Valdecoxib

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Valdecoxib
Systematic (IUPAC) name
4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide
Identifiers
CAS number	181695-72-7
ATC code	M01AH03
PubChem	119607
DrugBank	APRD00183
Chemical data
Formula	C₁₆H₁₄N₂O₃S
Mol. mass	314.364 g/mol
Pharmacokinetic data
Bioavailability	83%
Protein binding	98%
Metabolism	Hepatic (CYP3A4 and 2C9 involved)
Half life	8 to 11 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C(AU) May cause premature closure of the ductus arteriosus
Legal status	Withdrawn in U.S., EU, Canada & parts of Asia
Routes	Oral

Valdecoxib is a prescription drug used in the treatment of osteoarthritis, rheumatoid arthritis, and painful menstruation and menstrual symptoms. It is classified as a nonsteroidal anti-inflammatory drug, or NSAID, and should not be taken by anyone allergic to these types of medications.

Valdecoxib was manufactured and marketed under the brand name Bextra by G. D. Searle & Company. It was available by prescription in tablet form until 2005, when it was removed from the market due to concerns about possible increased risk of heart attack and stroke.

[edit] Uses

Since its registration, Bextra was prescribed for pain associated with arthritis, menstrual discomfort, and other ailments.

[edit] Side-effects and withdrawal

On April 7, 2005, Pfizer withdrew Bextra from the U.S. market on recommendation by the FDA, citing an increased risk of heart attack and stroke and also the risk of a serious, sometimes fatal, skin reaction. This was a result of recent attention to prescription NSAIDs, such as Merck's Vioxx. Other reported side-effects were angina and Stevens-Johnson syndrome.

Pfizer first acknowledged cardiovascular risks associated with Bextra in October of 2004. The American Heart Association soon after was presented with a report indicating patients using Bextra while recovering from heart surgery were 2.19 times more likely to suffer a stroke or heart attack than those taking placebos.

Recently in a large study published in JAMA 2006, Valdecoxib appears less adverse for renal (kidney) disease and heart arrhythmia compared to Vioxx, however elevated renal risks was slightly suggested. Systematic review of adverse renal and arrhythmia risk of celecoxib and other COX-2 inhibitors, in JAMA 2006