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<span>Pharmacology</span> </div> </a> <button aria-controls="toc-Pharmacology-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 Pharmacology subsection</span> </button> <ul id="toc-Pharmacology-sublist" class="vector-toc-list"> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1</span> <span>Mechanism of action</span> </div> </a> <ul id="toc-Mechanism_of_action-sublist" class="vector-toc-list"> <li id="toc-Resistance" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Resistance"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.1.1</span> <span>Resistance</span> </div> </a> <ul id="toc-Resistance-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Pharmacokinetics" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pharmacokinetics"> <div class="vector-toc-text"> <span class="vector-toc-numb">5.2</span> <span>Pharmacokinetics</span> </div> </a> <ul id="toc-Pharmacokinetics-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> <span class="vector-toc-numb">6</span> <span>Chemistry</span> </div> </a> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Veterinary_uses" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Veterinary_uses"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Veterinary uses</span> </div> </a> <ul id="toc-Veterinary_uses-sublist" class="vector-toc-list"> </ul> </li> <li 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Available in 34 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-34" 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">34 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D8%A3%D9%85%D9%8A%D9%83%D8%A7%D8%B3%D9%8A%D9%86" title="أميكاسين – Arabic" lang="ar" hreflang="ar" data-title="أميكاسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A2%D9%85%DB%8C%DA%A9%D8%A7%D8%B3%DB%8C%D9%86" title="آمیکاسین – South Azerbaijani" lang="azb" hreflang="azb" data-title="آمیکاسین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%90%D0%BC%D0%B8%D0%BA%D0%B0%D1%86%D0%B8%D0%BD" title="Амикацин – Bulgarian" lang="bg" hreflang="bg" data-title="Амикацин" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target"><span>Български</span></a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Amikacina" title="Amikacina – Catalan" lang="ca" hreflang="ca" data-title="Amikacina" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Amicacin" title="Amicacin – Welsh" lang="cy" hreflang="cy" data-title="Amicacin" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Amikacin" title="Amikacin – German" lang="de" hreflang="de" data-title="Amikacin" 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/Amikacina" title="Amikacina – Spanish" lang="es" hreflang="es" data-title="Amikacina" 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/Amikazina" title="Amikazina – Basque" lang="eu" hreflang="eu" data-title="Amikazina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A2%D9%85%DB%8C%DA%A9%D8%A7%D8%B3%DB%8C%D9%86" title="آمیکاسین – Persian" lang="fa" hreflang="fa" data-title="آمیکاسین" 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/Amikacine" title="Amikacine – French" lang="fr" hreflang="fr" data-title="Amikacine" 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/Amicacina" title="Amicacina – Galician" lang="gl" hreflang="gl" data-title="Amicacina" 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/%EC%95%84%EB%AF%B8%EC%B9%B4%EC%8B%A0" title="아미카신 – Korean" lang="ko" hreflang="ko" data-title="아미카신" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D4%B1%D5%B4%D5%AB%D5%AF%D5%A1%D6%81%D5%AB%D5%B6" title="Ամիկացին – Armenian" lang="hy" hreflang="hy" data-title="Ամիկացին" 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/Amikasin" title="Amikasin – Indonesian" lang="id" hreflang="id" data-title="Amikasin" 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/Amikacina" title="Amikacina – Italian" lang="it" hreflang="it" data-title="Amikacina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%90%D7%9E%D7%99%D7%A7%D7%A6%D7%99%D7%9F" title="אמיקצין – Hebrew" lang="he" hreflang="he" data-title="אמיקצין" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target"><span>עברית</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Amikacine" title="Amikacine – Dutch" lang="nl" hreflang="nl" data-title="Amikacine" 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%A2%E3%83%9F%E3%82%AB%E3%82%B7%E3%83%B3" title="アミカシン – Japanese" lang="ja" hreflang="ja" data-title="アミカシン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%86%E0%AC%AE%E0%AC%BF%E0%AC%95%E0%AC%BE%E0%AC%B8%E0%AC%BF%E0%AC%A8" title="ଆମିକାସିନ – Odia" lang="or" hreflang="or" data-title="ଆମିକାସିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Amikatsin" title="Amikatsin – Uzbek" lang="uz" hreflang="uz" data-title="Amikatsin" 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/Amikacyna" title="Amikacyna – Polish" lang="pl" hreflang="pl" data-title="Amikacyna" 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/Amicacina" title="Amicacina – Portuguese" lang="pt" hreflang="pt" data-title="Amicacina" 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/Amikacin%C4%83" title="Amikacină – Romanian" lang="ro" hreflang="ro" data-title="Amikacină" 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%90%D0%BC%D0%B8%D0%BA%D0%B0%D1%86%D0%B8%D0%BD" title="Амикацин – Russian" lang="ru" hreflang="ru" data-title="Амикацин" 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/Amikacin" title="Amikacin – Slovenian" lang="sl" hreflang="sl" data-title="Amikacin" 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/Amikacin" title="Amikacin – Serbian" lang="sr" hreflang="sr" data-title="Amikacin" 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/Amikacin" title="Amikacin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Amikacin" 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/Amikasiini" title="Amikasiini – Finnish" lang="fi" hreflang="fi" data-title="Amikasiini" 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/Amikacin" title="Amikacin – Swedish" lang="sv" hreflang="sv" data-title="Amikacin" 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%B8%AD%E0%B8%B0%E0%B8%A1%E0%B8%B4%E0%B8%81%E0%B8%B2%E0%B8%8B%E0%B8%B4%E0%B8%99" title="อะมิกาซิน – Thai" lang="th" hreflang="th" data-title="อะมิกาซิน" 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/Amikasin" title="Amikasin – Turkish" lang="tr" hreflang="tr" data-title="Amikasin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%90%D0%BC%D1%96%D0%BA%D0%B0%D1%86%D0%B8%D0%BD" title="Амікацин – Ukrainian" lang="uk" hreflang="uk" data-title="Амікацин" 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/Amikacin" title="Amikacin – Vietnamese" lang="vi" hreflang="vi" data-title="Amikacin" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E9%98%BF%E7%B1%B3%E5%8D%A1%E6%98%9F" title="阿米卡星 – Chinese" lang="zh" hreflang="zh" data-title="阿米卡星" 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 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<button class="vector-pinnable-header-toggle-button vector-pinnable-header-pin-button" data-event-name="pinnable-header.vector-appearance.pin">move to sidebar</button> <button class="vector-pinnable-header-toggle-button vector-pinnable-header-unpin-button" data-event-name="pinnable-header.vector-appearance.unpin">hide</button> </div> </div> </div> </nav> </div> </div> <div id="bodyContent" class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Antibiotic medication</div> <p class="mw-empty-elt"> </p> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Amikacin">Amikacin</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size skin-invert-image" typeof="mw:File/Frameless"><a href="/wiki/File:Amikacin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Amikacin.svg/220px-Amikacin.svg.png" decoding="async" width="220" height="248" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Amikacin.svg/330px-Amikacin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Amikacin.svg/440px-Amikacin.svg.png 2x" data-file-width="720" data-file-height="810" /></a></span></td></tr><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Amikacin_3D_ball-and-stick_4P20.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Amikacin_3D_ball-and-stick_4P20.png/220px-Amikacin_3D_ball-and-stick_4P20.png" decoding="async" width="220" height="227" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Amikacin_3D_ball-and-stick_4P20.png/330px-Amikacin_3D_ball-and-stick_4P20.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/df/Amikacin_3D_ball-and-stick_4P20.png/440px-Amikacin_3D_ball-and-stick_4P20.png 2x" data-file-width="1200" data-file-height="1236" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Amikin, Amiglyde-V, Arikayce, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/amikacin-sulfate.html">Monograph</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><span title="medlineplus.gov"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a682661.html">a682661</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"> <ul><li><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Amikacin">Amikacin</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> D<sup id="cite_ref-Drugs.com_pregnancy_1-0" class="reference"><a href="#cite_note-Drugs.com_pregnancy-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li> <li class="mw-empty-elt"></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Intramuscular_injection" title="Intramuscular injection">Intramuscular</a>, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a>, <a href="/wiki/Inhalation_administration" class="mw-redirect" title="Inhalation administration">inhalation</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Aminoglycoside" title="Aminoglycoside">Aminoglycoside</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_D06" title="ATC code D06">D06AX12</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D06AX12">WHO</a></span>) <a href="/wiki/ATC_code_J01" title="ATC code J01">J01GB06</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J01GB06">WHO</a></span>), <a href="/wiki/ATC_code_S01" title="ATC code S01">S01AA21</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S01AA21">WHO</a></span>), <a href="/wiki/ATC_code_J01" title="ATC code J01">J01RA06</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J01RA06">WHO</a></span>), <a href="/wiki/ATC_code_D06" title="ATC code D06">QD06AX12</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QD06AX12">WHO</a></span>), <a href="/wiki/ATC_code_J01" title="ATC code J01">QJ01GB06</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QJ01GB06">WHO</a></span>), <a href="/wiki/ATC_code_S01" title="ATC code S01">QS01AA21</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QS01AA21">WHO</a></span>), <a href="/wiki/ATC_code_J01" title="ATC code J01">QJ01RA06</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QJ01RA06">WHO</a></span>)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Australia">AU</abbr>:</small> <a href="/wiki/Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons#Schedule_4" title="Standard for the Uniform Scheduling of Medicines and Poisons">S4</a> (Prescription only)<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United Kingdom">UK</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">POM</a> (Prescription only)<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></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Boxed_warning" title="Boxed warning"><span style="border:thin solid black;">WARNING</span></a><sup id="cite_ref-FDA-AllBoxedWarnings_2-0" class="reference"><a href="#cite_note-FDA-AllBoxedWarnings-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>Rx-only<sup id="cite_ref-Arikayce_FDA_label_5-0" class="reference"><a href="#cite_note-Arikayce_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> Rx-only<sup id="cite_ref-Arikayce_liposomal_EPAR_6-0" class="reference"><a href="#cite_note-Arikayce_liposomal_EPAR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">>90%<sup id="cite_ref-plumb_8-0" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">0–11%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data">Mostly unmetabolized</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">2–3 hours</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(2<i>S</i>)-4-Amino-<i>N</i>-[(2<i>S</i>,3<i>S</i>,4<i>R</i>,5<i>S</i>)-5-amino-2-[(2<i>S</i>,3<i>R</i>,4<i>S</i>,5<i>S</i>,6<i>R</i>)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2<i>R</i>,3<i>R</i>,4<i>S</i>,5<i>R</i>,6<i>R</i>)-6-(aminomethyl)-3,4,5-trihydroxy-oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxybutanamide</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=37517-28-5">37517-28-5</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/37768">37768</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00479">DB00479</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.34635.html">34635</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/84319SGC3C">84319SGC3C</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D02543">D02543</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li>as salt: <span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00865">D00865</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2637">CHEBI:2637</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL177">ChEMBL177</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID3022586">DTXSID3022586</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408529#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.048.653">100.048.653</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q408529#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>22</sub><span title="Hydrogen">H</span><sub>43</sub><span title="Nitrogen">N</span><sub>5</sub><span title="Oxygen">O</span><sub>13</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002585608000000000♠"></span>585.608</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28N%5BC%40H%5D3%5BC%40H%5D%28O%5BC%40H%5D1O%5BC%40%40H%5D%28%5BC%40%40H%5D%28O%29%5BC%40H%5D%28N%29%5BC%40H%5D1O%29CO%29%5BC%40%40H%5D%28O%29%5BC%40H%5D%28O%5BC%40H%5D2O%5BC%40H%5D%28CN%29%5BC%40%40H%5D%28O%29%5BC%40H%5D%28O%29%5BC%40H%5D2O%29%5BC%40%40H%5D%28N%29C3%29%5BC%40%40H%5D%28O%29CCN">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O=C(N[C@H]3[C@H](O[C@H]1O[C@@H]([C@@H](O)[C@H](N)[C@H]1O)CO)[C@@H](O)[C@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](N)C3)[C@@H](O)CCN</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:LKCWBDHBTVXHDL-RMDFUYIESA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464364466&page2=Amikacin">(verify)</a></span></span></td></tr></tbody></table> <p><b>Amikacin</b> is an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> medication used for a number of <a href="/wiki/Bacterial_infections" class="mw-redirect" title="Bacterial infections">bacterial infections</a>.<sup id="cite_ref-AHFS2016_9-0" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> This includes <a href="/wiki/Joint_infections" class="mw-redirect" title="Joint infections">joint infections</a>, <a href="/wiki/Intra-abdominal_infection" title="Intra-abdominal infection">intra-abdominal infections</a>, <a href="/wiki/Meningitis" title="Meningitis">meningitis</a>, <a href="/wiki/Pneumonia" title="Pneumonia">pneumonia</a>, <a href="/wiki/Sepsis" title="Sepsis">sepsis</a>, and <a href="/wiki/Urinary_tract_infection" title="Urinary tract infection">urinary tract infections</a>.<sup id="cite_ref-AHFS2016_9-1" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> It is also used for the treatment of <a href="/wiki/Multidrug-resistant_tuberculosis" title="Multidrug-resistant tuberculosis">multidrug-resistant tuberculosis</a>.<sup id="cite_ref-WHO2008_10-0" class="reference"><a href="#cite_note-WHO2008-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> It is used by injection <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">into a vein using an IV</a> or <a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular">into a muscle</a>.<sup id="cite_ref-AHFS2016_9-2" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Amikacin, like other <a href="/wiki/Aminoglycoside" title="Aminoglycoside">aminoglycoside antibiotics</a>, can cause <a href="/wiki/Hearing_loss" title="Hearing loss">hearing loss</a>, balance problems, and <a href="/wiki/Kidney_problems" class="mw-redirect" title="Kidney problems">kidney problems</a>.<sup id="cite_ref-AHFS2016_9-3" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Other side effects include <a href="/wiki/Paralysis" title="Paralysis">paralysis</a>, resulting in the inability to breathe.<sup id="cite_ref-AHFS2016_9-4" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> If used during <a href="/wiki/Pregnancy" title="Pregnancy">pregnancy</a> it may cause permanent deafness in the baby.<sup id="cite_ref-AHFS2016_9-5" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Drugs.com_pregnancy_1-1" class="reference"><a href="#cite_note-Drugs.com_pregnancy-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Amikacin works by blocking the function of the bacteria's <a href="/wiki/30S_ribosomal_subunit" class="mw-redirect" title="30S ribosomal subunit">30S ribosomal subunit</a>, making it unable to produce <a href="/wiki/Protein" title="Protein">proteins</a>.<sup id="cite_ref-AHFS2016_9-6" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Amikacin was patented in 1971, and came into commercial use in 1976.<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><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> It is on the <a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">World Health Organization's List of Essential Medicines</a>.<sup id="cite_ref-WHO23rd_13-0" class="reference"><a href="#cite_note-WHO23rd-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It is derived from <a href="/wiki/Kanamycin" class="mw-redirect" title="Kanamycin">kanamycin</a>.<sup id="cite_ref-AHFS2016_9-7" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<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=Amikacin&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amikacin is most often used for treating severe infections with <a href="/wiki/Multidrug_resistance" class="mw-redirect" title="Multidrug resistance">multidrug-resistant</a>, aerobic <a href="/wiki/Gram-negative" class="mw-redirect" title="Gram-negative">Gram-negative</a> bacteria, especially <i><a href="/wiki/Pseudomonas" title="Pseudomonas">Pseudomonas</a></i>, <i><a href="/wiki/Acinetobacter" title="Acinetobacter">Acinetobacter</a></i>, <i><a href="/wiki/Enterobacter" title="Enterobacter">Enterobacter</a></i>, <i><a href="/wiki/E._coli" class="mw-redirect" title="E. coli">E. coli</a></i>, <i><a href="/wiki/Proteus_(bacterium)" title="Proteus (bacterium)">Proteus</a></i>, <i><a href="/wiki/Klebsiella" title="Klebsiella">Klebsiella</a></i>, and <i><a href="/wiki/Serratia" title="Serratia">Serratia</a></i>.<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-0" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> The only <a href="/wiki/Gram-positive" class="mw-redirect" title="Gram-positive">Gram-positive</a> bacteria that amikacin strongly affects are <i><a href="/wiki/Staphylococcus" title="Staphylococcus">Staphylococcus</a></i><sup id="cite_ref-Amikacin_sulfate_FDA_label_14-1" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> and <i><a href="/wiki/Nocardia" title="Nocardia">Nocardia</a></i>.<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> Amikacin can also be used to treat non-tubercular <a href="/wiki/Mycobacterium" title="Mycobacterium">mycobacterial</a> infections and tuberculosis (if caused by sensitive strains) when first-line drugs fail to control the infection.<sup id="cite_ref-AHFS2016_9-8" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> It is rarely used alone.<sup id="cite_ref-cunha_16-0" class="reference"><a href="#cite_note-cunha-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>It is often used in the following situations:<sup id="cite_ref-AHFS2016_9-9" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <ul><li><a href="/wiki/Bronchiectasis" title="Bronchiectasis">Bronchiectasis</a><sup id="cite_ref-medscape_17-0" class="reference"><a href="#cite_note-medscape-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup></li> <li>Bone and joint infections</li> <li><a href="/wiki/Granulocytopenia" class="mw-redirect" title="Granulocytopenia">Granulocytopenia</a>, when combined with <a href="/wiki/Ticarcillin" title="Ticarcillin">ticarcillin</a>, in people with cancer<sup id="cite_ref-aronson_18-0" class="reference"><a href="#cite_note-aronson-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup></li> <li>Intra-abdominal infections (such as <a href="/wiki/Peritonitis" title="Peritonitis">peritonitis</a>) as an adjunct to other medicines, like <a href="/wiki/Clindamycin" title="Clindamycin">clindamycin</a>, <a href="/wiki/Metronidazole" title="Metronidazole">metronidazole</a>, <a href="/wiki/Piperacillin" title="Piperacillin">piperacillin</a>/<a href="/wiki/Tazobactam" title="Tazobactam">tazobactam</a>, or <a href="/wiki/Ampicillin" title="Ampicillin">ampicillin</a>/<a href="/wiki/Sulbactam" title="Sulbactam">sulbactam</a></li> <li><a href="/wiki/Meningitis" title="Meningitis">Meningitis</a>: <ul><li>for meningitis by <i>E. coli</i>, as an adjunct to <a href="/wiki/Imipenem" title="Imipenem">imipenem</a></li> <li>for meningitis caused by <i>Pseudomonas</i>, as an adjunct to <a href="/wiki/Meropenem" title="Meropenem">meropenem</a></li> <li>for meningitis caused by <i>Acinetobacter</i>, as an adjunct to imipenem or <a href="/wiki/Colistin" title="Colistin">colistin</a></li> <li>for <a href="/wiki/Neonatal_meningitis" title="Neonatal meningitis">neonatal meningitis</a> caused by <i><a href="/wiki/Streptococcus_agalactiae" title="Streptococcus agalactiae">Streptococcus agalactiae</a></i> or <i><a href="/wiki/Listeria_monocytogenes" title="Listeria monocytogenes">Listeria monocytogenes</a></i>, as an adjunct to ampicillin</li> <li>for neonatal meningitis caused by Gram negative bacteria such as <i>E. coli</i>, as adjunct to a <a href="/wiki/Cephalosporin#Classification" title="Cephalosporin">3rd-generation cephalosporin</a></li></ul></li> <li>Mycobacterial infections, including as a second-line agent for active <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a>.<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> It is also used for infections by <i><a href="/wiki/Mycobacterium_avium" class="mw-redirect" title="Mycobacterium avium">Mycobacterium avium</a></i>, <i><a href="/wiki/Mycobacterium_abscessus" class="mw-redirect" title="Mycobacterium abscessus">M. abcessus</a></i>, <i><a href="/wiki/Mycobacterium_chelonae" class="mw-redirect" title="Mycobacterium chelonae">M. chelonae</a></i>, and <i><a href="/wiki/Mycobacterium_fortuitum" title="Mycobacterium fortuitum">M. fortuitum</a></i>.</li> <li><i><a href="/wiki/Rhodococcus_equi" title="Rhodococcus equi">Rhodococcus equi</a></i>, which causes an infection resembling tuberculosis</li> <li>Respiratory tract infections, including as an adjunct to <a href="/wiki/Beta-lactam" class="mw-redirect" title="Beta-lactam">beta-lactams</a> or <a href="/wiki/Carbapenem" title="Carbapenem">carbapenem</a> for <a href="/wiki/Hospital-acquired_pneumonia" title="Hospital-acquired pneumonia">hospital-acquired pneumonia</a></li> <li><a href="/wiki/Sepsis" title="Sepsis">Sepsis</a>, including that in neonates,<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-2" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> as an adjunct to beta-lactams or carbapenem</li> <li>Skin and suture-site infections<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-3" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></li> <li><a href="/wiki/Urinary_tract_infection" title="Urinary tract infection">Urinary tract infections</a> that are caused by bacteria resistant to less toxic drugs (often by <i><a href="/wiki/Enterobacteriaceae" title="Enterobacteriaceae">Enterobacteriaceae</a></i> or <i>P. aeruginosa)</i></li></ul> <p>Amikacin may be combined with a beta-lactam antibiotic for <a href="/wiki/Empiric_therapy" title="Empiric therapy">empiric therapy</a> for people with <a href="/wiki/Neutropenia" title="Neutropenia">neutropenia</a> and <a href="/wiki/Fever" title="Fever">fever</a>.<sup id="cite_ref-AHFS2016_9-10" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Available_forms">Available forms</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amikacin&action=edit&section=2" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A liposome inhalation suspension is also available and approved to treat <a href="/wiki/Mycobacterium_avium_complex" title="Mycobacterium avium complex">Mycobacterium avium complex</a> (MAC) in the United States,<sup id="cite_ref-FDA_PR_20-0" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Arikayce_FDA_label_5-1" class="reference"><a href="#cite_note-Arikayce_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> and in the European Union.<sup id="cite_ref-Arikayce_liposomal_EPAR_6-1" class="reference"><a href="#cite_note-Arikayce_liposomal_EPAR-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Amikacin liposome inhalation suspension is the first drug approved under the US <a href="/w/index.php?title=Limited_population_pathway_for_antibacterial_and_antifungal_drugs&action=edit&redlink=1" class="new" title="Limited population pathway for antibacterial and antifungal drugs (page does not exist)">limited population pathway for antibacterial and antifungal drugs</a> (LPAD pathway).<sup id="cite_ref-FDA_PR_20-1" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> It also was approved under the <a href="/wiki/Accelerated_approval_(FDA)" title="Accelerated approval (FDA)">accelerated approval</a> pathway.<sup id="cite_ref-FDA_PR_20-2" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The US <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA) granted the application for amikacin liposome inhalation suspension <a href="/wiki/Fast_track_(FDA)" title="Fast track (FDA)">fast track</a>, <a href="/wiki/Breakthrough_therapy" title="Breakthrough therapy">breakthrough therapy</a>, <a href="/wiki/Priority_review" title="Priority review">priority review</a>, and <a href="/wiki/Food_and_Drug_Administration_Safety_and_Innovation_Act#GAIN" title="Food and Drug Administration Safety and Innovation Act">qualified infectious disease product</a> (QIDP) designations.<sup id="cite_ref-FDA_PR_20-3" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> The FDA granted approval of Arikayce to Insmed, Inc.<sup id="cite_ref-FDA_PR_20-4" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>The safety and efficacy of amikacin liposome inhalation suspension, an inhaled treatment taken through a nebulizer, was demonstrated in a randomized, controlled clinical trial where patients were assigned to one of two treatment groups.<sup id="cite_ref-FDA_PR_20-5" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> One group of patients received amikacin liposome inhalation suspension plus a background multi-drug antibacterial regimen, while the other treatment group received a background multi-drug antibacterial regimen alone.<sup id="cite_ref-FDA_PR_20-6" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> By the sixth month of treatment, 29 percent of patients treated with amikacin liposome inhalation suspension had no growth of mycobacteria in their sputum cultures for three consecutive months compared to 9 percent of patients who were not treated with amikacin liposome inhalation suspension.<sup id="cite_ref-FDA_PR_20-7" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Special_populations">Special populations</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amikacin&action=edit&section=3" title="Edit section: Special populations"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amikacin should be used in smaller doses in the elderly, who often have age-related decreases in kidney function, and children, whose kidneys are not fully developed yet. It is considered <a href="/wiki/Pregnancy_category" title="Pregnancy category">pregnancy category</a> D in both the United States and Australia, meaning they have a probability of harming the fetus.<sup id="cite_ref-AHFS2016_9-11" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Around 16% of amikacin crosses the placenta; while the half-life of amikacin in the mother is 2 hours, it is 3.7 hours in the fetus.<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-4" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> A pregnant woman taking amikacin with another aminoglycoside has a possibility of causing <a href="/wiki/Congenital_deafness" class="mw-redirect" title="Congenital deafness">congenital deafness</a> in her child. While it is known to cross the placenta, amikacin is only partially secreted in breast milk.<sup id="cite_ref-AHFS2016_9-12" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>In general, amikacin should be avoided in infants.<sup id="cite_ref-ettinger_21-0" class="reference"><a href="#cite_note-ettinger-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Infants also tend to have a larger volume of distribution due to their higher concentration of <a href="/wiki/Extracellular_fluid" title="Extracellular fluid">extracellular fluid</a>, where aminoglycosides reside.<sup id="cite_ref-plumb_8-1" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>The elderly tend to have amikacin stay longer in their system; while the average clearance of amikacin in a 20-year-old is 6 L/hr, it is 3 L/hr in an 80-year-old.<sup id="cite_ref-maire_22-0" class="reference"><a href="#cite_note-maire-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p><p>Clearance is even higher in people with cystic fibrosis.<sup id="cite_ref-eghianruwa_23-0" class="reference"><a href="#cite_note-eghianruwa-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p><p>In people with muscular disorders such as <a href="/wiki/Myasthenia_gravis" title="Myasthenia gravis">myasthenia gravis</a> or <a href="/wiki/Parkinson%27s_disease" title="Parkinson's disease">Parkinson's disease</a>, amikacin's paralytic effect on neuromuscular junctions can worsen muscle weakness.<sup id="cite_ref-AHFS2016_9-13" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<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=Amikacin&action=edit&section=4" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Side-effects of amikacin are similar to those of other aminoglycosides. <a href="/wiki/Nephrotoxicity" title="Nephrotoxicity">Kidney damage</a> and <a href="/wiki/Ototoxicity" title="Ototoxicity">ototoxicity</a> (which can lead to hearing loss) are the most important effects, occurring in 1–10% of users.<sup id="cite_ref-medscape_17-1" class="reference"><a href="#cite_note-medscape-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The nephro- and ototoxicity are thought to be due to aminoglycosides' tendency to accumulate in the kidneys and inner ear.<sup id="cite_ref-plumb_8-2" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Right_osseous_labyrinth_svg_hariadhi.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Right_osseous_labyrinth_svg_hariadhi.svg/300px-Right_osseous_labyrinth_svg_hariadhi.svg.png" decoding="async" width="300" height="300" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Right_osseous_labyrinth_svg_hariadhi.svg/450px-Right_osseous_labyrinth_svg_hariadhi.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/2d/Right_osseous_labyrinth_svg_hariadhi.svg/600px-Right_osseous_labyrinth_svg_hariadhi.svg.png 2x" data-file-width="512" data-file-height="512" /></a><figcaption>Diagram of the inner ear. Amikacin causes damage to the cochlea and vestibules.</figcaption></figure> <p>Amikacin can cause neurotoxicity if used at a higher dose or for longer than recommended. The resulting effects of neurotoxicity include <a href="/wiki/Vertigo" title="Vertigo">vertigo</a>, <a href="/wiki/Numbness" class="mw-redirect" title="Numbness">numbness</a>, <a href="/wiki/Paresthesia" title="Paresthesia">tingling</a> of the skin (<a href="/wiki/Paresthesia" title="Paresthesia">paresthesia</a>), muscle <a href="/wiki/Convulsion" title="Convulsion">twitching</a>, and <a href="/wiki/Seizures" class="mw-redirect" title="Seizures">seizures</a>.<sup id="cite_ref-AHFS2016_9-14" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Its toxic effect on the 8th <a href="/wiki/Cranial_nerve" class="mw-redirect" title="Cranial nerve">cranial nerve</a> causes ototoxicity, resulting in loss of balance and, more commonly, hearing loss.<sup id="cite_ref-plumb_8-3" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Damage to the <a href="/wiki/Cochlea" title="Cochlea">cochlea</a>, caused by the forced <a href="/wiki/Apoptosis" title="Apoptosis">apoptosis</a> of the <a href="/wiki/Hair_cell" title="Hair cell">hair cells</a>, leads to the loss of high-frequency hearing and happens before any clinical hearing loss can be detected.<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-5" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-morris_24-0" class="reference"><a href="#cite_note-morris-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Damage to the <a href="/wiki/Vestibule_of_the_ear" title="Vestibule of the ear">ear vestibules</a>, most likely by creating excessive oxidative <a href="/wiki/Free_radicals" class="mw-redirect" title="Free radicals">free radicals</a>. It does so in a time-dependent rather than dose-dependent manner, meaning that risk can be minimized by reducing the duration of use.<sup id="cite_ref-corti_25-0" class="reference"><a href="#cite_note-corti-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p><p>Amikacin causes nephrotoxicity (damage to the kidneys), by acting on the <a href="/wiki/Proximal_renal_tubule" class="mw-redirect" title="Proximal renal tubule">proximal renal tubules</a>. It easily ionizes to a <a href="/wiki/Cation" class="mw-redirect" title="Cation">cation</a> and binds to the <a href="/wiki/Anionic" class="mw-redirect" title="Anionic">anionic</a> sites of the epithelial cells of the proximal tubule as part of receptor-mediated <a href="/wiki/Pinocytosis" title="Pinocytosis">pinocytosis</a>. The concentration of amikacin in the <a href="/wiki/Renal_cortex" title="Renal cortex">renal cortex</a> becomes ten times that of amikacin in the plasma;<sup id="cite_ref-ettinger_21-1" class="reference"><a href="#cite_note-ettinger-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> it then most likely interferes with the metabolism of <a href="/wiki/Phospholipids" class="mw-redirect" title="Phospholipids">phospholipids</a> in the <a href="/wiki/Lysosomes" class="mw-redirect" title="Lysosomes">lysosomes</a>, which causes lytic enzymes to leak into the cytoplasm.<sup id="cite_ref-plumb_8-4" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Nephrotoxicity results in increased serum <a href="/wiki/Creatinine" title="Creatinine">creatinine</a>, <a href="/wiki/Blood_urea_nitrogen" title="Blood urea nitrogen">blood urea nitrogen</a>, <a href="/wiki/Red_blood_cells" class="mw-redirect" title="Red blood cells">red blood cells</a>, and <a href="/wiki/White_blood_cells" class="mw-redirect" title="White blood cells">white blood cells</a>, as well as <a href="/wiki/Albuminuria" title="Albuminuria">albuminuria</a> (increased output of <a href="/wiki/Albumin" title="Albumin">albumin</a> in the urine), <a href="/wiki/Glycosuria" title="Glycosuria">glycosuria</a> (excretion of glucose into the urine), decreased urine <a href="/wiki/Specific_gravity" class="mw-redirect" title="Specific gravity">specific gravity</a>, and <a href="/wiki/Oliguria" title="Oliguria">oliguria</a> (decrease in overall urine output).<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-6" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-morris_24-1" class="reference"><a href="#cite_note-morris-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> It can also cause <a href="/wiki/Urinary_casts" class="mw-redirect" title="Urinary casts">urinary casts</a> to appear.<sup id="cite_ref-plumb_8-5" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The changes in <a href="/wiki/Renal_tubular" class="mw-redirect" title="Renal tubular">renal tubular</a> function also change the electrolyte levels and acid-base balance in the body, which can lead to <a href="/wiki/Hypokalemia" title="Hypokalemia">hypokalemia</a> and <a href="/wiki/Acidosis" title="Acidosis">acidosis</a> or <a href="/wiki/Alkalosis" title="Alkalosis">alkalosis</a>.<sup id="cite_ref-corti_25-1" class="reference"><a href="#cite_note-corti-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> Nephrotoxicity is more common in those with pre-existing hypokalemia, <a href="/wiki/Hypocalcemia" title="Hypocalcemia">hypocalcemia</a>, <a href="/wiki/Hypomagnesemia" class="mw-redirect" title="Hypomagnesemia">hypomagnesemia</a>, acidosis, low <a href="/wiki/Renal_function#Glomerular_filtration_rate" class="mw-redirect" title="Renal function">glomerular filtration rate</a>, <a href="/wiki/Diabetes" title="Diabetes">diabetes</a> mellitus, dehydration, fever, and <a href="/wiki/Sepsis" title="Sepsis">sepsis</a>, as well as those taking <a href="/wiki/Prostaglandins" class="mw-redirect" title="Prostaglandins">antiprostaglandins</a>.<sup id="cite_ref-AHFS2016_9-15" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-ettinger_21-2" class="reference"><a href="#cite_note-ettinger-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-plumb_8-6" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-corti_25-2" class="reference"><a href="#cite_note-corti-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> The toxicity usually reverts once the antibiotic course has been completed,<sup id="cite_ref-plumb_8-7" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> and can be avoided altogether by less frequent dosing (such as once every 24 hours rather than once every 8 hours).<sup id="cite_ref-ettinger_21-3" class="reference"><a href="#cite_note-ettinger-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>Amikacin can cause neuromuscular blockade (including acute muscular paralysis) and respiratory paralysis (including <a href="/wiki/Apnea" title="Apnea">apnea</a>).<sup id="cite_ref-AHFS2016_9-16" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Rare side effects (occurring in fewer than 1% of users) include allergic reactions, <a href="/wiki/Skin_rash" class="mw-redirect" title="Skin rash">skin rash</a>, <a href="/wiki/Drug_fever" class="mw-redirect" title="Drug fever">fever</a>, <a href="/wiki/Headache" title="Headache">headaches</a>, <a href="/wiki/Tremor" title="Tremor">tremor</a>, <a href="/wiki/Nausea" title="Nausea">nausea</a> and <a href="/wiki/Vomiting" title="Vomiting">vomiting</a>, <a href="/wiki/Eosinophilia" title="Eosinophilia">eosinophilia</a>, <a href="/wiki/Arthralgia" title="Arthralgia">arthralgia</a>, <a href="/wiki/Anemia" title="Anemia">anemia</a>, <a href="/wiki/Hypotension" title="Hypotension">hypotension</a>, and hypomagnesemia. In intravitreous injections (where amikacin is injected into the eye), macular <a href="/wiki/Infarction" title="Infarction">infarction</a> can cause permanent vision loss.<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-7" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-medscape_17-2" class="reference"><a href="#cite_note-medscape-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>The amikacin liposome inhalation suspension prescribing information includes a boxed warning regarding the increased risk of respiratory conditions including hypersensitivity pneumonitis (inflamed lungs), bronchospasm (tightening of the airway), exacerbation of underlying lung disease and hemoptysis (spitting up blood) that have led to hospitalizations in some cases.<sup id="cite_ref-FDA_PR_20-8" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Arikayce_FDA_label_5-2" class="reference"><a href="#cite_note-Arikayce_FDA_label-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Other common side effects in patients taking amikacin liposome inhalation suspension are dysphonia (difficulty speaking), cough, ototoxicity (damaged hearing), upper airway irritation, musculoskeletal pain, fatigue, diarrhea and nausea.<sup id="cite_ref-FDA_PR_20-9" class="reference"><a href="#cite_note-FDA_PR-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Arikayce_FDA_label_5-3" class="reference"><a href="#cite_note-Arikayce_FDA_label-5"><span class="cite-bracket">[</span>5<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=Amikacin&action=edit&section=5" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amikacin should be avoided in those who are sensitive to <i>any</i> aminoglycoside, as they are cross-allergenic (that is, an allergy to one aminoglycoside also confers hypersensitivity to other aminoglycosides). It should also be avoided in those sensitive to <a href="/wiki/Sulfite" title="Sulfite">sulfite</a> (seen more among people with asthma),<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-8" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> since most amikacin usually comes with <a href="/wiki/Sodium_metabisulfite" title="Sodium metabisulfite">sodium metabisulfite</a>, which can cause an allergic reaction.<sup id="cite_ref-AHFS2016_9-17" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>In general, amikacin should not be used with or just before/after another drug that can cause neurotoxicity, ototoxicity, or nephrotoxicity. Such drugs include other aminoglycosides; the antiviral <a href="/wiki/Acyclovir" class="mw-redirect" title="Acyclovir">acyclovir</a>; the antifungal <a href="/wiki/Amphotericin_B" title="Amphotericin B">amphotericin B</a>; the antibiotics <a href="/wiki/Bacitracin" title="Bacitracin">bacitracin</a>, <a href="/wiki/Capreomycin" title="Capreomycin">capreomycin</a>, colistin, <a href="/wiki/Polymyxin_B" title="Polymyxin B">polymyxin B</a>, and <a href="/wiki/Vancomycin" title="Vancomycin">vancomycin</a>; and <a href="/wiki/Cisplatin" title="Cisplatin">cisplatin</a>, which is used in <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapy</a>.<sup id="cite_ref-AHFS2016_9-18" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Amikacin should not be used with <a href="/wiki/Neuromuscular_blocking_agents" class="mw-redirect" title="Neuromuscular blocking agents">neuromuscular blocking agents</a>, as they can increase muscle weakness and paralysis.<sup id="cite_ref-AHFS2016_9-19" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Interactions">Interactions</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amikacin&action=edit&section=6" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amikacin can be inactivated by other beta-lactams, though not to the extent as other aminoglycosides, and is still often used with <a href="/wiki/Penicillins" class="mw-redirect" title="Penicillins">penicillins</a> (a type of beta-lactam) to create an additive effect against certain bacteria, and carbapenems, which can have a synergistic effect against some Gram-positive bacteria. Another group of beta-lactams, the cephalosporins, can increase the nephrotoxicity of aminoglycoside as well as randomly elevating <a href="/wiki/Creatinine" title="Creatinine">creatinine</a> levels. The antibiotics <a href="/wiki/Chloramphenicol" title="Chloramphenicol">chloramphenicol</a>, clindamycin, and <a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a> have been known to inactivate aminoglycosides in general by pharmacological antagonism.<sup id="cite_ref-AHFS2016_9-20" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>The effect of amikacin is increased when used with drugs derived from the <a href="/wiki/Botulinum_toxin" title="Botulinum toxin">botulinum toxin</a>,<sup id="cite_ref-medscape_17-3" class="reference"><a href="#cite_note-medscape-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Anesthetic" title="Anesthetic">anesthetics</a>, neuromuscular blocking agents, or large doses of blood that contains <a href="/wiki/Citrate" class="mw-redirect" title="Citrate">citrate</a> as an <a href="/wiki/Anticoagulant" title="Anticoagulant">anticoagulant</a>.<sup id="cite_ref-AHFS2016_9-21" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Potent diuretics not only cause ototoxicity themselves, but they can also increase the concentration of amikacin in the serum and tissue, making the ototoxicity even more likely.<sup id="cite_ref-AHFS2016_9-22" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Quinidine" title="Quinidine">Quinidine</a> also increases levels of amikacin in the body.<sup id="cite_ref-medscape_17-4" class="reference"><a href="#cite_note-medscape-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The <a href="/wiki/NSAID" class="mw-redirect" title="NSAID">NSAID</a> <a href="/wiki/Indomethacin" class="mw-redirect" title="Indomethacin">indomethacin</a> can increase serum aminoglycoside levels in premature infants.<sup id="cite_ref-AHFS2016_9-23" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Contrast mediums such as <a href="/wiki/Ioversol" title="Ioversol">ioversol</a> increases the nephrotoxicity and otoxicity caused by amikacin.<sup id="cite_ref-medscape_17-5" class="reference"><a href="#cite_note-medscape-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Amikacin can decrease the effect certain vaccines, such as the live <a href="/wiki/BCG_vaccine" title="BCG vaccine">BCG vaccine</a> (used for tuberculosis), the <a href="/wiki/Cholera_vaccine" title="Cholera vaccine">cholera vaccine</a>, and the live <a href="/wiki/Typhoid_vaccine" title="Typhoid vaccine">typhoid vaccine</a> by acting as a pharmacological antagonist.<sup id="cite_ref-medscape_17-6" class="reference"><a href="#cite_note-medscape-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacology">Pharmacology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amikacin&action=edit&section=7" title="Edit section: Pharmacology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amikacin&action=edit&section=8" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:010_small_subunit-1FKA.gif" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/90/010_small_subunit-1FKA.gif/220px-010_small_subunit-1FKA.gif" decoding="async" width="220" height="220" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/9/90/010_small_subunit-1FKA.gif 1.5x" data-file-width="320" data-file-height="320" /></a><figcaption>The 30S subunit of the prokaryotic ribosome. The orange represents the 16S rRNA, and the blue represents the various proteins attached.</figcaption></figure> <p>Amikacin irreversibly binds to <a href="/wiki/16S_ribosomal_RNA" title="16S ribosomal RNA">16S rRNA</a> and the RNA-binding <a href="/wiki/Prokaryotic_small_ribosomal_subunit#Structure" title="Prokaryotic small ribosomal subunit">S12 protein</a> of the <a href="/wiki/30S" class="mw-redirect" title="30S">30S</a> subunit of prokaryotic <a href="/wiki/Ribosome" title="Ribosome">ribosome</a> and inhibits protein synthesis by changing the ribosome's shape so that it cannot read the <a href="/wiki/MRNA" class="mw-redirect" title="MRNA">mRNA</a> <a href="/wiki/Codon" class="mw-redirect" title="Codon">codons</a> correctly.<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-9" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-bauman_26-0" class="reference"><a href="#cite_note-bauman-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> It also interferes with the region that interacts with the <a href="/wiki/Wobble_base" class="mw-redirect" title="Wobble base">wobble base</a> of the <a href="/wiki/TRNA" class="mw-redirect" title="TRNA">tRNA</a> anticodon.<sup id="cite_ref-drugbank_27-0" class="reference"><a href="#cite_note-drugbank-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> It works in a concentration-dependent manner, and has better action in an alkaline environment.<sup id="cite_ref-plumb_8-8" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>At normal doses, amikacin-sensitive bacteria respond within 24–48 hours.<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-10" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Resistance">Resistance</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amikacin&action=edit&section=9" title="Edit section: Resistance"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amikacin evades attacks by all antibiotic-inactivating enzymes that are responsible for <a href="/wiki/Antibiotic_resistance" class="mw-redirect" title="Antibiotic resistance">antibiotic resistance</a> in bacteria, except for aminoacetyltransferase and <a href="/wiki/Nucleotidyltransferase" title="Nucleotidyltransferase">nucleotidyltransferase</a>.<sup id="cite_ref-mudd_28-0" class="reference"><a href="#cite_note-mudd-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> This is accomplished by the <small>L</small>-hydroxyaminobuteroyl amide (L-HABA) moiety attached to N-1 (compare to <a href="/wiki/Kanamycin" class="mw-redirect" title="Kanamycin">kanamycin</a>, which simply has a hydrogen), which blocks the access and decreases the affinity of aminoglycoside-inactivating enzymes.<sup id="cite_ref-mudd_28-1" class="reference"><a href="#cite_note-mudd-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-kondo_29-0" class="reference"><a href="#cite_note-kondo-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-park_30-0" class="reference"><a href="#cite_note-park-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup> Amikacin ends up with only one site where these enzymes can attack, while gentamicin and tobramycin have six.<sup id="cite_ref-cunha_16-1" class="reference"><a href="#cite_note-cunha-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>Bacteria that are resistant to <a href="/wiki/Streptomycin" title="Streptomycin">streptomycin</a> and capreomycin are still susceptible to amikacin; bacteria that are resistant to kanamycin have varying susceptibility to amikacin. Resistance to amikacin also confers resistance to kanamycin and capreomycin.<sup id="cite_ref-caminero_31-0" class="reference"><a href="#cite_note-caminero-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> </p><p>Resistance to amikacin and kanamycin in <i>Mycobacterium tuberculosis</i>, the causative agent of tuberculosis, is due to a mutation in the <i>rrs</i> gene, which codes for the 16S rRNA. Mutations such as these reduce the binding affinity of amikacin to the bacteria's ribosome.<sup id="cite_ref-ahmad_32-0" class="reference"><a href="#cite_note-ahmad-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> Variations of aminoglycoside <a href="/wiki/Acetyltransferase" title="Acetyltransferase">acetyltransferase</a> (AAC) and aminoglycoside <a href="/wiki/Adenylyltransferase" class="mw-redirect" title="Adenylyltransferase">adenylyltransferase</a> (AAD) also confer resistance: resistance in <i>Pseudomonas aeruginosa</i> is caused by AAC(6')-IV, which also confers resistance to kanamycin, gentamicin, and tobramycin, and resistance in <i><a href="/wiki/Staphylococcus_aureus" title="Staphylococcus aureus">Staphylococcus aureus</a></i> and <i><a href="/wiki/S._epidermidis" class="mw-redirect" title="S. epidermidis">S. epidermidis</a></i> is caused by AAD(4',4<i>), </i>which also confers resistance to kanamycin, tobramycin, and apramycin.<sup id="cite_ref-kondo_29-1" class="reference"><a href="#cite_note-kondo-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup> Some strains of <i>S. aureus</i> can also inactivate amikacin by phosphorylating it.<sup id="cite_ref-aronson_18-1" class="reference"><a href="#cite_note-aronson-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Pharmacokinetics">Pharmacokinetics</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amikacin&action=edit&section=10" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amikacin is not absorbed orally and thus must be administered parenterally. It reaches peak serum concentrations in 0.5–2 hours when administered intramuscularly. Less than 11% of the amikacin actually binds to plasma proteins. It is distributed into the <a href="/wiki/Heart" title="Heart">heart</a>, <a href="/wiki/Gallbladder" title="Gallbladder">gallbladder</a>, <a href="/wiki/Lungs" class="mw-redirect" title="Lungs">lungs</a>, and <a href="/wiki/Bone" title="Bone">bones</a>, as well as in <a href="/wiki/Bile" title="Bile">bile</a>, <a href="/wiki/Sputum" title="Sputum">sputum</a>, <a href="/wiki/Interstitial_fluid" class="mw-redirect" title="Interstitial fluid">interstitial fluid</a>, <a href="/wiki/Pleural_fluid" class="mw-redirect" title="Pleural fluid">pleural fluid</a>, and <a href="/wiki/Synovial_fluids" class="mw-redirect" title="Synovial fluids">synovial fluids</a>. It is usually found at low concentrations in the <a href="/wiki/Cerebrospinal_fluid" title="Cerebrospinal fluid">cerebrospinal fluid</a>, except when administered intraventricularly.<sup id="cite_ref-AHFS2016_9-24" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In infants, amikacin is normally found at 10–20% of plasma levels in the spinal fluid, but the amount reaches 50% in cases of meningitis.<sup id="cite_ref-Amikacin_sulfate_FDA_label_14-11" class="reference"><a href="#cite_note-Amikacin_sulfate_FDA_label-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> It does not easily cross the <a href="/wiki/Blood%E2%80%93brain_barrier" title="Blood–brain barrier">blood–brain barrier</a> or enter ocular tissue.<sup id="cite_ref-plumb_8-9" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>While the half-life of amikacin is normally two hours, it is 50 hours in those with end-stage renal disease.<sup id="cite_ref-cunha_16-2" class="reference"><a href="#cite_note-cunha-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p><p>The majority (95%) of amikacin from an intramuscular or intravenous dose is secreted unchanged via <a href="/wiki/Glomerular_filtration" class="mw-redirect" title="Glomerular filtration">glomerular filtration</a> and into the urine within 24 hours.<sup id="cite_ref-AHFS2016_9-25" class="reference"><a href="#cite_note-AHFS2016-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-cunha_16-3" class="reference"><a href="#cite_note-cunha-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Factors that cause amikacin to be excreted via urine include its relatively low molecular weight, high water solubility, and unmetabolized state.<sup id="cite_ref-ettinger_21-4" class="reference"><a href="#cite_note-ettinger-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amikacin&action=edit&section=11" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amikacin is derived from <a href="/wiki/Kanamycin_A" title="Kanamycin A">kanamycin A</a>:<sup id="cite_ref-kawaguchi_33-0" class="reference"><a href="#cite_note-kawaguchi-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-monteleone_34-0" class="reference"><a href="#cite_note-monteleone-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center skin-invert-image" typeof="mw:File"><a href="/wiki/File:Amikacin_synthesis_2.svg" class="mw-file-description" title="The synthesis of amikacin"><img alt="The synthesis of amikacin" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Amikacin_synthesis_2.svg/800px-Amikacin_synthesis_2.svg.png" decoding="async" width="800" height="587" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Amikacin_synthesis_2.svg/1200px-Amikacin_synthesis_2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Amikacin_synthesis_2.svg/1600px-Amikacin_synthesis_2.svg.png 2x" data-file-width="685" data-file-height="503" /></a><figcaption>The synthesis of amikacin</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Veterinary_uses">Veterinary uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Amikacin&action=edit&section=12" title="Edit section: Veterinary uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>While amikacin is only FDA-approved for use in dogs and for intrauterine infection in horses, it is one of the most common aminoglycosides used in veterinary medicine,<sup id="cite_ref-forney_35-0" class="reference"><a href="#cite_note-forney-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> and has been used in dogs, cats, <a href="/wiki/Guinea_pig" title="Guinea pig">guinea pigs</a>, <a href="/wiki/Chinchilla" title="Chinchilla">chinchillas</a>, <a href="/wiki/Hamster" title="Hamster">hamsters</a>, <a href="/wiki/Rat" title="Rat">rats</a>, <a href="/wiki/Mice" class="mw-redirect" title="Mice">mice</a>, <a href="/wiki/Prairie_dog" title="Prairie dog">prairie dogs</a>, <a href="/wiki/Cattle" title="Cattle">cattle</a>, <a href="/wiki/Bird" title="Bird">birds</a>, <a href="/wiki/Snake" title="Snake">snakes</a>, <a href="/wiki/Turtle" title="Turtle">turtles</a> and <a href="/wiki/Tortoise" title="Tortoise">tortoises</a>, <a href="/wiki/Crocodilia" title="Crocodilia">crocodilians</a>, <a href="/wiki/Frog" title="Frog">bullfrogs</a>, and <a href="/wiki/Fish" title="Fish">fish</a>.<sup id="cite_ref-plumb_8-10" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><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><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> It is often used for respiratory infections in snakes, bacterial shell disease in turtles, and <a href="/wiki/Sinusitis" title="Sinusitis">sinusitis</a> in <a href="/wiki/Macaw" title="Macaw">macaws</a>. It is generally contraindicated in <a href="/wiki/Rabbit" title="Rabbit">rabbits</a> and <a href="/wiki/Hare" title="Hare">hares</a> (though it has still been used) because it harms the balance of <a href="/wiki/Gut_flora" class="mw-redirect" title="Gut flora">intestinal microflora</a>.<sup id="cite_ref-plumb_8-11" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>In dogs and cats, amikacin is commonly used as a topical antibiotic for <a href="/wiki/Ear_infections" class="mw-redirect" title="Ear infections">ear infections</a> and for <a href="/wiki/Corneal_ulcers_in_animals" title="Corneal ulcers in animals">corneal ulcers</a>, especially those that are caused by <i>Pseudomonas aeruginosa</i>. The ears are often cleaned before administering the medication, since <a href="/wiki/Pus" title="Pus">pus</a> and cellular debris lessen the activity of amikacin.<sup id="cite_ref-forney_35-1" class="reference"><a href="#cite_note-forney-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Amikacin is administered to the eye when prepared as an ophthalmic ointment or solution, or when injected <a href="/wiki/Conjunctiva" title="Conjunctiva">subconjunctivally</a>.<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> Amikacin in the eye can be accompanied by <a href="/wiki/Cephazolin" class="mw-redirect" title="Cephazolin">cephazolin</a>. Despite its use there amikacin (and all aminoglycosides) are toxic to intraocular structures.<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>In horses, amikacin is FDA-approved for uterine infections (such as <a href="/wiki/Endometriosis" title="Endometriosis">endometriosis</a> and <a href="/wiki/Pyometra" title="Pyometra">pyometra</a>) when caused by susceptible bacteria.<sup id="cite_ref-Amiglyde-V_FDA_label_40-0" class="reference"><a href="#cite_note-Amiglyde-V_FDA_label-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> It is also used in topical medication for the eyes and <a href="/wiki/Arthroscopic_lavage" title="Arthroscopic lavage">arthroscopic lavage</a>; when combined with a cephalosporin, is used to treat <a href="/wiki/Subcutaneous_tissue" title="Subcutaneous tissue">subcutaneous</a> infections that are caused by <i>Staphylococcus</i>. For infections in the limbs or joints, it is often administered with a cephalosporin via <a href="/wiki/Limb_perfusion" title="Limb perfusion">limb perfusion</a> directly into the limb or <a href="/wiki/Joint_injection" title="Joint injection">injected into the joint</a>.<sup id="cite_ref-forney_35-2" class="reference"><a href="#cite_note-forney-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-orsini_41-0" class="reference"><a href="#cite_note-orsini-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup> Amikacin is also injected into the joints with the anti-arthritic medication <a href="/wiki/Adequan" class="mw-redirect" title="Adequan">Adequan</a> in order to prevent infection.<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><p>Side effects in animals include nephrotoxicity, ototoxicity, and <a href="/wiki/Injection_site_reaction" title="Injection site reaction">allergic reactions at IM injection sites</a>. Cats tend to be more sensitive to the vestibular damage caused by ototoxicity. Less frequent side effects include neuromuscular blockade, facial <a href="/wiki/Edema" title="Edema">edema</a>, and <a href="/wiki/Peripheral_neuropathy" title="Peripheral neuropathy">peripheral neuropathy</a>.<sup id="cite_ref-plumb_8-12" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-forney_35-3" class="reference"><a href="#cite_note-forney-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> </p><p>The half-life in most animals is one to two hours.<sup id="cite_ref-papich_43-0" class="reference"><a href="#cite_note-papich-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> </p><p>Treating overdoses of amikacin requires <a href="/wiki/Hemodialysis" title="Hemodialysis">kidney dialysis</a> or <a href="/wiki/Peritoneal_dialysis" title="Peritoneal dialysis">peritoneal dialysis</a>, which reduce serum concentrations of amikacin, and/or penicillins, some of which can form complexes with amikacin that deactivate it.<sup id="cite_ref-plumb_8-13" class="reference"><a href="#cite_note-plumb-8"><span class="cite-bracket">[</span>8<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=Amikacin&action=edit&section=13" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Drugs.com_pregnancy-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Drugs.com_pregnancy_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Drugs.com_pregnancy_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/pregnancy/amikacin.html">"Amikacin Use During Pregnancy"</a>. <i>Drugs.com</i>. 2 December 2019<span class="reference-accessdate">. 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Stockholm, Wisconsin; Ames, Iowa: Wiley. pp. <span class="nowrap">39–</span>43. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-470-95964-0" title="Special:BookSources/978-0-470-95964-0"><bdi>978-0-470-95964-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Amikacin+Sulfate&rft.btitle=Plumb%27s+Veterinary+Drug+Handbook&rft.place=Stockholm%2C+Wisconsin%3B+Ames%2C+Iowa&rft.pages=%3Cspan+class%3D%22nowrap%22%3E39-%3C%2Fspan%3E43&rft.edition=7th&rft.pub=Wiley&rft.date=2011&rft.isbn=978-0-470-95964-0&rft.aulast=Plumb&rft.aufirst=DC&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-AHFS2016-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-AHFS2016_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-11"><sup><i><b>l</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-12"><sup><i><b>m</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-13"><sup><i><b>n</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-14"><sup><i><b>o</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-15"><sup><i><b>p</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-16"><sup><i><b>q</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-17"><sup><i><b>r</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-18"><sup><i><b>s</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-19"><sup><i><b>t</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-20"><sup><i><b>u</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-21"><sup><i><b>v</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-22"><sup><i><b>w</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-23"><sup><i><b>x</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-24"><sup><i><b>y</b></i></sup></a> <a href="#cite_ref-AHFS2016_9-25"><sup><i><b>z</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/amikacin-sulfate.html">"Amikacin Sulfate"</a>. The American Society of Health-System Pharmacists. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161220231044/https://www.drugs.com/monograph/amikacin-sulfate.html">Archived</a> from the original on 20 December 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">8 December</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Amikacin+Sulfate&rft.pub=The+American+Society+of+Health-System+Pharmacists&rft_id=https%3A%2F%2Fwww.drugs.com%2Fmonograph%2Famikacin-sulfate.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-WHO2008-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-WHO2008_10-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWorld_Health_Organization2009" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). <i>WHO Model Formulary 2008</i>. World Health Organization. p. 137. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10665%2F44053">10665/44053</a></span>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9789241547659" title="Special:BookSources/9789241547659"><bdi>9789241547659</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=WHO+Model+Formulary+2008&rft.pages=137&rft.pub=World+Health+Organization&rft.date=2009&rft_id=info%3Ahdl%2F10665%2F44053&rft.isbn=9789241547659&rft.au=World+Health+Organization&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFFischerGanellin2006" class="citation book cs1">Fischer J, Ganellin CR (2006). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA507"><i>Analogue-based Drug Discovery</i></a>. John Wiley & Sons. p. 507. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9783527607495" title="Special:BookSources/9783527607495"><bdi>9783527607495</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20161220092307/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA507">Archived</a> from the original on 20 December 2016.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Analogue-based+Drug+Discovery&rft.pages=507&rft.pub=John+Wiley+%26+Sons&rft.date=2006&rft.isbn=9783527607495&rft.aulast=Fischer&rft.aufirst=J&rft.au=Ganellin%2C+CR&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DFjKfqkaKkAAC%26pg%3DPA507&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=5W-WBQAAQBAJ&pg=PT56"><i>Oxford Handbook of Infectious Diseases and Microbiology</i></a>. OUP Oxford. 2009. p. 56. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780191039621" title="Special:BookSources/9780191039621"><bdi>9780191039621</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20151124232554/https://books.google.ca/books?id=5W-WBQAAQBAJ&pg=PT56">Archived</a> from the original on 24 November 2015.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Oxford+Handbook+of+Infectious+Diseases+and+Microbiology&rft.pages=56&rft.pub=OUP+Oxford&rft.date=2009&rft.isbn=9780191039621&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5W-WBQAAQBAJ%26pg%3DPT56&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-WHO23rd-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-WHO23rd_13-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWorld_Health_Organization2023" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2023). <i>The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023)</i>. Geneva: World Health Organization. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/10665%2F371090">10665/371090</a></span>. WHO/MHP/HPS/EML/2023.02.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+selection+and+use+of+essential+medicines+2023%3A+web+annex+A%3A+World+Health+Organization+model+list+of+essential+medicines%3A+23rd+list+%282023%29&rft.place=Geneva&rft.pub=World+Health+Organization&rft.date=2023&rft_id=info%3Ahdl%2F10665%2F371090&rft.au=World+Health+Organization&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-Amikacin_sulfate_FDA_label-14"><span class="mw-cite-backlink">^ <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-9"><sup><i><b>j</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-10"><sup><i><b>k</b></i></sup></a> <a href="#cite_ref-Amikacin_sulfate_FDA_label_14-11"><sup><i><b>l</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=c0f57839-1c9b-49e5-8c7a-708e2d16495d">"Amikacin sulfate injection, solution"</a>. <i>DailyMed</i>. 10 April 2019<span class="reference-accessdate">. Retrieved <span class="nowrap">13 March</span> 2020</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=DailyMed&rft.atitle=Amikacin+sulfate+injection%2C+solution&rft.date=2019-04-10&rft_id=https%3A%2F%2Fdailymed.nlm.nih.gov%2Fdailymed%2FdrugInfo.cfm%3Fsetid%3Dc0f57839-1c9b-49e5-8c7a-708e2d16495d&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFScholarPratt2000" class="citation book cs1">Scholar EM, Pratt WB (22 May 2000). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=gACeB8XCnpgC&pg=PA15"><i>The Antimicrobial Drugs</i></a> (2nd ed.). Oxford University Press, USA. pp. <span class="nowrap">15–</span>19. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-975971-2" title="Special:BookSources/978-0-19-975971-2"><bdi>978-0-19-975971-2</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170910172330/https://books.google.com/books?id=gACeB8XCnpgC&pg=PA15">Archived</a> from the original on 10 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Antimicrobial+Drugs&rft.pages=%3Cspan+class%3D%22nowrap%22%3E15-%3C%2Fspan%3E19&rft.edition=2nd&rft.pub=Oxford+University+Press%2C+USA&rft.date=2000-05-22&rft.isbn=978-0-19-975971-2&rft.aulast=Scholar&rft.aufirst=EM&rft.au=Pratt%2C+WB&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DgACeB8XCnpgC%26pg%3DPA15&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-cunha-16"><span class="mw-cite-backlink">^ <a href="#cite_ref-cunha_16-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-cunha_16-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-cunha_16-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-cunha_16-3"><sup><i><b>d</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCunha2006" class="citation journal cs1">Cunha BA (November 2006). "New uses for older antibiotics: nitrofurantoin, amikacin, colistin, polymyxin B, doxycycline, and minocycline revisited". <i>The Medical Clinics of North America</i>. Antimicrobial Therapy. <b>90</b> (6): <span class="nowrap">1089–</span>1107. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.mcna.2006.07.006">10.1016/j.mcna.2006.07.006</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/17116438">17116438</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:30373734">30373734</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Medical+Clinics+of+North+America&rft.atitle=New+uses+for+older+antibiotics%3A+nitrofurantoin%2C+amikacin%2C+colistin%2C+polymyxin+B%2C+doxycycline%2C+and+minocycline+revisited&rft.volume=90&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1089-%3C%2Fspan%3E1107&rft.date=2006-11&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A30373734%23id-name%3DS2CID&rft_id=info%3Apmid%2F17116438&rft_id=info%3Adoi%2F10.1016%2Fj.mcna.2006.07.006&rft.aulast=Cunha&rft.aufirst=BA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-medscape-17"><span class="mw-cite-backlink">^ <a href="#cite_ref-medscape_17-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-medscape_17-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-medscape_17-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-medscape_17-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-medscape_17-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-medscape_17-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-medscape_17-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://reference.medscape.com/drug/amikin-amikacin-342516#0">"amikacin (Rx)"</a>. <i>Medscape</i>. WebMD. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170809083119/http://reference.medscape.com/drug/amikin-amikacin-342516">Archived</a> from the original on 9 August 2017<span class="reference-accessdate">. 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Boston: Academic Press. pp. <span class="nowrap">669–</span>675. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-411492-0" title="Special:BookSources/978-0-12-411492-0"><bdi>978-0-12-411492-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chapter+32%3A+Antimicobacterial+Drugs&rft.btitle=Synthesis+of+Best-Seller+Drugs&rft.place=Boston&rft.pages=%3Cspan+class%3D%22nowrap%22%3E669-%3C%2Fspan%3E675&rft.pub=Academic+Press&rft.date=2016&rft.isbn=978-0-12-411492-0&rft.aulast=Vardanyan&rft.aufirst=R&rft.au=Hruby%2C+V&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-FDA_PR-20"><span class="mw-cite-backlink">^ <a href="#cite_ref-FDA_PR_20-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-FDA_PR_20-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-FDA_PR_20-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-FDA_PR_20-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-FDA_PR_20-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-FDA_PR_20-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-FDA_PR_20-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-FDA_PR_20-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-FDA_PR_20-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-FDA_PR_20-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation pressrelease cs1"><a rel="nofollow" class="external text" href="https://www.fda.gov/news-events/press-announcements/fda-approves-new-antibacterial-drug-treat-serious-lung-disease-using-novel-pathway-spur-innovation">"FDA approves a new antibacterial drug to treat a serious lung disease using a novel pathway to spur innovation"</a>. <i>U.S. <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> (FDA)</i> (Press release)<span class="reference-accessdate">. Retrieved <span class="nowrap">12 November</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=FDA+approves+a+new+antibacterial+drug+to+treat+a+serious+lung+disease+using+a+novel+pathway+to+spur+innovation&rft_id=https%3A%2F%2Fwww.fda.gov%2Fnews-events%2Fpress-announcements%2Ffda-approves-new-antibacterial-drug-treat-serious-lung-disease-using-novel-pathway-spur-innovation&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span> <span class="noviewer" typeof="mw:File"><span><img alt="Public Domain" src="//upload.wikimedia.org/wikipedia/en/thumb/6/62/PD-icon.svg/12px-PD-icon.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/6/62/PD-icon.svg/18px-PD-icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/6/62/PD-icon.svg/24px-PD-icon.svg.png 2x" data-file-width="196" data-file-height="196" /></span></span> This article incorporates text from this source, which is in the <a href="/wiki/Public_domain" title="Public domain">public domain</a>.</span> </li> <li id="cite_note-ettinger-21"><span class="mw-cite-backlink">^ <a href="#cite_ref-ettinger_21-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-ettinger_21-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-ettinger_21-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-ettinger_21-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-ettinger_21-4"><sup><i><b>e</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEttingerFeldman2009" class="citation book cs1">Ettinger SJ, Feldman EC (24 December 2009). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=4Qzau1jagOYC&pg=PA1976"><i>Textbook of Veterinary Internal Medicine</i></a>. Elsevier Health Sciences. pp. 1976, 523. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4377-0282-8" title="Special:BookSources/978-1-4377-0282-8"><bdi>978-1-4377-0282-8</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170910172330/https://books.google.com/books?id=4Qzau1jagOYC&pg=PA1976">Archived</a> from the original on 10 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Textbook+of+Veterinary+Internal+Medicine&rft.pages=1976%2C+523&rft.pub=Elsevier+Health+Sciences&rft.date=2009-12-24&rft.isbn=978-1-4377-0282-8&rft.aulast=Ettinger&rft.aufirst=SJ&rft.au=Feldman%2C+EC&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D4Qzau1jagOYC%26pg%3DPA1976&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-maire-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-maire_22-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMaireBourguignonGoutelleDucher2017" class="citation book cs1">Maire P, Bourguignon L, Goutelle S, Ducher M, Jelliffe R (2017). 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Author House. p. 16. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4918-0000-3" title="Special:BookSources/978-1-4918-0000-3"><bdi>978-1-4918-0000-3</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170910172330/https://books.google.com/books?id=h4zCAgAAQBAJ&pg=PA16">Archived</a> from the original on 10 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Essential+Drug+Data+for+Rational+Therapy+in+Veterinary+Practice&rft.pages=16&rft.pub=Author+House&rft.date=2014&rft.isbn=978-1-4918-0000-3&rft.aulast=Eghianruwa&rft.aufirst=K&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dh4zCAgAAQBAJ%26pg%3DPA16&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-morris-24"><span class="mw-cite-backlink">^ <a href="#cite_ref-morris_24-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-morris_24-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMorrisKennis2012" class="citation book cs1">Morris DO, Kennis RA (11 October 2012). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=TsKQVAWxHg4C&pg=PA29"><i>Clinical Dermatology, An Issue of Veterinary Clinics: Small Animal Practice, E-Book</i></a>. Elsevier Health Sciences. p. 29. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-4557-7377-0" title="Special:BookSources/978-1-4557-7377-0"><bdi>978-1-4557-7377-0</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170910172330/https://books.google.com/books?id=TsKQVAWxHg4C&pg=PA29">Archived</a> from the original on 10 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Clinical+Dermatology%2C+An+Issue+of+Veterinary+Clinics%3A+Small+Animal+Practice%2C+E-Book&rft.pages=29&rft.pub=Elsevier+Health+Sciences&rft.date=2012-10-11&rft.isbn=978-1-4557-7377-0&rft.aulast=Morris&rft.aufirst=DO&rft.au=Kennis%2C+RA&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DTsKQVAWxHg4C%26pg%3DPA29&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-corti-25"><span class="mw-cite-backlink">^ <a href="#cite_ref-corti_25-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-corti_25-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-corti_25-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCortiTaegtmeyerImhof2011" class="citation journal cs1">Corti N, Taegtmeyer A, Imhof A (1 January 2011). 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Elsevier Health Sciences. p. 382. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-24293-6" title="Special:BookSources/978-0-323-24293-6"><bdi>978-0-323-24293-6</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170910172330/https://books.google.com/books?id=2phWAgAAQBAJ&pg=PA382">Archived</a> from the original on 10 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Current+Therapy+in+Reptile+Medicine+and+Surgery+%E2%80%93+E-Book&rft.pages=382&rft.pub=Elsevier+Health+Sciences&rft.date=2013-12-12&rft.isbn=978-0-323-24293-6&rft.aulast=Mader&rft.aufirst=DR&rft.au=Divers%2C+SJ&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D2phWAgAAQBAJ%26pg%3DPA382&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMaggsMillerOfri2013" class="citation book cs1">Maggs D, Miller P, Ofri R (7 August 2013). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=8QCduRN3zR0C&pg=PA37"><i>Slatter's Fundamentals of Veterinary Ophthalmology – E-Book</i></a>. 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"Update on Managing Serious Wound Infections in Horses: Wounds Involving Joints and Other Synovial Structures". <i>Journal of Equine Veterinary Science</i>. <b>55</b>: <span class="nowrap">115–</span>122. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.jevs.2017.01.016">10.1016/j.jevs.2017.01.016</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0737-0806">0737-0806</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Equine+Veterinary+Science&rft.atitle=Update+on+Managing+Serious+Wound+Infections+in+Horses%3A+Wounds+Involving+Joints+and+Other+Synovial+Structures&rft.volume=55&rft.pages=%3Cspan+class%3D%22nowrap%22%3E115-%3C%2Fspan%3E122&rft.date=2017-08-01&rft_id=info%3Adoi%2F10.1016%2Fj.jevs.2017.01.016&rft.issn=0737-0806&rft.aulast=Orsini&rft.aufirst=JA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFWanamakerMassey2014" class="citation book cs1">Wanamaker BP, Massey K (25 March 2014). <i>Applied Pharmacology for Veterinary Technicians – E-Book</i>. Elsevier Health Sciences. p. 392. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-29170-5" title="Special:BookSources/978-0-323-29170-5"><bdi>978-0-323-29170-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Applied+Pharmacology+for+Veterinary+Technicians+%E2%80%93+E-Book&rft.pages=392&rft.pub=Elsevier+Health+Sciences&rft.date=2014-03-25&rft.isbn=978-0-323-29170-5&rft.aulast=Wanamaker&rft.aufirst=BP&rft.au=Massey%2C+K&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> <li id="cite_note-papich-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-papich_43-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFPapich2015" class="citation book cs1">Papich MG (October 2015). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=ip8_CwAAQBAJ&pg=PA25">"Amikacin"</a>. <i>Saunders Handbook of Veterinary Drugs: Small and Large Animal</i> (4th ed.). Elsevier Health Sciences. pp. <span class="nowrap">25–</span>27. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-24485-5" title="Special:BookSources/978-0-323-24485-5"><bdi>978-0-323-24485-5</bdi></a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20170910172330/https://books.google.com/books?id=ip8_CwAAQBAJ&pg=PA25">Archived</a> from the original on 10 September 2017.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Amikacin&rft.btitle=Saunders+Handbook+of+Veterinary+Drugs%3A+Small+and+Large+Animal&rft.pages=%3Cspan+class%3D%22nowrap%22%3E25-%3C%2Fspan%3E27&rft.edition=4th&rft.pub=Elsevier+Health+Sciences&rft.date=2015-10&rft.isbn=978-0-323-24485-5&rft.aulast=Papich&rft.aufirst=MG&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Dip8_CwAAQBAJ%26pg%3DPA25&rfr_id=info%3Asid%2Fen.wikipedia.org%3AAmikacin" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output 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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/Chlortetracycline" title="Chlortetracycline">Chlortetracycline</a></li> <li><a href="/wiki/Demeclocycline" title="Demeclocycline">Demeclocycline</a></li> <li><a href="/wiki/Oxytetracycline" title="Oxytetracycline">Oxytetracycline</a></li> <li><a href="/wiki/Tetracycline" title="Tetracycline">Tetracycline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Others</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amphenicol" title="Amphenicol">Amphenicol</a>: <a href="/wiki/Chloramphenicol" title="Chloramphenicol">Chloramphenicol</a></li></ul> <ul><li><a href="/wiki/Aminoglycoside" title="Aminoglycoside">Aminoglycosides</a>: <a class="mw-selflink selflink">Amikacin</a></li> <li><a href="/wiki/Gentamicin" title="Gentamicin">Gentamicin</a></li> <li><a href="/wiki/Neomycin" title="Neomycin">Neomycin</a></li></ul> <ul><li><a href="/wiki/Quinolone_antibiotic" title="Quinolone antibiotic">Quinolones</a>: <a href="/wiki/Nadifloxacin" title="Nadifloxacin">Nadifloxacin</a></li></ul> <ul><li><a href="/wiki/Streptogramin" title="Streptogramin">Streptogramin</a>: <a href="/wiki/Virginiamycin" title="Virginiamycin">Virginiamycin</a></li></ul> <ul><li><a href="/wiki/Rifamycin" title="Rifamycin">Rifamycin</a>: <a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li></ul> <ul><li><i>other:</i> <a href="/wiki/Bacitracin" title="Bacitracin">Bacitracin</a></li> <li><a href="/wiki/Fusidic_acid" title="Fusidic acid">Fusidic acid</a></li> <li><a href="/wiki/Mupirocin" title="Mupirocin">Mupirocin</a></li> <li><a href="/wiki/Tyrothricin" title="Tyrothricin">Tyrothricin</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/Chemotherapy" title="Chemotherapy">Chemotherapeutics</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/Sulfonamide_(medicine)" title="Sulfonamide (medicine)">Sulfonamides</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/Mafenide" title="Mafenide">Mafenide</a></li> <li><a href="/wiki/Silver_sulfadiazine" title="Silver sulfadiazine">Silver sulfadiazine</a></li> <li><a href="/wiki/Sulfamerazine" title="Sulfamerazine">Sulfamerazine</a></li> <li><a href="/wiki/Sulfamethizole" title="Sulfamethizole">Sulfamethizole</a></li> <li><a href="/wiki/Sulfanilamide" title="Sulfanilamide">Sulfanilamide</a></li> <li><a href="/wiki/Sulfathiazole" title="Sulfathiazole">Sulfathiazole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antiviral_drug" title="Antiviral drug">Antivirals</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/Aciclovir" title="Aciclovir">Aciclovir</a></li> <li><a href="/wiki/Berdazimer_sodium" title="Berdazimer sodium">Berdazimer sodium</a></li> <li><a href="/wiki/Docosanol" class="mw-redirect" title="Docosanol">Docosanol</a></li> <li><a href="/wiki/Edoxudine" title="Edoxudine">Edoxudine</a></li> <li><a href="/wiki/Ibacitabine" title="Ibacitabine">Ibacitabine</a></li> <li><a href="/wiki/Idoxuridine" title="Idoxuridine">Idoxuridine</a></li> <li><a href="/wiki/Imiquimod" title="Imiquimod">Imiquimod</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Lysine" title="Lysine">Lysine</a></li> <li><a href="/wiki/Lysozyme" title="Lysozyme">Lysozyme</a></li> <li><a href="/wiki/Penciclovir" title="Penciclovir">Penciclovir</a></li> <li><a href="/wiki/Podophyllotoxin" title="Podophyllotoxin">Podophyllotoxin</a></li> <li><a href="/wiki/Resiquimod" title="Resiquimod">Resiquimod</a></li> <li><a href="/wiki/Tromantadine" title="Tromantadine">Tromantadine</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/Ingenol_mebutate" title="Ingenol mebutate">Ingenol mebutate</a></li> <li><a href="/wiki/Metronidazole" title="Metronidazole">Metronidazole</a></li> <li><a href="/wiki/Tirbanibulin" title="Tirbanibulin">Tirbanibulin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link 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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 class="mw-selflink selflink">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="Amphenicols15" 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 href="/wiki/Macrolide" title="Macrolide">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/Nafithromycin" title="Nafithromycin">Nafithromycin</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="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" 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