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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=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 ( + / - )

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
Noradrenoceptor antagonism with idazoxan improves L-dopa-induced dyskinesias in MPTP monkeys.
2000 Feb
Idazoxan is ineffective for levodopa-induced dyskinesias in Parkinson's disease.
2000 Mar
Hypoxic-ischaemic brain damage in immature rats: effects of adrenoceptor modulation.
2001
[Action of agmatine on tension of isolated aortic artery and its receptor mechanism in rats].
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
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
Differential responses of regional vascular beds to local injection of agmatine in rats.
2001 Dec
Functional and pharmacological characterization of the modulatory role of serotonin on the firing activity of locus coeruleus norepinephrine neurons.
2001 Dec 13
Role of alpha(2)-adrenoceptors in the sympathetic inhibition of motility reflexes of guinea-pig ileum.
2001 Jul 15
Inverse agonist activity at the alpha(2A)-adrenergic receptor.
2001 Mar
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
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
Involvement of imidazoline receptors in the baroreflex effects of rilmenidine in conscious rabbits.
2001 Sep
Agmatine: a mastoparan-like activity related to direct activation of heterotrimeric G proteins.
2002 Jan 18
Inhibition of pilocarpine-induced salivation in rats by central noradrenaline.
2002 Jun
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
Effects of serotonin (5-hydroxytryptamine, 5-HT) reuptake inhibition plus 5-HT(2A) receptor antagonism on the firing activity of norepinephrine neurons.
2002 Sep
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 14:53:05 UTC 2023
Edited
by admin
on Thu Jul 06 14:53:05 UTC 2023
Record UNII
15394QZS7A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IDAZOXAN HYDROCHLORIDE
MI  
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
Created by admin on Thu Jul 06 14:53:05 UTC 2023 , Edited by admin on Thu Jul 06 14:53:05 UTC 2023
SUPERSEDED
PUBCHEM
154494
Created by admin on Thu Jul 06 14:53:05 UTC 2023 , Edited by admin on Thu Jul 06 14:53:05 UTC 2023
PRIMARY
MERCK INDEX
M6198
Created by admin on Thu Jul 06 14:53:05 UTC 2023 , Edited by admin on Thu Jul 06 14:53:05 UTC 2023
PRIMARY Merck Index
CAS
79944-56-2
Created by admin on Thu Jul 06 14:53:05 UTC 2023 , Edited by admin on Thu Jul 06 14:53:05 UTC 2023
PRIMARY
CAS
109518-43-6
Created by admin on Thu Jul 06 14:53:05 UTC 2023 , Edited by admin on Thu Jul 06 14:53:05 UTC 2023
SUPERSEDED
FDA UNII
15394QZS7A
Created by admin on Thu Jul 06 14:53:05 UTC 2023 , Edited by admin on Thu Jul 06 14:53:05 UTC 2023
PRIMARY
EPA CompTox
DTXSID10920189
Created by admin on Thu Jul 06 14:53:05 UTC 2023 , Edited by admin on Thu Jul 06 14:53:05 UTC 2023
PRIMARY
Related Record Type Details
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ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE