Specificity of flurbiprofen and enantiomers for inhibition of prostaglandin synthesis in bovine iris/ciliary body

Prostaglandins and Other Lipid Mediators

Volumn 55, Issue 2-3, 1998, Pages 169-177

  Van Sorge, A A ^a   Van Delft, J L ^b   Bodelier, V M W ^c   Wijnen, P H ^d   Van Haeringen, N J ^c  

^a RIJNSTATE HOSPITAL   (Netherlands)

^b LEIDEN UNIVERSITY MEDICAL CENTER   (Netherlands)

^c NETHERLANDS INSTITUTE FOR NEUROSCIENCE   (Netherlands)

^d AKZO NOBEL CENTRAL RESEARCH   (Netherlands)

Author keywords

Bovine iris; Chiral inversion; Ciliary body; Cyclooxygenase; Flurbiprofen enantiomers; Prostaglandin E2

Indexed keywords

CYCLOOXYGENASE 1; EYE DROPS; FLURBIPROFEN; PROSTAGLANDIN E2;

ANIMAL TISSUE; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CATTLE; CILIARY BODY; CONCENTRATION RESPONSE; DRUG POTENCY; DRUG SPECIFICITY; DRUG STRUCTURE; ENANTIOMER; ENZYME ACTIVITY; ENZYME INHIBITION; IRIS; NONHUMAN; PROSTAGLANDIN SYNTHESIS INHIBITION; RACEMIC MIXTURE; STRUCTURE ACTIVITY RELATION; TOPICAL DRUG ADMINISTRATION;

EID: 0032001396     PISSN: 00906980     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0090-6980(98)00018-5     Document Type: Article

References (30)

1. Ambache N. Properties of irin, a physiological constituent of the rabbit's iris. J. Physiol. 135:1957;114-132.
2. Ambache N. Further studies on the preparation, purification and nature of irin. J. Physiol. 146:1959;255-294.
3. Eakins K.E., Whitelocke R.A.F., Perkins E.S., et al. Release of prostaglandins in ocular inflammation in the rabbit. Nature New Biol. 239:1972;248-249.
4. 2-like activity into the aqueous humor after paracentesis and its prevention by aspirin. Inv. Ophthalmol. Vis. Sci. 12:1973;939-942.
5. van Haeringen N.J., Oosterhuis J.A., van Delft J.L., Glasius E., Noach E.L. A comparison of the effects of non-steroidal compounds on the disruption of the blood-aqueous barrier. Exp. Eye Res. 35:1982;271-277.
6. DeWitt D.L., Meade E.A., Zeilhofer H.U. PGH Synthase isoenzyme selectivity The potential for safer nonsteroidal antiinflammatory drugs . Am. J. Med. 95:1993;40S-46S.
7. Mitchell J.A., Akarasereenont P., Thiemermann C., Flower R.J., Vane J.R. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc. Natl. Acad. Sci. USA. 90:1994;11693-11697.
8. Asakura T., Sano N., Stichi H. Prostaglandin synthesis and accumulation by porcine ciliary epithelium. J. Ocular Pharmacol. 8:1992;333-341.
9. Xie W., Robertson D.L., Simmons D.L. Mitogen-inducible prostaglandin G/H synthase A new target for nonsteroidal anti-inflammatory drugs . Drug Dev. Res. 25:1992;249-265.
10. Wilborn J., De Witt D.L., Peters-Golden M. Expression and role of cyclooxygenase isoforms in alveolar and peritoneal macrophages. Am. J. Physiol. 268:1995;L294-L301.
11. Feng L., Sun W., Xia Y., Tang W.W., Chanmugam P., Soyoola E., Wilson C.B., Hwang D. Cloning two isoforms of rat cyclooxygenase Differential regulation of their expression . Arch. Biochem. Biophys. 307:1993;361-368.
12. O'Neill G.P., Ford-Hutchinson A.W. Expression of mRNA for cyclooxygenase-1 and cyclooxygenase-2 in human tissues. FEBS Lett. 330:1993;156-160.
13. Slater D.M., Berger L., Newton R., Moore G.E., Bennett P.R. Expression of cyclo- oxygenase types1 and 2 in human fetal membranes at term. Am. J. Obstet. Gynecol. 172:1995;77-82.
14. Morham S.G., Langenbach R., Loftin C.D., Tiano H.F., Vouloumanos N., Jennette J.C., Mahler J.L., Kluckman K.D., Lee C.A., Smithies O. Prostaglandin synthase 2 gene disruption causes severe renal pathology in the mouse. Cell. 83:1995;473-482.
15. Langenbach R., Morham S.G., Tiano H.F., Loftin C.D., Ghanayem B.I., Chulada P.C., Mahler J.F., Lee C.A., Goulding E.H., Kluckman K.D., Kim H.S., Smithies O. Prostaglandin synthase 1 gene disruption in mice reduces arachidonic acid-induced inflammation and indomethacin-induced gastric ulceration. Cell. 83:1995;483-492.
16. Smith W.L., Willis A.L. Aspirin selectively inhibits prostaglandin production in human platelets. Nature New Biol. 31:1971;235-237.
17. Flach A.J. Cyclo-oxygenase inhibitors in ophthalmology. Therapeutic Review Survey Ophthalmol. 36:1992;259-284.
18. Hotchkiss M.L., Robin A.L., Pollack I.P., Quigley H.A. Nonsteroidal anti-inflammatory agents after argon laser trabeculoplasty A trial with flurbiprofen and indomethacin . Ophthalmology. 91:1984;969-976.
19. Pillunat L.E., Wagner P., Stodtmeister R. Comparison of topically applied prostaglandin synthesis inhibitors in Nd:Yag-laser surgery Preliminary results . Fortschr. Ophthalmol. 84:1987;583-586.
20. Geisslinger G., Menzel-Soglowek S., Schuster O., Brune K. Stereoselective high-performance liquid chromatographic determination of flurbiprofen in plasma. J. Chrom. 573:1992;163-167.
21. Gasper M.P., Berthod A., Nair U.B., Armstrong D.W. Comparison and modeling study of vancomycin, ristocetin A, and teicoplanin for CE enantioseparations. Anal. Chem. 68:1996;2501-2514.
22. Nielen M.B.W.F. Chiral separation of basic drugs using cyclodextrin-modified capillary zone electrophoresis. Anal. Chem. 65:1993;885-893.
23. Asakura T., Shichi H. Cytochrome P450-mediated prostaglandin ω/ω-1 hydroxylase activities in porcine ciliary epithelial cells. Exp. Eye Res. 55:1992;377-384.
24. Kulmacz R.J., Lands W.E.M. Stoichiometry and kinetics of the interaction of prostaglandin H synthase with anti-inflammatory agents. J. Biol. Chem. 260:1985;12572-12578.
25. Glaser K., Sung M., O'Neill K., Belfast M., Hartman D., Carlson R., Kreft A., Kubrak D., Hsiao C.-L., Weichman B. Etodolac selectively inhibits human prostaglandin G/H synthase 2 (PGHS-2) versus human PGHS-1. Eur. J. Pharmacol. 81:1995;107-111.
26. Markey C.M., Alward A., Weller P.E., Marnett L.J. Quantitative studies of hydroperoxide reduction by prostaglandin H synthase. J. Biol. Chem. 262:1987;6266-6279.
27. Evans A.M., Nation R.L., Sansom L.N., Bochner F., Somogyi A.A. Effect of racemic ibuprofen dose on the magnitude and duration of platelet cyclo-oxygenase inhibition Relationship between inhibition of thromboxane production and the plasma unbound concentration of S(+)-ibuprofen . Br. J. Clin. Pharmacol. 31:1991;131-138.
28. Menzel-Soglowek S., Geisslinger G., Beck W.S., Brune K. Variability of inversion of (R)-flurbiprofen in different species. J. Pharmac. Sci. 81:1992;888-891.
29. Carabaza A., Cabre F., Rotlan E., Gomez M., Gutierrez M., Garcia M.L., Mauleon D. Stereoslective inhibition of inducible cyclooxygenase by chiral nonsteroidal antiinflammatory drugs. J. Clin. Pharmacol. 36:1996;505-512.
30. Li Z.J., Grant D.J.W. Relationship between physical properties and crystal structures of chiral drugs. J. Pharm. Sci. 6:1997;1073-1078.