dapagliflozin   

GtoPdb Ligand ID: 4594

Synonyms: BMS-512148 | Farxiga® | Forxiga®
dapagliflozin is an approved drug (EMA (2012), FDA (2014))
Comment: Dapagliflozin is a derivative of naturally occurring dihydrocholine glucoside. It acts as a sodium-glucose cotransporter 2 (SGLT-2) inhibitor. In addition to clinical efficacy in type 2 diabetes. Evidence from clinical trial suggests that dapagliflozin is of benefit in treating heart failure with or without type 2 diabetes as a comorbidity [3].
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 99.38
Molecular weight 408.13
XLogP 2.94
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CCOc1ccc(cc1)Cc1cc(ccc1Cl)C1OC(CO)C(C(C1O)O)O
Isomeric SMILES CCOc1ccc(cc1)Cc1cc(ccc1Cl)[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1
InChI Key JVHXJTBJCFBINQ-ADAARDCZSA-N
Classification
Compound class Natural product or derivative
Approved drug? Yes (EMA (2012), FDA (2014))
IUPAC Name
(2S,3R,4R,5S,6R)-2-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-6-(hydroxymethyl)oxane-3,4,5-triol
International Nonproprietary Names
INN number INN
8886 dapagliflozin
Synonyms
BMS-512148 | Farxiga® | Forxiga®
Database Links
CAS Registry No. 461432-26-8
ChEBI CHEBI:85078
ChEMBL Ligand CHEMBL429910
DrugCentral Ligand 4304
GtoPdb PubChem SID 178101315
PubChem CID 9887712
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Wikipedia Dapagliflozin