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A1362

Sigma-Aldrich

Agomelatine

≥98% (HPLC)

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Synonym(s):
N-[2-(7-Methoxy-1-naphthalenyl)ethyl]-acetamide, S-20098
Empirical Formula (Hill Notation):
C15H17NO2
CAS Number:
138112-76-2
Molecular Weight:
243.30
MDL number:
MFCD00916659
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

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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)
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
Melatonin receptor stimulation by agomelatine prevents Abeta-induced tau phosphorylation and oxidative damage in PC12 cells
Yao K, et al.
Drug design, development and therapy, 13, 387-387 (2019)
Effect of agomelatine on adult hippocampus apoptosis and neurogenesis using the stress model of rats
Yucel A, et al.
Acta Histochemica, 118(3), 299-304 (2016)
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).
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