Sulfadiazine
Title: Sulfadiazine
CAS Registry Number: 68-35-9
CAS Name: 4-Amino-N-2-pyrimidinylbenzenesulfonamide
Additional Names: 2-sulfanilamidopyrimidine; N1-2-pyrimidinylsulfanilamide; N1-2-pyrimidylsulfanilamide; 2-sulfanilylaminopyrimidine; sulfapyrimidine
Trademarks: Adiazine (Recordati)
Molecular Formula: C10H10N4O2S
Molecular Weight: 250.28
Percent Composition: C 47.99%, H 4.03%, N 22.39%, O 12.79%, S 12.81%
Literature References: Prepd by condensing 2-aminopyrimidine with acetylsulfanilyl chloride followed by hydrolysis of the acetyl group with NaOH: Roblin et al., J. Am. Chem. Soc. 62, 2002 (1940); Barber, GB 557055 (1943); Sprague, US 2407966 (1946 to Sharp & Dohme); Winnek, Roblin, US 2410793 (1946 to Am. Cyanamid). Toxicological, chemotherapeutic and pharmacokinetic studies: Böhni et al., Chemotherapy 14, 195-226 (1969). In vitro activity of silver salt: Carr et al., Antimicrob. Agents Chemother. 4, 585 (1973). Use of silver salt in burns: C. L. Fox, Arch. Surg. 96, 184 (1968). Comprehensive description: H. Stober, W. DeWitte, Anal. Profiles Drug Subs. 11, 523-551 (1982).
Properties: White or slightly yellow powder. mp 252-256°. Sparingly sol in water at 37°: 13 mg/100 ml at pH 5.5; 200 mg/100 ml at pH 7.5. Sparingly sol in alcohol, acetone. One gram dissolves in about 620 ml of human serum at 37°. Freely sol in dil mineral acids and in solns of potassium and sodium hydroxides and in ammonia water.
Melting point: mp 252-256°
 
Derivative Type: Mixture with trimethoprim (usually 5:1)
Additional Names: Co-trimazine
Trademarks: Norodine (Norbrook); Scorprin (Fort Dodge); Tribrissen (Schering); Triglobe (AstraZeneca); Vesuprim (Novartis)
 
Derivative Type: Sodium salt
Additional Names: Sulfadiazine sodium; soluble sulfadiazine
Molecular Formula: C10H9N4NaO2S
Molecular Weight: 272.26
Percent Composition: C 44.11%, H 3.33%, N 20.58%, Na 8.44%, O 11.75%, S 11.78%
Properties: White powder. On prolonged exposure to humid air, it absorbs carbon dioxide with the liberation of sulfadiazine and becomes incompletely sol in water. One gram dissolves in about 2 ml of water. Slightly sol in alc. Solns are alkaline to phenolphthalein (pH 9-11).
 
Derivative Type: Silver salt
CAS Registry Number: 22199-08-2
Trademarks: Flamazine (Smith & Nephew); Flammazine (Solvay); Silvadene (King)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Synthetic); Sulfonamides.

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