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Chemical Compound Review

PubChem7615     4-nitro-3H-imidazole

Synonyms: SureCN44903, AGN-PC-0091PJ, CHEMBL135599, SureCN367374, ACMC-1AIMC, ...
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Disease relevance of NSC50359


High impact information on NSC50359


Chemical compound and disease context of NSC50359


Biological context of NSC50359


Anatomical context of NSC50359

  • 5-Nitroimidazole derivative in the concentration of 300 micrograms/mg protein inhibited significantly the non-irradiated erythrocyte membrane (Na+, K+) ATP-ase activity, while 4-NO2 in the concentration of 3 micrograms/mg protein influenced this activity, but only after an exposure at dose of 60 Krad [18].
  • Metronidazole, a 5-nitroimidazole drug has been reported to decrease testicular weight, testicular and epididymal spermatid counts and causes abnormal sperm morphology with degeneration of seminiferous tubules with 6 weeks treatment of metronidazole (400 mg/kg, day) [19].

Associations of NSC50359 with other chemical compounds


Gene context of NSC50359

  • Identification and DNA sequence of the mobilization region of the 5-nitroimidazole resistance plasmid pIP421 from Bacteroides fragilis [25].
  • Comparative efficacy of metronidazole and another 5-nitroimidazole, CG-10213-Go, in caecal amoebiasis in albino mice (Mus musculus) [26].
  • 5-Nitroimidazole resistance assessed by the disc diffusion technique is not helpful in predicting OCT failure, but the E-test may be of value [27].
  • We aimed to evaluate this using the disc diffusion technique (Mast Diagnostics, Bootle, UK) and E-test (Cambridge Diagnostics Services, Cambridge, UK) to assess 5-nitroimidazole resistance [27].
  • The multiwavelength method may be used for samples degraded at pH 6-12 if the amount of conserved 5-nitroimidazole species is at least 93 mol.% of the original; the amounts of tinidazole and its two known impurities may be determined simultaneously [28].

Analytical, diagnostic and therapeutic context of NSC50359


  1. Structural basis of 5-nitroimidazole antibiotic resistance: the crystal structure of NimA from Deinococcus radiodurans. Leiros, H.K., Kozielski-Stuhrmann, S., Kapp, U., Terradot, L., Leonard, G.A., McSweeney, S.M. J. Biol. Chem. (2004) [Pubmed]
  2. Nucleotide sequence analysis of two 5-nitroimidazole resistance determinants from Bacteroides strains and of a new insertion sequence upstream of the two genes. Haggoud, A., Reysset, G., Azeddoug, H., Sebald, M. Antimicrob. Agents Chemother. (1994) [Pubmed]
  3. Satranidazole: experimental evaluation of activity against anaerobic bacteria in vitro and in animal models of anaerobic infection. Gowrishankar, R., Phadke, R.P., Oza, S.D., Talwalker, S. J. Antimicrob. Chemother. (1985) [Pubmed]
  4. Reduction of 2-, 4- and 5-nitroimidazole drugs by hydrogenase 1 in Clostridium pasteurianum. Church, D.L., Rabin, H.R., Laishley, E.J. J. Antimicrob. Chemother. (1990) [Pubmed]
  5. Response of the solid Guerin epitheliomas of rats to fractionated irradiation and a new 4-nitroimidazole. Watras, J., Wideł, M., Suwiński, J. Br. J. Cancer (1979) [Pubmed]
  6. Subcurative chemotherapy and fatal post-treatment reactive encephalopathies in African trypanosomiasis. Hunter, C.A., Jennings, F.W., Adams, J.H., Murray, M., Kennedy, P.G. Lancet (1992) [Pubmed]
  7. 5-Nitroimidazole drugs effective against metronidazole-resistant Trichomonas vaginalis and Giardia duodenalis. Upcroft, J.A., Dunn, L.A., Wright, J.M., Benakli, K., Upcroft, P., Vanelle, P. Antimicrob. Agents Chemother. (2006) [Pubmed]
  8. Investigation of 5-nitrofuran derivatives: synthesis, antibacterial activity, and quantitative structure-activity relationships. Pires, J.R., Saito, C., Gomes, S.L., Giesbrecht, A.M., Amaral, A.T. J. Med. Chem. (2001) [Pubmed]
  9. BRU59-21, a second-generation 99mTc-labeled 2-nitroimidazole for imaging hypoxia in tumors. Melo, T., Duncan, J., Ballinger, J.R., Rauth, A.M. J. Nucl. Med. (2000) [Pubmed]
  10. Radiosensitization by metal complexes of 4(5)-nitroimidazole. Skov, K.A., Farrell, N.P. Int. J. Radiat. Biol. (1990) [Pubmed]
  11. Tinidazole--microbiology, pharmacology and efficacy in anaerobic infections. Nord, C.E., Kager, L. Infection (1983) [Pubmed]
  12. Nitroimidazoles, Part 2 : synthesis, Antiviral and Antitumor Activity of New 4-Nitroimidazoles. Al-Masoudi, N.A., Al-Soud, Y.A., Kalogerakis, A., Pannecouque, C., De Clercq, E. Chem. Biodivers. (2006) [Pubmed]
  13. A randomized, controlled, open-label trial of a single day of mebendazole versus a single dose of tinidazole in the treatment of giardiasis in children. Ca??ete, R., Escobedo, A.A., Gonz??lez, M.E., Almirall, P., Cantelar, N. Current medical research and opinion. (2006) [Pubmed]
  14. Genetics of resistance of Bacteroides species to 5-nitroimidazole. Reysset, G., Haggoud, A., Sebald, M. Clin. Infect. Dis. (1993) [Pubmed]
  15. Trichomonads, hydrogenosomes and drug resistance. Kulda, J. Int. J. Parasitol. (1999) [Pubmed]
  16. Current trends in research into the waterborne parasite Giardia. Lane, S., Lloyd, D. Crit. Rev. Microbiol. (2002) [Pubmed]
  17. Genetic analysis of the minimal replicon of plasmid pIP417 and comparison with the other encoding 5-nitroimidazole resistance plasmids from Bacteroides spp. Haggoud, A., Trinh, S., Moumni, M., Reysset, G. Plasmid (1995) [Pubmed]
  18. Effects of nitroheterocyclic sensitizers on erythrocyte membranes ATP-ase activity. Rybczyńska, M., Chmiel, J., Philips, H. Polish journal of pharmacology and pharmacy. (1984) [Pubmed]
  19. Effect of metronidazole on spermatogenesis and FSH, LH and testosterone levels of pre-pubertal rats. Grover, J.K., Vats, V., Srinivas, M., Das, S.N., Jha, P., Gupta, D.K., Mitra, D.K. Indian J. Exp. Biol. (2001) [Pubmed]
  20. In vitro and in vivo activities of the nitroimidazole CGI 17341 against Mycobacterium tuberculosis. Ashtekar, D.R., Costa-Perira, R., Nagrajan, K., Vishvanathan, N., Bhatt, A.D., Rittel, W. Antimicrob. Agents Chemother. (1993) [Pubmed]
  21. Evaluation of novel radiation sensitizers in vitro and in vivo. Adams, G.E., Sheldon, P.W., Stratford, I.J. Int. J. Radiat. Oncol. Biol. Phys. (1982) [Pubmed]
  22. Cytotoxic properties of a 4-nitroimidazole (NSC 38087): a radiosensitizer of hypoxic cells in vitro. Stratford, I.J., Williamson, C., Hardy, C. Br. J. Cancer (1981) [Pubmed]
  23. KIH-802: 2-nitroimidazole-1-acetohydroxamate as a hypoxic cell radiosensitizer. Hori, H., Murayama, C., Mori, T., Shibamoto, Y., Abe, M., Onoyama, Y., Inayama, S. Int. J. Radiat. Oncol. Biol. Phys. (1989) [Pubmed]
  24. Trypanosoma cruzi: effect and mode of action of nitroimidazole and nitrofuran derivatives. Maya, J.D., Bollo, S., Nuñez-Vergara, L.J., Squella, J.A., Repetto, Y., Morello, A., Périé, J., Chauvière, G. Biochem. Pharmacol. (2003) [Pubmed]
  25. Identification and DNA sequence of the mobilization region of the 5-nitroimidazole resistance plasmid pIP421 from Bacteroides fragilis. Trinh, S., Reysset, G. J. Bacteriol. (1997) [Pubmed]
  26. Comparative efficacy of metronidazole and another 5-nitroimidazole, CG-10213-Go, in caecal amoebiasis in albino mice (Mus musculus). Ray, D.K., Tendulkar, J.S., Shrivastava, V.B., Nagarajan, K. J. Antimicrob. Chemother. (1982) [Pubmed]
  27. Relevance of antibiotic sensitivities in predicting failure of omeprazole, clarithromycin, and tinidazole to eradicate Helicobacter pylori. Moayyedi, P., Ragunathan, P.L., Mapstone, N., Axon, A.T., Tompkins, D.S. J. Gastroenterol. (1998) [Pubmed]
  28. Two stability-indicating UV spectrophotometric methods for the analysis of hydrolyzed tinidazole. Salo, J.P., Salomies, H. Journal of pharmaceutical and biomedical analysis. (2003) [Pubmed]
  29. Detection by PCR of the nim genes encoding 5-nitroimidazole resistance in Bacteroides spp. Trinh, S., Reysset, G. J. Clin. Microbiol. (1996) [Pubmed]
  30. Studies on the action of nitroimidazole drugs. The products of nitroimidazole reduction. Knox, R.J., Knight, R.C., Edwards, D.I. Biochem. Pharmacol. (1983) [Pubmed]
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