Species comparison of enantioselective oral bioavailability and pharmacokinetics of ketoprofen

Research in Veterinary Science

Volumn 91, Issue 3, 2011, Pages 415-421

  Neirinckx, E ^a   Croubels, S ^a   De Boever, S ^a   Remon, J P ^a   Bosmans, T ^a   Daminet, S ^a   De Backer, P ^a   Vervaet, C ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Bioavailability; Enantiomers; Ketoprofen; Pharmacokinetics; Species differences

Indexed keywords

FENOPROFEN; KETOPROFEN;

ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; CHICKEN; CONTROLLED STUDY; DOG; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DISPOSITION; DRUG ELIMINATION; DRUG HALF LIFE; DRUG METABOLISM; DRUG PENETRATION; DRUG SOLUBILITY; ENANTIOMER; ENANTIOSELECTIVITY; FEMALE; FIRST PASS EFFECT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; SPECIES COMPARISON; SPECIES DIFFERENCE; STEREOSPECIFICITY; STOMACH EMPTYING; SWINE; TIME TO MAXIMUM PLASMA CONCENTRATION; TURKEY (BIRD);

ANIMALS; AREA UNDER CURVE; BIOLOGICAL AVAILABILITY; CROSS-OVER STUDIES; FEMALE; HALF-LIFE; KETOPROFEN; SPECIES SPECIFICITY;

CANIS FAMILIARIS; GALLUS GALLUS; SUIDAE;

EID: 80555136657     PISSN: 00345288     EISSN: 15322661     Source Type: Journal    
DOI: 10.1016/j.rvsc.2010.08.017     Document Type: Article

References (52)

1. Aberg G., Ciofalo V.B., Pendleton R.G., Ray G., Weddle D. Inversion of (R)- to (S)-ketoprofen in eight animal species. Chirality 1995, 7:383-387.
2. Arifah A.K., Landoni M.F., Frean S.P., Lees P. Pharmacodynamics and pharmacokinetics of ketoprofen enantiomers in sheep. American Journal of Veterinary Research 2001, 62(1):77-86.
3. Arifah A.K., Landoni M.F., Lees P. Pharmacodynamics, chiral pharmacokinetics and PK-PD modelling of ketoprofen in the goat. Journal of veterinary Pharmacology and Therapeutics 2003, 26:139-150.
4. Baert K., De Backer P. Comparative pharmacokinetics of three non-steroidal anti-inflammatory drugs in five bird species. Comparative Biochemistry and Physiology C - Toxicology and Pharmacology 2003, 134(1):25-33.
5. Caldwell J., Hutt A.J., Fournel-Gigleux S. The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences. Biochemical Pharmacology 1988, 37(1):105-114.
6. Campbell D.B. Stereoselectivity in clinical pharmacokinetics and drug development. European Journal of Drug Metabolism and Pharmacokinetics 1990, 15(2):109-125.
7. Castro E., Soraci A., Fogel F., Tapia O. Chiral inversion of R(-) fenoprofen and ketoprofen enantiomers in cats. Journal of Veterinary Pharmacology and Therapeutics 2000, 23:265-271.
8. Chakir S., Maurice M.H., Magdalou L., Leroy P., Lapicque F., Abdelhamid Z., Nicolas A. High-performance liquid-chromatographic enantio selective assay for the measurement of ketoprofen glucuronidation by liver-microsomes. Journal of Chromatography B - Biomedical Applications 1994, 654(1):61-68.
9. Delatour P., Benoit E., Bourdin M., Gobron M., Moysan E., Polonovski M.J., Aron M.E., Cara M.M., Auquier M.L. Enantioselectivity in the disposition of ketoprofen and carprofen in man and animals. Bulletin de l'Académie Nationale de Médecine 1993, 177(3):515-527.
10. Dorrestein G.M. Formulation and (bio)availability problems of drug formulations in birds. Journal of Veterinary Pharmacology and Therapeutics 1992, 15:143-150.
11. Foster R.T., Jamali F. Stereoselective pharmacokinetics of ketoprofen in the rat. Influence of route of administration. Drug Metabolism and Disposition 1988, 16(4):623-626.
12. Foster R.T., Jamali F., Russell A.S., Alballa S.R. Pharmacokinetics of ketoprofen enantiomers in healthy subjects following single and multiple doses. Journal of Pharmaceutical Sciences 1988, 77(1):70-73.
13. Garcia M.L., Tost D., Vilageliu J., Lopez S., Carganico G., Mauleon D. Bioavailability of S(+)-ketoprofen after oral administration of different mixtures of ketoprofen enantiomers to dogs. Journal of Clinical Pharmacology 1998, 38:22S-26S.
14. Gasthuys F., De Boever S., Schauvliege S., Reyns T., Levet T., Cornillie P., Casteleyn C., De Backer P., Croubels S. Transsplenic portal catheterization combined with a jugular double-lumen catheter for pharmacokinetic and presystemic metabolization studies in pigs. Journal of Veterinary Pharmacology and Therapeutics 2009, 32(2):137-145.
15. Graham J.E., Kollias-Baker C., Craigmill A.L., Thomasy S.M., Tell L.A. Pharmacokinetics of ketoprofen in Japanese quail (Coturnix japonica). Journal of Veterinary Pharmacology and Therapeutics 2005, 28:399-402.
16. Granero G.E., Amidon G.L. Possibility of enterohepatic recycling of ketoprofen in dogs. International Journal of Pharmaceutics 2008, 349:166-171.
17. Granero G.E., Ramachandran C., Amidon G.L. Rapid in vivo dissolution of ketoprofen: implications on the biopharmaceutics classification system. Pharmazie 2006, 61:673-676.
18. Hall S.D., Rudy A.C., Knight P.M., Brater D.C. Lack of presystemic inversion of (R)- to (S)-ibuprofen in humans. Clinical Pharmacology and Therapeutics 1993, 53:393-400.
19. Hayball P.J., Nation R.L., Bochner F. Enantioselective pharmacodynamics of the nonsteroidal antiinflammatory drug ketoprofen: in vitro inhibition of human platelet cyclooxygenase activity. Chirality 1992, 4:484-487.
20. Igarza L., Soraci A., Auza N., Zeballos H. Chiral inversion of (R)-ketoprofen: influence of age and differing physiological status in dairy cattle. Veterinary Research Communications 2002, 26:29-37.
21. Ishizaki T., Sasaki T., Suganuma T., Horai Y., Chiba K., Watanabe M., Asuke W., Hoshi H. Pharmacokinetics of ketoprofen following single oral, intramuscular and rectal doses and after repeated oral administration. European Journal of Clinical Pharmacology 1980, 18(5):407-414.
22. Jamali F., Brocks D.R. Clinical pharmacokinetics of ketoprofen and its enantiomers. Clinical Pharmacokinetics 1990, 19(3):197-217.
23. Jamali F., Lovlin R., Aberg G. Bi-directional chiral inversion of ketoprofen in CD-1 mice. Chirality 1997, 9(1):29-31.
24. Jaussaud P., Bellon C., Besse S., Courtot D., Delatour P. Enantioselective pharmacokinetics of ketoprofen in horses. Journal of Veterinary Pharmacology and Therapeutics 1993, 16:373-376.
25. Lam F.C., Hung C.T., Perrier D.G. Estimation of variance for harmonic mean half-lives. Journal of Pharmaceutical Sciences 1985, 74(2):229-231.
26. Landoni M.F., Comas W., Mucci N., Anglarilli G., Bidal D., Lees P. Enantiospecific pharmacokinetics and pharmacodynamics of ketoprofen in sheep. Journal of Veterinary Pharmacology and Therapeutics 1999, 22:349-359.
27. Landoni M.F., Cunningham F.M., Lees P. Pharmacokinetics and pharmacodynamics of ketoprofen in calves applying PK/PD modelling. Journal of Veterinary Pharmacology and Therapeutics 1995, 18:315-324.
28. Landoni M.F., Foot R., Frean S., Lees P. Effects of flunixin, tolfenamic acid, R(-) and S(+) ketoprofen on the response of equine synoviocytes to lipopolysaccharide stimulation. Equine Veterinary Journal 1996, 28(6):468-475.
29. Landoni M.F., Lees P. Pharmacokinetics and pharmacodynamics of ketoprofen enantiomers in calves. Chirality 1995, 7(8):586-597.
30. Larsen C., Jensen B.H. Bioavailability of ketoprofen from orally administered ketoprofen-dextran ester prodrugs in the pig. Acta Pharmaceutica Nordica 1991, 3(2):71-76.
31. Lees P., Landoni M.F., Giraudel J., Toutain P.L. Pharmacodynamics and pharmacokinetics of nonsteroidal anti-inflammatory drugs in species of Veterinary interest. Journal of Veterinary Pharmacology and Therapeutics 2004, 27:479-490.
32. Lees P., Taylor P.M., Landoni F.M., Arifah A.K., Waters C. Ketoprofen in the cat: pharmacodynamics and chiral pharmacokinetics. Veterinary Journal 2002, 165:21-35.
33. Lennernäs H. Intestinal permeability and its relevance for absorption and elimination. Xenobiotica 2007, 37(10-11):1015-1051.
34. Martinez, M.N., 2006. In vivo/in vitro correlation studies in dogs. In: 2nd Joint AAPS/AAVPT/CRS Workshop on Collaboration in the Research and Development of Veterinary Pharmaceuticals, October 27-29, San Antonio, Texas.
35. Martinez M., Amidon G., Clarke L., Jones W.W., Mitra A., Riviere J. Applying the biopharmaceutics classification system to veterinary pharmaceutical products Part II. Physiological considerations. Advanced Drug Delivery Reviews 2002, 54(6):825-850.
36. Martinez M., Augsburger L., Johnston T., Jones W.W. Applying the Biopharmaceutics classification system to veterinary pharmaceutical products Part I: Biopharmaceutics and formulation considerations. Advanced Drug Delivery Reviews 2002, 54(6):805-824.
37. Mauleon D., Artigas R., García M.L., Carganico G. Preclinical and clinical development of dexketoprofen. Drugs 1996, 52(Suppl. 5):24-46.
38. Mauleon D., Mis R., Ginesta J., Ortega E., Vilageliu J., Basi N., Carganico G. Pharmacokinetics of ketoprofen enantiomers in monkeys following single and multiple oral administration. Chirality 1994, 6(7):537-542.
39. Mehvar R., Jamali F. Pharmacokinetic analysis of enantiomeric inversion of chiral nonsteroidal anti-inflammatory drugs. Pharmaceutical Research 1988, 5:76-79.
40. Montoya L., Ambros L., Kreil V., Bonafine R., Albarellos G., Hallu R., Soraci A. A pharmacokinetic comparison of meloxicam and ketoprofen following oral administration to healthy dogs. Veterinary Research Communications 2004, 28(5):415-428.
41. Neirinckx E., Remon J.P., De Backer P., Vervaet C., Croubels S. The biopharmaceutics classification system in veterinary medicine: pH-solubility relationship of analgesic and anti-inflammatory drugs. In: Proceedings of the Tenth International EAVPT Congress. Journal of Veterinary Pharmacology and Therapeutics 2006, 26(Suppl. 1):287-288.
42. Neirinckx, E., Vervaet, C., De Boever, S., Remon, J.P., Gommeren, K., Daminet, S., De Backer, P., Croubels, S., in press. Species comparison of oral bioavailability, first-pass metabolism and pharmacokinetics of acetaminophen. Research in Veterinary Science.
43. Neirinckx, E., Croubels, S., Remon, J.P., De Backer, P., Vervaet, C., submitted for publication. Chiral inversion of R(-) to S(+) ketoprofen in pigs. Journal of Veterinary Pharmacology and Therapeutics.
44. Populaire P., Terlain B., Pascal S., Decouvelaere B., Renard A., Thomas J.-P. Comportement biologique: taux sériques, excrétion et biotransformation de l'acide (benzoyl-3 phényl)-2 propionique ou kétoprofène chez l'animal et chez l'homme. Annales Pharmaceutiques Françaises 1973, 31(12):735-749.
45. Raekallio M.R., Mustonen K.M., Heinonen M.L., Peltoniemi O.A.T., Säkkinen M.S., Peltoniemi S.M., Honkavaara J.M., Vainio O.M. Evaluation of bioequivalence after oral, intramuscular, and intravenous administration of racemic ketoprofen in pigs. American Journal of Veterinary Research 2008, 69(1):108-113.
46. Schmitt M., Guentert T.W. Biopharmaceutical evaluation of ketoprofen following intravenous, oral, and rectal administration to dogs. Journal of Pharmaceutical Sciences 1990, 79(7):614-616.
47. Sheng J.J., Kasim N.A., Chandrasekharan R., Amidon G.L. Solubilization and dissolution of insoluble weak acid, ketoprofen: effects of pH combined with surfactant. European Journal of Pharmaceutical Sciences 2006, 29(3-4):306-314.
48. Soars M.G., Riley R.J., Findlay K.A.B., Coffey M.J., Burchell B. Evidence for significant differences in microsomal drug glucuronidation by canine and human liver and kidney. Drug Metabolism and Disposition 2001, 29(2):121-126.
49. Souilem O., Gogny M. Particularités de la physiology digestive des volailles. Revue de Médecine Vétérinaire 1994, 145:525-537.
50. Suesa N., Fernandez M.F., Gutierrez M., Rufat M.J., Rotllan E., Calvo L., Mauleon D., Carganico G. Stereoselective cyclooxygenase inhibition in cellular models by the enantiomers of ketoprofen. Chirality 1993, 5(8):589-595.
51. Vermeulen B., Remon J.P. The oral bioavailability of ibuprofen enantiomers in broiler chickens. Journal of Veterinary Pharmacology and Therapeutics 2001, 24:105-109.
52. Walle T., Walle U.K. Pharmacokinetic parameters obtained with racemates. Trends in Pharmacological Sciences 1986, 7(4):155-158.