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Details

Stereochemistry ACHIRAL
Molecular Formula C15H17NO2
Molecular Weight 243.301
Optical Activity NONE
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
Molecular Formula C15H17NO2
Molecular Weight 243.301
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

CNS Activity

Originator

Approval Year

Unknown
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2662
 0.1 nM [Ki]
Agonist
2662
 0.12 nM [Ki]
Antagonist
2760
 6.2 null [pKi]
Antagonist
2760
 6.6 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8360
VALDOXAN

Approved Use

Treatment of major depressive episodes.

Launch Date

1.23491516E12
PubMed

PubMed

TitleDatePubMed
Anxiolytic-like action of the antidepressant agomelatine (S 20098) after a social defeat requires the integrity of the SCN.
2005 Oct
New directions for drug discovery.
2006
Future prospects in depression research.
2006
Therapeutic potential of melatonin ligands.
2006
Effects of melatonin and agomelatine in anxiety-related procedures in rats: interaction with diazepam.
2006 Aug
Clinical efficacy of agomelatine in depression: the evidence.
2006 Feb
Anxiolytic-like activity of agomelatine and melatonin in three animal models of anxiety.
2006 Feb
Placebo-controlled trial of agomelatine in the treatment of major depressive disorder.
2006 Feb
Agomelatine targets a range of major depressive disorder symptoms.
2006 Jul
Melatonin: Nature's most versatile biological signal?
2006 Jul
Agomelatine, a new antidepressant, induces regional changes in hippocampal neurogenesis.
2006 Jun 1
Prospects for the treatment of depression.
2006 May
[Agomelatine: the first "melatoninergic" antidepressant].
2006 Oct
New antidepressants or more of the same?
2007
Hippocampal neurogenesis, depressive disorders, and antidepressant therapy.
2007
Agomelatine and its therapeutic potential in the depressed patient.
2007 Aug
Agomelatine: a novel atypical antidepressant.
2007 Dec
A review of the efficacy and tolerability of agomelatine in the treatment of major depression.
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
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
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
[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
Melatonin receptor agonists: SAR and applications to the treatment of sleep-wake disorders.
2008
Agomelatine: AGO 178, AGO178, S 20098.
2008
Agomelatine treatment of major depressive disorder.
2008 Dec
Jet lag: therapeutic use of melatonin and possible application of melatonin analogs.
2008 Jan-Mar
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
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
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
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
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

Patents

07183318
3
07498465
4
JP2005239718A
3
JP2007182440A
3
JP2009137943A
3
JP2010037345A
3
JP2010280699A
3

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).
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:30:43 UTC 2023
Edited
by admin
on Wed Jul 05 23:30:43 UTC 2023
Record UNII
137R1N49AD
Record Status Validated (UNII)
Record Version
  • Download
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
Agomelatine [WHO-DD]
Common Name English
THYMANAX
Brand 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 Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
WHO-VATC QN06AX22
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
EMA ASSESSMENT REPORTS THYMANAX (AUTHORIZED: DEPRESSIVE DISORDER, MAJOR)
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
NCI_THESAURUS C28197
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
WHO-ATC N06AX22
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
EMA ASSESSMENT REPORTS VALDOXAN (REFUSED: DEPRESSIVE DISORDER, MAJOR)
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C72684
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
DRUG CENTRAL
99
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
FDA UNII
137R1N49AD
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
WIKIPEDIA
AGOMELATINE
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
DRUG BANK
DB06594
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
EVMPD
SUB05286MIG
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
ChEMBL
CHEMBL10878
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
CAS
138112-76-2
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
PUBCHEM
82148
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
INN
7392
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
MERCK INDEX
M1453
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3057642
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
SMS_ID
100000085257
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
IUPHAR
198
Created by admin on Wed Jul 05 23:30:43 UTC 2023 , Edited by admin on Wed Jul 05 23:30:43 UTC 2023
PRIMARY
Related Record Type Details
5-HYDROXYTRYPTAMINE RECEPTOR 2C
TARGET -> INHIBITOR
Structure of AGOMELATINE UREA
SALT/SOLVATE -> PARENT
MELATONIN MT2 RECEPTOR
TARGET -> AGONIST
Ki
MELATONIN MT1 RECEPTOR
TARGET -> AGONIST
AGONIST
Ki
5-HYDROXYTRYPTAMINE RECEPTOR 2B
TARGET -> INHIBITOR
Structure of AGOMELATINE CITRIC ACID
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of AGOMELATINE
ACTIVE MOIETY
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