基本情報
- 標準SMILES
Cc1cccc(N2CC(CO)OC2=O)c1- InChIKey
MXUNKHLAEDCYJL-UHFFFAOYSA-N- 分子式
- C11H13NO3
- 平均分子量
- 207.23 g/mol
- 単同位体質量
- 207.08954328
概要
5-(hydroxymethyl)-3-(3-methylphenyl)-1,3-oxazolidin-2-one is a member of the class of oxazolidinones that is 5-(hydroxymethyl)-1,3-oxazolidin-2-one substituted by a 3-methylphenyl group at position 3. It is a primary alcohol, a member of toluenes and an oxazolidinone.
名称と識別子
- 優先名称
- Toloxatone
- IUPAC
- 5-(hydroxymethyl)-3-(3-methylphenyl)-1,3-oxazolidin-2-one
- 現地名
- トロキサトン
- 英語名
- Toloxatone
- 分子式
- C11H13NO3
- 分子量
- 207.23
名称と別名
名称をさらに表示
データベース識別子
- CAS
29218-27-7- PubChem CID
- 34521
- DTXSID
DTXSID40865478- ChEMBL
CHEMBL18116- ChEBI
CHEBI:156575- UNII
- 5T206015T5
- EC Number
- 249-522-2
- Nikkaji
- J21.701H
物性
構造計算による物性
- XLogP
- 1.2
- 極性表面積
- 49.8 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 2
- 重原子数
- 15
- 形式電荷
- 0
- 複雑度
- 244
物理化学的性質
- 融点
- 76 ° · 76°
- 沸点
- 358.9 · 358.9±21.0 °C(Predicted)
- 比重(密度)
- 1.245 · 1.245±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · Inert atmosphere,2-8°C
- 溶解性
- 10 mg/mL · DMSO:>10mg/mL
- 外見
- 個体
- 酸解離定数(Pka)
- 14.05 · 14.05±0.10(Predicted)
- 色
- White to off-white
- InChI
- 1S/C11H13NO3/c1-8-3-2-4-9(5-8)12-6-10(7-13)15-11(12)14/h2-5,10,13H,6-7H2,1H3
- InChIKey
- MXUNKHLAEDCYJL-UHFFFAOYSA-N
- SMILES
- Cc1cccc(c1)N2CC(CO)OC2=O
安全と法規制
GHS分類
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
安全データ
- wgk
- 3
- rtecs
- RQ2867500
- ridadr
- 3249
- 毒性
- LD50 orally in mice (mg/kg): 1850 (Fauran); also reported as 1500 (Raynaud)
- risk_code
- 22
- hazard_code
- Xn
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard Classifications
- Acute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
N - Nervous system
QN - Nervous system
Mechanism of Action
This medication is a reversible inhibitor of monoamine oxidase type-A (also known as RIMA). MAO-A can be found in norepinephrinergic and serotonergic neurons and regulates the metabolism of serotonin and catecholamines, allowing for increased circulation in the synaptic cleft. Traditional monoamine oxidase inhibitors irreversibly inhibit monoamine oxidase and therefore, side effects, drug interactions, and food interactions persist as long as 2-3 weeks after discontinuing toloxatone. The elevation of serotonin and norepinephrine levels occurs rapidly after medication administration. However, the therapeutic relief of depressive symptoms requires weeks of daily treatment to observe results. Selective and reversible MAO-A inhibitors are more effective in treating major depression without several of the drug and food interactions associated with traditional monoamine oxidase inhibitors.
MeSH Pharmacological Classification
Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.
A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p414)
Absorption, Distribution and Excretion
Mainly hepatic 1% of drug is excreted unchanged in the urine
High hepatic excretion rate
応用分野
説明Toloxatone is a selective, reversible and competitive inhibitor of type A monoamine oxidase (MAO-A) which shows clinical utility as an antidepressant. It is reportedly free of the "cheese effect" in man, possibly due to the reversible nature of its inhibitory effect on intestinal MAO-A in the presence of high concentrations of tyramine.
使用Toloxatone is a monoamine oxidase-A (MAO-A) inhibitor.
上流・下流製品情報
上流原料
サプライヤー35 社
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