Details of the Drug

General Information of Drug (ID: DMABRJL)

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
Indication
Disease Entry ICD 11 Status REF
Coagulation defect 3B10.0 Withdrawn from market [1], [2]
Therapeutic Class
Anticoagulants
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 473.6
Topological Polar Surface Area (xlogp) 2.2
Rotatable Bond Count (rotbonds) 11
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Bioavailability
The bioavailability of drug is 20% [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 3 - 5 hours [4]
Metabolism
The drug is metabolized via the liver [3]
Chemical Identifiers
Formula
C24H35N5O5
IUPAC Name
ethyl 2-[[(1R)-1-cyclohexyl-2-[(2S)-2-[[4-[(Z)-N'-hydroxycarbamimidoyl]phenyl]methylcarbamoyl]azetidin-1-yl]-2-oxoethyl]amino]acetate
Canonical SMILES
CCOC(=O)CN[C@H](C1CCCCC1)C(=O)N2CC[C@H]2C(=O)NCC3=CC=C(C=C3)/C(=N/O)/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
Cross-matching ID
PubChem CID
9574101
ChEBI ID
CHEBI:136702
CAS Number
192939-46-1
DrugBank ID
DB04898
TTD ID
D0JQ7Y
VARIDT ID
DR01404
INTEDE ID
DR1720

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Coagulation factor IIa (F2) TT6L509 THRB_HUMAN Inhibitor [5], [6]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9)
Main DME 		DE5IED8 CP2C9_HUMAN Substrate [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Coagulation defect
ICD Disease Classification 3B10.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
P-glycoprotein 1 (ABCB1) DTP P-GP 7.23E-01 -8.20E-02 -3.22E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 9.09E-01 -9.26E-02 -3.68E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

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