7-({6-chloro-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)heptanoic acid

• ChemBase ID: 178621
• Molecular Formular: C21H25ClN2O4S
• Molecular Mass: 436.9522
• Monoisotopic Mass: 436.12235597
• SMILES: C1(c2c(N(S(=O)(=O)c3c1ccc(c3)Cl)C)cccc2)NCCCCCCC(=O)O
• Canonical SMILES: OC(=O)CCCCCCNC1c2ccccc2N(S(=O)(=O)c2c1ccc(c2)Cl)C
• 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)
• InChIKey: JICJBGPOMZQUBB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-({6-chloro-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)heptanoic acid
• IUPAC Traditional name: tianeptine
• Synonyms: 7-[(3-Chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic Acid S,S-Dioxide; (+/-)-7-[(3-Chloro-6,11-dihydro-6-methyldibenzo[c,f][1,2]thiazepin-11-yl)amino]heptanoic Acid S,S-Dioxide; Coaxil; Tianeptine

Database IDs

• CAS Number: 72797-41-2
• PubChem SID: 164234531
• PubChem CID: 68870

CALCULATED PROPERTIES

• Acid pKa: 4.215957
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.5208575
• LogD (pH = 7.4): 1.4687537
• Log P: 1.5311525
• Molar Refractivity: 113.4065 cm^3
• Polarizability: 44.95849 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 129-131°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T436800

Tricyclic compound with psychostimulant, anti-ulcer and anti-emetic properties. Antidepressant.

REFERENCES

• Malen, C., et al.: Experientia, 28, 811 (1972)
• Safa, A., et al.: J. Biol. Chem., 262, 7884 (1972)
• Ford, J.M., et al.: Pharmacol. Rev., 42, 155, (1972)
• Pierre, A., et a.: Cancer Res., 51, 2312 (1972)