ALCLOFENAC Chemical Properties

Melting point:

90-91°C

Boiling point:

324.6°C (rough estimate)

Density 

1.2401 (rough estimate)

refractive index 

1.4530 (estimate)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

pKa 10.3 (Uncertain)

form 

Solid

color 

Off-White to Pale Yellow

Water Solubility 

13.1mg/L(25 ºC)

Safety Information

Toxicity

LD50 in mice, rats (mg/kg): 1100, 1050 orally; 600, 630 s.c.; 555, 530 i.p. (Lambelin)

ALCLOFENAC Usage And Synthesis

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links an allyl group to the 4-position of (3-chlorophenyl)acetic acid.A non-steroidal anti-inflammatory drug, it was withdrawn from the UK market in 1979 due to concerns with its association with vasculitis and r sh.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).

ALCLOFENAC(22131-79-9)Related Product Information

• alclofenac epoxide
• SALOR-INT L129054-1EA
• 3-CHLORO-4-HYDROXYPHENYLACETIC ACID
• 3-CHLORO-4-METHOXYTOLUENE
• 2-(4-ETHOXYPHENYL)ETHANOL
• 4-Methoxyphenylacetic acid
• 3-chloro-4-methoxyphenylacetic acid
• 3-CHLORO-4-ETHOXY-BENZENEACETIC ACID
• 3-Chlorophenylacetic acid
• 3-CHLOROPHENETHYLALCOHOL
• ALCLOFENAC
• ALLYL 2-CHLOROPHENYL ETHER
• 4-ETHOXYPHENYLACETIC ACID