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Chemical Compound Review

Megalomicin     (3R,4S,5R,6R,7R,9R,11R,12R,13S ,14R)-4-[(2R...

Synonyms: Megalomicina, Megalomicine, Piperacilina, Megalomicinum, Piperacillina, ...
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Disease relevance of piperacillin


Psychiatry related information on piperacillin


High impact information on piperacillin


Chemical compound and disease context of piperacillin


Biological context of piperacillin


Anatomical context of piperacillin

  • Sepsis associated with urinary tract infection. Antibiotic treatment with piperacillin [19].
  • Megalomicin (MGM) has been shown to cause a dilation of the most distal cisternae of the Golgi complex [20].
  • Moreover, the patient's treatment serum, while the patient was receiving piperacillin, was able to trigger histamine release from passively sensitized basophils of a donor not allergic to penicillin, suggesting the presence of a sufficient amount of complete multivalent antigen to initiate release and/or desensitization [21].
  • Sputum and serum piperacillin levels were obtained from eight patients with bronchial disease receiving a five to seven day course (8 to 16 g/day) [22].
  • Mean peak muscle and adipose tissue piperacillin concentrations of 31 and 27 micrograms/g, respectively, were reached at between 2 and 3 h after the start of infusion [23].

Associations of piperacillin with other chemical compounds

  • RESULTS: As a single agent, ceftazidime was as effective as the combination of piperacillin and tobramycin (62.7% satisfactory responses compared with 61.1%; odds ratio, 1.07%; 95% Cl, 0.79 to 1.44; P > 0.2) [4].
  • By using low concentrations of the beta-lactams cephalexin and piperacillin to specifically inhibit FtsI (PBP3), an enzyme that synthesizes peptidoglycan at the division septum, we show that FtsZ ring constriction requires the transpeptidase activity of FtsI [24].
  • OBJECTIVE: To compare the safety and efficacy of intravenous (IV) ciprofloxacin plus IV metronidazole (CIP+MET) with that of IV piperacillin/tazobactam (PIP/TAZO) in adults with complicated intraabdominal infections, and to compare the efficacy of sequential IV-to-oral CIP+MET therapy with that of the IV CIP-only regimen [25].
  • A prospective randomized, double-blind study comparing imipenem with a control regimen of piperacillin plus amikacin as empiric antibiotic therapy of febrile granulocytopenic patients with cancer is currently underway at the University of Maryland Cancer Center [26].
  • Considering the extensive knowledge surrounding the genetic engineering of the erythromycin PKS and the familiarity with genetic manipulation and fermentation of S. erythraea, the ability to produce megalomicin in this strain should allow the engineering of novel megalomicin analogues with potentially improved therapeutic activities [14].

Gene context of piperacillin


Analytical, diagnostic and therapeutic context of piperacillin


  1. Adverse reactions to piperacillin in cystic fibrosis. Stead, R.J., Kennedy, H.G., Hodson, M.E., Batten, J.C. Lancet (1984) [Pubmed]
  2. Piperacillin and haemorrhagic cystitis. Joy, V.A. Lancet (1979) [Pubmed]
  3. Azlocillin, mezlocillin, and piperacillin: new broad-spectrum penicillins. Eliopoulos, G.M., Moellering, R.C. Ann. Intern. Med. (1982) [Pubmed]
  4. Ceftazidime compared with piperacillin and tobramycin for the empiric treatment of fever in neutropenic patients with cancer. A multicenter randomized trial. The Intercontinental Antimicrobial Study Group. De Pauw, B.E., Deresinski, S.C., Feld, R., Lane-Allman, E.F., Donnelly, J.P. Ann. Intern. Med. (1994) [Pubmed]
  5. Piperacillin to prevent cholangitis after endoscopic retrograde cholangiopancreatography. A randomized, controlled trial. van den Hazel, S.J., Speelman, P., Dankert, J., Huibregtse, K., Tytgat, G.N., van Leeuwen, D.J. Ann. Intern. Med. (1996) [Pubmed]
  6. Double-blind; placebo-controlled trial of piperacillin prophylaxis in preterm membrane rupture. Lockwood, C.J., Costigan, K., Ghidini, A., Wein, R., Chien, D., Brown, B.L., Alvarez, M., Cetrulo, C.L. Am. J. Obstet. Gynecol. (1993) [Pubmed]
  7. Single or triple dose piperacillin prophylaxis in elective cesarean section. Shah, S., Mazher, Y., John, I.S. International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics. (1998) [Pubmed]
  8. Antibiotic susceptibility among aerobic gram-negative bacilli in intensive care units in 5 European countries. French and Portuguese ICU Study Groups. Hanberger, H., Garcia-Rodriguez, J.A., Gobernado, M., Goossens, H., Nilsson, L.E., Struelens, M.J. JAMA (1999) [Pubmed]
  9. Filgrastim in patients with chemotherapy-induced febrile neutropenia. A double-blind, placebo-controlled trial. Maher, D.W., Lieschke, G.J., Green, M., Bishop, J., Stuart-Harris, R., Wolf, M., Sheridan, W.P., Kefford, R.F., Cebon, J., Olver, I., McKendrick, J., Toner, G., Bradstock, K., Lieschke, M., Cruickshank, S., Tomita, D.K., Hoffman, E.W., Fox, R.M., Morstyn, G. Ann. Intern. Med. (1994) [Pubmed]
  10. Beta-lactam antibiotic therapy in febrile granulocytopenic patients. A randomized trial comparing cefoperazone plus piperacillin, ceftazidime plus piperacillin, and imipenem alone. Winston, D.J., Ho, W.G., Bruckner, D.A., Champlin, R.E. Ann. Intern. Med. (1991) [Pubmed]
  11. Cecropin B enhances betalactams activities in experimental rat models of gram-negative septic shock. Ghiselli, R., Giacometti, A., Cirioni, O., Mocchegiani, F., Orlando, F., D'Amato, G., Sisti, V., Scalise, G., Saba, V. Ann. Surg. (2004) [Pubmed]
  12. Moxalactam plus piperacillin versus moxalactam plus amikacin in febrile granulocytopenic patients. Winston, D.J., Barnes, R.C., Ho, W.G., Young, L.S., Champlin, R.E., Gale, R.P. Am. J. Med. (1984) [Pubmed]
  13. Comparative trial of ticarcillin plus clavulanic acid and piperacillin in the treatment of acute bacterial infection. Pierce, M.A., Wofford, J.D., Cobbs, C.G. Am. J. Med. (1985) [Pubmed]
  14. Biosynthesis of the anti-parasitic agent megalomicin: transformation of erythromycin to megalomicin in Saccharopolyspora erythraea. Volchegursky, Y., Hu, Z., Katz, L., McDaniel, R. Mol. Microbiol. (2000) [Pubmed]
  15. Intra-Golgi transport inhibition by megalomicin. Bonay, P., Munro, S., Fresno, M., Alarcón, B. J. Biol. Chem. (1996) [Pubmed]
  16. A controlled study of ticarcillin plus clavulanic acid versus piperacillin as empiric therapy for fever in the immunocompromised host. Williams, M.E., Harman, C., Scheld, M., Hess, C.E., Donowitz, G.R. Am. J. Med. (1985) [Pubmed]
  17. A prospective evaluation of optimal sampling theory in the determination of the steady-state pharmacokinetics of piperacillin in febrile neutropenic cancer patients. Drusano, G.L., Forrest, A., Plaisance, K.I., Wade, J.C. Clin. Pharmacol. Ther. (1989) [Pubmed]
  18. Piperacillin kinetics. Batra, V.K., Morrison, J.A., Lasseter, K.C., Joy, V.A. Clin. Pharmacol. Ther. (1979) [Pubmed]
  19. Sepsis associated with urinary tract infection. Antibiotic treatment with piperacillin. Tunn, U.W., Thieme, H. Arch. Intern. Med. (1982) [Pubmed]
  20. Megalomicin disrupts lysosomal functions. Bonay, P., Fresno, M., Alarcón, B. J. Cell. Sci. (1997) [Pubmed]
  21. Basophil histamine release remains unaffected by clinical desensitization to penicillin. Pienkowski, M.M., Kazmier, W.J., Adkinson, N.F. J. Allergy Clin. Immunol. (1988) [Pubmed]
  22. Penetration of piperacillin into bronchial mucosa and sputum. Marlin, G.E., Burgess, K.R., Burgoyne, J., Funnell, G.R., Guinness, M.D. Thorax (1981) [Pubmed]
  23. Piperacillin distribution into bile, gallbladder wall, abdominal skeletal muscle, and adipose tissue in surgical patients. Russo, J., Thompson, M.I., Russo, M.E., Saxon, B.A., Matsen, J.M., Moody, F.G., Rikkers, L.F. Antimicrob. Agents Chemother. (1982) [Pubmed]
  24. Inactivation of FtsI inhibits constriction of the FtsZ cytokinetic ring and delays the assembly of FtsZ rings at potential division sites. Pogliano, J., Pogliano, K., Weiss, D.S., Losick, R., Beckwith, J. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  25. Comparison of intravenous/oral ciprofloxacin plus metronidazole versus piperacillin/tazobactam in the treatment of complicated intraabdominal infections. Cohn, S.M., Lipsett, P.A., Buchman, T.G., Cheadle, W.G., Milsom, J.W., O'Marro, S., Yellin, A.E., Jungerwirth, S., Rochefort, E.V., Haverstock, D.C., Kowalsky, S.F. Ann. Surg. (2000) [Pubmed]
  26. Potential of imipenem as single-agent empiric antibiotic therapy of febrile neutropenic patients with cancer. Wade, J.C., Standiford, H.C., Drusano, G.L., Johnson, D.E., Moody, M.R., Bustamante, C.I., Joshi, J.H., deJongh, C., Schimpff, S.C. Am. J. Med. (1985) [Pubmed]
  27. Simulation of human serum pharmacokinetics of cefazolin, piperacillin, and BRL 42715 in rats and efficacy against experimental intraperitoneal infections. Woodnutt, G., Berry, V., Mizen, L. Antimicrob. Agents Chemother. (1992) [Pubmed]
  28. Susceptibility of Escherichia coli isolates with TEM-1 beta-lactamase to combinations of BRL42715, tazobactam or clavulanate with piperacillin or amoxycillin . Livermore, D.M., Seetulsingh, P. J. Antimicrob. Chemother. (1991) [Pubmed]
  29. Behaviour of beta-lactamase-positive and -negative Staphylococcus aureus isolates in susceptibility tests with piperacillin/tazobactam and other beta-lactam/beta-lactamase inhibitor combinations. Bonfiglio, G., Livermore, D.M. J. Antimicrob. Chemother. (1993) [Pubmed]
  30. Comparative in vitro and in vivo activities of piperacillin combined with the beta-lactamase inhibitors tazobactam, clavulanic acid, and sulbactam. Kuck, N.A., Jacobus, N.V., Petersen, P.J., Weiss, W.J., Testa, R.T. Antimicrob. Agents Chemother. (1989) [Pubmed]
  31. Penicillin-binding proteins 2b and 2x of Streptococcus pneumoniae are primary resistance determinants for different classes of beta-lactam antibiotics. Grebe, T., Hakenbeck, R. Antimicrob. Agents Chemother. (1996) [Pubmed]
  32. Single-dose pharmacokinetics of piperacillin and tazobactam in patients with renal disease. Johnson, C.A., Halstenson, C.E., Kelloway, J.S., Shapiro, B.E., Zimmerman, S.W., Tonelli, A., Faulkner, R., Dutta, A., Haynes, J., Greene, D.S. Clin. Pharmacol. Ther. (1992) [Pubmed]
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