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Salicylic acid - Wikipedia
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<li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Chemical_synthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chemical_synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Chemical synthesis</span> </div> </a> <ul id="toc-Chemical_synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactions" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.3</span> <span>Reactions</span> </div> </a> <ul id="toc-Reactions-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dietary_sources" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Dietary_sources"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Dietary sources</span> </div> </a> <ul id="toc-Dietary_sources-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Plant_hormone" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Plant_hormone"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Plant hormone</span> </div> </a> <button aria-controls="toc-Plant_hormone-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Plant hormone subsection</span> </button> <ul id="toc-Plant_hormone-sublist" class="vector-toc-list"> <li id="toc-Signal_transduction" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Signal_transduction"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Signal transduction</span> </div> </a> <ul id="toc-Signal_transduction-sublist" class="vector-toc-list"> </ul> </li> </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">8</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">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-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">11</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Salicylic acid</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 60 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-60" 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">60 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/%D8%AD%D9%85%D8%B6_%D8%A7%D9%84%D8%B3%D8%A7%D9%84%D9%8A%D8%B3%D9%8A%D9%84%D9%8A%D9%83" title="حمض الساليسيليك – Arabic" lang="ar" hreflang="ar" data-title="حمض الساليسيليك" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D8%B3%DB%8C%D8%AF_%D8%B3%D8%A7%D9%84%DB%8C%D8%B3%DB%8C%D9%84%DB%8C%DA%A9" title="اسید سالیسیلیک – South Azerbaijani" lang="azb" hreflang="azb" data-title="اسید سالیسیلیک" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-be mw-list-item"><a href="https://be.wikipedia.org/wiki/%D0%A1%D0%B0%D0%BB%D1%96%D1%86%D1%8B%D0%BB%D0%B0%D0%B2%D0%B0%D1%8F_%D0%BA%D1%96%D1%81%D0%BB%D0%B0%D1%82%D0%B0" title="Саліцылавая кіслата – Belarusian" lang="be" hreflang="be" data-title="Саліцылавая кіслата" data-language-autonym="Беларуская" data-language-local-name="Belarusian" class="interlanguage-link-target"><span>Беларуская</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%A1%D0%B0%D0%BB%D0%B8%D1%86%D0%B8%D0%BB%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Салицилова киселина – Bulgarian" lang="bg" hreflang="bg" data-title="Салицилова киселина" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Salicilna_kiselina" title="Salicilna kiselina – Bosnian" lang="bs" hreflang="bs" data-title="Salicilna kiselina" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target"><span>Bosanski</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/%C3%80cid_salic%C3%ADlic" title="Àcid salicílic – Catalan" lang="ca" hreflang="ca" data-title="Àcid salicílic" 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/Kyselina_salicylov%C3%A1" title="Kyselina salicylová – Czech" lang="cs" hreflang="cs" data-title="Kyselina salicylová" 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/Asid_salicylig" title="Asid salicylig – Welsh" lang="cy" hreflang="cy" data-title="Asid salicylig" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Salicylsyre" title="Salicylsyre – Danish" lang="da" hreflang="da" data-title="Salicylsyre" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Salicyls%C3%A4ure" title="Salicylsäure – German" lang="de" hreflang="de" data-title="Salicylsäure" 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/Salits%C3%BC%C3%BClhape" title="Salitsüülhape – Estonian" lang="et" hreflang="et" data-title="Salitsüülhape" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%A3%CE%B1%CE%BB%CE%B9%CE%BA%CF%85%CE%BB%CE%B9%CE%BA%CF%8C_%CE%BF%CE%BE%CF%8D" title="Σαλικυλικό οξύ – Greek" lang="el" hreflang="el" data-title="Σαλικυλικό οξύ" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/%C3%81cido_salic%C3%ADlico" title="Ácido salicílico – Spanish" lang="es" hreflang="es" data-title="Ácido salicílico" 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/Salikata_acido" title="Salikata acido – Esperanto" lang="eo" hreflang="eo" data-title="Salikata acido" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target"><span>Esperanto</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Azido_saliziliko" title="Azido saliziliko – Basque" lang="eu" hreflang="eu" data-title="Azido saliziliko" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%D8%A7%D9%84%DB%8C%D8%B3%DB%8C%D9%84%DB%8C%DA%A9_%D8%A7%D8%B3%DB%8C%D8%AF" title="سالیسیلیک اسید – Persian" lang="fa" hreflang="fa" data-title="سالیسیلیک اسید" 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/Acide_salicylique" title="Acide salicylique – French" lang="fr" hreflang="fr" data-title="Acide salicylique" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ga mw-list-item"><a href="https://ga.wikipedia.org/wiki/Aig%C3%A9ad_salaicileach" title="Aigéad salaicileach – Irish" lang="ga" hreflang="ga" data-title="Aigéad salaicileach" data-language-autonym="Gaeilge" data-language-local-name="Irish" class="interlanguage-link-target"><span>Gaeilge</span></a></li><li class="interlanguage-link interwiki-gv mw-list-item"><a href="https://gv.wikipedia.org/wiki/Geayrag_halicylagh" title="Geayrag halicylagh – Manx" lang="gv" hreflang="gv" data-title="Geayrag halicylagh" data-language-autonym="Gaelg" data-language-local-name="Manx" class="interlanguage-link-target"><span>Gaelg</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/%C3%81cido_salic%C3%ADlico" title="Ácido salicílico – Galician" lang="gl" hreflang="gl" data-title="Ácido salicílico" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%82%B4%EB%A6%AC%EC%8B%A4%EC%82%B0" title="살리실산 – Korean" lang="ko" hreflang="ko" data-title="살리실산" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8D%D5%A1%D5%AC%D5%AB%D6%81%D5%AB%D5%AC%D5%A1%D5%A9%D5%A9%D5%B8%D6%82" title="Սալիցիլաթթու – Armenian" lang="hy" hreflang="hy" data-title="Սալիցիլաթթու" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A5%88%E0%A4%B2%E0%A4%BF%E0%A4%B8%E0%A4%BF%E0%A4%B2%E0%A4%BF%E0%A4%95_%E0%A4%85%E0%A4%AE%E0%A5%8D%E0%A4%B2" title="सैलिसिलिक अम्ल – Hindi" lang="hi" hreflang="hi" data-title="सैलिसिलिक अम्ल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Salicilna_kiselina" title="Salicilna kiselina – Croatian" lang="hr" hreflang="hr" data-title="Salicilna kiselina" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Asam_salisilat" title="Asam salisilat – Indonesian" lang="id" hreflang="id" data-title="Asam salisilat" 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-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Salis%C3%BDls%C3%BDra" title="Salisýlsýra – Icelandic" lang="is" hreflang="is" data-title="Salisýlsýra" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Acido_salicilico" title="Acido salicilico – Italian" lang="it" hreflang="it" data-title="Acido salicilico" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%97%D7%95%D7%9E%D7%A6%D7%94_%D7%A1%D7%9C%D7%99%D7%A6%D7%99%D7%9C%D7%99%D7%AA" title="חומצה סליצילית – Hebrew" lang="he" hreflang="he" data-title="חומצה סליצילית" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Asem_salisilat" title="Asem salisilat – Javanese" lang="jv" hreflang="jv" data-title="Asem salisilat" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target"><span>Jawa</span></a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/Salicilsk%C4%81be" title="Salicilskābe – Latvian" lang="lv" hreflang="lv" data-title="Salicilskābe" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target"><span>Latviešu</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Szalicilsav" title="Szalicilsav – Hungarian" lang="hu" hreflang="hu" data-title="Szalicilsav" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A1%D0%B0%D0%BB%D0%B8%D1%86%D0%B8%D0%BB%D0%BD%D0%B0_%D0%BA%D0%B8%D1%81%D0%B5%D0%BB%D0%B8%D0%BD%D0%B0" title="Салицилна киселина – Macedonian" lang="mk" hreflang="mk" data-title="Салицилна киселина" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B8%E0%B4%BE%E0%B4%B2%E0%B4%BF%E0%B4%B8%E0%B4%BF%E0%B4%B2%E0%B4%BF%E0%B4%95%E0%B5%8D_%E0%B4%85%E0%B4%AE%E0%B5%8D%E0%B4%B2%E0%B4%82" title="സാലിസിലിക് അമ്ലം – Malayalam" lang="ml" hreflang="ml" data-title="സാലിസിലിക് അമ്ലം" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Asid_salisilik" title="Asid salisilik – Malay" lang="ms" hreflang="ms" data-title="Asid salisilik" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Salicylzuur" title="Salicylzuur – Dutch" lang="nl" hreflang="nl" data-title="Salicylzuur" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B5%E3%83%AA%E3%83%81%E3%83%AB%E9%85%B8" title="サリチル酸 – Japanese" lang="ja" hreflang="ja" data-title="サリチル酸" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Salisylsyre" title="Salisylsyre – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Salisylsyre" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Salitsil_kislota" title="Salitsil kislota – Uzbek" lang="uz" hreflang="uz" data-title="Salitsil kislota" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Kwas_salicylowy" title="Kwas salicylowy – Polish" lang="pl" hreflang="pl" data-title="Kwas salicylowy" 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/%C3%81cido_salic%C3%ADlico" title="Ácido salicílico – Portuguese" lang="pt" hreflang="pt" data-title="Ácido salicílico" 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/Acid_salicilic" title="Acid salicilic – Romanian" lang="ro" hreflang="ro" data-title="Acid salicilic" 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%A1%D0%B0%D0%BB%D0%B8%D1%86%D0%B8%D0%BB%D0%BE%D0%B2%D0%B0%D1%8F_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Салициловая кислота – Russian" lang="ru" hreflang="ru" data-title="Салициловая кислота" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sco mw-list-item"><a href="https://sco.wikipedia.org/wiki/Salicylic_acid" title="Salicylic acid – Scots" lang="sco" hreflang="sco" data-title="Salicylic acid" data-language-autonym="Scots" data-language-local-name="Scots" class="interlanguage-link-target"><span>Scots</span></a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Acidi_salicilik" title="Acidi salicilik – Albanian" lang="sq" hreflang="sq" data-title="Acidi salicilik" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target"><span>Shqip</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Salicylic_acid" title="Salicylic acid – Simple English" lang="en-simple" hreflang="en-simple" data-title="Salicylic acid" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Kyselina_salicylov%C3%A1" title="Kyselina salicylová – Slovak" lang="sk" hreflang="sk" data-title="Kyselina salicylová" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Salicilna_kislina" title="Salicilna kislina – Slovenian" lang="sl" hreflang="sl" data-title="Salicilna kislina" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Salicilna_kiselina" title="Salicilna kiselina – Serbian" lang="sr" hreflang="sr" data-title="Salicilna kiselina" 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/Salicilna_kiselina" title="Salicilna kiselina – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Salicilna kiselina" 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/Salisyylihappo" title="Salisyylihappo – Finnish" lang="fi" hreflang="fi" data-title="Salisyylihappo" 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/Salicylsyra" title="Salicylsyra – Swedish" lang="sv" hreflang="sv" data-title="Salicylsyra" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%B8%E0%B0%BE%E0%B0%B2%E0%B0%BF%E0%B0%B8%E0%B0%BF%E0%B0%B2%E0%B0%BF%E0%B0%95%E0%B1%8D_%E0%B0%86%E0%B0%AE%E0%B1%8D%E0%B0%B2%E0%B0%82" title="సాలిసిలిక్ ఆమ్లం – Telugu" lang="te" hreflang="te" data-title="సాలిసిలిక్ ఆమ్లం" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target"><span>తెలుగు</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%81%E0%B8%A3%E0%B8%94%E0%B8%8B%E0%B8%B2%E0%B8%A5%E0%B8%B4%E0%B9%84%E0%B8%8B%E0%B8%A5%E0%B8%B4%E0%B8%81" title="กรดซาลิไซลิก – Thai" lang="th" hreflang="th" data-title="กรดซาลิไซลิก" 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/Salisilik_asit" title="Salisilik asit – Turkish" lang="tr" hreflang="tr" data-title="Salisilik asit" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A1%D0%B0%D0%BB%D1%96%D1%86%D0%B8%D0%BB%D0%BE%D0%B2%D0%B0_%D0%BA%D0%B8%D1%81%D0%BB%D0%BE%D1%82%D0%B0" title="Саліцилова кислота – Ukrainian" lang="uk" hreflang="uk" data-title="Саліцилова кислота" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D8%B3%D8%A7%D9%84%DB%8C%D8%B3%D8%A7%D8%A6%D9%84%DA%A9_%D8%AA%DB%8C%D8%B2%D8%A7%D8%A8" title="سالیسائلک تیزاب – Urdu" lang="ur" hreflang="ur" data-title="سالیسائلک تیزاب" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target"><span>اردو</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Acid_salicylic" title="Acid salicylic – Vietnamese" lang="vi" hreflang="vi" data-title="Acid salicylic" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E6%B0%B4%E6%9D%A8%E9%85%B8" title="水杨酸 – Wu" lang="wuu" hreflang="wuu" data-title="水杨酸" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E6%B0%B4%E6%A5%8A%E9%85%B8" title="水楊酸 – 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</div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" 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.ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}</style> </p> <table class="infobox ib-chembox"> <caption>Salicylic acid </caption> <tbody><tr> <td colspan="2" class="borderless" style="text-align:center"> <table border="0" style="width:100%;display:inline-table;"> <tbody><tr> <td style="border-right:1px solid #aaa; width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Salicylic-acid-skeletal.svg" class="mw-file-description" title="Skeletal formula of salicylic acid"><img alt="Skeletal formula of salicylic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Salicylic-acid-skeletal.svg/100px-Salicylic-acid-skeletal.svg.png" decoding="async" width="100" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Salicylic-acid-skeletal.svg/150px-Salicylic-acid-skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/8e/Salicylic-acid-skeletal.svg/200px-Salicylic-acid-skeletal.svg.png 2x" data-file-width="256" data-file-height="279" /></a><figcaption>Skeletal formula of salicylic acid</figcaption></figure> </td> <td style="width:50%;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Salicylic-acid-from-xtal-2006-3D-balls.png" class="mw-file-description" title="Ball-and-stick model of salicylic acid"><img alt="Ball-and-stick model of salicylic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Salicylic-acid-from-xtal-2006-3D-balls.png/100px-Salicylic-acid-from-xtal-2006-3D-balls.png" decoding="async" width="100" height="137" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Salicylic-acid-from-xtal-2006-3D-balls.png/150px-Salicylic-acid-from-xtal-2006-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fb/Salicylic-acid-from-xtal-2006-3D-balls.png/200px-Salicylic-acid-from-xtal-2006-3D-balls.png 2x" data-file-width="803" data-file-height="1100" /></a><figcaption>Ball-and-stick model of salicylic acid</figcaption></figure> </td></tr></tbody></table> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><span typeof="mw:File"><a href="/wiki/File:Kwas_salicylowy.jpg" class="mw-file-description" title="Salicylic acid"><img alt="Salicylic acid" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Kwas_salicylowy.jpg/220px-Kwas_salicylowy.jpg" decoding="async" width="220" height="162" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/71/Kwas_salicylowy.jpg/330px-Kwas_salicylowy.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/71/Kwas_salicylowy.jpg/440px-Kwas_salicylowy.jpg 2x" data-file-width="2380" data-file-height="1748" /></a></span> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">2-Hydroxybenzoic acid<sup id="cite_ref-iupac2013_1-0" class="reference"><a href="#cite_note-iupac2013-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=69-72-7">69-72-7</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28O%29c1ccccc1O">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=16914">CHEBI:16914</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/ChEMBL424">ChEMBL424</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.331.html">331</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00936">DB00936</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.648">100.000.648</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q193572#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>200-712-3</li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/IUPHAR/BPS" class="mw-redirect" title="IUPHAR/BPS">IUPHAR/BPS</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=summary&ligandId=4306">4306</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00097">D00097</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/338">338</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>VO0525000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/O414PZ4LPZ">O414PZ4LPZ</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID7026368">DTXSID7026368</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q193572#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YGSDEFSMJLZEOE-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></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YGSDEFSMJLZEOE-UHFFFAOYAQ</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal; background:transparent;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=C(O)c1ccccc1O</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>7</sub><span title="Hydrogen">H</span><sub>6</sub><span title="Oxygen">O</span><sub>3</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002138122000000000♠"></span>138.122</span> g/mol   </td></tr> <tr> <td>Appearance </td> <td>Colorless to white crystalline powder </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td>Odorless </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.443<span class="nowrap"> </span>g/cm<sup>3</sup> (20<span class="nowrap"> </span>°C)<sup id="cite_ref-crc_2-0" class="reference"><a href="#cite_note-crc-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>158.6 °C (317.5 °F; 431.8 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>211 °C (412 °F; 484 K)<br /> at 20<span class="nowrap"> </span>mmHg<sup id="cite_ref-crc_2-1" class="reference"><a href="#cite_note-crc-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pubchem_3-0" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><br /> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Sublimation_(phase_transition)" title="Sublimation (phase transition)">Sublimation<br />conditions</a></div> </td> <td>Sublimes at 76<span class="nowrap"> </span>°C<sup id="cite_ref-pubchem_3-1" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>1.24<span class="nowrap"> </span>g/L (0<span class="nowrap"> </span>°C)</li><li>2.48<span class="nowrap"> </span>g/L (25<span class="nowrap"> </span>°C)</li><li>4.14<span class="nowrap"> </span>g/L (40<span class="nowrap"> </span>°C)</li><li>17.41<span class="nowrap"> </span>g/L (75<span class="nowrap"> </span>°C)<sup id="cite_ref-pubchem_3-2" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li><li>77.79<span class="nowrap"> </span>g/L (100<span class="nowrap"> </span>°C)<sup id="cite_ref-sioc_4-0" class="reference"><a href="#cite_note-sioc-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Soluble in <a href="/wiki/Diethyl_ether" title="Diethyl ether">ether</a>, <a href="/wiki/Carbon_tetrachloride" title="Carbon tetrachloride">CCl<sub>4</sub></a>, <a href="/wiki/Benzene" title="Benzene">benzene</a>, <a href="/wiki/Propanol" title="Propanol">propanol</a>, <a href="/wiki/Acetone" title="Acetone">acetone</a>, <a href="/wiki/Ethanol" title="Ethanol">ethanol</a>, <a href="/wiki/Oil_of_turpentine" class="mw-redirect" title="Oil of turpentine">oil of turpentine</a>, <a href="/wiki/Toluene" title="Toluene">toluene</a> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Benzene" title="Benzene">benzene</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>0.46<span class="nowrap"> </span>g/100<span class="nowrap"> </span>g (11.7<span class="nowrap"> </span>°C)</li><li>0.775<span class="nowrap"> </span>g/100<span class="nowrap"> </span>g (25<span class="nowrap"> </span>°C)</li><li>0.991<span class="nowrap"> </span>g/100<span class="nowrap"> </span>g (30.5<span class="nowrap"> </span>°C)</li><li>2.38<span class="nowrap"> </span>g/100<span class="nowrap"> </span>g (49.4<span class="nowrap"> </span>°C)</li><li>4.4<span class="nowrap"> </span>g/100<span class="nowrap"> </span>g (64.2<span class="nowrap"> </span>°C)<sup id="cite_ref-pubchem_3-3" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-sioc_4-1" class="reference"><a href="#cite_note-sioc-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Chloroform" title="Chloroform">chloroform</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>2.22<span class="nowrap"> </span>g/100<span class="nowrap"> </span>mL (25<span class="nowrap"> </span>°C)<sup id="cite_ref-sioc_4-2" class="reference"><a href="#cite_note-sioc-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li><li>2.31<span class="nowrap"> </span>g/100<span class="nowrap"> </span>mL (30.5<span class="nowrap"> </span>°C)<sup id="cite_ref-pubchem_3-4" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Methanol" title="Methanol">methanol</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>40.67<span class="nowrap"> </span>g/100<span class="nowrap"> </span>g (−3<span class="nowrap"> </span>°C)</li><li>62.48<span class="nowrap"> </span>g/100<span class="nowrap"> </span>g (21<span class="nowrap"> </span>°C)<sup id="cite_ref-pubchem_3-5" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Olive_oil" title="Olive oil">olive oil</a> </td> <td>2.43<span class="nowrap"> </span>g/100<span class="nowrap"> </span>g (23<span class="nowrap"> </span>°C)<sup id="cite_ref-pubchem_3-6" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> in <a href="/wiki/Acetone" title="Acetone">acetone</a> </td> <td>39.6<span class="nowrap"> </span>g/100<span class="nowrap"> </span>g (23<span class="nowrap"> </span>°C)<sup id="cite_ref-pubchem_3-7" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Partition_coefficient" title="Partition coefficient">log <i>P</i></a> </td> <td>2.26 </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>10.93<span class="nowrap"> </span>mPa<sup id="cite_ref-pubchem_3-8" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Acid_dissociation_constant" title="Acid dissociation constant">Acidity</a> (p<i>K</i><sub>a</sub>) </td> <td><div><ol style="margin-left:0; list-style-position:inside;"><li>2.97 (25<span class="nowrap"> </span>°C)<sup id="cite_ref-drugbank_5-0" class="reference"><a href="#cite_note-drugbank-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li><li>13.82 (20<span class="nowrap"> </span>°C)<sup id="cite_ref-pubchem_3-9" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li></ol></div> </td></tr> <tr> <td><a href="/wiki/Ultraviolet%E2%80%93visible_spectroscopy" title="Ultraviolet–visible spectroscopy">UV-vis</a> (λ<sub>max</sub>) </td> <td>210<span class="nowrap"> </span>nm, 234<span class="nowrap"> </span>nm, 303<span class="nowrap"> </span>nm (4 mg/dL in ethanol)<sup id="cite_ref-pubchem_3-10" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Magnetic_susceptibility" title="Magnetic susceptibility">Magnetic susceptibility</a> (χ)</div> </td> <td>−72.23·10<sup>−6</sup><span class="nowrap"> </span>cm<sup>3</sup>/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Refractive_index" title="Refractive index">Refractive index</a> (<i>n</i><sub>D</sub>)</div> </td> <td>1.565 (20<span class="nowrap"> </span>°C)<sup id="cite_ref-crc_2-2" class="reference"><a href="#cite_note-crc-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Dipole#Molecular_dipoles" title="Dipole">Dipole moment</a></div> </td> <td>2.65 D </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Thermochemistry </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_formation" class="mw-redirect" title="Standard enthalpy change of formation">Std enthalpy of<br />formation</a> <span style="font-size:112%;">(Δ<sub>f</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>−589.9<span class="nowrap"> </span>kJ/mol </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Standard_enthalpy_change_of_combustion" class="mw-redirect" title="Standard enthalpy change of combustion">Std enthalpy of<br />combustion</a> <span style="font-size:112%;">(Δ<sub>c</sub><i>H</i><sup>⦵</sup><sub>298</sub>)</span></div> </td> <td>-3.025<span class="nowrap"> </span>MJ/mol<sup id="cite_ref-NIST_6-0" class="reference"><a href="#cite_note-NIST-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Pharmacology </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></div> </td> <td><a href="/wiki/ATC_code_A01" title="ATC code A01">A01AD05</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=A01AD05">WHO</a></span>) <a href="/wiki/ATC_code_B01" title="ATC code B01">B01AC06</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=B01AC06">WHO</a></span>) <a href="/wiki/ATC_code_D01" title="ATC code D01">D01AE12</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D01AE12">WHO</a></span>) <a href="/wiki/ATC_code_N02" title="ATC code N02">N02BA01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N02BA01">WHO</a></span>) <a href="/wiki/ATC_code_S01" title="ATC code S01">S01BC08</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S01BC08">WHO</a></span>) </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Eye hazards</div> </td> <td>Severe irritation </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Skin hazards</div> </td> <td>Mild irritation </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>:<sup id="cite_ref-sigma_7-0" class="reference"><a href="#cite_note-sigma-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-acid.svg" class="mw-file-description" title="GHS05: Corrosive"><img alt="GHS05: Corrosive" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/50px-GHS-pictogram-acid.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/75px-GHS-pictogram-acid.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/GHS-pictogram-acid.svg/100px-GHS-pictogram-acid.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> <span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-exclam.svg" class="mw-file-description" title="GHS07: Exclamation mark"><img alt="GHS07: Exclamation mark" src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/50px-GHS-pictogram-exclam.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/75px-GHS-pictogram-exclam.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c3/GHS-pictogram-exclam.svg/100px-GHS-pictogram-exclam.svg.png 2x" data-file-width="512" data-file-height="512" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H302: Harmful if swallowed">H302</abbr>, <abbr class="abbr" title="H318: Causes serious eye damage">H318</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.">P305+P351+P338</abbr> </td></tr> <tr> <td><a href="/wiki/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_482e25fdfe95519d" /></span><map name="ImageMap_482e25fdfe95519d"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform" class="notheme mw-no-invert">2</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil" class="notheme mw-no-invert">1</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>157 °C (315 °F; 430 K) <br /> closed cup<sup id="cite_ref-pubchem_3-11" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>540 °C (1,004 °F; 813 K)<sup id="cite_ref-pubchem_3-12" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>480<span class="nowrap"> </span>mg/kg (mice, oral) </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external text" href="http://avogadro.chem.iastate.edu/MSDS/salicylic_acid.htm">MSDS</a><sup class="noprint Inline-Template"><span style="white-space: nowrap;">[<i><a href="/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot"><span title=" Dead link tagged August 2023">dead link</span></a></i><span style="visibility:hidden; color:transparent; padding-left:2px">‍</span>]</span></sup> </td></tr> <tr> <th colspan="2" style="background: #f8eaba; text-align: center;">Related compounds </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Related compounds</div> </td> <td><a href="/wiki/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a>,<br /><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a>,<br /><a href="/wiki/Phenol" title="Phenol">Phenol</a>, <a href="/wiki/Aspirin" title="Aspirin">Aspirin</a>,<br /><a href="/wiki/4-Hydroxybenzoic_acid" title="4-Hydroxybenzoic acid">4-Hydroxybenzoic acid</a>,<br /> <a href="/wiki/Magnesium_salicylate" title="Magnesium salicylate">Magnesium salicylate</a>,<br /><a href="/wiki/Choline_salicylate" class="mw-redirect" title="Choline salicylate">Choline salicylate</a>,<br /><a href="/wiki/Bismuth_subsalicylate" title="Bismuth subsalicylate">Bismuth subsalicylate</a>,<br /><a href="/wiki/Sulfosalicylic_acid" class="mw-redirect" title="Sulfosalicylic acid">Sulfosalicylic acid</a>,<br /><a href="/wiki/Salicylate_synthase" title="Salicylate synthase">Salicylate synthase</a> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=477314005&page2=Salicylic+acid">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Salicylic acid</b> is an <a href="/wiki/Organic_compound" title="Organic compound">organic compound</a> with the formula HOC<sub>6</sub>H<sub>4</sub>COOH.<sup id="cite_ref-pubchem_3-13" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> A colorless (or white), bitter-tasting solid, it is a precursor to and a <a href="/wiki/Active_metabolite" title="Active metabolite">metabolite</a> of <a href="/wiki/Acetylsalicylic_acid" class="mw-redirect" title="Acetylsalicylic acid">acetylsalicylic acid</a> (aspirin).<sup id="cite_ref-pubchem_3-14" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is a <a href="/wiki/Plant_hormone" title="Plant hormone">plant hormone</a>,<sup id="cite_ref-Ullmann_8-0" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> and has been listed by the <a href="/wiki/EPA" class="mw-redirect" title="EPA">EPA</a> <a href="/wiki/Toxic_Substances_Control_Act" class="mw-redirect" title="Toxic Substances Control Act">Toxic Substances Control Act</a> (TSCA) Chemical Substance Inventory as an experimental <a href="/wiki/Teratogen" class="mw-redirect" title="Teratogen">teratogen</a>.<sup id="cite_ref-lewis08_9-0" class="reference"><a href="#cite_note-lewis08-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> The name is from <a href="/wiki/Latin" title="Latin">Latin</a> <span title="Latin-language text"><i lang="la"><a href="/wiki/Salix" class="mw-redirect" title="Salix">salix</a></i></span> for <a href="/wiki/Willow_tree" class="mw-redirect" title="Willow tree">willow tree</a>, from which it was initially identified and derived. It is an ingredient in some anti-<a href="/wiki/Acne" title="Acne">acne</a> products. Salts and <a href="/wiki/Ester" title="Ester">esters</a> of salicylic acid are known as <b>salicylates</b>.<sup id="cite_ref-pubchem_3-15" class="reference"><a href="#cite_note-pubchem-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="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=1" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Medicine">Medicine</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=2" title="Edit section: Medicine"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Medical_uses_of_salicylic_acid" title="Medical uses of salicylic acid">Medical uses of salicylic acid</a></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Salicylic_acid_pads.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Salicylic_acid_pads.jpg/220px-Salicylic_acid_pads.jpg" decoding="async" width="220" height="165" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Salicylic_acid_pads.jpg/330px-Salicylic_acid_pads.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b6/Salicylic_acid_pads.jpg/440px-Salicylic_acid_pads.jpg 2x" data-file-width="2048" data-file-height="1536" /></a><figcaption><a href="/wiki/Cotton" title="Cotton">Cotton</a> pads soaked in salicylic acid can be used to chemically <a href="/wiki/Exfoliation_(cosmetology)" title="Exfoliation (cosmetology)">exfoliate</a> skin.</figcaption></figure> <p>Salicylic acid as a medication is commonly used to remove the outermost layer of the <a href="/wiki/Skin" title="Skin">skin</a>. As such, it is used to treat <a href="/wiki/Wart" title="Wart">warts</a>, <a href="/wiki/Psoriasis" title="Psoriasis">psoriasis</a>, <a href="/wiki/Acne_vulgaris" class="mw-redirect" title="Acne vulgaris">acne vulgaris</a>, <a href="/wiki/Ringworm" class="mw-redirect" title="Ringworm">ringworm</a>, <a href="/wiki/Dandruff" title="Dandruff">dandruff</a>, and <a href="/wiki/Ichthyosis" title="Ichthyosis">ichthyosis</a>.<sup id="cite_ref-pubchem_3-16" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-MTM2017_10-0" class="reference"><a href="#cite_note-MTM2017-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-WHO2008_11-0" class="reference"><a href="#cite_note-WHO2008-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Similar to other hydroxy acids, salicylic acid is an ingredient in many <a href="/wiki/Skincare" class="mw-redirect" title="Skincare">skincare</a> products for the treatment of <a href="/wiki/Seborrhoeic_dermatitis" title="Seborrhoeic dermatitis">seborrhoeic dermatitis</a>, <a href="/wiki/Acne" title="Acne">acne</a>, <a href="/wiki/Psoriasis" title="Psoriasis">psoriasis</a>, <a href="/wiki/Callus" title="Callus">calluses</a>, <a href="/wiki/Corn_(medicine)" class="mw-redirect" title="Corn (medicine)">corns</a>, <a href="/wiki/Keratosis_pilaris" title="Keratosis pilaris">keratosis pilaris</a>, <a href="/wiki/Acanthosis_nigricans" title="Acanthosis nigricans">acanthosis nigricans</a>, ichthyosis, and warts.<sup id="cite_ref-Madan2014_12-0" class="reference"><a href="#cite_note-Madan2014-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Uses_in_manufacturing">Uses in manufacturing</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=3" title="Edit section: Uses in manufacturing"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Salicylic acid is used as a <a href="/wiki/Food_preservative" class="mw-redirect" title="Food preservative">food preservative</a>, a <a href="/wiki/Bactericide" title="Bactericide">bactericide</a>, and an <a href="/wiki/Antiseptic" title="Antiseptic">antiseptic</a>.<sup id="cite_ref-mnet_13-0" class="reference"><a href="#cite_note-mnet-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-greene13_14-0" class="reference"><a href="#cite_note-greene13-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Salicylic acid is used in the production of other pharmaceuticals, including <a href="/wiki/4-aminosalicylic_acid" class="mw-redirect" title="4-aminosalicylic acid">4-aminosalicylic acid</a>, <a href="/wiki/Sulpiride" title="Sulpiride">sandulpiride</a>, and <a href="/w/index.php?title=Landetimide&action=edit&redlink=1" class="new" title="Landetimide (page does not exist)">landetimide</a> (via <a href="/w/index.php?title=Salethamide&action=edit&redlink=1" class="new" title="Salethamide (page does not exist)">salethamide</a>).<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> It is also used in <a href="/wiki/Picric_acid" title="Picric acid">picric acid</a> production.<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> </p><p>Salicylic acid has long been a key starting material for making <a href="/wiki/Acetylsalicylic_acid" class="mw-redirect" title="Acetylsalicylic acid">acetylsalicylic acid</a> (ASA or aspirin).<sup id="cite_ref-Ullmann_8-1" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> ASA is prepared by the <a href="/wiki/Acetylation" title="Acetylation">acetylation</a> of salicylic acid with the acetyl group from <a href="/wiki/Acetic_anhydride" title="Acetic anhydride">acetic anhydride</a> or <a href="/wiki/Acetyl_chloride" title="Acetyl chloride">acetyl chloride</a>.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> ASA is the standard to which all the other non-steroidal anti-inflammatory drugs (<a href="/wiki/NSAID" class="mw-redirect" title="NSAID">NSAIDs</a>) are compared. In veterinary medicine, this group of drugs is mainly used for treatment of inflammatory musculoskeletal disorders.<sup id="cite_ref-emea99_18-0" class="reference"><a href="#cite_note-emea99-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Bismuth_subsalicylate" title="Bismuth subsalicylate">Bismuth subsalicylate</a>, a <a href="/wiki/Salt_(chemistry)" title="Salt (chemistry)">salt</a> of <a href="/wiki/Bismuth" title="Bismuth">bismuth</a> and salicylic acid, "displays anti-inflammatory action (due to salicylic acid) and also acts as an antacid and mild antibiotic".<sup id="cite_ref-pubchem_3-17" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is an active ingredient in stomach-relief aids such as <a href="/wiki/Pepto-Bismol" class="mw-redirect" title="Pepto-Bismol">Pepto-Bismol</a> and some formulations of <a href="/wiki/Kaopectate" title="Kaopectate">Kaopectate</a>. </p><p>Other derivatives include <a href="/wiki/Methyl_salicylate" title="Methyl salicylate">methyl salicylate</a>, used as a <a href="/wiki/Liniment" title="Liniment">liniment</a> to soothe joint and muscle pain, and <a href="/wiki/Choline_salicylate" class="mw-redirect" title="Choline salicylate">choline salicylate</a>, which is used topically to relieve the pain of <a href="/wiki/Aphthous_ulcer" class="mw-redirect" title="Aphthous ulcer">mouth ulcers</a>.<sup id="cite_ref-pubchem_3-18" class="reference"><a href="#cite_note-pubchem-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-drugs_19-0" class="reference"><a href="#cite_note-drugs-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><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> <a href="/wiki/Aminosalicylic_acid" title="Aminosalicylic acid">Aminosalicylic acid</a> is used to induce remission in <a href="/wiki/Ulcerative_colitis" title="Ulcerative colitis">ulcerative colitis</a>, and has been used as an <a href="/wiki/Antitubercular_agent" class="mw-redirect" title="Antitubercular agent">antitubercular agent</a> often administered in association with <a href="/wiki/Isoniazid" title="Isoniazid">isoniazid</a>.<sup id="cite_ref-drugbank1_21-0" class="reference"><a href="#cite_note-drugbank1-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a> is a useful <a href="/wiki/Phosphor" title="Phosphor">phosphor</a> in the <a href="/wiki/Vacuum_ultraviolet" class="mw-redirect" title="Vacuum ultraviolet">vacuum ultraviolet</a> spectral range, with nearly flat quantum efficiency for wavelengths between 10 and 100 nm.<sup id="cite_ref-samson76_22-0" class="reference"><a href="#cite_note-samson76-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> It fluoresces in the blue at 420 nm. It is easily prepared on a clean surface by spraying a saturated solution of the salt in <a href="/wiki/Methanol" title="Methanol">methanol</a> followed by evaporation.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2021)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=4" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Salicylic acid modulates <a href="/wiki/COX-1" class="mw-redirect" title="COX-1">COX-1</a> enzymatic activity to decrease the formation of pro-inflammatory prostaglandins. Salicylate may competitively inhibit prostaglandin formation. </p><p>Salicylic acid, when applied to the skin surface, works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Salicylic acid inhibits the oxidation of <a href="/wiki/Uridine_diphosphate_glucose" title="Uridine diphosphate glucose">uridine-5-diphosphoglucose</a> (UDPG) competitively with <a href="/wiki/Nicotinamide_adenine_dinucleotide" title="Nicotinamide adenine dinucleotide">NADH</a> and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of <a href="/w/index.php?title=Uridine-5-phosphoglucuronic_acid&action=edit&redlink=1" class="new" title="Uridine-5-phosphoglucuronic acid (page does not exist)">uridine-5-phosphoglucuronic acid</a> to the phenolic acceptor.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.<sup id="cite_ref-drugbank_5-1" class="reference"><a href="#cite_note-drugbank-5"><span class="cite-bracket">[</span>5<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=Salicylic_acid&action=edit&section=5" title="Edit section: Safety"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Salicylate_poisoning" title="Salicylate poisoning">Salicylate poisoning</a></div> <p>If high concentrations of salicylic ointment are used <a href="/wiki/Topical_medication" title="Topical medication">topically</a>, high levels of salicylic acid can enter the blood, requiring <a href="/wiki/Hemodialysis" title="Hemodialysis">hemodialysis</a> to avoid further complications.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Cosmetic applications of the drug pose no significant risk.<sup id="cite_ref-labib_25-0" class="reference"><a href="#cite_note-labib-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Even in a worst-case use scenario in which one was using multiple salicylic acid-containing topical products, the aggregate plasma concentration of salicylic acid was well below what was permissible for acetylsalicylic acid (aspirin).<sup id="cite_ref-labib_25-1" class="reference"><a href="#cite_note-labib-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Since oral aspirin (which produces much higher salicylic acid plasma concentrations than dermal salicylic acid applications) poses no significant adverse pregnancy outcomes in terms of frequency of stillbirth, birth defects or developmental delay, use of salicylic acid containing cosmetics is safe for pregnant women.<sup id="cite_ref-labib_25-2" class="reference"><a href="#cite_note-labib-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Salicylic acid is present in most fruits and vegetables as for example in greatest quantities in berries and in beverages like tea. </p> <div class="mw-heading mw-heading2"><h2 id="Production_and_chemical_reactions">Production and chemical reactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=6" title="Edit section: Production and chemical reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=7" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Salicylic acid is <a href="/wiki/Biosynthesis" title="Biosynthesis">biosynthesized</a> from the amino acid <a href="/wiki/Phenylalanine" title="Phenylalanine">phenylalanine</a>. In <i><a href="/wiki/Arabidopsis_thaliana" title="Arabidopsis thaliana">Arabidopsis thaliana</a></i>, it can be synthesized via a phenylalanine-independent pathway. </p> <div class="mw-heading mw-heading3"><h3 id="Chemical_synthesis">Chemical synthesis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=8" title="Edit section: Chemical synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Commercial vendors prepare <a href="/wiki/Sodium_salicylate" title="Sodium salicylate">sodium salicylate</a> by treating <a href="/wiki/Sodium_phenolate" class="mw-redirect" title="Sodium phenolate">sodium phenolate</a> (the sodium salt of <a href="/wiki/Phenol" title="Phenol">phenol</a>) with <a href="/wiki/Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> at high pressure (100<span class="nowrap"> </span>atm) and high temperature (115<span class="nowrap"> </span>°C) – a method known as the <a href="/wiki/Kolbe-Schmitt_reaction" class="mw-redirect" title="Kolbe-Schmitt reaction">Kolbe-Schmitt reaction</a>. Acidifying the product with <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> gives salicylic acid: </p> <dl><dd><span typeof="mw:File"><a href="/wiki/File:Salicylic-Acid_General_Synthesis_V.2.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Salicylic-Acid_General_Synthesis_V.2.svg/400px-Salicylic-Acid_General_Synthesis_V.2.svg.png" decoding="async" width="400" height="88" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Salicylic-Acid_General_Synthesis_V.2.svg/600px-Salicylic-Acid_General_Synthesis_V.2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Salicylic-Acid_General_Synthesis_V.2.svg/800px-Salicylic-Acid_General_Synthesis_V.2.svg.png 2x" data-file-width="942" data-file-height="207" /></a></span></dd></dl> <p>At the laboratory scale, it can also be prepared by the <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> of <a href="/wiki/Aspirin" title="Aspirin">aspirin</a> (acetylsalicylic acid)<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> or <a href="/wiki/Methyl_salicylate" title="Methyl salicylate">methyl salicylate</a> (oil of <a href="/wiki/Wintergreen" title="Wintergreen">wintergreen</a>) with a strong acid or base; these reactions reverse those chemicals' commercial syntheses. </p> <div class="mw-heading mw-heading3"><h3 id="Reactions">Reactions</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=9" title="Edit section: Reactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Upon heating, salicylic acid converts to <a href="/wiki/Phenyl_salicylate" title="Phenyl salicylate">phenyl salicylate</a>:<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Ullmann_8-2" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>2<span class="nowrap"> </span>HOC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>H → C<sub>6</sub>H<sub>5</sub>O<sub>2</sub>C<sub>6</sub>H<sub>4</sub>OH + CO<sub>2</sub> + H<sub>2</sub>O</dd></dl> <p>Further heating gives <a href="/wiki/Xanthone" title="Xanthone">xanthone</a>.<sup id="cite_ref-Ullmann_8-3" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Salicylic acid as its conjugate base is a chelating agent, with an affinity for iron(III).<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> </p><p>Salicylic acid slowly degrades to phenol and carbon dioxide at 200–230 °C:<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p> <dl><dd>C<sub>6</sub>H<sub>4</sub>OH(CO<sub>2</sub>H) → C<sub>6</sub>H<sub>5</sub>OH + CO<sub>2</sub></dd></dl> <p>All isomers of <a href="/wiki/Chlorosalicylic_acid" title="Chlorosalicylic acid">chlorosalicylic acid</a> and of <a href="/wiki/Dichlorosalicylic_acid" title="Dichlorosalicylic acid">dichlorosalicylic acid</a> are known. 5-Chlorosalicylic acid is produced by direct <a href="/wiki/Chlorination_reaction" class="mw-redirect" title="Chlorination reaction">chlorination</a> of salicylic acid.<sup id="cite_ref-Ullmann_8-4" class="reference"><a href="#cite_note-Ullmann-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=10" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/History_of_aspirin" title="History of aspirin">History of aspirin</a></div> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Thom%C3%A9_Salix_alba_clean.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/Thom%C3%A9_Salix_alba_clean.jpg/220px-Thom%C3%A9_Salix_alba_clean.jpg" decoding="async" width="220" height="364" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a1/Thom%C3%A9_Salix_alba_clean.jpg/330px-Thom%C3%A9_Salix_alba_clean.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a1/Thom%C3%A9_Salix_alba_clean.jpg/440px-Thom%C3%A9_Salix_alba_clean.jpg 2x" data-file-width="1386" data-file-height="2291" /></a><figcaption>White willow (<i><a href="/wiki/Salix_alba" title="Salix alba">Salix alba</a></i>) is a natural source of salicylic acid.</figcaption></figure> <p><a href="/wiki/Willow" title="Willow">Willow</a> has long been used for medicinal purposes. <a href="/wiki/Pedanius_Dioscorides" title="Pedanius Dioscorides">Dioscorides</a>, whose writings were highly influential for more than 1,500 years,<sup id="cite_ref-Dioscorides_30-0" class="reference"><a href="#cite_note-Dioscorides-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> used 'Itea' (which was possibly a species of willow) as a treatment for 'painful intestinal obstructions,' birth control, for 'those who spit blood,' to remove calluses and corns and, externally, as a 'warm pack for gout.' <a href="/wiki/William_Turner_(naturalist)" title="William Turner (naturalist)">William Turner</a>, in 1597, repeated this, saying that willow bark, 'being burnt to ashes, and steeped in vinegar, takes away corns and other like risings in the feet and toes.'<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Some of these cures may describe the action of salicylic acid, which can be derived from the <a href="/wiki/Salicin" title="Salicin">salicin</a> present in willow. It is, however, a modern myth that Hippocrates used willow as a painkiller.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Hippocrates" title="Hippocrates">Hippocrates</a>, <a href="/wiki/Galen" title="Galen">Galen</a>, <a href="/wiki/Pliny_the_Elder" title="Pliny the Elder">Pliny the Elder</a>, and others knew that decoctions containing salicylate could ease pain and reduce fevers.<sup id="cite_ref-DMA_33-0" class="reference"><a href="#cite_note-DMA-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>It was used in Europe and China to treat these conditions.<sup id="cite_ref-ummc_35-0" class="reference"><a href="#cite_note-ummc-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> This remedy is mentioned in texts from <a href="/wiki/Ancient_Egypt" title="Ancient Egypt">Ancient Egypt</a>, <a href="/wiki/Sumer" title="Sumer">Sumer</a>, and <a href="/wiki/Assyria" title="Assyria">Assyria</a>.<sup id="cite_ref-Goldberg_36-0" class="reference"><a href="#cite_note-Goldberg-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Cherokee" title="Cherokee">Cherokee</a> and other Native Americans use an infusion of the bark for fever and other medicinal purposes.<sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> In 2014, archaeologists identified traces of salicylic acid on seventh-century pottery fragments found in east-central Colorado.<sup id="cite_ref-wdo_38-0" class="reference"><a href="#cite_note-wdo-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/Edward_Stone_(clergyman)" class="mw-redirect" title="Edward Stone (clergyman)">Reverend Edward Stone</a>, a vicar from <a href="/wiki/Chipping_Norton,_Oxfordshire" class="mw-redirect" title="Chipping Norton, Oxfordshire">Chipping Norton, Oxfordshire</a>, England, reported in 1763 that the bark of the willow was effective in reducing a fever.<sup id="cite_ref-RoyalSoc1763EdmundStone_39-0" class="reference"><a href="#cite_note-RoyalSoc1763EdmundStone-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Florence_Nightingale_salicylic_silk_letter.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Florence_Nightingale_salicylic_silk_letter.jpg/160px-Florence_Nightingale_salicylic_silk_letter.jpg" decoding="async" width="160" height="248" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Florence_Nightingale_salicylic_silk_letter.jpg/240px-Florence_Nightingale_salicylic_silk_letter.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fd/Florence_Nightingale_salicylic_silk_letter.jpg/319px-Florence_Nightingale_salicylic_silk_letter.jpg 2x" data-file-width="600" data-file-height="931" /></a><figcaption>Letter from <a href="/wiki/Florence_Nightingale" title="Florence Nightingale">Florence Nightingale</a> on "salicylic silk" as a dressing for cancer patients.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup></figcaption></figure> <p>An extract of willow bark, called <a href="/wiki/Salicin" title="Salicin">salicin</a>, after the <a href="/wiki/Latin" title="Latin">Latin</a> name for the white willow (<i><a href="/wiki/Salix_alba" title="Salix alba">Salix alba</a></i>), was isolated and named by <a href="/wiki/Germans" title="Germans">German</a> chemist <a href="/wiki/Johann_Andreas_Buchner" title="Johann Andreas Buchner">Johann Andreas Buchner</a> in 1828.<sup id="cite_ref-buchner28_41-0" class="reference"><a href="#cite_note-buchner28-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> A larger amount of the substance was isolated in 1829 by Henri Leroux, a French pharmacist.<sup id="cite_ref-leroux30_42-0" class="reference"><a href="#cite_note-leroux30-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Raffaele_Piria" title="Raffaele Piria">Raffaele Piria</a>, an <a href="/wiki/Italy" title="Italy">Italian</a> chemist, was able to convert the substance into a sugar and a second component, which on oxidation becomes salicylic acid.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> Salicylic acid was also isolated from the herb meadowsweet (<i><a href="/wiki/Filipendula_ulmaria" title="Filipendula ulmaria">Filipendula ulmaria</a></i>, formerly classified as <i>Spiraea ulmaria</i>) by German researchers in 1839.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> Their extract caused digestive problems such as <a href="/wiki/Gastric_irritation" class="mw-redirect" title="Gastric irritation">gastric irritation</a>, <a href="/wiki/Bleeding" title="Bleeding">bleeding</a>, <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, and even death when consumed in high doses. </p><p>In 1874 the Scottish physician <a href="/wiki/Thomas_John_MacLagan" title="Thomas John MacLagan">Thomas MacLagan</a> experimented with salicin as a treatment for acute <a href="/wiki/Rheumatism" title="Rheumatism">rheumatism</a>, with considerable success, as he reported in The Lancet in 1876.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> Meanwhile, German scientists tried sodium salicylate with less success and more severe side effects.<sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>In 1979, salicylates were found to be involved in induced defenses of <a href="/wiki/Tobacco" title="Tobacco">tobacco</a> against <a href="/wiki/Tobacco_mosaic_virus" title="Tobacco mosaic virus">tobacco mosaic virus</a>.<sup id="cite_ref-raskin92_49-0" class="reference"><a href="#cite_note-raskin92-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> In 1987, salicylic acid was identified as the long-sought signal that causes <a href="/wiki/Thermogenic_plant" title="Thermogenic plant">thermogenic plants</a>, such as the voodoo lily, <i><a href="/wiki/Sauromatum_guttatum" class="mw-redirect" title="Sauromatum guttatum">Sauromatum guttatum</a></i>, to produce heat.<sup id="cite_ref-raskin87_50-0" class="reference"><a href="#cite_note-raskin87-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Dietary_sources">Dietary sources</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=11" title="Edit section: Dietary sources"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Salicylic acid occurs in plants as free salicylic acid and its carboxylated esters and phenolic glycosides. Several studies suggest that humans metabolize salicylic acid in measurable quantities from these plants.<sup id="cite_ref-Malakar_51-0" class="reference"><a href="#cite_note-Malakar-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> High-salicylate beverages and foods include <a href="/wiki/Beer" title="Beer">beer</a>, <a href="/wiki/Coffee" title="Coffee">coffee</a>, <a href="/wiki/Tea" title="Tea">tea</a>, numerous fruits and vegetables, <a href="/wiki/Sweet_potato" title="Sweet potato">sweet potato</a>, <a href="/wiki/Nut_(food)" class="mw-redirect" title="Nut (food)">nuts</a>, and <a href="/wiki/Olive_oil" title="Olive oil">olive oil</a>.<sup id="cite_ref-drugs_19-1" class="reference"><a href="#cite_note-drugs-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Meat, poultry, fish, eggs, dairy products, sugar, breads and cereals have low salicylate content.<sup id="cite_ref-drugs_19-2" class="reference"><a href="#cite_note-drugs-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Swain_52-0" class="reference"><a href="#cite_note-Swain-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p>Some people with sensitivity to dietary salicylates may have symptoms of <a href="/wiki/Allergic_reaction" class="mw-redirect" title="Allergic reaction">allergic reaction</a>, such as <a href="/wiki/Bronchial_asthma" class="mw-redirect" title="Bronchial asthma">bronchial asthma</a>, <a href="/wiki/Rhinitis" title="Rhinitis">rhinitis</a>, <a href="/wiki/Gastrointestinal_disorder" class="mw-redirect" title="Gastrointestinal disorder">gastrointestinal disorders</a>, or <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a>, so may need to adopt a low-salicylate diet.<sup id="cite_ref-drugs_19-3" class="reference"><a href="#cite_note-drugs-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Plant_hormone">Plant hormone</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=12" title="Edit section: Plant hormone"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Salicylic acid is a <a href="/wiki/Natural_phenol" class="mw-redirect" title="Natural phenol">phenolic</a> <a href="/wiki/Phytohormone" class="mw-redirect" title="Phytohormone">phytohormone</a>, and is found in plants with roles in plant growth and development, <a href="/wiki/Photosynthesis" title="Photosynthesis">photosynthesis</a>, <a href="/wiki/Transpiration" title="Transpiration">transpiration</a>, and <a href="/wiki/Ion" title="Ion">ion</a> uptake and transport.<sup id="cite_ref-Vlot-et-al-2009_53-0" class="reference"><a href="#cite_note-Vlot-et-al-2009-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> Salicylic acid is involved in <a href="/wiki/Endogenous" class="mw-redirect" title="Endogenous">endogenous</a> signaling, mediating plant defense against <a href="/wiki/Pathogens" class="mw-redirect" title="Pathogens">pathogens</a>.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> It plays a role in the resistance to pathogens (i.e. <a href="/wiki/Systemic_acquired_resistance" title="Systemic acquired resistance">systemic acquired resistance</a>) by inducing the production of <a href="/wiki/Pathogenesis-related_protein" title="Pathogenesis-related protein">pathogenesis-related proteins</a> and other defensive metabolites.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> SA's defense signaling role is most clearly demonstrated by experiments which do away with it: Delaney et al. 1994, Gaffney et al. 1993, Lawton et al. 1995, and Vernooij et al. 1994 each use <i><a href="/wiki/Nicotiana_tabacum" title="Nicotiana tabacum">Nicotiana tabacum</a></i> or <i><a href="/wiki/Arabidopsis_thaliana" title="Arabidopsis thaliana">Arabidopsis</a></i> expressing <i><a href="/w/index.php?title=NahG&action=edit&redlink=1" class="new" title="NahG (page does not exist)">nahG</a></i>, for <a href="/wiki/Salicylate_hydroxylase" class="mw-redirect" title="Salicylate hydroxylase">salicylate hydroxylase</a>. Pathogen inoculation did not produce the customarily high SA levels, SAR was not produced, and no <a href="/wiki/Pathogenesis-related_protein" title="Pathogenesis-related protein">pathogenesis-related</a> (PR) genes were <a href="/wiki/Gene_expression" title="Gene expression">expressed</a> in <a href="/w/index.php?title=Systemic_leaf&action=edit&redlink=1" class="new" title="Systemic leaf (page does not exist)">systemic leaves</a>. Indeed, the subjects were more susceptible to virulent – and even normally avirulent – pathogens.<sup id="cite_ref-Vlot-et-al-2009_53-1" class="reference"><a href="#cite_note-Vlot-et-al-2009-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Exogeny" title="Exogeny">Exogenously</a>, salicylic acid can aid plant development via enhanced seed germination, bud flowering, and fruit ripening, though too high of a concentration of salicylic acid can negatively regulate these developmental processes.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>The volatile methyl ester of salicylic acid, <a href="/wiki/Methyl_salicylate" title="Methyl salicylate">methyl salicylate</a>, can also diffuse through the air, facilitating plant-<a href="/wiki/Plant_communication" title="Plant communication">plant communication</a>.<sup id="cite_ref-Taiz-Zeiger-2002_57-0" class="reference"><a href="#cite_note-Taiz-Zeiger-2002-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Methyl salicylate is taken up by the <a href="/wiki/Stomata" class="mw-redirect" title="Stomata">stomata</a> of the nearby plant, where it can induce an immune response after being converted back to salicylic acid.<sup id="cite_ref-Chamovitz-2012_58-0" class="reference"><a href="#cite_note-Chamovitz-2012-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Signal_transduction">Signal transduction</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=13" title="Edit section: Signal transduction"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A number of proteins have been identified that interact with SA in plants, especially salicylic acid binding proteins (SABPs) and the NPR genes (nonexpressor of pathogenesis-related genes), which are putative receptors.<sup id="cite_ref-59" class="reference"><a href="#cite_note-59"><span class="cite-bracket">[</span>59<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=Salicylic_acid&action=edit&section=14" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239009302">.mw-parser-output .portalbox{padding:0;margin:0.5em 0;display:table;box-sizing:border-box;max-width:175px;list-style:none}.mw-parser-output .portalborder{border:1px solid var(--border-color-base,#a2a9b1);padding:0.1em;background:var(--background-color-neutral-subtle,#f8f9fa)}.mw-parser-output .portalbox-entry{display:table-row;font-size:85%;line-height:110%;height:1.9em;font-style:italic;font-weight:bold}.mw-parser-output .portalbox-image{display:table-cell;padding:0.2em;vertical-align:middle;text-align:center}.mw-parser-output .portalbox-link{display:table-cell;padding:0.2em 0.2em 0.2em 0.3em;vertical-align:middle}@media(min-width:720px){.mw-parser-output .portalleft{clear:left;float:left;margin:0.5em 1em 0.5em 0}.mw-parser-output .portalright{clear:right;float:right;margin:0.5em 0 0.5em 1em}}</style><ul role="navigation" aria-label="Portals" class="noprint portalbox portalborder portalright"> <li class="portalbox-entry"><span class="portalbox-image"><span class="noviewer" typeof="mw:File"><span><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/12px-WHO_Rod.svg.png" decoding="async" width="12" height="28" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/18px-WHO_Rod.svg.png 1.5x, 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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 class="citation book cs1">"Front Matter". <i>Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)</i>. Cambridge: <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">The Royal Society of Chemistry</a>. 2014. p. 64. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1039%2F9781849733069-FP001">10.1039/9781849733069-FP001</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-85404-182-4" title="Special:BookSources/978-0-85404-182-4"><bdi>978-0-85404-182-4</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Front+Matter&rft.btitle=Nomenclature+of+Organic+Chemistry%3A+IUPAC+Recommendations+and+Preferred+Names+2013+%28Blue+Book%29&rft.place=Cambridge&rft.pages=64&rft.pub=The+Royal+Society+of+Chemistry&rft.date=2014&rft_id=info%3Adoi%2F10.1039%2F9781849733069-FP001&rft.isbn=978-0-85404-182-4&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-crc-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-crc_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-crc_2-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-crc_2-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHaynes2011" class="citation book cs1">Haynes WM, ed. (2011). <i><a href="/wiki/CRC_Handbook_of_Chemistry_and_Physics" title="CRC Handbook of Chemistry and Physics">CRC Handbook of Chemistry and Physics</a></i> (92nd ed.). Boca Raton, FL: <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>. p. 3.306. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/1-4398-5511-0" title="Special:BookSources/1-4398-5511-0"><bdi>1-4398-5511-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=CRC+Handbook+of+Chemistry+and+Physics&rft.place=Boca+Raton%2C+FL&rft.pages=3.306&rft.edition=92nd&rft.pub=CRC+Press&rft.date=2011&rft.isbn=1-4398-5511-0&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-pubchem-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-pubchem_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pubchem_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pubchem_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-pubchem_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-pubchem_3-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-pubchem_3-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-pubchem_3-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-pubchem_3-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-pubchem_3-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-pubchem_3-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-pubchem_3-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-pubchem_3-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-pubchem_3-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-pubchem_3-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-pubchem_3-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-pubchem_3-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-pubchem_3-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-pubchem_3-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-pubchem_3-18"><sup><i><b>s</b></i></sup></a></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://pubchem.ncbi.nlm.nih.gov/compound/Salicylic-acid">"Salicylic acid"</a>. PubChem, US National Library of Medicine. 19 Nov 2023<span class="reference-accessdate">. Retrieved <span class="nowrap">19 Nov</span> 2023</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Salicylic+acid&rft.pub=PubChem%2C+US+National+Library+of+Medicine&rft.date=2023-11-19&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2FSalicylic-acid&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-sioc-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-sioc_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-sioc_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-sioc_4-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFAtherton_SeidellWilliam_F._Linke1952" class="citation book cs1">Atherton Seidell, William F. 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Wishart">Wishart DS</a>, Djombou Feunang Y, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. <a rel="nofollow" class="external text" href="https://go.drugbank.com/drugs/DB00936">"Salycylic acid | DrugBank Online"</a>. <i><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></i>. 5.0.</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=Salycylic+acid+%7C+DrugBank+Online&rft.aulast=Wishart&rft.aufirst=David+S.&rft.au=Djombou+Feunang%2C+Yannick&rft.au=Guo%2C+An+Chi&rft.au=Lo%2C+Elvis+J.&rft.au=Marcu%2C+Ana&rft.au=Grant%2C+Jason+R.&rft.au=Sajed%2C+Tanvir&rft.au=Johnson%2C+Daniel&rft.au=Li%2C+Carin&rft.au=Sayeeda%2C+Zinat&rft.au=Assempour%2C+Nazanin&rft.au=Iynkkaran%2C+Ithayavani&rft.au=Liu%2C+Yifeng&rft.au=Maciejewski%2C+Adam&rft.au=Gale%2C+Nicola&rft.au=Wilson%2C+Alex&rft.au=Chin%2C+Lucy&rft.au=Cummings%2C+Ryan&rft.au=Le%2C+Diana&rft.au=Pon%2C+Allison&rft.au=Knox%2C+Craig&rft.au=Wilson%2C+Michael&rft_id=https%3A%2F%2Fgo.drugbank.com%2Fdrugs%2FDB00936&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-NIST-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-NIST_6-0">^</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="http://webbook.nist.gov/cgi/cbook.cgi?ID=C69727&Type=HCOMBS">"Salicylic acid"</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170215084320/http://webbook.nist.gov/cgi/cbook.cgi?ID=C69727&Type=HCOMBS">Archived</a> from the original on 2017-02-15<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-08-17</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Salicylic+acid&rft_id=http%3A%2F%2Fwebbook.nist.gov%2Fcgi%2Fcbook.cgi%3FID%3DC69727%26Type%3DHCOMBS&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-sigma-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-sigma_7-0">^</a></b></span> <span class="reference-text"><a href="/wiki/Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich Co.</a>, <a rel="nofollow" class="external text" href="https://www.sigmaaldrich.com/catalog/product/aldrich/w398500">Salicylic acid</a>. </span> </li> <li id="cite_note-Ullmann-8"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_8-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_8-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_8-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Ullmann_8-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Ullmann_8-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBoullardLeblancBesson2000" class="citation book cs1">Boullard O, Leblanc H, Besson B (2000). 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"From willow bark to acetylsalicylic acid". <i>Dansk Medicinhistorisk Årbog</i> (in Danish). <b>37</b>: 79–98. <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/20509453">20509453</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:10053542">10053542</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Dansk+Medicinhistorisk+%C3%85rbog&rft.atitle=From+willow+bark+to+acetylsalicylic+acid&rft.volume=37&rft.pages=79-98&rft.date=2009&rft_id=info%3Apmid%2F20509453&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A10053542%23id-name%3DS2CID&rft.aulast=Norn&rft.aufirst=S&rft.au=Permin%2C+H&rft.au=Kruse%2C+PR&rft.au=Kruse%2C+E&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVane2000" class="citation journal cs1 cs1-prop-long-vol">Vane JR (2000). <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11192932/">"The fight against rheumatism: from willow bark to COX-1 sparing drugs"</a>. <i>J Physiol Pharmacol</i>. 51(4 Pt 1) (4 Pt 1): 573–86. <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/11192932">11192932</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J+Physiol+Pharmacol.&rft.atitle=The+fight+against+rheumatism%3A+from+willow+bark+to+COX-1+sparing+drugs&rft.volume=51%284+Pt+1%29&rft.issue=4+Pt+1&rft.pages=573-86&rft.date=2000&rft_id=info%3Apmid%2F11192932&rft.aulast=Vane&rft.aufirst=JR&rft_id=https%3A%2F%2Fpubmed.ncbi.nlm.nih.gov%2F11192932%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-ummc-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-ummc_35-0">^</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="http://www.umm.edu/altmed/articles/willow-bark-000281.htm">"Willow bark"</a>. <i>University of Maryland Medical Center</i>. <a href="/wiki/University_of_Maryland" class="mw-redirect" title="University of Maryland">University of Maryland</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20111224113137/http://www.umm.edu/altmed/articles/willow-bark-000281.htm">Archived</a> from the original on 24 December 2011<span class="reference-accessdate">. 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Retrieved <span class="nowrap">24 March</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemical+Heritage+Magazine&rft.atitle=Aspirin%3A+Turn+of+the+Century+Miracle+Drug&rft.ssn=summer&rft.volume=27&rft.issue=2&rft.pages=26-30&rft.date=2009&rft.aulast=Goldberg&rft.aufirst=DR&rft_id=https%3A%2F%2Fwww.sciencehistory.org%2Fdistillations%2Fmagazine%2Faspirin-turn-of-the-century-miracle-drug&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-37">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFHemelChiltoskey1975" class="citation book cs1">Hemel PB, Chiltoskey MU (1975). <i>Cherokee Plants and Their Uses – A 400 Year History</i>. 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Archived from <a rel="nofollow" class="external text" href="http://herb.umd.umich.edu/">the original</a> on 2007-12-06.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=A+Database+of+Foods%2C+Drugs%2C+Dyes+and+Fibers+of+Native+American+Peoples%2C+Derived+from+Plants&rft.aulast=Moerman&rft.aufirst=D&rft_id=http%3A%2F%2Fherb.umd.umich.edu%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span> A search of this database for "salix AND medicine" finds 63 entries.</span> </li> <li id="cite_note-wdo-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-wdo_38-0">^</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="http://westerndigs.org/prehistoric-pottery-found-in-colorado-contains-ancient-natural-aspirin/">"1,300-Year-Old Pottery Found in Colorado Contains Ancient 'Natural Aspirin'<span class="cs1-kern-right"></span>"</a>. 12 August 2014. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140813231049/http://westerndigs.org/prehistoric-pottery-found-in-colorado-contains-ancient-natural-aspirin/">Archived</a> from the original on 2014-08-13<span class="reference-accessdate">. Retrieved <span class="nowrap">2014-08-13</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=1%2C300-Year-Old+Pottery+Found+in+Colorado+Contains+Ancient+%27Natural+Aspirin%27&rft.date=2014-08-12&rft_id=http%3A%2F%2Fwesterndigs.org%2Fprehistoric-pottery-found-in-colorado-contains-ancient-natural-aspirin%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-RoyalSoc1763EdmundStone-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-RoyalSoc1763EdmundStone_39-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStoneEdmund1763" class="citation journal cs1">Stone, Edmund (1763). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=j0JFAAAAcAAJ&pg=PA195">"An Account of the Success of the Bark of the Willow in the Cure of Agues"</a>. <i>Philosophical Transactions of the Royal Society of London</i>. <b>53</b>: 195–200. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1098%2Frstl.1763.0033">10.1098/rstl.1763.0033</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Philosophical+Transactions+of+the+Royal+Society+of+London&rft.atitle=An+Account+of+the+Success+of+the+Bark+of+the+Willow+in+the+Cure+of+Agues&rft.volume=53&rft.pages=195-200&rft.date=1763&rft_id=info%3Adoi%2F10.1098%2Frstl.1763.0033&rft.au=Stone&rft.au=Edmund&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dj0JFAAAAcAAJ%26pg%3DPA195&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-40">^</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://collections.thackraymuseum.co.uk/object-2013-0503">"2013.0503 | Collections Online"</a>. <i>collections.thackraymuseum.co.uk</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2024-05-30</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=collections.thackraymuseum.co.uk&rft.atitle=2013.0503+%7C+Collections+Online&rft_id=https%3A%2F%2Fcollections.thackraymuseum.co.uk%2Fobject-2013-0503&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-buchner28-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-buchner28_41-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBuchner1828" class="citation book cs1"><a href="/wiki/Johann_Andreas_Buchner" title="Johann Andreas Buchner">Buchner A</a> (1828). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=r-40AQAAMAAJ&pg=PA405">"Ueber das Rigatellische Fiebermittel und über eine in der Weidenrinde entdeckte alcaloidische Substanz"</a> [On Rigatelli's antipyretic [i.e., anti-fever drug] and on an alkaloid substance discovered in willow bark]. <i>Repertorium für die Pharmacie</i>. Bei J. L. Schrag. pp. 405–. <q><span title="German-language text"><span lang="de"><i>Noch ist es mir aber nicht geglückt, den bittern Bestandtheil der Weide, den ich </i>Salicin<i> nennen will, ganz frei von allem Färbestoff darzustellen.</i></span></span></q> [I have still not succeeded in preparing the bitter component of willow, which I will name <i>salicin</i>, completely free from colored matter]</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Ueber+das+Rigatellische+Fiebermittel+und+%C3%BCber+eine+in+der+Weidenrinde+entdeckte+alcaloidische+Substanz&rft.btitle=Repertorium+f%C3%BCr+die+Pharmacie&rft.pages=405-&rft.pub=Bei+J.+L.+Schrag&rft.date=1828&rft.aulast=Buchner&rft.aufirst=A.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dr-40AQAAMAAJ%26pg%3DPA405&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-leroux30-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-leroux30_42-0">^</a></b></span> <span class="reference-text">See: <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLeroux1830" class="citation journal cs1">Leroux H (1830). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=TYIDAAAAYAAJ&pg=PA340">"Mémoire relatif à l'analyse de l'écorce de saule et à la découverte d'un principe immédiat propre à remplacer le sulfate de quinine"</a> [Memoir concerning the analysis of willow bark and the discovery of a substance immediately likely to replace quinine sulfate]. <i>Journal de Chimie Médicale, de Pharmacie et de Toxicologie</i>. <b>6</b>: 340–342.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+de+Chimie+M%C3%A9dicale%2C+de+Pharmacie+et+de+Toxicologie&rft.atitle=M%C3%A9moire+relatif+%C3%A0+l%27analyse+de+l%27%C3%A9corce+de+saule+et+%C3%A0+la+d%C3%A9couverte+d%27un+principe+imm%C3%A9diat+propre+%C3%A0+remplacer+le+sulfate+de+quinine&rft.volume=6&rft.pages=340-342&rft.date=1830&rft.aulast=Leroux&rft.aufirst=H.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DTYIDAAAAYAAJ%26pg%3DPA340&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></li> <li>A report on Leroux's presentation to the French Academy of Sciences also appeared in: <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=EVKATMXxkCAC&pg=PA20"><i>Mémoires de l'Académie des sciences de l'Institut de France</i></a>. Institut de France. 1838. pp. 20–.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=M%C3%A9moires+de+l%27Acad%C3%A9mie+des+sciences+de+l%27Institut+de+France&rft.pages=20-&rft.pub=Institut+de+France&rft.date=1838&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DEVKATMXxkCAC%26pg%3DPA20&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></li></ul> </span></li> <li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPiria1838" class="citation journal cs1">Piria (1838). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170727013453/http://gallica.bnf.fr/ark:/12148/bpt6k2965r/f621.image">"Sur de neuveaux produits extraits de la salicine"</a> [On new products extracted from salicine]. <i><a href="/wiki/Comptes_rendus" class="mw-redirect" title="Comptes rendus">Comptes rendus</a></i>. <b>6</b>: 620–624. Archived from <a rel="nofollow" class="external text" href="http://gallica.bnf.fr/ark:/12148/bpt6k2965r/f621.image">the original</a> on 2017-07-27. p. 622: <q>Piria mentions "Hydrure de salicyle" (hydrogen salicylate, i.e., salicylic acid).</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Comptes+rendus&rft.atitle=Sur+de+neuveaux+produits+extraits+de+la+salicine&rft.volume=6&rft.pages=620-624&rft.date=1838&rft.au=Piria&rft_id=http%3A%2F%2Fgallica.bnf.fr%2Fark%3A%2F12148%2Fbpt6k2965r%2Ff621.image&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFJeffreys2005" class="citation book cs1">Jeffreys D (2005). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=x-sL4iNQOgcC&pg=PA38"><i>Aspirin: the remarkable story of a wonder drug</i></a>. New York: Bloomsbury. pp. 38–40. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-58234-600-7" title="Special:BookSources/978-1-58234-600-7"><bdi>978-1-58234-600-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Aspirin%3A+the+remarkable+story+of+a+wonder+drug&rft.place=New+York&rft.pages=38-40&rft.pub=Bloomsbury&rft.date=2005&rft.isbn=978-1-58234-600-7&rft.aulast=Jeffreys&rft.aufirst=Diarmuid&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dx-sL4iNQOgcC%26pg%3DPA38&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLöwigWeidmann1839" class="citation journal cs1">Löwig C, Weidmann S (1839). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=iBcAAAAAMAAJ&pg=PA57">"III. Untersuchungen mit dem destillierten Wasser der Blüthen von <i>Spiraea Ulmaria</i>"</a> [III. Investigations of the water distilled from the blossoms of <i>Spiraea ulmaria</i>]. <i>Annalen der Physik und Chemie; Beiträge zur Organischen Chemie (Contributions to Organic Chemistry)</i> (46): 57–83.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Annalen+der+Physik+und+Chemie%3B+Beitr%C3%A4ge+zur+Organischen+Chemie+%28Contributions+to+Organic+Chemistry%29&rft.atitle=III.+Untersuchungen+mit+dem+destillierten+Wasser+der+Bl%C3%BCthen+von+Spiraea+Ulmaria&rft.issue=46&rft.pages=57-83&rft.date=1839&rft.aulast=L%C3%B6wig&rft.aufirst=C.&rft.au=Weidmann%2C+S.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DiBcAAAAAMAAJ%26pg%3DPA57&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span> Löwig and Weidman called salicylic acid <i>Spiräasaure</i> (spiraea acid)</span> </li> <li id="cite_note-46"><span class="mw-cite-backlink"><b><a href="#cite_ref-46">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMacLagan1876" class="citation journal cs1"><a href="/wiki/Thomas_John_MacLagan" title="Thomas John MacLagan">MacLagan TJ</a> (28 October 1876). <a rel="nofollow" class="external text" href="https://www.thelancet.com/journals/lancet/article/PIIS0140-6736(02)49509-8/fulltext">"The treatment of acute rheumatism by salicin"</a>. <i>The Lancet</i>. <b>108</b> (2774): 383. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0140-6736%2802%2949509-8">10.1016/S0140-6736(02)49509-8</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Lancet&rft.atitle=The+treatment+of+acute+rheumatism+by+salicin&rft.volume=108&rft.issue=2774&rft.pages=383&rft.date=1876-10-28&rft_id=info%3Adoi%2F10.1016%2FS0140-6736%2802%2949509-8&rft.aulast=MacLagan&rft.aufirst=TJ&rft_id=https%3A%2F%2Fwww.thelancet.com%2Fjournals%2Flancet%2Farticle%2FPIIS0140-6736%2802%2949509-8%2Ffulltext&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-47"><span class="mw-cite-backlink"><b><a href="#cite_ref-47">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFMacLagan1900" class="citation journal cs1">MacLagan T (1900). 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class="citation journal cs1">Koo YM, Heo AY, Choi HW (February 2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7012573">"Salicylic Acid as a Safe Plant Protector and Growth Regulator"</a>. <i>The Plant Pathology Journal</i>. <b>36</b> (1): 1–10. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.5423%2FPPJ.RW.12.2019.0295">10.5423/PPJ.RW.12.2019.0295</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7012573">7012573</a></span>. <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/32089657">32089657</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Plant+Pathology+Journal&rft.atitle=Salicylic+Acid+as+a+Safe+Plant+Protector+and+Growth+Regulator&rft.volume=36&rft.issue=1&rft.pages=1-10&rft.date=2020-02&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7012573%23id-name%3DPMC&rft_id=info%3Apmid%2F32089657&rft_id=info%3Adoi%2F10.5423%2FPPJ.RW.12.2019.0295&rft.aulast=Koo&rft.aufirst=YM&rft.au=Heo%2C+AY&rft.au=Choi%2C+HW&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7012573&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-Taiz-Zeiger-2002-57"><span class="mw-cite-backlink"><b><a href="#cite_ref-Taiz-Zeiger-2002_57-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTaizZeiger2002" class="citation book cs1">Taiz L, Zeiger E (2002). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20140305085915/http://www.scribd.com/doc/87221186/Plant-Physiology-3rd-Edition-Taiz-amp-Zeiger-2002"><i>Plant physiology</i></a>. Sunderland, Mass: Sinauer Associates. p. 306. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-87893-823-0" title="Special:BookSources/0-87893-823-0"><bdi>0-87893-823-0</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/50002466">50002466</a>. Archived from <a rel="nofollow" class="external text" href="https://www.scribd.com/doc/87221186/Plant-Physiology-3rd-Edition-Taiz-amp-Zeiger-2002">the original</a> on 2014-03-05.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Plant+physiology&rft.place=Sunderland%2C+Mass&rft.pages=306&rft.pub=Sinauer+Associates&rft.date=2002&rft_id=info%3Aoclcnum%2F50002466&rft.isbn=0-87893-823-0&rft.aulast=Taiz&rft.aufirst=L&rft.au=Zeiger%2C+E&rft_id=http%3A%2F%2Fwww.scribd.com%2Fdoc%2F87221186%2FPlant-Physiology-3rd-Edition-Taiz-amp-Zeiger-2002&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-Chamovitz-2012-58"><span class="mw-cite-backlink"><b><a href="#cite_ref-Chamovitz-2012_58-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFChamovitz2012" class="citation book cs1">Chamovitz D (2012). <i>What A Plant Knows - A Field Guide to the Senses of your Garden - and Beyond</i>. Oxford, England: Oneworld. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-85168-910-1" title="Special:BookSources/978-1-85168-910-1"><bdi>978-1-85168-910-1</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/775030365">775030365</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=What+A+Plant+Knows+-+A+Field+Guide+to+the+Senses+of+your+Garden+-+and+Beyond&rft.place=Oxford%2C+England&rft.pub=Oneworld&rft.date=2012&rft_id=info%3Aoclcnum%2F775030365&rft.isbn=978-1-85168-910-1&rft.aulast=Chamovitz&rft.aufirst=D&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></span> </li> <li id="cite_note-59"><span class="mw-cite-backlink"><b><a href="#cite_ref-59">^</a></b></span> <span class="reference-text">Kumar, D. 2014. Salicylic acid signaling in disease resistance. Plant Science 228:127–134.</span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=16" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSchrör2016" class="citation book cs1">Schrör K (2016). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=MaFtDAAAQBAJ&pg=PA9"><i>Acetylsalicylic Acid</i></a> (2 ed.). John Wiley & Sons. pp. 9–10. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-68502-8" title="Special:BookSources/978-3-527-68502-8"><bdi>978-3-527-68502-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Acetylsalicylic+Acid&rft.pages=9-10&rft.edition=2&rft.pub=John+Wiley+%26+Sons&rft.date=2016&rft.isbn=978-3-527-68502-8&rft.aulast=Schr%C3%B6r&rft.aufirst=K&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DMaFtDAAAQBAJ%26pg%3DPA9&rfr_id=info%3Asid%2Fen.wikipedia.org%3ASalicylic+acid" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Salicylic_acid&action=edit&section=17" title="Edit section: External links"><span>edit</span></a><span 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href="https://www.cdc.gov/niosh/ipcsneng/neng0563.html">International Chemical Safety Cards | CDC/NIOSH</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20171025010805/https://www.cdc.gov/niosh/ipcsneng/neng0563.html">Archived</a> 2017-10-25 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></li> <li><a rel="nofollow" class="external text" href="https://www.mjlphd.net/uploads/2/4/4/0/24404036/english_translation_of_on_the_synthesis_of_salicylic_acid_by_hermann_kolbe.pdf">"On the syntheses of salicylic acid"</a> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200806230710/https://www.mjlphd.net/uploads/2/4/4/0/24404036/english_translation_of_on_the_synthesis_of_salicylic_acid_by_hermann_kolbe.pdf">Archived</a> 2020-08-06 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a>: English Translation of Hermann Kolbe's seminal 1860 German article "Ueber Synthese der 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title="8-Hydroxyquinoline">8-Hydroxyquinoline</a></li> <li><a href="/wiki/Light_therapy" title="Light therapy">Blue light therapy</a></li> <li><a href="/wiki/Tea_tree_oil" title="Tea tree oil">Tea tree oil</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Keratolytic" title="Keratolytic">Keratolytic</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Glycolic_acid" title="Glycolic acid">Glycolic acid</a></li> <li><a class="mw-selflink selflink">Salicylic acid</a><sup>#</sup></li> <li><a href="/wiki/Sulfur_(pharmacy)" class="mw-redirect" title="Sulfur (pharmacy)">Sulfur</a></li> <li><a href="/wiki/Benzoyl_peroxide" title="Benzoyl peroxide">Benzoyl peroxide</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anti-inflammatory" title="Anti-inflammatory">Anti-inflammatory</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/Niacinamide" class="mw-redirect" title="Niacinamide">Niacinamide</a></li> <li><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a><sup>#</sup></li> <li><a href="/wiki/Aspirin" title="Aspirin">Aspirin</a><sup>#</sup></li> <li><a href="/wiki/Light_therapy" title="Light therapy">Red light therapy</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antibiotics" class="mw-redirect" title="Antibiotics">Antibiotics</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Dapsone" title="Dapsone">Dapsone</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li> <li><a href="/wiki/Sulfacetamide" title="Sulfacetamide">Sulfacetamide</a></li> <li><a href="/wiki/Tetracycline_antibiotics" title="Tetracycline antibiotics">Tetracyclines</a> (<a href="/wiki/Lymecycline" title="Lymecycline">Lymecycline</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/wiki/Doxycycline" title="Doxycycline">Doxycycline</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Hormone" title="Hormone">Hormonal</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/Antiandrogen" title="Antiandrogen">Antiandrogens</a> <ul><li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Cyproterone_acetate" title="Cyproterone acetate">Cyproterone acetate</a></li> <li><a href="/wiki/Drospirenone" title="Drospirenone">Drospirenone</a></li> <li><a href="/wiki/Flutamide" title="Flutamide">Flutamide</a></li> <li><a href="/wiki/Spironolactone" title="Spironolactone">Spironolactone</a>)</li></ul></li> <li><a href="/wiki/Estrogen" title="Estrogen">Estrogens</a> <ul><li><a href="/wiki/Estradiol" title="Estradiol">Estradiol</a></li> <li><a href="/wiki/Ethinylestradiol" title="Ethinylestradiol">Ethinylestradiol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Retinoid" title="Retinoid">Retinoids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Adapalene" title="Adapalene">Adapalene</a></li> <li><a href="/wiki/Isotretinoin" title="Isotretinoin">Isotretinoin</a></li> <li><a href="/wiki/Motretinide" title="Motretinide">Motretinide</a></li> <li><a href="/wiki/Tazarotene" title="Tazarotene">Tazarotene</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a></li> <li><a href="/wiki/Trifarotene" title="Trifarotene">Trifarotene</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Epristeride" title="Epristeride">Epristeride</a></li> <li><a href="/wiki/Mesulfen" title="Mesulfen">Mesulfen</a></li> <li><a href="/wiki/Pelretin" title="Pelretin">Pelretin</a></li> <li><a href="/wiki/Stridex" title="Stridex">Stridex</a></li> <li><a href="/wiki/Tioxolone" title="Tioxolone">Tioxolone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</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/Adapalene/benzoyl_peroxide" title="Adapalene/benzoyl peroxide">Adapalene/benzoyl peroxide</a></li> <li><a href="/wiki/Clindamycin/adapalene/benzoyl_peroxide" title="Clindamycin/adapalene/benzoyl peroxide">Clindamycin/adapalene/benzoyl peroxide</a></li> <li><a href="/wiki/Clindamycin/benzoyl_peroxide" title="Clindamycin/benzoyl peroxide">Clindamycin/benzoyl peroxide</a></li> <li><a href="/wiki/Clindamycin/tretinoin" title="Clindamycin/tretinoin">Clindamycin/tretinoin</a></li> <li><a href="/wiki/Erythromycin/benzoyl_peroxide" title="Erythromycin/benzoyl peroxide">Erythromycin/benzoyl peroxide</a></li> <li><a href="/wiki/Erythromycin/isotretinoin" title="Erythromycin/isotretinoin">Erythromycin/isotretinoin</a></li> <li><a href="/wiki/Sulfacetamide/sulfur" title="Sulfacetamide/sulfur">Sulfacetamide/sulfur</a></li> <li><a href="/wiki/Tretinoin/benzoyl_peroxide" title="Tretinoin/benzoyl peroxide">Tretinoin/benzoyl peroxide</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="Ancient_anaesthesia" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Ancient_anaesthesia" title="Template:Ancient anaesthesia"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Ancient_anaesthesia" title="Template talk:Ancient anaesthesia"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Ancient_anaesthesia" title="Special:EditPage/Template:Ancient anaesthesia"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Ancient_anaesthesia" style="font-size:114%;margin:0 4em"><a href="/wiki/History_of_general_anesthesia" title="History of general anesthesia">Ancient anaesthesia</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Plants / animals</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><i><a href="/wiki/Aconitum" title="Aconitum">Aconitum</a></i> (aconite)</li> <li><i><a href="/wiki/Atropa_belladonna" title="Atropa belladonna">Atropa belladonna</a></i> (belladonna)</li> <li><a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">Cannabis</a> <ul><li><a href="/wiki/Medical_cannabis" title="Medical cannabis">medical use</a></li></ul></li> <li><a href="/wiki/Castoreum" title="Castoreum">Castoreum</a></li> <li><a href="/wiki/Coca" title="Coca">Coca</a></li> <li><i><a href="/wiki/Conium" title="Conium">Conium</a></i> (hemlock)</li> <li><i><a href="/wiki/Datura_innoxia" title="Datura innoxia">Datura innoxia</a></i> (thorn-apple)</li> <li><i><a href="/wiki/Datura_metel" title="Datura metel">Datura metel</a></i> (devil's trumpet)</li> <li><i><a href="/wiki/Hyoscyamus_niger" title="Hyoscyamus niger">Hyoscyamus niger</a></i> (henbane)</li> <li><a href="/wiki/Lactucarium" title="Lactucarium">Lactucarium</a></li> <li><i><a href="/wiki/Mandragora_officinarum" title="Mandragora officinarum">Mandragora officinarum</a></i> (mandrake)</li> <li><a href="/wiki/Opium" title="Opium">Opium</a></li> <li><i><a href="/wiki/Saussurea" title="Saussurea">Saussurea</a></i> (saw-wort)</li> <li><a href="/wiki/Willow" title="Willow">Willow</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Preparations</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/Beer" title="Beer">Beer</a></li> <li><a href="/wiki/Wine" title="Wine">Wine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Compounds</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/Alcohol_(drug)" title="Alcohol (drug)">Ethanol</a> (<a href="/wiki/Alcohols_(medicine)" title="Alcohols (medicine)">medical use</a>)</li> <li><a href="/wiki/Aconitine" title="Aconitine">Aconitine</a></li> <li><a href="/wiki/Atropine" title="Atropine">Atropine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Coniine" title="Coniine">Coniine</a></li> <li><a href="/wiki/Hyoscine" class="mw-redirect" title="Hyoscine">Hyoscine</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Δ9-THC</a></li> <li><a href="/wiki/Hyoscyamine" title="Hyoscyamine">Hyoscyamine</a></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a></li> <li><a class="mw-selflink selflink">Salicylate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">People</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/Al-Zahrawi" title="Al-Zahrawi">Abulcasis</a></li> <li><a href="/wiki/Ibn_Zuhr" title="Ibn Zuhr">Avenzoar</a></li> <li><a href="/wiki/Avicenna" title="Avicenna">Avicenna</a></li> <li><a href="/wiki/Aulus_Cornelius_Celsus" title="Aulus Cornelius Celsus">Celsus</a></li> <li><a href="/wiki/Pedanius_Dioscorides" title="Pedanius Dioscorides">Dioscorides</a></li> <li><a href="/wiki/Galen" title="Galen">Galen</a></li> <li><a href="/wiki/Hippocrates" title="Hippocrates">Hippocrates</a></li> <li><a href="/wiki/Abu_Bakr_al-Razi" title="Abu Bakr al-Razi">Rhazes</a></li> <li><a href="/wiki/Sabuncuoglu_Sherefeddin" class="mw-redirect" title="Sabuncuoglu Sherefeddin">Sabuncuoğlu</a></li> <li><a href="/wiki/Sushruta_Samhita" title="Sushruta Samhita">Sushrutha</a></li> <li><a href="/wiki/Theophrastus" title="Theophrastus">Theophrastus</a></li> <li><a href="/wiki/Zhang_Zhongjing" title="Zhang Zhongjing">Zhang</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Antifungals_(D01_and_J02)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Antifungals" title="Template:Antifungals"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Antifungals" title="Template talk:Antifungals"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Antifungals" title="Special:EditPage/Template:Antifungals"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antifungals_(D01_and_J02)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antifungal" title="Antifungal">Antifungals</a> (<a href="/wiki/ATC_code_D01" title="ATC code D01">D01</a> and <a href="/wiki/ATC_code_J02" title="ATC code J02">J02</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Wall/<br />membrane</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/Ergosterol" title="Ergosterol">Ergosterol</a><br />inhibitors</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Azole" title="Azole">Azoles</a> (<a href="/wiki/Lanosterol_14%CE%B1-demethylase" class="mw-redirect" title="Lanosterol 14α-demethylase">lanosterol 14α-<br />demethylase</a> inhibitors)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Imidazole" title="Imidazole">Imidazoles</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>Topical: <a href="/wiki/Bifonazole" title="Bifonazole">bifonazole</a><sup>‡</sup></li> <li><a href="/wiki/Butoconazole" title="Butoconazole">butoconazole</a></li> <li><a href="/wiki/Chlormidazole" title="Chlormidazole">chlormidazole</a><sup>‡</sup></li> <li><a href="/wiki/Climbazole" title="Climbazole">climbazole</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">clotrimazole</a><sup>#</sup></li> <li><a href="/wiki/Croconazole" title="Croconazole">croconazole</a><sup>‡</sup></li> <li><a href="/wiki/Eberconazole" title="Eberconazole">eberconazole</a></li> <li><a href="/wiki/Econazole" title="Econazole">econazole</a></li> <li><a href="/wiki/Fenticonazole" title="Fenticonazole">fenticonazole</a><sup>‡</sup></li> <li><a href="/wiki/Flutrimazole" title="Flutrimazole">flutrimazole</a></li> <li><a href="/wiki/Isoconazole" title="Isoconazole">isoconazole</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">ketoconazole</a></li> <li><a href="/wiki/Luliconazole" title="Luliconazole">luliconazole</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">miconazole</a><sup>#</sup></li> <li><a href="/wiki/Neticonazole" title="Neticonazole">neticonazole</a><sup>‡</sup></li> <li><a href="/wiki/Omoconazole" title="Omoconazole">omoconazole</a><sup>‡</sup></li> <li><a href="/wiki/Oxiconazole" title="Oxiconazole">oxiconazole</a></li> <li><a href="/wiki/Sertaconazole" title="Sertaconazole">sertaconazole</a></li> <li><a href="/wiki/Sulconazole" title="Sulconazole">sulconazole</a></li> <li><a href="/wiki/Tioconazole" title="Tioconazole">tioconazole</a></li></ul> <ul><li>Systemic: ketoconazole</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triazole" title="Triazole">Triazoles</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>Topical: <a href="/wiki/Efinaconazole" title="Efinaconazole">efinaconazole</a></li> <li><a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a><sup>#</sup></li> <li><a href="/wiki/Terconazole" title="Terconazole">terconazole</a></li></ul> <ul><li>Systemic: <a href="/wiki/Fluconazole" title="Fluconazole">fluconazole</a><sup>#</sup></li> <li><a href="/wiki/Fosfluconazole" title="Fosfluconazole">fosfluconazole</a></li> <li><a href="/wiki/Fosravuconazole" title="Fosravuconazole">fosravuconazole</a></li> <li><a href="/wiki/Hexaconazole" title="Hexaconazole">hexaconazole</a><sup>‡</sup></li> <li><a href="/wiki/Isavuconazonium" title="Isavuconazonium">isavuconazole</a></li> <li><a href="/wiki/Itraconazole" title="Itraconazole">itraconazole</a><sup>#</sup></li> <li><a href="/wiki/Oteseconazole" title="Oteseconazole">oteseconazole</a></li> <li><a href="/wiki/Posaconazole" title="Posaconazole">posaconazole</a></li> <li><a href="/wiki/Voriconazole" title="Voriconazole">voriconazole</a><sup>#</sup></li></ul> <ul><li>Unknown: <a href="/wiki/Albaconazole" title="Albaconazole">albaconazole</a><sup>‡</sup></li> <li><a href="/wiki/Ravuconazole" title="Ravuconazole">ravuconazole</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thiazole" title="Thiazole">Thiazoles</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>Topical: <a href="/wiki/Abafungin" title="Abafungin">abafungin</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/Polyene_antimycotic" title="Polyene antimycotic">Polyene antimycotics</a><br />(<a href="/wiki/Ergosterol" title="Ergosterol">ergosterol</a> binding)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Hamycin" title="Hamycin">hamycin</a><sup>‡</sup></li> <li><a href="/wiki/Natamycin" title="Natamycin">natamycin</a></li> <li><a href="/wiki/Nystatin" title="Nystatin">nystatin</a><sup>#</sup><br />Systemic: <a href="/wiki/Amphotericin_B" title="Amphotericin B">amphotericin B</a><sup>#</sup>, hamycin<sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Squalene_monooxygenase" title="Squalene monooxygenase">Squalene monooxygenase</a><br />inhibitors</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Allylamine" title="Allylamine">Allylamines</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>Topical: <a href="/wiki/Naftifine" title="Naftifine">naftifine</a></li> <li><a href="/wiki/Terbinafine" title="Terbinafine">terbinafine</a><br />Systemic: terbinafine</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzylamine" title="Benzylamine">Benzylamines</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>Topical: <a href="/wiki/Butenafine" title="Butenafine">butenafine</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Amorolfine" title="Amorolfine">amorolfine</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/1,3-Beta-glucan_synthase" title="1,3-Beta-glucan synthase">β-glucan synthase</a><br />inhibitors</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Systemic: <a href="/wiki/Echinocandin" title="Echinocandin">echinocandins</a> (<a href="/wiki/Anidulafungin" title="Anidulafungin">anidulafungin</a></li> <li><a href="/wiki/Caspofungin" title="Caspofungin">caspofungin</a></li> <li><a href="/wiki/Cilofungin" title="Cilofungin">cilofungin</a></li> <li><a href="/wiki/Micafungin" title="Micafungin">micafungin</a></li> <li><a href="/wiki/Rezafungin" title="Rezafungin">rezafungin</a>)</li> <li><a href="/wiki/Ibrexafungerp" title="Ibrexafungerp">ibrexafungerp</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intracellular</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/Pyrimidine_analogue" title="Pyrimidine analogue">Pyrimidine analogues</a>/<br /><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">thymidylate synthase inhibitors</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>Systemic: <a href="/wiki/Flucytosine" title="Flucytosine">flucytosine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mitotic_inhibitor" title="Mitotic inhibitor">Mitotic 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>Systemic: <a href="/wiki/Griseofulvin" title="Griseofulvin">griseofulvin</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aminoacyl_tRNA_synthetase" title="Aminoacyl tRNA synthetase">Aminoacyl tRNA synthetase</a> inhibitors</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Topical: <a href="/wiki/Tavaborole" title="Tavaborole">tavaborole</a></li></ul> </div></td></tr></tbody></table><div></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/Bromochlorosalicylanilide" title="Bromochlorosalicylanilide">bromochlorosalicylanilide</a></li> <li><a href="/wiki/Chlorophetanol" title="Chlorophetanol">chlorophetanol</a></li> <li><a href="/wiki/Chlorphenesin" class="mw-redirect" title="Chlorphenesin">chlorphenesin</a></li> <li><a href="/wiki/Ciclopirox" title="Ciclopirox">ciclopirox</a></li> <li><a href="/wiki/Crystal_violet" title="Crystal violet">crystal violet</a></li> <li><a href="/wiki/Dimazole" title="Dimazole">dimazole</a></li> <li><a href="/wiki/Ethylparaben" title="Ethylparaben">ethylparaben</a></li> <li><a href="/wiki/Haloprogin" title="Haloprogin">haloprogin</a><sup>‡</sup></li> <li><a href="/wiki/Polynoxylin" title="Polynoxylin">polynoxylin</a></li> <li><a href="/wiki/Potassium_iodide" title="Potassium iodide">potassium iodide</a><sup>#</sup></li> <li><a class="mw-selflink selflink">salicylic acid</a></li> <li><a href="/wiki/Selenium_disulfide" title="Selenium disulfide">selenium disulfide</a><sup>#</sup></li> <li><a href="/wiki/Sodium_thiosulfate" title="Sodium thiosulfate">sodium thiosulfate</a><sup>#</sup></li> <li><a href="/wiki/Sulbentine" title="Sulbentine">sulbentine</a></li> <li><a href="/wiki/Taurolidine" title="Taurolidine">taurolidine</a></li> <li><a href="/wiki/Ticlatone" title="Ticlatone">ticlatone</a></li> <li><a href="/wiki/Tolciclate" title="Tolciclate">tolciclate</a></li> <li><a href="/wiki/Tolnaftate" title="Tolnaftate">tolnaftate</a></li> <li><a href="/wiki/Tribromometacresol" title="Tribromometacresol">tribromometacresol</a></li> <li><a href="/wiki/Undecylenic_acid" title="Undecylenic acid">undecylenic acid</a></li> <li><a href="/wiki/Whitfield%27s_ointment" title="Whitfield's ointment">Whitfield's ointment</a><sup>#</sup></li></ul> <ul><li><a href="/wiki/Citronella_oil" title="Citronella oil">citronella oil</a></li> <li><a href="/wiki/Lemon_grass" class="mw-redirect" title="Lemon grass">lemon grass</a></li> <li><a href="/wiki/Lemon_myrtle" class="mw-redirect" title="Lemon myrtle">lemon myrtle</a></li> <li><a href="/wiki/Orange_oil" title="Orange oil">orange oil</a></li> <li><a href="/wiki/Patchouli" title="Patchouli">patchouli</a></li> <li><a href="/wiki/Tea_tree_oil" title="Tea tree oil">tea tree oil</a></li> <li><a href="/wiki/Pneumocystis_pneumonia" title="Pneumocystis pneumonia">PCP</a>: <a href="/wiki/Atovaquone" title="Atovaquone">atovaquone</a></li> <li><a href="/wiki/Dapsone" title="Dapsone">dapsone</a></li> <li><a href="/wiki/Pentamidine" title="Pentamidine">pentamidine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><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="Non-steroidal_anti-inflammatory_drugs_(NSAIDs)_(primarily_M01A_and_M02A,_also_N02BA)" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Anti-inflammatory_products" title="Template:Anti-inflammatory products"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Anti-inflammatory_products" title="Template talk:Anti-inflammatory products"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Anti-inflammatory_products" title="Special:EditPage/Template:Anti-inflammatory products"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Non-steroidal_anti-inflammatory_drugs_(NSAIDs)_(primarily_M01A_and_M02A,_also_N02BA)" style="font-size:114%;margin:0 4em"><a href="/wiki/Non-steroidal_anti-inflammatory_drug" class="mw-redirect" title="Non-steroidal anti-inflammatory drug">Non-steroidal anti-inflammatory drugs</a> (NSAIDs) (primarily <a href="/wiki/ATC_code_M01#M01A" title="ATC code M01">M01A</a> and <a href="/wiki/ATC_code_M02#M02A" title="ATC code M02">M02A</a>, also <a href="/wiki/ATC_code_N02#N02BA" title="ATC code N02">N02BA</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrazolone" title="Pyrazolone">pyrazolones</a> /<br /><a href="/wiki/Pyrazolidine" title="Pyrazolidine">pyrazolidines</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></li> <li><a href="/wiki/Ampyrone" title="Ampyrone">Ampyrone</a></li> <li><a href="/wiki/Azapropazone" title="Azapropazone">Azapropazone</a></li> <li><a href="/wiki/Clofezone" title="Clofezone">Clofezone</a></li> <li><a href="/wiki/Difenamizole" title="Difenamizole">Difenamizole</a></li> <li><a href="/wiki/Famprofazone" title="Famprofazone">Famprofazone</a></li> <li><a href="/wiki/Feprazone" title="Feprazone">Feprazone</a></li> <li><a href="/wiki/Kebuzone" title="Kebuzone">Kebuzone</a></li> <li><a href="/wiki/Metamizole" title="Metamizole">Metamizole</a></li> <li><a href="/wiki/Mofebutazone" title="Mofebutazone">Mofebutazone</a></li> <li><a href="/wiki/Morazone" title="Morazone">Morazone</a></li> <li><a href="/wiki/Nifenazone" title="Nifenazone">Nifenazone</a></li> <li><a href="/wiki/Oxyphenbutazone" title="Oxyphenbutazone">Oxyphenbutazone</a></li> <li><a href="/wiki/Phenazone" title="Phenazone">Phenazone</a></li> <li><u><a href="/wiki/Phenylbutazone" title="Phenylbutazone">Phenylbutazone</a></u></li> <li><a href="/wiki/Propyphenazone" title="Propyphenazone">Propyphenazone</a></li> <li><a href="/wiki/Sulfinpyrazone" title="Sulfinpyrazone">Sulfinpyrazone</a></li> <li><a href="/wiki/Suxibuzone" title="Suxibuzone">Suxibuzone</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a class="mw-selflink selflink">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><u><a href="/wiki/Aspirin" title="Aspirin">Aspirin (acetylsalicylic acid)</a></u><sup>#</sup></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/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/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a></li> <li><a href="/wiki/Salsalate" title="Salsalate">Salsalate</a></li> <li><a href="/wiki/Salicin" title="Salicin">Salicin</a></li> <li><a href="/wiki/Salicylamide" title="Salicylamide">Salicylamide</a></li> <li><a class="mw-selflink selflink">Salicylic acid (salicylate)</a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Acetic_acid" title="Acetic acid">acetic acid</a> derivatives<br />and related substances</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/Aceclofenac" title="Aceclofenac">Aceclofenac</a></li> <li><a href="/wiki/Acemetacin" title="Acemetacin">Acemetacin</a></li> <li><a href="/wiki/Alclofenac" title="Alclofenac">Alclofenac</a></li> <li><a href="/wiki/Amfenac" title="Amfenac">Amfenac</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><u><a href="/wiki/Diclofenac" title="Diclofenac">Diclofenac</a></u></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/Fenclozic_acid" title="Fenclozic acid">Fenclozic acid</a></li> <li><a href="/wiki/Fentiazac" title="Fentiazac">Fentiazac</a></li> <li><a href="/wiki/Indometacin" title="Indometacin">Indometacin</a></li> <li><a href="/wiki/Indometacin_farnesil" title="Indometacin farnesil">Indometacin farnesil</a></li> <li><a href="/w/index.php?title=Isoxepac&action=edit&redlink=1" class="new" title="Isoxepac (page does not exist)">Isoxepac</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/Oxametacin" title="Oxametacin">Oxametacin</a></li> <li><a href="/w/index.php?title=Prodolic_acid&action=edit&redlink=1" class="new" title="Prodolic acid (page does not exist)">Prodolic acid</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=Tiopinac&action=edit&redlink=1" class="new" title="Tiopinac (page does not exist)">Tiopinac</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/Oxicam" title="Oxicam">oxicams</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/Ampiroxicam" title="Ampiroxicam">Ampiroxicam</a></li> <li><a href="/wiki/Droxicam" title="Droxicam">Droxicam</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><u><a href="/wiki/Piroxicam" title="Piroxicam">Piroxicam</a></u></li> <li><a href="/w/index.php?title=Pivoxicam&action=edit&redlink=1" class="new" title="Pivoxicam (page does not exist)">Pivoxicam</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%"><a href="/wiki/Propionic_acid" title="Propionic acid">propionic acid</a><br />derivatives (<a href="/wiki/Profens" class="mw-redirect" title="Profens">profens</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/Alminoprofen" title="Alminoprofen">Alminoprofen</a></li> <li><a href="/wiki/Benoxaprofen" title="Benoxaprofen">Benoxaprofen</a><sup>†</sup></li> <li><a href="/wiki/Carprofen" title="Carprofen">Carprofen</a><sup>‡</sup></li> <li><a href="/wiki/Dexibuprofen" title="Dexibuprofen">Dexibuprofen</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><u><a href="/wiki/Ibuprofen" title="Ibuprofen">Ibuprofen</a></u><sup>#</sup></li> <li><a href="/wiki/Ibuproxam" title="Ibuproxam">Ibuproxam</a></li> <li><a href="/wiki/Indoprofen" title="Indoprofen">Indoprofen</a><sup>†</sup></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><u><a href="/wiki/Naproxen" title="Naproxen">Naproxen</a></u></li> <li><a href="/wiki/Oxaprozin" title="Oxaprozin">Oxaprozin</a></li> <li><a href="/wiki/Pelubiprofen" title="Pelubiprofen">Pelubiprofen</a></li> <li><a href="/wiki/Piketoprofen" title="Piketoprofen">Piketoprofen</a></li> <li><a href="/wiki/Pirprofen" title="Pirprofen">Pirprofen</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><sup>‡</sup></li> <li><a href="/wiki/Tiaprofenic_acid" title="Tiaprofenic acid">Tiaprofenic acid</a></li> <li><a href="/wiki/Vedaprofen" title="Vedaprofen">Vedaprofen</a><sup>‡</sup></li> <li><a href="/wiki/Zaltoprofen" title="Zaltoprofen">Zaltoprofen</a></li> <li><i><a href="/wiki/COX-inhibiting_nitric_oxide_donator" title="COX-inhibiting nitric oxide donator">COX-inhibiting nitric oxide donator</a></i>: <a href="/wiki/Naproxcinod" title="Naproxcinod">Naproxcinod</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><i>n</i>-arylanthranilic<br />acids (<a href="/wiki/Fenamate" class="mw-redirect" title="Fenamate">fenamates</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/Azapropazone" title="Azapropazone">Azapropazone</a></li> <li><a href="/wiki/Clonixin" title="Clonixin">Clonixin</a></li> <li><a href="/wiki/Etofenamate" title="Etofenamate">Etofenamate</a></li> <li><a href="/wiki/Floctafenine" title="Floctafenine">Floctafenine</a></li> <li><a href="/wiki/Flufenamic_acid" title="Flufenamic acid">Flufenamic acid</a></li> <li><a href="/wiki/Flunixin" title="Flunixin">Flunixin</a></li> <li><a href="/w/index.php?title=Flutiazin&action=edit&redlink=1" class="new" title="Flutiazin (page does not exist)">Flutiazin</a></li> <li><a href="/wiki/Glafenine" title="Glafenine">Glafenine</a><sup>†</sup></li> <li><a href="/wiki/Meclofenamic_acid" title="Meclofenamic acid">Meclofenamic acid</a></li> <li><u><a href="/wiki/Mefenamic_acid" title="Mefenamic acid">Mefenamic acid</a></u></li> <li><a href="/wiki/Morniflumate" title="Morniflumate">Morniflumate</a></li> <li><a href="/wiki/Niflumic_acid" title="Niflumic acid">Niflumic 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/COX-2_inhibitor" class="mw-redirect" title="COX-2 inhibitor">COX-2 inhibitors</a><br />(coxibs)</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/Apricoxib" title="Apricoxib">Apricoxib</a></li> <li><u><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a></u> (<a href="/wiki/Celecoxib/tramadol" title="Celecoxib/tramadol">+tramadol</a>)</li> <li><a href="/wiki/Cimicoxib" title="Cimicoxib">Cimicoxib</a><sup>‡</sup></li> <li><a href="/wiki/Deracoxib" title="Deracoxib">Deracoxib</a><sup>‡</sup></li> <li><a href="/wiki/Etoricoxib" title="Etoricoxib">Etoricoxib</a></li> <li><a href="/wiki/Firocoxib" title="Firocoxib">Firocoxib</a><sup>‡</sup></li> <li><a href="/wiki/Lumiracoxib" title="Lumiracoxib">Lumiracoxib</a><sup>†</sup></li> <li><a href="/wiki/Mavacoxib" title="Mavacoxib">Mavacoxib</a><sup>‡</sup></li> <li><a href="/wiki/Parecoxib" title="Parecoxib">Parecoxib</a></li> <li><a href="/wiki/Robenacoxib" title="Robenacoxib">Robenacoxib</a><sup>‡</sup></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%">other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminopropionitrile" title="Aminopropionitrile">Aminopropionitrile</a></li> <li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Chondroitin_sulfate" title="Chondroitin sulfate">Chondroitin sulfate</a></li> <li><a href="/wiki/Diacerein" title="Diacerein">Diacerein</a></li> <li><a href="/wiki/Fluproquazone" title="Fluproquazone">Fluproquazone</a></li> <li><a href="/wiki/Glucosamine" title="Glucosamine">Glucosamine</a></li> <li><a href="/wiki/Glycosaminoglycan" title="Glycosaminoglycan">Glycosaminoglycan</a></li> <li><a href="/wiki/Hyperforin" title="Hyperforin">Hyperforin</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/Oxaceprol" title="Oxaceprol">Oxaceprol</a></li> <li><a href="/wiki/Proquazone" title="Proquazone">Proquazone</a></li> <li><a href="/wiki/Superoxide_dismutase" title="Superoxide dismutase">Superoxide dismutase / orgotein</a></li> <li><a href="/wiki/Tenidap" title="Tenidap">Tenidap</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">NSAID<br />combinations</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/Ibuprofen/famotidine" title="Ibuprofen/famotidine">Ibuprofen/famotidine</a></li> <li><a href="/wiki/Hydrocodone/ibuprofen" title="Hydrocodone/ibuprofen">Ibuprofen/hydrocodone</a></li> <li><a href="/wiki/Oxycodone/ibuprofen" title="Oxycodone/ibuprofen">Ibuprofen/oxycodone</a></li> <li><a href="/wiki/Ibuprofen/paracetamol" title="Ibuprofen/paracetamol">Ibuprofen/paracetamol</a></li> <li><a href="/wiki/Bupivacaine/meloxicam" title="Bupivacaine/meloxicam">Meloxicam/bupivacaine</a></li> <li><a href="/wiki/Naproxen/diphenhydramine" title="Naproxen/diphenhydramine">Naproxen/diphenhydramine</a></li> <li><a href="/wiki/Naproxen/esomeprazole" title="Naproxen/esomeprazole">Naproxen/esomeprazole</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">Key: <u>underline</u> indicates initially developed first-in-class compound of specific group; <sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-Essential Medicines</a>; <sup>†</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">withdrawn drugs</a>; <sup>‡</sup><a href="/wiki/Veterinary_medicine" title="Veterinary medicine">veterinary use</a>.</div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Anti-inflammatory_and_antirheumatic_products" title="Category:Anti-inflammatory and antirheumatic products">category</a></li> <li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <a href="https://commons.wikimedia.org/wiki/Category:Anti-inflammatory_drugs" class="extiw" title="commons:Category:Anti-inflammatory drugs">commons</a></li> <li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Symbol_portal_class.svg" class="mw-file-description" title="Portal"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/16px-Symbol_portal_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/23px-Symbol_portal_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/e/e2/Symbol_portal_class.svg/31px-Symbol_portal_class.svg.png 2x" data-file-width="180" data-file-height="185" /></a></span> <a href="/wiki/Portal:Medicine" title="Portal:Medicine">portal</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Analgesics_(N02A,_N02B)" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><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: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)" 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 href="/wiki/Phenacetin" title="Phenacetin">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 class="mw-selflink selflink">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></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="Plant_hormones" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2" style="background:#ABE0BF"><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:Plant_hormones" title="Template:Plant hormones"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Plant_hormones" title="Template talk:Plant hormones"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Plant_hormones" title="Special:EditPage/Template:Plant hormones"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Plant_hormones" style="font-size:114%;margin:0 4em"><a href="/wiki/Plant_hormone" title="Plant hormone">Plant hormones</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Abscisic_acid" title="Abscisic acid">Abscisic acid</a></li> <li><a href="/wiki/Auxin" title="Auxin">Auxins</a></li> <li><a href="/wiki/Brassinosteroid" title="Brassinosteroid">Brassinosteroids</a></li> <li><a href="/wiki/Cytokinin" title="Cytokinin">Cytokinins</a></li> <li><a href="/wiki/Ethylene" title="Ethylene">Ethylene</a></li> <li><a href="/wiki/Gibberellin" title="Gibberellin">Gibberellins</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0;font-size:80%;"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/24-Epibrassinolide" title="24-Epibrassinolide">24-Epibrassinolide</a></li> <li><a href="/wiki/Florigen" title="Florigen">Florigen</a></li> <li><a href="/wiki/Jasmonate" title="Jasmonate">Jasmonates</a></li> <li><a href="/wiki/Karrikin" title="Karrikin">Karrikins</a></li> <li><a href="/wiki/Plant_peptide_hormone" title="Plant peptide hormone">Plant peptide hormones</a></li> <li><a href="/wiki/Polyamine" title="Polyamine">Polyamine</a></li> <li><a class="mw-selflink selflink">Salicylic acid</a></li> <li><a href="/wiki/Strigolactone" title="Strigolactone">Strigolactones</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Salicylates" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Salicylates" title="Template:Salicylates"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Salicylates" title="Template talk:Salicylates"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Salicylates" title="Special:EditPage/Template:Salicylates"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Salicylates" style="font-size:114%;margin:0 4em"><a class="mw-selflink selflink">Salicylates</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a class="mw-selflink selflink">Salicylic acid</a></li> <li><a href="/wiki/Aspirin" title="Aspirin">Aspirin</a></li> <li><a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Methyl_salicylate" title="Methyl salicylate">Methyl salicylate</a></li> <li><a href="/wiki/Magnesium_salicylate" title="Magnesium salicylate">Magnesium salicylate</a></li> <li><a href="/wiki/Ethyl_salicylate" title="Ethyl salicylate">Ethyl salicylate</a></li> <li><a href="/wiki/Isopropyl_salicylate" title="Isopropyl salicylate">Isopropyl salicylate</a></li> <li><a href="/wiki/Bismuth_subsalicylate" title="Bismuth subsalicylate">Bismuth subsalicylate</a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a></li> <li><a href="/wiki/Salicylamide" title="Salicylamide">Salicylamide</a></li> <li><a href="/wiki/Salicin" title="Salicin">Salicin</a></li> <li><a href="/wiki/Benorilate" title="Benorilate">Benorilate</a></li> <li><a href="/wiki/Salsalate" title="Salsalate">Salsalate</a></li> <li><a href="/wiki/Ethenzamide" title="Ethenzamide">Ethenzamide</a></li> <li><a href="/wiki/Diflunisal" title="Diflunisal">Diflunisal</a></li> <li><a href="/wiki/Trolamine_salicylate" title="Trolamine salicylate">Trolamine salicylate</a></li> <li><a href="/wiki/Homosalate" title="Homosalate">Homosalate</a></li> <li><a href="/wiki/Salicylmethylecgonine" title="Salicylmethylecgonine">Salicylmethylecgonine</a></li> <li><a href="/wiki/2-Ethylhexyl_salicylate" title="2-Ethylhexyl salicylate">2-Ethylhexyl salicylate</a></li> <li><a href="/wiki/Aluminon" title="Aluminon">Aluminon</a></li> <li><a href="/wiki/Benzyl_salicylate" title="Benzyl salicylate">Benzyl salicylate</a></li> <li><a href="/wiki/Copper_aspirinate" title="Copper aspirinate">Copper aspirinate</a></li> <li><a href="/wiki/Potassium_salicylate" title="Potassium salicylate">Potassium salicylate</a></li></ul> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Phenolic_acids_(C6-C1)_and_their_glycosides" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Phenolic_acid" title="Template:Phenolic acid"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Phenolic_acid" title="Template talk:Phenolic acid"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Phenolic_acid" title="Special:EditPage/Template:Phenolic acid"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Phenolic_acids_(C6-C1)_and_their_glycosides" style="font-size:114%;margin:0 4em"><a href="/wiki/Phenolic_acid" title="Phenolic acid">Phenolic acids</a> (C6-C1) and their glycosides</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monohydroxybenzoic_acid" title="Monohydroxybenzoic acid">Monohydroxybenzoic acids</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/3-Hydroxybenzoic_acid" title="3-Hydroxybenzoic acid">3-Hydroxybenzoic acid</a></li> <li><a href="/wiki/4-Hydroxybenzoic_acid" title="4-Hydroxybenzoic acid">4-Hydroxybenzoic acid</a></li> <li><a class="mw-selflink selflink">Salicylic acid</a> (2-Hydroxybenzoic acid)</li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides</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/4-Hydroxybenzoic_acid_4-O-glucoside" title="4-Hydroxybenzoic acid 4-O-glucoside"><i>p</i>-Hydroxybenzoic acid glucoside</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alkylated</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/Methylparaben" title="Methylparaben">Methylparaben</a> (Methyl-<i>p</i>-hydroxybenzoic acid)</li></ul> </div></td></tr></tbody></table><div> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Dihydroxybenzoic_acid" title="Dihydroxybenzoic acid">Dihydroxybenzoic acids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/2,3-Dihydroxybenzoic_acid" title="2,3-Dihydroxybenzoic acid">2,3-Dihydroxybenzoic acid</a> (Hypogallic acid)</li> <li><a href="/wiki/2,4-Dihydroxybenzoic_acid" title="2,4-Dihydroxybenzoic acid">2,4-Dihydroxybenzoic acid</a></li> <li>2,5-Dihydroxybenzoic acid (<a href="/wiki/Gentisic_acid" title="Gentisic acid">Gentisic acid</a>)</li> <li><a href="/wiki/2,6-Dihydroxybenzoic_acid" title="2,6-Dihydroxybenzoic acid">2,6-Dihydroxybenzoic acid</a></li> <li>3,4-Dihydroxybenzoic acid (<a href="/wiki/Protocatechuic_acid" title="Protocatechuic acid">Protocatechuic acid</a>)</li> <li><a href="/wiki/3,5-Dihydroxybenzoic_acid" title="3,5-Dihydroxybenzoic acid">3,5-Dihydroxybenzoic acid</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Alkylated" scope="row" class="navbox-group" style="width:1%">Alkylated</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/Ethyl_protocatechuate" title="Ethyl protocatechuate">Ethyl protocatechuate</a></li> <li><a href="/wiki/Orsellinic_acid" title="Orsellinic acid">Orsellinic acid</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/Trihydroxybenzoic_acid" title="Trihydroxybenzoic acid">Trihydroxybenzoic acids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gallic_acid" title="Gallic acid">Gallic acid</a></li> <li><a href="/wiki/Phloroglucinol_carboxylic_acid" title="Phloroglucinol carboxylic acid">Phloroglucinol carboxylic acid</a></li></ul> </div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Glycosides</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/Bergenin" title="Bergenin">Bergenin</a></li> <li><a href="/wiki/Norbergenin" title="Norbergenin">Norbergenin</a></li> <li><a href="/wiki/Theogallin" title="Theogallin">Theogallin</a></li> <li><a href="/wiki/Chebulic_acid" title="Chebulic acid">Chebulic acid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Alkylated</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/Ethyl_gallate" title="Ethyl gallate">Ethyl gallate</a></li> <li><a href="/wiki/Eudesmic_acid" title="Eudesmic acid">Eudesmic acid</a></li> <li><a href="/wiki/Methyl_gallate" title="Methyl gallate">Methyl gallate</a></li> <li><a href="/wiki/Syringic_acid" title="Syringic acid">Syringic acid</a></li></ul> </div></td></tr></tbody></table><div> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Prostanoid_signaling_modulators" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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_modulators" 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="/w/index.php?title=Clonixeril&action=edit&redlink=1" class="new" title="Clonixeril (page does not exist)">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 href="/wiki/Phenacetin" title="Phenacetin">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> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1038841319"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q193572#identifiers" 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></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4178954-4">Germany</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85116754">United States</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Salicylique, Acide"><a rel="nofollow" class="external text" href="https://catalogue.bnf.fr/ark:/12148/cb13174049h">France</a></span></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="Salicylique, Acide"><a rel="nofollow" class="external text" href="https://data.bnf.fr/ark:/12148/cb13174049h">BnF data</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00570211">Japan</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007553430005171">Israel</a></span></li></ul></div></td></tr></tbody></table></div> <!-- NewPP limit report Parsed by mw‐web.codfw.main‐f69cdc8f6‐f9ddp Cached time: 20241122140417 Cache expiry: 2592000 Reduced expiry: false Complications: [vary‐revision‐sha1, show‐toc] CPU time usage: 2.056 seconds Real time usage: 2.526 seconds Preprocessor visited node count: 15616/1000000 Post‐expand include size: 581772/2097152 bytes Template argument size: 77389/2097152 bytes Highest expansion depth: 26/100 Expensive parser function count: 8/500 Unstrip recursion depth: 1/20 Unstrip post‐expand size: 320580/5000000 bytes Lua time usage: 1.013/10.000 seconds Lua memory usage: 27933352/52428800 bytes Lua Profile: ? 220 ms 17.7% recursiveClone <mwInit.lua:45> 160 ms 12.9% MediaWiki\Extension\Scribunto\Engines\LuaSandbox\LuaSandboxCallback::callParserFunction 140 ms 11.3% 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