Name: | Perhexiline |
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PubChem Compound ID: | 4746 |
Description: | 2-(2,2-Dicyclohexylethyl)piperidine. Coronary vasodilator used especially for angina of effort. It may cause neuropathy and hepatitis. |
Molecular formula: | C19H35N |
Molecular weight: | 277.488 g/mol |
Synonyms: |
Perhexilinum [INN-Latin]; Prestwick0_000286; Prestwick1_000286; KBio3_002618; DivK1c_000542; KBio2_000353; 2-(2,2-dicyclohexylethyl)piperidine; KBio2_005489; KBioSS_000353; NINDS_000542.
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Name: | Perhexiline |
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Name (isomeric): | DB01074 |
Drug Type: | small molecule |
Description: | 2-(2,2-Dicyclohexylethyl)piperidine. Coronary vasodilator used especially for angina of effort. It may cause neuropathy and hepatitis. |
Synonyms: |
2-(2,2-Dicyclohexylethyl)piperidine; Perhexilene; Perhexilinum [INN-Latin]; (-)-2-(2,2-Dicyclohexylethyl)piperidine; Perhexilline; Perhexilina [INN-Spanish]; (+)-2-(2,2-Dicyclohexylethyl)piperidine
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Category: | Vasodilator Agents, Calcium Channel Blockers, Cardiovascular Agents |
CAS number: | 6621-47-2 |
Indication: | For the management of severe angina pectoris. |
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Pharmacology: |
Used in the treatment of unresponsive or refractory angina. Perhexiline increases glucose metabolism at the expense of free-fatty-acid metabolism, enhancing oxygen efficiency during myocardial ischaemia. Perhexiline also potentiates platelet responsiveness to nitric oxide both in patients with angina and patients with acute coronary syndrome. The p...
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Mechanism of Action: |
Perhexiline binds to the mitochondrial enzyme carnitine palmitoyltransferase (CPT)-1 and CPT-2. It acts by shifting myocardial substrate utilisation from long chain fatty acids to carbohydrates through inhibition of CPT-1 and, to a lesser extent, CPT-2, resulting in increased glucose and lactate utilization. This results in increased ATP production...
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Absorption: | Well absorbed (>80%) from the gastrointestinal tract following oral administration. |
Protein binding: | Perhexiline and its metabolites are highly protein bound (>90%). |
Biotransformation: | The principal metabolites of perhexiline in man are monohydroxyperhexiline (which is excreted, in part, conjugated with glucuronic acid) and dihydroxyperhexiline that accounts for a relatively small proportion of the total metabolites. Two unidentified metabolites have also been found in the faeces. The pharmacological activity of the metabolites is not known. Hydroxylation of perhexiline is controlled by cytochrome P450 2D6 (CY P450 2D6). |
Half Life: | Variable and non-linear. Some reports show a half-life of 2-6 days, others indicate it could be as high as 30 days. |
Toxicity: | Oral LD50 rat: 2150 mg/kg; Oral LD50 Mouse: 2641 mg/kg. Short term adverse effects include nausea, transient dizziness, hypoglycaemia in diabetic patients, and torsade de pointes (rare). |
Affected organisms: | Humans and other mammals |