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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
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

Targets

Primary TargetPharmacologyConditionPotency
125.0 µM [IC50]
PubMed

PubMed

TitleDatePubMed
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 Sep
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 Jan 11
Resolution of venous thrombosis using a novel oral small-molecule inhibitor of P-selectin (PSI-697) without anticoagulation.
2007 Mar
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 Feb
P-selectin antagonism reduces thrombus formation in humans.
2009 Nov
Effect of PSI-697, a novel P-selectin inhibitor, on platelet-monocyte aggregate formation in humans.
2013 Jan 28
Patents

Sample Use Guides

600 mg/day
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:01:37 GMT 2023
Edited
by admin
on Sat Dec 16 04:01:37 GMT 2023
Record UNII
LH1XC916ME
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PSI-697
Common Name English
BENZO(H)QUINOLINE-4-CARBOXYLIC ACID, 2-((4-CHLOROPHENYL)METHYL)-7,8,9,10-TETRAHYDRO-3-HYDROXY-
Systematic Name English
2-(4-CHLOROBENZYL)-3-HYDROXY-7,8,9,10-TETRAHYDROBENZO(H)QUINOLINE-4-CARBOXYLIC ACID
Systematic Name English
Code System Code Type Description
SMS_ID
300000041344
Created by admin on Sat Dec 16 04:01:37 GMT 2023 , Edited by admin on Sat Dec 16 04:01:37 GMT 2023
PRIMARY
FDA UNII
LH1XC916ME
Created by admin on Sat Dec 16 04:01:37 GMT 2023 , Edited by admin on Sat Dec 16 04:01:37 GMT 2023
PRIMARY
DRUG BANK
DB12211
Created by admin on Sat Dec 16 04:01:37 GMT 2023 , Edited by admin on Sat Dec 16 04:01:37 GMT 2023
PRIMARY
PUBCHEM
12004316
Created by admin on Sat Dec 16 04:01:37 GMT 2023 , Edited by admin on Sat Dec 16 04:01:37 GMT 2023
PRIMARY
CAS
851546-61-7
Created by admin on Sat Dec 16 04:01:37 GMT 2023 , Edited by admin on Sat Dec 16 04:01:37 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY