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href="https://azb.wikipedia.org/wiki/%D9%BE%D8%B1%D9%88%D9%86%D8%AA%D9%88%D8%B3%DB%8C%D9%84" title="پرونتوسیل – South Azerbaijani" lang="azb" hreflang="azb" data-title="پرونتوسیل" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target"><span>تۆرکجه</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Sulfamidochrysoidin" title="Sulfamidochrysoidin – German" lang="de" hreflang="de" data-title="Sulfamidochrysoidin" 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/Prontosil" title="Prontosil – Spanish" lang="es" hreflang="es" data-title="Prontosil" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%BE%D8%B1%D9%88%D9%86%D8%AA%D9%88%D8%B3%DB%8C%D9%84" title="پرونتوسیل – Persian" lang="fa" hreflang="fa" data-title="پرونتوسیل" 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/Prontosil" title="Prontosil – French" lang="fr" hreflang="fr" data-title="Prontosil" 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/Prontosil" title="Prontosil – Italian" lang="it" hreflang="it" data-title="Prontosil" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/Prontozil" title="Prontozil – Hungarian" lang="hu" hreflang="hu" data-title="Prontozil" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target"><span>Magyar</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Sulfamidochryso%C3%AFdine" title="Sulfamidochrysoïdine – Dutch" lang="nl" hreflang="nl" data-title="Sulfamidochrysoïdine" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%97%E3%83%AD%E3%83%B3%E3%83%88%E3%82%B8%E3%83%AB" title="プロントジル – Japanese" lang="ja" hreflang="ja" data-title="プロントジル" 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 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српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Prontosiili" title="Prontosiili – Finnish" lang="fi" hreflang="fi" data-title="Prontosiili" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Prontosil" title="Prontosil – Swedish" lang="sv" hreflang="sv" data-title="Prontosil" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/Sulfamidochrysoidin" title="Sulfamidochrysoidin – Turkish" lang="tr" hreflang="tr" data-title="Sulfamidochrysoidin" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target"><span>Türkçe</span></a></li><li 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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">An early antimicrobial drug of nonantibiotic type</div> <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): Prontosil">Prontosil</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:Prontosil.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Prontosil.svg/220px-Prontosil.svg.png" decoding="async" width="220" height="117" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/89/Prontosil.svg/330px-Prontosil.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/89/Prontosil.svg/440px-Prontosil.svg.png 2x" data-file-width="1500" data-file-height="800" /></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;">Other names</th><td class="infobox-data">Sulfamidochrysoïdine, Rubiazol, Prontosil rubrum, Aseptil rojo, Streptocide, Sulfamidochrysoïdine hydrochloride</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="https://en.wiktionary.org/wiki/oral" class="extiw" title="wiktionary:oral">Oral</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-[(2,4-Diaminophenyl)azo]benzenesulfonamide</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"><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><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=103-12-8">103-12-8</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</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/66895">66895</a></span></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.16736190.html">16736190</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/Q64Q9N6Q6O">Q64Q9N6Q6O</a></span></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/chembldb/index.php/compound/inspect/ChEMBL488279">ChEMBL488279</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</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/DTXSID60145608">DTXSID60145608</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q418758#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/100.002.802">100.002.802</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q418758#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>12</sub><span title="Hydrogen">H</span><sub>13</sub><span title="Nitrogen">N</span><sub>5</sub><span title="Oxygen">O</span><sub>2</sub><span title="Sulfur">S</span></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="7002291330000000000♠"></span>291.33</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=NS%28%3DO%29%28%3DO%29c2ccc%28%2FN%3DN%2Fc1ccc%28N%29cc1N%29cc2">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">NS(=O)(=O)c2ccc(/N=N/c1ccc(N)cc1N)cc2</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/C12H13N5O2S/c13-8-1-6-12(11(14)7-8)17-16-9-2-4-10(5-3-9)20(15,18)19/h1-7H,13-14H2,(H2,15,18,19)<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:ABBQGOCHXSPKHJ-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"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><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> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=464215701&page2=Prontosil">(verify)</a></span></span></td></tr></tbody></table> <p><b>Prontosil</b> is an anti<a href="/wiki/Bacteria" title="Bacteria">bacterial</a> drug of the <a href="/wiki/Sulfonamide" title="Sulfonamide">sulfonamide</a> group. It has a relatively broad effect against <a href="/wiki/Gram-positive_bacteria" title="Gram-positive bacteria">gram-positive</a> <a href="/wiki/Coccus" class="mw-redirect" title="Coccus">cocci</a> but not against <a href="/wiki/Enterobacteriaceae" title="Enterobacteriaceae">enterobacteria</a>. One of the earliest <a href="/wiki/Antimicrobial" title="Antimicrobial">antimicrobial</a> drugs, it was widely used in the mid-20th century but is little used today because better options now exist. The discovery and development of this first <a href="/wiki/Sulfonamide_(medicine)" title="Sulfonamide (medicine)">sulfonamide</a> drug opened a new era in medicine,<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> because it greatly widened the success of <a href="/wiki/Antimicrobial_chemotherapy" title="Antimicrobial chemotherapy">antimicrobial chemotherapy</a> in an era when many physicians doubted its still largely untapped potential. At the time, <a href="/wiki/Disinfectant" title="Disinfectant">disinfectant</a> cleaners and topical <a href="/wiki/Antiseptic" title="Antiseptic">antiseptic</a> wound care were widely used but there were very few <a href="/wiki/Antimicrobial" title="Antimicrobial">antimicrobial</a> drugs to use safely inside living bodies. <a href="/wiki/Antibiotic" title="Antibiotic">Antibiotic</a> drugs derived from microbes, which are relied on heavily today, did not yet exist. Prontosil was discovered in 1932<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> by a research team at the <a href="/wiki/Bayer" title="Bayer">Bayer</a> Laboratories of the <a href="/wiki/IG_Farben" title="IG Farben">IG Farben</a> conglomerate in Germany led by <a href="/wiki/Gerhard_Domagk" title="Gerhard Domagk">Gerhard Domagk</a>. Domagk received the 1939 <a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Nobel Prize in Physiology or Medicine</a> for that discovery.<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> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Names">Names</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prontosil&action=edit&section=1" title="Edit section: Names"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The capitalized name "Prontosil" is Bayer's trade name; the nonproprietary names include sulfamidochrysoïdine, rubiazol, prontosil rubrum, prontosil flavum, aseptil rojo, streptocide, and sulfamidochrysoïdine hydrochloride. Because the drug predates the modern system of <a href="/wiki/Drug_nomenclature" title="Drug nomenclature">drug nomenclature</a>, which ensures that nonproprietary names are well known from the inception of marketing, it was generally known among the public only by its trade name, and the trade name was the origin of some of the nonproprietary names (as also happened with "<a href="/wiki/Aspirin#Trademark" title="Aspirin">aspirin</a>"). </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=Prontosil&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>This compound was first synthesized by Bayer chemists Josef Klarer and Fritz Mietzsch as part of a research program designed to find dyes that might act as antibacterial drugs in the body. The molecule was tested and in the late autumn of 1932 was found effective against some important bacterial infections in mice by <a href="/wiki/Gerhard_Domagk" title="Gerhard Domagk">Gerhard Domagk</a>, who subsequently received the 1939 <a href="/wiki/Nobel_Prize_in_Medicine" class="mw-redirect" title="Nobel Prize in Medicine">Nobel Prize in Medicine</a>. Prontosil was the result of five years of testing involving thousands of compounds related to <a href="/wiki/Azo_dye" title="Azo dye">azo dyes</a>. </p><p>The crucial test result (in a <a href="/wiki/Murine" class="mw-redirect" title="Murine">murine</a> model of <i><a href="/wiki/Streptococcus_pyogenes" title="Streptococcus pyogenes">Streptococcus pyogenes</a></i> systemic infection) that preliminarily established the antibacterial efficacy of Prontosil in mice dates from late December 1931. IG Farben filed a German patent application concerning its medical utility on December 25, 1932.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> The synthesis of the compound had been first reported by <a href="/wiki/Paul_Gelmo" title="Paul Gelmo">Paul Gelmo</a>, a chemistry student working at the <a href="/wiki/University_of_Vienna" title="University of Vienna">University of Vienna</a> in his 1909 thesis, although he had not realized its medical potential. </p><p>The readily water-soluble sodium salt of sulfonamidochrysoidine, which gives a burgundy red solution and was trademarked Prontosil Solubile, was clinically investigated between 1932 and 1934, first at the nearby hospital at <a href="/wiki/Wuppertal" title="Wuppertal">Wuppertal</a>-Elberfeld headed by Philipp Klee, and then at the <a href="/wiki/D%C3%BCsseldorf_University_Hospital" class="mw-redirect" title="Düsseldorf University Hospital">Düsseldorf University Hospital</a>. The results were published in a series of articles in the February 15, 1935 issue of Germany's then preeminent medical scientific journal, <i><a href="/wiki/Deutsche_Medizinische_Wochenschrift" title="Deutsche Medizinische Wochenschrift">Deutsche Medizinische Wochenschrift</a></i>,<sup id="cite_ref-Domagk_1935_5-0" class="reference"><a href="#cite_note-Domagk_1935-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> and were initially received with some skepticism by a medical community bent on <a href="/wiki/Vaccination" title="Vaccination">vaccination</a> and crude <a href="/wiki/Immunotherapy" title="Immunotherapy">immunotherapy</a>.<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. (March 2024)">clarification needed</span></a></i>]</sup> </p><p><a href="/wiki/Leonard_Colebrook" title="Leonard Colebrook">Leonard Colebrook</a> introduced it as a cure for <a href="/wiki/Puerperal_fever" class="mw-redirect" title="Puerperal fever">puerperal fever</a>.<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> As impressive clinical successes with Prontosil started to be reported from all over Europe, and especially after a widely published treatment in 1936<sup id="cite_ref-pmid18160700_7-0" class="reference"><a href="#cite_note-pmid18160700-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> of <a href="/wiki/Franklin_Delano_Roosevelt,_Jr." class="mw-redirect" title="Franklin Delano Roosevelt, Jr.">Franklin Delano Roosevelt, Jr.</a><sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> (a son of U.S. president <a href="/wiki/Franklin_D._Roosevelt" title="Franklin D. Roosevelt">Franklin D. Roosevelt</a>), acceptance was quick and dozens of medicinal chemistry teams set out to improve Prontosil. </p> <div class="mw-heading mw-heading2"><h2 id="Eclipse_and_legacy">Eclipse and legacy</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prontosil&action=edit&section=3" title="Edit section: Eclipse and legacy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Tube_of_Prontosil_tablets,_Germany,_1935-1950_Wellcome_L0057805.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Tube_of_Prontosil_tablets%2C_Germany%2C_1935-1950_Wellcome_L0057805.jpg/220px-Tube_of_Prontosil_tablets%2C_Germany%2C_1935-1950_Wellcome_L0057805.jpg" decoding="async" width="220" height="309" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/61/Tube_of_Prontosil_tablets%2C_Germany%2C_1935-1950_Wellcome_L0057805.jpg/330px-Tube_of_Prontosil_tablets%2C_Germany%2C_1935-1950_Wellcome_L0057805.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/61/Tube_of_Prontosil_tablets%2C_Germany%2C_1935-1950_Wellcome_L0057805.jpg/440px-Tube_of_Prontosil_tablets%2C_Germany%2C_1935-1950_Wellcome_L0057805.jpg 2x" data-file-width="3361" data-file-height="4727" /></a><figcaption>Tube of Prontosil tablets, Germany, 1935–1950 </figcaption></figure> <p>In late 1935, working at the <a href="/wiki/Pasteur_Institute" title="Pasteur Institute">Pasteur Institute</a> in Paris in the laboratory of Dr. <a href="/wiki/Ernest_Fourneau" title="Ernest Fourneau">Ernest Fourneau</a>, <a href="/wiki/Jacques_Tr%C3%A9fou%C3%ABl" title="Jacques Tréfouël">Jacques and Thérèse Tréfouël</a>, Dr. <a href="/wiki/Daniel_Bovet" title="Daniel Bovet">Daniel Bovet</a> and Federico Nitti discovered that Prontosil is metabolized to <a href="/wiki/Sulfanilamide" title="Sulfanilamide">sulfanilamide</a> (para-aminobenzenesulfonamide), a much simpler, colorless molecule, reclassifying Prontosil as a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a>.<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> <a href="/wiki/Prontalbin" class="mw-redirect" title="Prontalbin">Prontalbin</a> became the first oral version of sulfanilamide by Bayer, which had actually obtained a German patent on sulfanilamide as early as 1909, without realizing its medical potential at this time.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p><p>It has been argued that IG Farben might have made its breakthrough discovery with sulfanilamide in 1932 but, recognizing that it would not be patentable as an antibacterial, had spent the next three years developing Prontosil as a new, and therefore more easily patentable, compound.<sup id="cite_ref-pmid795333_11-0" class="reference"><a href="#cite_note-pmid795333-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> However Dr. Bovet, who has received a Nobel Prize for medicine, and one of the authors of the French discovery, wrote in 1988: "Today, we have the proof that the chemists of Elberfeld were unaware of the properties of sulfanilamide at the time of our discovery and that it was by our communication that they were informed. To be convinced about it, it is enough to attentively examine the monthly reports of work of Mietzsch and Klarer during years 1935–1936 and especially the Log Book of <a href="/wiki/Gerhard_Domagk" title="Gerhard Domagk">Gerhard Domagk</a>: the formula of sulphamide is consigned there – without comment – not before January 1936."<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>Dr. Alexander Ashley Weech (1895–1977), a pioneer pediatrician, while working at <a href="/wiki/Columbia_University" title="Columbia University">Columbia University</a>'s College of Physicians & Surgeons (in the affiliated New York Babies Hospital) treated the first patient in the United States with an antibiotic (sulfanilamide; prontosil) in 1935 which led to a new era of medicine across the Atlantic.<sup id="cite_ref-Famous_Men_of_Medicine_13-0" class="reference"><a href="#cite_note-Famous_Men_of_Medicine-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> Dr. Weech researched Domagk's work,<sup id="cite_ref-Domagk_1935_5-1" class="reference"><a href="#cite_note-Domagk_1935-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> translating the German article,<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> and "was so intrigued by [the] experiments and by the three accompanying clinical articles on Prontosil that he contacted a pharmaceutical house, obtained a supply of the drug, and proceeded to treat a patient [a daughter of a colleague<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup>] who had serious streptococcal disease."<sup id="cite_ref-pmid4565222_16-0" class="reference"><a href="#cite_note-pmid4565222-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> Dr. Perrin Long and Dr. <a href="/wiki/Eleanor_Albert_Bliss" title="Eleanor Albert Bliss">Eleanor Bliss</a> of Johns Hopkins University began their pioneering work later on prontosil and sulfanilamide which led to the large scale production of this new treatment saving the lives of millions with systemic bacterial infections.<sup id="cite_ref-Famous_Men_of_Medicine_13-1" class="reference"><a href="#cite_note-Famous_Men_of_Medicine-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Sulfanilamide was cheap to produce and (due to the early date of its original composition of matter patent which made no reference to a medical use) was already off-patent when its antibacterial properties were first made public. Since the sulfanilamide moiety was also easy to link into other molecules, chemists soon gave rise to hundreds of second-generation sulfonamide drugs. As a result, Prontosil failed to make the profits in the marketplace hoped for by Bayer. Although quickly eclipsed by these newer "<a href="/wiki/Sulfa_drug" class="mw-redirect" title="Sulfa drug">sulfa drugs</a>" and, in the mid-1940s and through the 1950s by <a href="/wiki/Penicillin" title="Penicillin">penicillin</a> and other antibacterials that proved more effective against more types of bacteria, Prontosil remained on the market until the 1960s. Prontosil's discovery ushered in the era of antibacterial drugs and had a profound effect on pharmaceutical research, drug laws, and medical history. </p><p>Sulfonamide-<a href="/wiki/Trimethoprim" title="Trimethoprim">trimethoprim</a> combinations (<a href="/wiki/Co-trimoxazole" class="mw-redirect" title="Co-trimoxazole">co-trimoxazole</a>) are still used extensively against opportunistic infections in patients with AIDS, urinary infections and in the treatment of burns. However, in many other situations, sulfa drugs have been replaced by <a href="/wiki/Beta-lactam" class="mw-redirect" title="Beta-lactam">beta-lactam</a> antibacterials. </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=Prontosil&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 32em;"> <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="CITEREFHager2006" class="citation book cs1">Hager T (2006). <i>The Demon Under the Microscope: From Battlefield Hospitals to Nazi Labs, One Doctor's Heroic Search for the World's First Miracle Drug</i>. Harmony Books. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/1-4000-8214-5" title="Special:BookSources/1-4000-8214-5"><bdi>1-4000-8214-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Demon+Under+the+Microscope%3A+From+Battlefield+Hospitals+to+Nazi+Labs%2C+One+Doctor%27s+Heroic+Search+for+the+World%27s+First+Miracle+Drug&rft.pub=Harmony+Books&rft.date=2006&rft.isbn=1-4000-8214-5&rft.aulast=Hager&rft.aufirst=Thomas&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProntosil" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation book cs1"><a rel="nofollow" class="external text" href="https://books.google.com/books?id=5W-WBQAAQBAJ&pg=PT56"><i>Oxford Handbook of Infectious Diseases and Microbiology</i></a>. OUP Oxford. 2009. p. 56. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780191039621" title="Special:BookSources/9780191039621"><bdi>9780191039621</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Oxford+Handbook+of+Infectious+Diseases+and+Microbiology&rft.pages=56&rft.pub=OUP+Oxford&rft.date=2009&rft.isbn=9780191039621&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3D5W-WBQAAQBAJ%26pg%3DPT56&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProntosil" class="Z3988"></span></span> </li> <li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.nobelprize.org/nobel_prizes/medicine/laureates/1939/press.html">"Physiology or Medicine 1939 – Presentation Speech"</a>. Nobel Foundation. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150114032532/http://www.nobelprize.org/nobel_prizes/medicine/laureates/1939/press.html">Archived</a> from the original on 14 January 2015<span class="reference-accessdate">. Retrieved <span class="nowrap">14 January</span> 2015</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Physiology+or+Medicine+1939+%E2%80%93+Presentation+Speech&rft.pub=Nobel+Foundation&rft_id=https%3A%2F%2Fwww.nobelprize.org%2Fnobel_prizes%2Fmedicine%2Flaureates%2F1939%2Fpress.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProntosil" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLesch2007" class="citation book cs1">Lesch JE (2007). "Chapter 3: Prontosil". <i>The first miracle drugs: how the sulfa drugs transformed medicine</i>. Oxford University Press. p. 51. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-19-518775-5" title="Special:BookSources/978-0-19-518775-5"><bdi>978-0-19-518775-5</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Chapter+3%3A+Prontosil&rft.btitle=The+first+miracle+drugs%3A+how+the+sulfa+drugs+transformed+medicine.&rft.pages=51&rft.pub=Oxford+University+Press&rft.date=2007&rft.isbn=978-0-19-518775-5&rft.aulast=Lesch&rft.aufirst=JE&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProntosil" class="Z3988"></span></span> </li> <li id="cite_note-Domagk_1935-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-Domagk_1935_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Domagk_1935_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFDomagk1935" class="citation journal cs1">Domagk G (15 February 1935). "Ein Beitrag zur Chemotherapie der bakteriellen Infektionen". <i>Dtsch. Med. 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"Dr Leonard Colebrook, FRS (1883-1967) and the chemotherapeutic conquest of puerperal infection". <i>Archives of Disease in Childhood. 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December 28, 1936. Archived from <a rel="nofollow" class="external text" href="http://www.time.com/time/magazine/article/0,9171,771900,00.html">the original</a> on 15 December 2008.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=TIME+Magazine&rft.atitle=Medicine%3A+Prontosil&rft.date=1936-12-28&rft_id=http%3A%2F%2Fwww.time.com%2Ftime%2Fmagazine%2Farticle%2F0%2C9171%2C771900%2C00.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProntosil" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFTréfouëlNittiBovet1935" class="citation journal cs1">Tréfouël JT, Nitti F, Bovet D (23 November 1935). "Activité du <i>p</i>-aminophénylsulfamide sur l'infection streptococcique expérimentale de la souris et du lapin". <i>C. R. Soc. 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New York: Dodd, Mead & Co.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Famous+Men+of+Medicine.&rft.place=New+York&rft.pub=Dodd%2C+Mead+%26+Co.&rft.date=1950&rft.aulast=Chandler&rft.aufirst=CA&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProntosil" class="Z3988"></span></span> </li> <li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFWeech1970" class="citation journal cs1">Weech AA (1970). 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Ashley Weech, MD". <i>American Journal of Diseases of Children</i>. <b>124</b> (6): 818–9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1001%2Farchpedi.1972.02110180020002">10.1001/archpedi.1972.02110180020002</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/4565222">4565222</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=American+Journal+of+Diseases+of+Children&rft.atitle=A.+Ashley+Weech%2C+MD&rft.volume=124&rft.issue=6&rft.pages=818-9&rft.date=1972-12&rft_id=info%3Adoi%2F10.1001%2Farchpedi.1972.02110180020002&rft_id=info%3Apmid%2F4565222&rft.aulast=Forbes&rft.aufirst=GB&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProntosil" class="Z3988"></span></span> </li> <li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.emedexpert.com/tips/antibiotics-facts.shtml">"Interesting Facts About Antibiotics"</a>. <i>emedexpert.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">12 December</span> 2014</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=emedexpert.com&rft.atitle=Interesting+Facts+About+Antibiotics&rft_id=http%3A%2F%2Fwww.emedexpert.com%2Ftips%2Fantibiotics-facts.shtml&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProntosil" class="Z3988"></span></span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Prontosil&action=edit&section=5" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239549316">.mw-parser-output .refbegin{margin-bottom:0.5em}.mw-parser-output .refbegin-hanging-indents>ul{margin-left:0}.mw-parser-output .refbegin-hanging-indents>ul>li{margin-left:0;padding-left:3.2em;text-indent:-3.2em}.mw-parser-output .refbegin-hanging-indents ul,.mw-parser-output .refbegin-hanging-indents ul li{list-style:none}@media(max-width:720px){.mw-parser-output .refbegin-hanging-indents>ul>li{padding-left:1.6em;text-indent:-1.6em}}.mw-parser-output .refbegin-columns{margin-top:0.3em}.mw-parser-output .refbegin-columns ul{margin-top:0}.mw-parser-output .refbegin-columns li{page-break-inside:avoid;break-inside:avoid-column}@media screen{.mw-parser-output .refbegin{font-size:90%}}</style><div class="refbegin" style=""> <p><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFLesch2007" class="citation book cs1">Lesch JE (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=AqzmCwAAQBAJ&q=history+of+prontosil"><i>The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine</i></a>. New York: Oxford University Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9780195187755" title="Special:BookSources/9780195187755"><bdi>9780195187755</bdi></a><span class="reference-accessdate">. Retrieved <span class="nowrap">29 December</span> 2017</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+First+Miracle+Drugs%3A+How+the+Sulfa+Drugs+Transformed+Medicine&rft.place=New+York&rft.pub=Oxford+University+Press&rft.date=2007&rft.isbn=9780195187755&rft.aulast=Lesch&rft.aufirst=John+E.&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DAqzmCwAAQBAJ%26q%3Dhistory%2Bof%2Bprontosil&rfr_id=info%3Asid%2Fen.wikipedia.org%3AProntosil" class="Z3988"></span> </p> </div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output 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.navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Antibacterials_that_inhibit_nucleic_acid_(J01E,_J01M)" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed 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"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar 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href="/wiki/Template:Nucleic_acid_inhibitors" title="Template:Nucleic acid inhibitors"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nucleic_acid_inhibitors" title="Template talk:Nucleic acid inhibitors"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nucleic_acid_inhibitors" title="Special:EditPage/Template:Nucleic acid inhibitors"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antibacterials_that_inhibit_nucleic_acid_(J01E,_J01M)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antibiotics" 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 class="mw-selflink selflink">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 href="/wiki/Norfloxacin" title="Norfloxacin">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 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"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" 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