Title: Oxaprozin
CAS Registry Number: 21256-18-8
CAS Name: 4,5-Diphenyl-2-oxazolepropanoic acid
Synonyms: b-(4,5-diphenyloxazol-2-yl)propionic acid
Manufacturers' Codes: Wy-21743
Trademarks: Alvo (Taisho); Daypro (Pfizer)
Molecular Formula: C18H15NO3
Molecular Weight: 293.32
Percent Composition: C 73.71%, H 5.15%, N 4.78%, O 16.36%
Literature References: First description of anti-inflammatory properties: K. Brown
et al., Nature 219, 164 (1968). Prepn:
FR 2001036 (1969 to Inst. Farm. Serono),
C.A. 72, 66930w (1970); K. Brown,
GB 1206403 and
US 3578671 (1970, 1971 both to Wyeth). Biochemical properties: M. W. Whitehouse
et al., Biochem. Pharmacol. 20, 2309 (1971). Metabolism: F. W. Janssen
et al., Drug Metab. Dispos. 6, 465 (1978). Pharmacology: D. A. Shriver
et al., Toxicol. Appl. Pharmacol. 42, 75 (1977); F. Awouters
et al., J. Pharm. Pharmacol. 30, 41 (1978). Clinical studies: R. Jamar, J. Dequeker,
Curr. Med. Res. Opin. 5, 433 (1978); J. A. Hubsher
et al., J. Int. Med. Res. 7, 69 (1979);
eidem, Arthritis Rheum. 25, S117 (1982). Protein binding and clearance: C. A. Homon
et al., Agents Actions 12, 211 (1982). Symposium on pharmacology and clinical efficacy:
Semin. Arthritis Rheum. 15, Suppl. 3, 1-107 (1986). Review of mechanism of action and clinical efficacy: F. Dallegri
et. al., Expert Opin. Pharmacother. 6, 777-785 (2005).
Properties: Crystals from methanol, mp 160.5-161.5°. Slightly sol in alcohol. Insol in water. Partition coefficient (octanol/water): 4.8 (pH 7.4). pKa 4.3.
Melting point: mp 160.5-161.5°
pKa: pKa 4.3
Log P: Partition coefficient (octanol/water): 4.8 (pH 7.4)
Therap-Cat: Anti-inflammatory.
Keywords: Anti-inflammatory (Nonsteroidal); Arylpropionic Acid Derivatives.
