TIANEPTINE

Possibly Marketed Outside US

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 Search

SMILES

CN1C2=CC=CC=C2C(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	( + / - )

Description
Sources: https://www.ema.europa.eu/en/documents/psusa/tianeptine-list-nationally-authorised-medicinal-products-psusa/00002943/201506_en.pdf | http://www.hmdb.ca/metabolites/HMDB0042038 | https://www.ncbi.nlm.nih.gov/pubmed/25026323

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu-type opioid receptor 61 Target ID: P35372\|\|\|G8XRH8\|\|\|Q5TDA1\|\|\|Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25026323	Agonist 2752		383.0 nM [Ki]

PubMed

Title	Date	PubMed
Current trends in the development of new antidepressants.	2001 Feb	11172668
A meta-analysis of randomized controlled trials of tianeptine versus SSRI in the short-term treatment of depression.	2002 Jul	15177089
Synaptic plasticity and tianeptine: structural regulation.	2002 Jul	15177087
[Efficacy and acceptability of tianeptine and sertraline in the acute treatment phase of depression].	2002 Jul-Aug	12232543
Overcoming the effects of stress on synaptic plasticity in the intact hippocampus: rapid actions of serotonergic and antidepressant agents.	2002 May 1	11978839
[The comparison of tianeptine and carbamazepine in benzodiazepines withdrawal symptoms].	2002 Nov-Dec	12647454
The antidepressant tianeptine persistently modulates glutamate receptor currents of the hippocampal CA3 commissural associational synapse in chronically stressed rats.	2002 Sep	12372016
[Clinical efficacy and tolerability of tianeptine in treatment of depression (Russian open multicenter trial)].	2003	14564774
[Therapy of affective disorders with tianeptine in patients with essential hypertension].	2003	12891255
The ELIXIR study: evaluation of sexual dysfunction in 4557 depressed patients in France.	2003	12740155
Switching to tianeptine in patients with antidepressant-induced sexual dysfunction.	2003 Jun	12766932
[Tianeptine induced acute hepatitis].	2003 Mar	12700528
[Misuse of tianeptine: five cases of abuse].	2003 Nov	14760227
Thyroid hormones in the rat amygdala as common targets for antidepressant drugs, mood stabilizers, and sleep deprivation.	2003 Nov 15	14625147
[Does addiction to antidepressants exist? About a case of one addiction to tianeptine].	2003 Sep-Oct	14615695
[Coaxil efficacy in depression in patients with chronic cerebral ischemia].	2004	15553381
[Preventive efficacy of tianeptine in recurrent depression with frequent exacerbations].	2004	15490938
[Clinical efficacy of tianeptine in patients with ischemic heart disease and comorbid depression].	2004	15489844
[Depressions and disorders of depressive spectrum in general medical practice. Results of the COMPAS program].	2004	15137385
Tianeptine as a slightly effective therapeutic option for attention-deficit hyperactivity disorder.	2004	15034228
Antidepressant treatment with tianeptine reduces apoptosis in the hippocampal dentate gyrus and temporal cortex.	2004 Apr 15	15050859
The effects of tianeptine or paroxetine on 35% CO2 provoked panic in panic disorder.	2004 Dec	15582922
From restoration of neuroplasticity to the treatment of depression: clinical experience.	2004 Dec	15550350
Preclinical research on stress, memory, and the brain in the development of pharmacotherapy for depression.	2004 Dec	15550347
Alterations of neuroplasticity in depression: the hippocampus and beyond.	2004 Dec	15550346
The selective serotonin reuptake inhibitor citalopram increases fear after acute treatment but reduces fear with chronic treatment: a comparison with tianeptine.	2004 Jun 15	15184036
Refractory pain-depression syndrome treated with tianeptine: a case report.	2004 Mar	14961940
Treatment of bronchial asthma with tianeptine.	2004 Nov	15632955
[Coaxil treatment of primary headaches comorbid with depression].	2005	15704486
Treatment of depression with the serotonin reuptake enhancer tianeptine in the primary care setting of India.	2005 Feb	16008321
[Synaptic plasticity and neuropathology: new approaches in drug discovery].	2005 Jan	15639031
Neurobiology of mood, anxiety, and emotions as revealed by studies of a unique antidepressant: tianeptine.	2005 Jun	15753957
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	16272152

Patents

Sample Use Guides

In Vitro Use Guide

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 `Wed Apr 02 08:24:09 GMT 2025` Edited by `admin` on `Wed Apr 02 08:24:09 GMT 2025`
Record UNII	0T493YFU8O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

STABLON

Preferred Name

English

TIANEPTINE

Official 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