has role ximelagatran (hydroxylamine form) secondary carboxamide tertiary carboxamide ethyl ester azetidines melagatran anticoagulant prodrug secondary amino compound serine protease inhibitor ximelagatran H 376/95 PMID:16123912 PMID:28338626 Drug_Central:2852 ximelagatranum Exanta ethyl N-{(1R)-1-cyclohexyl-2-[(2S)-2-{[4-(N'-hydroxycarbamimidoyl)benzyl]carbamoyl}azetidin-1-yl]-2-oxoethyl}glycinate Exarta Wikipedia:Ximelagatran PMID:15487959 PMID:16767816 ximelagatran (oxime form) PMID:16106594 CAS:192939-46-1 0 PMID:16511607 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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage. KEGG:D01981 H 37695 Reaxys:14559655 CHEBI:65172 PMID:16084146 PMID:12846595 ximelagatran PMID:20020269 C24H35N5O5 PMID:19028773 chebi_ontology 473.56520 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 PMID:17636192 [H][C@]1(CCN1C(=O)[C@H](NCC(=O)OCC)C1CCCCC1)C(=O)NCc1ccc(cc1)C(N)=NO DrugBank:DB04898 ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate ZXIBCJHYVWYIKI-PZJWPPBQSA-N PMID:17319469 H 376-95 473.26382 EC 3.4.21.5 (thrombin) inhibitor amidoxime