Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C21H24ClN2O4S.Na |
| Molecular Weight | 458.934 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CN1C2=C(C=CC=C2)C(NCCCCCCC([O-])=O)C3=CC=C(Cl)C=C3S1(=O)=O
InChI
InChIKey=ZLBSUOGMZDXYKE-UHFFFAOYSA-M
InChI=1S/C21H25ClN2O4S.Na/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);/q;+1/p-1
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C21H24ClN2O4S |
| Molecular Weight | 435.944 |
| Charge | -1 |
| 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.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| A meta-analysis of randomized controlled trials of tianeptine versus SSRI in the short-term treatment of depression. | 2002 Jul |
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| Structural plasticity and tianeptine: cellular and molecular targets. | 2002 Jul |
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| Synaptic plasticity and tianeptine: structural regulation. | 2002 Jul |
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| 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 |
|
| [A role of depression in chronic dorsalgia: approaches to therapeutic correction]. | 2004 |
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| [Coaxil efficacy in depression in patients with chronic cerebral ischemia]. | 2004 |
|
| [Preventive efficacy of tianeptine in recurrent depression with frequent exacerbations]. | 2004 |
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| [Clinical efficacy of tianeptine in patients with ischemic heart disease and comorbid depression]. | 2004 |
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| Behavioural effects of thieno and pyrazolo [2,1] benzothiazepine derivatives in mice. | 2004 |
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| 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 |
|
| Tianeptine as a slightly effective therapeutic option for attention-deficit hyperactivity disorder. | 2004 |
|
| Trends in the development of new antidepressants. Is there a light at the end of the tunnel? | 2004 Apr |
|
| 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 |
|
| 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 |
|
| [Detection of new antidepressive agents using thin-layer chromatography]. | 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| [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 |
|
| 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 |
|
| [Attention deficit hyperactivity: tianeptine open trial]. | 2005 Oct |
|
| 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 |
|
| 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
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
Edited
Fri Dec 15 19:02:12 GMT 2023
by
admin
on
Fri Dec 15 19:02:12 GMT 2023
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| Record UNII |
YG0E19592I
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| Record Status |
Validated (UNII)
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| Record Version |
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Tianeptine sodium
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m10845
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |