Structural Formula Vector Image
Title: Sulfasymazine
CAS Registry Number: 1984-94-7
CAS Name: 4-Amino-N-(4,6-diethyl-1,3,5-triazin-2-yl)benzenesulfonamide
Additional Names: 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
Trademarks: Symasul (Lederle); Prosymasul (Lederle)
Molecular Formula: C13H17N5O2S
Molecular Weight: 307.37
Percent Composition: C 50.80%, H 5.57%, N 22.78%, O 10.41%, S 10.43%
Literature 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).
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).
Melting point: mp 186.5-187.5° (Taft); 190-190.5° (Bader)
pKa: pKa (30% acetone) = 5.4
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); Sulfonamides.
Status: This monograph has been retired and is no longer subject to revision or update.

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