <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.wikipathways.org/index.php/Pathway:WP1531">"VitaminDSynthesis_WP1531"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=VitaminDSynthesis_WP1531&rft_id=http%3A%2F%2Fwww.wikipathways.org%2Findex.php%2FPathway%3AWP1531&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACalcifediol" class="Z3988"></span></span> </li> </ol></div></div> </div> <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=Calcifediol&action=edit&section=5" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Research in the laboratory of <a href="/wiki/Hector_DeLuca" title="Hector DeLuca">Hector DeLuca</a> identified 25(OH)D in 1968 and showed that the liver was necessary for its formation.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> The enzyme responsible for this synthesis, <a href="/wiki/Cholecalciferol_25-hydroxylase" class="mw-redirect" title="Cholecalciferol 25-hydroxylase">cholecalciferol 25-hydroxylase</a>, was isolated in the same laboratory by <a href="/wiki/Michael_F._Holick" title="Michael F. Holick">Michael F. Holick</a> in 1972.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Research">Research</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Calcifediol&action=edit&section=6" title="Edit section: Research"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Studies are ongoing comparing the effects of calcifediol with other forms of vitamin D including cholecalciferol in prevention and treatment of <a href="/wiki/Osteoporosis" title="Osteoporosis">osteoporosis</a>.<sup id="cite_ref-lpi_3-8" class="reference"><a href="#cite_note-lpi-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid31064117_20-3" class="reference"><a href="#cite_note-pmid31064117-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Other_Organisms">Other Organisms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Calcifediol&action=edit&section=7" title="Edit section: Other Organisms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Teleost_Fish">Teleost Fish</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Calcifediol&action=edit&section=8" title="Edit section: Teleost Fish"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In teleost fish, calcifediol is predominantly converted to <a href="/wiki/Calcitriol" title="Calcitriol">calcitriol</a> in the liver, rather than in the kidneys<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> which means circulating levels of calcifediol can be undetectable and alternative measures of vitamin D status are required. There has been some success in using dietary calcifediol supplementation in salmonids to improve growth and food conversion ratio.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Calcifediol&action=edit&section=9" 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-nomen-d-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-nomen-d_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-nomen-d_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-nomen-d_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-nomen-d_1-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation journal cs1"><a rel="nofollow" class="external text" href="https://doi.org/10.1111%2Fj.1432-1033.1982.tb06581.x">"IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN): Nomenclature of vitamin D. 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Vitamins" title="Template:Vitamins"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Vitamins" title="Template talk:Vitamins"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Vitamins" title="Special:EditPage/Template:Vitamins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Vitamins_(A11)" style="font-size:114%;margin:0 4em"><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a> (<a href="/wiki/ATC_code_A11" title="ATC code A11">A11</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fat <br />soluble</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_A" title="Vitamin A">A</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/%CE%91-Carotene" title="Α-Carotene">α-Carotene</a></li> <li><a href="/wiki/%CE%92-Carotene" title="Β-Carotene">β-Carotene</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a><sup>#</sup></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_D" title="Vitamin D">D</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>D<sub>2</sub> <ul><li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a><sup>#</sup></li></ul></li> <li>D<sub>3</sub> <ul><li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Previtamin_D3" title="Previtamin D3">Previtamin D<sub>3</sub></a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a><sup>#</sup></li> <li><a class="mw-selflink selflink">25-hydroxycholecalciferol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol (1,25-dihydroxycholecalciferol)</a></li> <li><a href="/wiki/Calcitroic_acid" title="Calcitroic acid">Calcitroic acid</a></li></ul></li> <li>D<sub>4</sub> <ul><li><a href="/wiki/22-Dihydroergocalciferol" title="22-Dihydroergocalciferol">Dihydroergocalciferol</a></li></ul></li> <li><a href="/wiki/Vitamin_D5" title="Vitamin D5">D<sub>5</sub></a></li> <li>D analogues <ul><li><a href="/wiki/Alfacalcidol" title="Alfacalcidol">Alfacalcidol</a></li> <li><a href="/wiki/Dihydrotachysterol" title="Dihydrotachysterol">Dihydrotachysterol</a></li> <li><a href="/wiki/Calcipotriol" title="Calcipotriol">Calcipotriol</a></li> <li><a href="/wiki/Tacalcitol" title="Tacalcitol">Tacalcitol</a></li> <li><a href="/wiki/Paricalcitol" title="Paricalcitol">Paricalcitol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_E" title="Vitamin E">E</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Tocopherol" title="Tocopherol">Tocopherol</a> <ul><li><a href="/wiki/%CE%91-Tocopherol" title="Α-Tocopherol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocopherol" title="Β-Tocopherol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocopherol" title="Γ-Tocopherol">Gamma</a></li> <li><a href="/wiki/%CE%94-Tocopherol" title="Δ-Tocopherol">Delta</a></li></ul></li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienol</a> <ul><li><a href="/wiki/%CE%91-Tocotrienol" title="Α-Tocotrienol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocotrienol" title="Β-Tocotrienol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocotrienol" title="Γ-Tocotrienol">Gamma</a></li> <li>Delta</li></ul></li> <li><a href="/wiki/Tocofersolan" title="Tocofersolan">Tocofersolan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_K" title="Vitamin K">K</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/1,4-Naphthoquinone" title="1,4-Naphthoquinone">Naphthoquinone</a></li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone (K<sub>1</sub>)</a><sup>#</sup></li> <li><a href="/wiki/Vitamin_K2" title="Vitamin K2">Menaquinones (K<sub>2</sub>)</a></li> <li><a href="/wiki/Menadione" title="Menadione">Menadione (K<sub>3</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/Vitamin_K4" class="mw-redirect" title="Vitamin K4">Various (K<sub>4</sub>)</a></li> <li><a href="/wiki/4-Amino-2-methyl-1-naphthol" title="4-Amino-2-methyl-1-naphthol">4-Amino-2-methyl-1-naphthol (K<sub>5</sub>)</a><sup>‡</sup></li> <li><a href="/wiki/2-Methylnaphthalene-1,4-diamine" title="2-Methylnaphthalene-1,4-diamine">2-Methylnaphthalene-1,4-diamine (K<sub>6</sub>)</a></li> <li><a href="/wiki/4-Amino-3-methyl-1-naphthol" title="4-Amino-3-methyl-1-naphthol">4-Amino-3-methyl-1-naphthol (K<sub>7</sub>)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Water <br />soluble</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/B_vitamins" title="B vitamins">B</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>B<sub>1</sub> <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B1_analogues" title="Vitamin B1 analogues">B<sub>1</sub> analogues</a> <ul><li><a href="/wiki/Acefurtiamine" title="Acefurtiamine">Acefurtiamine</a></li> <li><a href="/wiki/Allithiamine" title="Allithiamine">Allithiamine</a></li> <li><a href="/wiki/Benfotiamine" title="Benfotiamine">Benfotiamine</a></li> <li><a href="/wiki/Fursultiamine" title="Fursultiamine">Fursultiamine</a></li> <li><a href="/wiki/Octotiamine" title="Octotiamine">Octotiamine</a></li> <li><a href="/wiki/Prosultiamine" title="Prosultiamine">Prosultiamine</a></li> <li><a href="/wiki/Sulbutiamine" title="Sulbutiamine">Sulbutiamine</a></li></ul></li> <li>B<sub>2</sub> <ul><li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin</a><sup>#</sup></li></ul></li> <li><a href="/wiki/Vitamin_B3" title="Vitamin B3">B<sub>3</sub></a> <ul><li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Niacinamide</a><sup>#</sup></li></ul></li> <li>B<sub>5</sub> <ul><li><a href="/wiki/Pantothenic_acid" title="Pantothenic acid">Pantothenic acid</a></li> <li><a href="/wiki/Panthenol" title="Panthenol">Dexpanthenol</a></li> <li><a href="/wiki/Pantethine" title="Pantethine">Pantethine</a></li></ul></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">B<sub>6</sub></a> <ul><li><a href="/wiki/Pyridoxine" title="Pyridoxine">Pyridoxine</a><sup>#</sup>, <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">Pyridoxal phosphate</a></li> <li><a href="/wiki/Pyridoxamine" title="Pyridoxamine">Pyridoxamine</a></li> <li><a href="/wiki/Pyritinol" title="Pyritinol">Pyritinol</a></li></ul></li> <li>B<sub>7</sub> <ul><li><a href="/wiki/Biotin" title="Biotin">Biotin</a></li></ul></li> <li>B<sub>9</sub> <ul><li><a href="/wiki/Folate" title="Folate">Folic acid</a><sup>#</sup></li> <li><a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">Dihydrofolic acid</a></li> <li><a href="/wiki/Folinic_acid" title="Folinic acid">Folinic acid</a></li> <li><a href="/wiki/Levomefolic_acid" title="Levomefolic acid">Levomefolic acid</a></li></ul></li> <li><a href="/wiki/Vitamin_B12" title="Vitamin B12">B<sub>12</sub></a> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a><sup>#</sup></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_C" title="Vitamin C">C</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Vitamin_C" title="Vitamin C">Ascorbic acid</a><sup>#</sup></li> <li><a href="/wiki/Dehydroascorbic_acid" title="Dehydroascorbic acid">Dehydroascorbic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Multivitamin" title="Multivitamin">Multivitamins</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Calcium_homeostasis_(H05)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a 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style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abaloparatide" title="Abaloparatide">Abaloparatide</a></li> <li><a href="/wiki/Palopegteriparatide" title="Palopegteriparatide">Palopegteriparatide</a></li> <li><a href="/w/index.php?title=Parathyroid_gland_extract&action=edit&redlink=1" class="new" title="Parathyroid gland extract (page does not exist)">Parathyroid gland extract</a></li> <li><a href="/wiki/Teriparatide" title="Teriparatide">Teriparatide</a></li> <li><a href="/wiki/Recombinant_human_parathyroid_hormone" title="Recombinant human parathyroid hormone">Recombinant human parathyroid hormone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Anti-parathyroid hormone agents</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%">Calcitonin derivatives</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/Calcitonin" title="Calcitonin">Calcitonin</a></li> <li><a href="/wiki/Elcatonin" title="Elcatonin">Elcatonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Calcimimetics</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/Cinacalcet" title="Cinacalcet">Cinacalcet</a></li> <li><a href="/wiki/Etelcalcetide" title="Etelcalcetide">Etelcalcetide</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 class="mw-selflink selflink">Calcifediol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li> <li><a href="/wiki/Cinacalcet" title="Cinacalcet">Cinacalcet</a></li> <li><a href="/wiki/Doxercalciferol" title="Doxercalciferol">Doxercalciferol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li> <li><a href="/wiki/Etelcalcetide" title="Etelcalcetide">Etelcalcetide</a></li> <li><a href="/wiki/Evocalcet" title="Evocalcet">Evocalcet</a></li> <li><a href="/wiki/Paricalcitol" title="Paricalcitol">Paricalcitol</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="Vitamin_D_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:Vitamin_D_receptor_modulators" title="Template:Vitamin D receptor modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Vitamin_D_receptor_modulators" title="Template talk:Vitamin D receptor modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Vitamin_D_receptor_modulators" title="Special:EditPage/Template:Vitamin D receptor modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Vitamin_D_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Vitamin_D_receptor" title="Vitamin D receptor">Vitamin D 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/Vitamin_D_receptor" title="Vitamin D receptor"><abbr title="Vitamin D receptor">VDR</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 Vitamin D 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/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/w/index.php?title=25-Hydroxyergocalciferol&action=edit&redlink=1" class="new" title="25-Hydroxyergocalciferol (page does not exist)">25-Hydroxyergocalciferol</a></li> <li><a href="/wiki/Alfacalcidol" title="Alfacalcidol">Alfacalcidol</a></li> <li><a class="mw-selflink selflink">Calcifediol</a></li> <li><a href="/wiki/Calciferol" class="mw-redirect" title="Calciferol">Calciferol</a></li> <li><a href="/wiki/Calcipotriol" title="Calcipotriol">Calcipotriol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a> (<a href="/wiki/Vitamin_D3" class="mw-redirect" title="Vitamin D3">vitamin D<sub>3</sub></a>)</li> <li><a href="/wiki/Dihydrotachysterol" title="Dihydrotachysterol">Dihydrotachysterol</a></li> <li><a href="/wiki/Doxercalciferol" title="Doxercalciferol">Doxercalciferol</a></li> <li><a href="/w/index.php?title=EB-1089&action=edit&redlink=1" class="new" title="EB-1089 (page does not exist)">EB-1089</a></li> <li><a href="/wiki/Eldecalcitol" title="Eldecalcitol">Eldecalcitol</a></li> <li><a href="/w/index.php?title=Ercalcidiol&action=edit&redlink=1" class="new" title="Ercalcidiol (page does not exist)">Ercalcidiol</a></li> <li><a href="/w/index.php?title=Ercalcitriol&action=edit&redlink=1" class="new" title="Ercalcitriol (page does not exist)">Ercalcitriol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a> (<a href="/wiki/Vitamin_D2" class="mw-redirect" title="Vitamin D2">vitamin D<sub>2</sub></a>)</li> <li><a href="/wiki/Lithocholic_acid" title="Lithocholic acid">Lithocholic acid</a></li> <li><a href="/wiki/Maxacalcitol" title="Maxacalcitol">Maxacalcitol</a></li> <li><a href="/wiki/Paricalcitol" title="Paricalcitol">Paricalcitol</a></li> <li><a href="/wiki/Tacalcitol" title="Tacalcitol">Tacalcitol</a></li></ul> <ul><li><i>Antagonists:</i> <a href="/w/index.php?title=ZK159222&action=edit&redlink=1" class="new" title="ZK159222 (page does not exist)">ZK159222</a></li> <li><a href="/w/index.php?title=TEI-9647&action=edit&redlink=1" class="new" title="TEI-9647 (page does not exist)">TEI-9647</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> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output 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