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channel blocker, was used to treat patients with angina pectoris, but because of the QT prolongation, this drug was withdrawn from the market.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
[Prevention of isoproterenol-induced lesions in the rat myocardium by prenylamine].	1975 Sep-Oct	1214589
Overdrive pacing in quinidine syncope and other long QT-interval syndromes.	1980 Aug	7396607
Atrio-ventricular block after administration of lignocaine in patients treated with prenylamine.	1982 Mar	7100044
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
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