8339. Salsalate

Nomenclature

CAS number: 552-94-3
2-Hydroxybenzoic acid 2-carboxyphenyl ester; disalicylic acid; salicylic acid bimolecular ester; salicyloxysalicylic acid; salicylsalicylic acid; NSC-49171; Disalcid (3M); Disalgesic (3M); Mono-Gesic (Central); Salflex (Carnrick).
C14H10O5; mol wt 258.23.
C 65.12%, H 3.90%, O 30.98%.

Description and references

Nonacetylated aspirin analog. Prepn: DE 211403 and DE 214044 (1909, both to Boehringer, Mann.), Frdl. 9, 928 and C.A. 4, 368 (1910); W. Baker et al., J. Chem. Soc. 1951, 201. Metabolism: S. M. Dromgoole et al., J. Pharm. Sci. 73, 1657 (1984). Clinical evaluation in arthritis: T. C. McPherson, Clin. Ther. 6, 388 (1984). Mechanism of action studies: C. A. Divincenzo, F. R. Venezio, Curr. Ther. Res. 42, 720 (1987). HPLC determn in plasma and urine: L. I. Harrison et al., J. Pharm. Sci. 69, 1268 (1980). Review of chemistry, pharmacokinetics, safety and clinical efficacy: P. T. Singleton, Clin. Ther. 3, 80-102 (1980).

Chemical structure

Properties

Crystals from benzene. mp 148-149°. Practically insol in water but gradually hydrolyzed by it into 2 mols of salicylic acid. Sol in alc, ether; sparingly sol in benzene.

Therapeutic Category

Analgesic, anti-inflammatory.

Keywords

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