lifitegrast

Also known as compound 1g [PMID: 24900456], SAR 1118, SAR-1118, SAR-1118-023, Xiidra®, SAR1118

Lifitegrast, sold under the brand name Xiidra (), is a medication for the treatment of signs and symptoms of dry eye, a syndrome called keratoconjunctivitis sicca. Lifitegrast reduces inflammation by inhibiting inflammatory cell binding. It is often used as an alternative to ciclosporin (Ikervis, Restasis, Vevye, Verkazia or Cequa) for dry eye treatment including meibomian gland dysfunction and inflammatory dry eye.

Key facts

Drug.ChEBI: 133023
Drug.ChEMBL: 2048028
Drug.image: Lifitegrast skeletal.svg
Drug.image_class: skin-invert-image
Drug.tradename: Xiidra
Drug.MedlinePlus: a616039
Drug.pregnancy_AU: B1
Drug.routes_of_administration: Eye drops
Drug.ATC_prefix: S01
Drug.ATC_suffix: XA25
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_US: Rx-only
Drug.CAS_number: 1025967-78-5
Drug.PubChem: 11965427
Drug.DrugBank: DB11611
Drug.ChemSpiderID: 10139520
Drug.UNII: 038E5L962W

via Wikipedia infobox

Chemical data

Formula: C29H24Cl2N2O7S
Molecular weight: 615.5 g/mol
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
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
InChIKey: JFOZKMSJYSPYLN-QHCPKHFHSA-N
XLogP: 4.7
Polar surface area: 142 Å²
H-bond donors: 2
H-bond acceptors: 7
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2016
Admin. routes: topical
Indications: dry eye syndrome, allergic conjunctivitis, eye disease, graft versus host disease

via ChEMBL · EBI

Research

165 papers

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 614.068127
Has use: medication

Show 5 more facts

chemical formula: C₂₉H₂₄Cl₂N₂O₇S
canonical SMILES: CS(=O)(=O)C1=CC=CC(=C1)CC(C(=O)O)NC(=O)C2=C(C=C3CN(CCC3=C2Cl)C(=O)C4=CC5=C(C=C4)C=CO5)Cl
isomeric SMILES: CS(=O)(=O)C1=CC(C[C@H](NC(=O)C2=C(Cl)C3=C(CN(CC3)C(=O)C4=CC5=C(C=CO5)C=C4)C=C2Cl)C(O)=O)=CC=C1
subject has role: eye drop
Commons category: Lifitegrast

Sources (2)

via Wikidata · CC0

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