Structure and Reactivity
The molecular formula of benoxaprofen is C16H12ClNO3 and the systematic (IUPAC) name is 2-propionic acid. The molecule has a molecular mass of 301.050568 g/mol.
Benoxaprofen is essentially a planar molecule. This is due to the co-planarity of the benzoxazole and phenyl rings, but the molecule also has a non-planar side chain consisting of the propanoic acid moiety which acts as a carrier group. These findings were determined with the use of X-ray crystallographic measurements by the Lilly Research Centre Limited.
Furthermore, benoxaprofen is highly phototoxic. The free radical decarboxylated derivative of the drug is the toxic agent which, in the presence of oxygen, yields singlet oxygen and superoxy anion. Photochemical decarboxylation via a radical mechanism and in single-strand breaks of DNA is caused by irradiation of benoxaprofen in an aqueous solution. This also happens to ketoprofen and naproxen, other non-steroidal anti-inflammatory drugs, which are even more active in this respect than benoxaprofen.
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