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Details

Stereochemistry RACEMIC
Molecular Formula C21H25ClN2O4S
Molecular Weight 436.954
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIANEPTINE

SMILES

CN1c2ccccc2C(c3ccc(cc3S1(=O)=O)Cl)NCCCCCCC(=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
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
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
383 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
Effect of repeated treatment with tianeptine and fluoxetine on the central alpha(1)-adrenergic system.
2001 Sep
[The role of depressive disorders in hypertensive disease and possibilities of their correction: assessment of the effect of tianeptine].
2002
[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
[Efficacy and acceptability of tianeptine and sertraline in the acute treatment phase of depression].
2002 Jul-Aug
Effect of repeated treatment with tianeptine and fluoxetine on central dopamine D(2) /D(3) receptors.
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
Effect of antidepressant drugs on the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells.
2002 Nov-Dec
[Clinical efficacy and tolerability of tianeptine in treatment of depression (Russian open multicenter trial)].
2003
[Therapy of affective disorders with tianeptine in patients with essential hypertension].
2003
The ELIXIR study: evaluation of sexual dysfunction in 4557 depressed patients in France.
2003
Psychopharmacological effects of tianeptine analogous hetero[2,1] benzothiazepine derivatives.
2003
Clinical and neurobiological effects of tianeptine and paroxetine in major depression.
2003 Apr
Neuropharmacological study of hetero[2,1]benzothiazepine derivatives analogues of tianeptine.
2003 Jan
Chronic treatment with the antidepressant tianeptine attenuates lipopolysaccharide-induced Fos expression in the rat paraventricular nucleus and HPA axis activation.
2003 Jan
Local, but not systemic, administration of serotonergic antidepressants decreases hippocampal nitric oxide synthase activity.
2003 Jan 3
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
Switching to tianeptine in patients with antidepressant-induced sexual dysfunction.
2003 Jun
[Tianeptine induced acute hepatitis].
2003 Mar
[Therapy resistant major depression: improvement of symptomatology after combining antidepressants with Tianeptine (Stablon)].
2003 May
Neuroprotective properties of tianeptine: interactions with cytokines.
2003 May
Evaluation of cognitive function of fluoxetine, sertraline and tianeptine in isolation and chronic unpredictable mild stress-induced depressive Wistar rats.
2003 Nov
[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
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
[Coaxil efficacy in depression in patients with chronic cerebral ischemia].
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
Regulation of the human corticotropin-releasing-hormone gene promoter activity by antidepressant drugs in Neuro-2A and AtT-20 cells.
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
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
Acute stress-induced changes in hippocampal/prefrontal circuits in rats: effects of antidepressants.
2004 Feb
Tianeptine: a new exploratory therapy for asthma.
2004 Jan
The selective serotonin reuptake inhibitor citalopram increases fear after acute treatment but reduces fear with chronic treatment: a comparison with tianeptine.
2004 Jun 15
Differential regulation of variant glucocorticoid receptor mRNAs in the rat hippocampus by the antidepressant fluoxetine.
2004 Oct 22
[Comparison of two assessment tools of antidepressant side-effects: UKU scale versus spontaneous notification].
2004 Sep-Oct
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
[Synaptic plasticity and neuropathology: new approaches in drug discovery].
2005 Jan
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
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.
Name Type Language
TIANEPTINE
INN   MI   WHO-DD  
INN  
Official Name English
STABLON
Brand Name English
JNJ-39823277
Code English
(3-CHLORO-6-METHYL-5,5-DIOXO-6,11-DIHYDRODIBENZO(C,F)(1,2)THIAZEPIN-11-YL)-7-AMINOHEPTANOIC ACID
Systematic Name English
TPI-1062
Code English
7-((3-CHLORO-6,11-DIHYDRO-6-METHYLDIBENZO(C,F)(1,2)THIAZEPIN-11-YL)AMINO)HEPTANOIC ACID S,S-DIOXIDE
Common Name English
TIANEPTINE [INN]
Common Name English
TIANEPTINE [MI]
Common Name English
TIANEPTINE [WHO-DD]
Common Name English
TIANEPTINE [NFLIS-DRUG]
Common Name English
S-1574
Code English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
WHO-ATC N06AX14
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
FDA ORPHAN DRUG 627918
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
WHO-VATC QN06AX14
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
NCI_THESAURUS C28197
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
Code System Code Type Description
DRUG CENTRAL
2650
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
MERCK INDEX
M10845
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY Merck Index
EVMPD
SUB11007MIG
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
IUPHAR
7558
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
PUBCHEM
68870
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL1289110
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
CAS
72797-41-2
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
INN
4906
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
CAS
66981-73-5
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
SUPERSEDED
FDA UNII
0T493YFU8O
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
NCI_THESAURUS
C152599
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
MESH
C050504
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
RXCUI
38252
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB09289
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY
WIKIPEDIA
TIANEPTINE
Created by admin on Sat Jun 26 10:26:22 UTC 2021 , Edited by admin on Sat Jun 26 10:26:22 UTC 2021
PRIMARY