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Details

Stereochemistry RACEMIC
Molecular Formula C13H16N2O
Molecular Weight 216.2794
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EFAROXAN

SMILES

CCC1(Cc2ccccc2O1)C3=NCCN3

InChI

InChIKey=RATZLMXRALDSJW-UHFFFAOYSA-N
InChI=1S/C13H16N2O/c1-2-13(12-14-7-8-15-12)9-10-5-3-4-6-11(10)16-13/h3-6H,2,7-9H2,1H3,(H,14,15)

HIDE SMILES / InChI

Molecular Formula C13H16N2O
Molecular Weight 216.2794
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Efaroxan (RX 821037) is a potent and selective alpha(2)-adrenoceptor antagonist. Additionally, Efaroxan is a selective antagonist at the imidazoline I1 receptor. Efaroxan promotes insulin secretion, in the absence of exogenous agonists, by a mechanism that involves inhibition of ATP-regulated K+ channels. Efaroxan was in clinical trials for the treatment of diabetes mellitus however its development has been discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Desensitization of insulin secretion by depolarizing insulin secretagogues.
2004 Dec
Glucose dependence of imidazoline-induced insulin secretion: different characteristics of two ATP-Sensitive K+ channel-blocking compounds.
2004 Dec
The putative imidazoline receptor agonist, harmane, promotes intracellular calcium mobilisation in pancreatic beta-cells.
2004 Oct 6
Imidazoline receptors associated with noradrenergic terminals in the rostral ventrolateral medulla mediate the hypotensive responses of moxonidine but not clonidine.
2005
Noradrenergic modulation of XII motoneuron inspiratory activity does not involve alpha2-receptor inhibition of the Ih current or presynaptic glutamate release.
2005 Apr
Inhibition of perforant path input to the CA1 region by serotonin and noradrenaline.
2005 Aug
Identification of the central imidazoline receptor subtype involved in modulation of halothane-epinephrine arrhythmias in rats.
2005 Dec
Essential role of the imidazoline moiety in the insulinotropic effect but not the KATP channel-blocking effect of imidazolines; a comparison of the effects of efaroxan and its imidazole analogue, KU14R.
2005 Dec
Monomeric G-protein, Rhes, is not an imidazoline-regulated protein in pancreatic beta-cells.
2005 Dec 23
Rat clonidine mydriasis model: imidazoline receptors are not involved.
2005 Jan 15
[The role of alpha2-adrenergic and I1-imidazoline receptors in the effects of clonidine and moxonidine on isolated large intestine of mice].
2005 Jan-Feb
Neuronal norepinephrine responses of the rostral ventrolateral medulla and nucleus tractus solitarius neurons distinguish the I1- from the alpha2-receptor-mediated hypotension in conscious SHRs.
2005 Jul
Mechanisms involved in the antinociception caused by agmatine in mice.
2005 Jun
Urinary responses to acute moxonidine are inhibited by natriuretic peptide receptor antagonist.
2005 May
Site-dependent inhibition of neuronal c-jun in the brainstem elicited by imidazoline I1 receptor activation: role in rilmenidine-evoked hypotension.
2005 May 9
IRAS, a candidate for I1-imidazoline receptor, mediates inhibitory effect of agmatine on cellular morphine dependence.
2005 Oct 1
Involvement of supraspinal imidazoline receptors and descending monoaminergic pathways in tizanidine-induced inhibition of rat spinal reflexes.
2005 Sep
Mitogen-activated protein kinase phosphorylation in the rostral ventrolateral medulla plays a key role in imidazoline (i1)-receptor-mediated hypotension.
2005 Sep
Effect of BU98008, an imidazoline1-binding site ligand, on body temperature in mice.
2005 Sep 5
Involvement of phosphatidylcholine-selective phospholipase C in activation of mitogen-activated protein kinase pathways in imidazoline receptor antisera-selected protein.
2006 Aug 15
Involvement of I2-imidazoline binding sites in positive and negative morphine analgesia modulatory effects.
2006 Dec 28
Presynaptic I1-imidazoline receptors reduce GABAergic synaptic transmission in striatal medium spiny neurons.
2006 Feb 8
Theoretical study of structure, pKa, lipophilicity, solubility, absorption, and polar surface area of some centrally acting antihypertensives.
2006 Mar 15
Rhes expression in pancreatic beta-cells is regulated by efaroxan in a calcium-dependent process.
2006 Oct 20
Modulation of agmatine on calcium signal in morphine-dependent CHO cells by activation of IRAS, a candidate for imidazoline I1 receptor.
2006 Oct 24
RX871024 reduces NO production but does not protect against pancreatic beta-cell death induced by proinflammatory cytokines.
2006 Sep 8
Imidazoline receptors in relaxation of acetylcholine-constricted isolated rat jejunum.
2006 Sep-Oct
Sensitivity improvement of circular dichroism detection in HPLC by using a low-pass electronic noise filter: Application to the enantiomeric determination purity of a basic drug.
2007 Feb
Validation of a method using an achiral liquid chromatography sorbent and a circular dichroism detector. Analysis of the efaroxan enantiomers.
2007 Feb 9
Antagonism of the insulinotropic action of first generation imidazolines by openers of K(ATP) channels.
2007 Jan 1
Possible role of NMDA receptors in antinociception induced by rilmenidine in mice in the formalin test.
2007 Jul
Evidence for imidazoline receptors involvement in the agmatine antidepressant-like effect in the forced swimming test.
2007 Jun 22
Quantification of very low enantiomeric impurity of efaroxan using a dual cyclodextrin system by capillary electrophoresis.
2007 Jun 5
Characterization of an antiproliferative effect of imidazoline receptor ligands on PC12 cells.
2007 Nov-Dec
Sympathoexcitation of moxonidine in the caudal ventrolateral medulla is dependent on I1-imidazoline receptors in anesthetized rats.
2007 Oct 16
The imidazoline RX871024 induces death of proliferating insulin-secreting cells by activation of c-jun N-terminal kinase.
2008 Apr
Effect of agmatine on DAMGO-induced mu-opioid receptor down-regulation and internalization via activation of IRAS, a candidate for imidazoline I(1) receptor.
2008 Dec 3
Dexmedetomidine reduces long-term potentiation in mouse hippocampus.
2008 Jan
alpha2A-adrenoceptor antagonism increases insulin secretion and synergistically augments the insulinotropic effect of glibenclamide in mice.
2008 Jul
Imidazoline I(1) receptor-mediated reduction of muscle rigidity in the reserpine-treated murine model of Parkinson's disease.
2008 Jul 28
Effects of spinal alpha(2)-adrenoceptor and I(1)-imidazoline receptor activation on hindlimb movement induction in spinal cord-injured mice.
2008 Jun
Dexmedetomidine increases hippocampal phosphorylated extracellular signal-regulated protein kinase 1 and 2 content by an alpha 2-adrenoceptor-independent mechanism: evidence for the involvement of imidazoline I1 receptors.
2008 Mar
Caffeine and a selective adenosine A(2B) receptor antagonist but not imidazoline receptor antagonists modulate antinociception induced by diphenyl diselenide in mice.
2008 May 9
Effect of moxonidine on the uveoscleral outflow: role of alpha2-adrenoceptors or i1 imidazoline receptors.
2009 Apr
Dexmedetomidine, an alpha2-adrenergic agonist, inhibits neuronal delayed-rectifier potassium current and sodium current.
2009 Aug
Proinflammatory cytokines activate the intrinsic apoptotic pathway in beta-cells.
2009 Aug
Preventive mechanisms of agmatine against ischemic acute kidney injury in rats.
2009 Jan 28
Antineoplastic activity of idazoxan hydrochloride.
2009 Nov
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.
2009 Oct 23
Antidepressant like effect of selective serotonin reuptake inhibitors involve modulation of imidazoline receptors by agmatine.
2009 Sep
Patents
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:56:41 UTC 2021
Edited
by admin
on Fri Jun 25 21:56:41 UTC 2021
Record UNII
G00490L21H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EFAROXAN
INN  
INN  
Official Name English
2-(2-ETHYL-2,3-DIHYDRO-2-BENZOFURANYL)-4,5-DIHYDRO-1H-IMIDAZOLE
Systematic Name English
NSC-759562
Code English
1H-IMIDAZOLE, 2-(2-ETHYL-2,3-DIHYDRO-2-BENZOFURANYL)-4,5-DIHYDRO-
Systematic Name English
EFAROXAN [INN]
Common Name English
(+/-)-2-(2-ETHYL-2,3-DIHYDRO-2-BENZOFURANYL)-2-IMIDAZOLINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
Code System Code Type Description
EPA CompTox
89197-32-0
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
MESH
C062597
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
NCI_THESAURUS
C72923
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
CAS
89197-32-0
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
INN
6216
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
WIKIPEDIA
EFAROXAN
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL57895
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
EVMPD
SUB06462MIG
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
FDA UNII
G00490L21H
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
PUBCHEM
72016
Created by admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SHORT-ACTING
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY