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Details

Stereochemistry UNKNOWN
Molecular Formula C14H20N4O.ClH
Molecular Weight 296.796
Optical Activity ( - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IROXANADINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=AVKGCNAECFSXHH-UHFFFAOYSA-N
InChI=1S/C14H20N4O.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 ( + / - )

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
Pharmacologically activated migration of aortic endothelial cells is mediated through p38 SAPK.
2002 Jun
Pharmacological attenuation of apoptosis in reoxygenated endothelial cells.
2004 Dec
Reverse regulation of endothelial cells and myointimal hyperplasia on cell proliferation by a heatshock protein-coinducer after hypoxia.
2008 Mar
Restenosis and therapy.
2012
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:05:30 UTC 2023
Edited
by admin
on Sat Dec 16 09:05:30 UTC 2023
Record UNII
3NXX6SVU3A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IROXANADINE HYDROCHLORIDE
Common Name English
2H-1,2,4-OXADIAZINE, 5,6-DIHYDRO-5-(1-PIPERIDINYLMETHYL)-3-(3-PYRIDINYL)-, HYDROCHLORIDE (1:1), (-)-
Systematic Name English
IROXANADINE HYDROCHLORIDE, (-)-
Common Name English
2H-1,2,4-OXADIAZINE, 5,6-DIHYDRO-5-(1-PIPERIDINYLMETHYL)-3-(3-PYRIDINYL)-, MONOHYDROCHLORIDE, (-)-
Systematic Name English
Code System Code Type Description
CAS
276690-59-6
Created by admin on Sat Dec 16 09:05:30 UTC 2023 , Edited by admin on Sat Dec 16 09:05:30 UTC 2023
PRIMARY
FDA UNII
3NXX6SVU3A
Created by admin on Sat Dec 16 09:05:30 UTC 2023 , Edited by admin on Sat Dec 16 09:05:30 UTC 2023
PRIMARY
Related Record Type Details
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