Tianeptine

Tianeptine

Clinical data
Trade names	Coaxil, Stablon
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N06AX14 (WHO)
Legal status
Legal status	Rx-only (many countries); Legal (Unscheduled) (US); Controlled (FR, BH, SG)
Pharmacokinetic data
Bioavailability	99%
Protein binding	95%
Metabolism	Hepatic
Biological half-life	2.5-3 hours, 4-9 hours (elderly)
Excretion	Renal (65%),Faecal (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	66981-73-5 Y
PubChem CID	68870
IUPHAR/BPS	7558
ChemSpider	62102 Y
UNII	0T493YFU8O
KEGG	D02575 Y
ChEMBL	CHEMBL1289110 N
ECHA InfoCard	100.131.750
Chemical and physical data
Formula	C21H25ClN2O4S
Molar mass	436.953 g/mol
3D model (Jmol)	Interactive image
SMILES Clc1cc2c(cc1)C(c3c(N(C)S2(=O)=O)cccc3)NCCCCCCC(=O)O
InChI 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) Y Key:JICJBGPOMZQUBB-UHFFFAOYSA-N Y
NY (what is this?)

Tianeptine (brand names Stablon, Coaxil, Tatinol, Tianeurax and Salymbra) is a drug used primarily in the treatment of major depressive disorder, although it may also be used to treat asthma or irritable bowel syndrome. Chemically it is a tricyclic antidepressant (TCA), but it has different pharmacological properties than typical TCAs as recent research suggests that tianeptine produces its antidepressant effects through indirect alteration of glutamate receptor activity (i.e., AMPA receptors and NMDA receptors) and release of BDNF, in turn affecting neural plasticity.

Tianeptine has antidepressant and anxiolytic (anti-anxiety) properties with a relative lack of sedative, anticholinergic and cardiovascular adverse effects, thus suggesting it is particularly suitable for use in the elderly and in those following alcohol withdrawal; such persons can be more sensitive to the adverse effects of psychotropic drugs. Recent results indicate possible anticonvulsant (anti-seizure) and analgesic (painkilling) activity of tianeptine via immediate or downstream modulation of adenosine A₁ receptors (as the effects could be experimentally blocked by antagonists of this receptor).