Mefenamic Acid

Base Information

• Chemical Name: Mefenamic Acid
• CAS No.: 61-68-7
• Molecular Formula: C15H15NO2
• Molecular Weight: 241.29
• Hs Code.: 2922.49
• European Community (EC) Number: 200-513-1
• NSC Number: 757834,94437
• UNII: 367589PJ2C
• DSSTox Substance ID: DTXSID5023243
• Nikkaji Number: J2.344B
• Wikipedia: Mefenamic_acid
• Wikidata: Q284321
• NCI Thesaurus Code: C47599
• RXCUI: 6693
• Pharos Ligand ID: P8UZ3WH3XUYG
• Metabolomics Workbench ID: 43078
• ChEMBL ID: CHEMBL686
• Mol file: 61-68-7.mol

Synonyms:Acid, Mefenamic;Apo Mefenamic;Apo-Mefenamic;Contraflam;Coslan;Dysman;Mefac;Mefacit;Mefenamic Acid;Mefenaminic Acid;Mefic;Nu Mefenamic;Nu-Mefenamic;Parkemed;Pinalgesic;PMS Mefenamic Acid;PMS-Mefenamic Acid;Ponalar;Ponalgic;Ponmel;Ponstan;Ponstan Forte;Ponstel;Ponsyl;Pontal

Chemical Property of Mefenamic Acid

Chemical Property:

• Appearance/Colour: light yellow solid
• Vapor Pressure: 4.45E-07mmHg at 25°C
• Melting Point: 230 °C
• Refractive Index: 1.639
• Boiling Point: 398.8 °C at 760 mmHg
• PKA: 4.2(at 25℃)
• Flash Point: 195 °C
• PSA: 49.33000
• Density: 1.203 g/cm³
• LogP: 3.81820
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, slightly soluble in ethanol (96 per cent) and in methylene chloride. It dissolves in dilute solutions of alkali hydroxides
• Water Solubility.: It is soluble in acetone, chloroform, dichloromethane, methanol. Insoluble in water.
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 241.110278721
• Heavy Atom Count: 18
• Complexity: 292

Purity/Quality:

99%-101%, ^*data from raw suppliers

Mefenamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-40-20/21/22
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)NC2=CC=CC=C2C(=O)O)C
• Recent ClinicalTrials: Drug-drug Interaction Between Ciprofol and Mefanamic Acid or Valproate
• Recent EU Clinical Trials: International, prospective, double-blind, 3-arm comparative, randomized, placebo controlled phase IV study on the effect of counseling and either tranexamic acid or
• Recent NIPH Clinical Trials: The Effect of 0.2% Chlorhexidine Gel on Wound Healing after Tooth Extraction
• 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.
• Uses: Mefenamic acid is used for the same indications as flufenamic acid. Synonyms for this drug are parkemed, ponstan, ponstel, and others. For the treatment of rheumatoid arthritis, osteoarthritis, dysmenorrhea, and mild to moderate pain, inflammation, and fever.
• Indications: Mefenamic acid (Ponstel) is indicated only for analgesia and primary dysmenorrhea when therapy will not exceed 1 week.
• Therapeutic Function: Analgesic
• 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.
• Drug interactions: Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia. Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage). Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetics: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity.

Technology Process of Mefenamic Acid

There total 22 articles about Mefenamic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

mefenamic acid benzyl ester → mefenamic Acid (61-68-7)

Guidance literature:

With hydrogen; In methanol; at 50 ℃; under 3750.38 Torr; chemoselective reaction; Flow reactor;

DOI:10.1002/cctc.202000805

Reference yield: 94.8%

2,3-Dimethylaniline (87-59-2) + ortho-chlorobenzoic acid (118-91-2) → mefenamic Acid (61-68-7)

Guidance literature:

ortho-chlorobenzoic acid; With sodium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 0.5h;

2,3-Dimethylaniline; With manganese(II) acetate; In water; N,N-dimethyl-formamide; toluene; at 120 - 130 ℃; Reagent/catalyst;

Reference yield: 93.0%

2-Iodobenzoic acid (88-67-5) + 2,3-Dimethylaniline (87-59-2) → mefenamic Acid (61-68-7)

Guidance literature:

With sodium acetate; copper (I) acetate; In water; for 1.5h; Heating;

upstream raw materials:

1-(1',2'-dimethyl-phenyl)-1,2-dihydro-3,1-benzoxazin-4-one

1-(1',2'-dimethyl-phenyl)-2-methoxy-1,2-dihydro-3,1-benzoxazin-4-one

1-(1',2'-dimethyl-phenyl)-2-chloromethyl-1,2-dihydro-3,1-benzoxazin-4-one

1-(1',2'-dimethyl-phenyl)-2-ethoxy-1,2-dihydro-3,1-benzoxazin-4-one

Downstream raw materials:

methyl 2-[(2,3-dimethylphenyl)amino]benzoate

2-(2,3-Dimethyl-phenylamino)-benzoic acid 2-diethylamino-ethyl ester

2-(2,3-Dimethyl-phenylamino)-benzoic acid ethoxymethyl ester

1-(1',2'-dimethyl-phenyl)-1,2-dihydro-3,1-benzoxazin-4-one

Refernces

• 1、 Manna, Kartic,Ganguly, Tanusree,Baitalik, Sujoy,Jana, Ranjan. "Visible-Light- And PPh3-Mediated Direct C-N Coupling of Nitroarenes and Boronic Acids at Ambient Temperature". supporting information. p. 8634 - 8639. Retrieved 2021/11/01.
• 2、 Chang, Jia-jia,Hou, Shi,Lan, Xiu-juan,Li, Song,Li, Wei,Sun, Wei,Xiao, Jun-hai,Yan, Xin-lin,Yang, Xiao-hong. "Design, synthesis and biological evaluation of acridone analogues as novel STING receptor agonists". . . Retrieved 2020/01/09.