Phthalylsulfathiazole
Title: Phthalylsulfathiazole
CAS Registry Number: 85-73-4
CAS Name: 2-[[[4-[(2-Thiazolylamino)sulfonyl]phenyl]amino]carbonyl]benzoic acid
Additional Names: 4¢-(2-thiazolylsulfamyl)phthalanilic acid; 2-(N4-phthalylaminobenzenesulfonamido)thiazole; 2-(N4-phthalylsulfanilamido)thiazole; phthalylsulfonazole
Trademarks: Estreptocarbocaftiazol (Bago); Thalazole (M & B)
Molecular Formula: C17H13N3O5S2
Molecular Weight: 403.43
Percent Composition: C 50.61%, H 3.25%, N 10.42%, O 19.83%, S 15.90%
Literature 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 Söhne). Toxicity data: P. A. Mattis et al., J. Pharmacol. Exp. Ther. 81, 116 (1944).
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).
Melting point: mp 272-277° (dec) when the melting point bath is preheated to 220-225°
Toxicity data: LD50 i.p. in mice: 920 mg/kg (Mattis)
 
Derivative Type: 8-Hydroxyquinoline salt
Properties: Yellow crystals from dil methanol, dec above 220°. Split into its components by dil acids.
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Synthetic); Sulfonamides.

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