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Chemical Compound Review

LS-149976     7-[[(E)-2-(2-amino-1,3- thiazol-4-yl)-4...

Synonyms: LS-187379, AC1O44MA, C15H14N4O6S2
 
 
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Disease relevance of cis-Ceftibutin

 

Psychiatry related information on cis-Ceftibutin

 

High impact information on cis-Ceftibutin

  • Modifications of the cephem nucleus at position 7 by addition of methoxy groups increase beta-lactamase stability but decrease activity against gram-positive species because of lower affinity for penicillin-binding proteins [7].
  • beta-lactam antibiotics. Novel synthetic routes to cephem-ring system from beta-lactam thiazolines via hydrazinothioazetidinones [8].
  • In conclusion, PIP showed excellent activities against BLNAR strains in a manner different from those of cephem antibiotics, suggesting that it could be a candidate therapeutic agent for the treatment of meningitis caused by BLNAR strains [9].
  • Azithromycin was similar or superior to ceftibuten in mixed general practice populations of patients [10].
  • Nosocomial spread of cephem-resistant Escherichia coli strains carrying multiple Toho-1-like beta-lactamase genes [11].
 

Chemical compound and disease context of cis-Ceftibutin

 

Biological context of cis-Ceftibutin

  • Multiple-dose pharmacokinetics of ceftibuten in healthy volunteers [17].
  • Effect of protein binding in serum on therapeutic efficacy of cephem antibiotics [18].
  • Ceftibuten has a wide spectrum of antimicrobial activity against both Gram-positive and Gram-negative pathogens, and is stable to hydrolysis by a large number of beta-lactamases [19].
  • The nonlinear nature of these agents is reflected by decreasing maximal concentrations with escalating doses of cefixime and cefetamet pivoxil, decreasing area under the serum concentration-time curve with increasing doses for cefixime, and a reduced bioavailability with large doses of ceftibuten [20].
  • In the intraperitoneal infection caused by Staphylococcus aureus or Klebsiella pneumoniae, the 50% effective doses (ED50s) of the cephem antibiotics correlated with the area under the concentration-time curve (AUC) values of free levels in serum and the MICs but not with those of total levels in serum [18].
 

Anatomical context of cis-Ceftibutin

 

Associations of cis-Ceftibutin with other chemical compounds

  • Antimicrobial activity, spectrum, and recommendations for disk diffusion susceptibility testing of ceftibuten (7432-S; SCH 39720), a new orally administered cephalosporin [13].
  • Cefpodoxime proxetil is an oral cephem antibiotic of a new ester type, developed by Sankyo Co., Ltd in Japan. It has a broad antibacterial spectrum, which includes Staphylococcus, and a long half-life, allowing twice-daily administration [24].
  • The in vitro activity of Bay v 3522, a new aminobenzothiazol cephem, was compared with those of other oral beta-lactams [25].
  • In vitro and in vivo antibacterial properties of FK 027, a new orally active cephem antibiotic [26].
  • In vitro activities of ICI 194008 and ICI 193428, two new cephem antimicrobial agents [27].
 

Gene context of cis-Ceftibutin

  • Ceftibuten was found to be very stable in the presence of five commonly occurring beta-lactamases of both the chromosomal-mediated (P99, K1) and plasmid-mediated (CARB-2, OXA-1, TEM-1) types [28].
  • In the fourth approach, the human PEPT 1 was expressed in Xenopus laevis oocytes and PEPT 1-mediated transport of ceftibuten was investigated directly by electrophysiological methods [29].
  • In this approach also it was found that PEPT 2-mediated Gly-Sar uptake was inhibited by cefixime and ceftibuten [29].
  • Only Type Ia (P99) beta-lactamase was significantly inhibited by ceftibuten [28].
  • Flomoxef is a fourth generation cephem which has the same activity against gram-negative bacteria as the third generation cephems, but is also active against gram-positive organisms, especially most methicillin resistant Staphylococcus aureus (MRSA) [30].
 

Analytical, diagnostic and therapeutic context of cis-Ceftibutin

References

  1. Site-saturation studies of beta-lactamase: production and characterization of mutant beta-lactamases with all possible amino acid substitutions at residue 71. Schultz, S.C., Richards, J.H. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  2. In vitro activity of BMY-28100, a new oral cephalosporin. Eliopoulos, G.M., Reiszner, E., Wennersten, C., Moellering, R.C. Antimicrob. Agents Chemother. (1987) [Pubmed]
  3. Comparative in vitro activity of ceftibuten (Sch 39720) against bacterial enteropathogens. Shawar, R., LaRocco, M., Cleary, T.G. Antimicrob. Agents Chemother. (1989) [Pubmed]
  4. Alternative activity of beta-lactam antibiotics against methicillin- and cephem-resistant Staphylococcus aureus in the presence of respiratory tract mucus. Igarashi, K., Matsuyama, T. J. Infect. Dis. (1990) [Pubmed]
  5. Activities of ceftobiprole, a novel broad-spectrum cephalosporin, against Haemophilus influenzae and Moraxella catarrhalis. Bogdanovich, T., Clark, C., Ednie, L., Lin, G., Smith, K., Shapiro, S., Appelbaum, P.C. Antimicrob. Agents Chemother. (2006) [Pubmed]
  6. Comparison of the efficacy and tolerability of once-daily ceftibuten and twice-daily cefprozil in the treatment of children with acute otitis media. Blumer, J.L., Forti, W.P., Summerhouse, T.L. Clinical therapeutics. (1996) [Pubmed]
  7. Relation of structural properties of beta-lactam antibiotics to antibacterial activity. Neu, H.C. Am. J. Med. (1985) [Pubmed]
  8. beta-lactam antibiotics. Novel synthetic routes to cephem-ring system from beta-lactam thiazolines via hydrazinothioazetidinones. Franceschi, G., Foglio, M., Masi, P., Suarato, A., Palamidessi, G., Bernardi, L., Arcamone-Cainelli, G. J. Am. Chem. Soc. (1977) [Pubmed]
  9. In vitro activities of piperacillin against beta-lactamase-negative ampicillin-resistant Haemophilus influenzae. Morikawa, Y., Kitazato, M., Mitsuyama, J., Mizunaga, S., Minami, S., Watanabe, Y. Antimicrob. Agents Chemother. (2004) [Pubmed]
  10. Azithromycin. A review of its use in paediatric infectious diseases. Langtry, H.D., Balfour, J.A. Drugs (1998) [Pubmed]
  11. Nosocomial spread of cephem-resistant Escherichia coli strains carrying multiple Toho-1-like beta-lactamase genes. Yagi, T., Kurokawa, H., Senda, K., Ichiyama, S., Ito, H., Ohsuka, S., Shibayama, K., Shimokata, K., Kato, N., Ohta, M., Arakawa, Y. Antimicrob. Agents Chemother. (1997) [Pubmed]
  12. Penetration of ceftibuten into middle ear fluid. Lin, C., Kumari, P., Perrotta, R.J., Reidenberg, B.E. Antimicrob. Agents Chemother. (1996) [Pubmed]
  13. Antimicrobial activity, spectrum, and recommendations for disk diffusion susceptibility testing of ceftibuten (7432-S; SCH 39720), a new orally administered cephalosporin. Jones, R.N., Barry, A.L. Antimicrob. Agents Chemother. (1988) [Pubmed]
  14. Optimal times above MICs of ceftibuten and cefaclor in experimental intra-abdominal infections. Onyeji, C.O., Nicolau, D.P., Nightingale, C.H., Quintiliani, R. Antimicrob. Agents Chemother. (1994) [Pubmed]
  15. Production of low-affinity penicillin-binding protein by low- and high-resistance groups of methicillin-resistant Staphylococcus aureus. Murakami, K., Nomura, K., Doi, M., Yoshida, T. Antimicrob. Agents Chemother. (1987) [Pubmed]
  16. The relationship between an increase in beta-lactamase activity after oral administration of three new cephalosporins and protection against intestinal ecological disturbances. Edlund, C., Stark, C., Nord, C.E. J. Antimicrob. Chemother. (1994) [Pubmed]
  17. Multiple-dose pharmacokinetics of ceftibuten in healthy volunteers. Lin, C., Radwanski, E., Affrime, M., Cayen, M.N. Antimicrob. Agents Chemother. (1995) [Pubmed]
  18. Effect of protein binding in serum on therapeutic efficacy of cephem antibiotics. Tawara, S., Matsumoto, S., Kamimura, T., Goto, S. Antimicrob. Agents Chemother. (1992) [Pubmed]
  19. Ceftibuten pharmacokinetics and pharmacodynamics. Focus on paediatric use. Kearns, G.L., Young, R.A. Clinical pharmacokinetics. (1994) [Pubmed]
  20. Clinical pharmacokinetics of newer cephalosporins. Klepser, M.E., Marangos, M.N., Patel, K.B., Nicolau, D.P., Quintiliani, R., Nightingale, C.H. Clinical pharmacokinetics. (1995) [Pubmed]
  21. Pharmacokinetics of cephem antibiotics in exudate of pelvic retroperitoneal space after radical hysterectomy and pelvic lymphadenectomy. Ito, K., Hayasaki, M., Tamaya, T. Antimicrob. Agents Chemother. (1990) [Pubmed]
  22. Concentrations of cefixime in bronchial mucosa and sputum after three oral multiple dose regimens. Baldwin, D.R., Andrews, J.M., Ashby, J.P., Wise, R., Honeybourne, D. Thorax (1990) [Pubmed]
  23. Cephem sulfones as inactivators of human leukocyte elastase. 5. 7 alpha-Methoxy- and 7 alpha-chloro-1,1-dioxocephem 4-ketones. Alpegiani, M., Bissolino, P., Corigli, R., Del Nero, S., Perrone, E., Rizzo, V., Sacchi, N., Cassinelli, G., Franceschi, G., Baici, A. J. Med. Chem. (1994) [Pubmed]
  24. Summary of clinical experience with cefpodoxime proxetil in adults in Japan. Kumazawa, J. Drugs (1991) [Pubmed]
  25. In vitro activity of Bay v 3522, a new cephalosporin, compared with activities of other agents. Wise, R., Andrews, J.M., Ashby, J.P., Thornber, D. Antimicrob. Agents Chemother. (1990) [Pubmed]
  26. In vitro and in vivo antibacterial properties of FK 027, a new orally active cephem antibiotic. Kamimura, T., Kojo, H., Matsumoto, Y., Mine, Y., Goto, S., Kuwahara, S. Antimicrob. Agents Chemother. (1984) [Pubmed]
  27. In vitro activities of ICI 194008 and ICI 193428, two new cephem antimicrobial agents. Allan, J.D., Eliopoulos, G.M., Reiszner, E., Moellering, R.C. Antimicrob. Agents Chemother. (1987) [Pubmed]
  28. Ceftibuten (7432-S, SCH 39720): comparative antimicrobial activity against 4735 clinical isolates, beta-lactamase stability and broth microdilution quality control guidelines. Jones, R.N., Barry, A.L. Eur. J. Clin. Microbiol. Infect. Dis. (1988) [Pubmed]
  29. Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Ganapathy, M.E., Prasad, P.D., Mackenzie, B., Ganapathy, V., Leibach, F.H. Biochim. Biophys. Acta (1997) [Pubmed]
  30. The meaning of the development of flomoxef and clinical experience in Japan. Ito, M., Ishigami, T. Infection (1991) [Pubmed]
  31. Mechanism of inhibition of the PC1 beta-lactamase of Staphylococcus aureus by cephalosporins: importance of the 3'-leaving group. Faraci, W.S., Pratt, R.F. Biochemistry (1985) [Pubmed]
  32. Clinical evaluation of ceftibuten in gonorrhea. A pilot study in Hong Kong. Chong, L.Y., Cheung, W.M., Leung, C.S., Yu, C.W., Chan, L.Y. Sexually transmitted diseases. (1998) [Pubmed]
 
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