Tianeptine sodiumProduct ingredient for Tianeptine

Name
Tianeptine sodium
Drug Entry
Tianeptine

Tianeptine is a drug used primarily in the treatment of major depressive disorder and has been studied in the treatment of irritable bowel syndrome (IBS) 3. Structurally, it is classified as a tricyclic antidepressant (TCA), however, it possesses different pharmacological properties than typical tricyclic antidepressants 1.

Tianeptine was discovered and patented by The French Society of Medical Research in the 1960s 29. Currently, tianeptine is approved in France and manufactured and marketed by Laboratories Servier SA; it is also marketed in several 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, the U.K. or the U.S.

Accession Number
DBSALT001784
Structure
Thumb
Synonyms
Tianeptine sodium salt
UNII
YG0E19592I
CAS Number
30123-17-2
Weight
Average: 458.93
Monoisotopic: 458.1043004
Chemical Formula
C21H24ClN2NaO4S
InChI Key
ZLBSUOGMZDXYKE-UHFFFAOYSA-M
InChI
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
IUPAC Name
sodium 7-({6-chloro-10-methyl-9,9-dioxo-9λ⁶-thia-10-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-yl}amino)heptanoate
SMILES
[Na+].CN1C2=CC=CC=C2C(NCCCCCCC([O-])=O)C2=C(C=C(Cl)C=C2)S1(=O)=O
External Links
ChemSpider
4955382
BindingDB
50103632
ChEMBL
CHEMBL2361572
Wikipedia
Tianeptine
Predicted Properties
PropertyValueSource
Water Solubility0.00245 mg/mLALOGPS
logP3.73ALOGPS
logP1.54ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.22ChemAxon
pKa (Strongest Basic)7.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.54 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity124.24 m3·mol-1ChemAxon
Polarizability45.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon