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class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_metabolism"> <div class="vector-toc-text"> 3 Further metabolism </div> </a> <ul id="toc-Further_metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Activities" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Activities"> <div class="vector-toc-text"> 4 Activities </div> </a> <button aria-controls="toc-Activities-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Activities subsection </button> <ul id="toc-Activities-sublist" class="vector-toc-list"> <li id="toc-15(S)-HpETE_and_15(S)-HETE" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#15(S)-HpETE_and_15(S)-HETE"> <div class="vector-toc-text"> 4.1 15(S)-HpETE and 15(S)-HETE </div> </a> <ul id="toc-15(S)-HpETE_and_15(S)-HETE-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-15(R)-HETE" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#15(R)-HETE"> <div class="vector-toc-text"> 4.2 15(R)-HETE </div> </a> <ul id="toc-15(R)-HETE-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-15-Oxo-ETE" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#15-Oxo-ETE"> <div class="vector-toc-text"> 4.3 15-Oxo-ETE </div> </a> <ul id="toc-15-Oxo-ETE-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-5-Oxo-15(S)-hydroxy-ETE" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#5-Oxo-15(S)-hydroxy-ETE"> <div class="vector-toc-text"> 4.4 5-Oxo-15(S)-hydroxy-ETE </div> </a> <ul id="toc-5-Oxo-15(S)-hydroxy-ETE-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Lipoxins" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Lipoxins"> <div class="vector-toc-text"> 4.5 Lipoxins </div> </a> 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td+td{width:60%}</style> <table class="infobox ib-chembox"> <caption>15-Hydroxyeicosatetraenoic acid </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><a href="/wiki/File:15(S)-HETE.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/15%28S%29-HETE.svg/220px-15%28S%29-HETE.svg.png" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2b/15%28S%29-HETE.svg/330px-15%28S%29-HETE.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2b/15%28S%29-HETE.svg/440px-15%28S%29-HETE.svg.png 2x" data-file-width="512" data-file-height="385" /></a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(5Z,8Z,11Z,13E,15S)-15-Hydroxyicosa-5,8,11,13-tetraenoic acid</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">15-HETE, 15(S)-HETE, 15(S)-HETE</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=54845-95-3">54845-95-3</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CCCCC%5BC%40%40H%5D%28%2FC%3DC%2FC%3DC%5CC%2FC%3DC%5CC%2FC%3DC%5CCCCC%28%3DO%29O%29O">Interactive image</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4444307.html">4444307</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard">ECHA InfoCard</a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.214.805">100.214.805</a> <a href="https://www.wikidata.org/wiki/Q21099561#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=3401">3401</a></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/5280724">5280724</a></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/44JHK6G39Q">44JHK6G39Q</a> <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" />Y</li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: JSFATNQSLKRBCI-VAEKSGALSA-N</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">CCCCC[C@@H](/C=C/C=C\C/C=C\C/C=C\CCCC(=O)O)O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td>C20H32O3 </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td>320.473 g·mol−1 </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> 15-Hydroxyeicosatetraenoic acid (also termed 15-HETE, 15(S)-HETE, and 15S-HETE) is an <a href="/wiki/Eicosanoid" title="Eicosanoid">eicosanoid</a>, i.e. a metabolite of <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a>. Various cell types metabolize arachidonic acid to 15(S)-hydroperoxyeicosatetraenoic acid (15(S)-HpETE). This initial <a href="/wiki/Peroxide" title="Peroxide">hydroperoxide</a> product is extremely short-lived in cells: if not otherwise metabolized, it is rapidly reduced to 15(S)-HETE. Both of these metabolites, depending on the cell type which forms them, can be further metabolized to 15-oxo-eicosatetraenoic acid (15-oxo-ETE), 5(S),15(S)-dihydroxy-eicosatetraenoic acid (5(S),15(S)-diHETE), 5-oxo-15(S)-hydroxyeicosatetraenoic acid (5-oxo-15(S)-HETE), a subset of <a href="/wiki/Specialized_pro-resolving_mediators" title="Specialized pro-resolving mediators">specialized pro-resolving mediators</a> viz., the <a href="/wiki/Lipoxin" title="Lipoxin">lipoxins</a>, a class of pro-inflammatory mediators, the <a href="/wiki/Eoxin" title="Eoxin">eoxins</a>, and other products that have less well-defined activities and functions. Thus, 15(S)-HETE and 15(S)-HpETE, in addition to having intrinsic biological activities, are key precursors to numerous biologically active derivatives.<a href="#cite_note-New_aspects_of_the_role_of_hydroxyeicosatetraenoic_acids_in_cell_growth_and_cancer_development-1">[1]</a><a href="#cite_note-Cyclooxygenases_and_lipoxygenases_in_cancer-2">[2]</a> Some cell types (e.g. <a href="/wiki/Platelet" title="Platelet">platelets</a>) metabolize arachidonic acid to the <a href="/wiki/Stereoisomerism" title="Stereoisomerism">stereoisomer</a> of 15(S)-HpETE, 15(R)-HpETE. Both stereoisomers may also be formed as result of the metabolism of arachidonic acid by cellular microsomes or as a result of arachidonic acid <a href="/wiki/Auto-oxidation" class="mw-redirect" title="Auto-oxidation">auto-oxidation</a>. Similar to 15(S)-HpETEs, 15(R)-HpETE may be rapidly reduced to 15(R)-HETE. These R,S stereoisomers differ only in having their <a href="/wiki/Hydroxy_group" title="Hydroxy group">hydroxy</a> residue in opposite orientations. While the two R stereoisomers are sometimes referred to as 15-HpETE and 15-HETE, proper usage should identify them as R stereoisomers. 15(R)-HpETE and 15(R)-HETE lack some of the activity attributed to their S stereoisomers but can be further metabolized to bioactive products viz., the 15(R) class of <a href="/wiki/Lipoxin" title="Lipoxin">lipoxins</a> (also termed <a href="/wiki/Epi-lipoxin" title="Epi-lipoxin">epi-lipoxins</a>).<a href="#cite_note-resolve-3">[3]</a> 15(S)-HETE, 15(S)-HpETE, and many of their derivative metabolites are thought to have physiologically important functions. They appear to act as <a href="/wiki/Hormone" title="Hormone">hormone</a>-like <a href="/wiki/Autocrine_signaling" title="Autocrine signaling">autocrine</a> and <a href="/wiki/Paracrine_signaling" title="Paracrine signaling">paracrine signaling</a> agents that are involved in regulating <a href="/wiki/Inflammation" title="Inflammation">inflammatory</a> and perhaps other responses.<a href="#cite_note-New_aspects_of_the_role_of_hydroxyeicosatetraenoic_acids_in_cell_growth_and_cancer_development-1">[1]</a><a href="#cite_note-Cyclooxygenases_and_lipoxygenases_in_cancer-2">[2]</a><a href="#cite_note-4">[4]</a> Clinically, drugs that are stable analogs, and therefore mimic the anti-inflammatory actions of the lipoxins and drugs that block the production or actions of the pro-inflammatory eoxins may prove useful for treating acute and chronic <a href="/wiki/Inflammation" title="Inflammation">inflammatory</a> disorders.<a href="#cite_note-pmid8087575-5">[5]</a> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Nomenclature_and_stereoisomers">Nomenclature and stereoisomers</h2>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=1" title="Edit section: Nomenclature and stereoisomers">edit</a>]</div> 15(S)-HETE is unambiguously designated by a shortened version of its <a href="/wiki/IUPAC" class="mw-redirect" title="IUPAC">IUPAC</a> name viz., 15(S)-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid. In this terminology S refers to the <a href="/wiki/Absolute_configuration" title="Absolute configuration">absolute configuration</a> of the <a href="/wiki/Chirality_(chemistry)" title="Chirality (chemistry)">chirality</a> of the hydroxy <a href="/wiki/Functional_group" title="Functional group">functional group</a> at carbon position 15. Its 15(R) <a href="/wiki/Enantiomer" title="Enantiomer">enantiomer</a> is designated 15(R)-hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acid. Z and E give the <a href="/wiki/Cis%E2%80%93trans_isomerism" title="Cis–trans isomerism">cis–trans isomerism</a> about each <a href="/wiki/Double_bond" title="Double bond">double bond</a> at carbon positions 5, 8, 11, and 13 with Z indicating cis and E indicating trans isomerism. Both stereoisomers are produced from their corresponding S and R 15-HpETE stereoisomers, i.e. 15(S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (15(S)-HpETE) and 15(R)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (15(R)-HpETE). <div class="mw-heading mw-heading2"><h2 id="Production">Production</h2>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=2" title="Edit section: Production">edit</a>]</div> Human cells release <a href="/wiki/Arachidonic_acid" title="Arachidonic acid">arachidonic acid</a> (i.e. 5Z,8Z,11Z,14Z-eicosatetraenoic acid) from its storage site in <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a> by reactions that involve <a href="/wiki/Phospholipase_C" title="Phospholipase C">phospholipase C</a> and/or <a href="/wiki/Lipase" title="Lipase">lipase</a> enzymes. This release is stimulated or enhanced by cell stimulation. The freed arachidonic acid is then converted to 15-hydroperoxy/hydroxy products by one or more of the following five pathways. 15-Lipoxygenase-1: Cells metabolize arachidonic acid with 15-lipoxygenase-1 (i.e., 15-LO-1, <a href="/wiki/ALOX15" title="ALOX15">ALOX15</a>) to form 15(S)-HpETE as a major product and 12(S)-hydroperoxy-5Z,8Z,10E,15Z-eicosatetraenoic acid (12(S)-HpETE) and 14(S),15(S)-trans-oxido-5Z,8Z,11Z-14,15-leukotriene A4 as minor products; 15(S)-HpETE and 12(S)-HpETE are rapidly converted to 15(S)-HETE and 12(S)-hydroxy-5Z,8Z,10E,15Z-eicosatetraenoic acid (<a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12(S)-hydroxyeicosatetraenoic acid</a>), (i.e. 12(S)-HETE), respectively, or further metabolized through other enzyme pathways; 14(S),15(S)-trans-oxido-5Z,8Z,11Z-14,15-leukotriene A4 is metabolized by 15-LO-1 to various isomers of 8,15(S)-dihydroxy-5S,8S,11Z,13S-eicosatetraenoic acids, e.g. 8,15(S)-LTB4's.<a href="#cite_note-6">[6]</a><a href="#cite_note-7">[7]</a><a href="#cite_note-8">[8]</a><a href="#cite_note-9">[9]</a><a href="#cite_note-ReferenceA-10">[10]</a> 15-Lipoxygenase-2: Cells also used 15-lipoxygenase 2 (i.e. 15-LOX-2 or <a href="/wiki/ALOX15B" title="ALOX15B">ALOX15B</a>) to make 15(S)-HpETE and 15(S)-HETE. However this enzyme has a preference for metabolizing <a href="/wiki/Linoleic_acid" title="Linoleic acid">linoleic acid</a> rather than arachidonic acid. It therefore forms linoleic acid metabolites (e.g. <a href="/wiki/13-Hydroxyoctadecadienoic_acid" title="13-Hydroxyoctadecadienoic acid">13-hydoxyperoxy/hydroxy-octadecadienoic</a> and <a href="/wiki/9-Hydroxyoctadecadienoic_acid" title="9-Hydroxyoctadecadienoic acid">9-hydroperoxy/hydroxyl-octadecadienoic acids</a>) in greater amounts than 15(S)-HpETE and 15(S)-HETE. 15-LOX-2 also differs from 15-LOX-1 in that it does not make 12(S)-HpETE or the leukotriene A4 isomer cited above.<a href="#cite_note-ReferenceA-10">[10]</a> Cyclooxygenase: Cells can use <a href="/wiki/Prostaglandin-endoperoxide_synthase_1" class="mw-redirect" title="Prostaglandin-endoperoxide synthase 1">prostaglandin-endoperoxide synthase 1</a> (i.e. cyclooxygenenase-1 or COX-1) and <a href="/wiki/Prostaglandin-endoperoxide_synthase_2" class="mw-redirect" title="Prostaglandin-endoperoxide synthase 2">prostaglandin-endoperoxide synthase 2</a> (COX-2) to metabolize arachidonic acid primarily to <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandins</a> but also to small amounts of 11(R)-HETE and a racemic mixture of 15-HETEs composed of ~22% 15(R)-HETE and ~78% 15(S)-HETE.<a href="#cite_note-J._lipid_Res._51:575-585,_2010-11">[11]</a> When pretreated with <a href="/wiki/Aspirin" title="Aspirin">aspirin</a>, however, COX-1 is inactive while COX-2 attacks arachidonic acid to produce almost exclusively 15(R)-HETE along with its presumed precursor 15(R)-HpETE.<a href="#cite_note-J._lipid_Res._51:575-585,_2010-11">[11]</a><a href="#cite_note-12">[12]</a><a href="#cite_note-13">[13]</a> Microsome metabolism: Human and rat microsomal <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450s</a>, e.g. CYP2C19, metabolize arachidonic acid to a <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic mixture</a> of 15-HETEs, i.e., 15(R,S)-HETEs, >90% of which is the 15(R) stereoisomer.<a href="#cite_note-14">[14]</a><a href="#cite_note-15">[15]</a> Autoxidation: The spontaneous and non-enzymatically induced <a href="/wiki/Autoxidation" title="Autoxidation">autoxidation</a> of arachidonic acid yields 15(R,S)-hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acids. This non-enzymatic reaction is promoted in cells undergoing <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a>. Cells forming this <a href="/wiki/Racemic_mixture" title="Racemic mixture">racemic mixture</a> of 15-hydroperoxy products may convert then to 15(R,S)-HETEs and other products. However, the uncontrolled overproduction of the 15-hydroperoxy products may react with other elements to produce cell injury.<a href="#cite_note-16">[16]</a><a href="#cite_note-17">[17]</a> <div class="mw-heading mw-heading2"><h2 id="Further_metabolism">Further metabolism</h2>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=3" title="Edit section: Further metabolism">edit</a>]</div> The newly formed products formed by the pathways cited in the previous section are bioactive but may also flow into down-stream pathways to form other metabolites with a different sets of bioactivity. The initially formed 15(S)-HpETE may be further metabolized by its parent cell or pass it to nearby cell by a process termed <a href="/wiki/Eicosanoid#Peroxidation_and_reactive_oxygen_species" title="Eicosanoid">transcellular metabolism</a>. 15(S)-HpETE may be: <ul><li>Rapidly reduced to 15(S)-HETE by ubiquitous cellular <a href="/wiki/Peroxidase" title="Peroxidase">peroxidase</a> reactions including those possessed by <a href="/wiki/Prostaglandin-endoperoxide_synthase" class="mw-redirect" title="Prostaglandin-endoperoxide synthase">prostaglandin-endoperoxide synthase</a>-1 and -2,<a href="#cite_note-18">[18]</a> <a href="/wiki/Prostacyclin_synthase" title="Prostacyclin synthase">prostacyclin synthase</a>, <a href="/wiki/Thromboxane_synthase" class="mw-redirect" title="Thromboxane synthase">thromboxane synthase</a>,<a href="#cite_note-19">[19]</a> and various <a href="/wiki/Glutathione_peroxidase" title="Glutathione peroxidase">glutathione peroxidases</a>.<a href="#cite_note-20">[20]</a></li> <li><a href="/wiki/Acylated" class="mw-redirect" title="Acylated">Acylated</a> into membrane <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>, particularly <a href="/wiki/Phosphatidylinositol" title="Phosphatidylinositol">phosphatidylinositols</a><a href="#cite_note-ReferenceB-21">[21]</a><a href="#cite_note-J._Biol._CheM._266;7570-7577,_1991-22">[22]</a> and <a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">phosphatidylethanolamine</a>.<a href="#cite_note-ReferenceC-23">[23]</a><a href="#cite_note-J._Biol._Chem._287:41651-41666,_2012-24">[24]</a> The 15(S)-HpETE is bound primarily at the <a href="/wiki/Stereospecific_numbering" class="mw-redirect" title="Stereospecific numbering">sn</a>-2 position of these phospholipids (see <a href="/wiki/Phospholipase" title="Phospholipase">Phospholipase</a>) and may be reduced to 15(S)-HETE<a href="#cite_note-ReferenceB-21">[21]</a><a href="#cite_note-J._Biol._CheM._266;7570-7577,_1991-22">[22]</a><a href="#cite_note-ReferenceC-23">[23]</a><a href="#cite_note-J._Biol._Chem._287:41651-41666,_2012-24">[24]</a> thereby forming their 15(S)-HETE-bound phospholipoid analogs. Phosphatidylinositol phospholipids with 15(S)-HETE in the sn-2 position can be attacked by <a href="/wiki/Phospholipase_C" title="Phospholipase C">phospholipase C</a> to form corresponding <a href="/wiki/Diglyceride" title="Diglyceride">diglycerides</a> with 15(S)-HETE at their sn-2 positions.<a href="#cite_note-25">[25]</a></li> <li>Metabolized by 15-LO-1 to its 14,15-trans-epoxide, 14,15-trans-epoxide-oxido-5Z,8Z,10E,13E-eicosatetraenoic acid (i.e., <a href="/wiki/Eoxin" title="Eoxin">eoxin</a> A4 or EXA4), and thereafter to 14(R)-glutothionyl-15(S)-hydroxy-5Z,8Z,10E,13E-eicosatetraenoic acid (i.e. eoxin C4 or EXC4) by <a href="/wiki/Leukotriene_C4_synthase" title="Leukotriene C4 synthase">leukotriene C4 synthase</a>.<a href="#cite_note-Proc._Natl._Acad._Sci._105:680-685,_2008-26">[26]</a><a href="#cite_note-Claesson-27">[27]</a><a href="#cite_note-J._Allegy_Clin._Immunol_126:859-867,_2010-28">[28]</a> EXC4 contains <a href="/wiki/Glutathione" title="Glutathione">glutathione</a> (i.e. γ-L-glutamyl-L-cysteinylglycine) bound in the R configuration to carbon 14. EXC4 is further metabolized by removal of the γ-L-glutamyl residue to form EXD4 which is in turn further metabolized by removal of the glycine residue to form EXE4.<a href="#cite_note-Proc._Natl._Acad._Sci._105:680-685,_2008-26">[26]</a> These metabolic transformations are similar to those in the pathway that metabolizes arachidonic acid to <a href="/wiki/Leukotriene_A4" title="Leukotriene A4">LTA4</a>, <a href="/wiki/Leukotriene_C4" title="Leukotriene C4">LTC4</a>, <a href="/wiki/Leukotriene_D4" title="Leukotriene D4">LTD4</a>, and <a href="/wiki/Leukotriene_E4" title="Leukotriene E4">LTE4</a> and presumed to be conducted by the same enzymes <a href="#cite_note-Proc._Natl._Acad._Sci._105:680-685,_2008-26">[26]</a><a href="#cite_note-J._Allegy_Clin._Immunol_126:859-867,_2010-28">[28]</a><a href="#cite_note-Claesson-27">[27]</a> (Eoxins are also termed 14,15-leukotrienes or 14,15-LTs).</li> <li>Metabolized alternatively by 15-LO-1 to various 8,15-diHETEs including the two 8(R) and 8(S) <a href="/wiki/Diastereomer" title="Diastereomer">diastereomers</a> of 8,15(S)-dihydroxy-5,9,11,13-eicosatetraenoic acid (8,15-leukotrienes B4) and to two isomeric <a href="/wiki/Diastereomer#Erythro_/_threo" title="Diastereomer">erythro</a>-14,15-dihydroxy-5-cis-8,10,12-eicosatetraenoic acids (14,15-leukotrienes B4).<a href="#cite_note-29">[29]</a><a href="#cite_note-30">[30]</a><a href="#cite_note-31">[31]</a></li> <li>Metabolized by 15-LOX-2 to 11(S)-hydroxy-14(S),15(S)-epoxy-5(Z),8(Z),12(E)-eicosatrienoic acid and 13(R)-hydroxy-14(S),15(S)-epoxy-5(Z),8(Z),11(Z)-eicosatrienoic acid; these two products are novel <a href="/wiki/Hepoxilin" title="Hepoxilin">hepoxilins</a> produced by ALOX15 rather than ALOX12, the enzyme responsible for making the various other hepoxilins in humans.<a href="#cite_note-Lipids_4:69-79,_2011-32">[32]</a> The two novel hepoxilins are termed respectively 14,15-HXA3 and 14,15-HXB3. 14,15-HXA3 can be further metabolized by glutathione transferases to 11(S),15(S)-dihydroxy-14(R)-glutathionyl-(5Z),8(Z),12(E)-eicosatrienoic acid (14,15-HXA3C) which is then further metabolized to 11(S),15(S)-dihydroxy-14(R)-cysteinyl-glycyl-(5Z),8(Z),12(E)-eicosatrienoic acid (14,15-HXA3D).<a href="#cite_note-Lipids_4:69-79,_2011-32">[32]</a></li> <li><a href="/wiki/Isomer" title="Isomer">Isomerized</a> to 15(S)-hydroxy-11,12-cis-epoxy-5Z,8Z,13E-eicosatrienoic acid (i.e., 15-H-11,12-EETA) by a hydroperoxide isomerase activity and then to 11,12,15-trihydroxy-5Z,8Z,12E-eicosatrienoic acid (i.e. 11,12,15-THETA) and 11,14,15-trihydroxy-5Z,8Z,12E-eicosatrienoic acid (i.e., 11,14,15-THETA) by a soluble epoxide hydrolase activity or, by acid in a non-enzymatic reaction (the R, S configuration of the hydroxy residues in the latter two metabolites has not been defined).<a href="#cite_note-33">[33]</a></li> <li>Isomerized to <a href="/wiki/Diastereomer#Erythro_/_threo" title="Diastereomer">threo and erythro diastereoisomers</a> of 13-hydroxy-14,15-cis-epoxy-5Z,8Z,11Z-eicosatrienoic acid (i.e., 15-H-11,12-EETA) by a hydroperoxide isomerase activity, possibly a <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a>, i.e. CYP2J2.<a href="#cite_note-34">[34]</a></li> <li>Metabolized by <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> (CYP) enzymes such as <a href="/wiki/CYP1A1" title="CYP1A1">CYP1A1</a>, <a href="/wiki/CYP1A2" title="CYP1A2">CYP1A2</a>, <a href="/wiki/CYP1B1" title="CYP1B1">CYP1B1</a>, and <a href="/wiki/CYP2S1" title="CYP2S1">CYP2S1</a> to 15-oxo-ETE.<a href="#cite_note-35">[35]</a></li> <li>Metabolized in skin <a href="/wiki/Epidermis" title="Epidermis">epidermis</a> by epidermis-type lipoxygenase 3 (eLOX3, encoded by the <a href="/wiki/ALOXE3" title="ALOXE3">ALOXE3</a> gene) to make two products, <a href="/wiki/Hepoxilin" title="Hepoxilin">hepoxilin A3</a> (HxA3, i.e., 13R-hydroxy-14(S),15(S)-epoxy-5Z,8Z,11Z-eicosatetraenoic acid) and 15-oxo-ETE).<a href="#cite_note-36">[36]</a></li> <li>Converted to its 14,15-<a href="/wiki/Epoxide" title="Epoxide">epoxide</a> derivative, eoxin A4, and further metabolized to eoxin C4, eoxin D4, and eoxin E4 (there is no eoxin B4).<a href="#cite_note-pmid23921438-37">[37]</a></li> <li>Degraded non-enzymatically to various cell-injuring <a href="/wiki/Electrophile" title="Electrophile">electrophiles</a> such as <a href="/wiki/4-Hydroxynonenal" title="4-Hydroxynonenal">4-hydroxy-2(E)-nonenal</a> and <a href="/wiki/4-Oxo-2-nonenal" title="4-Oxo-2-nonenal">4-oxo-2(E)-nonenal</a>.<a href="#cite_note-J._Biol._Chem._280:28337-28346,_2005-38">[38]</a></li></ul> 15(S)-HETE may be: <ul><li><a href="/wiki/Oxidized" class="mw-redirect" title="Oxidized">Oxidized</a> to its <a href="/wiki/Ketone" title="Ketone">keto</a> analog, 15-oxo-ETE, by the same enzyme that converts <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandins</a> of the A, E, and F series to their 15-keto analogs viz., NAD+-dependent <a href="/wiki/15-hydroxyprostaglandin_dehydrogenase" title="15-hydroxyprostaglandin dehydrogenase">15-hydroxyprostaglandin dehydrogenase</a>; 15-oxo-ETE, similar to 15(S)-HETE, may be acylated into membrane phosphatidylethanolamine<a href="#cite_note-ReferenceC-23">[23]</a><a href="#cite_note-J._Biol._Chem._287:41651-41666,_2012-24">[24]</a> or, similar to 15(S)-HpETE, conjugated with <a href="/wiki/Glutathione" title="Glutathione">glutathione</a> to form a 13-cysteinyl-glycyl-glutamine adduct viz., 13-glutatione,15-oxo-5(S),8(Z),11(E)-eicosatrienoic acid; the latter metabolite is attacked by γ-glutamyl-transferase to form 13-cysteinyl-glycine,15-oxo-5(S),8(Z),11(E)-eicosatrienoic acid.<a href="#cite_note-Chem._Res_1675-39">[39]</a></li> <li>Acylated into membrane <a href="/wiki/Phospholipid" title="Phospholipid">phospholipids</a>, particularly <a href="/wiki/Phosphatidylinositol" title="Phosphatidylinositol">phosphatidylinositol</a> and <a href="/wiki/Phosphatidylethanolamine" title="Phosphatidylethanolamine">phosphatidylethanolamine</a>. Phospholipid products contain this 15(S)-HETE most likely at the sn-2 position. 15(S)-HETE-containing-phospholipids may also be made directly by the action of 15-LO-1 on membrane phosphatidylinositols or phosphatidylethanolamines containing arachidonic acid at the sn-2 positions.<a href="#cite_note-ReferenceB-21">[21]</a><a href="#cite_note-40">[40]</a><a href="#cite_note-41">[41]</a><a href="#cite_note-42">[42]</a> The phosphatidylethanolamine-bound 15-HETE may be converted to phosphatidylethanolamine-bound 15-oxo-ETE.<a href="#cite_note-J._Biol._Chem._287:41651-41666,_2012-24">[24]</a></li> <li>Oxygenated by 5-lipoxygenase (<a href="/wiki/ALOX5" class="mw-redirect" title="ALOX5">ALOX5</a>) to form its 5,6-trans epoxide derivative which may then rearrange to the <a href="/wiki/Lipoxin" title="Lipoxin">lipoxins</a> (LX), LXA4 (i.e. 5(S),6(R),15(S)-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid) and LXB4 (i.e., 5(S),14(R),15(S)-trihydroxy-6E,8Z,10E,12E-eicosatetraenoic acid)<a href="#cite_note-resolve-3">[3]</a> or to 5(S),15(S)-dihydroperoxy-6E,8Z,11Z,13E-eicosatetraenoate (i.e., 5(S),15(S)-diHETE).<a href="#cite_note-Prostaglandins_Leukot_Essent_Fatty_Acids_73:141-162,_2005-43">[43]</a><a href="#cite_note-44">[44]</a> 5(S),15(S)-diHETE may then be oxidized to 5-oxo-15(S)-hydroxy-6E,8Z,11Z,13E-eicosatetraenoate (i.e., 5-oxo-15(S)-hydroxy-ETE). The latter two metabolites may also be made by 15-LO's metabolism of <a href="/wiki/5-hydroxyeicosatetraenoic_acid" class="mw-redirect" title="5-hydroxyeicosatetraenoic acid">5-hydroxyeicosatetraenoic acid</a> (i.e. 5-HETE) and <a href="/wiki/5-oxo-eicosatetraenoic_acid" class="mw-redirect" title="5-oxo-eicosatetraenoic acid">5-oxo-eicosatetraenoic acid</a> (i.e. 5-oxo-ETE), respectively.<a href="#cite_note-45">[45]</a><a href="#cite_note-46">[46]</a></li></ul> 15(R)-HpETE may be: <ul><li>Reduced to 15(R)-HETE by the same pathway that reduces 5(S)-HpETE to 15(S)-HETE.<a href="#cite_note-J._Biol._Chem._280:28337-28346,_2005-38">[38]</a></li> <li>Similar to 15(S)-HpETE, subject to decomposition to form various bifuctional potentially toxic electrophiles such as 4-hydroxy-2(E)-nonenal and 4-oxo-2(E)-nonenal.<a href="#cite_note-J._Biol._Chem._280:28337-28346,_2005-38">[38]</a></li></ul> 15(R)-HETE may be: <ul><li>Similar to 15(S)-HETE, oxidized by NAD-dependent 5-hydroxyprostaglandin dehydrogenase to form 15-oxo-ETE which product can be converted its 13-cysteinyl-glycyl-glutamyl and then 13-cysteinyl-glycine products as described above for 5(S)-HETE.<a href="#cite_note-Chem._Res_1675-39">[39]</a></li> <li>Similar to 15(S)-HETE, oxygenated by ALOX5 to form its 5,6-oxido derivative which then rearranges to the 15(R) <a href="/wiki/Diastereomer" title="Diastereomer">diastereomers</a> of LXA4 and (LXB4 viz., 15-epi-LXA4 5(S),6(R),15(R)-trihydroxy-7E,9E,11Z,13E-eicosatetraenoic acid) and 15-epi-LXB4 (i.e., 5(S),14(R),15(S)-trihydroxy-6E,8Z,10E,12E-eicosatetraenoic acid, respectively.<a href="#cite_note-Prostaglandins_Leukot_Essent_Fatty_Acids_73:141-162,_2005-43">[43]</a><a href="#cite_note-resolve-3">[3]</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Activities">Activities</h2>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=4" title="Edit section: Activities">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="15(S)-HpETE_and_15(S)-HETE">15(S)-HpETE and 15(S)-HETE</h3>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=5" title="Edit section: 15(S)-HpETE and 15(S)-HETE">edit</a>]</div> Most studies have analyzed the action of 15(S)-HETE but not that of its less stable precursor 15(S)-HpETE. Since this precursor is rapidly converted to 15(S)-HETE in cells, it is likely that the two metabolites share similar activities. In many studies, however, is not clear that these activities reflect their intrinsic action or reflect their conversion to the metabolites sited above. 15(S)-HpETE and 15(S)-HETE bind to and activate the <a href="/wiki/G_protein-coupled_receptor" title="G protein-coupled receptor">G protein-coupled receptor</a>, <a href="/wiki/Leukotriene_B4_receptor_2" title="Leukotriene B4 receptor 2">leukotriene B4 receptor 2</a>, i.e. BLT2.<a href="#cite_note-47">[47]</a> This receptor activation may mediate, at least in part, certain cell-stimulating activities of the two metabolites. BLT2 may be responsible in part or whole for mediating the growth-promoting and anti-<a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a> (i.e. anti-cell death) activities of 15(S)-HETE in cultured human breast cancer cells;<a href="#cite_note-PLoS_One._2013_May_2;8(5):e63076._doi:_10.1371/journal.pone.0063076-48">[48]</a> human cancer colon cells,<a href="#cite_note-Int._J._Biochem_1628-49">[49]</a> human hepatocellular HepG2 and SMMC7721 cancer cells;<a href="#cite_note-50">[50]</a> mouse <a href="/wiki/3T3_cells" title="3T3 cells">3T3 cells</a> (a <a href="/wiki/Fibroblast" title="Fibroblast">fibroblast</a> cell line);<a href="#cite_note-J._Lipid_Res._47:2681-2689-51">[51]</a> rat PA adventitia fibroblasts;<a href="#cite_note-52">[52]</a> <a href="/wiki/Baby_hamster_kidney_cell" title="Baby hamster kidney cell">baby hamster kidney cells</a>;<a href="#cite_note-53">[53]</a> and diverse types of vascular <a href="/wiki/Endothelial_cell" class="mw-redirect" title="Endothelial cell">endothelial cells</a>.<a href="#cite_note-diction-54">[54]</a><a href="#cite_note-Inflamm._Res._61:707-718,_2012-55">[55]</a><a href="#cite_note-56">[56]</a><a href="#cite_note-57">[57]</a> These growth-stimulating effects could contribute to the progression of the cited cancer types in animal models or even humans<a href="#cite_note-PLoS_One._2013_May_2;8(5):e63076._doi:_10.1371/journal.pone.0063076-48">[48]</a><a href="#cite_note-Int._J._Biochem_1628-49">[49]</a> and the excess <a href="/wiki/Fibrosis" title="Fibrosis">fibrosis</a> that causes the narrowing of pulmonary arteries in hypoxia-induced <a href="/wiki/Pulmonary_hypertension" title="Pulmonary hypertension">pulmonary hypertension</a><a href="#cite_note-J._Lipid_Res._47:2681-2689-51">[51]</a> or narrowing of portal arteries in the <a href="/wiki/Portal_hypertension" title="Portal hypertension">portal hypertension</a> accompanying liver cirrhosis.<a href="#cite_note-58">[58]</a> 15(S)-HETE may also act through BLT2 to stimulate an immediate contractile response in rat pulmonary arteries<a href="#cite_note-59">[59]</a> and its <a href="/wiki/Angiogenesis" title="Angiogenesis">angiogenic</a> effect on human umbilical<a href="#cite_note-Inflamm._Res._61:707-718,_2012-55">[55]</a> and dermal<a href="#cite_note-diction-54">[54]</a> vascular endothelial cells. 15(S)-HpETE and 15(S)-HETE also directly bind with and activate <a href="/wiki/Peroxisome_proliferator-activated_receptor_gamma" title="Peroxisome proliferator-activated receptor gamma">peroxisome proliferator-activated receptor gamma</a>.<a href="#cite_note-Mol._Pharmacol._77:171-184,_2010-60">[60]</a> This activation may contribute to the ability of 15(S)-HETE to inhibit the growth of cultured human prostate cancer <a href="/wiki/PC-3" class="mw-redirect" title="PC-3">PC-3</a>, <a href="/wiki/LNCaP" title="LNCaP">LNCaP</a>, and <a href="/wiki/DU145" title="DU145">DU145</a> cell lines and non-malignant human prostate cells;<a href="#cite_note-61">[61]</a><a href="#cite_note-62">[62]</a> lung adenocarcinoma <a href="/wiki/A549_cell" title="A549 cell">A549 cells</a>;<a href="#cite_note-63">[63]</a> human colorectal cancer cells;<a href="#cite_note-64">[64]</a> corneal epithelial cells;<a href="#cite_note-65">[65]</a> and <a href="/wiki/Jurkat" class="mw-redirect" title="Jurkat">Jurkat</a> T-cell leukemia cells.<a href="#cite_note-appropo-66">[66]</a> The decline in the level of 15(S)-HpETE-forming enzymes and consequential fall in cellular 15-HETE production that occurs in human prostate cancer cells may be one mechanism by which this and perhaps other human cancer cells (e.g. those of the colon, rectum, and lung) avoid the apoptosis-inducing actions of 15(S)-HpETE and/or 15(S)-HETE and thereby proliferate and spread.<a href="#cite_note-67">[67]</a><a href="#cite_note-68">[68]</a> In this scenario, 15(S)-HETE and one of its forming enzymes, particularly 15-LOX-2, appear to act as tumor suppressors. Some of the inhibitory effects of 15(S)-HpETE and 15(S)-HETE, particularly when induced by high concentrations (e.g. >1-10 micromolar), may be due to a less specific mechanism: 15(S)-HpETE and to a lesser extent 15(S)-HETE induce the generation of <a href="/wiki/Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a>. These species trigger cells to activate their death programs, i.e. <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a>, and/or are openly toxic to the cells.<a href="#cite_note-69">[69]</a><a href="#cite_note-70">[70]</a><a href="#cite_note-appropo-66">[66]</a><a href="#cite_note-71">[71]</a><a href="#cite_note-72">[72]</a> 15(S)-HpETE and 15(S)-HETE inhibit angiogenesis and the growth of cultured human chronic myelogenous leukemia K-562 cells by a mechanism that is associated with the production of reactive oxygen species.<a href="#cite_note-Inflamm._Res._61:707-718,_2012-55">[55]</a><a href="#cite_note-73">[73]</a><a href="#cite_note-74">[74]</a> Several bifunctional electrophilic breakdown products of 15(S)-HpETE, e.g. 4-hydroxy-2(E)-nonenal, 4-hydroperoxy-2(E)-nonenal, 4-oxo-2(E)-nonenal, and cis-4,5-epoxy-2(E)-decanal, are <a href="/wiki/Mutagen" title="Mutagen">mutagens</a> in mammalian cells and thereby may contripute to the development and/or progression of human cancers.<a href="#cite_note-J._Biol._Chem._280:28337-28346,_2005-38">[38]</a> <div class="mw-heading mw-heading3"><h3 id="15(R)-HETE">15(R)-HETE</h3>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=6" title="Edit section: 15(R)-HETE">edit</a>]</div> Similar to 15(S)-HpETE and 15(S)-HETE and with similar potency, 15(R)-HETE binds with and activates peroxisome proliferator-activated receptor gamma.<a href="#cite_note-Mol._Pharmacol._77:171-184,_2010-60">[60]</a> The precursor of 15(R)-HETE, 15(R)-HpETE may, similar to 15(S)-HpETE, break down to the mutagenic products 4-hydroxy-2(E)-nonenal, 4-hydroperoxy-2(E)-nonenal, 4-oxo-2(E)-nonenal, and cis-4,5-epoxy-2(E)-decanal and therefore be involved in cancer development and/or progression.<a href="#cite_note-J._Biol._Chem._280:28337-28346,_2005-38">[38]</a> <div class="mw-heading mw-heading3"><h3 id="15-Oxo-ETE">15-Oxo-ETE</h3>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=7" title="Edit section: 15-Oxo-ETE">edit</a>]</div> In cultured human monocytes of the <a href="/wiki/THP1_cell_line" class="mw-redirect" title="THP1 cell line">THP1 cell line</a>, 15-oxo-ETE inactivates IKKβ (also known as <a href="/wiki/IKK2" title="IKK2">IKK2</a>) thereby blocking this cell's <a href="/wiki/NF-%CE%BAB" title="NF-κB">NF-κB</a>-mediated pro-inflammatory responses (e.g. <a href="/wiki/Lipopolysaccharide" title="Lipopolysaccharide">lipopolysaccharide</a>-induced production of <a href="/wiki/TNF%CE%B1" class="mw-redirect" title="TNFα">TNFα</a>, <a href="/wiki/Interleukin_6" title="Interleukin 6">interleukin 6</a>, and <a href="/wiki/IL1B" class="mw-redirect" title="IL1B">IL1B</a>) while concurrently activating anti-oxidant responses upregulated through the anti-oxidant response element (ARE) by forcing cytosolic <a href="/wiki/KEAP1" title="KEAP1">KEAP1</a> to release <a href="/wiki/NFE2L2" title="NFE2L2">NFE2L2</a> which then moves to the nucleus, binds ARE, and induces production of, e.g. hemoxygenase-1, NADPH-quinone oxidoreductase, and possibly glutamate-cysteine ligase modifier.<a href="#cite_note-dx.doi.org-75">[75]</a> By these actions, 15-oxo-ETE may dampen inflammatory and/or <a href="/wiki/Oxidative_stress" title="Oxidative stress">oxidative stress</a> responses. In a cell-free system, 15-oxo-ETE is a moderately potent (IC50=1 μM) inhibitor of <a href="/wiki/12-lipoxygenase" class="mw-redirect" title="12-lipoxygenase">12-lipoxygenase</a> but not other human lipoxygenases.<a href="#cite_note-Bioorg._Med._Chem._22:4293–4297-76">[76]</a> This effect could also have anti-inflammatory and anti-oxidative effects by blocking the formation of <a href="/wiki/12-HETE" class="mw-redirect" title="12-HETE">12-HETE</a> and <a href="/wiki/Hepoxilin" title="Hepoxilin">hepoxilins</a>. 15-Oxo-ETE is an example of an α,β unsaturated ketone <a href="/wiki/Electrophile" title="Electrophile">electrophile</a>. These ketones are highly reactive with <a href="/wiki/Nucleophile" title="Nucleophile">nucleophiles</a>, adducting to, for example, the cysteines in transcription and transcription-related regulatory factors and enzymes to form their alkylated and thereby often inactivated products.<a href="#cite_note-Bioorg._Med._Chem._22:4293–4297-76">[76]</a><a href="#cite_note-77">[77]</a> It is presumed that the preceding activities of 15-oxo-ETE reflect its adduction to the indicated elements.<a href="#cite_note-dx.doi.org-75">[75]</a> 15-Oxo-ETE, at 2-10 μM, also inhibits the proliferation of cultured <a href="/wiki/Human_umbilical_vein_endothelial_cell" title="Human umbilical vein endothelial cell">human umbilical vein endothelial cells</a> and <a href="/wiki/Mir-26_microRNA_precursor_family#miR-26b_roles" title="Mir-26 microRNA precursor family">LoVo</a> human <a href="/wiki/Colorectal_cancer" title="Colorectal cancer">colorectal cancer</a> cells <a href="#cite_note-78">[78]</a><a href="#cite_note-79">[79]</a> and at the extremely high concentration of 100 μM inhibits the proliferation of cultured MBA-MD-231 and MCF7 breast cancer cells as well as SKOV3 ovarian cancer cells.<a href="#cite_note-Biophysica_Acta_2005-80">[80]</a> They may use a similar "protein-adduction" mechanism; if so the target protein(s) for these effects have not been defined or even suggested. This 15-oxo-ETE action may prove to inhibit the remodeling of blood vessels and reduce the growth of the cited cell types and cancers. At sub-micromolar concentrations, 15-oxo-ETE has weak <a href="/wiki/Chemotaxis" title="Chemotaxis">chemotaxis</a> activity for human <a href="/wiki/Monocyte" title="Monocyte">monocytes</a> and could serve to recruit this <a href="/wiki/White_blood_cell" title="White blood cell">white blood cell</a> into <a href="/wiki/Inflammatory_response" class="mw-redirect" title="Inflammatory response">inflammatory responses</a>.<a href="#cite_note-81">[81]</a> <div class="mw-heading mw-heading3"><h3 id="5-Oxo-15(S)-hydroxy-ETE">5-Oxo-15(S)-hydroxy-ETE</h3>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=8" title="Edit section: 5-Oxo-15(S)-hydroxy-ETE">edit</a>]</div> 5-Oxo-15(S)-hydroxy-ETE is properly a member of the <a href="/wiki/5-HETE" class="mw-redirect" title="5-HETE">5-HETE</a> family of agonists which binds to the <a href="/wiki/Oxoeicosanoid_receptor_1" title="Oxoeicosanoid receptor 1">oxoeicosanoid receptor 1</a>, a <a href="/wiki/G_protein-coupled_receptor" title="G protein-coupled receptor">G protein-coupled receptor</a>, to activate its various target cells. As such, it is a potent stimulator of <a href="/wiki/Leukocyte" class="mw-redirect" title="Leukocyte">leukocytes</a>, particularly <a href="/wiki/Eosinophil" title="Eosinophil">eosinophils</a>, as well as other OXE1-bearing cells including <a href="/wiki/MDA-MB-231" class="mw-redirect" title="MDA-MB-231">MDA-MB-231</a>, <a href="/wiki/MCF7" class="mw-redirect" title="MCF7">MCF7</a>, and <a href="/w/index.php?title=SKOV3&action=edit&redlink=1" class="new" title="SKOV3 (page does not exist)">SKOV3</a> cancer cells (see <a href="/wiki/5-Hydroxyicosatetraenoic_acid" class="mw-redirect" title="5-Hydroxyicosatetraenoic acid">5-Hydroxyicosatetraenoic acid</a> and <a href="/wiki/5-Oxo-eicosatetraenoic_acid" title="5-Oxo-eicosatetraenoic acid">5-Oxo-eicosatetraenoic acid</a>).<a href="#cite_note-82">[82]</a> It also binds with and activates <a href="/wiki/PPAR%CE%B3" class="mw-redirect" title="PPARγ">PPARγ</a> and thereby can stimulate or inhibit cells independently of OXE1.<a href="#cite_note-Biophysica_Acta_2005-80">[80]</a> <div class="mw-heading mw-heading3"><h3 id="Lipoxins">Lipoxins</h3>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=9" title="Edit section: Lipoxins">edit</a>]</div> LXA4, LXB4, AT-LXA4, and AT-LXB4 are <a href="/wiki/Specialized_pro-resolving_mediators#Lipoxins" title="Specialized pro-resolving mediators">specialized proresolving mediators</a>, i.e. they potently inhibit the progression and contribute to the resolution of diverse inflammatory and allergic reactions. <div class="mw-heading mw-heading3"><h3 id="Eoxins">Eoxins</h3>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=10" title="Edit section: Eoxins">edit</a>]</div> <a href="/wiki/Eoxin_A4" title="Eoxin A4">Eoxin A4</a>, <a href="/wiki/Eoxin_C4" title="Eoxin C4">eoxin C4</a>, <a href="/wiki/Eoxin_D4" title="Eoxin D4">eoxin D4</a>, and <a href="/wiki/Eoxin_E4" title="Eoxin E4">eoxin E4</a> are analogs of <a href="/wiki/Leukotriene_A4" title="Leukotriene A4">leukotriene A4</a>, <a href="/wiki/Leukotriene_C4" title="Leukotriene C4">C4</a>, <a href="/wiki/Leukotriene_D4" title="Leukotriene D4">leukotriene D4</a>, and <a href="/wiki/Leukotriene_E4" title="Leukotriene E4">E4</a>. Formation of the leukotrienes is initiated by 5-lipoxygenase metabolism of arachidonic acid to form a 5,6-<a href="/wiki/Epoxide" title="Epoxide">epoxide</a> viz, leukotriene A4; the latter metabolite is then converted to C4, D4, and E4 in succession. Formation of the eoxins is initiated by a 15-lipoxyenase-mediated metabolism of arachiconic acid to a 14,15-epoxide, eoxin A4 followed by its serial conversion to epoxins C4, D4, and E4 using the same pathways and enzymes that metabolize leukotriene A4 to its down-stream products. Preliminary studies have found that the eoxins have pro-inflammatory actions, suggest that they are involved in severe asthma, aspirin-induced asthma attacks, and perhaps other allergic reactions. The production of eoxins by Reed-Sternburg cells has also led to suggestion that they are involve in the lymphoma of Hodgkins disease.<a href="#cite_note-Claesson-27">[27]</a> Drugs blocking the 15-lipoxygenases may be useful for inhibiting inflammation by reducing the production of the eoxins.<a href="#cite_note-pmid26560362-83">[83]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=11" title="Edit section: See also">edit</a>]</div> <ul><li><a href="/wiki/Epi-lipoxin" title="Epi-lipoxin">Epi-lipoxin</a></li> <li><a href="/wiki/Eoxin" title="Eoxin">Eoxin</a></li> <li><a href="/wiki/Specialized_pro-resolving_mediators" title="Specialized pro-resolving mediators">Specialized pro-resolving mediators</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=12" 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: 30em;"> <ol class="references"> <li id="cite_note-New_aspects_of_the_role_of_hydroxyeicosatetraenoic_acids_in_cell_growth_and_cancer_development-1">^ <a href="#cite_ref-New_aspects_of_the_role_of_hydroxyeicosatetraenoic_acids_in_cell_growth_and_cancer_development_1-0">a</a> <a href="#cite_ref-New_aspects_of_the_role_of_hydroxyeicosatetraenoic_acids_in_cell_growth_and_cancer_development_1-1">b</a> <style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFMoreno2009" class="citation journal cs1">Moreno, J. 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Journal of Immunology. 157 (1): 336–342. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.4049%2Fjimmunol.157.1.336">10.4049/jimmunol.157.1.336</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/8683135">8683135</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:35264541">35264541</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Immunology&rft.atitle=5-Oxo-eicosatetraenoate+is+a+broadly+active%2C+eosinophil-selective+stimulus+for+human+granulocytes&rft.volume=157&rft.issue=1&rft.pages=336-342&rft.date=1996&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A35264541%23id-name%3DS2CID&rft_id=info%3Apmid%2F8683135&rft_id=info%3Adoi%2F10.4049%2Fjimmunol.157.1.336&rft.aulast=O%27Flaherty&rft.aufirst=J.+T.&rft.au=Kuroki%2C+M&rft.au=Nixon%2C+A.+B.&rft.au=Wijkander%2C+J&rft.au=Yee%2C+E&rft.au=Lee%2C+S.+L.&rft.au=Smitherman%2C+P.+K.&rft.au=Wykle%2C+R.+L.&rft.au=Daniel%2C+L.+W.&rft_id=https%3A%2F%2Fdoi.org%2F10.4049%252Fjimmunol.157.1.336&rfr_id=info%3Asid%2Fen.wikipedia.org%3A15-Hydroxyeicosatetraenoic+acid" class="Z3988"> </li> <li id="cite_note-pmid26560362-83"><a href="#cite_ref-pmid26560362_83-0">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSadeghianJabbari2016" class="citation journal cs1">Sadeghian H, Jabbari A (2016). "15-Lipoxygenase inhibitors: a patent review". Expert Opinion on Therapeutic Patents. 26 (1): 65–88. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1517%2F13543776.2016.1113259">10.1517/13543776.2016.1113259</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/26560362">26560362</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:20192361">20192361</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Expert+Opinion+on+Therapeutic+Patents&rft.atitle=15-Lipoxygenase+inhibitors%3A+a+patent+review&rft.volume=26&rft.issue=1&rft.pages=65-88&rft.date=2016&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20192361%23id-name%3DS2CID&rft_id=info%3Apmid%2F26560362&rft_id=info%3Adoi%2F10.1517%2F13543776.2016.1113259&rft.aulast=Sadeghian&rft.aufirst=H&rft.au=Jabbari%2C+A&rfr_id=info%3Asid%2Fen.wikipedia.org%3A15-Hydroxyeicosatetraenoic+acid" class="Z3988"> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=15-Hydroxyeicosatetraenoic_acid&action=edit&section=13" title="Edit section: External links">edit</a>]</div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150317234714/http://atlasgeneticsoncology.org/Genes/GC_ALOX15.html">15-LOX Gene Atlas entry</a></li> <li><a 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href="/wiki/Eicosanoid" title="Eicosanoid">Eicosanoids</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Precursor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prostanoid" title="Prostanoid">Prostanoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prostaglandin" title="Prostaglandin">Prostaglandins</a> (PG)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Precursor</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Prostaglandin_H2" title="Prostaglandin H2">H2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Active</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">D/J</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">D2</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Prostaglandin_E" title="Prostaglandin E">E</a>/F</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">E2 (Dinoprostone)</a></li></ul> <ul><li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">E1 (Alprostadil)</a></li></ul> <ul><li><a href="/wiki/Prostaglandin_F2alpha" title="Prostaglandin F2alpha">F2α (Dinoprost)</a>:</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">I</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Prostacyclin" title="Prostacyclin">I2 (Prostacyclin/Epoprostenol)</a>:</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thromboxane" title="Thromboxane">Thromboxanes</a> (TX)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Thromboxane_A2" title="Thromboxane A2">A2</a></li> <li><a href="/wiki/Thromboxane_B2" title="Thromboxane B2">B2</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Leukotriene" title="Leukotriene">Leukotrienes</a> (LT)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Precursor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Arachidonic_acid_5-hydroperoxide" title="Arachidonic acid 5-hydroperoxide">Arachidonic acid 5-hydroperoxide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Initial</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Leukotriene_A4" title="Leukotriene A4">A4</a></li> <li><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">B4</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Slow-reacting_substance_of_anaphylaxis" title="Slow-reacting substance of anaphylaxis">SRS-A</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Leukotriene_C4" title="Leukotriene C4">C4</a></li> <li><a href="/wiki/Leukotriene_D4" title="Leukotriene D4">D4</a></li> <li><a href="/wiki/Leukotriene_E4" title="Leukotriene E4">E4</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Eoxin" title="Eoxin">Eoxins</a> (EX)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Precursor</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Arachidonic_acid_15-hydroperoxide&action=edit&redlink=1" class="new" title="Arachidonic acid 15-hydroperoxide (page does not exist)">Arachidonic acid 15-hydroperoxide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Eoxins</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Eoxin_A4" title="Eoxin A4">A4</a></li> <li><a href="/wiki/Eoxin_C4" title="Eoxin C4">C4</a></li> <li><a href="/wiki/Eoxin_D4" title="Eoxin D4">D4</a></li> <li><a href="/wiki/Eoxin_E4" title="Eoxin E4">E4</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nonclassic_eicosanoid" title="Nonclassic eicosanoid">Nonclassic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lipoxin" title="Lipoxin">Lipoxins</a> (LX) (<a href="/wiki/Lipoxin" title="Lipoxin">A4</a>, <a href="/wiki/Lipoxin" title="Lipoxin">B4</a>)</li> <li><a href="/wiki/Virodhamine" title="Virodhamine">Virodhamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">By function</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bronchoconstriction" title="Bronchoconstriction">bronchoconstriction</a> <ul><li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">PGD2</a></li> <li><a href="/wiki/Thromboxane_A2" title="Thromboxane A2">TXA2</a></li> <li><a href="/wiki/Leukotriene_C4" title="Leukotriene C4">LTC4</a></li> <li><a href="/wiki/Leukotriene_D4" title="Leukotriene D4">LTD4</a></li> <li><a href="/wiki/Leukotriene_E4" title="Leukotriene E4">LTE4</a></li></ul></li></ul> <ul><li><a href="/wiki/Vasoconstriction" title="Vasoconstriction">vasoconstriction</a> <ul><li><a href="/wiki/Prostaglandin_F2alpha" title="Prostaglandin F2alpha">PGF2α</a></li> <li><a href="/wiki/Thromboxane_A2" title="Thromboxane A2">TXA2</a></li> <li><a href="/wiki/Thromboxane_B2" title="Thromboxane B2">TXB2</a></li></ul></li> <li><a href="/wiki/Vasodilation" title="Vasodilation">vasodilation</a> <ul><li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">PGE2</a></li> <li><a href="/wiki/Prostacyclin" title="Prostacyclin">PGI2</a></li> <li><a href="/wiki/Leukotriene_C4" title="Leukotriene C4">LTC4</a></li> <li><a href="/wiki/Leukotriene_D4" title="Leukotriene D4">LTD4</a></li> <li><a href="/wiki/Leukotriene_E4" title="Leukotriene E4">LTE4</a></li></ul></li></ul> <ul><li><a href="/wiki/Platelet" title="Platelet">platelets</a>: induce <ul><li><a href="/wiki/Thromboxane_A2" title="Thromboxane A2">TXA2</a></li></ul></li> <li>inhibit <ul><li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">PGD2</a></li> <li><a href="/wiki/Prostacyclin" title="Prostacyclin">PGI2</a></li></ul></li> <li><a href="/wiki/Leukocyte" class="mw-redirect" title="Leukocyte">leukocytes</a>: induce <ul><li><a href="/wiki/Thromboxane_A2" title="Thromboxane A2">TXA2</a></li> <li><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">LTB4</a></li></ul></li> <li>inhibit <ul><li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">PGD2</a></li> <li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">PGE2</a></li></ul></li></ul> <ul><li><a href="/wiki/Fever" title="Fever">fever</a> stimulation: <ul><li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">PGE2</a></li></ul></li></ul> <ul><li><a href="/wiki/Childbirth" title="Childbirth">labor</a> stimulation: <ul><li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">PGE2</a> (Dinoprostone)</li> <li><a href="/wiki/Prostaglandin_F2alpha" title="Prostaglandin F2alpha">PGF2α</a> (Dinoprost)</li></ul></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="Leukotriene_signaling_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Leukotriene_signaling_modulators" title="Template:Leukotriene signaling modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Leukotriene_signaling_modulators" title="Template talk:Leukotriene signaling modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Leukotriene_signaling_modulators" title="Special:EditPage/Template:Leukotriene signaling modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Leukotriene_signaling_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Leukotriene" title="Leukotriene">Leukotriene</a> <a href="/wiki/Cell_signaling" title="Cell signaling">signaling</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Receptor_(biochemistry)" title="Receptor (biochemistry)">Receptor</a> (<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_receptor" title="Leukotriene B4 receptor"><abbr title="Leukotriene B4 receptor">BLT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene B4 receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_receptor_1" title="Leukotriene B4 receptor 1"><abbr title="Leukotriene B4 receptor 1">BLT1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene B4 receptor 1</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12-HETE</a></li> <li><a href="/w/index.php?title=20-Hydroxy-LTB4&action=edit&redlink=1" class="new" title="20-Hydroxy-LTB4 (page does not exist)">20-Hydroxy-LTB4</a></li> <li><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">Leukotriene B4</a></li> <li><a href="/w/index.php?title=LY-255283&action=edit&redlink=1" class="new" title="LY-255283 (page does not exist)">LY-255283</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=20-Carboxy-LTB4&action=edit&redlink=1" class="new" title="20-Carboxy-LTB4 (page does not exist)">20-Carboxy-LTB4</a></li> <li><a href="/w/index.php?title=Amelubant&action=edit&redlink=1" class="new" title="Amelubant (page does not exist)">Amelubant</a></li> <li><a href="/w/index.php?title=CGS-23131&action=edit&redlink=1" class="new" title="CGS-23131 (page does not exist)">CGS-23131 (LY-223982)</a></li> <li><a href="/w/index.php?title=CGS-25019C&action=edit&redlink=1" class="new" title="CGS-25019C (page does not exist)">CGS-25019C</a></li> <li><a href="/w/index.php?title=CP-105696&action=edit&redlink=1" class="new" title="CP-105696 (page does not exist)">CP-105696</a></li> <li><a href="/w/index.php?title=CP-195543&action=edit&redlink=1" class="new" title="CP-195543 (page does not exist)">CP-195543</a></li> <li><a href="/wiki/Etalocib" title="Etalocib">Etalocib</a></li> <li><a href="/w/index.php?title=LY-293111&action=edit&redlink=1" class="new" title="LY-293111 (page does not exist)">LY-293111</a></li> <li><a href="/w/index.php?title=Moxilubant&action=edit&redlink=1" class="new" title="Moxilubant (page does not exist)">Moxilubant</a></li> <li><a href="/w/index.php?title=ONO-4057&action=edit&redlink=1" class="new" title="ONO-4057 (page does not exist)">ONO-4057</a></li> <li><a href="/w/index.php?title=RG-14893&action=edit&redlink=1" class="new" title="RG-14893 (page does not exist)">RG-14893</a></li> <li><a href="/w/index.php?title=RP-69698&action=edit&redlink=1" class="new" title="RP-69698 (page does not exist)">RP-69698</a></li> <li><a href="/w/index.php?title=SB-209247&action=edit&redlink=1" class="new" title="SB-209247 (page does not exist)">SB-209247</a></li> <li><a href="/w/index.php?title=SC-53228&action=edit&redlink=1" class="new" title="SC-53228 (page does not exist)">SC-53228</a></li> <li><a href="/w/index.php?title=Ticolubant&action=edit&redlink=1" class="new" title="Ticolubant (page does not exist)">Ticolubant</a></li> <li><a href="/w/index.php?title=U-75302&action=edit&redlink=1" class="new" title="U-75302 (page does not exist)">U-75302</a></li> <li><a href="/w/index.php?title=ZK-158252&action=edit&redlink=1" class="new" title="ZK-158252 (page does not exist)">ZK-158252</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_receptor_2" title="Leukotriene B4 receptor 2"><abbr title="Leukotriene B4 receptor 2">BLT2</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene B4 receptor 2</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12-HETE</a></li> <li><a href="/wiki/12-Hydroxyheptadecatrienoic_acid" title="12-Hydroxyheptadecatrienoic acid">12-HHT</a></li> <li><a href="/w/index.php?title=12-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="12-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid (page does not exist)">12-HpETE</a></li> <li><a class="mw-selflink selflink">15-HETE</a></li> <li><a href="/w/index.php?title=15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (page does not exist)">15-HpETE</a></li> <li><a href="/w/index.php?title=20-Hydroxy-LTB4&action=edit&redlink=1" class="new" title="20-Hydroxy-LTB4 (page does not exist)">20-Hydroxy-LTB4</a></li> <li><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">Leukotriene B4</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=CP-195543&action=edit&redlink=1" class="new" title="CP-195543 (page does not exist)">CP-195543</a></li> <li><a href="/w/index.php?title=LY-255283&action=edit&redlink=1" class="new" title="LY-255283 (page does not exist)">LY-255283</a></li> <li><a href="/w/index.php?title=ZK-158252&action=edit&redlink=1" class="new" title="ZK-158252 (page does not exist)">ZK-158252</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor" title="Cysteinyl leukotriene receptor"><abbr title="Cysteinyl leukotriene receptor">CysLT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Cysteinyl leukotriene receptor</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor_1" title="Cysteinyl leukotriene receptor 1"><abbr title="Cysteinyl leukotriene receptor 1">CysLT1</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Cysteinyl leukotriene receptor 1</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Leukotriene_C4" title="Leukotriene C4">Leukotriene C4</a></li> <li><a href="/wiki/Leukotriene_D4" title="Leukotriene D4">Leukotriene D4</a></li> <li><a href="/wiki/Leukotriene_E4" title="Leukotriene E4">Leukotriene E4</a></li></ul> <ul><li>Antagonists: <a href="/wiki/Ablukast" title="Ablukast">Ablukast</a></li> <li><a href="/w/index.php?title=BAYu9773&action=edit&redlink=1" class="new" title="BAYu9773 (page does not exist)">BAYu9773</a></li> <li><a href="/w/index.php?title=BAYu9916&action=edit&redlink=1" class="new" title="BAYu9916 (page does not exist)">BAYu9916</a></li> <li><a href="/w/index.php?title=BAYx7195&action=edit&redlink=1" class="new" title="BAYx7195 (page does not exist)">BAYx7195</a></li> <li><a href="/w/index.php?title=Cinalukast&action=edit&redlink=1" class="new" title="Cinalukast (page does not exist)">Cinalukast</a></li> <li><a href="/w/index.php?title=FPL-55712&action=edit&redlink=1" class="new" title="FPL-55712 (page does not exist)">FPL-55712</a></li> <li><a href="/w/index.php?title=ICI-198615&action=edit&redlink=1" class="new" title="ICI-198615 (page does not exist)">ICI-198615</a></li> <li><a href="/w/index.php?title=Iralukast&action=edit&redlink=1" class="new" title="Iralukast (page does not exist)">Iralukast</a></li> <li><a href="/w/index.php?title=LY-170680&action=edit&redlink=1" class="new" title="LY-170680 (page does not exist)">LY-170680</a></li> <li><a href="/w/index.php?title=Masilukast&action=edit&redlink=1" class="new" title="Masilukast (page does not exist)">Masilukast</a></li> <li><a href="/w/index.php?title=MK-571&action=edit&redlink=1" class="new" title="MK-571 (page does not exist)">MK-571</a></li> <li><a href="/wiki/Montelukast" title="Montelukast">Montelukast</a></li> <li><a href="/w/index.php?title=ONO-1078&action=edit&redlink=1" class="new" title="ONO-1078 (page does not exist)">ONO-1078</a></li> <li><a href="/w/index.php?title=Pobilukast&action=edit&redlink=1" class="new" title="Pobilukast (page does not exist)">Pobilukast</a></li> <li><a href="/wiki/Pranlukast" title="Pranlukast">Pranlukast</a></li> <li><a href="/w/index.php?title=Ritolukast&action=edit&redlink=1" class="new" title="Ritolukast (page does not exist)">Ritolukast</a></li> <li><a href="/w/index.php?title=SKF-104353&action=edit&redlink=1" class="new" title="SKF-104353 (page does not exist)">SKF-104353</a></li> <li><a href="/w/index.php?title=SR-2640&action=edit&redlink=1" class="new" title="SR-2640 (page does not exist)">SR-2640</a></li> <li><a href="/w/index.php?title=Sulukast&action=edit&redlink=1" class="new" title="Sulukast (page does not exist)">Sulukast</a></li> <li><a href="/wiki/Tipelukast" title="Tipelukast">Tipelukast</a></li> <li><a href="/w/index.php?title=Tomelukast&action=edit&redlink=1" class="new" title="Tomelukast (page does not exist)">Tomelukast</a></li> <li><a href="/w/index.php?title=Verlukast&action=edit&redlink=1" class="new" title="Verlukast (page does not exist)">Verlukast</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/w/index.php?title=ZD-3523&action=edit&redlink=1" class="new" title="ZD-3523 (page does not exist)">ZD-3523</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor_2" title="Cysteinyl leukotriene receptor 2"><abbr title="Cysteinyl leukotriene receptor 2">CysLT2</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Cysteinyl leukotriene receptor 2</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Leukotriene_C4" title="Leukotriene C4">Leukotriene C4</a></li> <li><a href="/wiki/Leukotriene_D4" title="Leukotriene D4">Leukotriene D4</a></li> <li><a href="/wiki/Leukotriene_E4" title="Leukotriene E4">Leukotriene E4</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=BAYu9773&action=edit&redlink=1" class="new" title="BAYu9773 (page does not exist)">BAYu9773</a></li> <li><a href="/w/index.php?title=BAYu9916&action=edit&redlink=1" class="new" title="BAYu9916 (page does not exist)">BAYu9916</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Cysteinyl_leukotriene_receptor_E" class="mw-redirect" title="Cysteinyl leukotriene receptor E"><abbr title="Cysteinyl leukotriene receptor E">CysLTE</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Cysteinyl leukotriene receptor E</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Leukotriene_E4" title="Leukotriene E4">Leukotriene E4</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a> (<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Arachidonate_5-lipoxygenase" title="Arachidonate 5-lipoxygenase"><abbr title="Arachidonate 5-lipoxygenase">5-LOX</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Arachidonate 5-lipoxygenase</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2-TEDC&action=edit&redlink=1" class="new" title="2-TEDC (page does not exist)">2-TEDC</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/w/index.php?title=BW-A4C&action=edit&redlink=1" class="new" title="BW-A4C (page does not exist)">BW-A4C</a></li> <li><a href="/w/index.php?title=BW-B70C&action=edit&redlink=1" class="new" title="BW-B70C (page does not exist)">BW-B70C</a></li> <li><a href="/wiki/Caffeic_acid" title="Caffeic acid">Caffeic acid</a></li> <li><a href="/w/index.php?title=Cinnamyl-3,4-dihydroxy-%CE%B1-cyanocinnamate&action=edit&redlink=1" class="new" title="Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (page does not exist)">CDC</a></li> <li><a href="/w/index.php?title=CJ-13610&action=edit&redlink=1" class="new" title="CJ-13610 (page does not exist)">CJ-13610</a></li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/wiki/Fenleuton" title="Fenleuton">Fenleuton</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/wiki/Hypericum_perforatum" title="Hypericum perforatum">Hypericum perforatum (St. John's Wort)</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid (meclofenamate)</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/w/index.php?title=N-Stearoyldopamine&action=edit&redlink=1" class="new" title="N-Stearoyldopamine (page does not exist)">N-Stearoyldopamine</a></li> <li><a href="/w/index.php?title=Timegadine&action=edit&redlink=1" class="new" title="Timegadine (page does not exist)">Timegadine</a></li> <li><a href="/wiki/Zileuton" title="Zileuton">Zileuton</a></li></ul> <ul><li><a href="/wiki/Arachidonate_5-lipoxygenase-activating_protein" class="mw-redirect" title="Arachidonate 5-lipoxygenase-activating protein"><abbr title="Arachidonate 5-lipoxygenase-activating protein">FLAP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Arachidonate 5-lipoxygenase-activating protein inhibitors: <a href="/w/index.php?title=AM-103_(drug)&action=edit&redlink=1" class="new" title="AM-103 (drug) (page does not exist)">AM-103</a></li> <li><a href="/wiki/AM-679_(FLAP_inhibitor)" title="AM-679 (FLAP inhibitor)">AM-679</a></li> <li><a href="/w/index.php?title=BAYx1005&action=edit&redlink=1" class="new" title="BAYx1005 (page does not exist)">BAYx1005</a></li> <li><a href="/w/index.php?title=MK-591&action=edit&redlink=1" class="new" title="MK-591 (page does not exist)">MK-591</a></li> <li><a href="/wiki/MK-886" title="MK-886">MK-886</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Arachidonate_12-lipoxygenase" class="mw-redirect" title="Arachidonate 12-lipoxygenase"><abbr title="Arachidonate 12-lipoxygenase">12-LOX</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Arachidonate 12-lipoxygenase</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2-TEDC&action=edit&redlink=1" class="new" title="2-TEDC (page does not exist)">2-TEDC</a></li> <li><a href="/w/index.php?title=3-Methoxytropolone&action=edit&redlink=1" class="new" title="3-Methoxytropolone (page does not exist)">3-Methoxytropolone</a></li> <li><a href="/wiki/Baicalein" title="Baicalein">Baicalein</a></li> <li><a href="/w/index.php?title=Cinnamyl-3,4-dihydroxy-%CE%B1-cyanocinnamate&action=edit&redlink=1" class="new" title="Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (page does not exist)">CDC</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Arachidonate_15-lipoxygenase" class="mw-redirect" title="Arachidonate 15-lipoxygenase"><abbr title="Arachidonate 15-lipoxygenase">15-LOX</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Arachidonate 15-lipoxygenase</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=2-TEDC&action=edit&redlink=1" class="new" title="2-TEDC (page does not exist)">2-TEDC</a></li> <li><a href="/w/index.php?title=Cinnamyl-3,4-dihydroxy-%CE%B1-cyanocinnamate&action=edit&redlink=1" class="new" title="Cinnamyl-3,4-dihydroxy-α-cyanocinnamate (page does not exist)">CDC</a></li> <li><a href="/wiki/Luteolin" title="Luteolin">Luteolin</a></li> <li><a href="/w/index.php?title=PD-146176&action=edit&redlink=1" class="new" title="PD-146176 (page does not exist)">PD-146176</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_A4_hydrolase" class="mw-redirect" title="Leukotriene A4 hydrolase"><abbr title="Leukotriene A4 hydrolase">LTA4H</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene A4 hydrolase</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Acebilustat&action=edit&redlink=1" class="new" title="Acebilustat (page does not exist)">Acebilustat</a></li> <li><a href="/wiki/Captopril" title="Captopril">Captopril</a></li> <li><a href="/w/index.php?title=DG-051&action=edit&redlink=1" class="new" title="DG-051 (page does not exist)">DG-051</a></li> <li><a href="/wiki/Fosinoprilat" class="mw-redirect" title="Fosinoprilat">Fosinoprilat</a></li> <li><a href="/w/index.php?title=JNJ-26993135&action=edit&redlink=1" class="new" title="JNJ-26993135 (page does not exist)">JNJ-26993135</a></li> <li><a href="/w/index.php?title=SA-6541&action=edit&redlink=1" class="new" title="SA-6541 (page does not exist)">SA-6541</a></li> <li><a href="/w/index.php?title=SC-57461A&action=edit&redlink=1" class="new" title="SC-57461A (page does not exist)">SC-57461A</a></li> <li><a href="/wiki/Ubenimex" title="Ubenimex">Ubenimex (bestatin)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_B4_%CF%89-hydroxylase" class="mw-redirect" title="Leukotriene B4 ω-hydroxylase"><abbr title="Leukotriene B4 ω-hydroxylase">LTB4H</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene B4 ω-hydroxylase</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=17-Octadecynoic_acid&action=edit&redlink=1" class="new" title="17-Octadecynoic acid (page does not exist)">17-Octadecynoic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_C4_synthase" title="Leukotriene C4 synthase"><abbr title="Leukotriene C4 synthase">LTC4S</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene C4 synthase</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Azelastine" title="Azelastine">Azelastine</a></li> <li><a href="/wiki/MK-886" title="MK-886">MK-886</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_C4_hydrolase" title="Leukotriene C4 hydrolase"><abbr title="Leukotriene C4 hydrolase">LTC4H</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene C4 hydrolase</th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acivicin" title="Acivicin">Acivicin</a></li> <li><a href="/w/index.php?title=Serine-borate_complex&action=edit&redlink=1" class="new" title="Serine-borate complex (page does not exist)">Serine-borate complex</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Leukotriene_D4_hydrolase" class="mw-redirect" title="Leukotriene D4 hydrolase"><abbr title="Leukotriene D4 hydrolase">LTD4</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Leukotriene D4 hydrolase</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cilastatin" title="Cilastatin">Cilastatin</a></li> <li><a href="/wiki/Ubenimex" title="Ubenimex">Ubenimex (bestatin)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Precursors: <a href="/wiki/Linoleic_acid" title="Linoleic acid">Linoleic acid</a></li> <li><a href="/wiki/%CE%93-Linolenic_acid" title="Γ-Linolenic acid">γ-Linolenic acid (gamolenic acid)</a></li> <li><a href="/wiki/Dihomo-%CE%B3-linolenic_acid" title="Dihomo-γ-linolenic acid">Dihomo-γ-linolenic acid</a></li> <li><a href="/wiki/Diglyceride" title="Diglyceride">Diacylglycerol</a></li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li> <li><a href="/wiki/Arachidonic_acid_5-hydroperoxide" title="Arachidonic acid 5-hydroperoxide">5-HPETE (arachidonic acid 5-hydroperoxide)</a></li> <li><a href="/wiki/Leukotriene_A4" title="Leukotriene A4">Leukotriene A4</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Prostanoid_signaling_modulators" title="Template:Prostanoid signaling modulators">Prostanoid signaling modulators</a></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="PPARTooltip_Peroxisome_proliferator-activated_receptor_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:PPAR_modulators" title="Template:PPAR modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:PPAR_modulators" title="Template talk:PPAR modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:PPAR_modulators" title="Special:EditPage/Template:PPAR modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="PPARTooltip_Peroxisome_proliferator-activated_receptor_modulators" style="font-size:114%;margin:0 4em"><a href="/wiki/Peroxisome_proliferator-activated_receptor" title="Peroxisome proliferator-activated receptor"><abbr title="Peroxisome proliferator-activated receptor">PPAR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Peroxisome proliferator-activated receptor <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Peroxisome_proliferator-activated_receptor_alpha" title="Peroxisome proliferator-activated receptor alpha"><abbr title="Peroxisome proliferator-activated receptor alpha">PPARα</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Peroxisome proliferator-activated receptor alpha</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a class="mw-selflink selflink">15-HETE</a></li> <li><a href="/w/index.php?title=15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (page does not exist)">15-HpETE</a></li> <li><a href="/wiki/Aleglitazar" title="Aleglitazar">Aleglitazar</a></li> <li><a href="/wiki/Aluminium_clofibrate" title="Aluminium clofibrate">Aluminium clofibrate</a></li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li> <li><a href="/wiki/Bezafibrate" title="Bezafibrate">Bezafibrate</a></li> <li><a href="/wiki/Chiglitazar" title="Chiglitazar">Chiglitazar</a></li> <li><a href="/wiki/Clofibrate" title="Clofibrate">Clofibrate</a></li> <li><a href="/w/index.php?title=CP-775146&action=edit&redlink=1" class="new" title="CP-775146 (page does not exist)">CP-775146</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Dehydroepiandrosterone" title="Dehydroepiandrosterone">DHEA</a> (<a href="/wiki/Prasterone" title="Prasterone">prasterone</a>) (in rodents)</li> <li><a href="/wiki/Elafibranor" title="Elafibranor">Elafibranor</a></li> <li><a href="/wiki/Etomoxir" title="Etomoxir">Etomoxir</a></li> <li><a href="/wiki/Fenofibrate" title="Fenofibrate">Fenofibrate</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Gemfibrozil" title="Gemfibrozil">Gemfibrozil</a></li> <li><a href="/w/index.php?title=GW-7647&action=edit&redlink=1" class="new" title="GW-7647 (page does not exist)">GW-7647</a></li> <li><a href="/wiki/Lanifibranor" title="Lanifibranor">Lanifibranor</a></li> <li><a href="/wiki/Leukotriene_B4" title="Leukotriene B4">Leukotriene B4</a></li> <li><a href="/w/index.php?title=LG-101506&action=edit&redlink=1" class="new" title="LG-101506 (page does not exist)">LG-101506</a></li> <li><a href="/w/index.php?title=LG-100754&action=edit&redlink=1" class="new" title="LG-100754 (page does not exist)">LG-100754</a></li> <li><a href="/wiki/Lobeglitazone" title="Lobeglitazone">Lobeglitazone</a></li> <li><a href="/wiki/Muraglitazar" title="Muraglitazar">Muraglitazar</a></li> <li><a href="/wiki/Oleylethanolamide" class="mw-redirect" title="Oleylethanolamide">Oleylethanolamide</a></li> <li><a href="/wiki/Palmitoylethanolamide" title="Palmitoylethanolamide">Palmitoylethanolamide</a></li> <li><a href="/wiki/Pemafibrate" title="Pemafibrate">Pemafibrate</a></li> <li><a href="/wiki/Perfluorononanoic_acid" title="Perfluorononanoic acid">Perfluorononanoic acid</a></li> <li><a href="/wiki/Perfluorooctanoic_acid" title="Perfluorooctanoic acid">Perfluorooctanoic acid</a></li> <li><a href="/wiki/Pioglitazone" title="Pioglitazone">Pioglitazone</a></li> <li><a href="/wiki/Saroglitazar" title="Saroglitazar">Saroglitazar</a></li> <li><a href="/wiki/Sodelglitazar" title="Sodelglitazar">Sodelglitazar</a></li> <li><a href="/wiki/Tesaglitazar" title="Tesaglitazar">Tesaglitazar</a></li> <li><a href="/wiki/Tetradecylthioacetic_acid" title="Tetradecylthioacetic acid">Tetradecylthioacetic acid</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li> <li><a href="/w/index.php?title=WY-14643&action=edit&redlink=1" class="new" title="WY-14643 (page does not exist)">WY-14643</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=GW-6471&action=edit&redlink=1" class="new" title="GW-6471 (page does not exist)">GW-6471</a></li> <li><a href="/wiki/MK-886" title="MK-886">MK-886</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Peroxisome_proliferator-activated_receptor_delta" title="Peroxisome proliferator-activated receptor delta"><abbr title="Peroxisome proliferator-activated receptor delta">PPARδ</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Peroxisome proliferator-activated receptor delta</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a class="mw-selflink selflink">15-HETE</a></li> <li><a href="/w/index.php?title=15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (page does not exist)">15-HpETE</a></li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li> <li><a href="/wiki/Bezafibrate" title="Bezafibrate">Bezafibrate</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Elafibranor" title="Elafibranor">Elafibranor</a></li> <li><a href="/w/index.php?title=Fonadelpar&action=edit&redlink=1" class="new" title="Fonadelpar (page does not exist)">Fonadelpar</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/GW-0742" class="mw-redirect" title="GW-0742">GW-0742</a></li> <li><a href="/wiki/GW-501516" class="mw-redirect" title="GW-501516">GW-501516</a></li> <li><a href="/w/index.php?title=L-165,041&action=edit&redlink=1" class="new" title="L-165,041 (page does not exist)">L-165,041</a></li> <li><a href="/wiki/Lanifibranor" title="Lanifibranor">Lanifibranor</a></li> <li><a href="/w/index.php?title=LG-101506&action=edit&redlink=1" class="new" title="LG-101506 (page does not exist)">LG-101506</a></li> <li><a href="/wiki/Seladelpar" title="Seladelpar">Seladelpar</a></li> <li><a href="/wiki/Sodelglitazar" title="Sodelglitazar">Sodelglitazar</a></li> <li><a href="/wiki/Tetradecylthioacetic_acid" title="Tetradecylthioacetic acid">Tetradecylthioacetic acid</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=FH-535&action=edit&redlink=1" class="new" title="FH-535 (page does not exist)">FH-535</a></li> <li><a href="/w/index.php?title=GSK-0660&action=edit&redlink=1" class="new" title="GSK-0660 (page does not exist)">GSK-0660</a></li> <li><a href="/w/index.php?title=GSK-3787&action=edit&redlink=1" class="new" title="GSK-3787 (page does not exist)">GSK-3787</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Peroxisome_proliferator-activated_receptor_gamma" title="Peroxisome proliferator-activated receptor gamma"><abbr title="Peroxisome proliferator-activated receptor gamma">PPARγ</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Peroxisome proliferator-activated receptor gamma</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/w/index.php?title=5-Oxo-6E,8Z,11Z,14Z-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="5-Oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid (page does not exist)">5-Oxo-ETE</a></li> <li><a href="/w/index.php?title=5-Oxo-15-hydroxy-ETE&action=edit&redlink=1" class="new" title="5-Oxo-15-hydroxy-ETE (page does not exist)">5-Oxo-15-hydroxy-ETE</a></li> <li><a href="/wiki/15-Deoxy-%CE%9412,14-prostaglandin_J2" class="mw-redirect" title="15-Deoxy-Δ12,14-prostaglandin J2">15-Deoxy-Δ12,14-prostaglandin J2</a></li> <li><a class="mw-selflink selflink">15-HETE</a></li> <li><a href="/w/index.php?title=15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic_acid&action=edit&redlink=1" class="new" title="15-Hydroperoxy-5Z,8Z,11Z,13E-eicosatetraenoic acid (page does not exist)">15-HpETE</a></li> <li><a href="/wiki/Aleglitazar" title="Aleglitazar">Aleglitazar</a></li> <li><a href="/wiki/Arachidonic_acid" title="Arachidonic acid">Arachidonic acid</a></li> <li><a href="/w/index.php?title=Balaglitazone&action=edit&redlink=1" class="new" title="Balaglitazone (page does not exist)">Balaglitazone</a></li> <li><a href="/wiki/Berberine" title="Berberine">Berberine</a></li> <li><a href="/wiki/Bezafibrate" title="Bezafibrate">Bezafibrate</a></li> <li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/w/index.php?title=Cevoglitazar&action=edit&redlink=1" class="new" title="Cevoglitazar (page does not exist)">Cevoglitazar</a></li> <li><a href="/wiki/Chiglitazar" title="Chiglitazar">Chiglitazar</a></li> <li><a href="/wiki/Ciglitazone" title="Ciglitazone">Ciglitazone</a></li> <li><a href="/wiki/Daidzein" title="Daidzein">Daidzein</a></li> <li><a href="/wiki/Darglitazone" title="Darglitazone">Darglitazone</a></li> <li><a href="/w/index.php?title=Edaglitazone&action=edit&redlink=1" class="new" title="Edaglitazone (page does not exist)">Edaglitazone</a></li> <li><a href="/w/index.php?title=Efatutazone&action=edit&redlink=1" class="new" title="Efatutazone (page does not exist)">Efatutazone</a></li> <li><a href="/wiki/Englitazone" title="Englitazone">Englitazone</a></li> <li><a href="/wiki/Etalocib" title="Etalocib">Etalocib</a></li> <li><a href="/wiki/Farglitazar" title="Farglitazar">Farglitazar</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/w/index.php?title=GW-1929&action=edit&redlink=1" class="new" title="GW-1929 (page does not exist)">GW-1929</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a></li> <li><a href="/w/index.php?title=Imiglitazar&action=edit&redlink=1" class="new" title="Imiglitazar (page does not exist)">Imiglitazar</a></li> <li><a href="/wiki/Indeglitazar" class="mw-redirect" title="Indeglitazar">Indeglitazar</a></li> <li><a href="/wiki/Lanifibranor" title="Lanifibranor">Lanifibranor</a></li> <li><a href="/w/index.php?title=LG-100268&action=edit&redlink=1" class="new" title="LG-100268 (page does not exist)">LG-100268</a></li> <li><a href="/w/index.php?title=LG-100754&action=edit&redlink=1" class="new" title="LG-100754 (page does not exist)">LG-100754</a></li> <li><a href="/w/index.php?title=LG-101506&action=edit&redlink=1" class="new" title="LG-101506 (page does not exist)">LG-101506</a></li> <li><a href="/wiki/Lobeglitazone" title="Lobeglitazone">Lobeglitazone</a></li> <li><a href="/wiki/Muraglitazar" title="Muraglitazar">Muraglitazar (muroglitazar)</a></li> <li><a href="/w/index.php?title=NTZDpa&action=edit&redlink=1" class="new" title="NTZDpa (page does not exist)">nTZDpa</a></li> <li><a href="/w/index.php?title=Naveglitazar&action=edit&redlink=1" class="new" title="Naveglitazar (page does not exist)">Naveglitazar</a></li> <li><a href="/wiki/Netoglitazone" title="Netoglitazone">Netoglitazone</a></li> <li><a href="/w/index.php?title=Oxeglitazar&action=edit&redlink=1" class="new" title="Oxeglitazar (page does not exist)">Oxeglitazar</a></li> <li><a href="/w/index.php?title=Peliglitazar&action=edit&redlink=1" class="new" title="Peliglitazar (page does not exist)">Peliglitazar</a></li> <li><a href="/w/index.php?title=Pemaglitazar&action=edit&redlink=1" class="new" title="Pemaglitazar (page does not exist)">Pemaglitazar</a></li> <li><a href="/wiki/Perfluorononanoic_acid" title="Perfluorononanoic acid">Perfluorononanoic acid</a></li> <li><a href="/wiki/Pioglitazone" title="Pioglitazone">Pioglitazone</a></li> <li><a href="/w/index.php?title=Prostaglandin_J2&action=edit&redlink=1" class="new" title="Prostaglandin J2 (page does not exist)">Prostaglandin J2</a></li> <li><a href="/w/index.php?title=Ragaglitazar&action=edit&redlink=1" class="new" title="Ragaglitazar (page does not exist)">Ragaglitazar</a></li> <li><a href="/w/index.php?title=Reglitazar&action=edit&redlink=1" class="new" title="Reglitazar (page does not exist)">Reglitazar</a></li> <li><a href="/wiki/Rivoglitazone" title="Rivoglitazone">Rivoglitazone</a></li> <li><a href="/wiki/Rosiglitazone" title="Rosiglitazone">Rosiglitazone</a></li> <li><a href="/w/index.php?title=RS5444&action=edit&redlink=1" class="new" title="RS5444 (page does not exist)">RS5444</a></li> <li><a href="/wiki/Saroglitazar" title="Saroglitazar">Saroglitazar</a></li> <li><a href="/w/index.php?title=Sipoglitazar&action=edit&redlink=1" class="new" title="Sipoglitazar (page does not exist)">Sipoglitazar</a></li> <li><a href="/wiki/Sodelglitazar" title="Sodelglitazar">Sodelglitazar</a></li> <li><a href="/wiki/Telmisartan" title="Telmisartan">Telmisartan</a></li> <li><a href="/wiki/Tesaglitazar" title="Tesaglitazar">Tesaglitazar</a></li> <li><a href="/wiki/Troglitazone" title="Troglitazone">Troglitazone</a></li></ul> <ul><li><a href="/wiki/Selective_PPAR%CE%B3_modulator" class="mw-redirect" title="Selective PPARγ modulator"><abbr title="Selective PPARγ modulator">SPPARMs</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Selective PPARγ modulator: <a href="/wiki/Bisphenol_A_diglycidyl_ether" title="Bisphenol A diglycidyl ether">BADGE</a></li> <li><a href="/wiki/EPI-001" title="EPI-001">EPI-001</a></li> <li><a href="/w/index.php?title=INT-131&action=edit&redlink=1" class="new" title="INT-131 (page does not exist)">INT-131</a></li> <li><a href="/w/index.php?title=MK-0533&action=edit&redlink=1" class="new" title="MK-0533 (page does not exist)">MK-0533</a></li> <li><a href="/w/index.php?title=S26948&action=edit&redlink=1" class="new" title="S26948 (page does not exist)">S26948</a></li></ul> <ul><li>Antagonists: <a href="/w/index.php?title=FH-535&action=edit&redlink=1" class="new" title="FH-535 (page does not exist)">FH-535</a></li> <li><a href="/w/index.php?title=GW-9662&action=edit&redlink=1" class="new" title="GW-9662 (page does not exist)">GW-9662</a></li> <li><a href="/w/index.php?title=SR-202_(drug)&action=edit&redlink=1" class="new" title="SR-202 (drug) (page does not exist)">SR-202</a></li> <li><a href="/w/index.php?title=T-0070907&action=edit&redlink=1" class="new" title="T-0070907 (page does not exist)">T-0070907</a></li></ul> <ul><li>Unknown: <a href="/w/index.php?title=SR-1664&action=edit&redlink=1" class="new" title="SR-1664 (page does not exist)">SR-1664</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Non-selective</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Agonists: <a href="/wiki/Ciprofibrate" title="Ciprofibrate">Ciprofibrate</a></li> <li><a href="/wiki/Clinofibrate" title="Clinofibrate">Clinofibrate</a></li> <li><a href="/wiki/Clofibride" title="Clofibride">Clofibride</a></li> <li><a href="/wiki/Englitazone" title="Englitazone">Englitazone</a></li> <li><a href="/wiki/Etofibrate" title="Etofibrate">Etofibrate</a></li> <li><a href="/wiki/Farglitazar" title="Farglitazar">Farglitazar</a></li> <li><a href="/wiki/Netoglitazone" title="Netoglitazone">Netoglitazone</a></li> <li><a href="/wiki/Ronifibrate" title="Ronifibrate">Ronifibrate</a></li> <li><a href="/wiki/Rivoglitazone" title="Rivoglitazone">Rivoglitazone</a></li> <li><a href="/wiki/Simfibrate" title="Simfibrate">Simfibrate</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd></dl> </div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1&useformat=desktop" alt="" width="1" height="1" 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