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Compound Detail

CHEMBL24072

PRENYLAMINE
💊 Approved Drug
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💊 Approved Drug
CC(Cc1ccccc1)NCCC(c1ccccc1)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL24072
Name PRENYLAMINE
Phase Approved
Structure Type MOL
InChI Key IFFPICMESYHZPQ-UHFFFAOYSA-N

Known Names

B-436 Prenilamina Prenylamine Prenylamine lactate
7
Targets
10
Activities
3
Assay Types
0
PK Parameters
20
Publications
4
Known Names
1
Indications
2
Mechanisms

Molecular Properties

329.5
MW (Da)
5.43
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.58
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Racemic

Flags

Withdrawn Natural Product
USAN Year 1962

Extended Properties

Molecular Formula C24H27N
MW 329.49
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -0.32

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Sodium channel protein type V alpha subunit blocker BLOCKER Sodium channel protein type 5 subunit alpha ✓ ✓
Calmodulin inhibitor INHIBITOR Calmodulin-1 ✓ ✓

Indications

Cardiovascular Diseases

ATC Classification

C01DX02
prenylamine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY
C01DX52
prenylamine, combinations
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY

Drug Warnings

Withdrawn
General Warning
Polymorphic Ventricular Tachycardia and Death
Country: Worldwide   Year: 1989
Withdrawn
cardiotoxicity
reports of polymorphic ventricular tachycardia
Country: Worldwide   Year: 1989
Withdrawn
cardiotoxicity
Polymorphic Ventricular Tachycardia and Death
Country: Worldwide   Year: 1989

Activity Summary

IC50 5 meas. best 7.19
Kd 4 meas. best 6.68
EC50 1 meas. best 5.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 7.19 7.19 65.0 1
Voltage-gated L-type calcium channel
CHEMBL2095177
 Kd 6.68 6.68 209.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
 IC50 6.52 6.52 300.0 1
Unchecked
CHEMBL612545
 Kd 6.4 6.4 400.0 1
Calmodulin
CHEMBL6092
 Kd 6.3 6.025 500.0 2
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL2366456
 IC50 5.91 5.91 1240.0 2
Calmodulin
CHEMBL6092
 EC50 5.62 5.62 2400.0 1
Sodium channel protein type 5 subunit alpha
CHEMBL1980
 IC50 5.6 5.6 2520.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 65.0 nM 7.19 Inhibition of potassium current (Ikr) measured using whole-cell patch clamp expe... 21300721
Voltage-gated L-type calcium channel Kd = 209.0 nM 6.68 Inhibition of [3H]nitrendipine binding to calcium channel of rat brain membranes... -
Sodium channel alpha subunits; brain (Types I, II, III) IC50 = 300.0 nM 6.52 Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on vol... 2579237
Unchecked Kd = 400.0 nM 6.4 Displacement of [3H]bepridil from porcine brain CaM by Dixon analysis 27043269
Calmodulin Kd = 500.0 nM 6.3 Binding affinity to dansylated bovine testes CaM by fluorescence analysis in pre... 27043269
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 1240.0 nM 5.91 Inhibition of calcium current (ICaL) measured using whole-cell patch clamp exper... 21300721
Voltage-dependent L-type calcium channel subunit alpha-1C IC50 = 1240.0 nM 5.91 Inhibition of L-type calcium channel measured using whole-cell patch clamp in gu... 22761000
Calmodulin Kd = 1800.0 nM 5.75 Binding affinity to bovine brain CaM by FTPFACE analysis 27043269
Calmodulin EC50 = 2400.0 nM 5.62 Binding affinity to dansylated bovine brain CaM assessed as half maximal increas... 27043269
Sodium channel protein type 5 subunit alpha IC50 = 2520.0 nM 5.6 Inhibition of sodium current measured using whole-cell patch clamp experiments i... 21300721

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4651402 SARS-CoV-2 6
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
27043269 10.1016/j.ejmech.2016.03.045 Calmodulin 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
2579237 10.1021/jm00381a019 Sodium channel alpha subunits; brain (Types I, II, III) 2
37468498 10.1038/s41467-023-40064-9 Voltage-dependent L-type calcium channel subunit alpha-1C 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2
- 10.6019/CHEMBL4651402 Vero C1008 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 2
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 2
21300721 10.1093/cvr/cvr044 Voltage-gated inwardly rectifying potassium channel KCNH2 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
21300721 10.1093/cvr/cvr044 Voltage-dependent L-type calcium channel subunit alpha-1C 1
20020916 10.1080/15376510701857262 Phospholipidosis 1
20799726 10.1021/mp100103e Phospholipidosis 1

Data from ChEMBL 36 via Core Engine