8942. Sulfasalazine

Nomenclature

CAS number: 599-79-1
2-Hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]benzoic acid; 5-[p-(2-pyridylsulfamoyl)phenylazo]salicylic acid; salazosulfapyridine; 5-[4-(2-pyridylsulfamoyl)phenylazo]-2-hydroxybenzoic acid; 4-(pyridyl-2-amidosulfonyl)-3′-carboxy-4′-hydroxyazobenzene; salicylazosulfapyridine; sulphasalazine; Azulfidine (Pfizer); Colo-Pleon (Henning); Salazopyrin (Pfizer).
C18H14N4O5S; mol wt 398.39.
C 54.27%, H 3.54%, N 14.06%, O 20.08%, S 8.05%.

Description and references

Conjugate of 5-aminosalicylic acid and sulfapyridine, q.q.v. Prepn and bactericidal effect: E. E. A. Askelof et al., US 2396145 (1946 to Pharmacia); Doraswamy, Guha, J. Indian Chem. Soc. 23, 278 (1946). Physicochemical properties: B. Nygard et al., Acta Pharm. Suec. 3, 313-342 (1966). Metabolism studies: H. Schroder, D. E. S. Campbell, Clin. Pharmacol. Ther. 13, 539 (1972); M. A. Peppercorn, P. Goldman, J. Pharmacol. Exp. Ther. 181, 555 (1972). HPLC determn in biological fluids: R. A. Hogezand et al., J. Chromatogr. 305, 470 (1984). Clinical trial in rheumatoid arthritis: D. E. Bax, R. S. Amos, Ann. Rheum. Dis. 44, 194 (1985). Review of clinical pharmacokinetics: U. Klotz, Clin. Pharmacokinet. 10, 285-302 (1985); of pharmacology and clinical use in inflammatory bowel disease: M. A. Peppercorn, Ann. Intern. Med. 3, 377 (1984); G. Watkinson, Drugs 32, Suppl. 1, 1-11 (1986). Comprehensive description: J. P. McDonnell, Anal. Profiles Drug Subs. 5, 515-532 (1976).

Chemical structure

Properties

Minute, brownish-yellow crystals, dec 240-245°. uv max: 237 (E1%1cm ≈658) and 359 nm. Slightly sol in alc. Practically insol in water, benzene, chloroform, ether.

Therapeutic Category

Anti-inflammatory (gastrointestinal).

Therapeutic Category (Veterinary)

Has been used in granulomatous colitis.

Keywords

Anti-inflammatory (Gastrointestinal); Anti-inflammatory (Nonsteroidal); Salicylic Acid Derivatives