8937. Sulfapyrazine

Nomenclature

CAS number: 116-44-9
4-Amino-N-(pyrazinyl)benzenesulfonamide; N1-2-pyrazinylsulfanilamide; 2-sulfanilamidopyrazine.
C10H10N4O2S; mol wt 250.28.
C 47.99%, H 4.03%, N 22.39%, O 12.79%, S 12.81%.

Description and references

Prepd by reacting acetylsulfanilyl chloride with 2-aminopyrazine in pyridine, followed by hydrolysis and neutralization: Ellingson, US 2420703 (1947). Biological properties: Ghione et al., Chemotherapia 6, 344 (1962).

Chemical structure

Properties

Crystals, dec 250-254°. Very slightly sol in alc; slightly sol in acetone. Sol in aq solns of sodium, potassium, and barium hydroxides, in ammonia water, and in dil and concd mineral acid solns. Practically insol in water (5 mg/100 ml at 25°, and 5.2 mg/100 ml at 37°).

Derivative

Sodium salt monohydrate.
C10H9N4NaO2S.H2O; mol wt 290.27.
C 41.38%, H 3.82%, N 19.30%, Na 7.92%, O 16.54%, S 11.05%.

Properties

Bitter powder. Freely soluble in water (1 g/3.33 ml at 25°). Alkaline to litmus. pH of 10% aq soln 9.1. Very sol in acetone, slightly sol in alc. Insol in ether, chloroform. Aq solns of sulfapyrazine sodium may absorb carbon dioxide which causes precipitation of sulfapyrazine.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides