Nitrofurantoin

67-20-9

C8H6N4O5

238.16

Yellow crystalline powder

Soluble in DMF. Practically insoluble in aqueous solution.

Source: Synthetic
Water Content (Karl Fischer): < 1.0%
Assay: (On dried basis): 98.0-102.0%

≤30°C. Protect from light.

Spectrum: Nitrofurantoin is a broad-spectrum antibiotic frequently used to treat bacterial infections of the urinary tract. Nitrofurantoin has been found to be effective against certain β-lactam resistant strains of VRE or vancomycin resistant Enterococcus; a glycopeptide antibiotic resistant "superbug." Nitrofurantion is also used against Enterococci, Staphylococci, Streptococci, Corneybacteria, and E. coli. Most strains of Proteus spp. and Pseudomonas aeurginosa are resistant to Nitrofurantoin.

Microbiology Applications: Nitrofurantoin is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against Gram-positive and Gram-negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options. Representative MIC values include:
E. coli 32 µg/mL - 64 µg/mL

Nitrofurantoin can be used against Lysteria monocytogenes-persisters in vitro, and was effective against both growing and dormant cells (Knudsen et al, 2013).
In general, organisms are said to be susceptibile if the MIC is ≤ 32 µg/ml. The activity of this compound is pH- dependent, and the mean MIC rises sharply with pH >6.

Eukaryotic Cell Culture Applications: Nitrofuranton is toxic to human WI-38 fibroblasts in culture and antioxidants can mitigate effect. On a molecular basis, glutathione peroxidase was the most efficient at protection (Michiels and Remacle, 1988). Nitrofurantoin can alter the morphology, viability, and phagocytic activity of bovine mammary polymorphonuclear leukocytes in vitro, when added at 1 mg/ml (Nickerson et al, 1995).

Cancer Applications: Nitrofurantoin was evaluated for cytotoxic activity against bladder cancer cells using three transitional cell carcinoma lines (HTB9 (grade 2); T24 (gr 3) and TccSup (gr. 4) at 0-2000 µg/ml using the MTT assay. Significant, dose-dependent cytotoxicity was seen at 7.8 µg/ml in all 3 cell lines (Kamat and Lamm, 2004).