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
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)
| 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.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of tianeptine and mianserin on car driving skills. | 2001 Apr |
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| Tianeptine versus fluoxetine in the treatment of depression complicating Alzheimer's disease. | 2001 Nov |
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| Tianeptine and fluoxetine in major depression: a 6-week randomised double-blind study. | 2002 Aug |
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| The effects of paroxetine and tianeptine on peripheral biochemical markers in major depression. | 2002 Dec |
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| Mss4 gene is up-regulated in rat brain after chronic treatment with antidepressant and down-regulated when rats are anhedonic. | 2002 Dec |
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| Structural plasticity and tianeptine: cellular and molecular targets. | 2002 Jul |
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| [Efficacy and acceptability of tianeptine and sertraline in the acute treatment phase of depression]. | 2002 Jul-Aug |
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| Effect of antidepressant drugs on the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells. | 2002 Nov-Dec |
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| The antidepressant tianeptine persistently modulates glutamate receptor currents of the hippocampal CA3 commissural associational synapse in chronically stressed rats. | 2002 Sep |
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| Enhancement of stress-induced pituitary hormone release and cardiovascular activation by antidepressant treatment in healthy men. | 2002 Sep |
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| [Therapy of affective disorders with tianeptine in patients with essential hypertension]. | 2003 |
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| Psychopharmacological effects of tianeptine analogous hetero[2,1] benzothiazepine derivatives. | 2003 |
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| Treatment of major depression and anxiety with the selective serotonin re-uptake enhancer tianeptine in the outpatient psychiatric care setting of India. | 2003 Feb |
|
| 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: a novel strategy of psychopharmacological treatment of children with autistic disorder. | 2003 Jul |
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| Antidepressants: psychiatrists' opinions and clinical practice. | 2003 Jul |
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| [A meta-analysis of randomized controlled trials of tianeptine versus SSRI in the short-term treatment of depression]. | 2003 Jul-Aug |
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| Thyroid hormones in the rat amygdala as common targets for antidepressant drugs, mood stabilizers, and sleep deprivation. | 2003 Nov 15 |
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| [Preventive efficacy of tianeptine in recurrent depression with frequent exacerbations]. | 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 |
|
| Reboxetine: a norepinephrine selective reuptake pump inhibitor. | 2004 Jan |
|
| [Extrapyramidal syndrome worsened by tianeptine]. | 2004 Jul-Aug |
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| 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 |
|
| [Depression in patients with chronic dermatoses and its treatment with coaxil]. | 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 |
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| 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 |
|
| [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
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
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admin
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Sat Dec 16 10:25:44 GMT 2023
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| Record UNII |
AKU7QFL9ZT
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Validated (UNII)
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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ENANTIOMER -> ENANTIOMER |
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RACEMATE -> ENANTIOMER |
