Advertisement

Nitrofurans

  • D. R. McCalla
Part of the Antibiotics book series (ANTIBIOTICS, 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).

Keywords

Electron Spin Resonance Xanthine Oxidase Nitro Compound Xeroderma Pigmentosum Aldehyde Oxidase 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 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)PubMedGoogle Scholar
  2. Akao, M., Kuroda, K., Miyaki, K.: Metabolic degradations of nitrofurans by rat liver homogenate.Google Scholar
  3. Biochem. Pharmacol. 20, 3091–3096 (1971)Google Scholar
  4. 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)PubMedGoogle Scholar
  5. 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)PubMedGoogle Scholar
  6. Albert, P.S., Salerno, R.G., Kapoor, S.K., Davis, J.E.: The nitrofurans as sperm immobilizing agents. Urol. 113, 69–70 (1975)Google Scholar
  7. Andree, H., Koppensteiner, G.: Antimicrobial 5-nitrofurfural acetals, Patent — Germany (West). Chem. Abstr. 80, 120739w (1974)Google Scholar
  8. 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
  9. 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 1975Google Scholar
  10. 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)PubMedGoogle Scholar
  11. 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)PubMedGoogle Scholar
  12. Asnis, R.E., Cohen, F.B., Gots, J.S.: Studies on bacterial resistance to furacin. Antibiot. Chemother. 2, 123–129 (1952)Google Scholar
  13. 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)PubMedGoogle Scholar
  14. Beckett, A.H., Robinson, A.E.: Bacterial and chemical reduction of nitrofurazone. Chem. and Ind. 523–524 (1957)Google Scholar
  15. 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
  16. 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
  17. Bender, R.C., Paul, H.E.: Metabolism of the nitrofurans II. Incubation of furacin with mammalian tissues. J. Biol. Chem. 191, 217–222 (1951)PubMedGoogle Scholar
  18. 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)PubMedGoogle Scholar
  19. Boyland, E., Speyer, B.E.: Enzyme-catalysed reactions between some 2-substituted 5-nitrofuran derivatives and glutathione. Biochem. J. 119, 463–472 (1970)PubMedGoogle Scholar
  20. Brener, Z.: Biology of trypanosoma cruzi. Annu. Rev. Microbiol. 27, 347–382 (1973)PubMedGoogle Scholar
  21. 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)PubMedGoogle Scholar
  22. Brodie, A.F., Gots, J.S.: Nitrofurans as electron acceptors for certain respiratory enzymes. Arch. Biochem. Biophys. 39, 165–173 (1952 b)PubMedGoogle Scholar
  23. 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
  24. 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)PubMedGoogle Scholar
  25. 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
  26. Cançado, J.R., Salgado, A.A., Batista, S.M., Chiari, C.A.: Nifurtimox (Lampit). Rev. Goiana. Med. 31–44 (1976)Google Scholar
  27. 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
  28. 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
  29. Chatfield, D.H.: Disposition and metabolism of some nitrofurylthiazoles possessing antiparasitic activity. Xenobiotica 6, 509–520 (1976)PubMedGoogle Scholar
  30. Chatterjee, S.N., Maiti, M., Ghosh, S.: Interaction of furazolidone with DNA. Biochim. Biophys. Acta. 402, 161–165 (1975)PubMedGoogle Scholar
  31. Chernomordik, A.B.: Synergistic effect of antibiotics on Bac. pyocyaneus [Pseudonomonas aeruginosa]. Antibiotiki 12, 604–606 (1967)PubMedGoogle Scholar
  32. Chylak, J.: In vitro study of the combined effect of streptomycin and nitrofurantoin on Escherichia coli. Wiad. Lek. 26, 1413–1418 (1973)PubMedGoogle Scholar
  33. Cleaver, J.E., Bootsma, D.: Xeroderma Pigmentosum: Biochemical and genetic characteristics. Ann. Rev. Genet. 9, 19–38 (1975)PubMedGoogle Scholar
  34. Cohen, S.M., Bryan, G.T.: Carcinogenesis caused by nitrofuran derivatives. Proc. 5th Int. Congr. Pharmacol. 2, 164–170 (1973)Google Scholar
  35. 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)PubMedGoogle Scholar
  36. 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)PubMedGoogle Scholar
  37. 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)PubMedGoogle Scholar
  38. 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
  39. 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
  40. 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)Google Scholar
  41. Crain, E.M., Ray, W.H.: Metabolites of furazolidone in urine of chickens. J. Pharm. Sci. 61, 1495–1497 (1972)Google Scholar
  42. Dann, O., Möller, E.F.: Bakteriostatisch wirkende Nitro-verbindungen des Thiophens und Furans. Chem. Ber. 80, 23–36 (1947)Google Scholar
  43. 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
  44. 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
  45. Dietrich, R.A., Hellerman, L.: Diphosphopyridine nucleotide-linked aldehyde dehydrogenase II. Inhibitors. J. Biol. Chem. 238, 1683–1689 (1963)Google Scholar
  46. Dodd, M.C., Stillman, W.B.: The in vitro bacteriostatic action of some simple furan derivatives. J. Pharmacol. Exp. Ther. 82, 11–18 (1944)Google Scholar
  47. Ebetino, F.F., Carroll, J.J., Gever, G.: Reduction of nitrofurans I. Aminofurans. J. Med. Pharm. Chem. 5, 513–524 (1962)Google Scholar
  48. 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)PubMedGoogle Scholar
  49. 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)Google Scholar
  50. 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)Google Scholar
  51. 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)PubMedGoogle Scholar
  52. Elslager, E.F.: Antiamebic Agents.: Medicinal chemistry, 3rd. ed. Burger, A. (ed.), pp. 522–561. Wiley-Interscience 1970Google Scholar
  53. 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)Google Scholar
  54. 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)PubMedGoogle Scholar
  55. 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)PubMedGoogle Scholar
  56. 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)PubMedGoogle Scholar
  57. 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)PubMedGoogle Scholar
  58. 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)Google Scholar
  59. 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)PubMedGoogle Scholar
  60. 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)Google Scholar
  61. Feller, D.R., Morita, M., Gillette, J.R.: Enzymatic reduction of niridazole by rat liver microsomes. Biochem. Pharmacol. 20, 203–215 (1971 b)PubMedGoogle Scholar
  62. Finegold, S.M., Ziment, I.: Sulfonamides, nitrofurans and nalidixic acid. In: Antimicrobial therapy, pp. 102–118. Philadelphia: W.B. Saunders Co. 1970Google Scholar
  63. Fridovich, I.: Superoxide dismutases. Ann. Rev. Biochem. 44, 147–159 (1975)PubMedGoogle Scholar
  64. Gale, G.R.: The inhibition by furacin of adaptive enzyme formation in Mycobacterium butyricum. Science 114, 689–690 (1951)PubMedGoogle Scholar
  65. 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
  66. 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)PubMedGoogle Scholar
  67. 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
  68. 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
  69. 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)PubMedGoogle Scholar
  70. 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)PubMedGoogle Scholar
  71. Green, M.H.L., Muriel, W.J.: Mutagen testing using TRP+ reversion in Escherichia coli. Mutat. Res. 38, 3–32 (1976)PubMedGoogle Scholar
  72. 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)PubMedGoogle Scholar
  73. Green, M.N.: The effect of furacin (5-nitro-2-furaldehyde semicarbazone) on the metabolism of bacteria. Arch. Biochem. 19, 397–406 (1948)PubMedGoogle Scholar
  74. 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
  75. Grunberg, E., Titsworth, E.H.: Chemotherapeutic properties of heterocyclic compounds: Monocyclic compounds with five-membered rings. Ann. Rev. Microbiol. 27, 317–346 (1973)Google Scholar
  76. 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
  77. Hailey, J.F., Glascock, H.W., Hewitt, W.F.: Pleuropneumonie reactions to nitrofurantoin. N. Engl. J. Med. 281, 1087–1090 (1969)PubMedGoogle Scholar
  78. Hamilton-Miller, J.M.T., Brumfitt, W.: The versatility of nitro compounds. J. Antimicrob. Chemother. 2, 5–7 (1976)PubMedGoogle Scholar
  79. 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)PubMedGoogle Scholar
  80. 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
  81. 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)Google Scholar
  82. 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)PubMedGoogle Scholar
  83. I ARC: Monographs on the evaluation of carcinogenic risk of chemicals to man. 7, 170–179 (1974)Google Scholar
  84. 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)PubMedGoogle Scholar
  85. 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)PubMedGoogle Scholar
  86. 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)PubMedGoogle Scholar
  87. 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)PubMedGoogle Scholar
  88. Joner, P.E., Dahle, H.K., Aune, T., Dybing, E.: Mutagenicity of nitrovine — A nitrofuran feed additive. Mutat. Res. 48, 313–318 (1977)PubMedGoogle Scholar
  89. Kada, T.: Escherichia coli mutagenicity of furylfuramide. Jpn. J. Genet. 48, 301–305 (1973)Google Scholar
  90. 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
  91. Kastering, B.: Electrochemische Bildung, Reaktivität und Eigenschaften des nitrobenzolradikalanions. Electrochim. Acta 9, 241–245 (1964)Google Scholar
  92. Katae, H., Iwana, H., Takase, Y., Shimizu, M.: Antitumor activity of nitrofuran and nitrothiophene derivatives on Ehrlich ascites carcinoma. Arzneimittelforschung 17, 1030–1034 (1967)PubMedGoogle Scholar
  93. 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)PubMedGoogle Scholar
  94. 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)PubMedGoogle Scholar
  95. 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)PubMedGoogle Scholar
  96. Kefauver, D.F., Paberzs, I., McNamara, T.F.: Furaltadone — a new antibacterial nitrofuran. Antibiotics Annual 1958–1959, 81–87 (1959)Google Scholar
  97. 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)PubMedGoogle Scholar
  98. 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)PubMedGoogle Scholar
  99. 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
  100. Klein, H.: Alkohol and medikamente. I. Durch medikamente verursachte Alkoholunverträglichkeit und verstärkte Alkoholwirkung. Fortschr. Med. 82, 169–172 (1964)Google Scholar
  101. 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)PubMedGoogle Scholar
  102. 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
  103. 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)Google Scholar
  104. Kotani, Y., Kageyama, K.: Glyoxal and nitrofuran derivatives as deodorants. Patent — Japan. Chem. Abstr. 84, 184797 d (1976)Google Scholar
  105. 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)Google Scholar
  106. Kuroda, Y.: Mutagenesis in cultured human diploid cells III. induction of 8-azaguanine-resistant mutations by furylfuramide. Mutat. Res. 30, 229–237 (1975)PubMedGoogle Scholar
  107. 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)PubMedGoogle Scholar
  108. 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 1976Google Scholar
  109. 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)PubMedGoogle Scholar
  110. 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)PubMedGoogle Scholar
  111. McCalla, D.R.: Chloroplasts of Euglena gracilis affected by furadantin. Science 137, 225–226 (1962)PubMedGoogle Scholar
  112. McCalla, D.R.: Effects of some nitrofurans on DNA synthesis and prophage induction. Can. J. Biochem. 42, 1245–1247 (1964)PubMedGoogle Scholar
  113. McCalla, D.R.: Nitrofuran derivatives as radiomimetic agents; cross-resistance studies with Escherichia coli. Can. J. Microbiol. 11, 185–191 (1965 a)PubMedGoogle Scholar
  114. 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)PubMedGoogle Scholar
  115. McCalla, D.R.: Effect of nitrofurans on the chloroplast system of Euglena gracilis. J. Protozool. 12, 34–41 (1965 c)PubMedGoogle Scholar
  116. 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)Google Scholar
  117. McCalla, D.R., Voutsinos, D.: On the mutagenicity of nitrofurans. Mutat. Res. 26, 3–16 (1974)PubMedGoogle Scholar
  118. McCalla, D.R., Voutsinos, D.: Nitrofuran–reducing enzymes of Euglena. J. Protozool. 22, 130–134 (1975)PubMedGoogle Scholar
  119. McCalla, D.R., Reuvers, A., Kaiser, C.: Mode of action of nitrofurazone. J. Bacteriol. 104, 1126–1134 (1970)PubMedGoogle Scholar
  120. McCalla, D.R., Reuvers, A., Kaiser, C.: Breakage of bacterial DNA by nitrofuran derivatives. Cancer Res. 31, 2184–2188 (1971 a)PubMedGoogle Scholar
  121. McCalla, D.R., Reuvers, A., Kaiser, C.: Activation of nitrofurazone in animal tissues. Biochem. Pharmacol. 20, 3532–3537 (1971 b)PubMedGoogle Scholar
  122. 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)PubMedGoogle Scholar
  123. McCalla, D.R., Voutsinos, D., Olive, P.L.: Mutagen screening with bacteria: Niridazole and nitrofurans. Mutat. Res. 31, 31–37 (1975 b)PubMedGoogle Scholar
  124. McCalla, D.R., Kaiser, C., Green, M.H.L.: Genetics of nitrofurazone resistance in Escherichia coli. J. Bacteriol. 133, 10–16 (1978 a)PubMedGoogle Scholar
  125. 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)Google Scholar
  126. 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)PubMedGoogle Scholar
  127. 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)PubMedGoogle Scholar
  128. 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)Google Scholar
  129. 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)PubMedGoogle Scholar
  130. Miura, K., Reckendorf, H.K.: The nitrofurans. Prog. Med. Chem. 5, 320–381 (1967)PubMedGoogle Scholar
  131. 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)PubMedGoogle Scholar
  132. Miyaji, T.: Acute and chronic toxicity of furylfuramide in rats and mice. Tohoku J. Exp. Med. 103, 331–369 (1971)PubMedGoogle Scholar
  133. 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)PubMedGoogle Scholar
  134. 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)PubMedGoogle Scholar
  135. 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)PubMedGoogle Scholar
  136. 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)PubMedGoogle Scholar
  137. Nelson, W.O., Bunge, R.G.: The effect of therapeutic dosages of nitrofurantoin (furadantin) upon spermatogenesis in man. J. Urol. 77, 275–281 (1957)PubMedGoogle Scholar
  138. Nissim, J.A.: Increased pituitary gonadotrophin activity after degeneration of seminiferous tubules produced by nitrofurazone. Lancet 1, 304–305 (1957)Google Scholar
  139. Nomura, T.: Carcinogenicity of the food additive furylfuramide in foetal and young mice. Nature (London) 258, 610–611 (1975)Google Scholar
  140. Nomura, T., Kondo, S.: The enhancement effect of phenobarbital on toxicity of furylfuramide in mouse embryo. Mutat. Res. 35, 167–172 (1976)PubMedGoogle Scholar
  141. 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)Google Scholar
  142. 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)PubMedGoogle Scholar
  143. Olivard, J., Valenti, S., Buzard, J.A.: The metabolism of 5-nitro-2-furaldehyde acetylhydrazone. J. Med. Pharm. Chem. 5, 524–531 (1962)Google Scholar
  144. 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)PubMedGoogle Scholar
  145. Olive, P.L.: Damage to mammalian cell DNA by nitrofurans. Ph. D. Thesis, McMaster University (1976)Google Scholar
  146. Olive, P.L., McCalla, D.R.: Damage to mammalian cell DNA by nitrofurans. Cancer Res. 35, 781–784 (1975)PubMedGoogle Scholar
  147. Olive, P.L., McCalla, D.R.: Cytotoxicity and DNA damage to mammalian cells by nitrofurans. Chem. Biol. Interact. 16, 223–233 (1977)PubMedGoogle Scholar
  148. Ong, T.-M.: Mutagenicity of nitrofuran derivatives in Neurospora crassa. Mutat. Res. 26, 449–450 (1974)Google Scholar
  149. Ong, T-M., Shahin, M.M.: Mutagenic and recombinogenic activities of the food additive furylfuramide in Eukaryotes. Science 184, 1086–1087 (1974)PubMedGoogle Scholar
  150. 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)PubMedGoogle Scholar
  151. 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)PubMedGoogle Scholar
  152. 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)PubMedGoogle Scholar
  153. 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)PubMedGoogle Scholar
  154. 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)Google Scholar
  155. Pastan, I., Perlman, R.: Cyclic adenosine monophosphate in bacteria. Science 169, 339–344 (1970)Google Scholar
  156. 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 1964Google Scholar
  157. 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 1966Google Scholar
  158. 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)PubMedGoogle Scholar
  159. 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
  160. Paul, M.F., Harrington, C.: Nitrofurans and enzyme systems of the neonatal animal. Biochem. Pharmacol. 16, 2457–2460 (1967)PubMedGoogle Scholar
  161. 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)PubMedGoogle Scholar
  162. 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)Google Scholar
  163. Prior, J.T., Ferguson, J.H.: Cytotoxic effects of a nitrofuran on the rat testis. Cancer 3, 1062–1072 (1950)PubMedGoogle Scholar
  164. 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)PubMedGoogle Scholar
  165. 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)PubMedGoogle Scholar
  166. Ritzerfeld, W.: Enzyme alteration of the effects of antibiotics. Arzneimittelforschung 19, 674–676 (1969)PubMedGoogle Scholar
  167. 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
  168. Rosenkranz, H. S.: Studies on the mutagenicity of nitrofurans in Salmonella typhimurium. Biochem. Pharmacol. 26, 898–898 (1977)Google Scholar
  169. Rosenkranz, H.S., Speck, T.W.: Activation of nitrofurantoin to a mutagen by rat liver nitroreductase. Biochem. Pharmacol. 25, 1555–1556 (1976)PubMedGoogle Scholar
  170. Rotenberg, G.N.: Compendium of pharmaceuticals and specialities, 12 ed., pp. 318–319. Canadian Pharmaceutical Assoc. 1977Google Scholar
  171. 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)Google Scholar
  172. 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 1968Google Scholar
  173. Schiff, J.A., Lyman, H., Epstein, H.T.: Studies of chloroplast development in Euglena. Biochim. Biophys. Acta 51, 340–346 (1961)PubMedGoogle Scholar
  174. Schoog, M.: Untersuchungen zum Wirkungsablauf von Nitrofuranderivaten. Arzneimittelforsch. 6, 450–454 (1956)PubMedGoogle Scholar
  175. Shakhlin, V.V.: Study of the interaction of preparations (antibiotics) of the nitrofuran series with nucleic acids. Zhivotnovod. Med. 103–105 (1975)Google Scholar
  176. 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
  177. Siennicki, W.: Antibacterial properties of letilan surgical sutures. Polim. Med. 2, 393–407 (1972), seen as Chem. Abst. 79, 9858 z (1973)Google Scholar
  178. 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, 1976Google Scholar
  179. Soares, E.R., Sheridan, W.: Lack of induction of dominant lethals in mice by orally administered AF-2. Mutat. Res. 31, 235–240 (1975)PubMedGoogle Scholar
  180. Stein, R.J., Yost, O., Petroliunas, F., Von Esch, A.: Carcinogenic activity of nitrofurans: A histologic evaluation. Fed. Proc. 25, 291 (1966)Google Scholar
  181. Steinhoff, D., Grundmann, E.: Test for carcinogenicity of nifurtimox on oral and subcutaneous administration to rats. Arzneimittelforschung 22, 1607–1612 (1972)PubMedGoogle Scholar
  182. 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
  183. 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 1975Google Scholar
  184. 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)PubMedGoogle Scholar
  185. 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
  186. Szeczukowski, M.J., Daywitt, A.L.: Metastatic testicular tumor treated with nitrofurazone. J. Am. Med. Assoc. 167, 1066–1068 (1958)Google Scholar
  187. Szybalski, W.: Special microbiological systems. II. Observations on chemical mutagenesis, in microorganisms. Ann. N.Y. Acad. Sci. 76, 475–489 (1958)PubMedGoogle Scholar
  188. Szybalski, W., Nelson, T.C.: Genetics of bacterial resistance to nitrofurans and radiation. Bacteriol. Proc., 51–52 (1954)Google Scholar
  189. Tada, M., Tada, M.: Seryl-tRNA synthetase and activation of the carcinogen 4-nitroquinoline 1-oxide. Nature (London) 255, 510–512 (1975)Google Scholar
  190. 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)PubMedGoogle Scholar
  191. 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
  192. 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)PubMedGoogle Scholar
  193. 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)PubMedGoogle Scholar
  194. Tatsumi, K., Kitamura, S., Yoshimura, H.: Reduction of nitrofuran derivatives by xanthine oxidase and microsomes. Arch. Biochem. Biophys. 175, 131–137 (1976 a)PubMedGoogle Scholar
  195. 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)PubMedGoogle Scholar
  196. 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)PubMedGoogle Scholar
  197. 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
  198. Tazima, Y., Kada, T., Murakami, A.: Mutagenicity of nitrofuran derivatives, including furylfuramide, a food preservative. Mutat. Res. 32, 55–80 (1975)PubMedGoogle Scholar
  199. Tennett, D.M., Ray, W.H.: Urinary metabolites of furazolidone. Fed. Proc. 22, 367 (1963)Google Scholar
  200. 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)PubMedGoogle Scholar
  201. Tomcufcik, A.S.: Chemotherapy of Trypanosomaisis and other protozoan diseases. In: Medicinal chemistry, 3rd. ed. Berger, A. (ed.), pp. 562–582. Wiley-Interscience 1970Google Scholar
  202. 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)Google Scholar
  203. 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
  204. Toole, J.F., Parrish, M., Nitrofurantoin polyneuropathy. Neurology 23, 554–559 (1973)PubMedGoogle Scholar
  205. Toth, G., Toth, I.: Benzimidazole derivatives. Patent — Germany (West). Chem. Abstr. 84, 44064n (1976)Google Scholar
  206. Tu, Y., McCalla, D.R.: Effect of activated nitrofurans on DNA. Biochim. Biophys. Acta 402, 142–149 (1975)PubMedGoogle Scholar
  207. 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)PubMedGoogle Scholar
  208. Ujiie, T.: Experimental anticancer studies. XXVIII. Anticancer activity of some nitrofuran derivatives. Chem. Pharm. Bull. 14, 461–466 (1966)PubMedGoogle Scholar
  209. 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)PubMedGoogle Scholar
  210. Umeda, M., Tsutsui, T., Kikyo, S., Saito, M.: Mutagenic activity of furylfuramide on cultured mouse cells. Jpn. J. Exp. Med. 45, 161–170 (1975)PubMedGoogle Scholar
  211. Vig, B.K., Natarajan, A.T., Zimmermann, F.K.: Study on cytological effects of carofur — a new mutagen. Mutat. Res. 42, 109–115 (1977)PubMedGoogle Scholar
  212. 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)PubMedGoogle Scholar
  213. Wang, C.Y., Bryan, G.T.: Deacylation of carcinogenic 5-nitrofuran derivatives by mammalian tissues. Chem. Biol. Interact. 9, 423–428 (1974)PubMedGoogle Scholar
  214. 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
  215. 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)PubMedGoogle Scholar
  216. 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)PubMedGoogle Scholar
  217. 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)PubMedGoogle Scholar
  218. 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)PubMedGoogle Scholar
  219. 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)PubMedGoogle Scholar
  220. Waterbury, W.E., Freedman, R.: Induction of phage formation by nitrofurans. Can. J. Microbiol. 10, 932–934 (1964)PubMedGoogle Scholar
  221. 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
  222. Wegner, D.H.G., Rohwedder, R.W.: The effect of Nifurtimox in acute Chagas’ infection. Arzneimittelforschung (Drug Res.) 22, 1624–1635 (1972)Google Scholar
  223. Weiglepp, H., Hoyer, G.A., Kieslich, K.: Mikrobiologisch Spaltung eins nitrofuran-derivates. Chem. Ber. 106, 1303–1308 (1973)Google Scholar
  224. Westerholm, B.: Adverse reactions from chemotherapeutic agents as seen in a National Monitoring Centre. Int. J. Clin. Pharm. 9, 276–282 (1974)Google Scholar
  225. Westwood, G.P.C., Hooper, W.L.: Antagonism of oxolinic acid by nitrofurantoin. Lancet 1, 460 (1975)PubMedGoogle Scholar
  226. 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)PubMedGoogle Scholar
  227. Witkin, E.M.: Ultraviolet mutagenesis and inducible DNA repair in Escherichia coli. Bacteriol. Rev. 40, 869–907 (1976)PubMedGoogle Scholar
  228. Wolpert, M.K., Althaus, J.R., Johns, D.G.: Nitroreductase activity of mammalian liver aldehyde oxidase. J. Pharm. Exp. Ther. 185, 202–213 (1973)Google Scholar
  229. 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)PubMedGoogle Scholar
  230. 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)PubMedGoogle Scholar
  231. 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)PubMedGoogle Scholar
  232. 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)PubMedGoogle Scholar
  233. Zampieri, A., Greenberg, J.: Nitrofurazone as a mutagen in Escherichia coli. Biochem. Biophys. Res. Commun. 14, 172–176 (1964)PubMedGoogle Scholar
  234. 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

Copyright information

© Springer-Verlag Berlin · Heidelberg 1979

Authors and Affiliations

  • D. R. McCalla

There are no affiliations available

Personalised recommendations