ETAFENONE HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H27NO2.ClH
Molecular Weight	361.906
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CCN(CC)CCOC1=C(C=CC=C1)C(=O)CCC2=CC=CC=C2

InChI

InChIKey=BYWIEEUABBZFEE-UHFFFAOYSA-N

InChI=1S/C21H27NO2.ClH/c1-3-22(4-2)16-17-24-21-13-9-8-12-19(21)20(23)15-14-18-10-6-5-7-11-18;/h5-13H,3-4,14-17H2,1-2H3;1H

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23 | https://www.ncbi.nlm.nih.gov/pubmed/238542
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6482088 | https://www.ncbi.nlm.nih.gov/pubmed/582134 | https://www.ncbi.nlm.nih.gov/pubmed/469443 | https://www.ncbi.nlm.nih.gov/pubmed/94412 | http://www.drugfuture.com/chemdata/etafenone.html | https://www.ncbi.nlm.nih.gov/pubmed/582134 | https://www.ncbi.nlm.nih.gov/pubmed/94412 | https://www.ncbi.nlm.nih.gov/pubmed/1037264 | https://www.ncbi.nlm.nih.gov/pubmed/1786372

Etafenone is an antiarrhythmic and coronary vasodilator drug. Etafenone exerts negative inotropic action on myocardium. It is able to block calcium channels. As a coronary vasodilator which produces a decrease in the heart rate and myocardial oxygen consumption, etafenone has been used in the therapy of ischemic heart disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D1 receptor 106 Target ID: CHEMBL3071 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10888308	Binding Agent 1076	2.43 µM [Ki]
Dopamine D2 receptor 311 Target ID: CHEMBL3427 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10888308	Binding Agent 1076	3.92 µM [Ki]
Muscarinic acetylcholine receptor 162 Target ID: CHEMBL2097162 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10888308	Binding Agent 1076	0.184 µM [Ki]
vascular smooth muscle contraction 5 Target ID: GO:0014829 Sources: http://www.kegg.jp/entry/D01440 \| https://www.ncbi.nlm.nih.gov/pubmed/23 \| https://www.ncbi.nlm.nih.gov/pubmed/238542	Inhibitor 8504
Voltage-gated calcium channel 37 Target ID: CHEMBL2363032 Sources: http://www.drugfuture.com/chemdata/etafenone.html \| https://www.ncbi.nlm.nih.gov/pubmed/582134 \| https://www.ncbi.nlm.nih.gov/pubmed/94412 \| https://www.ncbi.nlm.nih.gov/pubmed/1037264 \| https://www.ncbi.nlm.nih.gov/pubmed/1786372	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Angina pectoris 110 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6482088	Primary		Approved 8583	DIALICOR Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 CYP1A2 2153 CYP2C19 2057	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3275#section=Biological-Test-Results Page: 2.0	inconclusive [IC50 2.1876 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3275#section=Biological-Test-Results Page: 53.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3275#section=Biological-Test-Results Page: 100.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3275#section=Biological-Test-Results Page: 100.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3275#section=Biological-Test-Results Page: 1.0	yes [IC50 0.1096 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3275#section=Biological-Test-Results Page: 4.0	yes [IC50 7.7619 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3275#section=Biological-Test-Results Page: 13 \| 91	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/3275#section=Biological-Test-Results Page: 2.0

PubMed

Title	Date	PubMed
Propiverine-induced Parkinsonism: a case report and a pharmacokinetic/pharmacodynamic study in mice.	2000-05	10888308
Effects of etafenone on myocardial energy metabolism as studied by an organ redoximeter and biochemical analyses.	1984-07	6482088
Effects of etafenone and antiarrhythmic drugs on Na and Ca channels of guinea pig atrial muscle.	1979-09-01	94412
Effect of etafenone on total and regional myocardial blood flow.	1975-09	23
Modification of the cardiostimulatory and coronary dilator effect of isopreenaline caused by etafenone.	1975-01	238542
[Pharmacological and toxicological studies on the effect characterization of etafenone].	1969-10	5395365
[Clinical study of a new synthetic drug with coronary-dilatatory action (LG-11457)].	1960-09-01	13722451
[Pharmacological study of some properties of LG-11457. Action on ventricular extrasystoles, on spasm of smooth muscles and on the peripheral circulation].	1960-09-01	13721592
[Preliminary observations on the treatment of coronary insufficiency with 2'-(2-diethylaminoethoxy)-3-phenylpropiophenone hydrochloride (LG--11457)].	1960-09-01	13692742

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Parenteral

In Vitro Use Guide

After etafenone 1 uM, there was a significant prolongation of the time to the detectable or the maximum increase in NADH fluorescence in isolated perfused guinea pig heart

Name

Type

Language

LG-11457

Preferred Name

English

ETAFENONE HYDROCHLORIDE

Common Name

English

NSC-166350

Code

English

Etafenone hydrochloride [WHO-DD]

Common Name

English

ETAFENONE HCL

Common Name

English

HEPTAPHENONE

Common Name

English

ETAFENONE HYDROCHLORIDE [JAN]

Common Name

English

2'-(2-DIETHYLAMINOETHOXY)-3-PHENYLPROPIOPHENONE HYDROCHLORIDE

Systematic Name

English

ETAFENONE HYDROCHLORIDE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149