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<span>History</span> </div> </a> <ul id="toc-History-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Uses</span> </div> </a> <ul id="toc-Uses-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Mechanism of action</span> </div> </a> <button aria-controls="toc-Mechanism_of_action-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 Mechanism of action subsection</span> </button> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> <li id="toc-Antibacterial" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antibacterial"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.1</span> <span>Antibacterial</span> </div> </a> <ul id="toc-Antibacterial-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Immunomodulation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Immunomodulation"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2</span> <span>Immunomodulation</span> </div> </a> <ul id="toc-Immunomodulation-sublist" class="vector-toc-list"> <li id="toc-Diffuse_panbronchiolitis" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Diffuse_panbronchiolitis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4.2.1</span> <span>Diffuse panbronchiolitis</span> </div> </a> <ul id="toc-Diffuse_panbronchiolitis-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </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">5</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-Antibiotic_macrolides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antibiotic_macrolides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Antibiotic macrolides</span> </div> </a> <ul id="toc-Antibiotic_macrolides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Ketolides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Ketolides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Ketolides</span> </div> </a> <ul id="toc-Ketolides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fluoroketolides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fluoroketolides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.3</span> <span>Fluoroketolides</span> </div> </a> <ul id="toc-Fluoroketolides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Non-antibiotic_macrolides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Non-antibiotic_macrolides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.4</span> <span>Non-antibiotic macrolides</span> </div> </a> <ul id="toc-Non-antibiotic_macrolides-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Antifungal_drugs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Antifungal_drugs"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.5</span> <span>Antifungal drugs</span> </div> </a> <ul id="toc-Antifungal_drugs-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Toxic_macrolides" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Toxic_macrolides"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.6</span> <span>Toxic macrolides</span> </div> </a> <ul id="toc-Toxic_macrolides-sublist" class="vector-toc-list"> </ul> </li> </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-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">7</span> <span>Side-effects</span> </div> </a> <ul id="toc-Side-effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Interactions" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Interactions"> <div class="vector-toc-text"> <span class="vector-toc-numb">8</span> <span>Interactions</span> </div> </a> <ul id="toc-Interactions-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> <span class="vector-toc-numb">9</span> <span>References</span> </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> <span class="vector-toc-numb">10</span> <span>Further reading</span> </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> </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">Macrolide</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 36 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-36" aria-hidden="true" ><span class="vector-icon mw-ui-icon-language-progressive mw-ui-icon-wikimedia-language-progressive"></span> <span class="vector-dropdown-label-text">36 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%85%D8%A7%D9%83%D8%B1%D9%88%D9%84%D9%8A%D8%AF" title="ماكروليد – Arabic" lang="ar" hreflang="ar" data-title="ماكروليد" 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/Macr%C3%B2lid" title="Macròlid – Catalan" lang="ca" hreflang="ca" data-title="Macròlid" 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/Makrolidy" title="Makrolidy – Czech" lang="cs" hreflang="cs" data-title="Makrolidy" 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/Makrolid" title="Makrolid – Danish" lang="da" hreflang="da" data-title="Makrolid" 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/Makrolide" title="Makrolide – German" lang="de" hreflang="de" data-title="Makrolide" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Macr%C3%B3lido" title="Macrólido – Spanish" lang="es" hreflang="es" data-title="Macrólido" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%85%D8%A7%DA%A9%D8%B1%D9%88%D9%84%DB%8C%D8%AF" title="ماکرولید – Persian" lang="fa" hreflang="fa" data-title="ماکرولید" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fo mw-list-item"><a href="https://fo.wikipedia.org/wiki/Makrolid" title="Makrolid – Faroese" lang="fo" hreflang="fo" data-title="Makrolid" data-language-autonym="Føroyskt" data-language-local-name="Faroese" class="interlanguage-link-target"><span>Føroyskt</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Macrolide" title="Macrolide – French" lang="fr" hreflang="fr" data-title="Macrolide" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Macr%C3%B3lido" title="Macrólido – Galician" lang="gl" hreflang="gl" data-title="Macrólido" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target"><span>Galego</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%A7%88%ED%81%AC%EB%A1%A4%EB%9D%BC%EC%9D%B4%EB%93%9C" title="마크롤라이드 – Korean" lang="ko" hreflang="ko" data-title="마크롤라이드" 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%84%D5%A1%D5%AF%D6%80%D5%B8%D5%AC%D5%AB%D5%A4%D5%B6%D5%A5%D6%80" title="Մակրոլիդներ – Armenian" lang="hy" hreflang="hy" data-title="Մակրոլիդներ" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target"><span>Հայերեն</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Makrolida" title="Makrolida – Indonesian" lang="id" hreflang="id" data-title="Makrolida" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target"><span>Bahasa Indonesia</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Macrolidi" title="Macrolidi – Italian" lang="it" hreflang="it" data-title="Macrolidi" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ht mw-list-item"><a href="https://ht.wikipedia.org/wiki/Makrolid" title="Makrolid – Haitian Creole" lang="ht" hreflang="ht" data-title="Makrolid" data-language-autonym="Kreyòl ayisyen" data-language-local-name="Haitian Creole" class="interlanguage-link-target"><span>Kreyòl ayisyen</span></a></li><li class="interlanguage-link interwiki-arz mw-list-item"><a href="https://arz.wikipedia.org/wiki/%D9%85%D8%A7%D9%83%D8%B1%D9%88%D9%84%D8%A7%D9%8A%D8%AF" title="ماكرولايد – Egyptian Arabic" lang="arz" hreflang="arz" data-title="ماكرولايد" data-language-autonym="مصرى" data-language-local-name="Egyptian Arabic" class="interlanguage-link-target"><span>مصرى</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Macrolide" title="Macrolide – Dutch" lang="nl" hreflang="nl" data-title="Macrolide" 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%83%9E%E3%82%AF%E3%83%AD%E3%83%A9%E3%82%A4%E3%83%89" title="マクロライド – Japanese" lang="ja" hreflang="ja" data-title="マクロライド" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Makrolidlar" title="Makrolidlar – Uzbek" lang="uz" hreflang="uz" data-title="Makrolidlar" 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/Makrolidy" title="Makrolidy – Polish" lang="pl" hreflang="pl" data-title="Makrolidy" 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/Macr%C3%B3lido" title="Macrólido – Portuguese" lang="pt" hreflang="pt" data-title="Macrólido" 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/Macrolid%C4%83" title="Macrolidă – Romanian" lang="ro" hreflang="ro" data-title="Macrolidă" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9C%D0%B0%D0%BA%D1%80%D0%BE%D0%BB%D0%B8%D0%B4%D1%8B" title="Макролиды – Russian" lang="ru" hreflang="ru" data-title="Макролиды" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Makrolid" title="Makrolid – Slovenian" lang="sl" hreflang="sl" data-title="Makrolid" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Makrolid" title="Makrolid – Serbian" lang="sr" hreflang="sr" data-title="Makrolid" 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/Makrolid" title="Makrolid – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Makrolid" 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/Makrolidit" title="Makrolidit – Finnish" lang="fi" hreflang="fi" data-title="Makrolidit" 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/Makrolid" title="Makrolid – Swedish" lang="sv" hreflang="sv" data-title="Makrolid" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B9%81%E0%B8%A1%E0%B9%82%E0%B8%84%E0%B8%A3%E0%B9%84%E0%B8%A5%E0%B8%94%E0%B9%8C" title="แมโครไลด์ – Thai" lang="th" hreflang="th" data-title="แมโครไลด์" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Makrolid" title="Makrolid – Turkish" lang="tr" hreflang="tr" data-title="Makrolid" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9C%D0%B0%D0%BA%D1%80%D0%BE%D0%BB%D1%96%D0%B4%D0%B8" title="Макроліди – Ukrainian" lang="uk" hreflang="uk" data-title="Макроліди" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Macrolide" title="Macrolide – Vietnamese" lang="vi" hreflang="vi" data-title="Macrolide" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wa mw-list-item"><a href="https://wa.wikipedia.org/wiki/Macrolide" title="Macrolide – Walloon" lang="wa" hreflang="wa" data-title="Macrolide" data-language-autonym="Walon" data-language-local-name="Walloon" class="interlanguage-link-target"><span>Walon</span></a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E5%A4%A7%E7%8E%AF%E5%86%85%E9%85%AF%E7%B1%BB%E6%8A%97%E7%94%9F%E7%B4%A0" title="大环内酯类抗生素 – Wu" lang="wuu" hreflang="wuu" data-title="大环内酯类抗生素" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target"><span>吴语</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E5%A4%A7%E7%92%B0%E5%85%A7%E9%85%AF" title="大環內酯 – Cantonese" lang="yue" hreflang="yue" data-title="大環內酯" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E5%A4%A7%E7%92%B0%E5%85%A7%E9%85%AF" title="大環內酯 – Chinese" lang="zh" hreflang="zh" data-title="大環內酯" 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/Q422687#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> </div> </div> </div> </header> <div class="vector-page-toolbar"> <div 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src="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Erythromycin_A.svg/150px-Erythromycin_A.svg.png" decoding="async" width="150" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Erythromycin_A.svg/225px-Erythromycin_A.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/65/Erythromycin_A.svg/300px-Erythromycin_A.svg.png 2x" data-file-width="624" data-file-height="484" /></a><figcaption><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a>. The macrolide ring is the <a href="/wiki/Lactone" title="Lactone">lactone</a> (cyclic <a href="/wiki/Ester" title="Ester">ester</a>) at upper left.</figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Clarithromycin_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Clarithromycin_structure.svg/150px-Clarithromycin_structure.svg.png" decoding="async" width="150" height="116" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Clarithromycin_structure.svg/225px-Clarithromycin_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Clarithromycin_structure.svg/300px-Clarithromycin_structure.svg.png 2x" data-file-width="620" data-file-height="481" /></a><figcaption><a href="/wiki/Clarithromycin" title="Clarithromycin">Clarithromycin</a></figcaption></figure> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Roxithromycin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Roxithromycin.svg/150px-Roxithromycin.svg.png" decoding="async" width="150" height="122" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Roxithromycin.svg/225px-Roxithromycin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d3/Roxithromycin.svg/300px-Roxithromycin.svg.png 2x" data-file-width="620" data-file-height="505" /></a><figcaption><a href="/wiki/Roxithromycin" title="Roxithromycin">Roxithromycin</a></figcaption></figure> <p><b>Macrolides</b> are a class of mostly <a href="/wiki/Natural_product" title="Natural product">natural products</a> with a large <a href="/wiki/Macrocycle" title="Macrocycle">macrocyclic</a> <a href="/wiki/Lactone" title="Lactone">lactone</a> ring to which one or more <a href="/wiki/Deoxy_sugar" title="Deoxy sugar">deoxy sugars</a>, usually <a href="/wiki/Cladinose" title="Cladinose">cladinose</a> and <a href="/wiki/Desosamine" title="Desosamine">desosamine</a>, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the <a href="/wiki/Polyketide" title="Polyketide">polyketide</a> class of natural products. Some macrolides have <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> or <a href="/wiki/Antifungal" title="Antifungal">antifungal</a> activity and are used as <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">pharmaceutical drugs</a>. <a href="/wiki/Rapamycin" class="mw-redirect" title="Rapamycin">Rapamycin</a> is also a macrolide and was originally developed as an antifungal, but has since been used as an <a href="/wiki/Immunosuppressant_drug" class="mw-redirect" title="Immunosuppressant drug">immunosuppressant drug</a> and is being investigated as a potential <a href="/wiki/Life_extension" title="Life extension">longevity therapeutic</a>.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Definition">Definition</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=1" title="Edit section: Definition"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In general, any macrocyclic lactone having greater than 8-membered rings are candidates for this class. The macrocycle may contain <a href="/wiki/Amine" title="Amine">amino</a> nitrogen, <a href="/wiki/Amide" title="Amide">amide</a> nitrogen (but should be differentiated from <a href="/wiki/Cyclopeptide" class="mw-redirect" title="Cyclopeptide">cyclopeptides</a>), an <a href="/wiki/Oxazole" title="Oxazole">oxazole</a> ring, or a <a href="/wiki/Thiazole" title="Thiazole">thiazole</a> ring. <a href="/wiki/Benzene" title="Benzene">Benzene</a> rings are excluded, in order to differentiate from <a href="/wiki/Tannin" title="Tannin">tannins</a>. Also <a href="/wiki/Lactam" title="Lactam">lactams</a> instead of lactones (as in the <a href="/wiki/Ansamycin" title="Ansamycin">ansamycin</a> family) are excluded. Included are not only 12-16 membered macrocycles but also larger rings as in <a href="/wiki/Tacrolimus" title="Tacrolimus">tacrolimus</a>.<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> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first macrolide discovered was <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a>, which was first used in 1952. Erythromycin was widely used as a substitute to <a href="/wiki/Penicillin" title="Penicillin">penicillin</a> in cases where patients were allergic to penicillin or had penicillin-resistant illnesses. Later macrolides developed, including <a href="/wiki/Azithromycin" title="Azithromycin">azithromycin</a> and <a href="/wiki/Clarithromycin" title="Clarithromycin">clarithromycin</a>, stemmed from chemically modifying erythromycin; these compounds were designed to be more easily absorbed and have fewer side-effects (erythromycin caused gastrointestinal side-effects in a significant proportion of users).<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> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=3" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Antibiotic macrolides are used to treat infections caused by <a href="/wiki/Gram-positive_bacteria" title="Gram-positive bacteria">Gram-positive bacteria</a> (e.g., <i><a href="/wiki/Streptococcus_pneumoniae" title="Streptococcus pneumoniae">Streptococcus pneumoniae</a></i>) and limited <a href="/wiki/Gram-negative_bacteria" title="Gram-negative bacteria">Gram-negative bacteria</a> (e.g., <i><a href="/wiki/Bordetella_pertussis" title="Bordetella pertussis">Bordetella pertussis</a></i>, <i><a href="/wiki/Haemophilus_influenzae" title="Haemophilus influenzae">Haemophilus influenzae</a></i>), and some respiratory tract and soft-tissue infections.<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> The antimicrobial spectrum of macrolides is slightly wider than that of <a href="/wiki/Penicillin" title="Penicillin">penicillin</a>, and, therefore, macrolides are a common substitute for patients with a penicillin allergy. Beta-hemolytic <a href="/wiki/Streptococcus" title="Streptococcus">streptococci</a>, <a href="/wiki/Pneumococci" class="mw-redirect" title="Pneumococci">pneumococci</a>, <a href="/wiki/Staphylococcus" title="Staphylococcus">staphylococci</a>, and <a href="/wiki/Enterococcus" title="Enterococcus">enterococci</a> are usually susceptible to macrolides. Unlike penicillin, macrolides have been shown to be effective against <i><a href="/wiki/Legionella_pneumophila" title="Legionella pneumophila">Legionella pneumophila</a></i>, <a href="/wiki/Mycoplasma" title="Mycoplasma">Mycoplasma</a>, <a href="/wiki/Mycobacterium" title="Mycobacterium">Mycobacterium</a>, some <a href="/wiki/Rickettsia" title="Rickettsia">Rickettsia</a>, and <a href="/wiki/Chlamydia_(bacterium)" class="mw-redirect" title="Chlamydia (bacterium)">Chlamydia</a>. </p><p>Macrolides are <i>not</i> to be used on non<a href="/wiki/Ruminant" title="Ruminant">ruminant</a> herbivores, such as horses and rabbits. They rapidly produce a reaction causing fatal digestive disturbance.<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> It can be used in horses less than one year old, but care must be taken that other horses (such as a foal's mare) do not come in contact with the macrolide treatment. </p><p>Macrolides can be administered in a variety of ways, including tablets, capsules, suspensions, injections and topically.<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="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=4" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Antibacterial">Antibacterial</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=5" title="Edit section: Antibacterial"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Macrolides are <a href="/wiki/Protein_synthesis_inhibitor" title="Protein synthesis inhibitor">protein synthesis inhibitors</a>. The <a href="/wiki/Mechanism_of_action" title="Mechanism of action">mechanism of action</a> of macrolides is <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibition</a> of bacterial <a href="/wiki/Protein_biosynthesis" title="Protein biosynthesis">protein biosynthesis</a>, and they are thought to do this by preventing <a href="/wiki/Peptidyltransferase" class="mw-redirect" title="Peptidyltransferase">peptidyltransferase</a> from adding the growing peptide attached to <a href="/wiki/Transfer_RNA" title="Transfer RNA">tRNA</a> to the next amino acid<sup id="cite_ref-pharmamotion_7-0" class="reference"><a href="#cite_note-pharmamotion-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> (similarly to <a href="/wiki/Chloramphenicol" title="Chloramphenicol">chloramphenicol</a><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>) as well as inhibiting <a href="/wiki/Bacterial_translation" title="Bacterial translation">bacterial ribosomal translation</a>.<sup id="cite_ref-pharmamotion_7-1" class="reference"><a href="#cite_note-pharmamotion-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Another potential mechanism is premature dissociation of the <a href="/wiki/Peptidyl-tRNA" class="mw-redirect" title="Peptidyl-tRNA">peptidyl-tRNA</a> from the ribosome.<sup id="cite_ref-lovmar_9-0" class="reference"><a href="#cite_note-lovmar-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Macrolide antibiotics bind reversibly to the P site on the <a href="/wiki/50S" class="mw-redirect" title="50S">50S</a> subunit of the bacterial <a href="/wiki/Ribosome" title="Ribosome">ribosome</a>. This action is considered to be <a href="/wiki/Bacteriostatic" class="mw-redirect" title="Bacteriostatic">bacteriostatic</a>. Macrolides are actively concentrated within <a href="/wiki/White_blood_cell" title="White blood cell">leukocytes</a>, and thus are transported into the site of infection.<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="Immunomodulation">Immunomodulation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=6" title="Edit section: Immunomodulation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Diffuse_panbronchiolitis">Diffuse panbronchiolitis</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=7" title="Edit section: Diffuse panbronchiolitis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The macrolide antibiotics erythromycin, clarithromycin, and roxithromycin have proven to be an effective long-term treatment for the <a href="/wiki/Idiopathic" class="mw-redirect" title="Idiopathic">idiopathic</a>, Asian-prevalent lung disease <a href="/wiki/Diffuse_panbronchiolitis" title="Diffuse panbronchiolitis">diffuse panbronchiolitis</a> (DPB).<sup id="cite_ref-mac_11-0" class="reference"><a href="#cite_note-mac-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-mac08_12-0" class="reference"><a href="#cite_note-mac08-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The successful results of macrolides in DPB stems from controlling symptoms through <a href="/wiki/Immunotherapy" title="Immunotherapy">immunomodulation</a> (adjusting the immune response),<sup id="cite_ref-mac08_12-1" class="reference"><a href="#cite_note-mac08-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> with the added benefit of <a href="/wiki/Dosing" title="Dosing">low-dose</a> requirements.<sup id="cite_ref-mac_11-1" class="reference"><a href="#cite_note-mac-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>With macrolide therapy in DPB, great reduction in bronchiolar inflammation and damage is achieved through suppression of not only <a href="/wiki/Neutrophil_granulocyte" class="mw-redirect" title="Neutrophil granulocyte">neutrophil granulocyte</a> proliferation but also <a href="/wiki/Lymphocyte" title="Lymphocyte">lymphocyte</a> activity and obstructive <a href="/wiki/Secretion" title="Secretion">secretions</a> in airways.<sup id="cite_ref-mac_11-2" class="reference"><a href="#cite_note-mac-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> The antimicrobial and antibiotic effects of macrolides, however, are not believed to be involved in their beneficial effects toward treating DPB.<sup id="cite_ref-mac04_13-0" class="reference"><a href="#cite_note-mac04-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> This is evident, as the treatment dosage is much too low to fight infection, and in DPB cases with the occurrence of the macrolide-resistant bacterium <i><a href="/wiki/Pseudomonas_aeruginosa" title="Pseudomonas aeruginosa">Pseudomonas aeruginosa</a></i>, macrolide therapy still produces substantial anti-inflammatory results.<sup id="cite_ref-mac_11-3" class="reference"><a href="#cite_note-mac-11"><span class="cite-bracket">[</span>11<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=Macrolide&action=edit&section=8" title="Edit section: Examples"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Antibiotic_macrolides">Antibiotic macrolides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=9" title="Edit section: Antibiotic macrolides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>US FDA-approved: </p> <ul><li><a href="/wiki/Azithromycin" title="Azithromycin">Azithromycin</a> –  unique; does not extensively inhibit <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a><sup id="cite_ref-pmid31628882_14-0" class="reference"><a href="#cite_note-pmid31628882-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Clarithromycin" title="Clarithromycin">Clarithromycin</a></li> <li><a href="/wiki/Dirithromycin" title="Dirithromycin">Dirithromycin</a> –  discontinued but was US FDA approved</li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a></li></ul> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Azithromycin_250mg.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Azithromycin_250mg.jpg/220px-Azithromycin_250mg.jpg" decoding="async" width="220" height="171" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/09/Azithromycin_250mg.jpg/330px-Azithromycin_250mg.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/09/Azithromycin_250mg.jpg/440px-Azithromycin_250mg.jpg 2x" data-file-width="2965" data-file-height="2310" /></a><figcaption><a href="/wiki/Azithromycin" title="Azithromycin">Azithromycin</a> capsules</figcaption></figure> <p>Not approved in the US by FDA but approved in the other countries by respective national authorities: </p> <ul><li><a href="/wiki/Carbomycin" title="Carbomycin">Carbomycin A</a></li> <li><a href="/wiki/Josamycin" title="Josamycin">Josamycin</a></li> <li><a href="/wiki/Kitasamycin" title="Kitasamycin">Kitasamycin</a></li> <li><a href="/wiki/Midecamycin" title="Midecamycin">Midecamycin</a>/<a href="/w/index.php?title=Midecamycin_acetate&action=edit&redlink=1" class="new" title="Midecamycin acetate (page does not exist)">midecamycin acetate</a></li> <li><a href="/wiki/Oleandomycin" title="Oleandomycin">Oleandomycin</a></li> <li><a href="/wiki/Spiramycin" title="Spiramycin">Spiramycin</a> –  approved in the EU, and in other countries</li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a> –  used in Italy and Turkey</li> <li><a href="/wiki/Tylosin" title="Tylosin">Tylosin</a>/<a href="/wiki/Tylocine" class="mw-redirect" title="Tylocine">tylocine</a> –  used in animals</li> <li><a href="/wiki/Roxithromycin" title="Roxithromycin">Roxithromycin</a></li></ul> <p>Not approved as a drug for medical use: </p> <ul><li><a href="/wiki/Boromycin" title="Boromycin">Boromycin</a><sup id="cite_ref-pmid17991498_15-0" class="reference"><a href="#cite_note-pmid17991498-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup></li></ul> <div class="mw-heading mw-heading3"><h3 id="Ketolides">Ketolides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=10" title="Edit section: Ketolides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Ketolide" title="Ketolide">Ketolides</a> are a class of antibiotics that are structurally related to the macrolides. They are used to treat respiratory tract infections caused by macrolide-resistant bacteria. Ketolides are especially effective, as they have two ribosomal binding sites. </p><p>Ketolides include: </p> <ul><li><a href="/wiki/Telithromycin" title="Telithromycin">Telithromycin</a> –  the first and only approved ketolide<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></li> <li><a href="/wiki/Cethromycin" title="Cethromycin">Cethromycin</a></li> <li><a href="/wiki/Solithromycin" title="Solithromycin">Solithromycin</a></li></ul> <div class="mw-heading mw-heading3"><h3 id="Fluoroketolides">Fluoroketolides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=11" title="Edit section: Fluoroketolides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Fluoroketolides are a class of antibiotics that are structurally related to the ketolides. The fluoroketolides have three ribosomal interaction sites. </p><p>Fluoroketolides include: </p> <ul><li><a href="/wiki/Solithromycin" title="Solithromycin">Solithromycin</a> –  the first and so far only fluoroketolide (not yet approved)</li></ul> <div class="mw-heading mw-heading3"><h3 id="Non-antibiotic_macrolides">Non-antibiotic macrolides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=12" title="Edit section: Non-antibiotic macrolides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The drugs <a href="/wiki/Tacrolimus" title="Tacrolimus">tacrolimus</a>, <a href="/wiki/Pimecrolimus" title="Pimecrolimus">pimecrolimus</a>, and <a href="/wiki/Sirolimus" title="Sirolimus">sirolimus</a>, which are used as <a href="/wiki/Immunosuppressant" class="mw-redirect" title="Immunosuppressant">immunosuppressants</a> or immunomodulators, are also macrolides. They have similar activity to <a href="/wiki/Ciclosporin" title="Ciclosporin">ciclosporin</a>. </p> <div class="mw-heading mw-heading3"><h3 id="Antifungal_drugs">Antifungal drugs</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=13" title="Edit section: Antifungal drugs"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/Polyene_antimycotic" title="Polyene antimycotic">Polyene antimycotics</a>, such as <a href="/wiki/Amphotericin_B" title="Amphotericin B">amphotericin B</a>, <a href="/wiki/Nystatin" title="Nystatin">nystatin</a> etc., are a subgroup of macrolides.<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/Cruentaren" title="Cruentaren">Cruentaren</a> is another example of an antifungal macrolide.<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> </p> <div class="mw-heading mw-heading3"><h3 id="Toxic_macrolides">Toxic macrolides</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=14" title="Edit section: Toxic macrolides"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A variety of toxic macrolides produced by bacteria have been isolated and characterized, such as the <a href="/wiki/Mycolactone" title="Mycolactone">mycolactones</a>. </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=Macrolide&action=edit&section=15" title="Edit section: Resistance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The primary means of <a href="/wiki/Antimicrobial_resistance" title="Antimicrobial resistance">bacterial resistance</a> to macrolides occurs by post-transcriptional methylation of the <a href="/wiki/23S_ribosomal_RNA" title="23S ribosomal RNA">23S</a> bacterial ribosomal RNA. This acquired resistance can be either <a href="/wiki/Plasmid" title="Plasmid">plasmid</a>-mediated or chromosomal, i.e., through mutation, and results in <a href="/wiki/Cross-resistance" title="Cross-resistance">cross-resistance</a> to macrolides, <a href="/wiki/Lincosamides" title="Lincosamides">lincosamides</a>, and <a href="/wiki/Streptogramin" title="Streptogramin">streptogramins</a> (an MLS-resistant phenotype).<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Two other forms of acquired resistance include the production of drug-inactivating enzymes (esterases<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><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> or kinases<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>), as well as the production of active ATP-dependent efflux proteins that transport the drug outside of the cell.<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>Azithromycin has been used to treat strep throat (<a href="/wiki/Group_A_streptococcal_infection" title="Group A streptococcal infection">Group A streptococcal (GAS) infection</a> caused by <i><a href="/wiki/Streptococcus_pyogenes" title="Streptococcus pyogenes">Streptococcus pyogenes</a></i>) in penicillin-sensitive patients; however, macrolide-resistant strains of GAS occur with moderate frequency. <a href="/wiki/Cephalosporin" title="Cephalosporin">Cephalosporin</a> is another option for these patients.<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-heading2"><h2 id="Side-effects">Side-effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=16" title="Edit section: Side-effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A 2008 <i><a href="/wiki/British_Medical_Journal" class="mw-redirect" title="British Medical Journal">British Medical Journal</a></i> article highlights that the combination of some macrolides and <a href="/wiki/Statins" class="mw-redirect" title="Statins">statins</a> (used for lowering cholesterol) is not advisable and can lead to debilitating <a href="/wiki/Myopathy" title="Myopathy">myopathy</a>.<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> This is because some macrolides (clarithromycin and erythromycin, not azithromycin) are potent <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitors</a> of the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> system, particularly of <a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a>. Macrolides, mainly erythromycin and clarithromycin, also have a class effect of <a href="/wiki/QT_prolongation" class="mw-redirect" title="QT prolongation">QT prolongation</a>, which can lead to <a href="/wiki/Torsades_de_pointes" title="Torsades de pointes">torsades de pointes</a>. Macrolides exhibit <a href="/wiki/Enterohepatic_recycling" class="mw-redirect" title="Enterohepatic recycling">enterohepatic recycling</a>; that is, the drug is absorbed in the gut and sent to the liver, only to be excreted into the <a href="/wiki/Duodenum" title="Duodenum">duodenum</a> in bile from the liver. This can lead to a buildup of the product in the system, thereby causing nausea. In infants the use of erythromycin has been associated with pyloric stenosis.<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><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> </p><p>Some macrolides are also known to cause <a href="/wiki/Cholestasis" title="Cholestasis">cholestasis</a>, a condition where bile cannot flow from the liver to the duodenum.<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> A study reported in 2019 found an association between erythromycin use during infancy and developing IHPS (Infantile hypertrophic pyloric stenosis) in infants.<sup id="cite_ref-:0_29-0" class="reference"><a href="#cite_note-:0-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> However, no significant association was found between macrolides use during pregnancy or breastfeeding.<sup id="cite_ref-:0_29-1" class="reference"><a href="#cite_note-:0-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> </p><p>A Cochrane review showed gastrointestinal symptoms to be the most frequent adverse event reported in literature.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=17" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p><a href="/wiki/CYP3A4" title="CYP3A4">CYP3A4</a> is an enzyme that metabolizes many drugs in the liver. Macrolides inhibit CYP3A4, which means they reduce its activity and increase the blood levels of the drugs that depend on it for elimination. This can lead to adverse effects or drug-drug interactions.<sup id="cite_ref-pmid32807049_31-0" class="reference"><a href="#cite_note-pmid32807049-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>Macrolides have cyclic structure with a <a href="/wiki/Lactone" title="Lactone">lactone</a> ring and sugar moieties. They can inhibit CYP3A4 by a mechanism called mechanism-based inhibition (MBI), which involves the formation of reactive metabolites that bind covalently and irreversibly to the enzyme, rendering it inactive. MBI is more serious and long-lasting than reversible inhibition, as it requires the synthesis of new enzyme molecules to restore the activity.<sup id="cite_ref-pmid31628882_14-1" class="reference"><a href="#cite_note-pmid31628882-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>The degree of MBI by macrolides depends on the size and structure of their lactone ring. <a href="/wiki/Clarithromycin" title="Clarithromycin">Clarithromycin</a> and <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a> have a 14-membered lactone ring, which is more prone to demethylation by CYP3A4 and subsequent formation of nitrosoalkenes, the reactive metabolites that cause MBI. <a href="/wiki/Azithromycin" title="Azithromycin">Azithromycin</a>, on the other hand, has a 15-membered lactone ring, which is less susceptible to demethylation and nitrosoalkene formation. Therefore, azithromycin is a weak inhibitor of CYP3A4, while clarithromycin and erythromycin are strong inhibitors which increase the area under the curve (AUC) value of co-administered drugs more than five-fold.<sup id="cite_ref-pmid31628882_14-2" class="reference"><a href="#cite_note-pmid31628882-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> AUC it is a measure of the drug exposure in the body over time. By inhibiting CYP3A4, macrolide antibitiotics, such as <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a> and <a href="/wiki/Clarithromycin" title="Clarithromycin">clarithromycin</a>, but not azithromycin, can significantly increase the AUC of the drugs that depend on it for clearance, which can lead to higher risk of adverse effects or drug-drug interactions. Azithromycin stands apart from other macrolide antibiotics because it is a weak inhibitor of CYP3A4, and does not significantly increase AUC value of co-administered drugs.<sup id="cite_ref-pmid11012550_32-0" class="reference"><a href="#cite_note-pmid11012550-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>The difference in CYP3A4 inhibition by macrolides has clinical implications, for example, for patients who take <a href="/wiki/Statin" title="Statin">statins</a>, which are cholesterol-lowering drugs that are mainly metabolized by CYP3A4. Co-administration of clarithromycin or erythromycin with statins can increase the risk of statin-induced myopathy, a condition that causes muscle pain and damage. Azithromycin, however, does not significantly affect the pharmacokinetics of statins and is considered a safer alternative. Another option is to use fluvastatin, a statin that is metabolized by CYP2C9, an enzyme that is not inhibited by clarithromycin.<sup id="cite_ref-pmid31628882_14-3" class="reference"><a href="#cite_note-pmid31628882-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>Macrolides, including azithromycin, should not be taken with <a href="/wiki/Colchicine" title="Colchicine">colchicine</a> as it may lead to colchicine toxicity. Symptoms of colchicine toxicity include gastrointestinal upset, fever, myalgia, pancytopenia, and organ failure.<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><sup id="cite_ref-pmid36104598_34-0" class="reference"><a href="#cite_note-pmid36104598-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Macrolide&action=edit&section=18" 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 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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 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Boston: Academic Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-526451-8" title="Special:BookSources/978-0-12-526451-8"><bdi>978-0-12-526451-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Macrolide+antibiotics%3A+chemistry%2C+biology%2C+and+practice&rft.place=Boston&rft.edition=2nd&rft.pub=Academic+Press&rft.date=2002&rft.isbn=978-0-12-526451-8&rft.aulast=%C5%8Cmura&rft.aufirst=S&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMacrolide" class="Z3988"></span></li> <li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFBryskier" class="citation web cs1">Bryskier A. <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">"Antibacterial Agents; Structure Activity Relationships"</a> <span class="cs1-format">(PDF)</span>. p. 143. Archived from <a rel="nofollow" class="external text" href="http://www.infectio-lille.com/diaporamas/invites/struct-act-duatb05-bryskier.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 2006-03-04.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Antibacterial+Agents%3B+Structure+Activity+Relationships&rft.pages=143&rft.aulast=Bryskier&rft.aufirst=Andr%C3%A9&rft_id=http%3A%2F%2Fwww.infectio-lille.com%2Fdiaporamas%2Finvites%2Fstruct-act-duatb05-bryskier.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMacrolide" class="Z3988"></span></li></ul> </div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline 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.navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Protein_synthesis_inhibitor_antibiotics" title="Template:Protein synthesis inhibitor antibiotics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Protein_synthesis_inhibitor_antibiotics" title="Template talk:Protein synthesis inhibitor antibiotics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Protein_synthesis_inhibitor_antibiotics" title="Special:EditPage/Template:Protein synthesis inhibitor antibiotics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antibacterials_that_inhibit_protein_synthesis_(J01A,_J01B,_J01F,_J01G,_QJ01XQ)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antibiotic" title="Antibiotic">Antibacterials</a> that <a href="/wiki/Protein_synthesis_inhibitor" title="Protein synthesis inhibitor">inhibit protein synthesis</a> (<a href="/wiki/ATC_code_J01#J01A" title="ATC code J01">J01A</a>, <a href="/wiki/ATC_code_J01#J01B" title="ATC code J01">J01B</a>, <a href="/wiki/ATC_code_J01#J01F" title="ATC code J01">J01F</a>, <a href="/wiki/ATC_code_J01#J01G" title="ATC code J01">J01G</a>, <a href="/wiki/ATC_code_J01#QJ01XQ" title="ATC code J01">QJ01XQ</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/30S" class="mw-redirect" title="30S">30S</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aminoglycoside" title="Aminoglycoside">Aminoglycosides</a><br />(<a href="/wiki/Bacterial_translation#Initiation" title="Bacterial translation">initiation</a> inhibitors)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">-mycin (<i><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a></i>)</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/Streptomycin" title="Streptomycin">Streptomycin</a><sup>#</sup></li> <li><a href="/wiki/Dihydrostreptomycin" title="Dihydrostreptomycin">Dihydrostreptomycin</a></li></ul> <ul><li><a href="/wiki/Neomycin" title="Neomycin">Neomycin</a><sup>#</sup> <ul><li><a href="/wiki/Framycetin" class="mw-redirect" title="Framycetin">Framycetin</a></li> <li><a href="/wiki/Paromomycin" title="Paromomycin">Paromomycin</a><sup>#</sup></li> <li><a href="/wiki/Ribostamycin" title="Ribostamycin">Ribostamycin</a></li></ul></li></ul> <ul><li><a href="/wiki/Kanamycin" class="mw-redirect" title="Kanamycin">Kanamycin</a> <ul><li><a href="/wiki/Amikacin" title="Amikacin">Amikacin</a><sup>#</sup></li> <li><a href="/wiki/Arbekacin" title="Arbekacin">Arbekacin</a></li> <li><a href="/wiki/Bekanamycin" title="Bekanamycin">Bekanamycin</a></li> <li><a href="/wiki/Dibekacin" title="Dibekacin">Dibekacin</a></li></ul></li></ul> <ul><li><a href="/wiki/Tobramycin" title="Tobramycin">Tobramycin</a> (<a href="/wiki/Loteprednol/tobramycin" title="Loteprednol/tobramycin">+loteprednol</a>)</li> <li><a href="/wiki/Spectinomycin" title="Spectinomycin">Spectinomycin</a><sup>#</sup></li> <li><a href="/wiki/Hygromycin_B" title="Hygromycin B">Hygromycin B</a></li> <li><a href="/wiki/Totomycin" title="Totomycin">Totomycin</a></li> <li><a href="/wiki/Apramycin" title="Apramycin">Apramycin</a></li> <li><a href="/wiki/Nourseothricin" title="Nourseothricin">Nourseothricin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">-micin (<i><a href="/wiki/Micromonospora" title="Micromonospora">Micromonospora</a></i>)</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/Gentamicin" title="Gentamicin">Gentamicin</a><sup>#</sup> <ul><li><a href="/wiki/Netilmicin" title="Netilmicin">Netilmicin</a></li> <li><a href="/wiki/Sisomicin" title="Sisomicin">Sisomicin</a></li> <li><a href="/wiki/Micronomicin" title="Micronomicin">Micronomicin</a></li> <li><a href="/wiki/Plazomicin" title="Plazomicin">Plazomicin</a><sup>#</sup></li> <li><a href="/wiki/Isepamicin" title="Isepamicin">Isepamicin</a></li></ul></li></ul> <ul><li><a href="/wiki/Verdamicin" title="Verdamicin">Verdamicin</a></li> <li><a href="/wiki/Astromicin" title="Astromicin">Astromicin</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><a href="/wiki/Butirosin" title="Butirosin">Butirosin</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/Tetracycline_antibiotics" title="Tetracycline antibiotics">Tetracycline antibiotics</a><br />(<a href="/wiki/Transfer_RNA" title="Transfer RNA">tRNA</a> binding)</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%">Tetracyclines</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/Doxycycline" title="Doxycycline">Doxycycline</a><sup>#</sup></li> <li><a href="/wiki/Chlortetracycline" title="Chlortetracycline">Chlortetracycline</a></li> <li><a href="/wiki/Clomocycline" title="Clomocycline">Clomocycline</a></li> <li><a href="/wiki/Demeclocycline" title="Demeclocycline">Demeclocycline</a></li> <li><a href="/wiki/Eravacycline" title="Eravacycline">Eravacycline</a></li> <li><a href="/wiki/Lymecycline" title="Lymecycline">Lymecycline</a></li> <li><a href="/wiki/Meclocycline" title="Meclocycline">Meclocycline</a><sup>‡</sup></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/wiki/Omadacycline" title="Omadacycline">Omadacycline</a></li> <li><a href="/wiki/Oxytetracycline" title="Oxytetracycline">Oxytetracycline</a></li> <li><a href="/wiki/Penimepicycline" title="Penimepicycline">Penimepicycline</a></li> <li><a href="/wiki/Rolitetracycline" title="Rolitetracycline">Rolitetracycline</a></li> <li><a href="/wiki/Sarecycline" title="Sarecycline">Sarecycline</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Glycylcycline" title="Glycylcycline">Glycylcyclines</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/Tigecycline" title="Tigecycline">Tigecycline</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/50S" class="mw-redirect" title="50S">50S</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/2-Oxazolidone" class="mw-redirect" title="2-Oxazolidone">Oxazolidinone</a><br />(<a href="/wiki/Bacterial_translation#Initiation" title="Bacterial translation">initiation</a> inhibitors)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Eperezolid" title="Eperezolid">Eperezolid</a></li> <li><a href="/wiki/Linezolid" title="Linezolid">Linezolid</a><sup>#</sup></li> <li><a href="/wiki/Posizolid" title="Posizolid">Posizolid</a></li> <li><a href="/wiki/Radezolid" title="Radezolid">Radezolid</a></li> <li><a href="/wiki/Ranbezolid" title="Ranbezolid">Ranbezolid</a></li> <li><a href="/wiki/Sutezolid" title="Sutezolid">Sutezolid</a></li> <li><a href="/wiki/Tedizolid" title="Tedizolid">Tedizolid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Peptidyl_transferase" class="mw-redirect" title="Peptidyl transferase">Peptidyl transferase</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 id="Amphenicols" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amphenicol" title="Amphenicol">Amphenicols</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/Chloramphenicol" title="Chloramphenicol">Chloramphenicol</a><sup>#</sup></li> <li><a href="/wiki/Azidamfenicol" title="Azidamfenicol">Azidamfenicol</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/Florfenicol" title="Florfenicol">Florfenicol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">MLS (<a href="/wiki/Bacterial_translation#Elongation" title="Bacterial translation">transpeptidation/translocation</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 selflink">Macrolides</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/Azithromycin" title="Azithromycin">Azithromycin</a><sup>#</sup></li> <li><a href="/wiki/Boromycin" title="Boromycin">Boromycin</a></li> <li><a href="/wiki/Carbomycin" title="Carbomycin">Carbomycin</a></li> <li><a href="/wiki/Carrimycin" title="Carrimycin">Carrimycin</a></li> <li><a href="/wiki/Clarithromycin" title="Clarithromycin">Clarithromycin</a><sup>#</sup></li> <li><a href="/wiki/Dirithromycin" title="Dirithromycin">Dirithromycin</a></li> <li><a href="/wiki/Erythromycin" title="Erythromycin">Erythromycin</a><sup>#</sup></li> <li><a href="/wiki/Flurithromycin" title="Flurithromycin">Flurithromycin</a></li> <li><a href="/wiki/Gamithromycin" title="Gamithromycin">Gamithromycin</a></li> <li><a href="/wiki/Josamycin" title="Josamycin">Josamycin</a></li> <li><a href="/wiki/Kitasamycin" title="Kitasamycin">Kitasamycin</a></li> <li><a href="/wiki/Midecamycin" title="Midecamycin">Midecamycin</a></li> <li><a href="/wiki/Miocamycin" title="Miocamycin">Miocamycin</a></li> <li><a href="/wiki/Oleandomycin" title="Oleandomycin">Oleandomycin</a></li> <li><a href="/wiki/Rokitamycin" title="Rokitamycin">Rokitamycin</a></li> <li><a href="/wiki/Roxithromycin" title="Roxithromycin">Roxithromycin</a></li> <li><a href="/wiki/Solithromycin" title="Solithromycin">Solithromycin</a></li> <li><a href="/wiki/Spiramycin" title="Spiramycin">Spiramycin</a></li> <li><a href="/wiki/Telithromycin" title="Telithromycin">Telithromycin</a></li> <li><a href="/wiki/Tildipirosin" title="Tildipirosin">Tildipirosin</a></li> <li><a href="/wiki/Tilmicosin" title="Tilmicosin">Tilmicosin</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/wiki/Tulathromycin" title="Tulathromycin">Tulathromycin</a></li> <li><a href="/wiki/Tylosin" title="Tylosin">Tylosin</a></li> <li><a href="/wiki/Tylvalosin" title="Tylvalosin">Tylvalosin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketolide" title="Ketolide">Ketolides</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/Telithromycin" title="Telithromycin">Telithromycin</a><sup>‡</sup></li> <li><a href="/wiki/Cethromycin" title="Cethromycin">Cethromycin</a></li> <li><a href="/wiki/Solithromycin" title="Solithromycin">Solithromycin</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lincosamides" title="Lincosamides">Lincosamides</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/Clindamycin" title="Clindamycin">Clindamycin</a><sup>#</sup></li> <li><a href="/wiki/Lincomycin" title="Lincomycin">Lincomycin</a></li> <li><a href="/wiki/Pirlimycin" title="Pirlimycin">Pirlimycin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Streptogramin" title="Streptogramin">Streptogramins</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/Pristinamycin" title="Pristinamycin">Pristinamycin</a> (<a href="/wiki/Pristinamycin_IA" title="Pristinamycin IA">IA</a>, <a href="/wiki/Pristinamycin_IIA" title="Pristinamycin IIA">IIA</a>, <a href="/wiki/Pristinamycin_IIB" title="Pristinamycin IIB">IIB</a>)</li> <li><a href="/wiki/NXL103" class="mw-redirect" title="NXL103">NXL103</a> (<a href="/wiki/Flopristin" title="Flopristin">Flopristin</a>, <a href="/wiki/Linopristin" title="Linopristin">Linopristin</a>)</li> <li><a href="/wiki/Quinupristin/dalfopristin" title="Quinupristin/dalfopristin">Quinupristin/dalfopristin</a> (<a href="/wiki/Dalfopristin" title="Dalfopristin">Dalfopristin</a>, <a href="/wiki/Quinupristin" title="Quinupristin">Quinupristin</a>)</li> <li><a href="/wiki/Streptogramin_A" title="Streptogramin A">Streptogramin A</a></li> <li><a href="/wiki/Streptogramin_B" title="Streptogramin B">Streptogramin B</a></li> <li><a href="/wiki/Virginiamycin" title="Virginiamycin">Virginiamycin</a> (<a href="/wiki/Virginiamycin_S1" title="Virginiamycin S1">S1</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q422687#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"><ul><li><span class="uid"><a rel="nofollow" class="external text" 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