SKU: N006  / 
    CAS Number: 67-20-9

    Nitrofurantoin

    $40.94 - $216.38

    Nitrofurantoin is a unique bacteriostatic antibiotic. Nitrofurantoin is practically insoluble in aqueous solution at 0.0795 mg/mL; however, it is soluble in DMF at 80 mg/mL.

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    ApplicationNitrofurantoin can be used to study antibiotic resistance.
    Mechanism of ActionNitrofurantoin has a unique mode of action in that it does not require growth or active metabolism to exert its effect. Upon entering a susceptible cell, nitrofurantoin is activated by bacterial enzymes (nitrofuran reductase) and targets ribosomes and nucleic acids which inhibit bacterial growth and leads to death of the bacterial cells. Resistance to Nitrofurantoin may be chromosomal or plasmid-mediated.
    SpectrumNitrofurantoin 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."
    It is also used agasint Enterococci, Staphylococci, Streptococci, Corneybacteria, and  E. coli.  Most strains of Proteus spp. and Pseudomonas aeurginosa are resistant to Nitrofurantoin.
    Impurity ProfileLimit of Nitrofurfural Diacetate: ≤ 1.0%
    Limit of Nitrofurazone: ≤ 0.01%
    Microbiology ApplicationsNitrofurantoin 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
    • For a representative list of nNtrofurantoin MIC values, click here.

    Nitrofurantoincan 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 ug/ml or less. The activity of this compound is pH dependent, and mean MIC rises sharply with pH >6.

    Eukaryotic Cell Culture ApplicationsNitrofuranton 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 its cytotoxic activity against bladder cancer cells using three transitional cell carcinoma lines (HTB9 (grade 2); T24 (gr 3) and TccSup (gr. 4) at concentrations ranging from 0 to 2000 ug/ml.   MTT assay.  Significant, dose-dependent cytotoxicity was seen at 7.8 ug/ml conc. in all 3 cell lines.  (Kamat and Lamm, 2004).

    Molecular FormulaC8H6N4O5
    Solubilitysoluble in DMF (80 mg/ml). Practically insoluble in aqueous solution at 0.0795 mg/mL
    References

    Fitzpatrick PM and Charles C. McOsker CM (1994)  Nitrofurantoin: Mechanism of action and implications for resistance development in common uropathogens. J. Antimicrob. Chemother. 33(Suppl A):23-30  PMID 7928834

    Kamat AM ad Lamm DL (2004)  Antitumor activity of common antibiotics against superficial bladder cancer. Urol. 63(3):457-460 PMID 15028437

    Knudsen GM, Ng Y and Gram L (2013)  Survival of bactericidal antibiotic treatment by a persister subpopulation of Listeria monocytogenes. App. Environ. Microbiol. 79(23):7390-7397  PMID 24056460

    Michiels C and Remacle J (1988)  Quantitative study of natural antioxidant systems for cellular nitrofurantoin toxicity. Biochim. Biophys. Acta 967(3):341-347  PMID 3196753

    Nickerson SC, Paape MJ, Dulin AM (1985)  Effect of antibiotics and vehicles on bovine mammary polymorphonuclear leukocyte morphologic features, viability, and phagocytic activity in vitro. Am J Vet Res. 46(11):2259-2265  PMID 4073636

    MICBacillus cereus (ML 98)| ≥25|| Bacillus subtilis| 1 - 12.5|| Bordetella bronchiseptica| >400|| Burkholderia cepacia| >400|| Edwardsiella hoshinae | 2 - 8|| Edwardsiella ictaluri | 1 - 4|| Edwardsiella tarda| 4 - 8|| Enterococcus faecalis| 8 - 12.5|| Enterococcus spp.| ≤32 - >64|| Escherichia coli| 4 - >64|| Helicobacter pylori| 1 - 2|| Klebsiella pneumonia| ≥25|| Klebsiella spp.| ≤32 - >64|| Lactobacillus acidophilus| 1 - ≥256|| Lactobacillus brevis| 16 - ≥256|| Lactobacillus casei| 64 - ≥256|| Lactobacillus curvatus| 128 - ≥256|| Lactobacillus delbrueckii| 8 - ≥256|| Lactobacillus fermentum| 32 - ≥256|| Lactobacillus gasseri| 1|| Lactobacillus johnsonii| >100|| Lactobacillus paracasei| >100|| Lactobacillus plantarum| 32 - ≥256|| Lactobacillus rhamnosus| 64 - ≥256|| Lactobacillus sakei| 128 - ≥256|| Lactobacillus salivarius| 10|| Lactobacillus sp.| 4 - 256|| Listeria spp.| 8 - >64|| Pediococcus acidilactici (HA-6111-2)| ≥16|| Proteus vulgaris| ≥100|| Pseudomonas aeruginosa| >64 - >400|| Shigella| 1 - 32|| Staphylococcus aureus| 2 - 25|| Stenotrophomonas maltophilia| ≥400|| Vibrio harveyi| 6.25||