Ecadotril

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

What is the Ecadotril?

The molecule Ecadotril presents a molecular formula of C21H23NO4S and its IUPAC name is benzyl 2-[[(2S)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate.

Ecadotril is a molecule that has been shown to be effective in the treatment of anxiety and depression. It is a derivative of the amino acid L-tryptophan, and works by inhibiting the reuptake of serotonin in the brain. This action results in increased levels of serotonin, which has been shown to be effective in the treatment of both anxiety and depression. Ecadotril has been shown to be as effective as the popular antidepressant fluoxetine (Prozac) in the treatment of anxiety and depression, with fewer side effects..

3D structure

Cartesian coordinates

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

2D drawing

 

Ecadotril ODUOJXZPIYUATO-LJQANCHMSA-N chemical compound 2D structure molecule svg
Ecadotril

 

Molecule descriptors

 
IUPAC namebenzyl 2-[[(2S)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate
InChI codeInChI=1S/C21H23NO4S/c1-16(23)27-15-19(12-17-8-4-2-5-9-17)21(25)22-13-20(24)26-14-18-10-6-3-7-11-18/h2-11,19H,12-15H2,1H3,(H,22,25)/t19-/m1/s1
InChI KeyODUOJXZPIYUATO-LJQANCHMSA-N
SMILESCC(=O)SC[C@@H](Cc1ccccc1)C(=O)NCC(=O)OCc1ccccc1

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.

  • (S)-Acetophan
  • (S)-Benzyl 2-(3-(acetylthio)-2-benzylpropanamido)acetate
  • (S)-N-(2-((Acetylthio)methyl)-1-oxo-3-phenylpropyl)glycine phenylmethyl ester
  • 112573-73-6
  • 6XSR933SRK
  • BAY y 7432
  • BAY-Y-7432
  • BAY-y 7432
  • BENZYL N-[(2S)-3-(ACETYLSULFANYL)-2-BENZYLPROPANOYL]GLYCINATE
  • BP 1.02
  • BP-1.02
  • D03929
  • DSSTox_CID_25513
  • DSSTox_GSID_45513
  • DSSTox_RID_80923
  • ECADOTRIL
  • Ecadotril
  • Ecadotril (USAN/INN)
  • Glycine, N-(2-((acetylthio)methyl)-1-oxo-3-phenylpropyl)-, phenylmethyl ester, (S)-
  • N-((S)-.ALPHA.-(MERCAPTOMETHYL)HYDROCINNAMOYL)GLYCINE, BENZYL ESTER, ACETATE (ESTER)
  • N-((S)-alpha-(Mercaptomethyl)hydrocinnamoyl)glycine, benzyl ester, acetate (ester)
  • N-(2-Acetylthiomethyl-1-oxo-3-phenylpropyl)glycine (S)(-)benzyl ester
  • NCGC00016945-01
  • NCGC00179511-03
  • PHENYLMETHYL2-[[(2S)-2-(ACETYLSULFANYLMETHYL)-3-PHENYLPROPANOYL]AMINO]ACETATE
  • Q5332138
  • Racecadotril (s)-form
  • S 049
  • S-049
  • S.049
  • S049
  • Sinorphan
  • benzyl 2-[[(2S)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1546844
  • CAS-81110-73-8
  • UNII-6XSR933SRK
  • AKOS015898894
  • DTXSID40861036
  • CHEMBL1516410
  • Tox21_110700
  • Tox21_110700_1
  • SCHEMBL48974

Physico-Chemical properties

IUPAC namebenzyl 2-[[(2S)-2-(acetylsulfanylmethyl)-3-phenylpropanoyl]amino]acetate
Molecular formulaC21H23NO4S
Molecular weight385.477
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity106.43
LogP3.4
Topological polar surface area97.8

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.