IROXANADINE, (+)-

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 Search

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

Molecular Formula	C14H20N4O
Molecular Weight	260.3348
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12055138 | https://www.ncbi.nlm.nih.gov/pubmed/22489270

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

Title	Date	PubMed
Restenosis and therapy.	2012	22489270
Reverse regulation of endothelial cells and myointimal hyperplasia on cell proliferation by a heatshock protein-coinducer after hypoxia.	2008-03	18239173
Pharmacological attenuation of apoptosis in reoxygenated endothelial cells.	2004-12	15583868
Pharmacologically activated migration of aortic endothelial cells is mediated through p38 SAPK.	2002-06	12055138

Patents

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:36:44 GMT 2025` Edited by `admin` on `Mon Mar 31 22:36:44 GMT 2025`
Record UNII	3JD92A4CWW
Record Status	`Validated (UNII)`
Record Version