tianeptine   Click here for help

GtoPdb Ligand ID: 7558

Synonyms: Stablon® | tianeptine sodium
Approved drug
tianeptine is an approved drug
Compound class: Synthetic organic
Comment: Chemically tianeptine can be classified as a tricyclic antidepressant (TCA), but evidence suggests that it has a quite different pharmacological mechanism of action compared to typical TCAs [2-4].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 95.09
Molecular weight 436.12
XLogP 4.27
No. Lipinski's rules broken 0
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Canonical SMILES OC(=O)CCCCCCNC1c2ccccc2N(S(=O)(=O)c2c1ccc(c2)Cl)C
Isomeric SMILES OC(=O)CCCCCCNC1c2ccccc2N(S(=O)(=O)c2c1ccc(c2)Cl)C
InChI InChI=1S/C21H25ClN2O4S/c1-24-18-9-6-5-8-16(18)21(23-13-7-3-2-4-10-20(25)26)17-12-11-15(22)14-19(17)29(24,27)28/h5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26)
1. Brink CB, Harvey BH, Brand L. (2006)
Tianeptine: a novel atypical antidepressant that may provide new insights into the biomolecular basis of depression.
Recent Pat CNS Drug Discov, 1 (1): 29-41. [PMID:18221189]
2. Kasper S, McEwen BS. (2008)
Neurobiological and clinical effects of the antidepressant tianeptine.
CNS Drugs, 22 (1): 15-26. [PMID:18072812]
3. McEwen BS, Chattarji S. (2004)
Molecular mechanisms of neuroplasticity and pharmacological implications: the example of tianeptine.
Eur Neuropsychopharmacol, 14 Suppl 5: S497-502. [PMID:15550348]
4. McEwen BS, Chattarji S, Diamond DM, Jay TM, Reagan LP, Svenningsson P, Fuchs E. (2010)
The neurobiological properties of tianeptine (Stablon): from monoamine hypothesis to glutamatergic modulation.
Mol Psychiatry, 15 (3): 237-49. [PMID:19704408]
5. Svenningsson P, Bateup H, Qi H, Takamiya K, Huganir RL, Spedding M, Roth BL, McEwen BS, Greengard P. (2007)
Involvement of AMPA receptor phosphorylation in antidepressant actions with special reference to tianeptine.
Eur J Neurosci, 26 (12): 3509-17. [PMID:18088278]
6. Szegedi V, Juhász G, Zhang X, Barkóczi B, Qi H, Madeira A, Kapus G, Svenningsson P, Spedding M, Penke B. (2011)
Tianeptine potentiates AMPA receptors by activating CaMKII and PKA via the p38, p42/44 MAPK and JNK pathways.
Neurochem Int, 59 (8): 1109-22. [PMID:22056552]