Valdecoxib

Valdecoxib
Clinical data
Trade namesBextra
Pregnancy
category
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability83%
Protein binding98%
MetabolismHepatic (CYP3A4 and 2C9 involved)
Elimination half-life8 to 11 hours
ExcretionRenal
Identifiers
  • 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.229.918 Edit this at Wikidata
Chemical and physical data
FormulaC16H14N2O3S
Molar mass314.36 g·mol−1
3D model (JSmol)
  • O=S(=O)(N)c3ccc(c2c(onc2c1ccccc1)C)cc3
  • InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20) checkY
  • Key:LNPDTQAFDNKSHK-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 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.

  1. ^ 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.
  2. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 52X. ISBN 9783527607495.
  3. ^ 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.
  4. ^ a b Gardiner H (2 September 2009). "Pfizer Pays $2.3 Billion to Settle Marketing Case". New York Times. Retrieved 28 December 2015.
  5. ^ "Valdecoxib. U.S. FDA Drug Approval". Thomson Micromedex. Retrieved June 8, 2007.
  6. ^ a b "Information for Healthcare Professionals: Valdecoxib (marketed as Bextra)". U.S. Food and Drug Administration. 2005. Retrieved 28 December 2015.
  7. ^ Elkind P, Reingold J (28 July 2011). "Inside Pfizer's palace coup". Fortune. Retrieved 28 December 2015.