8951. Sulfisomidine

Nomenclature

CAS number: 515-64-0
4-Amino-N-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide; N1-(2,6-dimethyl-4-pyrimidinyl)sulfanilamide; 2,6-dimethyl-4-sulfanilamidopyrimidine; 6-sulfanilamido-2,4-dimethylpyrimidine; 6-(sulfanilamido)-2,4-dimethyl-1,3-diazine; 6-(p-aminophenylsulfonamido)-2,4-dimethylpyrimidine; 6-(p-aminobenzenesulfonyl)amino-2,4-dimethylpyrimidine; sulfadimetine; sulfaisodimidine; sulphasomidine; Elkosin (Novartis); Elcosine; Elkosil; Domain; Aristamid (Nordmark).
C12H14N4O2S; mol wt 278.33.
C 51.78%, H 5.07%, N 20.13%, O 11.50%, S 11.52%.

Description and references

Prepn: FR 886009 (1943 to Nordmark); Gysin, US 2351333 (1944 to Geigy); Hartmann et al., US 2386852; US 2429184 (1945, 1947, both to Ciba); Matsukawa et al., J. Pharm. Soc. Jpn. 70, 283 (1950); Loop, Lührs, Ann. 580, 225 (1953).

Chemical structure

Properties

Needles from ethanol, mp 243°. Soly in water at 15°: 0.12 g/100 ml, at 30°: 0.30 g/100 ml. More sol in hot water (about 1:60). Aq solns are neutral to litmus. Soly in urine at 37°: 360 mg/100 ml at pH 5.5 to 1100 mg/100 ml at pH 7.5. Slightly sol in alcohol, acetone. Practically insol in benzene, ether, chloroform. Freely sol in dil HCl and NaOH. Compared with sulfanilamide it is but slightly acetylated in the body.

Note

Do not confuse with sulfamethazine, q.v.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antimicrobial.

Keywords

Antibacterial (Synthetic); Sulfonamides