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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
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.

Approval Year

PubMed

PubMed

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

Sample Use Guides

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.
Name Type Language
2H-1,2,4-OXADIAZINE, 5,6-DIHYDRO-5-(1-PIPERIDINYLMETHYL)-3-(3-PYRIDINYL)-, (+)-
Preferred Name English
IROXANADINE, (+)-
Common Name English
(+)-5,6-DIHYDRO-5-(1-PIPERIDINYLMETHYL)-3-(3-PYRIDINYL)-2H-1,2,4-OXADIAZINE
Common Name English
Code System Code Type Description
FDA UNII
3JD92A4CWW
Created by admin on Mon Mar 31 22:36:44 GMT 2025 , Edited by admin on Mon Mar 31 22:36:44 GMT 2025
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CAS
934838-71-8
Created by admin on Mon Mar 31 22:36:44 GMT 2025 , Edited by admin on Mon Mar 31 22:36:44 GMT 2025
PRIMARY