8877. Succinylsulfathiazole

Nomenclature

CAS number: 116-43-8
4-Oxo-4-[[4-[(2-thiazolylamino)sulfonyl]phenyl]amino]butanoic acid; 4′-(2-thiazolylsulfamoyl)succinanilic acid; p-2-thiazolylsulfamylsuccinanilic acid; 2-(N4-succinylsulfanilamido)thiazole; Sulfasuxidine (Merck & Co.).
C13H13N3O5S2; mol wt 355.39.
C 43.93%, H 3.69%, N 11.82%, O 22.51%, S 18.04%.

Description and references

Prepd by refluxing sulfathiazole with a slight excess of succinic anhydride in alcohol: Moore, Miller, J. Am. Chem. Soc. 64, 1572 (1942); US 2324013; US 2324014 (both 1943); by refluxing p-succinimidobenzenesulfonyl chloride with 2-aminothiazole in benzene: GB 578004 (1946). Toxicology: A. D. Welch et al., J. Pharmacol. Exp. Ther. 75, 231 (1942).

Chemical structure

Derivative

Monohydrate.

Properties

Crystals with unclear mp. Has been reported as mp 184-186°; also reported as mp 192-195°. Emits pungent fumes on heating to mp. One gram dissolves in about 4800 ml water. Soluble in solns of alkali hydroxides and in solns of sodium bicarbonate with the evolution of carbon dioxide; sparingly sol in alcohol and in acetone. Insol in chloroform and ether. LD50 i.p. in mice: ≈5.7 g/kg (Welch).

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial, esp in enteric infections.

Keywords

Antibacterial (Synthetic); Sulfonamides