Agomelatine
Grundinformationen
- CAS
138112-76-2- Standard-SMILES
COc1ccc2cccc(CCNC(C)=O)c2c1- InChIKey
YJYPHIXNFHFHND-UHFFFAOYSA-N- Summenformel
- C15H17NO2
- Durchschnittliche Molmasse
- 243,3 g/mol
- Monoisotopische Masse
- 243,12592879
Überblick
Agomelatine is a member of acetamides.
Namen und Bezeichner
- Bevorzugter Name
- Agomelatine
- IUPAC
- N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
- Englischer Name
- Agomelatine
- Summenformel
- C15H17NO2
- Molmasse
- 243.3
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
138112-76-2- PubChem CID
- 82148
- DTXSID
DTXSID3057642- ChEMBL
CHEMBL10878- ChEBI
CHEBI:134990- UNII
- 137R1N49AD
- EC Number
- 629-727-7
- Nikkaji
- J481.046E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,7
- Polarare Oberfläche (TPSA)
- 38,3 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 18
- Formalladung
- 0
- Komplexität
- 280
Experimentelle und physikochemische Eigenschaften
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
Physikochemische Eigenschaften
- Schmelzpunkt
- 107 · 107-109°C
- Siedepunkt
- 478.8 · 478.8±28.0 °C(Predicted)
- Dichte
- 1.109 · 1.109±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 50 mg/mL · DMSO: >50mg/mL
- Aggregatzustand
- powder
- pka
- 16.17 · 16.17±0.46(Predicted)
- Farbe
- white to off-white
- 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 Datenbank
- 138112 · 138112-76-2(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
Toxikologische Informationen
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 3077 9 / PGIII
- hs_code
- 29241990
- RTECS-Nr.
- AC5956323
- risk_code
- 50
- Toxizität
- mouse,LD50,oral,> 1gm/kg (1000mg/kg),United States Patent Document. Vol. #5318994,
- hazard_code
- N
- safety_code
- 61
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1
Chemie und Industrie
Pharmakologische Informationen
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
Verwendung und Herstellung
Anwendungen
BeschreibungAgomelatine 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.
VerwendenAgomelatine 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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