 Home > Encyclopedia > Agomelatine

Agomelatine

Agomelatine structure

CAS No:
138112-76-2
Formula:
C15H17NO2
Chemical Name:
Agomelatine
Synonyms:
Acetamide,N-[2-(7-methoxy-1-naphthalenyl)ethyl]-;N-[2-(7-Methoxy-1-naphthalenyl)ethyl]acetamide;S 20098;N-[2-(7-Methoxy-1-naphthyl)ethyl]acetamide;Agomelatine;Valdoxan;N-[2-(7-Methoxynaphthalen-1-yl)ethyl]acetamide;AGO 178;Thymanax
Categories:
Active Pharmaceutical Ingredients > Nervous System Drugs

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

Solid

Agomelatine is a member of acetamides.|Agomelatine is structurally closely related to melatonin. Agomelatine is a potent agonist at melatonin receptors and an antagonist at serotonin-2C (5-HT2C) receptors, tested in an animal model of depression. Agomelatine was developed in Europe by Servier Laboratories Ltd. and submitted to the European Medicines Agency (EMA) in 2005. The Committee for Medical Products for Human Use (CHMP) recommended refusal of marketing authorization on 27 July 2006. The major concern was that efficacy had not been sufficiently shown. In 2006 Servier sold the rights to develop Agomelatine in the US to Novartis. The development for the US market was discontinued in October 2011. It is currently sold in Australia under the Valdoxan trade name.

Agomelatine Basic Attributes

Molecular Weight：

243.30100

Exact Mass：

243.30

UNII：

137R1N49AD

DSSTox ID：

DTXSID3057642

ATC Code：

N06AX22|N - Nervous system

HScode：

2924199090

Characteristics

PSA：

38.33000

XLogP3：

2.7

Appearance：

white solid

Density：

1.109g/cm3

Melting Point：

109-110 °C @ Solvent: Toluene, Hexane

Boiling Point：

478.8ºC at 760 mmHg

Flash Point：

243.4ºC

Refractive Index：

1.582

Water Solubility：

7.76e-03 g/L

Collision Cross Section：

156.3 Å² [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Safety Information

Transport codes：

UN 3077 9 / PGIII

hazard class code：

safety instructions：

Marks：

Precautionary statement(s)：

P273

Hazard Statements：

H400

GHS Classification：

|Warning|H315 (23.08%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 53 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Protein Binding：

> 95%

Drug Information

Drug Indication：

Agomelatine is indicated to treat major depressive episodes in adults.|Treatment of major depressive episodes in adults.|Treatment of generalised anxiety disorder

Pharmacology：

Agomelatine resynchronises circadian rhythms in animal models of delayed sleep phase syndrome and other circadian rhythm disruptions. It increases noradrenaline and dopamine release specifically in the frontal cortex and has no influence on the extracellular levels of serotonin. Agomelatine has shown an antidepressant-like effect in animal depression models, (learned helplessness test, despair test, and chronic mild stress) circadian rhythm desynchronisation, and in stress and anxiety models. In humans, agomelatine has positive phase shifting properties; it induces a phase advance of sleep, body temperature decline and melatonin onset. Controlled studies in humans have shown that agomelatine is as effective as the SSRI antidepressants paroxetine and sertraline in the treatment of major depression

MeSH：

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

Absorption：

Bioavailability is less than 5%.

Metabolism/Metabolites：

Hepatic (90% CYP1A2 and 10% CYP2C9).

Biological Half-Life：

<2 hours

Mechanism of Action：

The novel antidepressant agent, agomelatine, behaves as an agonist at melatonin receptors (MT1 and MT2) and as an antagonist at serotonin (5-HT)(2C) receptors.

MeSH Entry Terms：

AGO 178

Agomelatine Use and Manufacturing

Uses

A melatoninergic agonist and selective antagonist of 5-HT2C receptors, and has been shown to be active in several animal models of depression. Agomelatine (S20098) displayed pKi values of 6. 4 and 6. 2 at native (porcine) and cloned, human (h)5-hydroxytry.

Use Classification：

Human drugs -> Thymanax -> EMA Drug Category|Psychoanaleptics -> Human pharmacotherapeutic group|Human drugs -> Valdoxan -> EMA Drug Category|Human Drugs -> EU pediatric investigation plans

Computed Properties

Molecular Weight:243.30
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:243.125928785
Monoisotopic Mass:243.125928785
Topological Polar Surface Area:38.3
Heavy Atom Count:18
Complexity:280
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

2-Naphthol

Dimethyl sulfate

Drug Function and Efficacy

1. Agomelatine is a melatonin receptor agonist and 5-HT2C receptor antagonist. It can correct the circadian rhythm of animal models of circadian rhythm disorders, restore the rhythm, and show antidepressant effects in various animal models of depression. 2. Agomelatine can specifically increase the release of norepinephrine and dopamine in the prefrontal cortex, and has no significant effect on the level of extracellular serotonin. 3. In human studies, agomelatine has a positive phase-adjusting effect on sleep, can induce an advance in the sleep phase, lower body temperature, and induce a melatonin-like effect.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Agomelatine tablets
Ingredients	Agomelatine.
Indication	1. Agomelatine is mainly metabolized by cytochrome P4501A2 (CYPIA2) (90%) and CYP2C9/19 (10%). Drugs that interact with these enzymes may reduce or increase the bioavailability of agomelatine. Vofloxamine is a strong CYPIA2 and moderate CYP2C9 inhibitor, which can significantly inhibit the metabolism of agomelatine and increase the exposure of agomelatine by 60 times (range 12-412). Therefore, this product is prohibited from being used in combination with strong CYPIA2 inhibitors (such as vofloxamine, ciprofloxacin). 2. When this product is used in combination with estrogen (moderate CYPIA2 inhibitor), the exposure of agomelatine will increase several times. Although 800 patients who used estrogen at the same time did not show specific safety issues
Specifications	25 mg

Agomelatine
Manufacturer	Jiangsu Hansoh Pharmaceutical Group Co., Ltd.

Agomelatine tablets
Specifications	25 mg

See More Related Drugs

Registered Holders

Beijing Lunarsun Pharmaceutical Co., Ltd.

China
Active
Biobetta Pharmaceuticals (Shanghai) Co., Ltd.

China
Active
Chongqing Pharscin Pharmaceutical Co., Ltd.

China
Active

See More Registered Holders

Recommended Suppliers of Agomelatine

Guangzhou Yaoguang Technology Co., Ltd. Contact Supplier

CN
5 YRS

Business licensed Certified factory

Manufactory Supplier of Custom Synthetic Chemicals,Biological Stains,Pharmaceutical Intermediates,Cosmetic Grade Chemicals,Enzyme,Nucleosides,Indicators,Speciality Chemicals,Biological Chemicals,Enzyme Substrates

AGOMELATINE, CAS:138112-76-2

Unit Price: $150-155 /KG FOB

CAS No.: 138112-76-2

Grade: Pharmaceutical Grade

Content: 99%

Inquiry
Echemi Pharmaceutical Contact Supplier

CN
8 YRS

Business licensed

Distributor Supplier of API,Intermediate

Agomelatine-ECHEMI

CAS No.: 138112-76-2

Grade: Pharmaceutical Grade

Inquiry
Eon Biotech Contact Supplier

GB
4 YRS

Business licensed

Trader Supplier of Nootropics,Sarms,Peptides,API,Intermediates

Agomelatine

CAS No.: 138112-76-2

Grade: Pharmaceutical Grade

Content: 98%

Inquiry
HANGZHOU HAILAN CHEMICAL CO.,LTD Contact Supplier

CN
4 YRS

Business licensed

Trader Supplier of intermediates ,fine chemical,food additives

Agomelatine

CAS No.: 138112-76-2

Inquiry
Hubei KDG Web Science&Technology Co.,Ltd Contact Supplier

CN
2 YRS

Business licensed

Trader Supplier of Peptide,API,HCG,Amino Acids,Plant Extract,Vitamin

Factory Made Agomelatine CAS 138112-76-2 Cheap Price Global Warehou

CAS No.: 138112-76-2

Grade: Pharmaceutical Grade

Content: 99%

Inquiry