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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): Tiazofurin">Tiazofurin</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:Tiazofurin.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Tiazofurin.svg/220px-Tiazofurin.svg.png" decoding="async" width="220" height="219" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/Tiazofurin.svg/330px-Tiazofurin.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/06/Tiazofurin.svg/440px-Tiazofurin.svg.png 2x" data-file-width="620" data-file-height="618" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">2-[(2<i>R</i>,3<i>R</i>,4<i>S</i>,5<i>R</i>)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carboxamide</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_L01" title="ATC code L01">L01XX18</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=L01XX18">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">(1<i>R</i>)-1-[4-(aminocarbonyl)-1,3-thiazol-2-yl]-1,4-anhydro-<small>D</small>-ribitol</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=60084-10-8">60084-10-8</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/457954">457954</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.403014.html">403014</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/ULJ82834RE">ULJ82834RE</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL108358">ChEMBL108358</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/DTXSID00208827">DTXSID00208827</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q7800305#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 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>9</sub><span title="Hydrogen">H</span><sub>12</sub><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>5</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="7002260260000000000♠"></span>260.26</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28c1nc%28sc1%29%5BC%40%40H%5D2O%5BC%40%40H%5D%28%5BC%40%40H%5D%28O%29%5BC%40H%5D2O%29CO%29N">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">O=C(c1nc(sc1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO)N</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/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5-,6-,7-/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:FVRDYQYEVDDKCR-DBRKOABJSA-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=470610083&page2=Tiazofurin">(verify)</a></span></span></td></tr></tbody></table> <p><b>Tiazofurin</b> is a drug which acts as an <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a> of the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/IMP_dehydrogenase" class="mw-redirect" title="IMP dehydrogenase">IMP dehydrogenase</a>. Tiazofurin and its analogues were under investigation for potential use in the treatment of <a href="/wiki/Cancer" title="Cancer">cancer</a>,<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> though side effects such as pleuro<a href="/wiki/Pericarditis" title="Pericarditis">pericarditis</a> and a flu-like syndrome precluded further development. They also show <a href="/wiki/Antiviral" class="mw-redirect" title="Antiviral">antiviral</a> effects and may be reevaluated as potential options in the treatment of newly emerging viral diseases.<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> </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=Tiazofurin&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Tiazofurin_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Tiazofurin_synthesis.svg/500px-Tiazofurin_synthesis.svg.png" decoding="async" width="500" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/62/Tiazofurin_synthesis.svg/750px-Tiazofurin_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/62/Tiazofurin_synthesis.svg/1000px-Tiazofurin_synthesis.svg.png 2x" data-file-width="512" data-file-height="174" /></a><figcaption><a rel="nofollow" class="external text" href="https://www.chemdrug.com/article/8/3284/16419504.html">ChemDrug</a> Synthesis:<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></figcaption></figure> <p>The treatment of 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose [6974-32-9] (1) with trimethylsilyl cyanide gives 2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl cyanide [23316-67-8] (2). Treatment with hydrogen sulfide led to (2R,3R,4R,5R)-2-((Benzoyloxy)methyl)-5-carbamothioyltetrahydrofuran-3,4-diyl dibenzoate, PC10907289 (3). Cyclization with Ethyl bromopyruvate [70-23-5] (4) led to 2-(2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl)-4-thiazolecarboxylic Acid Ethyl Ester [60084-09-5] (5). Removal of the protecting groups with sodium methoxide afforded 2-beta-D-Ribofuranosyl-4-thiazolecarboxylic Acid Ethyl Ester [95936-53-1] (6). Amide-ester interchange by treatment with dry ammonia completed the synthesis of Tiazofurin (7). </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=Tiazofurin&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="CITEREFPopsavinTorovićSvircev2006" class="citation journal cs1">Popsavin M, Torović L, Svircev M, et al. (2006). "Synthesis and antiproliferative activity of two new tiazofurin analogues with 2'-amido functionalities". <i>Bioorg. Med. Chem. Lett</i>. <b>16</b> (10): 2773–6. <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%2Fj.bmcl.2006.02.001">10.1016/j.bmcl.2006.02.001</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/16495053">16495053</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Bioorg.+Med.+Chem.+Lett.&rft.atitle=Synthesis+and+antiproliferative+activity+of+two+new+tiazofurin+analogues+with+2%27-amido+functionalities&rft.volume=16&rft.issue=10&rft.pages=2773-6&rft.date=2006&rft_id=info%3Adoi%2F10.1016%2Fj.bmcl.2006.02.001&rft_id=info%3Apmid%2F16495053&rft.aulast=Popsavin&rft.aufirst=M&rft.au=Torovi%C4%87%2C+L&rft.au=Svircev%2C+M&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATiazofurin" 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="CITEREFDe_Clercq2016" class="citation journal cs1">De Clercq E (March 2016). "C-Nucleosides To Be Revisited". <i>Journal of Medicinal Chemistry</i>. <b>59</b> (6): 2301–11. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Facs.jmedchem.5b01157">10.1021/acs.jmedchem.5b01157</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/26513594">26513594</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Medicinal+Chemistry&rft.atitle=C-Nucleosides+To+Be+Revisited&rft.volume=59&rft.issue=6&rft.pages=2301-11&rft.date=2016-03&rft_id=info%3Adoi%2F10.1021%2Facs.jmedchem.5b01157&rft_id=info%3Apmid%2F26513594&rft.aulast=De+Clercq&rft.aufirst=E&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATiazofurin" 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">Eastland, G.; Tiazofurine. Drugs Fut 1985, 10, 4, 304.</span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · 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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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template">e</abbr></a></li></ul></div><div id="Intracellular_chemotherapeutic_agents_/_antineoplastic_agents_(L01)" style="font-size:114%;margin:0 4em">Intracellular <a href="/wiki/Chemotherapy" title="Chemotherapy">chemotherapeutic agents</a> / <a href="/wiki/Antineoplastic" class="mw-redirect" title="Antineoplastic">antineoplastic agents</a> (<a href="/wiki/ATC_code_L01" title="ATC code L01">L01</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Spindle_poison" title="Spindle poison">SPs</a>/<a href="/wiki/Mitotic_inhibitor" title="Mitotic inhibitor">MIs</a><br />(<a href="/wiki/M_phase" class="mw-redirect" title="M phase">M phase</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%">Block <a href="/wiki/Microtubule" title="Microtubule">microtubule</a> assembly</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/Vinca_alkaloid" title="Vinca alkaloid">Vinca alkaloids</a></i> (<a href="/wiki/Vinblastine" title="Vinblastine">Vinblastine</a><sup>#</sup></li> <li><a href="/wiki/Vincristine" title="Vincristine">Vincristine</a><sup>#</sup></li> <li><a href="/wiki/Vindesine" title="Vindesine">Vindesine</a></li> <li><a href="/wiki/Vinflunine" title="Vinflunine">Vinflunine</a><sup>§</sup></li> <li><a href="/wiki/Vinorelbine" title="Vinorelbine">Vinorelbine</a><sup>#</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Block microtubule disassembly</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><i><a href="/wiki/Taxane" title="Taxane">Taxanes</a></i> (<a href="/wiki/Cabazitaxel" title="Cabazitaxel">Cabazitaxel</a></li> <li><a href="/wiki/Docetaxel" title="Docetaxel">Docetaxel</a><sup>#</sup></li> <li><a href="/wiki/Larotaxel" title="Larotaxel">Larotaxel</a></li> <li><a href="/wiki/Ortataxel" title="Ortataxel">Ortataxel</a><sup>†</sup></li> <li><a href="/wiki/Paclitaxel" title="Paclitaxel">Paclitaxel</a><sup>#</sup></li> <li><a href="/wiki/Tesetaxel" title="Tesetaxel">Tesetaxel</a>)</li> <li><i><a href="/wiki/Epothilone" title="Epothilone">Epothilones</a></i> (<a href="/wiki/Ixabepilone" title="Ixabepilone">Ixabepilone</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/DNA_replication" title="DNA replication">DNA replication</a><br />inhibitor</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%">DNA precursors/<br /><a href="/wiki/Antimetabolite" title="Antimetabolite">antimetabolites</a><br />(<a href="/wiki/S_phase" title="S phase">S phase</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/Antifolate" title="Antifolate">Folic acid</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><i><a href="/wiki/Dihydrofolate_reductase_inhibitor" title="Dihydrofolate reductase inhibitor">Dihydrofolate reductase inhibitor</a></i> (<a href="/wiki/Aminopterin" title="Aminopterin">Aminopterin</a></li> <li><a href="/wiki/Methotrexate" title="Methotrexate">Methotrexate</a><sup>#</sup></li> <li><a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Pralatrexate" title="Pralatrexate">Pralatrexate</a>)</li> <li><i><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">Thymidylate synthase inhibitor</a></i> (<a href="/wiki/Pemetrexed" title="Pemetrexed">Pemetrexed</a></li> <li><a href="/wiki/Raltitrexed" title="Raltitrexed">Raltitrexed</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Purine_analogue" title="Purine analogue">Purine</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><i><a href="/wiki/Adenosine_deaminase_inhibitor" class="mw-redirect" title="Adenosine deaminase inhibitor">Adenosine deaminase inhibitor</a></i> (<a href="/wiki/Pentostatin" title="Pentostatin">Pentostatin</a>)</li></ul> <ul><li><i><a href="/wiki/Halogenation" title="Halogenation">Halogenated</a>/<a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">ribonucleotide reductase inhibitors</a></i> (<a href="/wiki/Cladribine" title="Cladribine">Cladribine</a></li> <li><a href="/wiki/Clofarabine" title="Clofarabine">Clofarabine</a></li> <li><a href="/wiki/Fludarabine" title="Fludarabine">Fludarabine</a>)</li> <li><a href="/wiki/Nelarabine" title="Nelarabine">Nelarabine</a></li> <li><a href="/wiki/Rabacfosadine" title="Rabacfosadine">Rabacfosadine</a></li> <li><i><a href="/wiki/Thiopurine" title="Thiopurine">Thiopurine</a></i> (<a href="/wiki/Mercaptopurine" title="Mercaptopurine">Mercaptopurine</a><sup>#</sup></li> <li><a href="/wiki/Tioguanine" title="Tioguanine">Tioguanine</a><sup>#</sup>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pyrimidine_analogue" title="Pyrimidine analogue">Pyrimidine</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><i><a href="/wiki/Thymidylate_synthase_inhibitor" title="Thymidylate synthase inhibitor">Thymidylate synthase inhibitor</a></i> (<a href="/wiki/Capecitabine" title="Capecitabine">Capecitabine</a><sup>#</sup></li> <li><a href="/wiki/Carmofur" title="Carmofur">Carmofur</a></li> <li><a href="/wiki/Doxifluridine" title="Doxifluridine">Doxifluridine</a></li> <li><a href="/wiki/Floxuridine" title="Floxuridine">Floxuridine</a></li> <li><a href="/wiki/Fluorouracil" title="Fluorouracil">Fluorouracil</a><sup>#</sup></li> <li><a href="/wiki/Tegafur" title="Tegafur">Tegafur</a> (<a href="/wiki/Tegafur/gimeracil/oteracil" title="Tegafur/gimeracil/oteracil">+gimeracil/oteracil</a>))</li></ul> <ul><li><i><a href="/wiki/DNA_polymerase_inhibitor" class="mw-redirect" title="DNA polymerase inhibitor">DNA polymerase inhibitor</a></i> (<a href="/wiki/Cytarabine" title="Cytarabine">Cytarabine</a><sup>#</sup> <a href="/wiki/Daunorubicin/cytarabine" title="Daunorubicin/cytarabine">+daunorubicin</a>)</li></ul> <ul><li><i><a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">Ribonucleotide reductase inhibitor</a></i> (<a href="/wiki/Gemcitabine" title="Gemcitabine">Gemcitabine</a><sup>#</sup>)</li></ul> <ul><li><i><a href="/wiki/Hypomethylating_agent" title="Hypomethylating agent">Hypomethylating agent</a></i> (<a href="/wiki/Azacitidine" title="Azacitidine">Azacitidine</a></li> <li><a href="/wiki/Decitabine" title="Decitabine">Decitabine</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Deoxyribonucleotide" title="Deoxyribonucleotide">Deoxyribonucleotide</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><i><a href="/wiki/Ribonucleotide_reductase_inhibitor" title="Ribonucleotide reductase inhibitor">Ribonucleotide reductase inhibitor</a></i> (<a href="/wiki/Hydroxycarbamide" title="Hydroxycarbamide">Hydroxycarbamide</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/Topoisomerase_inhibitor" title="Topoisomerase inhibitor">Topoisomerase inhibitors</a><br />(<a href="/wiki/S_phase" title="S phase">S phase</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/Type_I_topoisomerase#Inhibition" title="Type I topoisomerase">I</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><i><a href="/wiki/Camptotheca" title="Camptotheca">Camptotheca</a></i> (<a href="/wiki/Belotecan" title="Belotecan">Belotecan</a></li> <li><a href="/wiki/Camptothecin" title="Camptothecin">Camptothecin</a></li> <li><a href="/w/index.php?title=Cositecan&action=edit&redlink=1" class="new" title="Cositecan (page does not exist)">Cositecan</a><sup>†</sup></li> <li><a href="/wiki/Etirinotecan_pegol" title="Etirinotecan pegol">Etirinotecan pegol</a><sup>†</sup></li> <li><a href="/wiki/Exatecan" title="Exatecan">Exatecan</a></li> <li><a href="/w/index.php?title=Gimatecan&action=edit&redlink=1" class="new" title="Gimatecan (page does not exist)">Gimatecan</a></li> <li><a href="/wiki/Irinotecan" title="Irinotecan">Irinotecan</a><sup>#</sup></li> <li><a href="/wiki/Lurtotecan" title="Lurtotecan">Lurtotecan</a><sup>‡</sup></li> <li><a href="/wiki/Rubitecan" title="Rubitecan">Rubitecan</a><sup>‡</sup></li> <li><a href="/w/index.php?title=Silatecan&action=edit&redlink=1" class="new" title="Silatecan (page does not exist)">Silatecan</a><sup>§</sup></li> <li><a href="/wiki/Topotecan" title="Topotecan">Topotecan</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_II_topoisomerase#Inhibition" title="Type II topoisomerase">II</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><i><a href="/wiki/Podophyllum_peltatum" title="Podophyllum peltatum">Podophyllum</a></i> (<a href="/wiki/Etoposide" title="Etoposide">Etoposide</a><sup>#</sup></li> <li><a href="/wiki/Teniposide" title="Teniposide">Teniposide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Type_II_topoisomerase#Inhibition" title="Type II topoisomerase">II</a>+<a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">Intercalation</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><i><a href="/wiki/Anthracycline" title="Anthracycline">Anthracyclines</a></i> (<a href="/wiki/Aclarubicin" title="Aclarubicin">Aclarubicin</a></li> <li><a href="/wiki/Amrubicin" title="Amrubicin">Amrubicin</a><sup>†</sup></li> <li><a href="/wiki/Daunorubicin" title="Daunorubicin">Daunorubicin</a><sup>#</sup> (<a href="/wiki/Daunorubicin/cytarabine" title="Daunorubicin/cytarabine">+cytarabine</a>)</li> <li><a href="/wiki/Doxorubicin" title="Doxorubicin">Doxorubicin</a><sup>#</sup></li> <li><a href="/wiki/Epirubicin" title="Epirubicin">Epirubicin</a></li> <li><a href="/wiki/Idarubicin" title="Idarubicin">Idarubicin</a></li> <li><a href="/wiki/Pirarubicin" title="Pirarubicin">Pirarubicin</a></li> <li><a href="/wiki/Valrubicin" title="Valrubicin">Valrubicin</a></li> <li><a href="/wiki/Zorubicin" title="Zorubicin">Zorubicin</a>)</li> <li><i><a href="/wiki/Anthraquinone" title="Anthraquinone">Anthracenediones</a></i> (<a href="/wiki/Losoxantrone" title="Losoxantrone">Losoxantrone</a></li> <li><a href="/wiki/Mitoxantrone" title="Mitoxantrone">Mitoxantrone</a></li> <li><a href="/wiki/Pixantrone" title="Pixantrone">Pixantrone</a>)</li> <li><a href="/wiki/Amsacrine" title="Amsacrine">Amsacrine</a></li> <li><a href="/wiki/Bisantrene" title="Bisantrene">Bisantrene</a></li> <li><a href="/wiki/Crisnatol" title="Crisnatol">Crisnatol</a></li> <li><a href="/wiki/Menogaril" title="Menogaril">Menogaril</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/Crosslinking_of_DNA" title="Crosslinking of DNA">Crosslinking of DNA</a><br />(<a href="/wiki/Cell-cycle_nonspecific_antineoplastic_agents" title="Cell-cycle nonspecific antineoplastic agents">CCNS</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/Alkylating_antineoplastic_agent" title="Alkylating antineoplastic agent">Alkylating</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><i><a href="/wiki/Nitrogen_mustard" title="Nitrogen mustard">Nitrogen mustards</a>:</i> <a href="/wiki/Bendamustine" title="Bendamustine">Bendamustine</a><sup>#</sup></li> <li><a href="/wiki/Chlormethine" title="Chlormethine">Chlormethine</a></li> <li><a href="/wiki/Cyclophosphamide" title="Cyclophosphamide">Cyclophosphamide</a><sup>#</sup> (<a href="/wiki/Ifosfamide" title="Ifosfamide">Ifosfamide</a><sup>#</sup></li> <li><a href="/wiki/Trofosfamide" title="Trofosfamide">Trofosfamide</a>)</li> <li><a href="/wiki/Chlorambucil" title="Chlorambucil">Chlorambucil</a><sup>#</sup></li> <li><a href="/wiki/Melphalan" title="Melphalan">Melphalan</a> (<a href="/wiki/Melphalan_flufenamide" title="Melphalan flufenamide">Melphalan flufenamide</a>)</li> <li><a href="/wiki/Prednimustine" title="Prednimustine">Prednimustine</a></li> <li><a href="/wiki/Uramustine" title="Uramustine">Uramustine</a></li></ul> <ul><li><i><a href="/wiki/Nitrosourea" title="Nitrosourea">Nitrosoureas</a>:</i> <a href="/wiki/Carmustine" title="Carmustine">Carmustine</a></li> <li><a href="/wiki/Fotemustine" title="Fotemustine">Fotemustine</a></li> <li><a href="/wiki/Lomustine" title="Lomustine">Lomustine</a> (<a href="/wiki/Semustine" title="Semustine">Semustine</a>)</li> <li><a href="/wiki/Nimustine" title="Nimustine">Nimustine</a></li> <li><a href="/wiki/Ranimustine" title="Ranimustine">Ranimustine</a></li> <li><a href="/wiki/Streptozotocin" title="Streptozotocin">Streptozocin</a></li></ul> <ul><li><i><a href="/wiki/Alkyl_sulfonate" title="Alkyl sulfonate">Alkyl sulfonates</a>:</i> <a href="/wiki/Busulfan" title="Busulfan">Busulfan</a> (<a href="/wiki/Mannosulfan" title="Mannosulfan">Mannosulfan</a></li> <li><a href="/wiki/Treosulfan" title="Treosulfan">Treosulfan</a>)</li></ul> <ul><li><i><a href="/wiki/Aziridine" title="Aziridine">Aziridines</a>:</i> <a href="/wiki/Carboquone" title="Carboquone">Carboquone</a></li> <li><a href="/wiki/Thiotepa" title="Thiotepa">Thiotepa</a></li> <li><a href="/wiki/Triaziquone" title="Triaziquone">Triaziquone</a></li> <li><a href="/wiki/Triethylenemelamine" title="Triethylenemelamine">Triethylenemelamine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Platinum-based_antineoplastic" title="Platinum-based antineoplastic">Platinum-based</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/Carboplatin" title="Carboplatin">Carboplatin</a><sup>#</sup></li> <li><a href="/wiki/Cisplatin" title="Cisplatin">Cisplatin</a><sup>#</sup></li> <li><a href="/wiki/Dicycloplatin" title="Dicycloplatin">Dicycloplatin</a></li> <li><a href="/wiki/Nedaplatin" title="Nedaplatin">Nedaplatin</a></li> <li><a href="/wiki/Oxaliplatin" title="Oxaliplatin">Oxaliplatin</a><sup>#</sup></li> <li><a href="/wiki/Satraplatin" title="Satraplatin">Satraplatin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Alkylating_antineoplastic_agent#Nonclassical" title="Alkylating antineoplastic agent">Nonclassical</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/Altretamine" title="Altretamine">Altretamine</a></li> <li><i><a href="/wiki/Hydrazine" title="Hydrazine">Hydrazines</a></i> (<a href="/wiki/Procarbazine" title="Procarbazine">Procarbazine</a><sup>#</sup>)</li> <li><a href="/wiki/Etoglucid" title="Etoglucid">Etoglucid</a></li> <li><a href="/wiki/Mitobronitol" title="Mitobronitol">Mitobronitol</a></li> <li><a href="/wiki/Pipobroman" title="Pipobroman">Pipobroman</a></li> <li><i><a href="/wiki/Triazene" title="Triazene">Triazenes</a></i> (<a href="/wiki/Dacarbazine" title="Dacarbazine">Dacarbazine</a><sup>#</sup></li> <li><a href="/wiki/Mitozolomide" title="Mitozolomide">Mitozolomide</a><sup>§</sup></li> <li><a href="/wiki/Temozolomide" title="Temozolomide">Temozolomide</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intercalation_(biochemistry)" title="Intercalation (biochemistry)">Intercalation</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/Streptomyces" title="Streptomyces">Streptomyces</a> (<a href="/wiki/Dactinomycin" title="Dactinomycin">Dactinomycin</a><sup>#</sup></li> <li><a href="/wiki/Bleomycin" title="Bleomycin">Bleomycin</a><sup>#</sup></li> <li><a href="/wiki/Mitomycins" title="Mitomycins">Mitomycins</a></li> <li><a href="/wiki/Plicamycin" title="Plicamycin">Plicamycin</a>)</li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Photosensitizer" title="Photosensitizer">Photosensitizers</a>/<a href="/wiki/Photodynamic_therapy" title="Photodynamic therapy">PDT</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Aminolevulinic_acid" title="Aminolevulinic acid">Aminolevulinic acid</a></li> <li><a href="/wiki/Efaproxiral" title="Efaproxiral">Efaproxiral</a></li> <li><a href="/wiki/Methyl_aminolevulinate" title="Methyl aminolevulinate">Methyl aminolevulinate</a></li> <li><a href="/wiki/Padeliporfin" title="Padeliporfin">Padeliporfin</a></li> <li><i><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrin derivatives</a></i> (<a href="/wiki/Porfimer_sodium" title="Porfimer sodium">Porfimer sodium</a></li> <li><a href="/wiki/Talaporfin" title="Talaporfin">Talaporfin</a></li> <li><a href="/wiki/Temoporfin" title="Temoporfin">Temoporfin</a></li> <li><a href="/wiki/Verteporfin" title="Verteporfin">Verteporfin</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"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">Enzyme inhibitors</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><i><a href="/wiki/Farnesyltransferase_inhibitor" title="Farnesyltransferase inhibitor">FI</a></i> (<a href="/wiki/Tipifarnib" title="Tipifarnib">Tipifarnib</a><sup>§</sup>)</li> <li><i><a href="/wiki/Cyclin-dependent_kinase" title="Cyclin-dependent kinase">CDK</a> <a href="/wiki/Protein_kinase_inhibitor" title="Protein kinase inhibitor">inhibitors</a></i> (<a href="/wiki/Abemaciclib" title="Abemaciclib">Abemaciclib</a></li> <li><a href="/wiki/Alvocidib" title="Alvocidib">Alvocidib</a><sup>†</sup></li> <li><a href="/wiki/Palbociclib" title="Palbociclib">Palbociclib</a></li> <li><a href="/wiki/Ribociclib" title="Ribociclib">Ribociclib</a></li> <li><a href="/wiki/Seliciclib" title="Seliciclib">Seliciclib</a><sup>†</sup>)</li> <li><i><a href="/wiki/Proteasome_inhibitor" title="Proteasome inhibitor">PrI</a></i> <ul><li><a href="/wiki/Bortezomib" title="Bortezomib">Bortezomib</a></li> <li><a href="/wiki/Carfilzomib" title="Carfilzomib">Carfilzomib</a></li> <li><a href="/wiki/Oprozomib" title="Oprozomib">Oprozomib</a></li> <li><a href="/wiki/Ixazomib" title="Ixazomib">Ixazomib</a></li></ul></li> <li><i><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">PhI</a></i> (<a href="/wiki/Anagrelide" title="Anagrelide">Anagrelide</a>)</li> <li><i><a href="/wiki/IMP_dehydrogenase" class="mw-redirect" title="IMP dehydrogenase">IMPDI</a></i> (<a class="mw-selflink selflink">Tiazofurin</a><sup>§</sup>)</li> <li><i><a href="/wiki/Lipoxygenase_inhibitor" class="mw-redirect" title="Lipoxygenase inhibitor">LI</a></i> (<a href="/wiki/Masoprocol" title="Masoprocol">Masoprocol</a>)</li> <li><i><a href="/wiki/PARP_inhibitor" title="PARP inhibitor">PARP inhibitor</a></i> (<a href="/wiki/Fuzuloparib" title="Fuzuloparib">Fuzuloparib</a></li> <li><a href="/wiki/Niraparib" title="Niraparib">Niraparib</a> <a href="/wiki/Niraparib/abiraterone_acetate" title="Niraparib/abiraterone acetate">+abiraterone acetate</a></li> <li><a href="/wiki/Olaparib" title="Olaparib">Olaparib</a></li> <li><a href="/wiki/Rucaparib" title="Rucaparib">Rucaparib</a>)</li> <li><i><a href="/wiki/Histone_deacetylase_inhibitor" title="Histone deacetylase inhibitor">HDAC</a></i> (<a href="/wiki/Belinostat" title="Belinostat">Belinostat</a></li> <li><a href="/wiki/Entinostat" title="Entinostat">Entinostat</a></li> <li><a href="/wiki/Panobinostat" title="Panobinostat">Panobinostat</a></li> <li><a href="/wiki/Romidepsin" title="Romidepsin">Romidepsin</a></li> <li><a href="/wiki/Vorinostat" title="Vorinostat">Vorinostat</a>)</li> <li><i><a href="/wiki/Phosphoinositide_3-kinase_inhibitor" title="Phosphoinositide 3-kinase inhibitor">PIKI</a> (Pi3K)</i> (<a href="/wiki/Alpelisib" title="Alpelisib">Alpelisib</a></li> <li><a href="/wiki/Copanlisib" title="Copanlisib">Copanlisib</a><sup>‡</sup></li> <li><a href="/wiki/Duvelisib" title="Duvelisib">Duvelisib</a></li> <li><a href="/wiki/Idelalisib" title="Idelalisib">Idelalisib</a></li> <li><a href="/wiki/Inavolisib" title="Inavolisib">Inavolisib</a></li> <li><a href="/wiki/Umbralisib" title="Umbralisib">Umbralisib</a><sup>‡</sup>)</li> <li><i><a href="/wiki/Isocitrate_dehydrogenase" title="Isocitrate dehydrogenase">IDH</a></i> (<a href="/wiki/Enasidenib" title="Enasidenib">Enasidenib</a></li> <li><a href="/wiki/Ivosidenib" title="Ivosidenib">Ivosidenib</a></li> <li><a href="/wiki/Olutasidenib" title="Olutasidenib">Olutasidenib</a></li> <li><a href="/wiki/Vorasidenib" title="Vorasidenib">Vorasidenib</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Receptor_antagonist" title="Receptor antagonist">Receptor antagonists</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><i><a href="/wiki/Endothelin_receptor_antagonist" title="Endothelin receptor antagonist">ERA</a></i> (<a href="/wiki/Atrasentan" title="Atrasentan">Atrasentan</a>)</li> <li><i><a href="/wiki/Retinoid_X_receptor" title="Retinoid X receptor">Retinoid X receptor</a></i> (<a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a>)</li> <li><i><a href="/wiki/Sex_steroid" class="mw-redirect" title="Sex steroid">Sex steroid</a></i> (<a href="/wiki/Testolactone" title="Testolactone">Testolactone</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/Adagrasib" title="Adagrasib">Adagrasib</a></li> <li><a href="/wiki/Aflibercept" title="Aflibercept">Aflibercept</a></li> <li><a href="/wiki/Arsenic_trioxide" title="Arsenic trioxide">Arsenic trioxide</a></li> <li><i><a href="/wiki/Asparagine" title="Asparagine">Asparagine depleters</a></i> (<a href="/wiki/Asparaginase" title="Asparaginase">Asparaginase</a><sup>#</sup>/<a href="/wiki/Pegaspargase" title="Pegaspargase">Pegaspargase</a>)</li> <li><a href="/wiki/Axicabtagene_ciloleucel" title="Axicabtagene ciloleucel">Axicabtagene ciloleucel</a></li> <li><a href="/wiki/Belzutifan" title="Belzutifan">Belzutifan</a></li> <li><a href="/wiki/Bexarotene" title="Bexarotene">Bexarotene</a></li> <li><a href="/wiki/Brexucabtagene_autoleucel" title="Brexucabtagene autoleucel">Brexucabtagene autoleucel</a></li> <li><a href="/wiki/Celecoxib" title="Celecoxib">Celecoxib</a></li> <li><a href="/wiki/Ciltacabtagene_autoleucel" title="Ciltacabtagene autoleucel">Ciltacabtagene autoleucel</a></li> <li><a href="/wiki/Demecolcine" title="Demecolcine">Demecolcine</a></li> <li><a href="/wiki/Denileukin_diftitox" title="Denileukin diftitox">Denileukin diftitox</a></li> <li><a href="/wiki/Eflornithine" title="Eflornithine">Eflornithine</a></li> <li><a href="/wiki/Elesclomol" title="Elesclomol">Elesclomol</a><sup>§</sup></li> <li><a href="/wiki/Elsamitrucin" title="Elsamitrucin">Elsamitrucin</a></li> <li><a href="/wiki/Epacadostat" title="Epacadostat">Epacadostat</a></li> <li><a href="/wiki/Eribulin" title="Eribulin">Eribulin</a></li> <li><a href="/wiki/Estramustine_phosphate" title="Estramustine phosphate">Estramustine</a></li> <li><a href="/wiki/Glasdegib" title="Glasdegib">Glasdegib</a></li> <li><a href="/wiki/Idecabtagene_vicleucel" title="Idecabtagene vicleucel">Idecabtagene vicleucel</a></li> <li><a href="/wiki/Imetelstat" title="Imetelstat">Imetelstat</a></li> <li><a href="/wiki/Lifileucel" title="Lifileucel">Lifileucel</a></li> <li><a href="/wiki/Lisocabtagene_maraleucel" title="Lisocabtagene maraleucel">Lisocabtagene maraleucel</a></li> <li><a href="/wiki/Lonidamine" title="Lonidamine">Lonidamine</a></li> <li><a href="/wiki/Lucanthone" title="Lucanthone">Lucanthone</a></li> <li><a href="/wiki/Lurbinectedin" title="Lurbinectedin">Lurbinectedin</a></li> <li><a href="/wiki/Mitoguazone" title="Mitoguazone">Mitoguazone</a></li> <li><a href="/wiki/Mitotane" title="Mitotane">Mitotane</a></li> <li><a href="/wiki/Nadofaragene_firadenovec" title="Nadofaragene firadenovec">Nadofaragene firadenovec</a></li> <li><a href="/wiki/Navitoclax" title="Navitoclax">Navitoclax</a></li> <li><a href="/wiki/Obecabtagene_autoleucel" title="Obecabtagene autoleucel">Obecabtagene autoleucel</a></li> <li><a href="/wiki/Oblimersen" title="Oblimersen">Oblimersen</a><sup>†</sup></li> <li><a href="/wiki/Omacetaxine_mepesuccinate" title="Omacetaxine mepesuccinate">Omacetaxine mepesuccinate</a></li> <li><a href="/wiki/Plitidepsin" title="Plitidepsin">Plitidepsin</a></li> <li><a href="/wiki/Tabelecleucel" title="Tabelecleucel">Tabelecleucel</a></li> <li><i><a href="/wiki/Retinoid" title="Retinoid">Retinoids</a></i> (<a href="/wiki/Alitretinoin" title="Alitretinoin">Alitretinoin</a></li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a><sup>#</sup>)</li> <li><a href="/wiki/Selinexor" title="Selinexor">Selinexor</a></li> <li><a href="/w/index.php?title=Sitimagene_ceradenovec&action=edit&redlink=1" class="new" title="Sitimagene ceradenovec (page does not exist)">Sitimagene ceradenovec</a></li> <li><a href="/wiki/Sotorasib" title="Sotorasib">Sotorasib</a></li> <li><a href="/wiki/Tagraxofusp" title="Tagraxofusp">Tagraxofusp</a></li> <li><a href="/wiki/Talimogene_laherparepvec" title="Talimogene laherparepvec">Talimogene laherparepvec</a></li> <li><a href="/wiki/Tazemetostat" title="Tazemetostat">Tazemetostat</a></li> <li><a href="/wiki/Tebentafusp" title="Tebentafusp">Tebentafusp</a></li> <li><a href="/wiki/Tiazofurine" class="mw-redirect" title="Tiazofurine">Tiazofurine</a></li> <li><a href="/wiki/Tigilanol_tiglate" title="Tigilanol tiglate">Tigilanol tiglate</a></li> <li><a href="/wiki/Tisagenlecleucel" title="Tisagenlecleucel">Tisagenlecleucel</a></li> <li><a href="/wiki/Trabectedin" title="Trabectedin">Trabectedin</a></li> <li><a href="/wiki/Veliparib" title="Veliparib">Veliparib</a></li> <li><a href="/wiki/Venetoclax" title="Venetoclax">Venetoclax</a></li> <li><a href="/w/index.php?title=Verdinexor&action=edit&redlink=1" class="new" title="Verdinexor (page does not exist)">Verdinexor</a></li> <li><a href="/wiki/Vosaroxin" title="Vosaroxin">Vosaroxin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="background: transparent; padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <p><br /> </p> <style data-mw-deduplicate="TemplateStyles:r1012311289">.mw-parser-output .asbox{position:relative;overflow:hidden}.mw-parser-output .asbox table{background:transparent}.mw-parser-output .asbox p{margin:0}.mw-parser-output .asbox p+p{margin-top:0.25em}.mw-parser-output .asbox-body{font-style:italic}.mw-parser-output .asbox-note{font-size:smaller}.mw-parser-output .asbox .navbar{position:absolute;top:-0.75em;right:1em;display:none}</style><div role="note" class="metadata plainlinks asbox stub"><table role="presentation"><tbody><tr class="noresize"><td><span typeof="mw:File"><a href="/wiki/File:Cisplatin-3D-vdW.png" class="mw-file-description"><img alt="Stub icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Cisplatin-3D-vdW.png/40px-Cisplatin-3D-vdW.png" decoding="async" width="40" height="35" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/77/Cisplatin-3D-vdW.png/60px-Cisplatin-3D-vdW.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/77/Cisplatin-3D-vdW.png/80px-Cisplatin-3D-vdW.png 2x" data-file-width="1100" data-file-height="949" /></a></span></td><td><p class="asbox-body">This <a href="/wiki/Antineoplastic" class="mw-redirect" title="Antineoplastic">antineoplastic</a> or <a href="/wiki/Immunomodulator" class="mw-redirect" title="Immunomodulator">immunomodulatory</a> <a href="/wiki/Pharmaceutical_drug" class="mw-redirect" title="Pharmaceutical drug">drug</a> article is a <a href="/wiki/Wikipedia:Stub" title="Wikipedia:Stub">stub</a>. 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