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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
 

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

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

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

c1(c(cccc1)C(=O)O)Nc1c(c(ccc1)C)C

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.