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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
Impaired tissue responsiveness to organic nitrates and nitric oxide: a new therapeutic frontier?
2007 Nov
In vitro detection of drug-induced phospholipidosis using gene expression and fluorescent phospholipid based methodologies.
2007 Sep
Metabolic therapy of heart failure.
2008
Modulation of cardiac metabolism during myocardial ischemia.
2008
The pathophysiology of heart failure: a tale of two old paradigms revisited.
2008 Apr
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.
2008 Dec
Management of the metabolic syndrome in cardiovascular disease.
2008 Feb
Overview of emerging pharmacologic agents for acute heart failure syndromes.
2008 Feb
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.
2008 Feb
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
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 Nov
Chronic stable angina pectoris.
2008 Sep
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
The metabolic treatment of coronary artery disease and heart failure.
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
Overview of therapeutic drug monitoring.
2009 Mar
Effect of intracellular lipid droplets on cytosolic Ca2+ and cell death during ischaemia-reperfusion injury in cardiomyocytes.
2009 Mar 15
Diabetic cardiomyopathy.
2009 May
Relationship between in vitro phospholipidosis assay using HepG2 cells and 2-week toxicity studies in rats.
2009 Oct
Determination of perhexiline and its metabolite hydroxyperhexiline in human plasma by liquid chromatography/tandem mass spectrometry.
2009 Oct 1
The adrenergic-fatty acid load in heart failure.
2009 Oct 27
Multi-centre experience on the use of perhexiline in chronic heart failure and refractory angina: old drug, new hope.
2009 Sep
Multiplexed assay panel of cytotoxicity in HK-2 cells for detection of renal proximal tubule injury potential of compounds.
2009 Sep
Screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mTORC1 signaling.
2009 Sep 22
Stereoselective Inhibition of the hERG1 Potassium Channel.
2010
Chemical inducers of autophagy that enhance the clearance of mutant proteins in neurodegenerative diseases.
2010 Apr 9
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
The pathophysiology of diastolic heart failure.
2010 Feb 24
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
Lack of effect of perhexiline in ischaemic heart failure.
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
Metabolic modulator perhexiline corrects energy deficiency and improves exercise capacity in symptomatic hypertrophic cardiomyopathy.
2010 Oct 19
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