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Details

Stereochemistry RACEMIC
Molecular Formula C11H12N2O2
Molecular Weight 204.2252
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IDAZOXAN

SMILES

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

InChI

InChIKey=HPMRFMKYPGXPEP-UHFFFAOYSA-N
InChI=1S/C11H12N2O2/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)

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 ( + / - )

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.71 null [pIC50]
8.08 null [pIC50]
7.27 null [pIC50]
Conditions
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
179.5 ng × h/mL
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
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
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
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
Hypoxic-ischaemic brain damage in immature rats: effects of adrenoceptor modulation.
2001
Co-transmitter function of ATP in central catecholaminergic neurons of the rat.
2001
[Action of agmatine on tension of isolated aortic artery and its receptor mechanism in rats].
2001 Apr
Modification of norepinephrine and serotonin, but not dopamine, neuron firing by sustained bupropion treatment.
2001 Apr
Alpha2A-adrenoceptor mediated tachypnea in awake goats.
2001 Apr
Agonist trafficking of G(i/o)-mediated alpha(2A)-adrenoceptor responses in HEL 92.1.7 cells.
2001 Apr
Nonnoradrenergic mechanism of reflex cutaneous vasoconstriction in men.
2001 Apr
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
The noradrenaline-dopamine interaction in the rat medial prefrontal cortex studied by multi-probe microdialysis.
2001 Apr 27
A morpholinocatechol compound (UK42620) with clonidine- and tyramine-like actions.
2001 Aug
S33005, a novel ligand at both serotonin and norepinephrine transporters: I. Receptor binding, electrophysiological, and neurochemical profile in comparison with venlafaxine, reboxetine, citalopram, and clomipramine.
2001 Aug
Nitric oxide-independent effects of tempol on sympathetic nerve activity and blood pressure in normotensive rats.
2001 Aug
Functional and pharmacological characterization of the modulatory role of serotonin on the firing activity of locus coeruleus norepinephrine neurons.
2001 Dec 13
Desensitization of insulin secretory response to imidazolines, tolbutamide, and quinine. II. Electrophysiological and fluorimetric studies.
2001 Dec 15
Presynaptic alpha2-adrenoceptor-mediated modulation of adenosine 5' triphosphate and noradrenaline corelease: differences in canine mesenteric artery and vein.
2001 Feb
Interactions of ligands at angiotensin II-receptors and imidazoline receptors.
2001 Feb
Differential effects of clonidine, dopamine, dobutamine, and dopexamine on basal and acid-stimulated mucosal blood flow in the rat stomach.
2001 Feb
Chronic treatment with desipramine facilitates its effect on extracellular noradrenaline in the rat hippocampus: studies on the role of presynaptic alpha2-adrenoceptors.
2001 Jan
Idazoxan, an alpha-2 antagonist, and L-DOPA-induced dyskinesias in patients with Parkinson's disease.
2001 Jul
Neural mechanisms underlying peak-dose dyskinesia induced by levodopa and apomorphine are distinct: evidence from the effects of the alpha(2) adrenoceptor antagonist idazoxan.
2001 Jul
Neuropharmacological profile of a selective sigma ligand, igmesine: a potential antidepressant.
2001 Jul
Rabbit alpha2-adrenoceptors: both platelets and adipocytes have alpha2A-pharmacology.
2001 Jul
Role of alpha(2)-adrenoceptors in the sympathetic inhibition of motility reflexes of guinea-pig ileum.
2001 Jul 15
Chronic subordination stress in male tree shrews: replacement of testosterone affects behavior and central alpha(2)-adrenoceptors.
2001 Jun
Differential effects of alpha-adrenoceptor agonists on human retinal microvessel diameter.
2001 Jun
Selective imidazoline I2 ligands do not show antidepressant-like activity in the forced swim test in mice.
2001 Mar
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
Morphine and clonidine activate different K+ channels on rat amygdala neurons.
2001 Mar 9
Analysis of ligand activation of alpha 2-adrenoceptor subtypes under conditions of equal G alpha protein stoichiometry.
2001 May
Antidepressant drug-induced alterations in neuron-localized tumor necrosis factor-alpha mRNA and alpha(2)-adrenergic receptor sensitivity.
2001 May
Evidence for co-release of noradrenaline and dopamine from noradrenergic neurons in the cerebral cortex.
2001 Nov
Evidence for alpha-2 adrenoreceptor modulation of arterial chemoreflexes in the caudal solitary nucleus of the rat.
2001 Nov
The involvement of alpha2-adrenoceptors in the anticonvulsive effect of swim stress in mice.
2001 Oct
Alpha 2-adrenoceptor antagonists: effects on ejaculation, penile erection and pelvic thrusting behavior in dogs.
2001 Sep
Involvement of imidazoline receptors in the baroreflex effects of rilmenidine in conscious rabbits.
2001 Sep
Chronic hypoxia alters prejunctional alpha(2)-receptor function in vascular adrenergic nerves of adult and fetal sheep.
2001 Sep
Alpha2-adrenoceptor activation increases a cationic conductance and spontaneous GABAergic synaptic activity in dopaminergic neurones of the rat substantia nigra.
2002
Interactions between cutaneous afferent inputs to a withdrawal reflex in the decerebrated rabbit and their control by descending and segmental systems.
2002
Intrathecal clonidine decreases spinal nitric oxide release in a rat model of complete Freund's adjuvant induced inflammatory pain.
2002 Aug
Agmatine: a mastoparan-like activity related to direct activation of heterotrimeric G proteins.
2002 Jan 18
Alpha2-adrenoreceptors profile modulation and high antinociceptive activity of (S)-(-)-2-[1-(biphenyl-2-yloxy)ethyl]-4,5-dihydro-1H-imidazole.
2002 Jan 3
Inhibition of pilocarpine-induced salivation in rats by central noradrenaline.
2002 Jun
Pre- and postjunctional alpha(2)-adrenergic receptors in fetal and adult ovine cerebral arteries.
2002 Jun
Different alpha-adrenoceptors mediate migration of vascular smooth muscle cells and adventitial fibroblasts in vitro.
2002 Jun
alpha(2B)-Adrenergic receptors activate MAPK and modulate proliferation of primary cultured proximal tubule cells.
2002 May
Central serotonergic and adrenergic/imidazoline inhibitory mechanisms on sodium and water intake.
2002 Nov 22
Adrenoceptors in avian and fish pigment cells.
2002 Oct
Effects of serotonin (5-hydroxytryptamine, 5-HT) reuptake inhibition plus 5-HT(2A) receptor antagonism on the firing activity of norepinephrine neurons.
2002 Sep
RX 821002 as a tool for physiological investigation of alpha(2)-adrenoceptors.
2002 Summer
Central alpha(2) adrenergic receptors and cholinergic-induced salivation in rats.
2003 Jan 30
Patents

Sample Use Guides

Parkinson's disease:single oral doses (10 mg, 20 mg, and 40 mg) of idazoxan
Route of Administration: Oral
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 Thu Jul 06 00:14:24 UTC 2023
Edited
by admin
on Thu Jul 06 00:14:24 UTC 2023
Record UNII
Y310PA316B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IDAZOXAN
INN   MI  
INN  
Official Name English
IDAZOXAN [MI]
Common Name English
DL-IDAZOXAN
Common Name English
NSC-759867
Code English
RACEMIC IDAZOXAN
Common Name English
2-(2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)-4,5-DIHYDRO-1H-IMIDAZOLE
Systematic Name English
idazoxan [INN]
Common Name English
1H-IMIDAZOLE, 2-(2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)-4,5-DIHYDRO-
Systematic Name English
2-IMIDAZOLINE, 2-(1,4-BENZODIOXAN-2-YL)-
Systematic Name English
(±)-2-(1,4-BENZODIOXAN-2-YL)-2-IMIDAZOLINE
Systematic Name English
(±)-IDAZOXAN
Common Name English
Code System Code Type Description
INN
5337
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
CAS
84720-37-6
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
SUPERSEDED
CAS
79944-58-4
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
NSC
759867
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
CHEBI
5862
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
MERCK INDEX
M6198
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY Merck Index
MESH
D019329
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
FDA UNII
Y310PA316B
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
DRUG BANK
DB12551
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
EVMPD
SUB08113MIG
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID6045161
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
SMS_ID
100000083695
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL10316
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
WIKIPEDIA
IDAZOXAN
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
NCI_THESAURUS
C170049
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
PUBCHEM
54459
Created by admin on Thu Jul 06 00:14:24 UTC 2023 , Edited by admin on Thu Jul 06 00:14:24 UTC 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY