Use of enzyme inhibitors to evaluate the conversion pathways of ester and amide prodrugs: A case study example with the prodrug ceftobiprole medocaril

Journal of Pharmaceutical Sciences

Volumn 101, Issue 3, 2012, Pages 1242-1252

  Eichenbaum, Gary ^a   Skibbe, Jennifer ^b   Parkinson, Andrew ^b,d   Johnson, Mark D ^a   Baumgardner, Dawn ^a   Ogilvie, Brian ^b   Usuki, Etsuko ^b   Tonelli, Fred ^a   Holsapple, Jeff ^b   Schmitt Hoffmann, Anne ^c  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

^b XenoTech LLC   (United States)

^c BASILEA PHARMACEUTICA INTERNATIONAL LTD   (Switzerland)

^d XPD Consulting   (United States)

Author keywords

Ceftobiprole; Conversion; Drug metabolizing enzymes; Enzymology; Esterase; Hydrolysis; In vitro models; Inhibition; Paraoxonase; Prodrug

Indexed keywords

ACETYLCHOLINESTERASE; AMIDASE; AMIDE; ARYLDIALKYLPHOSPHATASE; CARBOXYLESTERASE; CEFTOBIPROLE; CEFTOBIPROLE MEDOCARIL; CHOLINESTERASE; EDETIC ACID; ENZYME INHIBITOR; ESTER; SERINE PROTEINASE; SOLVENT;

ADOLESCENT; ARTICLE; DRUG HYDROLYSIS; ENVIRONMENTAL FACTOR; ENZYME ACTIVITY; ERYTHROCYTE; FEMALE; GENETIC POLYMORPHISM; HUMAN; HUMAN CELL; HYDROLYSIS; INTESTINE; KIDNEY; LIVER INJURY; MALE; NEWBORN; PLASMA; SUPERNATANT;

EID: 84855877824     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22816     Document Type: Article

References (25)

1. Costa LG, Vitalone A, Cole TB, Furlong CE. 2005. Modulation of paraoxonase (PON1) activity. Biochem Pharmacol 69:541-550.
2. Draganov DI, La Du BN. 2004. Pharmacogenetics of paraoxonases: A brief review. Naunyn Schmiedebergs Arch Pharmacol 369:78-88.
3. Marsillach J, Ferre N, Vila MC, Lligona A, Mackness B, Mackness M, Deulofeu R, Solá R, Parés A, Pedro-Botet J, Joven J, Caballeria J, Camps J. 2007. Serum paraoxonase-1 in chronic alcoholics: relationship with liver disease. Clin Biochem 40:645-650.
4. Liederer BM, Borchardt RT. 2006. Enzymes involved in the bioconversion of ester-based prodrugs. J Pharm Sci 95:1177-1195.
5. Sultatos LG, Minor LD. 1985. Biotransformation of paraoxon and p-nitrophenol by isolated perfused mouse livers. Toxicology 36:159-169.
6. McCracken NW, Blain PG, Williams FM. 1993. Human xenobiotic metabolizing esterases in liver and blood. Biochem Pharmacol 46:1125-1129.
7. Morgan EW, Yan B, Greenway D, Petersen DR, Parkinson A. 1994. Purification and characterization of two rat liver microsomal carboxylesterases (hydrolase A and B). Arch Biochem Biophys 315:495-512.
8. Sorenson RC, Primo-Parmo SL, Kuo CL, Adkins S, Lockridge O, La Du BN. 1995. Reconsideration of the catalytic center and mechanism of mammalian paraoxonase/arylesterase. Proc Natl Acad Sci U S A 92:7187-7191.
9. Tougou K, Nakamura A, Watanabe S, Okuyama Y, Morino A. 1998. Paraoxonase has a major role in the hydrolysis of prulifloxacin (NM441), a prodrug of a new antibacterial agent. Drug Metab Dispos 26:355-359.
10. Yoshigae Y, Imai T, Taketani M, Otagiri M. 1999. Characterization of esterases involved in the stereoselective hydrolysis of ester-type prodrugs of propranolol in rat liver and plasma. Chirality 11:10-13.
11. Li B, Sedlacek M, Manoharan I, Boopathy R, Duysen EG, Masson P, Lockridge O. 2005. Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol 70:1673-1684.
12. Charlton-Menys V, Liu Y, Durrington PN. 2006. Semiautomated method for determination of serum paraoxonase activity using paraoxon as substrate. Clin Chem 52:453-457.
13. Brandt E, Heymann E, Mentlein R. 1980. Selective inhibition of rat liver carboxylesterases by various organophosphorus diesters in vivo and in vitro. Biochem Pharmacol 29:1927-1931.
14. Mutch E, Nave R, McCracken N, Zech K, Williams FM. 2007. The role of esterases in the metabolism of ciclesonide to desisobutyryl-ciclesonide in human tissue. Biochem Pharmacol 73:1657-1664.
15. Davies TA, Page MGP, Shang W, Andrew T, Kania M, Bush K. 2007. Binding of ceftobiprole and comparators to the penicillin-binding proteins of Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Streptococcus pneumoniae. Antimicrob Agents Chemother 51:2621-2624.
16. Arias CA, Singh KV, Panesso D, Murray BE. 2007. Time-kill and synergism studies of ceftobiprole against Enterococcus faecalis, including beta-lactamase-producing and vancomycin-resistant isolates. Antimicrob Agents Chemother 51:2043-2047.
17. Jones RN, Deshpande LM, Mutnick AH, Biedenbach DJ. 2002. In vitro evaluation of BAL9141, a novel parenteral cephalosporin active against oxacillin-resistant staphylococci. J Antimicrob Chemother 50:915-932.
18. Issa NC, Rouse MS, Piper KE, Wilson WR, Steckelberg JM, Patel R. 2004. In vitro activity of BAL9141 against clinical isolates of Gram-negative bacteria. Diagn Microbiol Infect Dis 48:73-75.
19. Schmitt-Hoffmann A, Nyman L, Roos B, Schleimer M, Sauer J, Nashed N, Brown T, Man A, Weidekamm E. 2004. Multiple-dose pharmacokinetics and safety of a novel broad-spectrum cephalosporin (BAL5788) in healthy volunteers. Antimicrob Agents Chemother 48:2576-2580.
20. Schmitt-Hoffmann A, Roos B, Schleimer M, Sauer J, Man A, Nashed N, Brown T, Perez A, Weidekamm E, Kovács P. 2004. Single-dose pharmacokinetics and safety of a novel broad-spectrum cephalosporin (BAL5788) in healthy volunteers. Antimicrob Agents Chemother 48:2570-2575.
21. Murthy B, Schmitt-Hoffmann A. 2008. Pharmacokinetics and pharmacodynamics of ceftobiprole, an anti-MRSA cephalosporin with broad-spectrum activity. Clin Pharmacokinet 47:21-33.
22. Schindler R. 2001. Inhibition of purified pig and human liver retinyl ester hydrolase by pharmacologic agents. Lipids 36:543-548.
23. Parkinson A, Ogilvie B. 2008. Biotransformation of xenobiotics. In Casarett and Doull's toxicology: The basic science of poisons; Klassen C, Ed. New York: McGraw Hill, pp 161-304.
24. Pla A, Rodrigo L, Hernandez AF, Gil F, Lopez O. 2007. Effect of metal ions and calcium on purified PON1 and PON3 from rat liver. Chem Biol Interact 167:63-70.
25. Ginsberg G, Slikker W, Jr., Bruckner J, Sonawane B. 2004. Incorporating children's toxicokinetics into a risk framework. Environ Health Perspect 112:272-283.