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SML0120

Sigma-Aldrich

Perhexiline maleate salt

≥98% (HPLC)

Synonym(s):

2-(2,2-Dicyclohexylethyl)piperidine

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About This Item

Empirical Formula (Hill Notation):
C19H35N · C4H4O4
CAS Number:
6724-53-4
Molecular Weight:
393.56
EC Number:
229-775-5
MDL number:
MFCD00057329
UNSPSC Code:
12352200
PubChem Substance ID:
329825171
NACRES:
NA.25

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

OC(=O)\C=C/C(O)=O.C1CCC(CC1)C(CC2CCCCN2)C3CCCCC3

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-

InChI key

JDZOTSLZMQDFLG-BTJKTKAUSA-N

Gene Information

human ... CPT1B(1375) , CPT2(1376) , MTOR(2475)

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General description

Perhexiline maleate regulates coronary vasodilatation and blocks exercise-induced tachycardia. It is used to treat angina pectoris and variant angina. Perhexiline maleate functions as a cardiac metabolic agent. It is associated with peripheral neuropathy, high intracranial pressure with papilledema and proximal myopathy.

Application

Perhexiline maleate salt has been used as a stock for worm lifespan assay. It has also been used to block fatty acid oxidation.
Perhexiline maleate salt has been used to block fatty acid oxidation. It has also been used as 5′ adenosine monophosphate-activated protein kinase (AMPK) activator and in worm lifespan assay.

Biochem/physiol Actions

Perhexiline maleate is an anti-anginal metabolic modulator. It inhibits the mitochondrial enzyme carnitine palmitoyltransferase CPT-1 and to a lesser extent CPT-2. This causes a shift in myocardial substrate utilisation from long chain fatty acids to carbohydrates, resulting in increased glucose and lactate utilization and increased ATP production for the same O2 consumption as before and consequently increases myocardial efficiency. Perhexiline maleate was also recently found to inhibit the activity of mTORC1.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Harel Gilutz et al.
Therapeutic drug monitoring, 34(2), 227-231 (2012-02-11)
Concomitant treatment with amiodarone and perhsexiline has been considered to be relatively contraindicated because of the hypothetical risk of potentiated adverse effects mediated by additive inhibition of carnitine palmitoyl transferase 1. To study the prevalence of adverse effects associated with
Accurate Drug Repositioning through Non-tissue-Specific Core Signatures from Cancer Transcriptomes
Xu C, et al.
Testing, 25(2), 523-535 (2018)
V Shacoori et al.
Research communications in chemical pathology and pharmacology, 59(2), 161-172 (1988-02-01)
Human clinical observations and in vivo studies have shown that the amphiphilic drug perhexiline maleate is responsible for lipidosis storage disorders. When the drug was incubated in vivo with rat brain homogenates, the ouabain-sensitive (Na+,K+)-ATPase and the Mg++-ATPase activities were
J D Cooper et al.
Annals of clinical biochemistry, 22 ( Pt 6), 614-617 (1985-11-01)
Patients taking oral doses of perhexiline maleate have been examined. Measurement of serum perhexiline concentrations established that different dose requirements between patients were necessary due to the different doses at which drug saturation was achieved. Measurement of serum perhexiline concentrations
J D Horowitz et al.
International journal of cardiology, 13(2), 219-229 (1986-11-01)
Perhexiline maleate, which causes inhibition of myocardial fatty acid catabolism with a concomitant increase in glucose utilization, is particularly useful in the management of patients with severe angina pectoris. While perhexiline exerts no significant negative inotropic or dromotropic effects, its
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