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Substance Name: Flufenamic acid [USAN:INN:BAN:JAN]
RN: 530-78-9
UNII: 60GCX7Y6BH
InChIKey: LPEPZBJOKDYZAD-UHFFFAOYSA-N

Note

  • An anthranilic acid derivative with analgesic, anti-inflammatory, and antipyretic properties. It is used in musculoskeletal and joint disorders and administered by mouth and topically. (From Martindale, The Extra Pharmacopoeia, 30th ed, p16)

Molecular Formula

  • C14-H10-F3-N-O2

Molecular Weight

  • 281.232
 

Classification Codes

  • Anti-Inflammatory
  • Anti-Inflammatory Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Flufenamic acid
  • Flufenamic acid [USAN:INN:BAN:JAN]

MeSH Heading

  • Flufenamic acid

Synonyms

  • 2-((3-(Trifluoromethyl)phenyl)amino)benzoic acid
  • 2-((3-Trifluromethyl)phenyl)aminobenzoic acid
  • 3'-Trifluoromethyldiphenylamine-2-carboxylic acid
  • 3-14-00-00905 (Beilstein Handbook Reference)
  • Achless
  • Acide flufenamique
  • Acide flufenamique [INN-French]
  • Acido flufenamico
  • Acido flufenamico [INN-Spanish]
  • Acido flufenamico [Italian]
  • Acidum flufenamicum
  • Acidum flufenamicum [INN-Latin]
  • Ansatin
  • ANT-1
  • Arlef
  • Benzoic acid, 2-((3-(trifluoromethyl)phenyl)amino)-
  • BRN 1996069
  • C.I. 440
  • CCRIS 5266
  • CI 440
  • CN-27,554
  • EC 208-494-1
  • EINECS 208-494-1
  • Flufacid
  • Flufenamic acid
  • Flufenaminsaeure
  • Flufenaminsaeure [German]
  • Fluore-200
  • Fluphenamic acid
  • Fullsafe
  • INF 1837
  • INF-1837
  • Lanceat
  • Meralen
  • N-(3-Trifluoromethylphenyl)anthranilic acid
  • N-(alpha,alpha,alpha-Trifluoro-m-tolyl)anthranilic acid
  • N-(m-Trifluoromethylphenyl)-2-aminobenzoic acid
  • Nichisedan
  • NSC 219007
  • NSC-82699
  • Paraflu
  • Parlef
  • Parlif
  • Plostene
  • Reumajust A
  • Ristogen
  • Sastridex
  • Surika
  • Tecramine
  • TVX 916
  • UNII-60GCX7Y6BH

Systematic Names

  • Anthranilic acid, N-(alpha,alpha,alpha-trifluoro-m-tolyl)-
  • Benzoic acid, 2-((3-(trifluoromethyl)phenyl)amino)-
  • Flufenamic acid

Registry Numbers

CAS Registry Number

  • 530-78-9

FDA UNII

  • 60GCX7Y6BH

System Generated Number

  • 0000530789

Structure Descriptors

InChI

1S/C14H10F3NO2/c15-14(16,17)9-4-3-5-10(8-9)18-12-7-2-1-6-11(12)13(19)20/h1-8,18H,(H,19,20)

InChIKey

LPEPZBJOKDYZAD-UHFFFAOYSA-N

Smiles

c1c(c(Nc2cccc(c2)C(F)(F)F)ccc1)C(O)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 925mg/kg (925mg/kg)   Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 11, Pg. 220, 1974.
mouse LD50 intramuscular 500mg/kg (500mg/kg)   Pharmaceutical Chemistry Journal Vol. 17, Pg. 353, 1983.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 intravenous 158mg/kg (158mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 89, Pg. 1392, 1969.
mouse LD50 oral 490mg/kg (490mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 16, Pg. 1011, 1978.
mouse LD50 subcutaneous 620mg/kg (620mg/kg) BEHAVIORAL: ANTIPSYCHOTIC

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Oyo Yakuri. Pharmacometrics. Vol. 18, Pg. 845, 1979.
rat LD50 intraperitoneal 185mg/kg (185mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Oyo Yakuri. Pharmacometrics. Vol. 16, Pg. 1011, 1978.
rat LD50 intravenous 98mg/kg (98mg/kg)   Current Medical Research and Opinion. Vol. 4, Pg. 17, 1976.
rat LD50 oral 249mg/kg (249mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 221, Pg. 132, 1976.
rat LD50 subcutaneous 280mg/kg (280mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 18, Pg. 845, 1979.
rat LD50 subcutaneous 280mg/kg (280mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: ANTIPSYCHOTIC
Oyo Yakuri. Pharmacometrics. Vol. 18, Pg. 845, 1979.
women TDLo oral 2160mg/kg/26W (2160mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Postgraduate Medical Journal. Vol. 62, Pg. 773, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 133.5 deg C   EXP
log P (octanol-water) 5.25 (none)   EXP
Water Solubility 9.09 mg/L 25 EXP
Vapor Pressure 1.95E-06 mm Hg 25 EST
Henry's Law Constant 1.84E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.70E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.