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Chemical Compound Review

AC1NQXVM     (2R,3E,5R)-3-(2- hydroxyethylidene)-7-oxo-4...

Synonyms: SureCN2292022, C11833, 85-53-0, 62319-53-3, Isoclavulanic acid
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Disease relevance of CLAVULANIC ACID


Psychiatry related information on CLAVULANIC ACID


High impact information on CLAVULANIC ACID

  • Partially purified penicillinase from the S. faecalis strain hydrolyzed penicillin, ampicillin, and ureido-penicillins but not penicillinase-resistant semisynthetic penicillins, cephalosporins, or imipenem; hydrolysis was inhibited by clavulanic acid [7].
  • Microbiological, pharmacological, and clinical studies show that clavulanic acid in combination with amoxycillin is effective and safe in the treatment of urinary-tract infection caused by amoxycillin-resistant bacteria [8].
  • The enzyme beta-lactam synthetase (beta-LS) catalyzes the formation of the beta-lactam ring in clavulanic acid, a clinically important beta-lactamase inhibitor [9].
  • In contrast to the efficient iron-mediated oxidative cyclization of a tripeptide to isopenicillin N, the critical beta-lactam ring of clavulanic acid is demonstrated to form by intramolecular closure catalyzed by a new type of ATP/Mg2+-dependent enzyme, a beta-lactam synthetase (beta-LS) [10].
  • Insertional inactivation of its encoding gene in wild-type Streptomyces clavuligerus resulted in complete loss of clavulanic acid production and the accumulation of N2-(carboxyethyl)-L-arginine (CEA) [10].

Chemical compound and disease context of CLAVULANIC ACID


Biological context of CLAVULANIC ACID


Anatomical context of CLAVULANIC ACID

  • Clavulanic acid levels in cerebrospinal fluid were less than or equal to 0.05 micrograms/ml in 5 of 18 samples and ranged from 0.1 to 0.8 micrograms/ml in the others [20].
  • Two of 7 patients whose sputum cultures were positive for this organism at a review 2 to 4 weeks later were successfully treated with a further course of amoxycillin/clavulanic acid [21].
  • CONCLUSIONS--Amoxycillin and clavulanic acid are concentrated in bronchial mucosa and, even at the lowest dose of 375 mg orally, are likely to produce tissue levels in the lung sufficient to inhibit all the common community acquired respiratory pathogens [22].
  • Abnormal physiological properties and altered cell wall composition in Streptococcus pneumoniae grown in the presence of clavulanic acid [23].
  • Following the injection of 400 mg, mean concentrations of clavulanic acid in the fatty tissues were significantly increased at the time of opening (P < 0.02) [24].

Associations of CLAVULANIC ACID with other chemical compounds


Gene context of CLAVULANIC ACID

  • Unfortunately, the emergence of clavulanic acid-resistant variants of TEM-1 and SHV-1 beta-lactamase significantly compromise the efficacy of this combination [30].
  • (iii) NB2001 activity against beta-lactamase-producing E. coli is decreased in the presence of the beta-lactamase inhibitor clavulanic acid [31].
  • Transformation of S. clavuligerus 328, an argC auxotroph deficient in clavulanic acid biosynthesis, with plasmid pULML30, carrying the cloned argC gene, restored both prototrophy and antibiotic production [32].
  • One approach to counteracting this resistance mechanism has been through the development of beta-lactamase inactivators. beta-Lactamase inhibitors include clavulanic acid and sulbactam, molecules with minimal antibiotic activity [33].
  • The specificity of ORF17 as an N-glycyl-clavaminic acid synthetase, together with the reported accumulation of N-glycyl-clavaminic acid in orf15 and orf16 disruption mutants, suggested that N-glycyl-clavaminic acid is an intermediate in clavulanic acid biosynthesis [16].

Analytical, diagnostic and therapeutic context of CLAVULANIC ACID


  1. Clavulanic acid and susceptibility of Bacteroides fragilis to penicillin. Wise, R. Lancet (1977) [Pubmed]
  2. Beta-lactamase inhibitors and reversal of antibiotic resistance. Sutherland, R. Trends Pharmacol. Sci. (1991) [Pubmed]
  3. Systemic antibiotic prophylaxis after gastrointestinal hemorrhage in cirrhotic patients with a high risk of infection. Pauwels, A., Mostefa-Kara, N., Debenes, B., Degoutte, E., Lévy, V.G. Hepatology (1996) [Pubmed]
  4. Amoxicillin-clavulanic acid therapy of spontaneous bacterial peritonitis: a prospective study of twenty-seven cases in cirrhotic patients. Grange, J.D., Amiot, X., Grange, V., Gutmann, L., Biour, M., Bodin, F., Poupon, R. Hepatology (1990) [Pubmed]
  5. Understanding resistance to beta-lactams and beta-lactamase inhibitors in the SHV beta-lactamase: lessons from the mutagenesis of SER-130. Helfand, M.S., Bethel, C.R., Hujer, A.M., Hujer, K.M., Anderson, V.E., Bonomo, R.A. J. Biol. Chem. (2003) [Pubmed]
  6. Comparison of two clinical scales for causality assessment in hepatotoxicity. Lucena, M.I., Camargo, R., Andrade, R.J., Perez-Sanchez, C.J., Sanchez De La Cuesta, F. Hepatology (2001) [Pubmed]
  7. In vitro studies of plasmid-mediated penicillinase from Streptococcus faecalis suggest a staphylococcal origin. Murray, B.E., Mederski-Samoraj, B., Foster, S.K., Brunton, J.L., Harford, P. J. Clin. Invest. (1986) [Pubmed]
  8. Clavulanic acid and amoxycillin: a clinical, bacteriological, and pharmacological study. Ball, A.P., Geddes, A.M., Davey, P.G., Farrell, I.D., Brookes, G.R. Lancet (1980) [Pubmed]
  9. Structure of beta-lactam synthetase reveals how to synthesize antibiotics instead of asparagine. Miller, M.T., Bachmann, B.O., Townsend, C.A., Rosenzweig, A.C. Nat. Struct. Biol. (2001) [Pubmed]
  10. beta-Lactam synthetase: a new biosynthetic enzyme. Bachmann, B.O., Li, R., Townsend, C.A. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  11. Systemic antibiotic therapy prevents bacterial infection in cirrhotic patients with gastrointestinal hemorrhage. Blaise, M., Pateron, D., Trinchet, J.C., Levacher, S., Beaugrand, M., Pourriat, J.L. Hepatology (1994) [Pubmed]
  12. Noncomparative trial of ticarcillin plus clavulanic acid in skin and soft tissue infections. LeFrock, J.L., Johnson, E.S., Smith, L.G., Rosenberg, E. Am. J. Med. (1985) [Pubmed]
  13. Efficacy and safety of ticarcillin plus clavulanic acid and piperacillin in patients with lower respiratory tract infections. Link, A.S. Am. J. Med. (1985) [Pubmed]
  14. Comparative clinical evaluation of ticarcillin plus clavulanic acid versus clindamycin plus gentamicin in treatment of post-cesarean endomyometritis. Apuzzio, J.J., Kaminski, Z., Gamesh, V., Louria, D.B. Am. J. Med. (1985) [Pubmed]
  15. Comparison of ticarcillin plus clavulanic acid with cefoxitin in the treatment of female pelvic infection. Pastorek, J.G., Aldridge, K.E., Cunningham, G.L., Faro, S., Graffeo, S., McNeeley, G.S., Tan, J.S. Am. J. Med. (1985) [Pubmed]
  16. ORF17 from the clavulanic acid biosynthesis gene cluster catalyzes the ATP-dependent formation of N-glycyl-clavaminic acid. Arulanantham, H., Kershaw, N.J., Hewitson, K.S., Hughes, C.E., Thirkettle, J.E., Schofield, C.J. J. Biol. Chem. (2006) [Pubmed]
  17. Site-directed mutagenesis at the active site of Escherichia coli TEM-1 beta-lactamase. Suicide inhibitor-resistant mutants reveal the role of arginine 244 and methionine 69 in catalysis. Delaire, M., Labia, R., Samama, J.P., Masson, J.M. J. Biol. Chem. (1992) [Pubmed]
  18. Clinical pharmacology of timentin (ticarcillin and clavulanic acid). Bodey, G.P., Yeo, E., Ho, D.H., Rolston, K., LeBlanc, B. Clin. Pharmacol. Ther. (1985) [Pubmed]
  19. Class A beta-lactamases--enzyme-inhibitor interactions and resistance. Yang, Y., Rasmussen, B.A., Shlaes, D.M. Pharmacol. Ther. (1999) [Pubmed]
  20. Bactericidal activity against Haemophilus influenzae of cerebrospinal fluid of patients given amoxicillin-clavulanic acid. Decazes, J.M., Bure, A., Wolff, M., Kitzis, M.D., Pangon, B., Modai, J. Antimicrob. Agents Chemother. (1987) [Pubmed]
  21. Amoxycillin-clavulanic acid combination in bronchopulmonary infection due to beta-lactamase-producing Branhamella catarrhalis. Preliminary report. Thornley, P.E., Aitken, J.M., Nichol, G.M., Slevin, N.J. Drugs (1986) [Pubmed]
  22. Penetration of amoxycillin/clavulanic acid into bronchial mucosa with different dosing regimens. Gould, I.M., Harvey, G., Golder, D., Reid, T.M., Watt, S.J., Friend, J.A., Legge, J.S., Douglas, J.G. Thorax (1994) [Pubmed]
  23. Abnormal physiological properties and altered cell wall composition in Streptococcus pneumoniae grown in the presence of clavulanic acid. Severin, A., Severina, E., Tomasz, A. Antimicrob. Agents Chemother. (1997) [Pubmed]
  24. Comparison of concentrations of two doses of clavulanic acid (200 and 400 milligrams) administered with amoxicillin (2,000 milligrams) in tissues of patients undergoing colorectal surgery. Martin, C., Mallet, M.N., Sastre, B., Viviand, X., Martin, A., De Micco, P., Gouin, F. Antimicrob. Agents Chemother. (1995) [Pubmed]
  25. Risk of acute liver injury associated with the combination of amoxicillin and clavulanic acid. García Rodríguez, L.A., Stricker, B.H., Zimmerman, H.J. Arch. Intern. Med. (1996) [Pubmed]
  26. Safety and efficacy of ticarcillin plus clavulanic acid in the treatment of infections of soft tissue, bone, and joint. Johnson, C.C., Reinhardt, J.F., Wallace, S.L., Terpenning, M.S., Helsel, C.L., Mulligan, M.E., Finegold, S.M., George, W.L. Am. J. Med. (1985) [Pubmed]
  27. Different proteins bind to the butyrolactone receptor protein ARE sequence located upstream of the regulatory ccaR gene of Streptomyces clavuligerus. Santamarta, I., Pérez-Redondo, R., Lorenzana, L.M., Martín, J.F., Liras, P. Mol. Microbiol. (2005) [Pubmed]
  28. Ticarcillin plus clavulanic acid versus cefoxitin in the prophylaxis of infection after cesarean section. Saltzman, D.H., Eron, L.J., Toy, C., Protomastro, L.J., Sites, J.G. Am. J. Med. (1985) [Pubmed]
  29. Antibacterial activity of ticarcillin in the presence of clavulanate potassium. Sutherland, R., Beale, A.S., Boon, R.J., Griffin, K.E., Slocombe, B., Stokes, D.H., White, A.R. Am. J. Med. (1985) [Pubmed]
  30. Clavulanic acid inactivation of SHV-1 and the inhibitor-resistant S130G SHV-1 beta-lactamase. Insights into the mechanism of inhibition. Sulton, D., Pagan-Rodriguez, D., Zhou, X., Liu, Y., Hujer, A.M., Bethel, C.R., Helfand, M.S., Thomson, J.M., Anderson, V.E., Buynak, J.D., Ng, L.M., Bonomo, R.A. J. Biol. Chem. (2005) [Pubmed]
  31. NB2001, a novel antibacterial agent with broad-spectrum activity and enhanced potency against beta-lactamase-producing strains. Li, Q., Lee, J.Y., Castillo, R., Hixon, M.S., Pujol, C., Doppalapudi, V.R., Shepard, H.M., Wahl, G.M., Lobl, T.J., Chan, M.F. Antimicrob. Agents Chemother. (2002) [Pubmed]
  32. Characterization of the Streptomyces clavuligerus argC gene encoding N-acetylglutamyl-phosphate reductase: expression in Streptomyces lividans and effect on clavulanic acid production. Ludovice, M., Martin, J.F., Carrachas, P., Liras, P. J. Bacteriol. (1992) [Pubmed]
  33. Beta-lactamase inhibitors from laboratory to clinic. Bush, K. Clin. Microbiol. Rev. (1988) [Pubmed]
  34. Pharmacology of ticarcillin combined with clavulanic acid in humans. Scully, B.E., Chin, N.X., Neu, H.C. Am. J. Med. (1985) [Pubmed]
  35. VEB-1-like extended-spectrum beta-lactamases in Pseudomonas aeruginosa, Kuwait. Poirel, L., Rotimi, V.O., Mokaddas, E.M., Karim, A., Nordmann, P. Emerging Infect. Dis. (2001) [Pubmed]
  36. Pharmacokinetics of amoxicillin and clavulanic acid administered alone and in combination. Adam, D., de Visser, I., Koeppe, P. Antimicrob. Agents Chemother. (1982) [Pubmed]
  37. Positive direct antiglobulin tests due to clavulanic acid. Williams, M.E., Thomas, D., Harman, C.P., Mintz, P.D., Donowitz, G.R. Antimicrob. Agents Chemother. (1985) [Pubmed]
  38. Inhibition of TEM-2 beta-lactamase from Escherichia coli by clavulanic acid: observation of intermediates by electrospray ionization mass spectrometry. Brown, R.P., Aplin, R.T., Schofield, C.J. Biochemistry (1996) [Pubmed]
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