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A1362

Sigma-Aldrich

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:
138112-76-2
Molecular Weight:
243.30
MDL number:
MFCD00916659
UNSPSC Code:
12352200
PubChem Substance ID:
329770704
NACRES:
NA.77

Quality Level

100

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.

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

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’.

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Agomelatine modulates calcium signaling through protein kinase C and phospholipase C-mediated mechanisms in rat sensory neurons
Serhatlioglu I, et al.
Journal of Cellular Physiology, 234(7), 10741-10746 (2019)
Laurence Lanfumey et al.
Pharmacology & therapeutics, 138(2), 176-184 (2013-01-26)
Affective disorders such as major depression, bipolar disorders and seasonal affective disorders have been described as alterations of various neuronal systems. In addition to the classical monoaminergic hypotheses that have been long proposed to explain the pathophysiology of these disorders
Two cases of delirium with agomelatine therapy.
María Gabriela Viejo Sacha et al.
Annals of clinical psychiatry : official journal of the American Academy of Clinical Psychiatrists, 25(1), 67-68 (2013-02-05)
V E Medvedev
Zhurnal nevrologii i psikhiatrii imeni S.S. Korsakova, 112(5), 37-40 (2012-09-07)
According to data received from the study VREMYA, the combined therapy of moderate and severe non-psychotic depressions with Valdoxane and antidepressants of other pharmacological groups is effective and doesn't cause serious adverse events. These findings suggested using the indicated combination
Agomelatine may improve REM sleep behavior disorder symptoms.
Anastasios Bonakis et al.
Journal of clinical psychopharmacology, 32(5), 732-734 (2012-08-29)
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