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<span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Medical_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Medical_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Medical uses</span> </div> </a> <ul id="toc-Medical_uses-sublist" class="vector-toc-list"> </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">4</span> <span>Side effects</span> </div> </a> <button aria-controls="toc-Side_effects-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 Side effects subsection</span> </button> <ul id="toc-Side_effects-sublist" class="vector-toc-list"> <li id="toc-Allergic_hypersensitivity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Allergic_hypersensitivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Allergic hypersensitivity</span> </div> </a> <ul id="toc-Allergic_hypersensitivity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-MTT_side_chain" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#MTT_side_chain"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>MTT side chain</span> </div> </a> <ul id="toc-MTT_side_chain-sublist" class="vector-toc-list"> </ul> </li> </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-Resistance" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Resistance"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Resistance</span> </div> </a> <ul id="toc-Resistance-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Classification" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Classification"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Classification</span> </div> </a> <button aria-controls="toc-Classification-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 Classification subsection</span> </button> <ul id="toc-Classification-sublist" class="vector-toc-list"> <li id="toc-First_generation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#First_generation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>First generation</span> </div> </a> <ul id="toc-First_generation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Second_generation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Second_generation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Second generation</span> </div> </a> <ul id="toc-Second_generation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Third_generation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Third_generation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Third generation</span> </div> </a> <ul id="toc-Third_generation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fourth_generation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fourth_generation"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.4</span> <span>Fourth generation</span> </div> </a> <ul id="toc-Fourth_generation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_generations" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Further_generations"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.5</span> <span>Further generations</span> </div> </a> <ul id="toc-Further_generations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Naming" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Naming"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.6</span> <span>Naming</span> </div> </a> <ul id="toc-Naming-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Activity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.7</span> <span>Activity</span> </div> </a> <ul id="toc-Activity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Overview_table" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Overview_table"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.8</span> <span>Overview table</span> </div> </a> <ul id="toc-Overview_table-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-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">10</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" ><span class="vector-icon mw-ui-icon-listBullet mw-ui-icon-wikimedia-listBullet"></span> <span class="vector-dropdown-label-text">Toggle the table of contents</span> </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Cephalosporin</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 44 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-44" 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">44 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%B3%D9%8A%D9%81%D8%A7%D9%84%D9%88%D8%B3%D8%A8%D9%88%D8%B1%D9%8A%D9%86" title="سيفالوسبورين – Arabic" lang="ar" hreflang="ar" data-title="سيفالوسبورين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/Sefalosporinl%C9%99r" title="Sefalosporinlər – Azerbaijani" lang="az" hreflang="az" data-title="Sefalosporinlər" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target"><span>Azərbaycanca</span></a></li><li class="interlanguage-link interwiki-bn mw-list-item"><a href="https://bn.wikipedia.org/wiki/%E0%A6%B8%E0%A7%87%E0%A6%AB%E0%A6%BE%E0%A6%B2%E0%A7%8B%E0%A6%B8%E0%A7%8D%E0%A6%AA%E0%A7%8B%E0%A6%B0%E0%A6%BF%E0%A6%A8" title="সেফালোস্পোরিন – Bangla" lang="bn" hreflang="bn" data-title="সেফালোস্পোরিন" data-language-autonym="বাংলা" data-language-local-name="Bangla" class="interlanguage-link-target"><span>বাংলা</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Cefalosporina" title="Cefalosporina – Catalan" lang="ca" hreflang="ca" data-title="Cefalosporina" 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/Cefalosporin" title="Cefalosporin – Czech" lang="cs" hreflang="cs" data-title="Cefalosporin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Cefalosporin" title="Cefalosporin – Danish" lang="da" hreflang="da" data-title="Cefalosporin" 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/Cephalosporine" title="Cephalosporine – German" lang="de" hreflang="de" data-title="Cephalosporine" 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%9A%CE%B5%CF%86%CE%B1%CE%BB%CE%BF%CF%83%CF%80%CE%BF%CF%81%CE%AF%CE%BD%CE%B5%CF%82" title="Κεφαλοσπορίνες – Greek" lang="el" hreflang="el" data-title="Κεφαλοσπορίνες" 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/Cefalosporina" title="Cefalosporina – Spanish" lang="es" hreflang="es" data-title="Cefalosporina" 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/Zefalosporina" title="Zefalosporina – Basque" lang="eu" hreflang="eu" data-title="Zefalosporina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B3%D9%81%D8%A7%D9%84%D9%88%D8%B3%D9%BE%D9%88%D8%B1%DB%8C%D9%86" title="سفالوسپورین – Persian" lang="fa" hreflang="fa" data-title="سفالوسپورین" 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/C%C3%A9phalosporine" title="Céphalosporine – French" lang="fr" hreflang="fr" data-title="Céphalosporine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%84%B8%ED%8C%94%EB%A1%9C%EC%8A%A4%ED%8F%AC%EB%A6%B0" title="세팔로스포린 – Korean" lang="ko" hreflang="ko" data-title="세팔로스포린" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%91%D5%A5%D6%86%D5%A1%D5%AC%D5%B8%D5%BD%D5%BA%D5%B8%D6%80%D5%AB%D5%B6%D5%B6%D5%A5%D6%80" title="Ցեֆալոսպորիններ – Armenian" lang="hy" hreflang="hy" data-title="Ցեֆալոսպորիններ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B8%E0%A5%87%E0%A4%AB%E0%A4%BE%E0%A4%B2%E0%A5%8B%E0%A4%B8%E0%A5%8D%E0%A4%AA%E0%A5%8B%E0%A4%B0%E0%A4%BF%E0%A4%A8" title="सेफालोस्पोरिन – Hindi" lang="hi" hreflang="hi" data-title="सेफालोस्पोरिन" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target"><span>हिन्दी</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Cefalosporin" title="Cefalosporin – Croatian" lang="hr" hreflang="hr" data-title="Cefalosporin" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Sefalosporin" title="Sefalosporin – Indonesian" lang="id" hreflang="id" data-title="Sefalosporin" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/Kefal%C3%B3spor%C3%ADn" title="Kefalósporín – Icelandic" lang="is" hreflang="is" data-title="Kefalósporín" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target"><span>Íslenska</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cefalosporine" title="Cefalosporine – Italian" lang="it" hreflang="it" data-title="Cefalosporine" 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%A6%D7%A4%D7%9C%D7%95%D7%A1%D7%A4%D7%95%D7%A8%D7%99%D7%9F" title="צפלוספורין – Hebrew" lang="he" hreflang="he" data-title="צפלוספורין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-la mw-list-item"><a href="https://la.wikipedia.org/wiki/Cephalosporinum" title="Cephalosporinum – Latin" lang="la" hreflang="la" data-title="Cephalosporinum" data-language-autonym="Latina" data-language-local-name="Latin" class="interlanguage-link-target"><span>Latina</span></a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%A6%D0%B5%D1%84%D0%B0%D0%BB%D0%BE%D1%81%D0%BF%D0%BE%D1%80%D0%B8%D0%BD%D0%B8" title="Цефалоспорини – Macedonian" lang="mk" hreflang="mk" data-title="Цефалоспорини" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target"><span>Македонски</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Cefalosporines" title="Cefalosporines – Dutch" lang="nl" hreflang="nl" data-title="Cefalosporines" 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%BB%E3%83%95%E3%82%A1%E3%83%AD%E3%82%B9%E3%83%9D%E3%83%AA%E3%83%B3" title="セファロスポリン – Japanese" lang="ja" hreflang="ja" data-title="セファロスポリン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Sefalosporinlar" title="Sefalosporinlar – Uzbek" lang="uz" hreflang="uz" data-title="Sefalosporinlar" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target"><span>Oʻzbekcha / ўзбекча</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Cefalosporyny" title="Cefalosporyny – Polish" lang="pl" hreflang="pl" data-title="Cefalosporyny" 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/Cefalosporina" title="Cefalosporina – Portuguese" lang="pt" hreflang="pt" data-title="Cefalosporina" 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/Cefalosporin%C4%83" title="Cefalosporină – Romanian" lang="ro" hreflang="ro" data-title="Cefalosporină" 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%A6%D0%B5%D1%84%D0%B0%D0%BB%D0%BE%D1%81%D0%BF%D0%BE%D1%80%D0%B8%D0%BD%D1%8B" title="Цефалоспорины – Russian" lang="ru" hreflang="ru" data-title="Цефалоспорины" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Cephalosporin" title="Cephalosporin – Simple English" lang="en-simple" hreflang="en-simple" data-title="Cephalosporin" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Cefalospor%C3%ADn" title="Cefalosporín – Slovak" lang="sk" hreflang="sk" data-title="Cefalosporín" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target"><span>Slovenčina</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Cefalosporini" title="Cefalosporini – Slovenian" lang="sl" hreflang="sl" data-title="Cefalosporini" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%D8%B3%DB%8C%D9%81%D8%A7%D9%84%DB%86%D8%B3%D9%BE%DB%86%DA%95%DB%8C%D9%86" title="سیفالۆسپۆڕین – Central Kurdish" lang="ckb" hreflang="ckb" data-title="سیفالۆسپۆڕین" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target"><span>کوردی</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%A6%D0%B5%D1%84%D0%B0%D0%BB%D0%BE%D1%81%D0%BF%D0%BE%D1%80%D0%B8%D0%BD%D0%B8" title="Цефалоспорини – Serbian" lang="sr" hreflang="sr" data-title="Цефалоспорини" 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/Cefalosporin" title="Cefalosporin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Cefalosporin" 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/Kefalosporiinit" title="Kefalosporiinit – Finnish" lang="fi" hreflang="fi" data-title="Kefalosporiinit" 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/Cefalosporiner" title="Cefalosporiner – Swedish" lang="sv" hreflang="sv" data-title="Cefalosporiner" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li 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href="/wiki/Cyclosporin" class="mw-redirect" title="Cyclosporin">cyclosporin</a>.</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Class of pharmaceutical drugs</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox"><tbody><tr><th colspan="2" class="infobox-above" style="background-color: #ddbbee">Cephalosporin</th></tr><tr><td colspan="2" class="infobox-subheader"><i><a href="/wiki/Drug_class" title="Drug class">Drug class</a></i></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size skin-invert-image" typeof="mw:File/Frameless"><a href="/wiki/File:Cephalosporin_core_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Cephalosporin_core_structure.svg/280px-Cephalosporin_core_structure.svg.png" decoding="async" width="280" height="194" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Cephalosporin_core_structure.svg/420px-Cephalosporin_core_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a6/Cephalosporin_core_structure.svg/560px-Cephalosporin_core_structure.svg.png 2x" data-file-width="512" data-file-height="355" /></a></span><div class="infobox-caption">Core structure of the cephalosporins</div></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Class identifiers</th></tr><tr><th scope="row" class="infobox-label">Use</th><td class="infobox-data">Bacterial infection</td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><a href="/wiki/ATC_code_J01D" class="mw-redirect" title="ATC code J01D">J01D</a></td></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Biological_target" title="Biological target">Biological target</a></th><td class="infobox-data"><a href="/wiki/Penicillin_binding_proteins" class="mw-redirect" title="Penicillin binding proteins">Penicillin binding proteins</a></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Clinical data</th></tr><tr><th scope="row" class="infobox-label"><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/drug-class/cephalosporins.html">Drug Classes</a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">External links</th></tr><tr><th scope="row" class="infobox-label"><a href="/wiki/Medical_Subject_Headings" title="Medical Subject Headings">MeSH</a></th><td class="infobox-data"><span class="reflink plainlinks nourlexpansion"><a rel="nofollow" class="external text" href="https://meshb.nlm.nih.gov/record/ui?ui=D002511">D002511</a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background: #e8e8e8;">Legal status</th></tr><tr><td colspan="2" class="infobox-below" style="background: #e8e8e8; text-align: center"><a href="https://www.wikidata.org/wiki/Q271021" class="extiw" title="d:Q271021">In Wikidata</a></td></tr></tbody></table> <figure class="mw-default-size skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Cephalosporins_Generation1.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Cephalosporins_Generation1.svg/220px-Cephalosporins_Generation1.svg.png" decoding="async" width="220" height="591" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/be/Cephalosporins_Generation1.svg/330px-Cephalosporins_Generation1.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/be/Cephalosporins_Generation1.svg/440px-Cephalosporins_Generation1.svg.png 2x" data-file-width="744" data-file-height="2000" /></a><figcaption>Structure of the classical cephalosporins</figcaption></figure> <p>The <b>cephalosporins</b> (sg. <span class="rt-commentedText nowrap"><span class="IPA nopopups noexcerpt" lang="en-fonipa"><a href="/wiki/Help:IPA/English" title="Help:IPA/English">/<span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'s' in 'sigh'">s</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span><span title="'f' in 'find'">f</span><span title="/ə/: 'a' in 'about'">ə</span><span title="'l' in 'lie'">l</span><span title="/ə/: 'a' in 'about'">ə</span><span title="/ˈ/: primary stress follows">ˈ</span><span title="'s' in 'sigh'">s</span><span title="'p' in 'pie'">p</span><span title="/ɔːr/: 'ar' in 'war'">ɔːr</span><span title="/ɪ/: 'i' in 'kit'">ɪ</span><span title="'n' in 'nigh'">n</span></span>,<span class="wrap"> </span><span style="border-bottom:1px dotted"><span title="/ˌ/: secondary stress follows">ˌ</span><span title="'k' in 'kind'">k</span><span title="/ɛ/: 'e' in 'dress'">ɛ</span></span>-,<span class="wrap"> </span>-<span style="border-bottom:1px dotted"><span title="'l' in 'lie'">l</span><span title="/oʊ/: 'o' in 'code'">oʊ</span></span>-/</a></span></span><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>) are a class of <a href="/wiki/%CE%92-lactam_antibiotic" class="mw-redirect" title="Β-lactam antibiotic">β-lactam antibiotics</a> originally derived from the <a href="/wiki/Fungus" title="Fungus">fungus</a> <i><a href="/wiki/Acremonium" title="Acremonium">Acremonium</a></i>, which was previously known as <i>Cephalosporium</i>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Together with <a href="/wiki/Cephamycin" title="Cephamycin">cephamycins</a>, they constitute a subgroup of β-lactam antibiotics called <a href="/wiki/Cephem" title="Cephem">cephems</a>. Cephalosporins were discovered in 1945, and first sold in 1964.<sup id="cite_ref-4" class="reference"><a href="#cite_note-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="Discovery">Discovery</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=1" title="Edit section: Discovery"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The <a href="/wiki/Aerobic_organism" title="Aerobic organism">aerobic</a> <a href="/wiki/Mold" title="Mold">mold</a> which <a href="https://en.wiktionary.org/wiki/yield" class="extiw" title="wikt:yield">yielded</a> <a href="/wiki/Cephalosporin_C" title="Cephalosporin C">cephalosporin C</a> was found in the sea near a <a href="/w/index.php?title=Sewage_outfall&action=edit&redlink=1" class="new" title="Sewage outfall (page does not exist)">sewage outfall</a> in <a href="/w/index.php?title=Su_Siccu&action=edit&redlink=1" class="new" title="Su Siccu (page does not exist)">Su Siccu</a>, by <a href="/wiki/Cagliari" title="Cagliari">Cagliari</a> <a href="/wiki/Harbour" class="mw-redirect" title="Harbour">harbour</a> in <a href="/wiki/Sardinia" title="Sardinia">Sardinia</a>, by the <a href="/wiki/Italians" title="Italians">Italian</a> <a href="/wiki/Pharmacologist" class="mw-redirect" title="Pharmacologist">pharmacologist</a> <a href="/wiki/Giuseppe_Brotzu" title="Giuseppe Brotzu">Giuseppe Brotzu</a> in July 1945.<sup id="cite_ref-HoMBRG_5-0" class="reference"><a href="#cite_note-HoMBRG-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure">Structure</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=2" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cephalosporin contains a 6-membered dihydrothiazine ring. Substitutions at position 3 generally affect pharmacology; substitutions at position 7 affect antibacterial activity, but these cases are not always true.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <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=Cephalosporin&action=edit&section=3" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cephalosporins can be indicated for the <a href="/wiki/Prophylaxis" class="mw-redirect" title="Prophylaxis">prophylaxis</a> and treatment of infections caused by <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> susceptible to this particular form of antibiotic. First-generation cephalosporins are active predominantly against <a href="/wiki/Gram-positive" class="mw-redirect" title="Gram-positive">Gram-positive</a> bacteria, such as <i><a href="/wiki/Staphylococcus" title="Staphylococcus">Staphylococcus</a></i> and <i><a href="/wiki/Streptococcus" title="Streptococcus">Streptococcus</a></i>.<sup id="cite_ref-:0_7-0" class="reference"><a href="#cite_note-:0-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> They are therefore used mostly for skin and soft tissue infections and the prevention of hospital-acquired surgical infections.<sup id="cite_ref-:31424895_8-0" class="reference"><a href="#cite_note-:31424895-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Successive generations of cephalosporins have increased activity against <a href="/wiki/Gram-negative" class="mw-redirect" title="Gram-negative">Gram-negative</a> bacteria, albeit often with reduced activity against Gram-positive organisms.<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><p>The antibiotic may be used for patients who are allergic to penicillin due to the different <a href="/wiki/%CE%92-lactam_antibiotic" class="mw-redirect" title="Β-lactam antibiotic">β-lactam antibiotic</a> structure. The drug is able to be excreted in the urine.<sup id="cite_ref-:0_7-1" class="reference"><a href="#cite_note-:0-7"><span class="cite-bracket">[</span>7<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=Cephalosporin&action=edit&section=4" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Common <a href="/wiki/Adverse_drug_reaction" title="Adverse drug reaction">adverse drug reactions</a> (ADRs) (≥ 1% of patients) associated with the cephalosporin therapy include: diarrhea, nausea, rash, electrolyte disturbances, and pain and inflammation at injection site. Infrequent ADRs (0.1–1% of patients) include vomiting, headache, dizziness, oral and vaginal <a href="/wiki/Candidiasis" title="Candidiasis">candidiasis</a>, <a href="/wiki/Pseudomembranous_colitis" class="mw-redirect" title="Pseudomembranous colitis">pseudomembranous colitis</a>, <a href="/wiki/Superinfection" title="Superinfection">superinfection</a>, <a href="/wiki/Eosinophilia" title="Eosinophilia">eosinophilia</a>, <a href="/wiki/Nephrotoxicity" title="Nephrotoxicity">nephrotoxicity</a>, <a href="/wiki/Neutropenia" title="Neutropenia">neutropenia</a>, <a href="/wiki/Thrombocytopenia" title="Thrombocytopenia">thrombocytopenia</a>, and <a href="/wiki/Fever" title="Fever">fever</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="Allergic_hypersensitivity">Allergic hypersensitivity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=5" title="Edit section: Allergic hypersensitivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The commonly quoted figure of 10% of patients with allergic hypersensitivity to <a href="/wiki/Penicillin" title="Penicillin">penicillins</a> and/or <a href="/wiki/Carbapenem" title="Carbapenem">carbapenems</a> also having cross-reactivity with cephalosporins originated from a 1975 study looking at the original cephalosporins,<sup id="cite_ref-pmid1201975_9-0" class="reference"><a href="#cite_note-pmid1201975-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> and subsequent "safety first" policy meant this was widely quoted and assumed to apply to all members of the group.<sup id="cite_ref-Pegler_10-0" class="reference"><a href="#cite_note-Pegler-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Hence, it was commonly stated that they are contraindicated in patients with a history of severe, immediate allergic reactions (<a href="/wiki/Urticaria" class="mw-redirect" title="Urticaria">urticaria</a>, <a href="/wiki/Anaphylaxis" title="Anaphylaxis">anaphylaxis</a>, <a href="/wiki/Interstitial_nephritis" title="Interstitial nephritis">interstitial nephritis</a>, etc.) to penicillins or carbapenems.<sup id="cite_ref-AMH2006_11-0" class="reference"><a href="#cite_note-AMH2006-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>The contraindication, however, should be viewed in the light of recent epidemiological work suggesting, for many second-generation (or later) cephalosporins, the cross-reactivity rate with penicillin is much lower, having no significantly increased risk of reactivity over the first generation based on the studies examined.<sup id="cite_ref-Pegler_10-1" class="reference"><a href="#cite_note-Pegler-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid16451776_12-0" class="reference"><a href="#cite_note-pmid16451776-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/British_National_Formulary" title="British National Formulary">British National Formulary</a> previously issued blanket warnings of 10% cross-reactivity, but, since the September 2008 edition, suggests, in the absence of suitable alternatives, oral <a href="/wiki/Cefixime" title="Cefixime">cefixime</a> or cefuroxime and injectable cefotaxime, <a href="/wiki/Ceftazidime" title="Ceftazidime">ceftazidime</a>, and ceftriaxone can be used with caution, but the use of <a href="/wiki/Cefaclor" title="Cefaclor">cefaclor</a>, <a href="/wiki/Cefadroxil" title="Cefadroxil">cefadroxil</a>, <a href="/wiki/Cefalexin" title="Cefalexin">cefalexin</a>, and <a href="/wiki/Cefradine" title="Cefradine">cefradine</a> should be avoided.<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> A 2012 literature review similarly finds that the risk is negligible with third- and fourth-generation cephalosporins. The risk with first-generation cephalosporins having similar R1 sidechains was also found to be overestimated, with the real value closer to 1%.<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> <div class="mw-heading mw-heading3"><h3 id="MTT_side_chain">MTT side chain</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=6" title="Edit section: MTT side chain"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Disulfiram-like_drug" title="Disulfiram-like drug">Disulfiram-like drug</a></div> <div class="skin-invert-image"> <style data-mw-deduplicate="TemplateStyles:r1237032888/mw-parser-output/.tmulti">.mw-parser-output .tmulti .multiimageinner{display:flex;flex-direction:column}.mw-parser-output .tmulti .trow{display:flex;flex-direction:row;clear:left;flex-wrap:wrap;width:100%;box-sizing:border-box}.mw-parser-output .tmulti .tsingle{margin:1px;float:left}.mw-parser-output .tmulti .theader{clear:both;font-weight:bold;text-align:center;align-self:center;background-color:transparent;width:100%}.mw-parser-output .tmulti .thumbcaption{background-color:transparent}.mw-parser-output .tmulti .text-align-left{text-align:left}.mw-parser-output .tmulti .text-align-right{text-align:right}.mw-parser-output .tmulti .text-align-center{text-align:center}@media all and (max-width:720px){.mw-parser-output .tmulti .thumbinner{width:100%!important;box-sizing:border-box;max-width:none!important;align-items:center}.mw-parser-output .tmulti .trow{justify-content:center}.mw-parser-output .tmulti .tsingle{float:none!important;max-width:100%!important;box-sizing:border-box;text-align:center}.mw-parser-output .tmulti .tsingle .thumbcaption{text-align:left}.mw-parser-output .tmulti .trow>.thumbcaption{text-align:center}}@media screen{html.skin-theme-clientpref-night .mw-parser-output .tmulti .multiimageinner img{background-color:white}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .tmulti .multiimageinner img{background-color:white}}</style><div class="thumb tmulti tright"><div class="thumbinner multiimageinner" style="width:212px;max-width:212px"><div class="trow"><div class="theader">MTT and MTDT sidechains</div></div><div class="trow"><div class="tsingle" style="width:113px;max-width:113px"><div class="thumbimage" style="height:84px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:N-methylthiotetrazole.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/N-methylthiotetrazole.svg/111px-N-methylthiotetrazole.svg.png" decoding="async" width="111" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1d/N-methylthiotetrazole.svg/167px-N-methylthiotetrazole.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1d/N-methylthiotetrazole.svg/222px-N-methylthiotetrazole.svg.png 2x" data-file-width="209" data-file-height="160" /></a></span></div><div class="thumbcaption">Methylthiotetrazole</div></div><div class="tsingle" style="width:95px;max-width:95px"><div class="thumbimage" style="height:84px;overflow:hidden"><span typeof="mw:File"><a href="/wiki/File:N-methylthiodioxotriazine.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/N-methylthiodioxotriazine.svg/93px-N-methylthiodioxotriazine.svg.png" decoding="async" width="93" height="85" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/17/N-methylthiodioxotriazine.svg/140px-N-methylthiodioxotriazine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/17/N-methylthiodioxotriazine.svg/186px-N-methylthiodioxotriazine.svg.png 2x" data-file-width="333" data-file-height="303" /></a></span></div><div class="thumbcaption">Methylthiodioxotriazine</div></div></div></div></div></div> <p>Several cephalosporins are associated with <a href="/wiki/Hypoprothrombinemia" title="Hypoprothrombinemia">hypoprothrombinemia</a> and a <a href="/wiki/Disulfiram" title="Disulfiram">disulfiram</a>-like reaction with ethanol.<sup id="cite_ref-pmid3593530_15-0" class="reference"><a href="#cite_note-pmid3593530-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid3350995_16-0" class="reference"><a href="#cite_note-pmid3350995-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> These include <a href="/wiki/Latamoxef" title="Latamoxef">latamoxef</a> (<a href="/wiki/Moxalactam" class="mw-redirect" title="Moxalactam">moxalactam</a>), <a href="/wiki/Cefmenoxime" title="Cefmenoxime">cefmenoxime</a>, <a href="/wiki/Cefoperazone" title="Cefoperazone">cefoperazone</a>, <a href="/wiki/Cefamandole" title="Cefamandole">cefamandole</a>, <a href="/wiki/Cefmetazole" title="Cefmetazole">cefmetazole</a>, and <a href="/wiki/Cefotetan" title="Cefotetan">cefotetan</a>. This is thought to be due to the <a href="/w/index.php?title=Methylthiotetrazole&action=edit&redlink=1" class="new" title="Methylthiotetrazole (page does not exist)">methylthiotetrazole</a> side-chain of these cephalosporins, which blocks the enzyme <a href="/wiki/Vitamin_K_epoxide_reductase" title="Vitamin K epoxide reductase">vitamin K epoxide reductase</a> (likely causing hypothrombinemia) and <a href="/wiki/Aldehyde_dehydrogenase" title="Aldehyde dehydrogenase">aldehyde dehydrogenase</a> (causing alcohol intolerance).<sup id="cite_ref-Goldfrank_17-0" class="reference"><a href="#cite_note-Goldfrank-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> Thus, consumption of alcohol after taking these cephalosporin orally or intravenously is contraindicated, and in severe cases can lead to death.<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 methylthiodioxotriazine sidechain found in <a href="/wiki/Ceftriaxone" title="Ceftriaxone">ceftriaxone</a> has a similar effect. Cephalosporins without these structural elements are believed to be safe with alcohol.<sup id="cite_ref-Mergenhagen2020_19-0" class="reference"><a href="#cite_note-Mergenhagen2020-19"><span class="cite-bracket">[</span>19<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=Cephalosporin&action=edit&section=7" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cephalosporins are <a href="/wiki/Bactericidal" class="mw-redirect" title="Bactericidal">bactericidal</a> and, like other β-lactam antibiotics, disrupt the synthesis of the <a href="/wiki/Peptidoglycan" title="Peptidoglycan">peptidoglycan</a> layer forming the bacterial <a href="/wiki/Cell_wall" title="Cell wall">cell wall</a>. The peptidoglycan layer is important for cell wall structural integrity. The final transpeptidation step in the synthesis of the peptidoglycan is facilitated by <a href="/wiki/Penicillin-binding_protein" class="mw-redirect" title="Penicillin-binding protein">penicillin-binding proteins</a> (PBPs). PBPs bind to the D-Ala-D-Ala at the end of muropeptides (peptidoglycan precursors) to crosslink the peptidoglycan. Beta-lactam antibiotics mimic the D-Ala-D-Ala site, thereby irreversibly inhibiting PBP crosslinking of peptidoglycan.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Resistance">Resistance</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=8" title="Edit section: Resistance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Antimicrobial_resistance" title="Antimicrobial resistance">Resistance</a> to cephalosporin antibiotics can involve either reduced affinity of existing PBP components or the acquisition of a supplementary β-lactam-insensitive PBP. Compared to other β-lactam antibiotics (such as penicillins), they are less susceptible to <a href="/wiki/%CE%92-lactamase" class="mw-redirect" title="Β-lactamase">β-lactamases</a>. Currently, some <i><a href="/wiki/Citrobacter_freundii" title="Citrobacter freundii">Citrobacter freundii</a>, <a href="/wiki/Enterobacter_cloacae" title="Enterobacter cloacae">Enterobacter cloacae</a></i>, <i><a href="/wiki/Neisseria_gonorrhoeae" title="Neisseria gonorrhoeae">Neisseria gonorrhoeae</a></i>, and <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a></i> strains are resistant to cephalosporins. Some <i><a href="/wiki/Morganella_morganii" title="Morganella morganii">Morganella morganii</a></i>, <i><a href="/wiki/Proteus_vulgaris" title="Proteus vulgaris">Proteus vulgaris</a>, <a href="/wiki/Providencia_rettgeri" title="Providencia rettgeri">Providencia rettgeri</a>, <a href="/wiki/Pseudomonas_aeruginosa" title="Pseudomonas aeruginosa">Pseudomonas aeruginosa</a></i>, <i><a href="/wiki/Serratia_marcescens" title="Serratia marcescens">Serratia marcescens</a></i> and <i><a href="/wiki/Klebsiella_pneumoniae" title="Klebsiella pneumoniae">Klebsiella pneumoniae</a></i> strains have also developed resistance to cephalosporins to varying degrees.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Classification">Classification</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=9" title="Edit section: Classification"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The cephalosporin nucleus can be modified to gain different properties. Cephalosporins are sometimes grouped into "generations" by their <a href="/wiki/Antimicrobial" title="Antimicrobial">antimicrobial</a> properties.<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. (March 2023)">citation needed</span></a></i>]</sup> </p><p>The first cephalosporins were designated first-generation cephalosporins, whereas, later, more extended-<a href="/wiki/Spectrum#Biological_science" title="Spectrum">spectrum</a> cephalosporins were classified as second-generation cephalosporins. Each newer generation has significantly greater Gram-negative antimicrobial properties than the preceding generation, in most cases with decreased activity against Gram-positive organisms. Fourth-generation cephalosporins, however, have true broad-spectrum activity.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>The classification of cephalosporins into "generations" is commonly practised, although the exact categorization is often imprecise. For example, the fourth generation of cephalosporins is not recognized as such in Japan.<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. (September 2010)">citation needed</span></a></i>]</sup> In Japan, cefaclor is classed as a first-generation cephalosporin, though in the United States it is a second-generation one; and cefbuperazone, cefminox, and cefotetan are classed as second-generation cephalosporins. </p> <div class="mw-heading mw-heading3"><h3 id="First_generation">First generation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=10" title="Edit section: First generation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Cefalotin" title="Cefalotin">Cefalotin</a>, <a href="/wiki/Cefazolin" title="Cefazolin">cefazolin</a>, <a href="/wiki/Cefalexin" title="Cefalexin">cefalexin</a>, <a href="/wiki/Cefapirin" title="Cefapirin">cefapirin</a>, <a href="/wiki/Cefradine" title="Cefradine">cefradine</a>, and <a href="/wiki/Cefadroxil" title="Cefadroxil">cefadroxil</a> are drugs belonging to this group. </p> <div class="mw-heading mw-heading3"><h3 id="Second_generation">Second generation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=11" title="Edit section: Second generation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Cefoxitin" title="Cefoxitin">Cefoxitin</a>, <a href="/wiki/Cefuroxime" title="Cefuroxime">cefuroxime</a>, <a href="/wiki/Cefaclor" title="Cefaclor">cefaclor</a>, <a href="/wiki/Cefprozil" title="Cefprozil">cefprozil</a>, and <a href="/wiki/Cefmetazole" title="Cefmetazole">cefmetazole</a> are classed as second-generation cephems. </p> <div class="mw-heading mw-heading3"><h3 id="Third_generation">Third generation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=12" title="Edit section: Third generation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Ceftazidime" title="Ceftazidime">Ceftazidime</a>, <a href="/wiki/Ceftriaxone" title="Ceftriaxone">ceftriaxone</a>, and <a href="/wiki/Cefotaxime" title="Cefotaxime">cefotaxime</a> are classed as third-generation cephalosporins. Flomoxef and latamoxef are in a new, related class called <a href="/wiki/Oxacephem" title="Oxacephem">oxacephems</a>.<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> <div class="mw-heading mw-heading3"><h3 id="Fourth_generation">Fourth generation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=13" title="Edit section: Fourth generation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Drugs included in this group are <a href="/wiki/Cefepime" title="Cefepime">cefepime</a> and <a href="/wiki/Cefpirome" title="Cefpirome">cefpirome</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Further_generations">Further generations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=14" title="Edit section: Further generations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some state that cephalosporins can be divided into five or even six generations, although the usefulness of this organization system is of limited clinical relevance.<sup id="cite_ref-urlCase_Based_Pediatrics_Chapter_25-0" class="reference"><a href="#cite_note-urlCase_Based_Pediatrics_Chapter-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Naming">Naming</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=15" title="Edit section: Naming"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Most first-generation cephalosporins were originally spelled "ceph-" in English-speaking countries. This continues to be the preferred spelling in the United States, Australia, and New Zealand, while European countries (including the United Kingdom) have adopted the <a href="/wiki/International_Nonproprietary_Name" class="mw-redirect" title="International Nonproprietary Name">International Nonproprietary Names</a>, which are always spelled "cef-". Newer first-generation cephalosporins and all cephalosporins of later generations are spelled "cef-", even in the United States.<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. (April 2018)">citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Activity">Activity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=16" title="Edit section: Activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>There exist bacteria which cannot be treated with cephalosporins of generations first through fourth:<sup id="cite_ref-:1_26-0" class="reference"><a href="#cite_note-:1-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <ul><li><i><a href="/wiki/Listeria" title="Listeria">Listeria spp.</a></i></li> <li><a href="/wiki/Atypical_pneumonia" title="Atypical pneumonia">Atypicals</a> (including <i><a href="/wiki/Mycoplasma" title="Mycoplasma">Mycoplasma</a></i> and <i><a href="/wiki/Chlamydia" title="Chlamydia">Chlamydia</a></i>)</li> <li><a href="/wiki/Methicillin-resistant_Staphylococcus_aureus" title="Methicillin-resistant Staphylococcus aureus">MRSA</a></li> <li><a href="/wiki/Enterococci" class="mw-redirect" title="Enterococci">Enterococci</a></li></ul> <p>Fifth-generation cephalosporins (e.g. <a href="/wiki/Ceftaroline_fosamil" title="Ceftaroline fosamil">ceftaroline</a>) are effective against MRSA, <i>Listeria</i> <i>spp.</i>, and <i>Enterococcus faecalis</i>.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:1_26-1" class="reference"><a href="#cite_note-:1-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Overview_table">Overview table</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=17" title="Edit section: Overview table"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><span class="anchor" id="generations"></span> </p> <table class="wikitable"> <tbody><tr> <th rowspan="2" class="nowrap ts-vertical-header" style=""><div style=""><style data-mw-deduplicate="TemplateStyles:r1221560606">@supports(writing-mode:vertical-rl){.mw-parser-output .ts-vertical-header{line-height:1;max-width:1em;padding:0.4em;vertical-align:bottom;width:1em}html.client-js .mw-parser-output .sortable:not(.jquery-tablesorter) .ts-vertical-header:not(.unsortable),html.client-js .mw-parser-output .ts-vertical-header.headerSort{background-position:50%.4em;padding-right:0.4em;padding-top:21px}.mw-parser-output .ts-vertical-header.is-valign-top{vertical-align:top}.mw-parser-output .ts-vertical-header.is-valign-middle{vertical-align:middle}.mw-parser-output .ts-vertical-header.is-normal{font-weight:normal}.mw-parser-output .ts-vertical-header>*{display:inline-block;transform:rotate(180deg);writing-mode:vertical-rl}@supports(writing-mode:sideways-lr){.mw-parser-output .ts-vertical-header>*{transform:none;writing-mode:sideways-lr}}}</style>Generation</div> </th> <th colspan="3">Name </th> <th rowspan="2" class="nowrap ts-vertical-header" style=""><div style=""><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1221560606">Approval status</div> </th> <th rowspan="2" class="nowrap ts-vertical-header" style=""><div style=""><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1221560606">Coverage</div> </th> <th rowspan="2">Description </th></tr> <tr> <th><a href="/wiki/International_nonproprietary_name" title="International nonproprietary name">Common</a> </th> <th>Alternate name or spelling </th> <th>Brand </th></tr> <tr> <td colspan="4" style="border-style: none none none none; padding: 0em 0.5em;"><small>(#) = noncephalosporins similar to generation #</small> </td> <td colspan="3" style="border-style: none none none none; padding: 0em 0.5em;"><small>H, <a href="/wiki/Medicine" title="Medicine">human</a>; V, <a href="/wiki/Veterinary" class="mw-redirect" title="Veterinary">veterinary</a>; W, <a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">withdrawn</a>; P, <i><a href="/wiki/Pseudomonas" title="Pseudomonas">Pseudomonas</a></i>; MR, <a href="/wiki/Methicillin-resistant_Staphylococcus_aureus" title="Methicillin-resistant Staphylococcus aureus">methicillin-resistant <i>Staphylococcus aureus</i></a>; An, <a href="/wiki/Anaerobe" class="mw-redirect" title="Anaerobe">anaerobe</a></small> </td></tr> <tr style="border-top: 4px solid darkgray;"> <td rowspan="15" style="vertical-align: top; text-align: center; padding: 2.25em 0.5em;">1 </td> <td><a href="/wiki/Cefalexin" title="Cefalexin">Cefalexin</a></td> <td>cephalexin</td> <td>Keflex</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=cephalexin">H</a> <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=animal&query=cephalexin">V</a></td> <td> </td> <td rowspan="15"><b>Gram-positive:</b> Activity against penicillinase-producing, methicillin-susceptible <a href="/wiki/Staphylococcus" title="Staphylococcus">staphylococci</a> and <a href="/wiki/Streptococcus" title="Streptococcus">streptococci</a> (though they are not the drugs of choice for such infections). No activity against methicillin-resistant staphylococci or <a href="/wiki/Enterococcus" title="Enterococcus">enterococci</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. (April 2018)">citation needed</span></a></i>]</sup> <p><b>Gram-negative:</b> Activity against <i><a href="/wiki/Proteus_(bacterium)" title="Proteus (bacterium)">Proteus mirabilis</a></i>, some <i><a href="/wiki/Escherichia_coli" title="Escherichia coli">Escherichia coli</a></i>, and <i><a href="/wiki/Klebsiella_pneumoniae" title="Klebsiella pneumoniae">Klebsiella pneumoniae</a></i> ("PEcK"), but have no activity against <i><a href="/wiki/Bacteroides_fragilis" title="Bacteroides fragilis">Bacteroides fragilis</a></i>, <i><a href="/wiki/Pseudomonas" title="Pseudomonas">Pseudomonas</a></i>, <i><a href="/wiki/Acinetobacter" title="Acinetobacter">Acinetobacter</a></i>, <i><a href="/wiki/Enterobacter" title="Enterobacter">Enterobacter</a></i>, indole-positive <i><a href="/wiki/Proteus_(bacterium)" title="Proteus (bacterium)">Proteus</a></i>, or <i><a href="/wiki/Serratia" title="Serratia">Serratia</a></i>.<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. (April 2018)">citation needed</span></a></i>]</sup> </p> </td></tr> <tr> <td><a href="/wiki/Cefadroxil" title="Cefadroxil">Cefadroxil</a></td> <td>cefadroxyl</td> <td>Duricef</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefadroxil">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefazolin" title="Cefazolin">Cefazolin</a></td> <td>cephazolin</td> <td>Ancef, Kefzol</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefazolin">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefapirin" title="Cefapirin">Cefapirin</a></td> <td>cephapirin</td> <td>Cefadryl</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=animal&query=cephapirin">V</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefacetrile" title="Cefacetrile">Cefacetrile</a></td> <td>cephacetrile</td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefaloglycin" title="Cefaloglycin">Cefaloglycin</a></td> <td>cephaloglycin</td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefalonium" title="Cefalonium">Cefalonium</a></td> <td>cephalonium</td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefaloridine" class="mw-redirect" title="Cefaloridine">Cefaloridine</a></td> <td>cephaloradine</td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefalotin" title="Cefalotin">Cefalotin</a></td> <td>cephalothin</td> <td>Keflin</td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefatrizine" title="Cefatrizine">Cefatrizine</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefazaflur" title="Cefazaflur">Cefazaflur</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefazedone" title="Cefazedone">Cefazedone</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefradine" title="Cefradine">Cefradine</a></td> <td>cephradine</td> <td>Velosef</td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefroxadine" title="Cefroxadine">Cefroxadine</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Ceftezole" title="Ceftezole">Ceftezole</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr style="border-top: 4px solid darkgray;"> <td rowspan="6" style="vertical-align: top; text-align: center; padding: 2.25em 0.5em;">2 </td> <td><a href="/wiki/Cefuroxime" title="Cefuroxime">Cefuroxime</a></td> <td></td> <td>Altacef, Zefu, Zinnat, Zinacef, Ceftin, Biofuroksym,<sup id="cite_ref-biofuroksym_28-0" class="reference"><a href="#cite_note-biofuroksym-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Xorimax</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=cefuroxime">H</a></td> <td> </td> <td rowspan="6"><b>Gram-positive:</b> Less than first-generation.<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. (April 2018)">citation needed</span></a></i>]</sup> <p><b>Gram-negative:</b> Greater than first-generation: HEN <i><a href="/wiki/Haemophilus_influenzae" title="Haemophilus influenzae">Haemophilus influenzae</a></i>, <i><a href="/wiki/Enterobacter_aerogenes" class="mw-redirect" title="Enterobacter aerogenes">Enterobacter aerogenes</a></i> and some <i><a href="/wiki/Neisseria" title="Neisseria">Neisseria</a></i> + the PEcK described above.<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. (April 2018)">citation needed</span></a></i>]</sup> </p> </td></tr> <tr> <td><a href="/wiki/Cefprozil" title="Cefprozil">Cefprozil</a></td> <td>cefproxil</td> <td>Cefzil</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefprozil">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefaclor" title="Cefaclor">Cefaclor</a></td> <td></td> <td>Ceclor, Distaclor, Keflor, Raniclor</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefaclor">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefonicid" title="Cefonicid">Cefonicid</a></td> <td></td> <td>Monocid</td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefuzonam" title="Cefuzonam">Cefuzonam</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefamandole" title="Cefamandole">Cefamandole</a></td> <td></td> <td></td> <td>W</td> <td> </td></tr> <tr> <td rowspan="7" style="vertical-align: top; text-align: center; padding: 2.25em 0.5em;">(2) </td> <td><a href="/wiki/Cefoxitin" title="Cefoxitin">Cefoxitin</a></td> <td></td> <td>Mefoxin</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefoxitin">H</a></td> <td>An </td> <td rowspan="6"><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycins</a> sometimes grouped with second-generation cephalosporins </td></tr> <tr> <td><a href="/wiki/Cefotetan" title="Cefotetan">Cefotetan</a></td> <td></td> <td>Cefotan</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefotetan">H</a></td> <td>An </td></tr> <tr> <td><a href="/wiki/Cefmetazole" title="Cefmetazole">Cefmetazole</a></td> <td></td> <td>Zefazone</td> <td></td> <td>An </td></tr> <tr> <td><a href="/wiki/Cefminox" title="Cefminox">Cefminox</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefbuperazone" title="Cefbuperazone">Cefbuperazone</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefotiam" title="Cefotiam">Cefotiam</a></td> <td></td> <td>Pansporin</td> <td> </td> <td> </td></tr> <tr> <td><a href="/wiki/Loracarbef" title="Loracarbef">Loracarbef</a></td> <td></td> <td>Lorabid</td> <td></td> <td></td> <td>The <a href="/wiki/Carbacephem" title="Carbacephem">carbacephem</a> analog of cefaclor </td></tr> <tr style="border-top: 4px solid darkgray;"> <td rowspan="20" style="vertical-align: top; text-align: center; padding: 2.25em 0.5em;">3 </td> <td><a href="/wiki/Cefdinir" title="Cefdinir">Cefdinir</a></td> <td></td> <td>Sefdin, Zinir, Omnicef, Kefnir</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefdinir">H</a></td> <td> </td> <td rowspan="20"><b>Gram-positive:</b> Some members of this group (in particular, those available in an oral formulation, and those with antipseudomonal activity) have decreased activity against gram-positive organisms. <p>Activity against staphylococci and streptococci is less with the third-generation compounds than with the first- and second-generation compounds.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p><b>Gram-negative:</b> Third-generation cephalosporins have a broad spectrum of activity and further increased activity against gram-negative organisms. They may be particularly useful in treating <a href="/wiki/Nosocomial_infection" class="mw-redirect" title="Nosocomial infection">hospital-acquired infections</a>, although increasing levels of extended-spectrum beta-lactamases are reducing the clinical utility of this class of antibiotics. They are also able to penetrate the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>, making them useful against meningitis caused by pneumococci, meningococci, <i>H. influenzae</i>, and susceptible <i>E. coli</i>, <i>Klebsiella</i>, and penicillin-resistant <i>N. gonorrhoeae</i>. Since August 2012, the third-generation cephalosporin, ceftriaxone, is the only recommended treatment for gonorrhea in the United States (in addition to azithromycin or doxycycline for concurrent <i>Chlamydia</i> treatment). Cefixime is no longer recommended as a first-line treatment due to evidence of decreasing susceptibility.<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> </td></tr> <tr> <td><a href="/wiki/Ceftriaxone" title="Ceftriaxone">Ceftriaxone</a></td> <td></td> <td>Rocephin</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Ceftriaxone">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Ceftazidime" title="Ceftazidime">Ceftazidime</a></td> <td></td> <td>Meezat, Fortum, Fortaz</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Ceftazidime">H</a></td> <td>P </td></tr> <tr> <td><a href="/wiki/Cefixime" title="Cefixime">Cefixime</a></td> <td></td> <td>Fixx, Zifi, Suprax</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefixime">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefpodoxime" title="Cefpodoxime">Cefpodoxime</a></td> <td></td> <td>Vantin, PECEF, Simplicef</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefpodoxime">H</a> <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=animal&query=Cefpodoxime">V</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Ceftiofur" title="Ceftiofur">Ceftiofur</a></td> <td></td> <td>Naxcel, Excenel</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Ceftiofur">H</a> <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=animal&query=Ceftiofur">V</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefotaxime" title="Cefotaxime">Cefotaxime</a></td> <td></td> <td>Claforan</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefotaxime">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Ceftizoxime" title="Ceftizoxime">Ceftizoxime</a></td> <td></td> <td>Cefizox</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Ceftizoxime">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefditoren" title="Cefditoren">Cefditoren</a></td> <td></td> <td>Zostom-O</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefditoren">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Ceftibuten" title="Ceftibuten">Ceftibuten</a></td> <td></td> <td>Cedax</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2dd58c88-142f-41ad-bc31-0a4fff074970">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefovecin" title="Cefovecin">Cefovecin</a></td> <td></td> <td>Convenia</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2daeaf25-f98f-49d3-943c-f604a844d93c">V</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefdaloxime" title="Cefdaloxime">Cefdaloxime</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefcapene" title="Cefcapene">Cefcapene</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefetamet" title="Cefetamet">Cefetamet</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefmenoxime" title="Cefmenoxime">Cefmenoxime</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefodizime" title="Cefodizime">Cefodizime</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefpimizole" title="Cefpimizole">Cefpimizole</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefteram" title="Cefteram">Cefteram</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Ceftiolene" title="Ceftiolene">Ceftiolene</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefoperazone" title="Cefoperazone">Cefoperazone</a></td> <td></td> <td>Cefobid</td> <td>W<sup id="cite_ref-StatPearls_31-0" class="reference"><a href="#cite_note-StatPearls-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup></td> <td>P </td></tr> <tr> <td style="text-align: center;">(3) </td> <td><a href="/wiki/Latamoxef" title="Latamoxef">Latamoxef</a> </td> <td>moxalactam</td> <td></td> <td>W<sup id="cite_ref-StatPearls_31-1" class="reference"><a href="#cite_note-StatPearls-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup></td> <td></td> <td>An <a href="/wiki/Oxacephem" title="Oxacephem">oxacephem</a> sometimes grouped with third-generation cephalosporins </td></tr> <tr style="border-top: 4px solid darkgray;"> <td rowspan="8" style="vertical-align: top; text-align: center; padding: 2.25em 0.5em;">4 </td> <td><a href="/wiki/Cefepime" title="Cefepime">Cefepime</a></td> <td></td> <td>Maxipime</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=human&query=Cefepime">H</a></td> <td>P </td> <td rowspan="8"><b>Gram-positive:</b> They are extended-spectrum agents with similar activity against Gram-positive organisms as first-generation cephalosporins.<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. (April 2018)">citation needed</span></a></i>]</sup> <p><b>Gram-negative:</b> Fourth-generation cephalosporins are <a href="/wiki/Zwitterion" title="Zwitterion">zwitterions</a> that can penetrate the <a href="/wiki/Bacterial_outer_membrane" title="Bacterial outer membrane">outer membrane</a> of Gram-negative bacteria.<sup id="cite_ref-SweetGibbs2009_32-0" class="reference"><a href="#cite_note-SweetGibbs2009-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> They also have a greater resistance to β-lactamases than the third-generation cephalosporins. Many can cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> and are effective in <a href="/wiki/Meningitis" title="Meningitis">meningitis</a>. They are also used against <i><a href="/wiki/Pseudomonas_aeruginosa" title="Pseudomonas aeruginosa">Pseudomonas aeruginosa</a></i>.<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. (April 2018)">citation needed</span></a></i>]</sup> </p><p>Cefiderocol has been called a fourth-generation cephalosporin by only one source as of November 2019.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> </p> </td></tr> <tr> <td><a href="/wiki/Cefiderocol" title="Cefiderocol">Cefiderocol</a></td> <td></td> <td>Fetroja</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=75c0c785-38e0-4049-a6fb-b77581f5b35c">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a></td> <td></td> <td></td> <td>V </td></tr> <tr> <td><a href="/wiki/Cefclidine" class="mw-redirect" title="Cefclidine">Cefclidine</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefluprenam" title="Cefluprenam">Cefluprenam</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefoselis" title="Cefoselis">Cefoselis</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefozopran" title="Cefozopran">Cefozopran</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefpirome" title="Cefpirome">Cefpirome</a></td> <td></td> <td>Cefrom</td> <td></td> <td> </td></tr> <tr> <td style="text-align: center;">(4)</td> <td><a href="/wiki/Flomoxef" title="Flomoxef">Flomoxef</a></td> <td></td> <td></td> <td></td> <td></td> <td>An <a href="/wiki/Oxacephem" title="Oxacephem">oxacephem</a> sometimes grouped with fourth-generation cephalosporins </td></tr> <tr style="border-top: 4px solid darkgray;"> <td rowspan="3" style="vertical-align: top; text-align: center; padding: 2.25em 0.5em;">5 </td> <td><a href="/wiki/Ceftaroline" class="mw-redirect" title="Ceftaroline">Ceftaroline</a></td> <td></td> <td></td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3ecde48b-75a2-4beb-9999-369f3f61bb8a">H</a></td> <td>MR </td> <td rowspan="3"><a href="/wiki/Ceftobiprole" title="Ceftobiprole">Ceftobiprole</a> has been described as "fifth-generation" cephalosporin,<sup id="cite_ref-pmid18225983_34-0" class="reference"><a href="#cite_note-pmid18225983-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17613382_35-0" class="reference"><a href="#cite_note-pmid17613382-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> though acceptance for this terminology is not universal. Ceftobiprole has anti-<a href="/wiki/Pseudomonal" class="mw-redirect" title="Pseudomonal">pseudomonal</a> activity and <i>appears</i> to be less susceptible to development of resistance. <a href="/wiki/Ceftaroline" class="mw-redirect" title="Ceftaroline">Ceftaroline</a> has also been described as "fifth-generation" cephalosporin, but does not have the activity against <i>Pseudomonas aeruginosa</i> or vancomycin-resistant enterococci that ceftobiprole has.<sup id="cite_ref-pmid20001879_36-0" class="reference"><a href="#cite_note-pmid20001879-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Ceftolozane" class="mw-redirect" title="Ceftolozane">Ceftolozane</a> is an option for the treatment of complicated intra-abdominal infections and complicated urinary tract infections. It is combined with the <a href="/wiki/Beta-lactamase" title="Beta-lactamase">β-lactamase</a> inhibitor <a href="/wiki/Tazobactam" title="Tazobactam">tazobactam</a>, as multi-drug resistant bacterial infections will generally show resistance to all <a href="/wiki/Beta-lactam_antibiotic" class="mw-redirect" title="Beta-lactam antibiotic">β-lactam antibiotics</a> unless this enzyme is inhibited.<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><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-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><sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Ceftolozane" class="mw-redirect" title="Ceftolozane">Ceftolozane</a></td> <td></td> <td>Zerbaxa</td> <td><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=70ac1d90-eff3-4f0b-9f46-5846c571b32f">H</a></td> <td> </td></tr> <tr> <td><a href="/wiki/Ceftobiprole" title="Ceftobiprole">Ceftobiprole</a></td> <td></td> <td></td> <td></td> <td>MR </td></tr> <tr style="border-top: 4px solid darkgray;"> <td rowspan="15" style="vertical-align: top; text-align: center; padding: 2.25em 0.5em;">?</td> <td><a href="/w/index.php?title=Cefaloram&action=edit&redlink=1" class="new" title="Cefaloram (page does not exist)">Cefaloram</a></td> <td></td> <td></td> <td></td> <td> </td> <td rowspan="15">These cephems have progressed far enough to be named, but have not been assigned to a particular generation. <a href="/wiki/Nitrocefin" title="Nitrocefin">Nitrocefin</a> is a chromogenic cephalosporin substrate, and is used for detection of β-lactamases.<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. (April 2018)">citation needed</span></a></i>]</sup> </td></tr> <tr> <td><a href="/wiki/Cefaparole" title="Cefaparole">Cefaparole</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Cefcanel&action=edit&redlink=1" class="new" title="Cefcanel (page does not exist)">Cefcanel</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Cefedrolor&action=edit&redlink=1" class="new" title="Cefedrolor (page does not exist)">Cefedrolor</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Cefempidone&action=edit&redlink=1" class="new" title="Cefempidone (page does not exist)">Cefempidone</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Cefetrizole&action=edit&redlink=1" class="new" title="Cefetrizole (page does not exist)">Cefetrizole</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Cefivitril&action=edit&redlink=1" class="new" title="Cefivitril (page does not exist)">Cefivitril</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefmatilen" title="Cefmatilen">Cefmatilen</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Cefmepidium&action=edit&redlink=1" class="new" title="Cefmepidium (page does not exist)">Cefmepidium</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Cefoxazole&action=edit&redlink=1" class="new" title="Cefoxazole (page does not exist)">Cefoxazole</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Cefrotil&action=edit&redlink=1" class="new" title="Cefrotil (page does not exist)">Cefrotil</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Cefsumide" title="Cefsumide">Cefsumide</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Ceftioxide&action=edit&redlink=1" class="new" title="Ceftioxide (page does not exist)">Ceftioxide</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/w/index.php?title=Cefuracetime&action=edit&redlink=1" class="new" title="Cefuracetime (page does not exist)">Cefuracetime</a></td> <td></td> <td></td> <td></td> <td> </td></tr> <tr> <td><a href="/wiki/Nitrocefin" title="Nitrocefin">Nitrocefin</a></td> <td></td> <td></td> <td></td> <td> </td></tr></tbody></table> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cephalosporin&action=edit&section=18" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Discovery_and_development_of_cephalosporins" title="Discovery and development of cephalosporins">Discovery and development of cephalosporins</a></div> <p>Cephalosporin compounds were first isolated from cultures of <i><a href="/wiki/Acremonium_strictum" title="Acremonium strictum">Acremonium strictum</a></i> from a sewer in <a href="/wiki/Sardinia" title="Sardinia">Sardinia</a> in 1948 by Italian scientist <a href="/wiki/Giuseppe_Brotzu" title="Giuseppe Brotzu">Giuseppe Brotzu</a>.<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> He noticed these cultures produced substances that were effective against <i><a href="/wiki/Salmonella_typhi" class="mw-redirect" title="Salmonella typhi">Salmonella typhi</a></i>, the cause of <a href="/wiki/Typhoid_fever" title="Typhoid fever">typhoid fever</a>, which had β-lactamase. <a href="/wiki/Guy_Newton" title="Guy Newton">Guy Newton</a> and <a href="/wiki/Edward_Abraham" title="Edward Abraham">Edward Abraham</a> at the <a href="/wiki/Sir_William_Dunn_School_of_Pathology" title="Sir William Dunn School of Pathology">Sir William Dunn School of Pathology</a> at the <a href="/wiki/University_of_Oxford" title="University of Oxford">University of Oxford</a> isolated <a href="/wiki/Cephalosporin_C" title="Cephalosporin C">cephalosporin C</a>. The cephalosporin nucleus, <a href="/wiki/7-ACA" title="7-ACA">7-aminocephalosporanic acid</a> (7-ACA), was derived from cephalosporin C and proved to be analogous to the penicillin nucleus <a href="/wiki/6-APA" title="6-APA">6-aminopenicillanic acid</a> (6-APA), but it was not sufficiently potent for clinical use. Modification of the 7-ACA side chains resulted in the development of useful antibiotic agents, and the first agent, <a href="/wiki/Cefalotin" title="Cefalotin">cefalotin</a> (cephalothin), was launched by <a href="/wiki/Eli_Lilly_and_Company" title="Eli Lilly and Company">Eli Lilly and Company</a> in 1964.<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. (June 2020)">citation needed</span></a></i>]</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=Cephalosporin&action=edit&section=19" 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-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</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.merriam-webster.com/dictionary/cephalosporin">"cephalosporin"</a>. <i><a href="/wiki/Merriam-Webster" title="Merriam-Webster">Merriam-Webster.com Dictionary</a></i>. Merriam-Webster.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Merriam-Webster.com+Dictionary&rft.atitle=cephalosporin&rft_id=https%3A%2F%2Fwww.merriam-webster.com%2Fdictionary%2Fcephalosporin&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACephalosporin" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20120707015035/http://oxforddictionaries.com/definition/english/cephalosporin">"cephalosporin – definition of cephalosporin in English from the Oxford dictionary"</a>. <a href="/wiki/OxfordDictionaries.com" class="mw-redirect" title="OxfordDictionaries.com">OxfordDictionaries.com</a>. Archived from <a rel="nofollow" class="external text" href="https://www.oxforddictionaries.com/definition/english/cephalosporin">the original</a> on 7 July 2012<span class="reference-accessdate">. Retrieved <span class="nowrap">20 January</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=cephalosporin+%E2%80%93+definition+of+cephalosporin+in+English+from+the+Oxford+dictionary&rft.pub=OxfordDictionaries.com&rft_id=https%3A%2F%2Fwww.oxforddictionaries.com%2Fdefinition%2Fenglish%2Fcephalosporin&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACephalosporin" class="Z3988"></span> </span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20090628224336/http://www.mercksource.com/pp/us/cns/cns_hl_dorlands_split.jsp?pg=/ppdocs/us/common/dorlands/dorland/two/000019430.htm">"cephalosporin"</a> at <i><a href="/wiki/Dorland%27s_medical_reference_works" title="Dorland's medical reference works">Dorland's Medical Dictionary</a></i></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=5W-WBQAAQBAJ&pg=PT56"><i>Oxford Handbook of Infectious Diseases and Microbiology</i></a>. OUP Oxford. 2009. p. 56. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780191039621" title="Special:BookSources/9780191039621"><bdi>9780191039621</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Oxford+Handbook+of+Infectious+Diseases+and+Microbiology&rft.pages=56&rft.pub=OUP+Oxford&rft.date=2009&rft.isbn=9780191039621&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5W-WBQAAQBAJ%26pg%3DPT56&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACephalosporin" class="Z3988"></span></span> </li> <li id="cite_note-HoMBRG-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-HoMBRG_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTilli_TanseyLois_Reynolds2000" class="citation book cs1"><a href="/wiki/Tilli_Tansey" title="Tilli Tansey">Tilli Tansey</a>, Lois Reynolds, eds. 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Wellcome Witnesses to Contemporary Medicine. <a href="/wiki/History_of_Modern_Biomedicine_Research_Group" title="History of Modern Biomedicine Research Group">History of Modern Biomedicine Research Group</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-84129-012-6" title="Special:BookSources/978-1-84129-012-6"><bdi>978-1-84129-012-6</bdi></a>. <a href="/wiki/OL_(identifier)" class="mw-redirect" title="OL (identifier)">OL</a> <a rel="nofollow" class="external text" href="https://openlibrary.org/books/OL12568269M">12568269M</a>. <a href="/wiki/WDQ_(identifier)" class="mw-redirect" title="WDQ (identifier)">Wikidata</a> <a href="https://www.wikidata.org/wiki/Q29581637" class="extiw" title="d:Q29581637">Q29581637</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Post+Penicillin+Antibiotics%3A+From+acceptance+to+resistance%3F&rft.series=Wellcome+Witnesses+to+Contemporary+Medicine&rft.pub=History+of+Modern+Biomedicine+Research+Group&rft.date=2000&rft_id=https%3A%2F%2Fopenlibrary.org%2Fbooks%2FOL12568269M%23id-name%3DOL&rft.isbn=978-1-84129-012-6&rft_id=http%3A%2F%2Fwww.histmodbiomed.org%2Fwitsem%2Fvol6&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACephalosporin" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPrince" class="citation web cs1">Prince A. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20190819132837if_/http://www.columbia.edu:80/itc/hs/medical/pathophys/id/2004/lecture/notes/CephaloVanco_Prince.pdf">"Cephalosporins and vancomycin"</a> <span class="cs1-format">(PDF)</span>. Columbia University. Archived from <a rel="nofollow" class="external text" href="http://www.columbia.edu/itc/hs/medical/pathophys/id/2004/lecture/notes/CephaloVanco_Prince.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 19 August 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">15 October</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Cephalosporins+and+vancomycin&rft.pub=Columbia+University&rft.aulast=Prince&rft.aufirst=A&rft_id=http%3A%2F%2Fwww.columbia.edu%2Fitc%2Fhs%2Fmedical%2Fpathophys%2Fid%2F2004%2Flecture%2Fnotes%2FCephaloVanco_Prince.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACephalosporin" class="Z3988"></span></span> </li> <li id="cite_note-:0-7"><span class="mw-cite-backlink">^ <a href="#cite_ref-:0_7-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:0_7-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.merckmanuals.com/professional/infectious-diseases/bacteria-and-antibacterial-drugs/cephalosporins">"Cephalosporins – Infectious Diseases"</a>. <i>Merck Manuals Professional Edition</i><span class="reference-accessdate">. Retrieved <span class="nowrap">15 May</span> 2019</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Merck+Manuals+Professional+Edition&rft.atitle=Cephalosporins+%E2%80%93+Infectious+Diseases&rft_id=https%3A%2F%2Fwww.merckmanuals.com%2Fprofessional%2Finfectious-diseases%2Fbacteria-and-antibacterial-drugs%2Fcephalosporins&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACephalosporin" class="Z3988"></span></span> </li> <li id="cite_note-:31424895-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-:31424895_8-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPandeyCascella2020" class="citation book cs1">Pandey N, Cascella M (2020). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/books/NBK545311/">"Beta Lactam Antibiotics"</a>. <i>StatPearls</i>. 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(June 2020)">page needed</span></a></i>]</sup></span> </li> </ol></div></div> <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=Cephalosporin&action=edit&section=20" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20150921163439/http://www.courses.ahc.umn.edu/pharmacy/6124/remmel_notes/cephalosporins.pdf">Cephalosporins</a></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 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.navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><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)" 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"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template: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)" 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 class="mw-selflink selflink">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 class="mw-selflink-fragment" href="#First_generation">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 class="mw-selflink-fragment" href="#Second_generation">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 class="mw-selflink-fragment" href="#Third_generation">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 class="mw-selflink-fragment" href="#Fourth_generation">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 class="mw-selflink-fragment" href="#Fifth_generation">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 href="/wiki/Isoniazid" title="Isoniazid">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="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-labelledby="Authority_control_databases_frameless&#124;text-top&#124;10px&#124;alt=Edit_this_at_Wikidata&#124;link=https&#58;//www.wikidata.org/wiki/Q271021#identifiers&#124;class=noprint&#124;Edit_this_at_Wikidata" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" 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class="external text" href="https://data.bnf.fr/ark:/12148/cb11946796x">BnF data</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00570250">Japan</a></span></li><li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="cefalosporiny"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph119087&CON_LNG=ENG">Czech Republic</a></span></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://catalogo.bne.es/uhtbin/authoritybrowse.cgi?action=display&authority_id=XX530025">Spain</a></span></li><li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007284814205171">Israel</a></span></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 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