IDAZOXAN HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H12N2O2.ClH
Molecular Weight	240.686
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.C1CN=C(N1)C2COC3=CC=CC=C3O2

InChI

InChIKey=MYUBYOVCLMEAOH-UHFFFAOYSA-N

InChI=1S/C11H12N2O2.ClH/c1-2-4-9-8(3-1)14-7-10(15-9)11-12-5-6-13-11;/h1-4,10H,5-7H2,(H,12,13);1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C11H12N2O2
Molecular Weight	204.2252
Charge	0
Count

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

Description
Sources: http://adisinsight.springer.com/drugs/800000691 | https://www.ncbi.nlm.nih.gov/pubmed/2875218

Idazoxan is an alpha2 receptor antagonist which also shows activity at imidazoline I1 and I2 receptors and modulates the release of dopamine. Idazoxan was in phase II development in the US. Later the development of idazoxan for schizophrenia was discontinued. It was also in clinical trials for cognition disorders in United Kingdom, and was also discontinued. Idazoxan is used in scientific research as a tool for the study of alpha 2-adrenoceptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Alpha-2b adrenergic receptor 27 Target ID: CHEMBL1942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10636247	Antagonist 2737	7.71 null [pIC50]
Alpha-2a adrenergic receptor 60 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10636247	Antagonist 2737	8.08 null [pIC50]
Alpha-2c adrenergic receptor 37 Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10636247	Antagonist 2737	7.27 null [pIC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 288 Sources: http://adisinsight.springer.com/drugs/800000691 https://www.ncbi.nlm.nih.gov/pubmed/8733795	Primary		Phase II 1133	Unknown Approved Use Unknown
Major depressive disorder 172 Sources: https://clinicaltrials.gov/ct2/show/NCT00294944 http://adisinsight.springer.com/drugs/800000691	Primary		Phase III 651	Unknown Approved Use Unknown

AUC

Value	Dose	Co-administered	Analyte	Population
179.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2872058/	0.3 mg/kg single, oral dose: 0.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		IDAZOXAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
560.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2872058/	0.3 mg/kg single, intravenous dose: 0.3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		IDAZOXAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.59 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2872058/	0.3 mg/kg single, oral dose: 0.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		IDAZOXAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2872058/	0.3 mg/kg single, intravenous dose: 0.3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		IDAZOXAN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

PubMed

Title	Date	PubMed
Effects of the pesticide amitraz and its metabolite BTS 27271 on insulin and glucagon secretion from the perfused rat pancreas: involvement of alpha2D-adrenergic receptors.	1999 Nov	10582558
Effect of alpha-2 adrenoceptor antagonists on colonic function in rats.	2000 Jun	10867622
Hypoxic-ischaemic brain damage in immature rats: effects of adrenoceptor modulation.	2001	11277361
Co-transmitter function of ATP in central catecholaminergic neurons of the rat.	2001	11226696
Modification of norepinephrine and serotonin, but not dopamine, neuron firing by sustained bupropion treatment.	2001 Apr	11374336
Alpha2A-adrenoceptor mediated tachypnea in awake goats.	2001 Apr	11282385
Agonist trafficking of G(i/o)-mediated alpha(2A)-adrenoceptor responses in HEL 92.1.7 cells.	2001 Apr	11264241
Idazoxan and 8-OH-DPAT modify the behavioral effects induced by either NA, or 5-HT, or dual NA/5-HT reuptake inhibition in the rat forced swimming test.	2001 Apr	11182533
The noradrenaline-dopamine interaction in the rat medial prefrontal cortex studied by multi-probe microdialysis.	2001 Apr 27	11343687
Nitric oxide-independent effects of tempol on sympathetic nerve activity and blood pressure in normotensive rats.	2001 Aug	11454605
Differential responses of regional vascular beds to local injection of agmatine in rats.	2001 Dec	11930224
In vitro and in vivo impairment of alpha2-adrenergic receptor-dependent antilipolysis by fatty acids in human adipose tissue.	2001 Dec	11753754
Functional and pharmacological characterization of the modulatory role of serotonin on the firing activity of locus coeruleus norepinephrine neurons.	2001 Dec 13	11730697
Desensitization of insulin secretory response to imidazolines, tolbutamide, and quinine. II. Electrophysiological and fluorimetric studies.	2001 Dec 15	11755123
Desensitization of insulin secretory response to imidazolines, tolbutamide, and quinine. I. Secretory and morphological studies.	2001 Dec 15	11755122
Presynaptic alpha2-adrenoceptor-mediated modulation of adenosine 5' triphosphate and noradrenaline corelease: differences in canine mesenteric artery and vein.	2001 Feb	11422578
Imidazolines inhibit secretory responses of rat colonic mucosa to calcium-dependent but not cyclic AMP-dependent secretagogues.	2001 Feb	11273018
Differential effects of clonidine, dopamine, dobutamine, and dopexamine on basal and acid-stimulated mucosal blood flow in the rat stomach.	2001 Feb	11246314
Rabbit alpha2-adrenoceptors: both platelets and adipocytes have alpha2A-pharmacology.	2001 Jul	11408545
Differential [(3)H]idazoxan and [(3)H]2-(2-benzofuranyl)-2-imidazoline (2-BFI) binding to imidazoline I(2) receptors in human postmortem frontal cortex.	2001 Jul 6	11448473
The alpha 2 adrenoceptor antagonists RX 821002 and yohimbine delay-dependently impair choice accuracy in a delayed non-matching-to-position task in rats.	2001 Jun	11441427
Agmatine inhibits carotid sinus baroreflex in anesthetized rats.	2001 Mar	11742575
Receptor phosphorylation mediates estradiol reduction of alpha2-adrenoceptor coupling to G protein in the hypothalamus of female rats.	2001 Mar	11394633
Inverse agonist activity at the alpha(2A)-adrenergic receptor.	2001 Mar	11179449
The differential effects of prenatal stress in rats on the acoustic startle reflex under baseline conditions and in response to anxiogenic drugs.	2001 Mar 1	11314679
Posttraining infusion of norepinephrine and corticotropin releasing factor into the bed nucleus of the stria terminalis enhanced retention in an inhibitory avoidance task.	2001 Mar 31	11403518
Morphine and clonidine activate different K+ channels on rat amygdala neurons.	2001 Mar 9	11245859
Analysis of ligand activation of alpha 2-adrenoceptor subtypes under conditions of equal G alpha protein stoichiometry.	2001 May	11383713
Antidepressant drug-induced alterations in neuron-localized tumor necrosis factor-alpha mRNA and alpha(2)-adrenergic receptor sensitivity.	2001 May	11303058
Chronic hypoxia alters prejunctional alpha(2)-receptor function in vascular adrenergic nerves of adult and fetal sheep.	2001 Sep	11507010
Dopamine inhibits vasopressin action in the rat inner medullary collecting duct via alpha(2)-adrenoceptors.	2001 Sep	11504796
Alpha2-adrenoceptor activation increases a cationic conductance and spontaneous GABAergic synaptic activity in dopaminergic neurones of the rat substantia nigra.	2002	12453479
Changes of the excitability of rat trigeminal root ganglion neurons evoked by alpha(2)-adrenoreceptors.	2002	12435412
Intrathecal clonidine decreases spinal nitric oxide release in a rat model of complete Freund's adjuvant induced inflammatory pain.	2002 Aug	12184629
Effect of antisense knock-down of alpha(2a)- and alpha(2c)-adrenoceptors on the antinociceptive action of clonidine on trigeminal nociception in the rat.	2002 Jul	12098614
Involvement of imidazoline receptors in the centrally acting muscle-relaxant effects of tizanidine.	2002 Jun 12	12079683
Spinal noradrenergic activation mediates allodynia reduction from an allosteric adenosine modulator in a rat model of neuropathic pain.	2002 May	12031785
In vivo tonic modulation of the noradrenaline release in the rat cortex by locus coeruleus somatodendritic alpha(2)-adrenoceptors.	2002 May 10	12065075
Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina.	2002 Nov 1	12377271
Central serotonergic and adrenergic/imidazoline inhibitory mechanisms on sodium and water intake.	2002 Nov 22	12426052
RX 821002 as a tool for physiological investigation of alpha(2)-adrenoceptors.	2002 Summer	12177687
Central alpha(2) adrenergic receptors and cholinergic-induced salivation in rats.	2003 Jan 30	12507689

Patents

Sample Use Guides

In Vivo Use Guide

Parkinson's disease:single oral doses (10 mg, 20 mg, and 40 mg) of idazoxan

Route of Administration: Oral

In Vitro Use Guide

Idazoxan (10(-4) mol/L), an alpha 2-adrenergic receptor (alpha 2-AR) and imidazoline receptor (IR) antagonist, abolished the Agm-induced vasorelaxation completely under the condition of CaCl2-induced precontraction in the isolated aortic artery of rats..

Substance Class	Chemical Created by `admin` on `Sun Dec 18 01:58:14 UTC 2022` Edited by `admin` on `Sun Dec 18 01:58:14 UTC 2022`
Record UNII	15394QZS7A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IDAZOXAN HYDROCHLORIDE

Common Name

English

1H-IMIDAZOLE, 2-(2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)-4,5-DIHYDRO-, MONOHYDROCHLORIDE

Systematic Name

English

RX-781094

Code

English

1H-IMIDAZOLE, 2-(2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)-4,5-DIHYDRO-, HYDROCHLORIDE (1:1)

Systematic Name

English

(±)-IDAZOXAN MONOHYDROCHLORIDE

Common Name

English

RX-781094A

Code

English

2-(2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)-4,5-DIHYDRO-1H-IMIDAZOLE HYDROCHLORIDE

Systematic Name

English

IDAZOXAN HYDROCHLORIDE [MI]

Common Name

English

Code System Code Type Description

CAS

90755-83-2