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]

• ATC Code:
  S01XA25: lifitegrast
  S01XA: Other ophthalmologicals
  S01X: OTHER OPHTHALMOLOGICALS
  S01: OPHTHALMOLOGICALS
  S: SENSORY ORGANS
• Drug Type: Small molecular drug
• #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: CHEMBL133023
  CAS Number: 1025967-78-5
  UNII: 038E5L962W
  DrugBank ID: DB11611
  TTD ID: D0Q9EV
  VARIDT ID: DR00072
  ACDINA ID: D01208
• Drug-Molecule Activity Atlas (DMA)NEW: Click to Jump to the Detailed DMA Information of This Drug
• Drug ADMET Endpoint Profile (DAE)NEW: Click to Jump to the Detailed DAE Information of This Drug
• 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 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

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

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)