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530-78-9

530-78-9 structure
530-78-9 structure
  • Name: Flufenamic Acid
  • Chemical Name: flufenamic acid
  • CAS Number: 530-78-9
  • Molecular Formula: C14H10F3NO2
  • Molecular Weight: 281.230
  • Catalog: API Antipyretic analgesics Non-steroidal anti-inflammatory drugs
  • Create Date: 2018-09-14 11:41:03
  • Modify Date: 2024-01-02 08:01:14
  • Flufenamic acid is a non-steroidal anti-inflammatory agent, inhibits cyclooxygenase (COX), activates AMPK, and also modulates ion channels, blocking chloride channels and L-type Ca2+ channels, modulating non-selective cation channels (NSC), activating K+ channels.
Name flufenamic acid
Synonyms 2-(3-Trifluoromethylanilino)benzoic Acid
N-(3-Trifluoromethylphenyl)anthranilic Acid
2-{[3-(Trifluoromethyl)phenyl]amino}benzoic acid
Meralen
N-(a,a,a-Trifluoro-m-tolyl)anthranilic Acid
Paraflu
2-[(3-Trifluoromethylphenyl)amino]benzoic Acid
Alfenamin
Flufenamic Acid
EINECS 208-494-1
Surika
Sastridex
2-[3-(trifluoromethyl)anilino]benzoic acid
Opyrin
Achless
Benzoic acid, 2-[[3-(trifluoromethyl)phenyl]amino]-
Tecramine
2-[[3-(Trifluoromethyl)phenyl]amino]benzoic acid
Arlef
MFCD00002422
Ristogen
Parlef
2-((3-(Trifluoromethyl)phenyl)amino)benzoic acid
Description Flufenamic acid is a non-steroidal anti-inflammatory agent, inhibits cyclooxygenase (COX), activates AMPK, and also modulates ion channels, blocking chloride channels and L-type Ca2+ channels, modulating non-selective cation channels (NSC), activating K+ channels.
Related Catalog
Target

COX, Chloride Channel, Calcium Channel, Potassium Channel[1], AMPK[2]

In Vitro Flufenamic acid is a non-steroidal anti-inflammatory agent, inhibits cyclooxygenase (COX), and also modulates ion channels, blocking chloride channels and L-type Ca2+ channels, modulating non-selective cation channels (NSC), activating K+ channels. Flufenamic acid inhibits a wide spectrum of TRP channels, including: C3, C7, M2, M3, M4, M5, M7, M8, V1, V3, and V4 but activates at least two TRP channels (C6 and A1)[1]. Flufenamic acid induces AMPK activation in T84 cells, and such an effect is via a direct stimulation of calcium/calmodulin-dependent protein kinase kinase beta (CaMKKβ) activity[2]. Moreover, Flufenamic acid (FFA; 5-50 μM) dose-dependently inhibits cAMP-dependent Cl- secretion in intact T84 cells, suppresses CFTR-mediated apical ICl-, and blocks the Ca2+-dependent Cl- secretion in a dose-dependent manner with IC50 of appr 10 μM and near complete inhibition at 100 μM in T84 cell monolayers, but shows no effect on Na+-K+ ATPase or NKCC in T84 cells[3].
In Vivo Flufenamic acid (50 mg/kg, i.p.) has anti-inflammatory effect in a mouse model of Vibrio cholerae El Tor variant (EL)-induced diarrhea and significantly abrogates EL-induced intestinal fluid secretion and barrier disruption at 20 mg/kg. Furthermore, Flufenamic acid suppresses NF-κB nuclear translocation and expression of proinflammatory mediators and promotes AMPK phosphorylation in the EL-infected mouse intestine[2].
Cell Assay In brief, apical and basolateral chambers are filled symmetrically with Kreb's solutions. Thereafter, DMSO or Flufenamic acid is added into the basolateral chamber followed by apical membrane permealization by amphotericin B. After the amphotericin B-elicited Isc is stabilized, ouabain is added into the basolateral chamber. The ouabain sensitive Isc is used as an indicator of Na+-K+ ATPase activity[3].
Animal Admin Rats[2] Six-week-old male ICR outbred mice (weight 30-35 g) are fasted for 24 h before anesthesia using an intraperitoneal injection of nembutal (60 mg/kg). Following abdominal incision, the ileum is ligated (appr 3-4 cm long) and inoculated with 100 µL of PBS or PBS containing V. cholerae (105 CFU/loop) with or without a concomitant intraperitoneal injection of Flufenamic acid or metformin. Twelve hours post-inoculation, ileal loops are removed for weight/length ratio measurement, biochemical analysis and ultrastructural evaluation[2].
References

[1]. Guinamard R, et al. Flufenamic acid as an ion channel modulator. Pharmacol Ther. 2013 May;138(2):272-84.

[2]. Pongkorpsakol P, et al. Flufenamic acid protects against intestinal fluid secretion and barrier leakage in a mouse model of Vibrio cholerae infection through NF-κB inhibition and AMPK activation. Eur J Pharmacol. 2017 Mar 5;798:94-104.

[3]. Pongkorpsakol P, et al. Cellular mechanisms underlying the inhibitory effect of flufenamic acid on chloride secretion in human intestinal epithelial cells. J Pharmacol Sci. 2017 Jun;134(2):93-100.
Density 1.4±0.1 g/cm3
Boiling Point 373.9±42.0 °C at 760 mmHg
Melting Point 132-135 °C(lit.)
Molecular Formula C14H10F3NO2
Molecular Weight 281.230
Flash Point 179.9±27.9 °C
Exact Mass 281.066376
PSA 49.33000
LogP 5.62
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.585
Storage condition Refrigerator
Water Solubility 0.0265 g/L (37 ºC)

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CB4375000
CHEMICAL NAME :
Anthranilic acid, N-(alpha,alpha,alpha-trifluoro-m-tolyl)-
CAS REGISTRY NUMBER :
530-78-9
BEILSTEIN REFERENCE NO. :
1996069
LAST UPDATED :
199612
DATA ITEMS CITED :
17
MOLECULAR FORMULA :
C14-H10-F3-N-O2
MOLECULAR WEIGHT :
281.25
WISWESSER LINE NOTATION :
QVR BMR CXFFF

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
2160 mg/kg/26W-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
249 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
185 mg/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
280 mg/kg
TOXIC EFFECTS :
Behavioral - antipsychotic Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
98 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
490 mg/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
620 mg/kg
TOXIC EFFECTS :
Behavioral - antipsychotic Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
158 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
925 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3100 mg/kg/31D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes in urine composition Endocrine - changes in spleen weight Blood - changes in leukocyte (WBC) count
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1500 mg/kg/30D-C
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1350 mg/kg/90D-C
TOXIC EFFECTS :
Liver - changes in liver weight Endocrine - changes in spleen weight Related to Chronic Data - changes in ovarian weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3920 mg/kg/8W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - other changes in urine composition Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1 gm/kg
SEX/DURATION :
female 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - other measures of fertility

MUTATION DATA

TEST SYSTEM :
Human
DOSE/DURATION :
504 mg/kg/8W
REFERENCE :
STBIBN Studia Biophysica. (Akademie-Verlag GmbH, Postfach 1233, Berlin DDR-1086, Ger. Dem. Rep.) V.1- 1966- Volume(issue)/page/year: 50,172,1975
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301-H315-H319
Precautionary Statements P301 + P310-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn:Harmful;
Risk Phrases R22;R36/38
Safety Phrases S26
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS CB4375000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2922499990
HS Code 2922499990
Summary HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

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