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=CC=CN=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
Pharmacologically activated migration of aortic endothelial cells is mediated through p38 SAPK.	2002 Jun	12055138
Pharmacological attenuation of apoptosis in reoxygenated endothelial cells.	2004 Dec	15583868
Reverse regulation of endothelial cells and myointimal hyperplasia on cell proliferation by a heatshock protein-coinducer after hypoxia.	2008 Mar	18239173
Restenosis and therapy.	2012	22489270

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 `Fri Dec 15 17:26:55 GMT 2023` Edited by `admin` on `Fri Dec 15 17:26:55 GMT 2023`
Record UNII	6K69EJ1DL1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IROXANADINE

Official Name

English

(-)-5-(PIPERIDIN-1-YLMETHYL)-3-(PYRIDIN-3-YL)-5,6-DIHYDRO-2H-1,2,4-OXADIAZINE

Common Name

English

IROXANADINE, (-)-

Common Name

English

2H-1,2,4-OXADIAZINE, 5,6-DIHYDRO-5-(1-PIPERIDINYLMETHYL)-3-(3-PYRIDINYL)-, (-)-

Systematic Name

English

iroxanadine [INN]

Common Name

English

(-)-5,6-DIHYDRO-5-(1-PIPERIDINYLMETHYL)-3-(3-PYRIDINYL)-2H-1,2,4-OXADIAZINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2079