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.ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Rifalazil </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Rifalazil.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Rifalazil.svg/320px-Rifalazil.svg.png" decoding="async" width="320" height="222" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/84/Rifalazil.svg/480px-Rifalazil.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/84/Rifalazil.svg/640px-Rifalazil.svg.png 2x" data-file-width="512" data-file-height="355" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature" title="Chemical nomenclature">IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">(2<i>S</i>,16<i>Z</i>,18<i>E</i>,20<i>S</i>,21<i>S</i>,22<i>R</i>,23<i>R</i>,24<i>R</i>,25<i>S</i>,26<i>R</i>,27<i>S</i>,28<i>E</i>)-5,12,21,23-tetrahydroxy-27-methoxy-2,4,16,20,22,24,26-heptamethyl-10-[4-(2-methylpropyl)piperazin-1-yl]-1,6,15-trioxo-1,2-dihydro-6<i>H</i>-2,7-(epoxypentadeca[1,11,13]trienoimino)[1]benzofuro[4,5-a]phenoxazin-25-yl acetate</div> </td></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Chemical_nomenclature#Systematic_name" title="Chemical nomenclature">Systematic IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">(7<i>S</i>,9<i>E</i>,11<i>S</i>,12<i>R</i>,13<i>S</i>,14<i>R</i>,15<i>R</i>,16<i>R</i>,17<i>S</i>,18<i>S</i>,19<i>E</i>,21<i>Z</i>)-2,15,17,32-Tetrahydroxy-30-(4-isobutyl-1-piperazinyl)-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,37-trioxo-8,27,38-trioxa-24,34-diazahexacyclo[23.11;.1.1<sup>4,7</sup>.0<sup>5,36</sup>.0<sup>26,35</sup>.0<sup>28,33</sup>]octatriaconta-1(36),2,4,9,19,21,25,28,30,32,34-undecaen-13-yl acetate</div></div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><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=129791-92-0">129791-92-0</a></span><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></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><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=C%5BC%40H%5D1C%3DCC%3DC%28C%28%3DO%29N%3DC2C3%3DC%28C4%3DC5C%28%3DC%28C%28%3DC4C2%3DO%29O%29C%29O%5BC%40%40%5D%28C5%3DO%29%28OC%3DC%5BC%40%40H%5D%28%5BC%40H%5D%28%5BC%40H%5D%28%5BC%40%40H%5D%28%5BC%40%40H%5D%28%5BC%40%40H%5D%28%5BC%40H%5D1O%29C%29O%29C%29OC%28%3DO%29C%29C%29OC%29C%29NC6%3DC%28O3%29C%3DC%28C%3DC6O%29N7CCN%28CC7%29CC%28C%29C%29C">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><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.16736451.html">16736451</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><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/D02550">D02550</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><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/6540558">6540558</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><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/S1976TE8QK">S1976TE8QK</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> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C51H64N4O13/c1-24(2)23-54-16-18-55(19-17-54)32-21-33(57)39-35(22-32)67-48-40(52-39)36-37-44(60)30(8)47-38(36)49(62)51(10,68-47)65-20-15-34(64-11)27(5)46(66-31(9)56)29(7)43(59)28(6)42(58)25(3)13-12-14-26(4)50(63)53-41(48)45(37)61/h12-15,20-22,24-25,27-29,34,42-43,46,57-60H,16-19,23H2,1-11H3,(H,53,63)/b13-12+,20-15+,26-14-/t25-,27+,28+,29+,34-,42-,43+,46+,51-/m0/s1</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><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="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">C[C@H]1C=CC=C(C(=O)N=C2C3=C(C4=C5C(=C(C(=C4C2=O)O)C)O[C@@](C5=O)(OC=C[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)NC6=C(O3)C=C(C=C6O)N7CCN(CC7)CC(C)C)C</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>51</sub><span title="Hydrogen">H</span><sub>64</sub><span title="Nitrogen">N</span><sub>4</sub><span title="Oxygen">O</span><sub>13</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002941088000000000♠"></span>941.088</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>Very high water solubility around 2000 mg/mL at a pH of 2 and a low solubility of 0.5 mg/mL at a pH of 5 </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetics</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Biological_half-life" title="Biological half-life">Biological half-life</a></div> </td> <td>8.7±2.7 hours<sup id="cite_ref-tuberculosis_2-0" class="reference"><a href="#cite_note-tuberculosis-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li>Development terminated</li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Rifalazil</b> (also known as <b>KRM-1648</b> and <b>AMI-1648</b>)<sup id="cite_ref-tuberculosis_2-1" class="reference"><a href="#cite_note-tuberculosis-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> is an <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> substance that kills bacterial cells by blocking off the β-subunit in <a href="/wiki/RNA_polymerase" title="RNA polymerase">RNA polymerase</a>.<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> Rifalazil is used as a treatment for many different diseases. The most common are <a href="/wiki/Chlamydia_infection" class="mw-redirect" title="Chlamydia infection"><i>Chlamydia</i> infection</a>, <a href="/wiki/Clostridioides_difficile_infection" title="Clostridioides difficile infection"><i>Clostridioides difficile</i> associated diarrhea</a> (CDAD), and <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a> (TB). Using rifalazil and the effects that coincide with taking rifalazil for treating a bacterial disease vary from person to person, as does any drug put into the human body. Food interactions and genetic variation are a few causes for the variation in side effects from the use of rifalazil.<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> Its development was terminated in 2013 due to severe side effects.<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> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Biological_properties">Biological properties</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Rifalazil&action=edit&section=1" title="Edit section: Biological properties"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Rifalazil works well alone, and in conjunction with other antibiotics alone. In a study conducted in 2005, it was found that combining rifalazil with <a href="/wiki/Vancomycin" title="Vancomycin">vancomycin</a> increased bacterial killing by a factor of 3.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (January 2016)">medical citation needed</span></a></i>]</sup> Rifalazil also has a very long half-life which allows for more infrequent dosages as opposed to frequent small dosages of antibiotics.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Many different studies have been conducted that have researched the effect of rifalazil on certain strains of bacterial diseases. In a study conducted in 2004, it was found that rifalazil reduced <i>C. difficile</i> strains when studied <i><a href="/wiki/In_vitro" title="In vitro">in vitro</a></i>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Rifalazil&action=edit&section=2" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Rifalazil has been developed to treat cases of <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a> and <a href="/wiki/Chlamydia_(bacterium)" class="mw-redirect" title="Chlamydia (bacterium)">chlamydia</a>. It is a very good treatment for tuberculosis because rifalazil achieves a very high concentration in the blood cells and the lungs. In addition, rifalazil is becoming more widely used because it can be used along with many other indications, such as <a href="/wiki/HIV" title="HIV">HIV</a>, TB, and <a href="/wiki/Methicillin-resistant_Staphylococcus_aureus" title="Methicillin-resistant Staphylococcus aureus">MRSA</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> Rifalazil has a very long <a href="/wiki/Half-life" title="Half-life">half-life</a> which is very useful for certain medications. The drug is administered orally which is also convenient in terms of drug administration. A longer half-life allows for fewer treatments and dosages, which makes this an up-and-coming drug for tuberculosis, CDAD, and chlamydia. Although the uses for rifalazil seem very effective, there are negative side effects that make its use limited. Rifalazil interacts with other drugs and on top of that, rapid resistance develops to other drugs.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Identifying_reliable_sources_(medicine)" title="Wikipedia:Identifying reliable sources (medicine)"><span title="Material near this tag needs references to reliable medical sources. (January 2016)">medical citation needed</span></a></i>]</sup> </p> <div class="mw-heading mw-heading3"><h3 id="Tested_diseases_for_rifalazil_treatment">Tested diseases for rifalazil treatment</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Rifalazil&action=edit&section=3" title="Edit section: Tested diseases for rifalazil treatment"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a href="/wiki/Chlamydia_infection" class="mw-redirect" title="Chlamydia infection"><i>Chlamydia</i> infection</a></li> <li><a href="/wiki/Clostridioides_difficile_infection" title="Clostridioides difficile infection"><i>Clostridioides difficile</i> associated diarrhea</a></li> <li><a href="/wiki/Trachoma" title="Trachoma">Trachoma</a></li> <li><a href="/wiki/Tuberculosis" title="Tuberculosis">Tuberculosis</a></li> <li><a href="/wiki/Leprosy" title="Leprosy">Leprosy</a></li> <li><a href="/wiki/Buruli_ulcer" title="Buruli ulcer">Buruli ulcer</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></li></ul> <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=Rifalazil&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 reflist-columns-2"> <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 class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.chemicalbook.com/ChemicalProductProperty_EN_CB2437664.htm">"Rifalazil - 129791-92-0"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Rifalazil+-+129791-92-0&rft_id=http%3A%2F%2Fwww.chemicalbook.com%2FChemicalProductProperty_EN_CB2437664.htm&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARifalazil" class="Z3988"></span></span> </li> <li id="cite_note-tuberculosis-2"><span class="mw-cite-backlink">^ <a href="#cite_ref-tuberculosis_2-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-tuberculosis_2-1"><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 class="citation journal cs1">"Rifalazil". <i>Tuberculosis</i>. <b>88</b> (2): <span class="nowrap">148–</span>150. 2008. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS1472-9792%2808%2970023-4">10.1016/S1472-9792(08)70023-4</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/18486057">18486057</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Tuberculosis&rft.atitle=Rifalazil&rft.volume=88&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E148-%3C%2Fspan%3E150&rft.date=2008&rft_id=info%3Adoi%2F10.1016%2FS1472-9792%2808%2970023-4&rft_id=info%3Apmid%2F18486057&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARifalazil" 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 id="CITEREFOsburneMurphyRothstein2006" class="citation journal cs1">Osburne, Marcia S; Murphy, Christopher K; Rothstein, David M (2006). <a rel="nofollow" class="external text" href="https://doi.org/10.1038%2Fja.2006.43">"Enhanced Activity of Rifalazil in Combination with Levofloxacin, Linezolid, or Mupirocin against Staphylococcus aureus in vitro"</a>. <i>The Journal of Antibiotics</i>. <b>59</b> (5): <span class="nowrap">303–</span>8. <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/10.1038%2Fja.2006.43">10.1038/ja.2006.43</a></span>. <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/16883781">16883781</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Antibiotics&rft.atitle=Enhanced+Activity+of+Rifalazil+in+Combination+with+Levofloxacin%2C+Linezolid%2C+or+Mupirocin+against+Staphylococcus+aureus+in+vitro&rft.volume=59&rft.issue=5&rft.pages=%3Cspan+class%3D%22nowrap%22%3E303-%3C%2Fspan%3E8&rft.date=2006&rft_id=info%3Adoi%2F10.1038%2Fja.2006.43&rft_id=info%3Apmid%2F16883781&rft.aulast=Osburne&rft.aufirst=Marcia+S&rft.au=Murphy%2C+Christopher+K&rft.au=Rothstein%2C+David+M&rft_id=https%3A%2F%2Fdoi.org%2F10.1038%252Fja.2006.43&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARifalazil" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.healthanddna.com/drug-safety-dna-testing/rifalazil-side-effects">"Cannabis Ministry Amsterdam : Home : THC Ministry Amsterdam"</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=Cannabis+Ministry+Amsterdam+%3A+Home+%3A+THC+Ministry+Amsterdam&rft_id=http%3A%2F%2Fwww.healthanddna.com%2Fdrug-safety-dna-testing%2Frifalazil-side-effects&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARifalazil" class="Z3988"></span></span> </li> <li id="cite_note-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-5">^</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://adisinsight.springer.com/drugs/800006128">"AdisInsight: Rifalazil (ABI 1648; KRM 1648; PA 1648)"</a>. <i>Adis Insight</i>. Springer International Publishing AG<span class="reference-accessdate">. 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Antibiot</i>. <b>59</b> (2): <span class="nowrap">80–</span>85. <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/10.1038%2Fja.2006.11">10.1038/ja.2006.11</a></span>. <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/16629407">16629407</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Antibiot.&rft.atitle=In+vitro+time-kill+activities+of+rifalazil%2C+alone+and+in+combination+with+vancomycin%2C+against+logarithmic+and+stationary+cultures+of+Staphylococcus+aureus&rft.volume=59&rft.issue=2&rft.pages=%3Cspan+class%3D%22nowrap%22%3E80-%3C%2Fspan%3E85&rft.date=2006&rft_id=info%3Adoi%2F10.1038%2Fja.2006.11&rft_id=info%3Apmid%2F16629407&rft.aulast=Osburne&rft.aufirst=MS&rft.au=Rothstein%2C+DM&rft.au=Farquhar%2C+R&rft.au=Murphy%2C+CK&rft_id=https%3A%2F%2Fdoi.org%2F10.1038%252Fja.2006.11&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARifalazil" class="Z3988"></span></span> </li> <li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAntonO'BrienKokkotouEisenstein2004" class="citation journal cs1">Anton, P. M.; O'Brien, M.; Kokkotou, E.; Eisenstein, B.; Michaelis, A.; Rothstein, D.; Paraschos, S.; Kelly, C. P.; Pothoulakis, C. (2004). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC521872">"Rifalazil Treats and Prevents Relapse of Clostridium difficile-Associated Diarrhea in Hamsters"</a>. <i>Antimicrobial Agents and Chemotherapy</i>. <b>48</b> (10): <span class="nowrap">3975–</span>9. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FAAC.48.10.3975-3979.2004">10.1128/AAC.48.10.3975-3979.2004</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC521872">521872</a></span>. <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/15388461">15388461</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Antimicrobial+Agents+and+Chemotherapy&rft.atitle=Rifalazil+Treats+and+Prevents+Relapse+of+Clostridium+difficile-Associated+Diarrhea+in+Hamsters&rft.volume=48&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E3975-%3C%2Fspan%3E9&rft.date=2004&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC521872%23id-name%3DPMC&rft_id=info%3Apmid%2F15388461&rft_id=info%3Adoi%2F10.1128%2FAAC.48.10.3975-3979.2004&rft.aulast=Anton&rft.aufirst=P.+M.&rft.au=O%27Brien%2C+M.&rft.au=Kokkotou%2C+E.&rft.au=Eisenstein%2C+B.&rft.au=Michaelis%2C+A.&rft.au=Rothstein%2C+D.&rft.au=Paraschos%2C+S.&rft.au=Kelly%2C+C.+P.&rft.au=Pothoulakis%2C+C.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC521872&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARifalazil" class="Z3988"></span></span> </li> <li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</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://web.archive.org/web/20130203112858/http://www.activbioticspharma.com/rifalazil.html">"ActivBiotics Pharma - Rifalazil"</a>. Archived from <a rel="nofollow" class="external text" href="http://www.activbioticspharma.com/rifalazil.html">the original</a> on 2013-02-03<span class="reference-accessdate">. Retrieved <span class="nowrap">2012-11-20</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=ActivBiotics+Pharma+-+Rifalazil&rft_id=http%3A%2F%2Fwww.activbioticspharma.com%2Frifalazil.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ARifalazil" 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 class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20130810011631/http://www.activbioticspharma.com/rifalazil/neglecteddiseases.html">"Web Page Under Construction"</a>. 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inhibitor</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/Rifamycin" title="Rifamycin">Rifamycins</a>/<br /><a href="/wiki/RNA_polymerase" title="RNA polymerase">RNA polymerase</a> inhibitor</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/Rifampicin" title="Rifampicin">Rifampicin</a><sup>#</sup></li> <li><a href="/wiki/Rifabutin" title="Rifabutin">Rifabutin</a></li> <li><a href="/wiki/Rifapentine" title="Rifapentine">Rifapentine</a></li> <li><a class="mw-selflink selflink">Rifalazil</a><sup>§</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Antifolate" title="Antifolate">Antifolates</a>/<a href="/wiki/Dihydropteroate_synthetase_inhibitor" class="mw-redirect" title="Dihydropteroate synthetase inhibitor">DSI</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/Dapsone" title="Dapsone">Dapsone</a><sup>#</sup></li> <li><a href="/wiki/Acedapsone" title="Acedapsone">Acedapsone</a></li> <li><a href="/wiki/Diucifon" title="Diucifon">Diucifon</a></li> <li><a href="/wiki/Promin" title="Promin">Promin</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><tr><th scope="row" class="navbox-group" style="width:1%">ASA</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/4-Aminosalicylic_acid" title="4-Aminosalicylic acid">4-Aminosalicylic acid</a></i><sup>#</sup> (<a href="/wiki/Calcium_aminosalicylate" class="mw-redirect" title="Calcium aminosalicylate">Calcium aminosalicylate</a></li> <li><a href="/wiki/Sodium_aminosalicylate" class="mw-redirect" title="Sodium aminosalicylate">Sodium aminosalicylate</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Topoisomerase_inhibitor" title="Topoisomerase inhibitor">Topoisomerase inhibitors</a>/<br /><a href="/wiki/Quinolone_antibiotic" title="Quinolone antibiotic">quinolones</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/Gatifloxacin" title="Gatifloxacin">Gatifloxacin</a></li> <li><a href="/wiki/Moxifloxacin" title="Moxifloxacin">Moxifloxacin</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/Protein_synthesis_inhibitor" title="Protein synthesis inhibitor">Protein synthesis inhibitor</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Aminoglycoside" title="Aminoglycoside">Aminoglycosides</a></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/Amikacin" title="Amikacin">Amikacin</a><sup>#</sup></li> <li><a href="/wiki/Kanamycin" class="mw-redirect" title="Kanamycin">Kanamycin</a></li> <li><a href="/wiki/Streptomycin" title="Streptomycin">Streptomycin</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/2-Oxazolidone" class="mw-redirect" title="2-Oxazolidone">Oxazolidone</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/Linezolid" title="Linezolid">Linezolid</a></li> <li><a href="/wiki/Sutezolid" title="Sutezolid">Sutezolid</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Polypeptide_antibiotic" title="Polypeptide antibiotic">Polypeptide antibiotics</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/Capreomycin" title="Capreomycin">Capreomycin</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/Cell_envelope_antibiotic" title="Cell envelope antibiotic">Cell envelope antibiotic</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/Peptidoglycan" title="Peptidoglycan">Peptidoglycan</a> layer</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/Alanine" title="Alanine">Alanine</a> analogue: <a href="/wiki/Cycloserine" title="Cycloserine">Cycloserine</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Arabinogalactan" title="Arabinogalactan">Arabinogalactan</a> layer</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/Ethylenediamine" title="Ethylenediamine">Ethylenediamine</a>/<a href="/wiki/Arabinosyltransferase" title="Arabinosyltransferase">arabinosyltransferase</a> inhibitor: <a href="/wiki/Ethambutol" title="Ethambutol">Ethambutol</a><sup>#</sup></li></ul> <ul><li><a href="/wiki/SQ109" title="SQ109">SQ109</a><sup>†</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Mycolic_acid" title="Mycolic acid">Mycolic acid</a> layer</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/Hydrazide" title="Hydrazide">Hydrazides</a>/<a href="/wiki/Mycolic_acid" title="Mycolic acid">mycolic acid</a> synth. inhibition: <a href="/wiki/Isoniazid" title="Isoniazid">Isoniazid</a><sup>#</sup></li> <li><a href="/wiki/Methaniazide" title="Methaniazide">Methaniazide</a></li></ul> <ul><li><a href="/wiki/Thiocarbamide" class="mw-redirect" title="Thiocarbamide">Thiocarbamides</a>: <a href="/wiki/Ethionamide" title="Ethionamide">Ethionamide</a><sup>#</sup></li> <li><a href="/wiki/Prothionamide" title="Prothionamide">Prothionamide</a></li> <li><a href="/wiki/Thiocarlide" title="Thiocarlide">Thiocarlide</a></li></ul> <ul><li>Others/unsorted: <a href="/wiki/Thioacetazone" title="Thioacetazone">Thioacetazone (amithiozone)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other/unknown</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Phenazine" title="Phenazine">Phenazine</a></i> (<a href="/wiki/Clofazimine" title="Clofazimine">Clofazimine</a>)<sup>#</sup></li> <li><i><a href="/wiki/Pyrazine" title="Pyrazine">Pyrazine</a></i> (<a href="/wiki/Pyrazinamide" title="Pyrazinamide">Pyrazinamide</a><sup>#</sup>, <a href="/wiki/Morinamide" title="Morinamide">Morinamide</a>)</li> <li><i><a href="/wiki/Isoxazole" title="Isoxazole">Isoxazole</a></i> (<a href="/wiki/Terizidone" title="Terizidone">Terizidone</a>)</li> <li><a href="/wiki/Bedaquiline" title="Bedaquiline">Bedaquiline</a></li> <li><i><a href="/wiki/Nitroimidazole" title="Nitroimidazole">Nitroimidazole</a></i> (<i><a href="/wiki/Delamanid" title="Delamanid">Delamanid</a></i>, <i><a href="/wiki/Pretomanid" title="Pretomanid">Pretomanid</a></i>)</li></ul> </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 hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Ethambutol/isoniazid" title="Ethambutol/isoniazid">Ethambutol/isoniazid</a></li> <li><a href="/wiki/Ethambutol/isoniazid/pyrazinamide/rifampicin" title="Ethambutol/isoniazid/pyrazinamide/rifampicin">Ethambutol/isoniazid/pyrazinamide/rifampicin</a><sup>#</sup></li> <li><a href="/wiki/Ethambutol/isoniazid/rifampicin" title="Ethambutol/isoniazid/rifampicin">Ethambutol/isoniazid/rifampicin</a><sup>#</sup></li> <li><a href="/wiki/Isoniazid/pyridoxine/sulfamethoxazole/trimethoprim" title="Isoniazid/pyridoxine/sulfamethoxazole/trimethoprim">Isoniazid/pyridoxine/sulfamethoxazole/trimethoprim</a><sup>#</sup></li> <li><a href="/wiki/Rifampicin/isoniazid/pyrazinamide" title="Rifampicin/isoniazid/pyrazinamide">Rifampicin/isoniazid/pyrazinamide</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" 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" /><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)902" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a 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)902" 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> (<a href="/wiki/Sulfamethazine" class="mw-redirect" title="Sulfamethazine">Sulfamethazine</a>, <a href="/wiki/Sulfadimerazine" class="mw-redirect" title="Sulfadimerazine">Sulfadimerazine</a>, <a href="/wiki/Sulfadimezine" class="mw-redirect" title="Sulfadimezine">Sulfadimezine</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 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_derivatives30" 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 class="mw-selflink selflink">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="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div 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