CHEBI:70752 - dabigatran

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ChEBI Name dabigatran
ChEBI ID CHEBI:70752
Definition 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-β-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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H25N7O3
Net Charge 0
Average Mass 471.51110
Monoisotopic Mass 471.202
InChI InChI=1S/C25H25N7O3/c1-31-20-10-7-17(25(35)32(13-11-23(33)34)21-4-2-3-12-28-21)14-19(20)30-22(31)15-29-18-8-5-16(6-9-18)24(26)27/h2-10,12,14,29H,11,13,15H2,1H3,(H3,26,27)(H,33,34)
InChIKey YBSJFWOBGCMAKL-UHFFFAOYSA-N
SMILES Cn1c(CNc2ccc(cc2)C(N)=N)nc2cc(ccc12)C(=O)N(CCC(O)=O)c1ccccn1
Roles Classification
Biological Role(s): EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor
An EC 1.10.99.* (oxidoreductases acting on diphenols and related substances as donors, other acceptors) inhibitor that interferes with the action of ribosyldihydronicotinamide dehydrogenase (quinone), EC 1.10.99.2.
EC 3.4.21.5 (thrombin) inhibitor
An EC 3.4.21.* (serine endopeptidase) inhibitor that interferes with the action of thrombin (EC 3.4.21.5).
Application(s): anticoagulant
An agent that prevents blood clotting.
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ChEBI Ontology
Outgoing dabigatran (CHEBI:70752) has role anticoagulant (CHEBI:50249)
dabigatran (CHEBI:70752) has role EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor (CHEBI:77020)
dabigatran (CHEBI:70752) has role EC 3.4.21.5 (thrombin) inhibitor (CHEBI:65232)
dabigatran (CHEBI:70752) is a β-alanine derivative (CHEBI:22823)
dabigatran (CHEBI:70752) is a aromatic amide (CHEBI:62733)
dabigatran (CHEBI:70752) is a benzimidazoles (CHEBI:22715)
dabigatran (CHEBI:70752) is a carboxamidine (CHEBI:35359)
dabigatran (CHEBI:70752) is a pyridines (CHEBI:26421)
Incoming N-(4-aminobutyl)dabigatranamide (CHEBI:73197) has functional parent dabigatran (CHEBI:70752)
dabigatran etexilate (CHEBI:70746) has functional parent dabigatran (CHEBI:70752)
INN Source
dabigatran KEGG DRUG
Manual Xrefs Databases
D09707 KEGG DRUG
Dabigatran Wikipedia
US2006222640 Patent
US2008015176 Patent
US6087380 Patent
WO2004014894 Patent
WO2006004575 Patent
WO2006103206 Patent
WO2008009638 Patent
WO2008009639 Patent
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Registry Numbers Types Sources
211914-51-1 CAS Registry Number KEGG DRUG
9168207 Reaxys Registry Number Reaxys
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Last Modified
17 January 2014