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CHEBI:85078 - dapagliflozin

Default Structure
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 Roles:
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
antiviral agent  A substance that destroys or inhibits replication of viruses.
sodium-glucose transport protein subtype 2 inhibitor  Any inhibitor that interferes with the action of sodium-glucose transport protein subtype 2.
anti-obesity agent  Any substance which is used to reduce or control weight.
Applications:
anti-arrhythmia drug  A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
hypoglycemic agent  A drug which lowers the blood glucose level.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
renoprotective agent  Any compound that is able to prevent damage to the kidneys.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
insulin-sensitizing drug  An agent which overcomes insulin resistance by activation of the peroxisome proliferator activated receptor gamma (PPAR-gamma).
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
ChEBI Ontology
Outgoing Relation(s)
dapagliflozin (CHEBI:85078) has role anti-arrhythmia drug (CHEBI:38070)
dapagliflozin (CHEBI:85078) has role anti-inflammatory agent (CHEBI:67079)
dapagliflozin (CHEBI:85078) has role anti-obesity agent (CHEBI:74518)
dapagliflozin (CHEBI:85078) has role antidepressant (CHEBI:35469)
dapagliflozin (CHEBI:85078) has role antihypertensive agent (CHEBI:35674)
dapagliflozin (CHEBI:85078) has role antineoplastic agent (CHEBI:35610)
dapagliflozin (CHEBI:85078) has role antiviral agent (CHEBI:22587)
dapagliflozin (CHEBI:85078) has role cardiovascular drug (CHEBI:35554)
dapagliflozin (CHEBI:85078) has role geroprotector (CHEBI:176497)
dapagliflozin (CHEBI:85078) has role hepatoprotective agent (CHEBI:62868)
dapagliflozin (CHEBI:85078) has role hypoglycemic agent (CHEBI:35526)
dapagliflozin (CHEBI:85078) has role insulin-sensitizing drug (CHEBI:50864)
dapagliflozin (CHEBI:85078) has role renoprotective agent (CHEBI:231911)
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
INNs  Source
dapagliflozinKEGG DRUG
dapagliflozinaWHO MedNet
dapagliflozineWHO MedNet
Synonyms  Source
(2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolChemIDplus
LYN-045ChEMBL
Brand Names  Source
BMS 512148ChemIDplus
BMS-512148ChemIDplus
Dapagliflozin component of br1019ChEMBL
Dapagliflozin component of qternChEMBL
Dapagliflozin component of qternmetChEMBL
Dapagliflozin component of qternmet dapaglifozinChEMBL
Manual XrefsDatabases
4304DrugCentral
D08897KEGG DRUG
DapagliflozinWikipedia
DB06292DrugBank
Registry NumbersSources
Reaxys:11966426Reaxys
CAS:461432-26-8KEGG DRUG
CAS:461432-26-8ChemIDplus
Citations