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    Chemistry

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    Also known as: 1025967-78-5, Xiidra, Sar 1118, Sar-1118, Shp606, Shp-606
    Molecular Formula
    C29H24Cl2N2O7S
    Molecular Weight
    615.5  g/mol
    InChI Key
    JFOZKMSJYSPYLN-QHCPKHFHSA-N
    FDA UNII
    038E5L962W
    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.
    Lifitegrast is a Lymphocyte Function-Associated Antigen-1 Antagonist. The mechanism of action of lifitegrast is as a Lymphocyte Function-Associated Antigen-1 Antagonist.
    1 2D Structure

    Lifitegrast

    2 Identification
    2.1 Computed Descriptors
    2.1.1 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
    2.1.2 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
    2.1.3 InChI Key
    JFOZKMSJYSPYLN-QHCPKHFHSA-N
    2.1.4 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
    2.1.5 Isomeric 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
    2.2 Other Identifiers
    2.2.1 UNII
    038E5L962W
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2s)-2-(((2-(benzofuran-6-ylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6- Yl)carbonyl)amino)-3-(3-(methylsulfonyl)phenyl)propanoic Acid

    2. L-phenylalanine, N-((2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl)-3-(methylsulfonyl)-

    3. Lifitegrast Ophthalmic Solution

    4. Sar 1118

    5. Sar-1118

    6. Shp-606

    7. Shp606

    8. Xiidra

    2.3.2 Depositor-Supplied Synonyms

    1. 1025967-78-5

    2. Xiidra

    3. Sar 1118

    4. Sar-1118

    5. Shp606

    6. Shp-606

    7. (s)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic Acid

    8. Chembl2048028

    9. 038e5l962w

    10. (2s)-2-(((2-(benzofuran-6-ylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6- Yl)carbonyl)amino)-3-(3-(methylsulfonyl)phenyl)propanoic Acid

    11. L-phenylalanine, N-((2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl)-3-(methylsulfonyl)-

    12. L-phenylalanine, N-[[2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl]carbonyl]-3-(methylsulfonyl)-

    13. Lifitegrast [usan:inn]

    14. Unii-038e5l962w

    15. Sar1118

    16. Xiidra (tn)

    17. Lifitegrast [mi]

    18. Lifitegrast [inn]

    19. Lifitegrast (usan/inn)

    20. Lifitegrast [usan]

    21. Lifitegrast; Sar 1118

    22. Lifitegrast [who-dd]

    23. Lifitegrast Ophthalmic Solution

    24. Gtpl7533

    25. Schembl2632068

    26. Amy4450

    27. Dtxsid60145345

    28. Lifitegrast [orange Book]

    29. Chebi:133023

    30. Ex-a2582

    31. Bdbm50386331

    32. Mfcd28502439

    33. S3714

    34. Zinc84668739

    35. Ccg-270245

    36. Cs-6264

    37. Db11611

    38. Compound 1g [pmid: 24900456]

    39. Ac-32534

    40. Ds-20052

    41. Hy-19344

    42. D10374

    43. A900838

    44. Q23044263

    45. (2s)-2-[[2-(1-benzofuran-6-carbonyl)-5,7-dichloro3,4-dihydro-1h-isoquinoline-6-carbonyl]amino]-3-(3-methylsulfonylphenyl)propanoic Acid

    46. N-[[2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl]carbonyl]-3-(methylsulfonyl)-l-phenylalanine

    47. N-[2-(1-benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carbonyl]-3-(methanesulfonyl)-l-phenylalanine

    2.4 Create Date
    2006-12-18
    3 Chemical and Physical Properties
    Molecular Weight 615.5 g/mol
    Molecular Formula C29H24Cl2N2O7S
    XLogP34.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count7
    Exact Mass614.0681277 g/mol
    Monoisotopic Mass614.0681277 g/mol
    Topological Polar Surface Area142 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity1100
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of signs and symptoms of keratoconjunctivitis sicca (dry eye syndrome).

    FDA Label

    Treatment of dry eye disease

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Lifitegrast addresses both the symptoms and the resulting ocular surface damage by interfering with ocular inflammatory cycle. Lifitegrast is a lymphocyte functionassociated antigen-1 antagonist through direct competitive antagonism and sequentially inhibits the T-cell recruitment, activation, and proinflammatory cytokine release associated with dry eye syndrome.

    5.2 MeSH Pharmacological Classification

    Ophthalmic Solutions

    Sterile solutions that are intended for instillation into the eye. It does not include solutions for cleaning eyeglasses or CONTACT LENS SOLUTIONS. (See all compounds classified as Ophthalmic Solutions.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    LIFITEGRAST
    5.3.2 FDA UNII
    038E5L962W
    5.3.3 Pharmacological Classes
    Lymphocyte Function-Associated Antigen-1 Antagonists [MoA]; Lymphocyte Function-Associated Antigen-1 Antagonist [EPC]
    5.4 ATC Code

    S - Sensory organs

    S01 - Ophthalmologicals

    S01X - Other ophthalmologicals

    S01XA - Other ophthalmologicals

    S01XA25 - Lifitegrast

    5.5 Absorption, Distribution and Excretion

    Absorption

    The mean peak plasma concentration (Cmax) of 1.70ng/mL was reached within 15 minutes of application. Quantifiable trough plasma concentrations ranged from 0.55 ng/mL to 3.74 ng/mL. Observations show limited systemic exposure that produces significant clinical outcomes.

    Route of Elimination

    Not possible to perform mass balance study to determine the main route of elimination.

    Clearance

    Not possible to calculate clearance rate based on plasma concentrations of lifitegrast, but reported to be relatively fast in rat I.V. pharmacokinetics study. It is predicted that lifitegrast is cleared via nasal and subsequently gastrointestinal tract.

    5.6 Metabolism/Metabolites

    Based on the findings of an in vitro metabolism study using fresh human hepatocytes, lifitegrast does not appear to undergo significant metabolism.

    5.7 Biological Half-Life

    Not possible to calculate plasma elimination half-life based on plasma concentrations of lifitegrast, but reported to be relatively short in rat I.V. pharmacokinetics study.

    5.8 Mechanism of Action

    Lifitegrast binds to the integrin lymphocyte function-associated antigen-1 (LFA-1), a cell surface protein found on leukocytes and blocks the interaction of LFA-1 with its cognate ligand intercellular adhesion molecule-1 (ICAM-1). ICAM-1 may be overexpressed in corneal and conjunctival tissues in dry eye disease. LFA-1/ICAM-1 interaction can contribute to the formation of an immunological synapse resulting in T-cell proliferation/activation and migration to target tissues. In vitro studies demonstrated that lifitegrast may inhibit T-cell adhesion to ICAM-1 in a human T-cell line and may inhibit secretion of inflammatory cytokines, inflammatory mediators, chemokines, TNF-, and IL-1 in human peripheral blood mononuclear cells.

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    Lifitegrast

    Brand Name :

    Dosage Form : Ophthalmic Solution

    Dosage Strength : 50MG/ML

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    Regulatory Info : RX

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    LIFITEGRAST

    Brand Name : LIFITEGRAST

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

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    Approval Date : 2024-10-03

    Application Number : 215058

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    Brand Name : LIFITEGRAST

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

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    Approval Date : 2023-11-07

    Application Number : 215063

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    LIFITEGRAST

    Brand Name : XIIDRA

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

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    Approval Date : 2016-07-11

    Application Number : 208073

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    Brand Name : LIFITEGRAST

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

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    Approval Date : 2023-08-04

    Application Number : 215081

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    Regulatory Info : Prescription

    Registration Country : Canada

    LIFITEGRAST

    Brand Name : XIIDRA

    Dosage Form : SOLUTION

    Dosage Strength : 5%/W/V

    Packaging :

    Approval Date :

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    Regulatory Info : Prescription

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    Brand Name : LIFITEGRAST

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

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    Approval Date :

    Application Number : 215126

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    RLD : No

    TE Code : AB

    LIFITEGRAST

    Brand Name : LIFITEGRAST

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

    Approval Date : 2024-10-03

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    RX/OTC/DISCN : RX

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    EUGIA PHARMA

    India
    Compamed
    Not Confirmed
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    EUGIA PHARMA

    India
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    Compamed
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP
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    RLD : No

    TE Code :

    LIFITEGRAST

    Brand Name : LIFITEGRAST

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

    Approval Date : 2023-11-07

    Application Number : 215063

    RX/OTC/DISCN : DISCN

    RLD : No

    TE Code :

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    03

    BAUSCH AND LOMB INC

    Canada
    Compamed
    Not Confirmed
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    BAUSCH AND LOMB INC

    Canada
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    Compamed
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP
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    RLD : Yes

    TE Code : AB

    LIFITEGRAST

    Brand Name : XIIDRA

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

    Approval Date : 2016-07-11

    Application Number : 208073

    RX/OTC/DISCN : RX

    RLD : Yes

    TE Code : AB

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    04

    MICRO LABS

    India
    Compamed
    Not Confirmed
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    MICRO LABS

    India
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    Compamed
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP
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    RLD : No

    TE Code :

    LIFITEGRAST

    Brand Name : LIFITEGRAST

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

    Approval Date : 2023-08-04

    Application Number : 215081

    RX/OTC/DISCN : DISCN

    RLD : No

    TE Code :

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    05

    SUN PHARM INDS LTD

    India
    Compamed
    Not Confirmed
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    SUN PHARM INDS LTD

    India
    arrow
    Compamed
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP
    Virtual Booth Boost your online visibility by uploading your products, APIs, FDFs, intermediates, excipients, and services for free on PharmaCompass. Rank higher among suppliers and expand your reach across the internet efficiently and cost-effectively.
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    RLD :

    TE Code :

    LIFITEGRAST

    Brand Name : LIFITEGRAST

    Dosage Form : SOLUTION/DROPS;OPHTHALMIC

    Dosage Strength : 5%

    Approval Date :

    Application Number : 215126

    RX/OTC/DISCN :

    RLD :

    TE Code :

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    Listed Dossiers

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    01

    Pharmathen SA

    Greece
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    Compamed
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP

    Virtual BoothPharmathen provides life cycle Management solutions for branded pharma, as well as to develop & establish new technology platforms.

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    Regulatory Info :

    Registration Country : Greece

    Lifitegrast

    Brand Name :

    Dosage Form : Ophthalmic Solution

    Dosage Strength : 50MG/ML

    Packaging :

    Approval Date :

    Application Number :

    Regulatory Info :

    Registration Country : Greece

    Pharmathen

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    01

    Pharmathen SA

    Greece
    arrow
    Compamed
    Not Confirmed
    • fda
    • EDQM
    • WHO-GMP

    Virtual BoothPharmathen provides life cycle Management solutions for branded pharma, as well as to develop & establish new technology platforms.

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    Flag Greece
    Virtual Booth Virtual Booth
    Digital Content Digital Content

    Packaging :

    Regulatory Info :

    Lifitegrast

    Dosage : Ophthalmic Solution

    Dosage Strength : 50MG/ML

    Brand Name :

    Approval Date :

    Application Number :

    Registration Country : Greece

    Pharmathen

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