6924. Oxaprozin

Nomenclature

CAS number: 21256-18-8
4,5-Diphenyl-2-oxazolepropanoic acid; β-(4,5-diphenyloxazol-2-yl)propionic acid; Wy-21743; Alvo (Taisho); Daypro (Pfizer).
C18H15NO3; mol wt 293.32.
C 73.71%, H 5.15%, N 4.78%, O 16.36%.

Description and 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).

Chemical structure

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.

Therapeutic Category

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Arylpropionic Acid Derivatives