基本情報
- CAS
51234-28-7- 標準SMILES
CC(C(=O)O)c1ccc2oc(-c3ccc(Cl)cc3)nc2c1- InChIKey
MITFXPHMIHQXPI-UHFFFAOYSA-N- 分子式
- C16H12ClNO3
- 平均分子量
- 301.72 g/mol
- 単同位体質量
- 301.0505709
概要
Benoxaprofen is a monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group. It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects including liver necrosis, photosensitivity, and carcinogenicity in animals. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an antipsoriatic, a hepatotoxic agent, a nephrotoxic agent, a protein kinase C agonist and an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor. It is a monocarboxylic acid, a member of 1,3-benzoxazoles and a member of monochlorobenzenes. It is functionally related to a propionic acid.
名称と識別子
- 優先名称
- Benoxaprofen
- IUPAC
- 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
- 現地名
- ベノキサプロフェン
- 英語名
- Uniprofen
- 分子式
- C16H12ClNO3
- 分子量
- 301.73
名称と別名
Benoxaprofen51234-28-7OraflexCoxigonOprendl-BenoxaprofenBenoxaprofeneCompound 90459BenoxaprofenumBenoxaprofeno2-[2-(4-Chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acidLilly 90459
名称をさらに表示
化合物904592-[2-(4-クロロフェニル)ベンゾオキサゾール-5-イル]プロピオン酸2-[2-(p-クロロフェニル)ベンゾオキサゾール-5-イル]プロピオン酸2-(p-クロロフェニル)-α-メチル-5-ベンゾオキサゾール酢酸ベノキサプロフェンオラフレックス2-(4-クロロフェニル)-α-メチル-5-ベンゾオキサゾール酢酸2-[2-(4-クロロフェニル)ベンゾオキサゾール-5-イル]プロパン酸2-[2-(4-クロロフェニル)-1,3-ベンゾオキサゾール-5-イル]プロパン酸InflamidLY-90459UniprofenLRCL-3794NSC 299582Aids128826Lilly-90459
(+-)-benoxaprofen2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acidCOMPOUND-90459(1)-2-(4-Chlorophenyl)benzoxazole-5-propionic acidCOMPD 90459NSC-29958217SZX404IMCHEBI:76114
データベース識別子
物性
構造計算による物性
- XLogP
- 4.1
- 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
- 4
- 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
Human DrugsPharmaceuticals
物理化学的性質
- 融点
- 189.5 °C · 189.5°C
- 沸点
- 446.2 · 446.2±30.0 °C(Predicted)
- 比重(密度)
- 1.2411 · 1.2411 (rough estimate)
- 屈折率
- 1.647 · 1.6470 (estimate)
- 貯蔵温度
- Refrigerator
- 溶解性
- DMSO: slightly; Methanol: slightly, sonicated
- 外見
- A solid
- 酸解離定数(Pka)
- 4.36 · 4.36±0.30(Predicted)
- 色
- EtOH からのクリーム色の固体
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
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P273, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 3 (100%)
毒性情報
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Benoxaprofen
vMost-DILI-concern
8
Withdrawn
DOI:10.1016/j.drudis.2016.02.015
安全データ
- 毒性
- LD50 oral in rat: 118mg/kg
化学と産業
薬理情報
ATC Code
M - Musculo-skeletal system
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.
Drugs used to treat or prevent skin disorders or for the routine care of skin.
Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES.
用途と製造
Use ClassificationPharmaceuticals
応用分野
使用A non-steroidal anti-inflammatory ophthalmic agent.
上流・下流製品情報
上流原料
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