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<span>Medical uses</span> </div> </a> <button aria-controls="toc-Medical_uses-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 Medical uses subsection</span> </button> <ul id="toc-Medical_uses-sublist" class="vector-toc-list"> <li id="toc-Tuberculosis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Tuberculosis"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.1</span> <span>Tuberculosis</span> </div> </a> <ul id="toc-Tuberculosis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Non-tuberculous_mycobacteria" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Non-tuberculous_mycobacteria"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.2</span> <span>Non-tuberculous mycobacteria</span> </div> </a> <ul id="toc-Non-tuberculous_mycobacteria-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Special_populations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Special_populations"> <div class="vector-toc-text"> <span class="vector-toc-numb">2.3</span> <span>Special populations</span> </div> </a> <ul id="toc-Special_populations-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Side_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Side_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Side effects</span> </div> </a> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Drug_interactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Drug_interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Drug interactions</span> </div> </a> <ul id="toc-Drug_interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolism" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Metabolism"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Metabolism</span> </div> </a> <ul id="toc-Metabolism-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Preparation" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Preparation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Preparation</span> </div> </a> <ul id="toc-Preparation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Brand_names" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Brand_names"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Brand names</span> </div> </a> <ul id="toc-Brand_names-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Other_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Other uses</span> </div> </a> <button aria-controls="toc-Other_uses-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 Other uses subsection</span> </button> <ul id="toc-Other_uses-sublist" class="vector-toc-list"> <li id="toc-Chromatography" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Chromatography"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.1</span> <span>Chromatography</span> </div> </a> <ul id="toc-Chromatography-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Dogs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Dogs"> <div class="vector-toc-text"> <span class="vector-toc-numb">9.2</span> <span>Dogs</span> </div> </a> <ul id="toc-Dogs-sublist" class="vector-toc-list"> </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">10</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> <span class="vector-toc-numb">12</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" title="Table of Contents" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Isoniazid</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 40 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-40" 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">40 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Isoniasied" title="Isoniasied – Afrikaans" lang="af" hreflang="af" data-title="Isoniasied" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A2%D9%8A%D8%B2%D9%88%D9%86%D9%8A%D8%A7%D8%B2%D9%8A%D8%AF" title="آيزونيازيد – Arabic" lang="ar" hreflang="ar" data-title="آيزونيازيد" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%DB%8C%D8%B2%D9%88%D9%86%DB%8C%D8%A7%D8%B2%DB%8C%D8%AF" title="ایزونیازید – South Azerbaijani" lang="azb" hreflang="azb" data-title="ایزونیازید" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Isoniazida" title="Isoniazida – Catalan" lang="ca" hreflang="ca" data-title="Isoniazida" 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/Isoniazid" title="Isoniazid – Czech" lang="cs" hreflang="cs" data-title="Isoniazid" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Isoniasid" title="Isoniasid – Welsh" lang="cy" hreflang="cy" data-title="Isoniasid" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Isoniazid" title="Isoniazid – Danish" lang="da" hreflang="da" data-title="Isoniazid" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target"><span>Dansk</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Isoniazid" title="Isoniazid – German" lang="de" hreflang="de" data-title="Isoniazid" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%99%CF%83%CE%BF%CE%BD%CE%B9%CE%B1%CE%B6%CE%AF%CE%B4%CE%B7" title="Ισονιαζίδη – Greek" lang="el" hreflang="el" data-title="Ισονιαζίδη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Isoniacida" title="Isoniacida – Spanish" lang="es" hreflang="es" data-title="Isoniacida" 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/Isoniazida" title="Isoniazida – Basque" lang="eu" hreflang="eu" data-title="Isoniazida" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%DB%8C%D8%B2%D9%88%D9%86%DB%8C%D8%A7%D8%B2%DB%8C%D8%AF" title="ایزونیازید – Persian" lang="fa" hreflang="fa" data-title="ایزونیازید" 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/Isoniazide" title="Isoniazide – French" lang="fr" hreflang="fr" data-title="Isoniazide" 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%9D%B4%EC%86%8C%EB%8B%88%EC%95%84%EC%A7%80%EB%93%9C" title="이소니아지드 – Korean" lang="ko" hreflang="ko" data-title="이소니아지드" 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%BB%D5%A6%D5%B8%D5%B6%D5%AB%D5%A1%D5%A6%D5%AB%D5%A4" title="Իզոնիազիդ – Armenian" lang="hy" hreflang="hy" data-title="Իզոնիազիդ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Isoniazid" title="Isoniazid – Indonesian" lang="id" hreflang="id" data-title="Isoniazid" 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/Isoniazide" title="Isoniazide – Italian" lang="it" hreflang="it" data-title="Isoniazide" 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%90%D7%99%D7%96%D7%95%D7%A0%D7%99%D7%90%D7%96%D7%99%D7%93" title="איזוניאזיד – Hebrew" lang="he" hreflang="he" data-title="איזוניאזיד" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%90%E0%B2%B8%E0%B3%8A%E0%B2%A8%E0%B2%BF%E0%B2%AF%E0%B2%BE%E0%B2%9C%E0%B2%BF%E0%B2%A1%E0%B3%8D" title="ಐಸೊನಿಯಾಜಿಡ್ – Kannada" lang="kn" hreflang="kn" data-title="ಐಸೊನಿಯಾಜಿಡ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Izoniazidas" title="Izoniazidas – Lithuanian" lang="lt" hreflang="lt" data-title="Izoniazidas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target"><span>Lietuvių</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%90%E0%B4%B8%E0%B5%8B%E0%B4%A8%E0%B4%BF%E0%B4%AF%E0%B4%BE%E0%B4%B8%E0%B4%BF%E0%B4%A1%E0%B5%8D" title="ഐസോനിയാസിഡ് – Malayalam" lang="ml" hreflang="ml" data-title="ഐസോനിയാസിഡ്" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Isoniazide" title="Isoniazide – Dutch" lang="nl" hreflang="nl" data-title="Isoniazide" 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%A4%E3%82%BD%E3%83%8B%E3%82%A2%E3%82%B8%E3%83%89" title="イソニアジド – Japanese" lang="ja" hreflang="ja" data-title="イソニアジド" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Isoniazid" title="Isoniazid – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Isoniazid" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target"><span>Norsk bokmål</span></a></li><li class="interlanguage-link interwiki-nn mw-list-item"><a href="https://nn.wikipedia.org/wiki/Isoniazid" title="Isoniazid – Norwegian Nynorsk" lang="nn" hreflang="nn" data-title="Isoniazid" data-language-autonym="Norsk nynorsk" data-language-local-name="Norwegian Nynorsk" class="interlanguage-link-target"><span>Norsk nynorsk</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%86%E0%AC%87%E0%AC%B8%E0%AD%8B%E0%AC%A8%E0%AC%BF%E0%AC%86%E0%AC%9C%E0%AC%BF%E0%AC%A1" title="ଆଇସୋନିଆଜିଡ – Odia" lang="or" hreflang="or" data-title="ଆଇସୋନିଆଜିଡ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Izoniazyd" title="Izoniazyd – Polish" lang="pl" hreflang="pl" data-title="Izoniazyd" 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/Isoniazida" title="Isoniazida – Portuguese" lang="pt" hreflang="pt" data-title="Isoniazida" 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/Izoniazid%C4%83" title="Izoniazidă – Romanian" lang="ro" hreflang="ro" data-title="Izoniazidă" 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%98%D0%B7%D0%BE%D0%BD%D0%B8%D0%B0%D0%B7%D0%B8%D0%B4" title="Изониазид – Russian" lang="ru" hreflang="ru" data-title="Изониазид" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Izoniazid" title="Izoniazid – Slovenian" lang="sl" hreflang="sl" data-title="Izoniazid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Izoniazid" title="Izoniazid – Serbian" lang="sr" hreflang="sr" data-title="Izoniazid" 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/Izoniazid" title="Izoniazid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Izoniazid" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Isoniatsidi" title="Isoniatsidi – Finnish" lang="fi" hreflang="fi" data-title="Isoniatsidi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Isoniazid" title="Isoniazid – Swedish" lang="sv" hreflang="sv" data-title="Isoniazid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/%C4%B0zoniazid" title="İzoniazid – Turkish" lang="tr" hreflang="tr" data-title="İzoniazid" 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%86%D0%B7%D0%BE%D0%BD%D1%96%D0%B0%D0%B7%D0%B8%D0%B4" title="Ізоніазид – Ukrainian" lang="uk" hreflang="uk" data-title="Ізоніазид" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Isoniazid" title="Isoniazid – Vietnamese" lang="vi" hreflang="vi" data-title="Isoniazid" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%95%B0%E7%85%99%E8%82%BC" title="異煙肼 – Cantonese" lang="yue" hreflang="yue" data-title="異煙肼" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh 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class="infobox-title"><span title="International nonproprietary name (INN): Isoniazid">Isoniazid</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Isoniazid_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Isoniazid_skeletal.svg/160px-Isoniazid_skeletal.svg.png" decoding="async" width="160" height="100" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/48/Isoniazid_skeletal.svg/240px-Isoniazid_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/48/Isoniazid_skeletal.svg/320px-Isoniazid_skeletal.svg.png 2x" data-file-width="512" data-file-height="320" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="bg-transparent" typeof="mw:File"><a href="/wiki/File:Isoniazid_3d.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Isoniazid_3d.png/220px-Isoniazid_3d.png" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Isoniazid_3d.png/330px-Isoniazid_3d.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Isoniazid_3d.png/440px-Isoniazid_3d.png 2x" data-file-width="1024" data-file-height="1024" /></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">Hydra, Hyzyd, Isovit, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">isonicotinic acid hydrazide, isonicotinyl hydrazine, INH, INAH, INHA</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/monograph/isoniazid.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a682401.html">a682401</a></span></td></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">License data</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><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Isoniazid">Isoniazid</a></span></li></ul></div> </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"><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> A<sup id="cite_ref-Drugs.com_pregnancy_1-0" class="reference"><a href="#cite_note-Drugs.com_pregnancy-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li> <li class="mw-empty-elt"></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"><a href="/wiki/By_mouth" class="mw-redirect" title="By mouth">By mouth</a>, <a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular">intramuscular</a>, <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenous</a></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_J04" title="ATC code J04">J04AC01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AC01">WHO</a></span>) <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AC51</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AC51">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM01</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM01">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM02">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM03">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM04</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM04">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM05</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM05">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM06</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM06">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM07</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM07">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM08</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM08">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM09</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM09">WHO</a></span>), <a href="/wiki/ATC_code_J04" title="ATC code J04">J04AM12</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J04AM12">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="Canada">CA</abbr></small>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_2-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>Rx-only</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/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">Very low (0–10%)</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; CYP450: 2C19, 3A4 inhibitor</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">0.5–1.6h (fast acetylators), 2-5h (slow acetylators)</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 (primarily), feces</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%;">Pyridine-4-carbohydrazide</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=54-85-3">54-85-3</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3767">3767</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/DB00951">DB00951</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.3635.html">3635</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/V83O1VOZ8L">V83O1VOZ8L</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/D00346">D00346</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><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C07054">C07054</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6030">CHEBI:6030</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/ChEMBL64">ChEMBL64</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/NIAID_ChemDB" title="NIAID ChemDB">NIAID ChemDB</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemdb.niaid.nih.gov"><a rel="nofollow" class="external text" href="https://chemdb.niaid.nih.gov/CompoundDetails.aspx?AIDSNO=007657">007657</a></span></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/DTXSID8020755">DTXSID8020755</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q423169#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/100.000.195">100.000.195</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q423169#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>6</sub><span title="Hydrogen">H</span><sub>7</sub><span title="Nitrogen">N</span><sub>3</sub><span title="Oxygen">O</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="7002137142000000000♠"></span>137.142</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=C1%3DCN%3DCC%3DC1C%28%3DO%29NN">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%;">C1=CN=CC=C1C(=O)NN</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/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></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:QRXWMOHMRWLFEY-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=459455986&page2=Isoniazid">(verify)</a></span></span></td></tr></tbody></table> <p><b>Isoniazid</b>, also known as <b>isonicotinic acid hydrazide</b> (<b>INH</b>), is an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> used for the <a href="/wiki/Tuberculosis_management" class="mw-redirect" title="Tuberculosis management">treatment of tuberculosis</a>.<sup id="cite_ref-AHFS2016_4-0" class="reference"><a href="#cite_note-AHFS2016-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> For active tuberculosis, it is often used together with <a href="/wiki/Rifampicin" title="Rifampicin">rifampicin</a>, <a href="/wiki/Pyrazinamide" title="Pyrazinamide">pyrazinamide</a>, and either <a href="/wiki/Streptomycin" title="Streptomycin">streptomycin</a> or <a href="/wiki/Ethambutol" title="Ethambutol">ethambutol</a>.<sup id="cite_ref-WHO2008_5-0" class="reference"><a href="#cite_note-WHO2008-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> For latent tuberculosis, it is often used alone.<sup id="cite_ref-AHFS2016_4-1" class="reference"><a href="#cite_note-AHFS2016-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It may also be used for <a href="/wiki/Nontuberculous_mycobacteria" title="Nontuberculous mycobacteria">atypical types of mycobacteria</a>, such as <i><a href="/wiki/M._avium" class="mw-redirect" title="M. avium">M. avium</a></i>, <i><a href="/wiki/Mycobacterium_kansasii" title="Mycobacterium kansasii">M. kansasii</a></i>, and <i><a href="/wiki/Mycobacterium_xenopi" title="Mycobacterium xenopi">M. xenopi</a></i>.<sup id="cite_ref-AHFS2016_4-2" class="reference"><a href="#cite_note-AHFS2016-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> It is usually taken by mouth, but may be used by <a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular">injection into muscle</a>.<sup id="cite_ref-AHFS2016_4-3" class="reference"><a href="#cite_note-AHFS2016-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>After <a href="/wiki/Friedrich_Raschig" title="Friedrich Raschig">F. Raschig</a> developed <a href="/wiki/Olin_Raschig_process" title="Olin Raschig process">a method</a> to synthesize <a href="/wiki/Hydrazine" title="Hydrazine">hydrazine</a>, <a href="/wiki/Hans_Leopold_Meyer" title="Hans Leopold Meyer">Hans Meyer</a> and his doctoral student at the <a href="/wiki/German_University_in_Prague" class="mw-redirect" title="German University in Prague">German University in Prague</a> Josef Mally studied hydrazides of pyridinecarboxylic acids. By reacting ethyl isonicotinate with hydrazine hydrate they obtained a compound which, after a recrystallization, had a melting point of 163°C.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Despite their results published in 1912, its pharmaceutical properties weren't investigated for decades. </p><p>In the 1940s French physicians discovered that <a href="/wiki/Nicotinamide" title="Nicotinamide">nicotinamide</a> had some activity against tubercle bacilli in vitro and in infected guinea pigs.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Chakraborty_2015_8-0" class="reference"><a href="#cite_note-Chakraborty_2015-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> At the same time, German chemists led by <a href="/wiki/Gerhard_Domagk" title="Gerhard Domagk">G. Domagk</a> investigating <a href="/wiki/Sulfonamide_(medicine)" title="Sulfonamide (medicine)">sulfo drugs</a> at <a href="/wiki/Bayer" title="Bayer">Bayer</a> developed <a href="/wiki/Thioacetazone" title="Thioacetazone">thioacetazone</a>.<sup id="cite_ref-McDermott_1969_9-0" class="reference"><a href="#cite_note-McDermott_1969-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Chakraborty_2015_8-1" class="reference"><a href="#cite_note-Chakraborty_2015-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> After their findings were made public, in 1950 <a href="/w/index.php?title=Andr%C3%A9_Girard_(chemist)&action=edit&redlink=1" class="new" title="André Girard (chemist) (page does not exist)">A. Girard</a><span class="noprint" style="font-size:85%; font-style: normal;"> [<a href="https://fr.wikipedia.org/wiki/Andr%C3%A9_Girard_(chimiste)" class="extiw" title="fr:André Girard (chimiste)">fr</a>]</span> modified it to the less toxic <a href="/wiki/Thiosemicarbazone" title="Thiosemicarbazone">thiosemicarbazone</a> of <a href="/wiki/Pyridine-3-carbaldehyde" title="Pyridine-3-carbaldehyde">nicotinaldehyde</a><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> while H. H. Fox developed similar isonicotinaldehyde thiosemicarbazone.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Soon, multiple laboratories discovered anti-TB activity of isoniazid.<sup id="cite_ref-Chakraborty_2015_8-2" class="reference"><a href="#cite_note-Chakraborty_2015-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-McDermott_1969_9-1" class="reference"><a href="#cite_note-McDermott_1969-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>It's believed that Soviet physicians <a href="/w/index.php?title=Anatoliy_Kachugin&action=edit&redlink=1" class="new" title="Anatoliy Kachugin (page does not exist)">A. Kachugin</a><span class="noprint" style="font-size:85%; font-style: normal;"> [<a href="https://ru.wikipedia.org/wiki/%D0%9A%D0%B0%D1%87%D1%83%D0%B3%D0%B8%D0%BD,_%D0%90%D0%BD%D0%B0%D1%82%D0%BE%D0%BB%D0%B8%D0%B9_%D0%A2%D1%80%D0%BE%D1%84%D0%B8%D0%BC%D0%BE%D0%B2%D0%B8%D1%87" class="extiw" title="ru:Качугин, Анатолий Трофимович">ru</a>]</span> and Bella Keyfman also discovered this activity in 1949 but neither published their findings in a peer-reviewed article nor applied for an inventor's certificate.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Three pharmaceutical companies unsuccessfully attempted to patent the drug at the same time,<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> the most prominent one being <a href="/wiki/Roche" title="Roche">Roche</a> in January 1951,<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> which launched its version, Rimifon, in 1952.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>The drug was first tested at <a href="/wiki/Many_Farms,_Arizona" title="Many Farms, Arizona">Many Farms</a>, a <a href="/wiki/Navajo_Nation" title="Navajo Nation">Navajo</a> community in <a href="/wiki/Arizona" title="Arizona">Arizona</a>, due to the Navajo reservation's tuberculosis problem and because the population had not previously been treated with <a href="/wiki/Streptomycin" title="Streptomycin">streptomycin</a>, the main tuberculosis treatment at the time.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> The research was led by <a href="/wiki/Walsh_McDermott" title="Walsh McDermott">Walsh McDermott</a>, an infectious disease researcher with an interest in public health, who had previously taken isoniazid to treat his own tuberculosis.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Isoniazid and a related drug, <a href="/wiki/Iproniazid" title="Iproniazid">iproniazid</a>, were among the first drugs to be referred to as <a href="/wiki/Antidepressant" title="Antidepressant">antidepressants</a>.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> Psychiatric use stopped in 1961 following reports of hepatotoxicity. Use against tuberculosis continued, as isoniazid's effectiveness against the disease outweighs its risks.<sup id="cite_ref-mania_21-0" class="reference"><a href="#cite_note-mania-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>It is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<sup id="cite_ref-WHO21st_22-0" class="reference"><a href="#cite_note-WHO21st-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> The World Health Organization classifies isoniazid as critically important for human medicine.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> Isoniazid is available as a <a href="/wiki/Generic_medication" class="mw-redirect" title="Generic medication">generic medication</a>.<sup id="cite_ref-AHFS2016_4-4" class="reference"><a href="#cite_note-AHFS2016-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <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=Isoniazid&action=edit&section=2" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Tuberculosis">Tuberculosis</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=3" title="Edit section: Tuberculosis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Isoniazid is often used to treat latent and active tuberculosis infections. In persons with isoniazid-sensitive <i><a href="/wiki/Mycobacterium_tuberculosis" title="Mycobacterium tuberculosis">Mycobacterium tuberculosis</a></i> infection, drug regimens based on isoniazid are usually effective when persons adhere to the prescribed treatment. However, in persons with isoniazid-resistant <i>Mycobacterium tuberculosis</i> infection, drug regimens based on isoniazid have a high rate of failure.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> </p><p>Isoniazid has been approved as prophylactic therapy for the following populations: </p> <ul><li>People with HIV infection and a PPD (purified protein derivative) reaction of at least 5 mm induration</li> <li>Contacts of people with tuberculosis and who have a PPD reaction at least 5 mm induration</li> <li>People whose PPD reactions convert from negative to positive in a two-year period – at least 10 mm induration for those up to 35 years of age, and at least 15 mm induration for those at least 35 years old</li> <li>People with pulmonary damage on their chest X-ray that is likely to be due to healed tuberculosis and also have a PPD reaction at least 5 mm induration</li> <li>Injection drug users whose HIV status is negative who have a PPD reaction at least 10 mm induration</li> <li>People with a PPD of greater than or equal to 10 mm induration who are foreign-born from high prevalence geographical regions, low-income populations, and patients residing in long-term facilities<sup id="cite_ref-Isoniazid_2023_25-0" class="reference"><a href="#cite_note-Isoniazid_2023-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup></li></ul> <p>Isoniazid can be used alone or in combination with <a href="/wiki/Ethambutol/isoniazid/pyrazinamide/rifampicin" title="Ethambutol/isoniazid/pyrazinamide/rifampicin">Rifampin</a> for treatment of latent tuberculosis, or as part of a four-drug regimen for treatment of active tuberculosis.<sup id="cite_ref-Lewis_2013_27-0" class="reference"><a href="#cite_note-Lewis_2013-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> The drug regimen typically requires daily or weekly oral administration for a period of three to nine months, often under <a href="/wiki/Directly_observed_therapy" class="mw-redirect" title="Directly observed therapy">Directly Observed Therapy</a> (DOT) supervision.<sup id="cite_ref-Lewis_2013_27-1" class="reference"><a href="#cite_note-Lewis_2013-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Non-tuberculous_mycobacteria">Non-tuberculous mycobacteria</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=4" title="Edit section: Non-tuberculous mycobacteria"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Isoniazid was widely used in the treatment of <a href="/wiki/Mycobacterium_avium_complex" title="Mycobacterium avium complex"><i>Mycobacterium avium</i> complex</a> as part of a regimen including rifampicin and ethambutol.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Evidence suggests that isoniazid prevents mycolic acid synthesis in <i>M. avium</i> complex as in <i>M. tuberculosis</i><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> and although this is not bactericidal to <i>M. avium</i> complex, it greatly potentiates the effect of rifampicin. The introduction of macrolides led to this use greatly decreasing. However, since rifampicin is broadly underdosed in <i>M. avium</i> complex treatment, this effect may be worth re-investigating.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<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=Isoniazid&action=edit&section=5" title="Edit section: Special populations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It is recommended that women with active tuberculosis who are pregnant or breastfeeding take isoniazid. Preventive therapy should be delayed until after giving birth.<sup id="cite_ref-Isoniazid_label_31-0" class="reference"><a href="#cite_note-Isoniazid_label-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> Nursing mothers excrete a relatively low and non-toxic concentration of INH in breast milk, and their babies are at low risk for side effects. Both pregnant women and infants being breastfed by mothers taking INH should take <a href="/wiki/Vitamin_B6" title="Vitamin B6">vitamin B6</a> in its <a href="/wiki/Pyridoxine" title="Pyridoxine">pyridoxine</a> form to minimize the risk of peripheral nerve damage.<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> Vitamin B6 is used to prevent isoniazid-induced B6 deficiency and neuropathy in people with a risk factor, such as pregnancy, lactation, HIV infection, alcoholism, diabetes, kidney failure, or malnutrition.<sup id="cite_ref-Steichen_2006_33-0" class="reference"><a href="#cite_note-Steichen_2006-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>People with liver dysfunction are at a higher risk for hepatitis caused by INH, and may need a lower dose.<sup id="cite_ref-Isoniazid_label_31-1" class="reference"><a href="#cite_note-Isoniazid_label-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>Levels of liver enzymes in the bloodstream should be frequently checked in daily alcohol drinkers, pregnant women, IV drug users, people over 35, and those who have chronic liver disease, severe kidney dysfunction, peripheral neuropathy, or HIV infection since they are more likely to develop hepatitis from INH.<sup id="cite_ref-Isoniazid_label_31-2" class="reference"><a href="#cite_note-Isoniazid_label-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=6" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Up to 20% of people taking isoniazid experience <a href="/wiki/Peripheral_neuropathy" title="Peripheral neuropathy">peripheral neuropathy</a> when taking daily doses of 6 mg/kg of body weight or higher.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Gastrointestinal reactions include nausea and vomiting.<sup id="cite_ref-Isoniazid_2023_25-1" class="reference"><a href="#cite_note-Isoniazid_2023-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Aplastic_anemia" title="Aplastic anemia">Aplastic anemia</a>, <a href="/wiki/Thrombocytopenia" title="Thrombocytopenia">thrombocytopenia</a>, and <a href="/wiki/Agranulocytosis" title="Agranulocytosis">agranulocytosis</a> due to lack of production of red blood cells, platelets, and white blood cells by the bone marrow respectively, can also occur.<sup id="cite_ref-Isoniazid_2023_25-2" class="reference"><a href="#cite_note-Isoniazid_2023-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Hypersensitivity reactions are also common and can present with a <a href="/wiki/Maculopapular" class="mw-redirect" title="Maculopapular">maculopapular</a> rash and fever.<sup id="cite_ref-Isoniazid_2023_25-3" class="reference"><a href="#cite_note-Isoniazid_2023-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Gynecomastia" title="Gynecomastia">Gynecomastia</a> may occur.<sup id="cite_ref-Lewis_2013_27-2" class="reference"><a href="#cite_note-Lewis_2013-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p><p>Asymptomatic elevation of serum liver enzyme concentrations occurs in 10% to 20% of people taking INH, and liver enzyme concentrations usually return to normal even when treatment is continued.<sup id="cite_ref-cdc-ltbi_36-0" class="reference"><a href="#cite_note-cdc-ltbi-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Isoniazid has a boxed warning for severe and sometimes fatal hepatitis, which is age-dependent at a rate of 0.3% in people 21 to 35 years old and over 2% in those over age 50.<sup id="cite_ref-Isoniazid_2023_25-4" class="reference"><a href="#cite_note-Isoniazid_2023-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-37" class="reference"><a href="#cite_note-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> Symptoms suggestive of liver toxicity include nausea, vomiting, abdominal pain, dark urine, right upper quadrant pain, and loss of appetite.<sup id="cite_ref-Isoniazid_2023_25-5" class="reference"><a href="#cite_note-Isoniazid_2023-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Black and Hispanic women are at higher risk for isoniazid-induced hepatotoxicity.<sup id="cite_ref-Isoniazid_2023_25-6" class="reference"><a href="#cite_note-Isoniazid_2023-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> When it happens, isoniazid-induced liver toxicity has been shown to occur in 50% of patients within the first 2 months of therapy.<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> </p><p>Some recommend that liver function should be monitored carefully in all people receiving it,<sup id="cite_ref-Isoniazid_label_31-3" class="reference"><a href="#cite_note-Isoniazid_label-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> but others recommend monitoring only in certain populations.<sup id="cite_ref-cdc-ltbi_36-1" class="reference"><a href="#cite_note-cdc-ltbi-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p><p>Headache, poor concentration, weight gain, poor memory, insomnia, and depression have all been associated with isoniazid use.<sup id="cite_ref-Alao_1998_41-0" class="reference"><a href="#cite_note-Alao_1998-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-42" class="reference"><a href="#cite_note-42"><span class="cite-bracket">[</span>42<span class="cite-bracket">]</span></a></sup> All patients and healthcare workers should be aware of these serious side effects, especially if suicidal ideation or behavior are suspected.<sup id="cite_ref-Alao_1998_41-1" class="reference"><a href="#cite_note-Alao_1998-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> </p><p>Isoniazid is associated with <a href="/wiki/Pyridoxine" title="Pyridoxine">pyridoxine</a> (vitamin B6) deficiency because of its similar structure. Isoniazid is also associated with increased excretion of pyridoxine. Pyridoxal phosphate (a derivative of pyridoxine) is required for δ-<a href="/wiki/Aminolevulinic_acid_synthase" title="Aminolevulinic acid synthase">aminolevulinic acid synthase</a>, the enzyme responsible for the rate-limiting step in heme synthesis. Therefore, isoniazid-induced pyridoxine deficiency causes insufficient heme formation in early red blood cells, leading to <a href="/wiki/Sideroblastic_anemia" title="Sideroblastic anemia">sideroblastic anemia</a>.<sup id="cite_ref-Steichen_2006_33-1" class="reference"><a href="#cite_note-Steichen_2006-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p><p>Isoniazid was found to significantly elevate the in vivo concentration of <a href="/wiki/GABA" title="GABA">GABA</a> and <a href="/w/index.php?title=Homocarnosine&action=edit&redlink=1" class="new" title="Homocarnosine (page does not exist)">homocarnosine</a> in a single subject via <a href="/wiki/Magnetic_resonance_spectroscopy" class="mw-redirect" title="Magnetic resonance spectroscopy">magnetic resonance spectroscopy</a>.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Drug_interactions">Drug interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=7" title="Edit section: Drug interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>People taking isoniazid and acetaminophen are at risk of acetaminophen toxicity. Isoniazid is thought to induce a liver enzyme which causes a larger amount of acetaminophen to be metabolized to a toxic form.<sup id="cite_ref-46" class="reference"><a href="#cite_note-46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-47" class="reference"><a href="#cite_note-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup> </p><p>Isoniazid decreases the metabolism of carbamazepine, thus slowing down its clearance from the body. People taking carbamazepine should have their carbamazepine levels monitored and, if necessary, have their dose adjusted accordingly.<sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>It is possible that isoniazid may decrease the serum levels of ketoconazole after long-term treatment. This is seen with the simultaneous use of rifampin, isoniazid, and ketoconazole.<sup id="cite_ref-49" class="reference"><a href="#cite_note-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> </p><p>Isoniazid may increase the amount of phenytoin in the body. The doses of phenytoin may need to be adjusted when given with isoniazid.<sup id="cite_ref-Jonville_50-0" class="reference"><a href="#cite_note-Jonville-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<span class="cite-bracket">]</span></a></sup> </p><p>Isoniazid may increase the plasma levels of <a href="/wiki/Theophylline" title="Theophylline">theophylline</a>. There are some cases of theophylline slowing down isoniazid elimination. Both theophylline and isoniazid levels should be monitored.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Valproate" title="Valproate">Valproate</a> levels may increase when taken with isoniazid. Valproate levels should be monitored and its dose adjusted if necessary.<sup id="cite_ref-Jonville_50-1" class="reference"><a href="#cite_note-Jonville-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=8" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Isoniazid is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a> that inhibits the formation of the <a href="/wiki/Mycobacterium" title="Mycobacterium">mycobacterial</a> cell wall. Isoniazid must be activated by KatG, a bacterial catalase-peroxidase enzyme in <i><a href="/wiki/Mycobacterium_tuberculosis" title="Mycobacterium tuberculosis">Mycobacterium tuberculosis</a></i>.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> KatG catalyzes the formation of the isonicotinic acyl radical, which spontaneously couples with <a href="/wiki/NADH" class="mw-redirect" title="NADH">NADH</a> to form the nicotinoyl-NAD adduct. This complex binds tightly to the <a href="/wiki/Enoyl-acyl_carrier_protein_reductase" title="Enoyl-acyl carrier protein reductase">enoyl-acyl carrier protein reductase</a> InhA, thereby blocking the natural enoyl-AcpM substrate and the action of <a href="/wiki/Fatty_acid_synthase" title="Fatty acid synthase">fatty acid synthase</a>. This process inhibits the synthesis of <a href="/wiki/Mycolic_acids" class="mw-redirect" title="Mycolic acids">mycolic acids</a>, which are required components of the <a href="/wiki/Mycobacterium" title="Mycobacterium">mycobacterial</a> cell wall. A range of radicals are produced by KatG activation of isoniazid, including <a href="/wiki/Nitric_oxide" title="Nitric oxide">nitric oxide</a>,<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> which has also been shown to be important in the action of another antimycobacterial prodrug <a href="/wiki/Pretomanid" title="Pretomanid">pretomanid</a>.<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> </p><p><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Activation_of_isoniazid_with_NAD.jpg" class="mw-file-description" title="Isoniazid (INH) is activated by KatG to the isonicotinic acyl radical, which subsequently reacts with NAD to form the isonicotinic acyl-NADH complex."><img alt="Isoniazid (INH) is activated by KatG to the isonicotinic acyl radical, which subsequently reacts with NAD to form the isonicotinic acyl-NADH complex." src="//upload.wikimedia.org/wikipedia/commons/thumb/4/41/Activation_of_isoniazid_with_NAD.jpg/500px-Activation_of_isoniazid_with_NAD.jpg" decoding="async" width="500" height="164" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/4/41/Activation_of_isoniazid_with_NAD.jpg 1.5x" data-file-width="717" data-file-height="235" /></a></span> </p><p>Isoniazid is <a href="/wiki/Bactericidal" class="mw-redirect" title="Bactericidal">bactericidal</a> to rapidly dividing <a href="/wiki/Mycobacterium" title="Mycobacterium">mycobacteria</a>, but is <a href="/wiki/Bacteriostatic" class="mw-redirect" title="Bacteriostatic">bacteriostatic</a> if the mycobacteria are slow-growing.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> It inhibits the <a href="/wiki/Cytochrome_P450_system" class="mw-redirect" title="Cytochrome P450 system">cytochrome P450 system</a> and hence acts as a source of free radicals.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p><p>Isoniazid is a mild non-selective <a href="/wiki/Monoamine_oxidase_inhibitor" title="Monoamine oxidase inhibitor">monoamine oxidase inhibitor</a> (MAO-I).<sup id="cite_ref-maoi_58-0" class="reference"><a href="#cite_note-maoi-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> It inhibits <a href="/wiki/Diamine_oxidase" title="Diamine oxidase">diamine oxidase</a> more strongly. These two actions are possible explanations for its antidepressant action<sup id="cite_ref-isbn1-86036-010-6_59-0" class="reference"><a href="#cite_note-isbn1-86036-010-6-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> as well as its ability to cause mania.<sup id="cite_ref-mania_21-1" class="reference"><a href="#cite_note-mania-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=9" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Isoniazid reaches therapeutic concentrations in serum, <a href="/wiki/Cerebrospinal_fluid" title="Cerebrospinal fluid">cerebrospinal fluid</a>, and within <a href="/wiki/Caseous_necrosis" title="Caseous necrosis">caseous granulomas</a>. It is metabolized in the liver via <a href="/wiki/Acetylation" title="Acetylation">acetylation</a> into acetylhydrazine. Two forms of the enzyme are responsible for acetylation, so some patients metabolize the drug more quickly than others. Hence, the <a href="/wiki/Half-life" title="Half-life">half-life</a> is <a href="/wiki/Bimodal_distribution" class="mw-redirect" title="Bimodal distribution">bimodal</a>, with "slow acetylators" and "fast acetylators". A graph of number of people versus time shows peaks at one and three hours. The height of the peaks depends on the ethnicities of the people being tested. The metabolites are excreted in the urine. Doses do not usually have to be adjusted in case of <a href="/wiki/Renal_failure" class="mw-redirect" title="Renal failure">renal failure</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (August 2022)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading2"><h2 id="Preparation">Preparation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=10" title="Edit section: Preparation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Isoniazid is an <a href="/wiki/Isonicotinic_acid" title="Isonicotinic acid">isonicotinic acid</a> <a href="/wiki/Derivative_(chemistry)" title="Derivative (chemistry)">derivative</a>. It is manufactured using <a href="/w/index.php?title=4-cyanopyridine&action=edit&redlink=1" class="new" title="4-cyanopyridine (page does not exist)">4-cyanopyridine</a> and <a href="/wiki/Hydrazine_hydrate" class="mw-redirect" title="Hydrazine hydrate">hydrazine hydrate</a>.<sup id="cite_ref-William_60-0" class="reference"><a href="#cite_note-William-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> In another method, isoniazid was claimed to have been made from <a href="/wiki/Citric_acid" title="Citric acid">citric acid</a> starting material.<sup id="cite_ref-BaizerDub1956_61-0" class="reference"><a href="#cite_note-BaizerDub1956-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p><p>It can in theory be made from <a href="/wiki/Methyl_isonicotinate" title="Methyl isonicotinate">methyl isonicotinate</a>, which is labelled a <a href="/wiki/Semiochemical" title="Semiochemical">semiochemical</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Brand_names">Brand names</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=11" title="Edit section: Brand names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Hydra, Hyzyd, Isovit, Laniazid, Nydrazid, Rimifon, and Stanozide.<sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Other_uses">Other uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=12" title="Edit section: Other uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Chromatography">Chromatography</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=13" title="Edit section: Chromatography"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Isonicotinic acid hydrazide is also used in <a href="/wiki/Chromatography" title="Chromatography">chromatography</a> to differentiate between various degrees of <a href="/wiki/Conjugated_system" title="Conjugated system">conjugation</a> in <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> barring the <a href="/wiki/Ketone" title="Ketone">ketone</a> <a href="/wiki/Functional_group" title="Functional group">functional group</a>.<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> The test works by forming a <a href="/wiki/Hydrazone" title="Hydrazone">hydrazone</a> which can be detected by its <a href="/wiki/Bathochromic_shift" title="Bathochromic shift">bathochromic shift</a>.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (December 2022)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Dogs">Dogs</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=14" title="Edit section: Dogs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Isoniazid may be used for dogs, but there have been concerns it can cause seizures.<sup id="cite_ref-64" class="reference"><a href="#cite_note-64"><span class="cite-bracket">[</span>64<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=Isoniazid&action=edit&section=15" 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-Drugs.com_pregnancy-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-Drugs.com_pregnancy_1-0">^</a></b></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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/pregnancy/isoniazid.html">"Isoniazid (Nydrazid) Use During Pregnancy"</a>. <i>Drugs.com</i>. 7 October 2019<span class="reference-accessdate">. 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American Pharmaceutical Association</i>. <b>45</b> (7): <span class="nowrap">478–</span>480. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fjps.3030450714">10.1002/jps.3030450714</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/13345683">13345683</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+the+American+Pharmaceutical+Association.+American+Pharmaceutical+Association&rft.atitle=Synthesis+of+isoniazid+from+citric+acid&rft.volume=45&rft.issue=7&rft.pages=%3Cspan+class%3D%22nowrap%22%3E478-%3C%2Fspan%3E480&rft.date=1956-07&rft_id=info%3Adoi%2F10.1002%2Fjps.3030450714&rft_id=info%3Apmid%2F13345683&rft.aulast=Baizer&rft.aufirst=MM&rft.au=Dub%2C+M&rft.au=Gister%2C+S&rft.au=Steinberg%2C+NG&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsoniazid" class="Z3988"></span></span> </li> <li id="cite_note-62"><span class="mw-cite-backlink"><b><a href="#cite_ref-62">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm">"Drugs@FDA"</a>. <i>fda.gov</i>. United States Food and Drug Administration. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20120814072104/http://www.accessdata.fda.gov/Scripts/cder/DrugsatFDA/index.cfm">Archived</a> from the original on 14 August 2012<span class="reference-accessdate">. Retrieved <span class="nowrap">22 August</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=fda.gov&rft.atitle=Drugs%40FDA&rft_id=http%3A%2F%2Fwww.accessdata.fda.gov%2Fscripts%2Fcder%2Fdrugsatfda%2Findex.cfm&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsoniazid" class="Z3988"></span></span> </li> <li id="cite_note-63"><span class="mw-cite-backlink"><b><a href="#cite_ref-63">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSayginTabibBittarValenzi1959" class="citation journal cs1">Saygin D, Tabib T, Bittar HE, Valenzi E, Sembrat J, Chan SY, et al. (1959). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7052475">"Transcriptional profiling of lung cell populations in idiopathic pulmonary arterial hypertension"</a>. <i>Pulmonary Circulation</i>. <b>10</b> (1): <span class="nowrap">102–</span>105. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fac60145a020">10.1021/ac60145a020</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/PMC7052475">7052475</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/32166015">32166015</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pulmonary+Circulation&rft.atitle=Transcriptional+profiling+of+lung+cell+populations+in+idiopathic+pulmonary+arterial+hypertension&rft.volume=10&rft.issue=1&rft.pages=%3Cspan+class%3D%22nowrap%22%3E102-%3C%2Fspan%3E105&rft.date=1959&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7052475%23id-name%3DPMC&rft_id=info%3Apmid%2F32166015&rft_id=info%3Adoi%2F10.1021%2Fac60145a020&rft.aulast=Saygin&rft.aufirst=D&rft.au=Tabib%2C+T&rft.au=Bittar%2C+HE&rft.au=Valenzi%2C+E&rft.au=Sembrat%2C+J&rft.au=Chan%2C+SY&rft.au=Rojas%2C+M&rft.au=Lafyatis%2C+R&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7052475&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsoniazid" class="Z3988"></span></span> </li> <li id="cite_note-64"><span class="mw-cite-backlink"><b><a href="#cite_ref-64">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSykes2013" class="citation book cs1">Sykes JE (2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=cb0kTIlb8HgC&pg=PA425"><i>Canine and Feline Infectious Diseases</i></a> <span class="cs1-format">(E-Book)</span>. Elsevier Health Sciences. p. 425. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-24194-6" title="Special:BookSources/978-0-323-24194-6"><bdi>978-0-323-24194-6</bdi></a> – via Google Books.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Canine+and+Feline+Infectious+Diseases&rft.pages=425&rft.pub=Elsevier+Health+Sciences&rft.date=2013&rft.isbn=978-0-323-24194-6&rft.aulast=Sykes&rft.aufirst=JE&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dcb0kTIlb8HgC%26pg%3DPA425&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsoniazid" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=16" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFRomeroKuczler1998" class="citation journal cs1">Romero JA, Kuczler FJ (February 1998). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20111101092427/http://www.aafp.org/afp/980215ap/romero.html">"Isoniazid overdose: recognition and management"</a>. <i>American Family Physician</i>. <b>57</b> (4): <span class="nowrap">749–</span>752. <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/9490997">9490997</a>. Archived from <a rel="nofollow" class="external text" href="http://www.aafp.org/afp/980215ap/romero.html">the original</a> on 2011-11-01<span class="reference-accessdate">. Retrieved <span class="nowrap">2005-12-13</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Family+Physician&rft.atitle=Isoniazid+overdose%3A+recognition+and+management&rft.volume=57&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E749-%3C%2Fspan%3E752&rft.date=1998-02&rft_id=info%3Apmid%2F9490997&rft.aulast=Romero&rft.aufirst=JA&rft.au=Kuczler%2C+FJ&rft_id=http%3A%2F%2Fwww.aafp.org%2Fafp%2F980215ap%2Fromero.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AIsoniazid" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Isoniazid&action=edit&section=17" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Commons-logo.svg" class="mw-file-description"><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" /></a></span> Media related to <a href="https://commons.wikimedia.org/wiki/Category:Isoniazid" class="extiw" title="commons:Category:Isoniazid">Isoniazid</a> at Wikimedia Commons</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline 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title="Rifalazil">Rifalazil</a><sup>§</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antifolate" title="Antifolate">Antifolates</a>/<a href="/wiki/Dihydropteroate_synthetase_inhibitor" class="mw-redirect" title="Dihydropteroate synthetase inhibitor">DSI</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/Dapsone" title="Dapsone">Dapsone</a><sup>#</sup></li> <li><a href="/wiki/Acedapsone" title="Acedapsone">Acedapsone</a></li> <li><a href="/wiki/Diucifon" title="Diucifon">Diucifon</a></li> <li><a href="/wiki/Promin" title="Promin">Promin</a></li> <li><a href="/wiki/Solasulfone" title="Solasulfone">Solasulfone</a></li> <li><a href="/wiki/Sulfoxone" title="Sulfoxone">Sulfoxone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">ASA</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/4-Aminosalicylic_acid" title="4-Aminosalicylic acid">4-Aminosalicylic acid</a></i><sup>#</sup> (<a href="/wiki/Calcium_aminosalicylate" class="mw-redirect" title="Calcium aminosalicylate">Calcium aminosalicylate</a></li> <li><a href="/wiki/Sodium_aminosalicylate" class="mw-redirect" title="Sodium aminosalicylate">Sodium aminosalicylate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Topoisomerase_inhibitor" title="Topoisomerase inhibitor">Topoisomerase inhibitors</a>/<br /><a href="/wiki/Quinolone_antibiotic" title="Quinolone antibiotic">quinolones</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/Gatifloxacin" title="Gatifloxacin">Gatifloxacin</a></li> <li><a href="/wiki/Moxifloxacin" title="Moxifloxacin">Moxifloxacin</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/Protein_synthesis_inhibitor" title="Protein synthesis inhibitor">Protein synthesis inhibitor</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/Aminoglycoside" title="Aminoglycoside">Aminoglycosides</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/Amikacin" title="Amikacin">Amikacin</a><sup>#</sup></li> <li><a href="/wiki/Kanamycin" class="mw-redirect" title="Kanamycin">Kanamycin</a></li> <li><a href="/wiki/Streptomycin" title="Streptomycin">Streptomycin</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/2-Oxazolidone" class="mw-redirect" title="2-Oxazolidone">Oxazolidone</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/Linezolid" title="Linezolid">Linezolid</a></li> <li><a href="/wiki/Sutezolid" title="Sutezolid">Sutezolid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polypeptide_antibiotic" title="Polypeptide antibiotic">Polypeptide antibiotics</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/Capreomycin" title="Capreomycin">Capreomycin</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/Cell_envelope_antibiotic" title="Cell envelope antibiotic">Cell envelope antibiotic</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/Peptidoglycan" title="Peptidoglycan">Peptidoglycan</a> layer</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/Alanine" title="Alanine">Alanine</a> analogue: <a href="/wiki/Cycloserine" title="Cycloserine">Cycloserine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arabinogalactan" title="Arabinogalactan">Arabinogalactan</a> layer</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/Ethylenediamine" title="Ethylenediamine">Ethylenediamine</a>/<a href="/wiki/Arabinosyltransferase" title="Arabinosyltransferase">arabinosyltransferase</a> inhibitor: <a href="/wiki/Ethambutol" title="Ethambutol">Ethambutol</a><sup>#</sup></li></ul> <ul><li><a href="/wiki/SQ109" title="SQ109">SQ109</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mycolic_acid" title="Mycolic acid">Mycolic acid</a> layer</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/Hydrazide" title="Hydrazide">Hydrazides</a>/<a href="/wiki/Mycolic_acid" title="Mycolic acid">mycolic acid</a> synth. inhibition: <a class="mw-selflink selflink">Isoniazid</a><sup>#</sup></li> <li><a href="/wiki/Methaniazide" title="Methaniazide">Methaniazide</a></li></ul> <ul><li><a href="/wiki/Thiocarbamide" class="mw-redirect" title="Thiocarbamide">Thiocarbamides</a>: <a href="/wiki/Ethionamide" title="Ethionamide">Ethionamide</a><sup>#</sup></li> <li><a href="/wiki/Prothionamide" title="Prothionamide">Prothionamide</a></li> <li><a href="/wiki/Thiocarlide" title="Thiocarlide">Thiocarlide</a></li></ul> <ul><li>Others/unsorted: <a href="/wiki/Thioacetazone" title="Thioacetazone">Thioacetazone (amithiozone)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/unknown</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Phenazine" title="Phenazine">Phenazine</a></i> (<a href="/wiki/Clofazimine" title="Clofazimine">Clofazimine</a>)<sup>#</sup></li> <li><i><a href="/wiki/Pyrazine" title="Pyrazine">Pyrazine</a></i> (<a href="/wiki/Pyrazinamide" title="Pyrazinamide">Pyrazinamide</a><sup>#</sup>, <a href="/wiki/Morinamide" title="Morinamide">Morinamide</a>)</li> <li><i><a href="/wiki/Isoxazole" title="Isoxazole">Isoxazole</a></i> (<a href="/wiki/Terizidone" title="Terizidone">Terizidone</a>)</li> <li><a href="/wiki/Bedaquiline" title="Bedaquiline">Bedaquiline</a></li> <li><i><a href="/wiki/Nitroimidazole" title="Nitroimidazole">Nitroimidazole</a></i> (<i><a href="/wiki/Delamanid" title="Delamanid">Delamanid</a></i>, <i><a href="/wiki/Pretomanid" title="Pretomanid">Pretomanid</a></i>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethambutol/isoniazid" title="Ethambutol/isoniazid">Ethambutol/isoniazid</a></li> <li><a href="/wiki/Ethambutol/isoniazid/pyrazinamide/rifampicin" title="Ethambutol/isoniazid/pyrazinamide/rifampicin">Ethambutol/isoniazid/pyrazinamide/rifampicin</a><sup>#</sup></li> <li><a href="/wiki/Ethambutol/isoniazid/rifampicin" title="Ethambutol/isoniazid/rifampicin">Ethambutol/isoniazid/rifampicin</a><sup>#</sup></li> <li><a href="/wiki/Isoniazid/pyridoxine/sulfamethoxazole/trimethoprim" title="Isoniazid/pyridoxine/sulfamethoxazole/trimethoprim">Isoniazid/pyridoxine/sulfamethoxazole/trimethoprim</a><sup>#</sup></li> <li><a href="/wiki/Rifampicin/isoniazid/pyrazinamide" title="Rifampicin/isoniazid/pyrazinamide">Rifampicin/isoniazid/pyrazinamide</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /></div><div role="navigation" class="navbox" aria-labelledby="Antibacterials_active_on_the_cell_wall_and_envelope_(J01C-J01D)931" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cell_wall_disruptive_antibiotics" title="Template:Cell wall disruptive antibiotics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cell_wall_disruptive_antibiotics" title="Template talk:Cell wall disruptive antibiotics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cell_wall_disruptive_antibiotics" title="Special:EditPage/Template:Cell wall disruptive antibiotics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antibacterials_active_on_the_cell_wall_and_envelope_(J01C-J01D)931" style="font-size:114%;margin:0 4em"><a href="/wiki/Antibiotics" class="mw-redirect" title="Antibiotics">Antibacterials</a> active on the <a href="/wiki/Cell_wall" title="Cell wall">cell wall</a> and <a href="/wiki/Cell_envelope_antibiotic" title="Cell envelope antibiotic">envelope</a> (<a href="/wiki/ATC_code_J01#J01C" title="ATC code J01">J01C</a>-<a href="/wiki/ATC_code_J01#J01D" title="ATC code J01">J01D</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Beta-lactam_antibiotics" class="mw-redirect" title="Beta-lactam antibiotics">β-lactams</a><br /><small><span class="nobold">(inhibit synthesis<br />of peptidoglycan<br />layer of bacterial<br />cell wall by binding<br />to and inhibiting<br /><a href="/wiki/Penicillin-binding_proteins" title="Penicillin-binding proteins">PBPs</a>, a group of<br /><a href="/wiki/DD-Transpeptidase" title="DD-Transpeptidase"><small>D</small>-alanyl-<small>D</small>-alanine<br />transpeptidases</a>)</span></small></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/Penicillin" title="Penicillin">Penicillins</a> (<a href="/wiki/Penam" title="Penam">Penams</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_%CE%B2-lactam_antibiotics#Narrow-spectrum" title="List of β-lactam antibiotics">Narrow<br />spectrum</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_%CE%B2-lactam_antibiotics#Narrow-spectrum" title="List of β-lactam antibiotics">β-lactamase sensitive</a><br />(1st generation)</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/Benzylpenicillin" title="Benzylpenicillin">Benzylpenicillin (G)</a><sup>#</sup></li> <li><a href="/wiki/Benzathine_benzylpenicillin" title="Benzathine benzylpenicillin">Benzathine benzylpenicillin</a><sup>#</sup></li> <li><a href="/wiki/Procaine_benzylpenicillin" title="Procaine benzylpenicillin">Procaine benzylpenicillin</a><sup>#</sup></li> <li><a href="/wiki/Phenoxymethylpenicillin" title="Phenoxymethylpenicillin">Phenoxymethylpenicillin (V)</a><sup>#</sup></li> <li><a href="/wiki/Propicillin" title="Propicillin">Propicillin</a><sup>‡</sup></li> <li><a href="/wiki/Pheneticillin" title="Pheneticillin">Pheneticillin</a><sup>‡</sup></li> <li><a href="/wiki/Azidocillin" title="Azidocillin">Azidocillin</a><sup>‡</sup></li> <li><a href="/wiki/Clometocillin" title="Clometocillin">Clometocillin</a><sup>‡</sup></li> <li><a href="/wiki/Penamecillin" title="Penamecillin">Penamecillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_%CE%B2-lactam_antibiotics#β-lactamase-resistant" title="List of β-lactam antibiotics">β-lactamase resistant</a><br />(2nd generation)</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/Cloxacillin" title="Cloxacillin">Cloxacillin</a><sup>#</sup> (<a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Flucloxacillin" title="Flucloxacillin">Flucloxacillin</a>)</li> <li><a href="/wiki/Oxacillin" title="Oxacillin">Oxacillin</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Methicillin" title="Methicillin">Methicillin</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/Extended-spectrum_penicillin" title="Extended-spectrum penicillin">Extended<br />spectrum</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aminopenicillin" title="Aminopenicillin">Aminopenicillins</a> (3rd generation)</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/Amoxicillin" title="Amoxicillin">Amoxicillin</a><sup>#</sup></li> <li><a href="/wiki/Ampicillin" title="Ampicillin">Ampicillin</a><sup>#</sup> (<a href="/wiki/Pivampicillin" title="Pivampicillin">Pivampicillin</a></li> <li><a href="/wiki/Hetacillin" title="Hetacillin">Hetacillin</a><sup>‡</sup></li> <li><a href="/wiki/Bacampicillin" title="Bacampicillin">Bacampicillin</a><sup>‡</sup></li> <li><a href="/wiki/Lenampicillin" title="Lenampicillin">Lenampicillin</a></li> <li><a href="/wiki/Metampicillin" title="Metampicillin">Metampicillin</a><sup>‡</sup></li> <li><a href="/wiki/Talampicillin" title="Talampicillin">Talampicillin</a><sup>‡</sup>)</li> <li><a href="/wiki/Epicillin" title="Epicillin">Epicillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carboxypenicillin" title="Carboxypenicillin">Carboxypenicillins</a> (4th generation)</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/Ticarcillin" title="Ticarcillin">Ticarcillin</a></li> <li><a href="/wiki/Carbenicillin" title="Carbenicillin">Carbenicillin</a><sup>‡</sup> / <a href="/wiki/Carindacillin" title="Carindacillin">Carindacillin</a><sup>‡</sup></li> <li><a href="/wiki/Temocillin" title="Temocillin">Temocillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ureidopenicillin" title="Ureidopenicillin">Ureidopenicillins</a> (4th generation)</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/Piperacillin" title="Piperacillin">Piperacillin</a></li> <li><a href="/wiki/Azlocillin" title="Azlocillin">Azlocillin</a><sup>‡</sup></li> <li><a href="/wiki/Mezlocillin" title="Mezlocillin">Mezlocillin</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/Mecillinam" title="Mecillinam">Mecillinam</a> (<a href="/wiki/Pivmecillinam" title="Pivmecillinam">Pivmecillinam</a>)</li> <li><a href="/wiki/Sulbenicillin" title="Sulbenicillin">Sulbenicillin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbapenem" title="Carbapenem">Carbapenems</a> / <a href="/wiki/Penem" title="Penem">Penems</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>Carbapenems (<a href="/wiki/Ertapenem" title="Ertapenem">Ertapenem</a></li> <li><a href="/wiki/Antipseudomonal" class="mw-redirect" title="Antipseudomonal">Antipseudomonal</a> (<a href="/wiki/Doripenem" title="Doripenem">Doripenem</a></li> <li><a href="/wiki/Imipenem" title="Imipenem">Imipenem</a></li> <li><a href="/wiki/Meropenem" title="Meropenem">Meropenem</a>)</li> <li><a href="/wiki/Biapenem" title="Biapenem">Biapenem</a><sup>‡</sup></li> <li><a href="/wiki/Panipenem" title="Panipenem">Panipenem</a>)</li> <li>Penems (<a href="/wiki/Faropenem" title="Faropenem">Faropenem</a></li> <li><a href="/wiki/Ritipenem" title="Ritipenem">Ritipenem</a><sup>§</sup></li> <li><a href="/wiki/Sulopenem" title="Sulopenem">Sulopenem</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephem" title="Cephem">Cephems</a><br /><a href="/wiki/Cephalosporin" title="Cephalosporin">Cephalosporins</a><br /><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycins</a><br /><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephems</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#First_generation" title="Cephalosporin">1st generation</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/Cefazolin" title="Cefazolin">Cefazolin</a><sup>#</sup></li> <li><a href="/wiki/Cefalexin" title="Cefalexin">Cefalexin</a> <sup>#</sup></li> <li><a href="/wiki/Cefadroxil" title="Cefadroxil">Cefadroxil</a></li> <li><a href="/wiki/Cefapirin" title="Cefapirin">Cefapirin</a></li> <li><a href="/wiki/Cefazedone" title="Cefazedone">Cefazedone</a><sup>‡</sup></li> <li><a href="/wiki/Cefazaflur" title="Cefazaflur">Cefazaflur</a><sup>‡</sup></li> <li><a href="/wiki/Cefradine" title="Cefradine">Cefradine</a><sup>‡</sup></li> <li><a href="/wiki/Cefroxadine" title="Cefroxadine">Cefroxadine</a><sup>‡</sup></li> <li><a href="/wiki/Ceftezole" title="Ceftezole">Ceftezole</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloglycin" title="Cefaloglycin">Cefaloglycin</a><sup>‡</sup></li> <li><a href="/wiki/Cefacetrile" title="Cefacetrile">Cefacetrile</a><sup>‡</sup></li> <li><a href="/wiki/Cefalonium" title="Cefalonium">Cefalonium</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloridine" class="mw-redirect" title="Cefaloridine">Cefaloridine</a><sup>‡</sup></li> <li><a href="/wiki/Cefalotin" title="Cefalotin">Cefalotin</a></li> <li><a href="/wiki/Cefatrizine" title="Cefatrizine">Cefatrizine</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Second_generation" title="Cephalosporin">2nd generation</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/Cefaclor" title="Cefaclor">Cefaclor</a></li> <li><a href="/wiki/Cefprozil" title="Cefprozil">Cefprozil</a></li> <li><a href="/wiki/Cefuroxime" title="Cefuroxime">Cefuroxime</a></li> <li><a href="/wiki/Cefuroxime_axetil" title="Cefuroxime axetil">Cefuroxime axetil</a></li> <li><a href="/wiki/Cefamandole" title="Cefamandole">Cefamandole</a><sup>‡</sup></li> <li><a href="/wiki/Cefonicid" title="Cefonicid">Cefonicid</a><sup>‡</sup></li> <li><a href="/wiki/Ceforanide" title="Ceforanide">Ceforanide</a><sup>‡</sup></li> <li><a href="/wiki/Cefuzonam" title="Cefuzonam">Cefuzonam</a><sup>‡</sup></li> <li><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycin</a> (<a href="/wiki/Cefoxitin" title="Cefoxitin">Cefoxitin</a></li> <li><a href="/wiki/Cefotetan" title="Cefotetan">Cefotetan</a></li> <li><a href="/wiki/Cefminox" title="Cefminox">Cefminox</a><sup>‡</sup></li> <li><a href="/wiki/Cefbuperazone" title="Cefbuperazone">Cefbuperazone</a><sup>‡</sup></li> <li><a href="/wiki/Cefmetazole" title="Cefmetazole">Cefmetazole</a><sup>‡</sup>)</li> <li><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephem</a> (<a href="/wiki/Loracarbef" title="Loracarbef">Loracarbef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Third_generation" title="Cephalosporin">3rd generation</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/Cefixime" title="Cefixime">Cefixime</a><sup>#</sup></li> <li><a href="/wiki/Ceftriaxone" title="Ceftriaxone">Ceftriaxone</a><sup>#</sup></li> <li><a href="/wiki/Cefotaxime" title="Cefotaxime">Cefotaxime</a><sup>#</sup></li> <li>Antipseudomonal (<a href="/wiki/Ceftazidime" title="Ceftazidime">Ceftazidime</a><sup>#</sup></li> <li><a href="/wiki/Cefoperazone" title="Cefoperazone">Cefoperazone</a>)</li> <li><a href="/wiki/Cefdinir" title="Cefdinir">Cefdinir</a></li> <li><a href="/wiki/Cefcapene" title="Cefcapene">Cefcapene</a></li> <li><a href="/wiki/Cefdaloxime" title="Cefdaloxime">Cefdaloxime</a></li> <li><a href="/wiki/Ceftizoxime" title="Ceftizoxime">Ceftizoxime</a></li> <li><a href="/wiki/Cefmenoxime" title="Cefmenoxime">Cefmenoxime</a></li> <li><a href="/wiki/Cefpiramide" title="Cefpiramide">Cefpiramide</a></li> <li><a href="/wiki/Cefpodoxime" title="Cefpodoxime">Cefpodoxime</a></li> <li><a href="/wiki/Ceftibuten" title="Ceftibuten">Ceftibuten</a></li> <li><a href="/wiki/Cefditoren" title="Cefditoren">Cefditoren</a></li> <li><a href="/wiki/Cefotiam" title="Cefotiam">Cefotiam</a><sup>‡</sup></li> <li><a href="/wiki/Cefetamet" title="Cefetamet">Cefetamet</a><sup>‡</sup></li> <li><a href="/wiki/Cefodizime" title="Cefodizime">Cefodizime</a><sup>‡</sup></li> <li><a href="/wiki/Cefpimizole" title="Cefpimizole">Cefpimizole</a><sup>‡</sup></li> <li><a href="/wiki/Cefsulodin" title="Cefsulodin">Cefsulodin</a><sup>‡</sup></li> <li><a href="/wiki/Cefteram" title="Cefteram">Cefteram</a><sup>‡</sup></li> <li><a href="/wiki/Ceftiolene" title="Ceftiolene">Ceftiolene</a><sup>‡</sup></li> <li><a href="/wiki/Oxacephem" title="Oxacephem">Oxacephem</a> (<a href="/wiki/Flomoxef" title="Flomoxef">Flomoxef</a></li> <li><a href="/wiki/Latamoxef" title="Latamoxef">Latamoxef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fourth_generation" title="Cephalosporin">4th generation</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/Cefepime" title="Cefepime">Cefepime</a></li> <li><a href="/wiki/Cefozopran" title="Cefozopran">Cefozopran</a><sup>‡</sup></li> <li><a href="/wiki/Cefpirome" title="Cefpirome">Cefpirome</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fifth_generation" title="Cephalosporin">5th generation</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/Ceftaroline_fosamil" title="Ceftaroline fosamil">Ceftaroline fosamil</a></li> <li><a href="/wiki/Ceftolozane" class="mw-redirect" title="Ceftolozane">Ceftolozane</a></li> <li><a href="/wiki/Ceftobiprole" title="Ceftobiprole">Ceftobiprole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Siderophore" title="Siderophore">Siderophore</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/Cefiderocol" title="Cefiderocol">Cefiderocol</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Veterinary_medicine" title="Veterinary medicine">Veterinary</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/Ceftiofur" title="Ceftiofur">Ceftiofur</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a></li> <li><a href="/wiki/Cefovecin" title="Cefovecin">Cefovecin</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/Monobactam" title="Monobactam">Monobactams</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/Aztreonam" title="Aztreonam">Aztreonam</a></li> <li><a href="/wiki/Tigemonam" title="Tigemonam">Tigemonam</a><sup>‡</sup></li> <li><a href="/wiki/Carumonam" title="Carumonam">Carumonam</a><sup>‡</sup></li> <li><a href="/wiki/Nocardicin_A" title="Nocardicin A">Nocardicin A</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%92-Lactamase_inhibitor" title="Β-Lactamase inhibitor">β-lactamase 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/Penam" title="Penam">Penam</a> (<a href="/wiki/Sulbactam" title="Sulbactam">Sulbactam</a></li> <li><a href="/wiki/Tazobactam" title="Tazobactam">Tazobactam</a>)</li> <li><a href="/wiki/Clavam" title="Clavam">Clavam</a> (<a href="/wiki/Clavulanic_acid" title="Clavulanic acid">Clavulanic acid</a>)</li> <li>non-β-lactam (<a href="/wiki/Avibactam" title="Avibactam">Avibactam</a></li> <li><a href="/wiki/Durlobactam" title="Durlobactam">Durlobactam</a></li> <li><a href="/wiki/Relebactam" title="Relebactam">Relebactam</a></li> <li><a href="/wiki/Vaborbactam" title="Vaborbactam">Vaborbactam</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amoxicillin/clavulanic_acid" title="Amoxicillin/clavulanic acid">Amoxicillin/clavulanic acid</a><sup>#</sup></li> <li><a href="/wiki/Ampicillin/flucloxacillin" title="Ampicillin/flucloxacillin">Ampicillin/flucloxacillin</a></li> <li><a href="/wiki/Ampicillin/sulbactam" title="Ampicillin/sulbactam">Ampicillin/sulbactam</a> (<a href="/wiki/Sultamicillin" title="Sultamicillin">Sultamicillin</a>)</li> <li><a href="/wiki/Aztreonam/avibactam" title="Aztreonam/avibactam">Aztreonam/avibactam</a></li> <li><a href="/wiki/Benzathine_benzylpenicillin/procaine_benzylpenicillin" title="Benzathine benzylpenicillin/procaine benzylpenicillin">Benzathine benzylpenicillin/procaine benzylpenicillin</a></li> <li><a href="/wiki/Cefepime/enmetazobactam" title="Cefepime/enmetazobactam">Cefepime/enmetazobactam</a></li> <li><a href="/wiki/Cefoperazone/sulbactam" title="Cefoperazone/sulbactam">Cefoperazone/sulbactam</a></li> <li><a href="/wiki/Ceftazidime/avibactam" title="Ceftazidime/avibactam">Ceftazidime/avibactam</a></li> <li><a href="/wiki/Ceftolozane/tazobactam" title="Ceftolozane/tazobactam">Ceftolozane/tazobactam</a></li> <li><a href="/wiki/Imipenem/cilastatin" title="Imipenem/cilastatin">Imipenem/cilastatin</a><sup>#</sup></li> <li><a href="/wiki/Imipenem/cilastatin/relebactam" title="Imipenem/cilastatin/relebactam">Imipenem/cilastatin/relebactam</a></li> <li><a href="/wiki/Meropenem/vaborbactam" title="Meropenem/vaborbactam">Meropenem/vaborbactam</a></li> <li><a href="/wiki/Panipenem/betamipron" title="Panipenem/betamipron">Panipenem/betamipron</a></li> <li><a href="/wiki/Piperacillin/tazobactam" title="Piperacillin/tazobactam">Piperacillin/tazobactam</a></li> <li><a href="/wiki/Sulbactam/durlobactam" title="Sulbactam/durlobactam">Sulbactam/durlobactam</a></li> <li><a href="/wiki/Sulopenem/probenecid" title="Sulopenem/probenecid">Sulopenem/probenecid</a></li> <li><a href="/wiki/Ticarcillin/clavulanic_acid" title="Ticarcillin/clavulanic acid">Ticarcillin/clavulanic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polypeptide_antibiotic" title="Polypeptide antibiotic">Polypeptides</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/Lipopeptide" title="Lipopeptide">Lipopeptides</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>Insert into bacterial cell wall causing perforation and depolarization: <a href="/wiki/Daptomycin" title="Daptomycin">Daptomycin</a></li> <li><a href="/wiki/Surfactin" title="Surfactin">Surfactin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibits PG elongation and crosslinking: <a href="/wiki/Ramoplanin" title="Ramoplanin">Ramoplanin</a><sup>§</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intracellular</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibit <a href="/wiki/Peptidoglycan" title="Peptidoglycan">PG</a> subunit synthesis and transport: <a href="/wiki/N-Acetylmuramic_acid" title="N-Acetylmuramic acid">NAM</a> synthesis inhibition (<a href="/wiki/Fosfomycin" title="Fosfomycin">Fosfomycin</a>)</li> <li><a href="/wiki/D-alanine%E2%80%94D-alanine_ligase" title="D-alanine—D-alanine ligase">DADAL</a>/<a href="/wiki/Alanine_racemase" title="Alanine racemase">AR</a> inhibitors (<a href="/wiki/Cycloserine" title="Cycloserine">Cycloserine</a>)</li> <li><a href="/wiki/Bactoprenol" title="Bactoprenol">bactoprenol</a> inhibitors (<a href="/wiki/Bacitracin" title="Bacitracin">Bacitracin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Hydrolyze NAM-NAG <ul><li><a href="/wiki/Lysozyme" title="Lysozyme">lysozyme</a></li></ul></li> <li><a href="/wiki/Tyrothricin" title="Tyrothricin">Tyrothricin</a> <ul><li><a href="/wiki/Gramicidin" title="Gramicidin">Gramicidin</a></li> <li><a href="/wiki/Tyrocidine" title="Tyrocidine">Tyrocidine</a></li></ul></li> <li><a class="mw-selflink selflink">Isoniazid</a><sup>#</sup></li> <li><a href="/wiki/Teixobactin" title="Teixobactin">Teixobactin</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Monoamine_metabolism_modulators806" 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:Monoamine_metabolism_modulators" title="Template:Monoamine metabolism modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Monoamine_metabolism_modulators" title="Template talk:Monoamine metabolism modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Monoamine_metabolism_modulators" title="Special:EditPage/Template:Monoamine metabolism modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Monoamine_metabolism_modulators806" style="font-size:114%;margin:0 4em"><a href="/wiki/Monoamine_neurotransmitter" title="Monoamine neurotransmitter">Monoamine</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> <a href="/wiki/Enzyme_modulator" title="Enzyme modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Non-specific</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:4em;;text-align:center;"><a href="/wiki/Aromatic_L-amino_acid_decarboxylase" title="Aromatic L-amino acid decarboxylase"><abbr title="Aromatic L-amino acid decarboxylase">AAAD</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Aromatic L-amino acid decarboxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA (levodopa)</a>→<a href="/wiki/Dopamine" title="Dopamine">Dopamine</a></li> <li><a href="/wiki/5-HTP" class="mw-redirect" title="5-HTP">5-HTP</a>→<a href="/wiki/Serotonin" title="Serotonin">Serotonin</a></li> <li><a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><small>L</small>-Histidine</a>→<a href="/wiki/Histamine" title="Histamine">Histamine</a></li> <li><a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a>→<a href="/wiki/Phenethylamine" title="Phenethylamine">Phenethylamine</a></li> <li><a href="/wiki/L-Tyrosine" class="mw-redirect" title="L-Tyrosine"><small>L</small>-Tyrosine</a>→<a href="/wiki/Tyramine" title="Tyramine">Tyramine</a></li> <li><a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a>→<a href="/wiki/Tryptamine" title="Tryptamine">Tryptamine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Benserazide" title="Benserazide">Benserazide</a></li> <li><a href="/wiki/Carbidopa" title="Carbidopa">Carbidopa</a></li> <li><a href="/wiki/Alpha-Difluoromethyl-DOPA" class="mw-redirect" title="Alpha-Difluoromethyl-DOPA">DFMD</a></li> <li><a href="/wiki/Genistein" title="Genistein">Genistein</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Monoamine_oxidase" title="Monoamine oxidase"><abbr title="Monoamine oxidase">MAO</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Monoamine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products (with <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase"><abbr title="Aldehyde dehydrogenase">ALDH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Aldehyde dehydrogenase</span>/<a href="/wiki/Aldehyde_reductase" class="mw-redirect" title="Aldehyde reductase"><abbr title="Aldehyde reductase">ALR</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip ALR</span>):</b> <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a>→<a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">DHMA</a></li> <li><a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a>→<a href="/wiki/3-Methoxy-4-hydroxyphenylglycol" title="3-Methoxy-4-hydroxyphenylglycol">MHPG</a>/<a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">VMA</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a>→<a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">DHMA</a></li> <li><a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a>→<a href="/wiki/3-Methoxy-4-hydroxyphenylglycol" title="3-Methoxy-4-hydroxyphenylglycol">MHPG</a>/<a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">VMA</a></li> <li><a href="/wiki/Dopamine" title="Dopamine">Dopamine</a>→<a href="/wiki/3,4-Dihydroxyphenylacetic_acid" title="3,4-Dihydroxyphenylacetic acid">DOPAC</a></li> <li><a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a>→<a href="/wiki/Homovanillic_acid" title="Homovanillic acid">HVA</a></li> <li><a href="/wiki/Serotonin" title="Serotonin">Serotonin</a>→<a href="/wiki/5-Hydroxyindoleacetic_acid" title="5-Hydroxyindoleacetic acid">5-HIAA</a></li></ul> <ul><li><b>Inhibitors:</b> <i>Non-selective:</i> <a href="/wiki/Benmoxin" title="Benmoxin">Benmoxin</a></li> <li><a href="/wiki/Caroxazone" title="Caroxazone">Caroxazone</a></li> <li><a href="/wiki/Echinopsidine" title="Echinopsidine">Echinopsidine</a></li> <li><a href="/wiki/Furazolidone" title="Furazolidone">Furazolidone</a></li> <li><a href="/wiki/Guineesine" title="Guineesine">Guineesine</a></li> <li><a href="/wiki/Hydralazine" title="Hydralazine">Hydralazine</a></li> <li><a href="/wiki/Indantadol" title="Indantadol">Indantadol</a></li> <li><a href="/wiki/Iproclozide" title="Iproclozide">Iproclozide</a></li> <li><a href="/wiki/Iproniazid" title="Iproniazid">Iproniazid</a></li> <li><a href="/wiki/Isocarboxazid" title="Isocarboxazid">Isocarboxazid</a></li> <li><a class="mw-selflink selflink">Isoniazid</a></li> <li><a href="/wiki/Linezolid" title="Linezolid">Linezolid</a></li> <li><a href="/wiki/Mebanazine" title="Mebanazine">Mebanazine</a></li> <li><a href="/wiki/Metfendrazine" title="Metfendrazine">Metfendrazine</a></li> <li><a href="/wiki/Nialamide" title="Nialamide">Nialamide</a></li> <li><a href="/wiki/Octamoxin" title="Octamoxin">Octamoxin</a></li> <li><a href="/wiki/Paraxazone" title="Paraxazone">Paraxazone</a></li> <li><a href="/wiki/Phenelzine" title="Phenelzine">Phenelzine</a></li> <li><a href="/wiki/Pheniprazine" title="Pheniprazine">Pheniprazine</a></li> <li><a href="/wiki/Phenoxypropazine" title="Phenoxypropazine">Phenoxypropazine</a></li> <li><a href="/wiki/Pivhydrazine" title="Pivhydrazine">Pivhydrazine</a></li> <li><a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a></li> <li><a href="/wiki/Safrazine" title="Safrazine">Safrazine</a></li> <li><a href="/wiki/Tranylcypromine" title="Tranylcypromine">Tranylcypromine</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <i>MAO-A-selective:</i> <a href="/wiki/Amiflamine" title="Amiflamine">Amiflamine</a></li> <li><a href="/wiki/Bazinaprine" title="Bazinaprine">Bazinaprine</a></li> <li><a href="/wiki/Befloxatone" title="Befloxatone">Befloxatone</a></li> <li><a href="/wiki/Brofaromine" title="Brofaromine">Brofaromine</a></li> <li><a href="/wiki/Cimoxatone" title="Cimoxatone">Cimoxatone</a></li> <li><a href="/wiki/Clorgiline" title="Clorgiline">Clorgiline</a></li> <li><a href="/wiki/CX157" title="CX157">CX157 (Tyrima)</a></li> <li><a href="/wiki/Eprobemide" title="Eprobemide">Eprobemide</a></li> <li><a href="/wiki/Esuprone" title="Esuprone">Esuprone</a></li> <li><a href="/wiki/Harmala_alkaloid" title="Harmala alkaloid">Harmala alkaloids</a> (e.g., <a href="/wiki/Harmine" title="Harmine">harmine</a>, <a href="/wiki/Harmaline" title="Harmaline">harmaline</a>, <a href="/wiki/Harmane" title="Harmane">harman</a>, <a href="/wiki/Norharman" class="mw-redirect" title="Norharman">norharman</a>, <a href="/wiki/Tetrahydroharmine" title="Tetrahydroharmine">tetrahydroharmine</a>)</li> <li><a href="/wiki/Methylene_blue" title="Methylene blue">Methylene blue</a></li> <li><a href="/wiki/Metralindole" title="Metralindole">Metralindole</a></li> <li><a href="/wiki/Minaprine" title="Minaprine">Minaprine</a></li> <li><a href="/wiki/Moclobemide" title="Moclobemide">Moclobemide</a></li> <li><a href="/wiki/Pirlindole" title="Pirlindole">Pirlindole</a></li> <li><a href="/wiki/Sercloremine" title="Sercloremine">Sercloremine</a></li> <li><a href="/wiki/Tetrindole" title="Tetrindole">Tetrindole</a></li> <li><a href="/wiki/Toloxatone" title="Toloxatone">Toloxatone</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"> <ul><li><b>Inhibitors:</b> <i>MAO-B selective:</i> <a href="/wiki/Adarigiline" title="Adarigiline">Adarigiline</a></li> <li><a href="/wiki/Almoxatone" title="Almoxatone">Almoxatone</a></li> <li><a href="/wiki/D-Deprenyl" title="D-Deprenyl"><small>D</small>-Deprenyl</a></li> <li><a href="/wiki/Desmethylselegiline" title="Desmethylselegiline">Desmethylselegiline</a></li> <li><a href="/wiki/Ethanol" title="Ethanol">Ethanol</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Lazabemide" title="Lazabemide">Lazabemide</a></li> <li><a href="/wiki/Milacemide" title="Milacemide">Milacemide</a></li> <li><a href="/wiki/Mofegiline" title="Mofegiline">Mofegiline</a></li> <li><a href="/wiki/Nicotine" title="Nicotine">Nicotine</a></li> <li><a href="/wiki/Pargyline" title="Pargyline">Pargyline</a><sup>‡</sup></li> <li><a href="/wiki/Rasagiline" title="Rasagiline">Rasagiline</a></li> <li><a href="/wiki/Safinamide" title="Safinamide">Safinamide</a></li> <li><a href="/wiki/Selegiline" title="Selegiline">Selegiline (<small>L</small>-Deprenyl)</a></li> <li><a href="/wiki/Sembragiline" title="Sembragiline">Sembragiline</a></li> <li><a href="/wiki/Tisolagiline" title="Tisolagiline">Tisolagiline</a></li> <li><a href="/wiki/Vafidemstat" title="Vafidemstat">Vafidemstat</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Substituted_phenethylamine" title="Substituted phenethylamine">Phenethylamines</a><br /><small>(<a href="/wiki/Dopamine" title="Dopamine">dopamine</a>, <a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">epinephrine</a>,<br /><a href="/wiki/Norepinephrine" title="Norepinephrine">norepinephrine</a>)</small></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:4em;;text-align:center;"><a href="/wiki/Phenylalanine_hydroxylase" title="Phenylalanine hydroxylase"><abbr title="Phenylalanine hydroxylase">PAH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Phenylalanine hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Phenylalanine" title="Phenylalanine">Phenylalanine</a>→<a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/3,4-Dihydroxystyrene" title="3,4-Dihydroxystyrene">3,4-Dihydroxystyrene</a></li> <li><a href="/wiki/%CE%91-Methylphenylalanine" title="Α-Methylphenylalanine">α-Methylphenylalanine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Tyrosine_hydroxylase" title="Tyrosine hydroxylase"><abbr title="Tyrosine hydroxylase">TH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Tyrosine hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Tyrosine" title="Tyrosine">Tyrosine</a>→<a href="/wiki/L-DOPA" title="L-DOPA"><small>L</small>-DOPA (levodopa)</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/3-Iodotyrosine" title="3-Iodotyrosine">3-Iodotyrosine</a></li> <li><a href="/wiki/%CE%91-Methyl-5-hydroxytryptophan" title="Α-Methyl-5-hydroxytryptophan">α-Methyl-5-hydroxytryptophan (α-Me-5-HTP)</a></li> <li><a href="/wiki/%CE%91-Methylphenylalanine" title="Α-Methylphenylalanine">α-Methylphenylalanine</a></li> <li><a href="/wiki/Aquayamycin" title="Aquayamycin">Aquayamycin</a></li> <li><a href="/wiki/Bulbocapnine" title="Bulbocapnine">Bulbocapnine</a></li> <li><a href="/wiki/Methyldopa" title="Methyldopa">Methyldopa (α-methyl-<small>L</small>-DOPA)</a></li> <li><a href="/wiki/Metirosine" class="mw-redirect" title="Metirosine">Metirosine (α-methyl-<i>p</i>-tyrosine)</a></li> <li><a href="/wiki/Oudenone" title="Oudenone">Oudenone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Dopamine_beta-hydroxylase" title="Dopamine beta-hydroxylase"><abbr title="Dopamine beta-hydroxylase">DBH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Dopamine beta-hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Dopamine" title="Dopamine">Dopamine</a>→<a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (Noradrenaline)</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Bupicomide" title="Bupicomide">Bupicomide</a></li> <li><a href="/wiki/Disulfiram" title="Disulfiram">Disulfiram</a></li> <li><a href="/wiki/Dopastin" title="Dopastin">Dopastin</a></li> <li><a href="/wiki/Etamicastat" title="Etamicastat">Etamicastat</a></li> <li><a href="/wiki/Fusaric_acid" title="Fusaric acid">Fusaric acid</a></li> <li><a href="/wiki/Nepicastat" title="Nepicastat">Nepicastat</a></li> <li><a href="/wiki/Phenopicolinic_acid" title="Phenopicolinic acid">Phenopicolinic acid</a></li> <li><a href="/wiki/Tropolone" title="Tropolone">Tropolone</a></li> <li><a href="/wiki/Zamicastat" title="Zamicastat">Zamicastat</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Phenylethanolamine_N-methyltransferase" title="Phenylethanolamine N-methyltransferase"><abbr title="Phenylethanolamine N-methyltransferase">PNMT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Phenylethanolamine N-methyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine (noradrenaline)</a>→<a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine (adrenaline)</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/w/index.php?title=CGS-19281A&action=edit&redlink=1" class="new" title="CGS-19281A (page does not exist)">CGS-19281A</a></li> <li><a href="/w/index.php?title=SKF-64139&action=edit&redlink=1" class="new" title="SKF-64139 (page does not exist)">SKF-64139</a></li> <li><a href="/w/index.php?title=SKF-7698&action=edit&redlink=1" class="new" title="SKF-7698 (page does not exist)">SKF-7698</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Catechol-O-methyl_transferase" class="mw-redirect" title="Catechol-O-methyl transferase"><abbr title="Catechol-O-methyl transferase">COMT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Catechol-O-methyl transferase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Dopamine" title="Dopamine">Dopamine</a>→<a href="/wiki/3-Methoxytyramine" title="3-Methoxytyramine">3-Methoxytyramine</a></li> <li><a href="/wiki/DOPAC" class="mw-redirect" title="DOPAC">DOPAC</a>→<a href="/wiki/Homovanillic_acid" title="Homovanillic acid">Homovanillic acid</a></li> <li><a href="/wiki/Norepinephrine" title="Norepinephrine">Norepinephrine</a>→<a href="/wiki/Normetanephrine" title="Normetanephrine">Normetanephrine</a></li> <li><a href="/wiki/Epinephrine" class="mw-redirect" title="Epinephrine">Epinephrine</a>→<a href="/wiki/Metanephrine" title="Metanephrine">Metanephrine</a></li> <li><a href="/wiki/Dihydroxyphenylethylene_glycol" title="Dihydroxyphenylethylene glycol">DOPEG</a>→<a href="/wiki/Methoxyhydroxyphenylglycol" class="mw-redirect" title="Methoxyhydroxyphenylglycol">MOPEG</a></li> <li><a href="/wiki/3,4-Dihydroxymandelic_acid" title="3,4-Dihydroxymandelic acid">DOMA</a>→<a href="/wiki/Vanillylmandelic_acid" title="Vanillylmandelic acid">VMA</a></li> <li><a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a>→<a href="/wiki/2-Methoxyestradiol" title="2-Methoxyestradiol">2-Methoxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a>→<a href="/wiki/2-Methoxyestrone" title="2-Methoxyestrone">2-Methoxyestrone</a></li> <li><a href="/wiki/4-Hydroxyestradiol" title="4-Hydroxyestradiol">4-Hydroxyestradiol</a>→<a href="/wiki/4-Methoxyestradiol" title="4-Methoxyestradiol">4-Methoxyestradiol</a></li> <li><a href="/wiki/4-Hydroxyestrone" title="4-Hydroxyestrone">4-Hydroxyestrone</a>→<a href="/wiki/4-Methoxyestrone" title="4-Methoxyestrone">4-Methoxyestrone</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/2-Hydroxyestradiol" title="2-Hydroxyestradiol">2-Hydroxyestradiol</a></li> <li><a href="/wiki/2-Hydroxyestrone" title="2-Hydroxyestrone">2-Hydroxyestrone</a></li> <li><a href="/wiki/Entacapone" title="Entacapone">Entacapone</a></li> <li><a href="/wiki/Nebicapone" title="Nebicapone">Nebicapone</a></li> <li><a href="/wiki/Neluxicapone" title="Neluxicapone">Neluxicapone</a></li> <li><a href="/wiki/Nitecapone" title="Nitecapone">Nitecapone</a></li> <li><a href="/wiki/Opicapone" title="Opicapone">Opicapone</a></li> <li><a href="/wiki/Quinalizarin" title="Quinalizarin">Quinalizarin</a></li> <li><a href="/wiki/Tolcapone" title="Tolcapone">Tolcapone</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Substituted_tryptamine" title="Substituted tryptamine">Tryptamines</a><br /><small>(<a href="/wiki/Serotonin" title="Serotonin">serotonin</a>, <a href="/wiki/Melatonin" title="Melatonin">melatonin</a>)</small></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:4em;;text-align:center;"><a href="/wiki/Tryptophan_hydroxylase" title="Tryptophan hydroxylase"><abbr title="Tryptophan hydroxylase">TPH</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Tryptophan hydroxylase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Tryptophan" title="Tryptophan">Tryptophan</a>→<a href="/wiki/5-HTP" class="mw-redirect" title="5-HTP">5-HTP</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/AGN-2979" title="AGN-2979">AGN-2979</a></li> <li><a href="/wiki/Fenclonine" title="Fenclonine">Fenclonine (PCPA)</a></li> <li><a href="/wiki/Telotristat_ethyl" title="Telotristat ethyl">Telotristat ethyl</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Serotonin_N-acetyl_transferase" class="mw-redirect" title="Serotonin N-acetyl transferase"><abbr title="Serotonin N-acetyl transferase">AANAT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Serotonin N-acetyl transferase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Serotonin" title="Serotonin">Serotonin</a>→<a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">N-Acetylserotonin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Acetylserotonin_O-methyltransferase" title="Acetylserotonin O-methyltransferase"><abbr title="Acetylserotonin O-methyltransferase">ASMT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Acetylserotonin O-methyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/N-Acetylserotonin" title="N-Acetylserotonin">N-Acetylserotonin</a>→<a href="/wiki/Melatonin" title="Melatonin">Melatonin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Histamine" title="Histamine">Histamine</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:4em;;text-align:center;"><a href="/wiki/Histidine_decarboxylase" title="Histidine decarboxylase"><abbr title="Histidine decarboxylase">HDC</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Histidine decarboxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/L-Histidine" class="mw-redirect" title="L-Histidine"><small>L</small>-Histidine</a>→<a href="/wiki/Histamine" title="Histamine">Histamine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/(%2B)-Catechin" class="mw-redirect" title="(+)-Catechin">Catechin</a></li> <li><a href="/wiki/Alpha-Fluoromethylhistidine" class="mw-redirect" title="Alpha-Fluoromethylhistidine">Alpha-Fluoromethylhistidine</a></li> <li><a href="/wiki/Histidine_methyl_ester" title="Histidine methyl ester">Histidine methyl ester</a></li> <li><a href="/wiki/Meciadanol" title="Meciadanol">Meciadanol</a></li> <li><a href="/wiki/Naringenin" title="Naringenin">Naringenin</a></li> <li><a href="/wiki/Tritoqualine" title="Tritoqualine">Tritoqualine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Histamine_N-methyltransferase" title="Histamine N-methyltransferase"><abbr title="Histamine N-methyltransferase">HNMT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Histamine N-methyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Histamine" title="Histamine">Histamine</a>→<a href="/w/index.php?title=N-Methylhistamine&action=edit&redlink=1" class="new" title="N-Methylhistamine (page does not exist)">N-Methylhistamine</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Amodiaquine" title="Amodiaquine">Amodiaquine</a></li> <li><a href="/wiki/Diphenhydramine" title="Diphenhydramine">Diphenhydramine</a></li> <li><a href="/wiki/Harmaline" title="Harmaline">Harmaline</a></li> <li><a href="/wiki/Metoprine" title="Metoprine">Metoprine</a></li> <li><a href="/wiki/Quinacrine" class="mw-redirect" title="Quinacrine">Quinacrine</a></li> <li><a href="/wiki/SKF-91488" title="SKF-91488">SKF-91488</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:4em;;text-align:center;"><a href="/wiki/Diamine_oxidase" title="Diamine oxidase"><abbr title="Diamine oxidase">DAO</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Diamine oxidase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Substrates→Products:</b> <a href="/wiki/Histamine" title="Histamine">Histamine</a>→<a href="/w/index.php?title=Imidazole_acetic_acid&action=edit&redlink=1" class="new" title="Imidazole acetic acid (page does not exist)">Imidazole acetic acid</a></li></ul> <ul><li><b>Inhibitors:</b> <a href="/wiki/Pimagedine" title="Pimagedine">Pimagedine (aminoguanidine)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div><small><i><b>See also:</b> <a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> • <a href="/wiki/Template:Adrenergics" class="mw-redirect" title="Template:Adrenergics">Adrenergics</a> • <a href="/wiki/Template:Dopaminergics" class="mw-redirect" title="Template:Dopaminergics">Dopaminergics</a> • <a href="/wiki/Template:Melatonergics" class="mw-redirect" title="Template:Melatonergics">Melatonergics</a> • <a href="/wiki/Template:Serotonergics" class="mw-redirect" title="Template:Serotonergics">Serotonergics</a> • <a href="/wiki/Template:Monoamine_reuptake_inhibitors" title="Template:Monoamine reuptake inhibitors">Monoamine reuptake inhibitors</a> • <a href="/wiki/Template:Monoamine_releasing_agents" title="Template:Monoamine releasing agents">Monoamine releasing agents</a> • <a href="/wiki/Template:Monoamine_neurotoxins" class="mw-redirect" title="Template:Monoamine neurotoxins">Monoamine neurotoxins</a></i></small></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="GABATooltip_γ-Aminobutyric_acid_metabolism_and_transport_modulators899" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:GABA_metabolism_and_transport_modulators" title="Template:GABA metabolism and transport modulators"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:GABA_metabolism_and_transport_modulators" title="Template talk:GABA metabolism and transport modulators"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:GABA_metabolism_and_transport_modulators" title="Special:EditPage/Template:GABA metabolism and transport modulators"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="GABATooltip_γ-Aminobutyric_acid_metabolism_and_transport_modulators899" style="font-size:114%;margin:0 4em"><a href="/wiki/%CE%93-Aminobutyric_acid" class="mw-redirect" title="Γ-Aminobutyric acid"><abbr title="γ-Aminobutyric acid">GABA</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip γ-Aminobutyric acid</span> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/GABA_transporter" title="GABA transporter">transport</a> <a href="/wiki/Ligand_(biochemistry)" title="Ligand (biochemistry)">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:5em;text-align:center;"><a href="/wiki/GABA_transporter" title="GABA transporter"><abbr title="GABA transporter">GAT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip GABA transporter</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/w/index.php?title=4-Aminovaleric_acid&action=edit&redlink=1" class="new" title="4-Aminovaleric acid (page does not exist)">4-Aminovaleric acid</a></li> <li><a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Arecaidine" title="Arecaidine">Arecaidine</a></li> <li><a href="/wiki/CI-966" title="CI-966">CI-966</a></li> <li><a href="/wiki/2,4-Diaminobutyric_acid" title="2,4-Diaminobutyric acid">DABA</a></li> <li><a href="/wiki/Deramciclane" title="Deramciclane">Deramciclane (EGIS-3886, EGYT-3886)</a></li> <li><a href="/wiki/EF-1502" title="EF-1502">EF-1502</a></li> <li><a href="/wiki/Gabaculine" title="Gabaculine">Gabaculine</a></li> <li><a href="/wiki/Guvacine" title="Guvacine">Guvacine</a></li> <li><a href="/wiki/Ibotenic_acid" title="Ibotenic acid">Ibotenic acid</a></li> <li><a href="/wiki/Muscimol" title="Muscimol">Muscimol</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/w/index.php?title=NNC_05-2090&action=edit&redlink=1" class="new" title="NNC 05-2090 (page does not exist)">NNC 05-2090</a></li> <li><a href="/wiki/NO-711" class="mw-redirect" title="NO-711">NO-711</a></li> <li><a href="/wiki/Riluzole" title="Riluzole">Riluzole</a></li> <li><a href="/wiki/SKF-89976A" title="SKF-89976A">SKF-89976A</a></li> <li><a href="/w/index.php?title=SNAP-5114&action=edit&redlink=1" class="new" title="SNAP-5114 (page does not exist)">SNAP-5114</a></li> <li><a href="/w/index.php?title=Trans-4-Aminocrotonic_acid&action=edit&redlink=1" class="new" title="Trans-4-Aminocrotonic acid (page does not exist)">TACA</a></li> <li><a href="/wiki/Tiagabine" title="Tiagabine">Tiagabine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;text-align:center;"><a href="/wiki/Vesicular_inhibitory_amino_acid_transporter" title="Vesicular inhibitory amino acid transporter"><abbr title="Vesicular inhibitory amino acid transporter">VIAAT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Vesicular inhibitory amino acid transporter</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/wiki/%CE%92-Alanine" title="Β-Alanine">β-Alanine</a></li> <li><a href="/wiki/Bafilomycin_A1" class="mw-redirect" title="Bafilomycin A1">Bafilomycin A1</a></li> <li><a href="/w/index.php?title=Chicago_sky_blue_6B&action=edit&redlink=1" class="new" title="Chicago sky blue 6B (page does not exist)">Chicago sky blue 6B</a></li> <li><a href="/wiki/Evans_blue_(dye)" title="Evans blue (dye)">Evans blue</a></li> <li><a href="/wiki/GABA" title="GABA">GABA</a></li> <li><a href="/wiki/Glycine" title="Glycine">Glycine</a></li> <li><a href="/wiki/N-Butyric_acid" class="mw-redirect" title="N-Butyric acid">N-Butyric acid</a></li> <li><a href="/wiki/Nigericin" title="Nigericin">Nigericin</a></li> <li><a href="/wiki/Nipecotic_acid" title="Nipecotic acid">Nipecotic acid</a></li> <li><a href="/wiki/Valinomycin" title="Valinomycin">Valinomycin</a></li> <li><a href="/wiki/Vigabatrin" title="Vigabatrin">Vigabatrin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:5em;text-align:center;"><a href="/wiki/Glutamate_decarboxylase" title="Glutamate decarboxylase"><abbr title="Glutamate decarboxylase">GAD</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Glutamate decarboxylase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/wiki/3-Mercaptopropionic_acid" title="3-Mercaptopropionic acid">3-Mercaptopropionic acid</a></li> <li><a href="/wiki/Aminooxyacetic_acid" title="Aminooxyacetic acid">AAOA</a></li> <li><a href="/wiki/L-Allylglycine" class="mw-redirect" title="L-Allylglycine"><span style="font-size:85%;">L</span>-Allylglycine</a></li> <li><a href="/wiki/Semicarbazide" title="Semicarbazide">Semicarbazide</a></li></ul> <ul><li><i>Activators:</i> <a href="/wiki/3-Methyl-GABA" title="3-Methyl-GABA">3-Methyl-GABA</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:5em;text-align:center;"><a href="/wiki/%CE%93-Aminobutyrate_aminotransferase" class="mw-redirect" title="Γ-Aminobutyrate aminotransferase"><abbr title="γ-Aminobutyrate aminotransferase">GABA-T</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip γ-Aminobutyrate aminotransferase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><i>Inhibitors:</i> <a href="/w/index.php?title=3-Hydrazinopropionic_acid&action=edit&redlink=1" class="new" title="3-Hydrazinopropionic acid (page does not exist)">3-Hydrazinopropionic acid</a></li> <li><a href="/wiki/2,4-Diaminobutyric_acid" title="2,4-Diaminobutyric acid">DABA</a></li> <li><a href="/wiki/%CE%93-Acetylenic-GABA" class="mw-redirect" title="Γ-Acetylenic-GABA">γ-Acetylenic-GABA</a></li> <li><a href="/wiki/Aminooxyacetic_acid" title="Aminooxyacetic acid">AOAA</a></li> <li><a href="/wiki/Ethanolamine-O-sulfate" title="Ethanolamine-O-sulfate">EOS</a></li> <li><a href="/wiki/Gabaculine" title="Gabaculine">Gabaculine</a></li> <li><a class="mw-selflink selflink">Isoniazid</a></li> <li><a href="/wiki/L-Cycloserine" class="mw-redirect" title="L-Cycloserine"><small>L</small>-Cycloserine</a></li> <li><a href="/wiki/Phenelzine" title="Phenelzine">Phenelzine</a></li> <li><a href="/wiki/Phenylethylidenehydrazine" title="Phenylethylidenehydrazine">PEH</a></li> <li><a href="/wiki/Rosmarinic_acid" title="Rosmarinic acid">Rosmarinic acid</a> (<a href="/wiki/Lemon_balm" title="Lemon balm">lemon balm</a>)</li> <li><a href="/wiki/Sodium_valproate" class="mw-redirect" title="Sodium valproate">Sodium valproate</a></li> <li><a href="/wiki/Valnoctamide" title="Valnoctamide">Valnoctamide</a></li> <li><a href="/wiki/Valproate_pivoxil" title="Valproate pivoxil">Valproate pivoxil</a></li> <li><a href="/wiki/Valproate_semisodium" class="mw-redirect" title="Valproate semisodium">Valproate semisodium (divalproex sodium)</a></li> <li><a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">Valproic acid</a></li> <li><a href="/wiki/Valpromide" title="Valpromide">Valpromide</a></li> <li><a href="/wiki/Vigabatrin" title="Vigabatrin">Vigabatrin</a></li></ul> <ul><li><i>Activators:</i> <a href="/wiki/3-Methyl-GABA" title="3-Methyl-GABA">3-Methyl-GABA</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:5em;text-align:center;"><a href="/wiki/Antivitamin" class="mw-redirect" title="Antivitamin">Antivitamin B6</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ginkgotoxin" title="Ginkgotoxin">Ginkgotoxin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><i><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a> </i></dd> <dd><i><a href="/wiki/Template:GABA_receptor_modulators" title="Template:GABA receptor modulators">GABA receptor modulators</a> </i></dd> <dd><i><a href="/wiki/Template:GABAA_receptor_positive_modulators" title="Template:GABAA receptor positive modulators">GABA<sub>A</sub> receptor positive modulators</a> </i></dd> <dd><i><a href="/wiki/Template:Glutamate_metabolism_and_transport_modulators" title="Template:Glutamate metabolism and transport modulators">Glutamate metabolism/transport modulators</a> </i></dd></dl> </div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="Hydrazines14" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Hydrazines" title="Template:Hydrazines"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Hydrazines" title="Template talk:Hydrazines"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Hydrazines" title="Special:EditPage/Template:Hydrazines"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Hydrazines14" style="font-size:114%;margin:0 4em"><a href="/wiki/Hydrazines" title="Hydrazines">Hydrazines</a></div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/4-Phenylthiosemicarbazide" title="4-Phenylthiosemicarbazide">4-PTSC</a></li> <li><a href="/wiki/Acylhydrazine" class="mw-redirect" title="Acylhydrazine">Acylhydrazine</a></li> <li><a href="/wiki/Adipic_acid_dihydrazide" title="Adipic acid dihydrazide">ADH</a></li> <li><a href="/wiki/Adjudin" title="Adjudin">Adjudin</a></li> <li><a href="/wiki/Agaritine" title="Agaritine">Agaritine</a></li> <li><a href="/wiki/Benmoxin" title="Benmoxin">Benmoxin</a></li> <li><a href="/wiki/Cadralazine" title="Cadralazine">Cadralazine</a></li> <li><a href="/wiki/Carbazide" title="Carbazide">Carbazide</a></li> <li><a href="/wiki/Carbidopa" title="Carbidopa">Carbidopa</a></li> <li><a href="/wiki/Carbohydrazide" title="Carbohydrazide">Carbohydrazide</a></li> <li><a href="/wiki/Daminozide" title="Daminozide">Daminozide</a></li> <li><a href="/wiki/Dihydralazine" title="Dihydralazine">Dihydralazine</a></li> <li><a href="/wiki/2,4-Dinitrophenylhydrazine" title="2,4-Dinitrophenylhydrazine">DNPH</a></li> <li><a href="/wiki/Endralazine" title="Endralazine">Endralazine</a></li> <li><a href="/wiki/Gyromitrin" title="Gyromitrin">Gyromitrin</a></li> <li><a href="/wiki/HBT_(explosive)" title="HBT (explosive)">HBT</a></li> <li><a href="/wiki/Hydralazine" title="Hydralazine">Hydralazine</a></li> <li><a href="/wiki/Hydrazide" title="Hydrazide">Hydrazide</a></li> <li><a href="/wiki/Hydrazine" title="Hydrazine">Hydrazine</a></li> <li><a href="/wiki/Hydrazone" title="Hydrazone">Hydrazone</a></li> <li><a href="/wiki/Iproclozide" title="Iproclozide">Iproclozide</a></li> <li><a href="/wiki/Iproniazid" title="Iproniazid">Iproniazid</a></li> <li><a href="/wiki/Isocarboxazid" title="Isocarboxazid">Isocarboxazid</a></li> <li><a class="mw-selflink selflink">Isoniazid</a></li> <li><a href="/wiki/Mebanazine" title="Mebanazine">Mebanazine</a></li> <li><a href="/wiki/Metfendrazine" title="Metfendrazine">Metfendrazine</a></li> <li><a href="/wiki/Monomethylhydrazine" title="Monomethylhydrazine">MMH</a></li> <li><a href="/wiki/Nialamide" title="Nialamide">Nialamide</a></li> <li><a href="/wiki/Octamoxin" title="Octamoxin">Octamoxin</a></li> <li><a href="/wiki/Phenylethylidenehydrazine" title="Phenylethylidenehydrazine">PEH</a></li> <li><a href="/wiki/Phenelzine" title="Phenelzine">Phenelzine</a></li> <li><a href="/wiki/Pheniprazine" title="Pheniprazine">Pheniprazine</a></li> <li><a href="/wiki/Phenoxypropazine" title="Phenoxypropazine">Phenoxypropazine</a></li> <li><a href="/wiki/Phenylhydrazine" title="Phenylhydrazine">Phenylhydrazine</a></li> <li><a href="/wiki/Pildralazine" title="Pildralazine">Pildralazine</a></li> <li><a href="/wiki/Pimagedine" title="Pimagedine">Pimagedine</a></li> <li><a href="/wiki/Pivalylbenzhydrazine" class="mw-redirect" title="Pivalylbenzhydrazine">Pivalylbenzhydrazine</a></li> <li><a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a></li> <li><a href="/wiki/Safrazine" 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