In vitro characterisation of human renal and hepatic frusemide glucuronidation and identification of the UDP-glucuronosyltransferase enzymes involved in this pathway

Biochemical Pharmacology

Volumn 76, Issue 2, 2008, Pages 249-257

  Kerdpin, Oranun ^a,b   Knights, Kathleen M ^a   Elliot, David J ^a   Miners, John O ^a  

^a FLINDERS UNIVERSITY   (Australia)

^b NARESUAN UNIVERSITY   (Thailand)

Author keywords

Frusemide; Glucuronidation; Human kidney; Human liver; UDP glucuronosyltransferase

Indexed keywords

FLUCONAZOLE; FUROSEMIDE; GLUCURONOSYLTRANSFERASE; GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A10; GLUCURONOSYLTRANSFERASE 1A3; GLUCURONOSYLTRANSFERASE 1A6; GLUCURONOSYLTRANSFERASE 1A7; GLUCURONOSYLTRANSFERASE 1A9; GLUCURONOSYLTRANSFERASE 2B7; PHENYLBUTAZONE; SULFINPYRAZONE; ZIDOVUDINE;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; ENZYME ANALYSIS; ENZYME INHIBITION; ENZYME KINETICS; GLUCURONIDATION; HUMAN; HUMAN TISSUE; IN VITRO STUDY; KIDNEY CORTEX; KIDNEY DYSFUNCTION; KIDNEY MEDULLA; KIDNEY METABOLISM; LIVER METABOLISM; LIVER MICROSOME; MICHAELIS MENTEN KINETICS; PRIORITY JOURNAL; PROTEIN EXPRESSION;

DIURETICS; FUROSEMIDE; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; KIDNEY; LIVER; MICROSOMES; RECOMBINANT PROTEINS;

EID: 45649085605     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.04.014     Document Type: Article

References (43)

1. Brater D.C. Clinical pharmacology of loop diuretics. Drugs 41 Suppl 3 (1991) 14-22
2. Boles Ponto L.L., and Schoenwald R.D. Furosemide (frusemide)-A pharmacokinetic/pharmacodynamic review (part I). Clin Pharmacokinet 18 (1990) 381-408
3. Smith D.E., Lin E.T., and Benet L.Z. Absorption and disposition of furosemide in healthy volunteers, measured with a metabolite-specific assay. Drug Metab Dispos 8 (1980) 337-342
4. Hammarlund-Udenaes M., and Benet L.Z. Frusemide pharmacokinetics and pharmacodynamics in health and disease - An update. J Pharmacokinet Biopharmceut 17 (1989) 1-46
5. Pichette V., and du Souich P. Role of the kidneys in the metabolism of furosemide: its inhibition by probenecid. J Am Soc Nephrol 7 (1996) 345-349
6. Smith D.E., and Benet L.Z. Biotransformation of furosemide in kidney transplant patients. Eur J Clin Pharmacol 24 (1983) 787-790
7. Beermann B., Dalen E., and Lindstrom B. Elimination of furosemide in healthy subjects and in those with renal failure. Clin Pharmacol Ther 22 (1977) 70-78
8. Miners J.O., Smith P.A., Sorich M.J., McKinnon R.A., and Mackenzie P.I. Predicting human drug glucuronidation parameters: application of in vitro and in silico modeling approaches. Annu Rev Pharmacol Toxicol 44 (2004) 1-25
9. Mackenzie P.I., Bock K.W., Burchell B., Guillemette C., Ikushiro S., Iyanagi T., et al. Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15 (2005) 677-685
10. Tukey R.H., and Strassburg C.P. Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 40 (2000) 581-616
11. Gaganis P., Miners J.O., Brennan J.S., Thomas A., and Knights K.M. Human renal cortical and medullary UDP-glucuronosyltransferases (UGTs): immunohistochemical localization of UGT2B7 and UGT1A enzymes and kinetic characterization of S-naproxen glucuronidation. J Pharmacol Exp Ther 323 (2007) 422-430
12. Sutherland L., Ebner T., and Burchell B. The expression of UDP-glucuronosyltransferases of the UGT1 family in human liver and kidney and in response to drugs. Biochem Pharmacol 45 (1993) 295-301
13. McGurk K.A., Brierley C.H., and Burchell B. Drug glucuronidation by human renal UDP-glucuronosyltransferases. Biochem Pharmacol 55 (1998) 1005-1012
14. Raoof A.A., van Obbergh L.J., de Ville de Goyet J., and Verbeeck R.K. Extrahepatic glucuronidation of propofol in man: possible contribution of gut wall and kidney. Eur J Clin Pharmacol 50 (1996) 91-96
15. Hiraoka H., Yamamoto K., Miyoshi S., Morita T., Nakamura K., Kadoi Y., et al. Kidneys contribute to the extrahepatic clearance of propofol in humans, but not lungs and brain. Br J Clin Pharmacol 60 (2005) 176-182
16. Soars M.G., Riley R.J., Findlay K.A., Coffey M.J., and Burchell B. Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney. Drug Metab Dispos 29 (2001) 121-126
17. Bowalgaha K., and Miners J.O. The glucuronidation of mycophenolic acid by human liver, kidney and jejunum microsomes. Br J Clin Pharmacol 52 (2001) 605-609
18. Soars M.G., Burchell B., and Riley R.J. In vitro analysis of human drug glucuronidation and prediction of in vivo metabolic clearance. J Pharmacol Exp Ther 301 (2002) 382-390
19. Tsoutsikos P., Miners J.O., Stapleton A., Thomas A., Sallustio B.C., and Knights K.M. Evidence that unsaturated fatty acids are potent inhibitors of renal UDP-glucuronosyltransferases (UGT): kinetic studies using human kidney cortical microsomes and recombinant UGT1A9 and UGT2B7. Biochem Pharmacol 67 (2004) 191-199
20. Gaganis P., Miners J.O., and Knights K.M. Glucuronidation of fenamates: kinetic studies using human kidney cortical microsomes and recombinant UDP-glucuronosyltransfearse (UGT) 1A9 and 2B7. Biochem Pharmacol 73 (2007) 1683-1691
21. Bowalgaha K., Elliot D.J., Mackenzie P.I., Knights K.M., Swedmark S., and Miners J.O. 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 (2005) 423-433
22. Boase S., and Miners J.O. In vitro-in vivo correlations for drugs eliminated by glucuronidation: investigations with the model substrate zidovudine. Br J Clin Pharmacol 54 (2002) 493-503
23. Stone A.N., Mackenzie P.I., Galetin A., Houston J.B., and Miners J.O. Isoform selectivity and kinetics of morphine 3- and 6-glucuronidation by human udp-glucuronosyltransferases: evidence for atypical glucuronidation kinetics by UGT2B7. Drug Metab Dispos 31 (2003) 1086-1089
24. Uchaipichat V., Mackenzie P.I., Guo X.H., Gardner-Stephen D., Galetin A., Houston J.B., et al. 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 (2004) 413-423
25. Rowland A., Elliot D.J., Williams J.A., Mackenzie P.I., Dickinson R.G., and Miners J.O. In vitro characterization of lamotrigine N2-glucuronidation and the lamotrigine-valproic acid interaction. Drug Metab Dispos 34 (2006) 1055-1062
26. Uchaipichat V., Mackenzie P.I., Elliot D.J., and Miners J.O. Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human UDP-glucuronosyltransferases. Drug Metab Dispos 34 (2006) 449-456
27. Uchaipichat V., Winner L.K., Mackenzie P.I., Elliot D.J., Williams J.A., and Miners J.O. 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 61 (2006) 427-439
28. Kerdpin O., Elliot D.J., Mackenzie P.I., and Miners J.O. Sulfinpyrazone C-glucuronidation is catalyzed selectively by human UDP-glucuronosyltransferase 1A9. Drug Metab Dispos 34 (2006) 1950-1953
29. Court M.H., Krishnaswamy S., Hao Q., Duan X., Patten C.J., von Moltke L.L., et al. 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 (2002) 1125-1133
30. Nishiyama T., Kobori T., Arai K., Ogura K., Ohnuma T., Ishii K., et al. Identification of human UDP-glucuronosyltransferase isoform(s) responsible for the C-glucuronidation of phenylbutazone. Arch Biochem Biophys 454 (2006) 72-79
31. Rowland A., Gaganis P., Elliot D.J., Mackenzie P.I., Knights K.M., and Miners J.O. Binding of inhibitory fatty acids is responsible for the enhancement of UDP-glucuronosyltransferase 2B7 activity by albumin: implications for in vitro-in vivo extrapolation. J Pharmacol Exp Ther 321 (2007) 137-147
32. Rowland A., Knights K.M., Mackenzie P.I., and Miners J.O. The 'albumin effect' and drug glucuronidation: bovine serum albumin and fatty acid free human serum albumin enhance the glucuronidation of UGT1A9 substrates but not UGT1A1 and UGT1A6 activities. Drug Metab Dispos 36 (2008) 1056-1062
33. Sorich M.J., McKinnon R.A., Miners J.O., and Smith P.A. The importance of local chemical structure for chemical metabolism by human uridine 5'-diphosphate - glucuronosyltransferase. J Chem Inf Model 46 (2006) 2692-2697
34. Cheng Z., Radominska-Pandya A., and Tephly T.R. Studies of the substrate specificity of human intestinal UDP-glucuronosyltransferases 1A8 and 1A10. Drug Metab Dispos 27 (1999) 1165-1170
35. Court M.H. Isoform selective probe substrates for in vitro studies of human UDP-glucuronosyltransferases. Methods Enzymol 400 (2005) 104-116
36. Miners J.O., Knights K.M., Houston J.B., and Mackenzie P.I. In vitro-in vivo correlation for drugs and other compounds eliminated by glucuronidation in humans: pitfalls and promises. Biochem Pharmacol 71 (2006) 1531-1539
37. Miners J.O., McKinnon R.A., and Mackenzie P.I. Toxicological significance of genetic polymorphisms of UDP-glucuronosyltransferase. Toxicology 181-182 (2002) 453-456
38. Udomuksorn W., Elliot D.J., Lewis B.C., Mackenzie P.I., Yoovathaworn K., and Miners J.O. Influence of mutations associated with Gilbert and Crigler-Najjar type II syndromes on the glucuronidation kinetics of bilirubin and other UDP-glucuronosyltransferase 1A (UGT1A) substrates. Pharmacogenet Genomics 17 (2007) 1017-1029
39. Bhasker C.R., McKinnon W.M., Stone A.N., Kubota T., Ishizaki T., and Miners J.O. Genetic polymorphism of UDP-glucuronosyltransferase 2B7 (UGT2B7) at amino acid 268: ethnic diversity of alleles and potential clinical significance. Pharmacogenetics 10 (2000) 679-685
40. Girard H., Villeneuve L., Court M.H., Fortier L.-C., Caron P., Hao Q., et al. The novel UGT1A9 intronic I399 polymorphism appears as a predictor of 7-ethyl-10-hydroxycamptothecin glucuronidation levels in the liver. Drug Metab Dispos 34 (2006) 1220-1228
41. Villeneuve L., Girard H., Fortier L.-C., gagne J.-F., and Guillemette C. Novel functional polymorphisms in the UGT1A7 and UGT1A9 glucuronidating enzymes in Caucasian and African-American subjects and their impact on the metabolism of 7-ethyl-10-hydroxycamptothecin and flavopiridol anticancer drugs. J Pharmacol Exp Ther 307 (2003) 117-128
42. Rakhit A., Kochak G.M., Tipnis V., and Hurley M.E. Inhibition of renal clearance of furosemide by pentopril, an angiotensin converting enzyme inhibitor. Clin Pharmacol Ther 41 (1987) 580-586
43. Valentine J.F., Brater D.C., and Krejs G.J. Clearance of furosemide by the gastrointestinal tract. J Pharmacol Exp Ther 236 (1986) 177-180