Flurbiprofen: Synthesis and Application
Mar 16,2024
Synthesis of Flurbiprofen
Ethyl 2-fluoro-4-biphenylacetate,
prepared from 4-acetyl-2-fluorobiphenyl via the
Willgerodt reaction and subsequent esterification, is treated first with diethyl carbonate and
sodium ethoxide, then with dimethyl sulfate to
give diethyl 2-(2-fluoro-4-biphenylyl)-2-methyl
malonate. Saponification followed by acidification affords the malonic acid, which is decarboxylated at 180 – 200 ◦C to yield flurbiprofen.
Application of Flurbiprofen
Flurbiprofen has been used at 150 ~ 300 mg/d in the treatment of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. Gastrointestinal disturbances, particularly dyspepsia, are the principal adverse effects.
Trade names
Ansaid (Pharmacia & Upjohn, CIS; Upjohn, Canada, Czech Republic, Poland, USA), Cebutid (Knoll, France), Froben (Kanoldt, Germany; Ebewe, Austria; Boots, Spain, The Netherlands, Portugal), Tulip (Upjohn, Spain).
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