Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H18ClNO3 |
| Molecular Weight | 367.826 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=C2C=CC3=C(CCCC3)C2=NC(CC4=CC=C(Cl)C=C4)=C1O
InChI
InChIKey=DIEPFYNZGUUVHD-UHFFFAOYSA-N
InChI=1S/C21H18ClNO3/c22-14-8-5-12(6-9-14)11-17-20(24)18(21(25)26)16-10-7-13-3-1-2-4-15(13)19(16)23-17/h5-10,24H,1-4,11H2,(H,25,26)
| Molecular Formula | C21H18ClNO3 |
| Molecular Weight | 367.826 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
PSI-697 is a quinoline derivative patented by Wyeth, John, and Brother Ltd. as a selectin inhibitor useful for the treatment of acute coronary syndromes. Surface expression of P-selectin on activated platelets induces the formation of platelet-monocyte aggregates and promotes vascular inflammation and thrombosis. In cell-based assays, PSI-697 dose-dependently inhibits the binding of human P-selectin to human P-selectin glycoprotein ligand-1. In preclinical trials, PSI-697, promotes thrombus resolution and decreases inflammation in a baboon model of venous thrombosis. Animals receiving PSI-697 demonstrated significantly increased plasma D-dimer levels versus low-molecular-weight-heparin and control animals six hours post thrombus induction. Unfortunately, in clinical trials, PSI-697 did not inhibit basal or stimulated platelet-monocyte aggregate formation in humans
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL5378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18024786 |
125.0 µM [IC50] |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of PSI-697, a novel P-selectin inhibitor, on platelet-monocyte aggregate formation in humans. | 2013-01-28 |
|
| P-selectin antagonism reduces thrombus formation in humans. | 2009-11 |
|
| Characterization of the novel P-selectin inhibitor PSI-697 [2-(4-chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[h] quinoline-4-carboxylic acid] in vitro and in rodent models of vascular inflammation and thrombosis. | 2008-02 |
|
| Resolution of venous thrombosis using a novel oral small-molecule inhibitor of P-selectin (PSI-697) without anticoagulation. | 2007-03 |
|
| 2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H]quinoline-4-carboxylic acid (PSI-697): identification of a clinical candidate from the quinoline salicylic acid series of P-selectin antagonists. | 2007-01-11 |
|
| Treatment with an oral small molecule inhibitor of P selectin (PSI-697) decreases vein wall injury in a rat stenosis model of venous thrombosis. | 2006-09 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23525448
600 mg/day
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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LH1XC916ME
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