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Compound Detail

CHEMBL75880

PERHEXILINE
💊 Approved Drug
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💊 Approved Drug
C1CCC(C(CC2CCCCN2)C2CCCCC2)CC1

Basic Information

ChEMBL ID CHEMBL75880
Name PERHEXILINE
Phase Approved
Structure Type MOL
InChI Key CYXKNKQEMFBLER-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Perhexilina Perhexiline
20
Targets
41
Activities
3
Assay Types
5
PK Parameters
20
Publications
2
Known Names
5
Indications

Molecular Properties

277.5
MW (Da)
5.30
ALogP
1
HBA
1
HBD
12.0
PSA (Ų)
0.74
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1974
Availability Withdrawn
Chirality Racemic

Flags

Withdrawn Natural Product
USAN Year 1966

Extended Properties

Molecular Formula C19H35N
MW 277.50
Aromatic Rings 0
Heavy Atoms 20
NP-Likeness 0.31

Indications

Cardiovascular Diseases Cardiomyopathy, Hypertrophic Heart Failure Heart Failure, Diastolic Diabetic Cardiomyopathies

ATC Classification

C08EX02
perhexiline
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CALCIUM CHANNEL BLOCKERS

Activity Summary

IC50 31 meas. best 6.29
Ki 9 meas. best 6.33
Kd 1 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adrenergic receptor alpha-1
CHEMBL1907610
Kd 6.7 6.7 199.5 1
Unchecked
CHEMBL612545
Ki 6.33 6.08 465.8 3
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 6.3 6.3 500.9 1
Unchecked
CHEMBL612545
IC50 6.29 5.492 510.6 5
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 6.18 6.18 652.8 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 6.18 6.18 661.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 6.11 6.11 785.4 1
Cytochrome P450 2D6
CHEMBL289
IC50 6.03 6.03 940.8 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 5.96 5.96 1093.2 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 5.96 5.96 1092.4 1
Epidermal growth factor receptor
CHEMBL203
IC50 5.83 5.83 1485.2 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 5.58 5.58 2599.2 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 5.57 5.57 2710.5 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 5.51 5.51 3118.6 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.49 5.49 3267.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.48 5.48 3294.2 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 5.45 5.45 3591.9 1
Tyrosine-protein kinase Fyn
CHEMBL1841
IC50 5.39 5.39 4064.0 1
SARS-CoV-2
CHEMBL4303835
IC50 5.2 5.2 6380.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.11 5.11 7762.5 6
Carnitine O-palmitoyltransferase 1, muscle isoform
CHEMBL3216
IC50 4.96 4.96 11000.0 1
HepG2
CHEMBL395
IC50 4.95 4.95 11300.0 1
Bile salt export pump
CHEMBL6020
IC50 4.84 4.84 14360.0 1
KB
CHEMBL398
IC50 4.83 4.83 14800.0 1
Carnitine O-palmitoyltransferase 2, mitochondrial
CHEMBL3238
IC50 4.14 4.14 72800.0 1
Carnitine O-palmitoyltransferase 1, liver isoform
CHEMBL3858
IC50 4.11 4.11 77000.0 1
Carnitine O-palmitoyltransferase 2, mitochondrial
CHEMBL4037
IC50 4.11 4.105 77000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 2114.0 ng.hr.mL-1 Mus musculus
AUC 876.0 ng.hr.mL-1 Mus musculus
T1/2 0.2333 hr Homo sapiens
T1/2 0.35 hr Rattus norvegicus
T1/2 1.667 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adrenergic receptor alpha-1 Kd = 199.53 nM 6.7 Alpha adrenergic receptor activity in rat aorta 2903931
Unchecked Ki = 465.8 nM 6.33 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Muscarinic acetylcholine receptor M4 Ki = 500.9 nM 6.3 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked IC50 = 510.6 nM 6.29 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Muscarinic acetylcholine receptor M3 Ki = 661.0 nM 6.18 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M1 Ki = 652.8 nM 6.18 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 Ki = 785.4 nM 6.11 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked Ki = 939.4 nM 6.03 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Cytochrome P450 2D6 IC50 = 940.8 nM 6.03 DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Unchecked IC50 = 1056.9 nM 5.98 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Sigma non-opioid intracellular receptor 1 Ki = 1092.4 nM 5.96 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Muscarinic acetylcholine receptor M5 IC50 = 1093.2 nM 5.96 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked Ki = 1312.4 nM 5.88 DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand... -
Unchecked IC50 = 1349.9 nM 5.87 DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand... -
Epidermal growth factor receptor IC50 = 1485.2 nM 5.83 DRUGMATRIX: Protein Tyrosine Kinase, EGF Receptor enzyme inhibition (substrate: ... -
Sigma non-opioid intracellular receptor 1 IC50 = 2599.2 nM 5.58 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Muscarinic acetylcholine receptor M1 IC50 = 2710.5 nM 5.57 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 IC50 = 3118.6 nM 5.51 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Sodium-dependent noradrenaline transporter Ki = 3267.0 nM 5.49 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -
Sodium-dependent noradrenaline transporter IC50 = 3294.2 nM 5.48 DRUGMATRIX: Norepinephrine Transporter radioligand binding (ligand: [125I] RTI-5... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1376
- 10.6019/CHEMBL3885881 Rattus norvegicus 174
28277663 10.1021/acs.jmedchem.6b01592 ADMET 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
28277663 10.1021/acs.jmedchem.6b01592 Plasma 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
28277663 10.1021/acs.jmedchem.6b01592 Heart 3
17428028 10.1021/ci6004542 Phospholipidosis 3
21504156 10.1021/jm100809g Carnitine O-palmitoyltransferase 1, liver isoform 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
21504156 10.1021/jm100809g Unchecked 2
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 2
21504156 10.1021/jm100809g Carnitine O-palmitoyltransferase 2, mitochondrial 2
20553011 10.1021/tx1000865 Hepatotoxicity 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
28277663 10.1021/acs.jmedchem.6b01592 Liver 2
37468498 10.1038/s41467-023-40064-9 Glucocorticoid receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 2

Data from ChEMBL 36 via Core Engine