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Chemical Compound Review

Imipenem, Anhydrous     (5R,6S)-3-[2- (aminomethylideneamino) ethyls...

Synonyms: MK-787, LS-22373, AC1L2HU9, C12H17N3O4S, EINECS 264-734-5, ...
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Disease relevance of MK 0787


Psychiatry related information on MK 0787

  • The data indicate that exposure of E. coli and S. aureus to a sub-MIC of imipenem enhances the susceptibility of these potential pathogens to cellular and humoral host defense mechanisms [5].
  • One death in the comprehensive broad-spectrum empirical antimicrobial therapy group was associated with peritonitis from Clostridium perfringens that was sensitive to imipenem plus cilastin sodium, and the other was associated with peritonitis from Pseudomonas aeruginosa that was resistant to imipenem plus cilastin sodium [6].
  • It could be a factor of imipenem resistance if the antibiotic influx into the bacteria was decreased or if the beta-lactamase Id was synthesized at a high level [7].
  • We describe the case of an 84-year-old woman who developed a confusional state and suffered from a generalized tonic-clonic seizure while she was treated with imipenem, a beta-lactam antibiotic [8].

High impact information on MK 0787


Chemical compound and disease context of MK 0787


Biological context of MK 0787

  • Because IMP-1 has been found in several clinically important carbapenem-resistant pathogens, there is a need for inhibitors of this enzyme that could protect broad spectrum antibiotics such as imipenem from hydrolysis and thus extend their utility [16].
  • We have characterized the binding site in the protein D2 channel by studying the competitive inhibition, by various solutes, of imipenem diffusion into the periplasm [17].
  • Imipenem is highly stable against attack by beta-lactamases of both plasmid and chromosomal origin, and is more stable by several thousand-fold than earlier beta-lactamase stable compounds [18].
  • Several isolates were reported by the clinical microbiology laboratories as being susceptible to imipenem [19].
  • The amino acid sequence of OprE had some clusters of sequence homologous with that of OprD of P. aeruginosa, which might be responsible for the outer membrane permeability of imipenem and basic amino acids [20].

Anatomical context of MK 0787


Associations of MK 0787 with other chemical compounds


Gene context of MK 0787

  • Resistance to beta-lactam and FQ was correlated with ampC and mexC gene expression levels, respectively, whereas imipenem resistance was attributable to decreased oprD expression [28].
  • However, measurement of beta-lactamase activities (including measurements under conditions where TEM-1 beta-lactamase was inhibited) indicated that the imipenem-intermediate isolate expressed six- to eightfold less beta-lactamase than did the other isolates [29].
  • These results demonstrate that in clinical practice, gyrA mutations are the major mechanism of resistance to fluoroquinolones even in the strains of P. aeruginosa resistant to imipenem and lacking OprD, concomitant resistance to these drugs being the result of the addition of at least two independent mechanisms [30].
  • In mice with IL-6 levels >14,000 pg/ml, 25% survived if imipenem was started at 6 h, whereas none survived if antibiotics were started later (P < 0.05) [31].
  • The results showed that oprD was relatively stable against carbapenem antibiotics. oprM was induced significantly by imipenem in only one strain and oprN was induced by imipenem in most of the strains [32].

Analytical, diagnostic and therapeutic context of MK 0787


  1. Class restriction of cephalosporin use to control total cephalosporin resistance in nosocomial Klebsiella. Rahal, J.J., Urban, C., Horn, D., Freeman, K., Segal-Maurer, S., Maurer, J., Mariano, N., Marks, S., Burns, J.M., Dominick, D., Lim, M. JAMA (1998) [Pubmed]
  2. Clinical and molecular epidemiology of acinetobacter infections sensitive only to polymyxin B and sulbactam. Go, E.S., Urban, C., Burns, J., Kreiswirth, B., Eisner, W., Mariano, N., Mosinka-Snipas, K., Rahal, J.J. Lancet (1994) [Pubmed]
  3. Imipenem-resistant Escherichia coli. Brown, D.F., Farrington, M., Warren, R.E. Lancet (1993) [Pubmed]
  4. Simultaneous resistance to metronidazole, co-amoxiclav, and imipenem in clinical isolate of Bacteroides fragilis. Turner, P., Edwards, R., Weston, V., Gazis, A., Ispahani, P., Greenwood, D. Lancet (1995) [Pubmed]
  5. Enhanced phagocytosis, killing, and serum sensitivity of Escherichia coli and Staphylococcus aureus treated with sub-MICs of imipenem. Adinolfi, L.E., Bonventre, P.F. Antimicrob. Agents Chemother. (1988) [Pubmed]
  6. Management of intra-abdominal infections. The case for intraoperative cultures and comprehensive broad-spectrum antibiotic coverage. The Canadian Intra-abdominal Infection Study Group. Christou, N.V., Turgeon, P., Wassef, R., Rotstein, O., Bohnen, J., Potvin, M. Archives of surgery (Chicago, Ill. : 1960) (1996) [Pubmed]
  7. beta-Lactamase Id of ceftazidime-resistant Pseudomonas aeruginosa strains. Michel-Briand, Y., Nicolas, T., Godard, C., Plesiat, P. Microbiologica (1992) [Pubmed]
  8. Encephalopathy secondary to imipenem therapy. Fernández-Torre, J.L., Velasco, M., Gutiérrez, R., Fernández-Sampedro, M. Clinical EEG and neuroscience : official journal of the EEG and Clinical Neuroscience Society (ENCS). (2004) [Pubmed]
  9. Controlled clinical trial of pefloxacin versus imipenem in severe acute pancreatitis. Bassi, C., Falconi, M., Talamini, G., Uomo, G., Papaccio, G., Dervenis, C., Salvia, R., Minelli, E.B., Pederzoli, P. Gastroenterology (1998) [Pubmed]
  10. Enterococcal superinfection in paediatric oncology patients treated with imipenem. Gray, J.W., Pedler, S., Kernahan, J., Pearson, A.D., Craft, A.W. Lancet (1992) [Pubmed]
  11. Efficacy of imipenem in experimental Legionnaires' disease. Fitzgeorge, R.B., Gibson, D.H., Jepras, R.I., Baskerville, A. Lancet (1985) [Pubmed]
  12. Monotherapy for fever and neutropenia in cancer patients: a randomized comparison of ceftazidime versus imipenem. Freifeld, A.G., Walsh, T., Marshall, D., Gress, J., Steinberg, S.M., Hathorn, J., Rubin, M., Jarosinski, P., Gill, V., Young, R.C. J. Clin. Oncol. (1995) [Pubmed]
  13. Factors predisposing to seizures in seriously ill infected patients receiving antibiotics: experience with imipenem/cilastatin. Calandra, G., Lydick, E., Carrigan, J., Weiss, L., Guess, H. Am. J. Med. (1988) [Pubmed]
  14. Effect of the abscess environment on the antimicrobial activity of ciprofloxacin. Bryant, R.E., Mazza, J.A. Am. J. Med. (1989) [Pubmed]
  15. Use of ceftazidime in the treatment of nosocomial lower respiratory infections. Trenholme, G.M., Pottage, J.C., Karakusis, P.H. Am. J. Med. (1985) [Pubmed]
  16. Succinic acids as potent inhibitors of plasmid-borne IMP-1 metallo-beta-lactamase. Toney, J.H., Hammond, G.G., Fitzgerald, P.M., Sharma, N., Balkovec, J.M., Rouen, G.P., Olson, S.H., Hammond, M.L., Greenlee, M.L., Gao, Y.D. J. Biol. Chem. (2001) [Pubmed]
  17. Protein D2 channel of the Pseudomonas aeruginosa outer membrane has a binding site for basic amino acids and peptides. Trias, J., Nikaido, H. J. Biol. Chem. (1990) [Pubmed]
  18. Carbapenems: special properties contributing to their activity. Neu, H.C. Am. J. Med. (1985) [Pubmed]
  19. Rapid spread of carbapenem-resistant Klebsiella pneumoniae in New York City: a new threat to our antibiotic armamentarium. Bratu, S., Landman, D., Haag, R., Recco, R., Eramo, A., Alam, M., Quale, J. Arch. Intern. Med. (2005) [Pubmed]
  20. Cloning and nucleotide sequence of anaerobically induced porin protein E1 (OprE) of Pseudomonas aeruginosa PAO1. Yamano, Y., Nishikawa, T., Komatsu, Y. Mol. Microbiol. (1993) [Pubmed]
  21. Pharmacokinetic profile of imipenem/cilastatin in normal volunteers. Drusano, G.L., Standiford, H.C. Am. J. Med. (1985) [Pubmed]
  22. Comparative in vitro killing activities of meropenem, imipenem, ceftriaxone, and ceftriaxone plus vancomycin at clinically achievable cerebrospinal fluid concentrations against penicillin-resistant Streptococcus pneumoniae isolates from children with meningitis. Fitoussi, F., Doit, C., Benali, K., Bonacorsi, S., Geslin, P., Bingen, E. Antimicrob. Agents Chemother. (1998) [Pubmed]
  23. Clinical pharmacology of imipenem and cilastatin in premature infants during the first week of life. Reed, M.D., Kliegman, R.M., Yamashita, T.S., Myers, C.M., Blumer, J.L. Antimicrob. Agents Chemother. (1990) [Pubmed]
  24. Inhibition of the mammalian beta-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-(acylamino)-3-substituted-propenoic acids. Graham, D.W., Ashton, W.T., Barash, L., Brown, J.E., Brown, R.D., Canning, L.F., Chen, A., Springer, J.P., Rogers, E.F. J. Med. Chem. (1987) [Pubmed]
  25. Beta-lactamase activity of purified and partially characterized human renal dipeptidase. Campbell, B.J., Forrester, L.J., Zahler, W.L., Burks, M. J. Biol. Chem. (1984) [Pubmed]
  26. A comparison of imipenem to ceftazidime with or without amikacin as empiric therapy in febrile neutropenic patients. Rolston, K.V., Berkey, P., Bodey, G.P., Anaissie, E.J., Khardori, N.M., Joshi, J.H., Keating, M.J., Holmes, F.A., Cabanillas, F.F., Elting, L. Arch. Intern. Med. (1992) [Pubmed]
  27. Results of a randomized trial comparing sequential intravenous/oral treatment with ciprofloxacin plus metronidazole to imipenem/cilastatin for intra-abdominal infections. The Intra-Abdominal Infection Study Group. Solomkin, J.S., Reinhart, H.H., Dellinger, E.P., Bohnen, J.M., Rotstein, O.D., Vogel, S.B., Simms, H.H., Hill, C.S., Bjornson, H.S., Haverstock, D.C., Coulter, H.O., Echols, R.M. Ann. Surg. (1996) [Pubmed]
  28. Development and Persistence of Antimicrobial Resistance in Pseudomonas aeruginosa: a Longitudinal Observation in Mechanically Ventilated Patients. Reinhardt, A., Köhler, T., Wood, P., Rohner, P., Dumas, J.L., Ricou, B., van Delden, C. Antimicrob. Agents Chemother. (2007) [Pubmed]
  29. Carbapenem resistance in Escherichia coli associated with plasmid-determined CMY-4 beta-lactamase production and loss of an outer membrane protein. Stapleton, P.D., Shannon, K.P., French, G.L. Antimicrob. Agents Chemother. (1999) [Pubmed]
  30. Role of mutations in DNA gyrase genes in ciprofloxacin resistance of Pseudomonas aeruginosa susceptible or resistant to imipenem. Cambau, E., Perani, E., Dib, C., Petinon, C., Trias, J., Jarlier, V. Antimicrob. Agents Chemother. (1995) [Pubmed]
  31. Early antibiotic administration but not antibody therapy directed against IL-6 improves survival in septic mice predicted to die on basis of high IL-6 levels. Vyas, D., Javadi, P., Dipasco, P.J., Buchman, T.G., Hotchkiss, R.S., Coopersmith, C.M. Am. J. Physiol. Regul. Integr. Comp. Physiol. (2005) [Pubmed]
  32. Effect of carbapenems on the transcriptional expression of the oprD, oprM and oprN genes in Pseudomonas aeruginosa. Kolayli, F., Karadenizli, A., Savli, H., Ergen, K., Hatirnaz, O., Balikci, E., Budak, F., Vahaboglu, H. J. Med. Microbiol. (2004) [Pubmed]
  33. CzcR-CzcS, a two-component system involved in heavy metal and carbapenem resistance in Pseudomonas aeruginosa. Perron, K., Caille, O., Rossier, C., Van Delden, C., Dumas, J.L., Köhler, T. J. Biol. Chem. (2004) [Pubmed]
  34. Imipenem (N-F-thienamycin) versus netilmicin plus clindamycin. A controlled and randomized comparison in intra-abdominal infections. Gonzenbach, H.R., Simmen, H.P., Amgwerd, R. Ann. Surg. (1987) [Pubmed]
  35. Multiple-dose study of imipenem/cilastatin in patients with end-stage renal disease undergoing long-term hemodialysis. Berman, S.J., Sugihara, J.G., Nakamura, J.M., Kawahara, K.K., Wong, E.G., Musgrave, J.E., Wong, L.M., Siemsen, A.M. Am. J. Med. (1985) [Pubmed]
  36. Tissue distribution of imipenem in critically ill patients. Tegeder, I., Schmidtko, A., Bräutigam, L., Kirschbaum, A., Geisslinger, G., Lötsch, J. Clin. Pharmacol. Ther. (2002) [Pubmed]
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