Nitrofurans are a class of drugs typically used as antibiotics or antimicrobials. The defining structural component is a furan ring with a nitro group. These molecules undergo enzymatic nitro reduction in susceptible bacteria to generate reactive intermediates that cause DNA strand breakage and covalent modification of proteins and ribosomal components, which accounts for bactericidal activity against a range of Gram negative and some Gram positive organisms. Representative members include nitrofurantoin, nitrofurazone, furazolidone and furaltadone. Physicochemical properties vary by analog but commonly include low to moderate molecular weight, limited aqueous solubility for some derivatives, and the need for formulation strategies to achieve appropriate bioavailability. Clinical and regulatory practice reflects their pharmacokinetics, for example nitrofurantoin concentrates in urine and is therefore used primarily for lower urinary tract infections, while some nitrofurans have been used topically. Several nitrofurans are subject to regulatory restrictions in food-producing animals because of toxicological and residue concerns.
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