Abstract
Nitroimidazoles are imidazoles that contain a nitro group at position 2, 4, or 5 of the imidazole ring. These compounds may have various substitutions on the nitrogen at position 1 of the imidazole ring. The 5-nitroimidazoles are synthetic compounds that appear to be very potent anaerobicidal agents. Three derivatives are commonly used in clinical therapy: metronidazole [1-(2-hydroxyethyl)-2-methyl-5-nitro-imidazole], ornidazole [1-(3-chloro-2-hydroxy-propyl) 2-methyl-5-nitroimidazole], and tinidĪ±-zole (ethyl [2-(2-methyl-5-nitro-1-imidazolyl)-ethyl] sulfone). They are used extensively for treatment of infections from anaerobic eucaryotes (Entamoeba histolytica, Trichomonas vaginalis, Giardia) and anaerobic procaryotes, having a bactericidal effect against all anaerobic bacteria except the genera Bifidobacterium, Propionibacterium, and Actinomyces.
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References
Birnboim, H.C. and J. Doly. 1979. A rapid alkaline extraction procedure for screening recombinant plasmid DNA. Nucleic Acids Res. 7:1513ā1523.
Breuil, J., A. Dublanchet, N. Truffaut, and M. Sebald. 1989. Transferable 5-nitroimidazole resistance in the Bacteroides fragilisgroup. Plasmid 21:151ā154.
Britz, M.L. and R.G. Wilkinson. 1979. Isolation and properties of metronidazole-resistant mutants of Bacteroides fragilis. Antimicrob. Agents Chemother. 16:19ā27.
Cerkasovova, A., J. Cerkasov, and J. Kulda. 1988. Resistance of trichomonads to metronidazole. Acta Univ. Carol. Biol. 30:485ā503.
Church, D.L., H.R. Rabin, and E.J. Laishley. 1990. Reduction of 2-, 4- and 5-nitroimidazole drugs by hydrogenase 1 in Clostridium pasteurianum. J. Antimicrob. Chemother. 25:15ā23.
Cuchural, G.J., F.P. Tally, J.R. Storey, and M.H. Malamy. 1986. Transfer of Ī²-lactamase-associated cefoxitin resistance in Bacteroides fragilis. Antimicrob. Agents Chemother. 29:918ā920.
Dublanchet, A., J. Caillon, J.P. Emond, H. Chardon, and H.B. Drugeon. 1986. Isolation of Bacteroidesstrains with reduced sensitivity to 5-nitroimidazoles. Eur.] Clin. Microbiol. 5:346ā347.
Edwards, D.I., M. Dye, and H. Carne. 1973. The selective toxicity of antimicrobial nitrohetero-cyclic drugs. J. Gen. Microbiol. 76:135ā145.
Erne, M.A., J.F. Acar, and F.W. Goldstein. 1983. Bacteroides fragilisresistant to metronidazole. J. Antimicrob. Chemother. 12:523ā525.
Finegold, S.M. and the National Committee for Clinical Laboratory Standards Working Group on Anaerobic Susceptibility Testing. 1988. Susceptibility testing of anaerobic bacteria. J. Clin. Microbiol. 26:1253ā1256.
Hof, H., T. Chakraborty, R. Royer, and J.-P. Buisson. 1987. Mode of action of nitro-heterocyclic compounds on Escherichia coli. Drugs Exp. Clin. Res. 13:635ā639.
Ingham, H.R., S. Eaton, C.W. Venables, and P.C. Adams. 1978. Bacteroides fragilisresistant to metronidazole after long-term therapy. Lancet i:214.
Knight, R.C., I.M. Skolimowski, and D.I. Edwards. 1978. The interaction of reduced metronidazole with DNA. Biochem. Pharmacol. 27:2089ā2093.
Lamothe, F., C. Fijalkowski, F. Malouin, A.M. Bourgault, and L. Delorme. 1986. Bacteroides fragilisresistant to metronidazole and imipenem. J. Antimicrob. Chemother. 18:642ā643.
LaRusso, N.F., M. Tomasz, M. MĆ¼ller, and R. Lipman. 1977. Interaction of metronidazole with nucleic acids in vitro. Mol. Pharmacol. 13:872ā882.
McLafferty, M.A., R.L. Koch, and P. Goldman. 1982. Interaction of metronidazole with resistant and susceptible Bacteroides fragilis. Antimicrob. Agents Chemother. 21:131ā134.
Milne, S.E., E.J. Stokes, and P.M. Waterworth. 1978. Incomplete anaerobiosis as a cause of metronidazole āresistance.ā J. Clin. Pathol. 31:933ā935.
MĆ¼ller, M. 1986. Reductive activation of nitroimi-dazoles in anaerobic microorganisms. Biochem. Pharmacol. 35:37ā41.
MĆ¼ller, M., J.G. Lossick, and T.E. Gorrel. 1988. In vitro susceptibility of Trichomonas vaginalisto metronidazole and treatment outcome in vaginal trichomoniasis. Sex. Trans. Dis. 15:17ā24.
Narikawa, S. 1986. Distribution of metronidazole susceptibility factors in obligate anaerobes. J. Antimicrob. Chemother. 18:565ā574.
OāBrien, R.W. and J.G. Morris. 1972. Effect of metronidazole on hydrogen production by Clostridium acetobutylicum. Arch. Mikrobiol. 84:225ā233.
Odelson, D.A., J.L. Rasmussen, C.J. Smith, and F.L. Macrina. 1987. Extrachromosomal systems and gene transmission in anaerobic bacteria. Plasmid 17:87ā109.
Perez-Reyes, E., B. Kalyanarman, and R.P. Mason. 1980. The reductive metabolism of metronidazole and ronidazole by aerobic liver microsomes. Mol. Pharmacol. 17:239ā244.
Plant C.W. and D.I. Edwards. 1976. The effects of tinidazole, metronidazole and nitrofurazone on nucleic acid synthesis in Clostridium bifermen-tans. J. Antimicrob. Chemother. 2:203ā209.
Privitera, G., A. Dublanchet, and M. Sebald. 1979a. Transfer of multiple antibiotic resistance between subspecies of Bacteroides fragilis. J. Infect. Dis. 139:97ā101.
Privitera, G., M. Sebald, and F. Fayolle. 1979b. Common regulatory mechanism of expression and conjugative ability of a tetracycline resistance plasmid in Bacteroides fragilis. Nature(London) 278:657ā659.
Rashtchian, A., G.R. Dubes, and S.J. Booth. 1982. Transferable resistance to cefoxitin in Bacteroides thetaiotaomicron. Antimicrob. Agents Chemother. 22:701ā703.
Rotimi, V.O., B.I. Duerden, V. Ede, and A.E. Mackinnon. 1979. Metronidazole-resistant Bacteroidesfrom untreated patient. Lancet i:833.
Scher, K.S. 1988. Emergence of antibiotic resistant strains of Bacteroides fragilis. Surg. Gynecol. Obst. 167:175ā179.
Sebald, M., G. Reysset, and J. Breuil. 1990. Whatās new in 5-nitroimidazole resistance in the Bacteroides fragilisgroup. In: Clinical and Molecular Aspects of Anaerobes, S.P. Borriello, ed., pp. 217ā225. Petersfield: Wrightson Biomedical.
Smith, C.J. 1985a. Development and use of cloning systems for Bacteroides fragilis: cloning of a plasmid-encoded clindamycin resistance determinant. J. Bacteriol. 164:294ā301.
Smith, C.J. 1985b. Polyethylene glycol-facilitated transformation of Bacteroides fragiliswith plasmid DNA. J. Bacteriol. 164:466ā469.
Smith, C.J. and H. Spiegel. 1987. Transposition of Tn4552 in Bacteroides fragilis: identification and properties of a new transposon from Bacteroidesspp. J. Bacteriol. 169:3450ā3457.
Sprott, M.S. and A.M. Kearns. 1988. Metronidazole-resistant Bacteroides melaninogenicus. J. Antimicrob. Chemother. 22:951ā954.
Sprott, M.S., H.R. Ingham, J.E. Hickman, and P.R. Sisson. 1983. Metronidazole-resistant anaerobes. Lancet i:1220.
Tabaqchali, S., A. Pantosi, and S. Oldfield. 1983. Pyruvate dehydrogenase activity and metronidazole susceptibility in Bacteroides fragilis. J. Antimicrob. Chemother. 11:393ā400.
Tally, F.P. and M.H. Malamy. 1982. Mechanism of antimicrobial resistance and resistance transfer in anaerobic bacteria. Scand. J. Infect. Dis. 35:37ā44(Suppl.).
Yamaoka, K., K. Watanabe, Y. Muto, N. Katoh, K. Ueno, and F.P. Tally. 1990. R-plasmid mediated transfer of Ī²-lactam resistance in Bacteroides fragilis. J. Antibiot. (Jpn) 43:1302ā1306.
Yeung, T.-C, B.B. Beaulieu, M.A. McLafferty, and P. Goldman. 1984. Interaction of metronidazole with DNA repair mutants of Escherichia coli. Antimicrob. Agents Chemother. 25:65ā70.
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Reysset, G., Su, WJ., Sebald, M. (1993). Genetics of 5-Nitroimidazole Resistance in Bacteroides . In: Sebald, M. (eds) Genetics and Molecular Biology of Anaerobic Bacteria. Brock/Springer Series in Contemporary Bioscience. Springer, New York, NY. https://doi.org/10.1007/978-1-4615-7087-5_37
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DOI: https://doi.org/10.1007/978-1-4615-7087-5_37
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