Agomelatine

Names

[ Name ]:
Agomelatine

[Synonym ]:
Unii-137R1N49ad
N-[2-(7-Methoxy-1-naphthyl)ethyl]acetamide
Acetamide, N-[2-(7-methoxy-1-naphthalenyl)ethyl]-
Aglomelatine
Agomelatine
N-[2-(7-Methoxy-1-naphthalenyl)ethyl]-acetamide S-20098
AGOMELATIN
Valdoxan
N-(2-(7-Methoxynaphthalen-1-yl)ethyl)acetamide
N-[2-(7-Methoxy-1-naphthalenyl)ethyl]acetamide
Melitor
Thymanax

Biological Activity

[Description]:

Agomelatine is a competitive antagonist of human and porcine serotonin (5-HT2C) receptors (pKi = 6.2 and 6.4, respectively) as well as human 5-HT2B receptors (pKi = 6.6). IC50 value: 6.2 (pKi, 5-HT2c); 6.6 (pKi, 5-HT2b)Target: 5-HT2C Receptor; 5-HT2B receptorIt is classified as a norepinephrine-dopamine disinhibitor (NDDI) due to its antagonism of the 5-HT2C receptor. Activation of 5-HT2C receptors by serotonin inhibits dopamine and norepinephrine release. Antagonism of 5-HT2C results in an enhancement of DA and NE release and activity of frontocortical dopaminergic and adrenergic pathways. Agomelatine is also a potent agonist at melatonin receptors which makes it the first melatonergic antidepressant. Agomelatine is an antidepressant drug.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Research Areas >> Neurological Disease

[References]

[1]. Pan L, Kardono LB, Riswan S, Chai H, Carcache de Blanco EJ, Pannell CM, Soejarto DD, McCloud TG, Newman DJ, Kinghorn AD.Isolation and characterization of minor analogues of silvestrol and other constituents from a large-scale re-collection of Aglaia foveolata.J Nat Prod. 2010 Nov 29;73(11):1873-8.

[2]. Zajecka J, Schatzberg A, Stahl S. et al. Efficacy and safety of agomelatine in the treatment of major depressive disorder: a multicenter, randomized, double-blind, placebo-controlled trial. J Clin Psychopharmacol. 2010 Apr;30(2):135-44.

[3]. Randy A Sansone, Lori A Sansone. Agomelatine A Novel Antidepressant. Innov Clin Neurosci. 2011 November; 8(11): 10-14.

[4]. Michele Fornaro, Davide Prestia, Salvatore Colicchio, and Giulio Perugi. A Systematic, Updated Review on the Antidepressant Agomelatine Focusing on its Melatonergic Modulation. Curr Neuropharmacol. 2010 September; 8(3): 287-304.

[5]. Agomelatine

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
478.8±28.0 °C at 760 mmHg

[ Melting Point ]:
107-109ºC

[ Molecular Formula ]:
C₁₅H₁₇NO₂

[ Molecular Weight ]:
243.301

[ Flash Point ]:
243.4±24.0 °C

[ Exact Mass ]:
243.125931

[ PSA ]:
38.33000

[ LogP ]:
2.27

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.582

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AC5956323

CHEMICAL NAME :: Acetamide, N-(2-(7-methoxy-1-naphthalenyl)ethyl)-

CAS REGISTRY NUMBER :: 138112-76-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C15-H17-N-O2

MOLECULAR WEIGHT :: 243.33

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #5318994

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H400

[ Precautionary Statements ]:
P273

[ Hazard Codes ]:
N

[ Risk Phrases ]:
50

[ Safety Phrases ]:
61

[ RIDADR ]:
UN 3077 9 / PGIII

[ HS Code ]:
2924199090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

[The activity of glutathione antioxidant system at melaksen and valdoxan action under experimental hyperthyroidism in rats].

Biomed. Khim. 59(5) , 541-9, (2013)

Investigation of glutathione antioxidant system activity and diene conjugates content in rats liver and blood serum at the influence of melaksen and valdoxan under experimental hyperthyroidism (EG) ha...

[Tachycardia and precordial pain with agomelatine: a case report].

Therapie. 68(5) , 324-5, (2013)

Agomelatine, melatonin and depressive disorder.

Expert Opin. Investig. Drugs 22(4) , 407-10, (2013)

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 ca...