IMILOXAN HYDROCHLORIDE

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 Search

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

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 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20446913	Primary		Phase I 428	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 60 BSEP 402	P-gp 1537 UGTs 13

Drug as perpetrator

Target	Modality	Activity
CYP19A1 60	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743139#sid=144203726	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645842#sid=170466588	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170466588	no
BSEP 403	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466588	weak [IC50 61.65 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645840#sid=170466588	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
UGTs 13	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10950841/
P-gp 1537	substrate 3367 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1346987#sid=144203726	no

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
AN PharmaTech	AN-3505
Ambinter	Amb22734572	http://www.ambinter.com/reference/22734572
ChemShuttle	113757	http://www.chemshuttle.com/catalogsearch/result/?q=81167-16-0&cat=
Chemieliva Pharmaceutical Co., Ltd	PBCM0850033
DC Chemicals	DC7289	http://www.dcchemicals.com/product_show-Imiloxan.html
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
eNovation Chemicals	D676555	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676555

PubMed

Title	Date	PubMed
Assessment of imiloxan as a selective alpha 2B-adrenoceptor antagonist.	1990 Mar	1970500
Presynaptic alpha 2-autoreceptors in brain cortex: alpha 2D in the rat and alpha 2A in the rabbit.	1993 Jul	8397342
Pharmacological profile of the mechanisms involved in the external carotid vascular effects of the antimigraine agent isometheptene in anaesthetised dogs.	2001 Jul	11485035
The role of several alpha(1)- and alpha(2)-adrenoceptor subtypes mediating vasoconstriction in the canine external carotid circulation.	2001 Mar	11250880
Antinociceptive synergism of MD-354 and clonidine. Part II. The alpha-adrenoceptor component.	2010 Aug	20353485

Sample Use Guides

In Vivo Use Guide

Single dose - 500 mg

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

IMILOXAN HYDROCHLORIDE

Official Name

English

RS-21361

Code

English

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

Systematic Name

English

IMILOXAN HCL [INCI]

Common 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

IMILOXAN HCL

Official Name

English

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

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29713