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Details

Stereochemistry RACEMIC
Molecular Formula C21H25ClN2O4S.H2O4S
Molecular Weight 535.031
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIANEPTINE SULFATE

SMILES

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

InChI

InChIKey=SKEOVGLOOAJSTG-UHFFFAOYSA-N
InChI=1S/C21H25ClN2O4S.H2O4S/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;1-5(2,3)4/h5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26);(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula H2O4S
Molecular Weight 98.078
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
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
[The comparison of tianeptine and carbamazepine in benzodiazepines withdrawal symptoms].
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
Treatment of major depression and anxiety with the selective serotonin re-uptake enhancer tianeptine in the outpatient psychiatric care setting of India.
2003 Feb
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
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
[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
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
[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
[Depressions and disorders of depressive spectrum in general medical practice. Results of the COMPAS program].
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
From restoration of neuroplasticity to the treatment of depression: clinical experience.
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
Reboxetine: a norepinephrine selective reuptake pump inhibitor.
2004 Jan
Tianeptine: a new exploratory therapy for asthma.
2004 Jan
Differential regulation of variant glucocorticoid receptor mRNAs in the rat hippocampus by the antidepressant fluoxetine.
2004 Oct 22
[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
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
Social stress in tree shrews as an animal model of depression: an example of a behavioral model of a CNS disorder.
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 18:20:38 UTC 2023
Edited
by admin
on Sat Dec 16 18:20:38 UTC 2023
Record UNII
MS4R57MW7A
Record Status Validated (UNII)
Record Version
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Name Type Language
TIANEPTINE SULFATE
Common Name English
HEPTANOIC ACID, 7-((3-CHLORO-6,11-DIHYDRO-6-METHYL-5,5-DIOXIDODIBENZO(C,F)(1,2)THIAZEPIN-11-YL)AMINO)-, SULFATE
Systematic Name English
7-((3-CHLORO-6,11-DIHYDRO-6-METHYL-5,5-DIOXIDODIBENZO(C,F)(1,2)THIAZEPIN-11-YL)AMINO)HEPTANOIC ACID SULFATE
Systematic Name English
Code System Code Type Description
CAS
2093109-76-1
Created by admin on Sat Dec 16 18:20:38 UTC 2023 , Edited by admin on Sat Dec 16 18:20:38 UTC 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
MS4R57MW7A
Created by admin on Sat Dec 16 18:20:38 UTC 2023 , Edited by admin on Sat Dec 16 18:20:38 UTC 2023
PRIMARY
SMS_ID
100000182237
Created by admin on Sat Dec 16 18:20:38 UTC 2023 , Edited by admin on Sat Dec 16 18:20:38 UTC 2023
PRIMARY
PUBCHEM
68431515
Created by admin on Sat Dec 16 18:20:38 UTC 2023 , Edited by admin on Sat Dec 16 18:20:38 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY