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Chemical Compound Review

Bicillin     (2R,5R,6S)-3,3-dimethyl-7- oxo-6-(2...

Synonyms: Permapen, Pfizerpen, Ursopen, Penicillin, penicillin g, ...
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Disease relevance of Pfizerpen

  • The in vitro activities of four extended-spectrum cephalosporins and benzyl penicillin were evaluated against 698 clinical isolates of Streptococcus pneumoniae, including 130 (19%) penicillin-intermediate and 84 (12%) penicillin-resistant strains [1].
  • Most methicillin-resistant Staphylococcus aureus (MRSA) isolates identified among blood isolates collected in Denmark between 1957 and 1970 belonged to either phage group III or the closely related 83A complex and had a PSTM antibiotype (resistance to penicillin [P], streptomycin [S], tetracycline [T], and methicillin [M]) [2].
  • Of 259 patients who had received quinolone prophylaxis during the study period, 22 (8.5%) developed an episode of viridans streptococcal bacteremia as compared with three episodes (3.7%) in 82 patients who had received a quinolone and penicillin (P = .07) [3].
  • ELF and mucosal site concentrations were effective against Streptococcus pneumoniae (except one strain with reduced susceptibility to benzyl penicillin) and Haemophilus influenzae [4].
  • The diagnosis of betalactam hypersensitivity, classically based on skin testing with major and minor determinants of benzyl penicillin or in vitro IgE antibodies to BP, has been modified by the inclusion of different determinants generated from these compounds, for which amoxicillin (AX) is the most relevant, followed by cephalosporins [5].

High impact information on Pfizerpen

  • In sharp contrast, we show here that the dominant activating fadA allele, fadAG42R, stimulates transcription of a gene from the A. nidulans penicillin (PN) gene cluster and elevates penicillin production [6].
  • Two in vitro selection protocols were designed to extract from the library phage-enzymes characterised by a fast acylation by benzyl-penicillin (PenG) to yield either stable or very unstable acyl-enzymes [7].
  • The presence of the substrate benzyl penicillin has little effect on the equilibria or kinetics of the N-H transition [8].
  • Antibody levels to the serotype 2 outer membrane proteins were significantly elevated in C6-deficient patients compared with control groups (P = .001) [9].
  • Decarboxylation of the penicilloic acids from benzyl-penicillin, or from phenoxymethylpenicillin, leads to epimerization (at C-5) of the penilloic acid [10].

Chemical compound and disease context of Pfizerpen


Biological context of Pfizerpen

  • A model of the tetrahedral transition state associated with the acylation step by benzyl penicillin has been derived [15].
  • EPSP summation was linear after the IPSP had been blocked by benzyl penicillin application [16].
  • Adsorption rate was faster at higher mu values, positively correlated to cell size, and increased by pretreatment with low penicillin (Pn) concentrations; it was directly proportional to total cellular surface area, indicating a constant density of T4 receptors on cell envelopes irrespective of growth conditions [17].
  • Using [14C] benzyl penicillin, we determined the ability of penicillin to cross capillary membranes in the tibiae of dogs, the degree of protein-binding of penicillin in serum and tibial bone tissue, and the concentration of penicillin in the interstitial fluid space of tibial bone [18].
  • Most resistance was observed against penicillin, 39% of the isolates from older cows and 26% from first lactation cows being resistant to penicillin (P > 0.05) [19].

Anatomical context of Pfizerpen

  • Addition of benzyl penicillin (300 mug/ml) to growing protoplast cultures did not affect the net amount of PG fragments synthesized but resulted in inhibition of synthesis of dimer and trimer fractions by 27 and 59%, respectively [20].
  • Extraction studies demonstrated that the capillary membranes in bone were readily traversed by benzyl penicillin [18].
  • Studies of the distribution of benzyl penicillin showed that it was distributed in equal concentrations in the plasma and in the interstitial fluid spaces of bone [18].
  • In rabbits infected with strain 1 for 6 hours before treatment, most vegetations were sterile after 3 days therapy with each combination but not with P alone which had mean log10 colony forming units per gram of vegetation (log CFU) of 2 [21].
  • Bicuculline, benzyl penicillin, and inhibitory amino acids in the spinal cord of the cat [22].

Associations of Pfizerpen with other chemical compounds


Gene context of Pfizerpen

  • Antibiotic use in the previous month was associated with reduced susceptibility to penicillin (p = 0.007) and multidrug resistance (p = 0.012) [27].
  • It has been reported that certain nonpigmented, slow-growing mycobacteria do not have a constitutive beta-lactamase and are more sensitive to benzyl penicillin than M. tuberculosis [28].
  • Kinetics of drug decomposition. Part 62. Kinetics of penicillin G potassium salt (PGP) thermal degradation in solid phase [29].
  • Approximately 10(-5) transductant colonies per phage input were obtained and ultraviolet kinetics indicated that Pc was plasmid carried [30].
  • Very little cross-reactivity of CET and potassium benzyl penicillin (PcG) was noted when these antibiotics were used as the challenge antigens for PCA induced by corresponding murine antisera [31].

Analytical, diagnostic and therapeutic context of Pfizerpen


  1. In vitro activities of cefotaxime, ceftriaxone, ceftazidime, cefpirome, and penicillin against Streptococcus pneumoniae isolates. Barry, A.L., Brown, S.D., Novick, W.J. Antimicrob. Agents Chemother. (1995) [Pubmed]
  2. Origins and Evolution of Methicillin-Resistant Staphylococcus aureus Clonal Lineages. Gomes, A.R., Westh, H., de Lencastre, H. Antimicrob. Agents Chemother. (2006) [Pubmed]
  3. Bacteremia due to viridans streptococcus in neutropenic patients with cancer: clinical spectrum and risk factors. Bochud, P.Y., Eggiman, P., Calandra, T., Van Melle, G., Saghafi, L., Francioli, P. Clin. Infect. Dis. (1994) [Pubmed]
  4. Bronchoalveolar distribution of cefuroxime axetil and in-vitro efficacy of observed concentrations against respiratory pathogens. Baldwin, D.R., Andrews, J.M., Wise, R., Honeybourne, D. J. Antimicrob. Chemother. (1992) [Pubmed]
  5. Immediate hypersensitivity reactions to penicillins and other betalactams. Ant??nez, C., Mart??n, E., Cornejo-Garc??a, J.A., Blanca-Lopez, N., R-Pena, R., Mayorga, C., Torres, M.J., Blanca, M. Curr. Pharm. Des. (2006) [Pubmed]
  6. G-protein signalling mediates differential production of toxic secondary metabolites. Tag, A., Hicks, J., Garifullina, G., Ake, C., Phillips, T.D., Beremand, M., Keller, N. Mol. Microbiol. (2000) [Pubmed]
  7. Selection of beta-lactamases and penicillin binding mutants from a library of phage displayed TEM-1 beta-lactamase randomly mutated in the active site omega-loop. Vanwetswinkel, S., Avalle, B., Fastrez, J. J. Mol. Biol. (2000) [Pubmed]
  8. Effects of sulphate and urea on the stability and reversible unfolding of beta-lactamase from Staphylococcus aureus. Implications for the folding pathway of beta-lactamase. Mitchinson, C., Pain, R.H. J. Mol. Biol. (1985) [Pubmed]
  9. Prophylaxis against Neisseria meningitidis infections and antibody responses in patients with deficiency of the sixth component of complement. Potter, P.C., Frasch, C.E., van der Sande, W.J., Cooper, R.C., Patel, Y., Orren, A. J. Infect. Dis. (1990) [Pubmed]
  10. Reversible inhibitors of penicillinases. Kiener, P.A., Waley, S.G. Biochem. J. (1978) [Pubmed]
  11. Benzathine penicillin, metronidazole and benzyl penicillin in the treatment of tetanus: a randomized, controlled trial. Ganesh Kumar, A.V., Kothari, V.M., Krishnan, A., Karnad, D.R. Ann. Trop. Med. Parasitol. (2004) [Pubmed]
  12. Risk factors for colic in horses after general anaesthesia for MRI or nonabdominal surgery: absence of evidence of effect from perianaesthetic morphine. Andersen, M.S., Clark, L., Dyson, S.J., Newton, J.R. Equine Vet. J. (2006) [Pubmed]
  13. Treatment of bacterial meningitis in children without intravenous fluids. Shann, F., Germer, S. Med. J. Aust. (1981) [Pubmed]
  14. Intramuscular bipenicillin vs. intravenous penicillin in the treatment of erysipelas in adults: randomized controlled study. Zeglaoui, F., Dziri, C., Mokhtar, I., Ezzine, N., Kharfi, M., Zghal, M., Fazaa, B., Kamoun, M.R. Journal of the European Academy of Dermatology and Venereology : JEADV. (2004) [Pubmed]
  15. Structure of a phosphonate-inhibited beta-lactamase. An analog of the tetrahedral transition state/intermediate of beta-lactam hydrolysis. Chen, C.C., Rahil, J., Pratt, R.F., Herzberg, O. J. Mol. Biol. (1993) [Pubmed]
  16. Summation of excitatory postsynaptic potentials in hippocampal pyramidal cells. Langmoen, I.A., Andersen, P. J. Neurophysiol. (1983) [Pubmed]
  17. Bacteriophage T4 development depends on the physiology of its host Escherichia coli. Hadas, H., Einav, M., Fishov, I., Zaritsky, A. Microbiology (Reading, Engl.) (1997) [Pubmed]
  18. The transcapillary passage and interstitial fluid concentration of penicillin in canine bone. Bloom, J.D., Fitzgerald, R.H., Washington, J.A., Kelly, P.J. The Journal of bone and joint surgery. American volume. (1980) [Pubmed]
  19. Antimicrobial susceptibility of mastitis pathogens from first lactation and older cows. Rajala-Schultz, P.J., Smith, K.L., Hogan, J.S., Love, B.C. Vet. Microbiol. (2004) [Pubmed]
  20. Characterization of the presumed peptide cross-links in the soluble peptidoglycan fragments synthesized by protoplasts of Streptococcus faecalis. Rosenthal, R.S., Shockman, G.D. J. Bacteriol. (1975) [Pubmed]
  21. Antibiotic synergism in enterococcal endocarditis. Carrizosa, J., Kaye, D. J. Lab. Clin. Med. (1976) [Pubmed]
  22. Bicuculline, benzyl penicillin, and inhibitory amino acids in the spinal cord of the cat. Krnjević, K., Puil, E., Werman, R. Can. J. Physiol. Pharmacol. (1977) [Pubmed]
  23. Growth of Streptococcus mutans protoplasts is not inhibited by penicillin. Parks, L.C., Shockman, G.D., Higgins, M.L. J. Bacteriol. (1980) [Pubmed]
  24. Studies of the specificities of IgE antibodies found in sera from subjects with allergic reactions to penicillins. Moreno, F., Blanca, M., Mayorga, C., Terrados, S., Moya, M., Pérez, E., Suau, R., Vega, J.M., García, J., Miranda, A. Int. Arch. Allergy Immunol. (1995) [Pubmed]
  25. Mechanisms of action of corilagin and tellimagrandin I that remarkably potentiate the activity of beta-lactams against methicillin-resistant Staphylococcus aureus. Shiota, S., Shimizu, M., Sugiyama, J., Morita, Y., Mizushima, T., Tsuchiya, T. Microbiol. Immunol. (2004) [Pubmed]
  26. Simulation of concentration-time profiles of benzyl-penicillin, enrofloxacin and dihydrostreptomycin in tissue cages in calves. Bengtsson, B., Greko, C. J. Vet. Pharmacol. Ther. (2002) [Pubmed]
  27. Prevalence and patterns of resistance of Streptococcus pneumoniae strains isolated from carriers attending day care centers in the area of Athens. Tsolia, M., Kouppari, G., Zaphiropoulou, A., Gavrili, S., Tsirepa, M., Kafetzis, D., Karpathios, T. Microb. Drug Resist. (1999) [Pubmed]
  28. beta-Lactamase activity in slow-growing nonpigmented mycobacteria and their sensitivity to certain beta-lactam antibiotics. Kasik, J.E., Monick, M., Schwarz, B. Tubercle. (1980) [Pubmed]
  29. Kinetics of drug decomposition. Part 62. Kinetics of penicillin G potassium salt (PGP) thermal degradation in solid phase. Pawełczyk, E., Płotkowiak, Z., Knitter, K., Kozakiewicz-Wegner, B. Polish journal of pharmacology and pharmacy. (1980) [Pubmed]
  30. Transduction of penicillinase production and other antibiotic-resistance markers in Staphylococcus epidermidis. Poston, S.M., Palmer, T.J. J. Gen. Microbiol. (1977) [Pubmed]
  31. Detection and characterization of polymers in cephalothin by passive cutaneous anaphylaxis in mice. Iwata, M., Tokiwa, H., Matuhasi, T. Int. Arch. Allergy Appl. Immunol. (1983) [Pubmed]
  32. Epileptogenic action of penicillin derivatives: structure-activity relationship. Esplin, B., Théorêt, Y., Seward, E., Capek, R. Neuropharmacology (1985) [Pubmed]
  33. Streptococcus pneumoniae septic arthritis in adults. James, P.A., Thomas, M.G. Scand. J. Infect. Dis. (2000) [Pubmed]
  34. Chancre redux or reinfection? A case report in an HIV-positive man. McQuillan, O., Higgins, S.P. International journal of STD & AIDS. (2006) [Pubmed]
  35. Intraphagocytic protection of staphylococci from extracellular penicillin. Lam, C., Mathison, G.E. J. Med. Microbiol. (1982) [Pubmed]
  36. LOcal effects of antibacterial therapy (benzyl-penicillin) on missile wound infection rate and tissue devitalization when debridement is delayed for twelve hours. Dahlgren, B., Almskog, B., Berlin, R., Nordström, G., Rybeck, B., Schantz, B., Seeman, T. Acta chirurgica Scandinavica. Supplementum. (1982) [Pubmed]
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