U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ETAFENONE HYDROCHLORIDE

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
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 C21H27NO2
Molecular Weight 325.4446
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

CNS Active
4002
Curator's Comment: Etafenone induces catalepsy in mice. No human data available.

Originator

DiPaco, G.|Tauro,S.C.
2
Sources: G. DiPaco, S. C. Tauro, Ann. Chim. (Rome) 48, 1215 (1958)
Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/etafenone.html

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1076
 2.43 µM [Ki]
Binding Agent
1076
 3.92 µM [Ki]
Binding Agent
1076
 0.184 µM [Ki]
Inhibitor
8504
Blocker
555
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
DIALICOR

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP19A1
429

CYP1A2
2153

CYP2C19
2057
P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
2633
 inconclusive [IC50 2.1876 uM]
CYP19A1
430
 no
CYP2C19
2141
 no
CYP2C9
2497
 no
CYP2D6
2546
 yes [IC50 0.1096 uM]
CYP1A2
2333
 yes [IC50 7.7619 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Propiverine-induced Parkinsonism: a case report and a pharmacokinetic/pharmacodynamic study in mice.
2000-05
Effects of etafenone on myocardial energy metabolism as studied by an organ redoximeter and biochemical analyses.
1984-07
Effects of etafenone and antiarrhythmic drugs on Na and Ca channels of guinea pig atrial muscle.
1979-09-01
Effect of etafenone on total and regional myocardial blood flow.
1975-09
Modification of the cardiostimulatory and coronary dilator effect of isopreenaline caused by etafenone.
1975-01
[Pharmacological and toxicological studies on the effect characterization of etafenone].
1969-10
[Clinical study of a new synthetic drug with coronary-dilatatory action (LG-11457)].
1960-09-01
[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
[Preliminary observations on the treatment of coronary insufficiency with 2'-(2-diethylaminoethoxy)-3-phenylpropiophenone hydrochloride (LG--11457)].
1960-09-01
Patents

Patents

DE1265758
2

Sample Use Guides

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:28:19 GMT 2025
Edited
by admin
on Mon Mar 31 19:28:19 GMT 2025
Record UNII
NTS160XKGC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LG-11457
Preferred Name English
ETAFENONE HYDROCHLORIDE
JAN   MART.   WHO-DD  
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
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
Code System Code Type Description
SMS_ID
100000087296
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
CAS
2192-21-4
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
DRUG BANK
DBSALT002643
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
EVMPD
SUB01980MIG
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID60176336
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
FDA UNII
NTS160XKGC
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
NCI_THESAURUS
C95811
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
PUBCHEM
102220
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
ECHA (EC/EINECS)
218-587-9
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
MESH
C001162
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
NSC
166350
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
ChEMBL
CHEMBL1736151
Created by admin on Mon Mar 31 19:28:19 GMT 2025 , Edited by admin on Mon Mar 31 19:28:19 GMT 2025
PRIMARY
Related Record Type Details
Structure of ETAFENONE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ETAFENONE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966