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Details

Stereochemistry UNKNOWN
Molecular Formula C21H25ClN2O4S
Molecular Weight 436.952
Optical Activity ( - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIANEPTINE, (-)-

SMILES

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

InChI

InChIKey=JICJBGPOMZQUBB-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

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
The effects of paroxetine and tianeptine on peripheral biochemical markers in major depression.
2002 Dec
A meta-analysis of randomized controlled trials of tianeptine versus SSRI in the short-term treatment of depression.
2002 Jul
Structural plasticity and tianeptine: cellular and molecular targets.
2002 Jul
Synaptic plasticity and tianeptine: structural regulation.
2002 Jul
Effect of antidepressant drugs on the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells.
2002 Nov-Dec
Psychopharmacological effects of tianeptine analogous hetero[2,1] benzothiazepine derivatives.
2003
Clinical and neurobiological effects of tianeptine and paroxetine in major depression.
2003 Apr
State markers of depression in sleep EEG: dependency on drug and gender in patients treated with tianeptine or paroxetine.
2003 Feb
Neuropharmacological study of hetero[2,1]benzothiazepine derivatives analogues of tianeptine.
2003 Jan
Tianeptine may be a useful adjunct in the treatment of alcohol dependence of adolescents.
2003 Jan
Tianeptine, plasma serotonin, and pulmonary hypertension.
2003 Jan 4
Inhibition of microsomal triglyceride transfer protein: another mechanism for drug-induced steatosis in mice.
2003 Jul
Antidepressants: psychiatrists' opinions and clinical practice.
2003 Jul
[A meta-analysis of randomized controlled trials of tianeptine versus SSRI in the short-term treatment of depression].
2003 Jul-Aug
[Tianeptine induced acute hepatitis].
2003 Mar
Evaluation of cognitive function of fluoxetine, sertraline and tianeptine in isolation and chronic unpredictable mild stress-induced depressive Wistar rats.
2003 Nov
Prenatal stress in rats predicts immobility behavior in the forced swim test. Effects of a chronic treatment with tianeptine.
2003 Nov 7
[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
Behavioural effects of thieno and pyrazolo [2,1] benzothiazepine derivatives in mice.
2004
Plasticity at hippocampal to prefrontal cortex synapses is impaired by loss of dopamine and stress: importance for psychiatric diseases.
2004
[Depressions and disorders of depressive spectrum in general medical practice. Results of the COMPAS program].
2004
Trends in the development of new antidepressants. Is there a light at the end of the tunnel?
2004 Apr
Antidepressant treatment with tianeptine reduces apoptosis in the hippocampal dentate gyrus and temporal cortex.
2004 Apr 15
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
Chronic administration of tianeptine balances lipopolysaccharide-induced expression of cytokines in the spleen and hypothalamus of rats.
2004 Jul
[Extrapyramidal syndrome worsened by tianeptine].
2004 Jul-Aug
Behavioral and neuroendocrine changes during mental stress and repeated treatment with antidepressants in healthy men.
2004 Jun
The selective serotonin reuptake inhibitor citalopram increases fear after acute treatment but reduces fear with chronic treatment: a comparison with tianeptine.
2004 Jun 15
Refractory pain-depression syndrome treated with tianeptine: a case report.
2004 Mar
Treatment of bronchial asthma with tianeptine.
2004 Nov
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
Neuroendocrine predictors of the evolution of depression.
2005
Treatment of depression with the serotonin reuptake enhancer tianeptine in the primary care setting of India.
2005 Feb
[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
A comparative study of fluoxetine, moclobemide, and tianeptine in the treatment of posttraumatic stress disorder following an earthquake.
2006 Apr
Regulation of hippocampal gene expression is conserved in two species subjected to different stressors and antidepressant treatments.
2006 Feb 1
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
XV6773012I
Record Status Validated (UNII)
Record Version
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Name Type Language
TIANEPTINE, (-)-
Common Name English
(-)-TIANEPTINE
Common Name English
S-16191
Code English
HEPTANOIC ACID, 7-((3-CHLORO-6,11-DIHYDRO-6-METHYL-5,5-DIOXIDODIBENZO(C,F)(1,2)THIAZEPIN-11-YL)AMINO)-, (-)-
Systematic Name English
Code System Code Type Description
FDA UNII
XV6773012I
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
191172-75-5
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
RACEMATE -> ENANTIOMER
ENANTIOMER -> ENANTIOMER