EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:85078 - dapagliflozin

ChEBI IDCHEBI:85078
ChEBI Namedapagliflozin
Stars
DefinitionA 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 form of its propanediol monohydrate) to improve glycemic control, along with diet and exercise, in adults with type 2 diabetes.
Last Modified17 January 2024
SubmitterSteve
DownloadsMolfile
FormulaC21H25ClO6
Net Charge0
Average Mass408.878
Monoisotopic Mass408.13397
SMILESCCOc1ccc(Cc2cc([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)cc1
InChIInChI=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
InChIKeyJVHXJTBJCFBINQ-ADAARDCZSA-N
Wikipedia
Roles Classification
Biological Role:
sodium-glucose transport protein subtype 2 inhibitor  Any inhibitor that interferes with the action of sodium-glucose transport protein subtype 2.
Application:
hypoglycemic agent  A drug which lowers the blood glucose level.
ChEBI Ontology
Outgoing Relation(s)
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 monochlorobenzenes (CHEBI:83403)
Incoming Relation(s)
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
dapagliflozinKEGG DRUG
Synonym  Source
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolChemIDplus
Brand Names  Source
BMS 512148ChemIDplus
BMS-512148ChemIDplus
Manual XrefsDatabases
D08897KEGG DRUG
DapagliflozinWikipedia
DB06292DrugBank
4304DrugCentral
Registry NumbersSources
Reaxys:11966426Reaxys
CAS:461432-26-8KEGG DRUG
CAS:461432-26-8ChemIDplus
Citations