MECLOFENAMATE SODIUM Property

Melting point:

287-291 °C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

White solid.

color 

White to Off-White

Water Solubility 

Soluble in water at 50mg/ml. Also soluble in DMF, DMSO or ethanol

Merck 

14,5779

Stability:

Hygroscopic

Safety

WGK Germany 

3

RTECS 

CB2975500

HS Code 

2922498050

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

MECLOFENAMATE SODIUM Chemical Properties,Usage,Production

Description

Meclofenamate is a time-dependent, non-specific competitive inhibitor of COX-1 and -2. The IC₅₀ values for inhibition of human recombinant COX-1 and -2 are 1.5 and 9.7 μM, respectively for instantaneous inhibition. However, the IC₅₀ is much lower if pre-incubated with the enzyme.

Originator

Meclomen,Warner Lambert,US,1980

Uses

antiinflammatory, antipyretic

Uses

Meclofenamate Sodium is an NSAID used in the treatment of chronic pain.

Indications

Meclofenamate sodium (Meclomen) is prescribed for rheumatoid arthritis and osteoarthritis. The fenamates show no clear superiority in antiinflammatory activity and may produce more adverse effects than other NSAIDs.

Definition

ChEBI: An organic sodium salt derived from meclofenamic acid. Its monohydrate is used for the treatment of dysmenorrhoea (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).

Therapeutic Function

Antiinflammatory

General Description

Meclofenamate sodium (Meclomen) is available for use inthe treatment of acute and chronic RA, OA, and primarydysmenorrhea. It is metabolized in a similar manner tomefenamic acid discussed above, thus a similar restriction isalso applied to meclofenamate. The most significant side effectsare GI, including diarrhea.

Pharmacokinetics

Meclofenamate sodium is rapidly and almost completely absorbed following oral administration, reaching peak plasma levels within 2 hours. It is highly bound to plasma proteins (99%) and has a plasma half-life of 2 to 4 hours. Metabolism involves oxidation of the methyl group, aromatic hydroxylation, monodehalogenation, and conjugation. Urinary excretion accounts for approximately 75% of the administered dose. The major metabolite is the product of 3′-methyl oxidation and has been shown to possess anti-inflammatory activity.

Clinical Use

Meclofenamate sodium is indicated for the relief of mild to moderate pain, the acute and chronic treatment of rheumatoid arthritis and osteoarthritis, the treatment of primary dysmenorrhea, and the treatment of idiopathic, heavy menstrual blood loss.