An inhibitor of the LFA-1/ICAM-1 interaction
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Alternative(s)
22588Lifitegrast
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Lifitegrast (sodium salt)

Item No. 40427

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[[2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl]carbonyl]-3-(methylsulfonyl)-L-phenylalanine, monosodium salt
CAS Number
1119276-80-0
Synonyms
  • SAR 1118-023
Molecular Formula
C29H23Cl2N2O7S • Na
Formula Weight
637.5
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly solubleDMSO: SolubleWater: Slightly soluble
SMILES
CS(C1=CC=CC(C[C@@H](C([O-])=O)NC(C2=C(Cl)C=C(CN(C(C3=CC(OC=C4)=C4C=C3)=O)CC5)C5=C2Cl)=O)=C1)(=O)=O.[Na+]
InChi Code
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
InChi Key
BPWOKOSRORLLIN-BQAIUKQQSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

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    Cayman Chemical
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    Product Description

    Lifitegrast is an inhibitor of the protein-protein interaction between lymphocyte function-associated antigen-1 (LFA-1) and intercellular adhesion molecule-1 (ICAM-1).1 It binds to LFA-1 and blocks the adhesion of Jurkat T cells or HuT 78 cells to ICAM-1 (IC50s = 2.98 and 9 nM, respectively) and inhibits the secretion of various cytokines, including IFN-γ, TNF-α, IL-1β, and IL-6, from these cells.2,1 Lifitegrast increases tear production in dogs with idiopathic keratoconjunctivitis sicca.2 Topical application of lifitegrast inhibits LFA-1-dependent neutrophil recruitment to the eye in mouse models of contact lens-associated corneal inflammation induced by corneal abrasion and tobramycin-killed bacteria.3 Formulations containing lifitegrast have been used in the treatment of dry eye disease.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhong, M., Gadek, T.R., Bui, M., et al. Discovery and development of potent LFA-1/ICAM-1 antagonist SAR 1118 as an ophthalmic solution for treating dry eye. ACS Med. Chem. Lett. 3(3), 203-206 (2012).

    2. Murphy, C.J., Bentley, E., Miller, P.E., et al. The pharmacologic assessment of a novel lymphocyte function-associated antigen-1 antagonist (SAR 1118) for the treatment of keratoconjunctivitis sicca in dogs. Invest. Opthalmol. Vis. Sci. 52(6), 3174-3180 (2011).

    3. Sun, Y., Zhang, R., Gadek, T.R., et al. Corneal inflammation is inhibited by the LFA-1 antagonist, lifitegrast (SAR 1118). J. Ocul. Pharmacol. Ther. 29(4), 395-402 (2013).