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vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#In_popular_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>In popular culture</span> </div> </a> <ul id="toc-In_popular_culture-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Phenacetin</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 28 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-28" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">28 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D9%86%D8%A7%D8%B3%D9%8A%D8%AA%D9%8A%D9%86" title="فيناسيتين – Arabic" lang="ar" hreflang="ar" data-title="فيناسيتين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%BE%D9%86%D8%AA%D8%A7%DA%A9%D8%AA%DB%8C%D9%86" title="پنتاکتین – South Azerbaijani" lang="azb" hreflang="azb" data-title="پنتاکتین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A4%D0%B0%D0%BD%D0%B0%D1%86%D0%B5%D1%82%D0%B8%D0%BD" title="Фанацетин – Bulgarian" lang="bg" hreflang="bg" data-title="Фанацетин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Fenacetina" title="Fenacetina – Catalan" lang="ca" hreflang="ca" data-title="Fenacetina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Fenacetin" title="Fenacetin – Czech" lang="cs" hreflang="cs" data-title="Fenacetin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Ffenacetin" title="Ffenacetin – Welsh" lang="cy" hreflang="cy" data-title="Ffenacetin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Phenacetin" title="Phenacetin – German" lang="de" hreflang="de" data-title="Phenacetin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Fenatsetiin" title="Fenatsetiin – Estonian" lang="et" hreflang="et" data-title="Fenatsetiin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Fenacetina" title="Fenacetina – Spanish" lang="es" hreflang="es" data-title="Fenacetina" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Fenacetino" title="Fenacetino – Esperanto" lang="eo" hreflang="eo" data-title="Fenacetino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%81%D9%86%D8%A7%D8%B3%D8%AA%DB%8C%D9%86" title="فناستین – Persian" lang="fa" hreflang="fa" data-title="فناستین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Ph%C3%A9nac%C3%A9tine" title="Phénacétine – French" lang="fr" hreflang="fr" data-title="Phénacétine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-io mw-list-item"><a href="https://io.wikipedia.org/wiki/Fenacetino" title="Fenacetino – Ido" lang="io" hreflang="io" data-title="Fenacetino" data-language-autonym="Ido" data-language-local-name="Ido" class="interlanguage-link-target"><span>Ido</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Fenasetin" title="Fenasetin – Indonesian" lang="id" hreflang="id" data-title="Fenasetin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Fenacetina" title="Fenacetina – Italian" lang="it" hreflang="it" data-title="Fenacetina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Fenacetine" title="Fenacetine – Dutch" lang="nl" hreflang="nl" data-title="Fenacetine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%95%E3%82%A7%E3%83%8A%E3%82%BB%E3%83%81%E3%83%B3" title="フェナセチン – Japanese" lang="ja" hreflang="ja" data-title="フェナセチン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Fenacetyna" title="Fenacetyna – Polish" lang="pl" hreflang="pl" data-title="Fenacetyna" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target"><span>Polski</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Fenacetina" title="Fenacetina – Portuguese" lang="pt" hreflang="pt" data-title="Fenacetina" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Fenacetin%C4%83" title="Fenacetină – Romanian" lang="ro" hreflang="ro" data-title="Fenacetină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%A4%D0%B5%D0%BD%D0%B0%D1%86%D0%B5%D1%82%D0%B8%D0%BD" title="Фенацетин – Russian" lang="ru" hreflang="ru" data-title="Фенацетин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Fenacetin" title="Fenacetin – Serbian" lang="sr" hreflang="sr" data-title="Fenacetin" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Fenacetin" title="Fenacetin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Fenacetin" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Fenasetiini" title="Fenasetiini – Finnish" lang="fi" hreflang="fi" data-title="Fenasetiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Fenacetin" title="Fenacetin – Swedish" lang="sv" hreflang="sv" data-title="Fenacetin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%9F%E0%B8%B5%E0%B8%99%E0%B8%B2%E0%B9%80%E0%B8%8B%E0%B8%95%E0%B8%B4%E0%B8%99" title="ฟีนาเซติน – Thai" lang="th" hreflang="th" data-title="ฟีนาเซติน" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Fenasetin" title="Fenasetin – Turkish" lang="tr" hreflang="tr" data-title="Fenasetin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%9D%9E%E9%82%A3%E8%A5%BF%E4%B8%81" title="非那西丁 – Chinese" lang="zh" hreflang="zh" data-title="非那西丁" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet 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class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Phenacetin">Phenacetin</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Phenacetin_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Phenacetin_skeletal.svg/250px-Phenacetin_skeletal.svg.png" decoding="async" width="220" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Phenacetin_skeletal.svg/330px-Phenacetin_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/0f/Phenacetin_skeletal.svg/500px-Phenacetin_skeletal.svg.png 2x" data-file-width="505" data-file-height="250" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Phenacetin_molecule_ball.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Phenacetin_molecule_ball.png/250px-Phenacetin_molecule_ball.png" decoding="async" width="220" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Phenacetin_molecule_ball.png/330px-Phenacetin_molecule_ball.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/Phenacetin_molecule_ball.png/500px-Phenacetin_molecule_ball.png 2x" data-file-width="2000" data-file-height="1074" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><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 href="/wiki/ATC_code_N02" title="ATC code N02">N02BE03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N02BE03">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</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; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;"><i>N</i>-(4-Ethoxyphenyl)acetamide</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=62-44-2">62-44-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/4754">4754</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7402">7402</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB03783">DB03783</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.4590.html">4590</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/ER0CTH01H9">ER0CTH01H9</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00569">D00569</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8050">CHEBI:8050</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL16073">ChEMBL16073</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID1021116">DTXSID1021116</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419175#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.485">100.000.485</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q419175#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>10</sub><span title="Hydrogen">H</span><sub>13</sub><span title="Nitrogen">N</span><span title="Oxygen">O</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002179219000000000♠"></span>179.219</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28Nc1ccc%28OCC%29cc1%29C">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Density" title="Density">Density</a></th><td class="infobox-data">1.24 g/cm<sup>3</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">134 to 137.5 °C (273.2 to 279.5 °F)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></th><td class="infobox-data">0.766 g/L (25 °C (77 °F))</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O=C(Nc1ccc(OCC)cc1)C</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:CPJSUEIXXCENMM-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464199717&page2=Phenacetin">(verify)</a></span></span></td></tr></tbody></table> <p><b>Phenacetin</b> (<span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="'f' in 'find'">f</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'n' in 'nigh'">n</span><span title="/æ/: 'a' in 'bad'">æ</span><span title="'s' in 'sigh'">s</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'t' in 'tie'">t</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span></span>/</a></span> <span class="ext-phonos"><span data-nosnippet="" id="ooui-php-1" class="noexcerpt ext-phonos-PhonosButton ext-phonos-PhonosButton-emptylabel oo-ui-widget oo-ui-widget-enabled oo-ui-buttonElement oo-ui-buttonElement-frameless oo-ui-iconElement oo-ui-buttonWidget" data-ooui="{"_":"mw.Phonos.PhonosButton","href":"\/\/upload.wikimedia.org\/wikipedia\/commons\/transcoded\/c\/c0\/LL-Q1860_%28eng%29-Flame%2C_not_lame-phenacetin.wav\/LL-Q1860_%28eng%29-Flame%2C_not_lame-phenacetin.wav.mp3","rel":["nofollow"],"framed":false,"icon":"volumeUp","data":{"ipa":"","text":"","lang":"en","wikibase":"","file":"LL-Q1860 (eng)-Flame, not lame-phenacetin.wav"},"classes":["noexcerpt","ext-phonos-PhonosButton","ext-phonos-PhonosButton-emptylabel"]}"><a role="button" tabindex="0" href="//upload.wikimedia.org/wikipedia/commons/transcoded/c/c0/LL-Q1860_%28eng%29-Flame%2C_not_lame-phenacetin.wav/LL-Q1860_%28eng%29-Flame%2C_not_lame-phenacetin.wav.mp3" rel="nofollow" aria-label="Play audio" title="Play audio" class="oo-ui-buttonElement-button"><span class="oo-ui-iconElement-icon oo-ui-icon-volumeUp"></span><span class="oo-ui-labelElement-label"></span><span class="oo-ui-indicatorElement-indicator oo-ui-indicatorElement-noIndicator"></span></a></span><sup class="ext-phonos-attribution noexcerpt navigation-not-searchable"><a href="/wiki/File:LL-Q1860_(eng)-Flame,_not_lame-phenacetin.wav" title="File:LL-Q1860 (eng)-Flame, not lame-phenacetin.wav">ⓘ</a></sup></span></span>; <b>acetophenetidin</b>, <b><i>N</i>-(4-ethoxyphenyl)acetamide</b><sup id="cite_ref-canada_1-0" class="reference"><a href="#cite_note-canada-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>) is a <a href="/wiki/Analgesic" title="Analgesic">pain-relieving</a> and <a href="/wiki/Antipyretic" title="Antipyretic">fever-reducing</a> drug, which was widely used following its introduction in 1887. It was withdrawn from medicinal use as dangerous from the 1970s (e.g., withdrawn in Canada in 1973,<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and by the <a href="/wiki/U.S._Food_and_Drug_Administration" class="mw-redirect" title="U.S. Food and Drug Administration">U.S. Food and Drug Administration</a> in 1983<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>). </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenacetin was introduced in 1887 in <a href="/wiki/Elberfeld" title="Elberfeld">Elberfeld</a>, Germany by German company <a href="/wiki/Bayer" title="Bayer">Bayer</a>, and was used principally as an analgesic; it was one of the first synthetic fever reducers to go on the market. It is also known historically to be one of the first non-<a href="/wiki/Opioid" title="Opioid">opioid</a> analgesics without anti-inflammatory properties. Although <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> (acetaminophen) was produced earlier, a historical accident saw it ignored after <a href="/wiki/Joseph_von_Mering" title="Joseph von Mering">Joseph von Mering</a>'s 1893 assessment.<sup id="cite_ref-drugdiscov_4-0" class="reference"><a href="#cite_note-drugdiscov-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Prior to World War One, Britain imported phenacetin from Germany.<sup id="cite_ref-Creese1997_5-0" class="reference"><a href="#cite_note-Creese1997-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> During the war, a team including <a href="/wiki/Jocelyn_Field_Thorpe" title="Jocelyn Field Thorpe">Jocelyn Field Thorpe</a> and <a href="/wiki/Martha_Annie_Whiteley" title="Martha Annie Whiteley">Martha Annie Whiteley</a> developed a synthesis in Britain.<sup id="cite_ref-Creese1997_5-1" class="reference"><a href="#cite_note-Creese1997-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Known_mechanism_of_action">Known mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=2" title="Edit section: Known mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenacetin's analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action on the heart, where it acts as a negative <a href="/wiki/Inotrope" title="Inotrope">inotrope</a>. It is an <a href="/wiki/Antipyretic" title="Antipyretic">antipyretic</a>, acting on the brain to decrease the temperature set point. It is also used to treat <a href="/wiki/Rheumatoid_arthritis" title="Rheumatoid arthritis">rheumatoid arthritis</a> (subacute type) and intercostal <a href="/wiki/Neuralgia" title="Neuralgia">neuralgia</a>. </p><p>In vivo, one of two reactions occur. Usually phenacetin's <a href="/wiki/Ether" title="Ether">ether</a> is cleaved to leave <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> (acetaminophen), which is the clinically relevant analgesic. A minority of the time the acetyl group is removed from the amine, producing carcinogenic <a href="/wiki/P-Phenetidine" title="P-Phenetidine">p-phenetidine</a>. This reaction is quite rare, however, as evidenced by the fact that the drug was on the market for almost 100 years before a statistical link was established, when Canada, followed by the United States, withdrew it from the market. </p> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=3" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first synthesis was reported in 1878 by <a href="/wiki/Harmon_Northrop_Morse" title="Harmon Northrop Morse">Harmon Northrop Morse</a>. Morse's cited article describes the synthesis of paracetamol from 4-aminophenol and acetic acid.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Phenacetin may be synthesized as an example of the <a href="/wiki/Williamson_ether_synthesis" title="Williamson ether synthesis">Williamson ether synthesis</a>: <a href="/wiki/Ethyl_iodide" title="Ethyl iodide">ethyl iodide</a>, <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a>, and anhydrous <a href="/wiki/Potassium_carbonate" title="Potassium carbonate">potassium carbonate</a> are heated in <a href="/wiki/2-butanone" class="mw-redirect" title="2-butanone">2-butanone</a> to give the crude product, which is recrystallized from water.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=4" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Vicks_Double-Buffered_Cold_Tablets.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Vicks_Double-Buffered_Cold_Tablets.jpg/220px-Vicks_Double-Buffered_Cold_Tablets.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Vicks_Double-Buffered_Cold_Tablets.jpg/330px-Vicks_Double-Buffered_Cold_Tablets.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/cf/Vicks_Double-Buffered_Cold_Tablets.jpg/440px-Vicks_Double-Buffered_Cold_Tablets.jpg 2x" data-file-width="1373" data-file-height="1030" /></a><figcaption><a href="/wiki/Vicks" title="Vicks">Vicks</a> cold tablets, containing: <a href="/wiki/Salicylamide" title="Salicylamide">salicylamide</a>, phenacetin <style data-mw-deduplicate="TemplateStyles:r1154941027">.mw-parser-output .frac{white-space:nowrap}.mw-parser-output .frac .num,.mw-parser-output .frac .den{font-size:80%;line-height:0;vertical-align:super}.mw-parser-output .frac .den{vertical-align:sub}.mw-parser-output .sr-only{border:0;clip:rect(0,0,0,0);clip-path:polygon(0px 0px,0px 0px,0px 0px);height:1px;margin:-1px;overflow:hidden;padding:0;position:absolute;width:1px}</style><span class="frac">2<span class="sr-only">+</span><span class="num">1</span>⁄<span class="den">2</span></span> grs., <a href="/wiki/Pyrilamine_maleate" class="mw-redirect" title="Pyrilamine maleate">pyrilamine maleate</a>, caffeine, <a href="/wiki/Ephedrine_sulphate" class="mw-redirect" title="Ephedrine sulphate">ephedrine sulphate</a>, <a href="/wiki/Magnesium_hydroxide" title="Magnesium hydroxide">magnesium hydroxide</a>, and <a href="/wiki/Aluminum_hydroxide" class="mw-redirect" title="Aluminum hydroxide">aluminum hydroxide</a> complex (U.S. Pat. 2,446,981). That patent number is from 1948; these tablets would have been made shortly thereafter.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Medical">Medical</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=5" title="Edit section: Medical"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenacetin was widely used until the third quarter of the twentieth century, often in the form of an A.P.C., or "<a href="/wiki/Aspirin" title="Aspirin">aspirin</a>-phenacetin-<a href="/wiki/Caffeine" title="Caffeine">caffeine</a>" <a href="/wiki/Compound_analgesic" title="Compound analgesic">compound analgesic</a>, as a remedy for fever and pain. An early formulation (1919) was <a href="/wiki/Vincent%27s_APC" class="mw-redirect" title="Vincent's APC">Vincent's APC</a> in Australia. </p><p>In the United States, the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> ordered the withdrawal of drugs containing phenacetin in November 1983, due to its <a href="/wiki/Carcinogen" title="Carcinogen">carcinogenic</a> and kidney-damaging properties.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> It was also banned in India.<sup id="cite_ref-ban_9-0" class="reference"><a href="#cite_note-ban-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> As a result, some branded, and previously phenacetin-based, preparations continued to be sold, but with the phenacetin replaced by safer alternatives. A popular brand of phenacetin was <a href="/wiki/Hoffmann-La_Roche" class="mw-redirect" title="Hoffmann-La Roche">Roche</a>'s <a href="/wiki/Saridon" class="mw-redirect" title="Saridon">Saridon</a>, which was reformulated in 1983 to contain <a href="/wiki/Propyphenazone" title="Propyphenazone">propyphenazone</a>, <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> and <a href="/wiki/Caffeine" title="Caffeine">caffeine</a>. <a href="/wiki/Coricidin" title="Coricidin">Coricidin</a> was also reformulated without phenacetin. Paracetamol is a metabolite of phenacetin with similar analgesic and antipyretic effects, but the new formulation has not been found to have phenacetin's carcinogenicity. </p> <div class="mw-heading mw-heading3"><h3 id="Other">Other</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=6" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenacetin has been used as a <a href="/wiki/Cutting_agent" class="mw-redirect" title="Cutting agent">cutting agent</a> to adulterate <a href="/wiki/Cocaine" title="Cocaine">cocaine</a> in the UK and Canada, due to the similar physical properties.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> There, it has been given the nickname "magic". </p><p>Due to its low cost, phenacetin is used for research into the physical and refractive properties of crystals. It is an ideal compound for this type of research.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The reason for this is unclear. (January 2021)">why?</span></a></i>]</sup><sup id="cite_ref-canada_1-1" class="reference"><a href="#cite_note-canada-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>In Canada, phenacetin is used as a laboratory reagent, and in a few hair dye preparations (as a stabilizer for hydrogen peroxide). While it is considered a prescription drug, no marketed drugs contain phenacetin.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Safety">Safety</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=7" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Phenacetin, and products containing phenacetin, have been shown in an <a href="/wiki/Animal_model" class="mw-redirect" title="Animal model">animal model</a> to have the side effect and after-effect of <a href="/wiki/Carcinogenesis" title="Carcinogenesis">carcinogenesis</a>. In humans, many case reports have implicated products containing phenacetin in urothelial neoplasms, especially <a href="/wiki/Urothelial_carcinoma" class="mw-redirect" title="Urothelial carcinoma">urothelial carcinoma</a> of the <a href="/wiki/Renal_pelvis" title="Renal pelvis">renal pelvis</a>. Phenacetin is classified by the <a href="/wiki/International_Agency_for_Research_on_Cancer" title="International Agency for Research on Cancer">International Agency for Research on Cancer</a> (IARC) as carcinogenic to humans.<sup id="cite_ref-canada_1-2" class="reference"><a href="#cite_note-canada-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> In one prospective series, phenacetin was associated with an increased risk of death due to urologic or renal diseases, death due to cancers, and death due to cardiovascular diseases.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> In addition, people with <a href="/wiki/Glucose-6-phosphate_dehydrogenase_deficiency" title="Glucose-6-phosphate dehydrogenase deficiency">glucose-6-phosphate dehydrogenase deficiency</a> may experience acute <a href="/wiki/Hemolysis" title="Hemolysis">hemolysis</a>, or dissolution of blood cells, while taking this drug. Acute hemolysis is possible in the case of patients who develop an <a href="/wiki/IgM" class="mw-redirect" title="IgM">IgM</a> response to phenacetin leading to immune complexes that bind to <a href="/wiki/Erythrocytes" class="mw-redirect" title="Erythrocytes">erythrocytes</a> in blood. The erythrocytes are then lysed when the complexes activate the <a href="/wiki/Complement_system" title="Complement system">complement system</a>. </p><p>Chronic use of phenacetin is known to lead to <a href="/wiki/Analgesic_nephropathy" title="Analgesic nephropathy">analgesic nephropathy</a> characterized by <a href="/wiki/Renal_papillary_necrosis" title="Renal papillary necrosis">renal papillary necrosis</a>.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> This is a condition which results in destruction of some or all of the <a href="/wiki/Renal_papilla" class="mw-redirect" title="Renal papilla">renal papillae</a> in the kidneys. It is believed that the metabolite <a href="/wiki/P-Phenetidine" title="P-Phenetidine"><i>p</i>-phenetidine</a> is at least partly responsible for these effects.<sup id="cite_ref-Kankuri_17-0" class="reference"><a href="#cite_note-Kankuri-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>One notable death that can possibly be attributed to the use of this drug was that of the aviation pioneer <a href="/wiki/Howard_Hughes" title="Howard Hughes">Howard Hughes</a>. He had been using phenacetin extensively for the treatment of <a href="/wiki/Chronic_pain" title="Chronic pain">chronic pain</a>; it was stated during his autopsy that phenacetin use may have been the cause of his <a href="/wiki/Kidney_failure" title="Kidney failure">kidney failure</a>.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Askit_Powders" title="Askit Powders">Askit Powders</a>, a once-popular headache cure on the UK market, have been associated with kidney failure in chronic users due to containing phenacetin until 1966, when they were reformulated to remove it.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="In_popular_culture">In popular culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=8" title="Edit section: In popular culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 1974 episode of the <a href="/wiki/Yorkshire_Television" class="mw-redirect" title="Yorkshire Television">Yorkshire Television</a> series <a href="/wiki/Justice_(1971_TV_series)" title="Justice (1971 TV series)"><i>Justice</i></a>, "Duty of Care", features a court case that resulted from a woman dying of phenacetin poisoning, as a result of taking A.P.C. for five years. This explained that phenacetin caused renal papillary necrosis.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>In the book <i><a href="/wiki/Zen_and_the_Art_of_Motorcycle_Maintenance" title="Zen and the Art of Motorcycle Maintenance">Zen and the Art of Motorcycle Maintenance</a></i> chapter 4, "APCs for headaches" is included in a list of valuable things to take on motorcycle trips.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=9" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Bucetin" title="Bucetin">Bucetin</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Phenacetin&action=edit&section=10" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-canada-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-canada_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-canada_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-canada_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFGralakEnochTayeb2000" class="citation journal cs1">Gralak B, Enoch S, Tayeb G (June 2000). "Anomalous refractive properties of photonic crystals". <i>Journal of the Optical Society of America A</i>. <b>17</b> (6): <span class="nowrap">1012–</span>1020. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2000JOSAA..17.1012G">2000JOSAA..17.1012G</a>. <a href="/wiki/CiteSeerX_(identifier)" class="mw-redirect" title="CiteSeerX (identifier)">CiteSeerX</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://citeseerx.ist.psu.edu/viewdoc/summary?doi=10.1.1.462.8012">10.1.1.462.8012</a></span>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1364%2FJOSAA.17.001012">10.1364/JOSAA.17.001012</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/10850471">10850471</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+the+Optical+Society+of+America+A&rft.atitle=Anomalous+refractive+properties+of+photonic+crystals&rft.volume=17&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1012-%3C%2Fspan%3E1020&rft.date=2000-06&rft_id=https%3A%2F%2Fciteseerx.ist.psu.edu%2Fviewdoc%2Fsummary%3Fdoi%3D10.1.1.462.8012%23id-name%3DCiteSeerX&rft_id=info%3Apmid%2F10850471&rft_id=info%3Adoi%2F10.1364%2FJOSAA.17.001012&rft_id=info%3Abibcode%2F2000JOSAA..17.1012G&rft.aulast=Gralak&rft.aufirst=B&rft.au=Enoch%2C+S&rft.au=Tayeb%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenacetin" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB03783">"Phenacetin"</a>. <i>DrugBank</i><span class="reference-accessdate">. Retrieved <span class="nowrap">28 April</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DrugBank&rft.atitle=Phenacetin&rft_id=https%3A%2F%2Fwww.drugbank.ca%2Fdrugs%2FDB03783&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenacetin" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20140930103207/https://www.fda.gov/downloads/Drugs/DevelopmentApprovalProcess/DevelopmentResources/Over-the-CounterOTCDrugs/StatusofOTCRulemakings/UCM078577.pdf">"Drugs withdrawn from the market containing phenacetin"</a> <span class="cs1-format">(PDF)</span>. Department of Health and Human Services - FDA. 5 October 1983. Archived from <a rel="nofollow" class="external text" href="https://www.fda.gov/downloads/Drugs/DevelopmentApprovalProcess/DevelopmentResources/Over-the-CounterOTCDrugs/StatusofOTCRulemakings/UCM078577.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 30 September 2014.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Drugs+withdrawn+from+the+market+containing+phenacetin&rft.pub=Department+of+Health+and+Human+Services+-+FDA&rft.date=1983-10-05&rft_id=https%3A%2F%2Fwww.fda.gov%2Fdownloads%2FDrugs%2FDevelopmentApprovalProcess%2FDevelopmentResources%2FOver-the-CounterOTCDrugs%2FStatusofOTCRulemakings%2FUCM078577.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenacetin" class="Z3988"></span></span> </li> <li id="cite_note-drugdiscov-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-drugdiscov_4-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSneader2005" class="citation book cs1">Sneader W (2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=jglFsz5EJR8C&pg=PA439"><i>Drug Discovery: A History</i></a>. Hoboken, NJ: Wiley. p. 439. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0471899808" title="Special:BookSources/978-0471899808"><bdi>978-0471899808</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20160818021904/https://books.google.com/books?id=jglFsz5EJR8C&pg=PA439">Archived</a> from the original on 18 August 2016. <q>The eminent clinical pharmacologist Joseph von Mering collaborated with the Bayer Company in a trial of paracetamol in 1893. He found it to be an effective antipyretic and analgesic, but claimed it had a slight tendency to produce <a href="/wiki/Methemoglobinemia" title="Methemoglobinemia">methaemoglobinaemia</a>. This could conceivably have been caused by the contamination of his paracetamol with the 4-aminophenol from which it was synthesised.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Drug+Discovery%3A+A+History&rft.place=Hoboken%2C+NJ&rft.pages=439&rft.pub=Wiley&rft.date=2005&rft.isbn=978-0471899808&rft.aulast=Sneader&rft.aufirst=W&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DjglFsz5EJR8C%26pg%3DPA439&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenacetin" class="Z3988"></span></span> </li> <li id="cite_note-Creese1997-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Creese1997_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Creese1997_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCreese1997" class="citation journal cs1">Creese MR (1997). <a rel="nofollow" class="external text" href="http://www.scs.illinois.edu/~mainzv/HIST/bulletin_open_access/num20/num20%20p42-45.pdf">"Martha Annie Whiteley (1866-1956): Chemist and Editor"</a> <span class="cs1-format">(PDF)</span>. <i>Bulletin for the History of Chemistry</i>. <b>8</b>: <span class="nowrap">42–</span>45.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bulletin+for+the+History+of+Chemistry&rft.atitle=Martha+Annie+Whiteley+%281866-1956%29%3A+Chemist+and+Editor&rft.volume=8&rft.pages=%3Cspan+class%3D%22nowrap%22%3E42-%3C%2Fspan%3E45&rft.date=1997&rft.aulast=Creese&rft.aufirst=MR&rft_id=http%3A%2F%2Fwww.scs.illinois.edu%2F~mainzv%2FHIST%2Fbulletin_open_access%2Fnum20%2Fnum20%2520p42-45.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenacetin" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMorse1878" class="citation journal cs1">Morse HN (1878). <a rel="nofollow" class="external text" href="https://zenodo.org/record/1425148">"Ueber eine neue Darstellungsmethode der Acetylamidophenole"</a>. <i><a href="/wiki/Berichte_der_deutschen_chemischen_Gesellschaft" class="mw-redirect" title="Berichte der deutschen chemischen Gesellschaft">Berichte der deutschen chemischen Gesellschaft</a></i>. <b>11</b> (1): <span class="nowrap">232–</span>233. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.18780110151">10.1002/cber.18780110151</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+deutschen+chemischen+Gesellschaft&rft.atitle=Ueber+eine+neue+Darstellungsmethode+der+Acetylamidophenole&rft.volume=11&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E232-%3C%2Fspan%3E233&rft.date=1878&rft_id=info%3Adoi%2F10.1002%2Fcber.18780110151&rft.aulast=Morse&rft.aufirst=HN&rft_id=https%3A%2F%2Fzenodo.org%2Frecord%2F1425148&rfr_id=info%3Asid%2Fen.wikipedia.org%3APhenacetin" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20081202111801/http://wwwchem.csustan.edu/archive/Phenacetin.htm">"Conversion of Acetaminophen into Phenacetin"</a>. <i>Chemistry Department Master Experiment Archive</i>. <a href="/wiki/California_State_University_Stanislaus" class="mw-redirect" title="California State University Stanislaus">California State University Stanislaus</a>. 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href="https://en.wiktionary.org/wiki/Special:Search/phenacetin" class="extiw" title="wiktionary:Special:Search/phenacetin">phenacetin</a></b></i> in Wiktionary, the free dictionary.</div></div> </div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20120318172218/http://ntp.niehs.nih.gov/INDEX4E62.HTM?objectid=07039573-D7A5-91CA-B2D1FF0D1100CFB8">Carcinogen report from the NIH</a></li> <li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/iarc/suppl7/analgesicmx&phenacetin.html">IARC report</a></li> <li><a rel="nofollow" class="external text" href="http://physchem.ox.ac.uk/MSDS/PH/phenacetin.html">Safety (MSDS) data for phenacetin</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20060924185947/http://physchem.ox.ac.uk/MSDS/PH/phenacetin.html">Archived</a> 2006-09-24 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li></ul> <div class="navbox-styles"><style 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rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Analgesics" title="Template:Analgesics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Analgesics" title="Template talk:Analgesics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Analgesics" title="Special:EditPage/Template:Analgesics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Analgesics_(N02A,_N02B)251" style="font-size:114%;margin:0 4em"><a href="/wiki/Analgesic" title="Analgesic">Analgesics</a> (<a href="/wiki/ATC_code_N02#N02A" title="ATC code N02">N02A</a>, <a href="/wiki/ATC_code_N02#N02B" title="ATC code N02">N02B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid" title="Opioid">Opioids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opiate" title="Opiate">Opiates</a>/<a href="/wiki/Opium" title="Opium">opium</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/Codeine" title="Codeine">Codeine</a><sup>#</sup> <ul><li><a href="/wiki/Codeine/aspirin" class="mw-redirect" title="Codeine/aspirin">+aspirin</a></li> <li><a href="/wiki/Codeine/paracetamol" title="Codeine/paracetamol">+paracetamol</a></li></ul></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a><sup>#</sup> (<a href="/wiki/Morphine/naltrexone" title="Morphine/naltrexone">+naltrexone</a>)</li> <li><a href="/wiki/Opium" title="Opium">Opium</a></li> <li><a href="/wiki/Laudanum" title="Laudanum">Laudanum</a></li> <li><a href="/wiki/Paregoric" title="Paregoric">Paregoric</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Semisynthetic</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/Acetyldihydrocodeine" title="Acetyldihydrocodeine">Acetyldihydrocodeine</a></li> <li><a href="/wiki/Benzylmorphine" title="Benzylmorphine">Benzylmorphine</a></li> <li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a><span class="nowrap"> </span>(<a href="/wiki/Buprenorphine/naloxone" title="Buprenorphine/naloxone">+naloxone</a>)</li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Desomorphine" title="Desomorphine">Desomorphine</a></li> <li><a href="/wiki/Heroin" title="Heroin">Diamorphine (heroin)</a></li> <li><a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">Dihydrocodeine</a><span class="nowrap"> </span>(<a href="/wiki/Co-dydramol" title="Co-dydramol">+paracetamol</a>)</li> <li><a href="/wiki/Dihydromorphine" title="Dihydromorphine">Dihydromorphine</a></li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Ethylmorphine" title="Ethylmorphine">Ethylmorphine</a></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a><span class="nowrap"> </span>(<a href="/wiki/Hydrocodone/paracetamol" title="Hydrocodone/paracetamol">+paracetamol</a>, <a href="/wiki/Hydrocodone/ibuprofen" title="Hydrocodone/ibuprofen">+ibuprofen</a>, <a href="/wiki/Hydrocodone/aspirin" title="Hydrocodone/aspirin">+aspirin</a>)</li> <li><a href="/wiki/Hydromorphinol" title="Hydromorphinol">Hydromorphinol</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/wiki/Metopon" title="Metopon">Metopon</a></li> <li><a href="/wiki/Nalbuphine" title="Nalbuphine">Nalbuphine</a></li> <li><a href="/wiki/Nicocodeine" title="Nicocodeine">Nicocodeine</a></li> <li><a href="/wiki/Nicodicodine" title="Nicodicodine">Nicodicodine</a></li> <li><a href="/wiki/Nicomorphine" title="Nicomorphine">Nicomorphine</a></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a><span class="nowrap"> </span>(<a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">+paracetamol</a>, <a href="/wiki/Oxycodone/aspirin" title="Oxycodone/aspirin">+aspirin</a>, <a href="/wiki/Oxycodone/ibuprofen" title="Oxycodone/ibuprofen">+ibuprofen</a>, <a href="/wiki/Oxycodone/naloxone" title="Oxycodone/naloxone">+naloxone</a>, <a href="/w/index.php?title=Oxycodone/naltrexone&action=edit&redlink=1" class="new" title="Oxycodone/naltrexone (page does not exist)">+naltrexone</a>)</li> <li><a href="/wiki/Oxymorphone" title="Oxymorphone">Oxymorphone</a></li> <li><a href="/wiki/Papaveretum" title="Papaveretum">Papaveretum</a></li> <li><a href="/wiki/Thebacon" title="Thebacon">Thebacon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthetic</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/Alfentanil" title="Alfentanil">Alfentanil</a></li> <li><a href="/wiki/Prodine" title="Prodine">Alphaprodine</a></li> <li><a href="/wiki/Anileridine" title="Anileridine">Anileridine</a></li> <li><a href="/wiki/Bezitramide" title="Bezitramide">Bezitramide</a></li> <li><a href="/wiki/Carfentanil" title="Carfentanil">Carfentanil</a></li> <li><a href="/wiki/Dextromoramide" title="Dextromoramide">Dextromoramide</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dezocine" title="Dezocine">Dezocine</a></li> <li><a href="/wiki/Dimenoxadol" title="Dimenoxadol">Dimenoxadol</a></li> <li><a href="/wiki/Dipipanone" title="Dipipanone">Dipipanone</a></li> <li><a href="/wiki/Ethoheptazine" title="Ethoheptazine">Ethoheptazine</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a><sup>#</sup> (<a href="/wiki/Fentanyl/fluanisone" title="Fentanyl/fluanisone">+fluanisone</a>)</li> <li><a href="/wiki/Ketobemidone" title="Ketobemidone">Ketobemidone</a></li> <li><a href="/wiki/Lofentanil" title="Lofentanil">Lofentanil</a></li> <li><a href="/wiki/Meptazinol" title="Meptazinol">Meptazinol</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a><sup>#</sup></li> <li><a href="/wiki/NFEPP" title="NFEPP">NFEPP</a></li> <li><a href="/wiki/Norpipanone" title="Norpipanone">Norpipanone</a></li> <li><a href="/wiki/Oliceridine" title="Oliceridine">Oliceridine</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Phenadoxone" title="Phenadoxone">Phenadoxone</a></li> <li><a href="/wiki/Phenazocine" title="Phenazocine">Phenazocine</a></li> <li><a href="/wiki/Phenoperidine" title="Phenoperidine">Phenoperidine</a></li> <li><a href="/wiki/Piminodine" title="Piminodine">Piminodine</a></li> <li><a href="/wiki/Piritramide" title="Piritramide">Piritramide</a></li> <li><a href="/wiki/Proheptazine" title="Proheptazine">Proheptazine</a></li> <li><a href="/wiki/Propiram" title="Propiram">Propiram</a></li> <li><a href="/wiki/Remifentanil" title="Remifentanil">Remifentanil</a></li> <li><a href="/wiki/Sufentanil" title="Sufentanil">Sufentanil</a></li> <li><a href="/wiki/Tapentadol" title="Tapentadol">Tapentadol</a></li> <li><a href="/wiki/Tilidine" title="Tilidine">Tilidine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a><span class="nowrap"> </span>(<a href="/wiki/Celecoxib/tramadol" title="Celecoxib/tramadol">+celecoxib</a>, <a href="/wiki/Tramadol/paracetamol" title="Tramadol/paracetamol">+paracetamol</a>)</li> <li><a href="/wiki/Viminol" title="Viminol">Viminol</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/Paracetamol" title="Paracetamol">Paracetamol</a>-type</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetanilide" title="Acetanilide">Acetanilide</a><sup>‡</sup></li> <li><a href="/wiki/Bucetin" title="Bucetin">Bucetin</a><sup>‡</sup></li> <li><a href="/w/index.php?title=Butacetin&action=edit&redlink=1" class="new" title="Butacetin (page does not exist)">Butacetin</a><sup>‡</sup></li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a><sup>#</sup> <ul><li><a href="/wiki/Aspirin/paracetamol/caffeine" title="Aspirin/paracetamol/caffeine">+aspirin/caffeine</a></li> <li><a href="/wiki/Codeine/paracetamol" title="Codeine/paracetamol">+codeine</a></li> <li><a href="/wiki/Hydrocodone/paracetamol" title="Hydrocodone/paracetamol">+hydrocodone</a></li> <li><a href="/wiki/Ibuprofen/paracetamol" title="Ibuprofen/paracetamol">+ibuprofen</a></li> <li><a href="/wiki/Paracetamol/metoclopramide" title="Paracetamol/metoclopramide">+metoclopramide</a></li> <li><a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">+oxycodone</a></li> <li><a href="/wiki/Propyphenazone/paracetamol/caffeine" title="Propyphenazone/paracetamol/caffeine">+propyphenazone/caffeine</a></li> <li><a href="/wiki/Tramadol/paracetamol" title="Tramadol/paracetamol">+tramadol</a></li></ul></li> <li><a href="/w/index.php?title=Parapropamol&action=edit&redlink=1" class="new" title="Parapropamol (page does not exist)">Parapropamol</a><sup>‡</sup></li> <li><a class="mw-selflink selflink">Phenacetin</a><sup>‡</sup></li> <li><a href="/wiki/Propacetamol" title="Propacetamol">Propacetamol</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nonsteroidal_anti-inflammatory_drug" title="Nonsteroidal anti-inflammatory drug">NSAIDs</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Propionates</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/Benoxaprofen" title="Benoxaprofen">Benoxaprofen</a> <sup>‡</sup></li> <li><a href="/wiki/Fenoprofen" title="Fenoprofen">Fenoprofen</a></li> <li><a href="/wiki/Flurbiprofen" title="Flurbiprofen">Flurbiprofen</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a><sup>#</sup><span class="nowrap"> </span>(<a href="/wiki/Dexibuprofen" title="Dexibuprofen">Dexibuprofen</a>)<span class="nowrap"> </span>(<a href="/wiki/Ibuprofen/paracetamol" title="Ibuprofen/paracetamol">+paracetamol</a>)</li> <li><a href="/wiki/Ketoprofen" title="Ketoprofen">Ketoprofen</a><span class="nowrap"> </span>(<a href="/wiki/Dexketoprofen" title="Dexketoprofen">Dexketoprofen</a>)</li> <li><a href="/wiki/Loxoprofen" title="Loxoprofen">Loxoprofen</a></li> <li><a href="/wiki/Naproxen" title="Naproxen">Naproxen</a></li> <li><a href="/wiki/Oxaprozin" title="Oxaprozin">Oxaprozin</a></li> <li><a href="/wiki/Suprofen" title="Suprofen">Suprofen</a></li> <li><a href="/wiki/Tiaprofenic_acid" title="Tiaprofenic acid">Tiaprofenic acid</a></li> <li><a href="/wiki/Zaltoprofen" title="Zaltoprofen">Zaltoprofen</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxicams</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/Isoxicam" title="Isoxicam">Isoxicam</a></li> <li><a href="/wiki/Lornoxicam" title="Lornoxicam">Lornoxicam</a></li> <li><a href="/wiki/Meloxicam" title="Meloxicam">Meloxicam</a></li> <li><a href="/wiki/Piroxicam" title="Piroxicam">Piroxicam</a></li> <li><a href="/wiki/Tenoxicam" title="Tenoxicam">Tenoxicam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Acetates</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/Acemetacin" title="Acemetacin">Acemetacin</a></li> <li><a href="/wiki/Bromfenac" title="Bromfenac">Bromfenac</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></li> <li><a href="/wiki/Etodolac" title="Etodolac">Etodolac</a></li> <li><a href="/wiki/Indometacin" title="Indometacin">Indometacin</a><span class="nowrap"> </span>(<a href="/wiki/Indometacin_farnesil" title="Indometacin farnesil">Indometacin farnesil</a>)</li> <li><a href="/wiki/Ketorolac" title="Ketorolac">Ketorolac</a></li> <li><a href="/wiki/Sulindac" title="Sulindac">Sulindac</a></li> <li><a href="/wiki/Tolmetin" title="Tolmetin">Tolmetin</a></li> <li><a href="/wiki/Zomepirac" title="Zomepirac">Zomepirac</a> <sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/COX-2_inhibitor" class="mw-redirect" title="COX-2 inhibitor">COX-2 inhibitors</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/Celecoxib" title="Celecoxib">Celecoxib</a><span class="nowrap"> </span>(<a href="/wiki/Celecoxib/tramadol" title="Celecoxib/tramadol">+tramadol</a>)</li> <li><a href="/wiki/Etoricoxib" title="Etoricoxib">Etoricoxib</a></li> <li><a href="/wiki/Lumiracoxib" title="Lumiracoxib">Lumiracoxib</a> <sup>‡</sup></li> <li><a href="/wiki/Parecoxib" title="Parecoxib">Parecoxib</a></li> <li><a href="/wiki/Rofecoxib" title="Rofecoxib">Rofecoxib</a> <sup>‡</sup></li> <li><a href="/wiki/Valdecoxib" title="Valdecoxib">Valdecoxib</a> <sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Fenamic_acid" title="Fenamic acid">Fenamates</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/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylates</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/Aspirin" title="Aspirin">Aspirin (acetylsalicylic acid)</a><sup>#</sup> (<a href="/wiki/Aspirin/paracetamol/caffeine" title="Aspirin/paracetamol/caffeine">+paracetamol/caffeine</a>)</li> <li><a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Benorilate" title="Benorilate">Benorylate</a></li> <li><a href="/wiki/Carbasalate_calcium" title="Carbasalate calcium">Carbasalate calcium</a></li> <li><a href="/wiki/Choline_salicylate" class="mw-redirect" title="Choline salicylate">Choline salicylate</a></li> <li><a href="/wiki/Diflunisal" title="Diflunisal">Diflunisal</a></li> <li><a href="/wiki/Dipyrocetyl" title="Dipyrocetyl">Dipyrocetyl</a></li> <li><a href="/wiki/Ethenzamide" title="Ethenzamide">Ethenzamide</a></li> <li><a href="/wiki/Guacetisal" title="Guacetisal">Guacetisal</a></li> <li><a href="/wiki/Imidazole_salicylate" title="Imidazole salicylate">Imidazole salicylate</a></li> <li><a href="/wiki/Magnesium_salicylate" title="Magnesium salicylate">Magnesium salicylate</a></li> <li><a href="/wiki/Morpholine_salicylate" title="Morpholine salicylate">Morpholine salicylate</a></li> <li><a href="/wiki/Potassium_salicylate" title="Potassium salicylate">Potassium salicylate</a></li> <li><a href="/wiki/Salicin" title="Salicin">Salicin</a></li> <li><a href="/wiki/Salicylamide" title="Salicylamide">Salicylamide</a></li> <li><a href="/wiki/Salsalate" title="Salsalate">Salsalate</a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a></li> <li><a href="/wiki/Wintergreen" title="Wintergreen">Wintergreen</a><span class="nowrap"> </span>(<a href="/wiki/Methyl_salicylate" title="Methyl salicylate">methyl salicylate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrazolone" title="Pyrazolone">Pyrazolones</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/Aminophenazone" title="Aminophenazone">Aminophenazone</a><sup>‡</sup></li> <li><a href="/wiki/Ampyrone" title="Ampyrone">Ampyrone</a></li> <li><a href="/wiki/Metamizole" title="Metamizole">Metamizole (dipyrone)</a></li> <li><a href="/wiki/Nifenazone" title="Nifenazone">Nifenazone</a></li> <li><a href="/wiki/Phenazone" title="Phenazone">Phenazone</a></li> <li><a href="/wiki/Propyphenazone" title="Propyphenazone">Propyphenazone</a><span class="nowrap"> </span>(<a href="/wiki/Propyphenazone/paracetamol/caffeine" title="Propyphenazone/paracetamol/caffeine">+paracetamol/caffeine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">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><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Floctafenine" title="Floctafenine">Floctafenine</a></li> <li><a href="/wiki/Glafenine" title="Glafenine">Glafenine</a></li> <li><a href="/wiki/Nabumetone" title="Nabumetone">Nabumetone</a></li> <li><a href="/wiki/Nimesulide" title="Nimesulide">Nimesulide</a></li> <li><a href="/wiki/Proquazone" title="Proquazone">Proquazone</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/Cannabinoid" title="Cannabinoid">Cannabinoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">Cannabis</a></li> <li><a href="/wiki/Nabilone" title="Nabilone">Nabilone</a></li> <li><a href="/wiki/Nabiximols" title="Nabiximols">Nabiximols</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol (dronabinol)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Channel_modulator" title="Channel modulator">Ion channel<br />modulators</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Calcium blockers</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/Alcohol_(drug)" title="Alcohol (drug)">Alcohol (ethanol)</a></li> <li><a href="/wiki/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Gabapentin_enacarbil" title="Gabapentin enacarbil">Gabapentin enacarbil</a></li> <li><a href="/wiki/Leconotide" title="Leconotide">Leconotide</a></li> <li><a href="/wiki/Mirogabalin" title="Mirogabalin">Mirogabalin</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a></li> <li><a href="/wiki/Ziconotide" title="Ziconotide">Ziconotide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Sodium blockers</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/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Lacosamide" title="Lacosamide">Lacosamide</a></li> <li><a href="/wiki/Local_anesthetic" title="Local anesthetic">Local anesthetics</a> (e.g., <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Lidocaine" title="Lidocaine">lidocaine</a>)</li> <li><a href="/wiki/Mexiletine" title="Mexiletine">Mexiletine</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a><sup>#</sup>)</li></ul> <ul><li><i>Na<sub>v</sub>1.7/1.8-selective:</i> <a href="/wiki/DSP-2230" title="DSP-2230">DSP-2230</a><sup>§</sup></li> <li><a href="/wiki/Funapide" title="Funapide">Funapide</a><sup>§</sup></li> <li><a href="/wiki/PF-05089771" title="PF-05089771">PF-05089771</a><sup>§</sup></li> <li><a href="/wiki/Suzetrigine" title="Suzetrigine">Suzetrigine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium openers</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/Flupirtine" title="Flupirtine">Flupirtine</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Muscle_relaxant" title="Muscle relaxant">Myorelaxants</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Chlorzoxazone" title="Chlorzoxazone">Chlorzoxazone</a></li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/wiki/Mephenoxalone" title="Mephenoxalone">Mephenoxalone</a></li> <li><a href="/wiki/Methocarbamol" title="Methocarbamol">Methocarbamol</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Analgecine" title="Analgecine">Analgecine</a></li> <li><a href="/wiki/Analgesic_adjuvant" title="Analgesic adjuvant">Analgesic adjuvant</a></li> <li><a href="/wiki/Bedinvetmab" title="Bedinvetmab">Bedinvetmab</a></li> <li><a href="/wiki/Camphor" title="Camphor">Camphor</a></li> <li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Frunevetmab" title="Frunevetmab">Frunevetmab</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Phenazopyridine" title="Phenazopyridine">Phenazopyridine</a></li> <li><a href="/wiki/Proglumide" title="Proglumide">Proglumide</a></li> <li><a href="/wiki/Rimazolium" title="Rimazolium">Rimazolium</a></li> <li><a href="/wiki/Tanezumab" title="Tanezumab">Tanezumab</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Prostanoid_signaling_modulators402" 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:Prostanoid_signaling_modulators" title="Template:Prostanoid signaling modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Prostanoid_signaling_modulators" title="Template talk:Prostanoid signaling modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Prostanoid_signaling_modulators" title="Special:EditPage/Template:Prostanoid signaling modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Prostanoid_signaling_modulators402" style="font-size:114%;margin:0 4em"><a href="/wiki/Prostanoid" title="Prostanoid">Prostanoid</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><br /><small>(<a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">ligands</a>)</small></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:5em;;text-align:center;"><a href="/wiki/Prostaglandin_D2_receptor" title="Prostaglandin D2 receptor"><abbr title="Prostaglandin D2 receptor">DP (D<sub>2</sub>)</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 Prostaglandin D2 receptor</span></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:5em;;text-align:center;"><a href="/wiki/Prostaglandin_D2_receptor_1" class="mw-redirect" title="Prostaglandin D2 receptor 1"><abbr title="Prostaglandin D2 receptor 1">DP<sub>1</sub></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 Prostaglandin D2 receptor 1</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">Prostaglandin D<sub>2</sub></a></li> <li><a href="/wiki/Treprostinil" title="Treprostinil">Treprostinil</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=Asapiprant&action=edit&redlink=1" class="new" title="Asapiprant (page does not exist)">Asapiprant</a></li> <li><a href="/wiki/Laropiprant" title="Laropiprant">Laropiprant</a></li> <li><a href="/w/index.php?title=Vidupiprant&action=edit&redlink=1" class="new" title="Vidupiprant (page does not exist)">Vidupiprant</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_D2_receptor_2" class="mw-redirect" title="Prostaglandin D2 receptor 2"><abbr title="Prostaglandin D2 receptor 2">DP<sub>2</sub></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 Prostaglandin D2 receptor 2</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Indometacin" title="Indometacin">Indometacin</a></li> <li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">Prostaglandin D<sub>2</sub></a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=ADC-3680&action=edit&redlink=1" class="new" title="ADC-3680 (page does not exist)">ADC-3680</a></li> <li><a href="/w/index.php?title=AZD-1981&action=edit&redlink=1" class="new" title="AZD-1981 (page does not exist)">AZD-1981</a></li> <li><a href="/w/index.php?title=Bay_U3405&action=edit&redlink=1" class="new" title="Bay U3405 (page does not exist)">Bay U3405</a></li> <li><a href="/wiki/Fevipiprant" title="Fevipiprant">Fevipiprant</a></li> <li><a href="/w/index.php?title=MK-1029&action=edit&redlink=1" class="new" title="MK-1029 (page does not exist)">MK-1029</a></li> <li><a href="/w/index.php?title=MK-7246&action=edit&redlink=1" class="new" title="MK-7246 (page does not exist)">MK-7246</a></li> <li><a href="/w/index.php?title=QAV-680&action=edit&redlink=1" class="new" title="QAV-680 (page does not exist)">QAV-680</a></li> <li><a href="/wiki/Ramatroban" title="Ramatroban">Ramatroban</a></li> <li><a href="/wiki/Setipiprant" title="Setipiprant">Setipiprant</a></li> <li><a href="/w/index.php?title=Timapiprant&action=edit&redlink=1" class="new" title="Timapiprant (page does not exist)">Timapiprant</a></li> <li><a href="/w/index.php?title=TM30089&action=edit&redlink=1" class="new" title="TM30089 (page does not exist)">TM30089</a></li> <li><a href="/w/index.php?title=Vidupiprant&action=edit&redlink=1" class="new" title="Vidupiprant (page does not exist)">Vidupiprant</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_E2_receptor" title="Prostaglandin E2 receptor"><abbr title="Prostaglandin E2 receptor">EP (E<sub>2</sub>)</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 Prostaglandin E2 receptor</span></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:5em;;text-align:center;"><a href="/wiki/Prostaglandin_EP1_receptor" title="Prostaglandin EP1 receptor"><abbr title="Prostaglandin EP1 receptor">EP<sub>1</sub></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 Prostaglandin EP1 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Beraprost" title="Beraprost">Beraprost</a></li> <li><a href="/wiki/Enprostil" title="Enprostil">Enprostil</a></li> <li><a href="/wiki/Iloprost" title="Iloprost">Iloprost (ciloprost)</a></li> <li><a href="/wiki/Latanoprost" title="Latanoprost">Latanoprost</a></li> <li><a href="/wiki/Lubiprostone" title="Lubiprostone">Lubiprostone</a></li> <li><a href="/wiki/Misoprostol" title="Misoprostol">Misoprostol</a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">Prostaglandin E<sub>2</sub> (dinoprostone)</a></li> <li><a href="/wiki/Sulprostone" title="Sulprostone">Sulprostone</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=AH-6809&action=edit&redlink=1" class="new" title="AH-6809 (page does not exist)">AH-6809</a></li> <li><a href="/w/index.php?title=ONO-8130&action=edit&redlink=1" class="new" title="ONO-8130 (page does not exist)">ONO-8130</a></li> <li><a href="/w/index.php?title=SC-19220&action=edit&redlink=1" class="new" title="SC-19220 (page does not exist)">SC-19220</a></li> <li><a href="/w/index.php?title=SC-51089&action=edit&redlink=1" class="new" title="SC-51089 (page does not exist)">SC-51089</a></li> <li><a href="/w/index.php?title=SC-51322&action=edit&redlink=1" class="new" title="SC-51322 (page does not exist)">SC-51322</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_EP2_receptor" title="Prostaglandin EP2 receptor"><abbr title="Prostaglandin EP2 receptor">EP<sub>2</sub></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 Prostaglandin EP2 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=Butaprost&action=edit&redlink=1" class="new" title="Butaprost (page does not exist)">Butaprost</a></li> <li><a href="/wiki/Misoprostol" title="Misoprostol">Misoprostol</a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">Prostaglandin E<sub>2</sub> (dinoprostone)</a></li> <li><a href="/wiki/Treprostinil" title="Treprostinil">Treprostinil</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=AH-6809&action=edit&redlink=1" class="new" title="AH-6809 (page does not exist)">AH-6809</a></li> <li><a href="/w/index.php?title=PF-04418948&action=edit&redlink=1" class="new" title="PF-04418948 (page does not exist)">PF-04418948</a></li> <li><a href="/w/index.php?title=TG_4-155&action=edit&redlink=1" class="new" title="TG 4-155 (page does not exist)">TG 4-155</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_EP3_receptor" title="Prostaglandin EP3 receptor"><abbr title="Prostaglandin EP3 receptor">EP<sub>3</sub></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 Prostaglandin EP3 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Beraprost" title="Beraprost">Beraprost</a></li> <li><a href="/w/index.php?title=Carbacyclin&action=edit&redlink=1" class="new" title="Carbacyclin (page does not exist)">Carbacyclin</a></li> <li><a href="/w/index.php?title=Cicaprost&action=edit&redlink=1" class="new" title="Cicaprost (page does not exist)">Cicaprost</a></li> <li><a href="/wiki/Enprostil" title="Enprostil">Enprostil</a></li> <li><a href="/wiki/Iloprost" title="Iloprost">Iloprost (ciloprost)</a></li> <li><a href="/w/index.php?title=Isocarbacyclin&action=edit&redlink=1" class="new" title="Isocarbacyclin (page does not exist)">Isocarbacyclin</a></li> <li><a href="/wiki/Latanoprost" title="Latanoprost">Latanoprost</a></li> <li><a href="/wiki/Misoprostol" title="Misoprostol">Misoprostol</a></li> <li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">Prostaglandin D<sub>2</sub></a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">Prostaglandin E<sub>2</sub> (dinoprostone)</a></li> <li><a href="/w/index.php?title=Remiprostol&action=edit&redlink=1" class="new" title="Remiprostol (page does not exist)">Remiprostol</a></li> <li><a href="/wiki/Ricinoleic_acid" title="Ricinoleic acid">Ricinoleic acid</a></li> <li><a href="/wiki/Sulprostone" title="Sulprostone">Sulprostone</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=L-798106&action=edit&redlink=1" class="new" title="L-798106 (page does not exist)">L-798106</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_EP4_receptor" title="Prostaglandin EP4 receptor"><abbr title="Prostaglandin EP4 receptor">EP<sub>4</sub></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 Prostaglandin EP4 receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Lubiprostone" title="Lubiprostone">Lubiprostone</a></li> <li><a href="/wiki/Misoprostol" title="Misoprostol">Misoprostol</a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">Prostaglandin E<sub>2</sub> (dinoprostone)</a></li> <li><a href="/w/index.php?title=TCS-2510&action=edit&redlink=1" class="new" title="TCS-2510 (page does not exist)">TCS-2510</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/Grapiprant" title="Grapiprant">Grapiprant</a></li> <li><a href="/w/index.php?title=GW-627368&action=edit&redlink=1" class="new" title="GW-627368 (page does not exist)">GW-627368</a></li> <li><a href="/w/index.php?title=L-161982&action=edit&redlink=1" class="new" title="L-161982 (page does not exist)">L-161982</a></li> <li><a href="/w/index.php?title=ONO-AE3-208&action=edit&redlink=1" class="new" title="ONO-AE3-208 (page does not exist)">ONO-AE3-208</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;">Unsorted</th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=16,16-Dimethyl_Prostaglandin_E2&action=edit&redlink=1" class="new" title="16,16-Dimethyl Prostaglandin E2 (page does not exist)">16,16-Dimethyl Prostaglandin E<sub>2</sub></a></li> <li><a href="/w/index.php?title=Aganepag&action=edit&redlink=1" class="new" title="Aganepag (page does not exist)">Aganepag</a></li> <li><a href="/wiki/Carboprost" title="Carboprost">Carboprost</a></li> <li><a href="/w/index.php?title=Evatanepag&action=edit&redlink=1" class="new" title="Evatanepag (page does not exist)">Evatanepag</a></li> <li><a href="/wiki/Gemeprost" title="Gemeprost">Gemeprost</a></li> <li><a href="/w/index.php?title=Nocloprost&action=edit&redlink=1" class="new" title="Nocloprost (page does not exist)">Nocloprost</a></li> <li><a href="/wiki/Omidenepag" title="Omidenepag">Omidenepag</a></li> <li><a href="/wiki/Prostaglandin_F2%CE%B1" class="mw-redirect" title="Prostaglandin F2α">Prostaglandin F<sub>2α</sub> (dinoprost)</a></li> <li><a href="/w/index.php?title=Simenepag&action=edit&redlink=1" class="new" title="Simenepag (page does not exist)">Simenepag</a></li> <li><a href="/w/index.php?title=Taprenepag&action=edit&redlink=1" class="new" title="Taprenepag (page does not exist)">Taprenepag</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_F_receptor" title="Prostaglandin F receptor"><abbr title="Prostaglandin F receptor">FP (F<sub>2α</sub>)</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 Prostaglandin F receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/wiki/Alfaprostol" title="Alfaprostol">Alfaprostol</a></li> <li><a href="/wiki/Bimatoprost" title="Bimatoprost">Bimatoprost</a></li> <li><a href="/wiki/Carboprost" title="Carboprost">Carboprost</a></li> <li><a href="/wiki/Cloprostenol" title="Cloprostenol">Cloprostenol</a></li> <li><a href="/wiki/Enprostil" title="Enprostil">Enprostil</a></li> <li><a href="/w/index.php?title=Fluprostenol&action=edit&redlink=1" class="new" title="Fluprostenol (page does not exist)">Fluprostenol</a></li> <li><a href="/wiki/Latanoprost" title="Latanoprost">Latanoprost</a></li> <li><a href="/wiki/Prostaglandin_D2" title="Prostaglandin D2">Prostaglandin D<sub>2</sub></a></li> <li><a href="/wiki/Prostaglandin_F2%CE%B1" class="mw-redirect" title="Prostaglandin F2α">Prostaglandin F<sub>2α</sub> (dinoprost)</a></li> <li><a href="/w/index.php?title=Sulotroban&action=edit&redlink=1" class="new" title="Sulotroban (page does not exist)">Sulotroban</a></li> <li><a href="/wiki/Tafluprost" title="Tafluprost">Tafluprost</a></li> <li><a href="/wiki/Travoprost" title="Travoprost">Travoprost</a></li> <li><a href="/wiki/Unoprostone" title="Unoprostone">Unoprostone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostacyclin_receptor" title="Prostacyclin receptor"><abbr title="Prostacyclin receptor">IP (I<sub>2</sub>)</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 Prostacyclin receptor</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=ACT-333679&action=edit&redlink=1" class="new" title="ACT-333679 (page does not exist)">ACT-333679</a></li> <li><a href="/w/index.php?title=AFP-07&action=edit&redlink=1" class="new" title="AFP-07 (page does not exist)">AFP-07</a></li> <li><a href="/wiki/Beraprost" title="Beraprost">Beraprost</a></li> <li><a href="/w/index.php?title=BMY-45778&action=edit&redlink=1" class="new" title="BMY-45778 (page does not exist)">BMY-45778</a></li> <li><a href="/w/index.php?title=Carbacyclin&action=edit&redlink=1" class="new" title="Carbacyclin (page does not exist)">Carbacyclin</a></li> <li><a href="/w/index.php?title=Cicaprost&action=edit&redlink=1" class="new" title="Cicaprost (page does not exist)">Cicaprost</a></li> <li><a href="/wiki/Iloprost" title="Iloprost">Iloprost (ciloprost)</a></li> <li><a href="/w/index.php?title=Isocarbacyclin&action=edit&redlink=1" class="new" title="Isocarbacyclin (page does not exist)">Isocarbacyclin</a></li> <li><a href="/w/index.php?title=MRE-269&action=edit&redlink=1" class="new" title="MRE-269 (page does not exist)">MRE-269</a></li> <li><a href="/w/index.php?title=NS-304&action=edit&redlink=1" class="new" title="NS-304 (page does not exist)">NS-304</a></li> <li><a href="/wiki/Prostacyclin" title="Prostacyclin">Prostacyclin (prostaglandin I<sub>2</sub>, epoprostenol)</a></li> <li><a href="/wiki/Prostaglandin_E1" title="Prostaglandin E1">Prostaglandin E<sub>1</sub> (alprostadil)</a></li> <li><a href="/w/index.php?title=Ralinepag&action=edit&redlink=1" class="new" title="Ralinepag (page does not exist)">Ralinepag</a></li> <li><a href="/wiki/Selexipag" title="Selexipag">Selexipag</a></li> <li><a href="/w/index.php?title=Taprostene&action=edit&redlink=1" class="new" title="Taprostene (page does not exist)">Taprostene</a></li> <li><a href="/w/index.php?title=TRA-418&action=edit&redlink=1" class="new" title="TRA-418 (page does not exist)">TRA-418</a></li> <li><a href="/wiki/Treprostinil" title="Treprostinil">Treprostinil</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/w/index.php?title=RO1138452&action=edit&redlink=1" class="new" title="RO1138452 (page does not exist)">RO1138452</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Thromboxane_receptor" title="Thromboxane receptor"><abbr title="Thromboxane receptor">TP (TX<sub>A2</sub>)</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 Thromboxane receptor</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Agonists:</b> <a href="/w/index.php?title=Carbocyclic_thromboxane_A2&action=edit&redlink=1" class="new" title="Carbocyclic thromboxane A2 (page does not exist)">Carbocyclic thromboxane A<sub>2</sub></a></li> <li><a href="/w/index.php?title=I-BOP&action=edit&redlink=1" class="new" title="I-BOP (page does not exist)">I-BOP</a></li> <li><a href="/wiki/Thromboxane_A2" title="Thromboxane A2">Thromboxane A<sub>2</sub></a></li> <li><a href="/wiki/U-46619" class="mw-redirect" title="U-46619">U-46619</a></li> <li><a href="/w/index.php?title=Vapiprost&action=edit&redlink=1" class="new" title="Vapiprost (page does not exist)">Vapiprost</a></li></ul> <ul><li><b>Antagonists:</b> <a href="/wiki/12-Hydroxyeicosatetraenoic_acid" title="12-Hydroxyeicosatetraenoic acid">12-HETE</a></li> <li><a href="/w/index.php?title=13-APA&action=edit&redlink=1" class="new" title="13-APA (page does not exist)">13-APA</a></li> <li><a href="/w/index.php?title=AA-2414&action=edit&redlink=1" class="new" title="AA-2414 (page does not exist)">AA-2414</a></li> <li><a href="/wiki/Argatroban" title="Argatroban">Argatroban</a></li> <li><a href="/w/index.php?title=Bay_U3405&action=edit&redlink=1" class="new" title="Bay U3405 (page does not exist)">Bay U3405</a></li> <li><a href="/w/index.php?title=BMS-180,291&action=edit&redlink=1" class="new" title="BMS-180,291 (page does not exist)">BMS-180,291</a></li> <li><a href="/w/index.php?title=Daltroban&action=edit&redlink=1" class="new" title="Daltroban (page does not exist)">Daltroban</a></li> <li><a href="/w/index.php?title=Domitroban&action=edit&redlink=1" class="new" title="Domitroban (page does not exist)">Domitroban</a></li> <li><a href="/w/index.php?title=EP-045&action=edit&redlink=1" class="new" title="EP-045 (page does not exist)">EP-045</a></li> <li><a href="/w/index.php?title=GR-32191&action=edit&redlink=1" class="new" title="GR-32191 (page does not exist)">GR-32191</a></li> <li><a href="/w/index.php?title=ICI-185282&action=edit&redlink=1" class="new" title="ICI-185282 (page does not exist)">ICI-185282</a></li> <li><a href="/w/index.php?title=ICI-192605&action=edit&redlink=1" class="new" title="ICI-192605 (page does not exist)">ICI-192605</a></li> <li><a href="/wiki/Ifetroban" title="Ifetroban">Ifetroban</a></li> <li><a href="/w/index.php?title=Imitrodast&action=edit&redlink=1" class="new" title="Imitrodast (page does not exist)">Imitrodast</a></li> <li><a href="/w/index.php?title=L-655240&action=edit&redlink=1" class="new" title="L-655240 (page does not exist)">L-655240</a></li> <li><a href="/w/index.php?title=L-670596&action=edit&redlink=1" class="new" title="L-670596 (page does not exist)">L-670596</a></li> <li><a href="/w/index.php?title=Linotroban&action=edit&redlink=1" class="new" title="Linotroban (page does not exist)">Linotroban</a></li> <li><a href="/w/index.php?title=Mipitroban&action=edit&redlink=1" class="new" title="Mipitroban (page does not exist)">Mipitroban</a></li> <li><a href="/w/index.php?title=ONO-3708&action=edit&redlink=1" class="new" title="ONO-3708 (page does not exist)">ONO-3708</a></li> <li><a href="/w/index.php?title=ONO-11120&action=edit&redlink=1" class="new" title="ONO-11120 (page does not exist)">ONO-11120</a></li> <li><a href="/wiki/Picotamide" title="Picotamide">Picotamide</a></li> <li><a href="/w/index.php?title=Pinane_thromboxane_A2&action=edit&redlink=1" class="new" title="Pinane thromboxane A2 (page does not exist)">Pinane thromboxane A<sub>2</sub></a></li> <li><a href="/wiki/Ramatroban" title="Ramatroban">Ramatroban</a></li> <li><a href="/w/index.php?title=Ridogrel&action=edit&redlink=1" class="new" title="Ridogrel (page does not exist)">Ridogrel</a></li> <li><a href="/w/index.php?title=S-145&action=edit&redlink=1" class="new" title="S-145 (page does not exist)">S-145</a></li> <li><a href="/w/index.php?title=Samixogrel&action=edit&redlink=1" class="new" title="Samixogrel (page does not exist)">Samixogrel</a></li> <li><a href="/wiki/Seratrodast" title="Seratrodast">Seratrodast</a></li> <li><a href="/w/index.php?title=SQ-28,668&action=edit&redlink=1" class="new" title="SQ-28,668 (page does not exist)">SQ-28,668</a></li> <li><a href="/w/index.php?title=SQ-29,548&action=edit&redlink=1" class="new" title="SQ-29,548 (page does not exist)">SQ-29,548</a></li> <li><a href="/w/index.php?title=Sulotroban&action=edit&redlink=1" class="new" title="Sulotroban (page does not exist)">Sulotroban</a></li> <li><a href="/wiki/Terbogrel" title="Terbogrel">Terbogrel</a></li> <li><a href="/wiki/Terutroban" title="Terutroban">Terutroban</a></li> <li><a href="/w/index.php?title=TRA-418&action=edit&redlink=1" class="new" title="TRA-418 (page does not exist)">TRA-418</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;">Unsorted</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=Arbaprostil&action=edit&redlink=1" class="new" title="Arbaprostil (page does not exist)">Arbaprostil</a></li> <li><a href="/w/index.php?title=Ataprost&action=edit&redlink=1" class="new" title="Ataprost (page does not exist)">Ataprost</a></li> <li><a href="/w/index.php?title=Ciprostene&action=edit&redlink=1" class="new" title="Ciprostene (page does not exist)">Ciprostene</a></li> <li><a href="/w/index.php?title=Clinprost&action=edit&redlink=1" class="new" title="Clinprost (page does not exist)">Clinprost</a></li> <li><a href="/w/index.php?title=Cobiprostone&action=edit&redlink=1" class="new" title="Cobiprostone (page does not exist)">Cobiprostone</a></li> <li><a href="/w/index.php?title=Delprostenate&action=edit&redlink=1" class="new" title="Delprostenate (page does not exist)">Delprostenate</a></li> <li><a href="/w/index.php?title=Deprostil&action=edit&redlink=1" class="new" title="Deprostil (page does not exist)">Deprostil</a></li> <li><a href="/w/index.php?title=Dimoxaprost&action=edit&redlink=1" class="new" title="Dimoxaprost (page does not exist)">Dimoxaprost</a></li> <li><a href="/w/index.php?title=Doxaprost&action=edit&redlink=1" class="new" title="Doxaprost (page does not exist)">Doxaprost</a></li> <li><a href="/w/index.php?title=Ecraprost&action=edit&redlink=1" class="new" title="Ecraprost (page does not exist)">Ecraprost</a></li> <li><a href="/w/index.php?title=Eganoprost&action=edit&redlink=1" class="new" title="Eganoprost (page does not exist)">Eganoprost</a></li> <li><a href="/w/index.php?title=Enisoprost&action=edit&redlink=1" class="new" title="Enisoprost (page does not exist)">Enisoprost</a></li> <li><a href="/w/index.php?title=Eptaloprost&action=edit&redlink=1" class="new" title="Eptaloprost (page does not exist)">Eptaloprost</a></li> <li><a href="/w/index.php?title=Esuberaprost&action=edit&redlink=1" class="new" title="Esuberaprost (page does not exist)">Esuberaprost</a></li> <li><a href="/w/index.php?title=Etiproston&action=edit&redlink=1" class="new" title="Etiproston (page does not exist)">Etiproston</a></li> <li><a href="/w/index.php?title=Fenprostalene&action=edit&redlink=1" class="new" title="Fenprostalene (page does not exist)">Fenprostalene</a></li> <li><a href="/w/index.php?title=Flunoprost&action=edit&redlink=1" class="new" title="Flunoprost (page does not exist)">Flunoprost</a></li> <li><a href="/w/index.php?title=Froxiprost&action=edit&redlink=1" class="new" title="Froxiprost (page does not exist)">Froxiprost</a></li> <li><a href="/w/index.php?title=Lanproston&action=edit&redlink=1" class="new" title="Lanproston (page does not exist)">Lanproston</a></li> <li><a href="/w/index.php?title=Limaprost&action=edit&redlink=1" class="new" title="Limaprost (page does not exist)">Limaprost</a></li> <li><a href="/w/index.php?title=Luprostiol&action=edit&redlink=1" class="new" title="Luprostiol (page does not exist)">Luprostiol</a></li> <li><a href="/w/index.php?title=Meteneprost&action=edit&redlink=1" class="new" title="Meteneprost (page does not exist)">Meteneprost</a></li> <li><a href="/w/index.php?title=Mexiprostil&action=edit&redlink=1" class="new" title="Mexiprostil (page does not exist)">Mexiprostil</a></li> <li><a href="/w/index.php?title=Naxaprostene&action=edit&redlink=1" class="new" title="Naxaprostene (page does not exist)">Naxaprostene</a></li> <li><a href="/w/index.php?title=Nileprost&action=edit&redlink=1" class="new" title="Nileprost (page does not exist)">Nileprost</a></li> <li><a href="/w/index.php?title=Nocloprost&action=edit&redlink=1" class="new" title="Nocloprost (page does not exist)">Nocloprost</a></li> <li><a href="/w/index.php?title=Ornoprostil&action=edit&redlink=1" class="new" title="Ornoprostil (page does not exist)">Ornoprostil</a></li> <li><a href="/w/index.php?title=Oxoprostol&action=edit&redlink=1" class="new" title="Oxoprostol (page does not exist)">Oxoprostol</a></li> <li><a href="/w/index.php?title=Penprostene&action=edit&redlink=1" class="new" title="Penprostene (page does not exist)">Penprostene</a></li> <li><a href="/w/index.php?title=Pimilprost&action=edit&redlink=1" class="new" title="Pimilprost (page does not exist)">Pimilprost</a></li> <li><a href="/w/index.php?title=Piriprost&action=edit&redlink=1" class="new" title="Piriprost (page does not exist)">Piriprost</a></li> <li><a href="/w/index.php?title=Posaraprost&action=edit&redlink=1" class="new" title="Posaraprost (page does not exist)">Posaraprost</a></li> <li><a href="/w/index.php?title=Prostalene&action=edit&redlink=1" class="new" title="Prostalene (page does not exist)">Prostalene</a></li> <li><a href="/w/index.php?title=Rioprostil&action=edit&redlink=1" class="new" title="Rioprostil (page does not exist)">Rioprostil</a></li> <li><a href="/w/index.php?title=Rivenprost&action=edit&redlink=1" class="new" title="Rivenprost (page does not exist)">Rivenprost</a></li> <li><a href="/w/index.php?title=Rosaprostol&action=edit&redlink=1" class="new" title="Rosaprostol (page does not exist)">Rosaprostol</a></li> <li><a href="/w/index.php?title=Spiriprostil&action=edit&redlink=1" class="new" title="Spiriprostil (page does not exist)">Spiriprostil</a></li> <li><a href="/w/index.php?title=Tiaprost&action=edit&redlink=1" class="new" title="Tiaprost (page does not exist)">Tiaprost</a></li> <li><a href="/w/index.php?title=Tilsuprost&action=edit&redlink=1" class="new" title="Tilsuprost (page does not exist)">Tilsuprost</a></li> <li><a href="/w/index.php?title=Tiprostanide&action=edit&redlink=1" class="new" title="Tiprostanide (page does not exist)">Tiprostanide</a></li> <li><a href="/w/index.php?title=Trimoprostil&action=edit&redlink=1" class="new" title="Trimoprostil (page does not exist)">Trimoprostil</a></li> <li><a href="/w/index.php?title=Viprostol&action=edit&redlink=1" class="new" title="Viprostol (page does not exist)">Viprostol</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;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a>)</small></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:5em;;text-align:center;"><a href="/wiki/Cyclooxygenase" title="Cyclooxygenase"><abbr title="Cyclooxygenase">COX</abbr><br />(<abbr title="prostaglandin G/H synthase">PTGS</abbr>)</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Salicylic acids:</i> <a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Aspirin" title="Aspirin">Aspirin (acetylsalicylic acid)</a></li> <li><a href="/wiki/Benorilate" title="Benorilate">Benorilate (benorylate)</a></li> <li><a href="/wiki/Carbasalate_calcium" title="Carbasalate calcium">Carbasalate calcium</a></li> <li><a href="/wiki/Diflunisal" title="Diflunisal">Diflunisal</a></li> <li><a href="/wiki/Dipyrocetyl" title="Dipyrocetyl">Dipyrocetyl</a></li> <li><a href="/wiki/Ethenzamide" title="Ethenzamide">Ethenzamide</a></li> <li><a href="/wiki/Guacetisal" title="Guacetisal">Guacetisal</a></li> <li><a href="/wiki/Magnesium_salicylate" title="Magnesium salicylate">Magnesium salicylate</a></li> <li><a href="/wiki/Mesalazine" title="Mesalazine">Mesalazine (5-aminosalicylic acid)</a></li> <li><a href="/wiki/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a></li> <li><a href="/w/index.php?title=Salacetamide&action=edit&redlink=1" class="new" title="Salacetamide (page does not exist)">Salacetamide</a></li> <li><a href="/wiki/Salicin" title="Salicin">Salicin</a></li> <li><a href="/wiki/Salicylamide" title="Salicylamide">Salicylamide</a></li> <li><a href="/wiki/Salicylate" class="mw-redirect" title="Salicylate">Salicylate (salicylic acid)</a></li> <li><a href="/wiki/Salsalate" title="Salsalate">Salsalate</a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a></li> <li><a href="/wiki/Triflusal" title="Triflusal">Triflusal</a>; <i>Acetic acids:</i> <a href="/wiki/Aceclofenac" title="Aceclofenac">Aceclofenac</a></li> <li><a href="/wiki/Acemetacin" title="Acemetacin">Acemetacin</a></li> <li><a href="/w/index.php?title=Aclofenac&action=edit&redlink=1" class="new" title="Aclofenac (page does not exist)">Aclofenac</a></li> <li><a href="/wiki/Amfenac" title="Amfenac">Amfenac</a></li> <li><a href="/wiki/Alclofenac" title="Alclofenac">Alclofenac</a></li> <li><a href="/wiki/Bendazac" title="Bendazac">Bendazac</a></li> <li><a href="/wiki/Bromfenac" title="Bromfenac">Bromfenac</a></li> <li><a href="/wiki/Bufexamac" title="Bufexamac">Bufexamac</a></li> <li><a href="/wiki/Bumadizone" title="Bumadizone">Bumadizone</a></li> <li><a href="/w/index.php?title=Cinmetacin&action=edit&redlink=1" class="new" title="Cinmetacin (page does not exist)">Cinmetacin</a></li> <li><a href="/w/index.php?title=Clometacin&action=edit&redlink=1" class="new" title="Clometacin (page does not exist)">Clometacin</a></li> <li><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></li> <li><a href="/wiki/Difenpiramide" title="Difenpiramide">Difenpiramide</a></li> <li><a href="/wiki/Etodolac" title="Etodolac">Etodolac</a></li> <li><a href="/wiki/Felbinac" title="Felbinac">Felbinac</a></li> <li><a href="/wiki/Fenclofenac" title="Fenclofenac">Fenclofenac</a></li> <li><a href="/wiki/Fentiazac" title="Fentiazac">Fentiazac</a></li> <li><a href="/wiki/Glucametacin" title="Glucametacin">Glucametacin</a></li> <li><a href="/wiki/Indometacin" title="Indometacin">Indometacin (indomethacin)</a></li> <li><a href="/wiki/Indometacin_farnesil" title="Indometacin farnesil">Indometacin farnesil</a></li> <li><a href="/wiki/Ketorolac" title="Ketorolac">Ketorolac</a></li> <li><a href="/wiki/Lonazolac" title="Lonazolac">Lonazolac</a></li> <li><a href="/wiki/Mofezolac" title="Mofezolac">Mofezolac</a></li> <li><a href="/wiki/Nabumetone" title="Nabumetone">Nabumetone</a></li> <li><a href="/wiki/Oxametacin" title="Oxametacin">Oxametacin</a></li> <li><a href="/w/index.php?title=Oxindanac&action=edit&redlink=1" class="new" title="Oxindanac (page does not exist)">Oxindanac</a></li> <li><a href="/wiki/Proglumetacin" title="Proglumetacin">Proglumetacin</a></li> <li><a href="/wiki/Sulindac" title="Sulindac">Sulindac</a></li> <li><a href="/w/index.php?title=Sulindac_sulfide&action=edit&redlink=1" class="new" title="Sulindac sulfide (page does not exist)">Sulindac sulfide</a></li> <li><a href="/wiki/Tolmetin" title="Tolmetin">Tolmetin</a></li> <li><a href="/w/index.php?title=Zidometacin&action=edit&redlink=1" class="new" title="Zidometacin (page does not exist)">Zidometacin</a></li> <li><a href="/wiki/Zomepirac" title="Zomepirac">Zomepirac</a>; <i>Propionic acids:</i> <a href="/wiki/Alminoprofen" title="Alminoprofen">Alminoprofen</a></li> <li><a href="/wiki/Benoxaprofen" title="Benoxaprofen">Benoxaprofen</a></li> <li><a href="/w/index.php?title=Bucloxic_acid&action=edit&redlink=1" class="new" title="Bucloxic acid (page does not exist)">Bucloxic acid (blucloxate)</a></li> <li><a href="/w/index.php?title=Butibufen&action=edit&redlink=1" class="new" title="Butibufen (page does not exist)">Butibufen</a></li> <li><a href="/wiki/Carprofen" title="Carprofen">Carprofen</a></li> <li><a href="/wiki/Dexibuprofen" title="Dexibuprofen">Dexibuprofen</a></li> <li><a href="/w/index.php?title=Dexindoprofen&action=edit&redlink=1" class="new" title="Dexindoprofen (page does not exist)">Dexindoprofen</a></li> <li><a href="/wiki/Dexketoprofen" title="Dexketoprofen">Dexketoprofen</a></li> <li><a href="/wiki/Fenbufen" title="Fenbufen">Fenbufen</a></li> <li><a href="/wiki/Fenoprofen" title="Fenoprofen">Fenoprofen</a></li> <li><a href="/wiki/Flunoxaprofen" title="Flunoxaprofen">Flunoxaprofen</a></li> <li><a href="/wiki/Flurbiprofen" title="Flurbiprofen">Flurbiprofen</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a></li> <li><a href="/wiki/Ibuproxam" title="Ibuproxam">Ibuproxam</a></li> <li><a href="/wiki/Indoprofen" title="Indoprofen">Indoprofen</a></li> <li><a href="/wiki/Ketoprofen" title="Ketoprofen">Ketoprofen</a></li> <li><a href="/wiki/Loxoprofen" title="Loxoprofen">Loxoprofen</a></li> <li><a href="/wiki/Miroprofen" title="Miroprofen">Miroprofen</a></li> <li><a href="/wiki/Naproxen" title="Naproxen">Naproxen</a></li> <li><a href="/wiki/Naproxcinod" title="Naproxcinod">Naproxcinod</a></li> <li><a href="/wiki/Oxaprozin" title="Oxaprozin">Oxaprozin</a></li> <li><a href="/wiki/Pirprofen" title="Pirprofen">Pirprofen</a></li> <li><a href="/wiki/Pranoprofen" title="Pranoprofen">Pranoprofen</a></li> <li><a href="/wiki/Suprofen" title="Suprofen">Suprofen</a></li> <li><a href="/wiki/Tarenflurbil" title="Tarenflurbil">Tarenflurbil</a></li> <li><a href="/wiki/Tepoxalin" title="Tepoxalin">Tepoxalin</a></li> <li><a href="/wiki/Tiaprofenic_acid" title="Tiaprofenic acid">Tiaprofenic acid (tiaprofenate)</a></li> <li><a href="/wiki/Vedaprofen" title="Vedaprofen">Vedaprofen</a>; <i>Anthranilic acids (fenamic acids):</i> <a href="/wiki/Etofenamate" title="Etofenamate">Etofenamic acid (etofenamate)</a></li> <li><a href="/w/index.php?title=Floctafenic_acid&action=edit&redlink=1" class="new" title="Floctafenic acid (page does not exist)">Floctafenic acid (floctafenate)</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid (flufenamate)</a></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid (meclofenamate)</a></li> <li><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid (mefenamate)</a></li> <li><a href="/wiki/Morniflumate" title="Morniflumate">Morniflumic acid (morniflumate)</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic acid (niflumate)</a></li> <li><a href="/w/index.php?title=Talinflumic_acid&action=edit&redlink=1" class="new" title="Talinflumic acid (page does not exist)">Talinflumic acid (talinflumate)</a></li> <li><a href="/wiki/Tolfenamic_acid" title="Tolfenamic acid">Tolfenamic acid (tolfenamate)</a>; <i>Pyrazolones:</i> <a href="/wiki/Azapropazone" title="Azapropazone">Azapropazone</a></li> <li><a href="/wiki/Dipyrone" class="mw-redirect" title="Dipyrone">Dipyrone</a></li> <li><a href="/wiki/Isopyrin" class="mw-redirect" title="Isopyrin">Isopyrin</a></li> <li><a href="/wiki/Oxyphenbutazone" title="Oxyphenbutazone">Oxyphenbutazone</a></li> <li><a href="/wiki/Phenylbutazone" title="Phenylbutazone">Phenylbutazone</a>; <i>Enolic acids (oxicams):</i> <a href="/wiki/Ampiroxicam" title="Ampiroxicam">Ampiroxicam</a></li> <li><a href="/wiki/Droxicam" title="Droxicam">Droxicam</a></li> <li><a href="/w/index.php?title=Enolicam&action=edit&redlink=1" class="new" title="Enolicam (page does not exist)">Enolicam</a></li> <li><a href="/wiki/Isoxicam" title="Isoxicam">Isoxicam</a></li> <li><a href="/wiki/Lornoxicam" title="Lornoxicam">Lornoxicam</a></li> <li><a href="/wiki/Meloxicam" title="Meloxicam">Meloxicam</a></li> <li><a href="/wiki/Piroxicam" title="Piroxicam">Piroxicam</a></li> <li><a href="/wiki/Tenoxicam" title="Tenoxicam">Tenoxicam</a>; <i>4-Aminoquinolines:</i> <a href="/wiki/Antrafenine" title="Antrafenine">Antrafenine</a></li> <li><a href="/wiki/Floctafenine" title="Floctafenine">Floctafenine</a></li> <li><a href="/wiki/Glafenine" title="Glafenine">Glafenine</a>; <i>Quinazolines:</i> <a href="/wiki/Fluproquazone" title="Fluproquazone">Fluproquazone</a></li> <li><a href="/wiki/Proquazone" title="Proquazone">Proquazone</a>; <i>Aminonicotinic acids:</i> <a href="/wiki/Clonixeril" class="mw-redirect" title="Clonixeril">Clonixeril</a></li> <li><a href="/wiki/Clonixin" title="Clonixin">Clonixin</a></li> <li><a href="/wiki/Flunixin" title="Flunixin">Flunixin</a>; <i>Sulfonanilides:</i> <a href="/w/index.php?title=Flosulide&action=edit&redlink=1" class="new" title="Flosulide (page does not exist)">Flosulide</a></li> <li><a href="/wiki/Nimesulide" title="Nimesulide">Nimesulide</a>; <i>Aminophenols (anilines):</i> <a href="/wiki/Acetanilide" title="Acetanilide">Acetanilide</a></li> <li><a href="/wiki/AM404" title="AM404">AM-404 (N-arachidonoylaminophenol)</a></li> <li><a href="/wiki/Bucetin" title="Bucetin">Bucetin</a></li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a></li> <li><a href="/w/index.php?title=Parapropamol&action=edit&redlink=1" class="new" title="Parapropamol (page does not exist)">Parapropamol</a></li> <li><a class="mw-selflink selflink">Phenacetin</a></li> <li><a href="/wiki/Propacetamol" title="Propacetamol">Propacetamol</a>; <i>Selective COX-2 inhibitors (coxibs):</i> <a href="/wiki/Apricoxib" title="Apricoxib">Apricoxib</a></li> <li><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a></li> <li><a href="/wiki/Cimicoxib" title="Cimicoxib">Cimicoxib</a></li> <li><a href="/wiki/Deracoxib" title="Deracoxib">Deracoxib</a></li> <li><a href="/wiki/Etoricoxib" title="Etoricoxib">Etoricoxib</a></li> <li><a href="/wiki/Firocoxib" title="Firocoxib">Firocoxib</a></li> <li><a href="/wiki/Lumiracoxib" title="Lumiracoxib">Lumiracoxib</a></li> <li><a href="/wiki/Mavacoxib" title="Mavacoxib">Mavacoxib</a></li> <li><a href="/wiki/Parecoxib" title="Parecoxib">Parecoxib</a></li> <li><a href="/wiki/Polmacoxib" title="Polmacoxib">Polmacoxib</a></li> <li><a href="/wiki/Robenacoxib" title="Robenacoxib">Robenacoxib</a></li> <li><a href="/wiki/Rofecoxib" title="Rofecoxib">Rofecoxib</a></li> <li><a href="/wiki/Tilmacoxib" title="Tilmacoxib">Tilmacoxib</a></li> <li><a href="/wiki/Valdecoxib" title="Valdecoxib">Valdecoxib</a>; <i>Others/unsorted:</i> <a href="/wiki/Anitrazafen" title="Anitrazafen">Anitrazafen</a></li> <li><a href="/w/index.php?title=Clobuzarit&action=edit&redlink=1" class="new" title="Clobuzarit (page does not exist)">Clobuzarit</a></li> <li><a href="/wiki/Curcumin" title="Curcumin">Curcumin</a></li> <li><a href="/w/index.php?title=DuP-697&action=edit&redlink=1" class="new" title="DuP-697 (page does not exist)">DuP-697</a></li> <li><a href="/w/index.php?title=FK-3311&action=edit&redlink=1" class="new" title="FK-3311 (page does not exist)">FK-3311</a></li> <li><a href="/wiki/Flumizole" title="Flumizole">Flumizole</a></li> <li><a href="/w/index.php?title=FR-122047&action=edit&redlink=1" class="new" title="FR-122047 (page does not exist)">FR-122047</a></li> <li><a href="/wiki/Glimepiride" title="Glimepiride">Glimepiride</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</a></li> <li><a href="/w/index.php?title=Itazigrel&action=edit&redlink=1" class="new" title="Itazigrel (page does not exist)">Itazigrel</a></li> <li><a href="/w/index.php?title=L-655240&action=edit&redlink=1" class="new" title="L-655240 (page does not exist)">L-655240</a></li> <li><a href="/w/index.php?title=L-670596&action=edit&redlink=1" class="new" title="L-670596 (page does not exist)">L-670596</a></li> <li><a href="/wiki/Licofelone" title="Licofelone">Licofelone</a></li> <li><a href="/wiki/Menatetrenone" title="Menatetrenone">Menatetrenone (vitamin K<sub>2</sub>)</a></li> <li><a href="/w/index.php?title=NCX-466&action=edit&redlink=1" class="new" title="NCX-466 (page does not exist)">NCX-466</a></li> <li><a href="/w/index.php?title=NCX-4040&action=edit&redlink=1" class="new" title="NCX-4040 (page does not exist)">NCX-4040</a></li> <li><a href="/wiki/NS-398" title="NS-398">NS-398</a></li> <li><a href="/wiki/Pamicogrel" title="Pamicogrel">Pamicogrel</a></li> <li><a href="/wiki/Resveratrol" title="Resveratrol">Resveratrol</a></li> <li><a href="/w/index.php?title=Romazarit&action=edit&redlink=1" class="new" title="Romazarit (page does not exist)">Romazarit</a></li> <li><a href="/wiki/Rosmarinic_acid" title="Rosmarinic acid">Rosmarinic acid</a></li> <li><a href="/wiki/Rutecarpine" title="Rutecarpine">Rutecarpine</a></li> <li><a href="/w/index.php?title=Satigrel&action=edit&redlink=1" class="new" title="Satigrel (page does not exist)">Satigrel</a></li> <li><a href="/w/index.php?title=SC-236&action=edit&redlink=1" class="new" title="SC-236 (page does not exist)">SC-236</a></li> <li><a href="/w/index.php?title=SC-560&action=edit&redlink=1" class="new" title="SC-560 (page does not exist)">SC-560</a></li> <li><a href="/w/index.php?title=SC-58125&action=edit&redlink=1" class="new" title="SC-58125 (page does not exist)">SC-58125</a></li> <li><a href="/wiki/Tenidap" title="Tenidap">Tenidap</a></li> <li><a href="/w/index.php?title=Tiflamizole&action=edit&redlink=1" class="new" title="Tiflamizole (page does not exist)">Tiflamizole</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="/w/index.php?title=Trifenagrel&action=edit&redlink=1" class="new" title="Trifenagrel (page does not exist)">Trifenagrel</a></li> <li><a href="/w/index.php?title=Tropesin&action=edit&redlink=1" class="new" title="Tropesin (page does not exist)">Tropesin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_D_synthase" class="mw-redirect" title="Prostaglandin D synthase"><abbr title="Prostaglandin D synthase">PGD<sub>2</sub>S</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 Prostaglandin D synthase</span></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/Retinoid" title="Retinoid">Retinoids</a></li> <li><a href="/wiki/Selenium" title="Selenium">Selenium</a> (<a href="/wiki/Selenium_tetrachloride" title="Selenium tetrachloride">selenium tetrachloride</a>, <a href="/wiki/Sodium_selenite" title="Sodium selenite">sodium selenite</a>, <a href="/wiki/Selenium_disulfide" title="Selenium disulfide">selenium disulfide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_E_synthase" title="Prostaglandin E synthase"><abbr title="Prostaglandin E synthase">PGES</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 Prostaglandin E synthase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"><a href="/w/index.php?title=HQL-79&action=edit&redlink=1" class="new" title="HQL-79 (page does not exist)">HQL-79</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostaglandin_F_synthase" title="Prostaglandin F synthase"><abbr title="Prostaglandin F synthase">PGFS</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 Prostaglandin F synthase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"><a href="/wiki/Bimatoprost" title="Bimatoprost">Bimatoprost</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Prostacyclin_synthase" title="Prostacyclin synthase"><abbr title="Prostacyclin synthase">PGI<sub>2</sub>S</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 Prostacyclin synthase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;;text-align:center;"><a href="/wiki/Thromboxane_A_synthase" class="mw-redirect" title="Thromboxane A synthase"><abbr title="Thromboxane A synthase">TXAS</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 Thromboxane A synthase</span></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=Camonagrel&action=edit&redlink=1" class="new" title="Camonagrel (page does not exist)">Camonagrel</a></li> <li><a href="/w/index.php?title=Dazmegrel&action=edit&redlink=1" class="new" title="Dazmegrel (page does not exist)">Dazmegrel</a></li> <li><a href="/wiki/Dazoxiben" title="Dazoxiben">Dazoxiben</a></li> <li><a href="/wiki/Furegrelate" title="Furegrelate">Furegrelate</a></li> <li><a href="/w/index.php?title=Isbogrel&action=edit&redlink=1" class="new" title="Isbogrel (page does not exist)">Isbogrel</a></li> <li><a href="/w/index.php?title=Midazogrel&action=edit&redlink=1" class="new" title="Midazogrel (page does not exist)">Midazogrel</a></li> <li><a href="/w/index.php?title=Nafagrel&action=edit&redlink=1" class="new" title="Nafagrel (page does not exist)">Nafagrel</a></li> <li><a href="/w/index.php?title=Nicogrelate&action=edit&redlink=1" class="new" title="Nicogrelate (page does not exist)">Nicogrelate</a></li> <li><a href="/wiki/Ozagrel" title="Ozagrel">Ozagrel</a></li> <li><a href="/wiki/Picotamide" title="Picotamide">Picotamide</a></li> <li><a href="/w/index.php?title=Pirmagrel&action=edit&redlink=1" class="new" title="Pirmagrel (page does not exist)">Pirmagrel</a></li> <li><a href="/w/index.php?title=Ridogrel&action=edit&redlink=1" class="new" title="Ridogrel (page does not exist)">Ridogrel</a></li> <li><a href="/w/index.php?title=Rolafagrel&action=edit&redlink=1" class="new" title="Rolafagrel (page does not exist)">Rolafagrel</a></li> <li><a href="/w/index.php?title=Samixogrel&action=edit&redlink=1" class="new" title="Samixogrel (page does not exist)">Samixogrel</a></li> <li><a href="/wiki/Terbogrel" title="Terbogrel">Terbogrel</a></li> <li><a href="/w/index.php?title=U63557A&action=edit&redlink=1" class="new" title="U63557A (page does not exist)">U63557A</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><b>Precursors:</b> <a href="/wiki/Linoleic_acid" title="Linoleic acid">Linoleic acid</a></li> <li><a href="/wiki/Gamma-Linolenic_acid" class="mw-redirect" title="Gamma-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/Prostaglandin_G2" title="Prostaglandin G2">Prostaglandin G<sub>2</sub></a></li> <li><a href="/wiki/Prostaglandin_H2" title="Prostaglandin H2">Prostaglandin H<sub>2</sub></a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></i></dd> <dd><i><a href="/wiki/Template:Leukotriene_signaling_modulators" title="Template:Leukotriene signaling modulators">Leukotriene signaling modulators</a></i></dd></dl> 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