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Chemical Compound Review

Bicyclomycin     (1S,6R)-6-hydroxy-5- methylidene-1-(1,2,3...

Synonyms: CHEMBL352043, SureCN525536, CGP-3543
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Disease relevance of Bicozamycin

  • Studies of changes in predominant aerobic fecal flora among the 11 subjects treated with bicozamycin showed the appearance of only one highly resistant Citrobacter freundii at the end of 1 wk of therapy and only a total of six resistant isolates at the end of 3 wk [1].
  • Treatment failed in significantly fewer patients treated with bicozamycin than those treated with placebo when diarrhea was associated with Shigella, Salmonella or toxigenic E. coli [2].
  • The mean duration of illness was shorter in the bicozamycin than the placebo treatment groups for patients with diarrhea due to Shigella (37 versus 96 hours; p = 0.01), toxigenic Escherichia coli (31 versus 60 hours; p = 0.003), and unknown pathogens (18 versus 41 hours; p = 0.02) [2].
  • Bicyclomycin is a commercially important antibiotic that has been shown to be effective against many gram-negative bacteria [3].
  • Our results explain the lack of activity of bicyclomycin against many gram-positive bacteria and raise the possibility that the essentiality of rho may be the exception rather than the rule [4].

High impact information on Bicozamycin


Chemical compound and disease context of Bicozamycin


Biological context of Bicozamycin


Associations of Bicozamycin with other chemical compounds


Gene context of Bicozamycin

  • Resistance to teicoplanin rose 4-fold by insertional inactivation of tcaA or by deletion of the entire operon. tcaA encodes a hypothetical transmembrane protein with a metal-binding motif, possibly a sensor-transducer. tcaB codes for a membrane-associated protein, which has sequence homologies to a bicyclomycin resistance protein [16].
  • The antibiotic bicyclomycin inhibited the in vitro RNA-dependent ATPase activity of Rho 77, did not inhibit growth of streptomycetes but delayed the development of aerial mycelia [17].
  • The strain containing the G337S Rho mutation also has high bicyclomycin resistance, and the proximity of L208, S266 and G337 in the quaternary structure of the Rho model has enabled a candidate bicyclomycin-binding pocket to be delineated [18].
  • All but one of the resistant mutants displayed greatly increased tna operon expression when grown in the presence of bicyclomycin [19].
  • In this study we describe BI-K0058, a new inhibitor of the transcription-termination factor Rho belonging to a different chemical class from bicyclomycin, the only known antibiotic acting on Rho [20].

Analytical, diagnostic and therapeutic context of Bicozamycin

  • The efficacy of bicozamycin, a poorly absorbable antibiotic, in the treatment of acute diarrhea was assessed in a prospective, double-blind study of 140 adults from the United States visiting Guadalajara, Mexico. Patients randomly received bicozamycin (500 mg orally four times daily) or placebo for 3 days [2].
  • Development of a technique to determine bicyclomycin-rho binding and stoichiometry by isothermal titration calorimetry and mass spectrometry [21].
  • In one instance, the racemic analogue 10c (R1 = CH2Ph, R2 = OH, R3 = H) showed interesting antimicrobial activity against several Gram-positive organisms; the minimum inhibitory concentrations were of the same order of magnitude as bicyclomycin displays toward Gram-negative organisms [22].


  1. Efficacy of bicozamycin in preventing traveler's diarrhea. Ericsson, C.D., DuPont, H.L., Galindo, E., Mathewson, J.J., Morgan, D.R., Wood, L.V., Mendiola, J. Gastroenterology (1985) [Pubmed]
  2. Bicozamycin, a poorly absorbable antibiotic, effectively treats travelers' diarrhea. Ericsson, C.D., DuPont, H.L., Sullivan, P., Galindo, E., Evans, D.G., Evans, D.J. Ann. Intern. Med. (1983) [Pubmed]
  3. Effects of bicyclomycin on RNA- and ATP-binding activities of transcription termination factor Rho. Carrano, L., Bucci, C., De Pascalis, R., Lavitola, A., Manna, F., Corti, E., Bruni, C.B., Alifano, P. Antimicrob. Agents Chemother. (1998) [Pubmed]
  4. rho is not essential for viability or virulence in Staphylococcus aureus. Washburn, R.S., Marra, A., Bryant, A.P., Rosenberg, M., Gentry, D.R. Antimicrob. Agents Chemother. (2001) [Pubmed]
  5. ATP binding to Rho transcription termination factor. Mutant F355W ATP-induced fluorescence quenching reveals dynamic ATP binding. Xu, Y., Johnson, J., Kohn, H., Widger, W.R. J. Biol. Chem. (2003) [Pubmed]
  6. Evidence for the location of bicyclomycin binding to the Escherichia coli transcription termination factor Rho. Riba, I., Gaskell, S.J., Cho, H., Widger, W.R., Kohn, H. J. Biol. Chem. (1998) [Pubmed]
  7. The antibiotic bicyclomycin affects the secondary RNA binding site of Escherichia coli transcription termination factor Rho. Magyar, A., Zhang, X., Kohn, H., Widger, W.R. J. Biol. Chem. (1996) [Pubmed]
  8. Characterization of an unusual Rho factor from the high G + C gram-positive bacterium Micrococcus luteus. Nowatzke, W.L., Richardson, J.P. J. Biol. Chem. (1996) [Pubmed]
  9. Mechanism of action of bicyclomycin. Tanaka, N., Iseki, M., Miyoshi, T., Aoki, H., Imanaka, H. J. Antibiot. (1976) [Pubmed]
  10. Rho transcription factor: symmetry and binding of bicyclomycin. Vincent, F., Openshaw, M., Trautwein, M., Gaskell, S.J., Kohn, H., Widger, W.R. Biochemistry (2000) [Pubmed]
  11. Characterization of the detachable Rho-dependent transcription terminator of the fimE gene in Escherichia coli K-12. Hinde, P., Deighan, P., Dorman, C.J. J. Bacteriol. (2005) [Pubmed]
  12. Participation of Rho-dependent transcription termination in oxidative stress sensitivity caused by an rpoB mutation. Kawamura, N., Kurokawa, K., Ito, T., Hamamoto, H., Koyama, H., Kaito, C., Sekimizu, K. Genes Cells (2005) [Pubmed]
  13. Structural modification of Escherichia coli peptidoglycan induced by bicyclomycin. Pisabarro, A.G., Cañada, F.J., Vázquez, D., Arriaga, P., Rodríguez-Tébar, A. J. Antibiot. (1986) [Pubmed]
  14. Transcription termination factor rho: the site of bicyclomycin inhibition in Escherichia coli. Zwiefka, A., Kohn, H., Widger, W.R. Biochemistry (1993) [Pubmed]
  15. Antimicrobial therapy for travelers' diarrhea. DuPont, H.L., Ericsson, C.D., Reves, R.R., Galindo, E. Rev. Infect. Dis. (1986) [Pubmed]
  16. Inactivation of a novel three-cistronic operon tcaR-tcaA-tcaB increases teicoplanin resistance in Staphylococcus aureus. Brandenberger, M., Tschierske, M., Giachino, P., Wada, A., Berger-Bächi, B. Biochim. Biophys. Acta (2000) [Pubmed]
  17. Isolation and sequencing of the rho gene from Streptomyces lividans ZX7 and characterization of the RNA-dependent NTPase activity of the overexpressed protein. Ingham, C.J., Hunter, I.S., Smith, M.C. J. Biol. Chem. (1996) [Pubmed]
  18. The bicyclomycin sensitivities of 38 bicyclomycin-resistant mutants of transcription termination protein rho and the location of their mutations support a structural model of rho based on the F(1) ATPase. Moyse, K.A., Knight, J.S., Richardson, J.P. J. Mol. Biol. (2000) [Pubmed]
  19. Bicyclomycin sensitivity and resistance affect Rho factor-mediated transcription termination in the tna operon of Escherichia coli. Yanofsky, C., Horn, V. J. Bacteriol. (1995) [Pubmed]
  20. A new inhibitor of the transcription-termination factor Rho. Carrano, L., Alifano, P., Corti, E., Bucci, C., Donadio, S. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  21. Development of a technique to determine bicyclomycin-rho binding and stoichiometry by isothermal titration calorimetry and mass spectrometry. Brogan, A.P., Widger, W.R., Bensadek, D., Riba-Garcia, I., Gaskell, S.J., Kohn, H. J. Am. Chem. Soc. (2005) [Pubmed]
  22. Synthesis and antimicrobial evaluation of bicyclomycin analogues. Williams, R.M., Armstrong, R.W., Dung, J.S. J. Med. Chem. (1985) [Pubmed]
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