MCC-555

The peroxisome proliferator-activated receptor-gamma (PPARgamma) is the nuclear receptor responsible for transducing the therapeutic activity of the thiazolidinediones (TZDs), a group of structurally related synthetic agonists with antidiabetic actions in vivo. Rosiglitazone (BRL49653) is a prototypical TZD and has served as a reference compound for this class. MCC-555 is a structural homolog of rosiglitazone and the other TZDs. MCC-555 binds with about 1/10 the affinity of rosiglitazone to PPARgamma. Despite this, MCC-555 is a more potent antidiabetic agent in whole animal experiments than rosiglitazone and several other prototypic TZDs, the ED50 value in these experiments was 2.7 mg/kg for MCC-555 compared with 7.1 mg/kg for rosiglitazone. MCC-555 is therefore a unique new member of the TZD class and may be useful in differentiating some of the multiple activities attributed to this class of compounds.Formal Name: 5-[[6-[(2-fluorophenyl)methoxy]-2-naphthalenyl]methyl]-2,4-thiazolidinedione. CAS Number: 161600-01-7. Synonyms: Isaglitazone, Netoglitazone, RWJ 241947. Molecular Formula: C21H16FNO3S. Formula Weight: 381.4. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, DMSO:PBS (pH 7.2) (1:1): 1 mg/ml, Ethanol: 1 mg/ml. SMILES: FC1=CC=CC=C1COC2=CC(C=CC(CC3SC(NC3=O)=O)=C4)=C4C=C2. InChi Code: InChI=1S/C21H16FNO3S/c22-18-4-2-1-3-16(18)12-26-17-8-7-14-9-13(5-6-15(14)11-17)10-19-20(24)23-21(25)27-19/h1-9,11,19H,10,12H2,(H,23,24,25). InChi Key: PKWDZWYVIHVNKS-UHFFFAOYSA-N.