agomelatine   Click here for help

GtoPdb Ligand ID: 198

Synonyms: S20098 | Thymanax® | Valdoxan®
Approved drug PDB Ligand
agomelatine is an approved drug (EMA (2009))
Compound class: Synthetic organic
Comment: Agomelatine is a melatonergic (i.e. it acts as a a melatonin receptor agonist) antidepressant, devoid of the side-effects caused by SSRI, SNRI and tricyclic antidepressants. The drug also has low affinity for 5-HT2C receptors.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 38.33
Molecular weight 243.13
XLogP 2.76
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc2c(c1)c(CCNC(=O)C)ccc2
Isomeric SMILES COc1ccc2c(c1)c(CCNC(=O)C)ccc2
InChI 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)
1. Audinot V, Mailliet F, Lahaye-Brasseur C, Bonnaud A, Le Gall A, Amossé C, Dromaint S, Rodriguez M, Nagel N, Galizzi JP et al.. (2003)
New selective ligands of human cloned melatonin MT1 and MT2 receptors.
Naunyn Schmiedebergs Arch Pharmacol, 367 (6): 553-61. [PMID:12764576]
2. Beresford IJ, Browning C, Starkey SJ, Brown J, Foord SM, Coughlan J, North PC, Dubocovich ML, Hagan RM. (1998)
GR196429: a nonindolic agonist at high-affinity melatonin receptors.
J Pharmacol Exp Ther, 285 (3): 1239-45. [PMID:9618428]
3. Guardiola-Lemaitre B, De Bodinat C, Delagrange P, Millan MJ, Munoz C, Mocaër E. (2014)
Agomelatine: mechanism of action and pharmacological profile in relation to antidepressant properties.
Br J Pharmacol, 171 (15): 3604-19. [PMID:24724693]
4. Millan MJ, Gobert A, Lejeune F, Dekeyne A, Newman-Tancredi A, Pasteau V, Rivet JM, Cussac D. (2003)
The novel melatonin agonist agomelatine (S20098) is an antagonist at 5-hydroxytryptamine2C receptors, blockade of which enhances the activity of frontocortical dopaminergic and adrenergic pathways.
J Pharmacol Exp Ther, 306 (3): 954-64. [PMID:12750432]