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CHEBI:70746 - dabigatran etexilate

ChEBI IDCHEBI:70746
ChEBI Namedabigatran etexilate
Stars
DefinitionAn aromatic amide obtained by formal condensation of the carboxy group of 2-{[(4-{N'-[(hexyloxy)carbonyl]carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazole-5-carboxylic acid with the secondary amino group of ethyl N-pyridin-2-yl-β-alaninate. A prodrug for dabigatran, a thrombin inhibitor and anticoagulant which is used for the prevention of stroke and systemic embolism.
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC34H41N7O5
Net Charge0
Average Mass627.746
Monoisotopic Mass627.31692
SMILESCCCCCCOC(=O)/N=C(/N)c1ccc(NCc2nc3cc(C(=O)N(CCC(=O)OCC)c4ccccn4)ccc3n2C)cc1
InChIInChI=1S/C34H41N7O5/c1-4-6-7-10-21-46-34(44)39-32(35)24-12-15-26(16-13-24)37-23-30-38-27-22-25(14-17-28(27)40(30)3)33(43)41(20-18-31(42)45-5-2)29-11-8-9-19-36-29/h8-9,11-17,19,22,37H,4-7,10,18,20-21,23H2,1-3H3,(H2,35,39,44)
InChIKeyKSGXQBZTULBEEQ-UHFFFAOYSA-N
Roles Classification
Biological Role:
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).
Applications:
anticoagulant  An agent that prevents blood clotting.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
dabigatran etexilate (CHEBI:70746) has functional parent dabigatran (CHEBI:70752)
dabigatran etexilate (CHEBI:70746) has role anticoagulant (CHEBI:50249)
dabigatran etexilate (CHEBI:70746) has role EC 3.4.21.5 (thrombin) inhibitor (CHEBI:65232)
dabigatran etexilate (CHEBI:70746) has role prodrug (CHEBI:50266)
dabigatran etexilate (CHEBI:70746) is a aromatic amide (CHEBI:62733)
dabigatran etexilate (CHEBI:70746) is a benzimidazoles (CHEBI:22715)
dabigatran etexilate (CHEBI:70746) is a carboxamidine (CHEBI:35359)
dabigatran etexilate (CHEBI:70746) is a carboxylic ester (CHEBI:33308)
dabigatran etexilate (CHEBI:70746) is a pyridines (CHEBI:26421)
dabigatran etexilate (CHEBI:70746) is a β-alanine derivative (CHEBI:22823)
dabigatran etexilate (CHEBI:70746) is conjugate base of dabigatran etexilate(1+) (CHEBI:70751)
Incoming Relation(s)
dabigatran etexilate(1+) (CHEBI:70751) is conjugate acid of dabigatran etexilate (CHEBI:70746)
IUPAC Name 
ethyl N-[(2-{[(4-{N'-[(hexyloxy)carbonyl]carbamimidoyl}phenyl)amino]methyl}-1-methyl-1H-benzimidazol-5-yl)carbonyl]-N-pyridin-2-yl-β-alaninate
INN  Source
dabigatran etexilateKEGG DRUG
Manual XrefsDatabases
D07144KEGG DRUG
WO2012077136Patent
US2011275824Patent
WO2007047608Patent
HMDB0015641HMDB
WO2011061080Patent
WO2012027543Patent
776DrugCentral
Registry NumbersSources
Reaxys:15496119Reaxys
CAS:211915-06-9KEGG DRUG
CAS:211915-06-9ChemIDplus
Citations