Dabigatran
3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid
Molecular Identity
Dabigatran
3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acid
PubChem CID: 216210
Dabigatran is an aromatic amide obtained by formal condensation of the carboxy group of 2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl-1H-benzimidazole-5-carboxylic acid with the secondary amoino group of N-pyridin-2-yl-beta-alanine. The active metabolite of the prodrug dabigatran etexilate, it acts as an anticoagulant which is used for the prevention of stroke and systemic embolism. It has a role as an anticoagulant, an EC 3.4.21.5 (thrombin) inhibitor and an EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor. It is a member of benzimidazoles, a beta-alanine derivative, a member of pyridines, a carboxamidine and an aromatic amide.
2D Structure
Properties
C25H25N7O3
Molecular Formula
471.50
Molecular Weight
g/mol
471.2019
Exact Mass
Da
1.7
XLogP
Drug-like (Lipinski: < 5)
150
TPSA
May have limited oral absorption
4
H-Bond Donors
7
H-Bond Acceptors
757
Complexity
SMILES
Canonical SMILES
SMILES: CN1C2=C(C=C(C=C2)C(=O)N(CCC(=O)O)C3=CC=CC=N3)N=C1CNC4=CC=C(C=C4)C(=N)NIsomeric SMILES
SMILES: CN1C2=C(C=C(C=C2)C(=O)N(CCC(=O)O)C3=CC=CC=N3)N=C1CNC4=CC=C(C=C4)C(=N)NSynonyms(20)
Dabigatran211914-51-1BIBR-953Pradaxa (dabigatran)BIBR 953 ZW3-[[2-[(4-carbamimidoylanilino)methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acidI0VM4M70GCBIBR-953-ZWCHEBI:70752DTXSID50175419N-((2-((p-Amidinoanilino)methyl)-1-methyl-5-benzimidazolyl)carbonyl)-N-2-pyridyl-beta-alanine3-[[2-[[(4-carbamimidoylphenyl)amino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoic acidbeta-Alanine, N-((2-(((4-(aminoiminomethyl)phenyl)amino)methyl)-1-methyl-1H-benzimidazol-5-yl)carbonyl)-N-2-pyridinyl-3-((2-(((4-carbamimidoylphenyl)amino)methyl)-1-methylbenzimidazole-5-carbonyl)-pyridin-2-ylamino)propanoic acid3-((2-((4-carbamimidoylanilino)methyl)-1-methylbenzimidazole-5-carbonyl)-pyridin-2-ylamino)propanoic acid
Data from PubChem (NCBI)
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