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Meclofenamic acid

CAS No.644-62-2
Chemical Name:Meclofenamic acid
CBNumber:CB7875562
Molecular Formula:C14H11Cl2NO2
Formula Weight:296.15
MOL File:644-62-2.mol

Meclofenamic acid Property

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)
form Solid
pka pKa 4.0 (Uncertain)
color Off-White to Light Orange
FDA UNII 48I5LU4ZWD
ATC code M01AG04,M02AA18
EPA Substance Registry System Benzoic acid, 2-[(2,6-dichloro-3-methylphenyl)amino]- (644-62-2)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Hazard statements
Precautionary statements

Meclofenamic acid Chemical Properties,Usage,Production

Chemical Properties White Crystalline Solid
Originator Meclomen,Warner Lambert,US,1980
Uses Anti-inflammatory; antipyretic
Uses Meclofenamic acid is used for the same conditions as flufenamic acid.
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].
Toxics Screening Level The ITSL for meclofenamic acid has been changed from 0.04 μg/m3 to 0.1 μg/m3 based on an annual averaging time.