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Details

Stereochemistry RACEMIC
Molecular Formula C21H25ClN2O4S.ClH
Molecular Weight 473.413
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIANEPTINE HYDROCHLORIDE

SMILES

Cl.CN1C2=C(C=CC=C2)C(NCCCCCCC(O)=O)C3=CC=C(Cl)C=C3S1(=O)=O

InChI

InChIKey=VALUNVMGXVWSGM-UHFFFAOYSA-N
InChI=1S/C21H25ClN2O4S.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H25ClN2O4S
Molecular Weight 436.952
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

TIANEPTINE, a tricyclic antidepressant, is a drug used for the treatment of the major depressive disorder. It was discovered by The French Society of Medical Research in the 1980s. Unlike other tricyclic antidepressants, TIANEPTINE is a selective serotonin reuptake enhancer with minimal effects on norepinephrine and dopamine uptake. Also, it is a full agonist at the mu-opioid and delta-opioid receptors with no effect at the kappa-opioid receptors. Selective mu-opioid agonists typically induce euphoria, which may contribute to TIANEPTINE's antidepressant effect. It is marketed as Coaxil/Stablon in many European countries, but it is not available in the US.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
383.0 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Tianeptine versus fluoxetine in the treatment of depression complicating Alzheimer's disease.
2001 Nov
Asthma, asthma medication and autonomic nervous system dysfunction.
2001 Nov
[The level of 8-iso-prostaglandin F2 alpha, 4-hydroxynonenal and malondialdehyde in alcohol dependent men during combined therapy].
2002
Efficacy and safety of tianeptine in major depression: evidence from a 3-month controlled clinical trial versus paroxetine.
2002
Mss4 gene is up-regulated in rat brain after chronic treatment with antidepressant and down-regulated when rats are anhedonic.
2002 Dec
Structural plasticity and tianeptine: cellular and molecular targets.
2002 Jul
Effect of repeated treatment with tianeptine and fluoxetine on central dopamine D(2) /D(3) receptors.
2002 Mar
Effect of tianeptine and fluoxetine on the levels of Met-enkephalin and mRNA encoding proenkephalin in the rat.
2002 Mar
Tianeptine: 5-HT uptake sites and 5-HT(1-7) receptors modulate memory formation in an autoshaping Pavlovian/instrumental task.
2002 May
Overcoming the effects of stress on synaptic plasticity in the intact hippocampus: rapid actions of serotonergic and antidepressant agents.
2002 May 1
Modulation of tianeptine on ion currents induced by inhibitory neurotransmitters in acutely dissociated dorsal raphe neurons of Sprague-Dawley rats.
2002 Oct
Clinical and neurobiological effects of tianeptine and paroxetine in major depression.
2003 Apr
Chronic treatment with the antidepressant tianeptine attenuates lipopolysaccharide-induced Fos expression in the rat paraventricular nucleus and HPA axis activation.
2003 Jan
Effect of antidepressants on the phospholipase A2 activity in plasma membranes of the rat brain cortex.
2003 Jan-Feb
[A meta-analysis of randomized controlled trials of tianeptine versus SSRI in the short-term treatment of depression].
2003 Jul-Aug
[Misuse of tianeptine: five cases of abuse].
2003 Nov
Thyroid hormones in the rat amygdala as common targets for antidepressant drugs, mood stabilizers, and sleep deprivation.
2003 Nov 15
[Does addiction to antidepressants exist? About a case of one addiction to tianeptine].
2003 Sep-Oct
[A role of depression in chronic dorsalgia: approaches to therapeutic correction].
2004
[Coaxil efficacy in depression in patients with chronic cerebral ischemia].
2004
[Preventive efficacy of tianeptine in recurrent depression with frequent exacerbations].
2004
[Clinical efficacy of tianeptine in patients with ischemic heart disease and comorbid depression].
2004
Plasticity at hippocampal to prefrontal cortex synapses is impaired by loss of dopamine and stress: importance for psychiatric diseases.
2004
Tianeptine as a slightly effective therapeutic option for attention-deficit hyperactivity disorder.
2004
Regulation of the human corticotropin-releasing-hormone gene promoter activity by antidepressant drugs in Neuro-2A and AtT-20 cells.
2004 Apr
The effects of tianeptine or paroxetine on 35% CO2 provoked panic in panic disorder.
2004 Dec
From restoration of neuroplasticity to the treatment of depression: clinical experience.
2004 Dec
Molecular mechanisms of neuroplasticity and pharmacological implications: the example of tianeptine.
2004 Dec
Preclinical research on stress, memory, and the brain in the development of pharmacotherapy for depression.
2004 Dec
Alterations of neuroplasticity in depression: the hippocampus and beyond.
2004 Dec
Reboxetine: a norepinephrine selective reuptake pump inhibitor.
2004 Jan
[Detection of new antidepressive agents using thin-layer chromatography].
2004 Jan
Untreated depression and hippocampal volume loss.
2004 Jul
[Extrapyramidal syndrome worsened by tianeptine].
2004 Jul-Aug
Refractory pain-depression syndrome treated with tianeptine: a case report.
2004 Mar
Antidepressants in chronic unpredictable mild stress (CUMS)-induced deficit of fighting behavior.
2004 May-Jun
Differential regulation of variant glucocorticoid receptor mRNAs in the rat hippocampus by the antidepressant fluoxetine.
2004 Oct 22
Tianeptine: a facilitator of the reuptake of serotonin and norepinephrine as an antidepressant?
2004 Sep
[Depression in patients with chronic dermatoses and its treatment with coaxil].
2005
Neuroendocrine predictors of the evolution of depression.
2005
The pharmacological management of depression.
2005
[Depressive disorders in general medical practice in KOMPAS study: outlook of a cardiologist].
2005
[Evaluation of antidepressant activity in a model of depressionlike state due to social isolation in rats].
2005 Jul-Aug
Neurobiology of mood, anxiety, and emotions as revealed by studies of a unique antidepressant: tianeptine.
2005 Jun
Social stress in tree shrews as an animal model of depression: an example of a behavioral model of a CNS disorder.
2005 Mar
Investigation of the effects of tianeptine and fluoxetine on pentylenetetrazole-induced seizures in rats.
2005 Mar
[Comparative study of the antidepressant and anxiolytic activity of fluoxetine and tianeptine].
2005 May-Jun
[Attention deficit hyperactivity: tianeptine open trial].
2005 Oct
Regulation of hippocampal gene expression is conserved in two species subjected to different stressors and antidepressant treatments.
2006 Feb 1
Tyr-95 and Ile-172 in transmembrane segments 1 and 3 of human serotonin transporters interact to establish high affinity recognition of antidepressants.
2006 Jan 27
Patents

Patents

Sample Use Guides

Using radioligand binding and cell-based functional assays, including bioluminescence resonance energy transfer-based assays for G-protein activation and cAMP accumulation, tianeptine was identified as an efficacious mu-opioid receptor agonist (Ki of 383+/-183 nM and EC50 of 194+/-70 nM). Tianeptine was also a full delta-opioid receptor agonist, although with much lower potency (EC50 of 37.4+/-11.2 uM for G-protein activation). In contrast, tianeptine was inactive at the kappa-opioid receptor.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:25:43 UTC 2023
Edited
by admin
on Sat Dec 16 10:25:43 UTC 2023
Record UNII
2DUX8X079R
Record Status Validated (UNII)
Record Version
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Name Type Language
TIANEPTINE HYDROCHLORIDE
Common Name English
HEPTANOIC ACID, 7-((3-CHLORO-6,11-DIHYDRO-6-METHYL-5,5-DIOXIDODIBENZO(C,F)(1,2)THIAZEPIN-11-YL)AMINO)-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
2DUX8X079R
Created by admin on Sat Dec 16 10:25:43 UTC 2023 , Edited by admin on Sat Dec 16 10:25:43 UTC 2023
PRIMARY
CAS
1159812-13-1
Created by admin on Sat Dec 16 10:25:43 UTC 2023 , Edited by admin on Sat Dec 16 10:25:43 UTC 2023
PRIMARY
PUBCHEM
66524473
Created by admin on Sat Dec 16 10:25:43 UTC 2023 , Edited by admin on Sat Dec 16 10:25:43 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE