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<div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 22 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-22" 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">22 languages</span> </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%86%D9%88%D8%B1%D9%81%D9%84%D9%88%D9%83%D8%B3%D8%A7%D8%B3%D9%8A%D9%86" title="نورفلوكساسين – Arabic" lang="ar" hreflang="ar" data-title="نورفلوكساسين" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target"><span>العربية</span></a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Norfflocsacin" title="Norfflocsacin – Welsh" lang="cy" hreflang="cy" data-title="Norfflocsacin" 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/Norfloxacin" title="Norfloxacin – German" lang="de" hreflang="de" data-title="Norfloxacin" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%9D%CE%BF%CF%81%CF%86%CE%BB%CE%BF%CE%BE%CE%B1%CF%83%CE%AF%CE%BD%CE%B7" title="Νορφλοξασίνη – Greek" lang="el" hreflang="el" data-title="Νορφλοξασίνη" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target"><span>Ελληνικά</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Norfloxacino" title="Norfloxacino – Spanish" lang="es" hreflang="es" data-title="Norfloxacino" 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/Norfloxazino" title="Norfloxazino – Basque" lang="eu" hreflang="eu" data-title="Norfloxazino" 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/%D9%86%D9%88%D8%B1%D9%81%D9%84%D9%88%DA%A9%D8%B3%D8%A7%D8%B3%DB%8C%D9%86" title="نورفلوکساسین – Persian" lang="fa" hreflang="fa" data-title="نورفلوکساسین" 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/Norfloxacine" title="Norfloxacine – French" lang="fr" hreflang="fr" data-title="Norfloxacine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Norfloxacina" title="Norfloxacina – Italian" lang="it" hreflang="it" data-title="Norfloxacina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Norfloksatsin" title="Norfloksatsin – Uzbek" lang="uz" hreflang="uz" data-title="Norfloksatsin" 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/Norfloksacyna" title="Norfloksacyna – Polish" lang="pl" hreflang="pl" data-title="Norfloksacyna" 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/Norfloxacino" title="Norfloxacino – Portuguese" lang="pt" hreflang="pt" data-title="Norfloxacino" 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/Norfloxacin%C4%83" title="Norfloxacină – Romanian" lang="ro" hreflang="ro" data-title="Norfloxacină" 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%9D%D0%BE%D1%80%D1%84%D0%BB%D0%BE%D0%BA%D1%81%D0%B0%D1%86%D0%B8%D0%BD" title="Норфлоксацин – Russian" lang="ru" hreflang="ru" data-title="Норфлоксацин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Norfloksacin" title="Norfloksacin – Serbian" lang="sr" hreflang="sr" data-title="Norfloksacin" 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/Norfloksacin" title="Norfloksacin – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Norfloksacin" 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/Norfloksasiini" title="Norfloksasiini – Finnish" lang="fi" hreflang="fi" data-title="Norfloksasiini" 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%99%E0%B8%AD%E0%B8%A3%E0%B9%8C%E0%B8%9F%E0%B8%A5%E0%B8%AD%E0%B8%81%E0%B8%8B%E0%B8%B2%E0%B8%8B%E0%B8%B4%E0%B8%99" title="นอร์ฟลอกซาซิน – Thai" lang="th" hreflang="th" data-title="นอร์ฟลอกซาซิน" 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/Norfloksasin" title="Norfloksasin – Turkish" lang="tr" hreflang="tr" data-title="Norfloksasin" 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%9D%D0%BE%D1%80%D1%84%D0%BB%D0%BE%D0%BA%D1%81%D0%B0%D1%86%D0%B8%D0%BD" title="Норфлоксацин – Ukrainian" lang="uk" hreflang="uk" data-title="Норфлоксацин" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E6%B0%9F%E5%93%8C%E9%85%B8" title="氟哌酸 – Cantonese" lang="yue" hreflang="yue" data-title="氟哌酸" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target"><span>粵語</span></a></li><li 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</div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <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">Chemical compound, antibiotic</div> <p class="mw-empty-elt"> </p> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Norfloxacin">Norfloxacin</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:Norfloxacin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Norfloxacin.svg/220px-Norfloxacin.svg.png" decoding="async" width="220" height="119" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/81/Norfloxacin.svg/330px-Norfloxacin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/81/Norfloxacin.svg/440px-Norfloxacin.svg.png 2x" data-file-width="512" data-file-height="278" /></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">Noroxin, Chibroxin, Trizolin, 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/norfloxacin.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/a687006.html">a687006</a></span></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">Oral, ophthalmic</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"><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><a href="/wiki/ATC_code_J01" title="ATC code J01">J01MA06</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J01MA06">WHO</a></span>) <a href="/wiki/ATC_code_S01" title="ATC code S01">S01AE02</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S01AE02">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><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a></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/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">30 to 40%</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">10 to 15%</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"><a href="/wiki/Liver" title="Liver">Hepatic</a></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">3 to 4 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">Renal</a> and fecal</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%;">1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1<i>H</i>-quinoline-<br />3-carboxylic acid</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=70458-96-7">70458-96-7</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/4539">4539</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/DB01059">DB01059</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.4380.html">4380</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/N0F8P22L1P">N0F8P22L1P</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/D00210">D00210</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:100246">CHEBI:100246</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/ChEMBL9">ChEMBL9</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/DTXSID7037680">DTXSID7037680</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q417897#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/100.067.810">100.067.810</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q417897#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>16</sub><span title="Hydrogen">H</span><sub>18</sub><span title="Fluorine">F</span><span title="Nitrogen">N</span><sub>3</sub><span title="Oxygen">O</span><sub>3</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="7002319336000000000♠"></span>319.336</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%28O%29%5CC2%3DC%5CN%28c1cc%28c%28F%29cc1C2%3DO%29N3CCNCC3%29CC">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">220 to 221 °C (428 to 430 °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%;">O=C(O)\C2=C\N(c1cc(c(F)cc1C2=O)N3CCNCC3)CC</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/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)<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:OGJPXUAPXNRGGI-UHFFFAOYSA-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=461742799&page2=Norfloxacin">(verify)</a></span></span></td></tr></tbody></table> <p><b>Norfloxacin</b>, sold under the brand name <b>Noroxin</b> among others, is an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a><sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> that belongs to the class of <a href="/wiki/Quinolone_antibiotic" title="Quinolone antibiotic">fluoroquinolone antibiotics</a>. It is used to treat <a href="/wiki/Urinary_tract_infections" class="mw-redirect" title="Urinary tract infections">urinary tract infections</a>, gynecological infections, inflammation of the prostate gland, <a href="/wiki/Gonorrhea" title="Gonorrhea">gonorrhea</a> and bladder infection.<sup id="cite_ref-fda08_3-0" class="reference"><a href="#cite_note-fda08-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Davisnorflox_4-0" class="reference"><a href="#cite_note-Davisnorflox-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> Eye drops were approved for use in children older than one year of age.<sup id="cite_ref-accessdata.fda.gov_6-0" class="reference"><a href="#cite_note-accessdata.fda.gov-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Norfloxacin is associated with a number of rare serious adverse reactions as well as spontaneous <a href="/wiki/Tendon_ruptures" class="mw-redirect" title="Tendon ruptures">tendon ruptures</a><sup id="cite_ref-pmid26393387_7-0" class="reference"><a href="#cite_note-pmid26393387-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> and irreversible <a href="/wiki/Peripheral_neuropathy" title="Peripheral neuropathy">peripheral neuropathy</a>. Tendon problems may manifest long after therapy had been completed and in severe cases may result in lifelong disabilities. </p><p>It was patented in 1977 and approved for medical use in 1983.<sup id="cite_ref-Fis2006_8-0" class="reference"><a href="#cite_note-Fis2006-8"><span class="cite-bracket">[</span>8<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=Norfloxacin&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The initial approval by the <a href="/wiki/Food_and_Drug_Administration_(United_States)" class="mw-redirect" title="Food and Drug Administration (United States)">U.S. Food and Drug Administration</a> (FDA) in 1986 encompassed the following indications: </p> <ul><li>Uncomplicated urinary tract infections (including cystitis)</li> <li>Complicated urinary tract infections (restricted use) <sup id="cite_ref-docguide_9-0" class="reference"><a href="#cite_note-docguide-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup></li> <li>Uncomplicated urethral and cervical gonorrhea (<i>however this indication is no longer considered to be effective by some experts due to bacterial resistance</i>) <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><sup id="cite_ref-nycms.org_11-0" class="reference"><a href="#cite_note-nycms.org-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup></li> <li>Prostatitis due to <i>Escherichia coli</i>.<sup id="cite_ref-pmid1647371_12-0" class="reference"><a href="#cite_note-pmid1647371-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup></li> <li>Syphilis treatment: Norfloxacin has not been shown to be effective in the treatment of syphilis. Antimicrobial agents used in high doses for short periods of time to treat gonorrhea may mask or delay the symptoms of incubating syphilis.<sup id="cite_ref-fda06_13-0" class="reference"><a href="#cite_note-fda06-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup></li></ul> <p>Although fluoroquinolones are sometimes used to treat <a href="/wiki/Typhoid" class="mw-redirect" title="Typhoid">typhoid</a> and <a href="/wiki/Paratyphoid_fever" title="Paratyphoid fever">paratyphoid fever</a>, norfloxacin had more clinical failures than the other fluoroquinolones (417 participants, 5 trials).<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p>In ophthalmology, Norfloxacin licensed use is limited to the treatment of conjunctival infections caused by susceptible bacteria.<sup id="cite_ref-accessdata.fda.gov_6-1" class="reference"><a href="#cite_note-accessdata.fda.gov-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Norfloxacin has been restricted in the <a href="/wiki/Republic_of_Ireland" title="Republic of Ireland">Republic of Ireland</a> due to the risks of <i><a href="/wiki/Clostridioides_difficile_infection" title="Clostridioides difficile infection">C. difficile</a></i> super infections and permanent nerve as well as tendon injuries. Its licensed use in acute and chronic complicated kidney infections has been withdrawn as a result.<sup id="cite_ref-wottooa_15-0" class="reference"><a href="#cite_note-wottooa-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p><p>The <a href="/wiki/European_Medicines_Agency" title="European Medicines Agency">European Medicines Agency</a>, also in 2008, had recommended restricting the use of oral norfloxacin to treat urinary infections. CHMP had concluded that the marketing authorizations for norfloxacin, when used in the treatment of acute or chronic complicated pyelonephritis, should be withdrawn because the benefits do not outweigh their risks in this indication. CHMP stated that doctors should not prescribe oral norfloxacin for complicated pyelonephritis and should consider switching patients already taking oral norfloxacin for this type of infection to an alternative antibiotic.<sup id="cite_ref-docguide_9-1" class="reference"><a href="#cite_note-docguide-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> </p><p>Norfloxacin is used for prevention of <a href="/wiki/Spontaneous_bacterial_peritonitis" title="Spontaneous bacterial peritonitis">spontaneous bacterial peritonitis</a> in cirrhotic patients who have a low ascites fluid protein level, impaired renal function, severe liver disease, have had a prior episode of spontaneous bacterial peritonitis, or esophageal variceal bleeding.<sup id="cite_ref-pmid3770358_16-0" class="reference"><a href="#cite_note-pmid3770358-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17854593_17-0" class="reference"><a href="#cite_note-pmid17854593-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid9764990_18-0" class="reference"><a href="#cite_note-pmid9764990-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Note: Norfloxacin may be licensed for other uses, or restricted, by the various regulatory agencies worldwide. </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=Norfloxacin&action=edit&section=2" title="Edit section: Contraindications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>As noted above, under licensed use, norfloxacin is also now considered to be contraindicated for the treatment of certain sexually transmitted diseases by some experts due to bacterial resistance.<sup id="cite_ref-nycms.org_11-1" class="reference"><a href="#cite_note-nycms.org-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> </p><p>Norfloxacin is contraindicated in those with a history of tendonitis, tendon rupture and those with a hypersensitivity to fluoroquinolones.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>There are three contraindications found within the 2008 package<sup id="cite_ref-fda08_3-1" class="reference"><a href="#cite_note-fda08-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> insert: </p> <ul><li>"Noroxin (norfloxacin) is contraindicated in persons with a history of hypersensitivity, tendinitis, or tendon rupture associated with the use of norfloxacin or any member of the quinolone group of antimicrobial agents."</li> <li>"Quinolones, including norfloxacin, have been shown in vitro to inhibit CYP1A2. Concomitant use with drugs metabolized by CYP1A2 (e.g., caffeine, clozapine, ropinirole, tacrine, theophylline, tizanidine) may result in increased substrate drug concentrations when given in usual doses. Patients taking any of these drugs concomitantly with norfloxacin should be carefully monitored."</li> <li>"Concomitant administration with <a href="/wiki/Tizanidine" title="Tizanidine">tizanidine</a> is contraindicated"</li></ul> <p>Norfloxacin is also considered to be contraindicated within the pediatric population. </p> <ul><li><b>Pregnancy</b></li></ul> <p>Norfloxacin has been reported to rapidly cross the blood-placenta and blood-milk barrier, and is extensively distributed into the fetal tissues. For this reason norfloxacin and other fluoroquinolones are contraindicated during pregnancy due to the risk of spontaneous abortions and birth defects. The fluoroquinolones have also been reported as being present in the mother's milk and are passed on to the nursing child, which may increases the risk of the child having an adverse reaction even though the child had never been prescribed or taken any of the drugs found within this class.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> As safer alternatives are generally available norfloxacin is contraindicated during pregnancy, especially during the first trimester. The manufacturer only recommends use of norfloxacin during pregnancy when benefit outweighs risk.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <ul><li><b>Children</b></li></ul> <p>A 1998 retrospective survey found that numerous side effects have been recorded in reference to the unapproved use of norfloxacin in the pediatric population.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Fluoroquinolones are not licensed by the FDA for use in children due to the risk of fatalities<sup id="cite_ref-pmid1592498_25-0" class="reference"><a href="#cite_note-pmid1592498-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> as well as permanent injury to the musculoskeletal system, with two exceptions. <a href="/wiki/Ciprofloxacin" title="Ciprofloxacin">Ciprofloxacin</a> is being licensed for the treatment of Complicated Urinary Tract Infections and Pyelonephritis due to Escherichia coli and Inhalational Anthrax (post-exposure) and <a href="/wiki/Levofloxacin" title="Levofloxacin">levofloxacin</a> was recently licensed for the treatment of Inhalational Anthrax (post-exposure). However, the Fluoroquinolones are licensed to treat lower respiratory infections in children with <a href="/wiki/Cystic_fibrosis" title="Cystic fibrosis">cystic fibrosis</a> in the UK. </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=Norfloxacin&action=edit&section=3" title="Edit section: Adverse effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In general, fluoroquinolones are well tolerated, with most side-effects being mild to moderate.<sup id="cite_ref-Owens_RC,_Ambrose_PG_2005_S144–57_26-0" class="reference"><a href="#cite_note-Owens_RC,_Ambrose_PG_2005_S144–57-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> On occasion, serious <a href="/wiki/Adverse_effect" title="Adverse effect">adverse effects</a> occur.<sup id="cite_ref-pmid11172695_27-0" class="reference"><a href="#cite_note-pmid11172695-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> Common side-effects include gastrointestinal effects such as nausea, vomiting, and diarrhea, as well as headache and insomnia. </p><p>The overall rate of adverse events in patients treated with fluoroquinolones is roughly similar to that seen in patients treated with other antibiotic classes.<sup id="cite_ref-Levine_2006_28-0" class="reference"><a href="#cite_note-Levine_2006-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-30" class="reference"><a href="#cite_note-30"><span class="cite-bracket">[</span>30<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-31" class="reference"><a href="#cite_note-31"><span class="cite-bracket">[</span>31<span class="cite-bracket">]</span></a></sup> A U.S. Centers for Disease Control study found patients treated with fluoroquinolones experienced adverse events severe enough to lead to an emergency department visit more frequently than those treated with cephalosporins or macrolides, but less frequently than those treated with penicillins, clindamycin, sulfonamides, or vancomycin.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32"><span class="cite-bracket">[</span>32<span class="cite-bracket">]</span></a></sup> </p><p>Post-marketing surveillance has revealed a variety of relatively rare but serious adverse effects that are associated with all members of the fluoroquinolone antibacterial class. Among these, tendon problems and exacerbation of the symptoms of the neurological disorder <a href="/wiki/Myasthenia_gravis" title="Myasthenia gravis">myasthenia gravis</a> are the subject of "black box" warnings in the United States. The most severe form of tendonopathy associated with fluoroquinolone administration is tendon rupture, which in the great majority of cases involves the Achilles tendon. Younger people typically experience good recovery, but permanent disability is possible, and is more likely in older patients.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33"><span class="cite-bracket">[</span>33<span class="cite-bracket">]</span></a></sup> The overall frequency of fluoroquinolone-associated Achilles tendon rupture in patients treated with ciprofloxacin or levofloxacin has been estimated at 17 per 100,000 treatments.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34"><span class="cite-bracket">[</span>34<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-35" class="reference"><a href="#cite_note-35"><span class="cite-bracket">[</span>35<span class="cite-bracket">]</span></a></sup> Risk is substantially elevated in the elderly and in those with recent exposure to topical or systemic corticosteroid therapy. Simultaneous use of <a href="/wiki/Corticosteroids" class="mw-redirect" title="Corticosteroids">corticosteroids</a> is present in almost one-third of quinolone-associated tendon rupture.<sup id="cite_ref-pmid16139623_36-0" class="reference"><a href="#cite_note-pmid16139623-36"><span class="cite-bracket">[</span>36<span class="cite-bracket">]</span></a></sup> Tendon damage may manifest during, as well as up to a year after fluoroquinolone therapy has been completed.<sup id="cite_ref-pmid10970974_37-0" class="reference"><a href="#cite_note-pmid10970974-37"><span class="cite-bracket">[</span>37<span class="cite-bracket">]</span></a></sup> </p><p>FQs prolong the QT interval by blocking voltage-gated potassium channels.<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> Prolongation of the QT interval can lead to <a href="/wiki/Torsades_de_pointes" title="Torsades de pointes">torsades de pointes</a>, a life-threatening arrhythmia, but in practice, this appears relatively uncommon in part because the most widely prescribed fluoroquinolones (ciprofloxacin and levofloxacin) only minimally prolong the QT interval.<sup id="cite_ref-Rubinstein_39-0" class="reference"><a href="#cite_note-Rubinstein-39"><span class="cite-bracket">[</span>39<span class="cite-bracket">]</span></a></sup> </p><p><i>Clostridioides difficile</i>-associated diarrhea may occur in connection with the use of any antibacterial drug, especially those with a broad spectrum of activity such as clindamycin, cephalosporins, and fluoroquinolones. Fluoroquinoline treatment is associated with risk that is similar to<sup id="cite_ref-40" class="reference"><a href="#cite_note-40"><span class="cite-bracket">[</span>40<span class="cite-bracket">]</span></a></sup> or less <sup id="cite_ref-41" class="reference"><a href="#cite_note-41"><span class="cite-bracket">[</span>41<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Levine_2006_28-1" class="reference"><a href="#cite_note-Levine_2006-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> than that associated with broad spectrum cephalosporins. Fluoroquinolone administration may be associated with the acquisition and outgrowth of a particularly virulent <i>Clostridioides</i> strain.<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>The U.S. prescribing information contains a warning regarding uncommon cases of peripheral neuropathy, which can be permanent.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43"><span class="cite-bracket">[</span>43<span class="cite-bracket">]</span></a></sup> Other nervous system effects include insomnia, restlessness, and rarely, seizure, convulsions, and psychosis<sup id="cite_ref-44" class="reference"><a href="#cite_note-44"><span class="cite-bracket">[</span>44<span class="cite-bracket">]</span></a></sup> Other rare and serious adverse events have been observed with varying degrees of evidence for causation.<sup id="cite_ref-babar_45-0" class="reference"><a href="#cite_note-babar-45"><span class="cite-bracket">[</span>45<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Rouveix-_46-0" class="reference"><a href="#cite_note-Rouveix--46"><span class="cite-bracket">[</span>46<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17911203_47-0" class="reference"><a href="#cite_note-pmid17911203-47"><span class="cite-bracket">[</span>47<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-48" class="reference"><a href="#cite_note-48"><span class="cite-bracket">[</span>48<span class="cite-bracket">]</span></a></sup> </p><p>Events that may occur in acute overdose are rare, and include <a href="/wiki/Kidney_failure" title="Kidney failure">kidney failure</a> and <a href="/wiki/Seizure" title="Seizure">seizure</a>.<sup id="cite_ref-Gold2006_49-0" class="reference"><a href="#cite_note-Gold2006-49"><span class="cite-bracket">[</span>49<span class="cite-bracket">]</span></a></sup> Susceptible groups of patients, such as children and the elderly, are at greater risk of adverse reactions during therapeutic use.<sup id="cite_ref-Owens_RC,_Ambrose_PG_2005_S144–57_26-1" class="reference"><a href="#cite_note-Owens_RC,_Ambrose_PG_2005_S144–57-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid17559736_50-0" class="reference"><a href="#cite_note-pmid17559736-50"><span class="cite-bracket">[</span>50<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-51" class="reference"><a href="#cite_note-51"><span class="cite-bracket">[</span>51<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=Norfloxacin&action=edit&section=4" title="Edit section: Interactions"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The toxicity of drugs that are metabolised by the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> system is enhanced by concomitant use of some quinolones. Quinolones, including norfloxacin, may enhance the effects of oral anticoagulants, including warfarin or its derivatives or similar agents. When these products are administered concomitantly, prothrombin time or other suitable coagulation tests should be closely monitored. Coadministration may dangerously increase coumadin <a href="/wiki/Warfarin" title="Warfarin">warfarin</a> activity; INR should be monitored closely. <sup id="cite_ref-fda06_13-1" class="reference"><a href="#cite_note-fda06-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> They may also interact with the <a href="/wiki/GABA_A_receptor" class="mw-redirect" title="GABA A receptor">GABA A receptor</a> and cause neurological symptoms; this effect is augmented by certain <a href="/wiki/Non-steroidal_anti-inflammatory_drug" class="mw-redirect" title="Non-steroidal anti-inflammatory drug">non-steroidal anti-inflammatory drugs</a>.<sup id="cite_ref-52" class="reference"><a href="#cite_note-52"><span class="cite-bracket">[</span>52<span class="cite-bracket">]</span></a></sup> The concomitant administration of a non-steroidal anti-inflammatory drug (NSAID) with a quinolone, including norfloxacin, may increase the risk of CNS stimulation and convulsive seizures. Therefore, norfloxacin should be used with caution in individuals receiving NSAIDS concomitantly.<sup id="cite_ref-53" class="reference"><a href="#cite_note-53"><span class="cite-bracket">[</span>53<span class="cite-bracket">]</span></a></sup> </p><p>Elevated serum levels of cyclosporine have been reported with concomitant use of cyclosporine with norfloxacin. Therefore, cyclosporine serum levels should be monitored and appropriate cyclosporine dosage adjustments made when these drugs are used concomitantly. </p><p>The concomitant administration of quinolones including norfloxacin with glyburide (a <a href="/wiki/Sulfonylurea" title="Sulfonylurea">sulfonylurea</a> agent) has, on rare occasions, resulted in severe hypoglycemia. Therefore, monitoring of blood glucose is recommended when these agents are co-administered. </p> <div class="mw-heading mw-heading3"><h3 id="Medications">Medications</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Norfloxacin&action=edit&section=5" title="Edit section: Medications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Some quinolones exert an inhibitory effect on the cytochrome P-450 system, thereby reducing theophylline clearance and increasing theophylline blood levels. Coadministration of certain fluoroquinolones and other drugs primarily metabolized by CYP1A2 (e.g. theophylline, methylxanthines, tizanidine) results in increased plasma concentrations and could lead to clinically significant side effects of the coadministered drug. Additionally other fluoroquinolones, especially enoxacin, and to a lesser extent ciprofloxacin and pefloxacin, also inhibit the metabolic clearance of theophylline.<sup id="cite_ref-54" class="reference"><a href="#cite_note-54"><span class="cite-bracket">[</span>54<span class="cite-bracket">]</span></a></sup> </p><p>Such drug interactions are associated with the molecular structural modifications of the quinolone ring, specifically interactions involving <a href="/wiki/NSAIDS" class="mw-redirect" title="NSAIDS">NSAIDS</a> and <a href="/wiki/Theophylline" title="Theophylline">theophylline</a>. As such, these drug interactions involving the fluoroquinolones appear to be drug specific rather than a class effect. The fluoroquinolones have also been shown to interfere with the metabolism of caffeine<sup id="cite_ref-55" class="reference"><a href="#cite_note-55"><span class="cite-bracket">[</span>55<span class="cite-bracket">]</span></a></sup> and the absorption of levothyroxine. The interference with the metabolism of caffeine may lead to the reduced clearance of caffeine and a prolongation of its serum half-life, resulting in a caffeine overdose. This may lead to reduced clearance of caffeine and a prolongation of the plasma's half-life that may lead to accumulation of caffeine in plasma when products containing caffeine are consumed while taking norfloxacin. <sup id="cite_ref-fda06_13-2" class="reference"><a href="#cite_note-fda06-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> </p><p>The use of NSAIDs (Non Steroid Anti Inflammatory Drugs) while undergoing fluoroquinolone therapy is contra-indicated due to the risk of severe CNS adverse reactions, including but not limited to seizure disorders. Fluoroquinolones with an unsubstituted piperazinyl moiety at position 7 have the potential to interact with NSAIDs and/or their metabolites, resulting in antagonism of GABA neurotransmission.<sup id="cite_ref-56" class="reference"><a href="#cite_note-56"><span class="cite-bracket">[</span>56<span class="cite-bracket">]</span></a></sup> </p><p>The use of norfloxacin concomitantly has also been associated with transient elevations in serum creatinine in patients receiving cyclosporine, on rare occasions, resulted in severe hypoglycemia with sulfonylurea. Renal tubular transport of methotrexate may be inhibited by concomitant administration of norfloxacin, potentially leading to increased plasma levels of methotrexate. This might increase the risk of methotrexate toxic reactions. </p><p>Current or past treatment with oral corticosteroids is associated with an increased risk of Achilles tendon rupture, especially in elderly patients who are also taking the fluoroquinolones.<sup id="cite_ref-57" class="reference"><a href="#cite_note-57"><span class="cite-bracket">[</span>57<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Overdose">Overdose</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Norfloxacin&action=edit&section=6" title="Edit section: Overdose"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Treatment of overdose includes emptying of the stomach via induced vomiting or by <a href="/wiki/Gastric_lavage" title="Gastric lavage">gastric lavage</a>. Careful monitoring and supportive treatment, monitoring of renal and liver function, and maintaining adequate hydration is recommended by the manufacturer. Administration of magnesium, aluminum, or calcium containing antacids can reduce the absorption of norfloxacin.<sup id="cite_ref-fda08_3-2" class="reference"><a href="#cite_note-fda08-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Norfloxacin&action=edit&section=7" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Norfloxacin is a <a href="/wiki/Broad-spectrum_antibiotic" title="Broad-spectrum antibiotic">broad-spectrum antibiotic</a> that is active against both <a href="/wiki/Gram-positive" class="mw-redirect" title="Gram-positive">Gram-positive</a> and <a href="/wiki/Gram-negative" class="mw-redirect" title="Gram-negative">Gram-negative</a> bacteria. It functions by inhibiting <a href="/wiki/DNA_gyrase" title="DNA gyrase">DNA gyrase</a>, a type II <a href="/wiki/Topoisomerase" title="Topoisomerase">topoisomerase</a>, and topoisomerase IV,<sup id="cite_ref-58" class="reference"><a href="#cite_note-58"><span class="cite-bracket">[</span>58<span class="cite-bracket">]</span></a></sup> enzymes necessary to separate bacterial DNA, thereby inhibiting cell division. Norfloxacin does not bind to DNA gyrase but does bind to the substrate DNA.<sup id="cite_ref-pmid2982149_59-0" class="reference"><a href="#cite_note-pmid2982149-59"><span class="cite-bracket">[</span>59<span class="cite-bracket">]</span></a></sup> A review in 2001 suggests that <a href="/wiki/Cytotoxicity" title="Cytotoxicity">cytotoxicity</a> of fluoroquinolones is likely a 2-step process involving (1) conversion of the topoisomerase-quinolone-DNA complex to an irreversible form and (2) generation of a double-strand break by denaturation of the topoisomerase.<sup id="cite_ref-60" class="reference"><a href="#cite_note-60"><span class="cite-bracket">[</span>60<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Pharmacokinetics">Pharmacokinetics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Norfloxacin&action=edit&section=8" title="Edit section: Pharmacokinetics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>"Absorption of norfloxacin is rapid following single doses of 200 mg, 400 mg and 800 mg. At the respective doses, mean peak serum and plasma concentrations of 0.8, 1.5 and 2.4 μg/mL are attained approximately one hour after dosing. The effective half-life of norfloxacin in serum and plasma is 3–4 hours. Steady-state concentrations of norfloxacin will be attained within two days of dosing. Renal excretion occurs by both glomerular filtration and tubular secretion as evidenced by the high rate of renal clearance (approximately 275 mL/min). Within 24 hours of drug administration, 26 to 32% of the administered dose is recovered in the urine as norfloxacin with an additional 5-8% being recovered in the urine as six active metabolites of lesser antimicrobial potency. Only a small percentage (less than 1%) of the dose is recovered thereafter. Fecal recovery accounts for another 30% of the administered dose. Two to three hours after a single 400-mg dose, urinary concentrations of 200 μg/mL or more are attained in the urine. In healthy volunteers, mean urinary concentrations of norfloxacin remain above 30 μg/mL for at least 12 hours following a 400-mg dose. The urinary pH may affect the solubility of norfloxacin. Norfloxacin is least soluble at urinary pH of 7.5 with greater solubility occurring at pHs above and below this value. The serum protein binding of norfloxacin is between 10 and 15%." Quoting from the 2009 package insert for Noroxin.<sup id="cite_ref-fda08_3-3" class="reference"><a href="#cite_note-fda08-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p><p>Biotransformation is via the liver and kidneys, with a half-life of 3–4 hours.<sup id="cite_ref-DB01059_61-0" class="reference"><a href="#cite_note-DB01059-61"><span class="cite-bracket">[</span>61<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Norfloxacin&action=edit&section=9" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The first members of the quinolone antibacterial class were relatively low potency drugs such as <a href="/wiki/Nalidixic_acid" title="Nalidixic acid">nalidixic acid</a>, used mainly in the treatment of urinary tract infections owing to their renal excretion and propensity to be concentrated in urine.<sup id="cite_ref-accessdata.fda.gov_6-2" class="reference"><a href="#cite_note-accessdata.fda.gov-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-62" class="reference"><a href="#cite_note-62"><span class="cite-bracket">[</span>62<span class="cite-bracket">]</span></a></sup> In 1979 the publication of a patent<sup id="cite_ref-63" class="reference"><a href="#cite_note-63"><span class="cite-bracket">[</span>63<span class="cite-bracket">]</span></a></sup> filed by the pharmaceutical arm of Kyorin Seiyaku Kabushiki Kaisha disclosed the discovery of norfloxacin, and the demonstration that certain structural modifications including the attachment of a fluorine atom to the quinolone ring leads to dramatically enhanced antibacterial potency.<sup id="cite_ref-pmid6213200_64-0" class="reference"><a href="#cite_note-pmid6213200-64"><span class="cite-bracket">[</span>64<span class="cite-bracket">]</span></a></sup> </p><p>In spite of the substantial increase in antibacterial activity of norfloxacin relative to early fluoroquinolones, it did not become a widely used antibiotic. Other companies initiated fluoroquinolone discovery programs in the aftermath of the publication of the norfloxacin patent. Bayer Pharmaceuticals discovered that the addition of a single carbon atom to the norfloxacin structure provided another 4 to 10-fold improvement in activity.<sup id="cite_ref-65" class="reference"><a href="#cite_note-65"><span class="cite-bracket">[</span>65<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Ciprofloxacin" title="Ciprofloxacin">Ciprofloxacin</a> reached the market just one year after norfloxacin and achieved sales of 1.5 billion Euros at its peak.<sup id="cite_ref-66" class="reference"><a href="#cite_note-66"><span class="cite-bracket">[</span>66<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-67" class="reference"><a href="#cite_note-67"><span class="cite-bracket">[</span>67<span class="cite-bracket">]</span></a></sup> </p><p>Kyorin granted Merck & Company, Inc., an exclusive license (in certain countries, including the United States), to import and distribute Norfloxacin under the brand name Noroxin. The <a href="/wiki/Food_and_Drug_Administration_(United_States)" class="mw-redirect" title="Food and Drug Administration (United States)">U.S. Food and Drug Administration</a> (FDA) approved Noroxin for distribution in the United States on October 31, 1986.<sup id="cite_ref-68" class="reference"><a href="#cite_note-68"><span class="cite-bracket">[</span>68<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Availability">Availability</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Norfloxacin&action=edit&section=10" title="Edit section: Availability"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In most countries, all formulations require a prescription. In Colombia (South America) it is marketed under Ambigram from Laboratorios Bussié. </p><p>Noroxin was discontinued in the US as of April 2014 See the latest package insert for norfloxacin (Noroxin) for additional details. <sup id="cite_ref-fda08_3-4" class="reference"><a href="#cite_note-fda08-3"><span class="cite-bracket">[</span>3<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=Norfloxacin&action=edit&section=11" 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="CITEREFNelsonChillerPowersAngulo2007" class="citation journal cs1">Nelson JM, Chiller TM, Powers JH, Angulo FJ (April 2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1086%2F512369">"Fluoroquinolone-resistant Campylobacter species and the withdrawal of fluoroquinolones from use in poultry: a public health success story"</a>. <i>Clinical Infectious Diseases</i>. <b>44</b> (7): 977–980. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1086%2F512369">10.1086/512369</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a 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Retrieved <span class="nowrap">November 7,</span> 2018</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Federal+Register&rft.atitle=Determination+That+NOROXIN+%28Norfloxacin%29+Tablets%2C+400+Milligrams%2C+Was+Not+Withdrawn+From+Sale+for+Reasons+of+Safety+or+Effectiveness&rft.date=2017-12-12&rft_id=https%3A%2F%2Fwww.federalregister.gov%2Fdocuments%2F2017%2F12%2F12%2F2017-26693%2Fdetermination-that-noroxin-norfloxacin-tablets-400-milligrams-was-not-withdrawn-from-sale-for&rfr_id=info%3Asid%2Fen.wikipedia.org%3ANorfloxacin" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Norfloxacin&action=edit&section=12" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div 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class="mw-redirect" title="Antibiotics">Antibacterials</a> that <a href="/wiki/Nucleic_acid_inhibitor" title="Nucleic acid inhibitor">inhibit nucleic acid</a> (<a href="/wiki/ATC_code_J01#J01E" title="ATC code J01">J01E</a>, <a href="/wiki/ATC_code_J01#J01M" title="ATC code J01">J01M</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antifolate" title="Antifolate">Antifolates</a><br />(inhibit bacterial<br /><a href="/wiki/Purine_metabolism" title="Purine metabolism">purine metabolism</a>,<br />thereby inhibiting<br />DNA and RNA<br />synthesis)</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/Dihydrofolate_reductase_inhibitor" title="Dihydrofolate reductase inhibitor">DHFR inhibitor</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/2,4-Diaminopyrimidine" title="2,4-Diaminopyrimidine">2,4-Diaminopyrimidine</a> <ul><li><a href="/wiki/Brodimoprim" title="Brodimoprim">Brodimoprim</a></li> <li><a href="/wiki/Iclaprim" title="Iclaprim">Iclaprim</a><sup>†</sup></li> <li><a href="/wiki/Ormetoprim" title="Ormetoprim">Ormetoprim</a></li> <li><a href="/wiki/Pyrimethamine" title="Pyrimethamine">Pyrimethamine</a><sup>#</sup></li> <li><a href="/wiki/Tetroxoprim" title="Tetroxoprim">Tetroxoprim</a></li> <li><a href="/wiki/Trimethoprim" title="Trimethoprim">Trimethoprim</a><sup>#</sup></li></ul></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><br />(<a href="/wiki/Dihydropteroate_synthetase_inhibitor" class="mw-redirect" title="Dihydropteroate synthetase inhibitor">DHPS inhibitor</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/Sulfonamide_(medicine)#Short-acting" title="Sulfonamide (medicine)">Short-acting</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/Sulfisomidine" title="Sulfisomidine">Sulfaisodimidine</a></li> <li><a href="/wiki/Sulfamethizole" title="Sulfamethizole">Sulfamethizole</a></li> <li><a href="/wiki/Sulfadimidine" title="Sulfadimidine">Sulfadimidine</a></li> <li><a href="/wiki/Sulfapyridine" title="Sulfapyridine">Sulfapyridine</a> (<a href="/wiki/Sulfasalazine" title="Sulfasalazine">Sulfasalazine</a>)</li> <li><a href="/wiki/Sulfafurazole" title="Sulfafurazole">Sulfafurazole</a> (<a href="/w/index.php?title=Acetyl_sulfisoxazole&action=edit&redlink=1" class="new" title="Acetyl sulfisoxazole (page does not exist)">Acetyl sulfisoxazole</a>)</li> <li><a href="/wiki/Sulfanilamide" title="Sulfanilamide">Sulfanilamide</a> <ul><li><a href="/wiki/Prontosil" title="Prontosil">Prontosil</a></li></ul></li> <li><a href="/wiki/Sulfathiazole" title="Sulfathiazole">Sulfathiazole</a> (<a href="/wiki/Phthalylsulfathiazole" title="Phthalylsulfathiazole">Phthalylsulfathiazole</a>, <a href="/wiki/Succinylsulfathiazole" title="Succinylsulfathiazole">Succinylsulfathiazole</a>)</li> <li><a href="/wiki/Sulfathiourea" title="Sulfathiourea">Sulfathiourea</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfonamide_(medicine)#Intermediate-acting" title="Sulfonamide (medicine)">Intermediate-acting</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/Sulfamethoxazole" title="Sulfamethoxazole">Sulfamethoxazole</a></li> <li><a href="/wiki/Sulfadiazine" title="Sulfadiazine">Sulfadiazine</a><sup>#</sup></li> <li><a href="/wiki/Sulfamoxole" title="Sulfamoxole">Sulfamoxole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sulfonamide_(medicine)#Long-acting" title="Sulfonamide (medicine)">Long-acting</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/Sulfadimethoxine" title="Sulfadimethoxine">Sulfadimethoxine</a></li> <li><a href="/wiki/Sulfadoxine" title="Sulfadoxine">Sulfadoxine</a></li> <li><a href="/wiki/Sulfalene" title="Sulfalene">Sulfalene</a></li> <li><a href="/wiki/Sulfametomidine" title="Sulfametomidine">Sulfametomidine</a></li> <li><a href="/wiki/Sulfametoxydiazine" title="Sulfametoxydiazine">Sulfametoxydiazine</a></li> <li><a href="/wiki/Sulfamethoxypyridazine" title="Sulfamethoxypyridazine">Sulfamethoxypyridazine</a></li> <li><a href="/wiki/Sulfaperin" title="Sulfaperin">Sulfaperin</a></li> <li><a href="/wiki/Sulfamerazine" title="Sulfamerazine">Sulfamerazine</a></li> <li><a href="/wiki/Sulfaphenazole" title="Sulfaphenazole">Sulfaphenazole</a></li> <li><a href="/wiki/Sulfamazone" title="Sulfamazone">Sulfamazone</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/ungrouped</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/Sulfacetamide" title="Sulfacetamide">Sulfacetamide</a></li> <li><a href="/w/index.php?title=Sulfaclozine&action=edit&redlink=1" class="new" title="Sulfaclozine (page does not exist)">Sulfaclozine</a></li> <li><a href="/wiki/Sulfadicramide" title="Sulfadicramide">Sulfadicramide</a></li> <li><a href="/wiki/Sulfaguanidine" title="Sulfaguanidine">Sulfaguanidine</a></li> <li><a href="/wiki/Sulfametrole" title="Sulfametrole">Sulfametrole</a></li> <li><a href="/wiki/Sulfanitran" title="Sulfanitran">Sulfanitran</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</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/Trimethoprim/sulfamethoxazole" title="Trimethoprim/sulfamethoxazole">Trimethoprim/sulfamethoxazole</a><sup>#</sup></li> <li><a href="/wiki/Sulfadimethoxine#with_ormetoprim" title="Sulfadimethoxine">Ormetoprim/sulfadimethoxine</a></li> <li><a href="/w/index.php?title=Pyrimethamine/dapsone&action=edit&redlink=1" class="new" title="Pyrimethamine/dapsone (page does not exist)">Pyrimethamine/dapsone</a></li> <li><a href="/w/index.php?title=Pyrimethamine/sulfadoxine&action=edit&redlink=1" class="new" title="Pyrimethamine/sulfadoxine (page does not exist)">Pyrimethamine/sulfadoxine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other DHPS inhibitors</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/Acediasulfone" title="Acediasulfone">Acediasulfone</a></li> <li><a href="/wiki/Dapsone" title="Dapsone">Dapsone</a></li> <li><a href="/wiki/Solasulfone" title="Solasulfone">Solasulfone</a></li> <li><a href="/wiki/Sulfoxone" title="Sulfoxone">Sulfoxone</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/Quinolone_antibiotic" title="Quinolone antibiotic">Quinolones</a><br />(inhibit bacterial<br /><a href="/wiki/Topoisomerase_inhibitor" title="Topoisomerase inhibitor">topoisomerase</a><br />and/or <a href="/wiki/DNA_gyrase" title="DNA gyrase">DNA gyrase</a>,<br />thereby inhibiting<br /><a href="/wiki/DNA_replication" title="DNA replication">DNA replication</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/Quinolone_antibiotic#First_generation" title="Quinolone antibiotic">1st generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Cinoxacin" title="Cinoxacin">Cinoxacin</a><sup>‡</sup></li> <li><a href="/wiki/Flumequine" title="Flumequine">Flumequine</a><sup>‡</sup></li> <li><a href="/wiki/Nalidixic_acid" title="Nalidixic acid">Nalidixic acid</a><sup>‡</sup></li> <li><a href="/wiki/Oxolinic_acid" title="Oxolinic acid">Oxolinic acid</a><sup>‡</sup></li> <li><a href="/wiki/Pipemidic_acid" title="Pipemidic acid">Pipemidic acid</a><sup>‡</sup></li> <li><a href="/wiki/Piromidic_acid" title="Piromidic acid">Piromidic acid</a><sup>‡</sup></li> <li><a href="/wiki/Rosoxacin" title="Rosoxacin">Rosoxacin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic" title="Quinolone antibiotic">Fluoroquinolones</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/Quinolone_antibiotic#Second_generation" title="Quinolone antibiotic">2nd generation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ciprofloxacin" title="Ciprofloxacin">Ciprofloxacin</a><sup>#</sup></li> <li><a href="/wiki/Ofloxacin" title="Ofloxacin">Ofloxacin</a></li> <li><a href="/wiki/Enoxacin" title="Enoxacin">Enoxacin</a><sup>‡</sup></li> <li><a href="/wiki/Fleroxacin" title="Fleroxacin">Fleroxacin</a><sup>‡</sup></li> <li><a href="/wiki/Lomefloxacin" title="Lomefloxacin">Lomefloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Nadifloxacin" title="Nadifloxacin">Nadifloxacin</a><sup>‡</sup>/<a href="/wiki/Levonadifloxacin" title="Levonadifloxacin">Levonadifloxacin</a>/<a href="/wiki/Alalevonadifloxacin" title="Alalevonadifloxacin">Alalevonadifloxacin</a></li> <li><a class="mw-selflink selflink">Norfloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Pefloxacin" title="Pefloxacin">Pefloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Rufloxacin" title="Rufloxacin">Rufloxacin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic#Third_generation" title="Quinolone antibiotic">3rd generation</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Levofloxacin" title="Levofloxacin">Levofloxacin</a><sup>#</sup></li> <li><a href="/wiki/Balofloxacin" title="Balofloxacin">Balofloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Grepafloxacin" title="Grepafloxacin">Grepafloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Pazufloxacin" title="Pazufloxacin">Pazufloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Sparfloxacin" title="Sparfloxacin">Sparfloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Temafloxacin" title="Temafloxacin">Temafloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Tosufloxacin" title="Tosufloxacin">Tosufloxacin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic#Fourth_generation" title="Quinolone antibiotic">4th generation</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Besifloxacin" title="Besifloxacin">Besifloxacin</a></li> <li><a href="/wiki/Delafloxacin" title="Delafloxacin">Delafloxacin</a></li> <li><a href="/wiki/Gatifloxacin" title="Gatifloxacin">Gatifloxacin</a></li> <li><a href="/wiki/Finafloxacin" title="Finafloxacin">Finafloxacin</a></li> <li><a href="/wiki/Gemifloxacin" title="Gemifloxacin">Gemifloxacin</a></li> <li><a href="/wiki/Moxifloxacin" title="Moxifloxacin">Moxifloxacin</a><sup>#</sup></li> <li><a href="/wiki/Clinafloxacin" title="Clinafloxacin">Clinafloxacin</a><sup>†</sup></li> <li><a href="/wiki/Garenoxacin" title="Garenoxacin">Garenoxacin</a><sup>‡</sup></li> <li><a href="/wiki/Prulifloxacin" title="Prulifloxacin">Prulifloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Sitafloxacin" title="Sitafloxacin">Sitafloxacin</a><sup>‡</sup></li> <li><a href="/wiki/Trovafloxacin" title="Trovafloxacin">Trovafloxacin</a><sup>‡</sup>/<a href="/wiki/Alatrofloxacin" title="Alatrofloxacin">Alatrofloxacin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Quinolone_antibiotic#Veterinary_use" title="Quinolone antibiotic">Veterinary</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Danofloxacin" title="Danofloxacin">Danofloxacin</a></li> <li><a href="/wiki/Difloxacin" title="Difloxacin">Difloxacin</a></li> <li><a href="/wiki/Enrofloxacin" title="Enrofloxacin">Enrofloxacin</a></li> <li><a href="/wiki/Ibafloxacin" title="Ibafloxacin">Ibafloxacin</a></li> <li><a href="/wiki/Marbofloxacin" title="Marbofloxacin">Marbofloxacin</a></li> <li><a href="/wiki/Orbifloxacin" title="Orbifloxacin">Orbifloxacin</a></li> <li><a href="/wiki/Pradofloxacin" title="Pradofloxacin">Pradofloxacin</a></li> <li><a href="/wiki/Sarafloxacin" title="Sarafloxacin">Sarafloxacin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Newer non-fluorinated</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/Nemonoxacin" title="Nemonoxacin">Nemonoxacin</a></li> <li><a href="/wiki/Ozenoxacin" title="Ozenoxacin">Ozenoxacin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related (<a href="/wiki/DNA_gyrase" title="DNA gyrase">DG</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/Aminocoumarin" title="Aminocoumarin">Aminocoumarins</a>: <a href="/wiki/Novobiocin" title="Novobiocin">Novobiocin</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/Anaerobic_organism" title="Anaerobic organism">Anaerobic</a> DNA<br /><a href="/wiki/Nucleic_acid_inhibitor#DNA_inhibitors" title="Nucleic acid inhibitor">inhibitors</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 id="Nitroimidazole_derivatives" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitroimidazole" title="Nitroimidazole">Nitroimidazole</a> 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/Secnidazole" title="Secnidazole">Secnidazole</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/RNA" title="RNA">RNA</a> synthesis</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/Rifamycin" title="Rifamycin">Rifamycins</a>/<br /><a href="/wiki/RNA-dependent_RNA_polymerase" title="RNA-dependent RNA polymerase">RNA polymerase</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/Rifampicin" title="Rifampicin">Rifampicin</a><sup>#</sup></li> <li><a href="/wiki/Rifabutin" title="Rifabutin">Rifabutin</a><sup>#</sup></li> <li><a href="/wiki/Rifapentine" title="Rifapentine">Rifapentine</a><sup>#</sup></li> <li><a href="/wiki/Rifaximin" title="Rifaximin">Rifaximin</a></li> <li><a href="/wiki/Rifalazil" title="Rifalazil">Rifalazil</a><sup>§</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Lipiarmycin" class="mw-redirect" title="Lipiarmycin">Lipiarmycins</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/Fidaxomicin" title="Fidaxomicin">Fidaxomicin</a></li></ul> </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 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