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Selegiline, also known as L -deprenyl, is a substituted phenethylamine. At normal clinical doses, it is a selective irreversible MAO-B inhibitor. In larger doses it loses its specificity and also inhibits MAO-A. It is available in pill form under many brand names and is used to reduce symptoms in early-stage Parkinson’s disease. A transdermal patch (brand name, Emsam ) is used to treat depression.
Contents
1 Medical uses
1.1 Parkinson’s disease
1.2 Depression
1.3 Special populations
2 Adverse effects
3 Interactions
4 Pharmacology
4.1 Mechanism of action
4.2 Pharmacokinetics
4.2.1 Metabolism
4.2.2 Patch
5 Chemistry
6 History
7 Society and culture
8 Veterinary use
9 See also
10 References
Medical uses
Parkinson’s disease
In its pill form, selegiline is used to treat symptoms of Parkinson’s disease.
Selegiline has also been used off-label as a palliative treatment for dementia in Alzheimer’s disease.
Depression
Selegiline is also delivered via a transdermal patch used as a treatment for major depressive disorder.
A quantitative review published in 2015 found that for the pooled results of the pivotal trials, the number needed to treat (a sign of effect size, so a low number is better) for the patch for symptom reduction was 11, and for remission, was 9.
Special populations
For all human uses and all forms, selegiline is pregnancy category C: studies in pregnant lab animals have shown adverse effects on the fetus but there are no adequate studies in humans.
Adverse effects
Side effects of the pill form include, in decreasing order of frequency, nausea, hallucinations, confusion, depression, loss of balance, insomnia, increased involuntary movements, agitation, slow or irregular heart rate, delusions, hypertension, new or increased angina pectoris, and syncope.
The main side effects of the patch form for depression included application-site reactions, insomnia, diarrhea, and sore throat.
Interactions
Both the oral and patch forms come with strong warnings against combining selegiline with drugs that could produce serotonin syndrome, such as SSRIs and the cough medicine dextromethorphan.
Oral contraceptives increases selegiline’s bioavailability 10- to 20-fold.
Both forms of the drug carry warnings about food restrictions to avoid hypertensive crisis that are associated with MAO inhibitors.
Pharmacology
Mechanism of action
Selegiline is a selective inhibitor of MAO-B in the nigrostriatal pathway of the brain, irreversibly inhibiting it by binding to it covalently.
Selegiline also inhibits CYP2A6 and can increase the effects of nicotine as a result.
Pharmacokinetics
Selegiline has an oral bioavailability of about 10%, which increases when ingested together with fatty meal, as the molecule is fat soluble.
Selegiline is mostly metabolized in the gut wall and liver ; it and its metabolites are excreted in the urine.
Metabolism
Selegiline is metabolized by cytochrome P450 to L-desmethylselegiline and L-methylamphetamine, the latter being one of the enantiomers of methamphetamine. The amphetamine metabolites are hydroxylated and, in phase II, conjugated by glucuronyltransferase.
A newer anti-Parkinson MAO-B inhibitor, rasagiline, metabolizes into 1( R )-aminoindan, which has no amphetamine-like characteristics.
Patch
Following application of the patch to humans, an average of 25% to 30% of the selegiline content is delivered systemically over 24 hours. Transdermal dosing results in significantly higher exposure to selegiline and lower exposure to all metabolites when compared to oral dosing; this is due to the extensive first-pass metabolism of the pill form and low first-pass metabolism of the patch form. The site of application is not a significant factor in how the drug is distributed. In humans, selegiline does not accumulate in the skin, nor is it metabolized there.
Chemistry
Selegiline belongs to a class of drugs called phenethylamines. Selegiline is an L -methamphetamine derivative with a propargyl group attached to the nitrogen atom. This detail is borrowed from pargyline, an older phenethylamine MAO-B inhibitor.
Selegiline, N -methyl- N -(2-propynyl)-2-methyl-1-phenylethyl-2-amine, is synthesized by the alkylation of (–)- methamphetamine using propargyl bromide.
History
Following the discovery that the tuberculosis drug iproniazid elevated the mood of people taking it, and the subsequent discovery that the effect was likely due to inhibition of MAO, many people and companies started trying to discover MAO inhibitors to use as antidepressants. Selegiline was discovered by Z. Ecseri at the Hungarian drug company, Chinoin (part of Sanofi since 1993), : 67
Emsam transdermal patch, 6mg/24hr dose Deprenyl is a racemic compound a mixture of two isomers called enantiomers. Further work determined that the levorotatory enantiomer was a more potent MAO-inhibitor, which was published in 1967, and subsequent work was done with the single enantiomer L -deprenyl.
In 1971, Knoll showed that selegiline selectively inhibits the B-isoform of monoamine oxidase (MAO-B) and proposed that it is unlikely to cause the infamous “cheese effect” ( hypertensive crisis resulting from consuming foods containing tyramine ) that occurs with non-selective MAO inhibitors. A few years later, two Parkinson’s disease researchers based in Vienna, Peter Riederer and Walther Birkmayer, realized that selegiline could be useful in Parkinson’s disease. One of their colleagues, Prof. Moussa B.H. Youdim, visited Knoll in Budapest and took selegiline from him to Vienna. In 1975, Birkmayer’s group published the first paper on the effect of selegiline in Parkinson’s disease.
In the 1970s there was speculation that it could be useful as an anti-aging drug or aphrodisiac.
In 1987 Somerset Pharmaceuticals in New Jersey, which had acquired the US rights to develop selegiline, filed a new drug application (NDA) with the FDA to market the drug for Parkinson’s disease in the US.
In the 1990s, J. Alexander Bodkin at McLean Hospital, an affiliate of Harvard Medical School, began a collaboration with Somerset to develop delivery of selegiline via a transdermal patch in order to avoid the well known dietary restrictions of MAO inhibitors.
Society and culture
In E for Ecstasy (a book examining the uses of the street drug ecstasy in the UK) the writer, activist and ecstasy advocate Nicholas Saunders highlighted test results showing that certain consignments of the drug also contained selegiline.
Veterinary use
In veterinary medicine, selegiline is sold under the brand name Anipryl (manufactured by Zoetis ). It is used in dogs to treat canine cognitive dysfunction and, at higher doses, pituitary -dependent hyperadrenocorticism (PDH).
Selegiline’s efficacy in treating pituitary-dependent hyperadrenocorticism has been disputed.
Side effects in dogs are uncommon, but they include vomiting, diarrhea, diminished hearing, salivation, decreased weight and behavioral changes such as hyperactivity, listlessness, disorientation, and repetitive motions.
Selegiline does not appear to have a clinical effect on horses.
See also
D -Deprenyl
Rasagiline
Tranylcypromine

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