Selegiline
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| Image:Selegiline-2D-skeletal-alternative-view.png | |
| Image:Selegiline-3D-balls.png | |
| Selegiline
| |
| Systematic (IUPAC) name | |
| N-methyl-N-(1-methyl-2-phenyl-ethyl)-prop-2-yn-1-amine | |
| Identifiers | |
| CAS number | [14611-52-0] (HCl), [2079-54-1] (deprenyl.HCl), [4530-70-5] ((+-)-isomer), [1205-70-5] ((+-)-isomer, HCl), [2323-36-6] (cpd w/o isomeric designation; deprenyl), [4528-51-2] ((S)-isomer), [4528-52-3] ((S)-isomer, HCl) |
| ATC code | N04 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C13H17N |
| Mol. mass | 187.281 g/mol |
| Pharmacokinetic data | |
| Bioavailability | 4.4% |
| Protein binding | > 99.5% |
| Metabolism | liver |
| Half life | 2 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
C (US) |
| Legal status |
prescription only (unscheduled) (US) |
| Routes | Oral, transdermally |
Selegiline (l-deprenyl, Eldepryl® or Anipryl® veterinary) is a drug used for the treatment of early-stage Parkinson's disease and senile dementia. In normal clinical doses it is a selective irreversible MAO-B inhibitor, however in larger doses (>20 mg in a typical adult) it loses its specificity and also inhibits MAO-A. Dietary restrictions are common for MAOI treatments, however, since selegiline is selective for MAO-B, special dietary restrictions for lower doses have been found to be unnecessary.[1] The drug was researched by Joseph Knoll. Selegiline is most closely related to the phenylethylamines. The only difference between the two classes of drugs is the attachment of a propargyl group (three carbons with a triple bond between the second and third carbon) to the nitrogen.
Uses
It is sometimes used off-label to treat narcolepsy and as a nootropic, as well as for its published life-extending effects among several species of mammals. It is also reported to positively affect libido, particularly in older males. As of February 28, 2006, selegiline has also been approved by the Food and Drug Administration (FDA) to treat major depression using a transdermal patch (Emsam Patch).[1] Selegiline is also used (at extremely high dosages relative to humans) in veterinary medicine to treat the symptoms of Cushing's disease and so-called "cognitive dysfunction" in dogs. As of June 26, 2006, a selegiline transdermal patch is being tested for its effectiveness in treating ADHD.
Several clinical studies are currently underway to evaluate Selegiline's effectiveness in helping people stop smoking tobacco or marijuana.[1][1]
Mechanism of Action
Selegiline is a selective inhibitor of MAO-B; MAO-B metabolizes dopamine.[1] Selegiline exhibits little therapeutic benefit when used independently, but enhances and prolongs the anti-Parkinson effects of levodopa.[1]
Metabolites
Desmethylselegiline
Desmethylselegiline may have neuroprotective antiapoptotic properties. A large multicenter study suggests a decrease of in the disease progression of parkinsonism but may have reflected other symptomatic response.[1]
L-methamphetamine
Selegiline is partly metabolized to l-methamphetamine, a stereoisomer of methamphetamine in vivo.[1] This stereoisomer is not considered psychoactive and has little abuse potential. The stimulatory effect on locomotor activity and dopamine synthesis may be contributed to by the action of l-methamphetamine.
Due to this metabolite selegiline can cause false positives for amphetamine/methamphetamine on drug tests.
Legal Issues
Possibly due to the structural similarity to illegal stimulants, selegiline has been classified as a controlled substance in Japan and thus can only be obtained with a prescription or special government license. Selegiline is not a controlled substance in the US but a prescription is required to obtain it.
EMSAM
February 28, 2006 - The Food and Drug Administration approved Emsam (selegiline), the first skin (transdermal) patch for use in treating major depression. The once a day patch works by delivering selegiline, a monoamine oxidase inhibitor or MAOI, through the skin and into the bloodstream. At its lowest strength, Emsam can be used without the dietary restrictions that are needed for all oral MAO inhibitors that are approved for treating major depression. It comes in three sizes that deliver 6, 9, or 12 mg of selegiline per 24 hours. The patch is a matrix containing three layers consisting of a backing, and adhesive drug layer, and a release liner that is placed against the skin. EMSAM was developed by Somerset Pharmaceuticals, Inc. In December 2004, Bristol-Myers Squibb and Somerset entered into an agreement that provides Bristol-Myers Squibb with distribution rights to market EMSAM after approval in the United States.
References
External links
- Collection of Research Abstracts on Deprenyl
- An Interview with Dr. Joseph Knoll regarding longevity
- Deprenyl Improves Learning And Memory
- Deprenyl (Selegiline) Can Slow Parkinson's Disease Safely According to the British Medical Journal
- FDA Approves Emsam (Selegiline) as First Drug Patch for Depression
Anti-parkinson drugs: dopaminergic agents (N04B) | |
|---|---|
| Dopa and derivatives | Levodopa, Melevodopa, Etilevodopa |
| Adamantane derivatives | Amantadine |
| Dopamine agonists | Apomorphine, Bromocriptine, Cabergoline, Dihydrexidine, Dihydroergocryptine mesylate, Fenoldopam, Lisuride, Pergolide, Piribedil, Pramipexole, Quinpirole, Ropinirole, Rotigotine, SKF 38393, SKF 82958 |
| MAOIs | Selegiline, Rasagiline |
| Other | Tolcapone, Entacapone, Budipine |
| ||||
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
