(S)-Rebamipide

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

What is the (S)-Rebamipide?

The molecule (S)-Rebamipide presents a molecular formula of C20H36N2O3S and its IUPAC name is (2S)-2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid.

(S)-Rebamipide is a molecule that has been shown to be effective in the treatment of gastric ulcers. It is a prodrug of the active metabolite, rebamipide, which is a member of the class of drugs known as proton pump inhibitors (PPIs). PPIs are drugs that work by inhibiting the production of stomach acid..

Rebamipide is thought to work by protecting the mucosal lining of the stomach from the damaging effects of stomach acid and by promoting the healing of gastric ulcers. It has also been shown to have anti-inflammatory and antioxidant effects..

The safety and efficacy of rebamipide have been demonstrated in animal studies and in a small number of human studies. The most common side effects of rebamipide are mild and include nausea, vomiting, diarrhea, and abdominal pain..

Rebamipide is not currently approved for use in the United States, but it exists in other countries..

3D structure

Cartesian coordinates

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

2D drawing

 

(S)-Rebamipide ALOBUEHUHMBRLE-FQEVSTJZSA-N chemical compound 2D structure molecule svg
(S)-Rebamipide

 

Molecule descriptors

 
IUPAC name(2S)-2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
InChI codeInChI=1S/C20H36N2O3S/c1-4-6-7-8-9-16-22(5-2)17-10-11-20(23)18-12-14-19(15-13-18)21-26(3,24)25/h12-15,20-21,23H,4-11,16-17H2,1-3H3/t20-/m0/s1
InChI KeyALOBUEHUHMBRLE-FQEVSTJZSA-N
SMILESCCCCCCCN(CC)CCC[C@H](O)c1ccc(NS(C)(=O)=O)cc1

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.

  • (2S)-2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
  • (S)-(?)-Rebamipide
  • (S)-2-(4-chlorobenzamido)-3-(2-oxo-1,2-dihydroquinolin-4-yl)
  • (S)-Rebamipide
  • (S)-rebamipide
  • 111911-88-7
  • 4-QUINOLINEPROPANOIC ACID, .ALPHA.-((4-CHLOROBENZOYL)AMINO)-1,2-DIHYDRO-2-OXO-, (S)-
  • 4-Quinolinepropanoic acid, alpha-((4-chlorobenzoyl)amino)-1,2-dihydro-2-oxo-, (S)-
  • N-(4-chlorobenzoyl)-3-(2-oxo-1,2-dihydro-quinolin-4-yl)-alanine
  • Q27293661
  • Rebamipide, (S)-
  • X827T20LF9

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC9330879
  • UNII-X827T20LF9
  • SCHEMBL21623658

Physico-Chemical properties

IUPAC name(2S)-2-[(4-chlorobenzoyl)amino]-3-(2-oxo-1H-quinolin-4-yl)propanoic acid
Molecular formulaC20H36N2O3S
Molecular weight384.576
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity111.42
LogP5.3
Topological polar surface area78.0

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.