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id="toc-Ligands" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Ligands"> <div class="vector-toc-text"> 3 Ligands </div> </a> <ul id="toc-Ligands-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Epoxygenase_activity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Epoxygenase_activity"> <div class="vector-toc-text"> 4 Epoxygenase activity </div> </a> <ul id="toc-Epoxygenase_activity-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"> 5 See also </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div 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class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/CYP2C9" title="CYP2C9 – Spanish" lang="es" hreflang="es" data-title="CYP2C9" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/CYP2C9" title="CYP2C9 – Persian" lang="fa" hreflang="fa" data-title="CYP2C9" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/CYP2C9" title="CYP2C9 – Latin" lang="la" hreflang="la" data-title="CYP2C9" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target">Latina</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a 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</div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Enzyme protein</div> <table class="infobox" style="width:26.4em"><tbody><tr><th colspan="4" style="text-align:center;font-size:125%;font-weight:bold">CYP2C9</th></tr><tr><td colspan="4" style="text-align:center"><a href="/wiki/File:CYP2C9_1OG2.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/CYP2C9_1OG2.png/250px-CYP2C9_1OG2.png" decoding="async" width="250" height="262" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/29/CYP2C9_1OG2.png/375px-CYP2C9_1OG2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/29/CYP2C9_1OG2.png/500px-CYP2C9_1OG2.png 2x" data-file-width="1000" data-file-height="1047" /></a></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><table style="padding:0;border:none;margin:0;width:100%;text-align:left"><tbody><tr><th colspan="4" style="text-align:center;background-color:light-dark(#ddd, #404244) !important;color:inherit">Available structures</th></tr><tr><th rowspan="2" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit;width:43px"><a href="/wiki/Protein_Data_Bank" title="Protein Data Bank">PDB</a></th><td colspan="2" style="background-color:light-dark(#eee, #27292d) !important;color:inherit">Human UniProt search: <a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe/searchResults.html?display=both&term=P11712">PDBe</a> <a rel="nofollow" class="external text" href="https://www.rcsb.org/search?q=rcsb_polymer_entity_container_identifiers.reference_sequence_identifiers.database_name:UniProt%20AND%20rcsb_polymer_entity_container_identifiers.reference_sequence_identifiers.database_accession:P11712">RCSB</a> </td></tr><tr><td><table class="collapsible collapsed" style="padding:0;border:none;margin:0;width:100%;text-align:left"><tbody><tr style="text-align:center"><th colspan="2" style="background-color:light-dark(#ddd, #404244) !important;color:inherit">List of PDB id codes</th></tr><tr><td colspan="2" style="background-color:light-dark(#eee, #27292d) !important;color:inherit"><a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/1OG2">1OG2</a>, <a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/1OG5">1OG5</a>, <a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/1R9O">1R9O</a>, <a rel="nofollow" class="external text" href="https://www.rcsb.org/structure/4NZ2">4NZ2</a></td></tr></tbody></table></td></tr></tbody></table></td></tr><tr><th colspan="4" style="text-align:center;background-color:light-dark(#ddd, #404244) !important;color:inherit">Identifiers</th></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/Gene_nomenclature" title="Gene nomenclature">Aliases</a></th><td colspan="3" style="background:light-dark(#eee, #27292d) !important;color:inherit"><a rel="nofollow" class="external text" href="https://www.genenames.org/data/gene-symbol-report/#!/hgnc_id/2623">CYP2C9</a>, CPC9, CYP2C, CYP2C10, CYPIIC9, P450IIC9, cytochrome P450 family 2 subfamily C member 9, Cytochrome P450 2C9, P450-2C9</td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit">External IDs</th><td colspan="3" style="background-color:light-dark(#eee, #27292d) !important;color:inherit"><a href="/wiki/Mendelian_Inheritance_in_Man" class="mw-redirect" title="Mendelian Inheritance in Man">OMIM</a>: <a rel="nofollow" class="external text" href="https://omim.org/entry/601130">601130</a>; <a href="/wiki/Mouse_Genome_Informatics" title="Mouse Genome Informatics">MGI</a>: <a rel="nofollow" class="external text" href="http://www.informatics.jax.org/marker/MGI:1919553">1919553</a>; <a href="/wiki/HomoloGene" title="HomoloGene">HomoloGene</a>: <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=homologene&dopt=HomoloGene&list_uids=133566">133566</a>; <a href="/wiki/GeneCards" title="GeneCards">GeneCards</a>: <a rel="nofollow" class="external text" href="https://www.genecards.org/cgi-bin/carddisp.pl?gene=CYP2C9">CYP2C9</a>; <a href="/wiki/Orthologous_MAtrix" title="Orthologous MAtrix">OMA</a>:<a rel="nofollow" class="external text" href="https://omabrowser.org/oma/vps/ENSG00000138109">CYP2C9 - orthologs</a></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC number</a></th><td colspan="3" style="background-color:light-dark(#eee, #27292d) !important;color:inherit"><a rel="nofollow" class="external text" href="https://www.genome.jp/dbget-bin/www_bget?enzyme+1.14.14.51">1.14.14.51</a></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><table class="collapsible collapsed" style="padding:0;border:none;margin:0;width:100%;text-align:left"><tbody><tr><th colspan="4" style="text-align:center;background-color:light-dark(#ddd, #404244) !important;color:inherit">Gene location (<a href="/wiki/Human_genome" title="Human genome">Human</a>)</th></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><a href="/wiki/File:Ideogram_human_chromosome_10.svg" class="mw-file-description" title="Chromosome 10 (human)"><img alt="Chromosome 10 (human)" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Ideogram_human_chromosome_10.svg/300px-Ideogram_human_chromosome_10.svg.png" decoding="async" width="300" height="120" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Ideogram_human_chromosome_10.svg/450px-Ideogram_human_chromosome_10.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2f/Ideogram_human_chromosome_10.svg/600px-Ideogram_human_chromosome_10.svg.png 2x" data-file-width="474" data-file-height="189" /></a></td></tr><tr><th scope="row" width="15%" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/Chromosome" title="Chromosome">Chr.</a></th><td colspan="3" width="85%" style="background-color:light-dark(#eee, #27292d) !important;color:inherit"><a href="/wiki/Chromosome_10_(human)" class="mw-redirect" title="Chromosome 10 (human)">Chromosome 10 (human)</a><a href="#cite_note-refGRCh38Ensembl-1">[1]</a></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><div align="center"><div style="position: relative; width: 300px;"><a href="/wiki/File:Human_chromosome_10_ideogram.svg" class="mw-file-description" title="Chromosome 10 (human)"><img alt="Chromosome 10 (human)" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Human_chromosome_10_ideogram.svg/300px-Human_chromosome_10_ideogram.svg.png" decoding="async" width="300" height="58" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Human_chromosome_10_ideogram.svg/450px-Human_chromosome_10_ideogram.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e0/Human_chromosome_10_ideogram.svg/600px-Human_chromosome_10_ideogram.svg.png 2x" data-file-width="1125" data-file-height="216" /></a><div style="position: absolute; left: 203.36467528413px; top: 2px; padding: 0;"><a href="/wiki/File:HSR_1996_II_3.5e.svg" class="mw-file-description" title="Genomic location for CYP2C9"><img alt="Genomic location for CYP2C9" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/HSR_1996_II_3.5e.svg/14px-HSR_1996_II_3.5e.svg.png" decoding="async" width="14" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/HSR_1996_II_3.5e.svg/21px-HSR_1996_II_3.5e.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/HSR_1996_II_3.5e.svg/28px-HSR_1996_II_3.5e.svg.png 2x" data-file-width="142" data-file-height="142" /></a></div><div style="position: absolute; left: 209.4px; top: 19px; padding: 0;"><a href="/wiki/File:Red_rectangle_2x18.png" class="mw-file-description" title="Genomic location for CYP2C9"><img alt="Genomic location for CYP2C9" src="//upload.wikimedia.org/wikipedia/commons/6/6a/Red_rectangle_2x18.png" decoding="async" width="2" height="18" class="mw-file-element" data-file-width="2" data-file-height="18" /></a></div></div></div></td></tr><tr><th scope="row" rowspan="2" width="15%" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/Locus_(genetics)" title="Locus (genetics)">Band</a></th><td rowspan="2" width="35%" style="background-color:light-dark(#eee, #27292d) !important;color:inherit">10q23.33</td><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit">Start</th><td style="background-color:light-dark(#eee, #27292d) !important;color:inherit">94,938,658 <a href="/wiki/Base_pair" title="Base pair">bp</a><a href="#cite_note-refGRCh38Ensembl-1">[1]</a></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit">End</th><td style="background-color:light-dark(#eee, #27292d) !important;color:inherit">94,990,091 <a href="/wiki/Base_pair" title="Base pair">bp</a><a href="#cite_note-refGRCh38Ensembl-1">[1]</a></td></tr></tbody></table></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><table class="collapsible collapsed" style="padding:0;border:none;margin:0;width:100%;text-align:left"><tbody><tr><th colspan="4" style="text-align:center;background-color:light-dark(#ddd, #404244) !important;color:inherit">Gene location (<a href="/wiki/Laboratory_mouse" title="Laboratory mouse">Mouse</a>)</th></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><a href="/wiki/File:Ideogram_house_mouse_chromosome_19.svg" class="mw-file-description" title="Chromosome 19 (mouse)"><img alt="Chromosome 19 (mouse)" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Ideogram_house_mouse_chromosome_19.svg/330px-Ideogram_house_mouse_chromosome_19.svg.png" decoding="async" width="260" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/82/Ideogram_house_mouse_chromosome_19.svg/390px-Ideogram_house_mouse_chromosome_19.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/82/Ideogram_house_mouse_chromosome_19.svg/520px-Ideogram_house_mouse_chromosome_19.svg.png 2x" data-file-width="470" data-file-height="200" /></a></td></tr><tr><th scope="row" width="15%" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/Chromosome" title="Chromosome">Chr.</a></th><td colspan="3" width="85%" style="background-color:light-dark(#eee, #27292d) !important;color:inherit">Chromosome 19 (mouse)<a href="#cite_note-refGRCm38Ensembl-2">[2]</a></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><div align="center"><div style="position: relative; width: 300px;"><a href="/wiki/File:Ideogram_of_house_mouse_chromosome_19.svg" class="mw-file-description" title="Chromosome 19 (mouse)"><img alt="Chromosome 19 (mouse)" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Ideogram_of_house_mouse_chromosome_19.svg/330px-Ideogram_of_house_mouse_chromosome_19.svg.png" decoding="async" width="300" height="58" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Ideogram_of_house_mouse_chromosome_19.svg/500px-Ideogram_of_house_mouse_chromosome_19.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Ideogram_of_house_mouse_chromosome_19.svg/960px-Ideogram_of_house_mouse_chromosome_19.svg.png 2x" data-file-width="1200" data-file-height="231" /></a><div style="position: absolute; left: 181.64691802925px; top: 2px; padding: 0;"><a href="/wiki/File:HSR_1996_II_3.5e.svg" class="mw-file-description" title="Genomic location for CYP2C9"><img alt="Genomic location for CYP2C9" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/HSR_1996_II_3.5e.svg/14px-HSR_1996_II_3.5e.svg.png" decoding="async" width="14" height="14" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d8/HSR_1996_II_3.5e.svg/21px-HSR_1996_II_3.5e.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d8/HSR_1996_II_3.5e.svg/28px-HSR_1996_II_3.5e.svg.png 2x" data-file-width="142" data-file-height="142" /></a></div><div style="position: absolute; left: 187.6px; top: 19px; padding: 0;"><a href="/wiki/File:Red_rectangle_2x18.png" class="mw-file-description" title="Genomic location for CYP2C9"><img alt="Genomic location for CYP2C9" src="//upload.wikimedia.org/wikipedia/commons/6/6a/Red_rectangle_2x18.png" decoding="async" width="2" height="18" class="mw-file-element" data-file-width="2" data-file-height="18" /></a></div></div></div></td></tr><tr><th scope="row" rowspan="2" width="15%" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/Locus_(genetics)" title="Locus (genetics)">Band</a></th><td rowspan="2" width="35%" style="background-color:light-dark(#eee, #27292d) !important;color:inherit">19|19 C3</td><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit">Start</th><td style="background-color:light-dark(#eee, #27292d) !important;color:inherit">39,049,459 <a href="/wiki/Base_pair" title="Base pair">bp</a><a href="#cite_note-refGRCm38Ensembl-2">[2]</a></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit">End</th><td style="background-color:light-dark(#eee, #27292d) !important;color:inherit">39,082,388 <a href="/wiki/Base_pair" title="Base pair">bp</a><a href="#cite_note-refGRCm38Ensembl-2">[2]</a></td></tr></tbody></table></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><table class="collapsible collapsed" style="padding:0;border:none;margin:0;width:100%;text-align:left"><tbody><tr><th colspan="4" style="text-align:center;background-color:light-dark(#ddd, #404244) !important;color:inherit"><a href="/wiki/Gene_expression" title="Gene expression">RNA expression</a> pattern</th></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a rel="nofollow" class="external text" href="https://www.bgee.org/">Bgee</a></th><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:left"><tbody><tr><th><a href="/wiki/Human_genome" title="Human genome">Human</a></th><th><a href="/wiki/Laboratory_mouse" title="Laboratory mouse">Mouse</a> (ortholog)</th></tr><tr><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:center"><tbody><tr><td colspan="1"><a rel="nofollow" class="external text" href="https://www.bgee.org/gene/ENSG00000138109">Top expressed in</a></td></tr><tr><td colspan="1"><div class="plainlinks" style="margin:-12px 0px -10px 0px"><ul style="line-height:15%;margin:9px"><li style="line-height: 137%;">right lobe of liver</li> <li style="line-height: 137%;">jejunal mucosa</li> <li style="line-height: 137%;">pancreatic ductal cell</li> <li style="line-height: 137%;">mucosa of ileum</li> <li style="line-height: 137%;">duodenum</li> <li style="line-height: 137%;">gallbladder</li> <li style="line-height: 137%;">gingival epithelium</li> <li style="line-height: 137%;">epithelium of esophagus</li> <li style="line-height: 137%;">body of stomach</li> <li style="line-height: 137%;">gastric mucosa</li></ul></div></td></tr></tbody></table></td><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:center"><tbody><tr><td colspan="1"><a rel="nofollow" class="external text" href="https://www.bgee.org/gene/ENSMUSG00000067231">Top expressed in</a></td></tr><tr><td colspan="1"><div class="plainlinks" style="margin:-12px 0px -10px 0px"><ul style="line-height:15%;margin:9px"><li style="line-height: 137%;">duodenum</li> <li style="line-height: 137%;">jejunum</li> <li style="line-height: 137%;">ileum</li> <li style="line-height: 137%;">colon</li> <li style="line-height: 137%;">stomach</li> <li style="line-height: 137%;">esophagus</li> <li style="line-height: 137%;">embryo</li> <li style="line-height: 137%;">pancreas</li> <li style="line-height: 137%;">islet of Langerhans</li> <li style="line-height: 137%;">quadriceps femoris muscle</li></ul></div></td></tr></tbody></table></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><a rel="nofollow" class="external text" href="https://www.bgee.org/gene/ENSG00000138109">More reference expression data</a></td></tr></tbody></table></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a rel="nofollow" class="external text" href="http://biogps.org/">BioGPS</a></th><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:left"><tbody><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><a href="/wiki/File:PBB_GE_CYP2C9_214421_x_at_fs.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/PBB_GE_CYP2C9_214421_x_at_fs.png/250px-PBB_GE_CYP2C9_214421_x_at_fs.png" decoding="async" width="250" height="181" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/PBB_GE_CYP2C9_214421_x_at_fs.png/375px-PBB_GE_CYP2C9_214421_x_at_fs.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/PBB_GE_CYP2C9_214421_x_at_fs.png/500px-PBB_GE_CYP2C9_214421_x_at_fs.png 2x" data-file-width="732" data-file-height="530" /></a> <a href="/wiki/File:PBB_GE_CYP2C9_216025_x_at_fs.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/PBB_GE_CYP2C9_216025_x_at_fs.png/250px-PBB_GE_CYP2C9_216025_x_at_fs.png" decoding="async" width="250" height="181" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c8/PBB_GE_CYP2C9_216025_x_at_fs.png/375px-PBB_GE_CYP2C9_216025_x_at_fs.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c8/PBB_GE_CYP2C9_216025_x_at_fs.png/500px-PBB_GE_CYP2C9_216025_x_at_fs.png 2x" data-file-width="732" data-file-height="530" /></a> <a href="/wiki/File:PBB_GE_CYP2C9_216661_x_at_fs.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/PBB_GE_CYP2C9_216661_x_at_fs.png/250px-PBB_GE_CYP2C9_216661_x_at_fs.png" decoding="async" width="250" height="181" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/22/PBB_GE_CYP2C9_216661_x_at_fs.png/500px-PBB_GE_CYP2C9_216661_x_at_fs.png 1.5x" data-file-width="732" data-file-height="530" /></a></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><a rel="nofollow" class="external text" href="http://biogps.org/gene/1559/">More reference expression data</a></td></tr></tbody></table></td></tr></tbody></table></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><table class="collapsible collapsed" style="padding:0;border:none;margin:0;width:100%;text-align:left"><tbody><tr><th colspan="4" style="text-align:center;background-color:light-dark(#ddd, #404244) !important;color:inherit"><a href="/wiki/Gene_ontology" class="mw-redirect" title="Gene ontology">Gene ontology</a></th></tr><tr><td style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit;font-weight:bold">Molecular function</td><td style="background-color:light-dark(#eee, #27292d) !important;color:inherit"><div class="plainlinks"> <ul><li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0005506">iron ion binding</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0008392">arachidonic acid epoxygenase activity</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0046872">metal ion binding</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0008395">steroid hydroxylase activity</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0034875">caffeine oxidase activity</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0020037">heme binding</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0016705">oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0016491">oxidoreductase activity</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0004497">monooxygenase activity</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0016712">oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen</a></li></ul> </div></td></tr><tr><td style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit;font-weight:bold">Cellular component</td><td style="background-color:light-dark(#eee, #27292d) !important;color:inherit"><div class="plainlinks"> <ul><li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0031090">organelle membrane</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0005789">endoplasmic reticulum membrane</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0016020">membrane</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0043231">intracellular membrane-bounded organelle</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0005783">endoplasmic reticulum</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0005737">cytoplasm</a></li></ul> </div></td></tr><tr><td style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit;font-weight:bold">Biological process</td><td style="background-color:light-dark(#eee, #27292d) !important;color:inherit"><div class="plainlinks"> <ul><li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0008202">steroid metabolic process</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0006629">lipid metabolism</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0043603">cellular amide metabolic process</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0019373">epoxygenase P450 pathway</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0032787">monocarboxylic acid metabolic process</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0070989">oxidative demethylation</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0097267">omega-hydroxylase P450 pathway</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0016098">monoterpenoid metabolic process</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0006805">xenobiotic metabolic process</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0019627">urea metabolic process</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0042759">long-chain fatty acid biosynthetic process</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0006082">organic acid metabolic process</a></li> <li><a rel="nofollow" class="external text" href="http://amigo.geneontology.org/amigo/term/GO:0008210">estrogen metabolic process</a></li></ul> </div></td></tr><tr><td colspan="4" style="background-color:light-dark(#eee, #27292d) !important;color:inherit;text-align:center">Sources:<a rel="nofollow" class="external text" href="http://amigo.geneontology.org/">Amigo</a> / <a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/QuickGO/">QuickGO</a></td></tr></tbody></table></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><table class="collapsible" style="padding:0;border:none;margin:0;width:100%;text-align:left"><tbody><tr><th colspan="4" style="text-align:center;background-color:light-dark(#ddd, #404244) !important;color:inherit"><a href="/wiki/Orthologs" class="mw-redirect" title="Orthologs">Orthologs</a></th></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit">Species</th><td>Human</td><td>Mouse</td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/Entrez" title="Entrez">Entrez</a></th><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1"></th></tr><tr><td colspan="1"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=gene&cmd=retrieve&dopt=default&list_uids=1559&rn=1">1559</a></td></tr></tbody></table></td><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1"></th></tr><tr><td colspan="1"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=gene&cmd=retrieve&dopt=default&list_uids=72303&rn=1">72303</a></td></tr></tbody></table></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/Ensembl" class="mw-redirect" title="Ensembl">Ensembl</a></th><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1"></th></tr><tr><td colspan="1"><a rel="nofollow" class="external text" href="http://www.ensembl.org/Homo_sapiens/geneview?gene=ENSG00000138109;db=core">ENSG00000138109</a></td></tr></tbody></table></td><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1"></th></tr><tr><td colspan="1"><a rel="nofollow" class="external text" href="http://www.ensembl.org/Mus_musculus/geneview?gene=ENSMUSG00000067231;db=core">ENSMUSG00000067231</a></td></tr></tbody></table></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/UniProt" title="UniProt">UniProt</a></th><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1"></th></tr><tr><td colspan="1"><a rel="nofollow" class="external text" href="https://www.uniprot.org/uniprot/P11712">P11712</a></td></tr></tbody></table></td><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1"></th></tr><tr><td colspan="1">n/a</td></tr></tbody></table></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit">RefSeq (mRNA)</th><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1" class="plainlinks"></th></tr><tr><td colspan="1"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/viewer.fcgi?val=NM_000771">NM_000771</a></td></tr></tbody></table></td><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1" class="plainlinks"></th></tr><tr><td colspan="1"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/viewer.fcgi?val=NM_028191">NM_028191</a></td></tr></tbody></table></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit">RefSeq (protein)</th><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1" class="plainlinks"></th></tr><tr><td colspan="1"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/entrez/viewer.fcgi?val=NP_000762">NP_000762</a></td></tr></tbody></table></td><td><table class="none" style="padding:0;border:none;margin:0;width:100%;text-align:right"><tbody><tr><th colspan="1" class="plainlinks"></th></tr><tr><td colspan="1">n/a</td></tr></tbody></table></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit">Location (UCSC)</th><td><a rel="nofollow" class="external text" href="https://genome.ucsc.edu/cgi-bin/hgTracks?org=Human&db=hg38&position=chr10:94938658-94990091">Chr 10: 94.94 – 94.99 Mb</a></td><td><a rel="nofollow" class="external text" href="https://genome.ucsc.edu/cgi-bin/hgTracks?org=Mouse&db=mm0&position=chr19:39049459-39082388">Chr 19: 39.05 – 39.08 Mb</a></td></tr><tr><th scope="row" style="background-color:light-dark(#c3fdb8, #003500) !important;color:inherit"><a href="/wiki/PubMed" title="PubMed">PubMed</a> search</th><td><a href="#cite_note-3">[3]</a></td><td><a href="#cite_note-4">[4]</a></td></tr></tbody></table></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><a href="/wiki/Wikidata" title="Wikidata">Wikidata</a></td></tr><tr><td colspan="4" style="text-align:center;background-color:light-dark(#eee, #27292d) !important;color:inherit"><table style="padding:0;border:none;margin:0;width:100%;text-align:center"><tbody><tr><td colspan="2" style="background-color:light-dark(#eee, #27292d) !important;color:inherit;text-align:center"><a href="https://www.wikidata.org/wiki/Q14916181" class="extiw" title="d:Q14916181">View/Edit Human</a></td><td colspan="2" style="background-color:light-dark(#eee, #27292d) !important;color:inherit;text-align:center"><a href="https://www.wikidata.org/wiki/Q18265415" class="extiw" title="d:Q18265415">View/Edit Mouse</a></td></tr></tbody></table></td></tr></tbody></table> Cytochrome P450 family 2 subfamily C member 9 (abbreviated CYP2C9) is an <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Protein" title="Protein">protein</a>. The enzyme is involved in the metabolism, by oxidation, of both xenobiotics, including drugs, and endogenous compounds, including fatty acids. In humans, the protein is encoded by the CYP2C9 <a href="/wiki/Gene" title="Gene">gene</a>.<a href="#cite_note-pmid2009263-5">[5]</a><a href="#cite_note-pmid7841444-6">[6]</a> The gene is highly polymorphic, which affects the efficiency of the metabolism by the enzyme.<a href="#cite_note-ncbi1559-7">[7]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Function">Function</h2>[<a href="/w/index.php?title=CYP2C9&action=edit&section=1" title="Edit section: Function">edit</a>]</div> CYP2C9 is a crucial <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> enzyme, which plays a significant role in the metabolism, by oxidation, of both xenobiotic and endogenous compounds.<a href="#cite_note-ncbi1559-7">[7]</a> CYP2C9 makes up about 18% of the cytochrome P450 protein in liver microsomes. The protein is mainly expressed in the <a href="/wiki/Liver" title="Liver">liver</a>, <a href="/wiki/Duodenum" title="Duodenum">duodenum</a>, and <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a>.<a href="#cite_note-ncbi1559-7">[7]</a> About 100 therapeutic drugs are metabolized by CYP2C9, including drugs with a narrow therapeutic index such as <a href="/wiki/Warfarin" title="Warfarin">warfarin</a> and <a href="/wiki/Phenytoin" title="Phenytoin">phenytoin</a>, and other routinely prescribed drugs such as <a href="/wiki/Acenocoumarol" title="Acenocoumarol">acenocoumarol</a>, <a href="/wiki/Tolbutamide" title="Tolbutamide">tolbutamide</a>, <a href="/wiki/Losartan" title="Losartan">losartan</a>, <a href="/wiki/Glipizide" title="Glipizide">glipizide</a>, and some <a href="/wiki/Nonsteroidal_anti-inflammatory_drug" title="Nonsteroidal anti-inflammatory drug">nonsteroidal anti-inflammatory drugs</a>. By contrast, the known extrahepatic CYP2C9 often metabolizes important endogenous compounds such as serotonin and, owing to its <a href="/wiki/Epoxygenase" title="Epoxygenase">epoxygenase</a> activity, various <a href="/wiki/Polyunsaturated_fatty_acid" class="mw-redirect" title="Polyunsaturated fatty acid">polyunsaturated fatty acids</a>, converting these fatty acids to a wide range of biologically active products.<a href="#cite_note-pmid15822186-8">[8]</a><a href="#cite_note-pmid25093613-9">[9]</a> In particular, CYP2C9 metabolizes <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a> to the following <a href="/wiki/Eicosatrienoic_acid_epoxide" class="mw-redirect" title="Eicosatrienoic acid epoxide">eicosatrienoic acid epoxide</a> (EETs) <a href="/wiki/Stereoisomer" class="mw-redirect" title="Stereoisomer">stereoisomer</a> sets: 5R,6S-epoxy-8Z,11Z,14Z-eicosatetraenoic and 5S,6R-epoxy-8Z,11Z,14Z-eicosatetraenoic acids; 11R,12S-epoxy-8Z,11Z,14Z-eicosatetraenoic and 11S,12R-epoxy-5Z,8Z,14Z-eicosatetraenoic acids; and 14R,15S-epoxy-5Z,8Z,11Z-eicosatetraenoic and 14S,15R-epoxy-5Z,8Z,11Z-eicosatetraenoic acids. It likewise metabolizes <a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">docosahexaenoic acid</a> to <a href="/wiki/Epoxydocosapentaenoic_acid" title="Epoxydocosapentaenoic acid">epoxydocosapentaenoic acids</a> (EDPs; primarily 19,20-epoxy-eicosapentaenoic acid isomers [i.e. 10,11-EDPs]) and <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a> to <a href="/wiki/Epoxyeicosatetraenoic_acid" title="Epoxyeicosatetraenoic acid">epoxyeicosatetraenoic acids</a> (EEQs, primarily 17,18-EEQ and 14,15-EEQ isomers).<a href="#cite_note-10">[10]</a> Animal models and a limited number of human studies implicate these epoxides in reducing <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>; protecting against <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a> and other insults to the heart; promoting the growth and metastasis of certain cancers; inhibiting <a href="/wiki/Inflammation" title="Inflammation">inflammation</a>; stimulating blood vessel formation; and possessing a variety of actions on neural tissues including modulating <a href="/wiki/Neurohormone" title="Neurohormone">neurohormone</a> release and blocking pain perception (see <a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">epoxyeicosatrienoic acid</a> and <a href="/wiki/Epoxygenase" title="Epoxygenase">epoxygenase</a>).<a href="#cite_note-pmid25093613-9">[9]</a> In vitro studies on human and animal cells and tissues and in vivo animal model studies indicate that certain EDPs and EEQs (16,17-EDPs, 19,20-EDPs, 17,18-EEQs have been most often examined) have actions which often oppose those of another product of CYP450 enzymes (e.g. <a href="/w/index.php?title=CYP4A1&action=edit&redlink=1" class="new" title="CYP4A1 (page does not exist)">CYP4A1</a>, <a href="/wiki/CYP4A11" title="CYP4A11">CYP4A11</a>, <a href="/wiki/CYP4F2" title="CYP4F2">CYP4F2</a>, <a href="/w/index.php?title=CYP4F3A&action=edit&redlink=1" class="new" title="CYP4F3A (page does not exist)">CYP4F3A</a>, and <a href="/w/index.php?title=CYP4F3B&action=edit&redlink=1" class="new" title="CYP4F3B (page does not exist)">CYP4F3B</a>) viz., <a href="/wiki/20-Hydroxyeicosatetraenoic_acid" title="20-Hydroxyeicosatetraenoic acid">20-Hydroxyeicosatetraenoic acid</a> (20-HETE), principally in the areas of blood pressure regulation, blood vessel thrombosis, and cancer growth (see <a href="/wiki/20-Hydroxyeicosatetraenoic_acid" title="20-Hydroxyeicosatetraenoic acid">20-Hydroxyeicosatetraenoic acid</a>, <a href="/wiki/Epoxyeicosatetraenoic_acid" title="Epoxyeicosatetraenoic acid">epoxyeicosatetraenoic acid</a>, and <a href="/wiki/Epoxydocosapentaenoic_acid" title="Epoxydocosapentaenoic acid">epoxydocosapentaenoic acid</a> sections on activities and clinical significance). Such studies also indicate that the <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acids</a> and EEQs are: 1) more potent than EETs in decreasing hypertension and pain perception; 2) more potent than or equal in potency to the EETs in suppressing inflammation; and 3) act oppositely from the EETs in that they inhibit <a href="/wiki/Angiogenesis" title="Angiogenesis">angiogenesis</a>, endothelial cell migration, endothelial cell proliferation, and the growth and metastasis of human breast and prostate cancer cell lines whereas EETs have stimulatory effects in each of these systems.<a href="#cite_note-pmid25244930-11">[11]</a><a href="#cite_note-12">[12]</a><a href="#cite_note-13">[13]</a><a href="#cite_note-pmid25240260-14">[14]</a> Consumption of omega-3 fatty acid-rich diets dramatically raises the serum and tissue levels of EDPs and EEQs in animals as well as humans, and in humans is by far the most prominent change in the profile of <a href="/wiki/Polyunsaturated_fatty_acid" class="mw-redirect" title="Polyunsaturated fatty acid">polyunsaturated fatty acids</a> metabolites caused by dietary omega-3 fatty acids.<a href="#cite_note-pmid25244930-11">[11]</a><a href="#cite_note-pmid25240260-14">[14]</a><a href="#cite_note-pmid24634501-15">[15]</a> CYP2C9 may also metabolize <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a> to the potentially very toxic products, <a href="/wiki/Coronaric_acid" title="Coronaric acid">coronaric acid</a> (also termed leukotoxin) and <a href="/wiki/Vernolic_acid" title="Vernolic acid">vernolic acid</a> (also termed isoleukotoxin); these linoleic acid epoxides cause <a href="/wiki/Multiple_organ_failure" class="mw-redirect" title="Multiple organ failure">multiple organ failure</a> and <a href="/wiki/Acute_respiratory_distress" class="mw-redirect" title="Acute respiratory distress">acute respiratory distress</a> in animal models and may contribute to these syndromes in humans.<a href="#cite_note-pmid25093613-9">[9]</a> <div class="mw-heading mw-heading2"><h2 id="Pharmacogenomics">Pharmacogenomics</h2>[<a href="/w/index.php?title=CYP2C9&action=edit&section=2" title="Edit section: Pharmacogenomics">edit</a>]</div> The CYP2C9 gene is highly polymorphic.<a href="#cite_note-pmid31075510-16">[16]</a> At least 20 <a href="/wiki/Single_nucleotide_polymorphisms" class="mw-redirect" title="Single nucleotide polymorphisms">single nucleotide polymorphisms</a> (SNPs) have been reported to have functional evidence of altered enzyme activity.<a href="#cite_note-pmid31075510-16">[16]</a> In fact, <a href="/wiki/Adverse_drug_reactions" class="mw-redirect" title="Adverse drug reactions">adverse drug reactions</a> (ADRs) often result from unanticipated changes in CYP2C9 enzyme activity secondary to genetic polymorphisms. Especially for CYP2C9 substrates such as warfarin and phenytoin, diminished metabolic capacity because of genetic polymorphisms or drug-drug interactions can lead to toxicity at normal therapeutic doses.<a href="#cite_note-pmid16646575-17">[17]</a><a href="#cite_note-pmid18690857-18">[18]</a> Information about how human genetic variation of CYP2C9 affects response to medications can be found in databases such PharmGKB,<a href="#cite_note-19">[19]</a> Clinical Pharmacogenetics Implementation Consortium (CPIC).<a href="#cite_note-20">[20]</a> The label CYP2C9*1 is assigned by the <a href="/wiki/Pharmacogene_Variation_Consortium" title="Pharmacogene Variation Consortium">Pharmacogene Variation Consortium</a> (PharmVar) to the most commonly observed human gene variant.<a href="#cite_note-PharmVarDbPage-21">[21]</a> Other relevant variants are cataloged by PharmVar under consecutive numbers, which are written after an asterisk (star) character to form an allele label.<a href="#cite_note-pmid31260137-22">[22]</a><a href="#cite_note-pmid32602114-23">[23]</a> The two most well-characterized variant alleles are CYP2C9*2 (NM_000771.3:c.430C>T, p.Arg144Cys, rs1799853) and CYP2C9*3 (NM_000771.3:c.1075A>C, p. Ile359Leu, rs1057910),<a href="#cite_note-pmid8873220-24">[24]</a> causing reductions in enzyme activity of 30% and 80%, respectively.<a href="#cite_note-pmid31075510-16">[16]</a> <div class="mw-heading mw-heading3"><h3 id="Metabolizer_phenotypes">Metabolizer phenotypes</h3>[<a href="/w/index.php?title=CYP2C9&action=edit&section=3" title="Edit section: Metabolizer phenotypes">edit</a>]</div> On the basis of their ability to metabolize CYP2C9 substrates, individuals can be categorized by groups. The carriers of homozygous CYP2C9*1 variant, i.e. of the *1/*1 genotype, are designated extensive metabolizers (EM), or normal metabolizers.<a href="#cite_note-25">[25]</a> The carriers of the CYP2C9*2 or CYP2C9*3 alleles in a heterozygous state, i.e. just one of these alleles (*1/*2, *1/*3) are designated intermediate metabolizers (IM), and those carrying two of these alleles, i.e. homozygous (*2/*3, *2/*2 or *3/*3) – poor metabolizers (PM).<a href="#cite_note-pmid25099164-26">[26]</a><a href="#cite_note-27">[27]</a> As a result, the metabolic ratio – the ratio of unchanged drug to metabolite – is higher in PMs. A study of the ability to metabolize warfarin among the carriers of the most well-characterized CYP2C9 genotypes (*1, *2 and *3), expressed as a percentage of the mean dose in patients with wild-type alleles (*1/*1), concluded that the mean warfarin maintenance dose was 92% in *1/*2, 74% in *1/*3, 63% in *2/*3, 61% in *2/*2 and 34% in 3/*3.<a href="#cite_note-28">[28]</a> CYP2C9*3 reflects an <a href="/wiki/Isoleucine" title="Isoleucine">Ile</a>359-<a href="/wiki/Leucine" title="Leucine">Leu</a> (I359L) change in the <a href="/wiki/Amino_acid" title="Amino acid">amino acid</a> sequence,<a href="#cite_note-CYP2C9-29">[29]</a> and also has reduced catalytic activity compared with the wild type (CYP2C9*1) for substrates other than warfarin.<a href="#cite_note-30">[30]</a> Its prevalence varies with race as: <table class="wikitable"> <tbody><tr> <th colspan="6">Allele frequencies (%) of CYP2C9 polymorphism </th></tr> <tr> <th> </th> <th>African-American </th> <th>Black-African </th> <th>Pygmy </th> <th>Asian </th> <th>Caucasian </th></tr> <tr> <td>CYP2C9*3 </td> <td>2.0 </td> <td>0–2.3 </td> <td>0 </td> <td>1.1–3.6 </td> <td>3.3–16.2 </td></tr> </tbody></table> <div class="mw-heading mw-heading3"><h3 id="Test_panels_of_variant_alleles">Test panels of variant alleles</h3>[<a href="/w/index.php?title=CYP2C9&action=edit&section=4" title="Edit section: Test panels of variant alleles">edit</a>]</div> The Association for Molecular Pathology Pharmacogenomics (PGx) Working Group in 2019 has recommended a minimum panel of variant alleles (Tier 1) and an extended panel of variant alleles (Tier 2) to be included in assays for CYP2C9 testing. CYP2C9 variant alleles recommended as Tier 1 by the PGx Working Group include CYP2C9 *2, *3, *5, *6, *8, and *11. This recommendation was based on their well-established functional effects on CYP2C9 activity and drug response availability of reference materials, and their appreciable allele frequencies in major ethnic groups. The following CYP2C9 alleles are recommended for inclusion in tier 2: CYP2C9*12, *13, and *15.<a href="#cite_note-pmid31075510-16">[16]</a> CYP2C9*13 is defined by a missense variant in exon 2 (NM_000771.3:c.269T>C, p. Leu90Pro, rs72558187).<a href="#cite_note-pmid31075510-16">[16]</a> CYP2C9*13 prevalence is approximately 1% in the Asian population,<a href="#cite_note-Saikatikorn-2010-31">[31]</a> but in Caucasians this variant prevalence is almost zero.<a href="#cite_note-32">[32]</a> This variant is caused by a T269C mutation in the CYP2C9 gene which in turn results in the substitution of leucine at position-90 with proline (L90P) at the product enzyme protein. This residue is near the access point for substrates and the L90P mutation causes lower affinity and hence slower metabolism of several drugs that are metabolized CYP2C9 by such as <a href="/wiki/Diclofenac" title="Diclofenac">diclofenac</a> and <a href="/wiki/Flurbiprofen" title="Flurbiprofen">flurbiprofen</a>.<a href="#cite_note-Saikatikorn-2010-31">[31]</a> However, this variant is not included in the tier 1 recommendations of the PGx Working Group because of its very low multiethnic minor allele frequency and a lack of currently available reference materials.<a href="#cite_note-pmid31075510-16">[16]</a> As of 2020<a class="external text" href="https://en.wikipedia.org/w/index.php?title=CYP2C9&action=edit">[update]</a> the evidence level for CYP2C9*13 in the <a href="/wiki/Pharmacogene_Variation_Consortium" title="Pharmacogene Variation Consortium">PharmVar</a> database is limited, comparing to the tier 1 alleles, for which the evidence level is definitive.<a href="#cite_note-PharmVarDbPage-21">[21]</a> <div class="mw-heading mw-heading3"><h3 id="Additional_variants">Additional variants</h3>[<a href="/w/index.php?title=CYP2C9&action=edit&section=5" title="Edit section: Additional variants">edit</a>]</div> Not all clinically significant genetic variant alleles have been registered by <a href="/wiki/Pharmacogene_Variation_Consortium" title="Pharmacogene Variation Consortium">PharmVar</a>. For example, in a 2017 study, the variant rs2860905 showed stronger association with warfarin sensitivity (<4 mg/day) than common variants CYP2C9*2 and CYP2C9*3.<a href="#cite_note-33">[33]</a> Allele A (23% global frequency) is associated with a decreased dose of warfarin as compared to the allele G (77% global frequency). Another variant, rs4917639, according to a 2009 study, has a strong effect on warfarin sensitivity, almost the same as if CYP2C9*2 and CYP2C9*3 were combined into a single allele.<a href="#cite_note-34">[34]</a> The C allele at rs4917639 has 19% global frequency. Patients with the CC or CA genotype may require decreased dose of warfarin as compared to patients with the wild-type AA genotype.<a href="#cite_note-35">[35]</a> Another variant, rs7089580 with T allele having 14% global frequency, is associated with increased CYP2C9 gene expression. Carriers of AT and TT genotypes at rs7089580 had increased CYP2C9 expression levels compared to wild-type AA genotype. Increased gene expression due to rs7089580 T allele leads to an increased rate of warfarin metabolism and increased warfarin dose requirements. In a study published in 2014, the AT genotype showed slightly higher expression than TT, but both much higher than AA.<a href="#cite_note-36">[36]</a> Another variant, rs1934969 (in studies of 2012 and 2014) have been shown to affect the ability to metabolize losartan: carriers of the TT genotype have increased CYP2C9 hydroxylation capacity for losartan comparing to AA genotype, and, as a result, the lower metabolic ratio of losartan, i.e., faster losartan metabolism.<a href="#cite_note-37">[37]</a><a href="#cite_note-38">[38]</a> <div class="mw-heading mw-heading2"><h2 id="Ligands">Ligands</h2>[<a href="/w/index.php?title=CYP2C9&action=edit&section=6" title="Edit section: Ligands">edit</a>]</div> Most inhibitors of CYP2C9 are <a href="/wiki/Competitive_inhibition" title="Competitive inhibition">competitive inhibitors</a>. <a href="/wiki/Non-competitive_inhibition" title="Non-competitive inhibition">Noncompetitive inhibitors</a> of CYP2C9 include <a href="/wiki/Nifedipine" title="Nifedipine">nifedipine</a>,<a href="#cite_note-pmid9929518-39">[39]</a><a href="#cite_note-pmid15049511-40">[40]</a> <a href="/wiki/Phenethyl_isothiocyanate" title="Phenethyl isothiocyanate">phenethyl isothiocyanate</a>,<a href="#cite_note-pmid11454729-41">[41]</a> <a href="/wiki/Medroxyprogesterone_acetate" title="Medroxyprogesterone acetate">medroxyprogesterone acetate</a><a href="#cite_note-pmid16645869-42">[42]</a> and <a href="/wiki/6-hydroxyflavone" class="mw-redirect" title="6-hydroxyflavone">6-hydroxyflavone</a>. It was indicated that the noncompetitive binding site of <a href="/wiki/6-hydroxyflavone" class="mw-redirect" title="6-hydroxyflavone">6-hydroxyflavone</a> is the reported allosteric binding site of the CYP2C9 enzyme.<a href="#cite_note-pmid19074529-43">[43]</a> Following is a table of selected <a href="/wiki/Enzyme_substrate" class="mw-redirect" title="Enzyme substrate">substrates</a>, <a href="/wiki/Enzyme_induction_and_inhibition" title="Enzyme induction and inhibition">inducers</a> and <a href="/wiki/Enzyme_induction_and_inhibition" title="Enzyme induction and inhibition">inhibitors</a> of CYP2C9. Where classes of agents are listed, there may be exceptions within the class. Inhibitors of CYP2C9 can be classified by their <a href="/wiki/Potency_(pharmacology)" title="Potency (pharmacology)">potency</a>, such as: <ul><li>Strong being one that causes at least a 5-fold increase in the plasma <a href="/wiki/Area_under_the_curve_(pharmacokinetics)" title="Area under the curve (pharmacokinetics)">AUC values</a>, or more than 80% decrease in <a href="/wiki/Clearance_(medicine)" class="mw-redirect" title="Clearance (medicine)">clearance</a>.<a href="#cite_note-Flockhart-2007-44">[44]</a></li> <li>Moderate being one that causes at least a 2-fold increase in the plasma AUC values, or a 50–80% decrease in clearance.<a href="#cite_note-Flockhart-2007-44">[44]</a></li> <li>Weak being one that causes at least a 1.25-fold but less than 2-fold increase in the plasma AUC values, or 20–50% decrease in clearance.<a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-usfda-tsii-45">[45]</a></li></ul> <table class="wikitable"> <caption>Selected inducers, inhibitors and substrates of CYP2C9 </caption> <tbody><tr> <th>Substrates</th> <th>Inhibitors</th> <th>Inducers </th></tr> <tr style="vertical-align: top;"> <td> <ul><li>dietary <a href="/wiki/Flavonoid" title="Flavonoid">flavonoids</a> <ul><li><a href="/wiki/Naringenin" title="Naringenin">naringenin</a><a href="#cite_note-Sousa-2013-46">[46]</a></li> <li><a href="/wiki/Naringin" title="Naringin">naringin</a><a href="#cite_note-Sousa-2013-46">[46]</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">quercetin</a><a href="#cite_note-Sousa-2013-46">[46]</a></li> <li><a href="/wiki/Rutin" title="Rutin">rutin</a><a href="#cite_note-Sousa-2013-46">[46]</a></li></ul></li> <li><a href="/wiki/NSAID" class="mw-redirect" title="NSAID">NSAIDs</a> (<a href="/wiki/Analgesic" title="Analgesic">analgesic</a>, <a href="/wiki/Antipyretic" title="Antipyretic">antipyretic</a>, <a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">anti-inflammatory</a>) <ul><li><a href="/wiki/Celecoxib" title="Celecoxib">celecoxib</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Lornoxicam" title="Lornoxicam">lornoxicam</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-pmid15764711-48">[48]</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">diclofenac</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">ibuprofen</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Naproxen" title="Naproxen">naproxen</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Ketoprofen" title="Ketoprofen">ketoprofen</a><a href="#cite_note-Ketoprofen,_PubChem-49">[49]</a></li> <li><a href="/wiki/Piroxicam" title="Piroxicam">piroxicam</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Meloxicam" title="Meloxicam">meloxicam</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Suprofen" title="Suprofen">suprofen</a><a href="#cite_note-Flockhart-2007-44">[44]</a></li></ul></li> <li><a href="/wiki/Phenytoin" title="Phenytoin">phenytoin</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a> (<a href="/wiki/Antiepileptic" class="mw-redirect" title="Antiepileptic">antiepileptic</a>)</li> <li><a href="/w/index.php?title=2-oxo-clopidogrel&action=edit&redlink=1" class="new" title="2-oxo-clopidogrel (page does not exist)">2-oxo-clopidogrel</a> (an inactive metabolite of clopidogrel prodrug)<a href="#cite_note-50">[50]</a></li> <li><a href="/wiki/Fluvastatin" title="Fluvastatin">fluvastatin</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a> (<a href="/wiki/Statin" title="Statin">statin</a>)</li> <li><a href="/wiki/Sulfonylurea" title="Sulfonylurea">sulfonylureas</a> (<a href="/wiki/Antidiabetic" class="mw-redirect" title="Antidiabetic">antidiabetic</a>) <ul><li><a href="/wiki/Glipizide" title="Glipizide">glipizide</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Glibenclamide" title="Glibenclamide">glibenclamide</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Glimepiride" title="Glimepiride">glimepiride</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Tolbutamide" title="Tolbutamide">tolbutamide</a><a href="#cite_note-Flockhart-2007-44">[44]</a></li> <li><a href="/wiki/Glyburide" class="mw-redirect" title="Glyburide">glyburide</a><a href="#cite_note-Flockhart-2007-44">[44]</a></li></ul></li> <li><a href="/wiki/Angiotensin_II_receptor_antagonists" class="mw-redirect" title="Angiotensin II receptor antagonists">angiotensin II receptor antagonists</a> (in <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Diabetic_nephropathy" title="Diabetic nephropathy">diabetic nephropathy</a>, <a href="/wiki/Congestive_heart_failure" class="mw-redirect" title="Congestive heart failure">CHF</a>) <ul><li><a href="/wiki/Irbesartan" title="Irbesartan">irbesartan</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li> <li><a href="/wiki/Losartan" title="Losartan">losartan</a> (<a href="/wiki/Sensitive_substrate" class="mw-redirect" title="Sensitive substrate">sensitive substrate</a>)<a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a></li></ul></li> <li><a href="/wiki/S-warfarin" class="mw-redirect" title="S-warfarin">S-warfarin</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a> (<a href="/wiki/Anticoagulant" title="Anticoagulant">anticoagulant</a>)</li> <li><a href="/wiki/Sildenafil" title="Sildenafil">sildenafil</a><a href="#cite_note-FASS-47">[47]</a> (in <a href="/wiki/Erectile_dysfunction" title="Erectile dysfunction">erectile dysfunction</a>)</li> <li><a href="/wiki/Terbinafine" title="Terbinafine">terbinafine</a><a href="#cite_note-FASS-47">[47]</a> (<a href="/wiki/Antifungal_medication" class="mw-redirect" title="Antifungal medication">antifungal</a>)</li> <li><a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">tricyclic antidepressant</a>)</li> <li><a href="/wiki/Fluoxetine" title="Fluoxetine">fluoxetine</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Selective_serotonin_reuptake_inhibitor" title="Selective serotonin reuptake inhibitor">SSRI</a> antidepressant)</li> <li><a href="/wiki/Nateglinide" title="Nateglinide">nateglinide</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (antidiabetic)</li> <li><a href="/wiki/Rosiglitazone" title="Rosiglitazone">rosiglitazone</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Antidiabetic" class="mw-redirect" title="Antidiabetic">antidiabetic</a>)</li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">tamoxifen</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Selective_estrogen_receptor_modulator" title="Selective estrogen receptor modulator">SERM</a>)</li> <li><a href="/wiki/Torasemide" title="Torasemide">torasemide</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Loop_diuretic" title="Loop diuretic">loop diuretic</a>)</li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">THC</a><a href="#cite_note-pmid16112652-51">[51]</a></li> <li><a href="/wiki/JWH-018" title="JWH-018">JWH-018</a><a href="#cite_note-pmid29522717-52">[52]</a></li> <li><a href="/wiki/AM-2201" title="AM-2201">AM-2201</a><a href="#cite_note-53">[53]</a></li> <li><a href="/wiki/Limonene" title="Limonene">limonene</a><a href="#cite_note-54">[54]</a> (<a href="/wiki/Monoterpene" title="Monoterpene">monoterpene</a>)</li> <li><a href="/wiki/Tapentadol" title="Tapentadol">tapentadol</a> (<a href="/wiki/Analgesic" title="Analgesic">analgesic</a>)</li> <li><a href="/wiki/Polyunsaturated_fatty_acids" class="mw-redirect" title="Polyunsaturated fatty acids">polyunsaturated fatty acids</a></li> <li><a href="/wiki/Montelukast" title="Montelukast">montelukast</a> (<a href="/wiki/Leukotriene_receptor_antagonist" class="mw-redirect" title="Leukotriene receptor antagonist">leukotriene receptor antagonist</a>)</li> <li><a href="/wiki/Diltiazem" title="Diltiazem">diltiazem</a> (minor/<a href="/wiki/Moderate_sensitive_substrates" class="mw-redirect" title="Moderate sensitive substrates">moderate sensitive substrates</a>) <a href="#cite_note-pmid11560871-55">[55]</a><a href="#cite_note-pmid23785064-56">[56]</a></li> <li><a href="/wiki/Verapamil" title="Verapamil">verapamil</a> (minor/<a href="/wiki/Moderate_sensitive_substrates" class="mw-redirect" title="Moderate sensitive substrates">moderate sensitive substrates</a>)<a href="#cite_note-UpToDate-57">[57]</a></li> <li><a href="/wiki/Candesartan" title="Candesartan">candesartan</a> (<a href="/wiki/Moderate_sensitive_substrate" class="mw-redirect" title="Moderate sensitive substrate">Moderate sensitive substrate</a>)<a href="#cite_note-CANDESARTAN_2017-58">[58]</a></li> <li><a href="/wiki/Azilsartan" title="Azilsartan">azilsartan</a> (Minor substrate of CYP2C9)<a href="#cite_note-EDARBI_2018-59">[59]</a></li></ul> </td> <td> Strong <ul><li><a href="/wiki/Miconazole" title="Miconazole">miconazole</a><a href="#cite_note-FASS-47">[47]</a> (<a href="/wiki/Antifungal_medication" class="mw-redirect" title="Antifungal medication">antifungal</a>)</li> <li><a href="/wiki/Amentoflavone" title="Amentoflavone">amentoflavone</a><a href="#cite_note-pmid19883715-60">[60]</a> (constituent of <a href="/wiki/Ginkgo_biloba" title="Ginkgo biloba">Ginkgo biloba</a> and <a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">St. John's Wort</a>)<a href="#cite_note-pmid16084098-61">[61]</a></li> <li><a href="/wiki/Sulfaphenazole" title="Sulfaphenazole">sulfaphenazole</a><a href="#cite_note-FASS-47">[47]</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Antibacterial" class="mw-redirect" title="Antibacterial">antibacterial</a>)</li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a><a href="#cite_note-FASS-47">[47]</a> (<a href="/wiki/Anticonvulsant" title="Anticonvulsant">anticonvulsant</a>, <a href="/wiki/Mood-stabilizing" class="mw-redirect" title="Mood-stabilizing">mood-stabilizing</a>)</li> <li><a href="/wiki/Apigenin" title="Apigenin">Apigenin</a><a href="#cite_note-pmid19074529-43">[43]</a></li></ul> Moderate <ul><li><a href="/wiki/Amiodarone" title="Amiodarone">amiodarone</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Antiarrhythmic" class="mw-redirect" title="Antiarrhythmic">antiarrhythmic</a>)</li> <li><a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a><a href="#cite_note-FDA_drug_development-62">[62]</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Antifungal_medication" class="mw-redirect" title="Antifungal medication">antifungal</a>)</li> <li><a href="/wiki/Metronidazole" title="Metronidazole">metronidazole</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-63">[63]</a><a href="#cite_note-64">[64]</a> (<a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> and <a href="/wiki/Antiprotozoal_medication" class="mw-redirect" title="Antiprotozoal medication">antiprotozoal medication</a>)</li> <li><a href="/wiki/Phenylbutazone" title="Phenylbutazone">phenylbutazone</a><a href="#cite_note-Flockhart-2007-44">[44]</a></li></ul> Weak <ul><li><a href="/wiki/Ceritinib" title="Ceritinib">ceritinib</a><a href="#cite_note-Flockhart-2007-44">[44]</a></li> <li><a href="/wiki/Quercetin" title="Quercetin">quercetin</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-pmid19074529-43">[43]</a> (a plant-based <a href="/wiki/Flavonol" class="mw-redirect" title="Flavonol">flavonol</a>)</li></ul> Unspecified potency <ul><li><a href="/wiki/Antihistamine" title="Antihistamine">antihistamines</a> (<a href="/wiki/H1-receptor_antagonists" class="mw-redirect" title="H1-receptor antagonists">H1-receptor antagonists</a>) <ul><li><a href="/wiki/Cyclizine" title="Cyclizine">cyclizine</a><a href="#cite_note-pmid11936702-65">[65]</a></li> <li><a href="/wiki/Promethazine" title="Promethazine">promethazine</a><a href="#cite_note-pmid11936702-65">[65]</a></li></ul></li> <li><a href="/wiki/Bergaptol" title="Bergaptol">bergaptol</a><a href="#cite_note-pmid38338457-66">[66]</a></li> <li><a href="/wiki/Chloramphenicol" title="Chloramphenicol">chloramphenicol</a><a href="#cite_note-pmid14576103-67">[67]</a></li> <li><a href="/wiki/Fenofibrate" title="Fenofibrate">fenofibrate</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Fibrate" title="Fibrate">fibrate</a>)</li> <li><a href="/wiki/Flavones" title="Flavones">flavones</a><a href="#cite_note-pmid19074529-43">[43]</a></li> <li><a href="/wiki/Flavonols" title="Flavonols">flavonols</a><a href="#cite_note-pmid19074529-43">[43]</a></li> <li><a href="/wiki/Fluvastatin" title="Fluvastatin">fluvastatin</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Statin" title="Statin">statin</a>)</li> <li><a href="/wiki/Fluvoxamine" title="Fluvoxamine">fluvoxamine</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/SSRI" class="mw-redirect" title="SSRI">SSRI</a>)</li> <li><a href="/wiki/Isoniazid" title="Isoniazid">isoniazid</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (in <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a>)</li> <li><a href="/wiki/Lovastatin" title="Lovastatin">lovastatin</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Statin" title="Statin">statin</a>)</li> <li><a href="/wiki/Modafinil" title="Modafinil">modafinil</a><a href="#cite_note-pmid10820139-68">[68]</a></li> <li><a href="/wiki/Phenylbutazone" title="Phenylbutazone">phenylbutazone</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Non-steroidal_anti-inflammatory_drug" class="mw-redirect" title="Non-steroidal anti-inflammatory drug">NSAID</a>)</li> <li><a href="/wiki/Probenecid" title="Probenecid">probenecid</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Uricosuric" title="Uricosuric">uricosuric</a>)</li> <li><a href="/wiki/Sertraline" title="Sertraline">sertraline</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/SSRI" class="mw-redirect" title="SSRI">SSRI</a>)</li> <li><a href="/wiki/Sulfamethoxazole" title="Sulfamethoxazole">sulfamethoxazole</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a>)</li> <li><a href="/wiki/Teniposide" title="Teniposide">teniposide</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Chemotherapeutic" class="mw-redirect" title="Chemotherapeutic">chemotherapeutic</a>)</li> <li><a href="/wiki/Voriconazole" title="Voriconazole">voriconazole</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Antifungal_medication" class="mw-redirect" title="Antifungal medication">antifungal</a>)</li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">zafirlukast</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Leukotriene_antagonist" class="mw-redirect" title="Leukotriene antagonist">leukotriene antagonist</a>)</li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a>, <a href="/wiki/Cannabidiol" title="Cannabidiol">cannabidiol</a>, and <a href="/wiki/Cannabinol" title="Cannabinol">cannabinol</a> (cannabis constituents)<a href="#cite_note-69">[69]</a></li> <li><a href="/wiki/Sesamin" title="Sesamin">sesamin</a><a href="#cite_note-pmid30558213-70">[70]</a> (a <a href="/wiki/Lignan" title="Lignan">lignan</a> from <a href="/wiki/Fagara" class="mw-redirect" title="Fagara">fagara</a> and <a href="/wiki/Sesame" title="Sesame">sesame</a>)</li> <li><a href="/wiki/Resveratrol" title="Resveratrol">resveratrol</a><a href="#cite_note-pmid32985569-71">[71]</a> (a plant-based <a href="/wiki/Stilbenoid" title="Stilbenoid">stilbenoid</a>)</li></ul> </td> <td> Strong <ul><li><a href="/wiki/Rifampicin" title="Rifampicin">rifampicin</a><a href="#cite_note-Flockhart-2007-44">[44]</a><a href="#cite_note-FASS-47">[47]</a> (<a href="/wiki/Bactericidal" class="mw-redirect" title="Bactericidal">bactericidal</a>)</li> <li><a href="/wiki/Secobarbital" title="Secobarbital">secobarbital</a><a href="#cite_note-Flockhart-2007-44">[44]</a> (<a href="/wiki/Barbiturate" title="Barbiturate">barbiturate</a>)</li></ul> Weak <ul><li><a href="/wiki/Aprepitant" title="Aprepitant">aprepitant</a><a href="#cite_note-usfda-tsii-45">[45]</a></li> <li><a href="/wiki/Bosentan" title="Bosentan">bosentan</a><a href="#cite_note-usfda-tsii-45">[45]</a></li> <li><a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a><a href="#cite_note-usfda-tsii-45">[45]</a></li> <li><a href="/wiki/St_Johns_Wort" class="mw-redirect" title="St Johns Wort">St Johns Wort</a><a href="#cite_note-usfda-tsii-45">[45]</a></li></ul> </td></tr> </tbody></table> <div class="mw-heading mw-heading2"><h2 id="Epoxygenase_activity">Epoxygenase activity</h2>[<a href="/w/index.php?title=CYP2C9&action=edit&section=7" title="Edit section: Epoxygenase activity">edit</a>]</div> CYP2C9 attacks various long-chain polyunsaturated fatty acids at their double (i.e. <a href="/wiki/Alkene" title="Alkene">alkene</a>) bonds to form <a href="/wiki/Epoxide" title="Epoxide">epoxide</a> products that act as signaling molecules. It along with CYP2C8, <a href="/wiki/CYP2C19" title="CYP2C19">CYP2C19</a>, <a href="/wiki/CYP2J2" title="CYP2J2">CYP2J2</a>, and possibly <a href="/wiki/CYP2S1" title="CYP2S1">CYP2S1</a> are the principle enzymes which metabolizes 1) <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a> to various <a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">epoxyeicosatrienoic acids</a> (also termed EETs); 2) <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a> to 9,10-epoxy-octadecenoic acids (also termed <a href="/wiki/Coronaric_acid" title="Coronaric acid">coronaric acid</a>, linoleic acid 9,10-oxide, or leukotoxin) and 12,13-epoxy-octadecenoic acids (also termed <a href="/wiki/Vernolic_acid" title="Vernolic acid">vernolic acid</a>, linoleic acid 12,13-oxide, or isoleukotoxin); 3) <a href="/wiki/Docosahexaenoic_acid" title="Docosahexaenoic acid">docosahexaenoic acid</a> to various <a href="/wiki/Epoxydocosapentaenoic_acid" title="Epoxydocosapentaenoic acid">epoxydocosapentaenoic acids</a> (also termed EDPs); and 4) <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acid</a> to various epoxyeicosatetraenoic acids (also termed EEQs).<a href="#cite_note-pmid25093613-9">[9]</a> Animal model studies implicate these epoxides in regulating: <a href="/wiki/Hypertension" title="Hypertension">hypertension</a>, <a href="/wiki/Myocardial_infarction" title="Myocardial infarction">myocardial infarction</a> and other insults to the heart, the growth of various cancers, <a href="/wiki/Inflammation" title="Inflammation">inflammation</a>, blood vessel formation, and pain perception; limited studies suggest but have not proven that these epoxides may function similarly in humans (see <a href="/wiki/Epoxyeicosatrienoic_acid" title="Epoxyeicosatrienoic acid">Epoxyeicosatrienoic acid</a> and <a href="/wiki/Epoxygenase" title="Epoxygenase">Epoxygenase</a>).<a href="#cite_note-pmid25093613-9">[9]</a> Since the consumption of <a href="/wiki/Omega-3_fatty_acid" title="Omega-3 fatty acid">omega-3 fatty acid</a>-rich diets dramatically raises the serum and tissue levels of the EDP and EEQ metabolites of the omega-3 fatty acid, i.e. docosahexaenoic and eicosapentaenoic acids, in animals and humans and in humans is the most prominent change in the profile of <a href="/wiki/Polyunsaturated_fatty_acid" class="mw-redirect" title="Polyunsaturated fatty acid">polyunsaturated fatty acids</a> metabolites caused by dietary omega-3 fatty acids, <a href="/wiki/Eicosapentaenoic_acid" title="Eicosapentaenoic acid">eicosapentaenoic acids</a> and EEQs may be responsible for at least some of the beneficial effects ascribed to dietary omega-3 fatty acids.<a href="#cite_note-pmid25244930-11">[11]</a><a href="#cite_note-pmid25240260-14">[14]</a><a href="#cite_note-pmid24634501-15">[15]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=CYP2C9&action=edit&section=8" title="Edit section: See also">edit</a>]</div> <ul><li><a href="/wiki/Cytochrome_P450_oxidase" class="mw-redirect" title="Cytochrome P450 oxidase">Cytochrome P450 oxidase</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=CYP2C9&action=edit&section=9" title="Edit section: References">edit</a>]</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 reflist-columns references-column-width" style="column-width: 33em;"> <ol class="references"> <li id="cite_note-refGRCh38Ensembl-1">^ <a href="#cite_ref-refGRCh38Ensembl_1-0">a</a> <a href="#cite_ref-refGRCh38Ensembl_1-1">b</a> <a href="#cite_ref-refGRCh38Ensembl_1-2">c</a> <a rel="nofollow" class="external text" href="http://May2017.archive.ensembl.org/Homo_sapiens/Gene/Summary?db=core;g=ENSG00000138109">GRCh38: Ensembl release 89: ENSG00000138109</a> – <a href="/wiki/Ensembl_genome_database_project" title="Ensembl genome database project">Ensembl</a>, May 2017 </li> <li 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Retrieved 14 July 2020.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.pharmvar.org&rft.atitle=PharmVar&rft_id=https%3A%2F%2Fwww.pharmvar.org%2Fgene%2FCYP2C9&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACYP2C9" class="Z3988"> </li> <li id="cite_note-pmid31260137-22"><a href="#cite_ref-pmid31260137_22-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBottonLuZhaoRepnikova2019" class="citation journal cs1">Botton MR, Lu X, Zhao G, Repnikova E, Seki Y, Gaedigk A, Schadt EE, Edelmann L, Scott SA (November 2019). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6810756">"Structural variation at the CYP2C locus: Characterization of deletion and duplication alleles"</a>. Human Mutation. 40 (11): e37 – e51. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fhumu.23855">10.1002/humu.23855</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6810756">6810756</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/31260137">31260137</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Human+Mutation&rft.atitle=Structural+variation+at+the+CYP2C+locus%3A+Characterization+of+deletion+and+duplication+alleles&rft.volume=40&rft.issue=11&rft.pages=%3Cspan+class%3D%22nowrap%22%3Ee37+-%3C%2Fspan%3E+%3Cspan+class%3D%22nowrap%22%3Ee51%3C%2Fspan%3E&rft.date=2019-11&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6810756%23id-name%3DPMC&rft_id=info%3Apmid%2F31260137&rft_id=info%3Adoi%2F10.1002%2Fhumu.23855&rft.aulast=Botton&rft.aufirst=MR&rft.au=Lu%2C+X&rft.au=Zhao%2C+G&rft.au=Repnikova%2C+E&rft.au=Seki%2C+Y&rft.au=Gaedigk%2C+A&rft.au=Schadt%2C+EE&rft.au=Edelmann%2C+L&rft.au=Scott%2C+SA&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6810756&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACYP2C9" class="Z3988"> </li> <li id="cite_note-pmid32602114-23"><a href="#cite_ref-pmid32602114_23-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBottonWhirl-CarrilloTrediciSangkuhl2020" class="citation journal cs1">Botton, Whirl-Carrillo, Tredici, Sangkuhl, Cavallari, Agúndez, Duconge J, Lee, Woodahl, Claudio-Campos, Daly, Klein, Pratt, Scott, Gaedigk (June 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7769975">"PharmVar GeneFocus: CYP2C19"</a>. Clinical Pharmacology and Therapeutics. 109 (2): 352–366. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcpt.1973">10.1002/cpt.1973</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7769975">7769975</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32602114">32602114</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Clinical+Pharmacology+and+Therapeutics&rft.atitle=PharmVar+GeneFocus%3A+CYP2C19&rft.volume=109&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E352-%3C%2Fspan%3E366&rft.date=2020-06&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7769975%23id-name%3DPMC&rft_id=info%3Apmid%2F32602114&rft_id=info%3Adoi%2F10.1002%2Fcpt.1973&rft.au=Botton&rft.au=Whirl-Carrillo&rft.au=Tredici&rft.au=Sangkuhl&rft.au=Cavallari&rft.au=Ag%C3%BAndez&rft.au=Duconge%2C+J&rft.au=Lee&rft.au=Woodahl&rft.au=Claudio-Campos&rft.au=Daly&rft.au=Klein&rft.au=Pratt&rft.au=Scott&rft.au=Gaedigk&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7769975&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACYP2C9" class="Z3988"> </li> <li id="cite_note-pmid8873220-24"><a href="#cite_ref-pmid8873220_24-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSullivan-KloseGhanayemBellZhang1996" class="citation journal cs1">Sullivan-Klose TH, Ghanayem BI, Bell DA, Zhang ZY, Kaminsky LS, Shenfield GM, Miners JO, Birkett DJ, Goldstein JA (August 1996). "The role of the CYP2C9-Leu359 allelic variant in the tolbutamide polymorphism". Pharmacogenetics. 6 (4): 341–349. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1097%2F00008571-199608000-00007">10.1097/00008571-199608000-00007</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8873220">8873220</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacogenetics&rft.atitle=The+role+of+the+CYP2C9-Leu359+allelic+variant+in+the+tolbutamide+polymorphism&rft.volume=6&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E341-%3C%2Fspan%3E349&rft.date=1996-08&rft_id=info%3Adoi%2F10.1097%2F00008571-199608000-00007&rft_id=info%3Apmid%2F8873220&rft.aulast=Sullivan-Klose&rft.aufirst=TH&rft.au=Ghanayem%2C+BI&rft.au=Bell%2C+DA&rft.au=Zhang%2C+ZY&rft.au=Kaminsky%2C+LS&rft.au=Shenfield%2C+GM&rft.au=Miners%2C+JO&rft.au=Birkett%2C+DJ&rft.au=Goldstein%2C+JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACYP2C9" class="Z3988"> </li> <li id="cite_note-25"><a href="#cite_ref-25">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFTornioBackman2018" class="citation book cs1">Tornio A, Backman JT (2018). 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In Chan JH, Ong YS, Cho SB (eds.). International Conference on Computational Systems – Biology and Bioinformatics. Communications in Computer and Information Science. Vol. 115. Berlin, Heidelberg: Springer. pp. 26–35. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2F978-3-642-16750-8_3">10.1007/978-3-642-16750-8_3</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-642-16749-2" title="Special:BookSources/978-3-642-16749-2"><bdi>978-3-642-16749-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20240224233906/https://books.google.com/books?id=oHmqCAAAQBAJ&pg=PA27#v=onepage&q&f=false">Archived</a> from the original on 24 February 2024. Retrieved 24 January 2022.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Study+of+the+Structural+Pathology+Caused+by+CYP2C9+Polymorphisms+towards+Flurbiprofen+Metabolism+Using+Molecular+Dynamics+Simulation.&rft.btitle=International+Conference+on+Computational+Systems+%E2%80%93+Biology+and+Bioinformatics&rft.place=Berlin%2C+Heidelberg&rft.series=Communications+in+Computer+and+Information+Science&rft.pages=%3Cspan+class%3D%22nowrap%22%3E26-%3C%2Fspan%3E35&rft.pub=Springer&rft.date=2010-11&rft_id=info%3Adoi%2F10.1007%2F978-3-642-16750-8_3&rft.isbn=978-3-642-16749-2&rft.aulast=Saikatikorn&rft.aufirst=Y&rft.au=Lertkiatmongkol%2C+P&rft.au=Assawamakin%2C+A&rft.au=Ruengjitchatchawalya%2C+M&rft.au=Tongsima%2C+S&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DoHmqCAAAQBAJ%26pg%3DPA27&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACYP2C9" class="Z3988"> </li> <li id="cite_note-32"><a href="#cite_ref-32">^</a> <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.ncbi.nlm.nih.gov/snp/rs72558187#frequency_tab">"rs72558187 allele frequency"</a>. National Center for Biotechnology Information. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201020115858/https://www.ncbi.nlm.nih.gov/snp/rs72558187#frequency_tab">Archived</a> from the original on 20 October 2020. 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Scientific Reports. 10 (1): 15910. <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/2020NatSR..1015910H">2020NatSR..1015910H</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%2Fs41598-020-72694-0">10.1038/s41598-020-72694-0</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7522226">7522226</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32985569">32985569</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Scientific+Reports&rft.atitle=Resveratrol+stereoselectively+affected+%28%C2%B1%29warfarin+pharmacokinetics+and+enhanced+the+anticoagulation+effect&rft.volume=10&rft.issue=1&rft.pages=15910&rft.date=2020-09&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7522226%23id-name%3DPMC&rft_id=info%3Apmid%2F32985569&rft_id=info%3Adoi%2F10.1038%2Fs41598-020-72694-0&rft_id=info%3Abibcode%2F2020NatSR..1015910H&rft.aulast=Huang&rft.aufirst=TY&rft.au=Yu%2C+CP&rft.au=Hsieh%2C+YW&rft.au=Lin%2C+SP&rft.au=Hou%2C+YC&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7522226&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACYP2C9" class="Z3988"> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2>[<a href="/w/index.php?title=CYP2C9&action=edit&section=10" title="Edit section: Further reading">edit</a>]</div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Further_reading_cleanup plainlinks metadata ambox ambox-style" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/40px-Edit-clear.svg.png" decoding="async" width="40" height="40" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/60px-Edit-clear.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/f2/Edit-clear.svg/80px-Edit-clear.svg.png 2x" data-file-width="48" data-file-height="48" /></div></td><td class="mbox-text"><div class="mbox-text-span">This "<a href="/wiki/Wikipedia:Manual_of_Style/Layout#Further_reading" title="Wikipedia:Manual of Style/Layout">Further reading</a>" section may need cleanup. Please read the <a href="/wiki/Wikipedia:Further_reading" title="Wikipedia:Further reading">editing guide</a> and help improve the section. (November 2020) (<a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a>)</div></td></tr></tbody></table> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin refbegin-columns references-column-width" style="column-width: 33em"> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGoldsteinde_Morais1994" class="citation journal cs1">Goldstein JA, de Morais SM (December 1994). 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"Genetic regulation of warfarin metabolism and response". Seminars in Vascular Medicine. 03 (3): 231–238. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1055%2Fs-2003-44458">10.1055/s-2003-44458</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15199455">15199455</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:260370436">260370436</a>.</cite><span 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plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Category:CYP2C9" class="extiw" title="commons:Category:CYP2C9">CYP2C9</a>.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://www.pharmgkb.org/search/annotatedGene/cyp2c9/index.jsp">PharmGKB: Annotated PGx Gene Information for CYP2C9</a></li> <li><a rel="nofollow" class="external text" href="http://bioinformatics.charite.de/supercyp/">SuperCYP: Database for Drug-Cytochrome-Interactions</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20111103123642/http://bioinformatics.charite.de/supercyp/">Archived</a> 3 November 2011 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li> <li><a rel="nofollow" class="external text" href="https://www.pharmvar.org/gene/CYP2C9">PharmVar Database for CYP2C9</a></li> <li>Human <a rel="nofollow" class="external text" href="https://genome.ucsc.edu/cgi-bin/hgTracks?db=hg38&singleSearch=knownCanonical&position=CYP2C9">CYP2C9</a> genome location and <a rel="nofollow" class="external text" href="https://genome.ucsc.edu/cgi-bin/hgGene?db=hg38&hgg_type=knownGene&hgg_gene=CYP2C9">CYP2C9</a> gene details page in the <a href="/wiki/UCSC_Genome_Browser" title="UCSC Genome Browser">UCSC Genome Browser</a>.</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output 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srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e1/PDB_1og2_EBI.jpg/330px-PDB_1og2_EBI.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e1/PDB_1og2_EBI.jpg/500px-PDB_1og2_EBI.jpg 2x" data-file-width="800" data-file-height="600" /></a></div> <div class="gallerytext">1og2: STRUCTURE OF HUMAN CYTOCHROME P450 CYP2C9</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 210px;"><a href="/wiki/File:PDB_1og5_EBI.jpg" class="mw-file-description" title="1og5: STRUCTURE OF HUMAN CYTOCHROME P450 CYP2C9"><img alt="1og5: STRUCTURE OF HUMAN CYTOCHROME P450 CYP2C9" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/PDB_1og5_EBI.jpg/180px-PDB_1og5_EBI.jpg" decoding="async" width="180" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/PDB_1og5_EBI.jpg/270px-PDB_1og5_EBI.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/PDB_1og5_EBI.jpg/360px-PDB_1og5_EBI.jpg 2x" data-file-width="800" data-file-height="600" /></a></div> <div class="gallerytext">1og5: STRUCTURE OF HUMAN CYTOCHROME P450 CYP2C9</div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 210px;"><a href="/wiki/File:PDB_1r9o_EBI.jpg" class="mw-file-description" title="1r9o: Crystal Structure of P4502C9 with Flurbiprofen bound"><img alt="1r9o: Crystal Structure of P4502C9 with Flurbiprofen bound" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/PDB_1r9o_EBI.jpg/180px-PDB_1r9o_EBI.jpg" decoding="async" width="180" height="135" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7b/PDB_1r9o_EBI.jpg/270px-PDB_1r9o_EBI.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7b/PDB_1r9o_EBI.jpg/360px-PDB_1r9o_EBI.jpg 2x" data-file-width="800" data-file-height="600" /></a></div> <div class="gallerytext">1r9o: Crystal Structure of P4502C9 with Flurbiprofen bound</div> </li> </ul></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Cytochromes,_oxygenases:_cytochrome_P450_(Most_belong_to_EC_1.14)206" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#e7dcc3"><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:Cytochrome_P450" title="Template:Cytochrome P450"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cytochrome_P450" title="Template talk:Cytochrome P450"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cytochrome_P450" title="Special:EditPage/Template:Cytochrome P450"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Cytochromes,_oxygenases:_cytochrome_P450_(Most_belong_to_EC_1.14)206" style="font-size:114%;margin:0 4em"><a href="/wiki/Cytochrome" title="Cytochrome">Cytochromes</a>, <a href="/wiki/Oxygenase" title="Oxygenase">oxygenases</a>: <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> (Most belong to <a href="/wiki/Enzyme_Commission_number" title="Enzyme Commission number">EC</a> 1.14)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP1</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/CYP1A1" title="CYP1A1">A1</a></li> <li><a href="/wiki/CYP1A2" title="CYP1A2">A2</a></li> <li><a href="/w/index.php?title=CYP1A5&action=edit&redlink=1" class="new" title="CYP1A5 (page does not exist)">A5</a></li> <li><a href="/wiki/CYP1B1" title="CYP1B1">B1</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP2</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/CYP2A6" title="CYP2A6">A6</a></li> <li><a href="/wiki/CYP2A7" title="CYP2A7">A7</a></li> <li><a href="/wiki/CYP2A13" title="CYP2A13">A13</a></li> <li><a href="/wiki/CYP2B6" title="CYP2B6">B6</a></li> <li><a href="/wiki/CYP2C8" title="CYP2C8">C8</a></li> <li><a class="mw-selflink selflink">C9</a></li> <li><a href="/wiki/CYP2C18" title="CYP2C18">C18</a></li> <li><a href="/wiki/CYP2C19" title="CYP2C19">C19</a></li> <li><a href="/wiki/CYP2D6" title="CYP2D6">D6</a></li> <li><a href="/wiki/CYP2E1" title="CYP2E1">E1</a></li> <li><a href="/wiki/CYP2F1" title="CYP2F1">F1</a></li> <li><a href="/wiki/CYP2J2" title="CYP2J2">J2</a></li> <li><a href="/wiki/CYP2R1" title="CYP2R1">R1</a></li> <li><a href="/wiki/CYP2S1" title="CYP2S1">S1</a></li> <li><a href="/wiki/CYP2U1" title="CYP2U1">U1</a></li> <li><a href="/wiki/CYP2W1" title="CYP2W1">W1</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP3 (<a href="/wiki/CYP3A" title="CYP3A">CYP3A</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/CYP3A4" title="CYP3A4">A4</a></li> <li><a href="/wiki/CYP3A5" title="CYP3A5">A5</a></li> <li><a href="/wiki/CYP3A7" title="CYP3A7">A7</a></li> <li><a href="/w/index.php?title=CYP3A37&action=edit&redlink=1" class="new" title="CYP3A37 (page does not exist)">A37</a></li> <li><a href="/wiki/CYP3A43" title="CYP3A43">A43</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP4</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/CYP4A11" title="CYP4A11">A11</a></li> <li><a href="/wiki/CYP4A22" title="CYP4A22">A22</a></li> <li><a href="/wiki/CYP4B1" title="CYP4B1">B1</a></li> <li><a href="/wiki/CYP4F2" title="CYP4F2">F2</a></li> <li><a href="/wiki/CYP4F3" title="CYP4F3">F3</a></li> <li><a href="/wiki/CYP4F8" title="CYP4F8">F8</a></li> <li><a href="/wiki/CYP4F11" title="CYP4F11">F11</a></li> <li><a href="/wiki/CYP4F12" title="CYP4F12">F12</a></li> <li><a href="/wiki/CYP4F22" title="CYP4F22">F22</a></li> <li><a href="/wiki/CYP4V2" title="CYP4V2">V2</a></li> <li><a href="/wiki/CYP4X1" title="CYP4X1">X1</a></li> <li><a href="/wiki/CYP4Z1" title="CYP4Z1">Z1</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP5-20</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>CYP5 (<a href="/wiki/Thromboxane-A_synthase" title="Thromboxane-A synthase">A1</a>)</li> <li><a href="/wiki/CYP6_family" title="CYP6 family">CYP6</a> (<a href="/wiki/CYP6G1" title="CYP6G1">G1</a>, <a href="/wiki/CYP6M2" title="CYP6M2">M2</a>)</li> <li>CYP7 (<a href="/wiki/Cholesterol_7_alpha-hydroxylase" title="Cholesterol 7 alpha-hydroxylase">A1</a>, <a href="/wiki/CYP7B1" title="CYP7B1">B1</a>)</li> <li>CYP8 (<a href="/wiki/CYP8A1" class="mw-redirect" title="CYP8A1">A1</a>, <a href="/wiki/CYP8B1" title="CYP8B1">B1</a>)</li> <li><a href="/wiki/CYP9_family" title="CYP9 family">CYP9</a></li> <li><a href="/wiki/CYP10_family" title="CYP10 family">CYP10</a></li> <li><a href="/wiki/CYP11_family" title="CYP11 family">CYP11</a> (<a href="/wiki/Cholesterol_side-chain_cleavage_enzyme" title="Cholesterol side-chain cleavage enzyme">A1</a>, <a href="/wiki/CYP11A2" title="CYP11A2">A2</a>, <a href="/wiki/Steroid_11-beta-hydroxylase" class="mw-redirect" title="Steroid 11-beta-hydroxylase">B1</a>, <a href="/wiki/Aldosterone_synthase" title="Aldosterone synthase">B2</a>, <a href="/wiki/CYP11B3" title="CYP11B3">B3</a>, <a href="/wiki/CYP11C1" title="CYP11C1">C1</a>)</li> <li><a href="/wiki/CYP12_family" title="CYP12 family">CYP12</a></li> <li><a href="/wiki/CYP13_family" title="CYP13 family">CYP13</a></li> <li><a href="/wiki/CYP14_family" title="CYP14 family">CYP14</a></li> <li><a href="/wiki/CYP15_family" title="CYP15 family">CYP15</a></li> <li><a href="/wiki/CYP16_family" title="CYP16 family">CYP16</a></li> <li>CYP17 (<a href="/wiki/CYP17A1" title="CYP17A1">A1</a>)</li> <li><a href="/wiki/CYP18_family" title="CYP18 family">CYP18</a></li> <li>CYP19 (<a href="/wiki/Aromatase" title="Aromatase">A1</a>)</li> <li>CYP20 (<a href="/wiki/CYP20A1" title="CYP20A1">A1</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP21-49</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>CYP21 (<a href="/wiki/21-Hydroxylase" title="21-Hydroxylase">A2</a>)</li> <li>CYP22 (<a href="/wiki/Daf-9" title="Daf-9">A1</a>)</li> <li><a href="/wiki/CYP23_family" title="CYP23 family">CYP23</a></li> <li>CYP24 (<a href="/wiki/CYP24A1" title="CYP24A1">A1</a>)</li> <li><a href="/wiki/CYP25_family" title="CYP25 family">CYP25</a></li> <li><a href="/wiki/CYP26_family" title="CYP26 family">CYP26</a> (<a href="/wiki/CYP26A1" title="CYP26A1">A1</a>, <a href="/wiki/CYP26B1" title="CYP26B1">B1</a>, <a href="/wiki/CYP26C1" title="CYP26C1">C1</a>)</li> <li><a href="/wiki/CYP27_family" title="CYP27 family">CYP27</a> (<a href="/wiki/CYP27A1" title="CYP27A1">A1</a>, <a href="/wiki/25-Hydroxyvitamin_D3_1-alpha-hydroxylase" class="mw-redirect" title="25-Hydroxyvitamin D3 1-alpha-hydroxylase">B1</a>, <a href="/wiki/CYP27C1" title="CYP27C1">C1</a>)</li> <li>CYP28 (<a href="/wiki/CYP28A1" title="CYP28A1">A1</a>)</li> <li><a href="/w/index.php?title=CYP29_family&action=edit&redlink=1" class="new" title="CYP29 family (page does not exist)">CYP29</a></li> <li>CYP35 (<a href="/wiki/CYP35B1" title="CYP35B1">B1</a>)</li> <li>CYP39 (<a href="/wiki/CYP39A1" title="CYP39A1">A1</a>)</li> <li>CYP46 (<a href="/wiki/CYP46A1" class="mw-redirect" title="CYP46A1">A1</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP51-69</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/Sterol_14-demethylase" title="Sterol 14-demethylase">CYP51</a> (<a href="/wiki/Lanosterol_14_alpha-demethylase" title="Lanosterol 14 alpha-demethylase">A1</a>, <a href="/wiki/ERG11" title="ERG11">F1</a>)</li> <li><a href="/wiki/CYP52_family" title="CYP52 family">CYP52</a></li> <li><a href="/wiki/CYP53_family" title="CYP53 family">CYP53</a> <ul><li><a href="/wiki/Benzoate_4-monooxygenase" title="Benzoate 4-monooxygenase">A1</a></li></ul></li> <li><a href="/wiki/CYP55_family" title="CYP55 family">CYP55</a> <ul><li><a href="/wiki/Nitric_oxide_reductase_(NAD(P),_nitrous_oxide-forming)" title="Nitric oxide reductase (NAD(P), nitrous oxide-forming)">A1</a></li></ul></li> <li>CYP56 <ul><li><a href="/wiki/CYP56A1" title="CYP56A1">A1</a></li></ul></li> <li><a href="/wiki/ERG5" title="ERG5">CYP61</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP71-99</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>CYP71 (<a href="/wiki/3-hydroxyindolin-2-one_monooxygenase" title="3-hydroxyindolin-2-one monooxygenase">C1</a>, <a href="/wiki/Indolin-2-one_monooxygenase" title="Indolin-2-one monooxygenase">C2</a>, <a href="/wiki/2-Hydroxy-1,4-benzoxazin-3-one_monooxygenase" title="2-Hydroxy-1,4-benzoxazin-3-one monooxygenase">C3</a>, <a href="/wiki/Indole-2-monooxygenase" title="Indole-2-monooxygenase">C4</a>, <a href="/wiki/Ent-isokaurene_C2-hydroxylase" title="Ent-isokaurene C2-hydroxylase">Z6</a>, <a href="/wiki/Angelicin_synthase" title="Angelicin synthase">AJ4</a>, <a href="/wiki/Amorpha-4,11-diene_12-monooxygenase" title="Amorpha-4,11-diene 12-monooxygenase">AV1</a>, <a href="/wiki/Alpha-humulene_10-hydroxylase" title="Alpha-humulene 10-hydroxylase">BA1</a>)</li> <li><a href="/wiki/Secologanin_synthase" title="Secologanin synthase">CYP72A1</a></li> <li><a href="/wiki/Trans-cinnamate_4-monooxygenase" title="Trans-cinnamate 4-monooxygenase">CYP73A1</a></li> <li><a href="/wiki/CYP74_family" title="CYP74 family">CYP74</a> (<a href="/wiki/Colneleate_synthase" title="Colneleate synthase">D1</a>)</li> <li>CYP75 (<a href="/wiki/Flavonoid_3%27,5%27-hydroxylase" title="Flavonoid 3',5'-hydroxylase">A1</a>, <a href="/wiki/Flavonoid_3%27-monooxygenase" title="Flavonoid 3'-monooxygenase">B1</a>)</li> <li><a href="/wiki/CYP76_family" title="CYP76 family">CYP76</a> (<a href="/wiki/Geraniol_8-hydroxylase" title="Geraniol 8-hydroxylase">B6</a>, <a href="/wiki/Ent-cassa-12,15-diene_11-hydroxylase" title="Ent-cassa-12,15-diene 11-hydroxylase">M7</a>)</li> <li>CYP79 (<a href="/wiki/Tyrosine_N-monooxygenase" title="Tyrosine N-monooxygenase">A1</a>, <a href="/wiki/Phenylalanine_N-monooxygenase" title="Phenylalanine N-monooxygenase">A2</a>, <a href="/wiki/Tryptophan_N-monooxygenase" title="Tryptophan N-monooxygenase">B1</a>, <a href="/wiki/Tryptophan_N-monooxygenase" title="Tryptophan N-monooxygenase">B2</a>, <a href="/wiki/Tryptophan_N-monooxygenase" title="Tryptophan N-monooxygenase">B3</a>, <a href="/wiki/Valine_N-monooxygenase" title="Valine N-monooxygenase">D1</a>, <a href="/wiki/Valine_N-monooxygenase" title="Valine N-monooxygenase">D2</a>, <a href="/wiki/Isoleucine_N-monooxygenase" title="Isoleucine N-monooxygenase">D3</a>, <a href="/wiki/Isoleucine_N-monooxygenase" title="Isoleucine N-monooxygenase">D4</a>)</li> <li>CYP80 (<a href="/wiki/Berbamunine_synthase" title="Berbamunine synthase">A1</a>, <a href="/wiki/N-methylcoclaurine_3%27-monooxygenase" title="N-methylcoclaurine 3'-monooxygenase">B1</a>, <a href="/wiki/(S)-corytuberine_synthase" title="(S)-corytuberine synthase">G2</a>)</li> <li>CYP81 (<a href="/wiki/Isoflavone_2%27-hydroxylase" title="Isoflavone 2'-hydroxylase">E1</a>, <a href="/wiki/4%27-methoxyisoflavone_2%27-hydroxylase" title="4'-methoxyisoflavone 2'-hydroxylase">E3</a>, <a href="/wiki/4%27-methoxyisoflavone_2%27-hydroxylase" title="4'-methoxyisoflavone 2'-hydroxylase">E7</a>, <a href="/wiki/Isoflavone_3%27-hydroxylase" title="Isoflavone 3'-hydroxylase">E9</a>)</li> <li><a href="/wiki/Beta-amyrin_11-oxidase" title="Beta-amyrin 11-oxidase">CYP88D6</a></li> <li><a href="/wiki/3-Epi-6-deoxocathasterone_23-monooxygenase" title="3-Epi-6-deoxocathasterone 23-monooxygenase">CYP90C1</a></li> <li><a href="/wiki/Beta-amyrin_24-hydroxylase" title="Beta-amyrin 24-hydroxylase">CYP93E1</a></li> <li><a href="/wiki/Carotene_epsilon-monooxygenase" title="Carotene epsilon-monooxygenase">CYP97C1</a></li> <li><a href="/wiki/9beta-pimara-7,15-diene_oxidase" title="9beta-pimara-7,15-diene oxidase">CYP99A3</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP101-281</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/Camphor_5-monooxygenase" title="Camphor 5-monooxygenase">CYP101A1</a></li> <li><a href="/wiki/Cytochrome_P450_BM3" title="Cytochrome P450 BM3">CYP102A1</a></li> <li><a href="/wiki/CYP105_family" title="CYP105 family">CYP105</a> <ul><li><a href="/wiki/Vitamin_D3_dihydroxylase" title="Vitamin D3 dihydroxylase">A1</a></li> <li><a href="/wiki/Pentalenic_acid_synthase" title="Pentalenic acid synthase">D7</a></li></ul></li> <li><a href="/wiki/Steroid_15beta-monooxygenase" title="Steroid 15beta-monooxygenase">CYP106A2</a></li> <li><a href="/wiki/CYP107_family" title="CYP107 family">CYP107</a> <ul><li><a href="/wiki/Cytochrome_P450_eryF" title="Cytochrome P450 eryF">A1</a></li> <li><a href="/wiki/CYP107G1" title="CYP107G1">G1</a></li></ul></li> <li><a href="/wiki/CYP109_family" title="CYP109 family">CYP109</a> <ul><li><a href="/wiki/CYP109B1" title="CYP109B1">B1</a></li> <li><a href="/wiki/CYP109E1" title="CYP109E1">E1</a></li></ul></li> <li><a href="/wiki/Linalool_8-monooxygenase" title="Linalool 8-monooxygenase">CYP111</a></li> <li><a href="/wiki/Erythromycin_12_hydroxylase" title="Erythromycin 12 hydroxylase">CYP113A1</a></li> <li><a href="/wiki/CYP119A1" title="CYP119A1">CYP119A1</a></li> <li><a href="/wiki/CYP123_family" title="CYP123 family">CYP123</a></li> <li><a href="/wiki/Cholest-4-en-3-one_26-monooxygenase" title="Cholest-4-en-3-one 26-monooxygenase">CYP125A1</a></li> <li><a href="/wiki/CYP139_family" title="CYP139 family">CYP139</a></li> <li><a href="/wiki/CYP147_family" title="CYP147 family">CYP147</a></li> <li><a href="/wiki/Fatty-acid_peroxygenase" title="Fatty-acid peroxygenase">CYP152</a> <ul><li>A1</li> <li>B1</li></ul></li> <li><a href="/wiki/CYP154C3" title="CYP154C3">CYP154C3</a></li> <li><a href="/wiki/Biflaviolin_synthase" title="Biflaviolin synthase">CYP158A</a></li> <li><a href="/wiki/Pentalenolactone_synthase" title="Pentalenolactone synthase">CYP161C</a></li> <li>CYP170 <ul><li><a href="/wiki/Epi-isozizaene_5-monooxygenase" title="Epi-isozizaene 5-monooxygenase">A1</a></li> <li><a href="/wiki/CYP170B1" title="CYP170B1">B1</a></li></ul></li> <li><a href="/wiki/1,8-Cineole_2-endo-monooxygenase" title="1,8-Cineole 2-endo-monooxygenase">CYP176A1</a></li> <li><a href="/wiki/Pentalenene_oxygenase" title="Pentalenene oxygenase">CYP183A</a></li> <li><a href="/wiki/CYP197_family" title="CYP197 family">CYP197</a></li> <li><a href="/wiki/4-methoxybenzoate_monooxygenase_(O-demethylating)" title="4-methoxybenzoate monooxygenase (O-demethylating)">CYP199A2</a></li> <li><a href="/wiki/Cytochrome_P450_aromatic_O-demethylase" title="Cytochrome P450 aromatic O-demethylase">CYP255A</a> </li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP301-499</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/CYP303A1" title="CYP303A1">CYP303A1</a></li> <li><a href="/wiki/CYP305_family" title="CYP305 family">CYP305</a> <ul><li><a href="/wiki/CYP305M2" title="CYP305M2">M2</a></li></ul></li> <li><a href="/wiki/Halloween_genes" title="Halloween genes">Halloween genes</a> ( CYP302A1, CYP306A1, CYP307A1, CYP307A2, <a href="/wiki/Ecdysone_20-monooxygenase" title="Ecdysone 20-monooxygenase">CYP314A1</a>, CYP315A1)</li> <li><a href="/wiki/CYP318A1" title="CYP318A1">CYP318A1</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP501-699</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/Ent-kaurene_oxidase" title="Ent-kaurene oxidase">CYP503</a></li> <li><a href="/wiki/3-hydroxyphenylacetate_6-hydroxylase" title="3-hydroxyphenylacetate 6-hydroxylase">CYP504B1</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background-color: AntiqueWhite">CYP701-999</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/CYP704B22" class="mw-redirect" title="CYP704B22">CYP704B22</a></li> <li><a href="/wiki/CYP710_family" title="CYP710 family">CYP710</a></li> <li><a href="/wiki/Abietadienol_hydroxylase" title="Abietadienol hydroxylase">CYP720A1</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Enzymes56" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Enzymes" title="Template:Enzymes"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Enzymes" title="Template talk:Enzymes"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Enzymes" title="Special:EditPage/Template:Enzymes"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Enzymes56" style="font-size:114%;margin:0 4em"><a href="/wiki/Enzyme" title="Enzyme">Enzymes</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Activity</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/Active_site" title="Active site">Active site</a></li> <li><a href="/wiki/Binding_site" title="Binding site">Binding site</a></li> <li><a href="/wiki/Catalytic_triad" title="Catalytic triad">Catalytic triad</a></li> <li><a href="/wiki/Oxyanion_hole" title="Oxyanion hole">Oxyanion hole</a></li> <li><a href="/wiki/Enzyme_promiscuity" title="Enzyme promiscuity">Enzyme promiscuity</a></li> <li><a href="/wiki/Diffusion-limited_enzyme" title="Diffusion-limited enzyme">Diffusion-limited enzyme</a></li> <li><a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">Cofactor</a></li> <li><a href="/wiki/Enzyme_catalysis" title="Enzyme catalysis">Enzyme catalysis</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Regulation</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/Allosteric_regulation" title="Allosteric regulation">Allosteric regulation</a></li> <li><a href="/wiki/Cooperativity" title="Cooperativity">Cooperativity</a></li> <li><a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">Enzyme inhibitor</a></li> <li><a href="/wiki/Enzyme_activator" title="Enzyme activator">Enzyme activator</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Classification</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/Enzyme_Commission_number" title="Enzyme Commission number">EC number</a></li> <li><a href="/wiki/Protein_superfamily" title="Protein superfamily">Enzyme superfamily</a></li> <li><a href="/wiki/Protein_family" title="Protein family">Enzyme family</a></li> <li><a href="/wiki/List_of_enzymes" title="List of enzymes">List of enzymes</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Kinetics</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/Enzyme_kinetics" title="Enzyme kinetics">Enzyme kinetics</a></li> <li><a href="/wiki/Eadie%E2%80%93Hofstee_diagram" title="Eadie–Hofstee diagram">Eadie–Hofstee diagram</a></li> <li><a href="/wiki/Hanes%E2%80%93Woolf_plot" title="Hanes–Woolf plot">Hanes–Woolf plot</a></li> <li><a href="/wiki/Lineweaver%E2%80%93Burk_plot" title="Lineweaver–Burk plot">Lineweaver–Burk plot</a></li> <li><a href="/wiki/Michaelis%E2%80%93Menten_kinetics" title="Michaelis–Menten kinetics">Michaelis–Menten kinetics</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Types</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>EC1 <a href="/wiki/Oxidoreductase" title="Oxidoreductase">Oxidoreductases</a> (<a href="/wiki/List_of_EC_numbers_(EC_1)" title="List of EC numbers (EC 1)">list</a>)</li> <li>EC2 <a href="/wiki/Transferase" title="Transferase">Transferases</a> (<a href="/wiki/List_of_EC_numbers_(EC_2)" title="List of EC numbers (EC 2)">list</a>)</li> <li>EC3 <a href="/wiki/Hydrolase" title="Hydrolase">Hydrolases</a> (<a href="/wiki/List_of_EC_numbers_(EC_3)" title="List of EC numbers (EC 3)">list</a>)</li> <li>EC4 <a href="/wiki/Lyase" title="Lyase">Lyases</a> (<a href="/wiki/List_of_EC_numbers_(EC_4)" title="List of EC numbers (EC 4)">list</a>)</li> <li>EC5 <a href="/wiki/Isomerase" title="Isomerase">Isomerases</a> (<a href="/wiki/List_of_EC_numbers_(EC_5)" title="List of EC numbers (EC 5)">list</a>)</li> <li>EC6 <a href="/wiki/Ligase" title="Ligase">Ligases</a> (<a href="/wiki/List_of_EC_numbers_(EC_6)" title="List of EC numbers (EC 6)">list</a>)</li> <li>EC7 <a href="/wiki/Translocase" title="Translocase">Translocases</a> (<a href="/wiki/List_of_EC_numbers_(EC_7)" title="List of EC numbers (EC 7)">list</a>)</li></ul> </div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output 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