Details
Stereochemistry | RACEMIC |
Molecular Formula | C19H35N |
Molecular Weight | 277.4886 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CCC(CC1)C(CC2CCCCN2)C3CCCCC3
InChI
InChIKey=CYXKNKQEMFBLER-UHFFFAOYSA-N
InChI=1S/C19H35N/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18/h16-20H,1-15H2
Molecular Formula | C19H35N |
Molecular Weight | 277.4886 |
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8694852 |
77.0 µM [IC50] | ||
Target ID: CHEMBL3216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8694852 |
148.0 µM [IC50] | ||
Target ID: CHEMBL240 |
7.8 µM [IC50] | ||
Target ID: CHEMBL4306 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7616429 |
1.5 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 Date2.52374401E11 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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[Electrophysiological study of latent neuropathies induced by perhexiline]. | 1978 Nov |
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[The classic anti-anginal agents and molsidomine]. | 1983 Feb |
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Perhexilene neuropathy: a report of two cases. | 1984 Jun |
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Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985 Sep-Oct |
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Systematic review of the efficacy and safety of perhexiline in the treatment of ischemic heart disease. | 2001 |
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[Amphiphilic cationic drug myopathy, drug-induced lysosomal storage lipidosis]. | 2001 |
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New tricks for an old drug. | 2002 Dec |
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Leustroducsin B activates nuclear factor-kappaB via the acidic sphingomyelinase pathway in human bone marrow-derived stromal cell line KM-102. | 2002 Mar |
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Correlation of CYP2D6 genotype with perhexiline phenotypic metabolizer status. | 2003 Oct |
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Metabolic manipulation in ischaemic heart disease, a novel approach to treatment. | 2004 Apr |
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Design, synthesis, and biological evaluation of novel T-Type calcium channel antagonists. | 2004 Jul 16 |
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Determination of perhexiline and hydroxyperhexiline in plasma by liquid chromatography-mass spectrometry. | 2004 Jun 5 |
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Dissociation between metabolic and efficiency effects of perhexiline in normoxic rat myocardium. | 2005 Dec |
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Influence of different calcic antagonists on the Caco-2 cell monolayer integrity or "TEER, a measurement of toxicity?". | 2005 Jan-Jun |
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Individualized drug and dose: the clinical pharmacologist's calling or curse? | 2005 Nov |
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Metabolic modulation with perhexiline in chronic heart failure: a randomized, controlled trial of short-term use of a novel treatment. | 2005 Nov 22 |
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The influence of CYP2D6 genotype on trough plasma perhexiline and cis-OH-perhexiline concentrations following a standard loading regimen in patients with myocardial ischaemia. | 2006 Mar |
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Determination of the 4-monohydroxy metabolites of perhexiline in human plasma, urine and liver microsomes by liquid chromatography. | 2006 Nov 7 |
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Can pharmacogenetics help rescue drugs withdrawn from the market? | 2006 Sep |
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CYP2B6, CYP2D6, and CYP3A4 catalyze the primary oxidative metabolism of perhexiline enantiomers by human liver microsomes. | 2007 Jan |
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Acidic extracellular pH increases calcium influx-triggered phospholipase D activity along with acidic sphingomyelinase activation to induce matrix metalloproteinase-9 expression in mouse metastatic melanoma. | 2007 Jun |
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Impaired tissue responsiveness to organic nitrates and nitric oxide: a new therapeutic frontier? | 2007 Nov |
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Perhexiline. | 2007 Spring |
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Modulation of cardiac metabolism during myocardial ischemia. | 2008 |
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Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. | 2008 Dec |
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Phospholipidosis assay in HepG2 cells and rat or rhesus hepatocytes using phospholipid probe NBD-PE. | 2008 Jun |
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Gene expression profiling in rat liver treated with compounds inducing phospholipidosis. | 2008 Jun 15 |
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Metabolic agents in the management of diabetic coronary patients: a new era. | 2008 Jun 23 |
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Metabolic agents in the management of diabetic coronary patients: a new era. | 2008 Jun 23 |
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Steady-state pharmacokinetics of the enantiomers of perhexiline in CYP2D6 poor and extensive metabolizers administered Rac-perhexiline. | 2008 Mar |
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Steatohepatitis-inducing drugs trigger cytokeratin cross-links in hepatocytes. Possible contribution to Mallory-Denk body formation. | 2008 Sep |
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Ca2+-dependent functions in peptidoglycan-stimulated mouse dendritic cells. | 2009 |
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Effects of metabolic approach in diabetic patients with coronary artery disease. | 2009 |
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Agents with inotropic properties for the management of acute heart failure syndromes. Traditional agents and beyond. | 2009 Dec |
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Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
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Diabetic cardiomyopathy. | 2009 May |
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Relationship between in vitro phospholipidosis assay using HepG2 cells and 2-week toxicity studies in rats. | 2009 Oct |
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The adrenergic-fatty acid load in heart failure. | 2009 Oct 27 |
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Screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mTORC1 signaling. | 2009 Sep 22 |
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Stereoselective Inhibition of the hERG1 Potassium Channel. | 2010 |
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A novel screen using the Reck tumor suppressor gene promoter detects both conventional and metastasis-suppressing anticancer drugs. | 2010 Aug |
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Niclosamide prevents the formation of large ubiquitin-containing aggregates caused by proteasome inhibition. | 2010 Dec 23 |
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Modulation of myocardial metabolism: an emerging therapeutic principle. | 2010 Jul |
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Metabolic Fingerprinting in Toxicological Assessment Using FT-ICR MS. | 2010 Jun |
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Effects of perhexiline on myocardial deformation in patients with ischaemic left ventricular dysfunction. | 2010 Mar 4 |
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Glucagon-like peptide-1 and the exenatide analogue AC3174 improve cardiac function, cardiac remodeling, and survival in rats with chronic heart failure. | 2010 Nov 16 |
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Perhexiline and hypertrophic cardiomyopathy: a new horizon for metabolic modulation. | 2010 Oct 19 |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
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Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis. | 2011 Oct |
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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 Feb |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7749649
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
by
admin
on
Edited
Sat Jun 26 14:35:09 UTC 2021
by
admin
on
Sat Jun 26 14:35:09 UTC 2021
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Record UNII |
KU65374X44
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Record Status |
Validated (UNII)
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Record Version |
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-
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WHO-ATC |
C08EX02
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WHO-VATC |
QC08EX02
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2106
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CHEMBL75880
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PERHEXILINE
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KU65374X44
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4746
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6621-47-2
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M8548
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229-569-5
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DB01074
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6621-47-2
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D010480
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1850
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C170311
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8050
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SUB09726MIG
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |