Succinylsulfathiazole
Title: Succinylsulfathiazole
CAS Registry Number: 116-43-8
CAS Name: 4-Oxo-4-[[4-[(2-thiazolylamino)sulfonyl]phenyl]amino]butanoic acid
Additional Names: 4¢-(2-thiazolylsulfamoyl)succinanilic acid; p-2-thiazolylsulfamylsuccinanilic acid; 2-(N4-succinylsulfanilamido)thiazole
Trademarks: Sulfasuxidine (Merck & Co.)
Molecular Formula: C13H13N3O5S2
Molecular Weight: 355.39
Percent Composition: C 43.93%, H 3.69%, N 11.82%, O 22.51%, S 18.04%
Literature 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).
 
Derivative Type: 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).
Melting point: mp 184-186°; mp 192-195°
Toxicity data: LD50 i.p. in mice: ~5.7 g/kg (Welch)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial, esp in enteric infections.
Keywords: Antibacterial (Synthetic); Sulfonamides.

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