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Details

Stereochemistry RACEMIC
Molecular Formula C14H16N2O2.ClH
Molecular Weight 280.75
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IMILOXAN HYDROCHLORIDE

SMILES

Cl.CCN1C=CN=C1CC2COC3=CC=CC=C3O2

InChI

InChIKey=ANDJPJNFVJXEKX-UHFFFAOYSA-N
InChI=1S/C14H16N2O2.ClH/c1-2-16-8-7-15-14(16)9-11-10-17-12-5-3-4-6-13(12)18-11;/h3-8,11H,2,9-10H2,1H3;1H

HIDE SMILES / InChI
Molecular Formula C14H16N2O2
Molecular Weight 244.289
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

Imiloxan is a highly selective alpha2B adrenoceptor antagonist and was developed for depression in the 1980s. In Phase 1 clinical trials imiloxan dosing led to hypersensitivity reactions; the molecule's development was discontinued.

Originator

Roche
93
Curator's Comment: # Roche Bioscience - UCB

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Alpha-2B adrenergic receptor
13
Target ID: P18089
Gene ID: 151.0
Gene Symbol: ADRA2B
Target Organism: Homo sapiens (Human)
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
438
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP19A1
429

BSEP
550
P-gp
2052

UGTs
13
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP19A1
430
 no
CYP2C9
2497
 no
CYP3A4
2633
 no
BSEP
554
 weak [IC50 61.65 uM]
CYP2D6
2546
 yes [IC50 1.7377 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
UGTs
13
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY572843
https://www.001chemical.com/chem/81167-16-0
AAA Chemistry
AR-1A7844
ABI Chem
AC1L334I
ABI Chem
AC1Q7014
Ambinter
Amb22734572
http://www.ambinter.com/reference/22734572
AN PharmaTech
AN-3505
Chemieliva Pharmaceutical Co., Ltd
PBCM0850033
ChemShuttle
113757
http://www.chemshuttle.com/catalogsearch/result/?q=81167-16-0&cat=
DC Chemicals
DC7289
http://www.dcchemicals.com/product_show-Imiloxan.html
eNovation Chemicals
D676555
https://www.enovationchem.com/ProductDetails.asp?ProductID=D676555
Kingston Chemistry
KST-1A8980
Molcore
MC572843
https://www.molcore.com/product/81167-16-0
NovoSeek
133621
Sinfoo Biotech
S027350
http://www.sinfoobiotech.com/product/1030748
Smolecule
S530520
http://www.smolecule.com/products/s530520
Smolecule
S705424
https://www.smolecule.com/products/s705424
THE BioTek
bt-270733
https://www.thebiotek.com/product/inhibitors/bt-270733
PubMed

PubMed

TitleDatePubMed
Antinociceptive synergism of MD-354 and clonidine. Part II. The alpha-adrenoceptor component.
2010-08
Probable involvement of alpha(2C)-adrenoceptor subtype and endogenous opioid peptides in the peripheral antinociceptive effect induced by xylazine.
2009-04-17
Pharmacological profile of the clonidine-induced inhibition of vasodepressor sensory outflow in pithed rats: correlation with alpha(2A/2C)-adrenoceptors.
2008-05
Pharmacological evidence that alpha2A- and alpha2C-adrenoceptors mediate the inhibition of cardioaccelerator sympathetic outflow in pithed rats.
2007-01-12
Clonidine inhibits the canine external carotid vasodilatation to capsaicin by alpha2A/2C-adrenoceptors.
2006-08-14
Yohimbine acts as a putative in vivo alpha2A/D-antagonist in the rat prefrontal cortex.
2006-07-24
Alpha 2A-adrenoceptors enhance the serotonergic effects of fluoxetine.
2006-06-13
5-HT1B receptors, alpha2A/2C- and, to a lesser extent, alpha1-adrenoceptors mediate the external carotid vasoconstriction to ergotamine in vagosympathectomised dogs.
2004-07
5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine.
2004-01-26
1-(2-pyrimidinyl)-piperazine, a buspirone metabolite, modulates bladder function in the anesthetized rat.
2004
alpha2a adrenoceptors regulate phosphorylation of microtubule-associated protein-2 in cultured cortical neurons.
2004
Investigation of neurotransmission in vas deferens from alpha(2A/D)-adrenoceptor knockout mice.
2002-07
Presynaptic autoregulation of norepinephrine release from the sympathetic nerve fibers in the pineal gland of the domestic pig. Pharmacological characterization of alpha(2)adrenoceptors mediating this process.
2002-04
Pharmacological profile of the mechanisms involved in the external carotid vascular effects of the antimigraine agent isometheptene in anaesthetised dogs.
2001-07
The role of several alpha(1)- and alpha(2)-adrenoceptor subtypes mediating vasoconstriction in the canine external carotid circulation.
2001-03
Presynaptic alpha 2-autoreceptors in brain cortex: alpha 2D in the rat and alpha 2A in the rabbit.
1993-07
Assessment of imiloxan as a selective alpha 2B-adrenoceptor antagonist.
1990-03

Sample Use Guides

In Vivo Use Guide
Single dose - 500 mg
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Imiloxan was identified as a selective alpha 2B ligand of the adrenoceptor
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:30:06 GMT 2025
Edited
by admin
on Mon Mar 31 18:30:06 GMT 2025
Record UNII
X72FO6ZLZY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IMILOXAN HCL
INCI  
Preferred Name English
IMILOXAN HYDROCHLORIDE
USAN  
USAN  
Official Name English
RS-21361
Code English
(±)-2-((1-ETHYL-2-IMIDAZOLYL)METHYL)-1,4-BENZODIOXANE HYDROCHLORIDE
Systematic Name English
IMILOXAN HYDROCHLORIDE [USAN]
Common Name English
1H-IMIDAZOLE- 2-((2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)METHYL)-1-ETHYL-, MONOHYDROCHLORIDE, (±)-
Common Name English
(±)-2-(1,4-BENZODIOXAN-2-YLMETHYL)-1-ETHYLIMIDAZOLE MONOHYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Mon Mar 31 18:30:06 GMT 2025 , Edited by admin on Mon Mar 31 18:30:06 GMT 2025
Code System Code Type Description
FDA UNII
X72FO6ZLZY
Created by admin on Mon Mar 31 18:30:06 GMT 2025 , Edited by admin on Mon Mar 31 18:30:06 GMT 2025
PRIMARY
ChEMBL
CHEMBL347695
Created by admin on Mon Mar 31 18:30:06 GMT 2025 , Edited by admin on Mon Mar 31 18:30:06 GMT 2025
PRIMARY
CAS
86710-23-8
Created by admin on Mon Mar 31 18:30:06 GMT 2025 , Edited by admin on Mon Mar 31 18:30:06 GMT 2025
PRIMARY
USAN
W-2
Created by admin on Mon Mar 31 18:30:06 GMT 2025 , Edited by admin on Mon Mar 31 18:30:06 GMT 2025
PRIMARY
PUBCHEM
172975
Created by admin on Mon Mar 31 18:30:06 GMT 2025 , Edited by admin on Mon Mar 31 18:30:06 GMT 2025
PRIMARY
NCI_THESAURUS
C83793
Created by admin on Mon Mar 31 18:30:06 GMT 2025 , Edited by admin on Mon Mar 31 18:30:06 GMT 2025
PRIMARY
SMS_ID
300000055149
Created by admin on Mon Mar 31 18:30:06 GMT 2025 , Edited by admin on Mon Mar 31 18:30:06 GMT 2025
PRIMARY
Related Record Type Details
Structure of IMILOXAN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of IMILOXAN
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