8909. Sulfaguanole

Nomenclature

CAS number: 27031-08-9
4-Amino-N-[[(4,5-dimethyl-2-oxazolyl)amino]iminomethyl]benzenesulfonamide; N1-[(4,5-dimethyl-2-oxazolyl)amidino]sulfanilamide; 1-(4,5-dimethyloxazol-2-yl)-3-sulfanilylguanidine; 1-(p-aminophenylsulfonyl)-3-(4,5-dimethyl-2-oxazolyl)guanidine; sulfadimethyloxazolylguanidine; Enterocura (Nordmark).
C12H15N5O3S; mol wt 309.34.
C 46.59%, H 4.89%, N 22.64%, O 15.52%, S 10.37%.

Description and references

Prepn: Loop et al., GB 1185139 C.A. 73, 3909w (1970); eidem, US 3562258 (1970, 1971 both to Nordmark-Werke); Loop, Kohlmann, Arzneim.-Forsch. 23, 171 (1973). Toxicology: J. Kuhne et al., ibid. 178. Series of articles on pharmacology: ibid. 172-192.

Chemical structure

Properties

Almost colorless crystals from 9:1 acetone-water, mp 233-236°; from water-methanol, mp 228-230°. pKa 7.76. Practically insol in water. Sol in dil NaOH solns. No deaths in mice or rats for oral doses of 5 g/kg (Kuhne).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides