N-[[(5-methyl-3-phenylisoxazol-4-yl)phenyl] sulfonyl]propanamide, sodium salt, parecoxib sodium: A potent and selective inhibitor of COX-2 for parenteral administration

Journal of Medicinal Chemistry

Volumn 43, Issue 9, 2000, Pages 1661-1663

  Talley, John J ^a   Bertenshaw, Stephen R ^a   Brown, David L ^a   Carter, Jeffery S ^a   Graneto, Matthew J ^a   Kellogg, Michael S ^a   Koboldt, Carol M ^a   Yuan, Jinhua ^a   Zhang, Yan Y ^a   Seibert, Karen ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOOXYGENASE 2 INHIBITOR; PARECOXIB; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; DRUG ACTIVITY; DRUG EFFECT; DRUG POTENCY; DRUG STRUCTURE; ENZYME INHIBITION; LETTER; NONHUMAN;

ACYLATION; ANIMALS; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; CYCLOOXYGENASE INHIBITORS; DOGS; INJECTIONS; ISOENZYMES; ISOXAZOLES; MACACA FASCICULARIS; MALE; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; RATS;

EID: 0034030366     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000069h     Document Type: Letter

References (19)

1. DeWitt, D. L. Cox-2 Selective Inhibitors: The New Super Aspirins. Mol. Pharmacol. 1999, 55, 625-631.
2. Talley, J. J. Selective Inhibitors of COX-2. In Progress in Medicinal Chemistry 36; King, F. D., Oxford, A., Eds.; Elsevier: Amsterdam, 1999; pp 201-234.
3. Kalgutkar, A. S. Selective cyclooxygenase-2 inhibitors as non-ulcerogenic antiinflammatory agents. Exp. Opin. Ther. Patents 1999, 8, 831-849.
4. 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.; Miyahiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors: Identification of 4-[5-(4-Methylphe-nyl)-3-(trifluoromethyl)-1H-pyrazol-1-y1]benzenesulfonamide (SC-58635, Celecoxib). J. Med. Chem. 1997, 40, 1347-1365.
5. Prasit, P.; Wang, Z.; Brideau, C.; Chan, C.-C.; Charleson, S.; Cromlish, W.; Ethier, D.; Evans, J. F.; Ford-Hutchinson, A. W.; Gauthier, J. Y.; Gordon, R.; Guay, J.; Gresser, M.; Kargman, S.; Kennedy, B.; Leblanc, Y.; Leger, S.; Mancini, J.; O'Neil, G. P.; Quellet, M.; Percival, M. D.; Perrier, H.; Riendeau, D.; Rodger, I.; Tagari, P.; Therien, M.; Vickers, P.; Wong, E.; Xu, L.-J.; Young, R. N.; Zamboni, R.; Boyce, S.; Rupniak, N.; Forrest, M.; Visco, D.; Patrick, D. The discovery of rofecoxib, [MK 966, Vioxx, 4-(4′-methylsulfonylphenyl)-3-phenyl-2(5H)-furanone], an orally active cyclooxygenase-2 inhibitor. Bioorg. Med. Chem. Lett. 1999, 9, 1773-1778.
6. Muchowski, J. M.; Unger, S. H.; Ackrell, J.; Cheung, P.; Cooper, G. F.; Cook, J.; Gallegra, P.; Halpern, O.; Koehler, R.; Kluge, A. F.; Van Horn, A. R.; Antonio, Y.; Carpio, H.; Franco, F.; Galeazzi, E.; Garcia, I.; Greenhouse, R.; Guzman, A.; Iriarte, J.; Leon, A.; Pena, A.; Perez, V.; Valdez, D.; Ackerman, N.; Ballaron, S. A.; Krishna Murthy, D. V.; Rovito, J. R.; Tomolonis, A. J.; Young, J. M.; Rooks, W. H. Synthesis and Antiinflammatory and Analgesic Activity of 5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-α]pyrrole-1-carboxylic Acids and Related Compounds. J. Med. Chem. 1985, 28, 1037-1049.
7. Guzman, A.; Yuste, F.; Toscano, R. A.; Young, J. M.; Van Horn, A. R. ; Muchowski, J. M. Absolute Configuration of (-)-5-Benzoyl-1,2-dihydro-3H-pyrrolo[1,2-α]pyrrole-1-carboxylic Acid, the Active Enantiomer of Ketorolac. J. Med. Chem. 1986, 29, 589-591.
8. 2 Production. J. Pharmacol. Exp. Ther. 1997, 283, 1069-1075.
9. Strom, B. L.; Berlin, J. A.; Kinman, J. L.; Spitz, P. W.; Hennessy, S.; Feldman, H.; Kimmel, S.; Carson, J. L. Parenteral ketorolac and risk of gastro-intestinal and oprative side bleeding: A postmarketing survey. J. Am. Med. Assoc. 1996, 275, 376-382.
10. Choo, V.; Lewis, S. Ketorolac doses reduced. Lancet 1993, 342, 109.
11. Lewis, S. Ketorolac in Europe. Lancet 1994, 343, 784.
12. Jett, M. F.; Ramesha, C. S.; Brown, C. D.; Chiu, S.; Emmett, C.; Voronin, T.; Sun, T.; O'Yang, C.; Hunter, J. C.; Eglen, R. M.; Johnson, R. M. Characterization of the Analgesic and Antiinflammatory Activities of Ketorolac and Its Enantiomers in the Rat. J. Pharmacol. Exp. Ther. 1999, 288, 1288-1297.
13. Talley, J. J.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Rogers, R. S.; Shaffer, A. F.; Zhang, Y. Y.; Zweifel, B. S.; Seibert, K. 4-[5-Methyl-3-phenylisoxazol-4-yl]benzenesulfonamide, Valdecoxib: A Potent and Selective Inhibitor of COX-2. J. Med. Chem. 2000, 43, 775-777.
14. Larsen, J. D.; Bundgaard, H. Prodrug forms of the sulfonamide group. I. Evaluation of N-acyl derivatives, N-sulfonamidines, N-sulfonylsulfilimines and sulfonylureas as possible prodrug derivatives. Int. J. Pharm. 1987, 37, 87-95.
15. Larsen, J. D.; Bundgaard, H.; Lee, V. H. L. Prodrug forms for the sulfonamide group. II. Water soluble amino acid derivatives of N-methylsulfonamides as possible prodrugs. Int. J. Pharm. 1988, 47, 103-110.
16. Masferrer, J. L.; Zweifel, B. S.; Manning, P. T.; Hauser, S. D.; Leahey, 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. U.S.A. 1994, 91, 3228-3232.
17. Jaffee, B. D.; Kerr, J. S.; Jones, E. A.; Giannaras, J. V.; McGowan, M.; Ackerman, N. R. The Effect of Immunomodulating Drugs on Adjuvant-induced Arthritis in Lewis Rats. Agents Actions 1989, 27, 344-346.
18. Winter, C. A.; Risley, E. A.; Nuss, G. W. Carrageenan-Induced Edema in Hind Paw of the Rat as an Assay for Antiinflammatory Drugs. Proc. Soc. Exp. Biol. Med. 1962, 305, 479-484.
19. Hargreaves, K.; Dubner, R.; Brown, F.; Flores, C.; Joris, J. A. New and Sensitive Method for Measuring Thermal Nociception in Cutaneous Hyperalgesia. Pain 1988, 32, 77-88.