Rosiglitazone
SIGMA/R2408 - ≥98% (HPLC)
Synonym: Rosiglitazone; 5-
CAS Number: 122320-73-4
Empirical Formula (Hill Notation): C18H19N3O3S
Molecular Weight: 357.43
MDL Number: MFCD00871760
Linear Formula: C18H19N3O3S
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: R2408-10MG
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: R2408-50MG
| assay | ≥98% (HPLC) |
| form | powder |
| InChI | 1S/C18H19N3O3S/c1-21(16-4 |
| InChI key | YASAKCUCGLMORW-UHFFFAOYSA |
| originator | GlaxoSmithKline |
| Quality Level | 100  |
| SMILES string | CN(CCOc1ccc(CC2SC(=O)NC2= |
| solubility | DMSO: ≥10 mg/mL |
| storage temp. | 2-8°C |
| Application: | Rosiglitazone has been used: • as a medium constituent for adipocyte differentiation • in the cell proliferation assay in human colonic carcinoma cell lines • for Bcl-2-like protein 13 (Bcl2l13) expression in adipocytes • as a peroxisome proliferator-activated receptor gamma (PPARγ) ligand |
| Biochem/physiol Actions: | Potent agonist for PPARγ with an EC50 of 43 nM for the human receptor. |
| Biochem/physiol Actions: | Rosiglitazone is a potent agonist for PPARγ with an EC50 of 43 nM for the human receptor. It is antidiabetic, working as an insulin sensitizer by binding to the PPARγ receptors in fat cells and making the cells more responsive to insulin. |
| Features and Benefits: | This compound is a featured product for ADME Tox and Gene Regulation research. Discover more featured ADME Tox and Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm . |
| Features and Benefits: | This compound is featured on the AMPKs and Nuclear Receptors (PPARs) pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here . |
| Features and Benefits: | This compound was developed by GlaxoSmithKline . To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here . |
| General description: | Rosiglitazone is a member of the thiazolidinedione family. It effectively lowers glucose levels by enhancing the response of target cells to insulin, without causing increased stimulation and release of insulin by the pancreatic beta cells. Rosiglitazone functions by activating the nuclear peroxisome proliferator-activated (PPAR) receptor gamma, which plays a key role in regulating adipogenesis, glucose metabolism, and genetic networks. It exhibits high potency as a thiazolidinedione, with a binding affinity for PPAR-gamma that is 30-fold higher than pioglitazone. Furthermore, it increases insulin-stimulated IRS-1/2 in skeletal muscle and adipose tissue, leading to the expression of the GLUT4 glucose transporter. |
| Packaging: | 10, 50 mg in glass bottle |
| RIDADR | NONH for all modes of transport |
| WGK Germany | WGK 3 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥98% (HPLC); ≥98% (HPLC) |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352200 |