4-[5-(2,5-dimethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide

• ChemBase ID: 154818
• Molecular Formular: C18H16F3N3O2S
• Molecular Mass: 395.3987496
• Monoisotopic Mass: 395.09153243
• SMILES: Cc1ccc(c(c1)c1cc(nn1c1ccc(cc1)S(=O)(=O)N)C(F)(F)F)C
• Canonical SMILES: Cc1ccc(c(c1)c1cc(nn1c1ccc(cc1)S(=O)(=O)N)C(F)(F)F)C
• InChI: InChI=1S/C18H16F3N3O2S/c1-11-3-4-12(2)15(9-11)16-10-17(18(19,20)21)23-24(16)13-5-7-14(8-6-13)27(22,25)26/h3-10H,1-2H3,(H2,22,25,26)
• InChIKey: NTFOSUUWGCDXEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[5-(2,5-dimethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
• IUPAC Traditional name: 4-[5-(2,5-dimethylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
• Synonyms: 2,5-Dimethyl-celecoxib; 2,5-Dimethylcelecoxib; 4-[5-(2,5-dimethylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-benzenesulfonamide

Database IDs

• CAS Number: 457639-26-8
• MDL Number: MFCD19443858
• PubChem SID: 162248956
• PubChem CID: 11545682

CALCULATED PROPERTIES

• Acid pKa: 10.701063
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.52286
• LogD (pH = 7.4): 4.5226707
• Log P: 4.5228634
• Molar Refractivity: 97.2754 cm^3
• Polarizability: 38.13224 Å^3
• Polar Surface Area: 77.98 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥30 mg/mL
• Apperance: off-white to light yellow powder

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C18H16F3N3O2S

DETAILS

Sigma Aldrich - D7196

Biochem/physiol Actions
Celecoxib, and the inactive analog 2′,5′-dimethyl celecoxib both induce apoptosis in a many cancer cell lines by down-regulating the expression of survivin. This activiy is mediated via an AKT mediated pathway, and is unique to this class of cyclo-oxygenase inhibitors, as non-selective NSAIDs or other COX-2 specific inhibitors such as rofecoxib, do not effect survivin expression. Unlike celecoxib, 2′,5′-dimethyl celecoxib is devoid of any inhibitory activity against COX-2.

Sigma Aldrich - 35342

Biochem/physiol Actions
Celecoxib, and the inactive analog 2′,5′-dimethyl celecoxib both induce apoptosis in a many cancer cell lines by down-regulating the expression of survivin. This activiy is mediated via an AKT mediated pathway, and is unique to this class of cyclo-oxygenase inhibitors, as non-selective NSAIDs or other COX-2 specific inhibitors such as rofecoxib, do not effect survivin expression. Unlike celecoxib, 2′,5′-dimethyl celecoxib is devoid of any inhibitory activity against COX-2.
Legal Information
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