トロキサトン

Toloxatone

HCID 34521CAS 29218-27-7

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

Toloxatone29218-27-7HumorylPerenumToloxatona5-(Hydroxymethyl)-3-(3-methylphenyl)-2-oxazolidinoneToloxatonumTaloxotoneDelalande 692765-Hydroxymethyl-3-(m-tolyl)-2-oxazolidinoneDTXSID408654785T206015T5
名称をさらに表示
5-(ヒドロキシメチル)-3-(3-メチルフェニル)オキサゾリジン-2-オン5-(ヒドロキシメチル)-3-(m-トリル)オキサゾリジン-2-オン5-ヒドロキシメチル-3-(m-トリル)オキサゾリジン-2-オントロキサトン5-(ヒドロキシメチル)-3-(3-メチルフェニル)-1,3-オキサゾリジン-2-オン3-(3-メチルフェニル)-5-(ヒドロキシメチル)-2-オキサゾリジノン69276MDToloxatone USP/EP/BPToloxatone - MD 69276Toloxatone, 10 mM in DMSO
MD-69276(3-methyl)-3-phenyl-5-hydroxymethyl-2-oxazolidinoneRefChem:898548DTXCID10813880N06AG03CHEBI:134870249-522-25-(Hydroxymethyl)-3-(m-tolyl)oxazolidin-2-one

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

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

安全と法規制

GHS分類

GHS Classification · 4 件

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

Hazard Classes and CategoriesAcute Tox. 4 (100%)

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

化学と産業

薬理情報

ATC Code · 2 件

N - Nervous system

QN - Nervous system

PharmacodynamicsThis drug has been shown to help manage the symptoms of depression by maintaining neuro-synaptic levels of serotonin and catecholamines while regulating their metabolism, which leads to relief of depressive symptoms.
Mechanism of Action · 1 件

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.

Biological Half-Life1-3 h
MeSH Pharmacological Classification · 2 件

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 · 2 件

Mainly hepatic 1% of drug is excreted unchanged in the urine

High hepatic excretion rate

応用分野 · 2 件

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.

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