NAV

Iroxanadine

Identification

Generic Name
Iroxanadine
DrugBank Accession Number
DB05444
Background

BRX-235 (iroxanadine) is a a novel small molecule synthesized by Biorex, Hungary that acts as a cardioprotective agent. It induces phosphorylation of p38 SAPK, which plays an important role in EC homeostasis. endothelial cell (EC). EC function plays a central role in vascular diseases (e.g. atherosclerosis, restenosis, diabetic angiopathies, microvascular angina, peripheral arterial disease). BRX-235 also causes translocation of calcium-dependent protein kinase C isoform to membranes.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 260.3348
Monoisotopic: 260.163711282
Chemical Formula
C14H20N4O
Synonyms
  • Iroxanadine
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Pharmacology

Indication

Investigated for use/treatment in atherosclerosis and vascular diseases as a cardioprotective agent. Its use has also been suggested for the prevention of early restenosis following vascular surgery or balloon angioplasty.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

EC (endothelial cell) function plays a central role in vascular diseases (e.g. atherosclerosis, restenosis, diabetic angiopathies, microvascular angina, peripheral arterial disease). BRX-235 induces phosphorylation of p38 SAPK, which plays an important role in EC homeostasis.

Mechanism of action

BRX-235 induces phosphorylation of p38 SAPK, which plays an important role in EC (endothelial cell) homeostasis.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Not Available
Direct Parent
Pyridines and derivatives
Alternative Parents
Piperidines / Imidolactams / Heteroaromatic compounds / Trialkylamines / Propargyl-type 1,3-dipolar organic compounds / Oxacyclic compounds / Azacyclic compounds / Amidines / Organopnictogen compounds / Organooxygen compounds
show 1 more
Substituents
Amidine / Amine / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam / Organic 1,3-dipolar compound / Organic nitrogen compound / Organic oxygen compound
show 9 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6K69EJ1DL1
CAS number
276690-58-5
InChI Key
QWVRTSZDKPRPDF-UHFFFAOYSA-N
InChI
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)
IUPAC Name
5-[(piperidin-1-yl)methyl]-3-(pyridin-3-yl)-5,6-dihydro-2H-1,2,4-oxadiazine
SMILES
C(C1CONC(=N1)C1=CN=CC=C1)N1CCCCC1

References

General References
  1. Kabakov AE, Budagova KR, Malyutina YV, Latchman DS, Csermely P: Pharmacological attenuation of apoptosis in reoxygenated endothelial cells. Cell Mol Life Sci. 2004 Dec;61(24):3076-86. [Article]
  2. Denes L, Jednakovits A, Hargitai J, Penzes Z, Balla A, Talosi L, Krajcsi P, Csermely P: Pharmacologically activated migration of aortic endothelial cells is mediated through p38 SAPK. Br J Pharmacol. 2002 Jun;136(4):597-603. [Article]
PubChem Compound
6421776
PubChem Substance
175427005
ChemSpider
4927305
ChEMBL
CHEMBL2107433

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.908 mg/mLALOGPS
logP1.31ALOGPS
logP1.1Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)18.8Chemaxon
pKa (Strongest Basic)8.68Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area49.75 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity84.66 m3·mol-1Chemaxon
Polarizability28.6 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9936
Blood Brain Barrier+0.9182
Caco-2 permeable-0.5633
P-glycoprotein substrateSubstrate0.6293
P-glycoprotein inhibitor INon-inhibitor0.7307
P-glycoprotein inhibitor IINon-inhibitor0.7863
Renal organic cation transporterInhibitor0.6271
CYP450 2C9 substrateNon-substrate0.8019
CYP450 2D6 substrateNon-substrate0.6459
CYP450 3A4 substrateNon-substrate0.6835
CYP450 1A2 substrateInhibitor0.5847
CYP450 2C9 inhibitorNon-inhibitor0.835
CYP450 2D6 inhibitorNon-inhibitor0.8646
CYP450 2C19 inhibitorNon-inhibitor0.7799
CYP450 3A4 inhibitorNon-inhibitor0.7711
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.841
Ames testNon AMES toxic0.5639
CarcinogenicityNon-carcinogens0.8144
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3948 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5478
hERG inhibition (predictor II)Inhibitor0.519
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-19caabc0217e8526fac2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0090000000-0b2396e0f15ca07d3b65
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-88ab53bdcbc9156eb535
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0590000000-6c2659c9490a2267baa9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bta-3910000000-dd03205c4ee0053fbb8d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zor-5920000000-24e9b25a5f2dd601f964
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-160.03474
predicted
DeepCCS 1.0 (2019)
[M+H]+162.39275
predicted
DeepCCS 1.0 (2019)
[M+Na]+168.4859
predicted
DeepCCS 1.0 (2019)

Drug created at November 18, 2007 18:25 / Updated at February 21, 2021 18:51