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).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
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)
Akao, M., Kuroda, K., Miyaki, K.: Metabolic degradations of nitrofurans by rat liver homogenate.
Biochem. Pharmacol. 20, 3091–3096 (1971)
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)
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)
Albert, P.S., Salerno, R.G., Kapoor, S.K., Davis, J.E.: The nitrofurans as sperm immobilizing agents. Urol. 113, 69–70 (1975)
Andree, H., Koppensteiner, G.: Antimicrobial 5-nitrofurfural acetals, Patent — Germany (West). Chem. Abstr. 80, 120739w (1974)
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)
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
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)
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)
Asnis, R.E., Cohen, F.B., Gots, J.S.: Studies on bacterial resistance to furacin. Antibiot. Chemother. 2, 123–129 (1952)
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)
Beckett, A.H., Robinson, A.E.: Bacterial and chemical reduction of nitrofurazone. Chem. and Ind. 523–524 (1957)
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)
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)
Bender, R.C., Paul, H.E.: Metabolism of the nitrofurans II. Incubation of furacin with mammalian tissues. J. Biol. Chem. 191, 217–222 (1951)
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)
Boyland, E., Speyer, B.E.: Enzyme-catalysed reactions between some 2-substituted 5-nitrofuran derivatives and glutathione. Biochem. J. 119, 463–472 (1970)
Brener, Z.: Biology of trypanosoma cruzi. Annu. Rev. Microbiol. 27, 347–382 (1973)
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)
Brodie, A.F., Gots, J.S.: Nitrofurans as electron acceptors for certain respiratory enzymes. Arch. Biochem. Biophys. 39, 165–173 (1952 b)
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)
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)
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)
Cançado, J.R., Salgado, A.A., Batista, S.M., Chiari, C.A.: Nifurtimox (Lampit). Rev. Goiana. Med. 31–44 (1976)
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)
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)
Chatfield, D.H.: Disposition and metabolism of some nitrofurylthiazoles possessing antiparasitic activity. Xenobiotica 6, 509–520 (1976)
Chatterjee, S.N., Maiti, M., Ghosh, S.: Interaction of furazolidone with DNA. Biochim. Biophys. Acta. 402, 161–165 (1975)
Chernomordik, A.B.: Synergistic effect of antibiotics on Bac. pyocyaneus [Pseudonomonas aeruginosa]. Antibiotiki 12, 604–606 (1967)
Chylak, J.: In vitro study of the combined effect of streptomycin and nitrofurantoin on Escherichia coli. Wiad. Lek. 26, 1413–1418 (1973)
Cleaver, J.E., Bootsma, D.: Xeroderma Pigmentosum: Biochemical and genetic characteristics. Ann. Rev. Genet. 9, 19–38 (1975)
Cohen, S.M., Bryan, G.T.: Carcinogenesis caused by nitrofuran derivatives. Proc. 5th Int. Congr. Pharmacol. 2, 164–170 (1973)
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)
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)
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)
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)
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)
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)
Crain, E.M., Ray, W.H.: Metabolites of furazolidone in urine of chickens. J. Pharm. Sci. 61, 1495–1497 (1972)
Dann, O., Möller, E.F.: Bakteriostatisch wirkende Nitro-verbindungen des Thiophens und Furans. Chem. Ber. 80, 23–36 (1947)
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)
Demecko, J., Koneczy, V., Krutcsikova, A., Kovac, J.: 5-nitro-2-furfuryl nitrate, a fungicidal seed dressing. Patent — Czechoslovakia. Chem. Abstr. 86, 12696v (1977)
Dietrich, R.A., Hellerman, L.: Diphosphopyridine nucleotide-linked aldehyde dehydrogenase II. Inhibitors. J. Biol. Chem. 238, 1683–1689 (1963)
Dodd, M.C., Stillman, W.B.: The in vitro bacteriostatic action of some simple furan derivatives. J. Pharmacol. Exp. Ther. 82, 11–18 (1944)
Ebetino, F.F., Carroll, J.J., Gever, G.: Reduction of nitrofurans I. Aminofurans. J. Med. Pharm. Chem. 5, 513–524 (1962)
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)
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)
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)
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)
Elslager, E.F.: Antiamebic Agents.: Medicinal chemistry, 3rd. ed. Burger, A. (ed.), pp. 522–561. Wiley-Interscience 1970
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)
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)
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)
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)
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)
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)
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)
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)
Feller, D.R., Morita, M., Gillette, J.R.: Enzymatic reduction of niridazole by rat liver microsomes. Biochem. Pharmacol. 20, 203–215 (1971 b)
Finegold, S.M., Ziment, I.: Sulfonamides, nitrofurans and nalidixic acid. In: Antimicrobial therapy, pp. 102–118. Philadelphia: W.B. Saunders Co. 1970
Fridovich, I.: Superoxide dismutases. Ann. Rev. Biochem. 44, 147–159 (1975)
Gale, G.R.: The inhibition by furacin of adaptive enzyme formation in Mycobacterium butyricum. Science 114, 689–690 (1951)
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)
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)
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)
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)
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)
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)
Green, M.H.L., Muriel, W.J.: Mutagen testing using TRP+ reversion in Escherichia coli. Mutat. Res. 38, 3–32 (1976)
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)
Green, M.N.: The effect of furacin (5-nitro-2-furaldehyde semicarbazone) on the metabolism of bacteria. Arch. Biochem. 19, 397–406 (1948)
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)
Grunberg, E., Titsworth, E.H.: Chemotherapeutic properties of heterocyclic compounds: Monocyclic compounds with five-membered rings. Ann. Rev. Microbiol. 27, 317–346 (1973)
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)
Hailey, J.F., Glascock, H.W., Hewitt, W.F.: Pleuropneumonie reactions to nitrofurantoin. N. Engl. J. Med. 281, 1087–1090 (1969)
Hamilton-Miller, J.M.T., Brumfitt, W.: The versatility of nitro compounds. J. Antimicrob. Chemother. 2, 5–7 (1976)
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)
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)
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)
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)
I ARC: Monographs on the evaluation of carcinogenic risk of chemicals to man. 7, 170–179 (1974)
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)
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)
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)
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)
Joner, P.E., Dahle, H.K., Aune, T., Dybing, E.: Mutagenicity of nitrovine — A nitrofuran feed additive. Mutat. Res. 48, 313–318 (1977)
Kada, T.: Escherichia coli mutagenicity of furylfuramide. Jpn. J. Genet. 48, 301–305 (1973)
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)
Kastering, B.: Electrochemische Bildung, Reaktivität und Eigenschaften des nitrobenzolradikalanions. Electrochim. Acta 9, 241–245 (1964)
Katae, H., Iwana, H., Takase, Y., Shimizu, M.: Antitumor activity of nitrofuran and nitrothiophene derivatives on Ehrlich ascites carcinoma. Arzneimittelforschung 17, 1030–1034 (1967)
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)
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)
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)
Kefauver, D.F., Paberzs, I., McNamara, T.F.: Furaltadone — a new antibacterial nitrofuran. Antibiotics Annual 1958–1959, 81–87 (1959)
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)
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)
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)
Klein, H.: Alkohol and medikamente. I. Durch medikamente verursachte Alkoholunverträglichkeit und verstärkte Alkoholwirkung. Fortschr. Med. 82, 169–172 (1964)
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)
Komura, M., Deguchi, S., Tadano, K.: Deodorant containing 5-nitro-2-furfural semicarbazone for hygienic use. Patent — Japan. Chem. Abstr. 80, 149037b (1974)
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)
Kotani, Y., Kageyama, K.: Glyoxal and nitrofuran derivatives as deodorants. Patent — Japan. Chem. Abstr. 84, 184797 d (1976)
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)
Kuroda, Y.: Mutagenesis in cultured human diploid cells III. induction of 8-azaguanine-resistant mutations by furylfuramide. Mutat. Res. 30, 229–237 (1975)
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)
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
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)
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)
McCalla, D.R.: Chloroplasts of Euglena gracilis affected by furadantin. Science 137, 225–226 (1962)
McCalla, D.R.: Effects of some nitrofurans on DNA synthesis and prophage induction. Can. J. Biochem. 42, 1245–1247 (1964)
McCalla, D.R.: Nitrofuran derivatives as radiomimetic agents; cross-resistance studies with Escherichia coli. Can. J. Microbiol. 11, 185–191 (1965 a)
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)
McCalla, D.R.: Effect of nitrofurans on the chloroplast system of Euglena gracilis. J. Protozool. 12, 34–41 (1965 c)
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)
McCalla, D.R., Voutsinos, D.: On the mutagenicity of nitrofurans. Mutat. Res. 26, 3–16 (1974)
McCalla, D.R., Voutsinos, D.: Nitrofuran–reducing enzymes of Euglena. J. Protozool. 22, 130–134 (1975)
McCalla, D.R., Reuvers, A., Kaiser, C.: Mode of action of nitrofurazone. J. Bacteriol. 104, 1126–1134 (1970)
McCalla, D.R., Reuvers, A., Kaiser, C.: Breakage of bacterial DNA by nitrofuran derivatives. Cancer Res. 31, 2184–2188 (1971 a)
McCalla, D.R., Reuvers, A., Kaiser, C.: Activation of nitrofurazone in animal tissues. Biochem. Pharmacol. 20, 3532–3537 (1971 b)
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)
McCalla, D.R., Voutsinos, D., Olive, P.L.: Mutagen screening with bacteria: Niridazole and nitrofurans. Mutat. Res. 31, 31–37 (1975 b)
McCalla, D.R., Kaiser, C., Green, M.H.L.: Genetics of nitrofurazone resistance in Escherichia coli. J. Bacteriol. 133, 10–16 (1978 a)
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)
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)
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)
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)
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)
Miura, K., Reckendorf, H.K.: The nitrofurans. Prog. Med. Chem. 5, 320–381 (1967)
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)
Miyaji, T.: Acute and chronic toxicity of furylfuramide in rats and mice. Tohoku J. Exp. Med. 103, 331–369 (1971)
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)
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)
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)
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)
Nelson, W.O., Bunge, R.G.: The effect of therapeutic dosages of nitrofurantoin (furadantin) upon spermatogenesis in man. J. Urol. 77, 275–281 (1957)
Nissim, J.A.: Increased pituitary gonadotrophin activity after degeneration of seminiferous tubules produced by nitrofurazone. Lancet 1, 304–305 (1957)
Nomura, T.: Carcinogenicity of the food additive furylfuramide in foetal and young mice. Nature (London) 258, 610–611 (1975)
Nomura, T., Kondo, S.: The enhancement effect of phenobarbital on toxicity of furylfuramide in mouse embryo. Mutat. Res. 35, 167–172 (1976)
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)
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)
Olivard, J., Valenti, S., Buzard, J.A.: The metabolism of 5-nitro-2-furaldehyde acetylhydrazone. J. Med. Pharm. Chem. 5, 524–531 (1962)
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)
Olive, P.L.: Damage to mammalian cell DNA by nitrofurans. Ph. D. Thesis, McMaster University (1976)
Olive, P.L., McCalla, D.R.: Damage to mammalian cell DNA by nitrofurans. Cancer Res. 35, 781–784 (1975)
Olive, P.L., McCalla, D.R.: Cytotoxicity and DNA damage to mammalian cells by nitrofurans. Chem. Biol. Interact. 16, 223–233 (1977)
Ong, T.-M.: Mutagenicity of nitrofuran derivatives in Neurospora crassa. Mutat. Res. 26, 449–450 (1974)
Ong, T-M., Shahin, M.M.: Mutagenic and recombinogenic activities of the food additive furylfuramide in Eukaryotes. Science 184, 1086–1087 (1974)
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)
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)
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)
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)
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)
Pastan, I., Perlman, R.: Cyclic adenosine monophosphate in bacteria. Science 169, 339–344 (1970)
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
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
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)
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)
Paul, M.F., Harrington, C.: Nitrofurans and enzyme systems of the neonatal animal. Biochem. Pharmacol. 16, 2457–2460 (1967)
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)
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)
Prior, J.T., Ferguson, J.H.: Cytotoxic effects of a nitrofuran on the rat testis. Cancer 3, 1062–1072 (1950)
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)
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)
Ritzerfeld, W.: Enzyme alteration of the effects of antibiotics. Arzneimittelforschung 19, 674–676 (1969)
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)
Rosenkranz, H. S.: Studies on the mutagenicity of nitrofurans in Salmonella typhimurium. Biochem. Pharmacol. 26, 898–898 (1977)
Rosenkranz, H.S., Speck, T.W.: Activation of nitrofurantoin to a mutagen by rat liver nitroreductase. Biochem. Pharmacol. 25, 1555–1556 (1976)
Rotenberg, G.N.: Compendium of pharmaceuticals and specialities, 12 ed., pp. 318–319. Canadian Pharmaceutical Assoc. 1977
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)
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
Schiff, J.A., Lyman, H., Epstein, H.T.: Studies of chloroplast development in Euglena. Biochim. Biophys. Acta 51, 340–346 (1961)
Schoog, M.: Untersuchungen zum Wirkungsablauf von Nitrofuranderivaten. Arzneimittelforsch. 6, 450–454 (1956)
Shakhlin, V.V.: Study of the interaction of preparations (antibiotics) of the nitrofuran series with nucleic acids. Zhivotnovod. Med. 103–105 (1975)
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)
Siennicki, W.: Antibacterial properties of letilan surgical sutures. Polim. Med. 2, 393–407 (1972), seen as Chem. Abst. 79, 9858 z (1973)
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
Soares, E.R., Sheridan, W.: Lack of induction of dominant lethals in mice by orally administered AF-2. Mutat. Res. 31, 235–240 (1975)
Stein, R.J., Yost, O., Petroliunas, F., Von Esch, A.: Carcinogenic activity of nitrofurans: A histologic evaluation. Fed. Proc. 25, 291 (1966)
Steinhoff, D., Grundmann, E.: Test for carcinogenicity of nifurtimox on oral and subcutaneous administration to rats. Arzneimittelforschung 22, 1607–1612 (1972)
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)
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
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)
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)
Szeczukowski, M.J., Daywitt, A.L.: Metastatic testicular tumor treated with nitrofurazone. J. Am. Med. Assoc. 167, 1066–1068 (1958)
Szybalski, W.: Special microbiological systems. II. Observations on chemical mutagenesis, in microorganisms. Ann. N.Y. Acad. Sci. 76, 475–489 (1958)
Szybalski, W., Nelson, T.C.: Genetics of bacterial resistance to nitrofurans and radiation. Bacteriol. Proc., 51–52 (1954)
Tada, M., Tada, M.: Seryl-tRNA synthetase and activation of the carcinogen 4-nitroquinoline 1-oxide. Nature (London) 255, 510–512 (1975)
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)
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)
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)
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)
Tatsumi, K., Kitamura, S., Yoshimura, H.: Reduction of nitrofuran derivatives by xanthine oxidase and microsomes. Arch. Biochem. Biophys. 175, 131–137 (1976 a)
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)
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)
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)
Tazima, Y., Kada, T., Murakami, A.: Mutagenicity of nitrofuran derivatives, including furylfuramide, a food preservative. Mutat. Res. 32, 55–80 (1975)
Tennett, D.M., Ray, W.H.: Urinary metabolites of furazolidone. Fed. Proc. 22, 367 (1963)
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)
Tomcufcik, A.S.: Chemotherapy of Trypanosomaisis and other protozoan diseases. In: Medicinal chemistry, 3rd. ed. Berger, A. (ed.), pp. 562–582. Wiley-Interscience 1970
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)
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)
Toole, J.F., Parrish, M., Nitrofurantoin polyneuropathy. Neurology 23, 554–559 (1973)
Toth, G., Toth, I.: Benzimidazole derivatives. Patent — Germany (West). Chem. Abstr. 84, 44064n (1976)
Tu, Y., McCalla, D.R.: Effect of activated nitrofurans on DNA. Biochim. Biophys. Acta 402, 142–149 (1975)
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)
Ujiie, T.: Experimental anticancer studies. XXVIII. Anticancer activity of some nitrofuran derivatives. Chem. Pharm. Bull. 14, 461–466 (1966)
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)
Umeda, M., Tsutsui, T., Kikyo, S., Saito, M.: Mutagenic activity of furylfuramide on cultured mouse cells. Jpn. J. Exp. Med. 45, 161–170 (1975)
Vig, B.K., Natarajan, A.T., Zimmermann, F.K.: Study on cytological effects of carofur — a new mutagen. Mutat. Res. 42, 109–115 (1977)
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)
Wang, C.Y., Bryan, G.T.: Deacylation of carcinogenic 5-nitrofuran derivatives by mammalian tissues. Chem. Biol. Interact. 9, 423–428 (1974)
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)
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)
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)
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)
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)
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)
Waterbury, W.E., Freedman, R.: Induction of phage formation by nitrofurans. Can. J. Microbiol. 10, 932–934 (1964)
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)
Wegner, D.H.G., Rohwedder, R.W.: The effect of Nifurtimox in acute Chagas’ infection. Arzneimittelforschung (Drug Res.) 22, 1624–1635 (1972)
Weiglepp, H., Hoyer, G.A., Kieslich, K.: Mikrobiologisch Spaltung eins nitrofuran-derivates. Chem. Ber. 106, 1303–1308 (1973)
Westerholm, B.: Adverse reactions from chemotherapeutic agents as seen in a National Monitoring Centre. Int. J. Clin. Pharm. 9, 276–282 (1974)
Westwood, G.P.C., Hooper, W.L.: Antagonism of oxolinic acid by nitrofurantoin. Lancet 1, 460 (1975)
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)
Witkin, E.M.: Ultraviolet mutagenesis and inducible DNA repair in Escherichia coli. Bacteriol. Rev. 40, 869–907 (1976)
Wolpert, M.K., Althaus, J.R., Johns, D.G.: Nitroreductase activity of mammalian liver aldehyde oxidase. J. Pharm. Exp. Ther. 185, 202–213 (1973)
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)
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)
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)
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)
Zampieri, A., Greenberg, J.: Nitrofurazone as a mutagen in Escherichia coli. Biochem. Biophys. Res. Commun. 14, 172–176 (1964)
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)
Editor information
Editors and Affiliations
Rights 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