基本情報
- CAS
66934-18-7- 標準SMILES
C[C@H](C(=O)O)c1ccc2oc(-c3ccc(F)cc3)nc2c1- InChIKey
ARPYQKTVRGFPIS-VIFPVBQESA-N- 分子式
- C16H12FNO3
- 平均分子量
- 285.27 g/mol
- 単同位体質量
- 285.08012141
概要
Flunoxaprofen is a monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group (the S-enantiomer). Although it was shown to be effective in treatment of rheumatoid arthritis and osteoarthritis, the clinical use of flunoxaprofen was discontinued due to possible hepatotoxic side-effects. It has a role as a non-steroidal anti-inflammatory drug, an antirheumatic drug, a hepatotoxic agent and a protein kinase C agonist. It is a monocarboxylic acid, an organofluorine compound and a member of 1,3-benzoxazoles. It is functionally related to a propionic acid.
名称と識別子
- 優先名称
- Flunoxaprofen
- IUPAC
- (2S)-2-[2-(4-fluorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
- 現地名
- フルノキサプロフェン
- 英語名
- Flunoxaprofen
- 分子式
- C16H12FNO3
- 分子量
- 285.273
名称と別名
Flunoxaprofen66934-18-7Flunoxaprofeno(2s)-2-[2-(4-fluorophenyl)-1,3-benzoxazol-5-yl]propanoic acidFlunoxaprofenum(S)-(+)-FlunoxaprofenflunoxaprofeneUKU5U19W9M(S)-2-(4-Fluorophenyl)-alpha-methyl-5-benzoxazoleacetic acid(+)-2-(p-Fluorophenyl)-alpha-methyl-5-benzoxazoleacetic acidCHEBI:76154DTXSID00912311
名称をさらに表示
プリアキシムフルノキサプロフェン(S)-2-(4-フルオロフェニル)-α-メチル-5-ベンゾオキサゾール酢酸S-(+)-フルノキサプロフェン(2S)-2-[2-(4-フルオロフェニル)-1,3-ベンゾオキサゾール-5-イル]プロパン酸S-(+)-FlunoxaprofenFlunoxaprofen USP/EP/BP(S)-2-(4-Fluorophenyl)-α-methyl-5-benzoxazoleacetic acid5-Benzoxazoleacetic acid, 2-(4-fluorophenyl)-α-methyl-, (αS)-
(2S)-2-(2-(4-fluorophenyl)-1,3-benzoxazol-5-yl)propanoic acid(+)-FlunoxaprofenRefChem:599355G02CC04M01AE15DTXCID701341333PriaximFlunoxaprofen [INN]
データベース識別子
物性
構造計算による物性
- XLogP
- 3.6
- 極性表面積
- 63.3 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 5
- 回転可能結合数
- 3
- 重原子数
- 21
- 形式電荷
- 0
- 複雑度
- 384
実験および物理化学的性質
DrugsPharmaceuticals -> Musculo-skeletal system -> Anti-inflammatory and antirheumatic products
物理化学的性質
- 融点
- 162 · 162-164°
- 比旋光度
- 20 · D20 +50° (c = 2% in DMF)
- 沸点
- 419.4 · 419.4±30.0 °C(Predicted)
- 比重(密度)
- 1.334 · 1.334±0.06 g/cm3(Predicted)
- 酸解離定数(Pka)
- 4.36 · 4.36±0.30(Predicted)
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。
安全データ
- 毒性
- LD50 orally in mice: ~1200 mg/kg (Dunwell)
化学と産業
薬理情報
ATC Code
M - Musculo-skeletal system
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
QM - Musculo-skeletal system
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
応用分野
説明Flunoxaprofen is an antiinflammatory related to now withdrawn benoxaprofen, reportedly useful in the treatment of rheumatoid arthritis, myositis, synovitis and osteoarthritis. Its major mechanism of action is reported to be lipoxygenase inhibition, thus enabling the control of inflammation with less severe gastric disturbances.
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補足説明
定義ChEBI: A monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group (the S-enantiomer). Although it was shown to be effective in treatment of rheumatoid arthritis and osteoarthritis, the clinical use of flunoxaprofen was discontinued due to possible hepatotoxic side-effects.
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