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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
Structure of PSI-697

SMILES

OC(=O)C1=C(O)C(CC2=CC=C(Cl)C=C2)=NC3=C4CCCCC4=CC=C13

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)

HIDE SMILES / InChI

Molecular Formula C21H18ClNO3
Molecular Weight 367.826
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
125.0 µM [IC50]

PubMed

Sample Use Guides

In Vivo Use Guide
600 mg/day
Route of Administration: Oral
Substance Class Chemical
Record UNII
LH1XC916ME
Record Status Validated (UNII)
Record Version