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
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)
| 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.
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 |
|
| [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 |
|
| The effects of paroxetine and tianeptine on peripheral biochemical markers in major depression. | 2002 Dec |
|
| Mss4 gene is up-regulated in rat brain after chronic treatment with antidepressant and down-regulated when rats are anhedonic. | 2002 Dec |
|
| [Efficacy and acceptability of tianeptine and sertraline in the acute treatment phase of depression]. | 2002 Jul-Aug |
|
| 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 |
|
| Modulation of tianeptine on ion currents induced by inhibitory neurotransmitters in acutely dissociated dorsal raphe neurons of Sprague-Dawley rats. | 2002 Oct |
|
| The antidepressant tianeptine persistently modulates glutamate receptor currents of the hippocampal CA3 commissural associational synapse in chronically stressed rats. | 2002 Sep |
|
| Enhancement of stress-induced pituitary hormone release and cardiovascular activation by antidepressant treatment in healthy men. | 2002 Sep |
|
| [Clinical efficacy and tolerability of tianeptine in treatment of depression (Russian open multicenter trial)]. | 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 |
|
| 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 |
|
| Local, but not systemic, administration of serotonergic antidepressants decreases hippocampal nitric oxide synthase activity. | 2003 Jan 3 |
|
| 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 |
|
| [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 |
|
| [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 |
|
| 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 |
|
| Preclinical research on stress, memory, and the brain in the development of pharmacotherapy for depression. | 2004 Dec |
|
| Acute stress-induced changes in hippocampal/prefrontal circuits in rats: effects of antidepressants. | 2004 Feb |
|
| Tianeptine: a new exploratory therapy for asthma. | 2004 Jan |
|
| Untreated depression and hippocampal volume loss. | 2004 Jul |
|
| [Extrapyramidal syndrome worsened by tianeptine]. | 2004 Jul-Aug |
|
| 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 |
|
| Tianeptine: a facilitator of the reuptake of serotonin and norepinephrine as an antidepressant? | 2004 Sep |
|
| The pharmacological management of depression. | 2005 |
|
| [Depressive disorders in general medical practice in KOMPAS study: outlook of a cardiologist]. | 2005 |
|
| [Coaxil treatment of primary headaches comorbid with depression]. | 2005 |
|
| 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 |
|
| A comparative study of fluoxetine, moclobemide, and tianeptine in the treatment of posttraumatic stress disorder following an earthquake. | 2006 Apr |
|
| 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
Sat Dec 16 18:20:38 GMT 2023
by
admin
on
Sat Dec 16 18:20:38 GMT 2023
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| Record UNII |
MS4R57MW7A
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| Record Status |
Validated (UNII)
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| Record Version |
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2093109-76-1
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MS4R57MW7A
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100000182237
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68431515
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