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Details

Stereochemistry RACEMIC
Molecular Formula C24H24N4O5S.H2O4S
Molecular Weight 578.615
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOBEGLITAZONE SULFATE

SMILES

OS(O)(=O)=O.COC1=CC=C(OC2=CC(=NC=N2)N(C)CCOC3=CC=C(CC4SC(=O)NC4=O)C=C3)C=C1

InChI

InChIKey=IFBYQAMJTBOBHB-UHFFFAOYSA-N
InChI=1S/C24H24N4O5S.H2O4S/c1-28(21-14-22(26-15-25-21)33-19-9-7-17(31-2)8-10-19)11-12-32-18-5-3-16(4-6-18)13-20-23(29)27-24(30)34-20;1-5(2,3)4/h3-10,14-15,20H,11-13H2,1-2H3,(H,27,29,30);(H2,1,2,3,4)

HIDE SMILES / InChI

Description

Lobeglitazone (trade name Duvie; Chong Kun Dang Pharmaceutical Corporation) was developed as effective and safe antidiabetic TZD drug. Lobeglitazone is a peroxisome proliferator-activated receptor-γ agonist. Lobeglitazone was conceptually designed by modification of the rosiglitazone structure with a substituted pyrimidine. Lobeglitazone has a p-methoxyphenoxy group at the 4-position of the pyrimidine moiety. Lobeglitazone showed more potent activity than the reference compounds (pioglitazone and rosiglitazone) with an EC50 value of 0.018 uM in a type 2 diabetes animal model, which is 16 times lower than pioglitazone (EC50 0.30 uM). Lobeglitazone exhibited similar efficacy profiles in glycemic control and lipid modulation to pioglitazone, but with a 30 times smaller dose in clinical studies. Lobeglitazone displays 12 times higher affinity to PPARγ than rosiglitazone and pioglitazone. Lobeglitazone acts as an insulin sensitizer by binding and activating Peroxisome Proliferator-Activated Receptors (PPAR) gamma within fat cells. By promoting the binding of insulin at fat cells, lobeglitazone has been shown to reduce blood sugar levels, lower hemoglobain A1C (HbA1C) levels, and improve lipid and liver profiles. Lobeglitazone was approved by the Ministry of Food and Drug Safety (Korea) in 2013. Lobeglitazone is not approved for use by either the Food and Drug Administration (USA), Health Canada, or by the European Medicines Agency for use in the management of diabetes.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Diabetes Mellitus, Type 2: 0.5 mg/tablet, orally, 1 tablet once daily for 24 weeks or 52 weeks
Route of Administration: Oral