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Details

Stereochemistry ACHIRAL
Molecular Formula C15H17NO2
Molecular Weight 243.3015
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AGOMELATINE

SMILES

CC(=NCCc1cccc2ccc(cc21)OC)O

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
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12750432 | https://www.ncbi.nlm.nih.gov/pubmed/12764576 | http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/000915/WC500046227.pdf

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.1 nM [Ki]
0.12 nM [Ki]
6.2 null [pKi]
6.6 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VALDOXAN

Approved Use

Treatment of major depressive episodes.

Launch Date

1.23491516E12
PubMed

PubMed

TitleDatePubMed
[Agomelatine: the first "melatoninergic" antidepressant].
2006 Oct
New antidepressants or more of the same?
2007
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
Hippocampal neurogenesis, depressive disorders, and antidepressant therapy.
2007
Gateways to clinical trials.
2007 Apr
Agomelatine and its therapeutic potential in the depressed patient.
2007 Aug
Agomelatine: a novel atypical antidepressant.
2007 Dec
Emerging treatments for major depression.
2007 Feb
[New hypnotics: perspectives from sleep physiology].
2007 Jul-Aug
Gateways to clinical trials.
2007 Jun
Gateways to clinical trials.
2007 May
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
Efficacy of agomelatine, a MT1/MT2 receptor agonist with 5-HT2C antagonistic properties, in major depressive disorder.
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
Severe depression and antidepressants: focus on a pooled analysis of placebo-controlled studies on agomelatine.
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
Core symptoms of major depressive disorder: relevance to diagnosis and treatment.
2008
Promising avenues of therapeutics for bipolar illness.
2008
Melatonin receptor agonists: SAR and applications to the treatment of sleep-wake disorders.
2008
Agomelatine: AGO 178, AGO178, S 20098.
2008
Gateways to clinical trials.
2008 Apr
Agomelatine treatment of major depressive disorder.
2008 Dec
A double-blind comparison of sexual functioning, antidepressant efficacy, and tolerability between agomelatine and venlafaxine XR.
2008 Jun
Melatonin and its agonists: an update.
2008 Oct
Efficacy of agomelatine in generalized anxiety disorder: a randomized, double-blind, placebo-controlled study.
2008 Oct
Agomelatine adjunctive therapy for acute bipolar depression: preliminary open data.
2008 Sep
Addressing circadian rhythm disturbances in depressed patients.
2008 Sep
Innovation translates into antidepressant effectiveness.
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
Melatonin and melatonergic drugs on sleep: possible mechanisms of action.
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
Influence of the novel antidepressant and melatonin agonist/serotonin2C receptor antagonist, agomelatine, on the rat sleep-wake cycle architecture.
2009 Jul
Treatment-emergent sexual dysfunction related to antidepressants: a meta-analysis.
2009 Jun
Agomelatine improves symptoms of generalised anxiety disorder.
2009 May
Pharmacology of ramelteon, a selective MT1/MT2 receptor agonist: a novel therapeutic drug for sleep disorders.
2009 Winter
Better sexual acceptability of agomelatine (25 and 50 mg) compared with paroxetine (20 mg) in healthy male volunteers. An 8-week, placebo-controlled study using the PRSEXDQ-SALSEX scale.
2010 Jan
Patents

Sample Use Guides

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
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
S20098
Code 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
S-20098
Code English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
WHO-VATC QN06AX22
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
EMA ASSESSMENT REPORTS THYMANAX (AUTHORIZED: DEPRESSIVE DISORDER, MAJOR)
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
NCI_THESAURUS C28197
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
WHO-ATC N06AX22
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
EMA ASSESSMENT REPORTS VALDOXAN (REFUSED: DEPRESSIVE DISORDER, MAJOR)
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C72684
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
DRUG CENTRAL
99
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
FDA UNII
137R1N49AD
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
WIKIPEDIA
AGOMELATINE
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
DRUG BANK
DB06594
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
EVMPD
SUB05286MIG
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL10878
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
CAS
138112-76-2
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
PUBCHEM
82148
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
INN
7392
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
MERCK INDEX
M1453
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY Merck Index
EPA CompTox
138112-76-2
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY
IUPHAR
198
Created by admin on Fri Jun 25 22:17:30 UTC 2021 , Edited by admin on Fri Jun 25 22:17:30 UTC 2021
PRIMARY