Mefenamic acid CAS 61-68-7
Introduction：Basic information about Mefenamic acid CAS 61-68-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Mefenamic acid Basic informationDescription References
| Product Name: | Mefenamic acid |
| Synonyms: | Mefenamic Acid (200 mg);N-(2,3-Dimethylphenyl)anthranilic Acid2-(2,3-Dimethylphenylamino)benzoic Acid2-(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;61-68-7 |
| Mol File: | 61-68-7.mol |
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 |
| pka | 4.2(at 25℃) |
| form | Solid |
| color | White to Pale Yellow |
| Water Solubility | It is soluble in acetone, chloroform, dichloromethane, methanol. Insoluble in water. |
| Merck | 14,5798 |
| Major Application | forensics and toxicology pharmaceutical (small molecule) veterinary |
| InChI | 1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18) |
| InChIKey | HYYBABOKPJLUIN-UHFFFAOYSA-N |
| SMILES | Cc1cccc(Nc2ccccc2C(O)=O)c1C |
| LogP | 5.120 |
| CAS DataBase Reference | 61-68-7(CAS DataBase Reference) |
| NIST Chemistry Reference | Mefenamic acid(61-68-7) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-40-20/21/22 |
| Safety Statements | 22-36 |
| WGK Germany | 3 |
| RTECS | CB4550000 |
| HS Code | 28142000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Hazardous Substances Data | 61-68-7(Hazardous Substances Data) |
| Toxicity | LD50 orally in mice, rats: 630, 790 mg/kg (Jahn, Adrian) |
| 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 | white or light yellow crystalline powder, odorless, insoluble in water, slightly soluble in ethanol, chloroform, slightly soluble in ether. Melting point 230-231°C, mefenamic acid is an anti-inflammatory analgesic with antipyretic, analgesic and anti-inflammatory effects. |
| Originator | Ponstan,Parke Davis,UK,1963 |
| Uses | Mefenamic acid is used for the same indications as flufenamic acid. Synonyms for this drug areparkemed, ponstan, ponstel, and others. |
| Uses | For the treatment of rheumatoid arthritis, osteoarthritis, dysmenorrhea, and mild to moderate pain, inflammation, and fever. |
| 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. |
| Indications | Mefenamic acid (Ponstel) is indicated only for analgesiaand primary dysmenorrhea when therapy will not exceed1 week. |
| 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, Parke Davis, USA), Lysalgo (SIT, Italy), Opustan(Opus Pharm, UK), Parkemed (Parke Davis,Germany), Ponstan (Werner-Lambert, Switzerland), Pontal(Sankyo, Japan). |
| 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. |
| Biochem/physiol Actions | Mefenamic acid is an analgesic and anti-inflammatory drug. It acts as a cyclooxygenase (COX) enzyme inhibitor. It is hepatoxic and implicated in liver injury. Contrarily, mefenamic acid elicits neuroprotection in in vivo ischemic stroke models by inhibiting cell toxicity induced by glutamate. Mefenamic due its inhibitory effect on prostaglandin synthesis can be used in reducing edema and ache. |
| Mechanism of action | Mefenamic acid inhibits bothCOX isoforms with some preference for COX-2and modifies ion channels. |
| 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. Mefenamicacid is indicated for the short-term relief of moderate pain and for primary dysmenorrhea. |
| Safety | Mefenamic acid has mild anti-inflammatoryproperties and is used primarily as a short-termanalgesic. Gastrointestinal disturbances, including possibly allergic diarrhea and potential renaltoxicity, limit its use. |
| Synthesis | Mefenamic acid, N-(2,3-xylyl)anthranylic acid (3.2.19), is synthesizedin basically the same manner, by the reaction of the potassium salt of 2-bromobenzoic acidwith 2,3-dimethylaniline in the presence of copper (II) acetate [80,81]. Synthesis 2: mefenamic acid is prepared viathe Jourdan – Ullmann – Goldberg synthesis utilizing either anthranilic acid and 3-bromo-1,2-dimethylbenzene or 2,3-dimethylaniline and ano-halobenzoic acid in the presence of a coppercatalyst and a proton acceptor. |
| Metabolism | Mefenamic acid is absorbed rapidly following oral administration, with peak plasma levels being attained within 2 to 4hours. It is highly bound to plasma proteins (78.5%) and has a plasma half-life of 2 to 4 hours. Metabolism occursthrough 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 for6%, the 3′-hydroxymethyl metabolite (primarily as the glucuronide) accounting for 25%, and the remaining 20% as thedicarboxylic acid (of which 30% is the glucuronide conjugate). These metabolites are essentiallyinactive. |
| References | [1] Patent: CN105949075, 2016, A. Location in patent: Page/Page column 0029; 0030; 0032; 0034 [2] Bulletin de la Societe Chimique de France, 1982, vol. 2, # 5-6, p. 139 - 143 [3] Tetrahedron Letters, 1997, vol. 38, # 29, p. 5107 - 5110 [4] Synthetic Communications, 2013, vol. 43, # 9, p. 1270 - 1279 [5] Synthetic Communications, 1989, vol. 19, # 11-12, p. 2077 - 2080 |
Mefenamic acid Preparation Products And Raw materials
| Raw materials | 2,3-Dimethylaniline-->2-Chlorobenzoic acid-->Toluene-->Sodium carbonate-->N,N-Dimethylformamide-->Water-->MANGANESE(II) ACETATE TETRAHYDRATE |
