Agomelatine

HCID 82148

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

Agomelatine138112-76-2ThymanaxValdoxanS20098S-20098AgomelatinaAGO-178S 20098N-(2-(7-methoxy-1-naphthyl)ethyl)acetamideagomelatinumAGO178
Weitere Namen anzeigen
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

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

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

Pharmaceuticals

Pharmaceuticals -> Antidepressants

Pharmaceuticals -> Listed in ZINC15

Solubility · 2 Einträge

~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 Einträge

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)]

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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

Hazard Classes and CategoriesSkin Irrit. 2 (22.2%)

Toxikologische Informationen

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

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,

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

N06AX22

N - Nervous system

QN - Nervous system

Protein Binding> 95%
Pharmacodynamics · 1 Eintrag

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).

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >100
Anwendungen · 2 Einträge

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.

Anbieter100 Anbieter

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]

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