loading...| Preferred Name |
ximelagatran |
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| Synonyms |
ximelagatranum C24H35N5O5 H 376-95 Exanta ethyl 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-[({4-[(Z)-N'-hydroxycarbamimidoyl]phenyl}methyl)carbamoyl]azetidin-1-yl]-2-oxoethyl]amino}acetate H 376/95 ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate Exarta ximelagatran ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate H 37695 |
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| ID |
http://purl.obolibrary.org/obo/CHEBI_65172 |
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| ATCCode |
B01AE05 |
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| binds | ||
| CASRN |
192939-46-1 |
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| DBBrand |
exarta exanta |
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| DBSynonym |
h 376/95 |
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| Definition |
A member of the class of azetidines that is melagatran in which the carboxylic acid group has been converted to the corresponding ethyl ester and in which the amidine group has been converted to the corresponding amidoxime. A prodrug for melagatran, ximelagatran was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage. Ximelagatran (Exanta? or Exarta?, H 376/95) is an anticoagulant that has been investigated extensively as a replacement for warfarin that would overcome the problematic dietary, drug interaction, and monitoring issues associated with warfarin therapy. In 2006, its manufacturer AstraZeneca announced that it would not attempt to market ximelagatran after reports of hepatotoxicity (liver damage) during trials, and to discontinue its distribution in countries where the drug had been approved. |
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| has pharmacological target | ||
| has role |
http://purl.obolibrary.org/obo/CHEBI_50249 http://purl.obolibrary.org/obo/CHEBI_65232 |
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| InChI |
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 |
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| InChIKey |
InChIKey=ZXIBCJHYVWYIKI-PZJWPPBQSA-N |
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| inhibits | ||
| is metabolised by | ||
| is substrate of | ||
| label |
ximelagatran |
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| prefixIRI |
obo2:CHEBI_65172 |
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| prefLabel |
ximelagatran |
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| SMILES |
[H][C@]1(CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C(=O)NCc1ccc(cc1)C(N)=NO CCOC(=O)CN[C@@H](C(=O)N1CC[C@H]1C(=O)NCC1=CC=C(C=C1)C(\N)=N\O)C1CCCCC1 |
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| Synonym |
ximelagatranum C24H35N5O5 H 376-95 Exanta ethyl 2-{[(1R)-1-cyclohexyl-2-[(2S)-2-[({4-[(Z)-N'-hydroxycarbamimidoyl]phenyl}methyl)carbamoyl]azetidin-1-yl]-2-oxoethyl]amino}acetate H 376/95 ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate Exarta ximelagatran ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate H 37695 |
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| xref |
SUBMITTER:D01981 CiteXplore:12846595 CASRN:192939-46-1 CiteXplore:16084146 CiteXplore:19028773 PubChem Substance:46509040 ChemSpider:7848559 CiteXplore:16511607 CiteXplore:17636192 CiteXplore:20020269 CiteXplore:17319469 Reaxys:14559655 CiteXplore:16123912 PharmGKB:PA161748474 SUBMITTER:DB04898 Wikipedia:http://en.wikipedia.org/wiki/Ximelagatran CiteXplore:16106594 PubChem Compound:9574101 CiteXplore:15487959 Wikipedia:Ximelagatran ChEMBL:578003 CiteXplore:16767816 |
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| subClassOf |