Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human UDP-glucuronosyltransferases

Drug Metabolism and Disposition

Volumn 34, Issue 3, 2006, Pages 449-456

  Uchaipichat, Verawan ^a   Mackenzie, Peter I ^a   Elliot, David J ^a   Miners, John O ^a,b  

^a FLINDERS UNIVERSITY   (Australia)

^b FLINDERS MEDICAL CENTRE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AMITRIPTYLINE; ANDROSTERONE; CANRENOIC ACID; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A10; GLUCURONOSYLTRANSFERASE 1A3; GLUCURONOSYLTRANSFERASE 1A4; GLUCURONOSYLTRANSFERASE 1A6; GLUCURONOSYLTRANSFERASE 1A7; GLUCURONOSYLTRANSFERASE 1A8; GLUCURONOSYLTRANSFERASE 1A9; GLUCURONOSYLTRANSFERASE 2B15; GLUCURONOSYLTRANSFERASE 2B7; GLYCOPROTEIN P; HECOGENIN; PHENYLBUTAZONE; QUINIDINE; QUININE; RECOMBINANT PROTEIN; SULFINPYRAZONE; TRIFLUOPERAZINE; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN HEK293; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; DRUG SELECTIVITY; EMBRYO; ENZYME INHIBITION; GLUCURONIDATION; HUMAN; HUMAN CELL; IC 50; INHIBITION KINETICS; LIVER MICROSOME; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN EXPRESSION; STATISTICAL SIGNIFICANCE;

CELL LINE; ENZYME INHIBITORS; GLUCURONOSYLTRANSFERASE; HUMANS; KINETICS; MICROSOMES, LIVER; SUBSTRATE SPECIFICITY; TRIFLUOPERAZINE;

CINCHONA PUBESCENS;

EID: 33344473930     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.105.007369     Document Type: Article

References (38)

1. Aarbakke J (1978) Clinical pharmacokinetics of phenylbutazone. Clin Pharmacokinet 3:369-380.
2. Austin RP, Barton P, Cockroft SL, Wenlock MC, and Riley RJ (2002) The influence of nonspecific microsomal binding on apparent intrinsic clearance and its prediction from physicochemical properties. Drug Metab Dispos 30:1497-1503.
3. Boase S and Miners JO (2002) In vitro-in vivo correlations for drugs eliminated by glucuronidation: investigations with the model substrate zidovudine. Br J Clin Pharmacol 54:493-503.
4. Bowalgaha K, Elliot DJ, Mackenzie PI, Knights KM, Swedmark S, and Miners JO (2005) S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol 60:423-433.
5. Clarke SE (1998) In vitro assessment of human cytochrome P450. Xenobiotica 28:1167-1202.
6. Coffman BL, King CD, Rios GR, and Tephly TR (1998) The glucuronidation of opioids, other xenobiotics and androgens by human UGT2B7Y(268) and UGT2B7H(268). Drug Metab Dispos 26:73-77.
7. Court MH, Krishnaswamy S, Hao Q, Duan SX, Patten CJ, Von Moltke LL, and Greenblatt DJ (2003) Evaluation of 3′-azido-3′-deoxythymidine, morphine and codeine as probe substrates for UDP-glucuronosyltransferase 2B7 (UGT2B7) in human liver microsomes: specificity and influence of the UGT2B7*2 polymorphism. Drug Metab Dispos 31:1125-1133.
8. Dieterle W, Faigle JW, Mory H, Richter WJ, and Theobald W (1975) Biotransformation and pharmacokinetics of sulfinpyrazone (Anturan) in man. Eur J Clin Pharmacol 9:135-145.
9. Di Marco A, D'Antoni M, Attaccalite S, Carotenuto P, and Laufer R (2005) Determination of drug glucuronidation and UDP-glucuronosyltransferase selectivity using a 96-well radiometric assay. Drug Metab Dispos 33:812-819.
10. Egfjord M, Dahl HB, Kayser C, and Blaehr H (1999) Aldosterone metabolism in cultures of rat renal cortical and medullary cells. Scand J Clin Lab Investig 59:107-113.
11. Gall WE, Zawada G, Mojarrabi B, Tephly TR, Green MD, Coffman BL, Mackenzie PI, and Radominska-Pandya A (1999) Differential glucuronidation of bile acids, androgens and estrogens by human UGT1A3 and 2B7. J Steroid Biochem Mol Biol 70:101-108.
12. Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, and Zbaida S (2004) Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of posaconazole (Noxafil). Drug Metab Dispos 32:267-271.
13. Green MD and Tephly TR (1996) Glucuronidation of amines and hydroxylated xenobiotics and endobiotics catalyzed by expressed human UGT1.4 protein. Drug Metab Dispos 24:356-363.
14. Houston JB and Kenworthy KE (2000) In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metab Dispos 28:246-254.
15. Jin CJ, Mackenzie PI, and Miners JO (1997) The regio- and stereo-selectivity of C19 and C21 hydroxysteroid glucuronidation by UGT2B7 and UGT2B11. Arch Biochem Biophys 341:207-211.
16. Kharasch ED, Hoffer C, Whittington D, and Sheffels P (2003) Role of P-glycoprotein in the intestinal absorption and clinical effects of morphine. Clin Pharmacol Ther 74:543-554.
17. Kirkwood LC, Nation RL, and Somogyi AA (1998) Glucuronidation of dihydrocodeine by human liver microsomes and the effect of inhibitors. Clin Exp Pharmacol Physiol 25:266-270.
18. Lowry OH, Rosebrough NJ, Farr AL, and Randall RL (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275.
19. Mackenzie PI, Owens IS, Burchell B, Bock KW, Bairoch A, Belanger A, Fournel-Gigleux S, Green M, Hum DW, Iyanagi T, et al. (1997) The UDP glycosyltransferase gene superfamily: recommended nomenclature update based on evolutionary divergence. Pharmacogenetics 7:255-269.
20. McLure JA, Miners JO, and Birkett DJ (2000) Nonspecific binding of drugs to human liver microsomes. Br J Clin Pharmacol 49:453-461.
21. Miners JO, Lillywhite KJ, Matthews AP, Jones ME, and Birkett DJ (1988) Kinetic and inhibitor studies of 4-methylumbelliferone and 1-naphthol glucuronidation in human liver microsomes. Biochem Pharmacol 37:665-671.
22. Miners JO and Mackenzie PI (1991) Drug glucuronidation in humans. Pharmacol Ther 51:347-369.
23. Miners JO, Smith PA, Sorich MJ, McKinnon RA, and Mackenzie PI (2004) Predicting human drug glucuronidation parameters: application of in vitro and in silico modeling approaches. Annu Rev Pharmacol Toxicol 44:1-25.
24. Miners JO, Veronese ME, and Birkett DJ (1994) In vitro approaches for the prediction of human drug metabolism. Annu Rep Med Chem 29:307-316.
25. Mirghani RA, Hellgren U, Bertilsson L, Gustafsson LL, and Ericsson O (2003) Metabolism and elimination of quinine in healthy volunteers. Eur J Clin Pharmacol 59:423-427.
26. Obach RS (1999) Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: an examination of in vitro half-life approach and nonspecific binding to microsomes. Drug Metab Dispos 27:1350-1359.
27. Radominska-Pandya A, Czernik PJ, Little JM, Battaglia E, and Mackenzie PI (1999) Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev 31:817-899.
28. Rajaonarison JF, Lacarelle B, Catalin J, Placidi M, and Rahmani R (1992) 3′-Azido-3′-deoxythymidine drug interactions. Screening for inhibitors in human liver microsomes. Drug Metab Dispos 20:578-584.
29. Resetar A, Minick D, and Spector T (1991) Glucuronidation of 3′-azido-3′-deoxythymidine catalyzed by human liver UDP-glucuronosyltransferase. Significance of nucleoside hydrophobicity and inhibition by xenobiotics. Biochem Pharmacol 42:559-568.
30. Sorich MJ, Smith PA, McKinnon RA, and Miners JO (2002) Pharmacophore and quantitative structure activity relationship modelling of UDP- glucuronosyltransferase 1A1 (UGT1A1) substrates. Pharmacogenetics 12:635-645.
31. Stone AN, Mackenzie PI, Galetin A, Houston JB, and Miners JO (2003) Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human udp-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7 [erratum in Drug Metab Dispos (2003) 31:1541]. Drug Metab Dispos 31:1086-1089.
32. Tukey RH and Strassburg CP (2000) Human UDP-glucuronosyltransferases: metabolism, expression and disease. Annu Rev Pharmacol Toxicol 40:581-616.
33. Uchaipichat V, Mackenzie PI, Guo XH, Gardener-Stephen D, Galetin A, Houston JB, and Miners JO (2004) Human UDP-glucuronosyltransferases: isoform selectivity and kinetics of 4-methylumbelliferone and 1-naphthol glucuronidation, effects of organic solvents and inhibition by diclofenac and probenecid. Drug Metab Dispos 32:413-423.
34. Uchaipichat V, Winner LK, Mackenzie PI, Elliot DJ, Williams JA, and Miners JO (2006) Quantitative prediction of in vivo inhibitory interactions involving glucuronidated drugs from in vitro data: the effect of fluconazole on zidovudine glucuronidation. Br J Clin Pharmacol, in press.
35. Venkatakrishnan K, Von Moltke LL, and Greenblatt DJ (2001) Human drug metabolism and the cytochromes P450: application and relevance of in vitro models. J Clin Pharmacol 41:1149-1179.
36. Ventafridda V, Ripamonti C, De Conno F, Bianchi M, Pazzuconi F, and Panerai AE (1987) Antidepressants increase bioavailability of morphine in cancer patients. Lancet 1:1204.
37. Woosley RL and Shand DG (1978) Pharmacokinetics of antiarrhythmic drugs. Am J Cardiol 41:986-995.
38. Yue Q, von Bahr C, Odar-Cederlof I, and Sawe J (1990) Glucuronidation of codeine and morphine in human liver and kidney microsomes: effect of inhibitors. Pharmacol Toxicol 66:221-226.