Cox-2-selective inhibitors: The new super aspirins

Molecular Pharmacology

Volumn 55, Issue 4, 1999, Pages 625-631

  DeWitt, David L ^a  

^a Michigan State University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 [5 (4 BROMOPHENYL) 3 TRIFLUOROMETHYL 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 5 (4 FLUOROPHENYL) 1 [(4 METHYLSULFONYL)PHENYL] 3 TRIFLUOROMETHYLPYRAZOLE; 5 BROMO 2 (4 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL)THIOPHENE; 6 (2,4 DIFLUOROPHENYLTHIO) 5 METHANESULFONAMIDO 1 INDANONE; ACETYLSALICYLIC ACID; CELECOXIB; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITOR; DICLOFENAC; FLURBIPROFEN; IBUPROFEN; KETOPROFEN; MECLOFENAMIC ACID; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; NAPROXEN; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTACYCLIN; PROSTAGLANDIN; PYRAZOLE DERIVATIVE; ROFECOXIB; STILBENE; THROMBOXANE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIPYRETIC ACTIVITY; ARTHRITIS; ENZYME INHIBITION; GENE; HUMAN; NONHUMAN; PAIN; PRIORITY JOURNAL; PROSTAGLANDIN SYNTHESIS; REVIEW;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ASPIRIN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; DRUG DESIGN; HUMANS; ISOENZYMES; MEMBRANE PROTEINS; MODELS, MOLECULAR; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES;

EID: 0032916736     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (35)

1. Barnett J, Chow J, Ives D, Chiou M, Mackenzie R, Osen E, Nguyen B, Tsing S, Bach C, Freire J, Chan H, Sigal E and Ramesha C (1994) Purification, characterization and selective inhibition of human prostaglandin G/H synthase 1 and 2 expressed in the baculovirus system. Biochim Biophys Acta 1209:130-139.
2. Bhattacharyya DK, Lecomte M, Rieke CJ, Garavito M and Smith WL (1996) Involvement of arginine 120, glutamate 524, and tyrosine 355 in the binding of arachidonate and 2-phenylpropionic acid inhibitors to the cyclooxygenase active site of ovine prostaglandin endoperoxide H synthase-1. J Biol Chem 271:2179-2184.
3. Chan CC, Boyce S, Brideau C, Ford-Hutchinson AW, Gordon R, Guay D, Hill RG, Li CS, Mancini J and Penneton M (1995) Pharmacology of a selective cyclooxygenase-2 inhibitor, L-745,337: A novel nonsteroidal anti-inflammatory agent with an ulcerogenic sparing effect in rat and nonhuman primate stomach. J Pharmacol Exp Ther 274:1531-1537.
4. Chase M (1998) The race to make gentler painkiller faces high standards. Wall Street Journal, May 30.
5. Copeland RA, Williams JM, Giannaras J, Nurnberg S, Covington M, Pinto D, Pick S and Trzaskos JM (1994) Mechanism of selective inhibition of the inducible isoform of prostaglandin G/H synthase. Proc Natl Acad Sci USA 91:11202-11206.
6. Ehrich E, Schnitzer T, Kivitz A, Weaver A, Wolfe F, Morrison B, Zeng Q, Bolognese J and Seidenberg B (1997) MK-966, a highly selective Cox-2 inhibitor, was effective in the treatment of osteoarthritis (OA) of the knee and hip in a 6-week placebo controlled study. Arthritis Rheum 40 (Suppl S):330.
7. Futaki N, Yoshikawa K, Hamasaka Y, Arai I, Higuchi S, Iizuka H and Otomo S (1993) NS-398, a novel non-steroidal anti-inflammatory drug with potent analgesic and antipyretic effects, which causes minimal stomach lesions. Gen Pharmacol 24:105-110.
8. Gans KR, Galbraith W, Roman RJ, Haber SB, Kerr JS, Schmidt WK, Smith C, Hewes WE and Ackerman NR (1990) Anti-inflammatory and safety profile of DuP 697, a novel orally effective prostaglandin synthesis inhibitor. J Pharmacol Exp Ther 254:180-187.
9. Gierse JK, Hauser SD, Creely DP, Koboldt C, Rangwala SH, Isakson PC and Seibert K (1995) Expression and selective inhibition of the constitutive and inducible forms of human cyclooxygenase. Biochem J 305 (Pt 2):479-484.
10. Gierse JK, McDonald JJ, Hauser SD, Rangwala SH, Koboldt CM and Seibert K (1996) A single amino acid difference between cyclooxygenase-1 (COX-1) and -2 (COX-2) reverses the selectivity of COX-2 specific inhibitors. J Biol Chem 271: 15810-15814.
11. Greig GM, Francis DA, Falgueyret JP, Ouellet M, Percival MD, Roy P, Bayly C, Mancini JA and O'Neill GP (1997) The interaction of arginine 106 of human prostaglandin G/H synthase-2 with inhibitors is not a universal component of inhibition mediated by nonsteroidal anti-inflammatory drugs. Mol Pharmacol 52:829-838.
12. Guo Q, Wang LH, Ruan KH and Kulmacz RJ (1996) Role of Val509 in time-dependent inhibition of human prostaglandin H synthase-2 cyclooxygenase activity by isoform-selective agents. J Biol Chem 271:19134-19139.
13. Kargman S, Wong E, Greig GM, Falgueyret JP, Cromlish W, Ethier D, Yergey JA, Riendeau D, Evans JF, Kennedy B, Tagari P, Francis DA and O'Neill GP (1996b) Mechanism of selective inhibition of human prostaglandin G/H synthase-1 and -2 in intact cells. Biochem Pharmacol 52:1113-1125.
14. Kujubu DA, Fletcher BS, Varnum BC, Lim RW and Herschman HR (1991) TIS10, a phorbol ester tumor promoter inducible mRNA from Swiss 3T3 cells, encodes a novel prostaglandin synthase/cyclooxygenase homologue. J Biol Chem 266:12866-12872.
15. Kurumbail RG, Stevens AM, Gierse JK, McDonald JJ, Stegeman RA, Pak JY, Gildehaus D, Miyashiro JM, Penning TD, Seibert K, Isakson PC and Stallings WC (1996) Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents. Nature (London) 384:644-648.
16. Lane NE (1997) Pain management in osteoarthritis: The role of Cox-2 inhibitors. J Rheumatol 24 (Suppl 49):20-24.
17. Leblanc Y, Gauthier JY, Ethier D, Guay J, Mancini J, Riendeau D, Tagari P, Vickers P, Wong E and Prasit P (1995) Synthesis and biological evaluation of 2,3-diarylthiopenes as selective Cox-2 and Cox-1 inhibitors. Bioorg Med Chem Lett 5:2123-2128.
18. Lipsky PE and Isakson PC (1997) Outcome of specific Cox-2 inhibition in rheumatoid arthritis. J Rheumatol 24 (Suppl 49):9-14.
19. Luong C, Miler A, Barnett J, Chow J, Ramesha C and Browner MF (1996) Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat Struct Biol 3:927-933.
20. Mancini JA, Riendeau D, Falgueyret JP, Vickers PJ and O'Neill GP (1995) Arginine 120 of prostaglandin G/H synthase-1 is required for the inhibition by nonsteroidal anti-inflammatory drugs containing a carboxylic acid moiety. J Biol Chem 270: 29372-29377.
21. Marnett JL and Kalgutkar AS (1998) Design of selective inhibitor of cyclooxygenase-2 as non-ulcerogenic anti-inflammatory agents. Curr Opin Chem Biol 2:482-490.
22. Masferrer JL, Zweifel BS, Manning PT, Hauser SD, Leahy KM, Smith WG, Isakson PC and Seibert K (1994) Selective inhibition of inducible cyclooxygenase 2 in vivo is anti-inflammatory and nonulcerogenic. Proc Natl Acad Sci USA 91:3228-3232.
23. Meade EA, Smith WL and DeWitt DL (1993) Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other nonsteroidal anti-inflammatory drugs. J Biol Chem 268:6610-6614.
24. O'Neill GP, Mancini JA, Kargman S, Yergey J, Kwan MY, Falgueyret JP, Abramovitz M, Kennedy BP, Ouellet M and Cromlish W (1994) Overexpression of human prostaglandin G/H synthase-1 and -2 by recombinant vaccinia virus: Inhibition by nonsteroidal anti-inflammatory drugs and biosynthesis of 15-hydroxyeicosatetraenoic acid. Mol Pharmacol 45:245-254.
25. Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM, Rogers RS, Rogier DJ, Yu SS, Anderson GD, Burton EG, Cogburn JN, Gregory SA, Koboldt CM, Perkins WE, Seibert K, Veenhuizen AW, Zhang YY and Isakson PC (1997) 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 (SC58635, celecoxib). J Med Chem 40:1347-1365.
26. 2 synthase-1. Nature (London) 367:243-249.
27. Prasit P and Riendeau D (1997) Selective cyclooxygenase-2 inhibitors, in Annual Reports in Medicinal Chemistry: 32 (Hagmann WK ed) pp 211-220, Academic Press, San Diego.
28. Riendeau D, Boyce SP MD, Brideau C, Charleson W, Cromlish W, Ethier D, Evans J, Galgueyret JP, Ford-Huchinson AW, Gordon R, Greig G, Gresser M, Guay J, Kargman S, Leger S, Manicini JA, O'Neill G, Ouellet M, Rodger IW, Therien M, Wang Z, Webb JK, Wong I, Xu L, Young RN, Zamboni R, Prasit P and Chan CC (1997) Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective Cox-2 inhibitor. Br J Pharmacol 121:105-117.
29. Rome LH and Lands WEM (1975) Structural requirements for time-dependent inhibition of prostaglandin biosynthesis by anti-inflammatory drugs. Proc Natl Acad Sci USA 72:4863-4865.
30. Seibert K, Zhang Y, Leahy K, Hauser S, Masferrer J, Perkins W, Lee L and Isakson P (1994) Pharmacological and biochemical demonstration of the role of cyclooxygenase 2 in inflammation and pain. Proc Natl Acad Sci USA 91:12013-12017.
31. Simmons DL, Levy DB, Yannoni Y and Erikson RL (1989) Identification of a phorbol ester-repressible v-src-inducible gene. Proc Natl Acad Sci USA 86:1178-1182.
32. Smith WL, Garavito RM and DeWitt DL (1996) Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2. J Biol Chem 271:33157-33160.
33. Willard J, Lange RA and Hillis LD (1992) The use of aspirin in ischemic heart disease. N Engl J Med 327:175-181.
34. Wong E, Bayly C, Waterman HL, Riendeau D and Mancini JA (1997) Conversion of prostaglandin G/H synthase-1 into an enzyme sensitive to PGHS-2-selective inhibitors by a double His513 to Arg and Ile523 to Val mutation. J Biol Chem 272:9280-9286.
35. Zhao SZ, Hatoum HT, Hubbard RC, Koepp RJ, Dedhiya SD and Geis S (1997) Effect of celecoxib, a novel cox-2 inhibitor, on health-related quality of life in patients with osteoarthritis of the knee. Arthritis Rheum 40 (Suppl S):348.