アゴメラチン

Agomelatine

HCID 82148

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

Agomelatine138112-76-2ThymanaxValdoxanS20098S-20098AgomelatinaAGO-178S 20098N-(2-(7-methoxy-1-naphthyl)ethyl)acetamideagomelatinumAGO178
名称をさらに表示
アゴメラチンN-[2-(7-メトキシ-1-ナフタレニル)エチル]アセトアミドN-[2-(7-メトキシナフタレン-1-イル)エチル]アセトアミドN-[2-(7-メトキシ-1-ナフチル)エチル]アセトアミドAGOMELATINGOMELATINEMELITORAgomelatine original crystal formomeLatineAgomeLMelitorCS-1963
DTXSID3057642137R1N49ADN-[2-(7-methoxy-1-naphthyl)ethyl]acetamideDTXCID4031431RefChem:110192N06AX22N-(2-(7-Methoxynaphthalen-1-yl)ethyl)acetamideN-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide

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

実験および物理化学的性質

Drugs · 3 件

Pharmaceuticals

Pharmaceuticals -> Antidepressants

Pharmaceuticals -> Listed in ZINC15

Solubility · 2 件

~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 · 2 件

Breast Feeding; Lactation; Milk, Human; Antidepressants

EMA approved medicines: Human medicine

Physical DescriptionSolid
Collision Cross Section156.3 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

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

化学的性質

化学的特性White Solid

安全と法規制

GHS分類

GHS Classification · 5 件

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

Hazard Classes and CategoriesSkin Irrit. 2 (22.2%)

毒性情報

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

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

化学と産業

薬理情報

ATC Code · 3 件

N06AX22

N - Nervous system

QN - Nervous system

Protein Binding> 95%
Pharmacodynamics · 1 件

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

Mechanism of ActionThe novel antidepressant agent, agomelatine, behaves as an agonist at melatonin receptors (MT1 and MT2) and as an antagonist at serotonin (5-HT)(2C) receptors.
Biological Half-Life<2 hours
Metabolism/MetabolitesHepatic (90% CYP1A2 and 10% CYP2C9).

用途と製造

UsesUse (kg; approx.) in Germany (2009): >100
応用分野 · 2 件

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.

サプライヤー100 社

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
北京海步医药科技有限公司67886402 15600038801 · [email protected]
山东鲁宁药业有限公司13371546309;13305469775
INTATRADE GmbH+49 3493/605464 · [email protected]

関連反応

35 件

化合物ノート

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