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Substance Name: Mefenamic acid [USAN:USP:INN:BAN:JAN]
RN: 61-68-7
UNII: 367589PJ2C
InChIKey: HYYBABOKPJLUIN-UHFFFAOYSA-N
Note
- A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase.
Molecular Formula
- C15-H15-N-O2
Molecular Weight
- 241.2885
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Analgesic
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antirheumatic Agents
- Cyclooxygenase Inhibitors
- Drug / Therapeutic Agent
- Enzyme Inhibitors
- Human Data
- Peripheral Nervous System Agents
- Reproductive Effect
- Sensory System Agents
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Names and Synonyms
Name of Substance
- Mefenamic acid
- Mefenamic acid [USAN:USP:INN:BAN:JAN]
MeSH Heading
- Mefenamic acid
Synonyms
- 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]
- AGN-1255
- Anthranilic acid, N-2,3-xylyl-
- Bafameritin-M
- Bafhameritin-M
- Benzoic acid, 2-((2,3-dimethylphenyl)amino)-
- Benzoic acid, 2-(2,3-dimethylphenyl)amino-
- Bonabol
- BRN 2216243
- CI-473
- CL 473
- CN 35355
- CN-35355
- Coslan
- EINECS 200-513-1
- Fenamin
- HL 1
- HSDB 3115
- INF 3355
- INF-3355
- Lysalgo
- Mefacit
- Mefedolo
- Mefenamate
- Mefenamic acid
- Mefenaminsaeure
- Mefenaminsaeure [German]
- 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
- NSC 94437
- Parkemed
- Ponalar
- Ponstan
- Ponstan forte
- Ponstel
- Rolan
- Tamany Bonsan
- Tanston
- UNII-367589PJ2C
- Vialidon
Systematic Names
- Anthranilic acid, N-(2,3-xylyl)-
- Benzoic acid, 2-((2,3-dimethylphenyl)amino)-
- Mefenamic acid
Registry Numbers
CAS Registry Number
- 61-68-7
FDA UNII
- 367589PJ2C
System Generated Number
- 0000061687
Structure Descriptors
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)InChIKey
HYYBABOKPJLUIN-UHFFFAOYSA-NSmiles
Cc1cccc(Nc2ccccc2C(=O)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: ATAXIA BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) 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) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" LIVER: LIVER FUNCTION TESTS IMPAIRED 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: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: TOXIC PSYCHOSIS | 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. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 230-231 | deg C | EXP | |
pKa Dissociation Constant | 4.2 | (none) | EXP | |
log P (octanol-water) | 5.12 | (none) | EXP | |
Water Solubility | 20 | mg/L | 30 | EXP |
Vapor Pressure | 4.63E-07 | mm Hg | 25 | EST |
Henry's Law Constant | 2.57E-11 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 2.01E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.