基本情報
- CAS
138112-76-2- 標準SMILES
COc1ccc2cccc(CCNC(C)=O)c2c1- InChIKey
YJYPHIXNFHFHND-UHFFFAOYSA-N- 分子式
- C15H17NO2
- 平均分子量
- 243.3 g/mol
- 単同位体質量
- 243.12592879
概要
Agomelatine is a member of acetamides.
名称と識別子
- 優先名称
- Agomelatine
- IUPAC
- N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
- 現地名
- アゴメラチン
- 英語名
- Agomelatine
- 分子式
- C15H17NO2
- 分子量
- 243.3
名称と別名
名称をさらに表示
データベース識別子
- CAS
138112-76-2- PubChem CID
- 82148
- DTXSID
DTXSID3057642- ChEMBL
CHEMBL10878- ChEBI
CHEBI:134990- UNII
- 137R1N49AD
- EC Number
- 629-727-7
- Nikkaji
- J481.046E
物性
構造計算による物性
- XLogP
- 2.7
- 極性表面積
- 38.3 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 2
- 回転可能結合数
- 4
- 重原子数
- 18
- 形式電荷
- 0
- 複雑度
- 280
実験および物理化学的性質
Drugs
Pharmaceuticals
Pharmaceuticals -> Antidepressants
Pharmaceuticals -> Listed in ZINC15
Solubility
~0.5 mg/ml in 1:1 EtOH:PBS (pH 7.2); ~30 mg/ml in EtOH, DMF & DMSO
7.76e-03 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antidepressants
EMA approved medicines: Human medicine
物理化学的性質
- 融点
- 107 · 107-109°C
- 沸点
- 478.8 · 478.8±28.0 °C(Predicted)
- 比重(密度)
- 1.109 · 1.109±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 50 mg/mL · DMSO:>50mg/mL
- 外見
- 粉
- 酸解離定数(Pka)
- 16.17 · 16.17±0.46(Predicted)
- 色
- ホワイトからオフホワイト
- Merck
- 14 · 14,190
- InChI
- InChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17)
- InChIKey
- YJYPHIXNFHFHND-UHFFFAOYSA-N
- SMILES
- C(NCCC1=C2C(C=CC(OC)=C2)=CC=C1)(=O)C
- CAS データベース
- 138112 · 138112-76-2(CAS DataBase Reference)
化学的性質
化学的特性White Solid
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 1.9% (1 of 54) of reports.
Warning
H315 (22.2%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 54 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
毒性情報
安全データ
- wgk
- 3
- rtecs
- AC5956323
- ridadr
- UN 3077 9 / PGIII
- 毒性
- mouse,LD50,oral,> 1gm/kg (1000mg/kg),United States Patent Document. Vol. #5318994,
- hs_code
- 29241990
- risk_code
- 50
- hazard_code
- N
- safety_code
- 61
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
N06AX22
N - Nervous system
QN - Nervous system
Pharmacodynamics
Agomelatine resynchronises circadian rhythms in animal models of delayed sleep phase syndrome and other circadian rhythm disruptions. It increases noradrenaline and dopamine release specifically in the frontal cortex and has no influence on the extracellular levels of serotonin. Agomelatine has shown an antidepressant-like effect in animal depression models, (learned helplessness test, despair test, and chronic mild stress) circadian rhythm desynchronisation, and in stress and anxiety models. In humans, agomelatine has positive phase shifting properties; it induces a phase advance of sleep, body temperature decline and melatonin onset. Controlled studies in humans have shown that agomelatine is as effective as the SSRI antidepressants paroxetine and sertraline in the treatment of major depression
用途と製造
応用分野
説明Agomelatine is an agonist of melatonin (MT) receptors and a derivative of melatonin . It binds to MT1 and MT2 receptors (Kis = 0.14 and 0.41 nM, respectively) and has an EC50 value of 0.1 nM in a [35S]GTPγS binding assay using CHO cells expressing MT2 receptors. Agomelatine is also an antagonist of the serotonin (5-HT) receptor subtypes 5-HT2B and 5-HT2C (Kis = 0.26 and 0.71 nM, respectively, for the human receptors). Agomelatine (40 mg/kg) inhibits the penile erection response induced by the 5-HT2 agonist Ro 60-0175 in rats. It also increases extracellular levels of noradrenaline and dopamine in the frontal cortex of freely moving rats when administered at doses ranging from 20 to 80 mg/kg. Agomelatine (10 mg/kg) reduces immobility time in the forced swim test and increases the amount of time spent in the open arms of the elevated plus maze in mice, indicating antidepressant-like and anxiolytic-like activity, in a transgenic neuroendocrine model of depression. It also increases the rate of readjustment to circadian activity cycles following an induced phase shift.
使用Agomelatine is a melatoninergic agonist and selective antagonist of 5-HT2C receptors, and has been shown to be active in several animal models of depression. Agomelatine (S20098) displayed pKi values of 6.4 and 6.2 at native (porcine) and cloned, human (h)5-hydroxytryptamine (5-HT)2C receptors, respectively.
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