TIANEPTINE

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=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	( + / - )

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 2678		383.0 nM [Ki]

PubMed

Title	Date	PubMed
Current trends in the development of new antidepressants.	2001 Feb	11172668
Tianeptine versus fluoxetine in the treatment of depression complicating Alzheimer's disease.	2001 Nov	11746660
[The level of 8-iso-prostaglandin F2 alpha, 4-hydroxynonenal and malondialdehyde in alcohol dependent men during combined therapy].	2002	12043046
The effects of paroxetine and tianeptine on peripheral biochemical markers in major depression.	2002 Dec	12502009
Mss4 gene is up-regulated in rat brain after chronic treatment with antidepressant and down-regulated when rats are anhedonic.	2002 Dec	12435800
Synaptic plasticity and tianeptine: structural regulation.	2002 Jul	15177087
Tianeptine: 5-HT uptake sites and 5-HT(1-7) receptors modulate memory formation in an autoshaping Pavlovian/instrumental task.	2002 May	12034133
Effect of antidepressant drugs on the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells.	2002 Nov-Dec	12866730
Treatment of major depression and anxiety with the selective serotonin re-uptake enhancer tianeptine in the outpatient psychiatric care setting of India.	2003 Feb	12841497
Neuropharmacological study of hetero[2,1]benzothiazepine derivatives analogues of tianeptine.	2003 Jan	12595031
Inhibition of microsomal triglyceride transfer protein: another mechanism for drug-induced steatosis in mice.	2003 Jul	12829995
Switching to tianeptine in patients with antidepressant-induced sexual dysfunction.	2003 Jun	12766932
[Therapy resistant major depression: improvement of symptomatology after combining antidepressants with Tianeptine (Stablon)].	2003 May	12768529
Evaluation of cognitive function of fluoxetine, sertraline and tianeptine in isolation and chronic unpredictable mild stress-induced depressive Wistar rats.	2003 Nov	15332495
[A role of depression in chronic dorsalgia: approaches to therapeutic correction].	2004	15554142
[Coaxil efficacy in depression in patients with chronic cerebral ischemia].	2004	15553381
[Preventive efficacy of tianeptine in recurrent depression with frequent exacerbations].	2004	15490938
[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
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
Molecular mechanisms of neuroplasticity and pharmacological implications: the example of tianeptine.	2004 Dec	15550348
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
[Detection of new antidepressive agents using thin-layer chromatography].	2004 Jan	15035061
Untreated depression and hippocampal volume loss.	2004 Jul	15229074
[Extrapyramidal syndrome worsened by tianeptine].	2004 Jul-Aug	15559554
Treatment of bronchial asthma with tianeptine.	2004 Nov	15632955
[Depression in patients with chronic dermatoses and its treatment with coaxil].	2005	16250581
[Depressive disorders in general medical practice in KOMPAS study: outlook of a cardiologist].	2005	16091639
Social stress in tree shrews as an animal model of depression: an example of a behavioral model of a CNS disorder.	2005 Mar	15744220
[Attention deficit hyperactivity: tianeptine open trial].	2005 Oct	16205621
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 `Sat Dec 16 16:47:15 GMT 2023` Edited by `admin` on `Sat Dec 16 16:47:15 GMT 2023`
Record UNII	0T493YFU8O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TIANEPTINE

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