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
Tianeptine: a review of its use in depressive disorders.	2001	11463130
Effects of tianeptine and mianserin on car driving skills.	2001 Apr	11349388
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
Asthma, asthma medication and autonomic nervous system dysfunction.	2001 Nov	11722481
[The role of depressive disorders in hypertensive disease and possibilities of their correction: assessment of the effect of tianeptine].	2002	12494055
[The level of 8-iso-prostaglandin F2 alpha, 4-hydroxynonenal and malondialdehyde in alcohol dependent men during combined therapy].	2002	12043046
Tianeptine and fluoxetine in major depression: a 6-week randomised double-blind study.	2002 Aug	12404675
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
A meta-analysis of randomized controlled trials of tianeptine versus SSRI in the short-term treatment of depression.	2002 Jul	15177089
Structural plasticity and tianeptine: cellular and molecular targets.	2002 Jul	15177088
[Efficacy and acceptability of tianeptine and sertraline in the acute treatment phase of depression].	2002 Jul-Aug	12232543
Enhancement of stress-induced pituitary hormone release and cardiovascular activation by antidepressant treatment in healthy men.	2002 Sep	12236631
[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
Psychopharmacological effects of tianeptine analogous hetero[2,1] benzothiazepine derivatives.	2003	12608009
State markers of depression in sleep EEG: dependency on drug and gender in patients treated with tianeptine or paroxetine.	2003 Feb	12589388
Neuropharmacological study of hetero[2,1]benzothiazepine derivatives analogues of tianeptine.	2003 Jan	12595031
Tianeptine may be a useful adjunct in the treatment of alcohol dependence of adolescents.	2003 Jan	12544017
Chronic treatment with the antidepressant tianeptine attenuates lipopolysaccharide-induced Fos expression in the rat paraventricular nucleus and HPA axis activation.	2003 Jan	12445834
Local, but not systemic, administration of serotonergic antidepressants decreases hippocampal nitric oxide synthase activity.	2003 Jan 3	12480166
Tianeptine, plasma serotonin, and pulmonary hypertension.	2003 Jan 4	12517512
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
[Misuse of tianeptine: five cases of abuse].	2003 Nov	14760227
Prenatal stress in rats predicts immobility behavior in the forced swim test. Effects of a chronic treatment with tianeptine.	2003 Nov 7	14556947
[Does addiction to antidepressants exist? About a case of one addiction to tianeptine].	2003 Sep-Oct	14615695
[Clinical efficacy of tianeptine in patients with ischemic heart disease and comorbid depression].	2004	15489844
Plasticity at hippocampal to prefrontal cortex synapses is impaired by loss of dopamine and stress: importance for psychiatric diseases.	2004	15325962
Trends in the development of new antidepressants. Is there a light at the end of the tunnel?	2004 Apr	15078174
Antidepressant treatment with tianeptine reduces apoptosis in the hippocampal dentate gyrus and temporal cortex.	2004 Apr 15	15050859
Tianeptine: a new exploratory therapy for asthma.	2004 Jan	14718467
Chronic administration of tianeptine balances lipopolysaccharide-induced expression of cytokines in the spleen and hypothalamus of rats.	2004 Jul	15110927
Treatment of bronchial asthma with tianeptine.	2004 Nov	15632955
Differential regulation of variant glucocorticoid receptor mRNAs in the rat hippocampus by the antidepressant fluoxetine.	2004 Oct 22	15469896
[Comparison of two assessment tools of antidepressant side-effects: UKU scale versus spontaneous notification].	2004 Sep-Oct	15627047
Neuroendocrine predictors of the evolution of depression.	2005	16156385
[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
Regulation of hippocampal gene expression is conserved in two species subjected to different stressors and antidepressant treatments.	2006 Feb 1	16140276
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