Involvement of the rat gut epithelial and muscular layer, and microflora in chiral inversion and acyl-glucuronidation of R-fenoprofen

European Journal of Drug Metabolism and Pharmacokinetics

Volumn 22, Issue 2, 1997, Pages 97-101

  Sattari, S ^a,b   Jamali, F ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b TEHRAN UNIVERSITY OF MEDICAL SCIENCES   (Iran)

Author keywords

2 arylpropionates; Intestinal metabolism; Metabolic chiral inversion; Stereochemistry

Indexed keywords

ANTIBIOTIC AGENT; ERYTHROMYCIN; FENOPROFEN; IBUPROFEN; NEOMYCIN; NONSTEROID ANTIINFLAMMATORY AGENT;

ANIMAL TISSUE; ARTICLE; CHIRALITY; CONTROLLED STUDY; CULTURE MEDIUM; DRUG GLUCURONIDATION; ENANTIOMER; EPITHELIUM CELL; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; INTESTINE EPITHELIUM; INTESTINE MUSCLE; JEJUNUM; MICROFLORA; NONHUMAN; RAT; STEREOCHEMISTRY;

EID: 0030816676     PISSN: 03787966     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF03189791     Document Type: Article

References (22)

1. Hutt A.J., Caldwell J. (1983) : The metabolic chiral inversion of 2-arylpropionic acids - a novel route with pharmacological consequences. J. Pharm. Pharmacol., 35, 693-704.
2. Jamali F. (1988) : Pharmacokinetics of enantiomers of chiral non-steroidal anti-inflammatory drugs. Eur. J. Drug Metab. Pharmacokinet., 13, 1-9.
3. Wechter W.J., Loughheed D.G., Reischer R.J., Van Giessen G.J., Kaiser D.G. (1974) : Enzymatic inversion of saturated carbon: nature and mechanism of the inversion of R(-)-p-isobutyl hydratropic acid. Biochem. Biophys. Res. Commun., 61, 833-837.
4. Cox S.R. (1988) : Effect of route of administration on chiral inversion of R-(-)-ibuprofen. Clin. Pharmacol. Ther., 43, 146.
5. Berry B.W. Jamali F. (1991) : Presystemic and systemic chiral inversion of R-(-)-fenoprofen in the rat. J. Pharmacol. Exp. Ther., 258, 695-701.
6. Knihinicki R.D. Williams K.M. Day R.O. (1989) : Chiral inversion of 2-arylpropionic acid non-steroidal anti-inflammatory drugs: in vitro studies of ibuprofen and flurbiprofen. Biochem. Pharmacol., 38, 4389-4395.
7. Jamali F., Berry B.W. (1990) : Pharmacokinetics of ibuprofen enantiomers in the rat: effect of route of administration. Eur. J. Drug Metab. Pharmacokinet., 15, (Suppl.), S-402.
8. Jamali F. Singh N.N. Pasutto F.M. Russell A.S. Coutts R.T. (1988) : Pharmacokinetics of ibuprofen in humans following oral administration of tablets with different absorption rates. Pharm. Res., 5, 40-43.
9. Borin M.T., Cox S.R., Hageman J.M., Szpunar G.J. (1988) : Serum concentration of ibuprofen enantiomers following multiple dose administration of sustained release ibuprofen 800 mg tablets or Motrin 400 mg tablets. Pharm. Res., 10, 159S.
10. Jamali F., Mehvar R., Russell S.A,. Sattari S., Yakimets, Koo J. (1992) : Human pharmacokinetics of ibuprofen enantiomers following different doses and formulations: intestinal chiral inversion. J. Pharm. Sci., 81, 221-225.
11. Sattari S, Jamali F. (1994) : Evidence of absorption rate dependency of ibuprofen inversion in the rat. Chirality, 6, 435-439.
12. Simmonds R.G. Woodage T.J. Duff S.M. Green J.N. (1980) : Stereospecific inversion of R-(-)-benoxaprofen in rat and man. Eur. J. Drug Metab. Pharmacokinet., 5, 169-172.
13. Esposito G., Casky T.Z. (1974) : Extracellular space in the epithelium of rat's small intestine. Am. J. Physiol., 226, 50-55.
14. Konturex P.K. Brzozowski T. Konturex S.T. Dembinski A. (1990) : Role of epidermal growth factor, prostaglandins, and sulfhydryls in stress-induced gastric lesions. Gastroenterology, 9, 1607-1615.
15. Dawson J.R. Bridges J.W. (1979) : Xenobiotic metabolism by isolated intestinal epithelial cells from guinea-pigs. Biochem. Pharmacol., 28, 3299-3305.
16. Mehvar R. Jamali F. (1988) : Stereospecific high-performance liquid chromatographic (HPLC) assay of fenoprofen enantiomers in plasma and urine. Pharm. Res., 5, 53-56.
17. Rubin A. Knadler M.P. Ho P.K. Bechtol D.R. Wolen L.R. (1985) : Stereoselective inversion of (R)-fenoprofen to (S)-fenoprofen in humans. J. Pharm. Sci., 74, 82-84.
18. Hartiala K. (1973) : Metabolism of hormones, drugs and other substances by the gut. Pharmacol. Rev., 53, 496-534.
19. Koster A.S., Frankhijzen-Sierevogels A.C., Noordhoek J. (1978) : Distribution of glucuronidation capacity (1-naphthol and morphine) along the rat intestine. Biochem. Pharmacol., 34, 3527-3532.
20. Ilett K.F., Tee L.B.G., Reeves P.T., Minchin R.F. (1990) : Metabolism of drugs and other xenobiotics in the gut lumen and wall. Pharmacol. Ther., 46, 67-93.
21. Tracy T.S. Hall S.D. (1992) : Metabolic inversion of (R)-ibuprofen: epimerization and hydrolysis of ibuprofenyl-coenzyme A. Drug Metab. Dispos., 20, 322-327.
22. Jeffrey P., Tucker G.T., Bye A., Crewe H.K., Wright P.A. (1991) : The site of inversion of R(-)-ibuprofen: studies using rat in situ isolated perfused intestine/liver preparation. J. Pharm. Pharmacol., 43, 715-720.