CAS 14611-51-9|Gen-Selegiline|selegiline|Selegilinum [INN-Latin]|Emsam|selegiline|Nu-Selegiline|Selegeline Hcl|Sd Deprenyl|Carbex|L-Deprenalin|Apo-Selegiline|Jumex|Selegilina [INN-Spanish]|Eldepryl|...

General Information

Structure

Molecular Formula

C₁₃H₁₇N

Molecular Mass

187.28078

Exact Mass

187.13609955

Charge

InChI

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

InChIKey

MEZLKOACVSPNER-GFCCVEGCSA-N

Canonic Smiles

C[C@@H](N(CC#C)C)Cc1ccccc1

Isomeric Smiles

N([C@@H](Cc1ccccc1)C)(CC#C)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.15821154

LogD (pH = 7.4)

1.5548966

Log P

2.847962

Molar Refractivity

61.3547

Polarizability

23.641752

Polar Surface Area

3.24

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.08

LOG S

-3.87

Solubility (Water)

2.54e-02 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Brand Name

Gen-SelegilineEmsamNu-SelegilineSd DeprenylCarbexApo-SelegilineJumexEldeprylNovo-SelegilineZelapar

Synonyms

selegilineSelegilinum [INN-Latin]Selegeline HclL-DeprenalinSelegilina [INN-Spanish]Selegiline

IUPAC Traditional name

selegiline

IUPAC name

methyl[(2R)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amine

Names and Identifiers

Registration numbers

CAS Number

14611-51-9

PubChem CID

26757

PubChem SID

160964372

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.7

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB01037

Drug Groups

approved; investigational

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. [PubChem]

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 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)

Affected Organisms

Humans and other mammals

Absorption

Rapidly absorbed from the gastrointestinal tract.

Half Life

1.2-2 hours

Protein Binding

> 99.5%

References

• 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]

• Macleod AD, Counsell CE, Ives N, Stowe R: Monoamine oxidase B inhibitors for early Parkinson's 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]

• 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]

• Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [Pubmed]

• 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]

• Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. Pubmed

• Macleod AD, Counsell CE, Ives N, Stowe R: Monoamine oxidase B inhibitors for early Parkinson's disease. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD004898. Pubmed

• Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. Pubmed

• Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. Pubmed

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• Brand Name

• Synonyms

• IUPAC Traditional name

• IUPAC name

Registration numbers

• CAS Number

• PubChem CID

• PubChem SID

• Physical Property

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Brand Name

Gen-SelegilineEmsamNu-SelegilineSd DeprenylCarbexApo-SelegilineJumexEldeprylNovo-SelegilineZelapar

Synonyms

selegilineSelegilinum [INN-Latin]Selegeline HclL-DeprenalinSelegilina [INN-Spanish]Selegiline

IUPAC Traditional name

selegiline

IUPAC name

methyl[(2R)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amine

CAS Number

14611-51-9

PubChem SID

160964372

Physical Property

Hydrophobicity(logP)

2.7

DrugBank

DB01037

Drug Groups

approved; investigational

Description

Indication

Pharmacology

Toxicity

LD₅₀=63 mg/kg (rats, IV)

Affected Organisms

Humans and other mammals

Absorption

Rapidly absorbed from the gastrointestinal tract.

Half Life

1.2-2 hours

Protein Binding

> 99.5%

References

• Macleod AD, Counsell CE, Ives N, Stowe R: Monoamine oxidase B inhibitors for early Parkinson's 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]

• 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]

• Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. [Pubmed]

• Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

From Data Sources

• Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. Pubmed

• Macleod AD, Counsell CE, Ives N, Stowe R: Monoamine oxidase B inhibitors for early Parkinson's disease. Cochrane Database Syst Rev. 2005 Jul 20;(3):CD004898. Pubmed

• Deleu D, Northway MG, Hanssens Y: Clinical pharmacokinetic and pharmacodynamic properties of drugs used in the treatment of Parkinson's disease. Clin Pharmacokinet. 2002;41(4):261-309. Pubmed

• Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. Pubmed

• 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

Molecule

ID:909