Significance of reductive metabolism in human intestine and quantitative prediction of intestinal first-pass metabolism by cytosolic reductive enzymes

Drug Metabolism and Disposition

Volumn 41, Issue 5, 2013, Pages 1104-1111

  Nishimuta, Haruka ^a   Nakagawa, Tetsuya ^a   Nomura, Naruaki ^a   Yabuki, Masashi ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL REDUCTASE; DRUG METABOLIZING ENZYME; HALOPERIDOL; MEBENDAZOLE; MENADIONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; ZIPRASIDONE;

ARTICLE; ARTIFICIAL MEMBRANE; CELL FRACTIONATION; CELLULAR DISTRIBUTION; CONTROLLED STUDY; CYTOSOL; DRUG CLEARANCE; DRUG STRUCTURE; FIRST PASS EFFECT; HUMAN; HUMAN CELL; INTESTINE; LIVER CYTOSOL; MEMBRANE PERMEABILITY; MICROSOME; MODEL; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; REDUCTION;

CYTOSOL; HALOPERIDOL; HUMANS; INTESTINES; LIVER; MEBENDAZOLE; NADP; OXIDATION-REDUCTION; PIPERAZINES; THIAZOLES;

EID: 84876781495     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.113.051177     Document Type: Article

References (28)

1. Atalla A, Breyer-Pfaff U, and Maser E (2000) Purification and characterization of oxidoreductasescatalyzing carbonyl reduction of the tobacco-specific nitrosamine 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human liver cytosol. Xenobiotica 30:755-769.
2. Avdeef A, Artursson P, Neuhoff S, Lazorova L, Gråsjö J, and Tavelin S (2005) Caco-2 permeability of weakly basic drugs predicted with the double-sink PAMPA pKa(flux) method. Eur J Pharm Sci 24:333-349.
3. Beedham C, Miceli JJ, and Obach RS (2003) Ziprasidone metabolism, aldehyde oxidase, and clinical implications. J Clin Psychopharmacol 23:229-232.
4. 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.
5. Dawson M, Braithwaite PA, Roberts MS, and Watson TR (1985) The pharmacokinetics and bioavailability of a tracer dose of [3H]-mebendazole in man. Br J Clin Pharmacol 19: 79-86.
6. Forrest GL and Gonzalez B (2000) Carbonyl reductase. Chem Biol Interact 129:21-40.
7. Houston JB and Galetin A (2008) Methods for predicting in vivo pharmacokinetics using data from in vitro assays. Curr Drug Metab 9:940-951.
8. Kato M (2008) Intestinal first-pass metabolism of CYP3A4 substrates. Drug Metab Pharmacokinet 23:87-94.
9. Kemp DC, Fan PW, and Stevens JC (2002) Characterization of raloxifene glucuronidation in vitro: Contribution of intestinal metabolism to presystemic clearance. Drug Metab Dispos 30: 694-700.
10. Kudo S and Ishizaki T (1999) Pharmacokinetics of haloperidol: An update. Clin Pharmacokinet 37:435-456.
11. Maser E (1995) Xenobiotic carbonyl reduction and physiological steroid oxidoreduction. The pluripotency of several hydroxysteroid dehydrogenases. Biochem Pharmacol 49: 421-440.
12. Miao Z, Kamel A, and Prakash C (2005) Characterization of a novel metabolite intermediate of ziprasidone in hepatic cytosolic fractions of rat, dog, and human by ESI-MS/MS, hydrogen/ deuterium exchange, and chemical derivatization. Drug Metab Dispos 33:879-883.
13. Nishimura M and Naito S (2006) Tissue-specific mRNA expression profiles of human phase I metabolizing enzymes except for cytochrome P450 and phase II metabolizing enzymes. Drug Metab Pharmacokinet 21:357-374.
14. Nishimuta H, Sato K, Mizuki Y, Yabuki M, and Komuro S (2010) Prediction of the intestinal first-pass metabolism of CYP3A substrates in humans using cynomolgus monkeys. Drug Metab Dispos 38:1967-1975.
15. 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.
16. Obach RS (2001) The prediction of human clearance from hepatic microsomal metabolism data. Curr Opin Drug Discov Devel 4:36-44.
17. Obach RS, Huynh P, Allen MC, and Beedham C (2004) Human liver aldehyde oxidase: Inhibition by 239 drugs. J Clin Pharmacol 44:7-19.
18. Oppermann UC and Maser E (2000) Molecular and structural aspects of xenobiotic carbonyl metabolizing enzymes. Role of reductases and dehydrogenases in xenobiotic phase I reactions. Toxicology 144:71-81.
19. Parkinson A (1996) An overview of current cytochrome P450 technology for assessing the safety and efficacy of new materials. Toxicol Pathol 24:48-57.
20. Porter SJ, Somogyi AA, and White JM (2000) Kinetics and inhibition of the formation of 6betanaltrexol from naltrexone in human liver cytosol. Br J Clin Pharmacol 50:465-471.
21. Prakash C, Kamel A, Gummerus J, and Wilner K (1997) Metabolism and excretion of a new antipsychotic drug, ziprasidone, in humans. Drug Metab Dispos 25:863-872.
22. Rosemond MJ and Walsh JS (2004) Human carbonyl reduction pathways and a strategy for their study in vitro. Drug Metab Rev 36:335-361.
23. Someya T, Shibasaki M, Noguchi T, Takahashi S, and Inaba T (1992) Haloperidol metabolism in psychiatric patients: Importance of glucuronidation and carbonyl reduction. J Clin Psychopharmacol 12:169-174.
24. Varma MV, Obach RS, Rotter C, Miller HR, Chang G, Steyn SJ, El-Kattan A, and Troutman MD (2010) Physicochemical space for optimum oral bioavailability: Contribution of human intestinal absorption and first-pass elimination. J Med Chem 53:1098-1108.
25. von Richter O, Burk O, Fromm MF, Thon KP, Eichelbaum M, and Kivistö KT (2004) Cytochrome P450 3A4 and P-glycoprotein expression in human small intestinal enterocytes and hepatocytes: A comparative analysis in paired tissue specimens. Clin Pharmacol Ther 75: 172-183.
26. Wirth H and Wermuth B (1992) Immunohistochemical localization of carbonyl reductase in human tissues. J Histochem Cytochem 40:1857-1863.
27. Wu CY, Benet LZ, Hebert MF, Gupta SK, Rowland M, Gomez DY, and Wacher VJ (1995) Differentiation of absorption and first-pass gut and hepatic metabolism in humans: Studies with cyclosporine. Clin Pharmacol Ther 58:492-497.
28. Zientek M, Jiang Y, Youdim K, and Obach RS (2010) In vitro-in vivo correlation for intrinsic clearance for drugs metabolized by human aldehyde oxidase. Drug Metab Dispos 38: 1322-1327.