8920. Sulfametrole

Nomenclature

CAS number: 32909-92-5
4-Amino-N-(4-methoxy-1,2,5-thiadiazol-3-yl)benzenesulfonamide; N1-(4-methoxy-1,2,5-thiadiazol-3-yl)sulfanilamide; 3-methoxy-4-(4′-aminobenzenesulfonamido)-1,2,5-thiadiazole.
C9H10N4O3S2; mol wt 286.33.
C 37.75%, H 3.52%, N 19.57%, O 16.76%, S 22.40%.

Description and references

Anti-infective sulfanilamide, related structurally to sulfadiazine, q.v. Prepn: BE 629551 corresp to K. Menzl, US 3247193 (1963, 1966 both to OSSW). Improved prepn: idem, US 4151164 (1979 to Chemie Linz). Bacteriological study (of mixture with trimethoprim): G. Nabert-Bock, H. Grims, Arzneim.-Forsch. 27, 1109 (1977). Tolerance, therapeutic effect, pharmacokinetics: S. Breyer et al., Wien. Med. Wochenschr. 130, 448 (1980). Renal excretion mechanism, pharmacokinetics: T. B. Vree et al., Eur. J. Clin. Pharmacol. 20, 283 (1981). Pharmacokinetics of sulfametrole and its metabolite in man: Y. A. Hester et al., J. Antimicrob. Chemother. 8, 133 (1981). Crystal and molecular structures: C. H. Koo et al., Bull. Korean Chem. Soc. 3, 9 (1982), C.A. 96, 208771 (1982). Single-dose therapy of chancroid with trimethoprim-sulfametrole: F. A. Plummer et al., N. Engl. J. Med. 309, 67 (1983).

Chemical structure

Properties

Cryst from dilute acetic acid, mp 149-150°.

Derivative

Mixture with trimethoprim.

Nomenclature

CAS number: 63749-94-0
Lidaprim (Nycomed); Maderan (Nycomed).

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides