The manufacturer of Valdecoxib (Bextra) has announced a voluntary withdrawal of the drug from the US market. This withdrawal is caused by safety concerns over an increased risk of heart attack and stroke in patients taking non-steroidal anti-inflammatory drugs (Bextra is a "COX-2" selective non-steroidal anti-inflammatory drug), and an increased risk of rare but serious skin reactions.
Bextra, sometimes called Valdecoxib, is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs), and works by reducing substances in the body that cause inflammation, pain, and fever.
Bextra is used to reduce pain, inflammation, and stiffness caused by osteoarthritis and adult rheumatoid arthritis, and for painful menstruation.
Be sure to tell your doctor of any allergies you have whether it is to medication or food, preservatives, or dyes. Tell your doctor immediately if you are, or become pregnant, or are breastfeeding. Also tell your doctor of any other medications you are taking, including vitamins and supplements, and any medical conditions you may have.
It is very important that you take this medicine exactly as your doctor tells you to. If you miss a dose of this medicine, take it as soon as you remember, unless it is almost time for your next dose. Do NOT double doses.
Serious skin reactions have occurred in patients taking Bextra. Though most of these reactions occur the first two weeks of treatment, they may occur at any time during treatment.
Stop taking Bextra immediately and to your doctor right away if you develop a skin rash; hives; itching; difficulty breathing; swelling of the lips, tongue or face; or other symptoms of an allergic reaction; abdominal pain, tenderness, or discomfort; nausea; bloody vomit; bloody, black, or tarry stools; unexplained weight gain; swelling or water retention; fatigue or lethargy; a skin rash; itching; yellowing of the skin or eyes; "flu-like" symptoms; or unusual bruising or bleeding.
Check with your doctor if you experience any of the following: diarrhea; nausea or upset stomach; or headache.
Valdecoxib is chemically designated as 4-(5-methyl-3-phenyl-4-isoxazolyl) benzenesulfonamide and is a diaryl substituted isoxazole.
The empirical formula for valdecoxib is C16H14N2O3S, and the molecular weight is 314.36. Valdecoxib is a white crystalline powder that is relatively insoluble in water (10 µg/mL) at 25C and pH 7.0, soluble in methanol and ethanol, and freely soluble in organic solvents and alkaline (pH=12) aqueous solutions.
BEXTRA Tablets for oral administration contain either 10 mg or 20 mg of valdecoxib. Inactive ingredients include lactose monohydrate, microcrystalline cellulose, pregelatinized starch, croscarmellose sodium, magnesium stearate, hydroxypropyl methylcellulose, polyethylene glycol, polysorbate 80, and titanium dioxide.
The structural formula is: