8915. Sulfamethazine

Nomenclature

CAS number: 57-68-1
4-Amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide; N1-(4,6-dimethyl-2-pyrimidinyl)sulfanilamide; N1-(4,6-dimethyl-2-pyrimidyl)sulfanilamide; 4,6-dimethyl-2-sulfanilamidopyrimidine; sulfamezathine; sulfadimerazine; sulfadimidine; sulfamidine; sulfadimethylpyrimidine; Diazil (Bracco); Sulfadine (Ayerst); S-Dimidine (Protea); Dimidin-R (Chassot); Neazina (Centralvet); Sulmet (Am. Cyanamid).
C12H14N4O2S; mol wt 278.33.
C 51.78%, H 5.07%, N 20.13%, O 11.50%, S 11.52%.

Description and references

Prepn: Caldwell et al., J. Am. Chem. Soc. 63, 2188 (1941); Roblin et al., ibid. 64, 567 (1942); Weisner, Katscher, GB 546158 (1942 to Ward, Blenkinsop); Sprague, US 2407966 (1946 to Sharp & Dohme). Alternate prepn: Haworth, Rose, GB 552887 (1943 to I.C.I.); Garzia, US 3119818 (1964 to Ist. Chemioterap. Ital.). Anticoccidiosis activity: Zarin, Feodorova, C.A. 66, 114, 435p-436q (1967). Metabolic studies: Turco et al., Clin. Pharmacol. Ther. 7, 603 (1966); Parker et al., Hum. Hered. 19, 402 (1969). Solubility studies: Shkadova et al., Farm. Zh. (Kiev) 24, 39 (1969). Acute toxicity: B. Bobranski et al., Arch. Immunol. Ther. Exp. 16, 804 (1968). Comprehensive description: C. Papostephanou, M. Frantz, Anal. Profiles Drug Subs. 7, 401-422 (1978).

Chemical structure

Properties

Crystals from dioxane-water, mp 176° (also reported as mp 178-179°; mp 198-199°; mp 205-207°). uv max (water, pH 6.6): 241 nm (E1%1cm 670); (0.01N NaOH): 243, 257 nm (E1%1cm 765, 776); (0.01N HCl): 241, 297 nm (E1%1cm 561, 266). Soly in water at 29°: 150 mg/100 ml; at 37°: 192 mg/100 ml at pH 7.0. pK1 7.4±0.2, pK2 2.65±0.2. The soly increases rapidly with an increase in pH. LD50 i.p. in mice: 1.06 g/kg (Bobranski).

Derivative

Sodium salt.

Nomenclature

CAS number: 1981-58-4
Intradine (Norbrook); Sulfoxine 33 (Univet); Vesadin (Rhne-Mérieux).
C12H13N4NaO2S; mol wt 300.31.
C 47.99%, H 4.36%, N 18.66%, Na 7.66%, O 10.66%, S 10.68%.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides