U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of IDAZOXAN HYDROCHLORIDE

SMILES

Cl.C1CN=C(N1)C2COC3=C(O2)C=CC=C3

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 C11H12N2O2
Molecular Weight 204.2252
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
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

Description

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 7.71 null [pIC50]
Antagonist
2849
 8.08 null [pIC50]
Antagonist
2849
 7.27 null [pIC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase III
665
Unknown

Approved Use

Unknown
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

PubMed

TitleDatePubMed
Central alpha(2) adrenergic receptors and cholinergic-induced salivation in rats.
2003-01-30
Involvement of I(1)-imidazoline receptors in baroreceptor reflex in the caudal ventrolateral medulla of rats.
2003-01-17
Different roles for Gi and Go proteins in modulation of adenylyl cyclase type-2 activity.
2002-12
Agmatine inhibits arginine vasopressin-stimulated urea transport in the rat inner medullary collecting duct.
2002-12
Central serotonergic and adrenergic/imidazoline inhibitory mechanisms on sodium and water intake.
2002-11-22
Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina.
2002-11-01
Effects of medullary alpha2-adrenoceptor blockade in the rat.
2002-10-25
Adrenoceptors in avian and fish pigment cells.
2002-10
Alpha(1)-adrenoceptor stimulation directly induces growth of vascular wall in vivo.
2002-10
Effects of serotonin (5-hydroxytryptamine, 5-HT) reuptake inhibition plus 5-HT(2A) receptor antagonism on the firing activity of norepinephrine neurons.
2002-09
Distribution of [(3)H]BU224, a selective imidazoline I(2) binding site ligand, in rat brain.
2002-08-16
Intrathecal clonidine decreases spinal nitric oxide release in a rat model of complete Freund's adjuvant induced inflammatory pain.
2002-08
Enhanced stability of wild-type and constitutively active alpha(2A)-adrenoceptors by ligands with agonist, silent and inverse agonist properties.
2002-08
Prenatal cocaine exposure alters sensitivity to the effects of idazoxan in a distraction task.
2002-07-18
Tonic immobility in guinea pigs: a behavioural response for detecting an anxiolytic-like effect?
2002-07
Actions of alpha-2 noradrenergic agonists on spatial working memory and blood pressure in rhesus monkeys appear to be mediated by the same receptor subtype.
2002-07
Effect of antisense knock-down of alpha(2a)- and alpha(2c)-adrenoceptors on the antinociceptive action of clonidine on trigeminal nociception in the rat.
2002-07
Involvement of imidazoline receptors in the centrally acting muscle-relaxant effects of tizanidine.
2002-06-12
Characterization of [(3)H]idazoxan binding sites on human platelets.
2002-06
Inhibition of pilocarpine-induced salivation in rats by central noradrenaline.
2002-06
Imidazoline(2) (I(2)) binding site- and alpha(2)-adrenoceptor-mediated modulation of central noradrenergic and HPA axis function in control rats and chronically stressed rats with adjuvant-induced arthritis.
2002-06
Pre- and postjunctional alpha(2)-adrenergic receptors in fetal and adult ovine cerebral arteries.
2002-06
Different alpha-adrenoceptors mediate migration of vascular smooth muscle cells and adventitial fibroblasts in vitro.
2002-06
alpha(2)-Adrenergic receptors in NTS facilitate baroreflex function in adult spontaneously hypertensive rats.
2002-06
In vivo tonic modulation of the noradrenaline release in the rat cortex by locus coeruleus somatodendritic alpha(2)-adrenoceptors.
2002-05-10
Spinal noradrenergic activation mediates allodynia reduction from an allosteric adenosine modulator in a rat model of neuropathic pain.
2002-05
Role of histamine H3 receptors in control of mouse intestinal motility in vivo and in vitro: comparison with alpha2-adrenoceptors.
2002-05
alpha(2B)-Adrenergic receptors activate MAPK and modulate proliferation of primary cultured proximal tubule cells.
2002-05
Imidazoline drugs stabilize lysosomes and inhibit oxidative cytotoxicity in astrocytes.
2002-03-01
Seasonal changes in the densities of alpha(2) noradrenergic receptors are inversely related to changes in testosterone and the volumes of song control nuclei in male European starlings.
2002-02-25
Comparison of the ORL1 receptor-mediated inhibition of noradrenaline release in human and rat neocortical slices.
2002-02
Mechanisms involved in the water intake-related pressor response in the rat.
2002-02
Agmatine: a mastoparan-like activity related to direct activation of heterotrimeric G proteins.
2002-01-18
Alpha2-adrenoreceptors profile modulation and high antinociceptive activity of (S)-(-)-2-[1-(biphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole.
2002-01-03
Testosterone dependence of salt-induced hypertension in Sabra rats and role of renal alpha(2)-adrenoceptor subtypes.
2002-01
Alpha2-adrenoceptor activation increases a cationic conductance and spontaneous GABAergic synaptic activity in dopaminergic neurones of the rat substantia nigra.
2002
Changes of the excitability of rat trigeminal root ganglion neurons evoked by alpha(2)-adrenoreceptors.
2002
RX 821002 as a tool for physiological investigation of alpha(2)-adrenoceptors.
2002
Interactions between cutaneous afferent inputs to a withdrawal reflex in the decerebrated rabbit and their control by descending and segmental systems.
2002
Desensitization of insulin secretory response to imidazolines, tolbutamide, and quinine. II. Electrophysiological and fluorimetric studies.
2001-12-15
Desensitization of insulin secretory response to imidazolines, tolbutamide, and quinine. I. Secretory and morphological studies.
2001-12-15
Functional and pharmacological characterization of the modulatory role of serotonin on the firing activity of locus coeruleus norepinephrine neurons.
2001-12-13
Differential responses of regional vascular beds to local injection of agmatine in rats.
2001-12
Combined alpha 2-adrenergic/D2 dopamine receptor blockade fails to reproduce the ability of clozapine to reverse phencyclidine-induced deficits in prepulse inhibition of startle.
2001-12
In vitro and in vivo impairment of alpha2-adrenergic receptor-dependent antilipolysis by fatty acids in human adipose tissue.
2001-12
Hemodynamic effects of agmatine in Dahl salt-sensitive hypertensive and Dahl salt-resistant rats.
2001-10
The involvement of alpha2-adrenoceptors in the anticonvulsive effect of swim stress in mice.
2001-10
A morpholinocatechol compound (UK42620) with clonidine- and tyramine-like actions.
2001-08
Down-regulation of MAO-B activity and imidazoline receptors in rat brain following chronic treatment of morphine.
2001-07
Agmatine inhibits carotid sinus baroreflex in anesthetized rats.
2001-03
Patents

Patents

20010041702
4
20050176798
2
20100173951
2
JP2003509371A
9

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 Mon Mar 31 22:38:51 GMT 2025
Edited
by admin
on Mon Mar 31 22:38:51 GMT 2025
Record UNII
15394QZS7A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IDAZOXAN HYDROCHLORIDE
MI  
Common Name English
RX-781094
Preferred Name English
1H-IMIDAZOLE, 2-(2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)-4,5-DIHYDRO-, MONOHYDROCHLORIDE
Systematic Name 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
Created by admin on Mon Mar 31 22:38:51 GMT 2025 , Edited by admin on Mon Mar 31 22:38:51 GMT 2025
SUPERSEDED
PUBCHEM
154494
Created by admin on Mon Mar 31 22:38:51 GMT 2025 , Edited by admin on Mon Mar 31 22:38:51 GMT 2025
PRIMARY
MERCK INDEX
m6198
Created by admin on Mon Mar 31 22:38:51 GMT 2025 , Edited by admin on Mon Mar 31 22:38:51 GMT 2025
PRIMARY Merck Index
CAS
79944-56-2
Created by admin on Mon Mar 31 22:38:51 GMT 2025 , Edited by admin on Mon Mar 31 22:38:51 GMT 2025
PRIMARY
CAS
109518-43-6
Created by admin on Mon Mar 31 22:38:51 GMT 2025 , Edited by admin on Mon Mar 31 22:38:51 GMT 2025
SUPERSEDED
FDA UNII
15394QZS7A
Created by admin on Mon Mar 31 22:38:51 GMT 2025 , Edited by admin on Mon Mar 31 22:38:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID10920189
Created by admin on Mon Mar 31 22:38:51 GMT 2025 , Edited by admin on Mon Mar 31 22:38:51 GMT 2025
PRIMARY
Related Record Type Details
Structure of IDAZOXAN
PARENT -> SALT/SOLVATE
Structure of IDAZOXAN HYDROCHLORIDE, (S)-
ENANTIOMER -> RACEMATE
Structure of IDAZOXAN HYDROCHLORIDE, (R)-
ENANTIOMER -> RACEMATE
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966