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Perhexiline

Catalog No. DB01074 Name DrugBank
CAS Number 6621-47-2 Website http://www.ualberta.ca/
M. F. C19H35N Telephone (780) 492-3111
M. W. 277.4879 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 945

SYNONYMS

IUPAC name
2-(2,2-dicyclohexylethyl)piperidine
IUPAC Traditional name
@perhexiline
Synonyms
Perhexilina [INN-Spanish]
2-(2,2-Dicyclohexylethyl)piperidine
Perhexilene
Perhexilinum [INN-Latin]
(-)-2-(2,2-Dicyclohexylethyl)piperidine
(+)-2-(2,2-Dicyclohexylethyl)piperidine
Perhexilline

DATABASE IDS

CAS Number 6621-47-2
PubChem CID 4746
PubChem SID 46504471

PROPERTIES

Hydrophobicity(logP) 6.2
Solubility 0.0608 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
Description 2-(2,2-Dicyclohexylethyl)piperidine. Coronary vasodilator used especially for angina of effort. It may cause neuropathy and hepatitis. [PubChem]
Indication For the management of severe angina pectoris.
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 predominant mechanism of this particular perhexiline effect is an increase in platelet cGMP responsiveness. Perhexiline also may reduce the potential for nitric oxide clearance by neutrophil-derived oxygen. Perhexiline relieves symptoms of angina, improves exercise tolerance, and increases the workload needed to induce ischaemia when used as monotherapy. The primary therapeutic roles for perhexiline are as short-term therapy (less than 3 months duration) in patients with severe ischaemia awaiting coronary revascularisation or long-term therapy in patients with ischaemic symptoms refractory to other therapeutic measures.
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
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).
Absorption Well absorbed (>80%) from the gastrointestinal tract following oral administration.
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.
Protein Binding Perhexiline and its metabolites are highly protein bound (>90%).
External Links
Wikipedia

REFERENCES