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Available in 28 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-28" 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">28 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%88%D9%83%D8%B3%D9%8A_%D8%AA%D8%AA%D8%B1%D8%A7%D8%B3%D9%83%D9%84%D9%8A%D9%86" title="أوكسي تتراسكلين – Arabic" lang="ar" hreflang="ar" data-title="أوكسي تتراسكلين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D8%A7%D9%88%DA%A9%D8%B3%DB%8C_%D8%AA%D8%AA%D8%B1%D8%A7%D8%B3%D8%A7%DB%8C%DA%A9%D9%84%DB%8C%D9%86" title="اوکسی تتراسایکلین – South Azerbaijani" lang="azb" hreflang="azb" data-title="اوکسی تتراسایکلین" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Oxytetracyklin" title="Oxytetracyklin – Czech" lang="cs" hreflang="cs" data-title="Oxytetracyklin" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target"><span>Čeština</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Ocsytetracyclin" title="Ocsytetracyclin – Welsh" lang="cy" hreflang="cy" data-title="Ocsytetracyclin" 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/Oxytetracyclin" title="Oxytetracyclin – German" lang="de" hreflang="de" data-title="Oxytetracyclin" 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/Oxitetraciclina" title="Oxitetraciclina – Spanish" lang="es" hreflang="es" data-title="Oxitetraciclina" 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/Oxitetraziklina" title="Oxitetraziklina – Basque" lang="eu" hreflang="eu" data-title="Oxitetraziklina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target"><span>Euskara</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%A7%DA%A9%D8%B3%DB%8C_%D8%AA%D8%AA%D8%B1%D8%A7%D8%B3%D8%A7%DB%8C%DA%A9%D9%84%DB%8C%D9%86" title="اکسی تتراسایکلین – Persian" lang="fa" hreflang="fa" data-title="اکسی تتراسایکلین" 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/Oxyt%C3%A9tracycline" title="Oxytétracycline – French" lang="fr" hreflang="fr" data-title="Oxytétracycline" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EC%98%A5%EC%8B%9C%ED%85%8C%ED%8A%B8%EB%9D%BC%EC%82%AC%EC%9D%B4%ED%81%B4%EB%A6%B0" title="옥시테트라사이클린 – Korean" lang="ko" hreflang="ko" data-title="옥시테트라사이클린" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Oksitetrasiklin" title="Oksitetrasiklin – Indonesian" lang="id" hreflang="id" data-title="Oksitetrasiklin" 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/Ossitetraciclina" title="Ossitetraciclina – Italian" lang="it" hreflang="it" data-title="Ossitetraciclina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-kn mw-list-item"><a href="https://kn.wikipedia.org/wiki/%E0%B2%86%E0%B2%95%E0%B3%8D%E0%B2%B8%E0%B2%BF%E0%B2%9F%E0%B3%86%E0%B2%9F%E0%B3%8D%E0%B2%B0%E0%B2%B8%E0%B3%88%E0%B2%95%E0%B3%8D%E0%B2%B2%E0%B3%80%E0%B2%A8%E0%B3%8D" title="ಆಕ್ಸಿಟೆಟ್ರಸೈಕ್ಲೀನ್ – Kannada" lang="kn" hreflang="kn" data-title="ಆಕ್ಸಿಟೆಟ್ರಸೈಕ್ಲೀನ್" data-language-autonym="ಕನ್ನಡ" data-language-local-name="Kannada" class="interlanguage-link-target"><span>ಕನ್ನಡ</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Oxitetraciklin" title="Oxitetraciklin – Hungarian" lang="hu" hreflang="hu" data-title="Oxitetraciklin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%93%E0%B4%95%E0%B5%8D%E2%80%8C%E0%B4%B8%E0%B4%BF%E0%B4%9F%E0%B5%86%E0%B4%9F%E0%B5%8D%E0%B4%B0%E0%B4%BE%E0%B4%B8%E0%B5%88%E0%B4%95%E0%B5%8D%E0%B4%B2%E0%B4%BF%E0%B5%BB" title="ഓക്‌സിടെട്രാസൈക്ലിൻ – Malayalam" lang="ml" hreflang="ml" data-title="ഓക്‌സിടെട്രാസൈക്ലിൻ" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target"><span>മലയാളം</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%AA%E3%82%AD%E3%82%B7%E3%83%86%E3%83%88%E3%83%A9%E3%82%B5%E3%82%A4%E3%82%AF%E3%83%AA%E3%83%B3" title="オキシテトラサイクリン – Japanese" lang="ja" hreflang="ja" data-title="オキシテトラサイクリン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%85%E0%AC%95%E0%AD%8D%E0%AC%B8%E0%AC%BF%E0%AC%9F%E0%AD%87%E0%AC%9F%E0%AD%8D%E0%AC%B0%E0%AC%BE%E0%AC%B8%E0%AC%BE%E0%AC%87%E0%AC%95%E0%AD%8D%E0%AC%B2%E0%AC%BF%E0%AC%A8" title="ଅକ୍ସିଟେଟ୍ରାସାଇକ୍ଲିନ – Odia" lang="or" hreflang="or" data-title="ଅକ୍ସିଟେଟ୍ରାସାଇକ୍ଲିନ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Oksytetracyklina" title="Oksytetracyklina – Polish" lang="pl" hreflang="pl" data-title="Oksytetracyklina" 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/Oxitetraciclina" title="Oxitetraciclina – Portuguese" lang="pt" hreflang="pt" data-title="Oxitetraciclina" 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/Oxitetraciclin%C4%83" title="Oxitetraciclină – Romanian" lang="ro" hreflang="ro" data-title="Oxitetraciclină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Oksitetraciklin" title="Oksitetraciklin – Serbian" lang="sr" hreflang="sr" data-title="Oksitetraciklin" 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/Oksitetraciklin" title="Oksitetraciklin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Oksitetraciklin" 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/Oksitetrasykliini" title="Oksitetrasykliini – Finnish" lang="fi" hreflang="fi" data-title="Oksitetrasykliini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%AD%E0%B8%AD%E0%B8%81%E0%B8%8B%E0%B8%B4%E0%B9%80%E0%B8%95%E0%B8%95%E0%B8%A3%E0%B8%B2%E0%B9%84%E0%B8%8B%E0%B8%84%E0%B8%A5%E0%B8%B5%E0%B8%99" title="ออกซิเตตราไซคลีน – Thai" lang="th" hreflang="th" data-title="ออกซิเตตราไซคลีน" 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/Oksitetrasiklin" title="Oksitetrasiklin – Turkish" lang="tr" hreflang="tr" data-title="Oksitetrasiklin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Oxytetracycline" title="Oxytetracycline – Vietnamese" lang="vi" hreflang="vi" data-title="Oxytetracycline" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li><li class="interlanguage-link interwiki-wa mw-list-item"><a href="https://wa.wikipedia.org/wiki/Ocsitetraciclene" title="Ocsitetraciclene – Walloon" lang="wa" hreflang="wa" data-title="Ocsitetraciclene" data-language-autonym="Walon" data-language-local-name="Walloon" class="interlanguage-link-target"><span>Walon</span></a></li><li class="interlanguage-link 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</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</div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output 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Unsourced material may be challenged and removed.<br /><small><span class="plainlinks"><i>Find sources:</i> <a rel="nofollow" class="external text" href="https://www.google.com/search?as_eq=wikipedia&q=%22Oxytetracycline%22">"Oxytetracycline"</a> – <a rel="nofollow" class="external text" href="https://www.google.com/search?tbm=nws&q=%22Oxytetracycline%22+-wikipedia&tbs=ar:1">news</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?&q=%22Oxytetracycline%22&tbs=bkt:s&tbm=bks">newspapers</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.google.com/search?tbs=bks:1&q=%22Oxytetracycline%22+-wikipedia">books</a> <b>·</b> <a rel="nofollow" class="external text" href="https://scholar.google.com/scholar?q=%22Oxytetracycline%22">scholar</a> <b>·</b> <a rel="nofollow" class="external text" href="https://www.jstor.org/action/doBasicSearch?Query=%22Oxytetracycline%22&acc=on&wc=on">JSTOR</a></span></small></span> <span class="date-container"><i>(<span class="date">December 2022</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <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): Oxytetracycline">Oxytetracycline</span></caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Oxytetracycline.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Oxytetracycline.svg/220px-Oxytetracycline.svg.png" decoding="async" width="220" height="123" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/01/Oxytetracycline.svg/330px-Oxytetracycline.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/01/Oxytetracycline.svg/440px-Oxytetracycline.svg.png 2x" data-file-width="512" data-file-height="286" /></a></span></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><span class="mw-default-size" typeof="mw:File/Frameless"><a href="/wiki/File:Oxytetracycline-from-xtal-Mercury-3D-balls.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Oxytetracycline-from-xtal-Mercury-3D-balls.png/220px-Oxytetracycline-from-xtal-Mercury-3D-balls.png" decoding="async" width="220" height="173" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Oxytetracycline-from-xtal-Mercury-3D-balls.png/330px-Oxytetracycline-from-xtal-Mercury-3D-balls.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7a/Oxytetracycline-from-xtal-Mercury-3D-balls.png/440px-Oxytetracycline-from-xtal-Mercury-3D-balls.png 2x" data-file-width="2000" data-file-height="1576" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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">Terramycin</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"><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="Australia">AU</abbr>:</small> D</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/Oral_administration" title="Oral administration">By mouth</a>, <a href="/wiki/Topical_medication" title="Topical medication">topical</a> (<a href="/wiki/Eye_drop" title="Eye drop">eye drop</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">D06AA03</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=D06AA03">WHO</a></span>) <a href="/wiki/ATC_code_A01" title="ATC code A01">A01AB25</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=A01AB25">WHO</a></span>), <a href="/wiki/ATC_code_G01" title="ATC code G01">G01AA07</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=G01AA07">WHO</a></span>), <a href="/wiki/ATC_code_J01" title="ATC code J01">J01AA06</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J01AA06">WHO</a></span>), <a href="/wiki/ATC_code_S01" title="ATC code S01">S01AA04</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S01AA04">WHO</a></span>), <a href="/wiki/ATC_code_A01" title="ATC code A01">QA01AB25</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QA01AB25">WHO</a></span>), <a href="/wiki/ATC_code_J51" class="mw-redirect" title="ATC code J51">QJ51AA06</a> (<span title="www.whocc.no/atcvet"><a rel="nofollow" class="external text" href="https://www.whocc.no/atcvet/atcvet_index/?code=QJ51AA06">WHO</a></span>)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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>In general: ℞ (Prescription only)</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><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/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">6–8 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">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%;">(4<i>S</i>,4a<i>R</i>,5<i>S</i>,5a<i>R</i>,6<i>S</i>,12a<i>S</i>)-4-(Dimethylamino)-3,5,6,10,11,12a-hexahydroxy-6-methyl-1,12-dioxo-1,4,4a,5,5a,6,12,12a-octahydrotetracene-2-carboxamide</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=79-57-2">79-57-2</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/54675779">54675779</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/DB00595">DB00595</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.10482174.html">10482174</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/SLF0D9077S">SLF0D9077S</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/C06624">C06624</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:27701">CHEBI:27701</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/ChEMBL1517">ChEMBL1517</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/Protein_Data_Bank" title="Protein Data Bank">PDB ligand</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li>OAQ (<span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/pdbe-srv/PDBeXplore/ligand/?ligand=OAQ">PDBe</a></span>, <span title="www.rcsb.org"><a rel="nofollow" class="external text" href="https://www.rcsb.org/ligand/OAQ">RCSB PDB</a></span>)</li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/E_number" title="E number"><span title="E number (food additive code)">E number</span></a></th><td class="infobox-data">E703 <a href="/wiki/E_number#E700–E799" title="E number">(antibiotics)</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q411646#P628" 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 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/DTXSID1034260">DTXSID1034260</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q411646#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/100.001.103">100.001.103</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q411646#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">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>24</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>9</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="7002460439000000000♠"></span>460.439</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=CN%28C%29%5BC%40%40H%5D3C%28%5CO%29%3DC%28%5CC%28N%29%3DO%29C%28%3DO%29%5BC%40%40%5D4%28O%29C%28%2FO%29%3DC2%2FC%28%3DO%29c1c%28cccc1O%29%5BC%40%40%5D%28C%29%28O%29%5BC%40H%5D2%5BC%40H%5D%28O%29%5BC%40%40H%5D34">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">181 to 182 °C (358 to 360 °F)</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%;">CN(C)[C@@H]3C(\O)=C(\C(N)=O)C(=O)[C@@]4(O)C(/O)=C2/C(=O)c1c(cccc1O)[C@@](C)(O)[C@H]2[C@H](O)[C@@H]34</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/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25,27-29,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/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:IWVCMVBTMGNXQD-PXOLEDIWSA-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=464196886&page2=Oxytetracycline">(verify)</a></span></span></td></tr></tbody></table> <p><b>Oxytetracycline</b> is a <a href="/wiki/Broad-spectrum_antibiotic" title="Broad-spectrum antibiotic">broad-spectrum</a> <a href="/wiki/Tetracycline_antibiotics" title="Tetracycline antibiotics">tetracycline antibiotic</a>, the second of the group to be discovered. </p><p>Oxytetracycline works by interfering with the ability of bacteria to produce essential proteins. Without these proteins, the bacteria cannot grow, multiply and increase in numbers. Oxytetracycline therefore stops the spread of the infection, and the remaining bacteria are killed by the immune system or eventually die. </p><p>Oxytetracycline is active against a wide variety of bacteria. However, some strains of bacteria have developed resistance to this antibiotic, which has reduced its effectiveness for treating some types of infections. </p><p>Oxytetracycline is used to treat infections caused by <i><a href="/wiki/Chlamydia_infection" class="mw-redirect" title="Chlamydia infection">Chlamydia</a></i>, such as <a href="/wiki/Psittacosis" title="Psittacosis">psittacosis</a>, <a href="/wiki/Trachoma" title="Trachoma">trachoma</a>, and <a href="/wiki/Urethritis" title="Urethritis">urethritis</a>, and infections caused by <i><a href="/wiki/Mycoplasma" title="Mycoplasma">Mycoplasma</a></i> organisms, such as <a href="/wiki/Walking_pneumonia" class="mw-redirect" title="Walking pneumonia">pneumonia</a>. </p><p>Oxytetracycline is used to treat <a href="/wiki/Acne" title="Acne">acne</a>, due to its activity against the bacteria on the skin that influence the development of acne (<i><a href="/wiki/Cutibacterium_acnes" title="Cutibacterium acnes">Cutibacterium acnes</a></i>). It is used to treat flare-ups of <a href="/wiki/Chronic_bronchitis" class="mw-redirect" title="Chronic bronchitis">chronic bronchitis</a>, due to its activity against <i><a href="/wiki/Haemophilus_influenzae" title="Haemophilus influenzae">Haemophilus influenzae</a></i>. Oxytetracycline may be used to treat other rarer infections, such as those caused by a group of microorganisms called <a href="/wiki/Rickettsiae" class="mw-redirect" title="Rickettsiae">rickettsiae</a> (e.g., <a href="/wiki/Rocky_Mountain_spotted_fever" title="Rocky Mountain spotted fever">Rocky Mountain spotted fever</a>). To make sure the bacteria causing an infection are susceptible to it, a tissue sample is usually taken; for example, a swab from the infected area or a urine or blood sample.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2024)">citation needed</span></a></i>]</sup> </p><p>Oxytetracycline was patented in 1949 and came into commercial use in 1950.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> 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> as an alternative to <a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a>.<sup id="cite_ref-WHO22nd_2-0" class="reference"><a href="#cite_note-WHO22nd-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <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=Oxytetracycline&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxytetracycline, like other <a href="/wiki/Tetracycline_antibiotics" title="Tetracycline antibiotics">tetracyclines</a>, is used to treat many infections, both common and rare. Its better absorption profile makes it preferable to tetracycline for moderately severe <a href="/wiki/Acne_vulgaris" class="mw-redirect" title="Acne vulgaris">acne</a> at a dosage of 250–500 mg four times a day for usually six to eight weeks at a time, but alternatives should be sought if no improvement occurs by three months.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>It is sometimes used to treat <a href="/wiki/Spirochaetal" class="mw-redirect" title="Spirochaetal">spirochaetal</a> infections, <a href="/wiki/Clostridial" class="mw-redirect" title="Clostridial">clostridial</a> wound infection, and <a href="/wiki/Anthrax" title="Anthrax">anthrax</a> in patients sensitive to <a href="/wiki/Penicillin" title="Penicillin">penicillin</a>. Oxytetracycline is used to treat infections of the respiratory and urinary tracts, skin, ear, eye and <a href="/wiki/Gonorrhoea" class="mw-redirect" title="Gonorrhoea">gonorrhoea</a>, although its use for such purposes has declined in recent years due to large increases in <a href="/wiki/Bacterial_resistance" class="mw-redirect" title="Bacterial resistance">bacterial resistance</a> to this class of drugs. The drug is particularly useful when penicillins and/or <a href="/wiki/Macrolide" title="Macrolide">macrolides</a> cannot be used due to allergy. It may be used to treat <a href="/wiki/Legionnaire%27s_disease" class="mw-redirect" title="Legionnaire's disease">Legionnaire's disease</a> as a substitute for a macrolide or <a href="/wiki/Quinolone" title="Quinolone">quinolone</a>. </p><p>Oxytetracycline is especially valuable in treating nonspecific urethritis, <a href="/wiki/Lyme_disease" title="Lyme disease">Lyme disease</a>, <a href="/wiki/Brucellosis" title="Brucellosis">brucellosis</a>, <a href="/wiki/Cholera" title="Cholera">cholera</a>, <a href="/wiki/Typhus" title="Typhus">typhus</a>, <a href="/wiki/Tularaemia" class="mw-redirect" title="Tularaemia">tularaemia</a>, and infections caused by <i>Chlamydia, Mycoplasma</i>, and <i>Rickettsia</i>. Doxycycline is now preferred to oxytetracycline for many of these indications because it has improved pharmacologic features.<sup class="noprint Inline-Template" style="margin-left:0.1em; white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Please_clarify" title="Wikipedia:Please clarify"><span title="The text near this tag may need clarification or removal of jargon. (January 2024)">clarification needed</span></a></i>]</sup> </p><p>The standard dose is 250 to 500 mg every six hours by mouth. In particularly severe infections, this dose may be increased accordingly. Occasionally, oxytetracycline is given by <a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular">intramuscular</a> injection or <a href="/wiki/Topical" class="mw-redirect" title="Topical">topically</a> in the form of creams, ophthalmic <a href="/wiki/Ointment" class="mw-redirect" title="Ointment">ointments</a>, or eye drops. </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxytetracycline&action=edit&section=2" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Side effects are mainly gastrointestinal and <a href="/wiki/Photosensitivity" title="Photosensitivity">photosensitive</a> allergic reactions common to the <a href="/wiki/Tetracycline_antibiotics" title="Tetracycline antibiotics">tetracycline antibiotics</a> group. It can damage calcium-rich organs, such as teeth and bones, although this is very rare. It sometimes causes nasal cavities to erode; because of this, tetracyclines should not be used to treat pregnant or lactating women and children under age twelve except in certain conditions where it has been approved by a specialist because there are no obvious substitutes.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2024)">citation needed</span></a></i>]</sup> <a href="/wiki/Candidiasis" title="Candidiasis">Candidiasis</a> (thrush) is not uncommon following treatment with broad-spectrum antibiotics. </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxytetracycline&action=edit&section=3" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>It was first found near <a href="/wiki/Pfizer" title="Pfizer">Pfizer</a> laboratories in a soil sample yielding the <a href="/wiki/Actinomycete" class="mw-redirect" title="Actinomycete">actinomycete</a> <i><a href="/wiki/Streptomyces_rimosus" title="Streptomyces rimosus">Streptomyces rimosus</a></i> by Finlay et al. In 1950, a group at Pfizer led by Francis A. Hochstein, working in a loose collaboration with the Harvard <a href="/wiki/Organic_chemist" class="mw-redirect" title="Organic chemist">organic chemist</a> <a href="/wiki/Robert_B._Woodward" class="mw-redirect" title="Robert B. Woodward">Robert B. Woodward</a>, worked out the chemical structure of oxytetracycline, enabling Pfizer to <a href="/wiki/Mass_production" title="Mass production">mass-produce</a> the drug under the trade name Terramycin.<sup id="cite_ref-pmid15428258_4-0" class="reference"><a href="#cite_note-pmid15428258-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid20522541_5-0" class="reference"><a href="#cite_note-pmid20522541-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> This discovery was a major advancement in tetracycline research and paved the way for the discovery of an oxytetracycline derivative, <a href="/wiki/Doxycycline" title="Doxycycline">doxycycline</a>, which is one of the most popularly used antibiotics today.<sup id="cite_ref-pmid20522541_5-1" class="reference"><a href="#cite_note-pmid20522541-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxytetracycline&action=edit&section=4" title="Edit section: Biosynthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxytetracycline belongs to a structurally diverse class of aromatic <a href="/wiki/Polyketide" title="Polyketide">polyketide</a> antibiotics, also known as bacterial aromatic polyketides, produced by <i><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a></i> via type II <a href="/wiki/Polyketide_synthases" class="mw-redirect" title="Polyketide synthases">polyketide synthases</a> (PKSs).<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Other compounds produced via type II PKSs are important bioactive compounds ranging from anticancer agents like <a href="/wiki/Doxorubicin" title="Doxorubicin">doxorubicin</a> to antibiotics such as <a href="/wiki/Tetracycline" title="Tetracycline">tetracycline</a>. The biosynthesis of oxytetracycline can be broken down into three general portions:<sup id="cite_ref-pmid20522541_5-2" class="reference"><a href="#cite_note-pmid20522541-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> first is the formation of an amidated polyketide backbone with minimal <a href="/wiki/Polyketide_synthases" class="mw-redirect" title="Polyketide synthases">polyketide synthases</a> (PKSs), second is the cyclization of the polyketide backbone, and finally, the formation of anhydrotetracycline—a shared intermediate with tetracycline—to produce oxytetracycline. </p><p>The biosynthesis of oxytetracycline begins with the utilization of PKS enzymes <a href="/wiki/Ketosynthase" class="mw-redirect" title="Ketosynthase">ketosynthase</a> (KS), the chain length factor (CLF), the <a href="/wiki/Acyl_carrier_protein" title="Acyl carrier protein">acyl carrier protein</a> (ACP), and an <a href="/wiki/Acyltransferase" title="Acyltransferase">acyltransferase</a> (encoded as <i>OxyA</i>, <i>OxyB</i>, <i>OxyC</i> and <i>OxyP</i> in the oxytetracycline <a href="/wiki/Gene_cluster" title="Gene cluster">gene cluster</a>)<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> to <a href="/wiki/Catalysis" title="Catalysis">catalyze</a> the extension of the malonamyl-CoA starting unit with eight <a href="/wiki/Malonyl-CoA" title="Malonyl-CoA">malonyl-CoA</a> extender units. The process of elongating the polypeptide skeleton occurs through a series of <a href="/wiki/Claisen_condensation" title="Claisen condensation">Claisen</a>-like <a href="/wiki/Decarboxylation" title="Decarboxylation">decarboxylation</a> reactions until the linear tetracyclic skeleton is formed.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Thus, minimal PKSs form a completed <a href="/wiki/Amide" title="Amide">amidated</a> polyketide backbone without any additional post-synthase tailoring enzymes (Figure 1). </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Biosynthesis_of_the_Amidated_Polyketide_Backbone.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/73/Biosynthesis_of_the_Amidated_Polyketide_Backbone.png/660px-Biosynthesis_of_the_Amidated_Polyketide_Backbone.png" decoding="async" width="660" height="179" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/7/73/Biosynthesis_of_the_Amidated_Polyketide_Backbone.png 1.5x" data-file-width="974" data-file-height="264" /></a><figcaption>Figure 1. The oxytetracycline gene cluster extends the malonamyl-CoA starting unit with 8 × malonyl-CoA to form an amidated polyketide backbone en route to Oxytetracycline.</figcaption></figure> <p>Following the formation of the linear tetracyclic skeleton, four successive <a href="/wiki/Cyclization" class="mw-redirect" title="Cyclization">cyclization</a> reactions must occur in a <a href="/wiki/Regioselective" class="mw-redirect" title="Regioselective">regioselective</a> manner to produce the <a href="/wiki/Aromatic" class="mw-redirect" title="Aromatic">aromatic</a> natural product known as pretetramid, a common precursor to both oxytetracycline and other tetracycline antibiotics.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In the oxytetracycline gene cluster, these enzymes are encoded as <i>OxyK</i> (<a href="/wiki/Aromatase" title="Aromatase">aromatase</a>), <i>OxyN</i> (<a href="/wiki/Cyclase" title="Cyclase">cyclase</a>), and <i>OxyI</i> (cyclase).<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> Formation of pretetramid allows for one of the most important intermediates en route to the biosynthesis of oxytetracycline; this is the generation of anhydrotetracycline.<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 class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources#What_information_to_include" title="Wikipedia:Citing sources"><span title="A complete citation is needed. (November 2023)">full citation needed</span></a></i>]</sup> Anhydrotetracycline contains the first functionalized <a href="/wiki/Tetracycline_antibiotics" title="Tetracycline antibiotics">A ring</a> in this biosynthetic pathway. </p><p>After the formation of anhydrotetracycline, ATC <a href="/wiki/Monooxygenase" title="Monooxygenase">monooxygenase</a> (<i>OxyS</i>) <a href="/wiki/Oxidize" class="mw-redirect" title="Oxidize">oxidizes</a> the C-6 position in an <a href="/wiki/Enantioselective" class="mw-redirect" title="Enantioselective">enantioselective</a> manner in the presence of the <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> <a href="/wiki/NADPH" class="mw-redirect" title="NADPH">NADPH</a> and <a href="/wiki/Atmospheric_oxygen" class="mw-redirect" title="Atmospheric oxygen">atmospheric oxygen</a> to produce 5a,11a-dehydrotetracycline.<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> Next, a <a href="/wiki/Hydroxylation" title="Hydroxylation">hydroxylation</a> occurs at the C-5 position of 5a,11a-dehydrotetracycline via the <a href="/wiki/Oxygenase" title="Oxygenase">oxygenase</a> encoded as <i>OxyE</i> in the oxytetracycline gene cluster. This produces the intermediate 5a,11a-dehydro-oxytetracycline. However, the exact mechanism of this step remains unclear. The final step of this biosynthesis occurs through the <a href="/wiki/Reduction_(chemistry)" class="mw-redirect" title="Reduction (chemistry)">reduction</a> of a <a href="/wiki/Double_bond" title="Double bond">double bond</a> in the <a href="/wiki/Enone" class="mw-redirect" title="Enone">α, β—unsaturated ketone</a> of 5a,11a-dehydro-oxytetracycline. In this final step, the cofactor NADPH is employed by <i>TchA</i> (<a href="/wiki/Reductase" class="mw-redirect" title="Reductase">reductase</a>) as the <a href="/wiki/Reducing_agent" title="Reducing agent">reducing agent</a>. Upon reduction, the <a href="/wiki/Enol" title="Enol">enol</a> form is favored due to <a href="/wiki/Conjugated_system" title="Conjugated system">conjugation</a>, thus producing the aromatic polyketide oxytetracycline. Figure 2 shows the biosynthesis as described above, as well as an arrow-pushing mechanism of NADPH being used as the final cofactor in the biosynthesis of oxytetracycline. </p> <figure class="mw-default-size mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Biosynthesis_of_Oxytetracycline.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Biosynthesis_of_Oxytetracycline.png/880px-Biosynthesis_of_Oxytetracycline.png" decoding="async" width="880" height="368" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Biosynthesis_of_Oxytetracycline.png/1320px-Biosynthesis_of_Oxytetracycline.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5c/Biosynthesis_of_Oxytetracycline.png/1760px-Biosynthesis_of_Oxytetracycline.png 2x" data-file-width="8979" data-file-height="3756" /></a><figcaption>Figure 2. Biosynthesis of oxytetracycline starting from the intermediate anhydrotetracycline. Bottom: Proposed arrow-pushing mechanism of oxytetracycline formation.</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Veterinary_indications">Veterinary indications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Oxytetracycline&action=edit&section=5" title="Edit section: Veterinary indications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxytetracycline is used to control the outbreak of <a href="/wiki/Diseases_of_the_honeybee" class="mw-redirect" title="Diseases of the honeybee">American foulbrood and European foulbrood</a> in <a href="/wiki/Honeybee" class="mw-redirect" title="Honeybee">honeybees</a>. </p><p>Oxytetracycline can be used to correct breathing disorders in <a href="/wiki/Livestock" title="Livestock">livestock</a>. It is administered in a powder or through an intramuscular injection. American livestock producers apply oxytetracycline to livestock feed to prevent diseases and infections in cattle and poultry. The antibiotic is partially absorbed in the <a href="/wiki/Gastrointestinal_tract" title="Gastrointestinal tract">gastrointestinal tract</a> of the animal and the remaining is deposited in manure. Researchers at the <a href="/wiki/Agricultural_Research_Service" title="Agricultural Research Service">Agricultural Research Service</a> studied the breakdown of oxytetracycline in manure depending on various environmental conditions. They found the breakdown slowed with increased saturation of the manure and concluded this was a result of decreased oxygen levels.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> This research helps producers understand the effects of oxytetracycline in animal feed on the environment, bacteria, and antimicrobial resistance. </p><p>Oxytetracycline is used to mark fish which are released and later recaptured. The oxytetracycline interferes with bone deposition, leaving a visible mark on growing bones. </p><p>Oxytetracycline has been formulated as a broad-spectrum <a href="/wiki/Anti-infective" class="mw-redirect" title="Anti-infective">anti-infective</a> for fish under the name Terramycin 200 (TM200).<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> It is used to control certain diseases that adversely affect <a href="/wiki/Aquaculture_of_salmonids" title="Aquaculture of salmonids">salmonids</a>, <a href="/wiki/Catfish" title="Catfish">catfish</a>, and <a href="/wiki/Lobster" title="Lobster">lobsters</a>. </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=Oxytetracycline&action=edit&section=6" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite 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=PA489"><i>Analogue-based Drug Discovery</i></a>. John Wiley & Sons. p. 489. <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>.</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=489&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%3DPA489&rfr_id=info%3Asid%2Fen.wikipedia.org%3AOxytetracycline" class="Z3988"></span></span> </li> <li id="cite_note-WHO22nd-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-WHO22nd_2-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWorld_Health_Organization2021" class="citation book cs1"><a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> (2021). <i>World Health Organization model list of essential medicines: 22nd list (2021)</i>. 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href="/wiki/Antibiotic" title="Antibiotic">Antibiotics</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/Tetracycline" title="Tetracycline">Tetracycline</a> and derivatives</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/Demeclocycline" title="Demeclocycline">Demeclocycline</a></li> <li><a href="/wiki/Chlortetracycline" title="Chlortetracycline">Chlortetracycline</a></li> <li><a class="mw-selflink selflink">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 href="/wiki/Neomycin" title="Neomycin">Neomycin</a></li> <li><a href="/wiki/Gentamicin" title="Gentamicin">Gentamicin</a></li> <li><a href="/wiki/Amikacin" title="Amikacin">Amikacin</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/Fusidic_acid" title="Fusidic acid">Fusidic acid</a></li> <li><a href="/wiki/Bacitracin" title="Bacitracin">Bacitracin</a></li> <li><a href="/wiki/Tyrothricin" title="Tyrothricin">Tyrothricin</a></li> <li><a href="/wiki/Mupirocin" title="Mupirocin">Mupirocin</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/Silver_sulfadiazine" title="Silver sulfadiazine">Silver sulfadiazine</a></li> <li><a href="/wiki/Sulfathiazole" title="Sulfathiazole">Sulfathiazole</a></li> <li><a href="/wiki/Mafenide" title="Mafenide">Mafenide</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/Sulfamerazine" title="Sulfamerazine">Sulfamerazine</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/Penciclovir" title="Penciclovir">Penciclovir</a></li> <li><a href="/wiki/Idoxuridine" title="Idoxuridine">Idoxuridine</a></li> <li><a href="/wiki/Edoxudine" title="Edoxudine">Edoxudine</a></li> <li><a href="/wiki/Imiquimod" title="Imiquimod">Imiquimod</a></li> <li><a href="/wiki/Resiquimod" title="Resiquimod">Resiquimod</a></li> <li><a href="/wiki/Podophyllotoxin" title="Podophyllotoxin">Podophyllotoxin</a></li> <li><a href="/wiki/Docosanol" class="mw-redirect" title="Docosanol">Docosanol</a></li> <li><a href="/wiki/Tromantadine" title="Tromantadine">Tromantadine</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Lysozyme" title="Lysozyme">Lysozyme</a></li> <li><a href="/wiki/Ibacitabine" title="Ibacitabine">Ibacitabine</a></li> <li><a href="/wiki/Lysine" title="Lysine">Lysine</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 rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Gynecological_anti-infectives_and_antiseptics_(G01)" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a 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title="ATC code G01">G01</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antibacterial" class="mw-redirect" title="Antibacterial">Antibiotics</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Candicidin" title="Candicidin">Candicidin</a></li> <li><a href="/wiki/Chloramphenicol" title="Chloramphenicol">Chloramphenicol</a></li> <li><a href="/wiki/Hachimycin" title="Hachimycin">Hachimycin</a></li> <li><a class="mw-selflink selflink">Oxytetracycline</a></li> <li><a href="/wiki/Carfecillin" title="Carfecillin">Carfecillin</a></li> <li><a href="/wiki/Mepartricin" title="Mepartricin">Mepartricin</a></li> <li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a></li> <li><a href="/wiki/Pentamycin" title="Pentamycin">Pentamycin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arsenic" title="Arsenic">Arsenic</a> compounds</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Acetarsol" title="Acetarsol">Acetarsol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinoline" title="Quinoline">Quinoline</a> derivatives</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Diiodohydroxyquinoline" title="Diiodohydroxyquinoline">Diiodohydroxyquinoline</a></li> <li><a href="/wiki/Clioquinol" title="Clioquinol">Clioquinol</a></li> <li><a href="/wiki/Chlorquinaldol" title="Chlorquinaldol">Chlorquinaldol</a></li> <li><a href="/wiki/Dequalinium" title="Dequalinium">Dequalinium</a></li> <li><a href="/wiki/Broxyquinoline" title="Broxyquinoline">Broxyquinoline</a></li> <li><a href="/wiki/8-Hydroxyquinoline" title="8-Hydroxyquinoline">Oxyquinoline</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Organic_acid" title="Organic acid">Organic acids</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Lactic_acid" title="Lactic acid">Lactic acid</a></li> <li><a href="/wiki/Acetic_acid" title="Acetic acid">Acetic acid</a></li> <li><a href="/wiki/Ascorbic_acid" class="mw-redirect" title="Ascorbic acid">Ascorbic acid</a></li></ul> </div></td></tr><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 hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Sulfatolamide" title="Sulfatolamide">Sulfatolamide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antifungal_medication" class="mw-redirect" title="Antifungal medication">Antifungals</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/Imidazole" title="Imidazole">Imidazoles</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/Metronidazole" title="Metronidazole">Metronidazole</a></li> <li><a href="/wiki/Clotrimazole" title="Clotrimazole">Clotrimazole</a></li> <li><a href="/wiki/Miconazole" title="Miconazole">Miconazole</a></li> <li><a href="/wiki/Econazole" title="Econazole">Econazole</a></li> <li><a href="/wiki/Ornidazole" title="Ornidazole">Ornidazole</a></li> <li><a href="/wiki/Isoconazole" title="Isoconazole">Isoconazole</a></li> <li><a href="/wiki/Tioconazole" title="Tioconazole">Tioconazole</a></li> <li><a href="/wiki/Ketoconazole" title="Ketoconazole">Ketoconazole</a></li> <li><a href="/wiki/Fenticonazole" title="Fenticonazole">Fenticonazole</a></li> <li><a href="/wiki/Azanidazole" title="Azanidazole">Azanidazole</a></li> <li><a href="/wiki/Propenidazole" title="Propenidazole">Propenidazole</a></li> <li><a href="/wiki/Butoconazole" title="Butoconazole">Butoconazole</a></li> <li><a href="/wiki/Omoconazole" title="Omoconazole">Omoconazole</a></li> <li><a href="/wiki/Oxiconazole" title="Oxiconazole">Oxiconazole</a></li> <li><a href="/wiki/Flutrimazole" title="Flutrimazole">Flutrimazole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Triazole" title="Triazole">Triazoles</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/Terconazole" title="Terconazole">Terconazole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polyene_antimycotic" title="Polyene antimycotic">Polyenes</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/Nystatin" title="Nystatin">Nystatin</a></li> <li><a href="/wiki/Natamycin" title="Natamycin">Natamycin</a></li> <li><a href="/wiki/Amphotericin_B" title="Amphotericin B">Amphotericin B</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/Ciclopirox" title="Ciclopirox">Ciclopirox</a></li> <li><a href="/wiki/Crystal_violet" title="Crystal violet">Methylrosaniline</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Clodantoin" class="mw-redirect" title="Clodantoin">Clodantoin</a></li> <li><a href="/wiki/Inosine" title="Inosine">Inosine</a></li> <li><a href="/wiki/Policresulen" title="Policresulen">Policresulen</a></li> <li><a href="/wiki/Nifuratel" title="Nifuratel">Nifuratel</a></li> <li><a href="/wiki/Furazolidone" title="Furazolidone">Furazolidone</a></li> <li><a href="/wiki/Povidone-iodine" title="Povidone-iodine">Povidone-iodine</a></li> <li><a href="/wiki/Protiofate" title="Protiofate">Protiofate</a></li> <li><i><a href="/wiki/Lactobacillus_fermentum" class="mw-redirect" title="Lactobacillus fermentum">Lactobacillus fermentum</a></i></li> <li><a href="/wiki/Copper_usnate" title="Copper usnate">Copper usnate</a></li></ul> </div></td></tr></tbody></table></div> <div 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href="/wiki/ATC_code_J01#J01G" title="ATC code J01">J01G</a>, <a href="/wiki/ATC_code_J01#QJ01XQ" title="ATC code J01">QJ01XQ</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/30S" class="mw-redirect" title="30S">30S</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aminoglycoside" title="Aminoglycoside">Aminoglycosides</a><br />(<a href="/wiki/Bacterial_translation#Initiation" title="Bacterial translation">initiation</a> inhibitors)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">-mycin (<i><a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a></i>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Streptomycin" title="Streptomycin">Streptomycin</a><sup>#</sup></li> <li><a href="/wiki/Dihydrostreptomycin" title="Dihydrostreptomycin">Dihydrostreptomycin</a></li></ul> <ul><li><a href="/wiki/Neomycin" title="Neomycin">Neomycin</a><sup>#</sup> <ul><li><a href="/wiki/Framycetin" class="mw-redirect" title="Framycetin">Framycetin</a></li> <li><a href="/wiki/Paromomycin" title="Paromomycin">Paromomycin</a><sup>#</sup></li> <li><a href="/wiki/Ribostamycin" title="Ribostamycin">Ribostamycin</a></li></ul></li></ul> <ul><li><a href="/wiki/Kanamycin" class="mw-redirect" title="Kanamycin">Kanamycin</a> <ul><li><a href="/wiki/Amikacin" title="Amikacin">Amikacin</a><sup>#</sup></li> <li><a href="/wiki/Arbekacin" title="Arbekacin">Arbekacin</a></li> <li><a href="/wiki/Bekanamycin" title="Bekanamycin">Bekanamycin</a></li> <li><a href="/wiki/Dibekacin" title="Dibekacin">Dibekacin</a></li></ul></li></ul> <ul><li><a href="/wiki/Tobramycin" title="Tobramycin">Tobramycin</a> (<a href="/wiki/Loteprednol/tobramycin" title="Loteprednol/tobramycin">+loteprednol</a>)</li> <li><a href="/wiki/Spectinomycin" title="Spectinomycin">Spectinomycin</a><sup>#</sup></li> <li><a href="/wiki/Hygromycin_B" title="Hygromycin B">Hygromycin B</a></li> <li><a href="/wiki/Totomycin" title="Totomycin">Totomycin</a></li> <li><a href="/wiki/Apramycin" title="Apramycin">Apramycin</a></li> <li><a href="/wiki/Nourseothricin" title="Nourseothricin">Nourseothricin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">-micin (<i><a href="/wiki/Micromonospora" title="Micromonospora">Micromonospora</a></i>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Gentamicin" title="Gentamicin">Gentamicin</a><sup>#</sup> <ul><li><a href="/wiki/Netilmicin" title="Netilmicin">Netilmicin</a></li> <li><a href="/wiki/Sisomicin" title="Sisomicin">Sisomicin</a></li> <li><a href="/wiki/Micronomicin" title="Micronomicin">Micronomicin</a></li> <li><a href="/wiki/Plazomicin" title="Plazomicin">Plazomicin</a><sup>#</sup></li> <li><a href="/wiki/Isepamicin" title="Isepamicin">Isepamicin</a></li></ul></li></ul> <ul><li><a href="/wiki/Verdamicin" title="Verdamicin">Verdamicin</a></li> <li><a href="/wiki/Astromicin" title="Astromicin">Astromicin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Butirosin" title="Butirosin">Butirosin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Tetracycline_antibiotics" title="Tetracycline antibiotics">Tetracycline antibiotics</a><br />(<a href="/wiki/Transfer_RNA" title="Transfer RNA">tRNA</a> binding)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%">Tetracyclines</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Doxycycline" title="Doxycycline">Doxycycline</a><sup>#</sup></li> <li><a href="/wiki/Chlortetracycline" title="Chlortetracycline">Chlortetracycline</a></li> <li><a href="/wiki/Clomocycline" title="Clomocycline">Clomocycline</a></li> <li><a href="/wiki/Demeclocycline" title="Demeclocycline">Demeclocycline</a></li> <li><a href="/wiki/Eravacycline" title="Eravacycline">Eravacycline</a></li> <li><a href="/wiki/Lymecycline" title="Lymecycline">Lymecycline</a></li> <li><a href="/wiki/Meclocycline" title="Meclocycline">Meclocycline</a><sup>‡</sup></li> <li><a href="/wiki/Metacycline" title="Metacycline">Metacycline</a></li> <li><a href="/wiki/Minocycline" title="Minocycline">Minocycline</a></li> <li><a href="/wiki/Omadacycline" title="Omadacycline">Omadacycline</a></li> <li><a class="mw-selflink selflink">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" title="2-Oxazolidone">Oxazolidinone</a><br />(<a href="/wiki/Bacterial_translation#Initiation" title="Bacterial translation">initiation</a> inhibitors)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Eperezolid" title="Eperezolid">Eperezolid</a></li> <li><a href="/wiki/Linezolid" title="Linezolid">Linezolid</a><sup>#</sup></li> <li><a href="/wiki/Posizolid" title="Posizolid">Posizolid</a></li> <li><a href="/wiki/Radezolid" title="Radezolid">Radezolid</a></li> <li><a href="/wiki/Ranbezolid" title="Ranbezolid">Ranbezolid</a></li> <li><a href="/wiki/Sutezolid" title="Sutezolid">Sutezolid</a></li> <li><a href="/wiki/Tedizolid" title="Tedizolid">Tedizolid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Peptidyl_transferase" class="mw-redirect" title="Peptidyl transferase">Peptidyl transferase</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Amphenicols" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amphenicol" title="Amphenicol">Amphenicols</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Chloramphenicol" title="Chloramphenicol">Chloramphenicol</a><sup>#</sup></li> <li><a href="/wiki/Azidamfenicol" title="Azidamfenicol">Azidamfenicol</a></li> <li><a href="/wiki/Thiamphenicol" title="Thiamphenicol">Thiamphenicol</a></li> <li><a href="/wiki/Florfenicol" title="Florfenicol">Florfenicol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">MLS (<a href="/wiki/Bacterial_translation#Elongation" title="Bacterial translation">transpeptidation/translocation</a>)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a 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/Oleandomycin" title="Oleandomycin">Oleandomycin</a></li> <li><a href="/wiki/Rokitamycin" title="Rokitamycin">Rokitamycin</a></li> <li><a href="/wiki/Roxithromycin" title="Roxithromycin">Roxithromycin</a></li> <li><a href="/wiki/Solithromycin" title="Solithromycin">Solithromycin</a></li> <li><a href="/wiki/Spiramycin" title="Spiramycin">Spiramycin</a></li> <li><a href="/wiki/Telithromycin" title="Telithromycin">Telithromycin</a></li> <li><a href="/wiki/Tildipirosin" title="Tildipirosin">Tildipirosin</a></li> <li><a href="/wiki/Tilmicosin" title="Tilmicosin">Tilmicosin</a></li> <li><a href="/wiki/Troleandomycin" title="Troleandomycin">Troleandomycin</a></li> <li><a href="/wiki/Tulathromycin" title="Tulathromycin">Tulathromycin</a></li> <li><a href="/wiki/Tylosin" title="Tylosin">Tylosin</a></li> <li><a href="/wiki/Tylvalosin" title="Tylvalosin">Tylvalosin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ketolide" title="Ketolide">Ketolides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Telithromycin" title="Telithromycin">Telithromycin</a><sup>‡</sup></li> <li><a href="/wiki/Cethromycin" title="Cethromycin">Cethromycin</a></li> <li><a href="/wiki/Solithromycin" title="Solithromycin">Solithromycin</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lincosamides" title="Lincosamides">Lincosamides</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Clindamycin" title="Clindamycin">Clindamycin</a><sup>#</sup></li> <li><a href="/wiki/Lincomycin" title="Lincomycin">Lincomycin</a></li> <li><a href="/wiki/Pirlimycin" title="Pirlimycin">Pirlimycin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Streptogramin" title="Streptogramin">Streptogramins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Pristinamycin" title="Pristinamycin">Pristinamycin</a> (<a href="/wiki/Pristinamycin_IA" title="Pristinamycin IA">IA</a>, <a href="/wiki/Pristinamycin_IIA" title="Pristinamycin IIA">IIA</a>, <a href="/wiki/Pristinamycin_IIB" title="Pristinamycin IIB">IIB</a>)</li> <li><a href="/wiki/NXL103" class="mw-redirect" title="NXL103">NXL103</a> (<a href="/wiki/Flopristin" title="Flopristin">Flopristin</a>, <a href="/wiki/Linopristin" title="Linopristin">Linopristin</a>)</li> <li><a href="/wiki/Quinupristin/dalfopristin" title="Quinupristin/dalfopristin">Quinupristin/dalfopristin</a> (<a href="/wiki/Dalfopristin" title="Dalfopristin">Dalfopristin</a>, <a href="/wiki/Quinupristin" title="Quinupristin">Quinupristin</a>)</li> <li><a href="/wiki/Streptogramin_A" title="Streptogramin A">Streptogramin A</a></li> <li><a href="/wiki/Streptogramin_B" title="Streptogramin B">Streptogramin B</a></li> <li><a href="/wiki/Virginiamycin" title="Virginiamycin">Virginiamycin</a> (<a href="/wiki/Virginiamycin_S1" title="Virginiamycin S1">S1</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?type=1x1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Oxytetracycline&oldid=1257247208">https://en.wikipedia.org/w/index.php?title=Oxytetracycline&oldid=1257247208</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Tetracycline_antibiotics" title="Category:Tetracycline antibiotics">Tetracycline antibiotics</a></li><li><a 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