ALPRAFENONE

Details

Stereochemistry	RACEMIC
Molecular Formula	C25H35NO4
Molecular Weight	413.5497
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(C)(C)NCC(O)COC1=C(OC)C=CC(CCC(=O)C2=CC=C(C)C=C2)=C1

InChI

InChIKey=WUUQBRHWNUFEEB-UHFFFAOYSA-N

InChI=1S/C25H35NO4/c1-6-25(3,4)26-16-21(27)17-30-24-15-19(10-14-23(24)29-5)9-13-22(28)20-11-7-18(2)8-12-20/h7-8,10-12,14-15,21,26-27H,6,9,13,16-17H2,1-5H3

HIDE SMILES / InChI

Molecular Formula	C25H35NO4
Molecular Weight	413.5497
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/7528297 | https://adisinsight.springer.com/drugs/800002255

Alprafenone [AH 141], a phenylpropanone derivative, is presently classified as a class Ic antiarrhythmic agent, it is a sodium channel antagonist. Alprafenone's range of actions is consistent with that of other effective antiarrhythmic drugs and is very similar to that of propafenone. Alprafenone was under preclinical development with Helopharm (Germany), but later this development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Negative inotropic effects of the new class I antiarrhythmic agents berlafenone and alprafenone on electrically stimulated isolated cardiomyocytes.	1992 Mar	1497686
Electrophysiologic effects of alprafenone on canine cardiac tissue.	1994 Sep	7528297

Patents

Sample Use Guides

In Vitro Use Guide

In canine Purkinje fibers (PF) with normal maximum diastolic potentials (MDPs), alprafenone (5 x 10(-8)-1 x 10(-6) M) produced concentration-dependent decreases in AP amplitude (APA), Vmax, AP duration (APD), and conduction velocity. Alprafenone produced a reduction in contraction amplitude of rat electrically stimulated myocytes with a similar dose-response relationship (IC50 approx. 10 umol/l).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:34:38 GMT 2023` Edited by `admin` on `Fri Dec 15 16:34:38 GMT 2023`
Record UNII	D5H25D039V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALPRAFENONE

Official Name

English

(±)-3-(3-(2-HYDROXY-3-(TERT-PENTYLAMINO)PROPOXY)-4-METHOXYPHENYL)-4'-METHYLPROPIOPHENONE

Systematic Name

English

alprafenone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47793