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
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
Effect of antidepressant drugs on the human corticotropin-releasing-hormone gene promoter activity in neuro-2A cells.	2002 Nov-Dec	12866730
[The comparison of tianeptine and carbamazepine in benzodiazepines withdrawal symptoms].	2002 Nov-Dec	12647454
[Therapy of affective disorders with tianeptine in patients with essential hypertension].	2003	12891255
Clinical and neurobiological effects of tianeptine and paroxetine in major depression.	2003 Apr	12640217
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
State markers of depression in sleep EEG: dependency on drug and gender in patients treated with tianeptine or paroxetine.	2003 Feb	12589388
Tianeptine may be a useful adjunct in the treatment of alcohol dependence of adolescents.	2003 Jan	12544017
Effect of antidepressants on the phospholipase A2 activity in plasma membranes of the rat brain cortex.	2003 Jan-Feb	12856820
Tianeptine: a novel strategy of psychopharmacological treatment of children with autistic disorder.	2003 Jul	12858327
Inhibition of microsomal triglyceride transfer protein: another mechanism for drug-induced steatosis in mice.	2003 Jul	12829995
Antidepressants: psychiatrists' opinions and clinical practice.	2003 Jul	12807374
[A meta-analysis of randomized controlled trials of tianeptine versus SSRI in the short-term treatment of depression].	2003 Jul-Aug	14615702
[Tianeptine induced acute hepatitis].	2003 Mar	12700528
[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
[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
[Clinical efficacy of tianeptine in patients with ischemic heart disease and comorbid depression].	2004	15489844
Behavioural effects of thieno and pyrazolo [2,1] benzothiazepine derivatives in mice.	2004	15344839
[Depressions and disorders of depressive spectrum in general medical practice. Results of the COMPAS program].	2004	15137385
Trends in the development of new antidepressants. Is there a light at the end of the tunnel?	2004 Apr	15078174
Regulation of the human corticotropin-releasing-hormone gene promoter activity by antidepressant drugs in Neuro-2A and AtT-20 cells.	2004 Apr	14735130
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
Acute stress-induced changes in hippocampal/prefrontal circuits in rats: effects of antidepressants.	2004 Feb	14704220
Reboxetine: a norepinephrine selective reuptake pump inhibitor.	2004 Jan	15334987
Untreated depression and hippocampal volume loss.	2004 Jul	15229074
Chronic administration of tianeptine balances lipopolysaccharide-induced expression of cytokines in the spleen and hypothalamus of rats.	2004 Jul	15110927
Behavioral and neuroendocrine changes during mental stress and repeated treatment with antidepressants in healthy men.	2004 Jun	15240411
Tianeptine: a facilitator of the reuptake of serotonin and norepinephrine as an antidepressant?	2004 Sep	15361747
[Comparison of two assessment tools of antidepressant side-effects: UKU scale versus spontaneous notification].	2004 Sep-Oct	15627047
[Depression in patients with chronic dermatoses and its treatment with coaxil].	2005	16250581
Neuroendocrine predictors of the evolution of depression.	2005	16156385
The pharmacological management of depression.	2005	16156378
[Depressive disorders in general medical practice in KOMPAS study: outlook of a cardiologist].	2005	16091639
[Coaxil therapy of affective disorders in brain vascular pathology].	2005	15984189
[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
[Evaluation of antidepressant activity in a model of depressionlike state due to social isolation in rats].	2005 Jul-Aug	16193649
Neurobiology of mood, anxiety, and emotions as revealed by studies of a unique antidepressant: tianeptine.	2005 Jun	15753957
Investigation of the effects of tianeptine and fluoxetine on pentylenetetrazole-induced seizures in rats.	2005 Mar	15589568
[Comparative study of the antidepressant and anxiolytic activity of fluoxetine and tianeptine].	2005 May-Jun	16047671
[Attention deficit hyperactivity: tianeptine open trial].	2005 Oct	16205621
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