Details
| Stereochemistry | UNKNOWN |
| Molecular Formula | C19H35N.C4H4O4 |
| Molecular Weight | 393.5601 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.C(C(C1CCCCC1)C2CCCCC2)C3CCCCN3
InChI
InChIKey=JDZOTSLZMQDFLG-BTJKTKAUSA-N
InChI=1S/C19H35N.C4H4O4/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18;5-3(6)1-2-4(7)8/h16-20H,1-15H2;1-2H,(H,5,6)(H,7,8)/b;2-1-
| Molecular Formula | C4H4O4 |
| Molecular Weight | 116.0722 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
| Molecular Formula | C19H35N |
| Molecular Weight | 277.4879 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Perhexiline, 2-(2,2-dicyclohexylethyl)piperidine, is an anti-anginal drug. Perhexiline reduces fatty acid metabolism through the inhibition of carnitine palmitoyltransferase, the enzyme responsible for mitochondrial uptake of long-chain fatty acids. Perhexiline is used for reducing the frequency of moderate to severe attacks of angina pectoris due to coronary artery disease in patients who have not responded to other conventional therapy or in whom such therapy may be contraindicated. Heart Metabolics Limited is developing perhexiline for the treatment of hypertrophic cardiomyopathy
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3858 |
77.0 µM [IC50] | ||
Target ID: CHEMBL3216 |
148.0 µM [IC50] | ||
Target ID: CHEMBL240 |
7.8 µM [IC50] | ||
Target ID: CHEMBL4306 |
1.5 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | PEXSIG Approved UseTo reduce the frequency of moderate to severe attacks of angina pectoris due to coronary artery disease in patients who have not responded to other conventional therapy or in whom such therapy may be contraindicated. Launch Date1977 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
66.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7264901/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PERHEXILINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
274 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7264901/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
PERHEXILINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1010 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7264901/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PERHEXILINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
5110 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7264901/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
PERHEXILINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7264901/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PERHEXILINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
19.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7264901/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
PERHEXILINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27518281/ |
PERHEXILINE plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
6500 mg single, oral Accidental dose Dose: 6500 mg Route: oral Route: single Dose: 6500 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Other AEs: Nausea, Vomiting... |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Parkinsonism, Peripheral neuropathy... AEs leading to discontinuation/dose reduction: Parkinsonism (grade 1) Sources: Peripheral neuropathy |
300 mg 3 times / day multiple, oral Studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Other AEs: Cirrhosis liver... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nausea | 6500 mg single, oral Accidental dose Dose: 6500 mg Route: oral Route: single Dose: 6500 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
|
| Vomiting | 6500 mg single, oral Accidental dose Dose: 6500 mg Route: oral Route: single Dose: 6500 mg Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
|
| Peripheral neuropathy | Disc. AE | 100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Parkinsonism | grade 1 Disc. AE |
100 mg 3 times / day multiple, oral Recommended Dose: 100 mg, 3 times / day Route: oral Route: multiple Dose: 100 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Cirrhosis liver | grade 5 | 300 mg 3 times / day multiple, oral Studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis. | 2013-02 |
|
| Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis. | 2011-10 |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011-07-14 |
|
| Niclosamide prevents the formation of large ubiquitin-containing aggregates caused by proteasome inhibition. | 2010-12-23 |
|
| Glucagon-like peptide-1 and the exenatide analogue AC3174 improve cardiac function, cardiac remodeling, and survival in rats with chronic heart failure. | 2010-11-16 |
|
| Metabolic modulator perhexiline corrects energy deficiency and improves exercise capacity in symptomatic hypertrophic cardiomyopathy. | 2010-10-19 |
|
| Perhexiline and hypertrophic cardiomyopathy: a new horizon for metabolic modulation. | 2010-10-19 |
|
| A novel screen using the Reck tumor suppressor gene promoter detects both conventional and metastasis-suppressing anticancer drugs. | 2010-08 |
|
| Modulation of myocardial metabolism: an emerging therapeutic principle. | 2010-07 |
|
| Metabolic Fingerprinting in Toxicological Assessment Using FT-ICR MS. | 2010-06 |
|
| Chemical inducers of autophagy that enhance the clearance of mutant proteins in neurodegenerative diseases. | 2010-04-09 |
|
| Effects of perhexiline on myocardial deformation in patients with ischaemic left ventricular dysfunction. | 2010-03-04 |
|
| Lack of effect of perhexiline in ischaemic heart failure. | 2010-03-04 |
|
| The pathophysiology of diastolic heart failure. | 2010-02-24 |
|
| Stereoselective Inhibition of the hERG1 Potassium Channel. | 2010 |
|
| Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009-12-02 |
|
| Agents with inotropic properties for the management of acute heart failure syndromes. Traditional agents and beyond. | 2009-12 |
|
| The adrenergic-fatty acid load in heart failure. | 2009-10-27 |
|
| Determination of perhexiline and its metabolite hydroxyperhexiline in human plasma by liquid chromatography/tandem mass spectrometry. | 2009-10-01 |
|
| Relationship between in vitro phospholipidosis assay using HepG2 cells and 2-week toxicity studies in rats. | 2009-10 |
|
| Screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mTORC1 signaling. | 2009-09-22 |
|
| Multi-centre experience on the use of perhexiline in chronic heart failure and refractory angina: old drug, new hope. | 2009-09 |
|
| Multiplexed assay panel of cytotoxicity in HK-2 cells for detection of renal proximal tubule injury potential of compounds. | 2009-09 |
|
| Diabetic cardiomyopathy. | 2009-05 |
|
| Effect of intracellular lipid droplets on cytosolic Ca2+ and cell death during ischaemia-reperfusion injury in cardiomyocytes. | 2009-03-15 |
|
| Overview of therapeutic drug monitoring. | 2009-03 |
|
| Ca2+-dependent functions in peptidoglycan-stimulated mouse dendritic cells. | 2009 |
|
| Effects of metabolic approach in diabetic patients with coronary artery disease. | 2009 |
|
| The metabolic treatment of coronary artery disease and heart failure. | 2009 |
|
| Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. | 2008-12 |
|
| Drug binding to the inactivated state is necessary but not sufficient for high-affinity binding to human ether-à-go-go-related gene channels. | 2008-11 |
|
| Chronic stable angina pectoris. | 2008-09 |
|
| Steatohepatitis-inducing drugs trigger cytokeratin cross-links in hepatocytes. Possible contribution to Mallory-Denk body formation. | 2008-09 |
|
| Metabolic agents in the management of diabetic coronary patients: a new era. | 2008-06-23 |
|
| Metabolic agents in the management of diabetic coronary patients: a new era. | 2008-06-23 |
|
| Gene expression profiling in rat liver treated with compounds inducing phospholipidosis. | 2008-06-15 |
|
| Phospholipidosis assay in HepG2 cells and rat or rhesus hepatocytes using phospholipid probe NBD-PE. | 2008-06 |
|
| The pathophysiology of heart failure: a tale of two old paradigms revisited. | 2008-04 |
|
| Steady-state pharmacokinetics of the enantiomers of perhexiline in CYP2D6 poor and extensive metabolizers administered Rac-perhexiline. | 2008-03 |
|
| Management of the metabolic syndrome in cardiovascular disease. | 2008-02 |
|
| Overview of emerging pharmacologic agents for acute heart failure syndromes. | 2008-02 |
|
| Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment. | 2008-02 |
|
| Metabolic therapy of heart failure. | 2008 |
|
| Modulation of cardiac metabolism during myocardial ischemia. | 2008 |
|
| Impaired tissue responsiveness to organic nitrates and nitric oxide: a new therapeutic frontier? | 2007-11 |
|
| In vitro detection of drug-induced phospholipidosis using gene expression and fluorescent phospholipid based methodologies. | 2007-09 |
|
| Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985-09-01 |
|
| Perhexilene neuropathy: a report of two cases. | 1984-06 |
|
| [The classic anti-anginal agents and molsidomine]. | 1983-02 |
|
| [Electrophysiological study of latent neuropathies induced by perhexiline]. | 1978-11 |
Patents
Sample Use Guides
Commence therapy with 100mg daily. Adjust progressively, up or down, at 2 to 4 weekly intervals based on the results of plasma level monitoring. It is generally advised not to administer more than 300mg per day, in divided doses, but in certain cases it may be necessary to use 400mg per day. The maintenance dose must be the minimum dose that is effective and well tolerated.
Route of Administration:
Oral
Perhexiline maleate was more potent on basal LH release from rat anterior pituitary cell aggregates than on LH stimulated by LHRH. The increases of basal LH secretion induced by perhexiline maleate were 69% (p < 0.001) at a concentration of 10(-7)M, 130% (p < 0.001) at a concentration of 10(-5)M and 250% (p < 0.001) at a concentration of 10(-4)M. Perhexiline maleate also increased the LHRH-stimulated LH release by 25.5% (p < 0.05) at a concentration of 10(-5)M and by 74.5% (p < 0.01) at the concentration of 10(-4)M.
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 23:19:31 GMT 2025
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Mon Mar 31 23:19:31 GMT 2025
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| Record UNII |
84LEC42PQ8
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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Common Name | English | ||
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Systematic Name | English |
| Code System | Code | Type | Description | ||
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5284439
Created by
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103516-75-2
Created by
admin on Mon Mar 31 23:19:31 GMT 2025 , Edited by admin on Mon Mar 31 23:19:31 GMT 2025
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84LEC42PQ8
Created by
admin on Mon Mar 31 23:19:31 GMT 2025 , Edited by admin on Mon Mar 31 23:19:31 GMT 2025
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| Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER |
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ENANTIOMER -> ENANTIOMER |
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