Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties

Drug Metabolism and Disposition

Volumn 36, Issue 4, 2008, Pages 688-694

  Ohno, Shuji ^a   Kawana, Kiyoshi ^a   Nakajin, Shizuo ^a  

^a HOSHI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A8; GLUCURONOSYLTRANSFERASE 2B7; ISOENZYME; MESSENGER RNA; MORPHINE; MORPHINE 3 GLUCURONIDE; MORPHINE 6 GLUCURONIDE; URIDINE DIPHOSPHATE GLUCURONIC ACID;

ANIMAL CELL; ARTICLE; BACULOVIRUS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME SUBSTRATE; FLUORESCENCE; GLUCURONIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; IN VIVO STUDY; INHIBITION KINETICS; MICHAELIS CONSTANT; MICROSOME; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION;

ADOLESCENT; ADULT; AGED; ANIMALS; BACULOVIRIDAE; CELL LINE; FEMALE; GLUCURONOSYLTRANSFERASE; HUMANS; INSECTS; ISOENZYMES; MALE; MIDDLE AGED; MORPHINE DERIVATIVES; RECOMBINANT PROTEINS; RNA;

HEXAPODA;

EID: 41549129500     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.107.019281     Document Type: Article

References (34)

1. Beaulieu M, Levesque E, Hum DW, and Belanger A (1998) Isolation and characterization of a human orphan UDP-glucuronosyltransferase, UGT2B11. Biochem Biophys Res Commun 248:44-50.
2. Cheng Z, Radominska-Pandya A, and Tephly TR (1998) Cloning and expression of human UDP-glucuronosyltransferase (UGT) 1A8. Arch Biochem Biophys 356:301-305.
3. Cheng Z, Radominska-Pandya A, and Tephly TR (1999) Studies on the substrate specificity of human intestinal UDP-glucuronosyltransferases 1A8 and 1A10. Drug Metab Dispos 27:1165-1170.
4. Christrup LL (1997) Morphine metabolites. Acta Anaesthesiol Scand 41:116-122.
5. 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.
6. Coffman BL, Rios GR, King CD, and Tephly TR (1997) Human UGT2B7 catalyzes morphine glucuronidation. Drug Metab Dispos 25:1-4.
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. Dennis GC, Soni D, Dehkordi O, Millis RM, James H, West WL, and Taylor RE (1999) Analgesic responses to intrathecal morphine in relation to CSF concentrations of morphine-3,β-glucuronide and morphine-6,β- glucuronide. Life Sci 64:1725-1731.
9. Faura CC, Moore RA, Horga JF, Hand CW, and McQuay HJ (1996) Morphine and morphine-6-glucuronide plasma concentrations and effect in cancer pain. J Pain Symptom Manage 11:95-102.
10. Green MD, King CD, Mojarrabi B, Mackenzie PI, and Tephly TR (1998) Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos 26:507-512.
11. 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.
12. Hartley R, Green M, Quinn M, and Levene MI (1993) Analysis of morphine and its 3- and 6-glucuronides by high performance liquid chromatography with fluorimetric detection following solid phase extraction from neonatal plasma. Biomed Chromatogr 7:34-37.
13. Hasselström J, Alexander N, Bringel C, Svensson JO, and Sawe J (1991) Single-dose and steady-state kinetics of morphine and its metabolites in cancer patients - a comparison of two oral formulations. Eur J Clin Pharmacol 40:585-591.
14. Hasselström J and Sawe J (1993) Morphine pharmacokinetics and metabolism in humans: enterohepatic cycling and relative contribution of metabolites to active opioid concentrations. Clin Pharmacokinet 24:344-354.
15. 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.
16. Jin CJ, Miners JO, Lillywhite KJ, and Mackenzie PI (1993) cDNA cloning and expression of two new members of the human liver UDP-glucuronosyltransferase 2B subfamily. Biochem Biophys Res Commun 194:496-503.
17. Kilpatrick GJ and Smith TW (2005) Morphine-6-glucuronide: actions and mechanisms. Med Res Rev 25:521-544.
18. Klepstad P, Dale O, Kaasa S, Zahlsen K, Aamo T, Fayers P, and Borchgrevink PC (2003) Influences on serum concentrations of morphine, M6G and M3G during routine clinical drug monitoring: a prospective survey in 300 adult cancer patients. Acta Anaesthesiol Scand 47:725-731.
19. Klepstad P, Hilton P, Moen J, Kaasa S, Borchgrevink PC, Zahlsen K, and Dale O (2004) Day-to-day variations during clinical drug monitoring of morphine, morphine-3-glucuronide and morphine-6-glucuronide serum concentrations in cancer patients: a prospective observational study. BMC Clin Pharmacol 4:7.
20. Klepstad P, Kaasa S, and Borchgrevink PC (2000) Start of oral morphine to cancer patients: effective serum morphine concentrations and contribution from morphine-6-glucuronide to the analgesia produced by morphine. Eur J Clin Pharmacol 55:713-719.
21. Kobayashi K, Nakajima M, Oshima K, Shimada N, Yokoi T, and Chiba K (1999) Involvement of CYP2E1 as A low-affinity enzyme in phenacetin O-deethylation in human liver microsomes. Drug Metab Dispos 27:860-865.
22. Lötsch J and Geisslinger G (2001) Morphine-6-glucuronide: an analgesic of the future? Clin Pharmacokinet 40:485-499.
23. Lötsch J, Stockmann A, Kobal G, Brune K, Waibel R, Schmidt N, and Geisslinger G (1996) Pharmacokinetics of morphine and its glucuronides after intravenous infusion of morphine and morphine-6-glucuronide in healthy volunteers. Clin Pharmacol Ther 60:316-325.
24. Mackenzie PI, Bock KW, Burchell B, Guillemette C, Ikushiro S, Iyanagi T, Miners JO, Owens IS, and Nebert DW (2005) Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677-685.
25. McQuay HJ, Carroll D, Faura CC, Gavaghan DJ, Hand CW, and Moore RA (1990) Oral morphine in cancer pain: influences on morphine and metabolite concentration. Clin Pharmacol Ther 48:236-244.
26. Meng QC, Cepeda MS, Kramer T, Zou H, Matoka DJ, and Farrar J (2000) High-performance liquid chromatographic determination of morphine and its 3- and 6-glucuronide metabolites by two-step solid-phase extraction. J Chromatogr B Biomed Sci Appl 742:115-123.
27. Naidong W, Lee JW, Jiang X, Wehling M, Hulse JD, and Lin PP (1999) Simultaneous assay of morphine, morphine-3-glucuronide and morphine-6- glucuronide in human plasma using normal-phase liquid chromatography-tandem mass spectrometry with a silica column and an aqueous organic mobile phase. J Chromatogr B Biomed Sci Appl 735:255-269.
28. Osborne R, Joel S, Trew D, and Slevin M (1990) Morphine and metabolite behavior after different routes of morphine administration: demonstration of the importance of the active metabolite morphine-6-glucuronide. Clin Pharmacol Ther 47:12-19.
29. Portenoy RK, Thaler HT, Inturrisi CE, Friedlander-Klar H, and Foley KM (1992) The metabolite morphine-6-glucuronide contributes to the analgesia produced by morphine infusion in patients with pain and normal renal function. Clin Pharmacol Ther 51:422-431.
30. Soars MG, Ring BJ, and Wrighton SA (2003) The effect of incubation conditions on the enzyme kinetics of udp-glucuronosyltransferases. Drug Metab Dispos 31:762-767.
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. Drug Metab Dispos 31:1086-1089.
32. Tighe KE, Webb AM, and Hobbs GJ (1999) Persistently high plasma morphine-6-glucuronide levels despite decreased hourly patient-controlled analgesia morphine use after single-dose diclofenac: potential for opioid-related toxicity. Anesth Analg 88:1137-1142.
33. Tiseo PJ, Thaler HT, Lapin J, Inturrisi CE, Portenoy RK, and Foley KM (1995) Morphine-6-glucuronide concentrations and opioid-related side effects: a survey in cancer patients. Pain 61:47-54.
34. Tukey RH and Strassburg CP (2000) Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu Rev Pharmacol Toxicol 40:581-616.