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Compound

Valdecoxib

Also called Bextra, Valdyn, Kudeq

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Part of the metabolic pathway of Valdecoxib. See the timeline on the metabolic highway.

Enzymes that break it down: CYP3A4. Wikipedia’s drug infobox says: “Hepatic (CYP3A4 and 2C9 involved)” (revision 1354232170).

Overview

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.[1] WP

Valdecoxib was manufactured and marketed under the brand name Bextra by G. D. Searle & Company as an anti-inflammatory arthritis drug. It was approved by the United States Food and Drug Administration (FDA) on November 20, 2001, to treat arthritis and menstrual cramps, 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. 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."[2–5] WP

In 2009, Bextra was at the center of the "largest health-care fraud settlement and the largest criminal fine of any kind ever." 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."[2][3][6] WP

A water-soluble and injectable prodrug of valdecoxib, parecoxib, is marketed in the European Union under the tradename Dynastat. WP

Chemistry

Formula
C16H14N2O3S PC
CAS number
181695-72-7 PC
Molar mass (g/mol)
314.4 PC
IUPAC name (computed by PubChem)
4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide PC
SMILES
CC1=C(C(=NO1)C2=CC=CC=C2)C3=CC=C(C=C3)S(=O)(=O)N PC
InChIKey
LNPDTQAFDNKSHK-UHFFFAOYSA-N PC
PubChem CID
119607

Harm reduction information

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Sources

  1. Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006
  2. Other Pfizer fined $2.3B in record fraud settlement Pharma giant illegally promoted product: Justice Department says, in largest health care fraud settlement in history. 2 September 2009
  3. Other Gardiner H. Pfizer Pays $2.3 Billion to Settle Marketing Case. 2 September 2009
  4. Other Valdecoxib. U.S. FDA Drug Approval
  5. Journal / agency Information for Healthcare Professionals: Valdecoxib (marketed as Bextra). 2005
  6. Other Elkind P, Reingold J. Inside Pfizer's palace coup. 28 July 2011

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.