8916. Sulfamethizole

Nomenclature

CAS number: 144-82-1
4-Amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide; N1-(5-methyl-1,3,4-thiadiazol-2-yl)sulfanilamide; 2-sulfanilamido-5-methyl-1,3,4-thiadiazole; 5-methyl-2-sulfanilamido-1,3,4-thiadiazole; 2-(p-aminobenzenesulfonamido)-5-methylthiadiazole; sulfamethylthiadiazole; Lucosil (Lundbeck); Rufol (Fournier); Urolucosil (Lundbeck).
C9H10N4O2S2; mol wt 270.33.
C 39.99%, H 3.73%, N 20.73%, O 11.84%, S 23.72%.

Description and references

Prepn: Hübner, US 2447702 (1948 to Lundbeck).

Chemical structure

Properties

Crystals from water, mp 208°. pKa 5.45. One gram dissolves in 4000 ml water at pH 6.5, in 5 ml water at pH 7.5, in 40 g methanol, in 30 g ethanol, in 10 g acetone, in 1370 g ether, in 2800 g chloroform. Practically insol in benzene.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides