Hepatic, intestinal, renal, and plasma hydrolysis of prodrugs in human, cynomolgus monkey, dog, and rat: Implications for in vitro-in vivo extrapolation of clearance of prodrugs

Drug Metabolism and Disposition

Volumn 42, Issue 9, 2014, Pages 1522-1531

  Nishimuta, Haruka ^a,b   Houston, J Brian ^a   Galetin, Aleksandra ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLDIALKYLPHOSPHATASE; CARBOXYLESTERASE; CARBOXYMETHYLENEBUTENOLIDASE; CYTOCHROME P450; PRODRUG;

ANIMAL; DOG; HUMAN; HYDROLYSIS; INTESTINE; KIDNEY; LIVER; LIVER CELL; LIVER MICROSOME; MACACA FASCICULARIS; MALE; METABOLIC CLEARANCE RATE; METABOLISM; PHYSIOLOGY; PLASMA; RAT; SPRAGUE DAWLEY RAT;

ANIMALS; ARYLDIALKYLPHOSPHATASE; CARBOXYLIC ESTER HYDROLASES; CYTOCHROME P-450 ENZYME SYSTEM; DOGS; HEPATOCYTES; HUMANS; HYDROLYSIS; INTESTINES; KIDNEY; LIVER; MACACA FASCICULARIS; MALE; METABOLIC CLEARANCE RATE; MICROSOMES, LIVER; PLASMA; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 84906874604     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.114.057372     Document Type: Article

References (44)

1. Bahar FG, Ohura K, Ogihara T, and Imai T (2012) Species difference of esterase expression and hydrolase activity in plasma. J Pharm Sci 101:3979-3988.
2. Berry LM, Wollenberg L, and Zhao Z (2009) Esterase activities in the blood, liver and intestine of several preclinical species and humans. Drug Metab Lett 3:70-77.
3. Cubitt HE, Houston JB, and Galetin A (2009) Relative importance of intestinal and hepatic glucuronidation-impact on the prediction of drug clearance. Pharm Res 26:1073-1083.
4. Cubitt HE, Houston JB, and Galetin A (2011) Prediction of human drug clearance by multiple metabolic pathways: integration of hepatic and intestinal microsomal and cytosolic data. Drug Metab Dispos 39:864-873.
5. Dahan A, Khamis M, Agbaria R, and Karaman R (2012) Targeted prodrugs in oral drug delivery: the modern molecular biopharmaceutical approach. Expert Opin Drug Deliv 9:1001-1013.
6. Detroja C, Chavhan S, and Sawant K (2011) Enhanced antihypertensive activity of candesartan cilexetil nanosuspension: formulation, characterization and pharmacodynamic study. Sci Pharm 79:635-651.
7. Fujiyama N, Miura M, Kato S, Sone T, Isobe M, and Satoh S (2010) Involvement of carboxylesterase 1 and 2 in the hydrolysis of mycophenolate mofetil. Drug Metab Dispos 38:2210-2217.
8. Fukami T and Yokoi T (2012) The emerging role of human esterases. Drug Metab Pharmacokinet 27:466-477.
9. Galetin A and Houston JB (2006) Intestinal and hepatic metabolic activity of five cytochrome P450 enzymes: impact on prediction of first-pass metabolism. J Pharmacol Exp Ther 318:1220-1229. (Pubitemid 44268329)
10. Gertz M, Harrison A, Houston JB, and Galetin A (2010) Prediction of human intestinal first-pass metabolism of 25 CYP3A substrates from in vitro clearance and permeability data. Drug Metab Dispos 38:1147-1158.
11. Gill KL, Houston JB, and Galetin A (2012) Characterization of in vitro glucuronidation clearance of a range of drugs in human kidney microsomes: comparison with liver and intestinal glucuronidation and impact of albumin. Drug Metab Dispos 40:825-835.
12. Gupta D, Varghese Gupta S, Dahan A, Tsume Y, Hilfinger J, Lee KD, and Amidon GL (2013) Increasing oral absorption of polar neuraminidase inhibitors: a prodrug transporter approach applied to oseltamivir analogue. Mol Pharm 10:512-522.
13. Hallifax D, Foster JA, and Houston JB (2010) Prediction of human metabolic clearance from in vitro systems: retrospective analysis and prospective view. Pharm Res 27:2150-2161.
14. Hallifax D and Houston JB (2006) Binding of drugs to hepatic microsomes: comment and assessment of current prediction methodology with recommendation for improvement. Drug Metab Dispos 34:724-726, author reply 727.
15. Hosea NA, Collard WT, Cole S, Maurer TS, Fang RX, Jones H, Kakar SM, Nakai Y, Smith BJ, and Webster R, et al. (2009) Prediction of human pharmacokinetics from preclinical information: comparative accuracy of quantitative prediction approaches. J Clin Pharmacol 49:513-533.
16. Hosokawa M (2008) Structure and catalytic properties of carboxylesterase isozymes involved in metabolic activation of prodrugs. Molecules 13:412-431.
17. Houston JB and Galetin A (2008) Methods for predicting in vivo pharmacokinetics using data from in vitro assays. Curr Drug Metab 9:940-951.
18. Huttunen KM, Raunio H, and Rautio J (2011) Prodrugs - from serendipity to rational design. Pharmacol Rev 63:750-771.
19. Imai T (2006) Human carboxylesterase isozymes: catalytic properties and rational drug design. Drug Metab Pharmacokinet 21:173-185.
20. Imai T and Ohura K (2010) The role of intestinal carboxylesterase in the oral absorption of prodrugs. Curr Drug Metab 11:793-805.
21. Ishizuka T, Fujimori I, Kato M, Noji-Sakikawa C, Saito M, Yoshigae Y, Kubota K, Kurihara A, Izumi T, and Ikeda T, et al. (2010) Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine. J Biol Chem 285:11892-11902.
22. Ishizuka T, Fujimori I, Nishida A, Sakurai H, Yoshigae Y, Nakahara K, Kurihara A, Ikeda T, and Izumi T (2012) Paraoxonase 1 as a major bioactivating hydrolase for olmesartan medoxomil in human blood circulation: molecular identification and contribution to plasma metabolism. Drug Metab Dispos 40:374-380.
23. Ishizuka T, Yoshigae Y, Murayama N, and Izumi T (2013) Different hydrolases involved in bioactivation of prodrug-type angiotensin receptor blockers: carboxymethylenebutenolidase and carboxylesterase 1. Drug Metab Dispos 41:1888-1895.
24. Kilford PJ, Gertz M, Houston JB, and Galetin A (2008) Hepatocellular binding of drugs: correction for unbound fraction in hepatocyte incubations using microsomal binding or drug lipophilicity data. Drug Metab Dispos 36:1194-1197. (Pubitemid 351929330)
25. Kilford PJ, Stringer R, Sohal B, Houston JB, and Galetin A (2009) Prediction of drug clearance by glucuronidation from in vitro data: use of combined cytochrome P450 and UDP-glucuronosyltransferase cofactors in alamethicin-activated human liver microsomes. Drug Metab Dispos 37:82-89.
26. Kleingeist B, Böcker R, Geisslinger G, and Brugger R (1998) Isolation and pharmacological characterization of microsomal human liver flumazenil carboxylesterase. J Pharm Pharm Sci 1:38-46.
27. Laizure SC, Herring V, Hu Z, Witbrodt K, and Parker RB (2013) The role of human carboxylesterases in drug metabolism: have we overlooked their importance? Pharmacotherapy 33:210-222.
28. Lennernäs H (2014) Human in vivo regional intestinal permeability: importance for pharmaceutical drug development. Mol Pharm 11:12-23.
29. Li B, Sedlacek M, Manoharan I, Boopathy R, Duysen EG, Masson P, and Lockridge O (2005) Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol 70:1673-1684. (Pubitemid 41540360)
30. Li F, Maag H, and Alfredson T (2008) Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting. J Pharm Sci 97:1109-1134.
31. Morgan ET, Goralski KB, Piquette-Miller M, Renton KW, Robertson GR, Chaluvadi MR, Charles KA, Clarke SJ, Kacevska M, and Liddle C, et al. (2008) Regulation of drugmetabolizing enzymes and transporters in infection, inflammation, and cancer. Drug Metab Dispos 36:205-216. (Pubitemid 351185732)
32. Nishimuta H, Sato K, Yabuki M, and Komuro S (2011) Prediction of the intestinal first-pass metabolism of CYP3A and UGT substrates in humans from in vitro data. Drug Metab Pharmacokinet 26:592-601.
33. Paine MF, Hart HL, Ludington SS, Haining RL, Rettie AE, and Zeldin DC (2006) The human intestinal cytochrome P450 "pie". Drug Metab Dispos 34:880-886.
34. Pang KS and Rowland M (1977) Hepatic clearance of drugs. I. Theoretical considerations of a "well-stirred" model and a "parallel tube" model. Influence of hepatic blood flow, plasma and blood cell binding, and the hepatocellular enzymatic activity on hepatic drug clearance. J Pharmacokinet Biopharm 5:625-653. (Pubitemid 8253670)
35. Prueksaritanont T, Gorham LM, Hochman JH, Tran LO, and Vyas KP (1996) Comparative studies of drug-metabolizing enzymes in dog, monkey, and human small intestines, and in Caco-2 cells. Drug Metab Dispos 24:634-642. (Pubitemid 26170714)
36. Quinney SK, Sanghani SP, Davis WI, Hurley TD, Sun Z, Murry DJ, and Bosron WF (2005) Hydrolysis of capecitabine to 5′-deoxy-5-fluorocytidine by human carboxylesterases and inhibition by loperamide. J Pharmacol Exp Ther 313:1011-1016. (Pubitemid 40727004)
37. Sato Y, Miyashita A, Iwatsubo T, and Usui T (2012) Simultaneous absolute protein quantification of carboxylesterases 1 and 2 in human liver tissue fractions using liquid chromatographytandem mass spectrometry. Drug Metab Dispos 40:1389-1396.
38. Satoh T and Hosokawa M (1998) The mammalian carboxylesterases: from molecules to functions. Annu Rev Pharmacol Toxicol 38:257-288. (Pubitemid 28231496)
39. Satoh T, Taylor P, Bosron WF, Sanghani SP, Hosokawa M, and La Du BN (2002) Current progress on esterases: from molecular structure to function. Drug Metab Dispos 30:488-493. (Pubitemid 34456967)
40. Stella VJ (2010) Prodrugs: Some thoughts and current issues. J Pharm Sci 99:4755-4765.
41. Taketani M, Shii M, Ohura K, Ninomiya S, and Imai T (2007) Carboxylesterase in the liver and small intestine of experimental animals and human. Life Sci 81:924-932. (Pubitemid 47374212)
42. Williams ET, Bacon JA, Bender DM, Lowinger JJ, Guo WK, Ehsani ME, Wang X, Wang H, Qian YW, and Ruterbories KJ, et al. (2011) Characterization of the expression and activity of carboxylesterases 1 and 2 from the beagle dog, cynomolgus monkey, and human. Drug Metab Dispos 39:2305-2313.
43. Williams ET, Wang H, Wrighton SA, Qian YW, and Perkins EJ (2010) Genomic analysis of the carboxylesterases: identification and classification of novel forms. Mol Phylogenet Evol 57:23-34.
44. Yoshigae Y, Imai T, Horita A, Matsukane H, and Otagiri M (1998) Species differences in stereoselective hydrolase activity in intestinal mucosa. Pharm Res 15:626-631. (Pubitemid 28214958)