melatonin   Click here for help

GtoPdb Ligand ID: 224

Abbreviated name: MLT
Synonyms: Circadin®
Approved drug PDB Ligand Immunopharmacology Ligand
melatonin is an approved drug (EMA (2007))
Comment: Melatonin is a hormone involved in regulating circadian rhythms in animals. Melatonin activates a family of melatonin receptors.

SARS-CoV-2 and COVID-19: The effect of viral infection (including by influenza and SARS-CoV-2) on the melatonergic pathway, and how this might modulate the inflammatory response was reviewed by Anderson and Reiter in May 2020 [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 54.12
Molecular weight 232.12
XLogP 1.6
No. Lipinski's rules broken 0
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Canonical SMILES COc1ccc2c(c1)c(CCNC(=O)C)c[nH]2
Isomeric SMILES COc1ccc2c(c1)c(CCNC(=O)C)c[nH]2
InChI InChI=1S/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)
1. Anderson G, Reiter RJ. (2020)
Melatonin: Roles in influenza, Covid-19, and other viral infections.
Rev Med Virol, 30 (3): e2109. DOI: 10.1002/rmv.2109 [PMID:32314850]
2. 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]
3. Calvo JR, González-Yanes C, Maldonado MD. (2013)
The role of melatonin in the cells of the innate immunity: a review.
J Pineal Res, 55 (2): 103-20. [PMID:23889107]
4. Carlberg C. (2000)
Gene regulation by melatonin.
Ann N Y Acad Sci, 917: 387-96. [PMID:11268365]
5. Carrillo-Vico A, Lardone PJ, Alvarez-Sánchez N, Rodríguez-Rodríguez A, Guerrero JM. (2013)
Melatonin: buffering the immune system.
Int J Mol Sci, 14 (4): 8638-83. [PMID:23609496]
6. Dubocovich ML. (1985)
Characterization of a retinal melatonin receptor.
J Pharmacol Exp Ther, 234 (2): 395-401. [PMID:2991499]
7. Dubocovich ML, Masana MI, Iacob S, Sauri DM. (1997)
Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor.
Naunyn Schmiedebergs Arch Pharmacol, 355 (3): 365-75. [PMID:9089668]
8. Huang SH, Cao XJ, Wei W. (2008)
Melatonin decreases TLR3-mediated inflammatory factor expression via inhibition of NF-kappa B activation in respiratory syncytial virus-infected RAW264.7 macrophages.
J Pineal Res, 45 (1): 93-100. [PMID:18312297]
9. Jahanban-Esfahlan R, Mehrzadi S, Reiter RJ, Seidi K, Majidinia M, Baghi HB, Khatami N, Yousefi B, Sadeghpour A. (2018)
Melatonin in regulation of inflammatory pathways in rheumatoid arthritis and osteoarthritis: involvement of circadian clock genes.
Br J Pharmacol, 175 (16): 3230-3238. [PMID:28585236]
10. 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]
11. Steinhilber D, Brungs M, Werz O, Wiesenberg I, Danielsson C, Kahlen JP, Nayeri S, Schräder M, Carlberg C. (1995)
The nuclear receptor for melatonin represses 5-lipoxygenase gene expression in human B lymphocytes.
J Biol Chem, 270 (13): 7037-40. [PMID:7706239]
12. Xia MZ, Liang YL, Wang H, Chen X, Huang YY, Zhang ZH, Chen YH, Zhang C, Zhao M, Xu DX et al.. (2012)
Melatonin modulates TLR4-mediated inflammatory genes through MyD88- and TRIF-dependent signaling pathways in lipopolysaccharide-stimulated RAW264.7 cells.
J Pineal Res, 53 (4): 325-34. [PMID:22537289]
13. Xu X, Wang G, Ai L, Shi J, Zhang J, Chen YX. (2018)
Melatonin suppresses TLR9-triggered proinflammatory cytokine production in macrophages by inhibiting ERK1/2 and AKT activation.
Sci Rep, 8 (1): 15579. [PMID:30349079]