Analgesic, antiinflammatory, and antipyretic effects of S(+)-ketoprofen in vivo

Journal of Clinical Pharmacology

Volumn 38, Issue 12 SUPPL., 1998, Pages

  Cabré, Francesc ^a   Fernández, M Francisca ^a   Calvo, Lidia ^a   Ferrer, Xavier ^a   García, M Luisa ^a   Mauleón, David ^a  

^a Laboratorios Menarini SA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DEXKETOPROFEN; DICLOFENAC;

ADOLESCENT; ANALGESIC ACTIVITY; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ANTIPYRETIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFECT; DRUG POTENCY; ENANTIOMER; INTRAVENOUS DRUG ADMINISTRATION; MALE; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; RAT; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0032416944     PISSN: 00912700     EISSN: None     Source Type: Journal    
DOI: 10.1002/jcph.1998.38.s1.3     Document Type: Article

References (45)

1. Vane J: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin like drugs. Nature 1971;231:232-235.
2. Geisslinger G, Schaible HG: New insights into the site and mode of antinociceptive action of flurbiprofen enantiomers. J Clin Pharmacol 1996;36:513-520.
3. Urquart E: Central analgesic activity of nonsteroidal anti-inflammatory drugs in animal and human pain models. Semin Arthritis Rheum 1993;23:198-205.
4. Malmberg AB, Yaksh TL: Spinal actions of non-steroidal anti-inflammatory drugs: evidence for a central role of prostanoids in nociceptive processing. Prog Pharmacol Clin Pharmacol 1993;10: 91-110.
5. Neugebauer V, Schaible HG, He X, Lücke T, Güdling P, Schmidt RF: Electrophysiological evidence for a spinal antinociceptive action of dipyrone. Agents Actions 1994;41:62-70.
6. 2 release. Eur J Pharmacol 1997;331:155-160.
7. Kaufmann WE, Andreasson KL, Isakson PC, Worley PF: Cyclooxygenases and the central nervous system. Prostaglandins 1997;54:601-624.
8. Gaut ZN, Baruth H, Randall LO, Ashley C, Paulsrud JR: Stereoisometric relationship among anti-inflammatory activity, inhibition of platelet aggregation, and inhibition of prostaglandin synthetase. Prostaglandins 1975;10:59-66.
9. Ku EC, Wasvary JM: Inhibition of prostaglandin synthase by pirofen. Studies with sheep seminal vesicle enzyme. Biochim Biophys Acta 1975;384:360-368.
10. Adams SS, Bresloff P, Mason GC: Pharmacological differences between tho optical isomers of ibuprofen: evidence for metabolic inversion of the (-)-isomer. J Pharm Pharmacol 1976;28:256-257.
11. Buttinoni A, Ferrari M, Colombo M, Ceserani R: Biological activity of indoprofen and its optical isomers. J Pharm Pharmacol 1983;35:603-604.
12. Geisslinger G, Stock KP, Bach GL, Loew D, Brune K: Pharmacological differences between R(-)- and S(+)-ibuprofen. Agents Actions 1989;26:455-457.
13. Cerletti C, Manarini S, Colombo M, Tavani M: The (+)-enantiomer is responsible for the antiplatelet and anti-inflammatory activity of (±)-indobufen. J Pharm Pharmacol 1990;42:885-887.
14. Patrignani P, Volpi D, Ferrario R, Romanzini L, Di Somma M, Patrono C: Effects of racemic, S- and R-indobufen on cyclooxygenase and lipoxygenase activities in human whole blood. Eur J Pharmacol 1990;191:83-88.
15. Peskar BM, Kulge S, Peskar BA, Soglowek SM, Brune K: Effects of pure enantiomers of flurbiprofen in comparison to racemic flurbiprofen on eicosanoid release from various rat organs ex vivo. Prostaglandins 1991;42:515-531.
16. Hayball PJ, Nation RL, Bochner F: Enantioselective pharmacodynamics of the nonsteroidal antiinflammatory drug ketoprofen: in vitro inhibition of human platelet cyclooxygenase activity. Chirality 1992;4:484-487.
17. Suesa N, Fernández MF, Gutiérrez M, Rufat MJ, Rotllan E, Calvo L, Mauleón D, Carganico G: Stereoselective cyclooxygenase inhibition in cellular models by the enantiomers of ketoprofen. Chirality 1993;5:589-595.
18. Carabaza A, Cabré F, Gutiérrez M, Rotllan E, Gómez M, García ML, Mauleón D: Stereoselective inhibition of inducible cyclooxygenase by chiral nonsteroidal antiinflammatory drugs. J Clin Pharmacol 1996;36:505-512.
19. Boneberg EM, Zou MH, Ullrich V: Inhibition of cyclooxygenase-1 and -2 by R(-)- and S(+)-ibuprofen. J Clin Pharmacol 1996; 36:16S-19S.
20. Jamali F, Brocks DR: Clinical pharmacokinetics of ketoprofen and its isomers. Clin Pharmacokinet 1990;19:197-217.
21. Hayball PJ, Nation RL, Bockner F, Sanson LN, Ahern MJ, Smith MD: The influence of renal function on the enantioselective pharmacokinetics and pharmacodynamics of ketoprofen in patients with rheumatoid arthritis. Br J Clin Pharmacol 1993;32: 185-193.
22. Wechter WJ, Bigornia AE, Murray ED, Levine BH, Young JW: Rac-Flurbiprofen is more ulcerogenic than its (S)-enantiomer. Chirality 1993;5:492-494.
23. Malmberg AB, Yaksh TL: Antinociceptive actions of spinal non-steroidal anti-inflammatory agents on the formalin test in the rat. J Pharmacol Exp Ther 1992;263:136-146.
24. Malmberg AB, Yaksh TL: Antinociception produced by spinal delivery of the S and R enantiomers of flurbiprofen in the formalin test. Eur J Pharmacol 1994;256:205-209.
25. Neugebauer V, Geisslinger G, Rümenapp P, Weiretter F, Szelenyi I, Brune K, Schaible HG: Antinociceptive effects of R(-)-and S(+)-flurbiprofen on rat spinal dorsal horn neurons rendered hyperexcitable by acute knee joint inflammation. J Pharmacol Exp Ther 1995;275:618-628.
26. Veys EM: 20 years' experience with ketoprofen. Scand J Rheumatol 1991;(Suppl. 90):3-44.
27. Mauleón 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;6:537-542.
28. Aberg G, Ciofalo VB, Pendleton RG, Ray G, Weddle D: Inversion of (R)- to (S)-ketoprofen in eight animal species. Chirality 1995;7:383-387.
29. Palomer A, Cabré M, Ginesta J, Mauleón D, Carganico G: Resolution of rac-ketoprofen esters by enzymatic reactions in organic media. Chirality 1993;5:320-328.
30. Otterness IG, Bliven ML: Laboratory models for testing non-steroidal antiinflammatory drugs, in, Lombardino JG (ed): Nonsteroidal Antiinflammatory Drugs. New York: John Wiley & Sons, 1985;111-252.
31. Siegmund E, Cadmus R, Lu G: A method for evaluating both non-narcotic and narcotic analgesics. Proc Soc Exp Biol Med 1957;95:729-731.
32. Gong QL, Hedner J, Björkman R, Hedner T: Morphine-3-glucoronide may functionally antagonize morphine-6-glucoronide induced antinociception and ventilatory depression in the rat. Pain 1992;48:249-255.
33. Winter CA, Risley EA, Nuss GW: Carrageenan-induced edema in the hind paw of the rat as an assay for anti-inflammatory activity. Proc Soc Exp Biol Med 1962;111:544-547.
34. Foster RT, Jamali F, Russell AS, Alballa SR: Pharmacokinetics of ketoprofen enantiomers in healthy subjects following single and multiple doses. J Pharm Sci 1988;77:70-73.
35. Foster RT, Jamali F: Stereoselective pharmacokinetics of ketoprofen in the rat: influence of route of administration. Drug Metab Dispos 1988;16:623-626.
36. Carabaza A, Suesa N, Tost D, Pascual J, Gómez M, Gutiérrez M, Ortega E, Montserrat X, García AM, Mis R, Cabré F, Mauleón D, Carganico G: Stereoselective metabolic pathways of ketoprofen in the rat: incorporation into triacylglycerols and enantiomeric inversion. Chirality 1996;8:163-172.
37. Abas A, Meffin PJ: Enantioselective disposition of 2-aryl propionic acid non-steroidal anti-inflammatory drugs. IV. Ketoprofen disposition. J Pharmacol Exp Ther 1987;240:637-641.
38. Landoni MF, Lees P: Pharmacokinetics and pharmacodynamics of ketoprofen enantiomers in calves. Chirality 1995;7:586-589.
39. Delatour P, Benoit E, Bourdin M, Gobron M, Moysan F: Enantiosélectivite comparée de la disposition de deux anti-inflammatoires non stéroidienes, le ketoprofene et le carprofene, chez l'homme et l'animal. Bull Acad Natl Med 1993;177: 515-527.
40. Chau T, Walter T, Zimmerman J, Hartman D, Ochalski S, Weichman B: Analgesic activities of PEM-420, the active eutomer of pemedolac. Agents Actions 1993;39:C27-C29.
41. Mis R, Tost D, Ortega E, Mauleón D, Carganico G: Bioinversion of ketoprofen enantiomers in several species [Abstract]. Methods Find Exp Clin Pharmacol 1994;16:81.
42. 2+ dependent process. Prostaglandins 1979;18:179-190.
43. Kusuhara H, Fukunari A, Matsuyuki H, Okumoto T: Principal involvement of cyclooxygenase-1-derived prostaglandins in the c-fos expression of the rat hind brain following visceral stimulation with acetic acid. Mol Brain Res 1997;52:151-156.
44. Willingale HL, Gardiner NJ, McLymont N, Giblett S, Grubb BD: Prostanoids synthesized by cyclo-oxygenase isoforms in rat spinal cord and their contribution to the development of neuronal hyperexcitability. Br J Pharmacol 1997;122: 1593-1604.
45. Cashman J, McAnulty G: Nonsteroidal anti-inflammatory drugs in perisurgical pain management. Mechanisms of action and rationale for optimum use. Drugs 1995;49:51-70.