sodium 7-({10-methyl-9,9-dioxo-9λ6-thia-10-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}amino)heptanoate

• ChemBase ID: 120172
• Molecular Formular: C21H25N2NaO4S
• Molecular Mass: 424.48897
• Monoisotopic Mass: 424.14327257
• SMILES: S1(=O)(=O)N(c2c(C(c3c1cccc3)NCCCCCCC(=O)[O-])cccc2)C.[Na+]
• Canonical SMILES: [O-]C(=O)CCCCCCNC1c2ccccc2N(S(=O)(=O)c2c1cccc2)C.[Na+]
• InChI: InChI=1S/C21H26N2O4S.Na/c1-23-18-12-7-5-10-16(18)21(22-15-9-3-2-4-14-20(24)25)17-11-6-8-13-19(17)28(23,26)27;/h5-8,10-13,21-22H,2-4,9,14-15H2,1H3,(H,24,25);/q;+1/p-1
• InChIKey: AXJHQFRTPADQIP-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 7-({10-methyl-9,9-dioxo-9λ^6-thia-10-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}amino)heptanoate
• IUPAC Traditional name: sodium 7-({10-methyl-9,9-dioxo-9λ^6-thia-10-azatricyclo[9.4.0.0^3,^8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}amino)heptanoate
• Synonyms: sodium 7-((6-methyl-5,5-dioxido-6,11-dihydrodibenzo[c,f][1,2]thiazepin-11-yl)amino)heptanoate; Coaxil; Stablon; Tatinol; Tianeptine sodium

Database IDs

• CAS Number: 30123-17-2
• PubChem SID: 162214525
• PubChem CID: 51052081

CALCULATED PROPERTIES

• Acid pKa: 4.2222996
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.9134344
• LogD (pH = 7.4): 0.87591434
• Log P: 0.9243535
• Molar Refractivity: 119.4388 cm^3
• Polarizability: 42.95313 Å^3
• Polar Surface Area: 89.54 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Selective serotonin 5-HT reuptake enhancer

Product Information

• Salt Data: Na+
• Application(s): Analgesic; Anticonvulsant; Antidepressant; Anxiolytic; Effective for asthma treatment; Neuroprotective

REFERENCES

• 1. Mennini T, Mocaer E, Garattini S. Tianeptine, a selective enhancer of serotonin uptake in rat brain. Naunyn Schmiedebergs Arch Pharmacol. 1987 Nov;336(5):478-82.
• 2. Kato G, Weitsch AF. Neurochemical profile of tianeptine, a new antidepressant drug. Clin Neuropharmacol. 1988;11 Suppl 2:S43-50.
• 3. Uzbay IT, Cinar MG, Aytemir M, Tuglular I. Analgesic effect of tianeptine in mice. Life Sci. 1999;64(15):1313-9.
• 4. Plaisant F, Dommergues MA, Spedding M, Cecchelli R, Brillault J, Kato G, Munoz C, Gressens P. Neuroprotective properties of tianeptine: interactions with cytokines.
• Neuropharmacology. 2003 May;44(6):801-9.
• 5. Lechin F, van der Dijs B, Orozco B, Jara H, Rada I, Lechin ME, Lechin AE.
• The serotonin uptake-enhancing drug tianeptine suppresses asthmatic symptoms in children: a double-blind, crossover, placebo-controlled study. J Clin Pharmacol. 1998 Oct;38(10):918-25.