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
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)
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.