8924. Sulfamoxole

Nomenclature

CAS number: 729-99-7
4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulfonamide; N1-(4,5-dimethyl-2-oxazolyl)sulfanilamide; 2-(p-aminobenzenesulfonamido)-4,5-dimethyloxazole; 4,5-dimethyl-2-sulfanilamidooxazole; p-aminobenzenesulfonyl-2-amino-4,5-dimethyloxazole; sulfadimethyloxazole; Justamil (Anphar-Rolland); Sulfmidil (Tika); Sulfuno (Nordmark); Tardamide (Grünenthal).
C11H13N3O3S; mol wt 267.30.
C 49.43%, H 4.90%, N 15.72%, O 17.96%, S 12.00%.

Description and references

Prepn: Loop et al., US 2809966 (1957 to Nordmark-Werke). Series of articles on antimicrobial activity, pharmacology and clinical efficacy of mixture with trimethoprim: Arzneim.-Forsch. 26, 595-684 (1976). Toxicity data: F. Lagler et al., ibid. 634.

Chemical structure

Properties

Crystals, mp 193-194°. Soly in mg/100 ml at 20°: water 85; 0.01N HCl 163; 0.01N NaOH 196; methanol 2315; chloroform 240. uv max (4.91 μg/ml methanol): 210, 250, 270 nm (ε 740, 546, 857). LD50 in mice, rats (g/kg): >10.0, >12.5 orally; 1.80, ≈2.50 i.p. (Lagler).

Derivative

Mixture with trimethoprim.

Nomenclature

CAS number: 57197-43-0
Co-trifamole; CN-3123; Co-Fram (Abbott); Dibactil (Roemmers); Nevin (Grünenthal); Supristol (Gallier).

Properties

LD50 in mice, rats (g/kg): >12.0, 14.0 orally; 1.87, 2.00 i.p. (Lagler).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides