has role has attribute value has attribute anticoagulant prodrug organic molecular entity serine protease inhibitor ximelagatran 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 into 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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage. CAS:192939-46-1 CHEBI:65172 DrugBank:DB04898 Drug_Central:2852 Exanta Exarta H 376-95 H 376/95 H 37695 PMID:12846595 PMID:15487959 PMID:16084146 PMID:16106594 PMID:16123912 PMID:16511607 PMID:16767816 PMID:17319469 PMID:17636192 PMID:19028773 PMID:20020269 PMID:28338626 Reaxys:14559655 ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate ximelagatran ximelagatran (oxime form) ximelagatranum EC 3.4.21.5 (thrombin) inhibitor drug liver toxicity Most-DILI-Concern