IMILOXAN

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H16N2O2
Molecular Weight	244.289
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1C=CN=C1CC2COC3=CC=CC=C3O2

InChI

InChIKey=UXABARREKCJULM-UHFFFAOYSA-N

InChI=1S/C14H16N2O2/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

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20446913

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alpha-2B adrenergic receptor 13 Target ID: P18089 Gene ID: 151.0 Gene Symbol: ADRA2B Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1970500	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20446913	Primary		Phase I 438	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 BSEP 550	P-gp 2052 UGTs 13

Drug as perpetrator

Target	Modality	Activity
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144203726	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170466588	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466588	no
BSEP 554	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466588	weak [IC50 61.65 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466588	yes [IC50 1.7377 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144203726	no
UGTs 13	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10950841/ \| https://www.tandfonline.com/doi/abs/10.3109/00498259209046622	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Antinociceptive synergism of MD-354 and clonidine. Part II. The alpha-adrenoceptor component.	2010-08	20353485
Probable involvement of alpha(2C)-adrenoceptor subtype and endogenous opioid peptides in the peripheral antinociceptive effect induced by xylazine.	2009-04-17	19236861
Pharmacological profile of the clonidine-induced inhibition of vasodepressor sensory outflow in pithed rats: correlation with alpha(2A/2C)-adrenoceptors.	2008-05	18297098
Pharmacological evidence that alpha2A- and alpha2C-adrenoceptors mediate the inhibition of cardioaccelerator sympathetic outflow in pithed rats.	2007-01-12	17109851
Clonidine inhibits the canine external carotid vasodilatation to capsaicin by alpha2A/2C-adrenoceptors.	2006-08-14	16814767
Yohimbine acts as a putative in vivo alpha2A/D-antagonist in the rat prefrontal cortex.	2006-07-24	16697527
Alpha 2A-adrenoceptors enhance the serotonergic effects of fluoxetine.	2006-06-13	16714015
5-HT1B receptors, alpha2A/2C- and, to a lesser extent, alpha1-adrenoceptors mediate the external carotid vasoconstriction to ergotamine in vagosympathectomised dogs.	2004-07	15224175
5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine.	2004-01-26	14744615
1-(2-pyrimidinyl)-piperazine, a buspirone metabolite, modulates bladder function in the anesthetized rat.	2004	15382198
alpha2a adrenoceptors regulate phosphorylation of microtubule-associated protein-2 in cultured cortical neurons.	2004	14698748
Investigation of neurotransmission in vas deferens from alpha(2A/D)-adrenoceptor knockout mice.	2002-07	12110610
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	12019363
Pharmacological profile of the mechanisms involved in the external carotid vascular effects of the antimigraine agent isometheptene in anaesthetised dogs.	2001-07	11485035
The role of several alpha(1)- and alpha(2)-adrenoceptor subtypes mediating vasoconstriction in the canine external carotid circulation.	2001-03	11250880
Presynaptic alpha 2-autoreceptors in brain cortex: alpha 2D in the rat and alpha 2A in the rabbit.	1993-07	8397342
Assessment of imiloxan as a selective alpha 2B-adrenoceptor antagonist.	1990-03	1970500

Sample Use Guides

In Vivo Use Guide

Single dose - 500 mg

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:33:44 GMT 2025` Edited by `admin` on `Mon Mar 31 18:33:44 GMT 2025`
Record UNII	ZJ56PS1DWK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IMILOXAN

Official Name

English

1H-IMIDAZOLE- 2-((2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)METHYL)-1-ETHYL-, (±)-

Preferred Name

English

imiloxan [INN]

Common Name

English

(±)-2-((1-ETHYL-2-IMIDAZOLYL)METHYL)-1,4-BENZODIOXANE

Systematic Name

English

(±)-2-(1,4-BENZODIOXAN-2-YLMETHYL)-1-ETHYLIMIDAZOLE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713