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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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)
InChI Key JICJBGPOMZQUBB-UHFFFAOYSA-N
References
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]