dabigatran etexilate   Click here for help

GtoPdb Ligand ID: 6379

Synonyms: BIBR 1048 | Pradaxa®
Approved drug
dabigatran etexilate is an approved drug (EMA (2008), FDA (2010))
Compound class: Synthetic organic
Comment: Prodrug metabolised to the active drug dabigatran.
Marketed formulations contain dabigatran etexilate mesilate (PubChem CID 10439877).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 2
Rotatable bonds 19
Topological polar surface area 154.03
Molecular weight 627.32
XLogP 5.72
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCOC(=O)N=C(c1ccc(cc1)NCc1nc2c(n1C)ccc(c2)C(=O)N(c1ccccn1)CCC(=O)OCC)N
Isomeric SMILES CCCCCCOC(=O)/N=C(/c1ccc(cc1)NCc1nc2c(n1C)ccc(c2)C(=O)N(c1ccccn1)CCC(=O)OCC)\N
InChI InChI=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)
InChI Key KSGXQBZTULBEEQ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA (2008), FDA (2010))
Is prodrug? Yes
Active form dabigatran
IUPAC Name Click here for help
ethyl 3-[[2-[[[4-(N'-hexoxycarbonylcarbamimidoyl)phenyl]amino]methyl]-1-methylbenzimidazole-5-carbonyl]-pyridin-2-ylamino]propanoate
International Nonproprietary Names Click here for help
INN number INN
8028 dabigatran etexilate
Synonyms Click here for help
BIBR 1048 | Pradaxa®
Database Links Click here for help
CAS Registry No. 211915-06-9
ChEMBL Ligand CHEMBL539697
DrugBank Ligand DB06695
DrugCentral Ligand 776
GtoPdb PubChem SID 178102997
PubChem CID 6445226
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Wikipedia Dabigatran