COX-2 inhibitors: Current state and prospects;COX-2-inhibitoren: Aktueller stand und ausblick

Pharmazie in Unserer Zeit

Volumn 29, Issue 2, 2000, Pages 100-106

  Dannhardt, Gerd ^a,b,c   Hahn, Linda ^d  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

^c JOHANNES GUTENBERG UNIVERSITY   (Germany)

^d GOETHE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 FLUOROPHENYL) 2 [(4 METHYLSULFONYL)PHENYL]CYCLOPENTENE; 4 [5 (4 BROMOPHENYL) 3 TRIFLUOROMETHYL 1H PYRAZOL 1 YL]BENZENESULFONAMIDE; 5 BROMO 2 (4 FLUOROPHENYL) 3 (4 METHYLSULFONYLPHENYL)THIOPHENE; 6 (2,4 DIFLUOROPHENYLTHIO) 5 METHANESULFONAMIDO 1 INDANONE; ACETYLSALICYLIC ACID; ANTIINFLAMMATORY AGENT; CELECOXIB; CL 1004; CYCLOOXYGENASE 2 INHIBITOR; ETODOLAC; FLOSULIDE; FLURBIPROFEN; IBUPROFEN; INDOMETACIN; L 748780; L 761066; MEFENAMIC ACID; MELOXICAM; N (2 CYCLOHEXYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; NIMESULIDE; NONSTEROID ANTIINFLAMMATORY AGENT; PIROXICAM; ROFECOXIB; RS 104894; RS 57067; S 2474;

DRUG CONTRAINDICATION; DRUG INDICATION; DRUG MECHANISM; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME INHIBITOR INTERACTION; HUMAN; HUMAN CELL; HUMAN TISSUE; INHIBITION KINETICS; REVIEW; STRUCTURE ACTIVITY RELATION;

CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; HUMANS; ISOENZYMES; MEMBRANE PROTEINS; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES;

EID: 0034009775     PISSN: 00483664     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1615-1003(200002)29:2<100::AID-PAUZ100>3.0.CO;2-V     Document Type: Review

References (52)

1. Vane, J.R.: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs, Nat. New Biol. 231 (1971), 232-235.
2. Smith, W.L., Willis, A.L.: Aspirin selectively inhibits prostaglandin production in human platelets, Nat. New Biol. 231 (1971), 235-237.
3. Mutschler, E.: Arzneimittelwirkungen: Lehrbuch der Pharmakologie und Toxikologie. 7. Auflage, Stuttgart, Wiss. Verl. Ges., 1996.
4. Xie, W., Chipman, J.G., Robenson, D.L., Erickson, R.L., Simmons, D.L.: Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing, Inflamm. Res. 47 Suppl. 2 (1998), 78-87.
5. Crofford, L.J.: Inflammation. The role of COX-2 in Health and Disease. Paris 1999.
6. Masferrer, J.L., Zweifel, B.S., Manning, P.T., Hauser, S.D., Leahy, K.M., Smith, W.G., Isakson, P.C., Seibert, K.: Selective inhibition of inducible cyclooxygenase-2 in vivo is antiinflammatory and nonulcerogenic, Proc. Natl Acad. Sci USA 91 (1994), 3228-3232.
7. Engelhardt, G., Bögel, R., Schnitzer, C., Utzmann, R.: Meloxicam: influence on arachidonic acid metabolism, part I: in vitro findings, Biochem. Pharmacol. 51 (1996), 21-28.
8. Lancuville, O., Breuer, D.K., Dewitt, D.L., Hla, T., Funk, C.D., Smith, W.L.: Differential inhibition of human prostaglandin endoperoxide H synthase1 and -2 by nonsteroidal anti-inflammatory drugs, J. Pharmacol. Exp. Ther. 271 (1994), 927-934.
9. Patrignani, P., Panara, M.R., Sciulli, M.G., Santini, G., Renda, G., Patrono, C.: Differential inhibition of human prostaglandin endoperoxide synthase-1 and -2 by nonsteroidal anti-inflammatory drugs, J. Physiol. Pharmacol. 48 (1997), 623-631.
10. Kurumbail, R.G., Stevens, A.M., Gierse, J.K., McDonald, J.J., Stegeman, R.A., Pak, J.Y., Gildehaus, D., Miyashiro, J.M., Penning, T.D., Seibert, K., Isakson, P.C., Stalling, W.C.: Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents, Nature 384 (1996), 644-648.
11. 523 → Val mutation, J. Biol. Chem. 272 (1997), 9280-9286.
12. Griswold, D.E., Adams, J.L., Constitutive cyclooxygenase (COX-1) and inducible cyclooxygenase (COX-2): rationale for selective inhibition and progress to date, Med. Res. Rev. 16 (1996), 181-206.
13. Copeland, R.A., Williams, J.M., Giannaras, J., Nurnberg, S., Convington, M., Pinto, D., Pick, S., Trzaskos, J.M.: Mechanism of selective inhibition of the inducible isoform of prostaglandin G/H synthase, Proc. Natl. Acad. Sci. USA 91 (1994), 11202-11206.
14. So, O.Y., Scarafia, E., Mak, A.Y., Callan, O.H., Swinney, D.C.: The dynamics of prostaglandin H synthases. Studies with prostaglandin H synthase 2 Y355F unmask mechanisms of time-depent inhibition and allosteric activation, J. Biol. Chem. 273 (1998), 5801-5807.
15. Swinney, D.C., Mak, A.Y., Barnett, J., Ramesha, C.S.: Differential allosteric regulation of prostaglandin H synthase 1 and 2 by arachidonic acid, J. Biol. Chem. 272 (1997), 12393-12398.
16. Gierse, J.K., McDonald, J.J., Hauser, S.D., Rangwala, S.H., Koboldt, C.M., Seibert, K.: 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 (1996), 15810-15814.
17. Dannhardt, G., Laufer, S.: Structural approches to explain the selectivity of COX-2 inhibitors: is there a common pharmacophore?, Curr. Med. Chem. 7 (2000), in press.
18. Harrington, J.K., Robertson, J.E., Kvam, D.C., Hamilton, R.R., McGurran, K.T., Trancik, R.J., Swingle, K.F., Moore, G.G., Gerster, J.E: Antiinflammatory agents. I. 3-Benzoylfluoralkanesul-fonanilides, J. Med. Chem. 13 (1970), 137.
19. Futaki, N., Takahashi, S., Yokoyama, M., Arai, I., Higuchi, S., Otomo, S.: NS-398, a new anti-inflammatory agent selectively inhibits prostaglandin G/H synthase / cyclooxygenase (COX-2) activity in vitro, Prostaglandins 47 (1994), 55-59.
20. Huff, R., Collins, P., Kramer, S., Seibert, K., Koboidt, C., Gregory, S., Isakson, P.: A structural feature of N-[2-(cyclohexyloxy)4-nitrophenyl]-methansulfonamid (NS-398) that governs ist selectivity and affinity for cyclooxygenase 2 (COX-2), Inflamm. Res. 44 Suppl. 2 (1995), 145-146.
21. Davis, R., Grogden, R.N., Drugs 48 (1994), 431.
22. Garcia Rodriguez, L.A., Arch. Int. Med. 158 (1998), 33.
23. Pairet, M., van Ryn, J., Distel, M.: Overview of COX-2 in inflammation: from the biology to the clinic. In: Willoughby, D.A., Tomlinson, A. [Eds.]: Inducible enzymes in the inflammatory response. Birkhäuser Verlag Basel/Switzerland, 1999.
24. Li, C.S., Black, W.C., Chan, C.C., Ford-Hutchinson, A.W., Gauthier, J.Y., Gordon, R., Guay, D., Kargman, S., Lau, C.K., Mancini, J., Ouimet, N., Roy, P., Vickers, P., Wong, E., Young, R.N., Zamboni, R., Prasit, P.: Cyciooxygenase-2 inhibitors. Synthesis and pharmacological activities of 5-methanesolfonamido-1-indanone derivatives, J. Med. Chem. 38 (1995), 4897-4905.
25. Prasit, P., Black, W.C., Chan, C.C. et al, J. Med. Chem. Res. 5 (1995), 364.
26. st communication: Antiinflammatory, analgesic and other related properties, Arzneim. Forsch. Drug Res. 42 (1992), 935-945.
27. Talley, J.J.: Selective inhibitors of cyclooxygenase-2, Exp. Opin. Ther. Patents 7 (1997), 55-62.
28. Li, J.J., Anderson, G.D., Burton, E.G., Cogburn, J.N., Collins, J.T., Garland, D.J., Gregory, S.A., Huang, H.C., Isakson, P.C., Kobold, C.M., Logusch, E.W., Norton, M.B., Perkins, W.E., Reinhard, E.J., Seibert, K., Veenhuizen, A. W., Zhang, Y., Reitz, D.B.: 1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents, J. Med. Chem. 38 (1995), 4570-4578.
29. Gans, K.R., Galbraith, W., Roman, R.J., Haber, S.B., Kerr, J.S., Schmidt, W.K., Smith, C., Hewes, W.E., Ackerman, N.R.: Anti-inflammatory and safety profile of DuP 697, a novel orally effective prostaglandin synthesis inhibitor, J. Pharmacol. Exp. Ther. 254 (1990), 180-187.
30. Hubbard, R.C., Koepp, R.J., Yu, S., Talwalker, S., Geis, G.S., Wiesenhutter, C.W., Makarowski, W.S., Paulus, H.A.: SC-58635 (celecoxib), a novel COX-2 selective inhibitor, is effective as a treatment for osteoarthritis (OA) in a short-term pilot study, Arthritis. Rheum. 39 Suppl (1996), Abstr. 1188.
31. Simon, L.S., Lanza, F.L., Lipsky, P.E., Hubbard, R.C., Tolwalker, S., Schwarz, B.D., Isakson, P.C., Geis, G.S.: Preliminary study of the safety and efficacy and safety in two placebo-controlled trials in osteoarthritis and rheumatoid arthritis, and studies of gastrointestinal and platelet effects, Arthritis Rheum. 41 (1998), 1591-1602.
32. Ehrlich, E.W., Dallob, A., De Lepeleire, I., Van Hecken, A., Riendeau, D., Yuan, W., Porras, A., Wittreich, J., Seiboid, J., De Schepper, P., Mehlisch, D.R., Gertz, B.J.: Characterization of rofecoxib as a cyclooxygenasc-2 isoform inhibitor and demonstration of analgesia in the dental pain model, Clin. Pharmacol. Ther. 65 (1999), 336-347.
33. Black, W.C., Bayly, M., Chan, C.C., Charleson, S., Denis, D., Gauthier, J.Y., Gordon, R., Guay, D., Kargman, S., Lau, C.K., Leblanc, Y., Mancini, J., Oullet, M., Percival, D., Roy, P., Skorey, K., Tagari, P., Vickers, P., Wong, E., Xu, L., Prasit, P.: From indomethacin to a selective COX-2 inhibitor: development of indolalkanoic acids as potent and selective cyclooxygenase-2 inhibitors, Bioorg. Med. Chem. Lett. 6 (1996), 725-730.
34. Kalgutkar, A.S., Crews, B.C., Rowlinson, S.W., Gamer, C., Seibert, K., Marnett, L.J.: Aspirinlike molekules that covalently inactivate cyclooxygenase-2, Science 280 (1998), 1268-1270.
35. Distel, M., Mueller, C., Bluhmki, E., Fries, J.: Safety of meloxicam: a global analysis of clinical trials, Br. J. Rheumatol. 35 (1996), 68-77.
36. Hawkey, C., Kahan, A., Steinbrück, K., Alegre, C., Baumelou, E., Bégaud, B., Dequeker, J., Isomaki, H., Littlejohn, G., Mau, J., Papazoglou, S.: Gastrointestinal tolerability of meloxicam compared to diclofenac in osteoarthritis patients, International MELISSA Study Group. Meloxicam Large-scale International Study Safety Assessment, Br. J. Rheumatol. 37 (1998), 937-945.
37. Dequeker, J., Hawkey, C., Kahan, A., Steinbruck, K., Alegre, C., Baumelou, E., Bégaud, B., Dequeker, J., Isomaki, H., Littlejohn, G., Mau, J., Papazoglou, S.: Improvement in gastrointestinal torelability of the selective cyclooxygenase(COX)-2 inhibitor meloxicam, compared with piroxicam: results of the Safety and Efficacy Large-scale Evaluation of COX-inhibiting Therapies (SELECT) trial in osteoarthritis, Br. J. Rheumatol. 37 (1998), 946-951.
38. Lanza, F., Rack, M.F., Lynn, M., Wolf, J., Sanda, M.: An endoscopie comparison of the effects of etodolac, indometacin, ibuprofen, naproxen and placebo on the gastrointestinal mucosa, J. Rheumatol. 14 (1987), 338-341.
39. Beiche, F., Scheuerer, S., Brune, K., Geisslinger, G., Goppelt-Struebe, M.: Upregulation of cyclooxygenase-2 mRNA in the rat spinal cord following peripheral inflammation, FEBS Lett. 390 (1996), 165-169.
40. Asano, K., Lilly, C.M., Drazen, J.M.: Prostaglandin G/H synthase-2 is the constitutive and dominant isoform in cultured human lung epithelial cells, Am. J. Physiol. 271 (1996), L126-131.
41. Morham, S.G., Langenbach, R., Loftin, C.D., Tiano, H.F., Vouloumanos, N., Jennette, J.C., Mahler, J.F., Kluckman, K.D., Ledford, A., Lee, C.A.: Prostaglandin synthase 2 gene disruption causes severe renal pathology in the mouse, Cell 83 (1995), 473-482.
42. Harris, R.C., McKanna, J.A., Akai, Y., Jacobson, H.R., Dubois, R.N., Breyer, M.D.: Cyclooxygenase-2 is associated with the macula densa of rat kidney and increases with solt restriction, J. Clin. Invest. 94 (1994), 2504-2510.
43. Chakraborty, I., Das, S.K., Wang, J., Dey, S.K.: Developmental expression of the cyclooxygenase-1 and cyclooxygenase-2 genes in the periimplantation mouse uterus and their differential regulation by the blastocyst and ovarian steroids, J. Mol. Endocrinol. 16 (1996), 107-122.
44. Mitchel, J.A., Evans, T.W.: Cyclooxygenase-2 as a therapeutic target, Inflamm. Res. 47 Suppl. 2 (1998), 88-92.
45. Mtzuno, H., Sakamoto, C., Matsuda, K., Wada, K., Uchida, T., Noguchi, H., Akamatsu, T., Kasuga, M.: Induction of cyclooxygenase 2 in gastric mucosal lesions and ist inhibition by the specific antagonist delays healing in mice, Gastroenterology 112 (1997), 387-397.
46. Sawdy, R., Slater, D., Fisk, N., Ecmonds, D.K., Bennett, P.: Use of a cvclooxvgenase type-2-selective non-steroidal anti-intlammatory agent to prevent preterm delivery, Lancet 350 (1997), 265-266.
47. Stewart, W.F., Kiwas, C., Corrada, M., Metter, E.J.: Risk of Alzheimer's disease and duration of NSAID use, Neurology 48 (1997), 626-632.
48. Kutchera, W., Jones, D.A., Matsunami, N., Groden, J., McIntyre, T.M., Zimmerman, G.A., White, R.L., Prescott, S.M.: Prostaglandin H synthase 2 is expressed abnormally in human colon cancer: evidence for a transcriptional effect, Proc. Natl. Acad. Sci. U.S.A. 93 (1996), 4816-4820.
49. 7:6 knockout mice by inhibition of cyclooxygenasc 2 (COX-2), Cell 87 (1996), 803-809.
50. Parrett, M.L., Harris, R.E., Joarder, F.S., Ross, M.S., Clausen, K.P., Robertson, F.M.: Cyclooxygenase-2 gene expression in human breast cancer, Int. J. Oncol. 10 (1997), 503-507.
51. Ristimäki, A., Honkanen, N., Jänkälä, H., Sipponen, P., Härkönen, M.: Expression of cyclooxygenase-2 in human gastric carcinoma. Cancer Res. 57 (1997), 1276-1280.
52. van Ryn, J., Trummlitz, G., Pairet, M.: COX-2 selectivity and inflammatory processes, Curr. Med. Chem, 7 (2000), in press.