Evaluation of COX-1/COX-2 selectivity and potency of a new class of COX-2 inhibitors

European Journal of Pharmacology

Volumn 588, Issue 1, 2008, Pages 93-98

  Gierse, James ^a   Nickols, Maureen ^a   Leahy, Kathleen ^a   Warner, James ^a   Zhang, Yan ^b   Cortes Burgos, Luz ^a   Carter, Jeffery ^a   Seibert, Karen ^a   Masferrer, Jaime ^a  

^a PFIZER INC   (United States)

^b Kalypsys Inc   (United States)

Author keywords

COX 2; Cyclooxygenase; Inhibitor; Selectivity

Indexed keywords

6 CHLORO 7 (1,1 DIMETHYLETHYL) 2 (TRIFLUOROMETHYL) 2H 1 BENZOPYRAN 3 CARBOXYLIC ACID; CARRAGEENAN; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; GABAPENTIN; INDOMETACIN; INTERLEUKIN 1BETA; LIPOPOLYSACCHARIDE; MORPHINE; NAPROXEN; PARACETAMOL; PROSTAGLANDIN E2; RECOMBINANT ENZYME; SC 75416; THROMBOXANE;

ADJUVANT ARTHRITIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG BIOAVAILABILITY; DRUG DOSE COMPARISON; DRUG EFFICACY; DRUG HALF LIFE; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; EDEMA; FEMALE; HUMAN; HUMAN CELL; HYPERALGESIA; IC 50; INFLAMMATION; MALE; MUTATION; NEUROPATHIC PAIN; NONHUMAN; PRIORITY JOURNAL; PROSTAGLANDIN RELEASE; RAT; SINGLE DRUG DOSE; SYNOVIOCYTE; THROMBOCYTE;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ARTHRITIS, EXPERIMENTAL; ARTHRITIS, RHEUMATOID; BENZOPYRANS; BLOOD PLATELETS; CARRAGEENAN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; FIBROBLASTS; HUMANS; INFLAMMATION; LIGATION; MUTAGENESIS; PAIN MEASUREMENT; RATS; RATS, INBRED LEW; RATS, SPRAGUE-DAWLEY; RECOMBINANT PROTEINS; SPINAL NERVES; SUBSTRATE SPECIFICITY; SYNOVIAL MEMBRANE;

EID: 44249120031     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2008.03.057     Document Type: Article

References (26)

1. Bingham S., Beswick P.J., Bountra C., Brown T., Campbell I.B., Chessell I.P., Clayton N., Collins S.D., Davey P.T., Goodland H., Gray N., Haslam C., Hatcher J.P., Hunter A.J., Lucas F., Murkitt G., Naylor A., Pickup E., Sargent B., Summerfield S.G., Stevens A., Stratton S.C., and Wiseman J. The cyclooxygenase-2 inhibitor GW406381X [2-(4-ethoxyphenyl)-3-[4-(methylsulfonyl)phenyl]-pyrazolo[1,5-b]pyridazine] is effective in animal models of neuropathic pain and central sensitization. J. Pharmacol. Exp. Ther. 312 (2005) 1161-1169
2. Black W.C., Brideau C., Chan C.C., Charleson S., Chauret N., Claveau D., Ethier D., Gordon R., Greig G., Guay J., Hughes G., Jolicoeur P., Leblanc Y., Nicoll-Griffith D., Ouimet N., Riendeau D., Visco D., Wang Z., Xu L., and Prasit P. 2,3-Diarylcyclopentenones as orally active, highly selective cyclooxygenase-2 inhibitors. J. Med. Chem. 42 (1999) 1274-1281
3. Copeland R.A., Williams J.M., Giannaras J., Nurnberg S., Covington M., Pinto D., Pick S., and Trzaskos J.M. Mechanism of selective inhibition of the inducible isoform of prostaglandin G/H synthase. Proc. Natl. Acad. Sci. U. S. A. 91 (1994) 11202-11206
4. Crofford L.J. COX-1 and COX-2 tissue expression: implications and predictions. J. Rheumatol., Suppl. 49 (1997) 15-19
5. Gierse J.K., Hauser S.D., Creely D.P., Koboldt C., Rangwala S.H., Isakson P.C., and Seibert K. Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase. Biochem. J. 305 Pt 2 (1995) 479-484
6. Gierse J.K., Koboldt C.M., Walker M.C., Seibert K., and Isakson P.C. Kinetic basis for selective inhibition of cyclo-oxygenases. Biochem. J. 339 Pt 3 (1999) 607-614
7. Gierse J.K., Zhang Y., Hood W.F., Walker M.C., Trigg J.S., Maziasz T.J., Koboldt C.M., Muhammad J.L., Zweifel B.S., Masferrer J.L., Isakson P.C., and Seibert K. Valdecoxib: assessment of cyclooxygenase-2 potency and selectivity. J. Pharmacol. Exp. Ther. 312 (2005) 1206-1212
8. Hargreaves K., Dubner R., Brown F., Flores C., and Joris J. A new and sensitive method for measuring thermal nociception in cutaneous hyperalgesia. Pain 32 (1988) 77-88
9. Kishore N., Sommers C., Mathialagan S., Guzova J., Yao M., Hauser S., Huynh K., Bonar S., Mielke C., Albee L., Weier R., Graneto M., Hanau C., Perry T., and Tripp C.S. A selective IKK-2 inhibitor blocks NF-kappa B-dependent gene expression in interleukin-1 beta-stimulated synovial fibroblasts. J. Biol. Chem. 278 (2003) 32861-32871
10. Kowalski K.G., Olson S., Remmers A.E., and Hutmacher M.M. Modeling and simulation to support dose selection and clinical development of SC-75416, a selective COX-2 inhibitor for the treatment of acute and chronic pain. Clin. Pharmacol. Ther. (2007)
11. Masferrer J.L., and Seibert K. Regulation of prostaglandin synthesis by glucocorticoids. Receptor 4 (1994) 25-30
12. Masferrer J.L., Zweifel B.S., Manning P.T., Hauser S.D., Leahy K.M., Smith W.G., Isakson P.C., and Seibert K. Selective inhibition of inducible cyclooxygenase 2 in vivo is antiinflammatory and nonulcerogenic. Proc. Natl. Acad. Sci. U. S. A. 91 (1994) 3228-3232
13. Meade E.A., Smith W.L., and DeWitt D.L. Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs. J. Biol. Chem. 268 (1993) 6610-6614
14. Mitchell J.A., Akarasereenont P., Thiemermann C., Flower R.J., and Vane J.R. Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc. Natl. Acad. Sci. U. S. A. 90 (1993) 11693-11697
15. Patrignani P., Panara M.R., Sciulli M.G., Santini G., Renda G., and Patrono C. Differential inhibition of human prostaglandin endoperoxide synthase-1 and -2 by nonsteroidal anti-inflammatory drugs. J. Physiol. Pharmacol. 48 (1997) 623-631
16. Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., AndersonGd, Burton E.G., Cogburn J.N., Gregory S.A., Koboldt C.M., Perkins W.E., Seibert K., Veenhuizen A.W., Zhang Y.Y., and Isakson P.C. Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib). J. Med. Chem. 40 (1997) 1347-1365
17. Portanova J.P., Zhang Y., Anderson G.D., Hauser S.D., Masferrer J.L., Seibert K., Gregory S.A., and Isakson P.C. Selective neutralization of prostaglandin E2 blocks inflammation, hyperalgesia, and interleukin 6 production in vivo. J. Exp. Med. 184 (1996) 883-891
18. Riendeau D., Percival M.D., Boyce S., Brideau C., Charleson S., Cromlish W., Ethier D., Evans J., Falgueyret J.P., Ford-Hutchinson A.W., Gordon R., Greig G., Gresser M., Guay J., Kargman S., Leger S., Mancini J.A., O'Neill G., Ouellet M., Rodger I.W., Therien M., Wang Z., Webb J.K., Wong E., Chan C.C., et al. Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor. Br. J. Pharmacol. 121 (1997) 105-117
19. Schafers M., Marziniak M., Sorkin L.S., Yaksh T.L., and Sommer C. Cyclooxygenase inhibition in nerve-injury- and TNF-induced hyperalgesia in the rat. Exp. Neurol. 185 (2004) 160-168
20. Seibert K., and Masferrer J.L. Role of inducible cyclooxygenase (COX-2) in inflammation. Receptor 4 (1994) 17-23
21. Seibert K., Zhang Y., Leahy K., Hauser S., Masferrer J., Perkins W., Lee L., and Isakson P. Pharmacological and biochemical demonstration of the role of cyclooxygenase 2 in inflammation and pain. Proc. Natl. Acad. Sci. U. S. A. 91 (1994) 12013-12017
22. Seibert K., Zhang Y., Leahy K., Hauser S., Masferrer J., and Isakson P. Distribution of COX-1 and COX-2 in normal and inflamed tissues. Adv. Exp. Med. Biol. 400A (1997) 167-170
23. Smith W.L., and Song I. The enzymology of prostaglandin endoperoxide H synthases-1 and -2. Prostaglandins Other Lipid Mediat. 68-69 (2002) 115-128
24. Smith C.J., Zhang Y., Koboldt C.M., Muhammad J., Zweifel B.S., Shaffer A., Talley J.J., Masferrer J.L., Seibert K., and Isakson P.C. Pharmacological analysis of cyclooxygenase-1 in inflammation. Proc. Natl. Acad. Sci. U. S. A. 95 (1998) 13313-13318
25. Walker M.C., Kurumbail R.G., Kiefer J.R., Moreland K.T., Koboldt C.M., Isakson P.C., Seibert K., and Gierse J.K. A three-step kinetic mechanism for selective inhibition of cyclo-oxygenase-2 by diarylheterocyclic inhibitors. Biochem. J. 357 (2001) 709-718
26. Zhang Y., Shaffer A., Portanova J., Seibert K., and Isakson P.C. Inhibition of cyclooxygenase-2 rapidly reverses inflammatory hyperalgesia and prostaglandin E2 production. J. Pharmacol. Exp. Ther. 283 (1997) 1069-1075