Name | 2-chloro-5-nitro-N-phenylbenzamide |
Synonyms | GW9662 CS-762 GW 9662 GW 9662 TIMTEC-BB SBB006523 2-CHLORO-5-NITROBENZANILIDE 2-chloro-5-nitro-N-phenylbenzamide 2-CHLORO-5-NITRO-N-PHENYLBENZAMIDE |
CAS | 22978-25-2 |
EINECS | 636-590-7 |
InChI | InChI=1/C13H9ClN2O3/c14-12-7-6-10(16(18)19)8-11(12)13(17)15-9-4-2-1-3-5-9/h1-8H,(H,15,17) |
InChIKey | DNTSIBUQMRRYIU-UHFFFAOYSA-N |
Molecular Formula | C13H9ClN2O3 |
Molar Mass | 276.68 |
Density | 1.440±0.06 g/cm3(Predicted) |
Melting Point | 158-159 °C (lit.) |
Boling Point | 360.9±32.0 °C(Predicted) |
Flash Point | 172°C |
Solubility | Soluble in DMSO (26 mg/ml), methanol, 100% ethanol (10 mg/ml), DMF (~35 mg/ml), and 1: |
Vapor Presure | 2.15E-05mmHg at 25°C |
Appearance | solid |
Color | white |
pKa | 11.77±0.70(Predicted) |
Storage Condition | 2-8°C |
Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
Refractive Index | 1.676 |
MDL | MFCD01215270 |
Use | A selective, irreversible, and effective PPARγ antagonist that also acts as a FXR and PXR agonist. |
In vitro study | GW9662 binds to Cys(285) on PPAR gamma, which is conserved among the three PPAR. GW9662 is a PPARγ antagonist used to inhibit adipocyte differentiation. GW9662 inhibits PPAR gamma activation and inhibits the growth of human breast cancer tumor cell lines (MCF7, MDA-MB-468, MDA-MB-231) with an IC50 of 20 μm -30 μm, the PPAR gamma agonist properties or PPAR gamma independent growth inhibition mechanism of GW9662 are indicated. The combination of Rosiglitazone(50 μm) and GW9662(10 μm) on MDA-MB-231 cells resulted in a statistically lower number of viable cells after 7 days. PPARγ1 ligand was able to inhibit RANKL-induced osteoclast formation in primary murine bone marrow (BMs) and RAW264.7 cells. Importantly, GW 9662(2 μm) reverses the inhibition of these ligands in a concentration-dependent manner. GW 9662(2 μm) acts on BMs, blocking IL-4 inhibition of osteoclast formation. GW 9662(1 μm) acts on RAW264.7 cells to inhibit the RANKL activation of NF-κB. GW9662(10 μm) acts on primary preadipocytes in patients with thyroid ophthalmopathy and inhibits hormone and agonist-induced adipocyte differentiation. |
In vivo study | Pretreatment of rats with LPS(1 mg/kg, I. P.) significantly attenuated all markers of renal injury and dysfunction-induced ischemia/reperfusion (I/R) injury. Most notably, GW9662(1 mg/kg, I. P.) abolished the protective effect of LPS. |
Hazard Symbols | Xi - Irritant |
Risk Codes | R36 - Irritating to the eyes R43 - May cause sensitization by skin contact |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S24/25 - Avoid contact with skin and eyes. S22 - Do not breathe dust. |
WGK Germany | 3 |
HS Code | 29242990 |
Reference Show more | 1. [IF=5.279] Jing Zhou et al."Ginsenoside F2 Suppresses Adipogenesis in 3T3-L1 Cells and Obesity in Mice via the AMPK Pathway."J Agr Food Chem. 2021;69(32):9299–9312 |