Flunoxaprofen
chemical compound
Flunoxaprofen, also known as Priaxim, is a chiral nonsteroidal anti-inflammatory drug (NSAID). It is closely related to naproxen, which is also an NSAID. Flunoxaprofen has been shown to significantly improve the symptoms of osteoarthritis and rheumatoid arthritis. The clinical use of flunoxaprofen has ceased due to concerns of potential hepatotoxicity.
Structure
Flunoxaprofen is a two-ring heterocyclic compound derived from benzoxazole. It also contains a fluorine atom and a propanoyl group.
Synthesis
The overall synthesis is similar to that for benoxaprofen; in this case, para-fluorobenzoyl chloride is used when forming the benzoxazole ring..
A Sandmeyer reaction by diazotisation of 2-(4-aminophenyl)propanenitrile (1) followed by acid hydrolysis leads to the phenol (2), which is nitrated and reduced using stannous chloride or catalytic hydrogenation to give the aminophenol (4). Hydrolysis of the nitrile produces the carboxylic acid (5), which is converted to racemic flunoxaprofen by acylation with p-fluorobenzoyl chloride, followed by cyclisation.
Preparations
Because flunoxaprofen has limited water-solubility, additional steps must be taken in order to prepare syrups, creams, suppositories, etc. In order to make flunoxaprofen water-soluble, yet still active and efficient, it must be mixed with lysine and then suspended in an organic solvent that is soluble in water.
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