Inhibition of the rat hepatic microsomal flurbiprofen acyl glucuronidation by bile acids

Journal of Pharmaceutical Sciences

Volumn 92, Issue 10, 2003, Pages 2098-2108

  Mano, Nariyasu ^a   Goto, Takaaki ^a   Nikaido, Ayako ^a   Narui, Takashi ^a,c   Goto, Junichi ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY HOSPITAL   (Japan)

^c SSP CO LTD   (Japan)

Author keywords

Acyl glucuronide; Bile acid; Detoxification mechanism; Flurbiprofen; Inhibition

Indexed keywords

CARBOXYLIC ACID; CHENODEOXYCHOLIC ACID; FLURBIPROFEN; GLUCURONOSYLTRANSFERASE; GLYCINE; TAURINE;

ANIMAL CELL; ARTICLE; CATALYSIS; COVALENT BOND; DETOXIFICATION; DRUG GLUCURONIDATION; DRUG HYPERSENSITIVITY; DRUG URINE LEVEL; ENZYME KINETICS; LIVER MICROSOME; MALE; MASS SPECTROMETRY; NONHUMAN; RAT;

EID: 0141731262     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.10475     Document Type: Article

References (30)

1. Mills RF, Adams SS, Cliffe EE, Dickinson W, Nicholson JS. 1973. The metabolism of ibuprofen. Xenobiotica 3:589-598.
2. Bopp RJ, Nash JF, Ridolfo AS, Shepard ER. 1979. Stereoselective inversion of (R)-(-)-benoxaprofen to the (S)-(+)-enantiomer in humans. Drug Metab Dispos 7:356-359.
3. Lee EJ, Williams K, Day R, Graham G, Champion D. 1985. Stereoselective disposition of ibuprofen enantiomers in man. Br J Clin Pharmacol 19:669-674.
4. Knihinicki RD, Williams KM, Day RO. 1989. Chiral inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs-1. In vitro studies of ibuprofen and flurbiprofen. Biochem Pharmacol 38:4389-4395.
5. Knadler MP, Hall SD. 1990. Stereoselective aryl-propionyl-CoA thioester formation in vitro. Chirality 2:67-73.
6. Jamali F, Berry BW, Tehrami MR, Russell AS. 1988. Stereoselective pharmacokinetics of flurbiprofen in humans and rats. J Pharm Sci 77:666-669.
7. Dutton GJ. 1980. Glucuronidation of drugs and other compounds. Boca Raton, FL: CER Press.
8. Magdalou J, Chajes V, Lafaurie C, Siest G. 1990. Glucuronidation of 2-arylpropionic acids pirprofen, flurbiprofen, and ibuprofen by liver microsomes. Drug Metab Dispos 18:692-697.
9. Ikegawa S, Murao N, Oohashi J, Goto J. 1998. Separatory determination of diastereomeric ibuprofen glucuronides in human urine by liquid chromatography/electrospray ionization-mass spectrometry. Biomed Chromatogr 12:317-321.
10. Pauson SK, Hribar JD, Liu NW, Hajdu E, Bible RH Jr, Piergies A, Larim A. 2000. Metabolism and excretion of [14C]celecoxib in healthy male volunteers. Drug Metab Dispos 28:308-314.
11. Ding A, Ojingwa JC, McDonagh AF, Burlingame AL, Benet LZ. 1993. Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry. Proc Natl Acad Sci USA 90:3797-3801.
12. Smith PC, Liu JH. 1993. Covalent. binding of suprofen acyl glucuronide to albumin in vitro. Xenobiotica 23:337-348.
13. Ikegawa S, Murao N, Nagata M, Ohba S, Goto J. 1999. Covalent binding of bile acid acyl glucuronide with protein. Anal Sci 15:213-215.
14. Worrall S, Dickinson RG. 1995. Rat serum albumin modified by diflunisal acyl glucuronide is immunogenic in rats. Life Sci 56:1921-1930.
15. Smith PC, Liu JH. 1995. Covalent binding of suprofen to renal tissue of rat correlates with excretion of its acyl glucuronide. Xenobiotica 25:531-540.
16. El Mouelhi M, Bock KW. 1991. Stereoselective (S)- and (R)-naproxen glucuronosyltransferases of rat liver. Drug Metab Dispos 19:304-308.
17. El Mouelhi M, Beck S, Bock KW. 1993. Stereoselective glucuronidation of (R)- and (S)-naproxen by recombinant rat phenol UDP-glucuronosyltransferase (UGT1A1) and its human orthologue. Biochem Pharmacol 46:1298-1300.
18. Hamdoune M, Mounie J, Magdalou J, Masmoudi T, Goudonnet H, Escousse A. 1995. Characterization of the in vitro glucuronidation of flurbiprofen enantiomers. Drug Metab Dispos 23:343-348.
19. Mano N, Narui T, Nikaido A, Goto J. 2002. Separation and determination of diastereomeric flurbiprofen acyl glucuronides in human urine by LC/ESI-MS with a simple column-switching technique. Drug Metabol Pharmacokinet 17:142-149.
20. Mano N, Nishimura K, Narui T, Ikegawa S, Goto J. 2002. Characterization of rat liver bile acid acyl glucuronosyltransferase. Steroids 67:257-262.
21. Radominska A, Little JN, Lester R, Mackenzie PI. 1994. Bile acid glucuronidation by rat liver microsomes and cDNA-expressed UDP-glucuronosyltransferases. Biochim Biophys Acta 1205:75-82.
22. Mano N, Nikaido A, Narui T, Yamasaki D, Goto J. 2002. Rapid and simple quantitative assay method for diastereomeric flurbiprofen glucuronides in the incubation mixture. J Chromatogr B 776:125-131.
23. Eneroth P, Nyströn E. 1968. Quantification of cholesteryl sulfate and neutral sterol derivatives in human faces after purification on lipophilic sephadex gels. Steroids 11:187-205.
24. Goto J, Murao N, Oohashi J, Ikegawa S. 1998. Synthesis of bile acid 24-acyl glucuronides. Steroids 63:180-185.
25. Matern H, Matern S, Schelzig Ch, Gerok W. 1980. Bile acid UDP-glucuronosyltransferase from human liver. Properties and studies on aglycone substrate specificity. FEBS Lett 118:251-254.
26. Bradford MM, 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
27. Kretz-Rommel A, Boelsterli UA. 1993. Diclofenac covalent protein binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes. Toxicol Appl Pharmacol 120:155-161.
28. Greim H, Trülzsch D, Roboz J, Dressler K, Czygan P, Hutterer F, Schaffner F, Popper H. 1972. Mechanism of cholestasis. 5. Bile acids in normal rat livers and in those after bile duct ligation. Gastroenterology 63:837-845.
29. Greim H, Czygan P, Schaffner F, Popper H. 1973. Determination of bile acids in needle biopsies of human liver. Biochem Med 8:280-286.
30. Ishii Y, Sakai Y, Matsuda T, Nozu K, Inoue M, Tono M, Ofuji T. 1975. Absorption, distribution, metabolism and excretion of 2-(2-fluoro-4-biphenylyl) propionic acid (flurbiprofen). Pharmacometrics 5:645-652.