Description
Fenbufen has been found to be an effective, well-tolerated drug for the treatment of
rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. Fenbufen is prepared by the Friedel-Crafts (aluminum chloride – nitrobenzene)
acylation of biphenyl with succinic anhydride. The compound is metabolized
in humans first to 4-hydroxy-4-biphenylbutyric
acid (tmax 2.5 h) then to 4-biphenyl acetic acid
(tmax 7.5 h). Both metabolites are more active
than fenbufen itself and circulate for several
hours (t1/2 10 h). This slow conversion of fenbufen to active metabolites having relatively
long plasma half-lives allows for once a day dosing with this agent.
Chemical Properties
White Solid
Originator
Cinopal,Cyanamid,Italy,1976
Uses
muscle relaxant (smooth)
Uses
Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory
Definition
ChEBI: Fenbufen is a member of biphenyls and a 4-oxo monocarboxylic acid. It has a role as a non-steroidal anti-inflammatory drug.
Manufacturing Process
135 g of aluminum chloride is dissolved in 500 ml of nitrobenzene, the
solution being held below 10°C by external cooling. A finely ground mixture of
50 g of succinic anhydride and 75 g of biphenyl is added to the stirred
solution, the temperature being held below 10°C. It is then held at room
temperature for four days. After pouring the reaction mixture into a solution
of 150 ml of concentrated hydrochloric acid in 1 liter of ice water, the
nitrobenzene is removed by steam distillation. The solid is collected, dissolved
in 4 liters of 3% hot sodium carbonate solution, clarified, and reprecipitated
by the addition of excess 6N sulfuric acid solution. The crude product is
collected, dried, and recrystallized from ethanol to give the pure subject
compound, MP 185°C to 187°C.
Therapeutic Function
Antiinflammatory
General Description
Fenbufen belongs to the class of non-steroidal anti-inflammatory drugs, widely used as an antipyretic and analgesic in medical applications. Its mode of action involves the inhibition of cyclooxygenase enzyme and thereby prevents the synthesis of certain prostaglandins.
Trade name
Clincopal (Lederle, Spain),
Lederfen (Lederle, UK), Napanol (Lederle,
Japan).
Safety Profile
Poison by ingestion,intraperitoneal, and subcutaneous routes. Human systemiceffects by ingestion: cough, sweating, body temperature.An experimental teratogen. Other experimentalreproductive effects. An anti-inflammatory agent. Whenheated to decomposi
