LIFITEGRAST

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Search structure


Trade Names	XIIDRA
Synonyms	Lifitegrast SAR 1118 SAR-1118 SHP-606 SHP606 Xiidra
Status
Molecule Category	UNKNOWN
ATC	S01XA25
UNII	038E5L962W
EPA CompTox	DTXSID60145345


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	JFOZKMSJYSPYLN-QHCPKHFHSA-N
Smiles	CS(=O)(=O)c1cccc(C[C@H](NC(=O)c2c(Cl)cc3c(c2Cl)CCN(C(=O)c2ccc4ccoc4c2)C3)C(=O)O)c1
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C29H24Cl2N2O7S
Molecular Weight	615.49
AlogP	4.77
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	7.0
Polar Surface Area	133.99
Molecular species	ACID
Aromatic Rings	4.0
Heavy Atoms	41.0

Bioactivity

Mechanism of Action	Action	Reference
Integrin alpha-L/beta-2 (LFA-1) antagonist	ANTAGONIST	PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Adhesion	-	9-74	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9	-	3000	-	-	-
Membrane receptor	-	9-74	-	-	-

Assay Description	Organism	Bioactivity	Reference
Antagonist activity at LFA-1/ICAM-1 in human HuT-78 T-cells assessed as inhibition of cell adhesion after 1 hr by p-nitrophenyl n-acetyl-beta-D-glucosaminide method	Homo sapiens	9.0 nM
Antagonist activity at LFA-1/ICAM-1 in human HuT-78 T-cells assessed as inhibition of cell adhesion after 1 hr by p-nitrophenyl n-acetyl-beta-D-glucosaminide method in presence of 10% human serum	Homo sapiens	74.0 nM
Inhibition of human recombinant ICAM-1 adhesion into human Jurkat cells after 1 hr	Homo sapiens	2.98 nM

Cross References

Resources	Reference
ChEBI	133023
ChEMBL	CHEMBL2048028
DrugBank	DB11611
DrugCentral	5174
FDA SRS	038E5L962W
Guide to Pharmacology	7533
PubChem	11965427
SureChEMBL	SCHEMBL2632068
ZINC	ZINC000084668739

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).