Lifitegrast - Moligand™, ≥97% , Integrin alpha-L/beta-2 (LFA-1) antagonist, CAS No.1025967-78-5, Integrin alpha-L/beta-2 (LFA-1) antagonist

CAS: 1025967-78-5 Cat. No.: L171714 Molecular Weight: 615.48 EC Number: 813-044-8

GRADE & PURITY Moligand™, ≥97%

Synonyms

EN300-20605731 | 7-hydroxy-2-methyl-3-phenoxy-chromone | s3714 | A900838 | Q23044263 | N-(2-(1-benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carbonyl)-3-(methanesulfonyl)-L-phenylalanine | (2S)-2-{[2-(1-benzofuran-6-carbonyl)-5,7-di

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

LFA-1 (lymphocyte function-associated antigen-1) antagonist.

Specifications

Synonyms

EN300-20605731 | 7-hydroxy-2-methyl-3-phenoxy-chromone | s3714 | A900838 | Q23044263 | N-(2-(1-benzofuran-6-carbonyl)-5, 7-dichloro-1, 2, 3, 4-tetrahydroisoquinoline-6-carbonyl)-3-(methanesulfonyl)-L-phenylalanine | (2S)-2-{[2-(1-benzofuran-6-carbonyl)-5, 7-di

Specifications & Purity

Moligand™, ≥97%

Biochemical and Physiological Mechanisms

LFA-1 (lymphocyte function-associated antigen-1) antagonist, used to treat ocular vascular complications. Lifitegrast\xa0 is a new type of T cell integrin antagonist designed to mimic the binding epitope of ICAM-1.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

ANTAGONIST

Mechanism of action

Integrin alpha-L/beta-2 (LFA-1) antagonist

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥97%

Product Properties

• ALogP: 4.7

Names and Identifiers

• Pubchem Sid: 504766848
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504766848
• 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
• 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
• InChIKey: JFOZKMSJYSPYLN-QHCPKHFHSA-N
• 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
• 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
• Molecular Weight: 615.48
• Reaxy-Rn: 42812549
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=42812549&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Phenylalanine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Phenylalanine and derivatives
• Alternative Parents: N-acyl-alpha amino acids Phenylpropanoic acids Tetrahydroisoquinolines 2-halobenzoic acids and derivatives Amphetamines and derivatives Benzenesulfonyl compounds Benzofurans Aryl chlorides Vinylogous halides Tertiary carboxylic acid amides Sulfones Furans Heteroaromatic compounds Secondary carboxylic acid amides Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Organochlorides Carbonyl compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Phenylalanine or derivatives - N-acyl-alpha amino acid or derivatives - N-acyl-alpha-amino acid - 3-phenylpropanoic-acid - Amphetamine or derivatives - Tetrahydroisoquinoline - 2-halobenzoic acid or derivatives - Halobenzoic acid or derivatives - Benzofuran - Benzenesulfonyl group - Aryl halide - Benzenoid - Aryl chloride - Monocyclic benzene moiety - Furan - Vinylogous halide - Sulfonyl - Sulfone - Tertiary carboxylic acid amide - Heteroaromatic compound - Carboxamide group - Secondary carboxylic acid amide - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Azacycle - Carboxylic acid - Oxacycle - Organonitrogen compound - Organochloride - Organohalogen compound - Organic nitrogen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Organosulfur compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as phenylalanine and derivatives. These are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ICAM1 Tchem Intercellular adhesion molecule 1 (1 Activities)

Discover Target: ICAM1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ITGAL Tclin Integrin alpha-L (0 Activities)

Discover Target: ITGAL

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ICAM1 Tchem Intercellular adhesion molecule-1 (260 Activities)

Discover Target: ICAM1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Liver microsomes (16955 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Salmonella typhimurium (15756 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Canis familiaris (36305 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 615.500 g/mol
• XLogP3: 4.700
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 614.068 Da
• Monoisotopic Mass: 614.068 Da
• Topological Polar Surface Area: 142.000 Ų
• Heavy Atom Count: 41
• Formal Charge: 0
• Complexity: 1100.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xin Meng, Ye Wang.  (2021)  Drug Repurposing for Influenza Virus Polymerase Acidic (PA) Endonuclease Inhibitor.  MOLECULES,  26  (23): (7326).  [PMID:34885905] [10.3390/molecules26237326]

2. Han Sun, Xu Pang, Jian-Rui Li, Hu Li, Mei Tang, Tao Zhang, Li-Yan Yu, Zong-Gen Peng.  (2024)  Isoechinulin B, a natural product from Antarctic fungus, attenuates acute liver injury by inhibiting excessive cell adhesion.  EUROPEAN JOURNAL OF PHARMACOLOGY,      [PMID:39427860] [10.1016/j.ejphar.2024.177065]