945. Balsalazide

Nomenclature

CAS number: 80573-04-2
5-[(1E)-[4-[[(2-Carboxyethyl)amino]carbonyl]phenyl]azo]-2-hydroxybenzoic acid; (E)-5-[[p-[(2-carboxyethyl)carbamoyl]phenyl]azo]-2-salicylic acid.
C17H15N3O6; mol wt 357.32.
C 57.14%, H 4.23%, N 11.76%, O 26.87%.

Description and references

Analog of sulfasalazine, q.v. Prodrug of 5-aminosalicylic acid where carrier molecule is 4-aminobenzoyl-β-alanine. Prepn: R. P. K. Chan, GB 2080796; idem, US 4412992 (1982, 1983 both to Biorex). Toxicology study and clinical metabolism: idem et al., Dig. Dis. Sci. 28, 609 (1983). Review of pharmacology and clinical efficacy in ulcerative colitis: A. Prakash, C. M. Spencer, Drugs 56, 83 (1998).

Chemical structure

Properties

Crystals from hot ethanol, mp 254-255°.

Derivative

Disodium salt dihydrate.

Nomenclature

CAS number: 150399-21-6; 82101-18-6 (anhydrous)
BX-661A; Colazal (Salix); Colazide (Shire).
C17H13N3Na2O6.2H2O; mol wt 437.31.
C 46.69%, H 3.92%, N 9.61%, Na 10.51%, O 29.27%.

Properties

Orange to yellow microcrystalline powder, mp >350°. Nonhygroscopic. Freely sol in water, isotonic saline; sparingly sol in methanol, ethanol. Practically insol in organic solvents.

Therapeutic Category

Anti-inflammatory (gastrointestinal).

Keywords

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