Valdecoxib

Valdecoxib

Clinical data
Trade names	Bextra
Pregnancy category	AU: C May cause premature closure of the ductus arteriosus
Routes of administration	Oral
ATC code	M01AH03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) Withdrawn in U.S., EU, Canada & parts of Asia
Pharmacokinetic data
Bioavailability	83%
Protein binding	98%
Metabolism	Hepatic (CYP3A4 and 2C9 involved)
Biological half-life	8 to 11 hours
Excretion	Renal
Identifiers
IUPAC name 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide
CAS Number	181695-72-7 N
PubChem CID	119607
IUPHAR/BPS	2894
DrugBank	DB00580 Y
ChemSpider	106796 Y
UNII	2919279Q3W
KEGG	D02709 Y
ChEBI	CHEBI:63634 N
ChEMBL	CHEMBL865 Y
ECHA InfoCard	100.229.918
Chemical and physical data
Formula	C16H14N2O3S
Molar mass	314.364 g/mol
3D model (Jmol)	Interactive image
SMILES O=S(=O)(N)c3ccc(c2c(onc2c1ccccc1)C)cc3
InChI 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) Y Key:LNPDTQAFDNKSHK-UHFFFAOYSA-N Y
NY (what is this?)

Valdecoxib is a non-steroidal 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.

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 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 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."

In September 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 and Upjohn, a Pfizer subsidiary, violated the United States Food, Drug and Cosmetic Act for misbranding Bextra "with the intent to defraud or mislead."

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

In the United States, the Food and Drug Administration (FDA) approved valdecoxib for the treatment of osteoarthritis, adult rheumatoid arthritis, and primary dysmenorrhea.