C&EN: LATEST NEWS - Investigating Vioxx Toxicity
C&EN: LATEST NEWS - Investigating Vioxx Toxicity
Oxidation to a maleic anhydride derivative may be a factor in the long-term toxicity of rofecoxib (Vioxx), a new report suggests. This previously unknown reactivity is not shared by other cyclooxygenase-2 (COX-2) inhibitors, such as celecoxib (Celebrex), valdecoxib (Bextra), and lumiracoxib (Prexige). The hypothesis, if proven true, runs counter to the assumption that other COX-2 inhibitors pose the same risk to humans as Vioxx.
Vioxx was withdrawn from the market last September by its manufacturer, Merck, after a clinical trial indicated that it poses an increased risk of cardiovascular events.
Vioxx is a weak acid, and the anion formed when it releases its acidic proton is highly reactive toward atmospheric oxygen, according to laboratory studies by Harvard University chemists Leleti Rajender Reddy and E. J. Corey. The products are principally a maleic anhydride and lesser amounts of a -hydroxybutenolide [Tetrahedron Lett., published online Dec. 25, 2004, http://dx.doi.org/10.1016/j.tetlet.2004.12.055].
Oxidation to a maleic anhydride derivative may be a factor in the long-term toxicity of rofecoxib (Vioxx), a new report suggests. This previously unknown reactivity is not shared by other cyclooxygenase-2 (COX-2) inhibitors, such as celecoxib (Celebrex), valdecoxib (Bextra), and lumiracoxib (Prexige). The hypothesis, if proven true, runs counter to the assumption that other COX-2 inhibitors pose the same risk to humans as Vioxx.
Vioxx was withdrawn from the market last September by its manufacturer, Merck, after a clinical trial indicated that it poses an increased risk of cardiovascular events.
Vioxx is a weak acid, and the anion formed when it releases its acidic proton is highly reactive toward atmospheric oxygen, according to laboratory studies by Harvard University chemists Leleti Rajender Reddy and E. J. Corey. The products are principally a maleic anhydride and lesser amounts of a -hydroxybutenolide [Tetrahedron Lett., published online Dec. 25, 2004, http://dx.doi.org/10.1016/j.tetlet.2004.12.055].
posted by Chris Placitella at 5:03 AM
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