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Mefenamic acid

Basic information Description References Safety Supplier Related

Mefenamic acid Basic information

Product Name:
Mefenamic acid
Synonyms:
  • Mefenamic Acid (200 mg)
  • N-(2,3-Dimethylphenyl)anthranilic Acid 2-(2,3-Dimethylphenylamino)benzoic Acid 2-(2,3-Xylidino)benzoic Acid
  • CI 473,CN-35355
  • Mefenamic acid Solution, 100ppm
  • MefenaMic Aicd (API)
  • 2’,3’-dimethyl-2-diphenylaminecarboxylicaci
  • 2-Diphenylaminecarboxylic acid, 2',3'-dimethyl-
  • ac.mefenamico
CAS:
61-68-7
MF:
C15H15NO2
MW:
241.29
EINECS:
200-513-1
Product Categories:
  • PONSTEL
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • Amino Acids 13C, 2H, 15N
  • Amino Acids & Derivatives
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • API's
Mol File:
61-68-7.mol
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Mefenamic acid Chemical Properties

Melting point:
230 °C
Boiling point:
384.06°C (rough estimate)
Density 
1.0944 (rough estimate)
refractive index 
1.5200 (estimate)
storage temp. 
2-8°C
solubility 
Practically insoluble in water, slightly soluble in ethanol (96 per cent) and in methylene chloride. It dissolves in dilute solutions of alkali hydroxides
form 
neat
pka
4.2(at 25℃)
Water Solubility 
It is soluble in acetone, chloroform, dichloromethane, methanol. Insoluble in water.
Merck 
14,5798
InChIKey
HYYBABOKPJLUIN-UHFFFAOYSA-N
CAS DataBase Reference
61-68-7(CAS DataBase Reference)
NIST Chemistry Reference
Mefenamic acid(61-68-7)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22-40-20/21/22
Safety Statements 
22-36
WGK Germany 
3
RTECS 
CB4550000
HS Code 
28142000
Hazardous Substances Data
61-68-7(Hazardous Substances Data)
Toxicity
LD50 orally in mice, rats: 630, 790 mg/kg (Jahn, Adrian)

MSDS

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Mefenamic acid Usage And Synthesis

Description

Mefenamic acid is a kind of nonsteroidal anti-inflammatory (NSAID) drug belonging to the anthranilic acid derivatives class. It is mainly used for the short-term treatment of mild to moderate pain from various conditions. It is also used for reducing the pain and blood loss from menstrual condition as well as prevention of migraines. Moreover, it may also be used for treating gout attacks. Its mechanism is through inhibiting both the isoforms of COX and preventing the formation of prostaglandins. It is manufactured from 2-chlorobenzoic acid and 2,3-dimethylaniline. 

References

http://www.webmd.com/drugs/2/drug-11586/mefenamic-acid-oral/details
https://en.wikipedia.org/wiki/Mefenamic_acid

Chemical Properties

Light Yellow Solid

Originator

Ponstan,Parke Davis,UK,1963

Uses

Mefenamic acid is used for the same indications as flufenamic acid. Synonyms for this drug are parkemed, ponstan, ponstel, and others.

Uses

For the treatment of rheumatoid arthritis, osteoarthritis, dysmenorrhea, and mild to moderate pain, inflammation, and fever.

Uses

Anti-inflammatory; analgesic.

Indications

Mefenamic acid (Ponstel) is indicated only for analgesia and primary dysmenorrhea when therapy will not exceed 1 week.

Definition

ChEBI: An aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to b minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.

Manufacturing Process

A mixture of 800 g of potassium o-bromo-benzoate, 1,500 ml of bis-(2- methoxyethyl)ether, 355 g of N-ethyl-morpholine, 375 g of 2,3- dimethylaniline, and 30 g of cupric acetate is heated gradually with stirring to 140°C over a period of 90 minutes. The hot reaction mixture is then acidified with 260 mi of concentrated hydrochloric acid and the acidified mixture divided into 2 equal portions. One liter of water is added to each portion and the mixtures allowed to cool. The N-(2,3-dimethylphenyl)anthranilic acid which separates upon cooling is collected by filtration and recrystallized from bis(2-methoxyethyl)ether; MP 229° to 230°C (corr.).

brand name

Ponstel (Sciele).

Therapeutic Function

Analgesic

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 2127, 1980 DOI: 10.1021/jo01299a020

General Description

Mefenamic acid (Ponstel, Ponstan) is one of the oldestNSAIDs, introduced into the market in 1967 for mild tomoderate pain and for primary dysmenorrhea. It is rapidly absorbed with peak plasma levels occurring 2 to 4 hoursafter oral administration. It undergoes hepatic benzylic hydroxylationof its 3'methyl group regioselectively into twoinactive metabolites, 3'-hydroxymethylmefenamic acid andthe 3'carboxylate metabolite (via further oxidation of thebenzylic alcohol group). The parent drugs and these metabolitesare conjugated with glucuronic acid and excreted primarilyin the urine. Thus, although patients with knownliver deficiency may be given lower doses, it is contraindicatedin patients with preexisting renal dysfunction.
Common side effects associated with its use include diarrhea,drowsiness, and headache. The possibility of blood disordershas also prompted limitation of its administration to 7days. It is not recommended for children or during pregnancy.

Clinical Use

Mefenamic acid is synthesized from o-chlorobenzoic acid and 2,3-dimethylaniline under catalytic conditions. Mefenamic acid is the only fenamic acid derivative that produces analgesia centrally and peripherally. Mefenamic acid is indicated for the short-term relief of moderate pain and for primary dysmenorrhea.

Chemical Synthesis

Mefenamic acid, N-(2,3-xylyl)anthranylic acid (3.2.19), is synthesized in basically the same manner, by the reaction of the potassium salt of 2-bromobenzoic acid with 2,3-dimethylaniline in the presence of copper (II) acetate [80,81].

Metabolism

Mefenamic acid is absorbed rapidly following oral administration, with peak plasma levels being attained within 2 to 4 hours. It is highly bound to plasma proteins (78.5%) and has a plasma half-life of 2 to 4 hours. Metabolism occurs through regioselective oxidation of the 3′-methyl group and glucuronidation of mefenamic acid and its metabolites. Urinary excretion accounts for approximately 50 to 55% of an administered dose, with unchanged drug accounting for 6%, the 3′-hydroxymethyl metabolite (primarily as the glucuronide) accounting for 25%, and the remaining 20% as the dicarboxylic acid (of which 30% is the glucuronide conjugate). These metabolites are essentially inactive.

Mefenamic acid Preparation Products And Raw materials

Raw materials

Mefenamic acid Supplier

Shaanxi Baoxin Pharmaceutical Co., Ltd. Gold
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