8918. Sulfamethoxazole

Nomenclature

CAS number: 723-46-6
4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide; N1-(5-methyl-3-isoxazolyl)sulfanilamide; 5-methyl-3-sulfanilamidoisoxazole; 3-sulfanilamido-5-methylisoxazole; 3-(p-aminophenylsulfonamido)-5-methylisoxazole; sulfisomezole; sulfamethylisoxazole; sulfamethoxizole; Gantanol (Roche); Sinomin (Shionogi).
C10H11N3O3S; mol wt 253.28.
C 47.42%, H 4.38%, N 16.59%, O 18.95%, S 12.66%.

Description and 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).

Chemical structure

Properties

Bitter crystals from dil ethanol, mp 167°. LD50 orally in mice: 3662 mg/kg (Yamamoto).

Derivative

Mixture with trimethoprim.

Nomenclature

CAS number: 8064-90-2
Co-trimoxazole; 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 (Grünenthal); Suprim (Valeas); Teleprim (Procter & Gamble); Thiocuran (Sagitta); Trigonyl (Hoyer); Trimesulf (LPB); Uroplus (Shionogi).

Properties

LD50 orally in mice: 5513 mg/kg (Yamamoto).

Derivative

N4-Acetylsulfamethoxazole.

Nomenclature

CAS number: 21312-10-7

Properties

Crystals from alcohol, mp 209-210°.

Therapeutic Category

Antibacterial; antipneumocystic.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides; Antipneumocystic