Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1720)
Drug Name
Ximelagatran
Prodrug Info Ximelagatran is the prodrug of OH-melagatran
Synonyms
Ximelagatran; Ximelagatran [USAN:INN]; Glycine, N-((1)1-cyclohexyl-2-((2)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-, ethyl ester; Exanta; Exarta; 192939-46-1; Glycine, N-((1R)-1-cyclohexyl-2-((2S)-2-((((4-(hydroxyamino)iminomethyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)-2-oxoethyl)-, ethyl ester; H 376-95; H 376/95; H 37695; NCGC00183598-01
Indication Coagulation defect [ICD11: 3B10] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 473.6 Topological Polar Surface Area 146
Heavy Atom Count 34 Rotatable Bond Count 11
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
9574101
PubChem SID
7849043 ; 12015148 ; 14785299 ; 14858738 ; 14883129 ; 14883130 ; 23997623 ; 44712163 ; 46509040 ; 49973459 ; 57372958 ; 79267685 ; 87225336 ; 124894453 ; 134338458 ; 135106952 ; 137002923 ; 137726685 ; 140950577 ; 142578696 ; 144207182 ; 160645186 ; 160967831 ; 164235510 ; 164766173 ; 180370510 ; 226396762 ; 226396763 ; 233586233 ; 251971104
ChEBI ID
CHEBI:65172
CAS Number
192939-46-1
TTD Drug ID
D0JQ7Y
Formula
C24H35N5O5
Canonical SMILES
CCOC(=O)CNC(C1CCCCC1)C(=O)N2CCC2C(=O)NCC3=CC=C(C=C3)C(=NO)N
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
InChIKey
ZXIBCJHYVWYIKI-PZJWPPBQSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Ethyl-melagatran DM016340
71763914
Reduction - Reduction 1 [3]
OH-melagatran DM015556
9889723
Hydrolysis - Hydrolysis 1 [3]
Melagatran DM015243
183797
Hydrolysis - Hydrolysis 2 [3]
Melagatran DM015243
183797
Reduction - Reduction 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009640 Ximelagatran OH-melagatran Hydrolysis - Hydrolysis Unclear [3]
MR009642 Ximelagatran Ethyl-melagatran Reduction - Reduction Unclear [3]
MR009643 Ethyl-melagatran Melagatran Hydrolysis - Hydrolysis Unclear [3]
MR009641 OH-melagatran Melagatran Reduction - Reduction Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
References
1 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
2 Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet. 2005;44(12):1227-46.
3 Biliary excretion of ximelagatran and its metabolites and the influence of erythromycin following intraintestinal administration to healthy volunteers

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