PRENYLAMINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C24H27N
Molecular Weight	329.4779
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(CC1=CC=CC=C1)NCCC(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=IFFPICMESYHZPQ-UHFFFAOYSA-N

InChI=1S/C24H27N/c1-20(19-21-11-5-2-6-12-21)25-18-17-24(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,20,24-25H,17-19H2,1H3

HIDE SMILES / InChI

Molecular Formula	C24H27N
Molecular Weight	329.4779
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/13978340 | https://doi.org/10.1177/2042098618780854 | https://www.ncbi.nlm.nih.gov/pubmed/2933041

Prenylamine, a slow Ca2+ channel blocker, was used to treat patients with angina pectoris, but because of the QT prolongation, this drug was withdrawn from the market. Prenylamine binds to calmodulin section and inhibits myosin light chain kinase.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.sciencedirect.com/science/article/pii/B9780128012383993838	Blocker 537
Sodium channel protein type V alpha subunit 49 Target ID: CHEMBL1980 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12130695	Blocker 537	0.72 µM [IC50]
Calmodulin 17 Target ID: CHEMBL6093 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2933041	Binding Agent 1064
Myosin light chain kinase 2, skeletal/cardiac muscle 3 Target ID: Q9H1R3 Gene ID: 85366.0 Gene Symbol: MYLK2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2933041	Inhibitor 8297

PubMed

Title	Date	PubMed
[Prevention of isoproterenol-induced lesions in the rat myocardium by prenylamine].	1975 Sep-Oct	1214589
Protective effect of creatinol O-phosphate (COP) on ventricular fibrillation and death induced by intravenous CaCl2 in mice.	1979	575496
Overdrive pacing in quinidine syncope and other long QT-interval syndromes.	1980 Aug	7396607
An overall review on prenylamine mechanisms of action in experimental models of myocardial damage.	1982	6293707
Atrio-ventricular block after administration of lignocaine in patients treated with prenylamine.	1982 Mar	7100044
Prevention of adriamycin-induced cardiotoxicity by prenylamine: a pilot double blind study.	1987	3427552
Female gender as a risk factor for torsades de pointes associated with cardiovascular drugs.	1993 Dec 1	8230644
[Modulation of serine/threonine protein kinase activity in chloramphenicol-resistant mutants of Streptomyces avermitilis].	2004 May-Jun	15285607
Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs.	2006 Mar	16278312
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.	2013 Dec	24052561

Sample Use Guides

In Vivo Use Guide

270 mg of prenylamine per day for one month

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:00:55 GMT 2023` Edited by `admin` on `Fri Dec 15 17:00:55 GMT 2023`
Record UNII	K2OH82Z000
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRENYLAMINE

Official Name

English

PRENYLAMINE [MART.]

Common Name

English

BENZENEPROPANAMINE, N-(1-METHYL-2-PHENYLETHYL)-.GAMMA.-PHENYL-

Systematic Name

English

PRENYLAMINE [MI]

Common Name

English

Prenylamine [WHO-DD]

Common Name

English

prenylamine [INN]

Common Name

English

B-436

Code

English

N-(3,3-Diphenylpropyl)-α-methylphenethylamine

Systematic Name

English

PRENYLAMINE [USAN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

C01DX02