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Chemical Compound Review

Thienamycin     (5R,6S)-3-(2- aminoethylsulfanyl)-6-(1...

Synonyms: CHEMBL278773, SureCN160509, AG-G-14273, AC1L9ALF, CTK1H0525, ...
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Disease relevance of Thienamycin


High impact information on Thienamycin


Chemical compound and disease context of Thienamycin


Biological context of Thienamycin


Anatomical context of Thienamycin

  • After a single intravenous dose of 25 mg/kg, a peak N-formimidoyl thienamycin concentration in cerebrospinal fluid (CSF) of 2.5 micrograms/ml was attained at 45 min [19].
  • N-Formimidoyl thienamycin penetrated uninflamed meninges, and peak concentrations were significantly augmented by coadministration of MK791 [20].
  • N-formimidoyl thienamycin initially caused the formation of abnormally shaped cells which developed into spheroplasts [21].
  • Phagocytic function and antibody-dependent cellular cytotoxicity of human neutrophils in the presence of N-formimidoyl thienamycin [22].

Associations of Thienamycin with other chemical compounds


Gene context of Thienamycin

  • Lamoxactam and azthreonam failed to inhibit the TEM-1 enzyme, whereas N-formimidoyl thienamycin was a competitive inhibitor [18].
  • Comparative in vitro activity of N-formimidoyl thienamycin against gram-positive and gram-negative aerobic and anaerobic species and its beta-lactamase stability [27].
  • Metabolism of thienamycin and related carbapenem antibiotics by the renal dipeptidase, dehydropeptidase [28].
  • delta 1-Thienamycin (2), a double-bond isomer of thienamycin, was prepared by isomerizing N-[[(p-nitrobenzyl)oxy]-carbonyl]thienamycin p-nitrobenzyl ester (5b) with DBU in Me2SO followed by hydrogenolysis of the protecting groups [29].
  • The antibacterial activity of thienamycin against multiresistant bacteria-comparison with beta-lactamase stable compounds [30].

Analytical, diagnostic and therapeutic context of Thienamycin

  • The susceptibilities of 462 clinical anaerobic bacterial isolates to N-formimidoyl thienamycin and 16 other currently available and investigational antibiotics were determined by the agar dilution technique [5].
  • High-performance liquid chromatographic (HPLC) methods using ultraviolet (UV) detection have been developed for the assay of the antibiotic imipenem (N-formimidoyl thienamycin) in human plasma and urine [31].
  • N-formimidoyl thienamycin is a new semisynthetic beta-lactam antibiotic still awaiting clinical trials [32].
  • The transformant No. 12 produced a thienamycin-like substance identified by paper chromatography and HPLC analysis [33].


  1. Biosynthesis of the beta-lactam antibiotic, thienamycin, by Streptomyces cattleya. Williamson, J.M., Inamine, E., Wilson, K.E., Douglas, A.W., Liesch, J.M., Albers-Schönberg, G. J. Biol. Chem. (1985) [Pubmed]
  2. Comparative in vitro activities of third-generation cephalosporins. Fass, R.J. Arch. Intern. Med. (1983) [Pubmed]
  3. Inhibition of transpeptidase activity in Escherichia coli by thienamycin. Moore, B.A., Jevons, S., Brammer, K.W. Antimicrob. Agents Chemother. (1979) [Pubmed]
  4. Activity of N-formimidoyl thienamycin and cephalosporins against isolates from nosocomially acquired bacteremia. Gutiérrez-Núñez, J., Harrington, P.T., Ramirez-Ronda, C.H. Antimicrob. Agents Chemother. (1982) [Pubmed]
  5. Susceptibilities of anaerobic bacteria to N-formimidoyl thienamycin (MK0787) and to other antibiotics. Kesado, T., Watanabe, K., Asahi, Y., Isono, M., Ueno, K. Antimicrob. Agents Chemother. (1982) [Pubmed]
  6. The biosynthetic gene cluster for the beta-lactam carbapenem thienamycin in Streptomyces cattleya. Núñez, L.E., Méndez, C., Braña, A.F., Blanco, G., Salas, J.A. Chem. Biol. (2003) [Pubmed]
  7. Imipenem/cilastatin. A review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Clissold, S.P., Todd, P.A., Campoli-Richards, D.M. Drugs (1987) [Pubmed]
  8. Reverse transsulfuration and its relationship to thienamycin biosynthesis in Streptomyces cattleya. Williamson, J.M., Meyer, R., Inamine, E. Antimicrob. Agents Chemother. (1985) [Pubmed]
  9. Postantibiotic effect of imipenem on Pseudomonas aeruginosa. Bustamante, C.I., Drusano, G.L., Tatem, B.A., Standiford, H.C. Antimicrob. Agents Chemother. (1984) [Pubmed]
  10. Chemoprophylaxis of experimental rabbit endocarditis with N-formimidoyl thienamycin. Guze, P.A., Kalmanson, G.M., Ishida, K., Freedman, L.R., Guze, L.B. J. Infect. Dis. (1984) [Pubmed]
  11. Ocular penetration of N-formimidoyl thienamycin (MK-787) and potentiation by dipeptidase inhibitor (MK-791). Finlay, K.R., Carlson, C.L., Chow, A.W. Invest. Ophthalmol. Vis. Sci. (1983) [Pubmed]
  12. Comparative activities of N-formimidoyl thienamycin, ticarcillin, and tobramycin against experimental Pseudomonas aeruginosa pneumonia. Pennington, J.E., Johnson, C.E. Antimicrob. Agents Chemother. (1982) [Pubmed]
  13. MK0787 (N-formimidoyl thienamycin): evaluation of in vitro and in vivo activities. Kropp, H., Sundelof, J.G., Kahan, J.S., Kahan, F.M., Birnbaum, J. Antimicrob. Agents Chemother. (1980) [Pubmed]
  14. Comparative activities of 13 beta-lactam antibiotics. Muytjens, H.L., van der Ros-van de Repe, J. Antimicrob. Agents Chemother. (1982) [Pubmed]
  15. Pharmacokinetics and tolerance of N-formimidoyl thienamycin (MK0787) in humans. Norrby, S.R., Alestig, K., Ferber, F., Huber, J.L., Jones, K.H., Kahan, F.M., Meisinger, M.A., Rogers, J.D. Antimicrob. Agents Chemother. (1983) [Pubmed]
  16. Inhibition of beta-lactam antibiotics at two different times in the cell cycle of Streptococcus faecium ATCC 9790. Pucci, M.J., Hinks, E.T., Dicker, D.T., Higgins, M.L., Daneo-Moore, L. J. Bacteriol. (1986) [Pubmed]
  17. Gene localization and expression of thienamycin cyclase gene in Streptomyces lividans TK24. Li, R., Wang, Y. Chin. J. Biotechnol. (1996) [Pubmed]
  18. Investigations on beta-lactamase stability of recently developed beta-lactam compounds: study of enzyme kinetics. Cullmann, W., Dick, W. Zentralblatt für Bakteriologie, Mikrobiologie und Hygiene. 1. Abt. Originale A, Medizinische Mikrobiologie, Infektionskrankheiten und Parasitologie = International journal of microbiology and hygiene. A, Medical microbiology, infectiousdiseases, para... (1983) [Pubmed]
  19. Pharmacokinetics and bacteriological efficacy of N-formimidoyl thienamycin in experimental Escherichia coli meningitis. Patamasucon, P., McCracken, G.H. Antimicrob. Agents Chemother. (1982) [Pubmed]
  20. Intrathecal penetration of N-formimidoyl thienamycin in normal rabbits: potentiation by coadministration of renal dipeptidase enzyme inhibitor. Chow, A.W., Finlay, K.R., Stiver, H.G., Carlson, C.L. Antimicrob. Agents Chemother. (1983) [Pubmed]
  21. The morphological response of Pseudomonas aeruginosa to azthreonam, cefoperazone, ceftazidime and N-formimidoyl thienamycin. Elliott, T.S., Greenwood, D. J. Med. Microbiol. (1984) [Pubmed]
  22. Phagocytic function and antibody-dependent cellular cytotoxicity of human neutrophils in the presence of N-formimidoyl thienamycin. Rodriguez, A.B., Barriga, C., de la Fuente, M. Agents Actions (1990) [Pubmed]
  23. Susceptibility of pneumococci to 14 beta-lactam agents: comparison of strains resistant, intermediate-resistant, and susceptible to penicillin. Ward, J.I., Moellering, R.C. Antimicrob. Agents Chemother. (1981) [Pubmed]
  24. Use of an in-vitro kinetic model to study antibiotic combinations. Zinner, S.H., Blaser, J., Stone, B.B., Groner, M.C. J. Antimicrob. Chemother. (1985) [Pubmed]
  25. Susceptibility of penicillin-resistant pneumococci to eighteen antimicrobials: implications for treatment of meningitis. Tweardy, D.J., Jacobs, M.R., Speck, W.T. J. Antimicrob. Chemother. (1983) [Pubmed]
  26. Imipenem (N-formimidoyl thienamycin): in vitro antimicrobial activity and beta-lactamase stability. Barry, A.L., Jones, R.N., Thornsberry, C., Ayers, L.W., Kundargi, R. Diagn. Microbiol. Infect. Dis. (1985) [Pubmed]
  27. Comparative in vitro activity of N-formimidoyl thienamycin against gram-positive and gram-negative aerobic and anaerobic species and its beta-lactamase stability. Neu, H.C., Labthavikul, P. Antimicrob. Agents Chemother. (1982) [Pubmed]
  28. Metabolism of thienamycin and related carbapenem antibiotics by the renal dipeptidase, dehydropeptidase. Kropp, H., Sundelof, J.G., Hajdu, R., Kahan, F.M. Antimicrob. Agents Chemother. (1982) [Pubmed]
  29. Preparation and antibacterial activity of delta 1-thienamycin. Shih, D.H., Ratcliffe, R.W. J. Med. Chem. (1981) [Pubmed]
  30. The antibacterial activity of thienamycin against multiresistant bacteria-comparison with beta-lactamase stable compounds. Romagnoli, M.F., Fu, K.P., Neu, H.C. J. Antimicrob. Chemother. (1980) [Pubmed]
  31. Determination of imipenem (N-formimidoyl thienamycin) in human plasma and urine by high-performance liquid chromatography, comparison with microbiological methodology and stability. Gravallese, D.A., Musson, D.G., Pauliukonis, L.T., Bayne, W.F. J. Chromatogr. (1984) [Pubmed]
  32. The in vitro activity of N-formimidoyl thienamycin compared with other broad-spectrum cephalosporins and with clindamycin and metronidazole. Tischhauser, G., Kayser, F.H. Infection (1983) [Pubmed]
  33. Cloning of thienamycin biosynthetase genes from Streptomyces cattleya. Li, R., Wang, Y., Zeng, Y. Chin. J. Biotechnol. (1993) [Pubmed]
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