QuickView for Selegiline (compound)

Summary
General Info

PubChem

PubChem Compound 199604

Name:	Selegiline
PubChem Compound ID:	199604
Description:	A selective, irreversible inhibitor of Type B monoamine oxidase. It is used in newly diagnosed patients with Parkinson's disease. It may slow progression of the clinical disease and delay the requirement for levodopa therapy. It also may be given with levodopa upon onset of disability. (From AMA Drug Evaluations Annual, 1994, p385) The compound without isomeric designation is Deprenyl.
Molecular formula:	C₁₃H₁₈ClN
Molecular weight:	223.741 g/mol
Synonyms:	(+)-E-250; Phenethylamine, N,alpha-dimethyl-N-2-propynyl-, hydrochloride, D-(+)-; (+)-Phenylisopropylmethylpropynylamine hydrochloride; EU-0100842; (+)-Deprenil hydrochloride; 4528-52-3; Benzeneethanamine, N,alpha-dimethyl-N-2-propynyl-, hydrochloride, (S)- (9CI); (+)-Deprenyl hydrochloride; (+)-N,alpha-Dimethyl-N-2-propynylphenethylamine hydrochloride

DrugBank

Identification

Name:	Selegiline
Name (isomeric):	DB01037
Drug Type:	small molecule
Description:	A selective, irreversible inhibitor of Type B monoamine oxidase. It is used in newly diagnosed patients with Parkinson's disease. It may slow progression of the clinical disease and delay the requirement for levodopa therapy. It also may be given with levodopa upon onset of disability. (From AMA Drug Evaluations Annual, 1994, p385) The compound without isomeric designation is Deprenyl.
Synonyms:	Selegilinum [INN-Latin]; L-Deprenalin; Selegilina [INN-Spanish]; Selegeline Hcl
Brand:	Gen-Selegiline, Carbex, Apo-Selegiline, Sd Deprenyl, Nu-Selegiline, Jumex, Zelapar, Eldepryl, Novo-Selegiline, Emsam
Category:	Antidyskinetics, Monoamine Oxidase Inhibitors, Antiparkinson Agents, Neuroprotective Agents, Central Nervous System Agents, Dopaminergics
CAS number:	14611-51-9

Pharmacology

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.
Pharmacology:	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 se... show more » 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. show less «
Mechanism 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 ... show more » 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. show less «
Absorption:	Rapidly absorbed from the gastrointestinal tract.
Protein binding:	> 99.5%
Half Life:	1.2-2 hours
Toxicity:	LD₅₀=63 mg/kg (rats, IV)
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Food increases the oral bioavailability by 3-5 fold.

Drug interaction:

Fluoxetine	Possible severe adverse reaction with this combination
Fluvoxamine	Possible severe adverse reaction with this combination
Dextromethorphan	Combination associated with possible serotoninergic syndrome
Brimonidine	MAO Inhibitors like selegiline may enhance the hypertensive effect of Alpha2-Agonists (Ophthalmic). The concomitant use of monoamine oxidase inhibitors and ophthalmic alpha2 agonists is contraindicated.
Tetrabenazine	Tetrabenazine may increase the adverse/toxic effects of Selegiline. Concomitant therapy is contraindicated.

Fluoxetine	Possible severe adverse reaction with this combination
Fluvoxamine	Possible severe adverse reaction with this combination
Dextromethorphan	Combination associated with possible serotoninergic syndrome
Brimonidine	MAO Inhibitors like selegiline may enhance the hypertensive effect of Alpha2-Agonists (Ophthalmic). The concomitant use of monoamine oxidase inhibitors and ophthalmic alpha2 agonists is contraindicated.
Tetrabenazine	Tetrabenazine may increase the adverse/toxic effects of Selegiline. Concomitant therapy is contraindicated.
Tranylcypromine	Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
Citalopram	Possible severe adverse reaction with this combination
Moclobemide	Decrease in selectivity
Buprenorphine	Buprenorphine may enhance the adverse/toxic effect of MAO Inhibitors like selegiline. When possible, avoid use of buprenorphine in patients who have used a monoamine oxidase inhibitor within the past 14 days due to possible severe adverse effects.
Zolmitriptan	The MAO inhibitor, selegiline, may increase the serum concentration of zolmitriptan by decreasing its metabolism. Concomitant therapy and use of zolmitriptan within two weeks of discontinuing selegiline are contraindicated.
Tolcapone	Tolcapone and Selegiline decrease the metabolism of endogenous catecholamines. Concomitant therapy may result in increased catecholamine effects. Consider alternate therapy or use cautiously and monitor for increased catecholamine effects.
Vilazodone	MAO Inhibitors may enhance the serotonergic effect of Selective Serotonin Reuptake Inhibitors. This may cause serotonin syndrome. Avoid combination.
Thiotepa	Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Selegiline, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Selegiline if Thiotepa is initiated, discontinued or dose changed.
Desvenlafaxine	Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.
Escitalopram	Possible severe adverse reaction with this combination
Meperidine	Potentially fatal adverse effects
Tramadol	Tramadol increases the risk of serotonin syndrome and seizure induction by the MAO inhibitor, Selegiline.
Paroxetine	Possible severe adverse reaction with this combination
Bezafibrate	MAO Inhibitors may enhance the adverse/toxic effect of Bezafibrate. Avoid concomitant use of bezafibrate with monoamine oxidase inhibitors (MAOIs) like selegiline.
Trimipramine	Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Avoid combination or monitor for symptoms of serotonin syndrome and/or hypertensive crisis.
Trazodone	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Venlafaxine	Increased risk of serotonin syndrome. Ensure adequate washout period between therapies to avoid toxicity. Concurrent therapy should be avoided.

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Targets

Amine oxidase [flavin-containing] B

Amine oxidase [flavin-containing] A

Enzymes

Transporters

Multidrug resistance protein 1