Product Name

Selegiline

CAS Number

14611-51-9

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Product Name:
Selegiline
CAS Number:
14611-51-9
Indication:
Monotherapy for initial treatment of Parkinson's disease, as well as an adjunct therapy in patients with a decreased response to levodopa/carbadopa. Also used for the palliative treatment of mild to moderate Alzheimer's disease and at higher doses, for the treatment of depression.
Mode of Action:

Although the mechanisms for selegiline's beneficial action in the treatment of Parkinson's disease are not fully understood, the selective, irreversible inhibition of monoamine oxidase type B (MAO-B) is thought to be of primary importance. MAO-B is involved in the oxidative deamination of dopamine in the brain. Selegiline binds to MAO-B within the nigrostriatal pathways in the central nervous system, thus blocking microsomal metabolism of dopamine and enhancing the dopaminergic activity in the substantial nigra. Selegiline may also increase dopaminergic activity through mechanisms other than inhibition of MAO-B. At higher doses, selegiline can also inhibit monozmine oxidase type A (MAO-A), allowing it to be used for the treatment of depression.

Pharmacodynamics:

Dopamine is an essential chemical that occurs in many parts of the body. It is the premature degradation of dopamine that results in the symptoms of Parkinson's disease. Monoamine oxidase (MAO) is an enzyme which accelerates the breakdown of dopamine. Selegiline can prolong the effects of dopamine in the brain by preventing its breakdown through seletively blocking MAO-B. It also may prevent the removal of dopamine between nerve endings and enhance release of dopamine from nerve cells.

Toxicity:

LD50=63 mg/kg (rats, IV)

IUPAC:
Benzeneethanamine, N, alpha-dimethyl-N-2-propynyl-, (R)-
ATC:
N04BD01
PubChem:
26757
DrugBank:
DB01037 (APRD00525)
Formula:
C13-H17-N
Molecular Mass:
187.2843
Synonyms:
(-)-(N)-Methyl-N-((1R)-1-methyl-2-phenylethyl)prop-2-yn-1-amine, (-)-Deprenil, (-)-Selegiline, (R)-(-)-N,alpha-Dimethyl-N-2-propinylphenethylamine, (R)-(-)-N-Methyl-N-(1-phenyl-2-propyl)-2-propinylamin, (R)-(-)-Selegiline, Anipryl, Benzeneethanamine, N,alpha-methyl-N-2-propynyl-, (alphaR)-, Carbex, Eldepryl, Emsam, Jumex, L-Deprenalin, l-Deprenyl, l-E 250, Selegilina, Selegilina [INN-Spanish], Selegiline, Selegilinum, Selegilinum [INN-Latin], Selgene, UNII-2K1V7GP655, Zalapar
SMILES:
C[C@H](Cc1ccccc1)N(C)CC#C
AHFS Code:
92:00.00 28:92.00
InChi:
1S/C13H17N/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13/h1,5-9,12H,10-11H2,2-3H3/t12-/m1/s1
General Reference:
General Reference:

  1. Engberg G, Elebring T, Nissbrandt H: 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. 1991 Nov;259(2):841-7. Pubmed
  2. Macleod AD, Counsell CE, Ives N, Stowe R: Monoamine oxidase B inhibitors for early Parkinsonês disease. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD004898. Pubmed# Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. Pubmed
  3. Heinonen EH, Anttila MI, Lammintausta RA: Pharmacokinetic aspects of l-deprenyl (selegiline) and its metabolites. Clin Pharmacol Ther. 1994 Dec;56(6 Pt 2):742-9. Pubmed
  4. Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinsonês disease. Clin Pharmacokinet. 2002;41(4):261-309. Pubmed
  5. Culpepper L, Kovalick LJ: A review of the literature on the selegiline transdermal system: an effective and well-tolerated monoamine oxidase inhibitor for the treatment of depression. Prim Care Companion J Clin Psychiatry. 2008;10(1):25-30. Pubmed
  6. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. Pubmed

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