2-chloro-5-nitro-N-phenylbenzamide

• ChemBase ID: 5496
• Molecular Formular: C13H9ClN2O3
• Molecular Mass: 276.67516
• Monoisotopic Mass: 276.03016984
• SMILES: Clc1ccc([N+](=O)[O-])cc1C(=O)Nc1ccccc1
• Canonical SMILES: Clc1ccc(cc1C(=O)Nc1ccccc1)[N+](=O)[O-]
• InChI: InChI=1S/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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-5-nitro-N-phenylbenzamide
• IUPAC Traditional name: 2-chloro-5-nitrobenzanilide
• Synonyms: GW9662; 2-Chloro-5-nitro-N-4-phenylbenzamide; 2-chloro-5-nitro-N-phenylbenzamide; 2-Chloro-5-nitro-N-phenylbenzamide; GW9662; GW9662; 2-Chloro-5-nitrobenzanilide; 2-氯-5-硝基-N-苯基苯酰胺

Database IDs

• CAS Number: 22978-25-2
• MDL Number: MFCD01215270
• PubChem SID: 24278560; 99444334; 160968924; 24883187
• PubChem CID: 644213

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.418081
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.609159
• LogD (pH = 7.4): 3.60912
• Log P: 3.6091595
• Molar Refractivity: 72.7168 cm^3
• Polarizability: 26.737232 Å^3
• Polar Surface Area: 72.24 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.39
• LOG S: -4.74
• Solubility (Water): 5.01e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble26 mg/mL; H2O: insoluble
• Apperance: Off-White Solid; white powder
• Melting Point: 158-159 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36-43
• Safety Statements: 26-36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H319
• GHS Precautionary statements: P280-P305 + P351 + P338
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: PPAR
• Gene Information: human ... PPARG(5468)

Product Information

• Purity: >98% (HPLC); 97%
• Salt Data: Free Base
• Linear Formula: ClC6H3(NO2)CONHC6H5
• Empirical Formula (Hill Notation): C13H9ClN2O3

DETAILS

DrugBank - DB07863

Drug information: experimental

Sigma Aldrich - M6191

Legal Information
Sold for research purposes only, under agreement from Glaxo-Smith-Kline
Biochem/physiol Actions
GW9662 is an irreversible PPARγ antagonist. GW9662 inhibits connective tissue growth factor and activation of CD36 by IL-4.

Sigma Aldrich - 642355

Packaging
25 g in glass bottle

Toronto Research Chemicals - C374050

A cell-permeable, selective and irreversible PPARγ antagonist (IC50 = 3.3 nM, 32 nM, and 2 μM for PPARγ, PPARα, and PPARδ, respectively). Reported to covalently modify a cysteine residue in the binding site of PPAR. At a concentration of 10 μM, also acts as an agonist of human pregnane X receptor (PXR) and farnesoid X receptor (FXR). Does not activate liver X receptor-a (LXRa), retinoic acid receptor (RAR), retinoid X receptor-a (RXRa) and thyroid receptors a and b (TRa and TRb)

REFERENCES

• Huang, J.T., et al.: Nature, 400, 378 (1999)
• Wilson, T.M., et al.: J. Med. Chem., 43, 527 (1999)
• Leesnitzer, L.M., et al.: Biochemistry, 41, 6640 (2002)