Flufenamic Acid

Modify Date: 2024-01-02 08:01:14

Flufenamic Acid structure	Common Name	Flufenamic Acid
	CAS Number	530-78-9	Molecular Weight	281.230
	Density	1.4±0.1 g/cm3	Boiling Point	373.9±42.0 °C at 760 mmHg
	Molecular Formula	C₁₄H₁₀F₃NO₂	Melting Point	132-135 °C(lit.)
	MSDS	Chinese USA	Flash Point	179.9±27.9 °C
	Symbol	GHS06	Signal Word	Danger

Use of Flufenamic Acid

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
Synonym	More Synonyms

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	Signaling Pathways >> Epigenetics >> AMPK Signaling Pathways >> PI3K/Akt/mTOR >> AMPK Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Signaling Pathways >> Membrane Transporter/Ion Channel >> Chloride Channel Signaling Pathways >> Immunology/Inflammation >> COX Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel Research Areas >> Inflammation/Immunology
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)

Flufenamic Acid MSDS(Chinese)

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
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

Precursor 7
CAS#:2765-91-5 methyl 2-[3-(tr... CAS#:98-16-8 3-(Trifluoromet... CAS#:118-91-2 2-Chlorobenzoic acid CAS#:17763-70-1 Benzoic acid, 2...
CAS#:1977-00-0 sodium 2-[[3-(t... CAS#:32509-03-8 1-[3-(trifluoro... CAS#:137488-39-2 1-(3'-trifluoro...
DownStream 5
CAS#:92-30-8 2-(Triflouometh... CAS#:29098-19-9 acetyloxymethyl... CAS#:29261-37-8 benzoyloxymethy... CAS#:2765-91-5 methyl 2-[3-(tr...
CAS#:32509-03-8 1-[3-(trifluoro...

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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Flufenamic Acid

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