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Details

Stereochemistry RACEMIC
Molecular Formula C24H27N.C6H12O7
Molecular Weight 525.6332
Optical Activity ( + / - )
Defined Stereocenters 4 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRENYLAMINE GLUCONATE

SMILES

OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O.CC(CC1=CC=CC=C1)NCCC(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=XWLQOHKWSBPMOX-IFWQJVLJSA-N
InChI=1S/C24H27N.C6H12O7/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;7-1-2(8)3(9)4(10)5(11)6(12)13/h2-16,20,24-25H,17-19H2,1H3;2-5,7-11H,1H2,(H,12,13)/t;2-,3-,4+,5-/m.1/s1

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channel blocker, was used to treat patients with angina pectoris, but because of the QT prolongation, this drug was withdrawn from the market.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

Targets

Primary TargetPharmacologyConditionPotency
0.72 µM [IC50]
Target ID: Q9H1R3
Gene ID: 85366.0
Gene Symbol: MYLK2
Target Organism: Homo sapiens (Human)
PubMed

PubMed

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

Sample Use Guides

270 mg of prenylamine per day for one month
Route of Administration: Oral
Name Type Language
PRENYLAMINE GLUCONATE
Common Name English
PHENETHYLAMINE, N-(3,3-DIPHENYLPROPYL)-.ALPHA.-METHYL-, D-GLUCONATE
Common Name English
D-GLUCONIC ACID, COMPD. WITH N-(1-METHYL-2-PHENYLETHYL)-.GAMMA.-PHENYLBENZENEPROPANAMINE (1:1)
Systematic Name English
GLUCONIC ACID, D-, COMPD. WITH N-(3,3-DIPHENYLPROPYL)-.ALPHA.-METHYLPHENETHYLAMINE (1:1)
Systematic Name English
PRENYLAMINE D-GLUCONATE
Common Name English
BENZENEPROPANAMINE, N-(1-METHYL-2-PHENYLETHYL)-.GAMMA.-PHENYL-, D-GLUCONATE
Common Name English
Code System Code Type Description
PUBCHEM
167965
Created by admin on Sat Dec 16 18:35:02 GMT 2023 , Edited by admin on Sat Dec 16 18:35:02 GMT 2023
PRIMARY
FDA UNII
Q09085O516
Created by admin on Sat Dec 16 18:35:02 GMT 2023 , Edited by admin on Sat Dec 16 18:35:02 GMT 2023
PRIMARY
CAS
21156-48-9
Created by admin on Sat Dec 16 18:35:02 GMT 2023 , Edited by admin on Sat Dec 16 18:35:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID10943479
Created by admin on Sat Dec 16 18:35:02 GMT 2023 , Edited by admin on Sat Dec 16 18:35:02 GMT 2023
PRIMARY