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Chemical Compound Review

CHEMBL105851     (2R,4R)-2-[(S)- ethylcarbamoyl-(2...

Synonyms: C2-sym dimer, AC1L9RSE, 142762-73-0, penicillin deriv. 3, Penicillin Et(NH)2 dimer
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Disease relevance of penicillin g


Psychiatry related information on penicillin g


High impact information on penicillin g


Chemical compound and disease context of penicillin g


Biological context of penicillin g

  • Treatment and follow-up of the pharyngeal infections were available only for the men seen at the Clark Public Health Clinic. These men responded to penicillin G procaine for penicillin-sensitive N gonorrhoeae and to spectinomycin hydrochloride for PPNG [15].
  • This disorder was characterised by: prolongation of bleeding-time, appearing immediately after penicillin-G administration and persisting until 4 days after withdrawal of therapy; disturbance of collagen-induced and ristocetin-induced platelet aggregation; increase of antithrombin-III activity; and inhibition of factor-xa activity [16].
  • A coagulation disorder was seen after penicillin-G administration (10 million units/day) in uraemic patients and after high-dose penicillin G (40 million units/day) in patients with a normal glomerular filtration-rate (5 patients after cardiac surgery) [16].
  • In cells grown at 24 degrees C the localization of beta-lactamase on the cell surface was almost quantitative (greater than 80% of the enzymatically active protein was exposed to the extracellular fluid) as determined by nitrocefin and penicillin G hydrolysis and trypsin accessibility [17].
  • These data establish that the hydroxylaminolysis is an enzymatically catalyzed process suggesting that penicillin G is bound to an enzymatically active site [18].

Anatomical context of penicillin g

  • Intravenous administration of a total dose of more than 200 million IU of penicillin-G led to sensitisation of lymphocytes and formation of specific anti-penicilloyl antibodies of the IgG class [19].
  • Granulocyte colony-stimulating factor versus placebo in addition to penicillin G in a randomized blinded study of gram-negative pneumonia sepsis: analysis of survival and multisystem organ failure [20].
  • Two cell lines that were multidrug resistant showed no enhanced resistance to NHPAP +/- penicillin G amidase [21].
  • T cell clones specific for penicillin G or BPO-HSA were established and their phenotype and reactivity to both forms of the beta-lactam were analyzed [22].
  • Infrared spectroscopy analysis using isogenic penicillin-susceptible strains and strains with reduced susceptibility to penicillin G suggested that the meningococcal cell wall is also modified in a penA-dependent manner [23].

Associations of penicillin g with other chemical compounds


Gene context of penicillin g


Analytical, diagnostic and therapeutic context of penicillin g


  1. The response of symptomatic neurosyphilis to high-dose intravenous penicillin G in patients with human immunodeficiency virus infection. Gordon, S.M., Eaton, M.E., George, R., Larsen, S., Lukehart, S.A., Kuypers, J., Marra, C.M., Thompson, S. N. Engl. J. Med. (1994) [Pubmed]
  2. A pharmacologic evaluation of penicillin in children with purulent meningitis. Hieber, J.P., Nelson, J.D. N. Engl. J. Med. (1977) [Pubmed]
  3. National gonorrhea therapy monitoring study: in vitro antibiotic susceptibility and its correlation with treatment results. Jaffe, H.W., Biddle, J.W., Thornsberry, C., Johnson, R.E., Kaufman, R.E., Reynolds, G.H., Wiesner, P.J. N. Engl. J. Med. (1976) [Pubmed]
  4. Paradoxical action of penicillin G on Staphylococcus aureus: a time study of the effect of a zonal antibiotic concentration gradient on bacterial growth. Yourassowsky, E., Vanderlinden, M.P., Lismont, M.J., Schoutens, E. Antimicrob. Agents Chemother. (1975) [Pubmed]
  5. H+ISFET-based biosensor for determination of penicillin G. Liu, J., Liang, L., Li, G., Han, R., Chen, K. Biosensors & bioelectronics. (1998) [Pubmed]
  6. Hyperendemic Streptococcus pyogenes infection despite prophylaxis with penicillin G benzathine. Gray, G.C., Escamilla, J., Hyams, K.C., Struewing, J.P., Kaplan, E.L., Tupponce, A.K. N. Engl. J. Med. (1991) [Pubmed]
  7. Risk factors and response to antibiotic therapy in adults with bacteremic pneumonia caused by penicillin-resistant pneumococci. Pallares, R., Gudiol, F., Liñares, J., Ariza, J., Rufi, G., Murgui, L., Dorca, J., Viladrich, P.F. N. Engl. J. Med. (1987) [Pubmed]
  8. Spectinomycin versus tetracycline for the treatment of gonorrhea. Karney, W.W., Pedersen, A.H., Nelson, M., Adams, H., Pfeifer, R.T., Holmes, K.K. N. Engl. J. Med. (1977) [Pubmed]
  9. Molecular structure of the acyl-enzyme intermediate in beta-lactam hydrolysis at 1.7 A resolution. Strynadka, N.C., Adachi, H., Jensen, S.E., Johns, K., Sielecki, A., Betzel, C., Sutoh, K., James, M.N. Nature (1992) [Pubmed]
  10. Intrathecal gentamicin for refractory gram-positive meningitis. Shuman, R.D., Smith, C.R. JAMA (1978) [Pubmed]
  11. Short-term therapy for streptococcal infective endocarditis. Combined intramuscular administration of penicillin and streptomycin. Wilson, W.R., Thompson, R.L., Wilkowske, C.J., Washington, J.A., Giuliani, E.R., Geraci, J.E. JAMA (1981) [Pubmed]
  12. Ceftriaxone sodium therapy of penicillin G-susceptible streptococcal endocarditis. Wilson, W.R. JAMA (1992) [Pubmed]
  13. The 'borderline' smear in men with urethritis. Arnold, A.J., Kleris, G.S. JAMA (1980) [Pubmed]
  14. Treatment of aspiration pneumonia and primary lung abscess. Penicillin G vs clindamycin. Bartlett, J.G., Gorbach, S.L. JAMA (1975) [Pubmed]
  15. Pharyngeal gonorrhea. Tice, A.W., Rodriguez, V.L. JAMA (1981) [Pubmed]
  16. Penicillin-induced coagulation disorder. Andrassy, K., Ritz, E., Hasper, B., Scherz, M., Walter, E., Storch, H. Lancet (1976) [Pubmed]
  17. Transport and anchoring of beta-lactamase to the external surface of Escherichia coli. Francisco, J.A., Earhart, C.F., Georgiou, G. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  18. Hydroxylaminolysis of penicillin binding componenets is enzymatically catalyzed. Kozarich, J.W., Nishino, T., Willoughby, E., Strominger, J.L. J. Biol. Chem. (1977) [Pubmed]
  19. Effect of storage of penicillin-G solutions on sensitisation to penicillin-G after intravenous administration. Neftel, K.A., Wälti, M., Spengler, H., de Weck, A.L. Lancet (1982) [Pubmed]
  20. Granulocyte colony-stimulating factor versus placebo in addition to penicillin G in a randomized blinded study of gram-negative pneumonia sepsis: analysis of survival and multisystem organ failure. Smith, W.S., Sumnicht, G.E., Sharpe, R.W., Samuelson, D., Millard, F.E. Blood (1995) [Pubmed]
  21. N-(4'-hydroxyphenylacetyl)palytoxin: a palytoxin prodrug that can be activated by a monoclonal antibody-penicillin G amidase conjugate. Bignami, G.S., Senter, P.D., Grothaus, P.G., Fischer, K.J., Humphreys, T., Wallace, P.M. Cancer Res. (1992) [Pubmed]
  22. Heterogeneous T cell responses to beta-lactam-modified self-structures are observed in penicillin-allergic individuals. Brander, C., Mauri-Hellweg, D., Bettens, F., Rolli, H., Goldman, M., Pichler, W.J. J. Immunol. (1995) [Pubmed]
  23. Correlation between alterations of the penicillin-binding protein 2 and modifications of the peptidoglycan structure in Neisseria meningitidis with reduced susceptibility to penicillin G. Antignac, A., Boneca, I.G., Rousselle, J.C., Namane, A., Carlier, J.P., Vázquez, J.A., Fox, A., Alonso, J.M., Taha, M.K. J. Biol. Chem. (2003) [Pubmed]
  24. Comparative study of ceftriaxone and spectinomycin for treatment of pharyngeal and anorectal gonorrhea. Judson, F.N., Ehret, J.M., Handsfield, H.H. JAMA (1985) [Pubmed]
  25. Penicillin levels in blood and CSF achieved by treatment of syphilis. Dunlop, E.M., Al-Egaily, S.S., Houang, E.T. JAMA (1979) [Pubmed]
  26. Carbenicillin and penicillin G inhibit platelet function in vitro by impairing the interaction of agonists with the platelet surface. Shattil, S.J., Bennett, J.S., McDonough, M., Turnbull, J. J. Clin. Invest. (1980) [Pubmed]
  27. A potent new mode of beta-lactamase inhibition revealed by the 1.7 A X-ray crystallographic structure of the TEM-1-BLIP complex. Strynadka, N.C., Jensen, S.E., Alzari, P.M., James, M.N. Nat. Struct. Biol. (1996) [Pubmed]
  28. Antigen-dependent and -independent IFN-gamma modulation by penicillins. Padovan, E., von Greyerz, S., Pichler, W.J., Weltzien, H.U. J. Immunol. (1999) [Pubmed]
  29. Highly Th2-skewed cytokine profile of beta-lactam-specific T cells from nonatopic subjects with adverse drug reactions. Brugnolo, F., Annunziato, F., Sampognaro, S., Campi, P., Manfredi, M., Matucci, A., Blanca, M., Romagnani, S., Maggi, E., Parronchi, P. J. Immunol. (1999) [Pubmed]
  30. In vitro interferon producing activity of peripheral mononuclear cells in patients with chronic liver disease. Matsushita, K., Arima, T., Nagashima, H. Gastroenterol. Jpn. (1987) [Pubmed]
  31. Localization of multidrug transporter substrates within model membranes. Siarheyeva, A., Lopez, J.J., Glaubitz, C. Biochemistry (2006) [Pubmed]
  32. Characterization of methotrexate transport and its drug interactions with human organic anion transporters. Takeda, M., Khamdang, S., Narikawa, S., Kimura, H., Hosoyamada, M., Cha, S.H., Sekine, T., Endou, H. J. Pharmacol. Exp. Ther. (2002) [Pubmed]
  33. Distribution of mefE and ermB genes in macrolide-resistant strains of Streptococcus pneumoniae and their variable susceptibility to various antibiotics. Nishijima, T., Saito, Y., Aoki, A., Toriya, M., Toyonaga, Y., Fujii, R. J. Antimicrob. Chemother. (1999) [Pubmed]
  34. Penicillin in infants weighing two kilograms or less with early-onset Group B streptococcal disease. Pyati, S.P., Pildes, R.S., Jacobs, N.M., Ramamurthy, R.S., Yeh, T.F., Raval, D.S., Lilien, L.D., Amma, P., Metzger, W.I. N. Engl. J. Med. (1983) [Pubmed]
  35. Skin tests, penicillin G procaine, and pseudoanaphylaxis. Mirel, R.D., Garnick, M.B. JAMA (1978) [Pubmed]
  36. Accidental intra-arterial injection of penicillin G. A preventable catastrophe. Schanzer, H., Gribetz, I., Jacobson, J.H. JAMA (1979) [Pubmed]
  37. Low dosage and long treatment duration of beta-lactam: risk factors for carriage of penicillin-resistant Streptococcus pneumoniae. Guillemot, D., Carbon, C., Balkau, B., Geslin, P., Lecoeur, H., Vauzelle-Kervroëdan, F., Bouvenot, G., Eschwége, E. JAMA (1998) [Pubmed]
  38. On-line analysis of penicillin blood levels in the live rat by combined microdialysis/fast-atom bombardment mass spectrometry. Caprioli, R.M., Lin, S.N. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
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