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Coagulation defect	3B10.0	Withdrawn from market	[1]

Therapeutic Class

Anticoagulants

Affected Organisms

Humans and other mammals

ATC Code

B01AE05: Ximelagatran

B01AE: Direct thrombin inhibitors

B01A: ANTITHROMBOTIC AGENTS

B01: ANTITHROMBOTIC AGENTS

B: BLOOD AND BLOOD FORMING ORGANS

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

473.6

Logarithm of the Partition Coefficient (xlogp)

2.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Bioavailability: The bioavailability of drug is 20% []
Half-life: The concentration or amount of drug in body reduced by one-half in 3 - 5 hours [2]
Metabolism: The drug is metabolized via the liver []

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: CHEMBL522038
CAS Number: 192939-46-1
UNII: 49HFB70472
DrugBank ID: DB04898
TTD ID: D0JQ7Y
VARIDT ID: DR01404
INTEDE ID: DR1720

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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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	[3]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[4]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2C9 (CYP2C9)_{Main DME}	DE5IED8	CP2C9_HUMAN	Substrate	[5]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Prothrombin (F2)	OTNFSM49	THRB_HUMAN	Protein Interaction/Cellular Processes	[6]

Molecular Interaction Atlas (MIA)

MIA Detail

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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)

MEA Detail

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6381).
2	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	Ximelagatran increases membrane fluidity and changes membrane lipid composition in primary human hepatocytes. Toxicol In Vitro. 2009 Oct;23(7):1305-10.
4	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
5	Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet. 2005;44(12):1227-46.
6	Long-term treatment with ximelagatran, an oral direct thrombin inhibitor, persistently reduces the coagulation activity after a myocardial infarction. J Thromb Haemost. 2005 Oct;3(10):2245-53. doi: 10.1111/j.1538-7836.2005.01557.x.