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

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	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 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
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 Apr	12019363
Investigation of neurotransmission in vas deferens from alpha(2A/D)-adrenoceptor knockout mice.	2002 Jul	12110610
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
5-HT1B receptors and alpha 2A/2C-adrenoceptors mediate external carotid vasoconstriction to dihydroergotamine.	2004 Jan 26	14744615
5-HT1B receptors, alpha2A/2C- and, to a lesser extent, alpha1-adrenoceptors mediate the external carotid vasoconstriction to ergotamine in vagosympathectomised dogs.	2004 Jul	15224175
Clonidine inhibits the canine external carotid vasodilatation to capsaicin by alpha2A/2C-adrenoceptors.	2006 Aug 14	16814767
Yohimbine acts as a putative in vivo alpha2A/D-antagonist in the rat prefrontal cortex.	2006 Jul 24	16697527
Alpha 2A-adrenoceptors enhance the serotonergic effects of fluoxetine.	2006 Jun 13	16714015
Pharmacological evidence that alpha2A- and alpha2C-adrenoceptors mediate the inhibition of cardioaccelerator sympathetic outflow in pithed rats.	2007 Jan 12	17109851
Pharmacological profile of the clonidine-induced inhibition of vasodepressor sensory outflow in pithed rats: correlation with alpha(2A/2C)-adrenoceptors.	2008 May	18297098
Probable involvement of alpha(2C)-adrenoceptor subtype and endogenous opioid peptides in the peripheral antinociceptive effect induced by xylazine.	2009 Apr 17	19236861
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:30:48 GMT 2023` Edited by `admin` on `Fri Dec 15 16:30:48 GMT 2023`
Record UNII	X72FO6ZLZY
Record Status	`Validated (UNII)`
Record Version

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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