Structure via PubChem · Public domain (PubChem)
perhexiline
Sign in to saveAlso known as Pexsig, (-)-2-(2,2-Dicyclohexylethyl)piperidine, Perhexilline, 2-(2,2-Dicyclohexylethyl)piperidine, (+)-2-(2,2-Dicyclohexylethyl)piperidine, Perhexilene, Perhexilina
Perhexiline (Pexsig) is a prophylactic antianginal agent used primarily in Australia and New Zealand. Perhexiline is thought to act by inhibiting mitochondrial carnitine palmitoyltransferase-1. This shifts myocardial metabolism from fatty acid to glucose utilisation which results in increased ATP production for the same O2 consumption and consequently increases myocardial efficiency. Its clinical use has been limited by its narrow therapeutic index and high inter- and intra-individual pharmacokinetic variability. It was outlawed in many countries due to its adverse effects on poor metabolisers
Chemical data
- Formula
- C19H35N
- Molecular weight
- 277.5 g/mol
- IUPAC name
- 2-(2,2-dicyclohexylethyl)piperidine
- SMILES
- C1CCC(CC1)C(CC2CCCCN2)C3CCCCC3
- InChIKey
- CYXKNKQEMFBLER-UHFFFAOYSA-N
- XLogP
- 6.8
- Polar surface area
- 12 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1974
- Indications
- hypertrophic cardiomyopathy, heart failure, diastolic heart failure, diabetic cardiomyopathy
via ChEMBL · EBI
Research
703 papers- Perhexiline.Cardiovascular drug reviews · 2007
- Perhexiline: Old Drug, New Tricks? A Summary of Its Anti-Cancer Effects.Molecules (Basel, Switzerland) · 2023
- Perhexiline Demonstrates FYN-mediated Antitumor Activity in Glioblastoma.Molecular cancer therapeutics · 2020
- Perhexiline: lessons for heart failure therapeutics.JACC. Heart failure · 2015
- Perhexiline maleate-induced cirrhosis.Gastroenterology · 1979
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 277.27695
- Has use
- medication
Show 3 more facts
- chemical formula
- C₁₉H₃₅N
- canonical SMILES
- C1CCC(CC1)C(CC2CCCCN2)C3CCCCC3
- physically interacts with
- carnitine palmitoyltransferase 2
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
5 sectionsContents
- Perhexiline metabolism
- Poor metabolisers
- Hydroxyperhexiline:perhexiline ratio
- Perhexiline toxicity
- References
Perhexiline (Pexsig) is a prophylactic antianginal agent used primarily in Australia and New Zealand. Perhexiline is thought to act by inhibiting mitochondrial carnitine palmitoyltransferase-1. This shifts myocardial metabolism from fatty acid to glucose utilisation which results in increased ATP production for the same O2 consumption and consequently increases myocardial efficiency. Its clinical use has been limited by its narrow therapeutic index and high inter- and intra-individual pharmacokinetic variability. It was outlawed in many countries due to its adverse effects on poor metabolisers (PM). The product has been reintroduced for patients who have contraindications, or have not responded to other treatments for angina.
==Perhexiline metabolism== The major route of perhexiline metabolism in humans is hydroxylation by microsomal CYP2D6. The two main metabolites of perhexiline are the cis and trans isomers of hydroxyperhexiline. CYP2D6 accounts for only a small percentage of total hepatic CYP450s but it is one of the main pathways for phase one metabolism of xenobiotics. The limited availability of CYP2D6 means perhexiline metabolism is a saturable process.
Excerpted from Wikipedia’s “perhexiline” article, available under the CC BY-SA 4.0 licence.