Agomelatine

HCID 82148
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Substructure searchFind similar structures

Basic information

CAS
138112-76-2
Standard SMILES
COc1ccc2cccc(CCNC(C)=O)c2c1
InChIKey
YJYPHIXNFHFHND-UHFFFAOYSA-N
Molecular formula
C15H17NO2
Average molar mass
243.3 g/mol
Monoisotopic mass
243.12592879

Overview

Agomelatine is a member of acetamides.

Names & identifiers

Preferred name
Agomelatine
IUPAC
N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide
English name
Agomelatine
Molecular formula
C15H17NO2
Molecular weight
243.3

Names & synonyms

Agomelatine138112-76-2ThymanaxValdoxanS20098S-20098AgomelatinaAGO-178S 20098N-(2-(7-methoxy-1-naphthyl)ethyl)acetamideagomelatinumAGO178
Show more names
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

Database identifiers

CAS
138112-76-2
PubChem CID
82148
DTXSID
DTXSID3057642
ChEMBL
CHEMBL10878
ChEBI
CHEBI:134990
UNII
137R1N49AD
EC Number
629-727-7
Nikkaji
J481.046E

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
38.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
4
Heavy atoms
18

Experimental & physicochemical properties

Drugs · 3 items

Pharmaceuticals

Pharmaceuticals -> Antidepressants

Pharmaceuticals -> Listed in ZINC15

Solubility · 2 items

~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 items

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)]

Physicochemical properties

Melting point
107 · 107-109°C
Boiling point
478.8 · 478.8±28.0 °C(Predicted)
Density
1.109 · 1.109±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
50 mg/mL · DMSO: >50mg/mL
form
powder

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (22.2%)

Toxicology

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
3
rtecs
AC5956323
ridadr
UN 3077 9 / PGIII
hs_code
29241990
Toxicity
mouse,LD50,oral,> 1gm/kg (1000mg/kg),United States Patent Document. Vol. #5318994,
risk_code
50

Chemistry & industry

Pharmacology

ATC Code · 3 items

N06AX22

N - Nervous system

QN - Nervous system

Protein Binding> 95%
Pharmacodynamics · 1 item

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).

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >100
Applications · 5 items

UsesMelatonin drugs.

DescriptionAgomelatine 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.

UsesAgomelatine 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.

UsesAgomelatine has been used: to study its effects on adult neurogenesis and hippocampus apoptosis using the stress-induced depression model of rats to explore its effects on tau protein phosphorylation and to study its neuroprotective mechanism to study its effects on intracellular calcium ([Ca2+]i) signaling in peripheral neurons of rat dorsal root ganglion (DRG) neurons

UsesAgomelatine is an antidepressant drug. It is classified as a norepinephrine-dopamine disinhibitor (NDDI) due to its antagonism of the 5-HT2C receptor. Activation of 5-HT2C receptors by serotonin inhibits dopamine and norepinephrine release. Antagonism of

Upstream & downstream products

Suppliers100 total

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]

Additional notes

DefinitionChEBI: Agomelatine is a member of acetamides.

Related reactions

35 records
New reaction record

Compound notes

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