Lifitegrast

Lifitegrast

Clinical data
Trade names	Xiidra
Other names	SAR-1118
AHFS/Drugs.com	Monograph
MedlinePlus	a616039
Pregnancy category	AU: B1
Routes of administration	Eye drops
ATC code	S01XA25 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Identifiers
IUPAC name N-{[2-(1-Benzofuran-6-ylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl]carbonyl}-3-(methylsulfonyl)-L-phenylalanine
CAS Number	1025967-78-5
PubChem CID	11965427
ChemSpider	10139520
UNII	038E5L962W
KEGG	D10374
ChEBI	CHEBI:133023 Y
ChEMBL	ChEMBL2048028
CompTox Dashboard (EPA)	DTXSID60145345
ECHA InfoCard	100.245.695
Chemical and physical data
Formula	C29H24Cl2N2O7S
Molar mass	615.48 g·mol−1
3D model (JSmol)	Interactive image
SMILES CS(=O)(=O)c1cccc(c1)C[C@@H](C(=O)O)NC(=O)c2c(cc3c(c2Cl)CCN(C3)C(=O)c4ccc5ccoc5c4)Cl
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 Key:JFOZKMSJYSPYLN-QHCPKHFHSA-N

Lifitegrast, sold under the brand name Xiidra (/ˈzaɪdrə/), 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 in conjunction with ciclosporin (Ikervis, Restasis, or Cequa) for dry eye treatment including meibomian gland dysfunction and inflammatory dry eye.

Adverse effects

Common side effects in clinical trials were eye irritation, discomfort, blurred vision, and dysgeusia (a distortion of the sense of taste).

Pharmacology

Lifitegrast is supplied as an eye drop.

Mechanism of action

Lifitegrast inhibits an integrin, lymphocyte function-associated antigen 1 (LFA-1), from binding to intercellular adhesion molecule 1 (ICAM-1). This mechanism down-regulates inflammation mediated by T lymphocytes.

History

Lifitegrast was initially designed and developed by SARcode Bioscience which was acquired by Shire in 2013, which submitted a new drug application to the US Food and Drug Administration (FDA) in March 2015. The FDA granted Shire a priority review a month later, and requested additional clinical data, which were supplied in January 2016; approval was granted on 11 July 2016. Lifitegrast was approved by Health Canada in January 2018, and available in Canadian pharmacies as of March 2018.

Shire was acquired by Takeda Pharmaceutical Company in late 2018. In May 2019 Novartis reached an agreement to purchase the assets associated with Lifitegrast. Novartis will pay Takeda an upfront payment of $3.4 billion, while the latter drugmaker is eligible for milestone payments of as much as $1.9 billion. Novartis noted that the drug amassed approximately $400 million in revenue in 2018.

See also

• Restasis (ciclosporin eye drops for keratoconjunctivitis sicca)