Ximelagatran
ethyl 2-[[(1R)-1-cyclohexyl-2-[(2S)-2-[[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methylcarbamoyl]azetidin-1-yl]-2-oxoethyl]amino]acetate
Molecular Identity
Ximelagatran
ethyl 2-[[(1R)-1-cyclohexyl-2-[(2S)-2-[[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methylcarbamoyl]azetidin-1-yl]-2-oxoethyl]amino]acetate
PubChem CID: 9574101
Ximelagatran is 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was the first orally available direct thrombin inhibitor to be brought to market as an anticoagulant, but was withdrawn in 2006 following reports of it causing liver damage. It has a role as an anticoagulant, a prodrug, a serine protease inhibitor and an EC 3.4.21.5 (thrombin) inhibitor. It is a secondary carboxamide, a tertiary carboxamide, an ethyl ester, a carboxamide, a member of azetidines, a secondary amino compound and an amidoxime. It is functionally related to a melagatran. It is a tautomer of a ximelagatran (hydroxylamine form).
2D Structure
Properties
C24H35N5O5
Molecular Formula
473.60
Molecular Weight
g/mol
473.2638
Exact Mass
Da
2.2
XLogP
Drug-like (Lipinski: < 5)
146
TPSA
May have limited oral absorption
4
H-Bond Donors
7
H-Bond Acceptors
731
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Ximelagatran192939-46-1H 376/95xi-melagatranH 376-95ximelagatranumH 37695Exanta (proposed)DTXSID5049075CHEBI:65172Glycine, N-((1)1-cyclohexyl-2-((2)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl esterDTXCID502900149HFB70472glycine, N-((1R)1-cyclohexyl-2-((2S)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl esterH-376/95
Data from PubChem (NCBI)
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Trials and conditions connected to Ximelagatran
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