Flufenamic Acid (HCID 3371)

概要

Flufenamic acid is an aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. An analgesic and anti-inflammatory, it is used in rheumatic disorders. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor. It is an aromatic amino acid and an organofluorine compound. It is functionally related to an anthranilic acid, a (trifluoromethyl)benzene and a diphenylamine. It is a conjugate acid of a flufenamate.

名称と識別子

優先名称: Flufenamic Acid
IUPAC: 2-[3-(trifluoromethyl)anilino]benzoic acid
現地名: フルフェナム酸
英語名: Flufenamic acid
分子式: C14H10F3NO2
分子量: 281.23

名称と別名

flufenamic acid530-78-9ArlefFluphenamic acidAchless2-((3-(Trifluoromethyl)phenyl)amino)benzoic acidAcido flufenamicoN-(3-Trifluoromethylphenyl)anthranilic acidFlufenaminsaeureMeralenAcide flufenamique2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid

名称をさらに表示

N-(3-トリフルオロメチルフェニル)アントラニル酸2-[3-(トリフルオロメチル)アニリノ]安息香酸2-[3-(トリフルオロメチル)フェニルアミノ]安息香酸o-[m-(トリフルオロメチル)アニリノ]安息香酸3-トリフルオロメチル-2'-カルボキシジフェニルアミンアーレフフルフェナム酸N-[3-(トリフルオロメチル)フェニル]アントラニル酸フルセーフテクラミン2-[[3-(トリフルオロメチル)フェニル]アミノ]安息香酸アクレス2-[(α,α,α-トリフルオロ-m-トリル)アミノ]安息香酸パラフルフルフェナミン酸2-(3-トリフルオロメチルアニリノ)安息香酸2-[(3-トリフルオロメチルフェニル)アミノ]安息香酸3-トリフロロメチル-2’-カルボキシ-ジフェニルアミン2-{[3-(トリフルオロメチル)フェニル]アミノ}安息香酸フルフェナム酸, 97%FAFFAFlufenamicX25CyaYFARRci440ANT-1

2-[3-(Trifluoromethyl)anilino]benzoic acidCI 440NSC-82699Acidum flufenamicum2-[[3-(Trifluoromethyl)phenyl]amino]benzoic acidCN-27,5543'-Trifluoromethyldiphenylamine-2-carboxylic acidINF-1837

データベース識別子

CAS: 530-78-9
PubChem CID: 3371
DTXSID: DTXSID7023063
ChEMBL: CHEMBL23588
ChEBI: CHEBI:42638
UNII: 60GCX7Y6BH
EC Number: 208-494-1
Nikkaji: J2.064H

物性

構造計算による物性

XLogP: 5.2
極性表面積: 49.3 Å²
水素結合供与体数: 2
水素結合受容体数: 6
回転可能結合数: 3
重原子数: 20
形式電荷: 0
複雑度: 346

実験および物理化学的性質

PFASPFAS -> PFAS identified in REACH Regulation EC No. 1272/2008

Drugs · 3 件

Pharmaceuticals

Pharmaceuticals -> Musculo-skeletal system -> Anti-inflammatory and antirheumatic products

Pharmaceuticals -> Listed in ZINC15

LogP4.47

Solubility>42.2 [ug/mL] (The mean of the results at pH 7.4)

Human DrugsPharmaceuticals

Dissociation Constants4.09

物理化学的性質

融点: 132 · 132-135 °C(lit.)
沸点: 373.9 · 373.9±42.0 °C(Predicted)
比重(密度): 1.338 · 1.3380 (estimate)
蒸気圧: 0 Pa · 0Pa at 25℃
貯蔵温度: Keep in dark place,Inert atmosphere,Room temperature
溶解性: 11 mg/ml、39 · エタノール、DMSO、ジメチルホルムアミドなどの有機溶媒に可溶。これらの溶媒におけるフルフェナム酸の溶解度は、それぞれ約 11 mg/ml、39 mg/ml、および 59 mg/ml です。
酸解離定数(Pka): 3.9 · pKa 3.9 (Uncertain);3.85 (Uncertain)
外見: 結晶性粉末またはチャンク
色: オフホワイトからグレーグリーン
水溶解度: 0.0265 g/L · 0.0265g/L (37℃)
Merck: 14 · 14,4132
BRN: 1996069 · 1996069
主な用途: 法医学と毒物学医薬品（低分子化合物）獣医
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: OC(=O)c1ccccc1Nc2cccc(c2)C(F)(F)F
LogP: 5.25 · 5.25
CAS データベース: 530 · 530-78-9(CAS DataBase Reference)
NISTの化学物質情報: Flufenamic acid(530-78-9)

化学的性質 · 1 件

化学的特性Fluomic acid is a Pale-Yellow or light yellow-green crystal or crystalline powder with bitter taste. It is almost insoluble in water and can be dissolved in 50% ethanol. It is a non-hormonal anti-inflammatory and analgesic drug. It was prepared by photolysis of the corresponding benzotriazinone.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 0.8% (1 of 120) of reports.

Danger

H301 (95.8%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 120 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationREACH registered substance: Flufenamic acid (EC: 208-494-1)

Other Safety InformationIMAP assessments - Benzoic acid, 2-[[3-(trifluoromethyl)phenyl]amino]-: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 3 (95.8%)

安全データ

wgk: 3
rtecs: CB4375000
ridadr: UN 2811 6.1/PG 3
毒性: LD50 in mice: 715 mg/kg orally (Zoni)
hs_code: 29224999
risk_code: 22-36/38
化審法: (3)-1493, (3)-3002, (9)-907
hazard_code: Xn
safety_code: 26
hazard_class: 6.1(b)
packing_group: III
Hazard Classifications: Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2
ストレージクラス: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects

化学と産業

薬理情報

ATC Code · 2 件

M - Musculo-skeletal system

QM - Musculo-skeletal system

MeSH Pharmacological ClassificationSubstances that reduce or suppress INFLAMMATION.

用途と製造

UsesUse (kg; approx.) in Germany (2009): >250

Use ClassificationPharmaceuticals

応用分野 · 2 件

解説フルフェナム酸，フルフェナムサン，N-(3-trifluoromethylphenyl)anthranilic acid．C14H10F3NO2(281.23)．o-ヨード安息香酸とm-トリフルオロメチルアニリンとを銅触媒の存在下に縮合させると得られる．黄色の結晶．融点132～135 ℃．pKa 3.85．λmax 283 nm．エタノール，クロロホルム，アルカリ性水溶液に可溶，水に不溶．非ステロイド系抗炎症剤として，慢性関節リウマチ，関節炎の治療薬として使用される．LD50 715 mg/kg(ネズミ，経口)．

使用Flufenamic acid is used for moderate pain and dysmenorrhea, but it should not be used for more than 1 week due to the possibility of nephrotoxicity, gastrointestinal toxicity, and anemia. It is frequently used in combination with the anticoagulant warfarin, the effect of which is strengthened when combined with flufenamic acid.

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フルフェナム酸

基本情報

概要