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href="#Overdose"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Overdose</span> </div> </a> <ul id="toc-Overdose-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Physicochemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Physicochemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Physicochemistry</span> </div> </a> <ul id="toc-Physicochemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pharmacology" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Pharmacology"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Pharmacology</span> </div> </a> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> </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">6</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Society and culture</span> </div> </a> <button aria-controls="toc-Society_and_culture-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 Society and culture subsection</span> </button> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> <li id="toc-Legal_status" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Legal_status"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>Legal status</span> </div> </a> <ul id="toc-Legal_status-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brand_names" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Brand_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Brand names</span> </div> </a> <ul id="toc-Brand_names-sublist" class="vector-toc-list"> <li id="toc-Analgin" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Analgin"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2.1</span> <span>Analgin</span> </div> </a> <ul id="toc-Analgin-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span 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Available in 36 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-36" 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">36 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D9%8A%D8%AA%D8%A7%D9%85%D9%8A%D8%B2%D9%88%D9%84" title="ميتاميزول – Arabic" lang="ar" hreflang="ar" data-title="ميتاميزول" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ast mw-list-item"><a href="https://ast.wikipedia.org/wiki/Metamizol" title="Metamizol – Asturian" lang="ast" hreflang="ast" data-title="Metamizol" data-language-autonym="Asturianu" data-language-local-name="Asturian" class="interlanguage-link-target"><span>Asturianu</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Metamizol" title="Metamizol – Azerbaijani" lang="az" hreflang="az" data-title="Metamizol" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%9D%D0%BE%D1%80%D0%B0%D0%BC%D0%B8%D0%B4%D0%BE%D0%BF%D0%B8%D1%80%D0%B8%D0%BD" title="Норамидопирин – Bulgarian" lang="bg" hreflang="bg" data-title="Норамидопирин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Metamizole" title="Metamizole – Catalan" lang="ca" hreflang="ca" data-title="Metamizole" 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/Metamizol" title="Metamizol – Czech" lang="cs" hreflang="cs" data-title="Metamizol" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Metamizol-Natrium" title="Metamizol-Natrium – German" lang="de" hreflang="de" data-title="Metamizol-Natrium" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Metamizol" title="Metamizol – Spanish" lang="es" hreflang="es" data-title="Metamizol" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/Metamizol" title="Metamizol – Basque" lang="eu" hreflang="eu" data-title="Metamizol" 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/%D9%85%D8%AA%D8%A7%D9%85%DB%8C%D8%B2%D9%88%D9%84" title="متامیزول – Persian" lang="fa" hreflang="fa" data-title="متامیزول" 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/Noramidopyrine" title="Noramidopyrine – French" lang="fr" hreflang="fr" data-title="Noramidopyrine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%84%A4%ED%94%BC%EB%A6%B0" title="설피린 – Korean" lang="ko" hreflang="ko" data-title="설피린" 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/%D4%B1%D5%B6%D5%A1%D5%AC%D5%A3%D5%AB%D5%B6" title="Անալգին – Armenian" lang="hy" hreflang="hy" data-title="Անալգին" 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%AE%E0%A5%87%E0%A4%9F%E0%A4%BE%E0%A4%AE%E0%A4%BF%E0%A4%9C%E0%A5%8B%E0%A4%B2" title="मेटामिजोल – Hindi" lang="hi" hreflang="hi" data-title="मेटामिजोल" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Metamizol" title="Metamizol – Indonesian" lang="id" hreflang="id" data-title="Metamizol" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Metamizolo" title="Metamizolo – Italian" lang="it" hreflang="it" data-title="Metamizolo" 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%93%D7%99%D7%A4%D7%99%D7%A8%D7%95%D7%9F" title="דיפירון – Hebrew" lang="he" hreflang="he" data-title="דיפירון" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%90%D0%BD%D0%B0%D0%BB%D1%8C%D0%B3%D0%B8%D0%BD" title="Анальгин – Kazakh" lang="kk" hreflang="kk" data-title="Анальгин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target"><span>Қазақша</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Metamizol-n%C3%A1trium" title="Metamizol-nátrium – Hungarian" lang="hu" hreflang="hu" data-title="Metamizol-nátrium" 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%9C%D0%B5%D1%82%D0%B0%D0%BC%D0%B8%D0%B7%D0%BE%D0%BB" title="Метамизол – Macedonian" lang="mk" hreflang="mk" data-title="Метамизол" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Metamizol" title="Metamizol – Dutch" lang="nl" hreflang="nl" data-title="Metamizol" 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%B9%E3%83%AB%E3%83%94%E3%83%AA%E3%83%B3" title="スルピリン – Japanese" lang="ja" hreflang="ja" data-title="スルピリン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%AE%E0%AD%87%E0%AC%9F%E0%AC%BE%E0%AC%AE%E0%AC%BF%E0%AC%9C%E0%AD%8B%E0%AC%B2" title="ମେଟାମିଜୋଲ – Odia" lang="or" hreflang="or" data-title="ମେଟାମିଜୋଲ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Analgin" title="Analgin – Uzbek" lang="uz" hreflang="uz" data-title="Analgin" 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/Metamizol" title="Metamizol – Polish" lang="pl" hreflang="pl" data-title="Metamizol" 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/Metamizol" title="Metamizol – Portuguese" lang="pt" hreflang="pt" data-title="Metamizol" 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/Metamizol" title="Metamizol – Romanian" lang="ro" hreflang="ro" data-title="Metamizol" 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%9C%D0%B5%D1%82%D0%B0%D0%BC%D0%B8%D0%B7%D0%BE%D0%BB_%D0%BD%D0%B0%D1%82%D1%80%D0%B8%D1%8F" title="Метамизол натрия – Russian" lang="ru" hreflang="ru" data-title="Метамизол натрия" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Metamizol" title="Metamizol – Slovak" lang="sk" hreflang="sk" data-title="Metamizol" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Metamizol" title="Metamizol – Serbian" lang="sr" hreflang="sr" data-title="Metamizol" 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/Metamizol" title="Metamizol – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Metamizol" 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-tt mw-list-item"><a href="https://tt.wikipedia.org/wiki/%D0%9D%D0%B0%D1%82%D1%80%D0%B8%D0%B9_%D0%BC%D0%B5%D1%82%D0%B0%D0%BC%D0%B8%D0%B7%D0%BE%D0%BB%D1%8B" title="Натрий метамизолы – Tatar" lang="tt" hreflang="tt" data-title="Натрий метамизолы" data-language-autonym="Татарча / tatarça" data-language-local-name="Tatar" class="interlanguage-link-target"><span>Татарча / tatarça</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Metamizol" title="Metamizol – Turkish" lang="tr" hreflang="tr" data-title="Metamizol" 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%90%D0%BD%D0%B0%D0%BB%D1%8C%D0%B3%D1%96%D0%BD" title="Анальгін – Ukrainian" lang="uk" hreflang="uk" data-title="Анальгін" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E5%AE%89%E4%B9%83%E8%BF%91" title="安乃近 – Wu" lang="wuu" hreflang="wuu" data-title="安乃近" 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 mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%AE%89%E4%B9%83%E8%BF%91" title="安乃近 – Chinese" lang="zh" hreflang="zh" data-title="安乃近" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit 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noexcerpt noprint searchaux" style="display:none">Medication</div> <p class="mw-empty-elt"> </p> <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">Not to be confused with <a href="/wiki/Thiamazole" title="Thiamazole">methimazole</a> or <a href="/wiki/Methazolamide" title="Methazolamide">methazolamide</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Metamizole">Metamizole</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size skin-invert-image" typeof="mw:File/Frameless"><a href="/wiki/File:Metamizole2DACS.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Metamizole2DACS.svg/220px-Metamizole2DACS.svg.png" decoding="async" width="220" height="91" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Metamizole2DACS.svg/330px-Metamizole2DACS.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a4/Metamizole2DACS.svg/440px-Metamizole2DACS.svg.png 2x" data-file-width="727" data-file-height="301" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Metamizole_monohydrate_3D_ball-and-stick.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Metamizole_monohydrate_3D_ball-and-stick.png/250px-Metamizole_monohydrate_3D_ball-and-stick.png" decoding="async" width="250" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Metamizole_monohydrate_3D_ball-and-stick.png/375px-Metamizole_monohydrate_3D_ball-and-stick.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Metamizole_monohydrate_3D_ball-and-stick.png/500px-Metamizole_monohydrate_3D_ball-and-stick.png 2x" data-file-width="2000" data-file-height="1260" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Novalgin, Algocalmin,<sup id="cite_ref-Brune_1-0" class="reference"><a href="#cite_note-Brune-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Analgin, others<sup id="cite_ref-EMA-list_2-0" class="reference"><a href="#cite_note-EMA-list-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Dipyrone (<a href="/wiki/British_Approved_Name" title="British Approved Name">BAN</a> <abbr title="United Kingdom">UK</abbr>, <a href="/wiki/United_States_Adopted_Name" title="United States Adopted Name">USAN</a> <abbr title="United States">US</abbr>), Sulpyrine (<a href="/wiki/Japanese_Accepted_Name" title="Japanese Accepted Name">JAN</a> <small><abbr title="Japan">JP</abbr></small>)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/metamizole.html">International Drug Names</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li>None assigned; no evidence of <a href="/wiki/Teratology" title="Teratology">teratogenicity</a> in animal studies, but use in the third trimester may cause adverse effects in the newborn or <a href="/wiki/Ductus_arteriosus" title="Ductus arteriosus">ductus arteriosus</a> (a heart defect) due to its weak NSAID activity.<sup id="cite_ref-Pharmaceuticale_Press-2009_3-0" class="reference"><a href="#cite_note-Pharmaceuticale_Press-2009-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-0" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data">Oral, IM, IV, rectal</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_N02" title="ATC code N02">N02BB02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N02BB02">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> Withdrawn</li> <li><small><abbr class="country-name" title="Brazil">BR</abbr>:</small> <a href="/wiki/Brazilian_Controlled_Drugs_and_Substances_Act#OTC" title="Brazilian Controlled Drugs and Substances Act">OTC</a> (Over the counter)</li> <li><small><abbr class="country-name" title="Canada">CA</abbr></small>: Veterinary only<sup id="cite_ref-Government_of_Canada-2022_5-0" class="reference"><a href="#cite_note-Government_of_Canada-2022-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="Germany">DE</abbr></small>: § 48 <a href="/wiki/List_of_German_drug_laws#AMG" title="List of German drug laws">AMG</a>/§ 1 <a href="/wiki/List_of_German_drug_laws#MPAV" title="List of German drug laws">MPAV</a> (Prescription only)<sup id="cite_ref-Bundesinstitut_für_Arzneimittel_und_Medizinprodukte_(Federal_Institute_for_Pharmaceuticals_and_Medical_Products)-2009_10-0" class="reference"><a href="#cite_note-Bundesinstitut_für_Arzneimittel_und_Medizinprodukte_(Federal_Institute_for_Pharmaceuticals_and_Medical_Products)-2009-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="New Zealand">NZ</abbr></small>: Prescription only<sup id="cite_ref-NZ-prescription_6-0" class="reference"><a href="#cite_note-NZ-prescription-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-medsafe.govt.nz-2019_7-0" class="reference"><a href="#cite_note-medsafe.govt.nz-2019-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> Withdrawn</li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> Veterinary only (horses)<sup id="cite_ref-FDA2019horse_8-0" class="reference"><a href="#cite_note-FDA2019horse-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Legally available<sup id="cite_ref-EMA2018_9-0" class="reference"><a href="#cite_note-EMA2018-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">100% (active metabolites)<sup id="cite_ref-deranaes2008_11-0" class="reference"><a href="#cite_note-deranaes2008-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">48–58% (active metabolites)<sup id="cite_ref-deranaes2008_11-1" class="reference"><a href="#cite_note-deranaes2008-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data">Liver<sup id="cite_ref-deranaes2008_11-3" class="reference"><a href="#cite_note-deranaes2008-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">14 minutes (parent compound; parenteral);<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-1" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> metabolites: <span class="nowrap"><span data-sort-value="7003720000000000000♠"></span>2–4 h</span><sup id="cite_ref-deranaes2008_11-2" class="reference"><a href="#cite_note-deranaes2008-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pharmacodynamics#Duration_of_action" title="Pharmacodynamics">Duration of action</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7004144000000000000♠"></span>4–6 h</span><sup id="cite_ref-y0_12-0" class="reference"><a href="#cite_note-y0-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data">Urine (96%, IV; 85%, oral), faeces (4%, IV).<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-2" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">[(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1<i>H</i>-pyrazol-4-yl)methylamino] methanesulfonic acid</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=50567-35-6">50567-35-6</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> <br />68-89-3 (sodium salt)</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3111">3111</a></span></li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/522325">522325</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB04817">DB04817</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.3000.html">3000</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/934T64RMNJ">934T64RMNJ</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D08188">D08188</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:62088">CHEBI:62088</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL461522">ChEMBL461522</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID8020543">DTXSID8020543</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q422761#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.000.631">100.000.631</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q422761#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>13</sub><span title="Hydrogen">H</span><sub>17</sub><span title="Nitrogen">N</span><sub>3</sub><span title="Oxygen">O</span><sub>4</sub><span title="Sulfur">S</span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002311360000000000♠"></span>311.36</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=c1ccccc1N2N%28C%29C%28C%29%3DC%28C2%3DO%29N%28C%29CS%28%3DO%29%28%3DO%29O">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">c1ccccc1N2N(C)C(C)=C(C2=O)N(C)CS(=O)(=O)O</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H17N3O4S/c1-10-12(14(2)9-21(18,19)20)13(17)16(15(10)3)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3,(H,18,19,20)<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:LVWZTYCIRDMTEY-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><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> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464373286&page2=Metamizole">(verify)</a></span></span></td></tr></tbody></table> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Dipirona_PNG.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Dipirona_PNG.png/220px-Dipirona_PNG.png" decoding="async" width="220" height="311" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Dipirona_PNG.png/330px-Dipirona_PNG.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Dipirona_PNG.png/440px-Dipirona_PNG.png 2x" data-file-width="2480" data-file-height="3508" /></a><figcaption>Oral solution bottle of dypirone in its packaging (Portuguese lettering)</figcaption></figure> <p><b>Metamizole</b> or <b>dipyrone</b> is a <a href="/wiki/Analgesic" title="Analgesic">painkiller</a>, <a href="/wiki/Antispasmodic" title="Antispasmodic">spasm reliever</a>, and <a href="/wiki/Antipyretic" title="Antipyretic">fever reliever</a> drug. It is most commonly given by mouth or by intravenous infusion.<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013a_13-0" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013a-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-deranaes2008_11-4" class="reference"><a href="#cite_note-deranaes2008-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-deranaes2004_14-0" class="reference"><a href="#cite_note-deranaes2004-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> It belongs to the <a href="/wiki/Ampyrone" title="Ampyrone">ampyrone</a> <a href="/wiki/Sulfonate" title="Sulfonate">sulfonate</a> family of medicines and was patented in 1922. Metamizole is marketed under various trade names.<sup id="cite_ref-EMA-list_2-1" class="reference"><a href="#cite_note-EMA-list-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pharmaceuticale_Press-2009_3-1" class="reference"><a href="#cite_note-Pharmaceuticale_Press-2009-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It was first used medically in Germany under the brand name "Novalgin", <sup id="cite_ref-Fis20064_15-0" class="reference"><a href="#cite_note-Fis20064-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> later becoming widely known in <a href="/wiki/Slavs" title="Slavs">Slavic</a> nations and India under the name "Analgin".<sup id="cite_ref-pmid26019521_16-0" class="reference"><a href="#cite_note-pmid26019521-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Business_Standard_India-2014_17-0" class="reference"><a href="#cite_note-Business_Standard_India-2014-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Sale of Metamizole is restricted in some jurisdictions following studies in the 1970s which correlated it to severe adverse effects, including <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>.<sup id="cite_ref-United_Nations_Department_of_Economic_and_Social_Affairs-2005_18-0" class="reference"><a href="#cite_note-United_Nations_Department_of_Economic_and_Social_Affairs-2005-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Other studies have disputed this judgement, instead claiming that it is a safer drug than other painkillers.<sup id="cite_ref-pmid31433499-2_19-0" class="reference"><a href="#cite_note-pmid31433499-2-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NikolovaTencheva20144_20-0" class="reference"><a href="#cite_note-NikolovaTencheva20144-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Metamizole is popular in many countries, where it is typically available as an <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">over-the-counter</a> medication. <sup id="cite_ref-pmid35584441_21-0" class="reference"><a href="#cite_note-pmid35584441-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metamizole, with its potent <a href="/wiki/Analgesic" title="Analgesic">analgesic</a> (pain relief), <a href="/wiki/Antipyretic" title="Antipyretic">antipyretic</a> (fever reduction), and <a href="/wiki/Spasmolytics" class="mw-redirect" title="Spasmolytics">spasmolytic</a> (relax muscle contractions) properties, is utilized in the management of acute pain, fever, and pain caused by <a href="/wiki/Muscle_spasms" class="mw-redirect" title="Muscle spasms">muscle spasms</a>.<sup id="cite_ref-pmid25199942_22-0" class="reference"><a href="#cite_note-pmid25199942-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>It is primarily used for <a href="/wiki/Perioperative" title="Perioperative">perioperative</a> pain, acute injury, <a href="/wiki/Colic" title="Colic">colic</a>, cancer pain, other acute/chronic forms of pain and high fever unresponsive to other agents.<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-3" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Metamizole also effectively manages biliary and intestinal colic-like pain, and reduces the spasm of the <a href="/wiki/Smooth_muscle" title="Smooth muscle">smooth muscle</a> of the <a href="/wiki/Sphincter_of_Oddi" title="Sphincter of Oddi">sphincter of Oddi</a>.<sup id="cite_ref-pmid30652827_23-0" class="reference"><a href="#cite_note-pmid30652827-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Special_populations">Special populations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=2" title="Edit section: Special populations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Its use in pregnancy is advised against, although animal studies are reassuring in that they show minimal risk of birth defects. Its use in the elderly and those with liver or kidney impairment is advised against, but if these groups of people must be treated, a lower dose and caution is usually advised. Its use during lactation is advised against, as it is excreted in breast milk.<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-4" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=3" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While metamizole is a relatively safe medication,<sup id="cite_ref-pmid24724493_24-0" class="reference"><a href="#cite_note-pmid24724493-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> it is not entirely devoid of adverse effects.<sup id="cite_ref-pmid24724493_24-1" class="reference"><a href="#cite_note-pmid24724493-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Metamizole has a potential of blood-related toxicity (blood <a href="/wiki/Dyscrasia" title="Dyscrasia">dyscrasias</a>), but causes less <a href="/wiki/Renal" class="mw-redirect" title="Renal">kidney</a>, <a href="/wiki/Cardiovascular" class="mw-redirect" title="Cardiovascular">cardiovascular</a>, and gastrointestinal toxicity than <a href="/wiki/Non-steroidal_anti-inflammatory_drugs" class="mw-redirect" title="Non-steroidal anti-inflammatory drugs">non-steroidal anti-inflammatory drugs</a> (NSAIDs).<sup id="cite_ref-deranaes2008_11-5" class="reference"><a href="#cite_note-deranaes2008-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> Like NSAIDs, it can trigger bronchospasm or <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylaxis</a>, especially in those with <a href="/wiki/Asthma" title="Asthma">asthma</a>.<sup id="cite_ref-deranaes2004_14-1" class="reference"><a href="#cite_note-deranaes2004-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Serious side effects include <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>, <a href="/wiki/Aplastic_anaemia" class="mw-redirect" title="Aplastic anaemia">aplastic anaemia</a>, hypersensitivity reactions (like <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylaxis</a> and <a href="/wiki/Bronchospasm" title="Bronchospasm">bronchospasm</a>), <a href="/wiki/Toxic_epidermal_necrolysis" title="Toxic epidermal necrolysis">toxic epidermal necrolysis</a> and it may provoke acute attacks of <a href="/wiki/Porphyria" title="Porphyria">porphyria</a>, as it is chemically related to the <a href="/wiki/Sulfonamide" title="Sulfonamide">sulfonamides</a>.<sup id="cite_ref-Pharmaceuticale_Press-2009_3-2" class="reference"><a href="#cite_note-Pharmaceuticale_Press-2009-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-deranaes2008_11-6" class="reference"><a href="#cite_note-deranaes2008-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-deranaes2004_14-2" class="reference"><a href="#cite_note-deranaes2004-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> The relative risk for agranulocytosis appears to greatly vary according to the country of estimates on said rate and opinion on the risk is strongly divided.<sup id="cite_ref-Pharmaceuticale_Press-2009_3-3" class="reference"><a href="#cite_note-Pharmaceuticale_Press-2009-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-CurrOpAnesth2014rev_25-0" class="reference"><a href="#cite_note-CurrOpAnesth2014rev-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Reis2022_26-0" class="reference"><a href="#cite_note-Reis2022-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> Genetics may play a significant role in metamizole sensitivity.<sup id="cite_ref-PharmacogenetGenomics2015_27-0" class="reference"><a href="#cite_note-PharmacogenetGenomics2015-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> It is suggested that some populations are more prone to suffer from metamizole induced agranulocytosis than others. As an example, metamizole-related agranulocytosis seems to be an adverse effect more frequent in British population as opposed to Spaniards.<sup id="cite_ref-RevClinEsp2009_28-0" class="reference"><a href="#cite_note-RevClinEsp2009-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> An assessment report by the European Medicines Agency remarked that "the potential to induce agranulocytosis may be associated with genetic characteristics of the population studied".<sup id="cite_ref-European_Medicines_Agency,_Committee_for_Medicinal_Products_for_Human_Use_(CHMP)-2018_29-0" class="reference"><a href="#cite_note-European_Medicines_Agency,_Committee_for_Medicinal_Products_for_Human_Use_(CHMP)-2018-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>A 2015 meta-analysis concluded that on the evidence available "for short-term use in the hospital setting, metamizole seems to be a safe choice when compared to other widely used analgesics", but that the "results were limited by the mediocre overall quality of the reports" analysed.<sup id="cite_ref-pmid25875821_30-0" class="reference"><a href="#cite_note-pmid25875821-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p><p>A systematic review from 2016 found that metamizole significantly increased the <a href="/wiki/Relative_risk" title="Relative risk">relative risk</a> of upper gastrointestinal bleeding, by a factor of <span class="nowrap"><span data-sort-value="7000139999999999999♠"></span>1.4–2.7</span> times; however, none of the studies included in that review accounted for duration of therapy or dose.<sup id="cite_ref-pmid27422768_31-0" class="reference"><a href="#cite_note-pmid27422768-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> A study by one of the manufacturers of the drug found the risk of agranulocytosis within the first week of treatment to be a <span class="nowrap"><span data-sort-value="7000110000000000000♠"></span>1.1</span> in a million,<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> versus <span class="nowrap"><span data-sort-value="7000590000000000000♠"></span>5.9</span> in a million for <a href="/wiki/Diclofenac" title="Diclofenac">diclofenac</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (April 2024)">medical citation needed</span></a></i>]</sup> Therapeutic effect of metamizole on intestinal colic is attributed to its analgesic properties, with no evidence of interference in small bowel or colon motility.<sup id="cite_ref-pmid30652827_23-1" class="reference"><a href="#cite_note-pmid30652827-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>Metamizole has potential for hepatotoxicity.<sup id="cite_ref-pmid31433499_33-0" class="reference"><a href="#cite_note-pmid31433499-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Contraindications">Contraindications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=4" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Previous hypersensitivity (such as <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a> or <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylaxis</a>) to metamizole or any of the <a href="/wiki/Excipients" class="mw-redirect" title="Excipients">excipients</a> (e.g. <a href="/wiki/Lactose" title="Lactose">lactose</a>) in the preparation used, acute <a href="/wiki/Porphyria" title="Porphyria">porphyria</a>, impaired <a href="/wiki/Haematopoiesis" title="Haematopoiesis">haematopoiesis</a> (such as due to treatment with <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a> agents), third trimester of pregnancy (potential for adverse effects in the newborn), lactation, children with a body weight below 16 kg, history of aspirin-induced asthma and other hypersensitivity reactions to analgesics.<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-5" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>In 2018, the <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a> (EMA) reviewed the safety of metamizole and concluded it to be generally safe for the general population. However, they advised against its use in the third trimester of pregnancy or while breastfeeding due to risks of <a href="/wiki/Renal_impairment" class="mw-redirect" title="Renal impairment">renal impairment</a> or <a href="/wiki/Ductus_arteriosus" title="Ductus arteriosus">ductus arteriosus</a> to the fetus or infant.<sup id="cite_ref-EMA2018_9-1" class="reference"><a href="#cite_note-EMA2018-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=5" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A clinically severe interaction has been identified between aspirin and metamizole for patients who regularly take aspirin to manage vascular disease: this interaction occurs due to steric hindrance at the active aspirin binding site of <a href="/wiki/Cyclooxygenase-1" title="Cyclooxygenase-1">COX-1</a> by metamizole; to manage this interaction, it is recommended to make a delay between the intake of each of these drugs, with aspirin being taken at least 30 minutes before metamizole.<sup id="cite_ref-pmid37109738_34-0" class="reference"><a href="#cite_note-pmid37109738-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Known interactions </caption> <tbody><tr> <th>Drug(s)</th> <th>Interaction/reason for theoretical potential for interaction </th></tr> <tr> <td><a href="/wiki/Aspirin" title="Aspirin">Aspirin</a></td> <td>Platelet aggregation inhibition (PAI) by aspirin; metamizole prevents aspirin from inhibiting COX-1.<sup id="cite_ref-pmid37109738_34-1" class="reference"><a href="#cite_note-pmid37109738-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Ciclosporin" title="Ciclosporin">Ciclosporin</a></td> <td>Decreased serum levels of <a href="/wiki/Ciclosporin" title="Ciclosporin">ciclosporin</a>.<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-6" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Chlorpromazine" title="Chlorpromazine">Chlorpromazine</a></td> <td>Additive <a href="/wiki/Hypothermia" title="Hypothermia">hypothermia</a> (low body temperature) may result.<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-7" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Hydroxyethyl_starch" title="Hydroxyethyl starch">Hydroxyethyl starch</a></td> <td>Acute renal insufficiency. Low evidence, but discouraged simultaneous administration.<sup id="cite_ref-Meyler16_35-0" class="reference"><a href="#cite_note-Meyler16-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a></td> <td>Additive risk for haematologic (blood) toxicity.<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-8" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> More specifically, <a href="/wiki/Aplastic_anemia" title="Aplastic anemia">bone marrow aplasia</a>.<sup id="cite_ref-Meyler16_35-1" class="reference"><a href="#cite_note-Meyler16-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </td></tr></tbody></table> <p>Oral <a href="/wiki/Anticoagulants" class="mw-redirect" title="Anticoagulants">anticoagulants</a> (blood thinners), <a href="/wiki/Lithium_(medication)" title="Lithium (medication)">lithium</a>, <a href="/wiki/Captopril" title="Captopril">captopril</a>, <a href="/wiki/Triamterene" title="Triamterene">triamterene</a> and <a href="/wiki/Antihypertensive" title="Antihypertensive">antihypertensives</a> may also interact with metamizole, as other <a href="/wiki/Pyrazolone" title="Pyrazolone">pyrazolones</a> are known to interact adversely with these substances. </p> <div class="mw-heading mw-heading3"><h3 id="Overdose">Overdose</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=6" title="Edit section: Overdose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is considered fairly safe on overdose, but in these cases supportive measures are usually advised as well as measures to limit absorption (such as <a href="/wiki/Activated_charcoal" class="mw-redirect" title="Activated charcoal">activated charcoal</a>) and accelerate excretion (such as <a href="/wiki/Haemodialysis" class="mw-redirect" title="Haemodialysis">haemodialysis</a>).<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-9" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Physicochemistry">Physicochemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=7" title="Edit section: Physicochemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metamizole is a sulfonic acid and comes in <a href="/wiki/Calcium" title="Calcium">calcium</a>, <a href="/wiki/Sodium" title="Sodium">sodium</a> and <a href="/wiki/Magnesium" title="Magnesium">magnesium</a> salt forms.<sup id="cite_ref-Pharmaceuticale_Press-2009_3-4" class="reference"><a href="#cite_note-Pharmaceuticale_Press-2009-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Its sodium salt <a href="/wiki/Monohydrate" class="mw-redirect" title="Monohydrate">monohydrate</a> form is a white/almost crystalline powder that is unstable in the presence of light, highly soluble in water and <a href="/wiki/Ethanol" title="Ethanol">ethanol</a> but practically insoluble in <a href="/wiki/Dichloromethane" title="Dichloromethane">dichloromethane</a>.<sup id="cite_ref-Council_Of_Europe:_European_Directorate_for_the_Quality_of_Medicines_and_Healthcare-2013_36-0" class="reference"><a href="#cite_note-Council_Of_Europe:_European_Directorate_for_the_Quality_of_Medicines_and_Healthcare-2013-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=8" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The precise mechanism of action of metamizole is unknown, although it is believed that metamizole generally exerts its action by inhibiting the <a href="/wiki/Cyclooxygenase-3" title="Cyclooxygenase-3">COX-3</a> enzyme which is responsible for the biosynthesis of <a href="/wiki/Prostaglandin" title="Prostaglandin">prostaglandins</a> in the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> (CNS)—in the brain and spinal cord. Prostaglandins are lipid compounds that play a role in inflammation, pain, and fever. By inhibiting the COX-3 enzyme in the CNS, metamizole reduces the production of prostaglandins, thereby alleviating pain, reducing fever, and potentially lessening inflammation.<sup id="cite_ref-deranaes2004_14-3" class="reference"><a href="#cite_note-deranaes2004-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid31519356_37-0" class="reference"><a href="#cite_note-pmid31519356-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Activation of the <a href="/wiki/Endocannabinoid_system" title="Endocannabinoid system">endocannabinoid</a> and <a href="/wiki/Opioid_peptide" title="Opioid peptide">opioidergic</a> systems is also thought to play a role in analgesic effects of metamizole.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NikolovaTencheva20144_20-1" class="reference"><a href="#cite_note-NikolovaTencheva20144-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Metamizole is classified as an atypical <a href="/wiki/Nonsteroidal_anti-inflammatory_drug" title="Nonsteroidal anti-inflammatory drug">nonsteroidal anti-inflammatory drug</a> (NSAID). Unlike typical NSAIDs, metamizole exhibits weak or no anti-inflammatory properties (at least in therapeutic doses),<sup id="cite_ref-pmid25199942_22-1" class="reference"><a href="#cite_note-pmid25199942-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid31519356_37-1" class="reference"><a href="#cite_note-pmid31519356-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> but possesses potent analgesic effects via its action in the CNS: this central action distinguishes it from other NSAIDs, which generally exert their effects peripherally.<sup id="cite_ref-pmid31519356_37-2" class="reference"><a href="#cite_note-pmid31519356-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> The inhibition of <a href="/wiki/Cyclooxygenase-1" title="Cyclooxygenase-1">COX-1</a> and <a href="/wiki/Cyclooxygenase-2" title="Cyclooxygenase-2">COX-2</a> by metamizole is less potent than the inhibition of these enzymes by traditional NSAIDs.<sup id="cite_ref-y0_12-1" class="reference"><a href="#cite_note-y0-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Metamizole is metabolized in the liver, where it is converted into active metabolites through the process of N-demethylation.<sup id="cite_ref-pmid29746911_39-0" class="reference"><a href="#cite_note-pmid29746911-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> The mechanism of action of metamizole is believed to be exerted via its active metabolites, specifically, <a href="/w/index.php?title=Arachidonoyl-4-methylaminoantipyrine&action=edit&redlink=1" class="new" title="Arachidonoyl-4-methylaminoantipyrine (page does not exist)">arachidonoyl-4-methylaminoantipyrine</a> (ARA-4-MAA) and <a href="/w/index.php?title=Arachidonoyl-4-aminoantipyrine&action=edit&redlink=1" class="new" title="Arachidonoyl-4-aminoantipyrine (page does not exist)">arachidonoyl-4-aminoantipyrine</a> (ARA-4-AA).<sup id="cite_ref-pmid36364259_40-0" class="reference"><a href="#cite_note-pmid36364259-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid31433499-2_19-1" class="reference"><a href="#cite_note-pmid31433499-2-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid24724493_24-2" class="reference"><a href="#cite_note-pmid24724493-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> This mechanism of action has been compared to <a href="/wiki/Paracetamol" title="Paracetamol">paracetamol</a> and its active arachidonic acid metabolite <a href="/wiki/AM404" title="AM404">AM404</a>. The CB1 receptor inverse agonist AM-251 was able to reduce the cataleptic response and thermal analgesia of metamizole.<sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Another study found its antihyperalgesic effect reversed by the CB2 inverse agonist AM-630<sup id="cite_ref-pmid32057719_42-0" class="reference"><a href="#cite_note-pmid32057719-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> Although it seems to inhibit fevers caused by prostaglandins, especially <a href="/wiki/Prostaglandin_E2" title="Prostaglandin E2">prostaglandin E2</a>,<sup id="cite_ref-pmid24712707_43-0" class="reference"><a href="#cite_note-pmid24712707-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> metamizole appears to produce its therapeutic effects by means of its metabolites, especially <i>N</i>-methyl-4-aminoantipyrine (MAA) and <a href="/wiki/Ampyrone" title="Ampyrone">4-aminoantipyrine</a> (AA) which form through the FAAH enzyme to create arachidonoyl-4-methylaminoantipyrine (ARA-4-MAA) and arachidonoyl-4-aminoantipyrine (ARA-4-AA).<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-10" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Metamizole likely induces the CYP2B6 and CYP3A4 enzymes.<sup id="cite_ref-pmid25199942_22-2" class="reference"><a href="#cite_note-pmid25199942-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <table class="wikitable"> <caption>Pharmacokinetics of metamizole's major metabolites<sup id="cite_ref-Winthrop_Arzneimittel_GmbH-2013_4-11" class="reference"><a href="#cite_note-Winthrop_Arzneimittel_GmbH-2013-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </caption> <tbody><tr> <th>Metabolite</th> <th>Acronym</th> <th>Biologically active?</th> <th>Pharmacokinetic properties </th></tr> <tr> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;"><span typeof="mw:File"><a href="/wiki/File:N-methyl-4-aminoantipyrine2DACS.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/N-methyl-4-aminoantipyrine2DACS.svg/200px-N-methyl-4-aminoantipyrine2DACS.svg.png" decoding="async" width="200" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/N-methyl-4-aminoantipyrine2DACS.svg/300px-N-methyl-4-aminoantipyrine2DACS.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/N-methyl-4-aminoantipyrine2DACS.svg/400px-N-methyl-4-aminoantipyrine2DACS.svg.png 2x" data-file-width="745" data-file-height="434" /></a></span><br /><i>N</i>-methyl-4-aminoantipyrine</div></td> <td>MAA</td> <td>Yes</td> <td>Bioavailability≈90%. Plasma protein binding: 58%. Excreted in the urine as 3±1% of the initial (oral) dose </td></tr> <tr> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;"><span typeof="mw:File"><a href="/wiki/File:4-aminoantipyrine2DACS.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/4-aminoantipyrine2DACS.svg/200px-4-aminoantipyrine2DACS.svg.png" decoding="async" width="200" height="112" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/10/4-aminoantipyrine2DACS.svg/300px-4-aminoantipyrine2DACS.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/10/4-aminoantipyrine2DACS.svg/400px-4-aminoantipyrine2DACS.svg.png 2x" data-file-width="741" data-file-height="414" /></a></span><br />4-aminoantipyrine</div></td> <td>AA</td> <td>Yes</td> <td>Bioavailability≈22.5%. Plasma protein binding: 48%. Excreted in the urine as 6±3% of the initial (oral) dose </td></tr> <tr> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;"><span typeof="mw:File"><a href="/wiki/File:N-formyl-4-aminoantipyrine2DACS.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/N-formyl-4-aminoantipyrine2DACS.svg/200px-N-formyl-4-aminoantipyrine2DACS.svg.png" decoding="async" width="200" height="98" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/05/N-formyl-4-aminoantipyrine2DACS.svg/300px-N-formyl-4-aminoantipyrine2DACS.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/05/N-formyl-4-aminoantipyrine2DACS.svg/400px-N-formyl-4-aminoantipyrine2DACS.svg.png 2x" data-file-width="733" data-file-height="358" /></a></span><br /><i>N</i>-formyl-4-aminoantipyrine</div></td> <td>FAA</td> <td>No</td> <td>Plasma protein binding: 18%. Excretion in the urine as 23±4% of the initial oral dose </td></tr> <tr> <td><div class="center" style="width:auto; margin-left:auto; margin-right:auto;"><span typeof="mw:File"><a href="/wiki/File:N-acetyl-4-aminoantipyrine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/N-acetyl-4-aminoantipyrine.svg/250px-N-acetyl-4-aminoantipyrine.svg.png" decoding="async" width="200" height="101" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/N-acetyl-4-aminoantipyrine.svg/330px-N-acetyl-4-aminoantipyrine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/N-acetyl-4-aminoantipyrine.svg/500px-N-acetyl-4-aminoantipyrine.svg.png 2x" data-file-width="739" data-file-height="375" /></a></span><br /><i>N</i>-acetyl-4-aminoantipyrine</div></td> <td>AAA</td> <td>No</td> <td>Plasma protein binding: 14%. Excretion in the urine as 26±8% of the initial oral dose </td></tr></tbody></table> <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=Metamizole&action=edit&section=9" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Ludwig_Knorr" title="Ludwig Knorr">Ludwig Knorr</a> was a student of <a href="/wiki/Hermann_Emil_Fischer" class="mw-redirect" title="Hermann Emil Fischer">Emil Fischer</a>, who won the Nobel Prize for his work on purines and sugars, which included the discovery of <a href="/wiki/Phenylhydrazine" title="Phenylhydrazine">phenylhydrazine</a>.<sup id="cite_ref-Brune_1-1" class="reference"><a href="#cite_note-Brune-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Nobel_Committee_44-0" class="reference"><a href="#cite_note-Nobel_Committee-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> In the 1880s, Knorr was trying to make <a href="/wiki/Quinine" title="Quinine">quinine</a> derivatives from phenylhydrazine, and instead made a <a href="/wiki/Pyrazole" title="Pyrazole">pyrazole</a> derivative, which after a methylation, he made into <a href="/wiki/Phenazone" title="Phenazone">phenazone</a>, also called antipyrine, which has been called "the 'mother' of all modern antipyretic analgesics."<sup id="cite_ref-Brune_1-2" class="reference"><a href="#cite_note-Brune-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Raviña_Rubira-2011_45-0" class="reference"><a href="#cite_note-Raviña_Rubira-2011-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 26–27">: 26–27 </span></sup> Sales of that drug exploded, and in the 1890s chemists at Teerfarbenfabrik Meister, Lucius & Co. (a precursor of <a href="/wiki/Hoechst_AG" title="Hoechst AG">Hoechst AG</a> which is now <a href="/wiki/Sanofi" title="Sanofi">Sanofi</a>), made another derivative called <a href="/wiki/Pyramidon" class="mw-redirect" title="Pyramidon">pyramidon</a> which was three times more active than antipyrine.<sup id="cite_ref-Brune_1-3" class="reference"><a href="#cite_note-Brune-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>In 1893, a derivative of antipyrine, <a href="/wiki/Aminopyrine" class="mw-redirect" title="Aminopyrine">aminopyrine</a>, was made by <a href="/wiki/Friedrich_Stolz" title="Friedrich Stolz">Friedrich Stolz</a> at Hoechst.<sup id="cite_ref-Raviña_Rubira-2011_45-1" class="reference"><a href="#cite_note-Raviña_Rubira-2011-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 26–27">: 26–27 </span></sup> Yet later, chemists at Hoechst made a derivative, melubrine (sodium antipyrine aminomethanesulfonate), which was introduced in 1913;<sup id="cite_ref-JAMA-1913_46-0" class="reference"><a href="#cite_note-JAMA-1913-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup> finally in 1920, metamizole was synthesized.<sup id="cite_ref-NikolovaTencheva20144_20-2" class="reference"><a href="#cite_note-NikolovaTencheva20144-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Metamizole is a methyl derivative of melubrine and is also a more soluble prodrug of pyramidon.<sup id="cite_ref-Brune_1-4" class="reference"><a href="#cite_note-Brune-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Raviña_Rubira-2011_45-2" class="reference"><a href="#cite_note-Raviña_Rubira-2011-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup class="reference nowrap"><span title="Page / location: 26–27">: 26–27 </span></sup> Metamizole was first marketed in Germany as "Novalgin" in 1922.<sup id="cite_ref-Brune_1-5" class="reference"><a href="#cite_note-Brune-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NikolovaTencheva20144_20-3" class="reference"><a href="#cite_note-NikolovaTencheva20144-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=10" title="Edit section: Society and culture"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Legal_status">Legal status</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=11" title="Edit section: Legal status"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Metamizole_(Dipyrone)_Availability_World_Map.svg" class="mw-file-description"><img alt="World map of availability of Metamizole" src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Metamizole_%28Dipyrone%29_Availability_World_Map.svg/200px-Metamizole_%28Dipyrone%29_Availability_World_Map.svg.png" decoding="async" width="200" height="102" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Metamizole_%28Dipyrone%29_Availability_World_Map.svg/300px-Metamizole_%28Dipyrone%29_Availability_World_Map.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Metamizole_%28Dipyrone%29_Availability_World_Map.svg/400px-Metamizole_%28Dipyrone%29_Availability_World_Map.svg.png 2x" data-file-width="2754" data-file-height="1398" /></a><figcaption> <table style=""> <tbody><tr> <td><div style="text-align:center">World map of availability of Metamizole (Dipyrone)</div> <style data-mw-deduplicate="TemplateStyles:r981673959">.mw-parser-output .legend{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .legend-color{display:inline-block;min-width:1.25em;height:1.25em;line-height:1.25;margin:1px 0;text-align:center;border:1px solid black;background-color:transparent;color:black}.mw-parser-output .legend-text{}</style><div class="legend"><span class="legend-color mw-no-invert" style="background-color:#40D0FF; color:black;-webkit-print-color-adjust: exact; print-color-adjust: exact;"> </span>  Over-the-counter with limited restrictions. </div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959" /><div class="legend"><span class="legend-color mw-no-invert" style="background-color:#4080FF; color:black;-webkit-print-color-adjust: exact; print-color-adjust: exact;"> </span>  Available, but no data on the requirement of prescriptions. </div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959" /><div class="legend"><span class="legend-color mw-no-invert" style="background-color:#3465A4; color:white;-webkit-print-color-adjust: exact; print-color-adjust: exact;"> </span>  Prescription-only, with fairly limited restrictions on its use. </div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959" /><div class="legend"><span class="legend-color mw-no-invert" style="background-color:#f57900; color:black;-webkit-print-color-adjust: exact; print-color-adjust: exact;"> </span>  Prescription-only, with extensive restrictions on its use. </div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959" /><div class="legend"><span class="legend-color mw-no-invert" style="background-color:#cc0000; color:white;-webkit-print-color-adjust: exact; print-color-adjust: exact;"> </span>  Banned for human use. It may still be used by veterinary cases in some countries. </div><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r981673959" /><div class="legend"><span class="legend-color mw-no-invert" style="background-color:#b9b9b9; color:black;-webkit-print-color-adjust: exact; print-color-adjust: exact;"> </span>  No data. </div> </td></tr></tbody></table></figcaption></figure> <p>Metamizole is banned in several countries, available by prescription in others (sometimes with strong warnings, sometimes without), and available <a href="/wiki/Over_the_counter" class="mw-redirect" title="Over the counter">over the counter</a> in yet others.<sup id="cite_ref-United_Nations_Department_of_Economic_and_Social_Affairs-2005_18-1" class="reference"><a href="#cite_note-United_Nations_Department_of_Economic_and_Social_Affairs-2005-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-UNList2_47-0" class="reference"><a href="#cite_note-UNList2-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-NR12_48-0" class="reference"><a href="#cite_note-NR12-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> For example, approval was withdrawn in Sweden (1974), the US (1977),<sup id="cite_ref-FR1977_49-0" class="reference"><a href="#cite_note-FR1977-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> and India (2013, ban lifted in 2014).<sup id="cite_ref-pmid23833116_50-0" class="reference"><a href="#cite_note-pmid23833116-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Business_Standard_India-2014_17-1" class="reference"><a href="#cite_note-Business_Standard_India-2014-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Panda-2014_51-0" class="reference"><a href="#cite_note-Panda-2014-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p><p>Although metamizole is banned in the US because of its risk of <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a>,<sup id="cite_ref-pmid12042592_52-0" class="reference"><a href="#cite_note-pmid12042592-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> it was reported by small surveys that 28% of Hispanics in Miami have possession of it,<sup id="cite_ref-pmid17004525_53-0" class="reference"><a href="#cite_note-pmid17004525-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> and 38% of Hispanics in <a href="/wiki/San_Diego" title="San Diego">San Diego</a> reported some usage.<sup id="cite_ref-pmid11527837_54-0" class="reference"><a href="#cite_note-pmid11527837-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p><p>There were unauthorized sales and use of metamizole in horses in the US. After reviewing trial data on its safety, the FDA approved it for treating fever in equines.<sup id="cite_ref-FDA2019horse_8-1" class="reference"><a href="#cite_note-FDA2019horse-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>Amid the <a href="/wiki/Opioid_epidemic" title="Opioid epidemic">opioid crisis</a>, a study pointed out that the legal status of metamizole has a relation to the consumption of <a href="/wiki/Oxycodone" title="Oxycodone">oxycodone</a>, showing the use of those drugs were inversely correlated. Its use could be beneficial when adjusted for the addictive risk of opioids, especially on limited and controlled use of metamizole.<sup id="cite_ref-cdrr1_55-0" class="reference"><a href="#cite_note-cdrr1-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> A 2019 Israeli conference also justified the approved status as a preventive to opioid dependence, and metamizole being safer than most analgesics for renal impaired patients.<sup id="cite_ref-pmid31721040_56-0" class="reference"><a href="#cite_note-pmid31721040-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>Metamizole is the most sold medication in <a href="/wiki/S%C3%A3o_Paulo" title="São Paulo">São Paulo</a>, Brazil, accounting for 488 tons in 2016.<sup id="cite_ref-pmid33237204_57-0" class="reference"><a href="#cite_note-pmid33237204-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> Given this contrasting consumption compared to other countries, the <a href="/wiki/Brazilian_Health_Regulatory_Agency" title="Brazilian Health Regulatory Agency">Brazilian Health Regulatory Agency (ANVISA)</a> convened an international panel for evaluating its safety in 2001, and the conclusion was that the benefits substantially outweighed the risks, and imposing restrictions would lead to significant negative consequences to the population.<sup id="cite_ref-ANVISA2001_58-0" class="reference"><a href="#cite_note-ANVISA2001-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Reis2022_26-1" class="reference"><a href="#cite_note-Reis2022-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> It is also highly popular in Latin America overall. In 2022 in Brazil alone over 215 million doses were administered.<sup id="cite_ref-Biernath-2023_59-0" class="reference"><a href="#cite_note-Biernath-2023-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> </p><p>The Bulgarian pharmaceutical <a href="/w/index.php?title=Sopharma&action=edit&redlink=1" class="new" title="Sopharma (page does not exist)">Sopharma</a> produces it under the brand Analgin, which as of 2014, has been the top-selling analgesic in Bulgaria for over a decade.<sup id="cite_ref-pmid26019521_16-1" class="reference"><a href="#cite_note-pmid26019521-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>In Germany, the drug is the most commonly prescribed painreliever.<sup id="cite_ref-cdrr1_55-1" class="reference"><a href="#cite_note-cdrr1-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p>In 2012, headache accounts for 70% of its use in Indonesia.<sup id="cite_ref-Kurniawati-2012_60-0" class="reference"><a href="#cite_note-Kurniawati-2012-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p><p>In 2018, investigators in Spain looked into Nolotil (as metamizole is known in Spain) after the death of several British people in Spain. A possible factor in these deaths might have been a side effect of metamizole that can cause agranulocytosis (a lowering of <a href="/wiki/White_blood_cell" title="White blood cell">white blood cell</a> count).<sup id="cite_ref-Exclusive-2018_61-0" class="reference"><a href="#cite_note-Exclusive-2018-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Brand_names">Brand names</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=12" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Metamizole is the <a href="/wiki/International_nonproprietary_name" title="International nonproprietary name">international nonproprietary name</a>, and in countries where it is marketed, it is available under many brand names.<sup id="cite_ref-EMA-list_2-2" class="reference"><a href="#cite_note-EMA-list-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>In Romania metamizole is available as the original marketed pharmaceutical product by Zentiva as Algocalmin, as 500 mg immediate release tablets. It's also available as an injection with 1 g of metamizole sodium dissolved in 2 ml of solvent. </p><p>In Israel it is sold under the brand name "Optalgin" (<a href="/wiki/Hebrew_language" title="Hebrew language">Hebrew</a>: <span lang="he" dir="rtl">אופטלגין</span>), manufactured by <a href="/wiki/Teva_Pharmaceuticals" title="Teva Pharmaceuticals">Teva</a>. </p><p>In <a href="/wiki/Czech_Republic" title="Czech Republic">Czechia</a> it is available under the brand name "Algifen Neo" in the form of drops containing 500 mg/ml of Metamizole and 5 mg/ml of <a href="/wiki/Pitofenone" title="Pitofenone">Pitofenone</a>, manufactured by Teva. </p><p>It is known as Sulpyrin and Sulpyrine in South Korea (<span title="Korean-language text"><span lang="ko">설피린</span></span>) and Japan. (<span title="Japanese-language text"><span lang="ja">スルピリン</span></span>)<sup id="cite_ref-Kim-2004_62-0" class="reference"><a href="#cite_note-Kim-2004-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Pharmaceutical_and_Medical_Device_Regulatory_Science_Society_of_Japan-2022_63-0" class="reference"><a href="#cite_note-Pharmaceutical_and_Medical_Device_Regulatory_Science_Society_of_Japan-2022-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Analgin">Analgin</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=13" title="Edit section: Analgin"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Analgin (Russian: <span lang="ru">Анальгин</span>) is a <a href="/wiki/Generic_term" class="mw-redirect" title="Generic term">generic name</a> used in the former <a href="/wiki/Soviet_Union" title="Soviet Union">USSR</a> <a href="/wiki/Pharmacopeia" class="mw-redirect" title="Pharmacopeia">pharmacopeia</a>,<sup id="cite_ref-Ministry_of_Health_of_the_USSR-1968_64-0" class="reference"><a href="#cite_note-Ministry_of_Health_of_the_USSR-1968-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> continuing in use in <a href="/wiki/Slavs" title="Slavs">Slavic</a> nations. A firm in Russia tried unsuccessfully in 2011 to claim the name as their trademark.<sup id="cite_ref-Ovchinnikov-2011_65-0" class="reference"><a href="#cite_note-Ovchinnikov-2011-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EPAM_Law-2012_66-0" class="reference"><a href="#cite_note-EPAM_Law-2012-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup> In Bulgaria, <a href="/w/index.php?title=Sopharma&action=edit&redlink=1" class="new" title="Sopharma (page does not exist)">Sopharma</a> succeeded in registering Analgin as a trademark in 2004.<sup id="cite_ref-FFBH-2004_67-0" class="reference"><a href="#cite_note-FFBH-2004-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p><p>Analgin is also the common term used in the Indian pharmacopeia.<sup id="cite_ref-Ministry_of_Health_and_Family_Welfare-2007_68-0" class="reference"><a href="#cite_note-Ministry_of_Health_and_Family_Welfare-2007-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Metamizole&action=edit&section=14" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Brune-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Brune_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Brune_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Brune_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Brune_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Brune_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Brune_1-5"><sup><i><b>f</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFBrune1997" class="citation journal cs1">Brune K (December 1997). 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Retrieved <span class="nowrap">2023-08-14</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=European+Medicines+Agency&rft.atitle=Metamizole+Annex+I+-+List+of+nationally+authorised+medicinal+products&rft.date=2018-06-01&rft_id=https%3A%2F%2Fwww.ema.europa.eu%2Fen%2Fdocuments%2Freferral%2Fmetamizole-article-31-referral-annex-i_en.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-Pharmaceuticale_Press-2009-3"><span class="mw-cite-backlink">^ <a href="#cite_ref-Pharmaceuticale_Press-2009_3-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Pharmaceuticale_Press-2009_3-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Pharmaceuticale_Press-2009_3-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Pharmaceuticale_Press-2009_3-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Pharmaceuticale_Press-2009_3-4"><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="CITEREFMartindaleSweetman2009" class="citation book cs1">Martindale W, Sweetman SC, eds. 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Retrieved <span class="nowrap">2017-06-14</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Nobel+Committee&rft.atitle=Emil+Fischer+%E2%80%93+Biographical&rft_id=https%3A%2F%2Fwww.nobelprize.org%2Fnobel_prizes%2Fchemistry%2Flaureates%2F1902%2Ffischer-bio.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-Raviña_Rubira-2011-45"><span class="mw-cite-backlink">^ <a href="#cite_ref-Raviña_Rubira-2011_45-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Raviña_Rubira-2011_45-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Raviña_Rubira-2011_45-2"><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="CITEREFRaviña_Rubira2011" class="citation book cs1">Raviña Rubira E (2011). <i>The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs</i>. 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(January 2012). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3248997">"Novel bioactive metabolites of dipyrone (metamizol)"</a>. <i>Bioorganic & Medicinal Chemistry</i>. <b>20</b> (1): <span class="nowrap">101–</span>107. <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%2Fj.bmc.2011.11.028">10.1016/j.bmc.2011.11.028</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/PMC3248997">3248997</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/22172309">22172309</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorganic+%26+Medicinal+Chemistry&rft.atitle=Novel+bioactive+metabolites+of+dipyrone+%28metamizol%29&rft.volume=20&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E101-%3C%2Fspan%3E107&rft.date=2012-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3248997%23id-name%3DPMC&rft_id=info%3Apmid%2F22172309&rft_id=info%3Adoi%2F10.1016%2Fj.bmc.2011.11.028&rft.aulast=Rogosch&rft.aufirst=T&rft.au=Sinning%2C+C&rft.au=Podlewski%2C+A&rft.au=Watzer%2C+B&rft.au=Schlosburg%2C+J&rft.au=Lichtman%2C+AH&rft.au=Cascio%2C+MG&rft.au=Bisogno%2C+T&rft.au=Di+Marzo%2C+V&rft.au=N%C3%BCsing%2C+R&rft.au=Imming%2C+P&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3248997&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-FR1977-49"><span class="mw-cite-backlink"><b><a href="#cite_ref-FR1977_49-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGardner1977" class="citation report cs1">Gardner S (1977-06-07). <a rel="nofollow" class="external text" href="https://www.govinfo.gov/app/details/FR-1977-06-17">Drug products containing dipyrone - Withdrawal of Approval of New Drug Applications</a> (Report). Vol. 42. Federal Register (published 1977-06-17). pp. <span class="nowrap">30893–</span>4. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0097-6326">0097-6326</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20200929015340/https://www.govinfo.gov/app/details/FR-1977-06-17">Archived</a> from the original on 2020-09-29<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-08-04</span></span>. <q>This notice withdraws approval of the new drug applications (NDA's) for drug products containing dipyrone. The drug products have been used to reduce fever, but they are not shown to be safe for use. On the basis of new evidence, not contained in the applications or not available until after the applications were approved, evaluated together with the evidence available when the applications were approved, the Commissioner of Food and Drugs finds that such drugs have not been shown to be safe for use upon the basis of which the applications were approved. (...) approval of the NDA's providing for the drug products named above, and all amendments and supplements applying thereto, is withdrawn effective June 27,1977. Shipment in interstate commerce of the above-listed products or of any identical, related, or similar product, not the subject of an approved NDA, will then be unlawful.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=Drug+products+containing+dipyrone+-+Withdrawal+of+Approval+of+New+Drug+Applications&rft.pages=%3Cspan+class%3D%22nowrap%22%3E30893-%3C%2Fspan%3E4&rft.pub=Federal+Register&rft.date=1977-06-07&rft.issn=0097-6326&rft.aulast=Gardner&rft.aufirst=S&rft_id=https%3A%2F%2Fwww.govinfo.gov%2Fapp%2Fdetails%2FFR-1977-06-17&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-pmid23833116-50"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid23833116_50-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBhaumik2013" class="citation journal cs1">Bhaumik S (July 2013). 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Retrieved <span class="nowrap">27 April</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Exclusive%3A+southern+spain+hospitals+in+british+expat+hotspot+issue+warning+for+%27lethal%27+painkiller+nolotil&rft.date=2018-04-23&rft_id=http%3A%2F%2Fwww.theolivepress.es%2Fspain-news%2F2018%2F04%2F23%2Fexclusive-southern-spain-hospitals-in-british-expat-hotspot-issue-warning-for-lethal-painkiller-nolotil%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-Kim-2004-62"><span class="mw-cite-backlink"><b><a href="#cite_ref-Kim-2004_62-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFKim2004" class="citation web cs1 cs1-prop-foreign-lang-source">Kim CH (2004-08-26). <a rel="nofollow" class="external text" href="http://www.kgnews.co.kr/news/article.html?no=66244">"해열진통제 '설피린' 국내사용 논란"</a> [Controversy over domestic use of antipyretic analgesic Sulpyrin]. <i>경기신문 [kgnews]</i> (in Korean). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230814051807/https://www.kgnews.co.kr/news/article.html?no=66244">Archived</a> from the original on 2023-08-14<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-08-14</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=%EA%B2%BD%EA%B8%B0%EC%8B%A0%EB%AC%B8+%5Bkgnews%5D&rft.atitle=%ED%95%B4%EC%97%B4%EC%A7%84%ED%86%B5%EC%A0%9C+%27%EC%84%A4%ED%94%BC%EB%A6%B0%27+%EA%B5%AD%EB%82%B4%EC%82%AC%EC%9A%A9+%EB%85%BC%EB%9E%80&rft.date=2004-08-26&rft.aulast=Kim&rft.aufirst=CH&rft_id=http%3A%2F%2Fwww.kgnews.co.kr%2Fnews%2Farticle.html%3Fno%3D66244&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-Pharmaceutical_and_Medical_Device_Regulatory_Science_Society_of_Japan-2022-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-Pharmaceutical_and_Medical_Device_Regulatory_Science_Society_of_Japan-2022_63-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPharmaceutical_and_Medical_Device_Regulatory_Science_Society_of_Japan2022" class="citation book cs1">Pharmaceutical and Medical Device Regulatory Science Society of Japan (2022). <a rel="nofollow" class="external text" href="https://jpdb.nihs.go.jp/kyokuhou/files/000904449.pdf"><i>The Japanese Pharmacopoeia</i></a> <span class="cs1-format">(PDF)</span> (18th English ed.). Yakuji Nippo-sha. p. 1760. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-4-8408-1589-5" title="Special:BookSources/978-4-8408-1589-5"><bdi>978-4-8408-1589-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230120063124/https://jpdb.nihs.go.jp/kyokuhou/files/000904449.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2023-01-20<span class="reference-accessdate">. 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Moscow: Медицина [Medicine]. p. 94.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=%D0%93%D0%BE%D1%81%D1%83%D0%B4%D0%B0%D1%80%D1%81%D1%82%D0%B2%D0%B5%D0%BD%D0%BD%D0%B0%D1%8F+%D0%A4%D0%B0%D1%80%D0%BC%D0%B0%D0%BA%D0%BE%D0%BF%D0%B5%D1%8F+%D0%A1%D0%BE%D1%8E%D0%B7%D0%B0+%D0%A1%D0%BE%D0%B2%D0%B5%D1%82%D1%81%D0%BA%D0%B8%D1%85+%D0%A1%D0%BE%D1%86%D0%B8%D0%B0%D0%BB%D0%B8%D1%81%D1%82%D0%B8%D1%87%D0%B5%D1%81%D0%BA%D0%B8%D1%85+%D0%A0%D0%B5%D1%81%D0%BF%D1%83%D0%B1%D0%BB%D0%B8%D0%BA&rft.place=Moscow&rft.pages=94&rft.edition=10th&rft.pub=%D0%9C%D0%B5%D0%B4%D0%B8%D1%86%D0%B8%D0%BD%D0%B0+%5BMedicine%5D&rft.date=1968&rft.au=Ministry+of+Health+of+the+USSR&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-Ovchinnikov-2011-65"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ovchinnikov-2011_65-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFOvchinnikov2011" class="citation web cs1 cs1-prop-foreign-lang-source">Ovchinnikov R (2011-12-22). <a rel="nofollow" class="external text" href="https://iz.ru/news/510490">"Анальгин хотят отпустить в одни руки"</a> [Analgin want to let go in one hand]. <i>Известия</i> (in Russian). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230812060914/https://iz.ru/news/510490">Archived</a> from the original on 2023-08-12.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=%D0%98%D0%B7%D0%B2%D0%B5%D1%81%D1%82%D0%B8%D1%8F&rft.atitle=%D0%90%D0%BD%D0%B0%D0%BB%D1%8C%D0%B3%D0%B8%D0%BD+%D1%85%D0%BE%D1%82%D1%8F%D1%82+%D0%BE%D1%82%D0%BF%D1%83%D1%81%D1%82%D0%B8%D1%82%D1%8C+%D0%B2+%D0%BE%D0%B4%D0%BD%D0%B8+%D1%80%D1%83%D0%BA%D0%B8&rft.date=2011-12-22&rft.aulast=Ovchinnikov&rft.aufirst=R&rft_id=https%3A%2F%2Fiz.ru%2Fnews%2F510490&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-EPAM_Law-2012-66"><span class="mw-cite-backlink"><b><a href="#cite_ref-EPAM_Law-2012_66-0">^</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="https://epam.ru/en/media/view/pavel-sadovsky-comments-on-trademarks-registering-for-ria-novosti">"Pavel Sadovsky comments on trademarks registering for RIA Novosti - Insights"</a>. <i>EPAM Law</i>. 2012-02-22. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20210225185525/https://epam.ru/en/media/view/pavel-sadovsky-comments-on-trademarks-registering-for-ria-novosti">Archived</a> from the original on 2021-02-25<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-08-14</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=EPAM+Law&rft.atitle=Pavel+Sadovsky+comments+on+trademarks+registering+for+RIA+Novosti+-+Insights&rft.date=2012-02-22&rft_id=https%3A%2F%2Fepam.ru%2Fen%2Fmedia%2Fview%2Fpavel-sadovsky-comments-on-trademarks-registering-for-ria-novosti&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-FFBH-2004-67"><span class="mw-cite-backlink"><b><a href="#cite_ref-FFBH-2004_67-0">^</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="https://www.ffbh.bg/en/post/sopharma-wins-tm-battle-over-analgesic-drug-analgin-x000d--158997700025989">"Sopharma wins TM battle over analgesic drug Analgin"</a>. <i>FFBH</i>. 2004-08-05. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230814025944/https://www.ffbh.bg/en/post/sopharma-wins-tm-battle-over-analgesic-drug-analgin-x000d--158997700025989">Archived</a> from the original on 2023-08-14<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-08-14</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=FFBH&rft.atitle=Sopharma+wins+TM+battle+over+analgesic+drug+Analgin&rft.date=2004-08-05&rft_id=https%3A%2F%2Fwww.ffbh.bg%2Fen%2Fpost%2Fsopharma-wins-tm-battle-over-analgesic-drug-analgin-x000d--158997700025989&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> <li id="cite_note-Ministry_of_Health_and_Family_Welfare-2007-68"><span class="mw-cite-backlink"><b><a href="#cite_ref-Ministry_of_Health_and_Family_Welfare-2007_68-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMinistry_of_Health_and_Family_Welfare2007" class="citation book cs1">Ministry of Health and Family Welfare (2007). <a rel="nofollow" class="external text" href="https://www.planetayurveda.com/ayurveda-ebooks/indian-pharmacopoea.pdf"><i>Indian Pharmacopeia</i></a> <span class="cs1-format">(PDF)</span>. Vol. 2. Ghaziabad, India: Indian Pharmacopoeia Commission. p. 117. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20230728083229/https://www.planetayurveda.com/ayurveda-ebooks/indian-pharmacopoea.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2023-07-28<span class="reference-accessdate">. Retrieved <span class="nowrap">2023-08-13</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Indian+Pharmacopeia&rft.place=Ghaziabad%2C+India&rft.pages=117&rft.pub=Indian+Pharmacopoeia+Commission&rft.date=2007&rft.au=Ministry+of+Health+and+Family+Welfare&rft_id=https%3A%2F%2Fwww.planetayurveda.com%2Fayurveda-ebooks%2Findian-pharmacopoea.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMetamizole" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl 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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)808" 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 class="mw-selflink selflink">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 href="/wiki/Salicylic_acid" title="Salicylic acid">salicylates</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><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 href="/wiki/Salicylic_acid" title="Salicylic acid">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/Meloxicam/rizatriptan" title="Meloxicam/rizatriptan">Meloxicam/rizatriptan</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/20px-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/40px-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/20px-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/40px-Symbol_portal_class.svg.png 1.5x" 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)251" 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)251" style="font-size:114%;margin:0 4em"><a href="/wiki/Analgesic" title="Analgesic">Analgesics</a> (<a href="/wiki/ATC_code_N02#N02A" title="ATC code N02">N02A</a>, <a href="/wiki/ATC_code_N02#N02B" title="ATC code N02">N02B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opioid" title="Opioid">Opioids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Opiate" title="Opiate">Opiates</a>/<a href="/wiki/Opium" title="Opium">opium</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Codeine" title="Codeine">Codeine</a><sup>#</sup> <ul><li><a href="/wiki/Codeine/aspirin" class="mw-redirect" title="Codeine/aspirin">+aspirin</a></li> <li><a href="/wiki/Codeine/paracetamol" title="Codeine/paracetamol">+paracetamol</a></li></ul></li> <li><a href="/wiki/Morphine" title="Morphine">Morphine</a><sup>#</sup> (<a href="/wiki/Morphine/naltrexone" title="Morphine/naltrexone">+naltrexone</a>)</li> <li><a href="/wiki/Opium" title="Opium">Opium</a></li> <li><a href="/wiki/Laudanum" title="Laudanum">Laudanum</a></li> <li><a href="/wiki/Paregoric" title="Paregoric">Paregoric</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Semisynthetic</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetyldihydrocodeine" title="Acetyldihydrocodeine">Acetyldihydrocodeine</a></li> <li><a href="/wiki/Benzylmorphine" title="Benzylmorphine">Benzylmorphine</a></li> <li><a href="/wiki/Buprenorphine" title="Buprenorphine">Buprenorphine</a><span class="nowrap"> </span>(<a href="/wiki/Buprenorphine/naloxone" title="Buprenorphine/naloxone">+naloxone</a>)</li> <li><a href="/wiki/Butorphanol" title="Butorphanol">Butorphanol</a></li> <li><a href="/wiki/Desomorphine" title="Desomorphine">Desomorphine</a></li> <li><a href="/wiki/Heroin" title="Heroin">Diamorphine (heroin)</a></li> <li><a href="/wiki/Dihydrocodeine" title="Dihydrocodeine">Dihydrocodeine</a><span class="nowrap"> </span>(<a href="/wiki/Co-dydramol" title="Co-dydramol">+paracetamol</a>)</li> <li><a href="/wiki/Dihydromorphine" title="Dihydromorphine">Dihydromorphine</a></li> <li><a href="/wiki/Etorphine" title="Etorphine">Etorphine</a></li> <li><a href="/wiki/Ethylmorphine" title="Ethylmorphine">Ethylmorphine</a></li> <li><a href="/wiki/Hydrocodone" title="Hydrocodone">Hydrocodone</a><span class="nowrap"> </span>(<a href="/wiki/Hydrocodone/paracetamol" title="Hydrocodone/paracetamol">+paracetamol</a>, <a href="/wiki/Hydrocodone/ibuprofen" title="Hydrocodone/ibuprofen">+ibuprofen</a>, <a href="/wiki/Hydrocodone/aspirin" title="Hydrocodone/aspirin">+aspirin</a>)</li> <li><a href="/wiki/Hydromorphinol" title="Hydromorphinol">Hydromorphinol</a></li> <li><a href="/wiki/Hydromorphone" title="Hydromorphone">Hydromorphone</a></li> <li><a href="/wiki/Levorphanol" title="Levorphanol">Levorphanol</a></li> <li><a href="/wiki/Metopon" title="Metopon">Metopon</a></li> <li><a href="/wiki/Nalbuphine" title="Nalbuphine">Nalbuphine</a></li> <li><a href="/wiki/Nicocodeine" title="Nicocodeine">Nicocodeine</a></li> <li><a href="/wiki/Nicodicodine" title="Nicodicodine">Nicodicodine</a></li> <li><a href="/wiki/Nicomorphine" title="Nicomorphine">Nicomorphine</a></li> <li><a href="/wiki/Oxycodone" title="Oxycodone">Oxycodone</a><span class="nowrap"> </span>(<a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">+paracetamol</a>, <a href="/wiki/Oxycodone/aspirin" title="Oxycodone/aspirin">+aspirin</a>, <a href="/wiki/Oxycodone/ibuprofen" title="Oxycodone/ibuprofen">+ibuprofen</a>, <a href="/wiki/Oxycodone/naloxone" title="Oxycodone/naloxone">+naloxone</a>, <a href="/w/index.php?title=Oxycodone/naltrexone&action=edit&redlink=1" class="new" title="Oxycodone/naltrexone (page does not exist)">+naltrexone</a>)</li> <li><a href="/wiki/Oxymorphone" title="Oxymorphone">Oxymorphone</a></li> <li><a href="/wiki/Papaveretum" title="Papaveretum">Papaveretum</a></li> <li><a href="/wiki/Thebacon" title="Thebacon">Thebacon</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Synthetic</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alfentanil" title="Alfentanil">Alfentanil</a></li> <li><a href="/wiki/Prodine" title="Prodine">Alphaprodine</a></li> <li><a href="/wiki/Anileridine" title="Anileridine">Anileridine</a></li> <li><a href="/wiki/Bezitramide" title="Bezitramide">Bezitramide</a></li> <li><a href="/wiki/Carfentanil" title="Carfentanil">Carfentanil</a></li> <li><a href="/wiki/Dextromoramide" title="Dextromoramide">Dextromoramide</a></li> <li><a href="/wiki/Dextropropoxyphene" title="Dextropropoxyphene">Dextropropoxyphene</a></li> <li><a href="/wiki/Dezocine" title="Dezocine">Dezocine</a></li> <li><a href="/wiki/Dimenoxadol" title="Dimenoxadol">Dimenoxadol</a></li> <li><a href="/wiki/Dipipanone" title="Dipipanone">Dipipanone</a></li> <li><a href="/wiki/Ethoheptazine" title="Ethoheptazine">Ethoheptazine</a></li> <li><a href="/wiki/Fentanyl" title="Fentanyl">Fentanyl</a><sup>#</sup> (<a href="/wiki/Fentanyl/fluanisone" title="Fentanyl/fluanisone">+fluanisone</a>)</li> <li><a href="/wiki/Ketobemidone" title="Ketobemidone">Ketobemidone</a></li> <li><a href="/wiki/Lofentanil" title="Lofentanil">Lofentanil</a></li> <li><a href="/wiki/Meptazinol" title="Meptazinol">Meptazinol</a></li> <li><a href="/wiki/Methadone" title="Methadone">Methadone</a><sup>#</sup></li> <li><a href="/wiki/NFEPP" title="NFEPP">NFEPP</a></li> <li><a href="/wiki/Norpipanone" title="Norpipanone">Norpipanone</a></li> <li><a href="/wiki/Oliceridine" title="Oliceridine">Oliceridine</a></li> <li><a href="/wiki/Pentazocine" title="Pentazocine">Pentazocine</a></li> <li><a href="/wiki/Pethidine" title="Pethidine">Pethidine (meperidine)</a></li> <li><a href="/wiki/Phenadoxone" title="Phenadoxone">Phenadoxone</a></li> <li><a href="/wiki/Phenazocine" title="Phenazocine">Phenazocine</a></li> <li><a href="/wiki/Phenoperidine" title="Phenoperidine">Phenoperidine</a></li> <li><a href="/wiki/Piminodine" title="Piminodine">Piminodine</a></li> <li><a href="/wiki/Piritramide" title="Piritramide">Piritramide</a></li> <li><a href="/wiki/Proheptazine" title="Proheptazine">Proheptazine</a></li> <li><a href="/wiki/Propiram" title="Propiram">Propiram</a></li> <li><a href="/wiki/Remifentanil" title="Remifentanil">Remifentanil</a></li> <li><a href="/wiki/Sufentanil" title="Sufentanil">Sufentanil</a></li> <li><a href="/wiki/Tapentadol" title="Tapentadol">Tapentadol</a></li> <li><a href="/wiki/Tilidine" title="Tilidine">Tilidine</a></li> <li><a href="/wiki/Tramadol" title="Tramadol">Tramadol</a><span class="nowrap"> </span>(<a href="/wiki/Celecoxib/tramadol" title="Celecoxib/tramadol">+celecoxib</a>, <a href="/wiki/Tramadol/paracetamol" title="Tramadol/paracetamol">+paracetamol</a>)</li> <li><a href="/wiki/Viminol" title="Viminol">Viminol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol</a>-type</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetanilide" title="Acetanilide">Acetanilide</a><sup>‡</sup></li> <li><a href="/wiki/Bucetin" title="Bucetin">Bucetin</a><sup>‡</sup></li> <li><a href="/w/index.php?title=Butacetin&action=edit&redlink=1" class="new" title="Butacetin (page does not exist)">Butacetin</a><sup>‡</sup></li> <li><a href="/wiki/Paracetamol" title="Paracetamol">Paracetamol (acetaminophen)</a><sup>#</sup> <ul><li><a href="/wiki/Aspirin/paracetamol/caffeine" title="Aspirin/paracetamol/caffeine">+aspirin/caffeine</a></li> <li><a href="/wiki/Codeine/paracetamol" title="Codeine/paracetamol">+codeine</a></li> <li><a href="/wiki/Hydrocodone/paracetamol" title="Hydrocodone/paracetamol">+hydrocodone</a></li> <li><a href="/wiki/Ibuprofen/paracetamol" title="Ibuprofen/paracetamol">+ibuprofen</a></li> <li><a href="/wiki/Paracetamol/metoclopramide" title="Paracetamol/metoclopramide">+metoclopramide</a></li> <li><a href="/wiki/Oxycodone/paracetamol" title="Oxycodone/paracetamol">+oxycodone</a></li> <li><a href="/wiki/Propyphenazone/paracetamol/caffeine" title="Propyphenazone/paracetamol/caffeine">+propyphenazone/caffeine</a></li> <li><a href="/wiki/Tramadol/paracetamol" title="Tramadol/paracetamol">+tramadol</a></li></ul></li> <li><a href="/w/index.php?title=Parapropamol&action=edit&redlink=1" class="new" title="Parapropamol (page does not exist)">Parapropamol</a><sup>‡</sup></li> <li><a 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 href="/wiki/Salicylic_acid" title="Salicylic acid">Salicylates</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aspirin" title="Aspirin">Aspirin (acetylsalicylic acid)</a><sup>#</sup> (<a href="/wiki/Aspirin/paracetamol/caffeine" title="Aspirin/paracetamol/caffeine">+paracetamol/caffeine</a>)</li> <li><a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Benorilate" title="Benorilate">Benorylate</a></li> <li><a href="/wiki/Carbasalate_calcium" title="Carbasalate calcium">Carbasalate calcium</a></li> <li><a href="/wiki/Choline_salicylate" class="mw-redirect" title="Choline salicylate">Choline salicylate</a></li> <li><a href="/wiki/Diflunisal" title="Diflunisal">Diflunisal</a></li> <li><a href="/wiki/Dipyrocetyl" title="Dipyrocetyl">Dipyrocetyl</a></li> <li><a href="/wiki/Ethenzamide" title="Ethenzamide">Ethenzamide</a></li> <li><a href="/wiki/Guacetisal" title="Guacetisal">Guacetisal</a></li> <li><a href="/wiki/Imidazole_salicylate" title="Imidazole salicylate">Imidazole salicylate</a></li> <li><a href="/wiki/Magnesium_salicylate" title="Magnesium salicylate">Magnesium salicylate</a></li> <li><a href="/wiki/Morpholine_salicylate" title="Morpholine salicylate">Morpholine salicylate</a></li> <li><a href="/wiki/Potassium_salicylate" title="Potassium salicylate">Potassium salicylate</a></li> <li><a href="/wiki/Salicin" title="Salicin">Salicin</a></li> <li><a href="/wiki/Salicylamide" title="Salicylamide">Salicylamide</a></li> <li><a href="/wiki/Salsalate" title="Salsalate">Salsalate</a></li> <li><a href="/wiki/Sodium_salicylate" title="Sodium salicylate">Sodium salicylate</a></li> <li><a href="/wiki/Wintergreen" title="Wintergreen">Wintergreen</a><span class="nowrap"> </span>(<a href="/wiki/Methyl_salicylate" title="Methyl salicylate">methyl salicylate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrazolone" title="Pyrazolone">Pyrazolones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminophenazone" title="Aminophenazone">Aminophenazone</a><sup>‡</sup></li> <li><a href="/wiki/Ampyrone" title="Ampyrone">Ampyrone</a></li> <li><a class="mw-selflink selflink">Metamizole (dipyrone)</a></li> <li><a href="/wiki/Nifenazone" title="Nifenazone">Nifenazone</a></li> <li><a href="/wiki/Phenazone" title="Phenazone">Phenazone</a></li> <li><a href="/wiki/Propyphenazone" title="Propyphenazone">Propyphenazone</a><span class="nowrap"> </span>(<a href="/wiki/Propyphenazone/paracetamol/caffeine" title="Propyphenazone/paracetamol/caffeine">+paracetamol/caffeine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzydamine" title="Benzydamine">Benzydamine</a></li> <li><a href="/wiki/Floctafenine" title="Floctafenine">Floctafenine</a></li> <li><a href="/wiki/Glafenine" title="Glafenine">Glafenine</a></li> <li><a href="/wiki/Nabumetone" title="Nabumetone">Nabumetone</a></li> <li><a href="/wiki/Nimesulide" title="Nimesulide">Nimesulide</a></li> <li><a href="/wiki/Proquazone" title="Proquazone">Proquazone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cannabinoid" title="Cannabinoid">Cannabinoids</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cannabidiol" title="Cannabidiol">Cannabidiol</a></li> <li><a href="/wiki/Cannabis_(drug)" title="Cannabis (drug)">Cannabis</a></li> <li><a href="/wiki/Nabilone" title="Nabilone">Nabilone</a></li> <li><a href="/wiki/Nabiximols" title="Nabiximols">Nabiximols</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol (dronabinol)</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Channel_modulator" title="Channel modulator">Ion channel<br />modulators</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Calcium_channel_blocker" title="Calcium channel blocker">Calcium blockers</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Alcohol_(drug)" title="Alcohol (drug)">Alcohol (ethanol)</a></li> <li><a href="/wiki/Gabapentin" title="Gabapentin">Gabapentin</a></li> <li><a href="/wiki/Gabapentin_enacarbil" title="Gabapentin enacarbil">Gabapentin enacarbil</a></li> <li><a href="/wiki/Leconotide" title="Leconotide">Leconotide</a></li> <li><a href="/wiki/Mirogabalin" title="Mirogabalin">Mirogabalin</a></li> <li><a href="/wiki/Pregabalin" title="Pregabalin">Pregabalin</a></li> <li><a href="/wiki/Ziconotide" title="Ziconotide">Ziconotide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">Sodium blockers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carbamazepine" title="Carbamazepine">Carbamazepine</a></li> <li><a href="/wiki/Lacosamide" title="Lacosamide">Lacosamide</a></li> <li><a href="/wiki/Local_anesthetic" title="Local anesthetic">Local anesthetics</a> (e.g., <a href="/wiki/Cocaine" title="Cocaine">cocaine</a>, <a href="/wiki/Lidocaine" title="Lidocaine">lidocaine</a>)</li> <li><a href="/wiki/Mexiletine" title="Mexiletine">Mexiletine</a></li> <li><a href="/wiki/Nefopam" title="Nefopam">Nefopam</a></li> <li><a href="/wiki/Tricyclic_antidepressant" title="Tricyclic antidepressant">Tricyclic antidepressants</a> (e.g., <a href="/wiki/Amitriptyline" title="Amitriptyline">amitriptyline</a><sup>#</sup>)</li></ul> <ul><li><i>Na<sub>v</sub>1.7/1.8-selective:</i> <a href="/wiki/DSP-2230" title="DSP-2230">DSP-2230</a><sup>§</sup></li> <li><a href="/wiki/Funapide" title="Funapide">Funapide</a><sup>§</sup></li> <li><a href="/wiki/PF-05089771" title="PF-05089771">PF-05089771</a><sup>§</sup></li> <li><a href="/wiki/Suzetrigine" title="Suzetrigine">Suzetrigine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Potassium_channel_opener" title="Potassium channel opener">Potassium openers</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Flupirtine" title="Flupirtine">Flupirtine</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Muscle_relaxant" title="Muscle relaxant">Myorelaxants</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Carisoprodol" title="Carisoprodol">Carisoprodol</a></li> <li><a href="/wiki/Chlorzoxazone" title="Chlorzoxazone">Chlorzoxazone</a></li> <li><a href="/wiki/Cyclobenzaprine" title="Cyclobenzaprine">Cyclobenzaprine</a></li> <li><a href="/wiki/Mephenoxalone" title="Mephenoxalone">Mephenoxalone</a></li> <li><a href="/wiki/Methocarbamol" title="Methocarbamol">Methocarbamol</a></li> <li><a href="/wiki/Orphenadrine" title="Orphenadrine">Orphenadrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Analgecine" title="Analgecine">Analgecine</a></li> <li><a href="/wiki/Analgesic_adjuvant" title="Analgesic adjuvant">Analgesic adjuvant</a></li> <li><a href="/wiki/Bedinvetmab" title="Bedinvetmab">Bedinvetmab</a></li> <li><a href="/wiki/Camphor" title="Camphor">Camphor</a></li> <li><a href="/wiki/Capsaicin" title="Capsaicin">Capsaicin</a></li> <li><a href="/wiki/Clonidine" title="Clonidine">Clonidine</a></li> <li><a href="/wiki/Frunevetmab" title="Frunevetmab">Frunevetmab</a></li> <li><a href="/wiki/Ketamine" title="Ketamine">Ketamine</a></li> <li><a href="/wiki/Menthol" title="Menthol">Menthol</a></li> <li><a href="/wiki/Methoxyflurane" title="Methoxyflurane">Methoxyflurane</a></li> <li><a href="/wiki/Phenazopyridine" title="Phenazopyridine">Phenazopyridine</a></li> <li><a href="/wiki/Proglumide" title="Proglumide">Proglumide</a></li> <li><a href="/wiki/Rimazolium" title="Rimazolium">Rimazolium</a></li> <li><a href="/wiki/Tanezumab" title="Tanezumab">Tanezumab</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox authority-control" aria-label="Navbox390" 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/Q422761#identifiers" title="Edit 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