Lifitegrast

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

What is the Lifitegrast?

The molecule Lifitegrast presents a molecular formula of C29H24Cl2N2O7S and its IUPAC name is (2S)-2-[[2-(1-benzofuran-6-carbonyl)-5,7-dichloro-3,4-dihydro-1H-isoquinoline-6-carbonyl]amino]-3-(3-methylsulfonylphenyl)propanoic acid.

Lifitegrast (trade name Xiidra) is a medication used to treat the dry eye disease. It is a Rho-associated protein kinase 2 (ROCK2) inhibitor..

Dry eye disease is a common and often chronic condition that occurs when the eyes do not make enough tears, or when the tears evaporate too quickly. This can lead to symptoms such as burning, stinging, itching, and redness..

Lifitegrast works by inhibiting ROCK2, which participes in the inflammation process. In clinical trials, lifitegrast has been shown to reduce the signs and symptoms of dry eye disease..

Lifitegrast exists as a 5% solution for use in the eye. It is typically used twice daily, in the morning and evening..

Common side effects of lifitegrast include eye irritation, burning, stinging, and redness..

Lifitegrast is a safe and effective medication for the treatment of dry eye disease. It is well tolerated, with the most common side effects being mild and temporary..

3D structure

Cartesian coordinates

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

2D drawing

 

Lifitegrast JFOZKMSJYSPYLN-QHCPKHFHSA-N chemical compound 2D structure molecule svg
Lifitegrast

 

Molecule descriptors

 
IUPAC name(2S)-2-[[2-(1-benzofuran-6-carbonyl)-5,7-dichloro-3,4-dihydro-1H-isoquinoline-6-carbonyl]amino]-3-(3-methylsulfonylphenyl)propanoic acid
InChI codeInChI=1S/C29H24Cl2N2O7S/c1-41(38,39)20-4-2-3-16(11-20)12-23(29(36)37)32-27(34)25-22(30)13-19-15-33(9-7-21(19)26(25)31)28(35)18-6-5-17-8-10-40-24(17)14-18/h2-6,8,10-11,13-14,23H,7,9,12,15H2,1H3,(H,32,34)(H,36,37)/t23-/m0/s1
InChI KeyJFOZKMSJYSPYLN-QHCPKHFHSA-N
SMILESCS(=O)(=O)c1cccc(C[C@H](NC(=O)c2c(Cl)cc3c(c2Cl)CCN(C(=O)c2ccc4ccoc4c2)C3)C(=O)O)c1

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-(((2-(Benzofuran-6-ylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6- yl)carbonyl)amino)-3-(3-(methylsulfonyl)phenyl)propanoic acid
  • (2S)-2-[[2-(1-benzofuran-6-carbonyl)-5,7-dichloro3,4-dihydro-1H-isoquinoline-6-carbonyl]amino]-3-(3-methylsulfonylphenyl)propanoic acid
  • (S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid
  • 038E5L962W
  • 1025967-78-5
  • A900838
  • AC-32534
  • AMY4450
  • BDBM50386331
  • CCG-270245
  • CS-6264
  • D10374
  • DB11611
  • DS-20052
  • EX-A2582
  • GTPL7533
  • HY-19344
  • L-Phenylalanine, N-((2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl)-3-(methylsulfonyl)-
  • L-Phenylalanine, N-[[2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl]carbonyl]-3-(methylsulfonyl)-
  • Lifitegrast
  • Lifitegrast (USAN/INN)
  • Lifitegrast ophthalmic solution
  • Lifitegrast; SAR 1118
  • MFCD28502439
  • N-[2-(1-benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carbonyl]-3-(methanesulfonyl)-L-phenylalanine
  • N-[[2-(6-Benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl]carbonyl]-3-(methylsulfonyl)-L-phenylalanine
  • Q23044263
  • SAR 1118
  • SAR-1118
  • SAR1118
  • SHP-606
  • SHP606
  • Xiidra
  • s3714

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC84668739
  • UNII-038E5L962W
  • DTXSID60145345
  • CHEMBL2048028
  • CHEBI:133023
  • SCHEMBL2632068

Physico-Chemical properties

IUPAC name(2S)-2-[[2-(1-benzofuran-6-carbonyl)-5,7-dichloro-3,4-dihydro-1H-isoquinoline-6-carbonyl]amino]-3-(3-methylsulfonylphenyl)propanoic acid
Molecular formulaC29H24Cl2N2O7S
Molecular weight615.481
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity157.35
LogP6.2
Topological polar surface area142.4

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.