Lifitegrast
(2S)-2-[[2-(1-benzofuran-6-carbonyl)-5,7-dichloro-3,4-dihydro-1H-isoquinoline-6-carbonyl]amino]-3-(3-methylsulfonylphenyl)propanoic acid
Molecular Identity
Lifitegrast
(2S)-2-[[2-(1-benzofuran-6-carbonyl)-5,7-dichloro-3,4-dihydro-1H-isoquinoline-6-carbonyl]amino]-3-(3-methylsulfonylphenyl)propanoic acid
PubChem CID: 11965427
Lifitegrast is an N-acyl-L-alpha-amino acid obtained by formal condensation of the carboxy group of N-[2-(1-benzofuran-6-carbonyl)]-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid with the amino group of 3-(methanesulfonyl)-L-phenylalanine. Used for treatment of keratoconjunctivitis sicca (dry eye syndrome). It has a role as a lymphocyte function-associated antigen-1 antagonist and an anti-inflammatory drug. It is a member of isoquinolines, a sulfone, a member of 1-benzofurans, a N-acyl-L-alpha-amino acid and a L-phenylalanine derivative.
2D Structure
Properties
C29H24Cl2N2O7S
Molecular Formula
615.50
Molecular Weight
g/mol
614.0681
Exact Mass
Da
4.7
XLogP
Drug-like (Lipinski: < 5)
142
TPSA
May have limited oral absorption
2
H-Bond Donors
7
H-Bond Acceptors
1100
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Lifitegrast1025967-78-5XiidraSAR-1118SAR 1118SHP606SHP-606L-Phenylalanine, N-[[2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl]carbonyl]-3-(methylsulfonyl)-038E5L962WCHEBI:133023DTXSID60145345L-Phenylalanine, N-((2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl)-3-(methylsulfonyl)-(2S)-2-(((2-(benzofuran-6-ylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-yl)carbonyl)amino)-3-(3-(methylsulfonyl)phenyl)propanoic acidlifitegrastum(2S)-2-((2-(1-benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-yl)formamido)-3-(3-methanesulfonylphenyl)propanoic acid
Data from PubChem (NCBI)
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