Identification of valproic acid glucuronide hydrolase as a key enzyme for the interaction of valproic acid with carbapenem antibiotics

Drug Metabolism and Disposition

Volumn 38, Issue 9, 2010, Pages 1538-1544

  Suzuki, Eiko ^a   Yamamura, Naotoshi ^a   Ogura, Yuji ^a   Nakai, Daisuke ^a   Kubota, Kazuishi ^a   Kobayashi, Nobuhiro ^a   Miura, Shin Ichi ^a   Okazaki, Osamu ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLOROMERCURIBENZOIC ACID; 5,5' DITHIOBIS(2 NITROBENZOIC ACID); ACYLAMINO ACID RELEASING ENZYME; BETA GLUCURONIDASE; CARBAPENEM; CARBOXYLESTERASE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; DYFLOS; HYDROLASE; PANIPENEM; SACCHAROLACTONE; UNCLASSIFIED DRUG; VALPROIC ACID; VALPROIC ACID DERIVATIVE; VALPROIC ACID GLUCURONIDE;

ARTICLE; CHROMATOGRAPHY; CONTROLLED STUDY; DEPLETION; DRUG HYDROLYSIS; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG MECHANISM; ENZYME ACTIVITY; HUMAN; HUMAN CELL; LIVER CYTOSOL; NONHUMAN; PRIORITY JOURNAL;

ANTI-BACTERIAL AGENTS; BLOTTING, WESTERN; GLUCURONIDASE; GLUCURONIDES; HUMANS; HYDROLASES; HYDROLYSIS; LIVER; VALPROIC ACID;

EID: 77955992055     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.110.032938     Document Type: Article

References (28)

1. Akao T, Akao T, and Kobashi K (1987) Glycyrrhizin β-D-glucuronidase of Eubacterium sp. from human intestinal flora. Chem Pharm Bull 35:705-710.
2. Beem EP, Hillebrand MJ, Benckhuijsen C, and Overdijk B (1987) Origin of the increased activity of β-glucuronidase in the soluble fraction of rat mammary tumors during ovariectomy-induced regression. Cancer Res 47:3980-3987.
3. De Turck BJ, Diltoer MW, Cornelis PJ, Maes V, Spapen HD, Camu F, and Huyghens LP (1998) Lowering of plasma valproic acid concentrations during concomitant therapy with meropenem and amikacin. J Antimicrob Chemother 42:563-564.
4. Fudio S, Carcas A, Piñana E, and Ortega R (2006) Epileptic seizures caused by low valproic acid levels from an interaction with meropenem. J Clin Pharm Ther 31:393-396. (Pubitemid 44060205)
5. Giardina T, Biagini A, Massey-Harroche D, and Puigserver A (1999) Distribution and subcellular localization of acylpeptide hydrolase and acylase I along the hog gastro-intestinal tract. Biochimie 81:1049-1055.
6. Granai F, Smart HL, and Triger DR (1992) A study of the penetration of meropenem into bile using endoscopic retrograde cholangiography. J Antimicrob Chemother 29:711-718.
7. Gu J and Huang Y (2009) Effect of concomitant administration of meropenem and valproic acid in an elderly Chinese patient. Am J Geriatr Pharmacother 7:26-33.
8. Kojima S, Nadai M, Kitaichi K, Wang L, Nabeshima T, and Hasegawa T (1998) Possible mechanism by which the carbapenem antibiotic panipenem decreases the concentration of valproic acid in plasma in rats. Antimicrob Agents Chemother 42:3136-3140.
9. Lunde JL, Nelson RE, and Storandt HF (2007) Acute seizures in a patient receiving divalproex sodium after starting ertapenem therapy. Pharmacotherapy 27:1202-1205.
10. Mori H, Takahashi K, and Mizutani T (2007) Interaction between valproic acid and carbapenem antibiotics. Drug Metab Rev 39:647-657. (Pubitemid 350208726)
11. Morimoto K, Kinoshita H, Nakatani S, Sakai K, Fujimoto M, Ohno K, Ueda T, Hirata S, Muramatsu H, Mizugami K, et al. (1991) Panipenem/betamipron in the treatment of patients with surgical infections. Jpn J Chemother 39 (Suppl 3):572-584.
12. Nagai K, Shimizu T, Togo A, Takeya M, Yokomizo Y, Sakata Y, Matsuishi T, and Kato H (1997) Decrease in serum levels of valproic acid during treatment with a new carbapenem, panipenem/betamipron. J Antimicrob Chemother 39:295-296.
13. Nakajima Y, Mizobuchi M, Nakamura M, Takagi H, Inagaki H, Kominami G, Koike M, and Yamaguchi T (2004) Mechanism of the drug interaction between valproic acid and carbapenem antibiotics in monkeys and rats. Drug Metab Dispos 32:1383-1391.
14. Nakamura Y, Nakahira K, and Mizutani T (2008) Decreased valproate level caused by VPA-glucuronidase inhibition by carbapenem antibiotics. Drug Metab Lett 2:280-285.
15. Omoda K, Murakami T, Yumoto R, Nagai J, Maeda Y, Kiribayashi Y, and Takano M (2005) Increased erythrocyte distribution of valproic acid in pharmacokinetic interaction with carbapenem antibiotics in rat and human. J Pharm Sci 94:1685-1693.
16. Perrier J, Durand A, Giardina T, and Puigserver A (2005) Catabolism of intracellular N-terminal acetylated proteins: involvement of acylpeptide hydrolase and acylase. Biochimie 87:673-685. (Pubitemid 41058899)
17. Raphel V, Giardina T, Guevel L, Perrier J, Dupuis L, Guo XJ, and Puigserver A (1999) Cloning, sequencing and further characterization of acylpeptide hydrolase from porcine intestinal mucosa. Biochim Biophys Acta 1432:371-381.
18. Rimmer EM and Richens A (1985) An update on sodium valproate. Pharmacotherapy 5:171-184.
19. Scaloni A, Barra D, Jones WM, and Manning JM (1994) Human acylpeptide hydrolase. Studies on its thiol groups and mechanism of action. J Biol Chem 269:15076-15084.
20. Shiramatsu K, Hirata K, Yamada T, Kimura H, Someya T, Usuki T, Karasawa G, and Hayasaka H (1988) Ceftazidime concentration in gallbladder tissue and excretion in bile. Antimicrob Agents Chemother 32:1588-1589.
21. Soars MG, Riley RJ, Findlay KA, Coffey MJ, and Burchell B (2001) Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney. Drug Metab Dispos 29:121-126.
22. Thomas MH, Dash CH, Burnand KG, and Woodyer AB (1981) The excretion of cefuroxime in human bile. Br J Surg 68:290-291.
23. Torii M, Takiguchi Y, Saito F, Izumi M, and Yokota M (2001) Inhibition by carbapenem antibiotic imipenem of intestinal absorption of valproic acid in rats. J Pharm Pharmacol 53:823-829. (Pubitemid 32529725)
24. Yamagata T, Momoi MY, Murai K, Ikematsu K, Suwa K, Sakamoto K, and Fujimura A (1998) Panipenem-betamipron and decreases in serum valproic acid concentration. Ther Drug Monit 20:396-400.
25. Yamamura N, Imura K, Naganuma H, and Nishimura K (1999) Panipenem, a carbapenem antibiotic, enhances the glucuronidation of intravenously administered valproic acid in rats. Drug Metab Dispos 27:724-730.
26. Yamamura N, Imura-Miyoshi K, and Naganuma H (2000) Panipenum, a carbapenem antibiotic, increases the level of hepatic UDP-glucuronic acid in rats. Drug Metab Dispos 28:1484-1486.
27. Yamamura N, Müeller J, Hoepner U, Roos-Poppe U, Miyoshi K, Naganuma H, and Ikeda T (2001) Metabolism-based drug interaction between valproic acid and carbapenem antibiotics. 6th International ISSX Meeting; 2001 Oct 7-11; Munich, Germany. Abstract 333. International Society for the Study of Xenobiotics, Washington, DC.
28. Yokogawa K, Iwashita S, Kubota A, Sasaki Y, Ishizaki J, Kawahara M, Matsushita R, Kimura K, Ichimura F, and Miyamoto K (2001) Effect of meropenem on disposition kinetics of valproate and its metabolites in rabbits. Pharm Res 18:1320-1326.