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class="vector-toc-numb">1.3</span> <span>Pneumonia</span> </div> </a> <ul id="toc-Pneumonia-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Bloodstream_infections" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bloodstream_infections"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.4</span> <span>Bloodstream infections</span> </div> </a> <ul id="toc-Bloodstream_infections-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Spectrum_of_activity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Spectrum_of_activity"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5</span> <span>Spectrum of activity</span> </div> </a> <ul id="toc-Spectrum_of_activity-sublist" class="vector-toc-list"> <li id="toc-Gram-negative_pathogens" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Gram-negative_pathogens"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5.1</span> <span>Gram-negative pathogens</span> </div> </a> <ul id="toc-Gram-negative_pathogens-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Gram-positive_pathogens" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Gram-positive_pathogens"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5.2</span> <span>Gram-positive pathogens</span> </div> </a> <ul id="toc-Gram-positive_pathogens-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Other"> <div class="vector-toc-text"> <span class="vector-toc-numb">1.5.3</span> <span>Other</span> </div> </a> <ul id="toc-Other-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Contraindications" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Contraindications"> <div class="vector-toc-text"> <span class="vector-toc-numb">2</span> <span>Contraindications</span> </div> </a> <ul id="toc-Contraindications-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Adverse_effects" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Adverse_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Adverse effects</span> </div> </a> <ul id="toc-Adverse_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Examples" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Examples"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Examples</span> </div> </a> <button aria-controls="toc-Examples-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 Examples subsection</span> </button> <ul id="toc-Examples-sublist" class="vector-toc-list"> <li id="toc-Approved_for_clinical_use" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Approved_for_clinical_use"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Approved for clinical use</span> </div> </a> <ul id="toc-Approved_for_clinical_use-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Unapproved/experimental" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Unapproved/experimental"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Unapproved/experimental</span> </div> </a> <ul id="toc-Unapproved/experimental-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Bacterial_resistance" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Bacterial_resistance"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Bacterial resistance</span> </div> </a> <button aria-controls="toc-Bacterial_resistance-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 Bacterial resistance subsection</span> </button> <ul id="toc-Bacterial_resistance-sublist" class="vector-toc-list"> <li id="toc-Enterobacteriaceae" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Enterobacteriaceae"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Enterobacteriaceae</span> </div> </a> <ul id="toc-Enterobacteriaceae-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pseudomonas_aeruginosa_and_Acinetobacter_baumannii" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pseudomonas_aeruginosa_and_Acinetobacter_baumannii"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span><i>Pseudomonas aeruginosa</i> and <i>Acinetobacter baumannii</i></span> </div> </a> <ul id="toc-Pseudomonas_aeruginosa_and_Acinetobacter_baumannii-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Groups" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Groups"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Groups</span> </div> </a> <ul id="toc-Groups-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Biosynthesis</span> </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Administration" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Administration"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>Administration</span> </div> </a> <ul id="toc-Administration-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>See also</span> </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">11</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">12</span> <span>External links</span> </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" 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Available in 30 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-30" 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">30 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Karbapenem" title="Karbapenem – Afrikaans" lang="af" hreflang="af" data-title="Karbapenem" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target"><span>Afrikaans</span></a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%83%D8%A7%D8%B1%D8%A8%D8%A7%D8%A8%D9%8A%D9%86%D9%8A%D9%85" title="كاربابينيم – Arabic" lang="ar" hreflang="ar" data-title="كاربابينيم" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Carbapenem" title="Carbapenem – Catalan" lang="ca" hreflang="ca" data-title="Carbapenem" 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/Karbapenem" title="Karbapenem – Czech" lang="cs" hreflang="cs" data-title="Karbapenem" 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/Carbapenem" title="Carbapenem – Danish" lang="da" hreflang="da" data-title="Carbapenem" 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/Carbapeneme" title="Carbapeneme – German" lang="de" hreflang="de" data-title="Carbapeneme" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Karbapeneemid" title="Karbapeneemid – Estonian" lang="et" hreflang="et" data-title="Karbapeneemid" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9A%CE%B1%CF%81%CE%B2%CE%B1%CF%80%CE%B5%CE%BD%CE%AD%CE%BC%CE%B5%CF%82" title="Καρβαπενέμες – Greek" lang="el" hreflang="el" data-title="Καρβαπενέμες" 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/Carbapenem" title="Carbapenem – Spanish" lang="es" hreflang="es" data-title="Carbapenem" 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/Karbapenemiko" title="Karbapenemiko – Basque" lang="eu" hreflang="eu" data-title="Karbapenemiko" 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/%DA%A9%D8%A7%D8%B1%D8%A8%D8%A7%D9%BE%D9%86%D9%85" title="کارباپنم – Persian" lang="fa" hreflang="fa" data-title="کارباپنم" 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/Carbap%C3%A9n%C3%A8me" title="Carbapénème – French" lang="fr" hreflang="fr" data-title="Carbapénème" 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%B9%B4%EB%B0%94%ED%8E%98%EB%84%B4" title="카바페넴 – Korean" lang="ko" hreflang="ko" data-title="카바페넴" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Karbapenem" title="Karbapenem – Indonesian" lang="id" hreflang="id" data-title="Karbapenem" 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/Carbapenem" title="Carbapenem – Icelandic" lang="is" hreflang="is" data-title="Carbapenem" 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/Carbapenemi" title="Carbapenemi – Italian" lang="it" hreflang="it" data-title="Carbapenemi" 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%A7%D7%A8%D7%91%D7%A4%D7%A0%D7%9D" title="קרבפנם – Hebrew" lang="he" hreflang="he" data-title="קרבפנם" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Karbapenem" title="Karbapenem – Malay" lang="ms" hreflang="ms" data-title="Karbapenem" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target"><span>Bahasa Melayu</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Carbapenem" title="Carbapenem – Dutch" lang="nl" hreflang="nl" data-title="Carbapenem" 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%AB%E3%83%AB%E3%83%90%E3%83%9A%E3%83%8D%E3%83%A0%E7%B3%BB%E6%8A%97%E7%94%9F%E7%89%A9%E8%B3%AA" title="カルバペネム系抗生物質 – Japanese" lang="ja" hreflang="ja" data-title="カルバペネム系抗生物質" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Karbapenemy" title="Karbapenemy – Polish" lang="pl" hreflang="pl" data-title="Karbapenemy" 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/Carbapenema" title="Carbapenema – Portuguese" lang="pt" hreflang="pt" data-title="Carbapenema" 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/Carbapenem%C4%83" title="Carbapenemă – Romanian" lang="ro" hreflang="ro" data-title="Carbapenemă" 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%9A%D0%B0%D1%80%D0%B1%D0%B0%D0%BF%D0%B5%D0%BD%D0%B5%D0%BC%D1%8B" title="Карбапенемы – Russian" lang="ru" hreflang="ru" data-title="Карбапенемы" 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/Carbapenem" title="Carbapenem – Simple English" lang="en-simple" hreflang="en-simple" data-title="Carbapenem" 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-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Karbapenemi" title="Karbapenemi – Slovenian" lang="sl" hreflang="sl" data-title="Karbapenemi" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Karbapeneemit" title="Karbapeneemit – Finnish" lang="fi" hreflang="fi" data-title="Karbapeneemit" 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/Karbapenemresistens" title="Karbapenemresistens – Swedish" lang="sv" hreflang="sv" data-title="Karbapenemresistens" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9A%D0%B0%D1%80%D0%B1%D0%B0%D0%BF%D0%B5%D0%BD%D0%B5%D0%BC%D0%B8" title="Карбапенеми – Ukrainian" lang="uk" hreflang="uk" data-title="Карбапенеми" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%A2%B3%E9%9D%92%E9%BB%B4%E7%83%AF" title="碳青黴烯 – Chinese" lang="zh" hreflang="zh" data-title="碳青黴烯" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target"><span>中文</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q410897#sitelinks-wikipedia" title="Edit interlanguage links" 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searchaux" style="display:none">Class of highly effective antibiotic agents</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Carbapenems_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Carbapenems_structure.svg/200px-Carbapenems_structure.svg.png" decoding="async" width="200" height="169" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/af/Carbapenems_structure.svg/300px-Carbapenems_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/af/Carbapenems_structure.svg/400px-Carbapenems_structure.svg.png 2x" data-file-width="512" data-file-height="433" /></a><figcaption>Backbone structure of a carbapenem.</figcaption></figure> <p><b>Carbapenems</b> are a class of very effective <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> agents most commonly used for treatment of severe bacterial <a href="/wiki/Infections" class="mw-redirect" title="Infections">infections</a>. This class of antibiotics is usually reserved for known or suspected <a href="/wiki/Multiple_drug_resistance" title="Multiple drug resistance">multidrug-resistant</a> (MDR) bacterial infections. Similar to <a href="/wiki/Penicillins" class="mw-redirect" title="Penicillins">penicillins</a> and <a href="/wiki/Cephalosporins" class="mw-redirect" title="Cephalosporins">cephalosporins</a>, carbapenems are members of the <a href="/wiki/Beta-lactam_antibiotics" class="mw-redirect" title="Beta-lactam antibiotics">beta-lactam antibiotics</a> drug class, which kill bacteria by binding to <a href="/wiki/Penicillin-binding_proteins" title="Penicillin-binding proteins">penicillin-binding proteins</a>, thus inhibiting bacterial cell wall synthesis. However, these agents individually exhibit a broader spectrum of activity compared to most cephalosporins and penicillins. Furthermore, carbapenems are typically unaffected by emerging <a href="/wiki/Antimicrobial_resistance" title="Antimicrobial resistance">antibiotic resistance</a>, even to other beta-lactams.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (July 2023)">medical citation needed</span></a></i>]</sup> </p><p>Carbapenem antibiotics were originally developed at <a href="/wiki/Merck_%26_Co." title="Merck & Co.">Merck & Co.</a> from the carbapenem <a href="/wiki/Thienamycin" title="Thienamycin">thienamycin</a>, a naturally derived product of <i><a href="/wiki/Streptomyces_cattleya" title="Streptomyces cattleya">Streptomyces cattleya</a></i>.<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> Concern has arisen in recent years over increasing rates of resistance to carbapenems, as there are few therapeutic options for treating infections caused by carbapenem-resistant bacteria (such as <i><a href="/wiki/Klebsiella_pneumoniae" title="Klebsiella pneumoniae">Klebsiella pneumoniae</a></i> and other <a href="/wiki/Carbapenem-resistant_enterobacteriaceae" title="Carbapenem-resistant enterobacteriaceae">carbapenem-resistant Enterobacteriaceae</a><sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup>).<sup id="cite_ref-Carbapenems_4-0" class="reference"><a href="#cite_note-Carbapenems-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ReferenceA_5-0" class="reference"><a href="#cite_note-ReferenceA-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><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> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <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=Carbapenem&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Intra-abdominal_infections">Intra-abdominal infections</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=2" title="Edit section: Intra-abdominal infections"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The carbapenem <a href="/wiki/Ertapenem" title="Ertapenem">ertapenem</a> is one of several first-line agents recommended by the <a href="/wiki/Infectious_Disease_Society_of_America" class="mw-redirect" title="Infectious Disease Society of America">Infectious Disease Society of America</a> for the empiric treatment of community-acquired intra-abdominal infections of mild-to-moderate severity. Agents with anti-pseudomonal activity, including <a href="/wiki/Doripenem" title="Doripenem">doripenem</a>, <a href="/wiki/Imipenem" title="Imipenem">imipenem</a>, and <a href="/wiki/Meropenem" title="Meropenem">meropenem</a>, are not recommended in this population. Doripenem, imipenem, and meropenem are recommended for high-risk community-acquired abdominal infections and for abdominal infections that are hospital-acquired.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Complicated_urinary_tract_infections">Complicated urinary tract infections</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=3" title="Edit section: Complicated urinary tract infections"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 2015 systematic review found little evidence that would support the identification of a best antimicrobial regimen for complicated <a href="/wiki/Urinary_tract_infections" class="mw-redirect" title="Urinary tract infections">urinary tract infections</a>, but identified three high-quality trials supporting high cure rates with doripenem, including in patients with <a href="/wiki/Levofloxacin" title="Levofloxacin">levofloxacin</a>-resistant <i><a href="/wiki/E._coli" class="mw-redirect" title="E. coli">E. coli</a></i> infections.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pneumonia">Pneumonia</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=4" title="Edit section: Pneumonia"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The carbapenems imipenem and meropenem are recommended by the <a href="/wiki/American_Thoracic_Society" title="American Thoracic Society">American Thoracic Society</a> and the Infectious Disease Society of America as one of several first-line therapy options for people with late-onset <a href="/wiki/Hospital-acquired_pneumonia" title="Hospital-acquired pneumonia">hospital-acquired</a> or <a href="/wiki/Ventilator-associated_pneumonia" title="Ventilator-associated pneumonia">ventilator-associated</a> pneumonia, especially when <i>Pseudomonas</i>, <i>Acinetobacter</i>, or <a href="/wiki/Extended_spectrum_beta-lactamase" class="mw-redirect" title="Extended spectrum beta-lactamase">extended spectrum beta-lactamase</a> producing <i>Enterobacteriaceae</i> are suspected pathogens. Combination therapy, typically with an <a href="/wiki/Aminoglycoside" title="Aminoglycoside">aminoglycoside</a>, is recommended for <i>Pseudomonas</i> infections to avoid resistance development during treatment.<sup id="cite_ref-ReferenceB_9-0" class="reference"><a href="#cite_note-ReferenceB-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Carbapenems are less commonly used in the treatment of community-acquired pneumonia, as community-acquired strains of the most common responsible pathogens (<i>Streptococcus pneumoniae</i>, <i>Haemophilus influenazae</i>, atypical bacteria, and Enterobactericeace) are typically susceptible to narrower spectrum and/or orally administered agents such as <a href="/wiki/Fluoroquinolones" class="mw-redirect" title="Fluoroquinolones">fluoroquinolones</a>, <a href="/wiki/Amoxicillin" title="Amoxicillin">amoxicillin</a>, or <a href="/wiki/Azithromycin" title="Azithromycin">azithromycin</a>. Imipenem and meropenem are useful in cases in which <i>P. aeruginosa</i> is a suspected pathogen.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Bloodstream_infections">Bloodstream infections</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=5" title="Edit section: Bloodstream infections"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 2015 meta analysis concluded that the anti-pseudomonal penicillin-beta lactamase inhibitor combination <a href="/wiki/Piperacillin-tazobactam" class="mw-redirect" title="Piperacillin-tazobactam">piperacillin-tazobactam</a> gives results equivalent to treatment with a carbapenem in patients with sepsis.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> In 2015, the <a href="/wiki/National_Institute_for_Health_and_Care_Excellence" title="National Institute for Health and Care Excellence">National Institute for Health and Care Excellence</a> recommended piperacillin-tazobactam as first line therapy for the treatment of bloodstream infections in neutropenic cancer patients.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>For bloodstream infections known to be due to extended spectrum beta-lactamase producing <i>Enterobacteriaceace</i>, carbapenems are superior to alternative treatments.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Spectrum_of_activity">Spectrum of activity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=6" title="Edit section: Spectrum of activity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbapenems exhibit broad spectrum activity against <a href="/wiki/Gram-negative" class="mw-redirect" title="Gram-negative">gram-negative</a> bacteria and somewhat narrower activity against <a href="/wiki/Gram-positive" class="mw-redirect" title="Gram-positive">gram-positive</a> bacteria. For <a href="/wiki/Empiric_therapy" title="Empiric therapy">empiric therapy</a> (treatment of infections prior to identification of the responsible pathogen) they are often combined with a second drug having broader spectrum gram-positive activity.<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> <div class="mw-heading mw-heading4"><h4 id="Gram-negative_pathogens">Gram-negative pathogens</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=7" title="Edit section: Gram-negative pathogens"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The spectrum of activity of the carbapenems imipenem, doripenem, and meropenem includes most <i>Enterobacteriaceace</i> species, including <i>Escherichia coli</i>, <i><a href="/wiki/Klebsiella_pneumoniae" title="Klebsiella pneumoniae">Klebsiella pneumoniae</a></i>, <i><a href="/wiki/Enterobacter_cloacae" title="Enterobacter cloacae">Enterobacter cloacae</a></i>, <i><a href="/wiki/Citrobacter_freundii" title="Citrobacter freundii">Citrobacter freundii</a></i>, <i><a href="/wiki/Proteus_mirabilis" title="Proteus mirabilis">Proteus mirabilis</a></i>, and <i><a href="/wiki/Serratia_marcescens" title="Serratia marcescens">Serratia marcescens</a></i>. Activity is maintained against most strains of <i>E. coli</i> and <i>K. pneumoniae</i> that are resistant to cephalosporins due to the production of <a href="/wiki/Extended_spectrum_beta-lactamase" class="mw-redirect" title="Extended spectrum beta-lactamase">extended spectrum beta-lactamases</a>. Imipenem, doripenem, and meropenem also exhibit good activity against most strains of <i>Pseudomonas aeruginosa</i> and <i>Acinetobacter</i> species. The observed activity against these pathogens is especially valued as they are intrinsically resistant to many other antibiotic classes.<sup id="cite_ref-Carbapenems_4-1" class="reference"><a href="#cite_note-Carbapenems-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Gram-positive_pathogens">Gram-positive pathogens</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=8" title="Edit section: Gram-positive pathogens"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The spectrum of activity of the carbapenems against gram-positive bacteria is fairly broad, but not as exceptionally so as in the case of gram-negative bacteria. Good activity is seen against methicillin-sensitive strains of <i>Staphylococcus</i> species, but many other antibiotics provide coverage for such infections. Good activity is also observed for most <i>Streptococcus</i> species, including penicillin-resistant strains. Carbapenems are not highly active against <a href="/wiki/Methicillin-resistant_Staphylococcus_aureus" title="Methicillin-resistant Staphylococcus aureus">methicillin-resistant <i>Staphylococcus aureus</i></a> or most <i><a href="/wiki/Enterococci" class="mw-redirect" title="Enterococci">enterococcal</a></i> infections because carbapenems do not bind to the penicillin-binding protein used by these pathogens.<sup id="cite_ref-Carbapenems_4-2" class="reference"><a href="#cite_note-Carbapenems-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Other">Other</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=9" title="Edit section: Other"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbapenems generally exhibit good activity against anaerobes such as <i><a href="/wiki/Bacteroides_fragilis" title="Bacteroides fragilis">Bacteroides fragilis</a></i>. Like other beta lactam antibiotics, they lack activity against atypical bacteria, which do not have a cell wall and are thus not affected by cell wall synthesis inhibitors.<sup id="cite_ref-Carbapenems_4-3" class="reference"><a href="#cite_note-Carbapenems-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Contraindications">Contraindications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=10" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbapenems are contraindicated in patients with prior allergic reactions to beta lactam antibiotics. In addition, as the <a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular">intramuscular</a> <a href="/wiki/Formulations" class="mw-redirect" title="Formulations">formulations</a> of ertapenem and imipenem are formulated with <a href="/wiki/Lidocaine" title="Lidocaine">lidocaine</a>, the intramuscular formulation of these two drugs are contraindicated in patients with prior adverse reactions to lidocaine.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> Furthermore, carbapenems are also contraindicated in patients who are taking <a href="/wiki/Valproic_acid" class="mw-redirect" title="Valproic acid">valproic acid</a> for seizures, as it has been shown to decrease valproic acid concentrations by as much as 90%.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Adverse_effects">Adverse effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=11" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Serious and occasionally fatal allergic reactions can occur in people treated with carbapenems.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Seizures" class="mw-redirect" title="Seizures">Seizures</a> are a dose-limiting <a href="/wiki/Toxicity" title="Toxicity">toxicity</a> for both imipenem and meropenem.<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> <i><a href="/wiki/Clostridioides_difficile" title="Clostridioides difficile">Clostridioides difficile</a></i>-related diarrhea may occur in people treated with carbapenems or other broad-spectrum antibiotics.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Those with an allergy to <a href="/wiki/Side_effects_of_penicillin" title="Side effects of penicillin">penicillin</a> may develop a cross sensitivity to carbapenems.<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="Examples">Examples</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=12" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Approved_for_clinical_use">Approved for clinical use</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=13" title="Edit section: Approved for clinical use"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Imipenem" title="Imipenem">Imipenem</a>, the first clinically used carbapenem, was developed at Merck and Co. It was approved for use in the United States in 1985.<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> Imipenem is hydrolyzed in the <a href="/wiki/Mammalian_kidney" title="Mammalian kidney">mammalian kidney</a> by a dehydropeptidase enzyme to a nephrotoxic intermediate, and thus is co-formulated with the dehydropeptidase inhibitor cilastatin.<sup id="cite_ref-ReferenceA_5-1" class="reference"><a href="#cite_note-ReferenceA-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Imipenem is available in both intravenous<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> and intramuscular<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> formulations.</li> <li><a href="/wiki/Meropenem" title="Meropenem">Meropenem</a> is stable to mammalian dehydropeptidases and does not require co-administration of cilastatin. It was approved for use in the United States in 1996. In most indications it is somewhat more convenient to administer than imipenem, 3 times a day rather than 4. Doses of less than one gram may be administered as an IV bolus, whereas imipenem is usually administered as a 20-minute to one hour infusion. Meropenem is somewhat less potent than imipenem against gram-positive pathogens, and somewhat more potent against gram-negative infections. Unlike imipenem, which produced an unacceptable rate of seizures in a phase 2 trial, meropenem is effective for the treatment of bacterial meningitis.<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> A systematic review performed by an employee of the company that markets meropenem concluded that it provides a higher bacterial response and lower adverse event rates than imipenem in people with severe infections, but no difference in mortality rate.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Ertapenem" title="Ertapenem">Ertapenem</a> is administered once daily as an intravenous infusion or intramuscular injection. It lacks useful activity against the <i>P. aeruginosa</i> and <i>Acinetobacter</i> species, both of which are important causes of hospital-acquired infections.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Doripenem" title="Doripenem">Doripenem</a> has a spectrum of activity very similar to that of meropenem. Its greater stability in solution allows the use of prolonged infusions and it is somewhat less likely to produce seizures than other carbapenems.<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></li> <li><a href="/wiki/Panipenem/betamipron" title="Panipenem/betamipron">Panipenem/betamipron</a> (Japanese approval 1993)</li> <li><a href="/wiki/Biapenem" title="Biapenem">Biapenem</a> (Japanese approval 2001) exhibits similar efficacy and adverse event rates as other carbapenems.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Tebipenem" title="Tebipenem">Tebipenem</a> (Japanese approval 2015) is the first carbapenem whose prodrug form, the pivalyl ester, is orally available.<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></li></ul> <div class="mw-heading mw-heading3"><h3 id="Unapproved/experimental"><span id="Unapproved.2Fexperimental"></span>Unapproved/experimental</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=14" title="Edit section: Unapproved/experimental"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Razupenem" title="Razupenem">Razupenem</a> (PZ-601) <ul><li>PZ-601 is a carbapenem antibiotic currently being tested as having a broad spectrum of activity including strains resistant to other carbapenems. Despite early Phase II promise, Novartis (who acquired PZ-601 in a merger deal with Protez Pharmaceuticals) recently dropped PZ-601, citing a high rate of adverse events in testing.<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></li></ul></li> <li><a href="/wiki/Lenapenem" title="Lenapenem">Lenapenem</a></li> <li><a href="/wiki/Sulopenem" title="Sulopenem">Sulopenem</a> is in clinical trials for drug resistant urinary tract infections</li> <li><a href="/wiki/Tomopenem" title="Tomopenem">Tomopenem</a></li> <li><a href="/wiki/Thienamycin" title="Thienamycin">Thienamycin</a> (thienpenem) the first discovered carbapenem</li> <li><a href="/wiki/Faropenem" title="Faropenem">Faropenem</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Bacterial_resistance">Bacterial resistance</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=15" title="Edit section: Bacterial resistance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Enterobacteriaceae">Enterobacteriaceae</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=16" title="Edit section: Enterobacteriaceae"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><i>Enterobacteriaceae</i> are common pathogens responsible for urinary tract infections,<sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> abdominal infections,<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> and hospital-acquired pneumonia.<sup id="cite_ref-ReferenceB_9-1" class="reference"><a href="#cite_note-ReferenceB-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Beta lactam resistance in these pathogens is most commonly due to the expression of beta lactamase enzymes.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p><p>Between 2007 and 2011, the percentage of <i>Escherichia coli</i> isolates from Canadian hospitals that produce <a href="/wiki/Extended_spectrum_beta-lactamase" class="mw-redirect" title="Extended spectrum beta-lactamase">extended spectrum beta lactamases</a> (ESBL) increased from 3.4% to 4.1%; among <i>Klebsiella pneumoniae</i> isolates ESBL producers increased from 1.5% to 4.0%. These strains are resistant to <a href="/wiki/Cephalosporins" class="mw-redirect" title="Cephalosporins">third generation cephalosporins</a> that were developed for the treatment of beta lactamase-producing <i>Enterobacteriaceae</i> and carbapenems are generally regarded as the treatment of choice.<sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> More recently, many countries have experienced a dramatic upswing in the prevalence of <i>Enterobacteriaceae</i> that produce both ESBLs and <a href="/wiki/Carbapenemase" class="mw-redirect" title="Carbapenemase">carbapenemases</a> such as the Klebsiella pneumoniae carbapenemase (KPC). As of 2013, 70% of Greek <i>Klebsiella pneumoniae</i> isolates are resistant to third generation cephalosporins and 60% are resistant to carbapenems.<sup id="cite_ref-36" class="reference"><a href="#cite_note-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> The growing prevalence and difficulty of treating such multi-drug resistant <i>Enterobacteriaceae</i> has led to a renaissance of the use of antibiotics such as <a href="/wiki/Colistin" title="Colistin">colistin</a>, which was discovered in the 1950s but rarely used until recently due to unattractive levels of toxicity.<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> </p><p>Prevalence of carbapenem-resistant <i>Enterobacteriaceae</i> in paediatric intensive care units (Cairo, Egypt) was 24% and various genes of carbapenemases were detected in 80% of carbapenem-resistant <i>Enterobacteriaceae</i> with dominance of <i>bla</i><sub>OXA-48.</sub><sup id="cite_ref-38" class="reference"><a href="#cite_note-38"><span class="cite-bracket">[</span>38<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pseudomonas_aeruginosa_and_Acinetobacter_baumannii"><i>Pseudomonas aeruginosa</i> and <i>Acinetobacter baumannii</i></h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=17" title="Edit section: Pseudomonas aeruginosa and Acinetobacter baumannii"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Infections caused by the non-fermenting gram-negative bacteria <i>Pseudomonas aeruginosa</i> and <i>Acinetobacter baumanni</i> are most commonly encountered in hospitalized people. These bacteria exhibit an unusually high level of intrinsic resistance to antibiotics due to their expression of a wide range of resistance mechanisms. Antibiotics cross the outer membrane of <i>Pseudomonas</i> and <i>Acinetobacter</i> approximately 100 times more slowly than they cross the outer membrane of <i>Enterobacteriaceae</i>, due in part to their use of <a href="/wiki/Porin_(protein)" title="Porin (protein)">porins</a> that can adopt a conformation having a very restricted entry channel. Further, the porin levels may be down-regulated in response to antibiotic exposure. Antibiotic molecules that successfully traverse the porin channels may be removed by efflux pumps. Downregulation of the porin OprD2 is an important contributor to imipenem resistance.<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> </p><p>Like the <i>Enterobacteriaceae</i>, <i>Pseudomonas</i> and <i>Acinetobacter</i> can express a wide range of antibiotic-deactivitating enzymes, including beta lactamases. <i>Pseudomonas</i> produces an inducible broad spectrum beta lactamase, AmpC, that is produced in response to beta lactam exposure. The combination of inducible AmpC expression, poor membrane permeability, and efflux pumps make <i>Pseudomonas</i> resistant to most beta lactams. The clinical efficacy of carbapenems in <i>Pseudomonas</i> infection arises in part because, while they are strong inducers of AmpC, they are poor substrates. The identification of <i>Pseudomonas</i> strains that produce beta lactamases capable of cleaving carbapenems, such as the <a href="/wiki/New_Delhi_metallo-beta-lactamase_1" title="New Delhi metallo-beta-lactamase 1">New Delhi metallo beta lactamase</a> has raised increasing concern regarding the potential for an era of untreatable <i>Pseudomonas</i> infections.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> </p> <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=Carbapenem&action=edit&section=18" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In terms of structure, the carbapenems are very similar to the <a href="/wiki/Penicillin" title="Penicillin">penicillins</a> (<a href="/wiki/Penam" title="Penam">penams</a>), but the sulfur atom in position 1 of the structure has been replaced with a carbon atom, and an <a href="/wiki/Degree_of_unsaturation" title="Degree of unsaturation">unsaturation</a> has been introduced—hence the name of the group, the carbapen<u>e</u>ms. </p> <div class="mw-heading mw-heading2"><h2 id="Groups">Groups</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=19" title="Edit section: Groups"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Carbapenems are further broken down into groups with ertapenem being the lone member of group 1. Group 2 carbapenems (imipenem, meropenem, and doripenem) are identified by their efficacy with respect to multiresistant gram-negative (<a href="/wiki/Multidrug-resistant_Gram-negative_bacteria" title="Multidrug-resistant Gram-negative bacteria">MDRGN</a>) bacteria such as Pseudomonas and Acinetobacter species. <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> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=20" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The carbapenems are thought to share their early biosynthetic steps in which the core ring system is formed. <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">Malonyl-CoA</a> is condensed with <a href="/wiki/Glutamate-5-semialdehyde" title="Glutamate-5-semialdehyde">glutamate-5-semialdehyde</a> with concurrent formation of the five-membered ring. Next, a β-lactam synthetase uses <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> to form the β-lactam and the saturated <a href="/wiki/Carbapenam" title="Carbapenam">carbapenam</a> core. Further oxidation and ring inversion provides the basic carbapenem <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. (October 2019)">citation needed</span></a></i>]</sup>. </p> <div class="mw-heading mw-heading2"><h2 id="Administration">Administration</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=21" title="Edit section: Administration"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Due to their expanded spectra, the desire to avoid generation of resistance and the fact that, in general, they have poor oral bioavailability, they are administered intravenously in hospital settings for more serious infections. However, research is underway to develop an effective oral carbapenem.<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> </p> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=22" title="Edit section: See also"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Faropenem" title="Faropenem">Faropenem</a> is closely related, but it is a <a href="/wiki/Penem" title="Penem">penem</a>, not a carbapenem.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Antimicrobial_resistance" title="Antimicrobial resistance">Antimicrobial resistance</a> <ul><li><a href="/wiki/New_Delhi_metallo-beta-lactamase_1" title="New Delhi metallo-beta-lactamase 1">NDM-1</a> is an enzyme that introduces bacterial resistance to carbapenem antibiotics via hydrolysis of the carbapenem backbone, thereby inactivating its ability to inhibit cell wall synthesis.</li></ul></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Carbapenem&action=edit&section=23" 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 reflist-columns references-column-width" style="column-width: 30em;"> <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 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Pharmacotherapy&rft.atitle=Chemical+and+Microbiologic+Aspects+of+Penems%2C+a+Distinct+Class+of+%CE%B2-Lactams%3A+Focus+on+Faropenem&rft.volume=23&rft.issue=11&rft.pages=1497-507&rft.date=2003-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A43705118%23id-name%3DS2CID&rft_id=info%3Apmid%2F14620395&rft_id=info%3Adoi%2F10.1592%2Fphco.23.14.1497.31937&rft.aulast=Hamilton-Miller&rft.aufirst=JM&rft_id=http%3A%2F%2Fwww.medscape.com%2Fviewarticle%2F464632_2&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACarbapenem" class="Z3988"></span></span> </li> </ol></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=Carbapenem&action=edit&section=24" 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/20060304094439/http://www.infectio-lille.com/diaporamas/invites/struct-act-duatb05-bryskier.pdf">Structure Activity Relationships</a> "Antibacterial Agents; Structure Activity Relationships," André Bryskier MD; beginning at pp131</li> <li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160303203442/http://www.sdshp.cshp.org/uploads/informulary/Informulary_Vol_3_Issue_3.pdf">Page 2: Ertapenem vs. Meropenem: Equivalency of Clinical and Microbiological Outcomes. 2010</a></li></ul> <div style="clear:both;" class=""></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output 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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 class="mw-selflink selflink">Carbapenems</a> / <a href="/wiki/Penem" title="Penem">Penems</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Carbapenems (<a href="/wiki/Ertapenem" title="Ertapenem">Ertapenem</a></li> <li><a href="/wiki/Antipseudomonal" class="mw-redirect" title="Antipseudomonal">Antipseudomonal</a> (<a href="/wiki/Doripenem" title="Doripenem">Doripenem</a></li> <li><a href="/wiki/Imipenem" title="Imipenem">Imipenem</a></li> <li><a href="/wiki/Meropenem" title="Meropenem">Meropenem</a>)</li> <li><a href="/wiki/Biapenem" title="Biapenem">Biapenem</a><sup>‡</sup></li> <li><a href="/wiki/Panipenem" title="Panipenem">Panipenem</a>)</li> <li>Penems (<a href="/wiki/Faropenem" title="Faropenem">Faropenem</a></li> <li><a href="/wiki/Ritipenem" title="Ritipenem">Ritipenem</a><sup>§</sup></li> <li><a href="/wiki/Sulopenem" title="Sulopenem">Sulopenem</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephem" title="Cephem">Cephems</a><br /><a href="/wiki/Cephalosporin" title="Cephalosporin">Cephalosporins</a><br /><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycins</a><br /><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephems</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#First_generation" title="Cephalosporin">1st generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefazolin" title="Cefazolin">Cefazolin</a><sup>#</sup></li> <li><a href="/wiki/Cefalexin" title="Cefalexin">Cefalexin</a> <sup>#</sup></li> <li><a href="/wiki/Cefadroxil" title="Cefadroxil">Cefadroxil</a></li> <li><a href="/wiki/Cefapirin" title="Cefapirin">Cefapirin</a></li> <li><a href="/wiki/Cefazedone" title="Cefazedone">Cefazedone</a><sup>‡</sup></li> <li><a href="/wiki/Cefazaflur" title="Cefazaflur">Cefazaflur</a><sup>‡</sup></li> <li><a href="/wiki/Cefradine" title="Cefradine">Cefradine</a><sup>‡</sup></li> <li><a href="/wiki/Cefroxadine" title="Cefroxadine">Cefroxadine</a><sup>‡</sup></li> <li><a href="/wiki/Ceftezole" title="Ceftezole">Ceftezole</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloglycin" title="Cefaloglycin">Cefaloglycin</a><sup>‡</sup></li> <li><a href="/wiki/Cefacetrile" title="Cefacetrile">Cefacetrile</a><sup>‡</sup></li> <li><a href="/wiki/Cefalonium" title="Cefalonium">Cefalonium</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloridine" class="mw-redirect" title="Cefaloridine">Cefaloridine</a><sup>‡</sup></li> <li><a href="/wiki/Cefalotin" title="Cefalotin">Cefalotin</a></li> <li><a href="/wiki/Cefatrizine" title="Cefatrizine">Cefatrizine</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Second_generation" title="Cephalosporin">2nd generation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefaclor" title="Cefaclor">Cefaclor</a></li> <li><a href="/wiki/Cefprozil" title="Cefprozil">Cefprozil</a></li> <li><a href="/wiki/Cefuroxime" title="Cefuroxime">Cefuroxime</a></li> <li><a href="/wiki/Cefuroxime_axetil" title="Cefuroxime axetil">Cefuroxime axetil</a></li> <li><a href="/wiki/Cefamandole" title="Cefamandole">Cefamandole</a><sup>‡</sup></li> <li><a href="/wiki/Cefonicid" title="Cefonicid">Cefonicid</a><sup>‡</sup></li> <li><a href="/wiki/Ceforanide" title="Ceforanide">Ceforanide</a><sup>‡</sup></li> <li><a href="/wiki/Cefuzonam" title="Cefuzonam">Cefuzonam</a><sup>‡</sup></li> <li><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycin</a> (<a href="/wiki/Cefoxitin" title="Cefoxitin">Cefoxitin</a></li> <li><a href="/wiki/Cefotetan" title="Cefotetan">Cefotetan</a></li> <li><a href="/wiki/Cefminox" title="Cefminox">Cefminox</a><sup>‡</sup></li> <li><a href="/wiki/Cefbuperazone" title="Cefbuperazone">Cefbuperazone</a><sup>‡</sup></li> <li><a href="/wiki/Cefmetazole" title="Cefmetazole">Cefmetazole</a><sup>‡</sup>)</li> <li><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephem</a> (<a href="/wiki/Loracarbef" title="Loracarbef">Loracarbef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Third_generation" title="Cephalosporin">3rd generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefixime" title="Cefixime">Cefixime</a><sup>#</sup></li> <li><a href="/wiki/Ceftriaxone" title="Ceftriaxone">Ceftriaxone</a><sup>#</sup></li> <li><a href="/wiki/Cefotaxime" title="Cefotaxime">Cefotaxime</a><sup>#</sup></li> <li>Antipseudomonal (<a href="/wiki/Ceftazidime" title="Ceftazidime">Ceftazidime</a><sup>#</sup></li> <li><a href="/wiki/Cefoperazone" title="Cefoperazone">Cefoperazone</a>)</li> <li><a href="/wiki/Cefdinir" title="Cefdinir">Cefdinir</a></li> <li><a href="/wiki/Cefcapene" title="Cefcapene">Cefcapene</a></li> <li><a href="/wiki/Cefdaloxime" title="Cefdaloxime">Cefdaloxime</a></li> <li><a href="/wiki/Ceftizoxime" title="Ceftizoxime">Ceftizoxime</a></li> <li><a href="/wiki/Cefmenoxime" title="Cefmenoxime">Cefmenoxime</a></li> <li><a href="/wiki/Cefpiramide" title="Cefpiramide">Cefpiramide</a></li> <li><a href="/wiki/Cefpodoxime" title="Cefpodoxime">Cefpodoxime</a></li> <li><a href="/wiki/Ceftibuten" title="Ceftibuten">Ceftibuten</a></li> <li><a href="/wiki/Cefditoren" title="Cefditoren">Cefditoren</a></li> <li><a href="/wiki/Cefotiam" title="Cefotiam">Cefotiam</a><sup>‡</sup></li> <li><a href="/wiki/Cefetamet" title="Cefetamet">Cefetamet</a><sup>‡</sup></li> <li><a href="/wiki/Cefodizime" title="Cefodizime">Cefodizime</a><sup>‡</sup></li> <li><a href="/wiki/Cefpimizole" title="Cefpimizole">Cefpimizole</a><sup>‡</sup></li> <li><a href="/wiki/Cefsulodin" title="Cefsulodin">Cefsulodin</a><sup>‡</sup></li> <li><a href="/wiki/Cefteram" title="Cefteram">Cefteram</a><sup>‡</sup></li> <li><a href="/wiki/Ceftiolene" title="Ceftiolene">Ceftiolene</a><sup>‡</sup></li> <li><a href="/wiki/Oxacephem" title="Oxacephem">Oxacephem</a> (<a href="/wiki/Flomoxef" title="Flomoxef">Flomoxef</a></li> <li><a href="/wiki/Latamoxef" title="Latamoxef">Latamoxef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fourth_generation" title="Cephalosporin">4th generation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefepime" title="Cefepime">Cefepime</a></li> <li><a href="/wiki/Cefozopran" title="Cefozopran">Cefozopran</a><sup>‡</sup></li> <li><a href="/wiki/Cefpirome" title="Cefpirome">Cefpirome</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fifth_generation" title="Cephalosporin">5th generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ceftaroline_fosamil" title="Ceftaroline fosamil">Ceftaroline fosamil</a></li> <li><a href="/wiki/Ceftolozane" class="mw-redirect" title="Ceftolozane">Ceftolozane</a></li> <li><a href="/wiki/Ceftobiprole" title="Ceftobiprole">Ceftobiprole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Siderophore" title="Siderophore">Siderophore</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cefiderocol" title="Cefiderocol">Cefiderocol</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Veterinary_medicine" title="Veterinary medicine">Veterinary</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ceftiofur" title="Ceftiofur">Ceftiofur</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a></li> <li><a href="/wiki/Cefovecin" title="Cefovecin">Cefovecin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Monobactam" title="Monobactam">Monobactams</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aztreonam" title="Aztreonam">Aztreonam</a></li> <li><a href="/wiki/Tigemonam" title="Tigemonam">Tigemonam</a><sup>‡</sup></li> <li><a href="/wiki/Carumonam" title="Carumonam">Carumonam</a><sup>‡</sup></li> <li><a href="/wiki/Nocardicin_A" title="Nocardicin A">Nocardicin A</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%92-Lactamase_inhibitor" title="Β-Lactamase inhibitor">β-lactamase inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Penam" title="Penam">Penam</a> (<a href="/wiki/Sulbactam" title="Sulbactam">Sulbactam</a></li> <li><a href="/wiki/Tazobactam" title="Tazobactam">Tazobactam</a>)</li> <li><a href="/wiki/Clavam" title="Clavam">Clavam</a> (<a href="/wiki/Clavulanic_acid" title="Clavulanic acid">Clavulanic acid</a>)</li> <li>non-β-lactam (<a href="/wiki/Avibactam" title="Avibactam">Avibactam</a></li> <li><a href="/wiki/Durlobactam" title="Durlobactam">Durlobactam</a></li> <li><a href="/wiki/Relebactam" title="Relebactam">Relebactam</a></li> <li><a href="/wiki/Vaborbactam" title="Vaborbactam">Vaborbactam</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amoxicillin/clavulanic_acid" title="Amoxicillin/clavulanic acid">Amoxicillin/clavulanic acid</a><sup>#</sup></li> <li><a href="/wiki/Ampicillin/flucloxacillin" title="Ampicillin/flucloxacillin">Ampicillin/flucloxacillin</a></li> <li><a href="/wiki/Ampicillin/sulbactam" title="Ampicillin/sulbactam">Ampicillin/sulbactam</a> (<a href="/wiki/Sultamicillin" title="Sultamicillin">Sultamicillin</a>)</li> <li><a href="/wiki/Aztreonam/avibactam" title="Aztreonam/avibactam">Aztreonam/avibactam</a></li> <li><a href="/wiki/Benzathine_benzylpenicillin/procaine_benzylpenicillin" title="Benzathine benzylpenicillin/procaine benzylpenicillin">Benzathine benzylpenicillin/procaine benzylpenicillin</a></li> <li><a href="/wiki/Cefepime/enmetazobactam" title="Cefepime/enmetazobactam">Cefepime/enmetazobactam</a></li> <li><a href="/wiki/Cefoperazone/sulbactam" title="Cefoperazone/sulbactam">Cefoperazone/sulbactam</a></li> <li><a href="/wiki/Ceftazidime/avibactam" title="Ceftazidime/avibactam">Ceftazidime/avibactam</a></li> <li><a href="/wiki/Ceftolozane/tazobactam" title="Ceftolozane/tazobactam">Ceftolozane/tazobactam</a></li> <li><a href="/wiki/Imipenem/cilastatin" title="Imipenem/cilastatin">Imipenem/cilastatin</a><sup>#</sup></li> <li><a href="/wiki/Imipenem/cilastatin/relebactam" title="Imipenem/cilastatin/relebactam">Imipenem/cilastatin/relebactam</a></li> <li><a href="/wiki/Meropenem/vaborbactam" title="Meropenem/vaborbactam">Meropenem/vaborbactam</a></li> <li><a href="/wiki/Panipenem/betamipron" title="Panipenem/betamipron">Panipenem/betamipron</a></li> <li><a href="/wiki/Piperacillin/tazobactam" title="Piperacillin/tazobactam">Piperacillin/tazobactam</a></li> <li><a href="/wiki/Sulbactam/durlobactam" title="Sulbactam/durlobactam">Sulbactam/durlobactam</a></li> <li><a href="/wiki/Sulopenem/probenecid" title="Sulopenem/probenecid">Sulopenem/probenecid</a></li> <li><a href="/wiki/Ticarcillin/clavulanic_acid" title="Ticarcillin/clavulanic acid">Ticarcillin/clavulanic acid</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polypeptide_antibiotic" title="Polypeptide antibiotic">Polypeptides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lipopeptide" title="Lipopeptide">Lipopeptides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Insert into bacterial cell wall causing perforation and depolarization: <a href="/wiki/Daptomycin" title="Daptomycin">Daptomycin</a></li> <li><a href="/wiki/Surfactin" title="Surfactin">Surfactin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibits PG elongation and crosslinking: <a href="/wiki/Ramoplanin" title="Ramoplanin">Ramoplanin</a><sup>§</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intracellular</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibit <a href="/wiki/Peptidoglycan" title="Peptidoglycan">PG</a> subunit synthesis and transport: <a href="/wiki/N-Acetylmuramic_acid" title="N-Acetylmuramic acid">NAM</a> synthesis inhibition (<a href="/wiki/Fosfomycin" title="Fosfomycin">Fosfomycin</a>)</li> <li><a href="/wiki/D-alanine%E2%80%94D-alanine_ligase" title="D-alanine—D-alanine ligase">DADAL</a>/<a href="/wiki/Alanine_racemase" title="Alanine racemase">AR</a> inhibitors (<a href="/wiki/Cycloserine" title="Cycloserine">Cycloserine</a>)</li> <li><a href="/wiki/Bactoprenol" title="Bactoprenol">bactoprenol</a> inhibitors (<a href="/wiki/Bacitracin" title="Bacitracin">Bacitracin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Hydrolyze NAM-NAG <ul><li><a href="/wiki/Lysozyme" title="Lysozyme">lysozyme</a></li></ul></li> <li><a href="/wiki/Tyrothricin" title="Tyrothricin">Tyrothricin</a> <ul><li><a href="/wiki/Gramicidin" title="Gramicidin">Gramicidin</a></li> <li><a href="/wiki/Tyrocidine" title="Tyrocidine">Tyrocidine</a></li></ul></li> <li><a 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><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Carbapenem&oldid=1252118198">https://en.wikipedia.org/w/index.php?title=Carbapenem&oldid=1252118198</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Category</a>: <ul><li><a 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