EFAROXAN

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H16N2O
Molecular Weight	216.2789
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1(CC2=C(O1)C=CC=C2)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	216.2789
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://adisinsight.springer.com/drugs/800000035 | https://www.ncbi.nlm.nih.gov/pubmed/12798376 | https://www.ncbi.nlm.nih.gov/pubmed/20504687 | https://www.ncbi.nlm.nih.gov/pubmed/1687123

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

Targets

Primary Target	Pharmacology	Condition	Potency
Alpha-2a adrenergic receptor 70 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27265687 \| https://www.ncbi.nlm.nih.gov/pubmed/23376415 \| https://www.ncbi.nlm.nih.gov/pubmed/14716222	Antagonist 2849		4.4 nM [Ki]
Nischarin 7 Target ID: CHEMBL3923 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18621536 \| https://www.ncbi.nlm.nih.gov/pubmed/23166584	Antagonist 2849		52.36 nM [Ki]

PubMed

Title	Date	PubMed
Antineoplastic activity of idazoxan hydrochloride.	2009-11	19308411
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.	2009-10-23	19725810
Antidepressant like effect of selective serotonin reuptake inhibitors involve modulation of imidazoline receptors by agmatine.	2009-09	19589348
Dexmedetomidine, an alpha2-adrenergic agonist, inhibits neuronal delayed-rectifier potassium current and sodium current.	2009-08	19542547
Proinflammatory cytokines activate the intrinsic apoptotic pathway in beta-cells.	2009-08	19470609
Effect of moxonidine on the uveoscleral outflow: role of alpha2-adrenoceptors or i1 imidazoline receptors.	2009-04	19373577
The insulinotropic effect of fluoroquinolones.	2009-03-15	19073153
Preventive mechanisms of agmatine against ischemic acute kidney injury in rats.	2009-01-28	19105953
Interruption of central neuronal pathway of imidazoline I1 receptor mediates the hypertensive effect of cyclosporine in rats.	2009-01-12	19028461
Effect of agmatine on DAMGO-induced mu-opioid receptor down-regulation and internalization via activation of IRAS, a candidate for imidazoline I(1) receptor.	2008-12-03	18845140
Imidazoline I(1) receptor-mediated reduction of muscle rigidity in the reserpine-treated murine model of Parkinson's disease.	2008-07-28	18602099
alpha2A-adrenoceptor antagonism increases insulin secretion and synergistically augments the insulinotropic effect of glibenclamide in mice.	2008-07	18493247
Effects of spinal alpha(2)-adrenoceptor and I(1)-imidazoline receptor activation on hindlimb movement induction in spinal cord-injured mice.	2008-06	18364473
Caffeine and a selective adenosine A(2B) receptor antagonist but not imidazoline receptor antagonists modulate antinociception induced by diphenyl diselenide in mice.	2008-05-09	18375062
Antihypertensive drug guanabenz is active in vivo against both yeast and mammalian prions.	2008-04-23	18431471
The imidazoline RX871024 induces death of proliferating insulin-secreting cells by activation of c-jun N-terminal kinase.	2008-04	18278435
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.	2008-03	18292683
Dexmedetomidine reduces long-term potentiation in mouse hippocampus.	2008-01	18156887
Sympathoexcitation of moxonidine in the caudal ventrolateral medulla is dependent on I1-imidazoline receptors in anesthetized rats.	2007-10-16	17889438
Characterization of an antiproliferative effect of imidazoline receptor ligands on PC12 cells.	2007-07-11	18195472
Possible role of NMDA receptors in antinociception induced by rilmenidine in mice in the formalin test.	2007-07	16934506
Evidence for imidazoline receptors involvement in the agmatine antidepressant-like effect in the forced swimming test.	2007-06-22	17445795
Quantification of very low enantiomeric impurity of efaroxan using a dual cyclodextrin system by capillary electrophoresis.	2007-06-05	17512818
Validation of a method using an achiral liquid chromatography sorbent and a circular dichroism detector. Analysis of the efaroxan enantiomers.	2007-02-09	17207805
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.	2007-02	17096379
Antagonism of the insulinotropic action of first generation imidazolines by openers of K(ATP) channels.	2007-01-01	17056015
Involvement of I2-imidazoline binding sites in positive and negative morphine analgesia modulatory effects.	2006-12-28	17081513
Modulation of agmatine on calcium signal in morphine-dependent CHO cells by activation of IRAS, a candidate for imidazoline I1 receptor.	2006-10-24	16962578
Rhes expression in pancreatic beta-cells is regulated by efaroxan in a calcium-dependent process.	2006-10-20	16945334
RX871024 reduces NO production but does not protect against pancreatic beta-cell death induced by proinflammatory cytokines.	2006-09-08	16870144
Involvement of phosphatidylcholine-selective phospholipase C in activation of mitogen-activated protein kinase pathways in imidazoline receptor antisera-selected protein.	2006-08-15	16598778
Theoretical study of structure, pKa, lipophilicity, solubility, absorption, and polar surface area of some centrally acting antihypertensives.	2006-03-15	16263295
Presynaptic I1-imidazoline receptors reduce GABAergic synaptic transmission in striatal medium spiny neurons.	2006-02-08	16467528
Monomeric G-protein, Rhes, is not an imidazoline-regulated protein in pancreatic beta-cells.	2005-12-23	16277977
Identification of the central imidazoline receptor subtype involved in modulation of halothane-epinephrine arrhythmias in rats.	2005-12	16301242
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.	2005-12	16283242
Imidazoline receptors in relaxation of acetylcholine-constricted isolated rat jejunum.	2005-11-25	17085862
IRAS, a candidate for I1-imidazoline receptor, mediates inhibitory effect of agmatine on cellular morphine dependence.	2005-10-01	16112088
Effect of BU98008, an imidazoline1-binding site ligand, on body temperature in mice.	2005-09-05	16109403
Involvement of supraspinal imidazoline receptors and descending monoaminergic pathways in tizanidine-induced inhibition of rat spinal reflexes.	2005-09	16127244
Mitogen-activated protein kinase phosphorylation in the rostral ventrolateral medulla plays a key role in imidazoline (i1)-receptor-mediated hypotension.	2005-09	15901801
Inhibition of perforant path input to the CA1 region by serotonin and noradrenaline.	2005-08	15888529
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.	2005-07	15965355
Mechanisms involved in the antinociception caused by agmatine in mice.	2005-06	15857629
Site-dependent inhibition of neuronal c-jun in the brainstem elicited by imidazoline I1 receptor activation: role in rilmenidine-evoked hypotension.	2005-05-09	15910806
Urinary responses to acute moxonidine are inhibited by natriuretic peptide receptor antagonist.	2005-05	15700025
Noradrenergic modulation of XII motoneuron inspiratory activity does not involve alpha2-receptor inhibition of the Ih current or presynaptic glutamate release.	2005-04	15579572
[The role of alpha2-adrenergic and I1-imidazoline receptors in the effects of clonidine and moxonidine on isolated large intestine of mice].	2005-03-25	15786962
Rat clonidine mydriasis model: imidazoline receptors are not involved.	2005-01-15	15620566
Imidazoline receptors associated with noradrenergic terminals in the rostral ventrolateral medulla mediate the hypotensive responses of moxonidine but not clonidine.	2005	15857704

Patents

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:58:58 GMT 2025` Edited by `admin` on `Wed Apr 02 07:58:58 GMT 2025`
Record UNII	G00490L21H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EFAROXAN

Official Name

English

1H-IMIDAZOLE, 2-(2-ETHYL-2,3-DIHYDRO-2-BENZOFURANYL)-4,5-DIHYDRO-

Preferred Name

English

2-(2-ETHYL-2,3-DIHYDRO-2-BENZOFURANYL)-4,5-DIHYDRO-1H-IMIDAZOLE

Systematic Name

English

NSC-759562

Code

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