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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 of PRENYLAMINE LACTATE

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)

HIDE SMILES / InChI
Molecular Formula C3H6O3
Molecular Weight 90.0779
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )
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

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channel blocker, was used to treat patients with angina pectoris, but because of the QT prolongation, this drug was withdrawn from the market.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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
555
Blocker
555
 0.72 µM [IC50]
Binding Agent
1076
Myosin light chain kinase 2, skeletal/cardiac muscle
3
Target ID: Q9H1R3
Gene ID: 85366.0
Gene Symbol: MYLK2
Target Organism: Homo sapiens (Human)
Inhibitor
8504
PubMed

PubMed

TitleDatePubMed
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.
2013-12
Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs.
2006-03
[Modulation of serine/threonine protein kinase activity in chloramphenicol-resistant mutants of Streptomyces avermitilis].
2004-08-03
Female gender as a risk factor for torsades de pointes associated with cardiovascular drugs.
1993-12-01
Prevention of adriamycin-induced cardiotoxicity by prenylamine: a pilot double blind study.
1987
Atrio-ventricular block after administration of lignocaine in patients treated with prenylamine.
1982-03
An overall review on prenylamine mechanisms of action in experimental models of myocardial damage.
1982
Overdrive pacing in quinidine syncope and other long QT-interval syndromes.
1980-08
Protective effect of creatinol O-phosphate (COP) on ventricular fibrillation and death induced by intravenous CaCl2 in mice.
1979
[Prevention of isoproterenol-induced lesions in the rat myocardium by prenylamine].
1975-09-01

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 Mon Mar 31 18:42:51 GMT 2025
Edited
by admin
on Mon Mar 31 18:42:51 GMT 2025
Record UNII
6J3J6SXI7V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRENYLAMINE LACTATE
JAN   MART.   MI   WHO-DD  
Systematic Name English
DL-PRENYLAMINE LACTATE
Preferred 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
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
MESH
C053347
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
SMS_ID
100000085078
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
RXCUI
34407
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID5045544
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
CAS
69-43-2
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
MERCK INDEX
m9125
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY Merck Index
PUBCHEM
65557
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
ChEMBL
CHEMBL24072
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
EVMPD
SUB04033MIG
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
DRUG BANK
DBSALT002856
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-705-5
Created by admin on Mon Mar 31 18:42:51 GMT 2025 , Edited by admin on Mon Mar 31 18:42:51 GMT 2025
PRIMARY
Related Record Type Details
Structure of PRENYLAMINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PRENYLAMINE
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