Rosiglitazone maleate , ≥99% , 155141-29-0

Synonym(s):
5-[[4-[2-(Methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione maleate salt;AMPK Signaling Activator X, 5-[4-(2-[methyl(pyridin-2-yl)amino]ethoxy)benzyl]thiazolidine-2,4-dione, BRL49653, Avandia, PPAR Agonist X, PPARγ Agonist IX;Rosiglitazone - CAS 155141-29-0 - Calbiochem

CAS NO.：155141-29-0

Empirical Formula: C22H23N3O7S

Molecular Weight: 473.5

MDL number: MFCD03427306

EINECS: 642-163-6

PRODUCT Properties

• Melting point: 235-240°C
• storage temp.: 2-8°C
• solubility: Soluble in DMSO (up to 50 mg/ml).
• pka: 6.1; 6.8(at 25℃)
• form: White powder
• color: White
• BCS Class: 1
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months
• InChIKey: HCDYSWMAMRPMST-NTCAYCPXSA-N
• CAS DataBase Reference: 155141-29-0(CAS DataBase Reference)

Description and Uses

Rosiglitazone maleate, belongs to a novel class of thiazolidine diones launched for the treatment of non-insulin-dependent diabetes mellitus (NIDDM), a disease characterized by a pancreatic β-cell defect and insulin resistance in the liver and peripheral tissues. The racemic base can be obtained by KnSvenagel condensation between 2, 4-thiazolidinedione and the corresponding 4-substituted benzaldehyde (itself prepared in 2 steps from 2-chloropyridine), followed by reduction of the benzylidene. Rosiglitazone was shown to be a potent agonist of peroxisome proliferator activated receptor-gamma (PPARgamma), a nuclear receptor involved in the differentiation of adipose tissue, without activating liver PPAR-alpha receptors. This activation of PPAR-gamma could mediate the down-regulation of leptin gene expression. In animal models, Rosiglitazone has been shown to normalize glucose metabolism and reduce the exogenous dose of insulin needed to achieve glycemic control. In patients with Type II diabetes, daily doses (4 or 8 mg) of Rosiglitazone significantly improved blood sugar control without affecting cardiac structure or function.

Thiazolidinediones (TZDs) are a group of structurally related peroxisome proliferator-activated receptor γ (PPARγ) agonists with antidiabetic actions in vivo. Rosiglitazone is a prototypical TZD that has served as a reference compound for this class. It is a potent and selective PPARγ ligand that binds to the PPARγ ligand-binding domain with a Kd value of 43 nM. It activates luciferase-based expression constructs PPARγ1 and PPARγ2 with EC50 values of approximately 30 nM and 100 nM, respectively. Rosiglitazone is active in vivo as an antidiabetic agent in the ob/ob mouse model, and has been used as an oral hypoglycemic agent in the treatment of type 2 diabetes in humans for many years.[Cayman Chemical]

Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H315-H319
• Precautionary statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
• Hazard Codes: Xi
• Risk Statements: 20/21/22-36/38
• Safety Statements: 24/25-37/39-26
• WGK Germany: 3