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Details

Stereochemistry MIXED
Molecular Formula 2C21H25ClN2O4S.C2H2O4
Molecular Weight 963.939
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIANEPTINE HEMIOXALATE

SMILES

OC(=O)C(O)=O.CN1C2=CC=CC=C2C(NCCCCCCC(O)=O)C3=CC=C(Cl)C=C3S1(=O)=O.CN4C5=CC=CC=C5C(NCCCCCCC(O)=O)C6=CC=C(Cl)C=C6S4(=O)=O

InChI

InChIKey=FREVTUJEYJFLAH-UHFFFAOYSA-N
InChI=1S/2C21H25ClN2O4S.C2H2O4/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;3-1(4)2(5)6/h2*5-6,8-9,11-12,14,21,23H,2-4,7,10,13H2,1H3,(H,25,26);(H,3,4)(H,5,6)

HIDE SMILES / InChI

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 C2H2O4
Molecular Weight 90.0349
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
Efficacy and safety of tianeptine in major depression: evidence from a 3-month controlled clinical trial versus paroxetine.
2002
The effects of paroxetine and tianeptine on peripheral biochemical markers in major depression.
2002 Dec
Effect of tianeptine and fluoxetine on the levels of Met-enkephalin and mRNA encoding proenkephalin in the rat.
2002 Mar
Tianeptine: 5-HT uptake sites and 5-HT(1-7) receptors modulate memory formation in an autoshaping Pavlovian/instrumental task.
2002 May
[The comparison of tianeptine and carbamazepine in benzodiazepines withdrawal symptoms].
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
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
Inhibition of microsomal triglyceride transfer protein: another mechanism for drug-induced steatosis in mice.
2003 Jul
Antidepressants: psychiatrists' opinions and clinical practice.
2003 Jul
[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
[Does addiction to antidepressants exist? About a case of one addiction to tianeptine].
2003 Sep-Oct
[Coaxil efficacy in depression in patients with chronic cerebral ischemia].
2004
[Preventive efficacy of tianeptine in recurrent depression with frequent exacerbations].
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
Molecular mechanisms of neuroplasticity and pharmacological implications: the example of tianeptine.
2004 Dec
Alterations of neuroplasticity in depression: the hippocampus and beyond.
2004 Dec
Acute stress-induced changes in hippocampal/prefrontal circuits in rats: effects of antidepressants.
2004 Feb
Untreated depression and hippocampal volume loss.
2004 Jul
Differential regulation of variant glucocorticoid receptor mRNAs in the rat hippocampus by the antidepressant fluoxetine.
2004 Oct 22
[Comparison of two assessment tools of antidepressant side-effects: UKU scale versus spontaneous notification].
2004 Sep-Oct
[Coaxil therapy of affective disorders in brain vascular pathology].
2005
Treatment of depression with the serotonin reuptake enhancer tianeptine in the primary care setting of India.
2005 Feb
Neurobiology of mood, anxiety, and emotions as revealed by studies of a unique antidepressant: tianeptine.
2005 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
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 18:20:40 UTC 2023
Edited
by admin
on Sat Dec 16 18:20:40 UTC 2023
Record UNII
N8GG84TJ4J
Record Status Validated (UNII)
Record Version
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Name Type Language
TIANEPTINE HEMIOXALATE
Common Name English
HEPTANOIC ACID, 7-((3-CHLORO-6,11-DIHYDRO-6-METHYL-5,5-DIOXIDODIBENZO(C,F)(1,2)THIAZEPIN-11-YL)AMINO)-, ETHANEDIOATE (2:1)
Systematic Name English
TIANEPTINE OXALATE (2:1)
Common Name English
Code System Code Type Description
CAS
2231739-19-6
Created by admin on Sat Dec 16 18:20:40 UTC 2023 , Edited by admin on Sat Dec 16 18:20:40 UTC 2023
PRIMARY
PUBCHEM
163203565
Created by admin on Sat Dec 16 18:20:40 UTC 2023 , Edited by admin on Sat Dec 16 18:20:40 UTC 2023
PRIMARY
FDA UNII
N8GG84TJ4J
Created by admin on Sat Dec 16 18:20:40 UTC 2023 , Edited by admin on Sat Dec 16 18:20:40 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY