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A1362

Sigma-Aldrich

Agomelatine

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C15H17NO2
Numéro CAS:
138112-76-2
Poids moléculaire :
243.30
Numéro MDL:
MFCD00916659
Code UNSPSC :
12352200
ID de substance PubChem :
329770704
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

DMSO: >50 mg/mL

Auteur

Servier

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

YJYPHIXNFHFHND-UHFFFAOYSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Environment
GHS09

Mention d'avertissement

Warning

Mentions de danger

H410

Conseils de prudence

P273 - P391 - P501

Classification des risques

Aquatic Acute 1 - Aquatic Chronic 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
Agomelatine may improve REM sleep behavior disorder symptoms.
Anastasios Bonakis et al.
Journal of clinical psychopharmacology, 32(5), 732-734 (2012-08-29)
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
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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