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Details

Stereochemistry UNKNOWN
Molecular Formula C14H20N4O
Molecular Weight 260.3348
Optical Activity ( - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IROXANADINE

SMILES

C(C1CONC(=N1)C2=CN=CC=C2)N3CCCCC3

InChI

InChIKey=QWVRTSZDKPRPDF-UHFFFAOYSA-N
InChI=1S/C14H20N4O/c1-2-7-18(8-3-1)10-13-11-19-17-14(16-13)12-5-4-6-15-9-12/h4-6,9,13H,1-3,7-8,10-11H2,(H,16,17)

HIDE SMILES / InChI

Description

IROXANADINE, a pyridine derivative, is under development for the treatment of atherosclerosis and the complications of atherosclerosis such as ischaemic heart disease, peripheral arterial disease, and restenosis. It induces phosphorylation of p38 stress-activated protein kinase, which plays an important role in endothelial cells (EC) homeostasis. EC function plays a central role in vascular diseases.

Originator

Approval Year

PubMed

Sample Use Guides

In Vitro Use Guide
Iroxanadine (BRX-235) may improve survival of vascular endothelial cells (ECs) following ischemia/reperfusion stress. ECs cultured from human umbilical veins were exposed to hypoxia/reoxygenation to mimic ischemia/reperfusion. Caspase activation and apoptosis were monitored in the reoxygenated cells. Addition of BRX-235 (0.1-1 microM) to culture medium prior to hypoxia or at start of reoxygenation significantly reduced the caspase-dependent apoptosis. The cytoprotection conferred by the pre-hypoxic drug administration was sensitive to quercetin and seems to be based on enhanced heat shock protein accumulation in stressed ECs.