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href="https://fa.wikipedia.org/wiki/%D9%84%D8%A7%D8%AA%D8%A7%D9%85%D9%88%DA%A9%D8%B3%D9%81" title="لاتاموکسف – Persian" lang="fa" hreflang="fa" data-title="لاتاموکسف" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Latamoxef" title="Latamoxef – Italian" lang="it" hreflang="it" data-title="Latamoxef" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Latamoxef" title="Latamoxef – Romanian" lang="ro" hreflang="ro" data-title="Latamoxef" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Latamoksef" title="Latamoksef – Serbian" lang="sr" hreflang="sr" data-title="Latamoksef" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Latamoksef" title="Latamoksef – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Latamoksef" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Latamoksefi" title="Latamoksefi – Finnish" lang="fi" hreflang="fi" data-title="Latamoksefi" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%A5%E0%B8%B2%E0%B8%97%E0%B8%B2%E0%B8%A1%E0%B8%AD%E0%B8%81%E0%B9%80%E0%B8%8B%E0%B8%9F" title="ลาทามอกเซฟ – Thai" lang="th" hreflang="th" data-title="ลาทามอกเซฟ" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target"><span>ไทย</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9B%D0%B0%D1%82%D0%B0%D0%BC%D0%BE%D0%BA%D1%81%D0%B5%D1%84" title="Латамоксеф – Ukrainian" lang="uk" hreflang="uk" data-title="Латамоксеф" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a href="https://www.wikidata.org/wiki/Special:EntityPage/Q3827439#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> 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.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): Latamoxef">Latamoxef</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:Latamoxef.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Latamoxef.svg/220px-Latamoxef.svg.png" decoding="async" width="220" height="87" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Latamoxef.svg/330px-Latamoxef.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c2/Latamoxef.svg/440px-Latamoxef.svg.png 2x" data-file-width="512" data-file-height="203" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/international/latamoxef.html">International Drug Names</a></span></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Intramuscular_injection" title="Intramuscular injection">Intramuscular</a>, <a href="/wiki/Intravenous_therapy" title="Intravenous therapy">intravenous</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><a href="/wiki/ATC_code_J01" title="ATC code J01">J01DD06</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=J01DD06">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">35 to 50%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data">Nil</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">2 hours</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data">Mostly <a href="/wiki/Kidney" title="Kidney">renal</a>, unchanged; also biliary</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%;">(6<i>R</i>,7<i>R</i>)-7-{[carboxy(4-hydroxyphenyl)acetyl]amino}-7-methoxy-3-{[(1-methyl-1<i>H</i>-tetrazol-5-yl)thio]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=64952-97-2">64952-97-2</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/47499">47499</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB04570">DB04570</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/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.43215.html">43215</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/VUF6C936Z3">VUF6C936Z3</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D08109">D08109</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:599928">CHEBI:599928</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/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL74632">ChEMBL74632</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9023338">DTXSID9023338</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3827439#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/100.059.334">100.059.334</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3827439#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>20</sub><span title="Hydrogen">H</span><sub>20</sub><span title="Nitrogen">N</span><sub>6</sub><span title="Oxygen">O</span><sub>9</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="7002520470000000000♠"></span>520.47</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC2N1%2FC%28%3DC%28%5CCO%5BC%40%40H%5D1%5BC%40%5D2%28OC%29NC%28%3DO%29C%28c3ccc%28O%29cc3%29C%28%3DO%29O%29CSc4nnnn4C%29C%28%3DO%29O">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Melting_point" title="Melting point">Melting point</a></th><td class="infobox-data">117 to 122 °C (243 to 252 °F) (dec.)</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O=C2N1/C(=C(\CO[C@@H]1[C@]2(OC)NC(=O)C(c3ccc(O)cc3)C(=O)O)CSc4nnnn4C)C(=O)O</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/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:JWCSIUVGFCSJCK-CAVRMKNVSA-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=408571626&page2=Latamoxef">(verify)</a></span></span></td></tr></tbody></table> <p><b>Latamoxef</b> (or <b>moxalactam</b>) is an <a href="/wiki/Oxacephem" title="Oxacephem">oxacephem</a> <a href="/wiki/Antibiotic" title="Antibiotic">antibiotic</a> usually grouped with the <a href="/wiki/Cephalosporin" title="Cephalosporin">cephalosporins</a>. In oxacephems such as latamoxef, the <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> atom of the cephalosporin core is replaced with an <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> atom. </p><p>Latamoxef has been associated with prolonged <a href="/wiki/Bleeding_time" title="Bleeding time">bleeding time</a>, and several cases of <a href="/wiki/Coagulopathy" title="Coagulopathy">coagulopathy</a>, some fatal, were reported during the 1980s.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> Latamoxef is no longer available in the United States. As with other cephalosporins with a methylthiotetrazole side chain, latamoxef causes a <a href="/wiki/Disulfiram" title="Disulfiram">disulfiram</a> reaction when mixed with alcohol. Additionally, the methylthiotetrazole side chain inhibits γ-carboxylation of glutamic acid; this can interfere with the actions of vitamin K.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (January 2023)">citation needed</span></a></i>]</sup> </p><p>It has been described as a third-generation cephalosporin.<sup id="cite_ref-pmid3296254_3-0" class="reference"><a href="#cite_note-pmid3296254-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Latamoxef&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Oxa-substituted third generation cephalosporin antibiotic (oxacephalosporin). </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Moxalactam_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Moxalactam_synthesis.svg/700px-Moxalactam_synthesis.svg.png" decoding="async" width="700" height="495" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Moxalactam_synthesis.svg/1050px-Moxalactam_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e3/Moxalactam_synthesis.svg/1400px-Moxalactam_synthesis.svg.png 2x" data-file-width="512" data-file-height="362" /></a><figcaption>Moxalactam synthesis:<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><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><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><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><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> (excerpt from Lednicer book 3)</figcaption></figure> <p>The <a href="/wiki/Benzhydrol" class="mw-redirect" title="Benzhydrol">benzhydrol</a> ester of 6-Aminopenicillanic acid (<a href="/wiki/6-APA" title="6-APA">6-APA</a>) is S-chlorinated and treated with base whereupon the intermediate <a href="/wiki/Sulfenyl_chloride" title="Sulfenyl chloride">sulfenyl chloride</a> fragments (to <b>2</b>). Next, displacement with <a href="/wiki/Propargyl_alcohol" title="Propargyl alcohol">propargyl alcohol</a> in the presence of <a href="/wiki/Zinc_chloride" title="Zinc chloride">zinc chloride</a> gives predominanntly the stereochemistry represented by diastereoisomer <b>3</b>. The side chain is protected as the phenylacetylamide; the triple bond is partially reduced with a 5% Pd-CaCO3 (<a href="/wiki/Lindlar_catalyst" title="Lindlar catalyst">Lindlar catalyst</a>) and then epoxidized with <a href="/wiki/MCPBA" class="mw-redirect" title="MCPBA">mCPBA</a> to give <b>4</b>. The epoxide is opened at the least hindered end with 1-methyl-1<i>H</i>-tetrazole-5-thiol to put in place the future C-3 side chain and give intermediate <b>5</b>. Jones oxidation followed in turn by ozonolysis (reductive work-up with zinc-AcOH) and reaction with <a href="/wiki/SOCl2" class="mw-redirect" title="SOCl2">SOCl2</a> and <a href="/wiki/Pyridine" title="Pyridine">pyridine</a> give halide <b>6</b>. The stage is now wet for intramolecular <a href="/wiki/Wittig_reaction" title="Wittig reaction">Wittig reaction</a>. Displacement with <a href="/wiki/PPh3" class="mw-redirect" title="PPh3">PPh3</a> and Wittig olefination gives 1-oxacephem <b>7</b>. Next a sequence is undertaken of side chain exchange and introduction of a 7-methoxyl group analogous to that which is present in <a href="/wiki/Cephamycins" class="mw-redirect" title="Cephamycins">cephamycins</a> and gives them the enhanced <a href="/wiki/Beta-lactamase" title="Beta-lactamase">beta-lactamase</a> stability. First <b>7</b> is converted to the imino chloride with <a href="/wiki/PCl5" class="mw-redirect" title="PCl5">PCl5</a> and then to the imino methyl ether (with <a href="/wiki/Methanol" title="Methanol">methanol</a>) and next hydrolyzed to the free amine (<b>8</b>). Imine formation with 3,5-di-t-butyl-4-hydroxybenzaldehyde is next carried out leading to <b>9</b>. Oxidation with <a href="/wiki/Nickel(III)_oxide" title="Nickel(III) oxide">nickel(III) oxide</a> gives iminoquinone methide <b>10</b>, to which methanol is added in a conjugate sense and in the sterechemistry represented by formula <b>11</b>. The imine is exchanged with <a href="/w/index.php?title=Girard%27s_reagent_T&action=edit&redlink=1" class="new" title="Girard's reagent T (page does not exist)">Girard's reagent T</a> to give <b>12</b>, and this is acylated by a suitable protected arylmalonate, as the hemiester hemiacid chloride so as to give 11. Deblocking with <a href="/wiki/Aluminium_chloride" title="Aluminium chloride">aluminium chloride</a> and anisole gives moxalactam <b>14</b>. </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=Latamoxef&action=edit&section=2" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><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="CITEREFWeitekampAber1983" class="citation journal cs1">Weitekamp MR, Aber RC (January 1983). "Prolonged bleeding times and bleeding diathesis associated with moxalactam administration". <i>JAMA</i>. <b>249</b> (1): 69–71. <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%2Fjama.249.1.69">10.1001/jama.249.1.69</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/6217353">6217353</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=JAMA&rft.atitle=Prolonged+bleeding+times+and+bleeding+diathesis+associated+with+moxalactam+administration&rft.volume=249&rft.issue=1&rft.pages=69-71&rft.date=1983-01&rft_id=info%3Adoi%2F10.1001%2Fjama.249.1.69&rft_id=info%3Apmid%2F6217353&rft.aulast=Weitekamp&rft.aufirst=MR&rft.au=Aber%2C+RC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALatamoxef" 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 id="CITEREFBrownKlarLemeshowTeres1986" class="citation journal cs1">Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M (November 1986). 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Statistical analysis within a defined population of 1493 patients". <i>Archives of Internal Medicine</i>. <b>146</b> (11): 2159–2164. <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%2Farchinte.146.11.2159">10.1001/archinte.146.11.2159</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/3778044">3778044</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+of+Internal+Medicine&rft.atitle=Enhanced+bleeding+with+cefoxitin+or+moxalactam.+Statistical+analysis+within+a+defined+population+of+1493+patients&rft.volume=146&rft.issue=11&rft.pages=2159-2164&rft.date=1986-11&rft_id=info%3Adoi%2F10.1001%2Farchinte.146.11.2159&rft_id=info%3Apmid%2F3778044&rft.aulast=Brown&rft.aufirst=RB&rft.au=Klar%2C+J&rft.au=Lemeshow%2C+S&rft.au=Teres%2C+D&rft.au=Pastides%2C+H&rft.au=Sands%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALatamoxef" class="Z3988"></span></span> </li> <li id="cite_note-pmid3296254-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid3296254_3-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFSalemMcIndoeMatkinLidou1987" class="citation journal cs1">Salem RR, McIndoe A, Matkin JA, Lidou AC, Clarke A, Wood CB (June 1987). 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Part 5. A Synthesis of 7b-Acylamino-3-methyl-1-oxadethia-3-cephem-4-carboxylic Acids"</a>. <i>Heterocycles</i>. <b>7</b> (2): 839. <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/10.3987%2FS-1977-02-0839">10.3987/S-1977-02-0839</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Heterocycles&rft.atitle=Synthetic+Studies+on+b-Lactam+Antibiotics.+Part+5.+A+Synthesis+of+7b-Acylamino-3-methyl-1-oxadethia-3-cephem-4-carboxylic+Acids&rft.volume=7&rft.issue=2&rft.pages=839&rft.date=1977&rft_id=info%3Adoi%2F10.3987%2FS-1977-02-0839&rft.aulast=Narisada&rft.aufirst=M&rft.au=Onoue%2C+H&rft.au=Nagata%2C+W&rft_id=https%3A%2F%2Fdoi.org%2F10.3987%252FS-1977-02-0839&rfr_id=info%3Asid%2Fen.wikipedia.org%3ALatamoxef" class="Z3988"></span></span> </li> </ol></div></div> <div 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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 ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output 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antibiotics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Antibacterials_active_on_the_cell_wall_and_envelope_(J01C-J01D)" style="font-size:114%;margin:0 4em"><a href="/wiki/Antibiotics" class="mw-redirect" title="Antibiotics">Antibacterials</a> active on the <a href="/wiki/Cell_wall" title="Cell wall">cell wall</a> and <a href="/wiki/Cell_envelope_antibiotic" title="Cell envelope antibiotic">envelope</a> (<a href="/wiki/ATC_code_J01#J01C" title="ATC code J01">J01C</a>-<a href="/wiki/ATC_code_J01#J01D" title="ATC code J01">J01D</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Beta-lactam_antibiotics" class="mw-redirect" title="Beta-lactam antibiotics">β-lactams</a><br /><small><span class="nobold">(inhibit synthesis<br />of peptidoglycan<br />layer of bacterial<br />cell wall by binding<br />to and inhibiting<br /><a href="/wiki/Penicillin-binding_proteins" title="Penicillin-binding proteins">PBPs</a>, a group of<br /><a href="/wiki/DD-Transpeptidase" title="DD-Transpeptidase"><small>D</small>-alanyl-<small>D</small>-alanine<br />transpeptidases</a>)</span></small></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/Penicillin" title="Penicillin">Penicillins</a> (<a href="/wiki/Penam" title="Penam">Penams</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/List_of_%CE%B2-lactam_antibiotics#Narrow-spectrum" title="List of β-lactam antibiotics">Narrow<br />spectrum</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/List_of_%CE%B2-lactam_antibiotics#Narrow-spectrum" title="List of β-lactam antibiotics">β-lactamase sensitive</a><br />(1st generation)</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/Benzylpenicillin" title="Benzylpenicillin">Benzylpenicillin (G)</a><sup>#</sup></li> <li><a href="/wiki/Benzathine_benzylpenicillin" title="Benzathine benzylpenicillin">Benzathine benzylpenicillin</a><sup>#</sup></li> <li><a href="/wiki/Procaine_benzylpenicillin" title="Procaine benzylpenicillin">Procaine benzylpenicillin</a><sup>#</sup></li> <li><a href="/wiki/Phenoxymethylpenicillin" title="Phenoxymethylpenicillin">Phenoxymethylpenicillin (V)</a><sup>#</sup></li> <li><a href="/wiki/Propicillin" title="Propicillin">Propicillin</a><sup>‡</sup></li> <li><a href="/wiki/Pheneticillin" title="Pheneticillin">Pheneticillin</a><sup>‡</sup></li> <li><a href="/wiki/Azidocillin" title="Azidocillin">Azidocillin</a><sup>‡</sup></li> <li><a href="/wiki/Clometocillin" title="Clometocillin">Clometocillin</a><sup>‡</sup></li> <li><a href="/wiki/Penamecillin" title="Penamecillin">Penamecillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_%CE%B2-lactam_antibiotics#β-lactamase-resistant" title="List of β-lactam antibiotics">β-lactamase resistant</a><br />(2nd generation)</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/Cloxacillin" title="Cloxacillin">Cloxacillin</a><sup>#</sup> (<a href="/wiki/Dicloxacillin" title="Dicloxacillin">Dicloxacillin</a></li> <li><a href="/wiki/Flucloxacillin" title="Flucloxacillin">Flucloxacillin</a>)</li> <li><a href="/wiki/Oxacillin" title="Oxacillin">Oxacillin</a></li> <li><a href="/wiki/Nafcillin" title="Nafcillin">Nafcillin</a></li> <li><a href="/wiki/Methicillin" title="Methicillin">Methicillin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Extended-spectrum_penicillin" title="Extended-spectrum penicillin">Extended<br />spectrum</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/Aminopenicillin" title="Aminopenicillin">Aminopenicillins</a> (3rd generation)</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/Amoxicillin" title="Amoxicillin">Amoxicillin</a><sup>#</sup></li> <li><a href="/wiki/Ampicillin" title="Ampicillin">Ampicillin</a><sup>#</sup> (<a href="/wiki/Pivampicillin" title="Pivampicillin">Pivampicillin</a></li> <li><a href="/wiki/Hetacillin" title="Hetacillin">Hetacillin</a><sup>‡</sup></li> <li><a href="/wiki/Bacampicillin" title="Bacampicillin">Bacampicillin</a><sup>‡</sup></li> <li><a href="/wiki/Lenampicillin" title="Lenampicillin">Lenampicillin</a></li> <li><a href="/wiki/Metampicillin" title="Metampicillin">Metampicillin</a><sup>‡</sup></li> <li><a href="/wiki/Talampicillin" title="Talampicillin">Talampicillin</a><sup>‡</sup>)</li> <li><a href="/wiki/Epicillin" title="Epicillin">Epicillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carboxypenicillin" title="Carboxypenicillin">Carboxypenicillins</a> (4th generation)</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/Ticarcillin" title="Ticarcillin">Ticarcillin</a></li> <li><a href="/wiki/Carbenicillin" title="Carbenicillin">Carbenicillin</a><sup>‡</sup> / <a href="/wiki/Carindacillin" title="Carindacillin">Carindacillin</a><sup>‡</sup></li> <li><a href="/wiki/Temocillin" title="Temocillin">Temocillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ureidopenicillin" title="Ureidopenicillin">Ureidopenicillins</a> (4th generation)</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/Piperacillin" title="Piperacillin">Piperacillin</a></li> <li><a href="/wiki/Azlocillin" title="Azlocillin">Azlocillin</a><sup>‡</sup></li> <li><a href="/wiki/Mezlocillin" title="Mezlocillin">Mezlocillin</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Mecillinam" title="Mecillinam">Mecillinam</a> (<a href="/wiki/Pivmecillinam" title="Pivmecillinam">Pivmecillinam</a>)</li> <li><a href="/wiki/Sulbenicillin" title="Sulbenicillin">Sulbenicillin</a><sup>‡</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Carbapenem" title="Carbapenem">Carbapenems</a> / <a href="/wiki/Penem" title="Penem">Penems</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>Carbapenems (<a href="/wiki/Ertapenem" title="Ertapenem">Ertapenem</a></li> <li><a href="/wiki/Antipseudomonal" class="mw-redirect" title="Antipseudomonal">Antipseudomonal</a> (<a href="/wiki/Doripenem" title="Doripenem">Doripenem</a></li> <li><a href="/wiki/Imipenem" title="Imipenem">Imipenem</a></li> <li><a href="/wiki/Meropenem" title="Meropenem">Meropenem</a>)</li> <li><a href="/wiki/Biapenem" title="Biapenem">Biapenem</a><sup>‡</sup></li> <li><a href="/wiki/Panipenem" title="Panipenem">Panipenem</a>)</li> <li>Penems (<a href="/wiki/Faropenem" title="Faropenem">Faropenem</a></li> <li><a href="/wiki/Ritipenem" title="Ritipenem">Ritipenem</a><sup>§</sup></li> <li><a href="/wiki/Sulopenem" title="Sulopenem">Sulopenem</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephem" title="Cephem">Cephems</a><br /><a href="/wiki/Cephalosporin" title="Cephalosporin">Cephalosporins</a><br /><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycins</a><br /><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephems</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/Cephalosporin#First_generation" title="Cephalosporin">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/Cefazolin" title="Cefazolin">Cefazolin</a><sup>#</sup></li> <li><a href="/wiki/Cefalexin" title="Cefalexin">Cefalexin</a> <sup>#</sup></li> <li><a href="/wiki/Cefadroxil" title="Cefadroxil">Cefadroxil</a></li> <li><a href="/wiki/Cefapirin" title="Cefapirin">Cefapirin</a></li> <li><a href="/wiki/Cefazedone" title="Cefazedone">Cefazedone</a><sup>‡</sup></li> <li><a href="/wiki/Cefazaflur" title="Cefazaflur">Cefazaflur</a><sup>‡</sup></li> <li><a href="/wiki/Cefradine" title="Cefradine">Cefradine</a><sup>‡</sup></li> <li><a href="/wiki/Cefroxadine" title="Cefroxadine">Cefroxadine</a><sup>‡</sup></li> <li><a href="/wiki/Ceftezole" title="Ceftezole">Ceftezole</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloglycin" title="Cefaloglycin">Cefaloglycin</a><sup>‡</sup></li> <li><a href="/wiki/Cefacetrile" title="Cefacetrile">Cefacetrile</a><sup>‡</sup></li> <li><a href="/wiki/Cefalonium" title="Cefalonium">Cefalonium</a><sup>‡</sup></li> <li><a href="/wiki/Cefaloridine" class="mw-redirect" title="Cefaloridine">Cefaloridine</a><sup>‡</sup></li> <li><a href="/wiki/Cefalotin" title="Cefalotin">Cefalotin</a></li> <li><a href="/wiki/Cefatrizine" title="Cefatrizine">Cefatrizine</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Second_generation" title="Cephalosporin">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/Cefaclor" title="Cefaclor">Cefaclor</a></li> <li><a href="/wiki/Cefprozil" title="Cefprozil">Cefprozil</a></li> <li><a href="/wiki/Cefuroxime" title="Cefuroxime">Cefuroxime</a></li> <li><a href="/wiki/Cefuroxime_axetil" title="Cefuroxime axetil">Cefuroxime axetil</a></li> <li><a href="/wiki/Cefamandole" title="Cefamandole">Cefamandole</a><sup>‡</sup></li> <li><a href="/wiki/Cefonicid" title="Cefonicid">Cefonicid</a><sup>‡</sup></li> <li><a href="/wiki/Ceforanide" title="Ceforanide">Ceforanide</a><sup>‡</sup></li> <li><a href="/wiki/Cefuzonam" title="Cefuzonam">Cefuzonam</a><sup>‡</sup></li> <li><a href="/wiki/Cephamycin" title="Cephamycin">Cephamycin</a> (<a href="/wiki/Cefoxitin" title="Cefoxitin">Cefoxitin</a></li> <li><a href="/wiki/Cefotetan" title="Cefotetan">Cefotetan</a></li> <li><a href="/wiki/Cefminox" title="Cefminox">Cefminox</a><sup>‡</sup></li> <li><a href="/wiki/Cefbuperazone" title="Cefbuperazone">Cefbuperazone</a><sup>‡</sup></li> <li><a href="/wiki/Cefmetazole" title="Cefmetazole">Cefmetazole</a><sup>‡</sup>)</li> <li><a href="/wiki/Carbacephem" title="Carbacephem">Carbacephem</a> (<a href="/wiki/Loracarbef" title="Loracarbef">Loracarbef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Third_generation" title="Cephalosporin">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/Cefixime" title="Cefixime">Cefixime</a><sup>#</sup></li> <li><a href="/wiki/Ceftriaxone" title="Ceftriaxone">Ceftriaxone</a><sup>#</sup></li> <li><a href="/wiki/Cefotaxime" title="Cefotaxime">Cefotaxime</a><sup>#</sup></li> <li>Antipseudomonal (<a href="/wiki/Ceftazidime" title="Ceftazidime">Ceftazidime</a><sup>#</sup></li> <li><a href="/wiki/Cefoperazone" title="Cefoperazone">Cefoperazone</a>)</li> <li><a href="/wiki/Cefdinir" title="Cefdinir">Cefdinir</a></li> <li><a href="/wiki/Cefcapene" title="Cefcapene">Cefcapene</a></li> <li><a href="/wiki/Cefdaloxime" title="Cefdaloxime">Cefdaloxime</a></li> <li><a href="/wiki/Ceftizoxime" title="Ceftizoxime">Ceftizoxime</a></li> <li><a href="/wiki/Cefmenoxime" title="Cefmenoxime">Cefmenoxime</a></li> <li><a href="/wiki/Cefpiramide" title="Cefpiramide">Cefpiramide</a></li> <li><a href="/wiki/Cefpodoxime" title="Cefpodoxime">Cefpodoxime</a></li> <li><a href="/wiki/Ceftibuten" title="Ceftibuten">Ceftibuten</a></li> <li><a href="/wiki/Cefditoren" title="Cefditoren">Cefditoren</a></li> <li><a href="/wiki/Cefotiam" title="Cefotiam">Cefotiam</a><sup>‡</sup></li> <li><a href="/wiki/Cefetamet" title="Cefetamet">Cefetamet</a><sup>‡</sup></li> <li><a href="/wiki/Cefodizime" title="Cefodizime">Cefodizime</a><sup>‡</sup></li> <li><a href="/wiki/Cefpimizole" title="Cefpimizole">Cefpimizole</a><sup>‡</sup></li> <li><a href="/wiki/Cefsulodin" title="Cefsulodin">Cefsulodin</a><sup>‡</sup></li> <li><a href="/wiki/Cefteram" title="Cefteram">Cefteram</a><sup>‡</sup></li> <li><a href="/wiki/Ceftiolene" title="Ceftiolene">Ceftiolene</a><sup>‡</sup></li> <li><a href="/wiki/Oxacephem" title="Oxacephem">Oxacephem</a> (<a href="/wiki/Flomoxef" title="Flomoxef">Flomoxef</a></li> <li><a class="mw-selflink selflink">Latamoxef</a><sup>‡</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fourth_generation" title="Cephalosporin">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/Cefepime" title="Cefepime">Cefepime</a></li> <li><a href="/wiki/Cefozopran" title="Cefozopran">Cefozopran</a><sup>‡</sup></li> <li><a href="/wiki/Cefpirome" title="Cefpirome">Cefpirome</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Cephalosporin#Fifth_generation" title="Cephalosporin">5th 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/Ceftaroline_fosamil" title="Ceftaroline fosamil">Ceftaroline fosamil</a></li> <li><a href="/wiki/Ceftolozane" class="mw-redirect" title="Ceftolozane">Ceftolozane</a></li> <li><a href="/wiki/Ceftobiprole" title="Ceftobiprole">Ceftobiprole</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Siderophore" title="Siderophore">Siderophore</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/Cefiderocol" title="Cefiderocol">Cefiderocol</a><sup>#</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Veterinary_medicine" title="Veterinary medicine">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/Ceftiofur" title="Ceftiofur">Ceftiofur</a></li> <li><a href="/wiki/Cefquinome" title="Cefquinome">Cefquinome</a></li> <li><a href="/wiki/Cefovecin" title="Cefovecin">Cefovecin</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/Monobactam" title="Monobactam">Monobactams</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/Aztreonam" title="Aztreonam">Aztreonam</a></li> <li><a href="/wiki/Tigemonam" title="Tigemonam">Tigemonam</a><sup>‡</sup></li> <li><a href="/wiki/Carumonam" title="Carumonam">Carumonam</a><sup>‡</sup></li> <li><a href="/wiki/Nocardicin_A" title="Nocardicin A">Nocardicin A</a><sup>‡</sup></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/%CE%92-Lactamase_inhibitor" title="Β-Lactamase inhibitor">β-lactamase inhibitors</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/Penam" title="Penam">Penam</a> (<a href="/wiki/Sulbactam" title="Sulbactam">Sulbactam</a></li> <li><a href="/wiki/Tazobactam" title="Tazobactam">Tazobactam</a>)</li> <li><a href="/wiki/Clavam" title="Clavam">Clavam</a> (<a href="/wiki/Clavulanic_acid" title="Clavulanic acid">Clavulanic acid</a>)</li> <li>non-β-lactam (<a href="/wiki/Avibactam" title="Avibactam">Avibactam</a></li> <li><a href="/wiki/Durlobactam" title="Durlobactam">Durlobactam</a></li> <li><a href="/wiki/Relebactam" title="Relebactam">Relebactam</a></li> <li><a href="/wiki/Vaborbactam" title="Vaborbactam">Vaborbactam</a>)</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-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amoxicillin/clavulanic_acid" title="Amoxicillin/clavulanic acid">Amoxicillin/clavulanic acid</a><sup>#</sup></li> <li><a href="/wiki/Ampicillin/flucloxacillin" title="Ampicillin/flucloxacillin">Ampicillin/flucloxacillin</a></li> <li><a href="/wiki/Ampicillin/sulbactam" title="Ampicillin/sulbactam">Ampicillin/sulbactam</a> (<a href="/wiki/Sultamicillin" title="Sultamicillin">Sultamicillin</a>)</li> <li><a href="/wiki/Aztreonam/avibactam" title="Aztreonam/avibactam">Aztreonam/avibactam</a></li> <li><a href="/wiki/Benzathine_benzylpenicillin/procaine_benzylpenicillin" title="Benzathine benzylpenicillin/procaine benzylpenicillin">Benzathine benzylpenicillin/procaine benzylpenicillin</a></li> <li><a href="/wiki/Cefepime/enmetazobactam" title="Cefepime/enmetazobactam">Cefepime/enmetazobactam</a></li> <li><a href="/wiki/Cefoperazone/sulbactam" title="Cefoperazone/sulbactam">Cefoperazone/sulbactam</a></li> <li><a href="/wiki/Ceftazidime/avibactam" title="Ceftazidime/avibactam">Ceftazidime/avibactam</a></li> <li><a href="/wiki/Ceftolozane/tazobactam" title="Ceftolozane/tazobactam">Ceftolozane/tazobactam</a></li> <li><a href="/wiki/Imipenem/cilastatin" title="Imipenem/cilastatin">Imipenem/cilastatin</a><sup>#</sup></li> <li><a href="/wiki/Imipenem/cilastatin/relebactam" title="Imipenem/cilastatin/relebactam">Imipenem/cilastatin/relebactam</a></li> <li><a href="/wiki/Meropenem/vaborbactam" title="Meropenem/vaborbactam">Meropenem/vaborbactam</a></li> <li><a href="/wiki/Panipenem/betamipron" title="Panipenem/betamipron">Panipenem/betamipron</a></li> <li><a href="/wiki/Piperacillin/tazobactam" title="Piperacillin/tazobactam">Piperacillin/tazobactam</a></li> <li><a href="/wiki/Sulbactam/durlobactam" title="Sulbactam/durlobactam">Sulbactam/durlobactam</a></li> <li><a href="/wiki/Sulopenem/probenecid" title="Sulopenem/probenecid">Sulopenem/probenecid</a></li> <li><a href="/wiki/Ticarcillin/clavulanic_acid" title="Ticarcillin/clavulanic acid">Ticarcillin/clavulanic acid</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/Polypeptide_antibiotic" title="Polypeptide antibiotic">Polypeptides</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/Lipopeptide" title="Lipopeptide">Lipopeptides</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>Insert into bacterial cell wall causing perforation and depolarization: <a href="/wiki/Daptomycin" title="Daptomycin">Daptomycin</a></li> <li><a href="/wiki/Surfactin" title="Surfactin">Surfactin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Inhibits PG elongation and crosslinking: <a href="/wiki/Ramoplanin" title="Ramoplanin">Ramoplanin</a><sup>§</sup></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Intracellular</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>Inhibit <a href="/wiki/Peptidoglycan" title="Peptidoglycan">PG</a> subunit synthesis and transport: <a href="/wiki/N-Acetylmuramic_acid" title="N-Acetylmuramic acid">NAM</a> synthesis inhibition (<a href="/wiki/Fosfomycin" title="Fosfomycin">Fosfomycin</a>)</li> <li><a href="/wiki/D-alanine%E2%80%94D-alanine_ligase" title="D-alanine—D-alanine ligase">DADAL</a>/<a href="/wiki/Alanine_racemase" title="Alanine racemase">AR</a> inhibitors (<a href="/wiki/Cycloserine" title="Cycloserine">Cycloserine</a>)</li> <li><a href="/wiki/Bactoprenol" title="Bactoprenol">bactoprenol</a> inhibitors (<a href="/wiki/Bacitracin" title="Bacitracin">Bacitracin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Other</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li>Hydrolyze NAM-NAG <ul><li><a href="/wiki/Lysozyme" title="Lysozyme">lysozyme</a></li></ul></li> <li><a href="/wiki/Tyrothricin" title="Tyrothricin">Tyrothricin</a> <ul><li><a href="/wiki/Gramicidin" title="Gramicidin">Gramicidin</a></li> <li><a href="/wiki/Tyrocidine" title="Tyrocidine">Tyrocidine</a></li></ul></li> <li><a href="/wiki/Isoniazid" title="Isoniazid">Isoniazid</a><sup>#</sup></li> <li><a href="/wiki/Teixobactin" title="Teixobactin">Teixobactin</a></li></ul> </div></td></tr><tr><td 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