U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H24Cl2N2O7S
Molecular Weight 615.4831
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LIFITEGRAST

SMILES

CS(=O)(=O)c1cccc(c1)C[C@@]([H])(C(=O)O)N=C(c2c(cc3CN(CCc3c2Cl)C(=O)c4ccc5ccoc5c4)Cl)O

InChI

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

HIDE SMILES / InChI

Molecular Formula C29H24Cl2N2O7S
Molecular Weight 615.4831
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Lifitegrast (under brand name Xiidra) was approved as an ophthalmic solution for the treatment of the signs and symptoms of dry eye disease. 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). This LFA-1/ICAM-1 interaction is a key step in the inflammatory cascade that contributes to dry eye disease. Besides lifitegrast participates in phase II clinical trials for prevention of the signs and symptoms of allergic conjunctivitis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P20701
Gene ID: 3683.0
Gene Symbol: ITGAL
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
XIIDRA

Approved Use

Xiidra™ (lifitegrast ophthalmic solution) 5% is indicated for the treatment of the signs and symptoms of dry eye disease (DED).

Launch Date

1.46551682E12
Preventing
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
126.383 ng/mL
5 % 3 times / day multiple, ocular
dose: 5 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
91.413 ng/mL
5 % 2 times / day multiple, ocular
dose: 5 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
10.756 ng/mL
0.3 % single, ocular
dose: 0.3 %
route of administration: Ocular
experiment type: SINGLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
24.395 ng/mL
0.3 % 2 times / day multiple, ocular
dose: 0.3 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
27.457 ng/mL
1 % 3 times / day multiple, ocular
dose: 1 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
74.792 ng/mL
5 % single, ocular
dose: 5 %
route of administration: Ocular
experiment type: SINGLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
16.222 ng/mL
1 % single, ocular
dose: 1 %
route of administration: Ocular
experiment type: SINGLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
34.763 ng/mL
1 % 2 times / day multiple, ocular
dose: 1 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.49 ng/mL
0.3 % 3 times / day multiple, ocular
dose: 0.3 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
101.009 ng × h/mL
5 % 3 times / day multiple, ocular
dose: 5 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
127.594 ng × h/mL
5 % 2 times / day multiple, ocular
dose: 5 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2.457 ng × h/mL
0.3 % single, ocular
dose: 0.3 %
route of administration: Ocular
experiment type: SINGLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
24.793 ng × h/mL
0.3 % 2 times / day multiple, ocular
dose: 0.3 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
29.537 ng × h/mL
1 % 3 times / day multiple, ocular
dose: 1 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
311.929 ng × h/mL
5 % single, ocular
dose: 5 %
route of administration: Ocular
experiment type: SINGLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
52.238 ng × h/mL
1 % single, ocular
dose: 1 %
route of administration: Ocular
experiment type: SINGLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
62.443 ng × h/mL
1 % 2 times / day multiple, ocular
dose: 1 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.432 ng × h/mL
0.3 % 3 times / day multiple, ocular
dose: 0.3 %
route of administration: Ocular
experiment type: MULTIPLE
co-administered:
LIFITEGRAST unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
unknown, ocular
LIFITEGRAST plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources: Page: p. 55
unhealthy, 58.6 years (range: 14 - 84 years)
n = 355
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.6 years (range: 14 - 84 years)
Sex: M+F
Population Size: 355
Sources: Page: p. 55
Disc. AE: Instillation site irritation, Headache...
AEs leading to
discontinuation/dose reduction:
Instillation site irritation (1.1%)
Headache (2 patients)
Sources: Page: p. 55
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources: Page: p. 55
unhealthy, 58.6 years (range: 14 - 84 years)
n = 355
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.6 years (range: 14 - 84 years)
Sex: M+F
Population Size: 355
Sources: Page: p. 55
Disc. AE: Instillation site reaction...
AEs leading to
discontinuation/dose reduction:
Instillation site reaction (1.4%)
Sources: Page: p. 55
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources:
unhealthy, 58.8 years (range: 21 - 89 years(
n = 220
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.8 years (range: 21 - 89 years(
Sex: M+F
Population Size: 220
Sources:
Disc. AE: Lacrimation increased, Instillation site reaction...
AEs leading to
discontinuation/dose reduction:
Lacrimation increased (1.4%)
Instillation site reaction (1.8%)
Visual acuity reduced (1.4%)
Dysgeusia (1.8%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Instillation site irritation 1.1%
Disc. AE
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources: Page: p. 55
unhealthy, 58.6 years (range: 14 - 84 years)
n = 355
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.6 years (range: 14 - 84 years)
Sex: M+F
Population Size: 355
Sources: Page: p. 55
Headache 2 patients
Disc. AE
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources: Page: p. 55
unhealthy, 58.6 years (range: 14 - 84 years)
n = 355
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.6 years (range: 14 - 84 years)
Sex: M+F
Population Size: 355
Sources: Page: p. 55
Instillation site reaction 1.4%
Disc. AE
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources: Page: p. 55
unhealthy, 58.6 years (range: 14 - 84 years)
n = 355
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.6 years (range: 14 - 84 years)
Sex: M+F
Population Size: 355
Sources: Page: p. 55
Lacrimation increased 1.4%
Disc. AE
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources:
unhealthy, 58.8 years (range: 21 - 89 years(
n = 220
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.8 years (range: 21 - 89 years(
Sex: M+F
Population Size: 220
Sources:
Visual acuity reduced 1.4%
Disc. AE
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources:
unhealthy, 58.8 years (range: 21 - 89 years(
n = 220
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.8 years (range: 21 - 89 years(
Sex: M+F
Population Size: 220
Sources:
Dysgeusia 1.8%
Disc. AE
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources:
unhealthy, 58.8 years (range: 21 - 89 years(
n = 220
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.8 years (range: 21 - 89 years(
Sex: M+F
Population Size: 220
Sources:
Instillation site reaction 1.8%
Disc. AE
5 % 2 times / day steady, ophthalmic
Recommended
Dose: 5 %, 2 times / day
Route: ophthalmic
Route: steady
Dose: 5 %, 2 times / day
Sources:
unhealthy, 58.8 years (range: 21 - 89 years(
n = 220
Health Status: unhealthy
Condition: dry eye disease
Age Group: 58.8 years (range: 21 - 89 years(
Sex: M+F
Population Size: 220
Sources:
PubMed

PubMed

TitleDatePubMed
The pharmacologic assessment of a novel lymphocyte function-associated antigen-1 antagonist (SAR 1118) for the treatment of keratoconjunctivitis sicca in dogs.
2011 May 16
Patents

Patents

Sample Use Guides

One drop twice daily in each eye (approximately 12 hours apart).
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:30:50 UTC 2021
Edited
by admin
on Sat Jun 26 10:30:50 UTC 2021
Record UNII
038E5L962W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LIFITEGRAST
DASH   INN   USAN   WHO-DD  
USAN   INN  
Official Name English
LIFITEGRAST [USAN]
Common Name English
SHP-606
Code English
LIFITEGRAST [INN]
Common Name English
SAR-1118
Code English
LIFITEGRAST [ORANGE BOOK]
Common Name English
LIFITEGRAST [MI]
Common Name English
LIFITEGRAST [WHO-DD]
Common Name English
XIIDRA
Brand Name English
SHP606
Code English
(2S)-2-(((2-(BENZOFURAN-6-YLCARBONYL)-5,7-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLIN-6- YL)CARBONYL)AMINO)-3-(3-(METHYLSULFONYL)PHENYL)PROPANOIC ACID
Systematic Name English
L-PHENYLALANINE, N-((2-(6-BENZOFURANYLCARBONYL)-5,7-DICHLORO-1,2,3,4-TETRAHYDRO-6-ISOQUINOLINYL)CARBONYL)-3-(METHYLSULFONYL)-
Systematic Name English
SAR 1118
Code English
Classification Tree Code System Code
WHO-ATC S01XA25
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
NDF-RT N0000192701
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
Code System Code Type Description
DRUG BANK
DB11611
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
DRUG CENTRAL
5174
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
INN
9584
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
FDA UNII
038E5L962W
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
PUBCHEM
11965427
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL2048028
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
MERCK INDEX
M11967
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
EVMPD
SUB184496
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
NCI_THESAURUS
C175726
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
NDF-RT
N0000192700
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY Lymphocyte Function-Associated Antigen-1 Antagonists [MoA]
LACTMED
Lifitegrast
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
CAS
1025967-78-5
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
RXCUI
1801820
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
EPA CompTox
1025967-78-5
Created by admin on Sat Jun 26 10:30:50 UTC 2021 , Edited by admin on Sat Jun 26 10:30:50 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INHIBITOR
IC50
TARGET -> INHIBITOR
ANTAGONIST
Related Record Type Details
ACTIVE MOIETY