13-09030. Sulfasymazine [Archived]

Nomenclature

CAS number: 1984-94-7
4-Amino-N-(4,6-diethyl-1,3,5-triazin-2-yl)benzenesulfonamide; N1-(4,6-diethyl-s-triazin-2-yl)sulfanilamide; 2-sulfanilamido-4,6-diethyl-1,3,5-triazine; 4,6-diethyl-2-sulfanilamido-1,3,5-triazine; sulphsymazine; Symasul (Lederle); Prosymasul (Lederle).
C13H17N5O2S; mol wt 307.37.
C 50.80%, H 5.57%, N 22.78%, O 10.41%, S 10.43%.

Description and references

Prepn by nucleophilic displacement of methoxy groups from 2-methoxy-4,6-disubstituted s-triazines with sulfanilamide anion: Taft et al., J. Med. Chem. 8, 784 (1965); Bader, US 3344137 (1967 to Am. Cyanamid). Pharmacological studies: Frisk, Hultman, Antimicrob. Agents Chemother. 1965, 672; Kruger-Thiemer et al., Chemotherapia 10, 325 (1966).

Chemical structure

Properties

White precipitate from ethanol, mp 186.5-187.5° (Taft); 190-190.5° (Bader). Tasteless. pKa (30% acetone) = 5.4. Sol in water, acetate buffer (1 mg/ml at pH 5.9); also sol in human urine at 37° (2 mg/ml at pH 6; >10 mg/ml at pH 7).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides

Status

This monograph has been retired and is no longer subject to revision or update.