IMILOXAN

Investigational

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Alpha-2B adrenergic receptor 13	Antagonist 2,778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 235	Primary		Phase I 428	Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 60 BSEP 402	P-gp 1,537 UGTs 13

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP19A1 60	inhibitor 3,277	no
CYP2C9 1,819	inhibitor 3,277	no
CYP3A4 1,925	inhibitor 3,277	no
BSEP 403	inhibitor 3,277	weak [IC50 61.65 uM]
CYP2D6 1,891	inhibitor 3,277	yes

Showing 1 to 5 of 5 entries

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
UGTs 13	substrate 3,367
P-gp 1,537	substrate 3,367	no

Showing 1 to 2 of 2 entries

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Sourcing

Sourcing

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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

Showing 1 to 5 of 17 entries

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PubMed

PubMed

Show entries

Title	Date	PubMed
Assessment of imiloxan as a selective alpha 2B-adrenoceptor antagonist.	1990 Mar	1970500
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
Yohimbine acts as a putative in vivo alpha2A/D-antagonist in the rat prefrontal cortex.	2006 Jul 24	16697527
Pharmacological profile of the clonidine-induced inhibition of vasodepressor sensory outflow in pithed rats: correlation with alpha(2A/2C)-adrenoceptors.	2008 May	18297098
Antinociceptive synergism of MD-354 and clonidine. Part II. The alpha-adrenoceptor component.	2010 Aug	20353485