4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide

• ChemBase ID: 462
• Molecular Formular: C16H14N2O3S
• Molecular Mass: 314.35896
• Monoisotopic Mass: 314.07251332
• SMILES: S(=O)(=O)(N)c1ccc(c2c(noc2C)c2ccccc2)cc1
• Canonical SMILES: Cc1onc(c1c1ccc(cc1)S(=O)(=O)N)c1ccccc1
• InChI: InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)
• InChIKey: LNPDTQAFDNKSHK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide
• IUPAC Traditional name: valdecoxib
• Brand Name: Bextra
• Synonyms: valdecoxib; Valdecoxib; 4-(5-METHYL-3-PHENYLISOXAZOL-4-YL)BENZENESULFONAMIDE; SC-65872; YM-974; 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide; Valdecoxib; Bextra; SC 65872; Valecoxib; Valus; Valz; 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide

Database IDs

• CAS Number: 181695-72-7
• MDL Number: MFCD00950568
• PubChem SID: 160963925; 46506229
• PubChem CID: 119607

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.057539
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.8236701
• LogD (pH = 7.4): 2.8228388
• Log P: 2.8236845
• Molar Refractivity: 84.708 cm^3
• Polarizability: 35.26279 Å^3
• Polar Surface Area: 86.19 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.32
• LOG S: -3.96
• Solubility (Water): 3.48e-02 g/l

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO: >25 mg/mL; Ethanol; Methanol
• Apperance: White Solid; white to off-white powder
• Melting Point: 162-164°C
• Hydrophobicity(logP): 3.2

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-48/22-51/53
• Safety Statements: 36/37-61
• GHS Pictograms: GHS08; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H361d-H373-H410
• GHS Precautionary statements: P273-P281-P501
• Storage Temperature: room temp

Pharmacology Properties

• Target: COX

Product Information

• Purity: ≥98% (HPLC); 98%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C16H14N2O3S

DETAILS

DrugBank - DB00580

• Drug Groups: withdrawn; investigational
• Description: Valdecoxib was removed from the Canadian, U.S., and E.U. markets in 2005 due to concerns about possible increased risk of heart attack and stroke.
• Indication: For the treatment of osteoarthritis and dysmenorrhoea
• Pharmacology: Valdecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is classified as a nonsteroidal anti-inflammatory drug (NSAID). Valdecoxib is used for its anti-inflammatory, analgesic, and antipyretic activities in the management of osteoarthritis (OA) and for the treatment of dysmenorrhea or acute pain. Unlike celecoxib, valdecoxib lacks a sulfonamide chain and does not require CYP450 enzymes for metabolism.
• Toxicity: Symptoms following acute NSAID overdoses are usually limited to lethargy, drowsiness, nausea, vomiting, and epigastric pain, which are generally reversible with supportive care. Gastrointestinal bleeding can occur. Hypertension, acute renal failure, respiratory depression and coma may occur, but are rare.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (involves CYP3A4 and 2C9)
• Absorption: Oral bioavailability is 83%.
• Half Life: 8-11 hours
• Protein Binding: 98%
• Elimination: Valdecoxib is eliminated predominantly via hepatic metabolism with less than 5% of the dose excreted unchanged in the urine and feces. About 70% of the dose is excreted in the urine as metabolites, and about 20% as valdecoxib N-glucuronide.
• Distribution: * 86 L
• Clearance: * oral cl=6 L/h; * 6 – 7 L/h [In patients undergoing hemodialysis]; * 6 – 7 L/h [healthy elderly subjects]
• External Links: Wikipedia; RxList; Drugs.com

DrugBank - DB07576

Drug information: experimental

Sigma Aldrich - PZ0179

Biochem/physiol Actions
Valdecoxib is a non-steroidal anti-inflammatory drug (NSAID), a cyclooxygenase-2 (COX-2) selective inhibitor.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - V090000

A nonsteroidal anti-inflammatory drug (NSAID) that exhibits anti-inflammatory, analgesic and antipyretic properties in animal models. An inhibitor of prostaglandin synthesis primarily through inhibition of COX-2.

REFERENCES

• Yuan, J., et al.: Drug Metab. Dispos., 30, 1013 (2002)
• Mahadik, K., et al.: J. Pharm. Biomed. Anal., 33, 545 (2002)
• Kaul, N., et al.: J. Pharm. Biomed. Anal., 37, 27 (2002)