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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H17N3O4S
Molecular Weight 395.432
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BALAGLITAZONE, (R)-

SMILES

CN1C(=O)C2=C(C=CC=C2)N=C1COC3=CC=C(C[C@H]4SC(=O)NC4=O)C=C3

InChI

InChIKey=IETKPTYAGKZLKY-MRXNPFEDSA-N
InChI=1S/C20H17N3O4S/c1-23-17(21-15-5-3-2-4-14(15)19(23)25)11-27-13-8-6-12(7-9-13)10-16-18(24)22-20(26)28-16/h2-9,16H,10-11H2,1H3,(H,22,24,26)/t16-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H17N3O4S
Molecular Weight 395.432
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Balaglitazone, also known as DRF-2593; NNC-61-0645; NNC-61-2344; NN-2344; NNC-610645; NNC-612344, is an agonist of peroxisome proliferator-activated receptor (PPAR)γ. Balaglitazone plays an important role in the regulation of insulin, triglycerides and lipid metabolism. It is an attractive target for the therapy of Type II Diabetes. Balaglitazone is a partial agonist of PPARγ. It has showed potent effects on lowering blood glucose in various animal models. Balaglitazone passed phase III clinical trial for the treatment of type 2 diabetes. However, Dr. Reddy's Laboratories decided to terminate further clinical development of balaglitazone. Balaglitazone exists as two enantiomers: BALAGLITAZONE, (S)- and BALAGLITAZONE, (R)-. A capillary electrophoresis method for separation of a racemic mixture of glitazone compounds has being used. The method separated the R and S enantiomers of balaglitazone, and showed that the samples contained an equal (50:50) quantity of the enantiomers as a mixture. The Rs for the separations were 3.5 for balaglitazone enantiomers.

Approval Year

TargetsConditions

Conditions

PubMed

PubMed

TitleDatePubMed
Generic, highly selective and robust capillary electrophoresis method for separation of a racemic mixture of glitazone compounds.
2004 Sep 17
Balaglitazone: a second generation peroxisome proliferator-activated receptor (PPAR) gamma (γ) agonist.
2012 Feb
Patents

Patents

Sample Use Guides

One arm balaglitazone 10mg, one arm balaglitazone 20mg, orally taken once daily.
Route of Administration: Oral
In a cell-based assay using HEK293 cells transfected with fused PPARγ, treatment of balaglitazone showed sigmoid activation with an EC50 value of 1.35uM. When combined with rosiglitazone, balaglitazone at increased concentrations resulted in the reduction of rosiglitazone’s activity to the level of balaglitazone alone at concentration of 100 nM
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:09:29 GMT 2023
Edited
by admin
on Sat Dec 16 09:09:29 GMT 2023
Record UNII
2U9J272649
Record Status Validated (UNII)
Record Version
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Name Type Language
BALAGLITAZONE, (R)-
Common Name English
2,4-THIAZOLIDINEDIONE, 5-((4-((3,4-DIHYDRO-3-METHYL-4-OXO-2-QUINAZOLINYL)METHOXY)PHENYL)METHYL), (R)-
Systematic Name English
Code System Code Type Description
PUBCHEM
76968728
Created by admin on Sat Dec 16 09:09:29 GMT 2023 , Edited by admin on Sat Dec 16 09:09:29 GMT 2023
PRIMARY
FDA UNII
2U9J272649
Created by admin on Sat Dec 16 09:09:29 GMT 2023 , Edited by admin on Sat Dec 16 09:09:29 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER