6841. Olsalazine

Nomenclature

CAS number: 15722-48-2
3,3′-Azobis(6-hydroxybenzoic acid); C.I. Mordant Yellow 5; 3,3′-dicarboxy-4,4′-dihydroxyazobenzene; 5,5′-azobis(salicylic acid); azodisal.
C14H10N2O6; mol wt 302.24.
C 55.63%, H 3.33%, N 9.27%, O 31.76%.

Description and references

Prodrug cleaved by colonic bacteria at the azo-position to give two molecules of mesalamine, q.v. Originally used as a mordant dye. Prepn: DE 278613; C. Mettler, US 1157169 (1914, 1915 both to J. R. Geigy). Improved prepn: K. H. Agback, A. S. Nygren, EP 36636; eidem, US 4528367 (1981, 1985 both to Pharmacia AB). HPLC determn in biological samples: R. A. van Hogezand et al., J. Chromatogr. 305, 470 (1984). In vitro effect on fecal bacteria: H. Sandberg-Gertzen et al., Scand. J. Gastroenterol. 20, 607 (1985). Clinical pharmacokinetics and metabolism: C. P. Willoughby et al., Gut 23, 1081 (1982). Clinical trial in ulcerative colitis: H. Sandberg-Gertzen et al., Gastroenterology 90, 1024 (1986). Review of clinical experience in inflammatory bowel disease: A. N. Wadworth, A. Fitton, Drugs 41, 647-664 (1991).

Chemical structure

Derivative

Disodium salt.

Nomenclature

CAS number: 6054-98-4
Azodisal sodium; disodium azodisalicylate; C.I. 14130; CJ-91B; Dipentum (Pfizer).
C14H8N2Na2O6; mol wt 346.20.
C 48.57%, H 2.33%, N 8.09%, Na 13.28%, O 27.73%.

Properties

Yellow crystalline powder, mp 240° (dec). Sol in water, DMSO. Practically insol in ethanol, chloroform, ether.

Therapeutic Category

Anti-inflammatory (gastrointestinal).

Therapeutic Category (Veterinary)

Anti-inflammatory (gastrointestinal).

Keywords

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