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Details

Stereochemistry ACHIRAL
Molecular Formula C15H17NO2
Molecular Weight 243.301
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AGOMELATINE

SMILES

COC1=CC2=C(CCNC(C)=O)C=CC=C2C=C1

InChI

InChIKey=YJYPHIXNFHFHND-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Agomelatine behaves both as a potent agonist at melatonin MT1 and MT2 receptors and as a neutral antagonist at 5-HT2C receptors. Accumulating evidence in a broad range of experimental procedures supports the notion that the psychotropic effects of agomelatine are due to the synergy between its melatonergic and 5-hydroxytryptaminergic effects. Agomelatine is indicated for the treatment of major depressive episodes.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Antidepressant-like effects of agomelatine, melatonin and the NK1 receptor antagonist GR205171 in impulsive-related behaviour in rats.
2005 Oct
Phase-shifts of 24-h rhythms of hormonal release and body temperature following early evening administration of the melatonin agonist agomelatine in healthy older men.
2005 Sep
Agomelatine: a preliminary review of a new antidepressant.
2006
New directions for drug discovery.
2006
Treatments in depression.
2006
Therapeutic potential of melatonin ligands.
2006
Effects of melatonin and agomelatine in anxiety-related procedures in rats: interaction with diazepam.
2006 Aug
Antidepressant-like effects of agomelatine (S 20098) in the learned helplessness model.
2006 Dec
Pharmacology of a new antidepressant: benefit of the implication of the melatonergic system.
2006 Feb
Agomelatine targets a range of major depressive disorder symptoms.
2006 Jul
Melatonin: Nature's most versatile biological signal?
2006 Jul
Homology modelling of the serotoninergic 5-HT2c receptor.
2006 Jun
Prospects for the treatment of depression.
2006 May
Could agomelatine be the ideal antidepressant?
2006 Nov
[Agomelatine: the first "melatoninergic" antidepressant].
2006 Oct
Role of the melatonin system in the control of sleep: therapeutic implications.
2007
The phase shift hypothesis for the circadian component of winter depression.
2007
Gateways to clinical trials.
2007 Apr
Agomelatine: a novel atypical antidepressant.
2007 Dec
A review of the efficacy and tolerability of agomelatine in the treatment of major depression.
2007 Dec
Non-REM sleep instability in patients with major depressive disorder: subjective improvement and improvement of non-REM sleep instability with treatment (Agomelatine).
2007 Dec
Emerging treatments for major depression.
2007 Feb
[New hypnotics: perspectives from sleep physiology].
2007 Jul-Aug
Gateways to clinical trials.
2007 Jun
Agomelatine in the treatment of seasonal affective disorder.
2007 Mar
Improvement in subjective sleep in major depressive disorder with a novel antidepressant, agomelatine: randomized, double-blind comparison with venlafaxine.
2007 Nov
The interaction between the internal clock and antidepressant efficacy.
2007 Oct
High-quality remission: potential benefits of the melatonergic approach for patients with major depressive disorder.
2007 Oct
Evidence of agomelatine's antidepressant efficacy: the key points.
2007 Oct
Major depressive disorder, sleep EEG and agomelatine: an open-label study.
2007 Oct
Agomelatine adjunctive therapy for acute bipolar depression: preliminary open data.
2007 Sep
[Pharmacotherapy of depression: recent developments].
2007 Sep 19
Cellular and molecular mechanisms in the long-term action of antidepressants.
2008
Effects of different antidepressant treatments on the core of depression.
2008
Promising avenues of therapeutics for bipolar illness.
2008
Agomelatine: AGO 178, AGO178, S 20098.
2008
Melatonergic drugs in clinical practice.
2008
Jet lag: therapeutic use of melatonin and possible application of melatonin analogs.
2008 Jan-Mar
A double-blind comparison of sexual functioning, antidepressant efficacy, and tolerability between agomelatine and venlafaxine XR.
2008 Jun
Agomelatine, a melatonin receptor agonist with 5-HT(2C) receptor antagonist properties, protects the developing murine white matter against excitotoxicity.
2008 Jun 24
Addressing circadian rhythm disturbances in depressed patients.
2008 Sep
Agomelatine, an innovative pharmacological response to unmet needs.
2008 Sep
Agomelatine: a novel mechanism of antidepressant action involving the melatonergic and the serotonergic system.
2008 Sep
Melatonin receptor agonist agomelatine: a new drug for treating unipolar depression.
2009
Insomnia in patients with depression: some pathophysiological and treatment considerations.
2009
Beyond the monoaminergic hypothesis: agomelatine, a new antidepressant with an innovative mechanism of action.
2009
Chronic mild stress (CMS) in mice: of anhedonia, 'anomalous anxiolysis' and activity.
2009
The effect of melatonergic and non-melatonergic antidepressants on sleep: weighing the alternatives.
2009
The antidepressant agomelatine blocks the adverse effects of stress on memory and enables spatial learning to rapidly increase neural cell adhesion molecule (NCAM) expression in the hippocampus of rats.
2009 Apr
Pathophysiology of depression: role of sleep and the melatonergic system.
2009 Feb 28
Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose is 25 mg once daily taken orally at bedtime. After two weeks of treatment, if there is no improvement of symptoms, the dose may be increased to 50 mg once daily, i.e. two 25 mg tablets, taken together at bedtime. Decision of dose increase has to be balanced with a higher risk of transaminases elevation. Any dose increase to 50 mg should be made on an individual patient benefit/risk basis and with strict respect of LFT monitoring.
Route of Administration: Oral
In Vitro Use Guide
hypothalamic suprachiasmatic nucleus firing rates were dose-dependently suppressed by 19.2-80.9% following perfusion of 0.04-0.32mM agomelatine (p<0.001, IC50=0.14mM).
Name Type Language
AGOMELATINE
EMA EPAR   INN   MART.   MI   WHO-DD  
INN  
Official Name English
AGOMELATINE [MI]
Common Name English
VALDOXAN
Brand Name English
THYMANAX
Brand Name English
AGOMELATINE [WHO-DD]
Common Name English
N-(2-(7-METHOXY-1-NAPHTHYL)ETHYL)ACETAMIDE
Systematic Name English
AGOMELATINE [EMA EPAR]
Common Name English
AGOMELATINE [INN]
Common Name English
AGOMELATINE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
WHO-VATC QN06AX22
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
EMA ASSESSMENT REPORTS THYMANAX (AUTHORIZED: DEPRESSIVE DISORDER, MAJOR)
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
NCI_THESAURUS C28197
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
WHO-ATC N06AX22
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
EMA ASSESSMENT REPORTS VALDOXAN (REFUSED: DEPRESSIVE DISORDER, MAJOR)
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C72684
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY
WIKIPEDIA
AGOMELATINE
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY
DRUG BANK
DB06594
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY
EVMPD
SUB05286MIG
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY
ChEMBL
CHEMBL10878
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY
CAS
138112-76-2
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY
PUBCHEM
82148
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY
INN
7392
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY
MERCK INDEX
M1453
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY Merck Index
EPA CompTox
138112-76-2
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY
IUPHAR
198
Created by admin on Mon Oct 21 23:42:18 UTC 2019 , Edited by admin on Mon Oct 21 23:42:18 UTC 2019
PRIMARY