3146. Diflunisal

Nomenclature

CAS number: 22494-42-4
2′,4′-Difluoro-4-hydroxy-[1,1′-biphenyl]-3-carboxylic acid; 2′,4′-difluoro-4-hydroxy-3-biphenylcarboxylic acid; 2′,4′-difluoro-4-hydroxy-[1′,1-diphenyl]-3-carboxylic acid; 2-(hydroxy)-5-(2,4-difluorophenyl)benzoic acid; 5-(2,4-difluorophenyl)salicylic acid; MK-647; Dolobid (Merck & Co.); Dolobis (Merck & Co.); Fluniget (Merck & Co.).
C13H8F2O3; mol wt 250.20.
C 62.41%, H 3.22%, F 15.19%, O 19.18%.

Description and references

Non-steroidal anti-inflammatory drug (NSAID). Prepn: W. V. Ruyle et al., ZA 6701021; eidem, FR 1522570; eidem, US 3714226 (1968, 1968, 1973, all to Merck & Co.); J. Hannah et al., J. Med. Chem. 21, 1093 (1978). HPLC determn in plasma and urine: M. Schwartz et al., J. Chromatogr. 380, 420 (1986). Metabolism: P. J. DeSchepper et al., Br. J. Clin. Pharmacol. 4, 645P (1977). Clinical studies: J. A. Wojtulewski et al., Curr. Med. Res. Opin. 5, 562 (1978); J. A. Hicklin, ibid. 572; in sickle cell anemia: E. A. Oyewo, Clin. Trials J. 24, 249 (1987). Review of chemistry, pharmacology, clinical pharmacology: S. L. Steelman et al., ibid. 506-514. Comprehensive description: M. Cotton, R. A. Hux, Anal. Profiles Drug Subs. 14, 491-526 (1985). Review: Br. J. Clin. Pharmacol. 4, Suppl. 1, 1S-52S (1977); C. A. Winter et al., in Pharmacological and Biochemical Properties of Drug Substances vol. 3, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1981) pp 291-323. Comprehensive review of pharmacological properties and therapeutic use in pain: R. N. Brogden et al., Drugs 19, 84-106 (1980); Pharmacotherapy 3, no. 2, pt. 2, 1S-82S (1983).

Chemical structure

Properties

White, crystals from toluene, mp 211-213°. Sol in most organic solvents including ethanol, methanol, and acetone. Practically insol in water at neutral or acidic pH. LD50 orally in female mice: 439 mg/kg (Stone).

Therapeutic Category

Analgesic; anti-inflammatory.

Keywords

Analgesic; Non-opioids; Salicylic Acid Derivatives; Anti-inflammatory (Nonsteroidal); Salicylic Acid Derivatives