7377. Phthalylsulfathiazole

Nomenclature

CAS number: 85-73-4
2-[[[4-[(2-Thiazolylamino)sulfonyl]phenyl]amino]carbonyl]benzoic acid; 4′-(2-thiazolylsulfamyl)phthalanilic acid; 2-(N4-phthalylaminobenzenesulfonamido)thiazole; 2-(N4-phthalylsulfanilamido)thiazole; phthalylsulfonazole; Estreptocarbocaftiazol (Bago); Thalazole (M & B).
C17H13N3O5S2; mol wt 403.43.
C 50.61%, H 3.25%, N 10.42%, O 19.83%, S 15.90%.

Description and references

May be prepd by condensing sulfathiazole with phthalic anhydride: M. L. Moore, US 2324013; US 2324015 (1943 to Sharp & Dohme). Prepn of 8-hydroxyquinoline salt: DE 1008296 (1957 to Geistlich S"ohne). Toxicity data: P. A. Mattis et al., J. Pharmacol. Exp. Ther. 81, 116 (1944).

Chemical structure

Properties

Crystals. Slightly bitter taste. Darkens on prolonged exposure to light. Effervesces at 244° to 250°. mp 272-277° (dec) when the melting point bath is preheated to 220-225°. Slightly sol in alcohol; very slightly sol in ether; readily sol in NaOH or KOH soln, ammonia water and concd HCl. Practically insol in chloroform and water. LD50 i.p. in mice: 920 mg/kg (Mattis).

Derivative

8-Hydroxyquinoline salt.

Properties

Yellow crystals from dil methanol, dec above 220°. Split into its components by dil acids.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides