アゴメラチン
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 · S-20098 · 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 · AGOMELATIN · Valdoxan · GOMELATINE
識別子と物理属性
| CAS No. | 138112-76-2 |
|---|---|
| 分子式 | C15H17NO2 |
| 平均分子量 | 243.3 g/mol |
| 単同位体質量 | 243.12592879 g/mol |
| SMILES | COc1ccc2cccc(CCNC(C)=O)c2c1 |
| InChIKey | YJYPHIXNFHFHND-UHFFFAOYSA-N |
| PubChem CID | 82148 |
| ChEMBL | CHEMBL10878 |
| ChEBI | CHEBI:134990 |
| EC No. | 629-727-7 |
| DTXSID | DTXSID3057642 |
| 現地名 | アゴメラチン |
化学・物理的性質
| XLogP | 2.7 |
|---|---|
| 極性表面積 | 38.3 |
| 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 |
| 医薬品 | PharmaceuticalsPharmaceuticals -> AntidepressantsPharmaceuticals -> Listed in ZINC15 |
| 溶解度 | ~0.5 mg/ml in 1:1 EtOH:PBS (pH 7.2)~30 mg/ml in EtOH, DMF & DMSO7.76e-03 g/LDMSO：>50mg/mL |
| Human Drugs | Breast FeedingLactationMilk, HumanAntidepressantsEMA approved medicines: Human medicine |
| Physical Description | Solid |
| Collision Cross Section | 156.3 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)] |
| 融点 | 107-109°C |
| 沸点 | 478.8±28.0 °C(Predicted) |
| 密度 | 1.109±0.06 g/cm3(Predicted) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 粉 |
| pKa（酸解離定数） | 16.17±0.46(Predicted) |
| 色 | ホワイトからオフホワイト |
| Merck | 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 | 138112-76-2(CAS DataBase Reference) |
化学的特性
White Solid
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 1.9% (1 of 54) of reports.WarningH315 (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. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (22.2%) |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | AC5956323 |
| 輸送番号（UN） | UN 3077 9 / PGIII |
| 毒性 | mouse,LD50,oral,> 1gm/kg (1000mg/kg),United States Patent Document. Vol. #5318994, |
| 税関コード | 29241990 |
| 危険文句（R） | 50 |
| 危険表示 | N |
| 安全措置（S） | 61 |
| 危険等級 | Aquatic Acute 1Aquatic Chronic 1 |
| 貯蔵分類 | 11 - Combustible Solids |
用途
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.