Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C21H25ClN2O4S.C2H2O4 |
| Molecular Weight | 526.987 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C(O)=O.CN1C2=CC=CC=C2C(NCCCCCCC(O)=O)C3=CC=C(Cl)C=C3S1(=O)=O
InChI
InChIKey=NDSDDKJOEBKUJI-UHFFFAOYSA-N
InChI=1S/C21H25ClN2O4S.C2H2O4/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;3-1(4)2(5)6/h5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26);(H,3,4)(H,5,6)
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 |
|---|---|---|
| [The role of depressive disorders in hypertensive disease and possibilities of their correction: assessment of the effect of tianeptine]. | 2002 |
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| Tianeptine and fluoxetine in major depression: a 6-week randomised double-blind study. | 2002 Aug |
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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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| Synaptic plasticity and tianeptine: structural regulation. | 2002 Jul |
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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 comparison of tianeptine and carbamazepine in benzodiazepines withdrawal symptoms]. | 2002 Nov-Dec |
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| [Clinical efficacy and tolerability of tianeptine in treatment of depression (Russian open multicenter trial)]. | 2003 |
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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 |
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| State markers of depression in sleep EEG: dependency on drug and gender in patients treated with tianeptine or paroxetine. | 2003 Feb |
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| Neuropharmacological study of hetero[2,1]benzothiazepine derivatives analogues of tianeptine. | 2003 Jan |
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| Tianeptine may be a useful adjunct in the treatment of alcohol dependence of adolescents. | 2003 Jan |
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| Chronic treatment with the antidepressant tianeptine attenuates lipopolysaccharide-induced Fos expression in the rat paraventricular nucleus and HPA axis activation. | 2003 Jan |
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| Local, but not systemic, administration of serotonergic antidepressants decreases hippocampal nitric oxide synthase activity. | 2003 Jan 3 |
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| Effect of antidepressants on the phospholipase A2 activity in plasma membranes of the rat brain cortex. | 2003 Jan-Feb |
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| [Therapy resistant major depression: improvement of symptomatology after combining antidepressants with Tianeptine (Stablon)]. | 2003 May |
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| Neuroprotective properties of tianeptine: interactions with cytokines. | 2003 May |
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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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| Prenatal stress in rats predicts immobility behavior in the forced swim test. Effects of a chronic treatment with tianeptine. | 2003 Nov 7 |
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| [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 |
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| [Preventive efficacy of tianeptine in recurrent depression with frequent exacerbations]. | 2004 |
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| Tianeptine as a slightly effective therapeutic option for attention-deficit hyperactivity disorder. | 2004 |
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| Trends in the development of new antidepressants. Is there a light at the end of the tunnel? | 2004 Apr |
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| Regulation of the human corticotropin-releasing-hormone gene promoter activity by antidepressant drugs in Neuro-2A and AtT-20 cells. | 2004 Apr |
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| Antidepressant treatment with tianeptine reduces apoptosis in the hippocampal dentate gyrus and temporal cortex. | 2004 Apr 15 |
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| The effects of tianeptine or paroxetine on 35% CO2 provoked panic in panic disorder. | 2004 Dec |
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| From restoration of neuroplasticity to the treatment of depression: clinical experience. | 2004 Dec |
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| Molecular mechanisms of neuroplasticity and pharmacological implications: the example of tianeptine. | 2004 Dec |
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| Preclinical research on stress, memory, and the brain in the development of pharmacotherapy for depression. | 2004 Dec |
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| Alterations of neuroplasticity in depression: the hippocampus and beyond. | 2004 Dec |
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| Reboxetine: a norepinephrine selective reuptake pump inhibitor. | 2004 Jan |
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| [Detection of new antidepressive agents using thin-layer chromatography]. | 2004 Jan |
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| Untreated depression and hippocampal volume loss. | 2004 Jul |
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| [Extrapyramidal syndrome worsened by tianeptine]. | 2004 Jul-Aug |
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| The selective serotonin reuptake inhibitor citalopram increases fear after acute treatment but reduces fear with chronic treatment: a comparison with tianeptine. | 2004 Jun 15 |
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| Refractory pain-depression syndrome treated with tianeptine: a case report. | 2004 Mar |
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| Antidepressants in chronic unpredictable mild stress (CUMS)-induced deficit of fighting behavior. | 2004 May-Jun |
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| Tianeptine: a facilitator of the reuptake of serotonin and norepinephrine as an antidepressant? | 2004 Sep |
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| [Depression in patients with chronic dermatoses and its treatment with coaxil]. | 2005 |
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| [Depressive disorders in general medical practice in KOMPAS study: outlook of a cardiologist]. | 2005 |
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| [Coaxil treatment of primary headaches comorbid with depression]. | 2005 |
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| Treatment of depression with the serotonin reuptake enhancer tianeptine in the primary care setting of India. | 2005 Feb |
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| [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 |
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| Social stress in tree shrews as an animal model of depression: an example of a behavioral model of a CNS disorder. | 2005 Mar |
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| [Attention deficit hyperactivity: tianeptine open trial]. | 2005 Oct |
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| 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.
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135186602
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300000005404
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2231739-18-5
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8UDR73X2CR
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admin on Sat Dec 16 19:01:42 GMT 2023 , Edited by admin on Sat Dec 16 19:01:42 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD
