Chemical Properties
White Crystalline Solid
Uses
Anti-inflammatory; antipyretic
Definition
ChEBI: An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,6-dichloro-3-methylphenyl group. A non-steroidal anti-inflammatory drug, it is used as the sodium salt for the treatment of dysmenorrhoe
(painful periods), osteoarthritis and rheumatoid arthritis.
Originator
Meclomen,Warner Lambert,US,1980
Manufacturing Process
A mixture consisting of 22.7 g potassium o-bromobenzoate, 16.6 g 2,6- dichloro-3-methylaniline, 12 ml N-ethylmorpholine, 60 ml diethylene glycol dimethyl ether, and 1.0 g anhydrous cupric bromide is heated in a nitrogen atmosphere at 145°C to 155°C for 2 hours. The reaction mixture is diluted with 60 ml diethylene glycol dimethyl ether and acidified with 25 ml concentrated hydrochloric acid. The acidic mixture is diluted with 100 ml of water and the liquid phase decanted from the insoluble oil. The insoluble oil is stirred with methanol and the crystalline N-(2,6-dichloro-3-methylphenyl) anthranilic acid which separates is collected and washed with methanol. The product, after recrystallization from acetone-water mixture, melts at 248°C to 250°C.
Brand name
Meclomen (Parke-Davis).
Therapeutic Function
Antiinflammatory
Clinical Use
Meclofenamat is a nonsteroidal
anti-inflammatory drug used for the
treatment of mild to moderate pain, musculoskeletal,
and joint disorders like rheumatoid
arthritis and osteoarthritis as well as dysmenorrhoea.
Meclofenamate inhibits COX-1 and
COX-2 and modifies ion channels.
Side effects
Meclofenamic acid is available as its sodium
salt hydrate. This drug is indicated for the relief
of acute and chronic rheumatoid arthritis and osteoarthritis. Gastrointestinal distress, including
diarrhea, nausea, vomiting, and abdominal pain,
is the most commonly reported adverse effect.
Synthesis
Meclofenamic acid, N-(2,6-dichloro-m-tolyl)anthranylic acid
(3.2.20), is synthesized analogous to flufenamic acid, by the reaction of potassium salt of
2-bromobenzoic acid with 2,6-dichloro-3-methylaniline in the presence of copper (II) bromide in a mixture of N-ethylmorpholine and diglyme [82,83].
