Details of the Drug

General Information of Drug (ID: DM4WVC5)

Drug Name
lifitegrast
Synonyms
Lifitegrast; Xiidra; 1025967-78-5; SAR-1118; SAR 1118; UNII-038E5L962W; CHEMBL2048028; 038E5L962W; (S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid; (S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid;(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid; SAR-1118; SAR-1119; SHP606; SPD606
Indication
Disease Entry ICD 11 Status REF
Dry eye disease 9E1Z Approved [1]
Allergic conjunctivitis 9A60.02 Phase 3 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 615.5
Logarithm of the Partition Coefficient (xlogp) 4.7
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 1.70 mcg/L [3]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 15 min [3]
Chemical Identifiers
Formula
C29H24Cl2N2O7S
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
Canonical SMILES
CS(=O)(=O)C1=CC=CC(=C1)C[C@@H](C(=O)O)NC(=O)C2=C(C=C3CN(CCC3=C2Cl)C(=O)C4=CC5=C(C=C4)C=CO5)Cl
InChI
InChI=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
InChIKey
JFOZKMSJYSPYLN-QHCPKHFHSA-N
Cross-matching ID
PubChem CID
11965427
ChEBI ID
CHEBI:133023
CAS Number
1025967-78-5
DrugBank ID
DB11611
TTD ID
D0Q9EV
VARIDT ID
DR00072
ACDINA ID
D01208
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Integrin alpha-L (ITGAL) TT48WR6 ITAL_HUMAN Modulator [4]
Intercellular adhesion molecule ICAM-1 (ICAM1) TTCT6F7 ICAM1_HUMAN Inhibitor [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTPFTEQ SO2B1_HUMAN Substrate [6]
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTE2B1D SO1A2_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Dry eye disease
ICD Disease Classification 9E1Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Intercellular adhesion molecule ICAM-1 (ICAM1) DTT ICAM1 5.21E-01 0.38 0.32
Organic anion transporting polypeptide 2B1 (SLCO2B1) DTP OATP2B1 2.89E-11 -1.11E+00 -2.81E+00
Organic anion transporting polypeptide 1A2 (SLCO1A2) DTP OATP1A2 5.20E-01 -2.26E-01 -4.65E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Hydrochloric acid E00015 313 Acidulant
Disodium hydrogenorthophosphate E00283 24203 Buffering agent; Complexing agent
Sodium chloride E00077 5234 Diluent; Tonicity agent
Sodium hydroxide E00234 14798 Alkalizing agent
Sodium thiosulfate E00300 24477 Antioxidant
Water E00035 962 Solvent
⏷ Show the Full List of 6 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Lifitegrast 50 mg/ml solution 50 mg/ml Solution Ophthalmic
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 2016 FDA drug approvals. Nat Rev Drug Discov. 2017 Feb 2;16(2):73-76.
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7533).
3 FDA Clinical Pharmacology and Biopharmaceutics Review
4 Corneal inflammation is inhibited by the LFA-1 antagonist, lifitegrast (SAR 1118). J Ocul Pharmacol Ther. 2013 May;29(4):395-402.
5 Discovery and Development of Potent LFA-1/ICAM-1 Antagonist SAR 1118 as an Ophthalmic Solution for Treating Dry Eye. ACS Med Chem Lett. 2012 Jan 31;3(3):203-6.
6 Clinical Pharmacology and Biopharmaceutics review(s)