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Details

Stereochemistry RACEMIC
Molecular Formula 2C21H25ClN2O4S.2H2O.H2O4S
Molecular Weight 1008.013
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIANEPTINE HEMISULFATE MONOHYDRATE

SMILES

O.O.OS(O)(=O)=O.CN1C2=C(C=CC=C2)C(NCCCCCCC(O)=O)C3=CC=C(Cl)C=C3S1(=O)=O.CN4C5=C(C=CC=C5)C(NCCCCCCC(O)=O)C6=CC=C(Cl)C=C6S4(=O)=O

InChI

InChIKey=KVVMXNNJBVTOSX-UHFFFAOYSA-N
InChI=1S/2C21H25ClN2O4S.H2O4S.2H2O/c2*1-24-18-9-6-5-8-16(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;;/h2*5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26);(H2,1,2,3,4);2*1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
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 ( + / - )

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

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
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
Tianeptine and fluoxetine in major depression: a 6-week randomised double-blind study.
2002 Aug
Mss4 gene is up-regulated in rat brain after chronic treatment with antidepressant and down-regulated when rats are anhedonic.
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
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
Effect of antidepressant drugs on the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells.
2002 Nov-Dec
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
Tianeptine may be a useful adjunct in the treatment of alcohol dependence of adolescents.
2003 Jan
Chronic treatment with the antidepressant tianeptine attenuates lipopolysaccharide-induced Fos expression in the rat paraventricular nucleus and HPA axis activation.
2003 Jan
Tianeptine, plasma serotonin, and pulmonary hypertension.
2003 Jan 4
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
Neuroprotective properties of tianeptine: interactions with cytokines.
2003 May
[Misuse of tianeptine: five cases of abuse].
2003 Nov
[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
[Clinical efficacy of tianeptine in patients with ischemic heart disease and comorbid depression].
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
Antidepressant treatment with tianeptine reduces apoptosis in the hippocampal dentate gyrus and temporal cortex.
2004 Apr 15
From restoration of neuroplasticity to the treatment of depression: clinical experience.
2004 Dec
Alterations of neuroplasticity in depression: the hippocampus and beyond.
2004 Dec
[Detection of new antidepressive agents using thin-layer chromatography].
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
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
[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
[Depressive disorders in general medical practice in KOMPAS study: outlook of a cardiologist].
2005
[Coaxil therapy of affective disorders in brain vascular pathology].
2005
[Coaxil treatment of primary headaches comorbid with 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
[Evaluation of antidepressant activity in a model of depressionlike state due to social isolation in rats].
2005 Jul-Aug
[Comparative study of the antidepressant and anxiolytic activity of fluoxetine and tianeptine].
2005 May-Jun
[Attention deficit hyperactivity: tianeptine open trial].
2005 Oct
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 08:32:50 UTC 2023
Edited
by admin
on Sat Dec 16 08:32:50 UTC 2023
Record UNII
4B136GSG9M
Record Status Validated (UNII)
Record Version
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Name Type Language
TIANEPTINE HEMISULFATE MONOHYDRATE
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, HYDRATE (2:1:2)
Common Name English
Code System Code Type Description
FDA UNII
4B136GSG9M
Created by admin on Sat Dec 16 08:32:50 UTC 2023 , Edited by admin on Sat Dec 16 08:32:50 UTC 2023
PRIMARY
PUBCHEM
45375836
Created by admin on Sat Dec 16 08:32:50 UTC 2023 , Edited by admin on Sat Dec 16 08:32:50 UTC 2023
PRIMARY
CAS
1224690-84-9
Created by admin on Sat Dec 16 08:32:50 UTC 2023 , Edited by admin on Sat Dec 16 08:32:50 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY