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interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D8%B2%DB%8C%D9%85%D9%84%D8%A7%DA%AF%D8%A7%D8%AA%D8%B1%D8%A7%D9%86" title="زیملاگاتران – Persian" lang="fa" hreflang="fa" data-title="زیملاگاتران" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Xim%C3%A9lagatran" title="Ximélagatran – French" lang="fr" hreflang="fr" data-title="Ximélagatran" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Ximelagatran" title="Ximelagatran – Italian" lang="it" hreflang="it" data-title="Ximelagatran" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Ximelagatran" title="Ximelagatran – Dutch" lang="nl" hreflang="nl" data-title="Ximelagatran" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Ximelagatrana" title="Ximelagatrana – Portuguese" lang="pt" hreflang="pt" data-title="Ximelagatrana" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Ximelagatran" title="Ximelagatran – Romanian" lang="ro" hreflang="ro" data-title="Ximelagatran" 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/Ksimelagatran" title="Ksimelagatran – Serbian" lang="sr" hreflang="sr" data-title="Ksimelagatran" 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/Ksimelagatran" title="Ksimelagatran – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Ksimelagatran" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</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/Q3570984#sitelinks-wikipedia" title="Edit interlanguage links" class="wbc-editpage">Edit links</a></span></div> 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(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Ximelagatran">Ximelagatran</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="dark_mode_safe" typeof="mw:File"><a href="/wiki/File:Ximelagatran.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Ximelagatran.svg/250px-Ximelagatran.svg.png" decoding="async" width="230" height="191" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/72/Ximelagatran.svg/500px-Ximelagatran.svg.png 1.5x" data-file-width="582" data-file-height="483" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Exanta</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Pregnancy_category" title="Pregnancy category">Pregnancy<br />category</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>Uncategorized</li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data">Oral (<a href="/wiki/Tablet_(pharmacy)" title="Tablet (pharmacy)">tablets</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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><a href="/wiki/ATC_code_B01" title="ATC code B01">B01AE05</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=B01AE05">WHO</a></span>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"> <ul><li>Withdrawn from market</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">20%</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">to <a href="/wiki/Melagatran" class="mw-redirect" title="Melagatran">melagatran</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">3–5 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">Renal (80%)</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">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%;">ethyl 2-[[(1<i>R</i>)-1-cyclohexyl-2-<br />[(2<i>S</i>)-2-[[4-(<i>N'</i>-hydroxycarbamimidoyl)<br />phenyl]methylcarbamoyl]azetidin-1-yl]-<br />2-oxo-ethyl]amino]acetate</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=192939-46-1">192939-46-1</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/9574101">9574101</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</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.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=6381">6381</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/DB04898">DB04898</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.7848559.html">7848559</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/49HFB70472">49HFB70472</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/D01981">D01981</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL522038">ChEMBL522038</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/DTXSID5049075">DTXSID5049075</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q3570984#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;color:inherit;">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>24</sub><span title="Hydrogen">H</span><sub>35</sub><span title="Nitrogen">N</span><sub>5</sub><span title="Oxygen">O</span><sub>5</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002473574000000000♠"></span>473.574</span> g·mol<sup>−1</sup> (429 g/mol after conversion)</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%28NCc1ccc%28C%28%3DN%5CO%29%5CN%29cc1%29%5BC%40H%5D3N%28C%28%3DO%29%5BC%40H%5D%28NCC%28%3DO%29OCC%29C2CCCCC2%29CC3">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(NCc1ccc(C(=N\O)\N)cc1)[C@H]3N(C(=O)[C@H](NCC(=O)OCC)C2CCCCC2)CC3</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/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/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:ZXIBCJHYVWYIKI-PZJWPPBQSA-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=470633864&page2=Ximelagatran">(verify)</a></span></span></td></tr></tbody></table> <p><b>Ximelagatran</b> (<b>Exanta</b> or <b>Exarta</b>, H 376/95) is an <a href="/wiki/Anticoagulant" title="Anticoagulant">anticoagulant</a> that has been investigated extensively as a replacement for <a href="/wiki/Warfarin" title="Warfarin">warfarin</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> that would overcome the problematic <a href="/wiki/Diet_(nutrition)" title="Diet (nutrition)">dietary</a>, <a href="/wiki/Drug_interaction" title="Drug interaction">drug interaction</a>, and <a href="/wiki/Therapeutic_drug_monitoring" title="Therapeutic drug monitoring">monitoring</a> issues associated with warfarin therapy. In 2006, its manufacturer <a href="/wiki/AstraZeneca" title="AstraZeneca">AstraZeneca</a> announced that it would withdraw pending applications for marketing approval after reports of <a href="/wiki/Hepatotoxicity" title="Hepatotoxicity">hepatotoxicity</a> (liver damage) during trials, and discontinue its distribution in countries where the drug had been approved (Germany, Portugal, Sweden, Finland, Norway, Iceland, Austria, Denmark, France, Switzerland, Argentina and Brazil).<sup id="cite_ref-az_2-0" class="reference"><a href="#cite_note-az-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Method_of_action">Method of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ximelagatran&action=edit&section=1" title="Edit section: Method of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ximelagatran, a <a href="/wiki/Direct_thrombin_inhibitor" title="Direct thrombin inhibitor">direct thrombin inhibitor</a>,<sup id="cite_ref-pmid17319469_3-0" class="reference"><a href="#cite_note-pmid17319469-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> was the first member of this class that can be taken orally. It acts solely by inhibiting the actions of <a href="/wiki/Thrombin" title="Thrombin">thrombin</a>. It is taken orally twice daily, and rapidly absorbed by the <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a>. Ximelagatran is a <a href="/wiki/Prodrug" title="Prodrug">prodrug</a>, being converted <i><a href="/wiki/In_vivo" title="In vivo">in vivo</a></i> to the active agent melagatran. This conversion takes place in the liver and many other tissues through <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> and <a href="/wiki/Dehydroxylation" class="mw-redirect" title="Dehydroxylation">dehydroxylation</a> (replacing the <a href="/wiki/Ethyl_group" title="Ethyl group">ethyl</a> and <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> groups with <a href="/wiki/Hydrogen" title="Hydrogen">hydrogen</a>). </p> <figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Ximelagatran_activation.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Ximelagatran_activation.svg/330px-Ximelagatran_activation.svg.png" decoding="async" width="330" height="111" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Ximelagatran_activation.svg/500px-Ximelagatran_activation.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Ximelagatran_activation.svg/960px-Ximelagatran_activation.svg.png 2x" data-file-width="1441" data-file-height="483" /></a><figcaption>The conversion of ximelagatran to melagatran. This conversion includes <a href="/wiki/Dealkylation" class="mw-redirect" title="Dealkylation">dealkylation</a> and <a href="/wiki/Dehydroxylation" class="mw-redirect" title="Dehydroxylation">dehydroxylation</a>.</figcaption></figure> <div style="clear:left;" class=""></div> <div class="mw-heading mw-heading2"><h2 id="Uses">Uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ximelagatran&action=edit&section=2" title="Edit section: Uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ximelagatran was expected to replace <a href="/wiki/Warfarin" title="Warfarin">warfarin</a> and sometimes <a href="/wiki/Aspirin" title="Aspirin">aspirin</a> and <a href="/wiki/Heparin" title="Heparin">heparin</a> in many therapeutic settings, including <a href="/wiki/Deep_venous_thrombosis" class="mw-redirect" title="Deep venous thrombosis">deep venous thrombosis</a>, prevention of secondary venous <a href="/wiki/Thromboembolism" title="Thromboembolism">thromboembolism</a> and complications of <a href="/wiki/Atrial_fibrillation" title="Atrial fibrillation">atrial fibrillation</a> such as stroke. The efficacy of ximelagatran for these indications had been well documented,<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> except for non valvular atrial fibrillation. </p><p>An advantage, according to early reports by its manufacturer, was that it could be taken orally without any monitoring of its anticoagulant properties. This would have set it apart from <a href="/wiki/Warfarin" title="Warfarin">warfarin</a> and <a href="/wiki/Heparin" title="Heparin">heparin</a>, which require monitoring of the <a href="/wiki/International_normalized_ratio" class="mw-redirect" title="International normalized ratio">international normalized ratio</a> (INR) and the <a href="/wiki/Partial_thromboplastin_time" title="Partial thromboplastin time">partial thromboplastin time</a> (PTT), respectively. A disadvantage recognised early was the absence of an <a href="/wiki/Antidote" title="Antidote">antidote</a> in case acute bleeding develops, while warfarin can be antagonised by <a href="/wiki/Prothrombin_complex_concentrate" title="Prothrombin complex concentrate">prothrombin complex concentrate</a> and/or <a href="/wiki/Vitamin_K" title="Vitamin K">vitamin K</a> and heparin by <a href="/wiki/Protamine_sulfate" title="Protamine sulfate">protamine sulfate</a>. </p> <div class="mw-heading mw-heading2"><h2 id="Side_effects">Side effects</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ximelagatran&action=edit&section=3" title="Edit section: Side effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ximelagatran was generally well tolerated in the trial populations, but a small proportion (5–6%) developed elevated <a href="/wiki/Liver_enzyme" class="mw-redirect" title="Liver enzyme">liver enzyme</a> levels, which prompted the <a href="/wiki/U.S._Food_and_Drug_Administration" class="mw-redirect" title="U.S. Food and Drug Administration">FDA</a> to reject an initial application for approval in 2004. The further development was discontinued in 2006 following reports of hepatotoxicity. Subsequent analysis of Phase 2 clinical study data using <a href="/wiki/Extreme_value_theory" title="Extreme value theory">extreme value modelling</a> showed that the elevated <a href="/wiki/Liver_enzyme" class="mw-redirect" title="Liver enzyme">liver enzyme</a> levels observed in Phase 3 clinical studies could have been predicted; if this had been known at the time, it might have affected decisions on future development of the compound.<sup id="cite_ref-Southworth_2014_7-0" class="reference"><a href="#cite_note-Southworth_2014-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>A chemically different but pharmacologically similar substance, <a href="/w/index.php?title=AZD-0837&action=edit&redlink=1" class="new" title="AZD-0837 (page does not exist)">AZD-0837</a>, was developed by AstraZeneca for similar indications.<sup id="cite_ref-az_2-1" class="reference"><a href="#cite_note-az-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is a prodrug of a potent, competitive, reversible inhibitor of free and fibrin-bound thrombin called <a href="/w/index.php?title=ARH0637&action=edit&redlink=1" class="new" title="ARH0637 (page does not exist)">ARH0637</a>.<sup id="cite_ref-Ahrens_8-0" class="reference"><a href="#cite_note-Ahrens-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> The development of AZD-0837 has been discontinued. Due to a limitation identified in long-term stability of the extended-release AZD-0837 drug product, a follow-up study from ASSURE on stroke prevention in patients with non-valvular atrial fibrillation, was prematurely closed in 2010 after 2 years. There was also a numerically higher mortality against warfarin.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> In a Phase 2 trial for AF the mean serum creatinine concentration increased by about 10% from baseline in patients treated with AZD-0837, which returned to baseline after cessation of therapy.<sup id="cite_ref-pmid19690349_12-0" class="reference"><a href="#cite_note-pmid19690349-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ximelagatran&action=edit&section=4" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFHirshO'DonnellEikelboom2007" class="citation journal cs1">Hirsh J, O'Donnell M, Eikelboom JW (July 2007). <a rel="nofollow" class="external text" href="https://doi.org/10.1161%2FCIRCULATIONAHA.106.685974">"Beyond unfractionated heparin and warfarin: current and 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Astrazenecaclinicaltrials.com<span class="reference-accessdate">. Retrieved <span class="nowrap">2012-10-16</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=AZD0837&rft.pub=Astrazenecaclinicaltrials.com&rft_id=http%3A%2F%2Fwww.astrazenecaclinicaltrials.com%2Fother-drug-products%2Fin_development_drugs%2FAZD0837%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXimelagatran" class="Z3988"></span></span> </li> <li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20131110014536/http://www.astrazenecaclinicaltrials.com/_mshost800325/content/clinical-trials/resources/pdf/D1250C00042">"Long-term treatment with the oral direct thrombin inhibitor AZD0837, compared to Vitamin-K antagonists, as stroke prevention in patients with non-valvular atrial fibrillation and one or more risk factors for stroke and systemic embolic events. A 5-year follow-up study study"</a>. <i>Clinical Study Report Synopsis</i>. AstraZeneca. 21 January 2010. Trial D1250C0004221. Archived from <a rel="nofollow" class="external text" href="http://www.astrazenecaclinicaltrials.com/_mshost800325/content/clinical-trials/resources/pdf/D1250C00042">the original</a> on 10 November 2013.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Clinical+Study+Report+Synopsis&rft.atitle=Long-term+treatment+with+the+oral+direct+thrombin+inhibitor+AZD0837%2C+compared+to+Vitamin-K+antagonists%2C+as+stroke+prevention+in+patients+with+non-valvular+atrial+fibrillation+and+one+or+more+risk+factors+for+stroke+and+systemic+embolic+events.+A+5-year+follow-up+study+study&rft.date=2010-01-21&rft_id=http%3A%2F%2Fwww.astrazenecaclinicaltrials.com%2F_mshost800325%2Fcontent%2Fclinical-trials%2Fresources%2Fpdf%2FD1250C00042&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXimelagatran" class="Z3988"></span></span> </li> <li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFEikelboomWeitz2010" class="citation journal cs1">Eikelboom JW, Weitz JI (April 2010). <a rel="nofollow" class="external text" href="https://doi.org/10.1161%2FCIRCULATIONAHA.109.853119">"New anticoagulants"</a>. <i>Circulation</i>. <b>121</b> (13): <span class="nowrap">1523–</span>1532. <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/10.1161%2FCIRCULATIONAHA.109.853119">10.1161/CIRCULATIONAHA.109.853119</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/20368532">20368532</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Circulation&rft.atitle=New+anticoagulants&rft.volume=121&rft.issue=13&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1523-%3C%2Fspan%3E1532&rft.date=2010-04&rft_id=info%3Adoi%2F10.1161%2FCIRCULATIONAHA.109.853119&rft_id=info%3Apmid%2F20368532&rft.aulast=Eikelboom&rft.aufirst=JW&rft.au=Weitz%2C+JI&rft_id=https%3A%2F%2Fdoi.org%2F10.1161%252FCIRCULATIONAHA.109.853119&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXimelagatran" class="Z3988"></span></span> </li> <li id="cite_note-pmid19690349-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-pmid19690349_12-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLipRasmussenOlssonJensen2009" class="citation journal cs1">Lip GY, Rasmussen LH, Olsson SB, Jensen EC, Persson AL, Eriksson U, Wåhlander KF (December 2009). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2785945">"Oral direct thrombin inhibitor AZD0837 for the prevention of stroke and systemic embolism in patients with non-valvular atrial fibrillation: a randomized dose-guiding, safety, and tolerability study of four doses of AZD0837 vs. vitamin K antagonists"</a>. <i>European Heart Journal</i>. <b>30</b> (23): <span class="nowrap">2897–</span>2907. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1093%2Feurheartj%2Fehp318">10.1093/eurheartj/ehp318</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2785945">2785945</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19690349">19690349</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=European+Heart+Journal&rft.atitle=Oral+direct+thrombin+inhibitor+AZD0837+for+the+prevention+of+stroke+and+systemic+embolism+in+patients+with+non-valvular+atrial+fibrillation%3A+a+randomized+dose-guiding%2C+safety%2C+and+tolerability+study+of+four+doses+of+AZD0837+vs.+vitamin+K+antagonists&rft.volume=30&rft.issue=23&rft.pages=%3Cspan+class%3D%22nowrap%22%3E2897-%3C%2Fspan%3E2907&rft.date=2009-12&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2785945%23id-name%3DPMC&rft_id=info%3Apmid%2F19690349&rft_id=info%3Adoi%2F10.1093%2Feurheartj%2Fehp318&rft.aulast=Lip&rft.aufirst=GY&rft.au=Rasmussen%2C+LH&rft.au=Olsson%2C+SB&rft.au=Jensen%2C+EC&rft.au=Persson%2C+AL&rft.au=Eriksson%2C+U&rft.au=W%C3%A5hlander%2C+KF&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2785945&rfr_id=info%3Asid%2Fen.wikipedia.org%3AXimelagatran" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ximelagatran&action=edit&section=5" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://druginfo.nlm.nih.gov/drugportal/name/ximelagatran">"Ximelagatran"</a>. <i>Drug Information Portal</i>. 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0.25em"> <ul><li><a href="/wiki/Aspirin" title="Aspirin">Acetylsalicylic acid/Aspirin</a><sup>#</sup></li> <li><a href="/wiki/Aloxiprin" title="Aloxiprin">Aloxiprin</a></li> <li><a href="/wiki/Carbasalate_calcium" title="Carbasalate calcium">Carbasalate calcium</a></li> <li><a href="/wiki/Indobufen" title="Indobufen">Indobufen</a></li> <li><a href="/wiki/Triflusal" title="Triflusal">Triflusal</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Thromboxane_inhibitors" class="mw-redirect" title="Thromboxane inhibitors">Thromboxane 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><a href="/wiki/Thromboxane_synthase_inhibitors" class="mw-redirect" title="Thromboxane synthase inhibitors">Thromboxane synthase inhibitors</a> <ul><li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a> (<a href="/wiki/Acetylsalicylic_acid/dipyridamole" title="Acetylsalicylic acid/dipyridamole">+ aspirin</a>)</li> <li><a href="/wiki/Picotamide" title="Picotamide">Picotamide</a></li> <li><a href="/wiki/Terbogrel" title="Terbogrel">Terbogrel</a></li></ul></li> <li><a href="/wiki/Thromboxane_receptor_antagonist" class="mw-redirect" title="Thromboxane receptor antagonist">Receptor antagonists</a> <ul><li><a href="/wiki/Terbogrel" title="Terbogrel">Terbogrel</a></li> <li><a href="/wiki/Terutroban" title="Terutroban">Terutroban</a><sup>§</sup></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phosphodiesterase_inhibitor" title="Phosphodiesterase inhibitor">Phosphodiesterase 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/Cilostazol" title="Cilostazol">Cilostazol</a></li> <li><a href="/wiki/Dipyridamole" title="Dipyridamole">Dipyridamole</a></li> <li><a href="/wiki/Triflusal" title="Triflusal">Triflusal</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><a href="/wiki/Cloricromen" title="Cloricromen">Cloricromen</a></li> <li><a href="/wiki/Ditazole" title="Ditazole">Ditazole</a></li> <li><a href="/wiki/Vorapaxar" title="Vorapaxar">Vorapaxar</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/Anticoagulant" title="Anticoagulant">Anticoagulants</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/Vitamin_K_antagonist" title="Vitamin K antagonist">Vitamin K antagonists</a><br />(inhibit <a href="/wiki/Thrombin" title="Thrombin">II</a>, <a href="/wiki/Factor_VII" title="Factor VII">VII</a>, <a href="/wiki/Factor_IX" title="Factor IX">IX</a>, <a href="/wiki/Factor_X" title="Factor X">X</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/Coumarin" title="Coumarin">Coumarins</a>: <a href="/wiki/Acenocoumarol" title="Acenocoumarol">Acenocoumarol</a></li> <li><a href="/wiki/Coumatetralyl" title="Coumatetralyl">Coumatetralyl</a></li> <li><a href="/wiki/Dicoumarol" title="Dicoumarol">Dicoumarol</a></li> <li><a href="/wiki/Ethyl_biscoumacetate" title="Ethyl biscoumacetate">Ethyl biscoumacetate</a></li> <li><a href="/wiki/Phenprocoumon" title="Phenprocoumon">Phenprocoumon</a></li> <li><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a><sup>#</sup></li> <li><a href="/wiki/1,3-Indandione" title="1,3-Indandione">1,3-Indandiones</a>: <a href="/wiki/Clorindione" title="Clorindione">Clorindione</a></li> <li><a href="/wiki/Diphenadione" title="Diphenadione">Diphenadione</a></li> <li><a href="/wiki/Phenindione" title="Phenindione">Phenindione</a></li> <li>Other: <a href="/wiki/Tioclomarol" title="Tioclomarol">Tioclomarol</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Factor_Xa" class="mw-redirect" title="Factor Xa">Factor Xa</a> inhibitors<br />(with some II inhibition)</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/Heparin" title="Heparin">Heparin</a> group/<br /><a href="/wiki/Glycosaminoglycan" title="Glycosaminoglycan">glycosaminoglycans</a>/<br />(bind <a href="/wiki/Antithrombin" title="Antithrombin">antithrombin</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/Low-molecular-weight_heparin" title="Low-molecular-weight heparin">Low-molecular-weight heparin</a> <ul><li><a href="/wiki/Bemiparin_sodium" title="Bemiparin sodium">Bemiparin</a></li> <li><a href="/wiki/Certoparin_sodium" title="Certoparin sodium">Certoparin</a></li> <li><a href="/wiki/Dalteparin_sodium" title="Dalteparin sodium">Dalteparin</a></li> <li><a href="/wiki/Enoxaparin_sodium" title="Enoxaparin sodium">Enoxaparin</a></li> <li><a href="/wiki/Nadroparin_calcium" title="Nadroparin calcium">Nadroparin</a></li> <li><a href="/wiki/Parnaparin_sodium" title="Parnaparin sodium">Parnaparin</a></li> <li><a href="/wiki/Reviparin_sodium" title="Reviparin sodium">Reviparin</a></li> <li><a href="/wiki/Tinzaparin_sodium" title="Tinzaparin sodium">Tinzaparin</a></li></ul></li> <li><a href="/wiki/Oligosaccharide" title="Oligosaccharide">Oligosaccharides</a> <ul><li><a href="/wiki/Fondaparinux" title="Fondaparinux">Fondaparinux</a></li> <li><a href="/wiki/Idraparinux" title="Idraparinux">Idraparinux</a><sup>§</sup></li></ul></li> <li><a href="/wiki/Heparinoid" title="Heparinoid">Heparinoids</a> <ul><li><a href="/wiki/Danaparoid" title="Danaparoid">Danaparoid</a></li> <li><a href="/wiki/Dermatan_sulfate" title="Dermatan sulfate">Dermatan sulfate</a></li> <li><a href="/wiki/Sulodexide" title="Sulodexide">Sulodexide</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Direct_factor_Xa_inhibitors" title="Direct factor Xa inhibitors">Direct Xa inhibitors</a> ("xabans")</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/Apixaban" title="Apixaban">Apixaban</a></li> <li><a href="/wiki/Betrixaban" title="Betrixaban">Betrixaban</a></li> <li><a href="/wiki/Darexaban" title="Darexaban">Darexaban</a><sup>§</sup></li> <li><a href="/wiki/Edoxaban" title="Edoxaban">Edoxaban</a></li> <li><a href="/wiki/Otamixaban" title="Otamixaban">Otamixaban</a><sup>§</sup></li> <li><a href="/wiki/Rivaroxaban" title="Rivaroxaban">Rivaroxaban</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/Direct_thrombin_inhibitor" title="Direct thrombin inhibitor">Direct thrombin (IIa) 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><a href="/wiki/Direct_thrombin_inhibitor#Bivalent" title="Direct thrombin inhibitor">Bivalent</a>: <a href="/wiki/Hirudin" title="Hirudin">Hirudin</a> <ul><li><a href="/wiki/Bivalirudin" title="Bivalirudin">Bivalirudin</a></li> <li><a href="/wiki/Desirudin" class="mw-redirect" title="Desirudin">Desirudin</a></li> <li><a href="/wiki/Lepirudin" title="Lepirudin">Lepirudin</a><sup>‡</sup></li></ul></li> <li><a href="/wiki/Direct_thrombin_inhibitor#Univalent" title="Direct thrombin inhibitor">Univalent</a>: <a href="/wiki/Argatroban" title="Argatroban">Argatroban</a></li> <li><a href="/wiki/Dabigatran" title="Dabigatran">Dabigatran</a></li> <li><a href="/w/index.php?title=Efegatran&action=edit&redlink=1" class="new" title="Efegatran (page does not exist)">Efegatran</a></li> <li><a href="/wiki/Inogatran" title="Inogatran">Inogatran</a><sup>§</sup></li> <li><a href="/wiki/Melagatran" class="mw-redirect" title="Melagatran">Melagatran</a><sup>‡</sup></li> <li><a class="mw-selflink selflink">Ximelagatran</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/Abelacimab" title="Abelacimab">Abelacimab</a></li> <li><a href="/wiki/Antithrombin" title="Antithrombin">Antithrombin III</a></li> <li><a href="/wiki/Defibrotide" title="Defibrotide">Defibrotide</a></li> <li><a href="/wiki/Fitusiran" title="Fitusiran">Fitusiran</a></li> <li><a href="/wiki/Nafamostat" title="Nafamostat">Nafamostat</a></li> <li><a href="/wiki/Protein_C" title="Protein C">Protein C</a> <ul><li><a href="/wiki/Drotrecogin_alfa" title="Drotrecogin alfa">Drotrecogin alfa</a><sup>‡</sup></li></ul></li> <li><a href="/wiki/Ramatroban" title="Ramatroban">Ramatroban</a></li> <li><a href="/wiki/REG1" title="REG1">REG1</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/Thrombolytic_drug" class="mw-redirect" title="Thrombolytic drug">Thrombolytic drugs</a>/<br /><a href="/wiki/Fibrinolytic" class="mw-redirect" title="Fibrinolytic">fibrinolytics</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/Plasminogen_activator" title="Plasminogen activator">Plasminogen activators</a>: <a href="/wiki/Recombinant_tissue_plasminogen_activators" class="mw-redirect" title="Recombinant tissue plasminogen activators">r-tPA</a> <ul><li><a href="/wiki/Alteplase" title="Alteplase">Alteplase</a><sup>#</sup></li> <li><a href="/wiki/Reteplase" title="Reteplase">Reteplase</a></li> <li><a href="/wiki/Tenecteplase" title="Tenecteplase">Tenecteplase</a></li> <li><a href="/wiki/Desmoteplase" title="Desmoteplase">Desmoteplase</a><sup>†</sup></li></ul></li> <li>UPA <ul><li><a href="/wiki/Saruplase" title="Saruplase">Saruplase</a></li> <li><a href="/wiki/Urokinase" title="Urokinase">Urokinase</a></li></ul></li> <li><a href="/wiki/Anistreplase" title="Anistreplase">Anistreplase</a></li> <li><a href="/wiki/Monteplase" title="Monteplase">Monteplase</a></li> <li><a href="/wiki/Streptokinase" title="Streptokinase">Streptokinase</a><sup>#</sup></li> <li>Other <a href="/wiki/Serine_endopeptidase" class="mw-redirect" title="Serine endopeptidase">serine endopeptidases</a>: <a href="/wiki/Ancrod" title="Ancrod">Ancrod</a><sup>‡</sup></li> <li><a href="/wiki/Brinase" title="Brinase">Brinase</a></li> <li><a href="/wiki/Fibrinolysin" title="Fibrinolysin">Fibrinolysin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Anticoagulant" title="Anticoagulant">Non-medicinal</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/Citrate" class="mw-redirect" title="Citrate">Citrate</a></li> <li><a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">EDTA</a></li> <li><a href="/wiki/Oxalate" title="Oxalate">Oxalate</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding: 0px;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235" /></div><div role="navigation" class="navbox" aria-labelledby="AstraZeneca299" style="padding:3px"><table class="nowraplinks hlist mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374" /><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231" /><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:AstraZeneca" title="Template:AstraZeneca"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:AstraZeneca" title="Template talk:AstraZeneca"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:AstraZeneca" title="Special:EditPage/Template:AstraZeneca"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="AstraZeneca299" style="font-size:114%;margin:0 4em"><a href="/wiki/AstraZeneca" title="AstraZeneca">AstraZeneca</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Products</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/Acalabrutinib" title="Acalabrutinib">Acalabrutinib</a></li> <li><a href="/wiki/Anastrozole" title="Anastrozole">Anastrozole</a></li> <li><a href="/wiki/Andexanet_alfa" title="Andexanet alfa">Andexanet alfa</a></li> <li><a href="/wiki/Anifrolumab" title="Anifrolumab">Anifrolumab</a></li> <li><a href="/wiki/Asfotase_alfa" title="Asfotase alfa">Asfotase alfa</a></li> <li><a href="/wiki/Atenolol" title="Atenolol">Atenolol</a></li> <li><a href="/wiki/Benralizumab" title="Benralizumab">Benralizumab</a></li> <li><a href="/wiki/Bicalutamide" title="Bicalutamide">Bicalutamide</a></li> <li><a href="/wiki/Brompheniramine" title="Brompheniramine">Brompheniramine</a></li> <li><a href="/wiki/Budesonide" title="Budesonide">Budesonide</a></li> <li><a href="/wiki/Budesonide/formoterol" title="Budesonide/formoterol">Budesonide/formoterol</a></li> <li><a href="/wiki/Budesonide/glycopyrronium_bromide/formoterol" title="Budesonide/glycopyrronium bromide/formoterol">Budesonide/glycopyrronium bromide/formoterol</a></li> <li><a href="/wiki/Candesartan" title="Candesartan">Candesartan</a></li> <li><a href="/wiki/Dapagliflozin" title="Dapagliflozin">Dapagliflozin</a></li> <li><a href="/wiki/Disufenton_sodium" title="Disufenton sodium">Disufenton sodium</a></li> <li><a href="/wiki/Durvalumab" title="Durvalumab">Durvalumab</a></li> <li><a href="/wiki/Eculizumab" title="Eculizumab">Eculizumab</a></li> <li><a href="/wiki/Esomeprazole" title="Esomeprazole">Esomeprazole</a></li> <li><a href="/wiki/Exenatide" title="Exenatide">Exenatide</a></li> <li><a href="/wiki/Live_attenuated_influenza_vaccine" title="Live attenuated influenza vaccine">FluMist</a></li> <li><a href="/wiki/Fulvestrant" title="Fulvestrant">Fulvestrant</a></li> <li><a href="/wiki/Gefitinib" title="Gefitinib">Gefitinib</a></li> <li><a href="/wiki/Glycopyrronium_bromide/formoterol" title="Glycopyrronium bromide/formoterol">Glycopyrronium bromide/formoterol</a></li> <li><a href="/wiki/Goserelin" title="Goserelin">Goserelin</a></li> <li><a href="/wiki/Isosorbide_mononitrate" title="Isosorbide mononitrate">Isosorbide mononitrate</a></li> <li><a href="/wiki/Metoprolol" title="Metoprolol">Metoprolol</a></li> <li><a href="/wiki/Motavizumab" title="Motavizumab">Motavizumab</a></li> <li><a href="/wiki/Olaparib" title="Olaparib">Olaparib</a></li> <li><a href="/wiki/Omeprazole" title="Omeprazole">Omeprazole</a></li> <li><a href="/wiki/Osimertinib" title="Osimertinib">Osimertinib</a></li> <li><a href="/wiki/Palivizumab" title="Palivizumab">Palivizumab</a></li> <li><a href="/wiki/Propofol" title="Propofol">Propofol</a></li> <li><a href="/wiki/Quetiapine" title="Quetiapine">Quetiapine</a></li> <li><a href="/wiki/Ravulizumab" title="Ravulizumab">Ravulizumab</a></li> <li><a href="/wiki/Roflumilast" title="Roflumilast">Roflumilast</a></li> <li><a href="/wiki/Rosuvastatin" title="Rosuvastatin">Rosuvastatin</a></li> <li><a href="/wiki/Roxadustat" title="Roxadustat">Roxadustat</a></li> <li><a href="/wiki/Salbutamol/budesonide" title="Salbutamol/budesonide">Salbutamol/budesonide</a></li> <li><a href="/wiki/Savolitinib" title="Savolitinib">Savolitinib</a></li> <li><a href="/wiki/Saxagliptin" title="Saxagliptin">Saxagliptin</a></li> <li><a href="/wiki/Sebelipase_alfa" title="Sebelipase alfa">Sebelipase alfa</a></li> <li><a href="/wiki/Selumetinib" title="Selumetinib">Selumetinib</a></li> <li><a href="/wiki/Sodium_zirconium_cyclosilicate" title="Sodium zirconium cyclosilicate">Sodium zirconium cyclosilicate</a></li> <li><a href="/wiki/Tamoxifen" title="Tamoxifen">Tamoxifen</a></li> <li><a href="/wiki/Ticagrelor" title="Ticagrelor">Ticagrelor</a></li> <li><a href="/wiki/Tixagevimab/cilgavimab" title="Tixagevimab/cilgavimab">Tixagevimab/cilgavimab</a></li> <li><a href="/wiki/Trastuzumab_deruxtecan" title="Trastuzumab deruxtecan">Trastuzumab deruxtecan</a></li> <li><a href="/wiki/Vandetanib" title="Vandetanib">Vandetanib</a></li> <li><a href="/wiki/Oxford%E2%80%93AstraZeneca_COVID-19_vaccine" title="Oxford–AstraZeneca COVID-19 vaccine">Vaxzevria</a></li> <li><a class="mw-selflink selflink">Ximelagatran</a></li> <li><a href="/wiki/Zafirlukast" title="Zafirlukast">Zafirlukast</a></li> <li><a href="/wiki/Zolmitriptan" title="Zolmitriptan">Zolmitriptan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Predecessors and<br />acquired companies</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/Astra_AB" title="Astra AB">Astra AB</a></li> <li><a href="/wiki/Alexion_Pharmaceuticals" title="Alexion Pharmaceuticals">Alexion Pharmaceuticals</a></li> <li><a href="/wiki/Cambridge_Antibody_Technology" title="Cambridge Antibody Technology">Cambridge Antibody Technology</a></li> <li><a href="/wiki/MedImmune" title="MedImmune">MedImmune</a></li> <li><a href="/wiki/Zeneca" title="Zeneca">Zeneca</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">People</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/Tom_McKillop" title="Tom McKillop">Tom McKillop</a></li> <li><a href="/wiki/Louis_Schweitzer_(CEO)" class="mw-redirect" title="Louis Schweitzer (CEO)">Louis Schweitzer</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight: bold;"><div> <ul><li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, 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