Meclofenamic acid Chemical Properties

Melting point:

257-259°C

Boiling point:

399.4±42.0 °C(Predicted)

Density 

1.3567 (rough estimate)

refractive index 

1.6070 (estimate)

storage temp. 

Refrigerator

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated)

pka

pKa 4.0 (Uncertain)

form 

Solid

color 

Off-White to Light Orange

EPA Substance Registry System

Benzoic acid, 2-[(2,6-dichloro-3-methylphenyl)amino]- (644-62-2)

Meclofenamic acid Usage And Synthesis

Chemical Properties

White Crystalline Solid

Originator

Meclomen,Warner Lambert,US,1980

Uses

Meclofenamic acid is used for the same conditions as flufenamic acid.

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.

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, Portugal, USA), Meclodol (Parke Davis, Italy), Stadium (Menarini, Belgium).

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].

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