Studies on the stereoselective internal acyl migration of ketoprofen glucuronides using 13C labeling and nuclear magnetic resonance spectroscopy

Drug Metabolism and Disposition

Volumn 26, Issue 5, 1998, Pages 457-464

  Akira, Kazuki ^a   Taira, Tadaaki ^b   Hasegawa, Hiroshi ^b   Sakuma, Chiseko ^b   Shinohara, Yoshihiko ^b  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

KETOPROFEN;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG DISPOSITION; DRUG HYDROLYSIS; ENANTIOMER; MATHEMATICAL MODEL; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ACYLATION; CARBON ISOTOPES; GLUCURONATES; HYDROLYSIS; KETOPROFEN; KINETICS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM;

EID: 0031925696     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. 13C-labeled ketoprofen glucuronides in human urine by nuclear magnetic resonance spectroscopy. Anal Chim Acta 334:67-74.
2. 13C-labeling and nuclear magnetic resonance spectroscopy to pharmacokinetic research: Measurement of metabolic rate of benzoic acid to hippuric acid in the rat. Anal Biochem 210:86-90.
3. 13C-labeling and nuclear magnetic resonance spectroscopy. J Pharmacol Toxicol Methods 37:237-243.
4. 13C-labelled (A)-and (S)-ketoprofens. J Labelled Compd Radiopharm 39:353-361.
5. 13C-labeling for pharmacokinetic research in man: Detection of benzoic acid conversion to hippuric acid. Biol Pharm Bull 18:643-647.
6. α glucuronide in cholestasis and during storage in vitro: Intramolecular rearrangement to positional isomers of glucuronic acid. Biochem J 171:203-214.
7. 9-11-carboxytetrahydrocannabinol glucuronide. Chem Res Toxicol 2:316-324.
8. Chakir S, Maurice MH, Magdalou J, Leroy P, Dubois N, Lapicque F, Abdelhamid Z and Nicolas A (1994) High-performance liquid chromatographic enantioselective assay for the measurement of ketoprofen glucuronidation by liver microsomes. J Chromatogr B 654:61-68.
9. Dickinson RG and King AR (1991) Studies on the reactivity of acyl glucuronides: II. Interaction of diflunisal acyl glucuronide and its isomers with human serum albumin in vitro. Biochem Pharmacol 42:2301-2306.
10. Dickinson RG, Kluck RM, Wood BT, Eadie MJ and Hooper WD (1986) Impaired biliary elimination of β-glucuronidase-resistant "glucuronides" of valproic acid after intravenous administration in the rat: Evidence for oxidative metabolism of the resistant isomers. Drug Metab Dispos 14:255-262.
11. Ding A, Zia-Amirhosseini P, McDonagh AF, Burlingame AL and Benet LZ (1995) Reactivity of tolmetin glucuronide with human serum albumin: Identification of binding sites and mechanisms of reaction by tandem mass spectrometry. Drug Metab Dispos 23:369-376.
12. Dubois N, Lapicque F, Maurice MH, Pritchard M, Fournel-Gigleux S, Magdalou J, Abiteboul M, Siest G and Netter P (1993) In vitro irreversible binding of ketoprofen glucuronide to plasma proteins. Drug Metab Dispos 21:617-623.
13. Dubois-Presle N, Lapicque F., Maurice MH, Foumel-Gigleux S, Magdalou J, Abiteboul M, Siest G and Netter P (1995) Stereoselective esterase activity of human serum albumin toward ketoprofen glucuronide. Mol Pharmacol 47:647-653.
14. Dutton GJ (1980) Glucuronidation of Drugs and Other Compounds, CRC Press, Boca Raton, FL.
15. Foster RT, Jamali F, Russell AS and Alballa SR (1988a) Pharmacokinetics of ketoprofen enantiomers in healthy subjects following single and multiple doses. J Pharm Sci 77:70-73.
16. Foster RT, Jamali F, Russell AS and Alballa SR (1988b) Pharmacokinetics of ketoprofen enantiomers in young and elderly arthritic patients following single and multiple doses. J Pharm Sci 77:191-195.
17. Grubb NG, Rudy DW and Hall SD (1996) Stereoselective high-performance liquid chromatographic analysis of ketoprofen and its acyl glucuronides in chronic renal insufficiency. J Chromatogr B 678:237-244.
18. Hamdoune M, Mounie J, Magdalou J, Masmoudi T, Goudonnet H and Escousse A (1995) Characterization of the in vitro glucuronidation of flurbiprofen enantiomers. Drug Metab Dispos 23:343-348.
19. Hansen-Moller J, Cornett C, Dalgaard L and Hansen SH (1988) Isolation and identification of the rearrangement products of diflunisal 1-O-acyl glucuronide. J Pharm Biomed Anal 6:229-240.
20. Hayball PJ, Nation RL and Bochner F (1992) Stereoselective interactions of ketoprofen glucuronides with human plasma protein and serum albumin. Biochem Pharmacol 44:291-299.
21. Iwakawa S, Spahn H, Benet LZ and Lin ET (1988) Carprofen glucuronides: Stereoselective degradation and interaction with human serum albumin. Pharm Res 5(Suppl.):S-214.
22. Iwaki M, Bischer A, Nguyen AC, McDonagh AF and Benet LZ (1995) Stereoselective disposition of naproxen glucuronide in the rat. Drug Metab Dispos 23:1099-1103.
23. Jamali F, Russell AS, Foster RT and Lemko C (1990) Ketoprofen pharmacokinetics in humans: Evidence of enantiomeric inversion and lack of interaction. J Pharm Sci 79:460-461.
24. Kaspersen FM and van Boeckel CAA (1987) A review of the methods of chemical synthesis of sulphate and glucuronide conjugates. Xenobiolica 17:1451-1471.
25. Kretz-Rommel A and Boelsterli UA (1994) Mechanism of covalent adduct formation of diclofenac to rat hepatic microsomal proteins: Retention of the glucuronic acid moiety in the adduct. Drug Metab Dispos 22:956-961.
26. 13C Labeling in studies of metabolic regulation. Prog Nucl Magn Res Spectrosc 20:337-383.
27. Mouelhi MEL, Ruelius HW, Fenselau C and Dulik DM (1987) Species-dependent enantioselective glucuronidation of three 2-arylpropionic acids: Naproxen, ibuprofen, and benoxaprofen. Drug Metab Dispos 15:767-772.
28. Nicholls AW, Akira K, Lindon JC, Farrant RD, Wilson ID, Harding J, Killic DA and Nicholson JK (1996) NMR spectroscopic and theoretical chemistry studies on the internal acyl migration reactions of the 1-O-acyl-β-D-glucopyranuronate conjugates of 2-, 3-, and 4-(trifluoromethyl)benzoic acids. Chem Res Toxicol 9:1414-1424.
29. Presle N, Lapicque F, Foumel-Gigleux S, Magdalou J and Netter P (1996) Stereoselective irreversible binding of ketoprofen glucuronides to albumin: Characterization of the site and the mechanism. Drug Metab Dispos 24:1050-1057.
30. Sidelmann UG, Lenz EM, Spraul M, Hofmann M, Troke J, Sanderson PN, Lindon JC, Wilson ID and Nicholson JK (1996a) 750 MHz HPLC-NMR spectroscopic studies on the separation and characterization of the positional isomers of the glucuronides of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-acetic acid. Anal Chem 68:106-110.
31. Sidelmann UG, Hansen SH, Gavaghan C, Carless HAJ, Lindon JC, Farrant RD, Wilson ID and Nicholson JK(1996b) Measurement of internal acyl migration reaction kinetics using directly coupled HPLC-NMR: Application for the positional isomers of synthetic (2-fluorobenzoyl)-D-glucopyranuronic acid. Anal Chem 68:2564-2572.
32. 1H NMR for the analysis of mixtures of isomeric ester glucuronide conjugates of trifluoromethylbenzoic acids. J Chromatogr A 728:377-385.
33. Smith PC, Benet LZ and McDonagh AF (1990) Covalent binding of zomepirac glucuronide to proteins: Evidence for a schiff base mechanism. Drug Metab Dispos 18:639-644.
34. Spann H (1988) Assay method for product formation in in vitro enzyme kinetic studies of undine diphosphate glucuronyltransferases: 2-Arylpropionic acid enantiomers. J Chromatogr 430: 368-375.
35. Spahn H, Iwakawa S, Lin ET and Benet LZ (1989) Procedures to characterize in vivo and in vitro enantioselective glucuronidation properly: Studies with benoxaprofen glucuronides. Pharm Res 6:125-132.
36. Spahn-Langguth H and Benet LZ (1992) Acyl glucuronides revisited: Is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab Rev 24:5-48.
37. Upton RA, Buskin JN, Williams RL, Holford NHG and Riegelman S (1980) Negligible excretion of unchanged ketoprofen, naproxen, and probenecid in urine. J Pharm Sci 69:1254-1257.
38. Volland C, Sun H, Dammeyer J and Benet LZ (1991) Stereoselective degradation of the fenoprofen acyl glucuronide enantiomers and irreversible binding to plasma protein. Drug Metab Dispos 19:1080-1086.
39. Worral S and Dickinson RG (1995) Rat serum albumin modified by diflunisal acyl glucuronide is immunogenic in rats. Life Sci 56:1921-1930.
40. Zia-Amirhosseini P, Harris RZ, Brodsky FM and Benet LZ (1995) Hypersensitivity to nonsteroidal anti-inflammatory drugs. Nat Med 1:2-4.