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
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)
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.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Desensitization of insulin secretion by depolarizing insulin secretagogues. | 2004 Dec |
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Glucose dependence of imidazoline-induced insulin secretion: different characteristics of two ATP-Sensitive K+ channel-blocking compounds. | 2004 Dec |
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The putative imidazoline receptor agonist, harmane, promotes intracellular calcium mobilisation in pancreatic beta-cells. | 2004 Oct 6 |
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Imidazoline receptors associated with noradrenergic terminals in the rostral ventrolateral medulla mediate the hypotensive responses of moxonidine but not clonidine. | 2005 |
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Noradrenergic modulation of XII motoneuron inspiratory activity does not involve alpha2-receptor inhibition of the Ih current or presynaptic glutamate release. | 2005 Apr |
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Inhibition of perforant path input to the CA1 region by serotonin and noradrenaline. | 2005 Aug |
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Identification of the central imidazoline receptor subtype involved in modulation of halothane-epinephrine arrhythmias in rats. | 2005 Dec |
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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 |
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Monomeric G-protein, Rhes, is not an imidazoline-regulated protein in pancreatic beta-cells. | 2005 Dec 23 |
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Anticataleptic properties of alpha2 adrenergic antagonists in the crossed leg position and bar tests: differential mediation by 5-HT1A receptor activation. | 2005 Feb |
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Rat clonidine mydriasis model: imidazoline receptors are not involved. | 2005 Jan 15 |
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[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 |
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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 |
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Mechanisms involved in the antinociception caused by agmatine in mice. | 2005 Jun |
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Urinary responses to acute moxonidine are inhibited by natriuretic peptide receptor antagonist. | 2005 May |
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Site-dependent inhibition of neuronal c-jun in the brainstem elicited by imidazoline I1 receptor activation: role in rilmenidine-evoked hypotension. | 2005 May 9 |
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IRAS, a candidate for I1-imidazoline receptor, mediates inhibitory effect of agmatine on cellular morphine dependence. | 2005 Oct 1 |
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Involvement of supraspinal imidazoline receptors and descending monoaminergic pathways in tizanidine-induced inhibition of rat spinal reflexes. | 2005 Sep |
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Mitogen-activated protein kinase phosphorylation in the rostral ventrolateral medulla plays a key role in imidazoline (i1)-receptor-mediated hypotension. | 2005 Sep |
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Effect of BU98008, an imidazoline1-binding site ligand, on body temperature in mice. | 2005 Sep 5 |
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Involvement of phosphatidylcholine-selective phospholipase C in activation of mitogen-activated protein kinase pathways in imidazoline receptor antisera-selected protein. | 2006 Aug 15 |
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Involvement of I2-imidazoline binding sites in positive and negative morphine analgesia modulatory effects. | 2006 Dec 28 |
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Presynaptic I1-imidazoline receptors reduce GABAergic synaptic transmission in striatal medium spiny neurons. | 2006 Feb 8 |
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Theoretical study of structure, pKa, lipophilicity, solubility, absorption, and polar surface area of some centrally acting antihypertensives. | 2006 Mar 15 |
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Rhes expression in pancreatic beta-cells is regulated by efaroxan in a calcium-dependent process. | 2006 Oct 20 |
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Modulation of agmatine on calcium signal in morphine-dependent CHO cells by activation of IRAS, a candidate for imidazoline I1 receptor. | 2006 Oct 24 |
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RX871024 reduces NO production but does not protect against pancreatic beta-cell death induced by proinflammatory cytokines. | 2006 Sep 8 |
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Imidazoline receptors in relaxation of acetylcholine-constricted isolated rat jejunum. | 2006 Sep-Oct |
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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 |
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Antagonism of the insulinotropic action of first generation imidazolines by openers of K(ATP) channels. | 2007 Jan 1 |
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Possible role of NMDA receptors in antinociception induced by rilmenidine in mice in the formalin test. | 2007 Jul |
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Characterization of an antiproliferative effect of imidazoline receptor ligands on PC12 cells. | 2007 Nov-Dec |
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The imidazoline RX871024 induces death of proliferating insulin-secreting cells by activation of c-jun N-terminal kinase. | 2008 Apr |
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Antihypertensive drug guanabenz is active in vivo against both yeast and mammalian prions. | 2008 Apr 23 |
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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 |
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Dexmedetomidine reduces long-term potentiation in mouse hippocampus. | 2008 Jan |
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alpha2A-adrenoceptor antagonism increases insulin secretion and synergistically augments the insulinotropic effect of glibenclamide in mice. | 2008 Jul |
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Imidazoline I(1) receptor-mediated reduction of muscle rigidity in the reserpine-treated murine model of Parkinson's disease. | 2008 Jul 28 |
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Effects of spinal alpha(2)-adrenoceptor and I(1)-imidazoline receptor activation on hindlimb movement induction in spinal cord-injured mice. | 2008 Jun |
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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 |
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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 |
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Effect of moxonidine on the uveoscleral outflow: role of alpha2-adrenoceptors or i1 imidazoline receptors. | 2009 Apr |
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Dexmedetomidine, an alpha2-adrenergic agonist, inhibits neuronal delayed-rectifier potassium current and sodium current. | 2009 Aug |
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Proinflammatory cytokines activate the intrinsic apoptotic pathway in beta-cells. | 2009 Aug |
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Interruption of central neuronal pathway of imidazoline I1 receptor mediates the hypertensive effect of cyclosporine in rats. | 2009 Jan 12 |
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Preventive mechanisms of agmatine against ischemic acute kidney injury in rats. | 2009 Jan 28 |
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The insulinotropic effect of fluoroquinolones. | 2009 Mar 15 |
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Antineoplastic activity of idazoxan hydrochloride. | 2009 Nov |
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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
Edited
Fri Jun 25 21:56:41 UTC 2021
by
admin
on
Fri Jun 25 21:56:41 UTC 2021
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Record UNII |
G00490L21H
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Record Status |
Validated (UNII)
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Record Version |
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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
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89197-32-0
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C062597
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C72923
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89197-32-0
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6216
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admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
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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
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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
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SUB06462MIG
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admin on Fri Jun 25 21:56:41 UTC 2021 , Edited by admin on Fri Jun 25 21:56:41 UTC 2021
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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
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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
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PRIMARY |
Related Record | Type | Details | ||
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TARGET -> AGONIST |
SHORT-ACTING
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |