dapagliflozin   Click here for help

GtoPdb Ligand ID: 4594

Synonyms: BMS-512148 | Farxiga® | Forxiga®
Approved drug PDB Ligand
dapagliflozin is an approved drug (EMA (2012), FDA (2014))
Compound class: Synthetic organic
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 [7].

SARS-CoV-2 and COVID-19: Based on the cardio- and renoprotective benefits of dapagliflozin in T2DM patients, it was evaluated vs. placebo in 1250 hospitalised COVID-19 patients (NCT04350593) [4], to determine if it would provide similar protection from organ damage caused by SARS-CoV-2 infection. The drug treatment effected a non-significant reduction in the risk of organ failure or death [5]. Subsequent to this finding, another approved SGLT2 inhibitor empagliflozin was added to the RECOVERY trial.
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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA (2012), FDA (2014))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
8886 dapagliflozin
Synonyms Click here for help
BMS-512148 | Farxiga® | Forxiga®
Database Links Click here for help
CAS Registry No. 461432-26-8
ChEMBL Ligand CHEMBL429910
DrugCentral Ligand 4304
GtoPdb PubChem SID 178101315
PubChem CID 9887712
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Wikipedia Dapagliflozin