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Details

Stereochemistry RACEMIC
Molecular Formula C21H25ClN2O4S
Molecular Weight 436.952
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIANEPTINE

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)

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 ( + / - )

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 and its enantiomers: effects on spatial memory in rats with medial septum lesions.
2001 Aug
Tianeptine versus fluoxetine in the treatment of depression complicating Alzheimer's disease.
2001 Nov
Asthma, asthma medication and autonomic nervous system dysfunction.
2001 Nov
[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
[Efficacy and acceptability of tianeptine and sertraline in the acute treatment phase of depression].
2002 Jul-Aug
Effect of repeated treatment with tianeptine and fluoxetine on central dopamine D(2) /D(3) receptors.
2002 Mar
Tianeptine: 5-HT uptake sites and 5-HT(1-7) receptors modulate memory formation in an autoshaping Pavlovian/instrumental task.
2002 May
Overcoming the effects of stress on synaptic plasticity in the intact hippocampus: rapid actions of serotonergic and antidepressant agents.
2002 May 1
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
The ELIXIR study: evaluation of sexual dysfunction in 4557 depressed patients in France.
2003
Neuropharmacological study of hetero[2,1]benzothiazepine derivatives analogues of tianeptine.
2003 Jan
Chronic treatment with the antidepressant tianeptine attenuates lipopolysaccharide-induced Fos expression in the rat paraventricular nucleus and HPA axis activation.
2003 Jan
Inhibition of microsomal triglyceride transfer protein: another mechanism for drug-induced steatosis in mice.
2003 Jul
Antidepressants: psychiatrists' opinions and clinical practice.
2003 Jul
[A meta-analysis of randomized controlled trials of tianeptine versus SSRI in the short-term treatment of depression].
2003 Jul-Aug
[Tianeptine induced acute hepatitis].
2003 Mar
Prenatal stress in rats predicts immobility behavior in the forced swim test. Effects of a chronic treatment with tianeptine.
2003 Nov 7
[A role of depression in chronic dorsalgia: approaches to therapeutic correction].
2004
Plasticity at hippocampal to prefrontal cortex synapses is impaired by loss of dopamine and stress: importance for psychiatric diseases.
2004
Trends in the development of new antidepressants. Is there a light at the end of the tunnel?
2004 Apr
Antidepressant treatment with tianeptine reduces apoptosis in the hippocampal dentate gyrus and temporal cortex.
2004 Apr 15
Molecular mechanisms of neuroplasticity and pharmacological implications: the example of tianeptine.
2004 Dec
Alterations of neuroplasticity in depression: the hippocampus and beyond.
2004 Dec
Reboxetine: a norepinephrine selective reuptake pump inhibitor.
2004 Jan
Tianeptine: a facilitator of the reuptake of serotonin and norepinephrine as an antidepressant?
2004 Sep
[Depression in patients with chronic dermatoses and its treatment with coaxil].
2005
Neuroendocrine predictors of the evolution 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
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

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 Thu Jul 06 22:14:19 UTC 2023
Edited
by admin
on Thu Jul 06 22:14:19 UTC 2023
Record UNII
0T493YFU8O
Record Status Validated (UNII)
Record Version
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Name Type Language
TIANEPTINE
INN   MI   WHO-DD  
INN  
Official Name English
STABLON
Brand Name English
JNJ-39823277
Code English
(3-CHLORO-6-METHYL-5,5-DIOXO-6,11-DIHYDRODIBENZO(C,F)(1,2)THIAZEPIN-11-YL)-7-AMINOHEPTANOIC ACID
Systematic Name English
TPI-1062
Code English
7-((3-CHLORO-6,11-DIHYDRO-6-METHYLDIBENZO(C,F)(1,2)THIAZEPIN-11-YL)AMINO)HEPTANOIC ACID S,S-DIOXIDE
Common Name English
tianeptine [INN]
Common Name English
TIANEPTINE [MI]
Common Name English
Gas station heroin
Common Name English
Tianeptine [WHO-DD]
Common Name English
TIANEPTINE [NFLIS-DRUG]
Common Name English
S-1574
Code English
Classification Tree Code System Code
NCI_THESAURUS C265
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
WHO-ATC N06AX14
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
FDA ORPHAN DRUG 627918
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
WIKIPEDIA Designer-drugs-Tianeptine
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
WHO-VATC QN06AX14
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
NCI_THESAURUS C28197
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
Code System Code Type Description
DRUG CENTRAL
2650
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
MERCK INDEX
M10845
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY Merck Index
EVMPD
SUB11007MIG
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
SMS_ID
100000082178
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
IUPHAR
7558
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID7048295
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
PUBCHEM
68870
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL1289110
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
CAS
72797-41-2
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
INN
4906
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
CAS
66981-73-5
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
SUPERSEDED
FDA UNII
0T493YFU8O
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
NCI_THESAURUS
C152599
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
MESH
C050504
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
RXCUI
38252
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB09289
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
WIKIPEDIA
TIANEPTINE
Created by admin on Thu Jul 06 22:14:20 UTC 2023 , Edited by admin on Thu Jul 06 22:14:20 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Ki
TARGET -> AGONIST
Atypical. G-protein activation
EC50
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY