monobactams

Summary

Summary: Monocyclic, bacterially produced or semisynthetic beta-lactam antibiotics. They lack the double ring construction of the traditional beta-lactam antibiotics and can be easily synthesized.

Top Publications

  1. Romano A, Gaeta F, Valluzzi R, Caruso C, Rumi G, Bousquet P. IgE-mediated hypersensitivity to cephalosporins: cross-reactivity and tolerability of penicillins, monobactams, and carbapenems. J Allergy Clin Immunol. 2010;126:994-9 pubmed publisher
    ..We sought to evaluate the possibility of using penicillins, monobactams, and carbapenems in subjects with cephalosporin allergy who especially require them...
  2. Torres M, Blanca M. The complex clinical picture of beta-lactam hypersensitivity: penicillins, cephalosporins, monobactams, carbapenems, and clavams. Med Clin North Am. 2010;94:805-20, xii pubmed publisher
    ..The natural history of IgE-mediated reactions indicates that the count of specific IgE antibodies decreases over time and that results of diagnostic tests can become negative...
  3. Mitton Fry M, Arcari J, Brown M, Casavant J, Finegan S, Flanagan M, et al. Novel monobactams utilizing a siderophore uptake mechanism for the treatment of gram-negative infections. Bioorg Med Chem Lett. 2012;22:5989-94 pubmed publisher
    Novel siderophore-linked monobactams with in vitro and in vivo anti-microbial activity against MDR Gram-negative pathogens are described.
  4. Li R, Oliver R, Townsend C. Identification and Characterization of the Sulfazecin Monobactam Biosynthetic Gene Cluster. Cell Chem Biol. 2017;24:24-34 pubmed publisher
    The monobactams, exemplified by the natural product sulfazecin, are the only class of ?-lactam antibiotics not inactivated by metallo-?-lactamases, which confer bacteria with extended-spectrum ?-lactam resistance...
  5. Luczkiewicz A, Kotlarska E, Artichowicz W, Tarasewicz K, Fudala Ksiazek S. Antimicrobial resistance of Pseudomonas spp. isolated from wastewater and wastewater-impacted marine coastal zone. Environ Sci Pollut Res Int. 2015;22:19823-34 pubmed publisher
    ..4th generation, extended-spectrum penicillins, as well as their combination with the β-lactamase inhibitors, monobactams, fluoroquinolones, and polymyxins...
  6. Danes C, Navia M, Ruiz J, Marco F, Jurado A, Jimenez de Anta M, et al. Distribution of beta-lactamases in Acinetobacter baumannii clinical isolates and the effect of Syn 2190 (AmpC inhibitor) on the MICs of different beta-lactam antibiotics. J Antimicrob Chemother. 2002;50:261-4 pubmed
    ..baumannii clinical isolates the increased production of AmpC, in combination or not with other resistance mechanisms, contributes to the resistance pattern in A. baumannii to beta-lactams. ..
  7. Yourassowsky E, van der Linden M, Lismont M, Crokaert F. Growth curve patterns of Escherichia coli, Serratia marcescens, and Proteus vulgaris submitted to different tigemonam concentrations. J Chemother. 1989;1 Suppl 2:49-53 pubmed
    ..At 6 hours, the killing rate was not dose-related. In conclusion, tigemonam and aztreonam induced first filament formation followed after a few hours by bactericidal activity. ..
  8. Prematta T, Shah S, Ishmael F. Physician approaches to beta-lactam use in patients with penicillin hypersensitivity. Allergy Asthma Proc. 2012;33:145-51 pubmed publisher
    ..For patients with a positive skin test to penicillin, only 45.1% of nonallergists were comfortable prescribing monobactams versus 62.5% of allergists; 30.3% of all responders would give a carbapenem...
  9. Guermazi Toumi S, Boujlel S, Assoudi M, Issaoui R, Tlili S, Hlaiem M. Susceptibility profiles of bacteria causing urinary tract infections in Southern Tunisia. J Glob Antimicrob Resist. 2018;12:48-52 pubmed publisher
    ..The resistance rate of E. coli and K. pneumoniae to amoxicillin and ticarcillin was elevated; however, monobactams and especially carbapenems (imipenem), colistin and amikacin retained good activity...

More Information

Publications62

  1. Yamaryo T, Oishi K, Yoshimine H, Tsuchihashi Y, Matsushima K, Nagatake T. Fourteen-member macrolides promote the phosphatidylserine receptor-dependent phagocytosis of apoptotic neutrophils by alveolar macrophages. Antimicrob Agents Chemother. 2003;47:48-53 pubmed
  2. Ramzan N. Traveler's diarrhea. Gastroenterol Clin North Am. 2001;30:665-78, viii pubmed
    ..Treatment and prevention of this common problem is described in some detail. Finally, a practical and cost-effective approach to evaluating and treating a returning traveler is presented. ..
  3. Tondi D, Cross S, Venturelli A, Costi M, Cruciani G, Spyrakis F. Decoding the Structural Basis For Carbapenem Hydrolysis By Class A ?-lactamases: Fishing For A Pharmacophore. Curr Drug Targets. 2016;17:983-1005 pubmed
    ..spectrum ?-lactamases (ESBL) in their ability to hydrolyze ?-lactams, cephalosporins and most importantly monobactams and carbapenems...
  4. Hunfeld K, Weigand J, Wichelhaus T, Kekoukh E, Kraiczy P, Brade V. In vitro activity of mezlocillin, meropenem, aztreonam, vancomycin, teicoplanin, ribostamycin and fusidic acid against Borrelia burgdorferi. Int J Antimicrob Agents. 2001;17:203-8 pubmed
    ..burgdorferi complex. The excellent in vitro effectiveness of acylamino-penicillin derivatives and their suitability for the therapy of Lyme disease is emphasised. ..
  5. Sandanayaka V, Prashad A. Resistance to beta-lactam antibiotics: structure and mechanism based design of beta-lactamase inhibitors. Curr Med Chem. 2002;9:1145-65 pubmed
  6. Kumar K, Anitha P, Sivasakthi V, Bag S, Lavanya P, Anbarasu A, et al. In silico study on Penicillin derivatives and Cephalosporins for upper respiratory tract bacterial pathogens. 3 Biotech. 2014;4:241-251 pubmed publisher
    ..Lactam antibiotics like Penicillin, Cephalosporins, Carbapenems and Monobactams inhibit bacterial cell wall synthesis by binding with PBPs...
  7. Harper T, June C, Taracila M, Bonomo R, Powers R, Leonard D. Multiple substitutions lead to increased loop flexibility and expanded specificity in Acinetobacter baumannii carbapenemase OXA-239. Biochem J. 2018;475:273-288 pubmed publisher
    ..three substitutions were selected to expand the substrate specificity profile of OXA-23 to cephalosporins and monobactams. The loss of activity against imipenem, however, suggests that there may be limits to the plasticity of class D ..
  8. Gibbs W, Cooper T, Bronze M, Greenfield R. Part V. Other beta-lactam antimicrobials. J Okla State Med Assoc. 2007;100:23-5 pubmed
  9. Lotz S, Starke A, Ziemann C, Morath S, Hartung T, Solbach W, et al. Beta-lactam antibiotic-induced release of lipoteichoic acid from Staphylococcus aureus leads to activation of neutrophil granulocytes. Ann Clin Microbiol Antimicrob. 2006;5:15 pubmed
    ..The findings suggest that, via the activation of PMN, antibiotic-induced LTA release from S. aureus leads to enhanced antimicrobial activity of the innate immune defense mechanisms. ..
  10. Nelson D, Young K. Penicillin binding protein 5 affects cell diameter, contour, and morphology of Escherichia coli. J Bacteriol. 2000;182:1714-21 pubmed
    ..We conclude that among the low-molecular-weight PBPs, PBP 5 plays a principle role in determining cell diameter, surface uniformity, and overall topology of the peptidoglycan sacculus. ..
  11. Sleeman M, MacKinnon C, Hewitson K, Schofield C. Enzymatic synthesis of monocyclic beta-lactams. Bioorg Med Chem Lett. 2002;12:597-9 pubmed
    ..The results suggest that a modified version of BLS might be used to catalyse the preparation of intermediates useful for the synthesis of beta-lactam antibiotics. ..
  12. Sun W, Cao P, Mei R, Li Y, Ma Y, Wu B. Palladium-catalyzed unactivated C(sp3)-H bond activation and intramolecular amination of carboxamides: a new approach to ?-lactams. Org Lett. 2014;16:480-3 pubmed publisher
    ..This method has been applied to the efficient synthesis of the ?-lactamase inhibitor MK-8712. ..
  13. Reck F, Bermingham A, Blais J, Capka V, Cariaga T, Casarez A, et al. Optimization of novel monobactams with activity against carbapenem-resistant Enterobacteriaceae - Identification of LYS228. Bioorg Med Chem Lett. 2018;28:748-755 pubmed publisher
    ..confers resistance in Gram-negative bacteria to all classes of β-lactam antibiotics, with the exception of monobactams, which are intrinsically stable to MBLs...
  14. van Delden C, Page M, Köhler T. Involvement of Fe uptake systems and AmpC ?-lactamase in susceptibility to the siderophore monosulfactam BAL30072 in Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2013;57:2095-102 pubmed publisher
    ..We conclude that the upregulation of the Fe-dicitrate system impacts the expression of other TonB-dependent iron transporters and that PiuA and PiuC contribute to the susceptibility of P. aeruginosa PAO1 to BAL30072. ..
  15. Jarrahpour A, Zarei M. Synthesis of novel N-sulfonyl monocyclic beta-lactams as potential antibacterial agents. Molecules. 2006;11:49-58 pubmed
  16. Shah P, Gänger Farshid G, Mulert R, Stille W. Bactericidal activity of tigemonam, alone and in combination with gentamicin. J Chemother. 1989;1 Suppl 2:45-8 pubmed
    ..The results found tigemonam to be rapidly bactericidal against most Enterobacteriaceae isolated. In addition, the killing curves indicated a synergism between tigemonam and subinhibitory concentrations of gentamicin. ..
  17. Jones R. A review of cephalosporin metabolism: a lesson to be learned for future chemotherapy. Diagn Microbiol Infect Dis. 1989;12:25-31 pubmed
    ..In the case of CTX/dCTX, the laboratory results for CTX will always underestimate its value or potency because of the contribution of the metabolite. ..
  18. Raponi G, Nazzari G, Lun M, Lorino G, Valentini T, Bronzini M, et al. Immunization of mice with antibiotic treated Escherichia coli. J Chemother. 1991;3 Suppl 1:136-40 pubmed
    ..coli. These findings seem to support the hypothesis that sub-MICs of antibiotics modify the bacterial surface influencing host-parasite relationships. ..
  19. Moynié L, Luscher A, Rolo D, Pletzer D, Tortajada A, Weingart H, et al. Structure and Function of the PiuA and PirA Siderophore-Drug Receptors from Pseudomonas aeruginosa and Acinetobacter baumannii. Antimicrob Agents Chemother. 2017;61: pubmed publisher
    ..BAL30072 and MC-1 are two monobactams conjugated to a dihydroxypyridone siderophore that are active against Pseudomonas aeruginosa and ..
  20. Pavanetto M, Zarpellon A, Giacomini D, Galletti P, Quintavalla A, Cainelli G, et al. Inhibitory effect by new monocyclic 4-alkyliden-beta-lactam compounds on human platelet activation. Platelets. 2007;18:357-64 pubmed
  21. Rubinstein E, Cammarata S, Oliphant T, Wunderink R. Linezolid (PNU-100766) versus vancomycin in the treatment of hospitalized patients with nosocomial pneumonia: a randomized, double-blind, multicenter study. Clin Infect Dis. 2001;32:402-12 pubmed
    ..Resistance to either treatment was not detected. Linezolid is a well-tolerated, effective treatment for adults with gram-positive nosocomial pneumonia. ..
  22. Hirasawa M, Takada K. Susceptibility of Streptococcus mutans and Streptococcus sobrinus to cell wall inhibitors and development of a novel selective medium for S. sobrinus. Caries Res. 2002;36:155-60 pubmed
    ..sobrinus on MS-SOB medium was 74.1% compared to that on MS medium. Seventy-eight percent of clinical samples in which S. sobrinus was detected yielded pure growth of S. sobrinus on MS-SOB medium...
  23. Ceccarelli D, van Essen Zandbergen A, Smid B, Veldman K, Boender G, Fischer E, et al. Competitive Exclusion Reduces Transmission and Excretion of Extended-Spectrum-β-Lactamase-Producing Escherichia coli in Broilers. Appl Environ Microbiol. 2017;83: pubmed publisher
    ..able to hydrolyze a large variety of β-lactam antibiotics, including third-generation cephalosporins and monobactams. Broilers and broiler meat products can be highly contaminated with ESBL- and pAmpC-producing Escherichia ..
  24. Walther Rasmussen J, Høiby N. Cefotaximases (CTX-M-ases), an expanding family of extended-spectrum beta-lactamases. Can J Microbiol. 2004;50:137-65 pubmed
    ..This group of beta-lactamases confers resistance to penicillins, extended-spectrum cephalosporins, and monobactams, and the enzymes are inhibited by clavulanate, sulbactam, and tazobactam...
  25. Bag S, Kundu R, Basak A, Slanina Z. Suppressed beta-effect of silicon in 3-silylated monocyclic beta-lactams: the role of antiaromaticity. Org Lett. 2009;11:5722-5 pubmed publisher
    ..From both the experimental and theoretical studies, it is demonstrated that antiaromaticity is playing the prime role in suppressing the beta-stabilizing effect of silicon. ..
  26. Kazmierczak K, Rabine S, Hackel M, McLaughlin R, Biedenbach D, Bouchillon S, et al. Multiyear, Multinational Survey of the Incidence and Global Distribution of Metallo-β-Lactamase-Producing Enterobacteriaceae and Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2016;60:1067-78 pubmed publisher
    Metallo-β-lactamases (MBLs) hydrolyze all classes of β-lactams except monobactams and are not inhibited by classic serine β-lactamase inhibitors...
  27. Goel R, Mahajan M, Kulkarni S. Evaluation of anti-hyperglycemic activity of some novel monocyclic beta lactams. J Pharm Pharm Sci. 2004;7:80-3 pubmed
    ..Present study concluded that these compounds have significant anti-hyperglycemic effect. Further studies are required to reveal the mechanism of action. ..
  28. Hornsey M, Phee L, Stubbings W, Wareham D. In vitro activity of the novel monosulfactam BAL30072 alone and in combination with meropenem versus a diverse collection of important Gram-negative pathogens. Int J Antimicrob Agents. 2013;42:343-6 pubmed publisher
    ..In addition, BAL30072 shows powerful synergistic activity in combination with meropenem, potentially expanding its coverage for the treatment of infections caused by problematic species. ..
  29. Jarrahpour A, Shekarriz M, Taslimi A. Synthesis and antimicrobial activity of some new sugar-based monocyclic beta-lactams. Molecules. 2004;9:29-38 pubmed
    ..Some of these novel beta-lactams were found to be active against Staphilococcus citrus, Klebsiella pneumoniae, Escherichia coli and Bacillus subtilis. ..
  30. Steen A, Schwartz T, Rosenkilde M. Targeting CXCR4 in HIV cell-entry inhibition. Mini Rev Med Chem. 2009;9:1605-21 pubmed
  31. Giamarellou H, Pephanis A, Grammatikou M, Avlamis A, Papoulias G. In vitro activity of tigemonam against multiresistant nosocomial Enterobacteriaceae. J Chemother. 1989;1 Suppl 2:32-5 pubmed
    ..It is concluded that tigemonam should play an important role in the treatment of nosocomial infections that do not require parenteral therapy and in the treatment of multiresistant community-acquired infections. ..
  32. Russo T, Page M, Beanan J, Olson R, Hujer A, Hujer K, et al. In vivo and in vitro activity of the siderophore monosulfactam BAL30072 against Acinetobacter baumannii. J Antimicrob Chemother. 2011;66:867-73 pubmed publisher
    ..Both BAL30072 and BAL30072 with meropenem were equally effective in vivo. These data support the continued evaluation of BAL30072 for use in the treatment of infections caused by MDR A. baumannii. ..
  33. Andrews J, Wise R. The in vitro activity of tigemonam: a comparison with other antimicrobial agents. J Chemother. 1989;1 Suppl 2:5-12 pubmed
    ..Pseudomonas, staphylococci, and Bacteroides sp. were less susceptible (MIC90 greater than 128 mg/L). Protein binding in human serum was found to be 62.5%; the presence of serum had only a modest effect on the activity of tigemonam. ..
  34. Chen D, Falsetti S, Frezza M, Milacic V, Kazi A, Cui Q, et al. Anti-tumor activity of N-thiolated beta-lactam antibiotics. Cancer Lett. 2008;268:63-9 pubmed publisher
    ..These results suggest that the synthetic antibiotic N-thiolated beta-lactams hold great potential to be developed as novel anti-cancer drugs. ..
  35. Rodríguez Julbe M, Ramirez Ronda C, Arroyo E, Maldonado G, Saavedra S, Meléndez B, et al. Antibiotics in older adults. P R Health Sci J. 2004;23:25-33 pubmed
    ..We present several groups: the penicillins, cephalosporins, monobactams, carbapenems and betalactamase inhibitors or the great betalactam group...
  36. van den Berg M, Gidijala L, Kiela J, Bovenberg R, Vander Keli I. Biosynthesis of active pharmaceuticals: ?-lactam biosynthesis in filamentous fungi. Biotechnol Genet Eng Rev. 2010;27:1-32 pubmed
    ..Also, the potential of using heterologous hosts for the development of novel ß-lactam antibiotics and non-ribosomal peptide synthetase-based peptides is discussed. ..
  37. Khan M, Shah S. Comparison of aztreonam against other antibiotics used in urinary tract infections. J Ayub Med Coll Abbottabad. 2001;13:22-4 pubmed
    ..3% (49), proteus species 5.2%(18) and pseudomonas aeruginosa were 3.8% (13). The aztreonam showed 78% sensitivity against gram negative bacilli which is better than norfloxacin which showed 62.2% sensitivity. ..
  38. Jarrahpour A, Shekarriz M, Taslimi A. Asymmetric synthesis and antimicrobial activity of some new mono and bicyclic beta-lactams. Molecules. 2004;9:939-48 pubmed
    ..The compounds prepared were tested against Escherichia coli, Staphilococcus citrus, Klebsiella pneumanie and Bacillus subtillis. Some of these compounds showed potential antimicrobial activities. ..
  39. Sendzik J, Stahlmann R. [Opposition to Ehrlich's paradigm of selective toxicity. Adverse effects of beta lactam antibiotics]. Pharm Unserer Zeit. 2006;35:432-7 pubmed
  40. Toyama K, Yaguchi M, Mizoguchi H, Masuda M, Urabe A, Ikeda Y, et al. Effect of recombinant human granulocyte colony-stimulating factor on combination therapy with aztreonam and clindamycin for infections in neutropenic patients with hematologic diseases. Kansenshogaku Zasshi. 1996;70:1242-53 pubmed
    ..These results suggest that rhG-CSF is of little benefit in the treatment of single infectious episodes in neutropenic patients, and that appropriate antibiotic therapy is more important. ..
  41. Rodriguez Martinez J, Nordmann P, Ronco E, Poirel L. Extended-spectrum cephalosporinase in Acinetobacter baumannii. Antimicrob Agents Chemother. 2010;54:3484-8 pubmed publisher
    An AmpC-type beta-lactamase conferring high-level resistance to expanded-spectrum cephalosporins and monobactams was characterized from an Acinetobacter baumannii clinical isolate...
  42. Cooper T, Gibbs W, Bronze M, Greenfield R. Part II. Introduction to the beta-lactam antibiotics. J Okla State Med Assoc. 2006;99:516-20 pubmed
  43. Adediran S, Lohier J, Cabaret D, Wakselman M, Pratt R. Synthesis and reactivity with beta-lactamases of a monobactam bearing a retro-amide side chain. Bioorg Med Chem Lett. 2006;16:869-71 pubmed
    ..The new compound is generally a poorer substrate than the analogous compound with a normal side chain but its formation of a transiently stable complex with a class C beta-lactamase sustains the retro-amide side-chain concept. ..
  44. Raimondi A, Cocuzza C. Antibacterial activity of tigemonam dicholate (SQ 30836) and interaction with beta-lactamases of gram-negative bacteria. J Chemother. 1989;1 Suppl 2:13-21 pubmed
    ..However, only levels of beta-lactamase, not hydrolysis rates or affinity, correlated to MICs of the two monobactams for the resistant Enterobacter and Citrobacter strains.
  45. Ogilvie W, Yoakim C, Do F, Haché B, Lagace L, Naud J, et al. Synthesis and antiviral activity of monobactams inhibiting the human cytomegalovirus protease. Bioorg Med Chem. 1999;7:1521-31 pubmed
  46. Luzzaro F, Pagani L, Porta F, Romero E. Extended-spectrum beta-lactamases conferring resistance to monobactams and oxyimino-cephalosporins in clinical isolates of Serratia marcescens. J Chemother. 1995;7:175-8 pubmed
    ..172 were obtained from February to October and presented the same pattern of antibiotic resistance, including monobactams and oxyimino-cephalosporins...
  47. Deshayes S, Coquerel A, Verdon R. Neurological Adverse Effects Attributable to ?-Lactam Antibiotics: A Literature Review. Drug Saf. 2017;40:1171-1198 pubmed publisher
    ..Otherwise, it appears that monobactams do not have serious neurological adverse drug reactions and that valproic acid and carbapenem combinations ..
  48. Brown M, Mitton Fry M, Arcari J, Barham R, Casavant J, Gerstenberger B, et al. Pyridone-conjugated monobactam antibiotics with gram-negative activity. J Med Chem. 2013;56:5541-52 pubmed publisher
    ..In addition, evidence is provided for a number of analogues suggesting that the siderophore receptors PiuA and PirA play a role in drug uptake in P. aeruginosa strain PAO1. ..
  49. Cipolla D, Chan H. Inhaled antibiotics to treat lung infection. Pharm Pat Anal. 2013;2:647-63 pubmed publisher
    ..This review addresses that missing piece. ..
  50. Nadjar D, Rouveau M, Verdet C, Donay L, Herrmann J, Lagrange P, et al. Outbreak of Klebsiella pneumoniae producing transferable AmpC-type beta-lactamase (ACC-1) originating from Hafnia alvei. FEMS Microbiol Lett. 2000;187:35-40 pubmed
    ..We used internal bla(ACC-1) primers, to sequence PCR products obtained from two unrelated strains of Hafnia alvei. Our results show that the ACC-1 beta-lactamase was derived from the chromosome-encoded AmpC-type enzyme of H. alvei...
  51. Llarrull L, Testero S, Fisher J, Mobashery S. The future of the ?-lactams. Curr Opin Microbiol. 2010;13:551-7 pubmed publisher
    ..We concisely summarize recent developments with respect to bacterial resistance, the identity of the new ?-lactams, and the emerging non-empirical strategies that will ensure that this incredible class of antibiotics has a future. ..
  52. Fernea A, Galleni M, Frère J. Kinetics of the Interaction between BAL29880 and LK157 and the Class C β-Lactamase CHE-1. Antimicrob Agents Chemother. 2016;60:1747-50 pubmed publisher
    ..However, the second-order rate constant for the inactivation by BAL29880 probably remains adequate for a rather rapid reaction with CHE-1 in the absence of protection by the substrate. ..
  53. Perilli M, Segatore B, De Massis M, Franceschini N, Bianchi C, Rossolini G, et al. Characterization of a new extended-spectrum beta-lactamase (TEM-87) isolated in Proteus mirabilis during an Italian survey. Antimicrob Agents Chemother. 2002;46:925-8 pubmed
    ..Kinetic analysis of TEM-87 revealed extended-spectrum activity against oxyimino cephalosporins (preferentially ceftazidime) and aztreonam. Expression of blaTEM-87 in Escherichia coli decreased the host susceptibility to these drugs...