Sulfamethoxazole
Title: Sulfamethoxazole
CAS Registry Number: 723-46-6
CAS Name: 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide
Additional Names: N1-(5-methyl-3-isoxazolyl)sulfanilamide; 5-methyl-3-sulfanilamidoisoxazole; 3-sulfanilamido-5-methylisoxazole; 3-(p-aminophenylsulfonamido)-5-methylisoxazole; sulfisomezole; sulfamethylisoxazole; sulfamethoxizole
Trademarks: Gantanol (Roche); Sinomin (Shionogi)
Molecular Formula: C10H11N3O3S
Molecular Weight: 253.28
Percent Composition: C 47.42%, H 4.38%, N 16.59%, O 18.95%, S 12.66%
Literature References: Prepn starting with ethyl 5-methylisoxazole-3-carbamate: Kano et al., US 2888455 (1959 to Shionogi); Annu. Rep. Shionogi Res. Lab. 7, 1 (1957), C.A. 51, 17889 (1957). Toxicity data: Yamamoto et al., Chemotherapy (Tokyo) 21, 187 (1973), C.A. 79, 73738n (1973). Clinical trial of mixture with trimethoprim in Pneumocystis carinii pneumonia: J. M. Wharton et al., Ann. Intern. Med. 105, 37 (1986). Comprehensive description: B. C. Rudy, B. Z. Senkowski, Anal. Profiles Drug Subs. 2, 467-486 (1973). Review of antibacterial activity and clinical efficacy of mixture with trimethoprim: G. P. Wormser et al., Drugs 24, 459-518 (1982). Symposium on clinical intravenous therapy: Rev. Infect. Dis. 9, Suppl. 2, S152-S229 (1987).
Properties: Bitter crystals from dil ethanol, mp 167°. LD50 orally in mice: 3662 mg/kg (Yamamoto).
Melting point: mp 167°
Toxicity data: LD50 orally in mice: 3662 mg/kg (Yamamoto)
 
Derivative Type: Mixture with trimethoprim
CAS Registry Number: 8064-90-2
Additional Names: Co-trimoxazole
Trademarks: Abacin (Benedetti); Apo-Sulfatrim (Apotex); Bactramin (Roche); Bactrim (Roche); Baktar (Shionogi); Chemotrim (Rosemont); Drylin (Merckle); Eusaprim (GSK); Fectrim (DDSA); Gantaprim (Lenza); Gantrim (Geymonat); Imexim (Cimex); Kepinol (Pfleger); Laratrim (Lagap); Linaris (R.A.N.); Microtrim (Chephasaar); Nopil (Mepha); Oraprim (A.T.I.); Septra (Monarch); Septrin (GSK); Sigaprim (Dumex); Sulfotrim (Nattermann); Sulprim (Polfa); Sumetrolim (EGYT); Supracombin (Grñenthal); Suprim (Valeas); Teleprim (Procter & Gamble); Thiocuran (Sagitta); Trigonyl (Hoyer); Trimesulf (LPB); Uroplus (Shionogi)
Properties: LD50 orally in mice: 5513 mg/kg (Yamamoto).
Toxicity data: LD50 orally in mice: 5513 mg/kg (Yamamoto)
 
Derivative Type: N4-Acetylsulfamethoxazole
CAS Registry Number: 21312-10-7
Properties: Crystals from alcohol, mp 209-210°.
Melting point: mp 209-210°
 
Therap-Cat: Antibacterial; antipneumocystic.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Synthetic); Sulfonamides; Antipneumocystic.

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