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Selegiline

 
Drug Info: Selegiline
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Brand names: Carbex®Eldepryl®Zelapar®

Chemical formula:



Selegiline Hydrochloride Oral capsule

What is this medicine?

SELEGILINE (se LE ji leen) is an monoamine oxidase inhibitor (MAOI). It is used with levodopa-carbidopa in the treatment of Parkinson's disease. It is usually added to therapy when there is a decrease in response to levodopa.
 
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
•frequently drink alcohol-containing beverages
•kidney disease
•liver disease
•an unusual or allergic reaction to selegiline, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding

How should I use this medicine?

Take this medicine by mouth with a glass of water. Follow the directions on the prescription label. Take your doses at regular intervals. Do not take your medicine more often than directed. Do not stop taking except on the advice of your doctor or health care professional.

Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What if I miss a dose?

If you miss a dose, take it as soon as you can if it is not more than four hours since your dose was due (except for Procanbid™ tablets which should not be taken unless 8 hours before the next dose.) If it is almost time for your next dose, take only that dose. Do not take double or extra doses. Consult your prescriber or health care professional if you are in doubt.

What may interact with this medicine?

Do not take this medicine with any of the following medications:
•altretamine
•atomoxetine
•caffeine
•carbamazepine
•cocaine
•dextromethorphan
•diphenoxylate
•ephedrine
•herbal medicines like ginseng, green tea, guarana, SAM-e, and St. John's Wort
•isoniazid
•linezolid
•local anesthetics
•medicines for mental depression
•medicines for migraine headaches
•meperidine
•procarbazine
•pseudoephedrine
•stimulants like amphetamine, dextroamphetamine or methylphenidate
•tramadol
•tryptophan

This medicine may also interact with the following medications:
•medicines for high blood pressure
•prescription pain medicines

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Visit your doctor or health care professional for regular checks on your progress. It can take up to 4 weeks to see the full effects of this medicine. Do not suddenly stop taking your medicine. This may make your condition worse or cause withdrawal symptoms. Ask your doctor or health care professional for advice about gradually reducing your dosage. Even after you stop taking this medicine the effects can last for at least two weeks.
 
Patients and their families should watch out for depression or thoughts of suicide that get worse. Also watch out for sudden or severe changes in feelings such as feeling anxious, agitated, panicky, irritable, hostile, aggressive, impulsive, severely restless, overly excited and hyperactive, or not being able to sleep. If this happens, especially at the beginning of antidepressant treatment or after a change in dose, call your health care professional.
 
If your doctor or health care professional increases the dose of this medicine to more than 10 mg a day, ask him/her about possible interactions with foods that contain tyramine. At higher doses, this medicine may interact with these foods to produce severe headaches, a rise in blood pressure, or irregular heart beat.
 
You may get drowsy, dizzy or have blurred vision. Do not drive, use machinery, or do anything that needs mental alertness until you know how this medicine affects you. Do not stand or sit up quickly, especially if you are an older patient. This reduces the risk of dizzy or fainting spells. Alcohol may increase dizziness or drowsiness. Do not drink alcoholic beverages while taking this medicine.
 
Your mouth may get dry. Chewing sugarless gum or sucking hard candy, and drinking plenty of water may help. Contact your doctor if the problem does not go away or is severe.
 
Do not treat yourself for coughs, colds, flu or allergies without asking your doctor or health care professional for advice. Do not take any medications for weight loss without advice either. Some ingredients in these products may increase possible side effects.
 
This medicine may affect blood sugar levels. If you have diabetes, check with your doctor or health care professional before you change your diet or the dose of your diabetic medicine.
 
Tell your health care professional that you are taking this medicine if you are scheduled to have any surgery, procedure or medical testing.
 
There have been reports of increased sexual urges or other strong urges such as gambling while taking some medicines for Parkinson's disease. If you experience any of these urges while taking this medicine, you should report it to your health care provider as soon as possible.
 
You should check your skin often for changes to moles and new growths while taking this medicine. Call your doctor if you notice any of these changes.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•angry, excitable, panic attack, mania, restless
•breathing problems
•chest pain
•difficulty passing urine
•eyes more sensitive to light, enlarged pupils
•feeling faint or lightheaded, falls
•fever, clammy skin, increased sweating, sore throat
•high blood pressure
•irregular heartbeat
•muscle or neck stiffness or spasm
•seizures
•suicidal thoughts or other mood changes
•trouble sleeping
•yellowing of the skin or eyes

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•change in sex drive or performance
•constipation or diarrhea
•increased appetite or weight increase
•increased sensitivity to sunlight
•muscle aches or pains, trembling
•nausea or vomiting
•swelling of the feet or legs
•tired or weak

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Throw away any unused medicine after the expiration date.

Last updated: 3/22/2006 10:15:00 AM

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

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Wikipedia: Selegiline
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Home > Library > Miscellaneous > Wikipedia
Selegiline
Systematic (IUPAC) name
(R)-N-methyl-N-(1-phenylpropan-2-yl)prop-2-yn-1-amine
Identifiers
CAS number 14611-51-9 [14611-52-0] (HCl)
ATC code N04BD01 QN06AX90
PubChem 26757
DrugBank APRD00525
ChemSpider 24930
Chemical data
Formula C13H17N 
Mol. mass 187.281 g/mol
Pharmacokinetic data
Bioavailability 4.4% (oral, fasted), 20% (oral, after food), 18% (patch)
Protein binding 90%
Metabolism liver
Half life 1.5 hours (oral, single dose), 9 hours (oral, chronic)
Excretion urine
Therapeutic considerations
Pregnancy cat.

C (US)
Legal status

prescription only (unscheduled) (US)
Routes Oral, transdermal, buccal
 Yes check.svgY(what is this?)  (verify)

Selegiline (l-deprenyl, Eldepryl) is a drug used for the treatment of early-stage Parkinson's disease, depression and senile dementia. In normal clinical doses it is a selective irreversible MAO-B inhibitor, however in larger doses it loses its specificity and also inhibits MAO-A. Dietary restrictions are common for MAOI treatments, but special dietary restrictions for lower doses have been found to be unnecessary.[1] The drug was researched by Jozsef Knoll et al. (Hungary). Selegiline belongs to a class of drugs called phenethylamines. Selegiline consists of a l-desoxyephedrine (levomethamphetamine) skeleton with a propargyl group attached to the nitrogen atom.

Contents

History

Selegiline was discovered in Hungary in the 1960s. Joseph Knoll, a chair of pharmacology at the Semmelweis University in Budapest, was interested in the physiology of "drive" and the differences between high- and low-performing individuals. For his research, he required a molecule that combined amphetamine-like psychostimulant effect with a "psycho-energic" effect of monoamine oxidase inhibitors (MAOI). To do that, he decided to combine in the same molecule the structural features of the MAOI pargyline and the psychostimulant amphetamine. Knoll was a close friend of Meszaros, the research director of Chinoin, a Hungarian pharmaceutical company (later part of Sanofi). For this project, Meszaros put Knoll in contact with a chemist called Ecsery who worked in Chinoin in the field of phenethylamines. Escery made about 30 compounds, and Knoll selected the molecule of E-250 (deprenyl) based on its surprising properties. "The great discovery" (in Knoll's words) was that the new molecule did not increase blood pressure, unlike amphetamine, and moreover, it inhibited the blood pressure raising effect of amphetamine. The first publication on deprenyl in Hungarian appeared in 1964, followed by a paper in English in 1965. Deprenyl is a racemic compound, a mixture of two isomers called enantiomers. For the further pharmaceutical development, Knoll chose the (-)-enantiomer of deprenyl, which caused less hypermotility than the opposite (+)-enantiomer. This (-)-enantiomer (l-deprenyl, R-deprenyl) later has come to be called selegiline.[2]

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 plagues non-selective MAO inhibitors. A few years later, two Parkinson's researchers based in Vienna, Peter Riederer and Walther Birkmayer, realized that selegiline could be useful in Parkinson's disease. One of their colleagues, Moussa Youdim, visited Knoll in Budapest and took selegiline from him to Vienna. In 1975, the Birkmayer's group published the first paper on the effect of selegiline in Parkinson's disease. [2][3]

In 1967, a Hungarian psychiatrist Ervin Varga observed that racemic deprenyl given in large doses has an antidepressant action.[4] This study was largely forgotten until the 2000s when Sommerset Pharmaceuticals developed selegiline patch for depression.

Uses

The main use of selegiline is in the treatment of Parkinson's disease. It can be used on its own or in a combination with another agent, most often L-DOPA.[5] For the newly diagnosed Parkinson's patients, selegiline appears to slow the progression of the disease. It delays the time point when the L-DOPA (levodopa) treatment becomes necessary from 10-12 to 18 months.[6] The idea behind adding selegiline to levodopa is to decrease the dose of levodopa and thus reduce the motor complications of levodopa therapy.[7] Comparisons of patients on levodopa + placebo vs levodopa + selegiline showed that selegiline allowed reduction of the levodopa dose by about 40%. Selegiline + levodopa also extended the time until the levodopa dose had to be increased from 2.6 to 4.9 years.[6] As a result there were fewer motor complications in selegiline groups.[7] In one trial, selegiline + levodopa completely halted the progress of Parkinson's disease over 14 months, while in the placebo + levodopa group the deterioration of the patients' condition continued. However, the interpretation of this trial as proving neuroprotective action of selegiline has been questioned.[6]

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).[8] 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.[9] As of June 26, 2006, a selegiline transdermal patch is being tested for its effectiveness in treating ADHD.[10]

Several clinical studies are currently underway to evaluate selegiline's effectiveness in helping people stop smoking tobacco or marijuana.[11][12]

Side effects

Due to the primary metabolites of L-amphetamine and L-methamphetamine, Selegiline shares many side effects seen with these sympathomimetic stimulants. Minor side effects such as dizziness, dry mouth, difficulty falling or staying asleep, muscle pain, rash, nausea and constipation have been seen. More serious side effects such as severe headache, tachycardia, arrhythmia, hallucinations, chorea, or difficulty breathing should be investigated by health professionals immediately. [13]

Pharmacology

Pharmacokinetics

Wiki letter w.svg This section requires expansion with:
please add citations detailing bioavailability.

Selegiline has a low oral bioavailability.

Selegiline's oral bioavailability is drastically increased in females taking oral contraceptives (10- to 20-fold).[14] This could lead to loss of MAO-B selectivity in favor of an MAO-A selectivity, which in turn would make patients suspectible to the usual risks of unselective MAOIs such as tyramine-induced hypertensive crisis and serotonin toxicity when combined with serotonergics such as SSRIs.[14]

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.[15] Desmethylselegiline is metabolized by CYP2C19.[16]

L-amphetamine and L-methamphetamine

Selegiline is partly metabolized to l-methamphetamine, one of the two enantiomers of methamphetamine in vivo.[17] A characteristic metabolic pattern was noted, exemplified by a ratio of l-methamphetamine to l-amphetamine of about 2.8.[18] This stereoisomer is not considered psychoactive and has little abuse potential.[19] The stimulatory effect on locomotor activity and dopamine synthesis may be contributed to by the action of l-methamphetamine. If anyone is prescribed and takes selegiline, they can and will test positive for amphetamine/methamphetamine on most drug tests, however the prescription for selegine would explain why they test positive for amphetamine/methamphetamine.

Mechanism of Action

Selegiline is a selective inhibitor of MAO-B; MAO-B metabolizes dopamine and phenylethylamine.[20] Selegiline exhibits little therapeutic benefit when used independently, but enhances and prolongs the anti-Parkinson effects of levodopa.[21]

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.

In E for Ecstasy[22] (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. Consignments of Ecstasy known as "Strawberry" contained what Saunders described as a "potentially dangerous combination of ketamine, ephedrine and selegiline," as did a consignment of "Sitting Duck" Ecstasy tablets.[23]

Selegiline is not a controlled substance in the US but a prescription is required to obtain it within the US.

Emsam

February 28, 2006 - The Food and Drug Administration approved Emsam (selegiline), the first transdermal patch for use in treating major depression. The once a day patch works by delivering selegiline 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.

Zelapar

Zelapar is a transmucosal preparation for human administration of selegiline. The quickly-dissolving lozenge is placed between cheek and gum and the medication enters the bloodstream directly. Because hepatic first-pass metabolism is bypassed, the effective dose is lower than oral (swallowed) selegiline. GI side effects are reportedly reduced compared to oral (swallowed) selegiline. Zelapar is manufactured by Valeant Pharmaceuticals [2].

References

  1. ^ Amsterdam, J. D. (2003-02). "A double-blind, placebo-controlled trial of the safety and efficacy of selegiline transdermal system without dietary restrictions in patients with major depressive disorder". Journal of Clinical Psychiatry 64 (2): 208–214. 
  2. ^ a b Healy, David (2000). "The psychopharmacology of life and death. Interview with Joseph Knoll.". The Psychopharmacologists, Vol. III: Interviews. London: Arnold. pp. 81–110. ISBN 0-340-761105. 
  3. ^ Birkmayer W, Riederer P, Youdim MB, Linauer W (1975). "The potentiation of the anti akinetic effect after L-dopa treatment by an inhibitor of MAO-B, Deprenil". J. Neural Transm. 36 (3-4): 303–26. doi:10.1007/BF01253131. PMID 1172524. http://link.springer.de/link/service/journals/00702/bibs/5036003/50360303.htm. 
  4. ^ Varga E, Tringer L (1967). "Clinical trial of a new type promptly acting psychoenergetic agent (phenyl-isopropyl-methylpropinyl-HCl, "E-250")". Acta Med Acad Sci Hung 23 (3): 289–95. PMID 6056555. 
  5. ^ Riederer P, Lachenmayer L, Laux G (August 2004). "Clinical applications of MAO-inhibitors". Curr. Med. Chem. 11 (15): 2033–43. PMID 15279566. http://www.bentham-direct.org/pages/content.php?CMC/2004/00000011/00000015/0007C.SGM. 
  6. ^ a b c Riederer P, Lachenmayer L (November 2003). "Selegiline's neuroprotective capacity revisited". J Neural Transm 110 (11): 1273–8. doi:10.1007/s00702-003-0083-x. PMID 14628191. 
  7. ^ a b Ives NJ, Stowe RL, Marro J, et al. (September 2004). "Monoamine oxidase type B inhibitors in early Parkinson's disease: meta-analysis of 17 randomised trials involving 3525 patients". BMJ 329 (7466): 593. doi:10.1136/bmj.38184.606169.AE. PMID 15310558. 
  8. ^ FDA Approves Emsam (Selegiline) as First Drug Patch for Depression
  9. ^ http://www.petplace.com/drug-library/selegiline-hcl-anipryl/page1.aspx
  10. ^ http://www.selegiline.com/adhd.html
  11. ^ "Effectiveness of Selegiline in Treating Marijuana Dependent Individuals". ClinicalTrials.gov. National Institute on Drug Abuse. March 2005. http://clinicaltrials.gov/show/NCT00218517. Retrieved 2007-02-16. 
  12. ^ "Usefulness of Selegiline as an Aid to Quit Smoking". ClinicalTrials.gov. National Institute on Drug Abuse. July 2004. http://clinicaltrials.gov/show/NCT00129311. Retrieved 2007-02-16. 
  13. ^ http://www.ncbi.nlm.nih.gov/bookshelf/br.fcgi?book=medmaster&part=a697046
  14. ^ a b Laine K, Anttila M, Helminen A, Karnani H, Huupponen R (March 1999). "Dose linearity study of selegiline pharmacokinetics after oral administration: evidence for strong drug interaction with female sex steroids". Br J Clin Pharmacol 47 (3): 249–54. doi:10.1046/j.1365-2125.1999.00891.x. PMID 10215747. PMC 2014223. http://www.blackwell-synergy.com/openurl?genre=article&sid=nlm:pubmed&issn=0306-5251&date=1999&volume=47&issue=3&spage=249. 
  15. ^ Katzung, Bertram G. Basic & Clinical Pharmacology. 9th Edition. 2004. page 453. Lange Medical Books - McGraw Hill Publishers.
  16. ^ http://www.blackwell-synergy.com/doi/abs/10.1034/j.1600-0773.2000.d01-38.x Selegiline Metabolism and Cytochrome P450 Enzymes
  17. ^ Engberg G, Elebring T, Nissbrandt H (1991). "Deprenyl (selegiline), a selective MAO-B inhibitor with active metabolites; effects on locomotor activity, dopaminergic neurotransmission and firing rate of nigral dopamine neurons". J. Pharmacol. Exp. Ther. 259 (2): 841–7. PMID 1658311. 
  18. ^ www.astm.org/JOURNALS/FORENSIC/PAGES/2587.htm
  19. ^ Are metabolites of l-deprenyl (selegiline) useful ...[J Neural Transm Suppl. 1996] - PubMed Result
  20. ^ Katzung, Bertram G. Basic & Clinical Pharmacology. 9th Edition. 2004. page 453. Lange Medical Books - McGraw Hill Publishers.
  21. ^ Katzung. Page 453
  22. ^ Saunders, N., & Heron, L., (1993) E for Ecstasy (Paperback), N. Saunders, London. (ISBN 0950162884)
  23. ^ See: [1] for details online.

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