Mefenamic acid

Iupac Name：2-(2,3-dimethylanilino)benzoic acid

CAS No.: 61-68-7

Molecular Weight：241.2851

Modify Date.: 2022-10-30 09:12

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: Mefenamic acid
1.2 Synonyms: 2-[(2,3-Dimethylphenyl)amino]benzoic acid 2’,3’-dimethyl-2-diphenylaminecarboxylicaci 2-Diphenylaminecarboxylic acid, 2',3'-dimethyl- ac.mefenamico Benzoic acid, 2-[(2,3-dimethylphenyl)amino]- CI 473，CN-35355 EINECS 200-513-1 Lysalgo Mefenacid Mefenamate Mefenamic Acid (200 mg) Mefenamic acid Solution, 100ppm MefenaMic Aicd (API) MFCD00051721 N-(2,3-Dimethylphenyl)anthranilic Acid 2-(2,3-Dimethylphenylamino)benzoic Acid 2-(2,3-Xylidino)benzoic Acid N-(2,3-Xylyl)anthranilic acid Parkemed Ponalar Ponstan Ponstel Ponstyl Pontal

1.3 CAS No.: 61-68-7

1.4 CID: 4044

1.5 EINECS(EC#): 200-513-1

1.6 Molecular Formula: C15H15NO2 (isomer)

1.7 Inchi: 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)

1.8 InChkey: HYYBABOKPJLUIN-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=C(C(=CC=C1)NC2=CC=CC=C2C(=O)O)C

1.10 Isomers Smiles: CC1=C(C(=CC=C1)NC2=CC=CC=C2C(=O)O)C

2. Properties

2.1 Density: 1.203

2.1 Melting point: 230 °C

2.1 Boiling point: 398.8 °C at 760 mmHg

2.1 Refractive index: 1.639

2.1 Flash Point: 195 °C

2.1 Precise Quality: 241.11000

2.1 PSA: 49.33000

2.1 logP: 3.81820

2.1 Appearance: light yellow solid

2.2 Storage: Refrigerator

2.3 Chemical Properties: Light Yellow Solid

2.4 Color/Form: Powder

2.5 pKa: 4.2(at 25℃)

2.6 Water Solubility: insoluble

2.7 Spectral Properties: MAX ABSORPTION (0.1 N NAOH): 285 NM, 340 NM

2.8 Stability: DARKENS ON PROLONGED EXPOSURE TO LIGHT, IS STABLE @ 25 DEG, 37 DEG, & 45 DEG C.

2.9 StorageTemp: Refrigerator

3. Use and Manufacturing

3.1 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.

3.2 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.

3.3 Usage: Mefenamic acid is used for the same indications as flufenamic acid. Synonyms for this drug areparkemed, ponstan, ponstel, and others.

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22

4.1 Safety Statements: S22;S36/37

4.1 Hazard Declaration: H302

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P301 + P312 + P330

4.1 Formulations/Preparations: CAPSULES: 250 MG.

4.2 WGK Germany: 3

4.2 RTECS: CB4550000

4.2 Safety: Safty information about Mefenamic acid (CAS NO.61-68-7) is:
Hazard Codes:?Xn
Risk Statements: 22-40-20/21/22?
R22:Harmful if swallowed.?
R40:Limited evidence of a carcinogenic effect.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36
S22:Do not breathe dust.?
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: CB4550000

4.3 Specification: ?Mefenamic acid , its cas register number is 61-68-7. It also can be called?Mefenamic acid [USAN:INN:BAN:JAN] ; 2-((2,3-Dimethylphenyl)amino)benzoic acid ; 2-Diphenylaminecarboxylic acid, 2',3'-dimethyl- ; Ac. mefenamico ; Ac. mefenamico [Italian] ; Acide mefenamique ; Acide mefenamique [French] ; Acide mefenamique [INN-French] ; Acido mefenamico ; Acido mefenamico [INN-Spanish] ; Acidum mefenamicum ; Acidum mefenamicum [INN-Latin] ; Anthranilic acid, N-2,3-xylyl- ; Bafhameritin-M ; Benzoic acid, 2-((2,3-dimethylphenyl)amino)- ; Benzoic acid, 2-(2,3-dimethylphenyl)amino- ; Bonabol ; Fenamin ; HL 1 ; Lysalgo ; Mefacit ; Mefedolo ; Mefenamate ; Mefenamic acid ; Mefenaminsaeure ; Mephenamic acid ; Mephenaminic acid ; Methenamic acid ; Mycasaal ; N-(2,3-Dimethylphenyl)anthranilic acid ; N-(2,3-Xylyl)-2-aminobenzoic acid ; N-2,3-Xylylanthranilic acid ; Namphen ; Parkemed ; Ponalar ; Ponstan ; Ponstan forte ; Ponstel ; Rolan ; Tamany Bonsan ; Tanston ; Vialidon . It is a?light yellow solid. Since?it plays a significant role in mefenamic acid elimination, patients with known liver deficiency may be prescribed lower doses. Kidney deficiency may also cause accumulation of the drug and its metabolites in the excretory system. Therefore patients suffering from renal conditions should not be prescribed mefenamic acid.

4.4 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LD50	intravenous	100mg/kg (100mg/kg)	?	Current Medical Research and Opinion. Vol. 4, Pg. 17, 1976.
man	TDLo	oral	14285ug/kg/3D (14.285mg/kg)	?	British Journal of Clinical Practice. Vol. 49, Pg. 161, 1995.
man	TDLo	oral	14285ug/kg/3D (14.285mg/kg)	?	British Journal of Clinical Practice. Vol. 49, Pg. 161, 1995.
man	TDLo	oral	257mg/kg/12D- (257mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	British Medical Journal. Vol. 291, Pg. 661, 1985.
man	TDLo	oral	840mg/kg/6W-I (840mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	British Medical Journal. Vol. 287, Pg. 1626, 1983.
mouse	LD50	intramuscular	400mg/kg (400mg/kg)	?	Pharmaceutical Chemistry Journal Vol. 17, Pg. 353, 1983.
mouse	LD50	intraperitoneal	120mg/kg (120mg/kg)	?	Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 36, 1969.
mouse	LD50	intravenous	96mg/kg (96mg/kg)	?	Yakugaku Zasshi. Journal of Pharmacy. Vol. 89, Pg. 1392, 1969.
mouse	LD50	oral	525mg/kg (525mg/kg)	?	Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
mouse	LDLo	subcutaneous	> 2gm/kg (2000mg/kg)	PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1579, 1970.
rat	LD50	intraperitoneal	327mg/kg (327mg/kg)	?	Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat	LD50	intravenous	112mg/kg (112mg/kg)	?	Current Medical Research and Opinion. Vol. 4, Pg. 17, 1976.
rat	LD50	oral	740mg/kg (740mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION	Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 28, Pg. 99, 1981.
women	LDLo	oral	280mg/kg/2W-I (280mg/kg)	LIVER: LIVER FUNCTION TESTS IMPAIRED KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA	Drug Safety. Vol. 6, Pg. 230, 1991.
women	TDLo	oral	20mg/kg/4D-I (20mg/kg)	GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS	Canadian Medical Association Journal. Vol. 126, Pg. 894, 1982.
women	TDLo	oral	450mg/kg (450mg/kg)	SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: TOXIC PSYCHOSIS BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	South African Medical Journal. Vol. 67, Pg. 823, 1985.
women	TDLo	unreported	120mg/kg/4D (120mg/kg)	BEHAVIORAL: WITHDRAWAL SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Lancet. Vol. 2, Pg. 745, 1980.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

Mass spectrum (electron ionization)

7. Other Information

7.0 Usage: Mefenamic acid has demonstrated antiproliferative activity against colorectal cancer cells. It has Analgesic, Anti-inflammatory activity. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis.

8. Computational chemical data

Molecular Weight: 241.2851g/mol
Molecular Formula: C₁₅H₁₅NO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 241.110278721
Monoisotopic Mass: 241.110278721
Complexity: 292
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 49.3
Heavy Atom Count: 18
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccByMAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAHgAQCAAADAiBmAAyyILAAgCIAiTSSACCAAAlAgAIiAEAbMgIJnrAlZGEcYhm0AHI2ceYyKCOgAAAQAASAAAAAACAACQAAAAAAAAAAA==

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