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Chemical Compound Review

MK-306     (6S,7S)-4- (aminocarbonyloxymethyl)-7...

Synonyms: LS-149937, AC1L1X8C, C16H17N3O7S2
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Disease relevance of cefoxitin


Psychiatry related information on cefoxitin


High impact information on cefoxitin

  • Our in vitro results show that cefoxitin causes an apparent rise in the serum creatinine level; the magnitude of the increase depends on the assay method and the concentration of cefoxitin [6].
  • Cefoxitin-resistant facultative or aerobic gram-negative bacilli in infections associated with the gastrointestinal tract [7].
  • The inactivation of RTEM-2 beta-lactamase and of Bacillus cereus beta-lactamase I is accelerated in the presence of A type substrates such as dicloxacillin, quinacillin, and cefoxitin, which are thought to expand or loosen the conformation of these enzymes [8].
  • Unexpectedly, the acyl enzyme complex with the beta-lactam inhibitor cefoxitin still has the catalytic water bound; this water had been predicted to be displaced by the unusual 7alpha-methoxy of the inhibitor [9].
  • In contrast to beta-lactam-based inhibitors clavulanate and cefoxitin, compound 10 did not up-regulate beta-lactamase expression in cell culture but simply inhibited the enzyme expressed by the resistant bacteria [10].

Chemical compound and disease context of cefoxitin


Biological context of cefoxitin


Anatomical context of cefoxitin


Associations of cefoxitin with other chemical compounds


Gene context of cefoxitin

  • Transformation of the transconjugant E. coli strain with plasmid pNH5 carrying the ampD gene (whose product decreases the level of expression of ampC) resulted in an eightfold decrease in the MIC of cefoxitin [29].
  • Typing by ERIC2-PCR indicated that the cefoxitin-resistant (FOXr) isolates were distinct. beta-Lactamase studies and hybridization experiments showed that most strains produced beta-lactamases related to the AmpC chromosomal cephalosporinase of Citrobacter freundii [30].
  • CONCLUSIONS: Cefoxitin resistance in E. coli N99-0001 was due to overexpression of ampC caused by an increase in promoter strength [31].
  • I made use of the unique RSAI values of SHV-1, TEM-1, and TEM-2 beta lactamases with cefoxitin to screen for the presence of these enzymes in Klebsiella aerogenes clinical isolates [32].
  • Mutations in the ampC promoter leading to increased production of the AmpC beta-lactamase were demonstrated in 11 cefoxitin-resistant or intermediate E. coli isolates [33].

Analytical, diagnostic and therapeutic context of cefoxitin


  1. Cefoxitin as a single-dose treatment for urethritis caused by penicillinase-producing Neisseria gonorrhoeae. Berg, S.W., Kilpatrick, M.E., Harrison, W.O., McCutchan, J.A. N. Engl. J. Med. (1979) [Pubmed]
  2. Cefamandole and cefoxitin. Sanders, C.V., Greenberg, R.N., Marier, R.L. Ann. Intern. Med. (1985) [Pubmed]
  3. Reversible acute leukopenia and cefoxitin. Shansky, M., Greenlaw, C.W. Ann. Intern. Med. (1980) [Pubmed]
  4. Ampicillin/sulbactam and cefoxitin in the treatment of cutaneous and other soft-tissue abscesses in patients with or without histories of injection drug abuse. Talan, D.A., Summanen, P.H., Finegold, S.M. Clin. Infect. Dis. (2000) [Pubmed]
  5. 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]
  6. Cefoxitin falsely elevates creatinine levels. Saah, A.J., Koch, T.R., Drusano, G.L. JAMA (1982) [Pubmed]
  7. Cefoxitin-resistant facultative or aerobic gram-negative bacilli in infections associated with the gastrointestinal tract. Saah, A.J., Drusano, G.L., Warren, J.W., Tenney, J.H., Caplan, E.S. Ann. Intern. Med. (1981) [Pubmed]
  8. Kinetics and mechanism of inactivation of the RTEM-2 beta-lactamase by phenylpropynal. Identification of the characteristic chromophore. Grace, M.E., Schenkein, D.P., Pratt, R.F. J. Biol. Chem. (1987) [Pubmed]
  9. Structure, function, and inhibition along the reaction coordinate of CTX-M beta-lactamases. Chen, Y., Shoichet, B., Bonnet, R. J. Am. Chem. Soc. (2005) [Pubmed]
  10. Structure-based optimization of a non-beta-lactam lead results in inhibitors that do not up-regulate beta-lactamase expression in cell culture. Tondi, D., Morandi, F., Bonnet, R., Costi, M.P., Shoichet, B.K. J. Am. Chem. Soc. (2005) [Pubmed]
  11. Enhanced activity of beta-lactam antibiotics with amdinocillin in vitro and and in vivo. Cleeland, R., Squires, E. Am. J. Med. (1983) [Pubmed]
  12. Identification and treatment of infections in multiply traumatized patients. Caplan, E.S., Hoyt, N.J. Am. J. Med. (1985) [Pubmed]
  13. In vitro activities of beta-lactam and aminoglycoside antibiotics. A comparative study of 20 parenterally administered drugs. Fass, R.J. Arch. Intern. Med. (1980) [Pubmed]
  14. Amdinocillin plus cefoxitin versus cefoxitin alone in therapy of mixed soft tissue infections (including diabetic foot infections). File, T.M., Tan, J.S. Am. J. Med. (1983) [Pubmed]
  15. Cefmenoxime versus cefoxitin in the treatment of serious bacterial infections. Tan, J.S., File, T.M. Am. J. Med. (1984) [Pubmed]
  16. Cefoxitin disposition in colorectal surgery. Implications for the effective use of prophylactic antibiotics. Alexander, D.P., Becker, J.M. Ann. Surg. (1988) [Pubmed]
  17. Use of adjuvants for enhancement of rectal absorption of cefoxitin in humans. Davis, S.S., Burnham, W.R., Wilson, P., O'Brien, J. Antimicrob. Agents Chemother. (1985) [Pubmed]
  18. Integron carrying a novel metallo-beta-lactamase gene, blaIMP-16, and a fused form of aminoglycoside-resistant gene aac(6')-30/aac(6')-Ib': report from the SENTRY Antimicrobial Surveillance Program. Mendes, R.E., Toleman, M.A., Ribeiro, J., Sader, H.S., Jones, R.N., Walsh, T.R. Antimicrob. Agents Chemother. (2004) [Pubmed]
  19. Transferable resistance to cefoxitin in Bacteroides thetaiotaomicron. Rashtchian, A., Dubes, G.R., Booth, S.J. Antimicrob. Agents Chemother. (1982) [Pubmed]
  20. Combination amdinocillin and cefoxitin therapy of multiply-resistant Serratia marcescens urinary tract infections. Ward, T.T., Amon, M.B., Krause, L.K. Am. J. Med. (1983) [Pubmed]
  21. Treatment of infections in hospitalized patients with ticarcillin plus clavulanic acid. A comparative study. Holloway, W.J. Am. J. Med. (1985) [Pubmed]
  22. Prevention of postsurgery-induced abdominal adhesions by electrospun bioabsorbable nanofibrous poly(lactide-co-glycolide)-based membranes. Zong, X., Li, S., Chen, E., Garlick, B., Kim, K.S., Fang, D., Chiu, J., Zimmerman, T., Brathwaite, C., Hsiao, B.S., Chu, B. Ann. Surg. (2004) [Pubmed]
  23. Reversible acute cardiac injury during cefoxitin-induced anaphylaxis in a patient with normal coronary arteries. Austin, S.M., Barooah, B., Kim, C.S. Am. J. Med. (1984) [Pubmed]
  24. Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients. Brown, R.B., Klar, J., Lemeshow, S., Teres, D., Pastides, H., Sands, M. Arch. Intern. Med. (1986) [Pubmed]
  25. Aminoglycosides in gynecologic infections. Ledger, W.J. Am. J. Med. (1986) [Pubmed]
  26. Addition of parenteral cefoxitin to regimen of oral antibiotics for elective colorectal operations. A randomized prospective study. Schoetz, D.J., Roberts, P.L., Murray, J.J., Coller, J.A., Veidenheimer, M.C. Ann. Surg. (1990) [Pubmed]
  27. Susceptibility of Neisseria gonorrhoeae associated with pelvic inflammatory disease to cefoxitin, ceftriaxone, clindamycin, gentamicin, doxycycline, azithromycin, and other antimicrobial agents. Rice, R.J., Knapp, J.S. Antimicrob. Agents Chemother. (1994) [Pubmed]
  28. Serum and tissue concentrations of cefoxitin and cefotaxime in women undergoing hysterectomy. White, R.L., Nightingale, C.H., Quintiliani, R., Whitaker, K.F., Jones, R.F., Tripp, W.H. Drugs (1988) [Pubmed]
  29. Salmonella enteritidis: AmpC plasmid-mediated inducible beta-lactamase (DHA-1) with an ampR gene from Morganella morganii. Barnaud, G., Arlet, G., Verdet, C., Gaillot, O., Lagrange, P.H., Philippon, A. Antimicrob. Agents Chemother. (1998) [Pubmed]
  30. Transferable class C beta-lactamases in Escherichia coli strains isolated in Greek hospitals and characterization of two enzyme variants (LAT-3 and LAT-4) closely related to Citrobacter freundii AmpC beta-lactamase. Gazouli, M., Tzouvelekis, L.S., Vatopoulos, A.C., Tzelepi, E. J. Antimicrob. Chemother. (1998) [Pubmed]
  31. Increase in ampC promoter strength due to mutations and deletion of the attenuator in a clinical isolate of cefoxitin-resistant Escherichia coli as determined by RT-PCR. Tracz, D.M., Boyd, D.A., Bryden, L., Hizon, R., Giercke, S., Van Caeseele, P., Mulvey, M.R. J. Antimicrob. Chemother. (2005) [Pubmed]
  32. Relative substrate affinity index values: a method for identification of beta-lactamase enzymes and prediction of successful beta-lactam therapy. James, R. J. Clin. Microbiol. (1983) [Pubmed]
  33. Prevalence of beta-lactamases among ampicillin-resistant Escherichia coli and Salmonella isolated from food animals in Denmark. Olesen, I., Hasman, H., Aarestrup, F.M. Microb. Drug Resist. (2004) [Pubmed]
  34. Antibiotic prophylaxis with cefoxitin in colorectal surgery: effect on the colon microflora and septic complications--a clinical model for prediction of the benefit and risks in using a new antibiotic in prophylaxis. Kager, L., Ljungdahl, I., Malmborg, A.S., Nord, C.E., Pieper, R., Dahlgren, P. Ann. Surg. (1981) [Pubmed]
  35. Antibiotic prophylaxis in acute nonperforated appendicitis. The Danish Multicenter Study Group III. Bauer, T., Vennits, B., Holm, B., Hahn-Pedersen, J., Lysen, D., Galatius, H., Kristensen, E.S., Graversen, P., Wilhelmsen, F., Skjoldborg, H. Ann. Surg. (1989) [Pubmed]
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