基本情報
- CAS
61-68-7- 標準SMILES
Cc1cccc(Nc2ccccc2C(=O)O)c1C- InChIKey
HYYBABOKPJLUIN-UHFFFAOYSA-N- 分子式
- C15H15NO2
- 平均分子量
- 241.28 g/mol
- 単同位体質量
- 241.11027872
概要
Mefenamic acid is an aminobenzoic acid that is anthranilic acid in which one of the hydrogens attached to the nitrogen is replaced by a 2,3-dimethylphenyl group. Although classed as a non-steroidal anti-inflammatory drug, its anti-inflammatory properties are considered to be minor. It is used to relieve mild to moderate pain, including headaches, dental pain, osteoarthritis and rheumatoid arthritis. It has a role as a non-steroidal anti-inflammatory drug, an analgesic, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, a xenobiotic, an antirheumatic drug and an environmental contaminant. It is an aminobenzoic acid and a secondary amino compound.
名称と識別子
- 優先名称
- Mefenamic Acid
- IUPAC
- 2-(2,3-dimethylanilino)benzoic acid
- 現地名
- メフェナム酸
- 英語名
- Mefenamic acid
- 分子式
- C15H15NO2
- 分子量
- 241.29
名称と別名
mefenamic acid61-68-7Ponstel2-[(2,3-dimethylphenyl)amino]benzoic acidMephenamic acid2-((2,3-Dimethylphenyl)amino)benzoic acidPonstanMephenaminic acidMethenamic acidLysalgoTanstonVialidon
名称をさらに表示
メフェナム酸ノイリトールCマイカサールN-(2,3-キシリル)アントラニル酸2-(2,3-ジメチルアニリノ)安息香酸ポンタックスo-(2,3-ジメチルアニリノ)安息香酸2-(2,3-ジメチルフェニルアミノ)安息香酸メフェナムサンo-(2,3-キシリルアミノ)安息香酸ヨウフェナムバファメリチンMルメンタールポンタール2-[(2,3-ジメチルフェニル)アミノ]安息香酸ミルレストワンメデー2-(2,3-キシリジノ)安息香酸N-(2,3-ジメチルフェニル)アントラニル酸メフェナム酸標準品MefenamicMefanamic acidMEFENAMATELFRINTLac.mefenamicoMefenamic Acid (200 mg)
Acide mefenamiqueMefenaminsaeureCN-35355N-2,3-Xylylanthranilic acidAcido mefenamicoMefenaminic AcidINF-3355Acidum mefenamicum
物性
構造計算による物性
- XLogP
- 5.1
- 極性表面積
- 49.3 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 3
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 292
実験および物理化学的性質
Drugs
DEA NFLIS-Drug Category -> Analgesics
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
Pharmaceuticals -> NSAIDs
LogP
4.2
4.38
Color/Form
CRYSTALS
WHITE TO OFF-WHITE, CRYSTALLINE POWDER
Solubility
WHITE POWDER; SOLUBILITY IN WATER: GREATER THAN 5 G/100 ML /SODIUM SALT/
IN WATER @ PH 7.1: 0.0041 G/100 ML @ 25 °C, 0.008 G/100 ML @ 37 °C; SOL IN SOLN OF ALKALI HYDROXIDES; SPARINGLY SOL IN ETHER, CHLOROFORM; SLIGHTLY SOL IN ETHANOL
1 G SOL IN 26 ML DIMETHYLFORMAMIDE & 220 ML ALCOHOL
1.37e-02 g/L
>36.2 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
Breast Feeding; Lactation; Milk, Human; Analgesic Agents; Antii-nflammatory Agents, Nonsteroidal
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Melting Point
230-231 °C
230-231 °C
DECARBOXYLATES @ TEMP ABOVE ITS MELTING POINT (@ 300 °C, 100% IS DECARBOXYLATED IN 3 MIN)
230 - 231 °C
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 0.8% (1 of 126) of reports.
Warning
H302 (99.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 126 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
危険有害性情報
Regulatory InformationMefenamic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzoic acid, 2-[(2,3-dimethylphenyl)amino]-: Environment tier I assessment
Hazard Classes and Categories
Acute Tox. 4 (99.2%)
Acute toxicity (Oral) - Category 4
毒性情報
Interactions
...WARFARIN CAN BE DISPLACED FROM PLASMA PROTEIN BY MEFENAMIC ACID...INCR IN FREE WARFARIN CAN RANGE FROM 66-400% WITH CORRESPONDING INCR IN ANTICOAGULANT ACTION. BECAUSE OF DOSAGES INVOLVED, INTERACTIONS ARE MORE LIKELY TO BE IMPORTANT IN PT TREATED WITH WARFARIN THAN IN WORKERS WHO USE IT AS PESTICIDE...
EFFECTS OF ORAL ANTICOAGULANT AGENTS ARE ENHANCED.
Hepatotoxicity
In prospective studies less than 5% of patients taking mefenamic acid experienced transient serum aminotransferase elevations. The abnormalities usually resolved even while continuing the drug and without dose modification. Marked aminotransferase elevations (>3 fold elevated) occurred in
化学と産業
薬理情報
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
Protein Binding90%
Pharmacodynamics
Mefenamic acid, an anthranilic acid derivative, is a member of the fenamate group of nonsteroidal anti-inflammatory drugs (NSAIDs). It exhibits anti-inflammatory, analgesic, and antipyretic activities. Similar to other NSAIDs, mefenamic acid inhibits prostaglandin synthetase.
Mechanism of Action
Mefenamic acid binds the prostaglandin synthetase receptors COX-1 and COX-2, inhibiting the action of prostaglandin synthetase. As these receptors have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity, the symptoms of pain are temporarily reduced.
Biological Half-Life
2 hours
...ABOUT 50%...IS EXCRETED IN URINE WITHIN 24 HR /HUMAN, ORAL/
Metabolism/Metabolites
Mefenamic acid undergoes metabolism by CYP2C9 to 3-hydroxymethyl mefenamic acid, and further oxidation to a 3-carboxymefenamic acid may occur. The activity of these metabolites has not been studied. Mefenamic acid is also glucuronidated directly.
MEFENAMIC ACID...IS TRANSFORMED TO HYDROXYMETHYL DERIVATIVE & TO ACID BY MAJOR, IF NOT ONLY, METABOLIC PATHWAY IN DOG, MONKEY, & HUMAN.
Mefenamic acid has known human metabolites that include 3-hydroxymethyl mefenamic aci.
FDA Pharmacological Classification
367589PJ2C
MEFENAMIC ACID
Mechanisms of Action [MoA] - Cyclooxygenase Inhibitors
Chemical Structure [CS] - Anti-Inflammatory Agents, Non-Steroidal
Established Pharmacologic Class [EPC] - Nonsteroidal Anti-inflammatory Drug
Mefenamic acid is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of mefenamic acid is as a Cyclooxygenase Inhibitor.
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