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

Details

Stereochemistry RACEMIC
Molecular Formula C11H12N2O2
Molecular Weight 204.2256
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IDAZOXAN

SMILES

c1ccc2c(c1)OCC(C3=NCCN3)O2

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 204.2256
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
[Action of agmatine on tension of isolated aortic artery and its receptor mechanism in rats].
2001 Apr
A morpholinocatechol compound (UK42620) with clonidine- and tyramine-like actions.
2001 Aug
Endogenous adrenergic control of reflexes evoked by mechanical stimulation of the heel in the decerebrated rabbit.
2001 Aug 10
Differential responses of regional vascular beds to local injection of agmatine in rats.
2001 Dec
In vitro and in vivo impairment of alpha2-adrenergic receptor-dependent antilipolysis by fatty acids in human adipose tissue.
2001 Dec
Desensitization of insulin secretory response to imidazolines, tolbutamide, and quinine. II. Electrophysiological and fluorimetric studies.
2001 Dec 15
Desensitization of insulin secretory response to imidazolines, tolbutamide, and quinine. I. Secretory and morphological studies.
2001 Dec 15
Down-regulation of MAO-B activity and imidazoline receptors in rat brain following chronic treatment of morphine.
2001 Jul
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
Role of alpha(2)-adrenoceptors in the sympathetic inhibition of motility reflexes of guinea-pig ileum.
2001 Jul 15
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
Hemodynamic effects of agmatine in Dahl salt-sensitive hypertensive and Dahl salt-resistant rats.
2001 Oct
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
Dopamine inhibits vasopressin action in the rat inner medullary collecting duct via alpha(2)-adrenoceptors.
2001 Sep
Evidence for the involvement of central I1 imidazoline receptor in ethanol counteraction of clonidine hypotension in spontaneously hypertensive rats.
2001 Sep
Changes of the excitability of rat trigeminal root ganglion neurons evoked by alpha(2)-adrenoreceptors.
2002
Intrathecal clonidine decreases spinal nitric oxide release in a rat model of complete Freund's adjuvant induced inflammatory pain.
2002 Aug
Enhanced stability of wild-type and constitutively active alpha(2A)-adrenoceptors by ligands with agonist, silent and inverse agonist properties.
2002 Aug
Distribution of [(3)H]BU224, a selective imidazoline I(2) binding site ligand, in rat brain.
2002 Aug 16
Agmatine inhibits arginine vasopressin-stimulated urea transport in the rat inner medullary collecting duct.
2002 Dec
Comparison of the ORL1 receptor-mediated inhibition of noradrenaline release in human and rat neocortical slices.
2002 Feb
Mechanisms involved in the water intake-related pressor response in the rat.
2002 Feb
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 Feb 25
Testosterone dependence of salt-induced hypertension in Sabra rats and role of renal alpha(2)-adrenoceptor subtypes.
2002 Jan
Tonic immobility in guinea pigs: a behavioural response for detecting an anxiolytic-like effect?
2002 Jul
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 Jul
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
Prenatal cocaine exposure alters sensitivity to the effects of idazoxan in a distraction task.
2002 Jul 18
Characterization of [(3)H]idazoxan binding sites on human platelets.
2002 Jun
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(2)-Adrenergic receptors in NTS facilitate baroreflex function in adult spontaneously hypertensive rats.
2002 Jun
Involvement of imidazoline receptors in the centrally acting muscle-relaxant effects of tizanidine.
2002 Jun 12
Imidazoline drugs stabilize lysosomes and inhibit oxidative cytotoxicity in astrocytes.
2002 Mar 1
Spinal noradrenergic activation mediates allodynia reduction from an allosteric adenosine modulator in a rat model of neuropathic pain.
2002 May
Role of histamine H3 receptors in control of mouse intestinal motility in vivo and in vitro: comparison with alpha2-adrenoceptors.
2002 May
alpha(2B)-Adrenergic receptors activate MAPK and modulate proliferation of primary cultured proximal tubule cells.
2002 May
Biochemical and functional characterization of alpha-adrenergic receptors in the rabbit vagina.
2002 Nov 1
Central serotonergic and adrenergic/imidazoline inhibitory mechanisms on sodium and water intake.
2002 Nov 22
Adrenoceptors in avian and fish pigment cells.
2002 Oct
Alpha(1)-adrenoceptor stimulation directly induces growth of vascular wall in vivo.
2002 Oct
Effects of medullary alpha2-adrenoceptor blockade in the rat.
2002 Oct 25
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
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 Fri Jun 25 21:53:19 UTC 2021
Edited
by admin
on Fri Jun 25 21:53:19 UTC 2021
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 Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
CAS
84720-37-6
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
SUPERSEDED
CAS
79944-58-4
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
MERCK INDEX
M6198
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY Merck Index
MESH
D019329
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
FDA UNII
Y310PA316B
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
DRUG BANK
DB12551
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
EVMPD
SUB08113MIG
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
EPA CompTox
79944-58-4
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
ChEMBL
CHEMBL10316
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
WIKIPEDIA
IDAZOXAN
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
NCI_THESAURUS
C170049
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
PUBCHEM
54459
Created by admin on Fri Jun 25 21:53:19 UTC 2021 , Edited by admin on Fri Jun 25 21:53:19 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
SHORT-ACTING
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY