Chemical Properties
Off-White to Pale Yellow Solid
Originator
Allopydin ,Chugai ,Japan ,1976
Uses
Analgesic; antipyretic; anti-inflammatory.
Definition
ChEBI: An aromatic ether in which the ether oxygen links an allyl group to the 4-position of (3-chlorophenyl)acetic acid.A non-steroidal anti-inflammatory drug, it was withdrawn from the UK market in 1979 due to concerns with its association with vasculitis and r
sh.
Manufacturing Process
103.7 grams of 3-chloro-4-allyloxyphenylacetonitrile in 500 cc of ethanol, 100
grams of potassium hydroxide and 100 cc of water are refluxed for 4 hours.
Maximum of alcohol is evaporated, the residue is diluted with water and ice,
and acidified with 20% HCl. The solid is filtered and washed with petroleum
ether. 91.5 grams of acid are obtained (Yield: 81%) which is recrystallized
from aqueous methanol; MP 92-93°C.
brand name
Mervan (Continental
Pharma, Belgium);Allopydinac;Alopidin;Alopydin;Argan;Darkeyfenac;Desinflam;Medifenac;Mevan;Mirvan a;Prinalgin;Vanadian;W-7320;Zubirol.
Therapeutic Function
Antiinflammatory
World Health Organization (WHO)
Alclofenac, a phenylacetic acid derivative with analgesic,
antipyretic and antiinflammatory activity, was introduced in 1972 for the treatment
of rheumatic disorders. In the late 1970s its use was associated with a high
incidence of adverse effects, mainly skin rashes, and a urinary metabolite was reported to have mutagenic activity (positive Ames test). This resulted in the
withdrawal of the drug, in some cases voluntarily, from several countries. In others
registration has been refused. The reported mutagenic potential has been
questioned by some investigators and the drug remains on the market in at least
three countries with highly evolved regulatory authorities.
Dosage
Alclofenac when used at 3 g/d in the treatment of rheumatoid arthritis is as effective
as 75 mg/d of indomethacin with fewer adverse effects. In the treatment of osteoarthritis 1500 mg/d is as effective and is better tolerated than 300 mg/d of phenylbutazone. Alclofenac has been withdrawn from the market in the United Kingdom because of skin rash and
vasculitis (blood vessel inflammation).
