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).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: dabigatran etexilate

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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)anilino]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, 776
GtoPdb PubChem SID 178102997
PubChem CID 135565674
Search Google for chemical match using the InChIKey KSGXQBZTULBEEQ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KSGXQBZTULBEEQ
Search PubMed clinical trials dabigatran etexilate
Search PubMed titles dabigatran etexilate
Search PubMed titles/abstracts dabigatran etexilate
UniChem Compound Search for chemical match using the InChIKey KSGXQBZTULBEEQ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KSGXQBZTULBEEQ-UHFFFAOYSA-N
Wikipedia Dabigatran