The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors: Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1 H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)
Open accessAbstract
A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC-236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3-(trifluoromethyl)- H-pyrazol-1-yl]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.
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Cites
Selective inhibition of inducible cyclooxygenase 2 in vivo is antiinflammatory and nonulcerogenic.
Masferrer, J. L., Zweifel, B. S., Manning, P. T., Hauser, S. D., Leahy, K. M., Smith, W. G., Isakson, P. C., & Seibert, K. (1994) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.91.8.3228 · Cited by 1,310
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Cited by
The Many Roles for Fluorine in Medicinal Chemistry
Hagmann, W. K. (2008) · Journal of Medicinal Chemistry · doi:10.1021/jm800219f · Cited by 3,578
Ecotoxicology of human pharmaceuticals
Fent, K., Weston, A. A., & Caminada, D. (2006) · Aquatic Toxicology · doi:10.1016/j.aquatox.2005.09.009 · Cited by 3,223
Rao, P., & Knaus, E. E. (2008) · Journal of Pharmacy & Pharmaceutical Sciences · doi:10.18433/j3t886 · Cited by 773
Clinical Pharmacokinetics and Pharmacodynamics of Celecoxib: A Selective Cyclo-Oxygenase-2 Inhibitor
Davies, N. M., McLachlan, A. J., Day, R. O., & Williams, K. M. (2000) · Clinical Pharmacokinetics · doi:10.2165/00003088-200038030-00003 · Cited by 424
Meta-analysis of Cyclooxygenase-2 Inhibitors and Their Effects on Blood Pressure
(2005) · Archives of Internal Medicine · doi:10.1001/archinte.165.5.ioi50013 · Cited by 329
Metadata
- Authors
- 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., Anderson, G. D., Burton, E. G., Cogburn, J. N., Gregory, S. A., Koboldt, C. M., Perkins, W. E., Seibert, K., Veenhuizen, A. W., Zhang, Y. Y., & Isakson, P. C.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1997-04-01
- Volume
- 40
- Issue
- 9
- Pages
- 1347-1365
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2033498682
- Cited by
- 1,965
- References
- 1
- FWCI
- 47.31
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors: Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1 H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib). https://app.cochat.ai/papers/10.1021/jm960803q
- The paper
- 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., Anderson, G. D., Burton, E. G., Cogburn, J. N., Gregory, S. A., Koboldt, C. M., Perkins, W. E., . . . Isakson, P. C. (1997). Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors: Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1 H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib). Journal of Medicinal Chemistry. https://doi.org/10.1021/jm960803q
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
