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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
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 .