Antibacterial Agents, Nitrofurans

Abstract

The nitrofurans encompass a class of synthetic antibacterials characterized by the 5‐nitro‐2‐furanyl group. Nitrofurans include furium, C 9 H 7 N 3 O 4 S; furazolidone, \documentclass{article}\usepackage{amssymb}\pagestyle{empty}\begin{document}${{\rm{C}}{_{14}}{\rm{H}} _{12}{\rm{N}}{_{6}}{\rm{O}}{_{6}}{\rm{{\cdot{}}}}{\rm{HCl}}}$\end{document} ; Z ‐furan, C 7 H 6 N 2 O 4 ; furylfuramide, C 11 H 8 N 2 O 5 ; nitrovin, \documentclass{article}\usepackage{amssymb}\pagestyle{empty}\begin{document}${{\rm{C}}{_{14}}{\rm{H}} _{12}{\rm{N}}{_{6}}{\rm{O}}{_{6}}{\rm{{\cdot{}}}}{\rm{HCl}}}$\end{document} ; furalazine C 9 H 7 N 5 O 3 ; acetylfuratrizine, C 11 H 9 N 5 O 4 ; panfuran‐S, C 11 H 11 N 5 O 5 ; nifuroxime, C 5 H 4 N 2 O 4 ; nitrofurazone, C 6 H 6 N 4 O 4 ; nifuraldezone, C 7 H 6 N 4 O 5 ; nihydrazone, C 7 H 7 N 3 O 4 ; nitrofurantoin, C 8 H 6 N 4 O 5 ; nifuratel, C 10 H 11 N 3 O 5 S; nitrofurathiazide, C 13 H 12 N 4 O 6 S; nifurtoinol, C 9 H 8 N 4 O 6 ; and nifurprinol, C 12 H 10 N 2 O 4 . Several nitrofurans have been marketed in the human and veterinary areas because of their broad spectrum of activity and relatively mild toxicity. Nitrofurans are generally stable, water‐insoluble crystalline solids, which decompose (darken) upon prolonged exposure to light or alkali. Nitrofurantoin is bactericidal at the concentrations achieved in the urinary tract and highly effective against the corresponding pathogens. Since its introduction for use in uncomplicated urinary tract infections, essentially no resistance development has occurred, unlike nearly all other antimicrobials. Nitrogurazone, furazolidone, and nitrofurantoin have been used therapeutically for over 30 yr with no reports of human neoplasia. Most commercial nitrofurans are derived from 5‐nitro‐2‐furancarboxaldehyde or the corresponding diacetate.

Crystallographic Study of Solvates and Solvate Hydrates of an Antibacterial Furazidin

“…16,17 In this study, we explored the solvate formation of furazidin (FUR Figure 1), also known under the name of furagin. FUR is a nitrofurantoin analogue with antibacterial activity 29 frequently used in the treatment of urinary tract infections mainly in eastern European countries. 30 Furazidin is known to exist in two polymorphs I and II 31,32 as well as two solvate hydrates: THF solvate hydrate (CSD refcode ASATIZ) and DMF solvate hydrate (ASATOF).…”

“…In this study, we explored the solvate formation of furazidin (FUR, 1-[(E)-[(E)-3-(5-nitrofuran-2-yl)­prop-2-enylidene]­amino]­imidazolidine-2,4-dione, molecular structure given in Figure ), also known under the name of furagin. FUR is a nitrofurantoin analogue with antibacterial activity frequently used in the treatment of urinary tract infections mainly in eastern European countries …”