A1362
Agomelatine
≥98% (HPLC)
Synonym(s):
N-[2-(7-Methoxy-1-naphthalenyl)ethyl]-acetamide, S-20098
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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
human ... HTR2C(3358) , MTNR1A(4543) , MTNR1B(4544)
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1
WGK
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’.
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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).
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
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
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
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
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