Title: Sulfaguanidine
CAS Registry Number: 57-67-0
CAS Name: 4-Amino-
N-(aminoiminomethyl)benzenesulfonamide
Synonyms: 4-amino-
N-(diaminomethylene)benzenesulfonamide;
N1-amidinosulfanilamide;
N1-guanylsulfanilamide;
p-aminobenzenesulfonylguanidine; sulfanilylguanidine
Manufacturers' Codes: RP-2275
Trademarks: Diacta (Nicholas); Ganidan (Specia); Guanicil (Cilag); Resulfon (Nordmark); Shigatox (Fawns & McAllan)
Molecular Formula: C7H10N4O2S
Molecular Weight: 214.24
Percent Composition: C 39.24%, H 4.70%, N 26.15%, O 14.94%, S 14.97%
Literature References: Prepd by condensing acetylsulfanilyl chloride with guanidine nitrate in the presence of much NaOH in water-acetone: Winnek,
US 2218490 (1940);
US 2229784 (1941);
US 2233569 (1941); or by fusing
N4-acetylsulfanilamide and dicyanodiamide: Haworth, Rose,
GB 551524 (1943). Additional syntheses:
ACS Monograph Series no. 106, entitled "Sulfonamides and Allied Compounds," E. H. Northey, Ed. (Reinhold, New York, 1948). Revised structure: G. R. Sullivan, J. D. Roberts,
J. Org. Chem. 42, 1095 (1977). Review of pharmacology: E. K. Marshall, Jr.
et al., Bull. Johns Hopkins Hosp. 67, 163-188 (1940); E. Pick,
J. Mt. Sinai Hosp. 10, 343-354 (1943).
Derivative Type: Monohydrate
Properties: Needles. When anhydr, mp 190-193°. One gram dissolves in about 1000 ml water at 25° and in about 10 ml at 100°. Sparingly sol in alcohol or acetone. Freely sol in dil mineral acids. Insol in NaOH solns at room temp.
Melting point: mp 190-193°
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antimicrobial. In enteric infections.
Keywords: Antibacterial (Synthetic); Sulfonamides.
