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Chemical Compound Review

Furfurin     [(5-nitro-2- furyl)methylideneamino]urea

Synonyms: SureCN25416, NSC-44009, NSC44009, CAS-59-87-0, ZINC00897369, ...
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Disease relevance of Furacin


High impact information on Furacin

  • After 8 hr of incubation of Chinese hamster ovary cells in 29 mM metronidazole or 500 muM nitrofurazone, the absolute plating efficiency remains relatively constant (80 to 40%) in the presence of air [6].
  • The oxygen-insensitive reductase does not form the nitro anion free radical nor in the presence of nitrofurazone does it stimulate oxygen consumption [2].
  • Rat hepatic microsomes appear to metabolize nitrofurazone in a manner similar to the oxygen-sensitive E. coli reductase [2].
  • Novel urinary catheters impregnated with nitrofurazone or minocycline and rifampin or coated with a silver alloy-hydrogel exhibit antiinfective surface activity that significantly reduces the risk of CAUTI for short-term catheterizations not exceeding 2-3 weeks [7].
  • These data confirm that N-acetyl-cysteine at the N terminus affects actomyosin interactions, probably by reducing formation of the initial actomyosin collision complex, a process known to involve the actin N terminus [8].

Chemical compound and disease context of Furacin


Biological context of Furacin


Anatomical context of Furacin

  • There have been few recent reviews of the nitrofurans in the literature, and none include recently available data on the use of nitrofurazone (nitrofural) in the prevention of catheter-associated urinary tract infection (CAUTI) [19].
  • Furthermore, the association of nebulin modules with the actin N-terminus in subdomain 1 supports the hypothesis that nebulin wraps around the outer edges of actin filaments where Sl, tropomyosin, and several actin binding proteins are known to interact [20].
  • With the latter, 50% inhibition of T cell mitogenesis was achieved by nifuroxime, nitrofurazone, and nitrofurantoin at 45-51 and 34-39 microM with PHA and ConA respectively [21].
  • Comparison of the rate of disappearance of nitrofurazone from anaerobic A549 cell suspensions with the rate of 14CO2 release suggests that the drug reduction in this cell line was catalyzed almost entirely by NADPH-requiring enzymes [11].
  • However, 5-nitro-2-furaldehyde semicarbazone was negative in both assays with hepatocytes of 2 species [22].

Associations of Furacin with other chemical compounds


Gene context of Furacin

  • No increase over the spontaneous mutation frequency was observed when recA or lexA strains were exposed to either AF2 or nitrofurazone in these experiments [27].
  • The involvement of the actin N-terminus in utrophin binding was also supported by competition binding assays using myosin subfragment S1, which also binds F-actin near its N-terminus [28].
  • The relative sensitivities to the antibacterial effects of AF2 of strains WP2, WP2 uvrA, CM561 (lexA) and CM571 (recA) were 1 : 1.6 : 3 : 7 and to nitrofurazone 1 : 1 : 25 : 50 [27].
  • In the dam mutant treated with nitrofurazone the resulting damage is not converted into DNA breaks but the high sensitivity is also suppressed by a mutH mutation [29].
  • Nitrofurazone at the same dose, however, reduced the increases in LH and PRL concentrations induced by LHRH and TRH, respectively [30].

Analytical, diagnostic and therapeutic context of Furacin


  1. Nitrofurazone in scabies. Chowdhurry, S.P. Lancet (1977) [Pubmed]
  2. Oxygen-sensitive and -insensitive nitroreduction by Escherichia coli and rat hepatic microsomes. Peterson, F.J., Mason, R.P., Hovsepian, J., Holtzman, J.L. J. Biol. Chem. (1979) [Pubmed]
  3. Activity of a nitrofurazone matrix urinary catheter against catheter-associated uropathogens. Johnson, J.R., Berggren, T., Conway, A.J. Antimicrob. Agents Chemother. (1993) [Pubmed]
  4. Chemosensitization in vitro: potentiation of melphalan toxicity by misonidazole, metronidazole and nitrofurazone. Smith, E., Lumley, C.E., Stratford, I.J., Adams, G.E. Int. J. Radiat. Oncol. Biol. Phys. (1982) [Pubmed]
  5. The bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954)--I. Purification and properties of a nitroreductase enzyme from Escherichia coli--a potential enzyme for antibody-directed enzyme prodrug therapy (ADEPT). Anlezark, G.M., Melton, R.G., Sherwood, R.F., Coles, B., Friedlos, F., Knox, R.J. Biochem. Pharmacol. (1992) [Pubmed]
  6. Increased cell killing by metronidazole and nitrofurazone of hypoxic compared to aerobic mammalian cells. Mohindra, J.K., Rauth, A.M. Cancer Res. (1976) [Pubmed]
  7. Engineering out the risk for infection with urinary catheters. Maki, D.G., Tambyah, P.A. Emerging Infect. Dis. (2001) [Pubmed]
  8. Drosophila ACT88F indirect flight muscle-specific actin is not N-terminally acetylated: a mutation in N-terminal processing affects actin function. Schmitz, S., Clayton, J., Nongthomba, U., Prinz, H., Veigel, C., Geeves, M., Sparrow, J. J. Mol. Biol. (2000) [Pubmed]
  9. Transferable nitrofuran resistance conferred by R-plasmids in clinical isolates of Escherichia coli. Breeze, A.S., Obaseiki-Ebor, E.E. J. Antimicrob. Chemother. (1983) [Pubmed]
  10. Effect of tinidazole, metronidazole and nitrofurazone on nucleic acid synthesis in Clostridium bifermentans. Plant, C.W., Edwards, D.I. J. Antimicrob. Chemother. (1976) [Pubmed]
  11. Nitroheterocycle metabolism in mammalian cells. Stimulation of the hexose monophosphate shunt. Varnes, M.E., Tuttle, S.W., Biaglow, J.E. Biochem. Pharmacol. (1984) [Pubmed]
  12. Influence of subcellular fractions of mammalian testes on the mutagenic activity of nitrofurans toward Escherichia coli; presence of a co-mutagen-like factor. Maier, P., Philpot, R.M., Mohn, G.R., Malling, H.V. Mutat. Res. (1979) [Pubmed]
  13. A new stable pluronic F68 gel carrier for antibiotics in contaminated wound treatment. Faulkner, D.M., Sutton, S.T., Hesford, J.D., Faulkner, B.C., Major, D.A., Hellewell, T.B., Laughon, M.M., Rodeheaver, G.T., Edlich, R.F. The American journal of emergency medicine. (1997) [Pubmed]
  14. Location of the binding site of the mannose-specific lectin comitin on F-actin. Fulgenzi, G., Graciotti, L., Granata, A.L., Corsi, A., Fucini, P., Noegel, A.A., Kent, H.M., Stewart, M. J. Mol. Biol. (1998) [Pubmed]
  15. Nitrofurazone: kinetics and oxidative stress in the singlepass isolated perfused rat liver. Hoener, B.A. Biochem. Pharmacol. (1988) [Pubmed]
  16. Structure/activity relationships for the enhancement by electron-affinic drugs of the anti-tumour effect of CCNU. Workman, P., Twentyman, P.R. Br. J. Cancer (1982) [Pubmed]
  17. Genetics of nitrofurazone resistance in Escherichia coli. McCalla, D.R., Kaiser, C., Green, M.H. J. Bacteriol. (1978) [Pubmed]
  18. Mutagen screening with bacteria: niridazole and nitrofurans. McCalla, D.R., Voutsinos, D., Olive, P.L. Mutat. Res. (1975) [Pubmed]
  19. An update on the role of nitrofurans in the management of urinary tract infections. Guay, D.R. Drugs (2001) [Pubmed]
  20. Molecular contacts between nebulin and actin: cross-linking of nebulin modules to the N-terminus of actin. Shih, C.L., Chen, M.J., Linse, K., Wang, K. Biochemistry (1997) [Pubmed]
  21. Inhibition of T cell mitogenesis by nitrofurans. Mercado, C., Molina, F., Navas, J., Quiñones, C., Eylar, E.H. Biochem. Pharmacol. (1991) [Pubmed]
  22. Genotoxicity of a variety of nitroarenes and other nitro compounds in DNA-repair tests with rat and mouse hepatocytes. Mori, H., Sugie, S., Yoshimi, N., Kinouchi, T., Ohnishi, Y. Mutat. Res. (1987) [Pubmed]
  23. Activities of a nitrofurazone-containing urinary catheter and a silver hydrogel catheter against multidrug-resistant bacteria characteristic of catheter-associated urinary tract infection. Johnson, J.R., Delavari, P., Azar, M. Antimicrob. Agents Chemother. (1999) [Pubmed]
  24. Oxygen-insensitive nitroreductases: analysis of the roles of nfsA and nfsB in development of resistance to 5-nitrofuran derivatives in Escherichia coli. Whiteway, J., Koziarz, P., Veall, J., Sandhu, N., Kumar, P., Hoecher, B., Lambert, I.B. J. Bacteriol. (1998) [Pubmed]
  25. The nitrofurans as sperm immobilizing agents. Albert, P.S., Salerno, R.G., Kapoor, S.N., Davis, J.E. J. Urol. (1975) [Pubmed]
  26. Aerobic reduction of 5-nitro-2-furaldehyde semicarbazone by rat liver xanthine dehydrogenase. Kutcher, W.W., McCalla, D.R. Biochem. Pharmacol. (1984) [Pubmed]
  27. Action of nitrofurans on E. coli: mutation and induction and repair of daughter-strand gaps in DNA. Lu, C., McCalla, D.R., Bryant, D.W. Mutat. Res. (1979) [Pubmed]
  28. Biochemical characterisation of the actin-binding properties of utrophin. Moores, C.A., Kendrick-Jones, J. Cell Motil. Cytoskeleton (2000) [Pubmed]
  29. Characterization of a dam mutant of Haemophilus influenzae Rd. Zaleski, P., Piekarowicz, A. Microbiology (Reading, Engl.) (2004) [Pubmed]
  30. Effects of furazolidone or nitrofurazone on the concentrations of hypothalamic amines and plasma luteinizing hormone (LH) and prolactin (PRL), levels in young turkeys. Ali, B.H., Silsby, J.L., Edens, F., el Halawani, M.E. Gen. Pharmacol. (1988) [Pubmed]
  31. Nitrofurazone: vas irrigation as adjunct in vasectomy. Albert, P.S., Seebode, J. Urology (1977) [Pubmed]
  32. Hepatic changes of the teleost, Oryzias latipes after treatment with AF-2 and nitrofurazone [proceedings]. Aoki, K., Taguchi, Y., Matsudaira, H., Ishikawa, T. Mutat. Res. (1976) [Pubmed]
  33. Electrochemical reduction of nitrofurazone and its determination in pharmaceutical dosage forms by d.c. polarography. Mishra, A.K., Gode, K.D. The Analyst. (1985) [Pubmed]
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