PRENYLAMINE LACTATE

Details

Stereochemistry	MIXED
Molecular Formula	C24H27N.C3H6O3
Molecular Weight	419.5558
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)C(O)=O.CC(CC1=CC=CC=C1)NCCC(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=QPOFIDVRLWJICD-UHFFFAOYSA-N

InChI=1S/C24H27N.C3H6O3/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;1-2(4)3(5)6/h2-16,20,24-25H,17-19H2,1H3;2,4H,1H3,(H,5,6)

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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channel blocker, was used to treat patients with angina pectoris, but because of the QT prolongation, this drug was withdrawn from the market.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
Protective effect of creatinol O-phosphate (COP) on ventricular fibrillation and death induced by intravenous CaCl2 in mice.	1979	575496
An overall review on prenylamine mechanisms of action in experimental models of myocardial damage.	1982	6293707
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
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

Name

Type

Language

PRENYLAMINE LACTATE

Systematic Name

English

DL-PRENYLAMINE LACTATE

Common Name

English

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

Systematic Name

English

LACTIC ACID, COMPD. WITH N-(3,3-DIPHENYLPROPYL)-.ALPHA.-METHYLPHENETHYLAMINE (1:1)

Common Name

English

PRENYLAMINE LACTATE [JAN]

Common Name

English

Prenylamine lactate [WHO-DD]

Common Name

English

PROPANOIC ACID, 2-HYDROXY-, COMPD. WITH N-(1-METHYL-2-PHENYLETHYL)-.GAMMA.-PHENYLBENZENEPROPANAMINE (1:1)

Common Name

English

PRENYLAMINE LACTATE [MI]

Common Name

English

PRENYLAMINE LACTATE [MART.]

Common Name

English

SEGONTIN

Common Name

English

Code System Code Type Description

FDA UNII

6J3J6SXI7V