Laropiprant

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

What is the Laropiprant?

The molecule Laropiprant presents a molecular formula of C21H19ClFNO4S and its IUPAC name is 2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid.

Laropiprant is a molecule that is being studied for its potential use in the treatment of various conditions, including inflammation and cardiovascular disease. Laropiprant belongs to a class of molecules known as prostaglandin D2 (PGD2) antagonists. PGD2 is a naturally occurring molecule that has various effects in the body, including acting as a mediator of inflammation. Laropiprant is thought to work by blocking the effects of PGD2..

Laropiprant is currently being investigated in clinical trials for its potential use in the treatment of atopic dermatitis, a condition characterized by chronic inflammation of the skin. Laropiprant is also being studied for its potential use in the treatment of other inflammatory conditions, such as asthma and inflammatory bowel disease. In addition, laropiprant is being investigated as a possible treatment for cardiovascular disease..

Laropiprant is a promising molecule with the potential to treat a variety of conditions. However, further research is needed to determine the safety and efficacy of laropiprant in humans..

3D structure

Cartesian coordinates

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

2D drawing

 

Laropiprant NXFFJDQHYLNEJK-CYBMUJFWSA-N chemical compound 2D structure molecule svg
Laropiprant

 

Molecule descriptors

 
IUPAC name2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid
InChI codeInChI=1S/C21H19ClFNO4S/c1-29(27,28)18-10-15(23)9-17-16-7-4-13(8-19(25)26)20(16)24(21(17)18)11-12-2-5-14(22)6-3-12/h2-3,5-6,9-10,13H,4,7-8,11H2,1H3,(H,25,26)/t13-/m1/s1
InChI KeyNXFFJDQHYLNEJK-CYBMUJFWSA-N
SMILESCS(=O)(=O)c1cc(F)cc2c3c(n(Cc4ccc(Cl)cc4)c12)[C@@H](CC(=O)O)CC3

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.

  • ((3R)-4-(4-Chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl)acetic acid
  • (-)-((3R)-4-(4-Chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl)acetic acid
  • 2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methanesulfonyl-1H,2H,3H,4H-cyclopenta[b]indol-3-yl]acetic acid
  • 2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid
  • 571170-77-9
  • A25234
  • AC-35835
  • AM81247
  • AMOT0189
  • AS-17012
  • AT34794
  • BCP02136
  • BCP9000944
  • BCPP000161
  • BDBM50205275
  • CS-0539
  • Cardaptive
  • Cardaptive; MK 0524; MK-0524
  • Cordaptive
  • Cyclopent(b)indole-3-acetic acid, 4-((4-chlorophenyl)methyl)-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)-, (3R)-
  • Cyclopent[b]indole-3-acetic acid, 4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)-, (3R)-
  • D08940
  • DB11629
  • EX-A2099
  • G7N11T8O78
  • GTPL3356
  • HY-50175
  • Laropiprant
  • Laropiprant (INN/USAN)
  • Laropiprant (MK-0524)
  • Laropiprant,CAS:571170-77-9
  • Laropiprant; MK-0524
  • Laropiprant;(R)-2-(4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
  • MK 0524
  • MK-0524
  • MK0524
  • NCGC00345790-10
  • Q412291
  • Tedaptive
  • [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid
  • [14C]-Laropiprant

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3961849
  • UNII-G7N11T8O78
  • AKOS030526850
  • DTXSID60205756
  • CHEMBL426559
  • CHEBI:135942
  • SCHEMBL991107

Physico-Chemical properties

IUPAC name2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid
Molecular formulaC21H19ClFNO4S
Molecular weight435.896
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity109.76
LogP5.5
Topological polar surface area84.8

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.