8908. Sulfaguanidine

Nomenclature

CAS number: 57-67-0
4-Amino-N-(aminoiminomethyl)benzenesulfonamide; 4-amino-N-(diaminomethylene)benzenesulfonamide; N1-amidinosulfanilamide; N1-guanylsulfanilamide; p-aminobenzenesulfonylguanidine; sulfanilylguanidine; RP-2275; Diacta (Nicholas); Ganidan (Specia); Guanicil (Cilag); Resulfon (Nordmark); Shigatox (Fawns & McAllan).
C7H10N4O2S; mol wt 214.24.
C 39.24%, H 4.70%, N 26.15%, O 14.94%, S 14.97%.

Description and 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).

Chemical structure

Derivative

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.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antimicrobial. In enteric infections.

Keywords

Antibacterial (Synthetic); Sulfonamides