fenclofenac

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.

Uses

Anti-inflammatory.

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].

Raw materials

Preparation Products