Bioinversion of R-flurbiprofen to S-flurbiprofen at various dose levels in rat, mouse, and monkey

Chirality

Volumn 16, Issue 6, 2004, Pages 379-387

  Leipold, Douglas D ^a   Kantoci, Darko ^a   Murray Jr , E David ^a   Quiggle, David D ^a   Wechter, William J ^a  

^a Encore Pharmaceuticals Inc   (United States)

Author keywords

Aryl propionic acids; Chiral bioinversion; Metabolism; Pharmacokinetics; Preclinical model

Indexed keywords

ARYLPROPIONIC ACID DERIVATIVE; FLURBIPROFEN; LEVO FLURBIPROFEN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOINVERSION; CHIRALITY; CONTROLLED STUDY; DOG; DOSE TIME EFFECT RELATION; DRUG DOSE REDUCTION; DRUG MECHANISM; EVALUATION; FEMALE; GUINEA PIG; LABORATORY DIAGNOSIS; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RABBIT; RACEMIC MIXTURE; RAT;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; AREA UNDER CURVE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; FLURBIPROFEN; HAPLORHINI; HUMANS; MALE; MICE; MICE, INBRED C57BL; MODELS, CHEMICAL; PROPIONIC ACIDS; RATS; RATS, SPRAGUE-DAWLEY; SEX FACTORS; SPECIES SPECIFICITY; STEREOISOMERISM; TIME FACTORS;

EID: 3042596290     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20053     Document Type: Article

References (31)

1. Brune K, Beck WS, Geisslinger G, Menzel-Soglowek S, Peskar BM, Peskar BA. Aspirin-like drugs may block pain independently of prostaglandin synthesis inhibition. Experientia 1991;47:257-261.
2. Brune K, Geisslinger G, Menzel-Soglowek S. Pure enantiomers of 2-arylpropionic acids: tools in pain research and improved drugs in rheumatology. J Clin Pharmacol 1992;32:944-952.
3. Carabaza A, Cabre F, Rotllan E, Gomez M, Gutierrez M, Garcia ML, Mauleon D. Stereoselective inhibition of inducible cyclooxygenase by chiral nonsteroidal anti-inflammatory drugs. J Clin Pharmacol 1996; 36:505-512.
4. Kulmacz RJ, Lands WEM. Stoichiometry and kinetics of the interaction of prostaglandin H synthetase with anti-inflammatory agents. J Biol Chem 1985;260:12572-12578.
5. Geisslinger G, Ferreira SH, Menzel S, Schlott D, Brune K. Antinociceptive actions of R (-) Flurbiprofen - a non-cyclooxygenase inhibiting 2-arylpropionic acid - in rats. Life Sci 1994;54:173-177.
6. Min/+ mouse model: implications for prophylaxis and treatment of colon cancer. Cancer Res 1997;57: 4316-4324.
7. Wechter WJ, Leipold DD, Murray Jr ED, Quiggle D, McCracken JD, Barrios RS, Greenberg NM. E-7869 (R-flurbiprofen) inhibits progression of prostate cancer in the TRAMP mouse. Cancer Res 2000;60: 2203-2208.
8. Rainsford KD. Gastrointestinal damage from nonsteroidal anti-inflammatory drugs. Toxicol Pathol 1988;16:251-259.
9. Wallace JL. Gastric ulceration: critical events at the neutrophil-endothelium interface. Can J Physiol Pharmacol 1993;71:98-102.
10. Riendeau D, Charleson S, Cromlish W, Mancini J, Wong E, Guay J. Comparison of the cyclooxygnease-1 inhibitory properties of non-steroidal anti-inflammatory drugs (NSAIDs) and selective COX-2 inhibitors, using sensitive microsomal and platelet assays. Can J Physiol Pharmacol 1997;75:1088-1095.
11. Wechter WJ, Bigornia AE, Murray Jr ED, Levine BH, Young JW. Racflurbiprofen is more ulcerogenic than its (S)-enantiomer. Chirality 1993;5:492-494.
12. Wechter WJ, McCracken JD, Kantoci D, Murray Jr ED, Quiggle DD, Leipold DD, Gibson K, Mineyama Y, Liu Y. Mechanism of enhancement of intestinal ulcerogenicity of S-aryl propionic acids by their R-enantiomers on the rat. Dig Dis Sci 1998;43:1264-1274.
13. Jamali F, Berry BW, Tehrani MR, Russell AS. Stereoselective pharmacokinetics of flurbiprofen in humans and rats. J Pharm Sci 1988;77: 666-669.
14. Jamali F, Berry BW, Wright MR. Dose-dependency of flurbiprofen enantiomer pharmacokinetics in the rat. J Pharm Sci 1994;83: 1077-1080.
15. Knadler MP, Brater DC, Hall SD. Stereoselective disposition of flurbiprofen in normal volunteers. Br J Clin Pharmacol 1992;33:369-375.
16. Davies NM. Clinical pharmacokinetics of flurbiprofen and its enantiomers. Clin Pharmacokinet 1995;28:100-114.
17. Berry BW, Jamali F. Enantiomeric interaction of flurbiprofen in the rat. J Pharm Sci 1989;78:632-634.
18. Geisslinger G, Lotsch J, Menzel S, Kobal G, Brune K. Stereoselective disposition of flurbiprofen in healthy subjects following administration of the single enantiomers. Br J Clin Pharmacol 1994; 37:392-394.
19. Knihinicki RD, Day RO, Graham GG, Williams KM. Stereoselective disposition of ibuprofen and flurbiprofen in rats. Chirality 1990;2: 134-140.
20. Menzel-Soglowek S, Geisslinger G, Beck WS, Brune K. Variability of bioinversion of R-flurbiprofen in different species. J Pharm Sci 1992; 81:888-891.
21. Tegeder I, Williams K, Geisslinger G. Metabolic chiral inversion of 2-arylpropionic acids. In: Eiclebaum M, Testa B, Samogyi A, editors. Stereochemical aspects of drug action and disposition. Berlin: Springer; 2003. p 341-354.
22. Quiggle DD, Lilly M, Murray ED, Gibson KM, Leipold DD, Gutierrez I, Loughman BE, Wechter WJ. PK guided multi-dose, tolerability and safety of E-7869 in prostate cancer patients. In: Proc American Association for Cancer Research, 2000;41:609 (abstract 3874).
23. Kantoci D, Wechter WJ. Calculation of bioinversion half-lives of aryl propionic acid class nonsteroidal antiinflammatory drugs. J Clin Pharmacol 1996;36:500-504.
24. Wechter WJ. On the mechanism of R-aryl propionic acid class NSAIDs. Epimerization in humans and the clinical implications for the use of racemates. J Clin Pharmacol 1994;34:1036-1042.
25. Muller S, Mayer JM, Etter JC, Testa B. Influence of palmitate and benzoate on the unidirectional chiral bioinversion of ibuprofen in isolated rat hepatocytes. Biochem Pharmacol 1992;44:1468-1470.
26. Porubek DJ, Sanins SM, Stephens JR, Grillo MP, Kaiser DG, Halstead GW, Adams WJ, Baillie TA. Metabolic chiral bioinversion of flurbiprofen-CoA in vitro. Biochem Pharmacol 1991;42:R1-R4.
27. Shieh WR, Chen CS. Purification and characterization of novel "2-arylpropionyl-CoA epimerases" for rat liver cytosol and mitochondria. J Biol Chem 1993;268:3487-3493.
28. Cantorna MT, Balish E. Inability of human clinical strains of Heliobacter pylori to colonize the alimentary tract of germfree rodents. Can J Microbiol 1990;36:237-241.
29. Sevoz C, Benoit E, Buronfosse T. Thioesterification of 2-arylpropionic acids by recombinant acyl-coenzyme A synthase (ACS 1 and ACS 2). Drug Metab Disp 2000;28:398-402.
30. Ghosh B, Barbosa E, Singh I. Molecular cloning and sequencing of human palmitoyl-CoA ligase and its tissue specific expression. Mol Cell Biochem 1995;111:197-203.
31. Minekura H, Fujino T, Kang MJ, Fujita T, Endo Y, Yamamoto T. Human acyl-coenzyme A synthetase 3 cDNA and localization of its gene (ACS3) to chromosome band 2q34-q35. Genomics 1997;42: 180-181.