Valdecoxib
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| Trade names | Bextra |
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| Routes of administration | Oral |
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| Pharmacokinetic data | |
| Bioavailability | 83% |
| Protein binding | 98% |
| Metabolism | Hepatic (CYP3A4 and 2C9 involved) |
| Elimination half-life | 8 to 11 hours |
| Excretion | Renal |
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| ECHA InfoCard | 100.229.918 |
| Chemical and physical data | |
| Formula | C16H14N2O3S |
| Molar mass | 314.36 g·mol−1 |
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Valdecoxib is a nonsteroidal anti-inflammatory drug (NSAID) used in the treatment of osteoarthritis, rheumatoid arthritis, and painful menstruation and menstrual symptoms. It is a selective cyclooxygenase-2 inhibitor. It was patented in 1995.[2]
Valdecoxib was manufactured and marketed under the brand name Bextra by G. D. Searle & Company as an anti-inflammatory arthritis drug.[3] It was approved by the United States Food and Drug Administration (FDA) on November 20, 2001, to treat arthritis and menstrual cramps,[4][5] and was available by prescription in tablet form until 2005 when the FDA requested that Pfizer (Searle's parent company) withdraw Bextra from the American market.[6] The FDA cited "potential increased risk for serious cardiovascular (CV) adverse events," an "increased risk of serious skin reactions" and the "fact that Bextra has not been shown to offer any unique advantages over the other available NSAIDs."[6]
In 2009, Bextra was at the center of the "largest health-care fraud settlement and the largest criminal fine of any kind ever."[4][7] Pfizer paid a $2.3 billion civil and criminal fine. Pharmacia & Upjohn, a Pfizer subsidiary, violated the United States Food, Drug and Cosmetic Act for misbranding Bextra "with the intent to defraud or mislead."[3]
A water-soluble and injectable prodrug of valdecoxib, parecoxib, is marketed in the European Union under the tradename Dynastat.
- ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 52X. ISBN 9783527607495.
- ^ a b "Pfizer fined $2.3B in record fraud settlement Pharma giant illegally promoted product: Justice Department says, in largest health care fraud settlement in history". Washington: CNN. 2 September 2009. Retrieved 28 December 2015.
- ^ a b Gardiner H (2 September 2009). "Pfizer Pays $2.3 Billion to Settle Marketing Case". New York Times. Retrieved 28 December 2015.
- ^ "Valdecoxib. U.S. FDA Drug Approval". Thomson Micromedex. Retrieved June 8, 2007.
- ^ a b "Information for Healthcare Professionals: Valdecoxib (marketed as Bextra)". U.S. Food and Drug Administration. 2005. Archived from the original on June 27, 2009. Retrieved 28 December 2015.
- ^ Elkind P, Reingold J (28 July 2011). "Inside Pfizer's palace coup". Fortune. Retrieved 28 December 2015.