TIANEPTINE SODIUM

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H24ClN2O4S.Na
Molecular Weight	458.934
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[Na+].CN1C2=C(C=CC=C2)C(NCCCCCCC([O-])=O)C3=C(C=C(Cl)C=C3)S1(=O)=O

InChI

InChIKey=ZLBSUOGMZDXYKE-UHFFFAOYSA-M

InChI=1S/C21H25ClN2O4S.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H24ClN2O4S
Molecular Weight	435.944
Charge	-1
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

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

Targets

Primary Target	Pharmacology	Condition	Potency
Mu-type opioid receptor 61	Agonist 2,752		383.0 nM [Ki]

PubMed

Show entries

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
Tianeptine and its enantiomers: effects on spatial memory in rats with medial septum lesions.	2001 Aug	11489464
Chronic treatment with the atypical antidepressant tianeptine attenuates sickness behavior induced by peripheral but not central lipopolysaccharide and interleukin-1beta in the rat.	2001 Feb	11292006
Current trends in the development of new antidepressants.	2001 Feb	11172668

Showing 1 to 5 of 31 entries

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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.