Skip to main content

Part of the book series: Antibiotics ((1512,volume 5 / 1))

Abstract

Since the first reports of the antibacterial action of nitrofuran derivatives in the 1940s (Dodd and Stillman, 1944; Dann and Möller, 1947) many hundreds of different nitrofuran derivatives have been synthesized and subjected to some degree of biological evalution. Several of these agents, including nitrofurantoin and furazolidone, have been adopted for extensive use in clinical and veterinary medicine. Others have been used as preservatives in human food (AF-2) or added to feed for poultry and swine (e.g., nitrofurazone, furazolidone, furaltadone). With the discovery that certain nitrofuran derivatives are carcinogenic, there has been some curtailment of the use of these agents and further restrictions have recently been proposed (Anon, 1976). Nevertheless, these compounds remain in widespread use and the synthesis of new nitrofuran derivatives continues apace. Indeed, 10% of the 671 references on nitrofurans which were retrieved during a computer search of Chemical Abstracts for the period 1971 to spring 1977 were journal articles dealing with synthesis of new derivatives while an additional 30% referred to patents. Included were items describing antibacterial soaps (Andree and Koppensteiner, 1974), use of nitrofurazone in deodorant (Komura et al., 1974; Kotani and Kageyama, 1976), use of nitrofurylacrylic acid as a stabilizer in wine (Farkas, 1975), nitrofuryl-benzimi-dazole derivatives for use as fungicides (Toth and Toth, 1976), methylthiocyanate derivatives for use in seed treatment (Demecko et al., 1977) and means of incorporating nitrofuryl groups into synthetic fibers to prevent microbial degradation (Gavilova et al., 1974) or to confer antibacterial properties (Siennicki, 1973).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Adams, G.E., Clarke, E.D., Jacobs, R.S., Stratford, I.J., Wallace, R.G., Wardman, P., Watts, M.E.: Mammalian cell toxicity of nitro compounds: Dependence upon reduction potential. Biochem. Biophys. Res. Commun. 72, 824–829 (1976)

    PubMed  CAS  Google Scholar 

  • Akao, M., Kuroda, K., Miyaki, K.: Metabolic degradations of nitrofurans by rat liver homogenate.

    Google Scholar 

  • Biochem. Pharmacol. 20, 3091–3096 (1971)

    Google Scholar 

  • Akao, M., Kuroda, K., Miyaki, K.: Selective inhibition of RNA polymerase activity in rat liver nuclei by 4- (dimethylamino) azobenzene, and effect of nitrofurans on liver RNA metabolism associated with prevention of carcinogenesis. Gann 63, 1–10 (1972)

    PubMed  CAS  Google Scholar 

  • Akao, M., Kuroda, K., Tsutsui, Y., Kanisawa, M., Miyaki, K.: Effect of nitrofurans antagonistic to 3′-methyl-4-dimethylaminoazobenzene in hepatocarcinogenesis and RNA polymerase activity of liver cell nuclei in rats. Cancer Res. 34, 1843–1850 (1974)

    PubMed  CAS  Google Scholar 

  • Albert, P.S., Salerno, R.G., Kapoor, S.K., Davis, J.E.: The nitrofurans as sperm immobilizing agents. Urol. 113, 69–70 (1975)

    CAS  Google Scholar 

  • Andree, H., Koppensteiner, G.: Antimicrobial 5-nitrofurfural acetals, Patent — Germany (West). Chem. Abstr. 80, 120739w (1974)

    Google Scholar 

  • Anon: New animal drug applications. Furaltadone (NF260), nitrofurazone (NF-73), nihydrazone (NF64). Opportunity for hearing on proposal to withdraw approval of certain new animal drug applications. Fed. Regist. 41, 34884–34921 (1976)

    Google Scholar 

  • Arai, T., Aoki, T., Egusa, S.: Mechanisms of decrease of nitrofuran sensitivity conferred by R. factors. In: Microbial Drug Resistance. Mitsuhashi, S., Hashimoto, H. (eds.), pp. 505–513. Baltimore, Maryland: Univ. Park Press 1975

    Google Scholar 

  • Asnis, R.E.: The reduction of furacin by cell-free extracts of furacin-resistant and parent-susceptible strains of Escherichia coli. Arch. Biochem. Biophys. 66, 208–216 (1957)

    PubMed  CAS  Google Scholar 

  • Asnis, R.E., Gots, J.S.: Studies on the action of nitrofurans on bacterial enzyme systems. I. Inhibition of bacterial respiration by furacin. Arch. Biochem. 30, 25–34 (1951)

    PubMed  CAS  Google Scholar 

  • Asnis, R.E., Cohen, F.B., Gots, J.S.: Studies on bacterial resistance to furacin. Antibiot. Chemother. 2, 123–129 (1952)

    CAS  Google Scholar 

  • Asnis, R.E., Glick, M.C., Fritz, ML: Effect of furacin on the dissimilation of pyruvate and formate by cell-free extracts of bacteria. J. Biol. Chem. 227, 863–869 (1957) Austin, F.L.: Reduction of nitrofurazone with Raney Nickel. Chem. and Ind. 523 (1957)

    PubMed  CAS  Google Scholar 

  • Beckett, A.H., Robinson, A.E.: Bacterial and chemical reduction of nitrofurazone. Chem. and Ind. 523–524 (1957)

    Google Scholar 

  • Beckett, A.H., Robinson, A.E.: The reactions of nitrofurans with bacteria — II. Reduction of a series of antibacterial nitrofurans by Aerobacter aerogenes. J. Med. and Pharm. Chem. I, 135–153 (1959 a)

    Google Scholar 

  • Beckett, A.H., Robinson, A.E.: The reaction of nitrofurans with bacteria III. Reduction of a series of antibacterial nitrofurans (type B compounds) by Aerobacter aerogenes. J. Med. Pharm. Chem. I, 155–164 (1959 b)

    Google Scholar 

  • Bender, R.C., Paul, H.E.: Metabolism of the nitrofurans II. Incubation of furacin with mammalian tissues. J. Biol. Chem. 191, 217–222 (1951)

    PubMed  CAS  Google Scholar 

  • Biaglow, J.E., Nygaard, O.F., Greenstock, C.L.: Electron transfer in Ehrlich ascites tumor cells in the presence of nitrofurans. Biochem. Pharmacol. 25, 393–398 (1976)

    PubMed  CAS  Google Scholar 

  • Boyland, E., Speyer, B.E.: Enzyme-catalysed reactions between some 2-substituted 5-nitrofuran derivatives and glutathione. Biochem. J. 119, 463–472 (1970)

    PubMed  CAS  Google Scholar 

  • Brener, Z.: Biology of trypanosoma cruzi. Annu. Rev. Microbiol. 27, 347–382 (1973)

    PubMed  CAS  Google Scholar 

  • Bridges, B.A., Dennis, R.E., Munson, R.J.: Differential induction and repair of ultra violet damage leading to true reversions and external suppressor mutations of an ochre codon in Escherichia coli B/r WP2. Genetics 57, 897–908 (1967)

    PubMed  CAS  Google Scholar 

  • Brodie, A.F., Gots, J.S.: Nitrofurans as electron acceptors for certain respiratory enzymes. Arch. Biochem. Biophys. 39, 165–173 (1952 b)

    PubMed  CAS  Google Scholar 

  • Buzard, J.A.: Direct conversion to naturally occuring products, a rarely considered pathway of drug metabolism. J. Am. Pharm. Assoc. Sci. Ser. B-XI (1962)

    Google Scholar 

  • Cançado, J.R., Marra, U.D., Brener, Z.: Ensaio terapeutico clinico com a 5-nitro-2-fural deidosemicarbazona (Nitrofurazona) na forma cronica da doenca de Chagas. Rev. Inst. Med. Trop. Sao Paulo 6, 12–16 (1964)

    PubMed  Google Scholar 

  • Cançado, J.R., Marra, U.D., Lopes, M., Mourão, O., Faria, C.A.F., Alvares, J.M., Salgado, A.D.A.: Toxicidad y valor terapeutico del bay 2502 en la enfermedad de Chagas cronica en tres esquemas posologicos. Bol. Chileno de Parasitol. 24, 28–32 (1969)

    Google Scholar 

  • Cançado, J.R., Salgado, A.A., Batista, S.M., Chiari, C.A.: Nifurtimox (Lampit). Rev. Goiana. Med. 31–44 (1976)

    Google Scholar 

  • Carey, W.F., Russell, H.E., O’Connor, J.R.: The effect of nitrofurans on the survival of bacteria in vivo. Antimicrob. Agents Ann. 152–158 (1960)

    Google Scholar 

  • Carey, W.F., Russell, H.E., O’Connor, J.R.: The effect of nitrofurans on the survival of bacteria in vivo. Antimicrob. Agents. Annu. 1960, pp. 152–158. New York: Plenum Press 1961 Chamberlain, R.E.: Chemotherapeutic properties of prominent nitrofurans. J. Antimicrob. Chemother. 2, 325–336 (1976)

    Google Scholar 

  • Chatfield, D.H.: Disposition and metabolism of some nitrofurylthiazoles possessing antiparasitic activity. Xenobiotica 6, 509–520 (1976)

    PubMed  CAS  Google Scholar 

  • Chatterjee, S.N., Maiti, M., Ghosh, S.: Interaction of furazolidone with DNA. Biochim. Biophys. Acta. 402, 161–165 (1975)

    PubMed  CAS  Google Scholar 

  • Chernomordik, A.B.: Synergistic effect of antibiotics on Bac. pyocyaneus [Pseudonomonas aeruginosa]. Antibiotiki 12, 604–606 (1967)

    PubMed  CAS  Google Scholar 

  • Chylak, J.: In vitro study of the combined effect of streptomycin and nitrofurantoin on Escherichia coli. Wiad. Lek. 26, 1413–1418 (1973)

    PubMed  CAS  Google Scholar 

  • Cleaver, J.E., Bootsma, D.: Xeroderma Pigmentosum: Biochemical and genetic characteristics. Ann. Rev. Genet. 9, 19–38 (1975)

    PubMed  CAS  Google Scholar 

  • Cohen, S.M., Bryan, G.T.: Carcinogenesis caused by nitrofuran derivatives. Proc. 5th Int. Congr. Pharmacol. 2, 164–170 (1973)

    CAS  Google Scholar 

  • Cohen, S.M., Ertürk, E., Bryan, G.T.: Production of leukemia and stomach neoplasms in Swiss, RF, BALB/c, and C3H Female mice by feeding N-[4- (5-nitro-2-furyl)-2-thiazolyl]acetamide. Cancer Res. 30, 2320–2325 (1970)

    PubMed  CAS  Google Scholar 

  • Cohen, S.M., Ertürk, E., Von Esch, A.M., Crovetti, A.J., Bryan, G.T.: Carcinogenicity of 5-nitrofurans, 5-nitroimidazoles, 4-nitrobenzenes and related compounds. J. Natl. Cancer Inst. 51, 403–417 (1973 a)

    PubMed  CAS  Google Scholar 

  • Cohen, S.M., Alter, A., Bryan, G.T.: Distribution of radioactivity and metabolism of formic acid 2-[4- (5-nitro-2-furyl)-2-14C-2-thiazolyl]hydrazide following oral administration to rats and mice. Cancer Res. 33, 2802–2809 (1973 b)

    PubMed  CAS  Google Scholar 

  • Cohen, S.M., Headley, D.B., Bryan, G.T.: Carcinogenesis and immunosuppression by N-[4- (5-nitro-2-furyl)-2-thiazolyl] acetamide (NFTA) and related 5-nitrofurans in BALB/c Mice. XI Int. Cancer Congr. 2, 40–41 (1974)

    Google Scholar 

  • Cole, W.H.: Chemotherapy of cancer, p. 168. Philadelphia: Lee and Febiger 1970 Conklin, J.D., Buzard, J. A.: Absorption and Distribution of oxafuradene in the dog. J. Pharm. Sci. 54, 1766–1770 (1965)

    Google Scholar 

  • Corvaja, C, Farina, G., Vianello, E.: Kinetics of decay of nitrophenol radical anions and reduction of nitrophenols in aqueous alkaline medium. Electrochim. Acta 11, 919–929 (1966)

    CAS  Google Scholar 

  • Crain, E.M., Ray, W.H.: Metabolites of furazolidone in urine of chickens. J. Pharm. Sci. 61, 1495–1497 (1972)

    Google Scholar 

  • Dann, O., Möller, E.F.: Bakteriostatisch wirkende Nitro-verbindungen des Thiophens und Furans. Chem. Ber. 80, 23–36 (1947)

    CAS  Google Scholar 

  • Dauvarte, A., Zidermane, A., Kainbergs, R., Lidaks, M., Kurgane, B., Sukhova, N.M., Hillers, S.: Antineoplastic activity of N,N-bis (2-chloroethyl)amino and N,N-bis (2-chloroethyl)hydrazino derivatives of aromatic and heterocyclic aldehydes. Protivoopukholevye Soedin 72, 33–44 (1973), seen as Chem. Abstr. 78, 92412x (1973)

    Google Scholar 

  • Demecko, J., Koneczy, V., Krutcsikova, A., Kovac, J.: 5-nitro-2-furfuryl nitrate, a fungicidal seed dressing. Patent — Czechoslovakia. Chem. Abstr. 86, 12696v (1977)

    Google Scholar 

  • Dietrich, R.A., Hellerman, L.: Diphosphopyridine nucleotide-linked aldehyde dehydrogenase II. Inhibitors. J. Biol. Chem. 238, 1683–1689 (1963)

    Google Scholar 

  • Dodd, M.C., Stillman, W.B.: The in vitro bacteriostatic action of some simple furan derivatives. J. Pharmacol. Exp. Ther. 82, 11–18 (1944)

    CAS  Google Scholar 

  • Ebetino, F.F., Carroll, J.J., Gever, G.: Reduction of nitrofurans I. Aminofurans. J. Med. Pharm. Chem. 5, 513–524 (1962)

    CAS  Google Scholar 

  • Ebringer, L., Krkoska, P., Macor, M., Jurasek, A., Kada, R.: Furan derivatives — their common molecular denominator responsible for bleaching of Euglena gracilis. Arch. Mikrobiol. 57, 61–67 (1967 a)

    PubMed  CAS  Google Scholar 

  • Ebringer, L., Jurasek, A., Kada, R.: Antibiotics and Apochlorosis III Effect of 5-nitrofurans on the chloroplast system of Euglena gracilis. Folia Microbiol. 12, 151–156 (1967 b)

    CAS  Google Scholar 

  • Ebringer, L., Jurasek, A., Kada, R., Krikoska, P., Foltinova, P.: New nitrofurans — a correlation study between chemical structures and biological activities. Adv. Antimicrob. Antineoplast. Chemother. 1, 873–876 (1972)

    CAS  Google Scholar 

  • Ebringer, L., Jurasek, A., Konicek, J., Konickova, M., Lahitova, N., Trubacik, S.: Mutagenic action of nitrofurans on Euglena gracilis and Mycobacterium phlei. Antimicrob. Agents Chemother. 9, 682–689 (1976)

    PubMed  CAS  Google Scholar 

  • Elslager, E.F.: Antiamebic Agents.: Medicinal chemistry, 3rd. ed. Burger, A. (ed.), pp. 522–561. Wiley-Interscience 1970

    Google Scholar 

  • Endo, H., Ishizawa, M., Kamiya, T., Kuwana, M.: A nitrofuran derivative, a new inducing agent for the phage development in lysogenic E. coli. Biochim. Biophys. Acta 68, 502–505 (1963)

    CAS  Google Scholar 

  • Ertürk, E., Price, J.M., Morris, J.E., Cohen, S., Leith, R.S., Von Esch, A.M., Crovetti, A.J.: The production of carcinoma of the urinary bladder in rats by feeding N-4-[5-nitro-2-furyl)-2-thiazolyl]formamide. Cancer Res. 27, 1998–2002 (1967)

    PubMed  Google Scholar 

  • Ertürk, E., Morris, J.E., Cohen, S.M., Price, J.M., Bryan, G.T.: Transplantable rat mammary tumors induced by 5-nitro-2-furaldehyde semicarbazone and by formic acid 2-[4- (5-nitro 2-furyl)-2-thiazolyl]hydrazide. Cancer Res. 30, 1409–1412 (1970 a)

    PubMed  Google Scholar 

  • Ertürk, E., Atassi, S.A., Yoshida, O., Cohen, S.M., Price, J.M., Bryan, G.T.: Comparative urinary and gallbladder carcinogenicity of N-[4- (5-nitro-2-furyl)-2-thiazolyl]formamide and N-[4- (5-nitro-2-furyl)-2-thiazolyl]acetamide in the dog. J. Natl. Cancer Inst. 45, 535–542 (1970 b)

    PubMed  Google Scholar 

  • Ertürk, E., Morris, J.E., Cohen, S.M., Von Esch, A.M., Crovetti, A.J., Price, J.M., Bryan, G.T.: Comparative carcinogenicity of formic acid 2-[4- (5-nitro-2-furyl)-2-thiazolyl]hydrazide and related chemicals in the rat. J. Natl. Cancer Inst. 47, 437–445 (1971)

    PubMed  Google Scholar 

  • Farkas, J.: 5-nitrofurylacrylic acid, a new conserving agent in vinification. Mitt. Hoeheren Bundeslehr-Versuchsanst. Wein-Obstbau, Kloster Neuburg 25, 279–284 (1975), seen as Chem. Abst. 84, 119900 (1976)

    CAS  Google Scholar 

  • Featherstone, R.M., Nelson, W.O., Weiden, F., Marberger, E., Boccabella, A., Boccabella, R.: Pyruvate oxidation in testicular tissues during furadroxyl-induced spermatogenic arrest. Endocrinology 56, 727–736 (1955)

    PubMed  CAS  Google Scholar 

  • Feller, D.R., Morita, M., Gillette, J.R.: Reduction of heterocyclic nitro compounds in the rat liver. Proc. Soc. Exp. Biol. Med. 137, 433–437 (1971 a)

    CAS  Google Scholar 

  • Feller, D.R., Morita, M., Gillette, J.R.: Enzymatic reduction of niridazole by rat liver microsomes. Biochem. Pharmacol. 20, 203–215 (1971 b)

    PubMed  CAS  Google Scholar 

  • Finegold, S.M., Ziment, I.: Sulfonamides, nitrofurans and nalidixic acid. In: Antimicrobial therapy, pp. 102–118. Philadelphia: W.B. Saunders Co. 1970

    Google Scholar 

  • Fridovich, I.: Superoxide dismutases. Ann. Rev. Biochem. 44, 147–159 (1975)

    PubMed  CAS  Google Scholar 

  • Gale, G.R.: The inhibition by furacin of adaptive enzyme formation in Mycobacterium butyricum. Science 114, 689–690 (1951)

    PubMed  CAS  Google Scholar 

  • Gavilova, L.M., Sorokin, E.Ya., Gopkin, D.D., Golikov, A.S., Vol’f, L.A., Danchenko, L.S.: Fibers resistant to bacteria and fungi. Patent — USSR. Chem. Abstr. 81, 107351q (1974)

    Google Scholar 

  • Gavin, J.J., Ebetino, F.F., Freedman, R., Waterbury, W.E.: The aerobic degradation of l- (5-nitrofurfuryl-ideneamino)-2-imidazolidinone (NF-246) by Escherichia coli. Arch. Biochem. Biophys. 113, 399–404 (1966)

    PubMed  CAS  Google Scholar 

  • German, A., Panouse-Perrin, J., Ardouin, A.C.: Delysogenation of lysogenized Staphylococcus aureus by mutagenic substances. Comparison of mitomycin C, nalidixic acid, nitrofurazone, nitrofurantoin and novobiocin. C.R. Acad. Sci. Ser. D 273, 432 –435 (1971)

    Google Scholar 

  • Glascock, H.W., MacLeod, P.F., Davis, J.B., Cuddihy, R.V., Anzlowar, B.R.: Is nitrofurazone a primary irritant or a potent sensitizer? Rev. Allergy 2, 52–58 (1969)

    Google Scholar 

  • Goodman, D.R., Hakkinen, P.J., Nemenzo, J.H., Vore, M.: Mutagenic evaluation of nitrofuran derivatives in Salmonella typhimurium, by the micronucleus test, and by in vivo cytogenetics. Mutat. Res. 48, 295–305 (1977)

    PubMed  CAS  Google Scholar 

  • Grant, D.J.W., De Szocs, J.: Inhibitor effects of some anti-inflammatory and other analgesics and nitrofurans on the induction of β-galactosidase synthesis in Klebsiella aerogenes. Biochem. Pharmacol. 20, 625–635 (1971)

    PubMed  CAS  Google Scholar 

  • Green, M.H.L., Muriel, W.J.: Mutagen testing using TRP+ reversion in Escherichia coli. Mutat. Res. 38, 3–32 (1976)

    PubMed  CAS  Google Scholar 

  • Green, M.H.L., Rogers, A.M., Muriel, W.J., Ward, A.C., McCalla, D.R.: Use of a simplified fluctuation test to detect and characterize mutagenesis by nitrofurans. Mutat. Res. 44, 139–143 (1977)

    PubMed  CAS  Google Scholar 

  • Green, M.N.: The effect of furacin (5-nitro-2-furaldehyde semicarbazone) on the metabolism of bacteria. Arch. Biochem. 19, 397–406 (1948)

    PubMed  CAS  Google Scholar 

  • Green, M.N., Heath, E.C., Yall, I.: Effect of furacin (5-nitro-2-furaldehyde semicarbazone) on various sulfhydryl and nonsulfhydryl enzymes. Proc. Soc. Exp. Biol. Med. 76, 152–155 (1955)

    Google Scholar 

  • Grunberg, E., Titsworth, E.H.: Chemotherapeutic properties of heterocyclic compounds: Monocyclic compounds with five-membered rings. Ann. Rev. Microbiol. 27, 317–346 (1973)

    CAS  Google Scholar 

  • Gruneberg, R.N.: The choice of treatment of urinary infection according to the sensitivities of the causative organisms. Adv. Antimicrob. Antineoplast. Chemother. 1, 749–750 (1972)

    Google Scholar 

  • Hailey, J.F., Glascock, H.W., Hewitt, W.F.: Pleuropneumonie reactions to nitrofurantoin. N. Engl. J. Med. 281, 1087–1090 (1969)

    PubMed  CAS  Google Scholar 

  • Hamilton-Miller, J.M.T., Brumfitt, W.: The versatility of nitro compounds. J. Antimicrob. Chemother. 2, 5–7 (1976)

    PubMed  CAS  Google Scholar 

  • Hayllar, B.L., O’Neal, A.H., Jr., Dotterer, J.A.: Metastatic testicular tumor treated with a maintenance dose of nitrofurazone. J. Urol. 84, 565–568 (1960)

    PubMed  CAS  Google Scholar 

  • Headley, D.B., Klopp, R.G., Ewenko, J.M., Bryan, G.T.: Effects of the carcinogens N-[4- (5-nitro-2-furyl)-2-thiazolyl]acetamide (NFTA) and (FANFT) and their non-nitro analogues on anti-body-mediated (AMI) and cell-mediated (CMI) murine immunity. Proc. Am. Assoc. Cancer Res. 243 (1977)

    Google Scholar 

  • Herrett, R.J., Williams, C.W., Heotis, J.P., Buzard, J.A.: Metabolism of 5-nitro-2-furaldehyde acetylhydrazone (nihydrazone) in the chick. J. Agric. Food Chem. 15, 433–438 (1967)

    CAS  Google Scholar 

  • Herrlich, P., Schweiger, M.: Nitrofurans, a group of synthetic antibiotics, with a new mode of action: Discrimination of specific messenger RNA classes. Proc. Natl. Acad. Sci. USA 73, 3386–3390 (1976)

    PubMed  CAS  Google Scholar 

  • I ARC: Monographs on the evaluation of carcinogenic risk of chemicals to man. 7, 170–179 (1974)

    Google Scholar 

  • Ikenaga, M., Ichikawa-Ryo, H., Kondo, S.: The major cause of inactivation and mutation by 4-nitroquinoline 1-oxide in Escherichia coli: Excisable 4NQO-Purine Adducts. J. Mol. Biol. 92, 341–356 (1975)

    PubMed  CAS  Google Scholar 

  • Inui, N., Kaketomi, M., Nishi, Y.: Mutagenic effects of AF-2 a food additive, on embryonic cells of the Syrian golden hamster on transplacental application. Mutat. Res. 41, 351–360 (1976)

    PubMed  CAS  Google Scholar 

  • Jacobs, J.B., Arai, M., Cohen, S.M., Friedell, G.H.: Light and scanning electron microscopy of exfoliated bladder epithelial cells in rats fed N-[4- (5-nitro-2-furyl)-2-thiazolyl]formamide. J. Natl. Cancer Inst. 57, 63–66 (1976)

    PubMed  CAS  Google Scholar 

  • Jenkins, S.T., Bennett, P.M.: Effect of mutations in DNA repair pathways on the sensitivity of Escherichia coli K12 strains to nitrofurantoin. J. Bacteriol. 125, 1214–1216 (1976)

    PubMed  CAS  Google Scholar 

  • Joner, P.E., Dahle, H.K., Aune, T., Dybing, E.: Mutagenicity of nitrovine — A nitrofuran feed additive. Mutat. Res. 48, 313–318 (1977)

    PubMed  CAS  Google Scholar 

  • Kada, T.: Escherichia coli mutagenicity of furylfuramide. Jpn. J. Genet. 48, 301–305 (1973)

    Google Scholar 

  • Kada, T.: Metabolic activation and Escherichia coli mutagenesis of furyl-furamide, a nitrofuran food additive. Ann. Rep. Natl. Inst. Genet. Jpn. 24, 39–41 (1974)

    Google Scholar 

  • Kastering, B.: Electrochemische Bildung, Reaktivität und Eigenschaften des nitrobenzolradikalanions. Electrochim. Acta 9, 241–245 (1964)

    Google Scholar 

  • Katae, H., Iwana, H., Takase, Y., Shimizu, M.: Antitumor activity of nitrofuran and nitrothiophene derivatives on Ehrlich ascites carcinoma. Arzneimittelforschung 17, 1030–1034 (1967)

    PubMed  CAS  Google Scholar 

  • Kato, K., Sugino, Y., Endo, H.: Effects of a prophage inducer, a nitrofuran derivative, on the DNA metabolism in Escherichia coli. Biochim. Biophys. Acta. 119, 309–321 (1966)

    PubMed  CAS  Google Scholar 

  • Kato, R., Takahashi, A., Oshima, T.: Characteristics of nitro reduction of the carcinogenic agent, 4-nitroquinolone N-oxide. Biochem. Pharmacol. 19, 45–55 (1970 a)

    PubMed  CAS  Google Scholar 

  • Kato, N., Okabayashi, K., Mizuno, D.: The degradation of ribosomal RNA in E. coli by mitomycin C and AF-5, preferential inhibitors of DNA synthesis. J. Biochem. 67, 175–184 (1970 b)

    PubMed  CAS  Google Scholar 

  • Kefauver, D.F., Paberzs, I., McNamara, T.F.: Furaltadone — a new antibacterial nitrofuran. Antibiotics Annual 1958–1959, 81–87 (1959)

    Google Scholar 

  • Kimbro, E.L., Sachs, M.W., Torbert, J.V.: Mechanism of the hemolytic anemia induced by nitrofurantoin (FuradantinR). Further observations on the incidence and significance of “primaquinesensitive” red cells. Bull. Johns Hopkins Hosp. 101, 245–257 (1957)

    PubMed  CAS  Google Scholar 

  • Kirby, E.P., Ruff, W.L., Goldthwait, D.A.: Cell division and prophage induction in Escherichia coli. Effects of pantoyl lactone and various furan derivatives. J. Bacteriol. 111, 447–453 (1972)

    PubMed  CAS  Google Scholar 

  • Kirpichev, V.I., Kulyash, Yu.V., Ivanovskii, N.N.: Effect of derivatives of 5-nitrofuran on carbohydrate metabolism in Staphylococcus aureus. Eksperimental Naya I Klinicheskaya Farmakoterapiya-cisti 5, 97–101 (1973), seen as Chem. Abst. 81, 298a (1974)

    Google Scholar 

  • Klein, H.: Alkohol and medikamente. I. Durch medikamente verursachte Alkoholunverträglichkeit und verstärkte Alkoholwirkung. Fortschr. Med. 82, 169–172 (1964)

    Google Scholar 

  • Koike, M., Iida, K., Nakashima, K., Tokunaga, J.: Small cell formation of Staphylococcus aureus by subinhibitory concentrations of nitrofuran derivatives. J. Bacteriol. 120, 524–526 (1974)

    PubMed  CAS  Google Scholar 

  • Komura, M., Deguchi, S., Tadano, K.: Deodorant containing 5-nitro-2-furfural semicarbazone for hygienic use. Patent — Japan. Chem. Abstr. 80, 149037b (1974)

    Google Scholar 

  • Kondracki, M.: The acquirement of resistance to antibiotics and nitrofuran compounds by E. coli isolated from calves with colibacillosis 1. in vitro studies. Bull. Vet. Inst. Pulway 17, 1–5 (1973)

    CAS  Google Scholar 

  • Kotani, Y., Kageyama, K.: Glyoxal and nitrofuran derivatives as deodorants. Patent — Japan. Chem. Abstr. 84, 184797 d (1976)

    Google Scholar 

  • Kunze, E., Schauer, A., Krusmann, G.: Focal loss of alkaline phosphatase and increase of proliferation in preneoplastic areas of the rat urothelium after administration of N-butyl-N- (4-hydroxybutyl)-nitrosamine and N-[4- (5-nitro-2-furyl)-2-thiazolyl]formamide. Z. Krebsforsch. 84, 143–160 (1975)

    CAS  Google Scholar 

  • Kuroda, Y.: Mutagenesis in cultured human diploid cells III. induction of 8-azaguanine-resistant mutations by furylfuramide. Mutat. Res. 30, 229–237 (1975)

    PubMed  CAS  Google Scholar 

  • Lan, S.J., Weliky, L, Schreiber, E.C.: Metabolic studies with trans-5-amino-3-[2- (5-nitro-2-furyl)-vinyl]-l,2,4-[5-14C] oxadiazole (SQ 18,506): 1. Reductive cleavage of the 1,2,4-oxidiazole ring. Xenobiotica 3, 97–102 (1973)

    PubMed  CAS  Google Scholar 

  • Maher, V.M., Curren, R.D., Ouellette, L.M., McCormick, J.J.: Effect of DNA repair on the frequency of mutations induced in human cells by ultraviolet irradiation and by chemical carcinogens. In: Fundamentals in cancer prevention. Magee, P., Takayama, S., Sugimura, T., Matsushima, T. (eds.), pp. 363–382. Univ. of Tokyo Press 1976

    Google Scholar 

  • Mason, R.P., Holtzman, J.L.: The role of catalytic superoxide formation in the O2 inhibition of nitroreductase. Biochem. Biophys. Res. Commun. 67, 1267–1274 (1975 a)

    PubMed  CAS  Google Scholar 

  • Mason, R.P., Holtzman, J.L.: The mechanism of microsomal and mitochondrial nitroreductase. Electron spin resonance evidence for nitroaromatic free radical intermediates. Biochemistry 14, 1626–1632 (1975 b)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R.: Chloroplasts of Euglena gracilis affected by furadantin. Science 137, 225–226 (1962)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R.: Effects of some nitrofurans on DNA synthesis and prophage induction. Can. J. Biochem. 42, 1245–1247 (1964)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R.: Nitrofuran derivatives as radiomimetic agents; cross-resistance studies with Escherichia coli. Can. J. Microbiol. 11, 185–191 (1965 a)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R.: Chloroplast mutagenesis: Effect of N-methyl-N′-Nitro-N-nitrosoguanidine and some other agents on Euglena. Science 148, 497–499 (1965 b)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R.: Effect of nitrofurans on the chloroplast system of Euglena gracilis. J. Protozool. 12, 34–41 (1965 c)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R., Reuvers, A.: Action of nitrofuran derivatives on the chloroplast system of Euglena gracilis: Effect of light. J. Protozool. 17, 129–134 (1970)

    CAS  Google Scholar 

  • McCalla, D.R., Voutsinos, D.: On the mutagenicity of nitrofurans. Mutat. Res. 26, 3–16 (1974)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R., Voutsinos, D.: Nitrofuran–reducing enzymes of Euglena. J. Protozool. 22, 130–134 (1975)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R., Reuvers, A., Kaiser, C.: Mode of action of nitrofurazone. J. Bacteriol. 104, 1126–1134 (1970)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R., Reuvers, A., Kaiser, C.: Breakage of bacterial DNA by nitrofuran derivatives. Cancer Res. 31, 2184–2188 (1971 a)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R., Reuvers, A., Kaiser, C.: Activation of nitrofurazone in animal tissues. Biochem. Pharmacol. 20, 3532–3537 (1971 b)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R., Olive, P., Tu, Y., Fan, M.L.: Nitrofurazone-reducing enzymes in E. coli and their role in drug activation in vivo. Can. J. Microbiol. 21, 1484–1491 (1975 a)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R., Voutsinos, D., Olive, P.L.: Mutagen screening with bacteria: Niridazole and nitrofurans. Mutat. Res. 31, 31–37 (1975 b)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R., Kaiser, C., Green, M.H.L.: Genetics of nitrofurazone resistance in Escherichia coli. J. Bacteriol. 133, 10–16 (1978 a)

    PubMed  CAS  Google Scholar 

  • McCalla, D.R., Arlett, C.F., Broughton, B.: The action of AF-2 on cultured hamster and human cells under aerobic and hypoxic conditions. Chem.-Biol. Interactions 21, 89–102 (1978 b)

    CAS  Google Scholar 

  • McCann, J., Spingarn, N.E., Kobori, J., Ames, B.N.: Detection of carcinogens as mutagens: Bacterial tester strains with R factor plasmids. Proc. Natl. Acad. Sci. USA 72, 979–983 (1975)

    PubMed  CAS  Google Scholar 

  • McGhie, D., Hutchison, J.G.P., Finch, R.G.: Stimulation of growth on a deficient medium of Klebsiella aerogenes species by sulphonamide, para-amino benzoic acid, nitrofurantoin and some other substances. J. Clin. Path. 25, 976–978 (1972)

    PubMed  CAS  Google Scholar 

  • McGrath, R.A., Williams, R.W.: Reconstruction in vivo of irradiated E. coli deoxyribonucleic acid: the rejoining of broken pieces. Nature (London) 212, 534–535 (1966)

    CAS  Google Scholar 

  • Miura, K., Okada, I.: Chemical and chemotherapeutical studies on the furan derivatives XXXVII. Studies on the phage inducing activity on Escherichia coli K 12 (γ) of nitrofuranquinoline compound. Chem. Pharm. Bull. 13, 525–528 (1965)

    PubMed  CAS  Google Scholar 

  • Miura, K., Reckendorf, H.K.: The nitrofurans. Prog. Med. Chem. 5, 320–381 (1967)

    PubMed  CAS  Google Scholar 

  • Miura, K., Ikeda, M., Oohashi, T., Okada, I., Igarski, Y: Chemical and chemotherapeutical studies on the furan derivatives. XXXV. Relation of antitumour effect and chemical structure of nitrofuran derivatives. Yakugaku Zasshi 84, 537–543 (1964)

    PubMed  CAS  Google Scholar 

  • Miyaji, T.: Acute and chronic toxicity of furylfuramide in rats and mice. Tohoku J. Exp. Med. 103, 331–369 (1971)

    PubMed  CAS  Google Scholar 

  • Mohindra, J.K., Rauth, A.M.: Increased cell killing by metronidazole and nitrofurazone of hypoxic compared to aerobic mammalian cells. Cancer Res. 36, 930–936 (1976)

    PubMed  CAS  Google Scholar 

  • Morris, J.E., Price, J.M., Lalich, J.J., Stein, R.J.: The carcinogenic activity of some 5-nitrofuran derivatives in the rat. Cancer Res. 29, 2145–2156 (1969)

    PubMed  CAS  Google Scholar 

  • Nakamura, S., Shimizu, P.M.: Inhibition of the synthesis of macromolecules in Escherichia coli by nitrofuran derivatives I. (5-nitro-2-furyl)vinylpyridines. Chem. Pharm. Bull. 21, 130–136 (1973 a)

    PubMed  CAS  Google Scholar 

  • Nakamura, N., Shimizu, P.M.: Inhibition of the synthesis of macromolecules in Escherichia coli by nitrofuran derivatives II various nitrofuran derivatives. Chem. Pharm. Bull. 21, 137–143 (1973 b)

    PubMed  CAS  Google Scholar 

  • Nelson, W.O., Bunge, R.G.: The effect of therapeutic dosages of nitrofurantoin (furadantin) upon spermatogenesis in man. J. Urol. 77, 275–281 (1957)

    PubMed  CAS  Google Scholar 

  • Nissim, J.A.: Increased pituitary gonadotrophin activity after degeneration of seminiferous tubules produced by nitrofurazone. Lancet 1, 304–305 (1957)

    Google Scholar 

  • Nomura, T.: Carcinogenicity of the food additive furylfuramide in foetal and young mice. Nature (London) 258, 610–611 (1975)

    CAS  Google Scholar 

  • Nomura, T., Kondo, S.: The enhancement effect of phenobarbital on toxicity of furylfuramide in mouse embryo. Mutat. Res. 35, 167–172 (1976)

    PubMed  CAS  Google Scholar 

  • Obatake, A., Karata, S.: Nitrofuran derivative as a food preservative. Microscopic studies on the effect of furylfuramide on germination and outgrowth of bacterial spores. Nippon Suisan Gakkaishi 38, 160–166 (1972)

    CAS  Google Scholar 

  • Okabayashi, T., Ide, M., Yoshimoto, A., Otsubo, M.: Mutagenic activity of 4-nitroquinoline 1-oxide and 4-hydroxyaminoquinoline 1-oxide on bacteria. Chem. Pharm. Bull. 13, 610–611 (1965)

    PubMed  CAS  Google Scholar 

  • Olivard, J., Valenti, S., Buzard, J.A.: The metabolism of 5-nitro-2-furaldehyde acetylhydrazone. J. Med. Pharm. Chem. 5, 524–531 (1962)

    CAS  Google Scholar 

  • Olivard, J., Rose, M.G., Klein, G.M., Heotis, J.P.: Metabolic and photochemical hydroxylation of 5-nitro-2-furancarboxaldehyde derivatives. J. Med. Chem. 19, 729–731 (1976)

    PubMed  CAS  Google Scholar 

  • Olive, P.L.: Damage to mammalian cell DNA by nitrofurans. Ph. D. Thesis, McMaster University (1976)

    Google Scholar 

  • Olive, P.L., McCalla, D.R.: Damage to mammalian cell DNA by nitrofurans. Cancer Res. 35, 781–784 (1975)

    PubMed  CAS  Google Scholar 

  • Olive, P.L., McCalla, D.R.: Cytotoxicity and DNA damage to mammalian cells by nitrofurans. Chem. Biol. Interact. 16, 223–233 (1977)

    PubMed  CAS  Google Scholar 

  • Ong, T.-M.: Mutagenicity of nitrofuran derivatives in Neurospora crassa. Mutat. Res. 26, 449–450 (1974)

    Google Scholar 

  • Ong, T-M., Shahin, M.M.: Mutagenic and recombinogenic activities of the food additive furylfuramide in Eukaryotes. Science 184, 1086–1087 (1974)

    PubMed  CAS  Google Scholar 

  • Ong, T-M., Callen, D.F., Huang, S.L., Batzinger, R.P., Bueding, E.: Mutation induction by the antischistosomal drug F 30066 in various test systems. Mutat. Res. 48, 37–42 (1977)

    PubMed  CAS  Google Scholar 

  • Osborn, M., Person, S.: Characterisation of revertants of E. coli WU 36-10 and WP2 using amber mutants and an ochre mutant of Bacteriophage T4. Mutat. Res. 4, 504–507 (1967)

    PubMed  CAS  Google Scholar 

  • Ou, T., Tatsumi, K., Yoshimura, H.: Isolation and identification of urinary metabolites of AF-2 (3- (5-nitro-2-furyl)-2- (2-furyl)acrylamide) in rabbits. Biochem. Biophys. Res. Commun. 75, 401–405 (1977)

    PubMed  CAS  Google Scholar 

  • Pai, S.H., Amaral, L., Werthamer, S., Zak, F.G.: Effect of the bladder carcinogen N-[4- (5-nitro-2-furyl)-2-thiazolyl] formamide on nucleic acids and total protein content of bladder epithelium undergoing malignant change. Invest. Urol. 11, 392–395 (1974)

    PubMed  CAS  Google Scholar 

  • Palermo, D., Gentile, G.: Studies on the presence of nitrofurazone residues in poultry muscle, internal organs, and poultry eggs. Arch. Vet. Ital. 26, 81–85 (1975), seen as Chem. Abstr. 85, 19201t (1976)

    CAS  Google Scholar 

  • Pastan, I., Perlman, R.: Cyclic adenosine monophosphate in bacteria. Science 169, 339–344 (1970)

    Google Scholar 

  • Paul, H.E., Paul, M.F.: The nitrofurans — chemotherapeutic properties. In: Experimental chemotherapy. Schnitzer, R.J. (ed.), Vol. II, pp. 307–370. New York, London: Academic Press 1964

    Google Scholar 

  • Paul, H.E., Paul, M.F.: The nitrofurans — Chemotherapeutic properties. In: Experimental chemotherapy. Schnitzer, R.J. (ed.), Vol. IV, pp. 521–536. New York, London: Academic Press 1966

    Google Scholar 

  • Paul, H.E., Austin, F.L., Paul, M.F., Ells, V.R.: Metabolism of the nitrofurans. Ultraviolet absorption studies of urinary end-products after oral administration. J. Biol. Chem. 180, 345–363 (1949)

    PubMed  CAS  Google Scholar 

  • Paul, H.E., Paul, M.F., Kopko, F., Bender, R.C., Everett, G.: Carbohydrate metabolism studies on the testis of rats fed certain nitrofurans. Endocrinology 52, 585–592 (1953)

    Google Scholar 

  • Paul, M.F., Harrington, C.: Nitrofurans and enzyme systems of the neonatal animal. Biochem. Pharmacol. 16, 2457–2460 (1967)

    PubMed  CAS  Google Scholar 

  • Payne, J.I., Hartman, P.E., Mudd, S., Phillips, A.W.: Cytological analysis of ultraviolet-irradiated Escherichia coli. III Reactions of a sensitive strain and its resistant mutants. J. Bacteriol. 72, 461–472 (1956)

    PubMed  CAS  Google Scholar 

  • Piguet, J.D., Rossi, M., Schmid, J.: In vitro inhibition of the bacteriostatic activity of nalidixic acid by nitrofurantoin. Ann. Inst. Pasteur. 116, 43–48 (1969)

    CAS  Google Scholar 

  • Prior, J.T., Ferguson, J.H.: Cytotoxic effects of a nitrofuran on the rat testis. Cancer 3, 1062–1072 (1950)

    PubMed  CAS  Google Scholar 

  • Pugh, D.L., Olivard, J., Snyder, H.R., Heotis, J.P.: Metabolism of l-[ (5-nitrofurfurylidene)amino]-2-imidazolidinone. J. Med. Chem. 15, 270–273 (1972)

    PubMed  CAS  Google Scholar 

  • Raychaudhuri, C., Chatterjee, S.N., Maiti, M.: Effects of furazolidone on the macromolecular synthesis and morphology of Vibrio cholerae cells. Biochim. Biophys. Acta 222, 637–646 (1970)

    PubMed  CAS  Google Scholar 

  • Ritzerfeld, W.: Enzyme alteration of the effects of antibiotics. Arzneimittelforschung 19, 674–676 (1969)

    PubMed  CAS  Google Scholar 

  • Röschenthaler, R., Kindler, P., Herrlich, P., Igbokwe, J.: The action of nitrofurantoin: Inhibition of growth of Escherichia coli K 12 and of IPTG-induced Beta-Galactosidase synthesis. Zentralbl. Bakteriol. I, 215, 203–211 (1970)

    Google Scholar 

  • Rosenkranz, H. S.: Studies on the mutagenicity of nitrofurans in Salmonella typhimurium. Biochem. Pharmacol. 26, 898–898 (1977)

    Google Scholar 

  • Rosenkranz, H.S., Speck, T.W.: Activation of nitrofurantoin to a mutagen by rat liver nitroreductase. Biochem. Pharmacol. 25, 1555–1556 (1976)

    PubMed  CAS  Google Scholar 

  • Rotenberg, G.N.: Compendium of pharmaceuticals and specialities, 12 ed., pp. 318–319. Canadian Pharmaceutical Assoc. 1977

    Google Scholar 

  • Sano, T., Kawachi, T., Matsukura, N., Sasajima, K., Sugimura, T.: Carcinogenicity of a food additive, AF-2 in hamsters and mice. Z. Krebsforsch. 89, 61–68 (1977)

    CAS  Google Scholar 

  • Schiff, J.A., Epstein, H.T.: The continuity of the chloroplast in Euglena. In: The biology of Euglena. Buetow, D.E. (ed.), pp. 285–333. New York, London: Academic Press 1968

    Google Scholar 

  • Schiff, J.A., Lyman, H., Epstein, H.T.: Studies of chloroplast development in Euglena. Biochim. Biophys. Acta 51, 340–346 (1961)

    PubMed  CAS  Google Scholar 

  • Schoog, M.: Untersuchungen zum Wirkungsablauf von Nitrofuranderivaten. Arzneimittelforsch. 6, 450–454 (1956)

    PubMed  CAS  Google Scholar 

  • Shakhlin, V.V.: Study of the interaction of preparations (antibiotics) of the nitrofuran series with nucleic acids. Zhivotnovod. Med. 103–105 (1975)

    Google Scholar 

  • Shakhlin, V.V., Kulyash, Yu.V.: Effect of solafur and furazolidone on the transforming activity of deoxyribonucleic acid isolated from Staphylococcus aureus. Zhivotnovod. Med. 105–107 (1975). Seen as Chem. Abst. 86, 165839u (1977) Shenderov, B.A.: Effect of 5-nitrofuran derivatives on the transmission of drug resistance by conjugation. Zh. Mikrobiol. Epidemiol. Immunobiol. 48, 77–81 (1971)

    Google Scholar 

  • Siennicki, W.: Antibacterial properties of letilan surgical sutures. Polim. Med. 2, 393–407 (1972), seen as Chem. Abst. 79, 9858 z (1973)

    CAS  Google Scholar 

  • Sims, P., Gutteridge, W.E.: Biochemical effects and mode of action of a 5-nitrofuran drug, SQ 18,506 on Trypanosoma cruzi. In: Biochemistry of parasites and host-parasite relationships. Von den Bossche, H. (ed.), pp. 485–491. Amsterdam: Elsevier, 1976

    Google Scholar 

  • Soares, E.R., Sheridan, W.: Lack of induction of dominant lethals in mice by orally administered AF-2. Mutat. Res. 31, 235–240 (1975)

    PubMed  CAS  Google Scholar 

  • Stein, R.J., Yost, O., Petroliunas, F., Von Esch, A.: Carcinogenic activity of nitrofurans: A histologic evaluation. Fed. Proc. 25, 291 (1966)

    Google Scholar 

  • Steinhoff, D., Grundmann, E.: Test for carcinogenicity of nifurtimox on oral and subcutaneous administration to rats. Arzneimittelforschung 22, 1607–1612 (1972)

    PubMed  CAS  Google Scholar 

  • Stradins, J.P., Hiller, S.A., Gavars, R.A., Reihmanis, G.O., Baumane, L.H.: Electrochemical properties and biological activity of nitrofurans. In: Biological aspects of electrochemistry (Symposium). Millazo, G., Jones, P.E., Rampazzo, L. (eds.), pp. 607–617. Experientia Supplementum 18. Basel and Stuttgart: Birkhauser Verlag (1971)

    Google Scholar 

  • Sugimura, T., Sato, S., Nagao, M., Yahagi, T., Matsushima, T., Seino, Y., Takeuchi, M., Kawachi, T.: Overlapping of carcinogens and mutagens. In: Fundamentals in cancer prevention. Magee, P.N., Takayama, S., Sugimura, T., Matsushima, T. (eds.), pp. 191–215. Univ. of Tokyo Press 1975

    Google Scholar 

  • Sugiyama, T., Goto, K., Uenaka, H.: Acute cytogenetic effect of 2- (2-furyl)-3- (5-nitro-2-furyl)acryl-amide (AF-2, A food preservative) on rat bone marrow cells in vivo. Mutat. Res. 31, 241–246 (1975)

    PubMed  CAS  Google Scholar 

  • Swaminathan, S., Wang, R.C., Lower, G.M., Bryan, G.T.: Binding of 2-amino-4- (5-nitro-2-furyl)-2-14C-thiazole (ANFT) to yeast transfer RNA using rat liver microsomes. Proc. Am. Assoc. Cancer Res. 18, 187 (1977)

    Google Scholar 

  • Szeczukowski, M.J., Daywitt, A.L.: Metastatic testicular tumor treated with nitrofurazone. J. Am. Med. Assoc. 167, 1066–1068 (1958)

    Google Scholar 

  • Szybalski, W.: Special microbiological systems. II. Observations on chemical mutagenesis, in microorganisms. Ann. N.Y. Acad. Sci. 76, 475–489 (1958)

    PubMed  CAS  Google Scholar 

  • Szybalski, W., Nelson, T.C.: Genetics of bacterial resistance to nitrofurans and radiation. Bacteriol. Proc., 51–52 (1954)

    Google Scholar 

  • Tada, M., Tada, M.: Seryl-tRNA synthetase and activation of the carcinogen 4-nitroquinoline 1-oxide. Nature (London) 255, 510–512 (1975)

    CAS  Google Scholar 

  • Takase, Y., Nakamura, S., Ishyama, M., Shimizu, M.: Inhibition of the synthesis of macromolecules in Escherichia coli by nitrofuran derivatives. III Nifurpirinol. Chem. Pharm. Bull. 21, 144–148 (1973)

    PubMed  CAS  Google Scholar 

  • Takashashi, K.: Statistical analysis on toxicity of a nitrofuran derivative, 2- (2-furyl)-3- (5-nitro-2-furyl)acrylamide. Tohoku J. Exp. Med. 115, 167–183 (1975)

    Google Scholar 

  • Tatsumi, K., Ou, T., Yamaguchi, T., Yoshimura, H.: Metabolism of drugs LXXIX. The metabolic fate of nitrofuran derivatives. (2) Degradation by small intestinal mucosa and absorption from gastrointestinal tract. Chem. Pharm. Bull. 21, 191–201 (1973 a)

    PubMed  CAS  Google Scholar 

  • Tatsumi, K., Yamaguchi, T., Yoshimura, H.: Metabolism of drugs LXXX. The metabolic fate of nitrofuran derivatives. (3). Studies of enzymes in small intestinal mucosa of rat catalysing degradation of nitrofuran derivatives. Chem. Pharm. Bull. 21, 622–628 (1973 b)

    PubMed  CAS  Google Scholar 

  • Tatsumi, K., Kitamura, S., Yoshimura, H.: Reduction of nitrofuran derivatives by xanthine oxidase and microsomes. Arch. Biochem. Biophys. 175, 131–137 (1976 a)

    PubMed  CAS  Google Scholar 

  • Tatsumi, K., Kitamura, S., Koga, N., Yoshimura, H., Kato, Y.: Cis-Trans isomerization of nitrofuran derivatives by xanthine oxidase. Biochem. Biophys. Res. Commun. 73, 947–952 (1976 b)

    PubMed  CAS  Google Scholar 

  • Taylor, J.D., Paul, H.D., Paul, F.M.: Metabolism of nitrofurans III. Studies with xanthine oxidase in vitro. J. Biol. Chem. 191, 223–231 (1951)

    PubMed  CAS  Google Scholar 

  • Tazima, Y., Onimaru, K.: Results of mutagenicity testing for some nitrofuran derivatives in a sensitive test system with silkworm oocytes. Mutat. Res. 26, 440 (1974)

    Google Scholar 

  • Tazima, Y., Kada, T., Murakami, A.: Mutagenicity of nitrofuran derivatives, including furylfuramide, a food preservative. Mutat. Res. 32, 55–80 (1975)

    PubMed  CAS  Google Scholar 

  • Tennett, D.M., Ray, W.H.: Urinary metabolites of furazolidone. Fed. Proc. 22, 367 (1963)

    Google Scholar 

  • Terawaki, A., Greenberg, J.: Effect of some radiomimetic agents on DNA synthesis in Escherichia coli and transformation in Bacillus subtilus. Biochim. Biophys. Acta 95, 170–173 (1965)

    PubMed  CAS  Google Scholar 

  • Tomcufcik, A.S.: Chemotherapy of Trypanosomaisis and other protozoan diseases. In: Medicinal chemistry, 3rd. ed. Berger, A. (ed.), pp. 562–582. Wiley-Interscience 1970

    Google Scholar 

  • Tomoeda, M., Kitamura, R., Yamada, M., Nakamura, S., Inuzuka, M.: The structure and biological activities of 3-amino-6-[2- (5-nitro-2-furyl)vinyl]-l,2,4-triazine and its derivatives: On the curing action of the agent on drug resistant bacteria. Chemotherapy 22, 1153–1158 (1974)

    CAS  Google Scholar 

  • Tonomura, A., Sasaki, M.S.: Chromosome aberrations and DNA repair synthesis in cultured human cells exposed to nitrofurans. Jpn. J. Genet. 48, 291–294 (1973)

    Google Scholar 

  • Toole, J.F., Parrish, M., Nitrofurantoin polyneuropathy. Neurology 23, 554–559 (1973)

    PubMed  CAS  Google Scholar 

  • Toth, G., Toth, I.: Benzimidazole derivatives. Patent — Germany (West). Chem. Abstr. 84, 44064n (1976)

    Google Scholar 

  • Tu, Y., McCalla, D.R.: Effect of activated nitrofurans on DNA. Biochim. Biophys. Acta 402, 142–149 (1975)

    PubMed  CAS  Google Scholar 

  • Tu, Y., McCalla, D.R.: Effect of nitrofurazone on bacterial RNA and ribosome synthesis and on the function of ribosomes. Chem. Biol. Interact. 14, 81–91 (1976)

    PubMed  CAS  Google Scholar 

  • Ujiie, T.: Experimental anticancer studies. XXVIII. Anticancer activity of some nitrofuran derivatives. Chem. Pharm. Bull. 14, 461–466 (1966)

    PubMed  CAS  Google Scholar 

  • Ujiie, T.: Anticancer activity of 2- (2- (5-nitro-2-furyl)vinyl)-8- (β- (N,N-diethylamino)ethoxy) quinoline. Chem. Pharm. Bull. 22, 2470–2475 (1974)

    PubMed  CAS  Google Scholar 

  • Umeda, M., Tsutsui, T., Kikyo, S., Saito, M.: Mutagenic activity of furylfuramide on cultured mouse cells. Jpn. J. Exp. Med. 45, 161–170 (1975)

    PubMed  CAS  Google Scholar 

  • Vig, B.K., Natarajan, A.T., Zimmermann, F.K.: Study on cytological effects of carofur — a new mutagen. Mutat. Res. 42, 109–115 (1977)

    PubMed  CAS  Google Scholar 

  • Walker, G.C.: Plasmid (pKM 101)-mediated enhancement of repair and mutagenesis: Dependence on chromosomal genes in Escherichia coli K-12. Mol. Gen. Genet. 152, 93–103 (1977)

    PubMed  CAS  Google Scholar 

  • Wang, C.Y., Bryan, G.T.: Deacylation of carcinogenic 5-nitrofuran derivatives by mammalian tissues. Chem. Biol. Interact. 9, 423–428 (1974)

    PubMed  CAS  Google Scholar 

  • Wang, C.Y., Hayasida, S.: Effect of phenathiazine, 5-di-o-acetyl-D-glucosaccharo- (l → 4) (6 → 3)-dilactone (SLA), caffeine, cysteamine and dexamethazone on the induction of bladder cancer in rats by N-[4- (5-nitro-2-furyl)thiazolyl]formamide (FANFT). Proc. Am. Assoc. Cancer Res. 18, 100 (1977)

    Google Scholar 

  • Wang, C.Y., Lee, H.L.: Mutagenic activity of carcinogenic and noncarcinogenic nitrofurans and of urine of rats fed these compounds. Chem. Biol. Interact. 15, 69–75 (1976)

    PubMed  CAS  Google Scholar 

  • Wang, C.Y., Behrens, B.C., Ichikawa, M., Bryan, G.T.: Nitroreduction of 5-nitrofuran derivatives by rat liver xanthine oxidase and reduced nicotinamide adenine dinucleotide phosphate-cytochrome c reductase. Biochem. Pharmacol. 23, 3395–3404 (1974)

    PubMed  CAS  Google Scholar 

  • Wang, F.Y., Chiu, C.W., Kaiman, B., Bryan, G.T.: Identification of 2-methyl-4- (5-amino-2-furyl)thiazole as the reduced metabolite of 2-methyl-4- (5-nitro-2-furyl)thiazole. Biochem. Pharmacol. 24, 291–293 (1975 a)

    PubMed  CAS  Google Scholar 

  • Wang, C.Y., Chiu, W.C., Bryan, G.T.: Metabolism and disposition of N-[4- (5-nitro-2-furyl)-[2-14C]thiazolyl]acetamide in the rat. Drug Metab. Dispos. 3, 89–95 (1975 b)

    PubMed  CAS  Google Scholar 

  • Wang, C.Y., Hayashida, S., Pamukcu, A.M., Bryan, G.T.: Enhancing effect of allopurinol on the induction of bladder cancer in rats by N-[4- (5-nitro-2-furyl)-2-thiazolyl]formamide. Cancer Res. 36, 1551–1555 (1976)

    PubMed  CAS  Google Scholar 

  • Waterbury, W.E., Freedman, R.: Induction of phage formation by nitrofurans. Can. J. Microbiol. 10, 932–934 (1964)

    PubMed  CAS  Google Scholar 

  • Waterbury, W.E., Boydstun, J., Castellani, A.G., Freedman, R., Gavin, J.J.: Effect of nitrofurans on cell wall synthesis and L-Phase growth of staphylococcus aureus. Antimicrob. Agents Chemother. 339–344 (1965)

    Google Scholar 

  • Wegner, D.H.G., Rohwedder, R.W.: The effect of Nifurtimox in acute Chagas’ infection. Arzneimittelforschung (Drug Res.) 22, 1624–1635 (1972)

    CAS  Google Scholar 

  • Weiglepp, H., Hoyer, G.A., Kieslich, K.: Mikrobiologisch Spaltung eins nitrofuran-derivates. Chem. Ber. 106, 1303–1308 (1973)

    Google Scholar 

  • Westerholm, B.: Adverse reactions from chemotherapeutic agents as seen in a National Monitoring Centre. Int. J. Clin. Pharm. 9, 276–282 (1974)

    CAS  Google Scholar 

  • Westwood, G.P.C., Hooper, W.L.: Antagonism of oxolinic acid by nitrofurantoin. Lancet 1, 460 (1975)

    PubMed  CAS  Google Scholar 

  • Wild, D.: Mutagenicity of the food additive AF-2, a nitrofuran, in Escherichia coli and Chinese hamster cells in culture. Mutat. Res. 31, 197–199 (1975)

    PubMed  CAS  Google Scholar 

  • Witkin, E.M.: Ultraviolet mutagenesis and inducible DNA repair in Escherichia coli. Bacteriol. Rev. 40, 869–907 (1976)

    PubMed  CAS  Google Scholar 

  • Wolpert, M.K., Althaus, J.R., Johns, D.G.: Nitroreductase activity of mammalian liver aldehyde oxidase. J. Pharm. Exp. Ther. 185, 202–213 (1973)

    CAS  Google Scholar 

  • Woody-Karrer, P., Greenberg, J.: Resistance and cross resistance of Escherichia coli S mutants to the radiomimetic agent nitrofurazone. J. Bacteriol. 85, 1208–1216 (1963)

    PubMed  CAS  Google Scholar 

  • Yahagi, T., Nagao, M., Hara, K., Matsushima, T., Sugimura, T., Gryan, G.T.: Relationships between the carcinogenic and mutagenic or DNA-modifying effects of nitrofuran derivatives, including 2- (2-furyl)-3- (5-nitro-2-furyl) acrylamide, a food additive. Cancer Res. 34, 2266–2273 (1974)

    PubMed  CAS  Google Scholar 

  • Yahagi, T., Matsushima, T., Nagao, M., Seino, Y., Sugimura, T., Bryan, G.T.: Mutagenicities of nitrofuran derivatives on a bacterial tester strain with an R. factor plasmid. Mutat. Res. 40, 9–14 (1976)

    PubMed  CAS  Google Scholar 

  • Yoshida, O., Erturk, E., Bryan, G.T., Lower, G.M., Jr.: The effect of gonadectomy and hormone administration on the urinary bladder carcinogenicity of N-[4- (5-nitro-2-furyl)-2-thiazolyl] formamide in male and female Swiss mice. Invest. Urol. 11, 216–220 (1973)

    PubMed  CAS  Google Scholar 

  • Zampieri, A., Greenberg, J.: Nitrofurazone as a mutagen in Escherichia coli. Biochem. Biophys. Res. Commun. 14, 172–176 (1964)

    PubMed  CAS  Google Scholar 

  • Zwart Voorspuij, A.J., Bokma, L.H.: The simultaneous action of two or more antibacterial agents. The action of the combination nitrofurantoin-chloramphenicol-erythromycin on Proteus vulgaris. Antibiot. Chemother. 9, 27–37 (1959)

    Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1979 Springer-Verlag Berlin · Heidelberg

About this chapter

Cite this chapter

McCalla, D.R. (1979). Nitrofurans. In: Hahn, F.E. (eds) Mechanism of Action of Antibacterial Agents. Antibiotics, vol 5 / 1. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-46403-4_11

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-46403-4_11

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-46405-8

  • Online ISBN: 978-3-642-46403-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics