8935. Sulfaphenazole

Nomenclature

CAS number: 526-08-9
4-Amino-N-(1-phenyl-1H-pyrazol-5-yl)benzenesulfonamide; N′-(1-phenylpyrazol-5-yl)sulfanilamide; 1-phenyl-5-sulfanilamidopyrazole; 3-(p-aminobenzenesulfonamido)-2-phenylpyrazole.
C15H14N4O2S; mol wt 314.36.
C 57.31%, H 4.49%, N 17.82%, O 10.18%, S 10.20%.

Description and references

Synthesis: Schmidt, Druey, Helv. Chim. Acta 41, 309 (1958); Druey, Schmidt, US 2858309 (1958 to Ciba). Toxicity study: Seki et al., Arzneim.-Forsch. 15, 1441 (1965).

Chemical structure

Properties

Crystals from alcohol, mp 179-183°. Very sparingly sol in water: 0.15 g/100 ml H2O at pH 7.0 and 25°. More sol in methanol, ethanol, glacial acetic acid. LD50 orally in mice: 5800 mg/kg (Seki).

Derivative

Sodium salt monohydrate.
C15H13N4NaO2S.H2O; mol wt 354.36.
C 50.84%, H 4.27%, N 15.81%, Na 6.49%, O 13.55%, S 9.05%.

Properties

White powder. Sol in water. A 10% soln (w/w) has a pH of ≈9.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides