Compound Detail
CHEMBL2048028
LIFITEGRAST 💊 Approved Drug
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💊 Approved Drug
CS(=O)(=O)c1cccc(C[C@H](NC(=O)c2c(Cl)cc3c(c2Cl)CCN(C(=O)c2ccc4ccoc4c2)C3)C(=O)O)c1
Basic Information
| ChEMBL ID | CHEMBL2048028 |
| Name | LIFITEGRAST |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | JFOZKMSJYSPYLN-QHCPKHFHSA-N |
| Therapeutic | ✓ Yes |
3
Targets
4
Activities
1
Assay Types
3
PK Parameters
9
Publications
6
Known Names
4
Indications
1
Mechanisms
Molecular Properties
615.5
MW (Da)
4.77
ALogP
6
HBA
2
HBD
134.0
PSA (Ų)
0.31
QED
1
Ro5 Violations
7
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 2016 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Integrin alpha-L/beta-2 (LFA-1) antagonist | ANTAGONIST | Integrin alpha-L/beta-2 (LFA-1) | ✓ | ✓ |
Indications
Dry Eye Syndromes Eye Diseases Conjunctivitis, Allergic Graft vs Host Disease
ATC Classification
S01XA25
lifitegrast
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
Activity Summary
IC50 4 meas. best 8.53
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Intercellular adhesion molecule 1 CHEMBL3070 | IC50 | 8.53 | 8.53 | 3.0 | 1 |
| Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 CHEMBL2096661 | IC50 | 8.05 | 7.59 | 9.0 | 2 |
| Cytochrome P450 2C9 CHEMBL3397 | IC50 | 5.52 | 5.52 | 3000.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 705.0 | ng.hr/Kg | Rattus norvegicus |
| CL | 139.2 | mL.min-1.kg-1 | Rattus norvegicus |
| T1/2 | 0.78 | hr | Rattus norvegicus |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Intercellular adhesion molecule 1 | IC50 | = | 2.98 | nM | 8.53 | Inhibition of human recombinant ICAM-1 adhesion into human Jurkat cells after 1 ... | 24900456 |
| Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 | IC50 | = | 9.0 | nM | 8.05 | Antagonist activity at LFA-1/ICAM-1 in human HuT-78 T-cells assessed as inhibiti... | 24900456 |
| Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 | IC50 | = | 74.0 | nM | 7.13 | Antagonist activity at LFA-1/ICAM-1 in human HuT-78 T-cells assessed as inhibiti... | 24900456 |
| Cytochrome P450 2C9 | IC50 | = | 3000.0 | nM | 5.52 | Inhibition of CYP2C9 | 24900456 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| 24900456 | 10.1021/ml2002482 | Intercellular adhesion molecule 1 | 7 |
| 24900456 | 10.1021/ml2002482 | Rattus norvegicus | 3 |
| 24900456 | 10.1021/ml2002482 | Intercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2 | 2 |
| 24900456 | 10.1021/ml2002482 | Liver microsomes | 2 |
| 24900456 | 10.1021/ml2002482 | Canis familiaris | 2 |
| 24900456 | 10.1021/ml2002482 | Salmonella typhimurium | 1 |
| 24900456 | 10.1021/ml2002482 | Cytochrome P450 3A4 | 1 |
| 24900456 | 10.1021/ml2002482 | Cytochrome P450 2C9 | 1 |
| 24900456 | 10.1021/ml2002482 | Voltage-gated inwardly rectifying potassium channel KCNH2 | 1 |
Data from ChEMBL 36 via Core Engine