Skip to Content
MilliporeSigma
All Photos(1)

Documents

A1362

Sigma-Aldrich

Agomelatine

≥98% (HPLC)

Synonym(s):

N-[2-(7-Methoxy-1-naphthalenyl)ethyl]-acetamide, S-20098

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C15H17NO2
CAS Number:
Molecular Weight:
243.30
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >50 mg/mL

originator

Servier

storage temp.

2-8°C

SMILES string

COc1ccc2cccc(CCNC(C)=O)c2c1

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)

InChI key

YJYPHIXNFHFHND-UHFFFAOYSA-N

Gene Information

Application

Agomelatine 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

Biochem/physiol Actions

Agomelatine is an extremely potent agonist at both melatonin receptors (MT1 and MT2), with additional antagonism at 5HT2C. It is a novel antidepressant with many desired in vivo properties, including neuroprotection and neurogenesis in depression-sensitive brain areas. Agomelatine′s efficacy appears to be due to both melatonergic and serotonergic properties. In neurogenesis assays, both in vitro and in vivo, the compound effects were differentially affected by antagonists for MT1/MT2 and 5HT2C, demonstrating actions through all three receptors.
Agomelatine modulates the sleep-wake cycle through its chronobiotic activity. It normalizes the sleep pattern in patients suffering from depression and seasonal mood disorder.

Features and Benefits

This compound is featured on the Melatonin Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Servier. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Environment

signalword

Warning

hcodes

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Trevor R Norman
Expert opinion on investigational drugs, 22(4), 407-410 (2013-03-15)
Alteration of nocturnal melatonin production, along with circadian rhythm disturbance, has been demonstrated in several psychiatric disorders. It has been postulated that such disturbances might be causal reflecting a more fundamental abnormality of the function of the suprachiasmatic nucleus (SCN).
Siegfried Kasper et al.
International clinical psychopharmacology, 28(1), 12-19 (2012-10-02)
Pooled analysis of individual patient data was used to compare the antidepressant efficacy of agomelatine with that of selective serotonin reuptake inhibitors (SSRIs) and serotonin and noradrenaline reuptake inhibitors (SNRIs). We sought head-to-head, double-blind, randomized studies without a placebo arm
Alejandro Martínez-Águila et al.
European journal of pharmacology, 701(1-3), 213-217 (2012-12-29)
In the search for new compounds to reduce intraocular pressure (IOP), with fewer side effects, we have found that agomelatine, a melatonin analogue, can reduce IOP being, therefore, interesting for the treatment of ocular hypertension and glaucoma. In normotensive conditions
Nikos Maniadakis et al.
BMC health services research, 13, 173-173 (2013-05-15)
Major depressive disorder (MDD) constitutes an important public health problem, as it is highly prevalent in the industrialized world and it is associated with substantial economic consequences for patients, health care providers, insurance and social security organizations and employers. To
Dan J Stein et al.
The Journal of clinical psychiatry, 73(7), 1002-1008 (2012-08-21)
This study evaluated the efficacy and tolerability of agomelatine in the prevention of relapse in patients with generalized anxiety disorder (GAD). Patients with GAD (Hamilton Anxiety Rating Scale [HARS] ≥ 22, with items 1 and 2 ≥ 2, item 1

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service