CHEBI:85078 - dapagliflozin

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ChEBI Name dapagliflozin
ChEBI ID CHEBI:85078
Definition A C-glycosyl comprising β-D-glucose in which the anomeric hydroxy group is replaced by a 4-chloro-3-(4-ethoxybenzyl)phenyl group. Used (in the formo f its propanediol monohydrate) to improve glycemic control, along with diet and exercise, in adults with type 2 diabetes.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H25ClO6
Net Charge 0
Average Mass 408.87300
Monoisotopic Mass 408.134
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
InChIKey JVHXJTBJCFBINQ-ADAARDCZSA-N
SMILES CCOc1ccc(Cc2cc(ccc2Cl)[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc1
Roles Classification
Biological Role(s): sodium-glucose transport protein subtype 2 inhibitor
An inhibitor that interferes with the action of sodium-glucose transport protein subtype 2.
Application(s): hypoglycemic agent
A drug which lowers the blood glucose level.
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ChEBI Ontology
Outgoing dapagliflozin (CHEBI:85078) has role hypoglycemic agent (CHEBI:35526)
dapagliflozin (CHEBI:85078) has role sodium-glucose transport protein subtype 2 inhibitor (CHEBI:73273)
dapagliflozin (CHEBI:85078) is a C-glycosyl compound (CHEBI:20857)
dapagliflozin (CHEBI:85078) is a aromatic ether (CHEBI:35618)
dapagliflozin (CHEBI:85078) is a organochlorine compound (CHEBI:36683)
Incoming dapagliflozin propanediol monohydrate (CHEBI:85079) has part dapagliflozin (CHEBI:85078)
IUPAC Name
(1S)-1,5-anhydro-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-D-glucitol
INN Source
dapagliflozin KEGG DRUG
Synonym Source
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol ChemIDplus
Brand Names Sources
BMS 512148 ChemIDplus
BMS-512148 ChemIDplus
Database Links Databases
4304 DrugCentral
D08897 KEGG DRUG
Dapagliflozin Wikipedia
DB06292 DrugBank
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Registry Numbers Types Sources
11966426 Reaxys Registry Number Reaxys
461432-26-8 CAS Registry Number ChemIDplus
461432-26-8 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017