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|ATC code||C01DX02 (WHO)|
|Chemical and physical data|
Systematic (IUPAC) name: (RS)-N-(1-methyl-2-phenylethyl)-3,3-diphenylpropan-1-amine
|3D model (Jmol)||Interactive image|
|Molar mass||329.48 g/mol|
|(what is this?)|
Prenylamine (Segontin) is a calcium channel blocker of the amphetamine chemical class which is used as a vasodilator in the treatment of angina pectoris. It has been shown to partially metabolize to amphetamine and can cause false positives for it in drug tests. Additionally, its use as a stimulant is prohibited by the World Anti-Doping Agency. Prenylamine also appears to act as a vesicular monoamine transporter inhibitor, and has been demonstrated to deplete vesicular monoamine neurotransmitter stores similarly to reserpine.
Common adverse effects include Long QT, torsade de pointe, mild sedation, headaches, dizziness, flushing, skin reaction, dyspepsia, gastric discomfort, vomiting, diarrhea, and increased liver enzymes.
Prenylamine is contraindicated in serious hepatic or renal impairment, gross arrhythmia and presence of uncompensated heart failure. Long term therapy may result in hyphenation and should avoid in the first trimester of pregnancy.
Mechanism of Action:
Prenylamine has two primary molecular target in human,Calmodulin and Myosin light-chain kinase 2 found in skeletal and cardiac muscle. Pharmacologically, it decreases the sympathetic stimulation on cardiac muscle predominantly through partial depletion of catecholamine via competitive inhibition of of reuptake by storage granule, which lead to further depletion due to spontaneous leakage as a result of disturbance of equilibrium.  This depletion mechanism is similar to reserpine because both agents target the same site on storage granule, however prenylamine shows a high affinity for cardiac tissue while reserpine is more selective toward brain tissue.  Prenylamine also slows cardiac metabolism via calcium transport delay by blockade of magnesium-dependent calcium transport ATPase. It also demonstrate a beta blocker-like activity that result in reduction of heart rate however shows opposing effect on tracheal tissue response. 
The onset of action when admistered orally is about 1 hour. It is metablized in the liver. The half-life when administered via IV is 14 hours and when administered orally is 7 hours The time to peak serum concentration is 60 to 90 minutes. It is excreted about 40% in urine and about 37% in feces.:
Prenylamine was originally manufactured under trade name Segotin® by German manufacturer Albert-Roussel pharma gmbh which is acquired by Hoechst AG in 1974. Hoechst AG is now a subsidiary of Sanofi Aventis since 2005. The prenylamine entered U.S. market in 1966 primarily for the treatment of Angina pectoris, however it has been withdrawal from market since 1988 due to major cardiac safety concern such as QT prolongation and Torsades de pointes result in sudden death.
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