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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
Structural plasticity and tianeptine: cellular and molecular targets.
2002 Jul
[The comparison of tianeptine and carbamazepine in benzodiazepines withdrawal symptoms].
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
Treatment of major depression and anxiety with the selective serotonin re-uptake enhancer tianeptine in the outpatient psychiatric care setting of India.
2003 Feb
Neuropharmacological study of hetero[2,1]benzothiazepine derivatives analogues of tianeptine.
2003 Jan
Effect of antidepressants on the phospholipase A2 activity in plasma membranes of the rat brain cortex.
2003 Jan-Feb
Tianeptine: a novel strategy of psychopharmacological treatment of children with autistic disorder.
2003 Jul
Inhibition of microsomal triglyceride transfer protein: another mechanism for drug-induced steatosis in mice.
2003 Jul
Antidepressants: psychiatrists' opinions and clinical practice.
2003 Jul
Switching to tianeptine in patients with antidepressant-induced sexual dysfunction.
2003 Jun
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
[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
Trends in the development of new antidepressants. Is there a light at the end of the tunnel?
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
Acute stress-induced changes in hippocampal/prefrontal circuits in rats: effects of antidepressants.
2004 Feb
[Detection of new antidepressive agents using thin-layer chromatography].
2004 Jan
Tianeptine: a new exploratory therapy for asthma.
2004 Jan
Untreated depression and hippocampal volume loss.
2004 Jul
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
The selective serotonin reuptake inhibitor citalopram increases fear after acute treatment but reduces fear with chronic treatment: a comparison with tianeptine.
2004 Jun 15
Antidepressants in chronic unpredictable mild stress (CUMS)-induced deficit of fighting behavior.
2004 May-Jun
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
[Comparison of two assessment tools of antidepressant side-effects: UKU scale versus spontaneous notification].
2004 Sep-Oct
[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
[Coaxil therapy of affective disorders in brain vascular pathology].
2005
[Synaptic plasticity and neuropathology: new approaches in drug discovery].
2005 Jan
[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
[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 10:25:44 UTC 2023
Edited
by admin
on Sat Dec 16 10:25:44 UTC 2023
Record UNII
AKU7QFL9ZT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIANEPTINE, (+)-
Common Name English
HEPTANOIC ACID, 7-((3-CHLORO-6,11-DIHYDRO-6-METHYLDIBENZO(C,F)(1,2)THIAZEPIN-11-YL)AMINO)-, S,S-DIOXIDE, (+)-
Systematic Name English
(+)-TIANEPTINE
Common Name English
S-16190
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
AKU7QFL9ZT
Created by admin on Sat Dec 16 10:25:44 UTC 2023 , Edited by admin on Sat Dec 16 10:25:44 UTC 2023
PRIMARY
PUBCHEM
68870
Created by admin on Sat Dec 16 10:25:44 UTC 2023 , Edited by admin on Sat Dec 16 10:25:44 UTC 2023
PRIMARY
CAS
169293-31-6
Created by admin on Sat Dec 16 10:25:44 UTC 2023 , Edited by admin on Sat Dec 16 10:25:44 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> ENANTIOMER
RACEMATE -> ENANTIOMER