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].

tianeptine is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used to treat major depressive disorder where approved. Follow this link to Drugs.com for a list of countries where this drug is available.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The precise protein target of tianeptine action is not fully resolved. Originally believed to enhance serotonin transporter activity, evidence is now emerging of further actions. It has been reported that tianeptine potentiates several signaling cascades associated with synaptic plasticity (eg PKA and Ca2+/calmodulin-dependent protein kinase II (CaMKII) phosphorylation, and MAPK pathway) and that a major effect is enhancement of glutamate neurotransmission via AMPA receptors [1,3,5-6]. Tianeptine appears to activate three separate mitogen-activated protein kinase (MAPK) pathways, the c-Jun N-terminal kinase (JNK), p42/44 and p38 MAPK pathways. This activity culminates in enhanced AMPA receptor function through phosphorylation by CaMKII and PKA. Tianeptine most probably enhances fEPSPs via the modulation of postsynaptic excitatory ionotropic receptors. GluA1 (GRIA1) subunit phosphorylation is critical in this effect .