In vitro drug metabolism by human carboxylesterase 1: Focus on angiotensin-converting enzyme inhibitors

Drug Metabolism and Disposition

Volumn 42, Issue 1, 2014, Pages 126-133

  Thomsen, Ragnar ^a   Rasmussen, Henrik B ^b   Linnet, Kristian ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b Mental Health Services CPH   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROPHENYL ACETATE; ACETIC ACID DERIVATIVE; CARBOXYLESTERASE; CARBOXYLESTERASE 1; CARBOXYLESTERASE 2; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ENALAPRIL; ISRADIPINE; RAMIPRIL; RECOMBINANT CARBOXYLESTERASE 1; RECOMBINANT CARBOXYLESTERASE 2; RECOMBINANT ENZYME; TACROLIMUS; TRANDOLAPRIL; UNCLASSIFIED DRUG;

ARTICLE; CONGESTIVE HEART FAILURE; CONTROLLED STUDY; DIABETES MELLITUS; DRUG ACTIVATION; DRUG CLEARANCE; DRUG HYDROLYSIS; DRUG METABOLISM; DRUG SAFETY; DRUG SCREENING; ENZYME SPECIFICITY; ENZYME SUBSTRATE COMPLEX; HUMAN; HYPERTENSION; IN VITRO STUDY; INHIBITION KINETICS; MICHAELIS MENTEN KINETICS; PRIORITY JOURNAL;

ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CARBOXYLESTERASE; CARBOXYLIC ESTER HYDROLASES; DILTIAZEM; DRUG INTERACTIONS; ENALAPRIL; ESTERS; HUMANS; HYDROLYSIS; INDOLES; KINETICS; LIVER; METABOLIC DETOXICATION, DRUG; MICROSOMES, LIVER; NITROPHENOLS; PRODRUGS; RAMIPRIL; RECOMBINANT PROTEINS; VERAPAMIL;

EID: 84890679243     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.113.053512     Document Type: Article

References (38)

1. Bouman HJ, Schömig E, van Werkum JW, Velder J, Hackeng CM, Hirschhäuser C, Waldmann C, Schmalz H-G, ten Berg JM, and Taubert D (2011) Paraoxonase-1 is a major determinant of clopidogrel efficacy. Nat Med 17:110-116.
2. Brzezinski MR, Abraham TL, Stone CL, Dean RA, and Bosron WF (1994) Purification and characterization of a human liver cocaine carboxylesterase that catalyzes the production of benzoylecgonine and the formation of cocaethylene from alcohol and cocaine. Biochem Pharmacol 48:1747-1755. (Pubitemid 24339001)
3. Brzezinski MR, Spink BJ, Dean RA, Berkman CE, Cashman JR, and Bosron WF (1997) Human liver carboxylesterase hCE-1: binding specificity for cocaine, heroin, and their metabolites and analogs. Drug Metab Dispos 25:1089-1096. (Pubitemid 27396498)
4. Böcker RH, Preuss E, and Peter R (1990) High-performance liquid chromatography of the metabolites of nitrendipine and investigation into the metabolic pathways of this dihydropyridine. J Chromatogr A 530:206-211. (Pubitemid 20256510)
5. Cornish-Bowden A (2012) Fundamentals of Enzyme Kinetics, 4th ed. Wiley-Blackwell, Weinheim, Germany.
6. Cross NB, Webster AC, Masson P, O'Connell PJ, and Craig JC (2009) Antihypertensive treatment for kidney transplant recipients. Cochrane Database Syst Rev (3):CD003598.
7. Dean RA, Christian CD, Sample RH, and Bosron WF (1991) Human liver cocaine esterases: ethanol-mediated formation of ethylcocaine. FASEB J 5:2735-2739. (Pubitemid 21905827)
8. Fujiyama N, Miura M, Kato S, Sone T, Isobe M, and Satoh S (2010) Involvement of carbox-ylesterase 1 and 2 in the hydrolysis of mycophenolate mofetil. Drug Metab Dispos 38: 2210-2217.
9. Fukami T, Takahashi S, Nakagawa N, Maruichi T, Nakajima M, and Yokoi T (2010) In vitro evaluation of inhibitory effects of antidiabetic and antihyperlipidemic drugs on human car-boxylesterase activities. Drug Metab Dispos 38:2173-2178.
10. Funaki T, Soons PA, Guengerich FP, and Breimer DD (1989) In vivo oxidative cleavage of a pyridine-carboxylic acid ester metabolite of nifedipine. Biochem Pharmacol 38:4213-4216. (Pubitemid 20009018)
11. Geshi E, Kimura T, Yoshimura M, Suzuki H, Koba S, Sakai T, Saito T, Koga A, Muramatsu M, and Katagiri T (2005) A single nucleotide polymorphism in the carboxylesterase gene is associated with the responsiveness to imidapril medication and the promoter activity. Hyper-tens Res 28:719-725. (Pubitemid 41723530)
12. Hatfield MJ, Tsurkan L, Hyatt JL, Yu X, Edwards CC, Hicks LD, Wadkins RM, and Potter PM (2010) Biochemical and molecular analysis of carboxylesterase- mediated hydrolysis of cocaine and heroin. Br J Pharmacol 160:1916-1928.
13. Hiremath S, Fergusson D, Doucette S, Mulay AV, and Knoll GA (2007) Renin angiotensin system blockade in kidney transplantation: a systematic review of the evidence. Am J Transplant 7:2350-2360. (Pubitemid 47347851)
14. Hu Z-Y, Parker RB, Herring VL, and Laizure SC (2013) Conventional liquid chromatography/triple quadrupole mass spectrometry based metabolite identification and semi-quantitative estimation approach in the investigation of in vitro dabigatran etexilate metabolism. Anal Bioanal Chem 405:1695-1704.
15. Imai T (2006) Human carboxylesterase isozymes: catalytic properties and rational drug design. Drug Metab Pharmacokinet 21:173-185.
16. Kamendulis LM, Brzezinski MR, Pindel EV, Bosron WF, and Dean RA (1996) Metabolism of cocaine and heroin is catalyzed by the same human liver carboxylesterases. J Pharmacol Exp Ther 279:713-717. (Pubitemid 27166843)
17. Katoh M, Nakajima M, Shimada N, Yamazaki H, and Yokoi T (2000) Inhibition of human cytochrome P450 enzymes by 1, 4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol 55:843-852. (Pubitemid 30201767)
18. Lewis JP, Horenstein RB, Ryan K, O'Connell JR, Gibson Q, Mitchell BD, Tanner K, Chai S, Bliden KP, and Tantry US, et al. (2013) The functional G143E variant of carboxylesterase 1 is associated with increased clopidogrel active metabolite levels and greater clopidogrel response. Pharmacogenet Genomics 23:1-8.
19. Meyer BH, Scholtz HE, Müller FO, Luus HG, de la Rey N, Seibert-Grafe M, Eckert HG, and Metzger H (1994) Lack of interaction between ramipril and simvastatin. Eur J Clin Pharmacol 47:373-375.
20. Pang KS, Cherry WF, and Ulm EH (1985) Disposition of enalapril in the perfused rat intestine-liver preparation: absorption, metabolism and first-pass effect. J Pharmacol Exp Ther 233: 788-795. (Pubitemid 15024450)
21. Sato Y, Miyashita A, Iwatsubo T, and Usui T (2012) Conclusive identification of the oxybutynin-hydrolyzing enzyme in human liver. Drug Metab Dispos 40:902-906.
22. Schwer H, Langmann T, Daig R, Becker A, Aslanidis C, and Schmitz G (1997) Molecular cloning and characterization of a novel putative carboxylesterase, present in human intestine and liver. Biochem Biophys Res Commun 233:117-120. (Pubitemid 27215920)
23. Shi D, Yang J, Yang D, LeCluyse EL, Black C, You L, Akhlaghi F, and Yan B (2006) Anti-influenza prodrug oseltamivir is activated by carboxylesterase human carboxylesterase 1, and the activation is inhibited by antiplatelet agent clopidogrel. J Pharmacol Exp Ther 319: 1477-1484.
24. Shionoiri H (1993) Pharmacokinetic drug interactions with ACE inhibitors. Clin Pharmacokinet 25:20-58. (Pubitemid 23184522)
25. Stopher DA, Beresford AP, Macrae PV, and Humphrey MJ (1988) The metabolism and phar-macokinetics of amlodipine in humans and animals. J Cardiovasc Pharmacol 12 (Suppl 7): S55-S59. (Pubitemid 19014188)
26. Sun Z, Murry DJ, Sanghani SP, Davis WI, Kedishvili NY, Zou Q, Hurley TD, and Bosron WF (2004) Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1. J Pharmacol Exp Ther 310:469-476. (Pubitemid 38988889)
27. Sutton D, Butler AM, Nadin L, and Murray M (1997) Role of CYP3A4 in human hepatic diltiazem N-demethylation: inhibition of CYP3A4 activity by oxidized diltiazem metabolites. J Pharmacol Exp Ther 282:294-300. (Pubitemid 27425554)
28. Takahashi S, Katoh M, Saitoh T, Nakajima M, and Yokoi T (2009) Different inhibitory effects in rat and human carboxylesterases. Drug Metab Dispos 37:956-961.
29. Takai S, Matsuda A, Usami Y, Adachi T, Sugiyama T, Katagiri Y, Tatematsu M, and Hirano K (1997) Hydrolytic profile for ester-or amide-linkage by carboxylesterases pI 5.3 and 4.5 from human liver. Biol Pharm Bull 20:869-873. (Pubitemid 27382753)
30. Tang M, Mukundan M, Yang J, Charpentier N, LeCluyse EL, Black C, Yang D, Shi D, and Yan B (2006) Antiplatelet agents aspirin and clopidogrel are hydrolyzed by distinct carbox-ylesterases, and clopidogrel is transesterificated in the presence of ethyl alcohol. J Pharmacol Exp Ther 319:1467-1476.
31. Tarkiainen EK, Backman JT, Neuvonen M, Neuvonen PJ, Schwab M, and Niemi M (2012) Carboxylesterase 1 polymorphism impairs oseltamivir bioactivation in humans. Clin Pharmacol Ther 92:68-71.
32. Wang YH, Jones DR, and Hall SD (2004) Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab Dispos 32:259-266. (Pubitemid 38176944)
33. Weidolf L, Borg KO, and Hoffmann KJ (1984) Urinary metabolites of felodipine, a new vasodilator drug, in man, dog, rat and mouse. Xenobiotica 14:657-666. (Pubitemid 14030242)
34. Williams ET, Carlson JE, Lai WG, Wong YN, Yoshimura T, Critchley DJ, and Narurkar M (2011) Investigation of the metabolism of rufinamide and its interaction with valproate. Drug Metab Lett 5:280-289.
35. Yanjiao X, Chengliang Z, Xiping L, Tao W, Xiuhua R, and Dong L (2013) Evaluation of the inhibitory effects of antihypertensive drugs on human carboxylesterase in vitro. Drug Metab Pharmacokinet [published ahead of print].
36. Zhang J, Burnell JC, Dumaual N, and Bosron WF (1999) Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. J Pharmacol Exp Ther 290:314-318. (Pubitemid 29302337)
37. Zhu H-J, Appel DI, Johnson JA, Chavin KD, and Markowitz JS (2009) Role of carboxylesterase 1 and impact of natural genetic variants on the hydrolysis of trandolapril. Biochem Pharmacol 77:1266-1272.
38. Zhu H-J, Patrick KS, Yuan H-J, Wang J-S, Donovan JL, DeVane CL, Malcolm R, Johnson JA, Youngblood GL, and Sweet DH, et al. (2008) Two CES1 gene mutations lead to dysfunctional carboxylesterase 1 activity in man: clinical significance and molecular basis. Am J Hum Genet 82:1241-1248.