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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
Structure of PERHEXILINE

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

HIDE SMILES / InChI

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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PEXSIG

Approved Use

To 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 Date

2.52374401E11
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Electrophysiological study of latent neuropathies induced by perhexiline].
1978 Nov
[The classic anti-anginal agents and molsidomine].
1983 Feb
Perhexilene neuropathy: a report of two cases.
1984 Jun
Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies.
1985 Sep-Oct
Systematic review of the efficacy and safety of perhexiline in the treatment of ischemic heart disease.
2001
[Amphiphilic cationic drug myopathy, drug-induced lysosomal storage lipidosis].
2001
New tricks for an old drug.
2002 Dec
Leustroducsin B activates nuclear factor-kappaB via the acidic sphingomyelinase pathway in human bone marrow-derived stromal cell line KM-102.
2002 Mar
Correlation of CYP2D6 genotype with perhexiline phenotypic metabolizer status.
2003 Oct
Metabolic manipulation in ischaemic heart disease, a novel approach to treatment.
2004 Apr
Design, synthesis, and biological evaluation of novel T-Type calcium channel antagonists.
2004 Jul 16
Determination of perhexiline and hydroxyperhexiline in plasma by liquid chromatography-mass spectrometry.
2004 Jun 5
Dissociation between metabolic and efficiency effects of perhexiline in normoxic rat myocardium.
2005 Dec
Influence of different calcic antagonists on the Caco-2 cell monolayer integrity or "TEER, a measurement of toxicity?".
2005 Jan-Jun
Individualized drug and dose: the clinical pharmacologist's calling or curse?
2005 Nov
Metabolic modulation with perhexiline in chronic heart failure: a randomized, controlled trial of short-term use of a novel treatment.
2005 Nov 22
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
Determination of the 4-monohydroxy metabolites of perhexiline in human plasma, urine and liver microsomes by liquid chromatography.
2006 Nov 7
Can pharmacogenetics help rescue drugs withdrawn from the market?
2006 Sep
CYP2B6, CYP2D6, and CYP3A4 catalyze the primary oxidative metabolism of perhexiline enantiomers by human liver microsomes.
2007 Jan
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
Impaired tissue responsiveness to organic nitrates and nitric oxide: a new therapeutic frontier?
2007 Nov
Perhexiline.
2007 Spring
Modulation of cardiac metabolism during myocardial ischemia.
2008
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.
2008 Dec
Phospholipidosis assay in HepG2 cells and rat or rhesus hepatocytes using phospholipid probe NBD-PE.
2008 Jun
Gene expression profiling in rat liver treated with compounds inducing phospholipidosis.
2008 Jun 15
Metabolic agents in the management of diabetic coronary patients: a new era.
2008 Jun 23
Metabolic agents in the management of diabetic coronary patients: a new era.
2008 Jun 23
Steady-state pharmacokinetics of the enantiomers of perhexiline in CYP2D6 poor and extensive metabolizers administered Rac-perhexiline.
2008 Mar
Steatohepatitis-inducing drugs trigger cytokeratin cross-links in hepatocytes. Possible contribution to Mallory-Denk body formation.
2008 Sep
Ca2+-dependent functions in peptidoglycan-stimulated mouse dendritic cells.
2009
Effects of metabolic approach in diabetic patients with coronary artery disease.
2009
Agents with inotropic properties for the management of acute heart failure syndromes. Traditional agents and beyond.
2009 Dec
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Diabetic cardiomyopathy.
2009 May
Relationship between in vitro phospholipidosis assay using HepG2 cells and 2-week toxicity studies in rats.
2009 Oct
The adrenergic-fatty acid load in heart failure.
2009 Oct 27
Screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mTORC1 signaling.
2009 Sep 22
Stereoselective Inhibition of the hERG1 Potassium Channel.
2010
A novel screen using the Reck tumor suppressor gene promoter detects both conventional and metastasis-suppressing anticancer drugs.
2010 Aug
Niclosamide prevents the formation of large ubiquitin-containing aggregates caused by proteasome inhibition.
2010 Dec 23
Modulation of myocardial metabolism: an emerging therapeutic principle.
2010 Jul
Metabolic Fingerprinting in Toxicological Assessment Using FT-ICR MS.
2010 Jun
Effects of perhexiline on myocardial deformation in patients with ischaemic left ventricular dysfunction.
2010 Mar 4
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
Perhexiline and hypertrophic cardiomyopathy: a new horizon for metabolic modulation.
2010 Oct 19
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis.
2011 Oct
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
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 Sat Jun 26 14:35:09 UTC 2021
Edited
by admin
on Sat Jun 26 14:35:09 UTC 2021
Record UNII
KU65374X44
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PERHEXILINE
INN   MI   WHO-DD  
INN  
Official Name English
2-(2,2-DICYCLOHEXYLETHYL)PIPERIDINE
Systematic Name English
PERHEXILINE [WHO-DD]
Common Name English
(+/-)-2-(2,2-DICYCLOHEXYLETHYL)PIPERIDINE
Systematic Name English
PERHEXILINE [INN]
Common Name English
PERHEXILINE [MI]
Common Name English
PIPERIDINE, 2-(2,2-DICYCLOHEXYLETHYL)-
Systematic Name English
Classification Tree Code System Code
WHO-ATC C08EX02
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
WHO-VATC QC08EX02
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
Code System Code Type Description
DRUG CENTRAL
2106
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL75880
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
WIKIPEDIA
PERHEXILINE
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
FDA UNII
KU65374X44
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
PUBCHEM
4746
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
CAS
6621-47-2
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
MERCK INDEX
M8548
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
229-569-5
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
DRUG BANK
DB01074
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
EPA CompTox
6621-47-2
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
MESH
D010480
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
INN
1850
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
NCI_THESAURUS
C170311
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
RXCUI
8050
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY RxNorm
EVMPD
SUB09726MIG
Created by admin on Sat Jun 26 14:35:10 UTC 2021 , Edited by admin on Sat Jun 26 14:35:10 UTC 2021
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
ENANTIOMER -> RACEMATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY