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Selegiline
Systematic (IUPAC) name
N-methyl-N-(1-methyl-2-phenyl-ethyl)-prop-2-yn-1-amine
Identifiers
CAS number 14611-51-9
[14611-52-0] (HCl), [2079-54-1] (deprenyl. IUPAC Nomenclature is a system of naming Chemical compounds and of describing the science of Chemistry in general CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to 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 N04BD01
PubChem 26757
DrugBank APRD00525
Chemical data
Formula C13H17N 
Mol. mass 187. The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs It is controlled by the WHO Collaborating Centre for Drug A section of the Anatomical Therapeutic Chemical Classification System. PubChem is a Database of chemical Molecules The system is maintained by the National Center for Biotechnology Information (NCBI a component The DrugBank database available at the University of Alberta is a unique Bioinformatics and Cheminformatics resource that combines detailed drug (i A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Carbon (kɑɹbən is a Chemical element with the symbol C and its Atomic number is 6 Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 Nitrogen (ˈnaɪtɹəʤɪn is a Chemical element that has the symbol N and Atomic number 7 and Atomic weight 14 The molecular mass (abbreviated m of a substance, more commonly referred to as molecular weight and abbreviated as MW, is the Mass of one 281 g/mol
Pharmacokinetic data
Bioavailability 4. In Pharmacology, bioavailability is used to describe the fraction of an administered Dose of unchanged drug that reaches the Systemic circulation, one of 4%
Protein binding > 99. A drug's efficiency may be affected by the degree to which it binds to the proteins within Blood plasma. 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, Zelapar, or Anipryl veterinary) is a drug used for the treatment of early-stage Parkinson's disease and senile dementia. Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems The biological half-life of a substance is the time it takes for a substance (drug radioactive nuclide or other to lose half of its pharmacologic physiologic or radiologic activity Excretion is the process of eliminating waste products of Metabolism and other non-useful materials The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical if it is used as directed by the mother during The United States of America —commonly referred to as the The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction The United States of America —commonly referred to as the In Pharmacology and Toxicology, a route Veterinary medicine the application of medical, diagnostic, and therapeutic principles to companion, domestic, exotic, wildlife Medication, also referred to as medicine, can be loosely defined as any substance intended for use in the diagnosis cure mitigation treatment or prevention of disease Parkinson's disease (also known as Parkinson disease or PD) is a degenerative disorder of the Central nervous system that often impairs the sufferer's Dementia (from Latin de- "apart away" + Mens ( genitive mentis) "mind" is the progressive decline 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. Monoamine oxidase inhibitors ( MAOIs) are a class of powerful antidepressant drugs prescribed for the treatment of depression. Dietary restrictions are common for MAOI treatments, but 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 Knoll József. Selegiline is most closely related to the phenylethylamines. Phenethylamine, or β -phenylethylamine or 2-phenylethylamine is an Alkaloid and Monoamine. 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. In Chemistry, propargyl is an Alkyl Functional group of 2- Propynyl with the structure HC≡C−CH2− derived from the Alkyne

Contents

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. Off-label use is the practice of prescribing drugs for a purpose outside the scope of the drug's approved label most often concerning the drug's indication. Narcolepsy is a Neurological condition most characterized by Excessive Daytime Sleepiness (EDS in which a person falls asleep during the day at inappropriate '''Nootropics''' popularly referred to as " smart drugs " " smart nutrients " " cognitive enhancers " and " brain enhancers It is also reported to positively affect libido, particularly in older males. Libido in its common usage means Sexual desire however more technical definitions such as those found in the work of Carl Jung, are more general referring to libido Male (♂ refers to the sex of an organism or part of an organism which produces small mobile Gametes called spermatozoa. 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). Major depressive disorder, also known as major depression, unipolar depression, unipolar disorder, clinical depression, or simply depression Emsam (selegiline transdermal system is a Transdermal patch using the Monoamine oxidase inhibitor (MAOI Selegiline. [2] 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. Veterinary medicine the application of medical, diagnostic, and therapeutic principles to companion, domestic, exotic, wildlife The dog ( Canis lupus familiaris) is a domesticated Subspecies of the gray wolf, a Mammal of the Canidae family of the order As of June 26, 2006, a selegiline transdermal patch is being tested for its effectiveness in treating ADHD. Attention-Deficit Hyperactivity Disorder (ADHD is a neurobehavioral developmental disorder affecting about 3-5% of the world's population

Several clinical studies are currently underway to evaluate Selegiline's effectiveness in helping people stop smoking tobacco or marijuana. Tobacco is an Agricultural product recognized as an addictive drug processed from the fresh Leaves of plants in the genus Nicotiana. Cannabis, also known as marijuana or marihuana, or ganja (from Hindi / Sanskrit: गांजा gānjā hemp) is a [3][4]

Pharmacology

Pharmacokinetics

Selegiline has a low oral bioavailability.

Selegiline's oral bioavailability is drastically increased in females taking oral contraceptives (10- to 20-fold). [5] This could lead to loss of MAO-B 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. Monoamine oxidase inhibitors ( MAOIs) are a class of powerful antidepressant drugs prescribed for the treatment of depression. In organic Chemistry tyramine (4-hydroxy- Phenethylamine, para-tyramine p-tyramine is a Monoamine compound derived from the [5]

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. [6] Desmethylselegiline is metabolized by CYP2C19. Cytochrome P450 2C19 (abbreviated CYP2C19) a member of the Cytochrome P450 mixed-function oxidase system is involved in the metabolism of Xenobiotics [7]

L-amphetamine and L-methamphetamine

Selegiline is partly metabolized to l-methamphetamine, a stereoisomer of methamphetamine in vivo. Drug metabolism is the Metabolism of drugs, their Biochemical modification or degradation usually through specialized enzymatic systems Stereoisomers are isomeric molecules that have the same molecular formula and sequence of bonded atoms (constitution but which differ in the three dimensional orientations In vivo ( Latin: within the living means that which takes place inside an organism. [8] A characteristic metabolic pattern was noted, exemplified by a ratio of 1-methamphetamine to 1-amphetamine of about 2. 8. [9] This stereoisomer is not considered psychoactive and has little abuse potential. [10] 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. Amphetamine, and related drugs such as Methamphetamine are a group of drugs that act by increasing levels of Norepinephrine, Serotonin, and Dopamine


Mechanism of Action

Selegiline is a selective inhibitor of MAO-B; MAO-B metabolizes dopamine. [11] Selegiline exhibits little therapeutic benefit when used independently, but enhances and prolongs the anti-Parkinson effects of levodopa. Parkinson's disease (also known as Parkinson disease or PD) is a degenerative disorder of the Central nervous system that often impairs the sufferer's [12]


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. Stimulant drugs are Drugs that temporarily increase alertness and awareness A controlled substance is generally a drug or chemical whose manufacture possession and use are regulated by a government For a topic outline on this subject see List of basic Japan topics. A prescription (℞ is a health-care program implemented by a Physician or other medical practitioner in the form of instructions that govern the plan of care for an individual 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.

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 [1]. Valeant Pharmaceuticals International is a pharmaceutical company with activities spanning the drug discovery pipeline from Target identification through

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. ^ FDA Approves Emsam (Selegiline) as First Drug Patch for Depression
  3. ^ Effectiveness of Selegiline in Treating Marijuana Dependent Individuals. ClinicalTrials. gov. National Institute on Drug Abuse (March 2005). Retrieved on 2007-02-16. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1249 - Andrew of Longjumeau is dispatched by Louis IX of France as his ambassador to meet with the Khan of the Mongols
  4. ^ Usefulness of Selegiline as an Aid to Quit Smoking. ClinicalTrials. gov. National Institute on Drug Abuse (July 2004). Retrieved on 2007-02-16. Year 2007 ( MMVII) was a Common year starting on Monday of the Gregorian calendar in the 21st century. Events 1249 - Andrew of Longjumeau is dispatched by Louis IX of France as his ambassador to meet with the Khan of the Mongols
  5. ^ 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. PMID 10215747. PMC:2014223. PubMed Central is a free digital database of full-text Scientific literature in biomedical and life sciences  
  6. ^ Katzung, Bertram G. Basic & Clinical Pharmacology. 9th Edition. 2004. page 453. Lange Medical Books - McGraw Hill Publishers.
  7. ^ http://www.blackwell-synergy.com/doi/abs/10.1034/j.1600-0773.2000.d01-38.x Selegiline Metabolism and Cytochrome P450 Enzymes
  8. ^ 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.  
  9. ^ www. astm. org/JOURNALS/FORENSIC/PAGES/2587. htm
  10. ^ Are metabolites of l-deprenyl (selegiline) useful ...[J Neural Transm Suppl. 1996] - PubMed Result
  11. ^ Katzung, Bertram G. Basic & Clinical Pharmacology. 9th Edition. 2004. page 453. Lange Medical Books - McGraw Hill Publishers.
  12. ^ Katzung. Page 453

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