Originator
Flenac,Reckitt and Colman
Uses
Fenclofenac is a non-steroidal anti-inflammatory agent functioning as a protein-pump inhibitor.
Uses
Fenclofenac is used for the same indications as diclofenac.
Definition
ChEBI: Fenclofenac is an aromatic ether.
Manufacturing Process
1-[2-(2,5-Dichloro-phenoxy)-phenyl]-ethanone was prepared from a mixture
of 2,4-dichlorphenol, 2-chloroacetophenone and copper catalyst (prepared
according to R.Q. Brewster and T. Groening Organic Syntheses, John Wiley
and Sons, Inc., New York, 1943, Coll. Vol.11, p.446). 1 mol of the above
phenoxy compound was mixed with 3 mol of sulfur and 3.5 mol of morpholine
and heated under gentle reflux for 72 hours. The mixture was evaporated,
water was added and extracted with ether. The aueous layer was then
acidified with concentrated hydrochloric acid and the product was extracted
into ether, the ether extract was dried and evaporated. The solid residue was
recrystallized from CCl4 to give [2-(2,4-dichlorophenoxy)-phenyl]acetic acid,
Yield 37%; MP: 134°-136°C.
Brand name
Feclan;Gidalon;Monosan;Rx 67408nac.
Therapeutic Function
Antiinflammatory
World Health Organization (WHO)
Fenclofenac, a nonsteroidal anti-inflammatory agent, was
introduced in 1978 for the treatment of rheumatic disorders. By 1984 its use in the
United Kingdom was associated with serious adverse effects, predominantly skin
rashes, some of which were fatal. This led to the UK Committee on Safety of
Medicine's refusal to renew the product licence and to the subsequent withdrawal
of the drug by the manufacturer in all countries in which it was marketed.
Synthesis
Fenclofenac, o-[2,4-dichlorophenoxy)phenyl]acetic acid (3.2.45), is synthesized from 2,4-dichlorophenol and 2-chloroacetophenone, the reaction of which in the
presence of sodium hydroxide and powdered copper forms the corresponding
2-acetyl-2??,4??-dichloro-diphenyl ester (3.2.43). The resulting product is reacted with sulfur
and morpholine according to Willgerodt method, giving thioamide (3.2.44), which is further
hydrolyzed to the desired fenclofenac [109,110].
