Drug Information

General Information
Drug ID
DR01404
Drug Name
Ximelagatran
Synonyms
Exanta; Exarta; H 376/95; Ximelagatran [USAN:INN]; 192939-46-1; H 376-95; H 37695; Glycine, N-((1)1-cyclohexyl-2-((2)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-, ethyl ester; NCGC00183598-01; Ethyl (((1R)-1-cyclohexyl-2-((2S)-2-((4-(hydroxycarbamimidoyl)benzyl)carbamoyl)azetidin-1-yl-2-oxoethyl)amino)acetate; Glycine, N-((1R)-1-cyclohexyl-2-((2S)-2-((((4-(hydroxyamino)iminomethyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)-2-oxoethyl)-, ethyl ester; H 376 95; Exanta (TN); Exarta (TN); Xi-melagatran; H-376/95; Ximelagatran (JAN/USAN/INN); Glycine, N-((1)1-cyclohexyl-2-((2)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl ester; Glycine, N-((1R)1-cyclohexyl-2-((2S)-((((4-(amino(hydroxyimino)methyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)2-oxoethyl)-ethyl ester; Glycine, N-((1R)-1-cyclohexyl-2-((2S)-2-((((4-((hydroxyamino)iminomethyl)phenyl)methyl)amino)carbonyl)-1-azetidinyl)-2-oxoethyl)-, ester ester; H376/95
Drug Type
Small molecular drug
Indication Discovery agent [ICD11:N.A.] Withdrawn [1]
Therapeutic Class
Anticoagulants
Structure
3D MOL 2D MOL
Formula
C24H35N5O5
Canonical SMILES
CCOC(=O)CNC(C1CCCCC1)C(=O)N2CCC2C(=O)NCC3=CC=C(C=C3)C(=NO)N
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
InChIKey
ZXIBCJHYVWYIKI-PZJWPPBQSA-N
CAS Number
CAS 192939-46-1
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
XLogP
2.2
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
TTD Drug ID
D0JQ7Y
DT(s) Transporting This Drug P-GP Transporter Info P-glycoprotein 1 Substrate [2]
References
1 ClinicalTrials.gov (NCT00206063) Long Term Open Follow-up With H376/95 vs. Warfarin. U.S. National Institutes of Health.
2 Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.

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