(R)-tianeptine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for (R)-tianeptine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the (R)-tianeptine?

The molecule (R)-tianeptine presents a molecular formula of C21H25ClN2O4S and its IUPAC name is 7-[[(11R)-3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl]amino]heptanoic acid.

Tianeptine is a drug used for treating depression, anxiety, and asthma. It is a tricyclic antidepressant (TCA) and is structurally similar to amitriptyline and imipramine. Tianeptine is unique among TCAs in that it has antidepressant, anxiolytic, and anti-inflammatory properties. It is thought to work by increasing levels of serotonin and norepinephrine in the brain..

Tianeptine has been shown to be effective in treating major depressive disorder, generalized anxiety disorder, and panic disorder. It has also been shown to be effective in treating asthmatic symptoms and improving quality of life in asthmatic patients. Tianeptine is generally well-tolerated, with the most common side effects being dry mouth, dizziness, and nausea..

If you are considering taking tianeptine for your depression, anxiety, or asthma, it is important to speak with your doctor first to discuss the potential risks and benefits..

3D structure

Cartesian coordinates

Geometry of (R)-tianeptine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

(R)-tianeptine JICJBGPOMZQUBB-OAQYLSRUSA-N chemical compound 2D structure molecule svg
(R)-tianeptine

 

Molecule descriptors

 
IUPAC name7-[[(11R)-3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl]amino]heptanoic acid
InChI codeInChI=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)/t21-/m1/s1
InChI KeyJICJBGPOMZQUBB-OAQYLSRUSA-N
SMILESCN1c2ccccc2[C@@H](NCCCCCCC(=O)O)c2ccc(Cl)cc2S1(=O)=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (R)-tianeptine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1846165
  • CHEBI:190007

Physico-Chemical properties

IUPAC name7-[[(11R)-3-chloro-6-methyl-5,5-dioxo-11H-benzo[c][2,1]benzothiazepin-11-yl]amino]heptanoic acid
Molecular formulaC21H25ClN2O4S
Molecular weight436.952
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity117.64
LogP5.7
Topological polar surface area95.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.