Lifitegrast sodiumProduct ingredient for Lifitegrast

Name
Lifitegrast sodium
Drug Entry
Lifitegrast

Lifitegrast is a FDA approved drug for the treatment of keratoconjunctivitis sicca (dry eye syndrome). It is a tetrahydroisoquinoline derivative and lymphocyte function-associated antigen-1 ( LFA-1) antagonist that was discovered through the rational design process. The ophthalmic solution was approved in July, 2016 under the trade name Xiidra. It has shown to protect the corneal surface and alleviate the symptoms of dry eye syndrome with fast onset of action and well tolerated profile in both local and systemic setting 2.

Accession Number
DBSALT001921
Structure
Synonyms
Not Available
External IDs
SAR 1118-023 / SAR-1118-023
UNII
QG18FLP1KP
CAS Number
1119276-80-0
Weight
Average: 637.46
Monoisotopic: 636.0500719
Chemical Formula
C29H23Cl2N2NaO7S
InChI Key
BPWOKOSRORLLIN-BQAIUKQQSA-M
InChI
InChI=1S/C29H24Cl2N2O7S.Na/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);/q;+1/p-1/t23-;/m0./s1
IUPAC Name
sodium (2S)-2-{[2-(1-benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-yl]formamido}-3-(3-methanesulfonylphenyl)propanoate
SMILES
[Na+].CS(=O)(=O)C1=CC(C[C@H](NC(=O)C2=C(Cl)C3=C(CN(CC3)C(=O)C3=CC=C4C=COC4=C3)C=C2Cl)C([O-])=O)=CC=C1
ChemSpider
28510148
ChEMBL
CHEMBL2048409
Predicted Properties
PropertyValueSource
Water Solubility0.00463 mg/mLALOGPS
logP4.55ALOGPS
logP4.02Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.27Chemaxon
pKa (Strongest Basic)-1.3Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area136.82 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity165.32 m3·mol-1Chemaxon
Polarizability59.04 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon