氟芬那酸

氟芬那酸用途

Flufenamic acid 是一种非甾体类抗炎剂,能够抑制 COX 的活性,激活 AMPK 的活性,调节离子通道,阻滞氯离子通道 (chloride channel) 和 L-型钙离子通道 (L-type Ca2+ channel),调节非选择性阳离子通道,激活钾离子通道 (K+ channel) 等。

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氟芬那酸名称

[ CAS 号 ]:
530-78-9

[ 中文名 ]:
氟灭酸

[ 英文名 ]:
Flufenamic Acid

[中文别名 ]:

[英文别名 ]:

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

氟芬那酸生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 表观遗传学 >> AMPK

信号通路 >> PI3K/Akt/mTOR 信号通路 >> AMPK

信号通路 >> 跨膜转运 >> 钙通道

信号通路 >> 跨膜转运 >> 氯离子通道

信号通路 >> 免疫及炎症 >> COX

信号通路 >> 跨膜转运 >> 钾通道

研究领域 >> 炎症/免疫

[ 靶点 ]

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

[体外研究]

氟芬那酸是非甾体抗炎剂,抑制环加氧酶(COX),还调节离子通道,阻断氯离子通道和L型Ca2 +通道,调节非选择性阳离子通道(NSC),激活K +通道。氟芬那酸抑制广谱的TRP通道,包括：C3,C7,M2,M3,M4,M5,M7,M8,V1,V3和V4,但激活至少两个TRP通道(C6和A1)[1]。氟芬那酸在T84细胞中诱导AMPK活化,这种作用是通过直接刺激钙/钙调蛋白依赖性蛋白激酶激酶β(CaMKKβ)活性[2]。此外,氟芬那酸(FFA;5-50μM)剂量依赖性地抑制完整T84细胞中cAMP依赖性Cl-分泌,抑制CFTR介导的顶端IC1-,并以剂量依赖性方式阻断Ca2 +依赖性Cl-分泌。在T84细胞单层中,IC50约为10μM,接近完全抑制在100μM,但对T84细胞中的Na + -K + ATP酶或NKCC没有影响[3]。

[体内研究]

氟虫胺酸(50mg/kg,ip)在霍乱弧菌El Tor变体(EL)诱导的腹泻的小鼠模型中具有抗炎作用,并且在20mg/kg时显着消除EL诱导的肠液分泌和屏障破坏。此外,氟芬那酸抑制NF-κB核转位和促炎介质的表达,并促进EL感染的小鼠肠中的AMPK磷酸化[2]。

[细胞实验]

简而言之，顶端和基底外侧腔室用Kreb溶液对称填充。此后，将DMSO或氟芬那酸加入基底外侧室中，然后通过两性霉素B进行顶膜渗透。在两性霉素B诱发的Isc稳定后，将哇巴因加入基底外侧室中。哇巴因敏感的Isc用作Na + -K + ATP酶活性的指标[3]。

[动物实验]

大鼠[2]使用腹膜内注射戊巴比妥（60mg / kg），在麻醉前将6周龄雄性ICR远交小鼠（体重30-35g）禁食24小时。腹部切口后，连接回肠（约3-4cm长），并接种100μL含有霍乱弧菌（105CFU /环）的PBS或PBS，同时或不同时腹膜内注射氟芬那酸或二甲双胍。接种后12小时，取出回肠环进行重量/长度比测量，生化分析和超微结构评估[2]。

[参考文献]

[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.

[相关活性小分子]

氟芬那酸物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
373.9±42.0 °C at 760 mmHg

[ 熔点 ]:
132-135 °C(lit.)

[ 分子式 ]:
C₁₄H₁₀F₃NO₂

[ 分子量 ]:
281.230

[ 闪点 ]:
179.9±27.9 °C

[ 精确质量 ]:
281.066376

[ PSA ]:
49.33000

[ LogP ]:
5.62

[ 外观性状 ]:
白色至淡黄色结晶粉末

[ 蒸汽压 ]:
0.0±0.9 mmHg at 25°C

[ 折射率 ]:
1.585

[ 储存条件 ]:
Refrigerator

[ 水溶解性 ]:
0.0265 g/L (37 ºC)

氟芬那酸MSDS

详细MSDS(安全技术说明书)

氟芬那酸毒性和生态

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

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氟芬那酸安全信息

[ 符号 ]:

GHS06

[ 信号词 ]:
Danger

[ 危害声明 ]:
H301-H315-H319

[ 警示性声明 ]:
P301 + P310-P305 + P351 + P338

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ 危害码 (欧洲) ]:
Xn:Harmful;

[ 风险声明 (欧洲) ]:
R22;R36/38

[ 安全声明 (欧洲) ]:
S26

[ 危险品运输编码 ]:
UN 2811 6.1/PG 3

[ WGK德国 ]:
3

[ RTECS号 ]:
CB4375000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1(b)

[ 海关编码 ]:
2922499990

氟芬那酸合成路线

详细合成路线

氟芬那酸上下游产品

氟芬那酸上游产品

氟芬那酸下游产品

氟芬那酸制备

由间氨基三氟甲苯与邻氯苯甲酸缩合而得。

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氟芬那酸海关

[ 海关编码 ]: 2922499990

[ 中文概述 ]:
2922499990 其他氨基酸及其酯及它们的盐（含有一种以上含氧基的除外）. 增值税率:17.0% 退税率:9.0% 监管条件:AB(入境货物通关单,出境货物通关单) 最惠国关税:6.5% 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 乙醇胺及其盐应报明色度, 乙醇胺及其盐应报明包装

[ 监管条件 ]: A.入境货物通关单 B.出境货物通关单

[ 检验检疫 ]: P.进境动植物、动植物产品检疫 Q.出境动植物、动植物产品检疫 R.进口食品卫生监督检验 S.出口食品卫生监督检验 M.进口商品检验 N.出口商品检验

[ 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%

氟芬那酸文献

Purinergic signaling via P2Y receptors up-mediates IL-6 production by liver macrophages/Kupffer cells.

J. Toxicol. Sci. 39(3) , 413-23, (2014)

Resident macrophages in the liver (Kupffer cells) produce various cytokines and chemokines, and have important roles in hepatitis and liver fibrosis. The cells are activated by various factors, for ex...

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Convenient QSAR model for predicting the complexation of structurally diverse compounds with β-cyclodextrins

Bioorg. Med. Chem. 17 , 896-904, (2009)

This paper reports a QSAR study for predicting the complexation of a large and heterogeneous variety of substances (233 organic compounds) with beta-cyclodextrins (beta-CDs). Several different theoret...

更多文献

氟芬那酸

氟芬那酸用途

氟芬那酸名称

氟芬那酸生物活性

氟芬那酸物理化学性质

氟芬那酸MSDS

详细MSDS(安全技术说明书)

氟芬那酸毒性和生态

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

氟芬那酸安全信息

氟芬那酸合成路线

详细合成路线

氟芬那酸上下游产品

氟芬那酸上游产品

氟芬那酸下游产品

氟芬那酸制备

氟芬那酸海关

氟芬那酸文献

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