Tianeptine

Tianeptine
Clinical data
Trade names	Stablon, Coaxil, Tatinol
Other names	Tia; ZaZa; S-1574; JNJ-39823277; TPI-1062
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
ATC code	N06AX14 (WHO) ;
Legal status
Legal status	BR: Class C1 (Other controlled substances); In general: Rx-only; US: Investigational New Drug ; AU: S4; Others: controlled in FR, IT, BH, SG;
Pharmacokinetic data
Bioavailability	99%
Protein binding	95%
Metabolism	Hepatic by β-oxidation
Elimination half-life	2.5–3 hours; 4–9 hours (elderly)
Excretion	Urine: 65%; Feces: 15%
Identifiers
	IUPAC name 7-[(3-Chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl)amino]heptanoic acid;
CAS Number	72797-41-2 ; 30123-17-2 (sodium); 1224690-84-9 (sulfate); 2231739-19-6 (hemioxalate);
PubChem CID	68870;
IUPHAR/BPS	7558;
ChemSpider	62102 ;
UNII	0T493YFU8O;
KEGG	D02575 ;
ChEBI	CHEBI:91749;
ChEMBL	ChEMBL1289110 ;
CompTox Dashboard (EPA)	DTXSID7048295 ;
ECHA InfoCard	100.131.750 100.069.844, 100.131.750
Chemical and physical data
Formula	C21H25ClN2O4S
Molar mass	436.95 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1cc2c(cc1)C(c3c(N(C)S2(=O)=O)cccc3)NCCCCCCC(=O)O;
	InChI InChI=1S/C21H24ClN2NaO4S/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) ; Key:JICJBGPOMZQUBB-UHFFFAOYSA-N ;
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Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.

Tianeptine has antidepressant and anxiolytic effects with a relative lack of sedative, anticholinergic, and cardiovascular side effects. It has been found to act as an atypical agonist of the μ-opioid receptor with clinically negligible effects on the δ- and κ-opioid receptors. This may explain part of its antidepressant and anxiolytic effects; however, it is thought that tianeptine also modulates glutamate receptors, and this may also explain tianeptine's antidepressant/anxiolytic effects.

Tianeptine was discovered and patented by the French Society of Medical Research in the 1960s. It was introduced for medical use in France in 1983. Currently, tianeptine is approved in France and manufactured and marketed by Laboratories Servier SA; it is also marketed in a number of other European countries under the trade name Coaxil as well as in Asia (including Singapore) and Latin America as Stablon and Tatinol but it is not available in Australia, Canada, New Zealand, Italy or the United Kingdom. In the US, it is an unregulated drug sold under several names and some of these products have been found to be adulterated with other recreational drugs. It is commonly known by the nickname "gas station heroin".