cephamycins

Summary

Summary: Naturally occurring family of beta-lactam cephalosporin-type antibiotics having a 7-methoxy group and possessing marked resistance to the action of beta-lactamases from gram-positive and gram-negative organisms.

Top Publications

  1. Zervosen A, Valladares M, Devreese B, Prosperi Meys C, Adolph H, Mercuri P, et al. Inactivation of Aeromonas hydrophila metallo-beta-lactamase by cephamycins and moxalactam. Eur J Biochem. 2001;268:3840-50 pubmed
    ..Interestingly, this reaction is catalyzed by cacodylate. ..
  2. Liras P, Demain A. Chapter 16. Enzymology of beta-lactam compounds with cephem structure produced by actinomycete. Methods Enzymol. 2009;458:401-29 pubmed publisher
    b>Cephamycins are beta-lactam antibiotics with a cephem structure produced by actinomycetes...
  3. Doi Y, Wachino J, Ishiguro M, Kurokawa H, Yamane K, Shibata N, et al. Inhibitor-sensitive AmpC beta-lactamase variant produced by an Escherichia coli clinical isolate resistant to oxyiminocephalosporins and cephamycins. Antimicrob Agents Chemother. 2004;48:2652-8 pubmed publisher
    ..To our knowledge, this is the first report to have characterized an E. coli ampC that encodes chromosomal AmpC beta-lactamase sensitive to the available beta-lactamase inhibitors...
  4. Forward K, Willey B, Low D, McGeer A, Kapala M, Kapala M, et al. Molecular mechanisms of cefoxitin resistance in Escherichia coli from the Toronto area hospitals. Diagn Microbiol Infect Dis. 2001;41:57-63 pubmed
    ..The majority of cephamycin resistant E. coli strains in Toronto have attenuator and/or promotor mutations upstream of the chromosomal ampC gene. ..
  5. Caroff N, Espaze E, Berard I, Richet H, Reynaud A. Mutations in the ampC promoter of Escherichia coli isolates resistant to oxyiminocephalosporins without extended spectrum beta-lactamase production. FEMS Microbiol Lett. 1999;173:459-65 pubmed
    ..The +24 mutation was detected in another strain associated with a 1-bp insertion between the -35 and -10 conserved sequences. None of these mutations was detected in the ampC beta-lactamase from the sensitive isolates. ..
  6. Neto A, Bustamante M, Oliveira J, Granato A, Bellão C, Badino A, et al. Preliminary studies for cephamycin C purification technique. Appl Biochem Biotechnol. 2012;166:208-21 pubmed publisher
    ..Some of the fractions obtained during purification were also analyzed by mass spectrometry (LC/MS and LC/MS/MS) to identify the cephamycin C molecule. These preliminary results proved the process feasibility. ..
  7. Leitão A, Enguita F, Martin J, Santos Oliveira J. Effect of exogenous lysine on the expression of early cephamycin C biosynthetic genes and antibiotic production in Nocardia lactamdurans MA4213. Appl Microbiol Biotechnol. 2001;56:670-5 pubmed
    ..These results indicate that L-lysine is required not only for antibiotic biosynthesis, but particularly as carbon or nitrogen source. ..
  8. Bussari B, Saudagar P, Shaligram N, Survase S, Singhal R. Production of cephamycin C by Streptomyces clavuligerus NT4 using solid-state fermentation. J Ind Microbiol Biotechnol. 2008;35:49-58 pubmed
    ..50 +/- 1.04 mg gds(-1) before optimization. Effect of various amino acids on cephamycin C production was further studied by using RSM, which resulted in increased yield of 27.41 +/- 0.65 mg gds(-1). ..
  9. Kagliwal L, Survase S, Singhal R. A novel medium for the production of cephamycin C by Nocardia lactamdurans using solid-state fermentation. Bioresour Technol. 2009;100:2600-6 pubmed publisher
    ..75+/-0.27 mg/gds of cephamycin C as compared to 8.37+/-0.23 mg/gds before optimization. Effect of 1,3-diaminopropane on cephamycin C production was further studied, which further increased the yield to 27.64+/-0.33 mg/gds...

More Information

Publications62

  1. Kays M, White R, Friedrich L, Del Bene V. Evaluation of cephalosporins/cephamycins with antianaerobic activity by integrating microbiologic and pharmacokinetic properties. Clin Ther. 1991;13:596-605 pubmed
    ..For B fragilis from our institution, the pharmacodynamic profile of unbound ceftizoxime is superior to the other antianaerobic cephalosporins/cephamycins tested.
  2. Thykaer J, Nielsen J. Metabolic engineering of beta-lactam production. Metab Eng. 2003;5:56-69 pubmed
    ..This minireview discusses the recent developments in metabolic engineering and the applications of this approach for improving beta-lactam production. ..
  3. Trepanier N, Jensen S, Alexander D, Leskiw B. The positive activator of cephamycin C and clavulanic acid production in Streptomyces clavuligerus is mistranslated in a bldA mutant. Microbiology. 2002;148:643-56 pubmed
    ..The role of codon context in bldA dependence is discussed. ..
  4. Berkeley A, Freedman K, Ledger W, Orr J, Benigno B, Gordon S, et al. Comparison of cefotetan and cefoxitin prophylaxis for abdominal and vaginal hysterectomy. Am J Obstet Gynecol. 1988;158:706-9 pubmed
  5. Zabransky R, Bobey D, Sheikh W. A multicenter study of the in vitro antianaerobic activity of cefotetan compared with other antimicrobial agents. Am J Surg. 1988;155:47-51 pubmed
    ..S. Food and Drug Administration- and NCCLS-recommended criteria. This study indicates that Bacteroides fragilis, Clostridium difficile, and most other clinically significant anaerobic bacteria are susceptible to cefotetan. ..
  6. Bloomberg R. Cefotetan-induced anaphylaxis. Am J Obstet Gynecol. 1988;159:125-6 pubmed
    ..During the 4-month interval that cefotetan was selectively used for surgical prophylaxis at our hospital, we observed a 1.4% incidence of anaphylactic hypersensitivity reactions associated with its use. ..
  7. Gazouli M, Tzouvelekis L, Prinarakis E, Miriagou V, Tzelepi E. Transferable cefoxitin resistance in enterobacteria from Greek hospitals and characterization of a plasmid-mediated group 1 beta-lactamase (LAT-2). Antimicrob Agents Chemother. 1996;40:1736-40 pubmed
    ..These elements have also been spread to Enterobacter aerogenes. The most common enzyme was a Citrobacter freundii-derived cephalosporinase (LAT-2) which differed from LAT-1 by three amino acids. ..
  8. Scher K. Studies on the duration of antibiotic administration for surgical prophylaxis. Am Surg. 1997;63:59-62 pubmed
    ..A second dose of antibiotic or a single preoperative dose of an extended half-life antibiotic are equally effective. There is no value to administering antibiotics after the operation has been completed. ..
  9. Orr J, Sisson P, Barrett J, Ellington J, Jennings R, Taylor D. Single-center study results of cefotetan and cefoxitin prophylaxis for abdominal or vaginal hysterectomy. Am J Obstet Gynecol. 1988;158:714-6 pubmed
    ..An overall infection rate of 1.2% was recorded. Bacteriologic and clinical success rates were not different between antibiotics. ..
  10. Fonzé E, Vanhove M, Dive G, Sauvage E, Frere J, Charlier P. Crystal structures of the Bacillus licheniformis BS3 class A beta-lactamase and of the acyl-enzyme adduct formed with cefoxitin. Biochemistry. 2002;41:1877-85 pubmed
  11. Tejedor Junco M, Gonzalez Martin M, Lupiola P, Gonzalez Lama Z. Type I beta-lactamases of Enterobacter cloacae and resistance to beta-lactam antibiotics. Folia Microbiol (Praha). 1998;43:683-6 pubmed
    ..Imipenem would therefore be the appropriate choice for therapy of infections caused by stably derepressed mutants of Enterobacter sp. producing type-I beta-lactamases. ..
  12. Park H, Merz K. Force field design and molecular dynamics simulations of the carbapenem- and cephamycin-resistant dinuclear zinc metallo-beta-lactamase from Bacteroides fragilis and its complex with a biphenyl tetrazole inhibitor. J Med Chem. 2005;48:1630-7 pubmed
  13. Satomi N, Sakurai A, Iimura F, Haranaka R, Haranaka K. Preventive effect of several drugs against Pseudomonas aeruginosa infection and the toxicity of combined tumor necrosis factor with lipopolysaccharide: relationship between lethality and the arachidonic cascade. Biotherapy. 1990;2:227-34 pubmed
    ..Following pretreatment with Shosaiko-to, suppression of LTs was dominant even with the combination of TNF and LPS, which might be related to the lethality of the infection or combined TNF with LPS. ..
  14. Lee S, Jeong S. Antibiotic susceptibility of bacterial strains isolated from patients with various infections. Lett Appl Microbiol. 2002;34:215-21 pubmed
    ..1998 and 1999 were identified and their susceptibility to third-generation cephalosporins, monobactams and/or cephamycins studied along with any production of ESBLs...
  15. Cornick N, Jacobus N, Gorbach S. Activity of cefmetazole against anaerobic bacteria. Antimicrob Agents Chemother. 1987;31:2010-2 pubmed
    ..It was somewhat less active than cefoxitin against Bacteroides thetaiotaomicron, B. ovatus, B. distasonis, and B. vulgatus and somewhat more active against Clostridium spp. ..
  16. Clarke B, Hiltz M, Musgrave H, Forward K. Cephamycin resistance in clinical isolates and laboratory-derived strains of Escherichia coli, Nova Scotia, Canada. Emerg Infect Dis. 2003;9:1254-9 pubmed
  17. Underwood S, Avison M. Citrobacter koseri and Citrobacter amalonaticus isolates carry highly divergent beta-lactamase genes despite having high levels of biochemical similarity and 16S rRNA sequence homology. J Antimicrob Chemother. 2004;53:1076-80 pubmed
    ..We measured sequence variation at the beta-lactamase structural gene among a group of clinical isolates originally identified as C. diversus by API 20E profiling...
  18. Schentag J, Welage L, Williams J, Wilton J, Adelman M, Rigan D, et al. Kinetics and action of N-methylthiotetrazole in volunteers and patients. Population-based clinical comparisons of antibiotics with and without this moiety. Am J Surg. 1988;155:40-4 pubmed
    ..In surveillance studies, NMTT-containing antibiotics were nor more frequently associated with hypoprothrombinemia or bleeding than antibiotics that lack this moiety. ..
  19. Naylor C, Steele L, Hsi R, Margolin M, Goldfinger D. Cefotetan-induced hemolysis associated with antibiotic prophylaxis for cesarean delivery. Am J Obstet Gynecol. 2000;182:1427-8 pubmed
    ..When postpartum anemia is associated with antibiotic use, immune hemolytic anemia should be considered and included in the differential diagnosis. ..
  20. Bauernfeind A, Stemplinger I, Jungwirth R, Giamarellou H. Characterization of the plasmidic beta-lactamase CMY-2, which is responsible for cephamycin resistance. Antimicrob Agents Chemother. 1996;40:221-4 pubmed
    ..The blaCMY-2 gene possibly was translocated onto a plasmid of C. freundii which spread to K. pneumoniae. ..
  21. Yilmaz E, Caydasi A, Ozcengiz G. Targeted disruption of homoserine dehydrogenase gene and its effect on cephamycin C production in Streptomyces clavuligerus. J Ind Microbiol Biotechnol. 2008;35:1-7 pubmed
    ..Disruption of hom gene resulted in up to 4.3-fold and twofold increases in intracellular free L-lysine concentration and specific cephamycin C production, respectively, during stationary phase in chemically defined medium. ..
  22. Sweet R, Gall S, Gibbs R, Hemsell D, Knuppel R, Lane T, et al. Multicenter clinical trials comparing cefotetan with moxalactam or cefoxitin as therapy for obstetric and gynecologic infections. Am J Surg. 1988;155:56-60 pubmed
    ..Cefotetan was well tolerated and produced no major adverse reactions. The mean amount of cefotetan given was lower than that of moxalactam or cefoxitin. ..
  23. Hemsell D, Wendel G, Gall S, Newton E, Gibbs R, Knuppel R, et al. Multicenter comparison of cefotetan and cefoxitin in the treatment of acute obstetric and gynecologic infections. Am J Obstet Gynecol. 1988;158:722-7 pubmed
    ..These results suggest the administration of cefotetan provided adequate clinical and bacteriologic effectiveness in the treatment of hospital- and community-acquired, polymicrobial obstetric and gynecologic pelvic infections. ..
  24. Martineau L, Shek P. Efficacy of liposomal antibiotic therapy in a rat infusion model of Escherichia coli peritonitis. Crit Care Med. 1999;27:1153-8 pubmed
    ..Liposomal cefoxitin enhanced bacterial killing in liver and spleen in this model of E. coli peritonitis. It also improved survival outcome relative to no treatment but not compared with free cefoxitin. ..
  25. Paradkar A, Mosher R, Anders C, Griffin A, Griffin J, Hughes C, et al. Applications of gene replacement technology to Streptomyces clavuligerus strain development for clavulanic acid production. Appl Environ Microbiol. 2001;67:2292-7 pubmed
    ..This represents the first report of the successful use of genetic engineering to eliminate undesirable metabolic pathways in an industrial strain used for the production of an antibiotic important in human medicine. ..
  26. Teng L, Hsueh P, Tsai J, Liaw S, Ho S, Luh K. High incidence of cefoxitin and clindamycin resistance among anaerobes in Taiwan. Antimicrob Agents Chemother. 2002;46:2908-13 pubmed
    ..fragilis strains by pulsed-field gel electrophoresis. The metronidazole-resistant B. fragilis strains showed genotypic heterogeneity, excluding the dissemination of a single clone. ..
  27. Ida S, Nishioka K, Takishima T, Satoh S, Kikuta Y, Ohnami K, et al. [Laboratory and clinical studies on cefotetan in respiratory tract infections]. Jpn J Antibiot. 1988;41:415-26 pubmed
    ..As to abnormal laboratory findings, blood transaminases were elevated during drug administration in 13 cases or 17.3%, but were reduced back to the normal level after the withdrawal of the drug. ..
  28. Jin W, Kim H, Kim J, Kang S, Lee S, Lee K. Cephamycin C production is regulated by relA and rsh genes in Streptomyces clavuligerus ATCC27064. J Biotechnol. 2004;114:81-7 pubmed
    ..Therefore, it is concluded that the stringent response of S. clavuligerus to starvation for nutrients is governed mainly by RelA rather than Rsh and that the response is more apparently regulated by the limitation of phosphate. ..
  29. Huelves L, Gracia M, del Prado G, Rodriguez Cerrato V, Martínez Marín C, Ponte C, et al. Efficacy of cefminox compared with amoxicillin/clavulanic acid as a single dose for the prevention of intra-abdominal sepsis in mice intraperitoneally infected with different strains of Escherichia coli and one strain of Bacteroides fragilis. Int J Antimicrob Agents. 2006;28:151-3 pubmed
  30. Jia L, Lu J, Ma X, Jiang H, Zhu Y, Liu Y, et al. [Analysis of risk factors of intra-abdominal infection after surgery for colorectal cancer]. Zhonghua Wei Chang Wai Ke Za Zhi. 2016;19:409-13 pubmed
    ..37, 95% CI: 0.23 to 0.60, P<0.01). Compared with prophylactic use of cephamycins plus metronidazole, cefuroxime plus metronidazole had a higher rate of IAI(OR=2.10, 95% CI:1.23 to 3.58, P=0...
  31. Muratani T, Kobayashi T, Matsumoto T. Emergence and prevalence of beta-lactamase-producing Klebsiella pneumoniae resistant to cephems in Japan. Int J Antimicrob Agents. 2006;27:491-9 pubmed
    ..The mechanisms of resistance of 44 of the 46 isolates to cephalosporins and cephamycins were ESBL production and/or plasmid-encoded AmpC beta-lactamase and/or IMP-1 beta-lactamase production...
  32. Migliavacca R, Nucleo E, D Andrea M, Spalla M, Giani T, Pagani L. Acquired AmpC type beta-lactamases: an emerging problem in Italian long-term care and rehabilitation facilities. New Microbiol. 2007;30:295-8 pubmed
    ..and rehabilitation facilities (LTCRFs) of Northern Italy, resistant to expanded-spectrum cephalosporins and cephamycins and producing an acquired ampC-like beta-lactamase, named CMY-16...
  33. Ozcengiz G, Okay S, Unsaldı E, Taskin B, Liras P, Piret J. Homologous expression of aspartokinase (ask) gene in Streptomyces clavuligerus and its hom-deleted mutant: effects on cephamycin C production. Bioeng Bugs. 2010;1:191-7 pubmed publisher
  34. Manchanda V, Singh N. Occurrence and detection of AmpC beta-lactamases among Gram-negative clinical isolates using a modified three-dimensional test at Guru Tegh Bahadur Hospital, Delhi, India. J Antimicrob Chemother. 2003;51:415-8 pubmed
    AmpC enzymes can be differentiated from other extended-spectrum beta-lactamases by their ability to hydrolyse cephamycins as well as other extended-spectrum cephalosporins...
  35. Quintiliani R, Nightingale C, Stevens R, Outman W, Deckers P, Martens M. Comparative pharmacokinetics of cefotetan and cefoxitin in patients undergoing hysterectomies and colorectal operations. Am J Surg. 1988;155:67-70 pubmed
    ..Although both antibiotics provide good concentrations during the early phase of surgery, cefotetan's concentrations persisted longer, which may be relevant in the prevention of infection in prolonged surgical procedures. ..
  36. Quiroga M, Franceschini N, Rossolini G, Gutkind G, Bonfiglio G, Franchino L, et al. Interaction of cefotetan and the metallo-beta-lactamases produced in Aeromonas spp. and in vitro activity. Chemotherapy. 2000;46:177-83 pubmed
    ..The direct hydrolysis of cefotetan showed that it was a poor substrate for both purified enzymes. In view of the minimum inhibitory concentrations, cefotetan shows to be a useful antimicrobial agent against Aeromonas spp. ..
  37. Fracchia G, Paita L, Maglio R, Malamani T. [Occupational asthma caused by cefmetazole and 7-aminocephalosporanic acid: description of a clinical case]. G Ital Med Lav. 1996;18:3-5 pubmed
    ..It is probable that the occurrence of the illness is due, in this case, to the ability of the inhaled substances to cause inflammation in a subject with bronchial hyperreactivity, without inducing an immunologic mechanism. ..
  38. Jones R. Cefotetan: a review of the microbiologic properties and antimicrobial spectrum. Am J Surg. 1988;155:16-23 pubmed
    ..Synergy between cefotetan and numerous other antibiotics has been reported, but antagonism has also been occasionally observed. ..
  39. Rodriguez A, Pariente J, Prieto J, Barriga C. Effects of cefmetazol, cefoxitin and imipenem on polymorphonuclear leukocytes. Gen Pharmacol. 1987;18:613-5 pubmed
    ..4. The capacity of the PMNs to phagocytize and produce lysis of Candida albicans is increased in Cefmetazol with therapeutic doses. Cefoxitin produced an increased lysis of candidas. ..
  40. Bergstrom R, Mueller G, Yankowitz J. A case illustrating the continued dilemmas in treating abdominal pregnancy and a potential explanation for the high rate of postsurgical febrile morbidity. Gynecol Obstet Invest. 1998;46:268-70 pubmed
    ..Placement of a sterile Foley bulb into the uterine cavity can confirm the extrauterine position of the pregnancy prior to undertaking surgery. ..
  41. Bauernfeind A, Wagner S, Jungwirth R, Schneider I, Meyer D. A novel class C beta-lactamase (FOX-2) in Escherichia coli conferring resistance to cephamycins. Antimicrob Agents Chemother. 1997;41:2041-6 pubmed
    An Escherichia coli strain resistant to a broad spectrum of beta-lactams, including cephamycins, was isolated from a patient suffering from urinary tract infection...
  42. Suzuki T, Soma H, Tazawa H, Hamada W, Sugihara K, Fukushi M, et al. [Clinical study of cefotetan in complicated urinary tract infections]. Hinyokika Kiyo. 1987;33:1917-20 pubmed
    ..Subjective side effects, nausea and abdominal discomfort, were observed in one patient. Abnormal laboratory findings were observed in 6 patients, eosinophilia in 3 patients and slight elevation of transaminase in 3 patients. ..
  43. Bignell D, Tahlan K, Colvin K, Jensen S, Leskiw B. Expression of ccaR, encoding the positive activator of cephamycin C and clavulanic acid production in Streptomyces clavuligerus, is dependent on bldG. Antimicrob Agents Chemother. 2005;49:1529-41 pubmed
    ..This makes bldG the first regulatory protein identified in S. clavuligerus that functions upstream of CcaR and ClaR in a regulatory cascade to control secondary metabolite production. ..
  44. Talan D, Summanen P, Finegold S. Ampicillin/sulbactam and cefoxitin in the treatment of cutaneous and other soft-tissue abscesses in patients with or without histories of injection drug abuse. Clin Infect Dis. 2000;31:464-71 pubmed
    ..9%. The 2 drugs were well tolerated. Ampicillin/sulbactam and cefoxitin were equally effective for the empirical treatment of cutaneous or other soft-tissue infections in injection drug abusers and patients who did not inject drugs. ..
  45. Gao H, Zhuo Y, Ashforth E, Zhang L. Engineering of a genome-reduced host: practical application of synthetic biology in the overproduction of desired secondary metabolites. Protein Cell. 2010;1:621-6 pubmed publisher
    ..This review will give an overview of the strategies used for constructing and engineering reduced-genome factories by synthetic biology to improve production of secondary metabolites. ..
  46. Santamarta I, Pérez Redondo R, Lorenzana L, Martin J, Liras P. Different proteins bind to the butyrolactone receptor protein ARE sequence located upstream of the regulatory ccaR gene of Streptomyces clavuligerus. Mol Microbiol. 2005;56:824-35 pubmed
    ..These results indicate that two different proteins bind specifically to the ARE sequence and modulate clavulanic acid and cephamycin C [corrected] biosynthesis by its action on ccaR gene expression. ..
  47. Barry A. Criteria for in vitro susceptibility testing of cefotetan. Correlations with clinical and bacteriologic responses. Am J Surg. 1988;155:24-9 pubmed
    ..Development of resistance during therapy or superinfections (1.7 percent) were not found to be clinically important problems with cefotetan chemotherapy. ..
  48. Santamarta I, Lopez Garcia M, Kurt A, Nárdiz N, Alvarez Alvarez R, Pérez Redondo R, et al. Characterization of DNA-binding sequences for CcaR in the cephamycin-clavulanic acid supercluster of Streptomyces clavuligerus. Mol Microbiol. 2011;81:968-81 pubmed publisher
    ..Footprinting experiments indicated that triple heptameric conserved sequences were protected by r-CcaR, and allowed identification of heptameric sequences as CcaR binding sites. ..
  49. Kikuchi S, Ando A, Minato K. [Acquired coagulopathy caused by administration of parenteral broad-spectrum antibiotics]. Rinsho Byori. 1991;39:83-90 pubmed
    ..The measurement of PIVKA-II seemed to be useful to diagnose the hemorrhagic diathesis caused by VK deficiency in the patients during administration of antibiotics. ..
  50. Song W, Cao J, Mei Y. Correlation between cephamycin consumption and the incidence of antimicrobial resistance in Acinetobacter baumannii at a university hospital in China from 2001 to 2009. Int J Clin Pharmacol Ther. 2011;49:765-71 pubmed
    ..b>Cephamycins consumption was expressed as defined daily dose (DDD) per 1,000 patient days by World Health Organization (WHO) ..
  51. McGregor J, Gordon S, Krotec J, Poindexter A. Results of a randomized, multicenter, comparative trial of a single dose of cefotetan versus multiple doses of cefoxitin as prophylaxis in cesarean section. Am J Obstet Gynecol. 1988;158:701-6 pubmed
  52. Nozoe T, Matsumata T, Sugimachi K. Significance of SIRS score in therapeutic strategy for acute appendicitis. Hepatogastroenterology. 2002;49:444-6 pubmed
    ..SIRS score is also useful as objective and auxiliary information to determine the surgical indication for acute appendicitis. ..
  53. Santamarta I, Rodríguez García A, Pérez Redondo R, Martin J, Liras P. CcaR is an autoregulatory protein that binds to the ccaR and cefD-cmcI promoters of the cephamycin C-clavulanic acid cluster in Streptomyces clavuligerus. J Bacteriol. 2002;184:3106-13 pubmed
    ..These findings confirm that CcaR is a positively acting autoregulatory protein able to bind to its own promoter as well as to the cefD-cmcI bidirectional promoter region. ..