Selegiline

CovInDB Drug

DB01037

Name

Selegiline

Molecular Formula

C₁₃H₁₇N

Molecular Weight

187.14 g/mol

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.

Status

approved, investigational, vet_approved

Structure

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SDF 2D SDF 3D

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.

Mechanism of action

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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.

IUPAC Name

(2R)-N-methyl-1-phenyl-N-prop-2-ynyl-propan-2-amine

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

InChI Key

MEZLKOACVSPNER-GFCCVEGCSA-N

Canonical SMILES

C[C@H](CC1=CC=CC=C1)N(C)CC#C

Reference

DrugBank

Warhead

Alkynyl

Target

MAO-B   [ UniProt: P27338 ]

Site

FAD cofactor

Inhibition Mechanism

Crystal Structures of Monoamine Oxidase B in Complex with Four Inhibitors of the N-Propargylaminoindan Class

logP

3.08

Computed by ALOGPS

logS

-3.87

Computed by ALOGPS

Heavy Atom Count

14

Computed by RDKit

Ring Count

1

Computed by RDKit

Hydrogen Bond Acceptor Count

1

Computed by RDKit

Hydrogen Bond Donor Count

0

Computed by RDKit

Rotatable Bond Count

4

Computed by RDKit

Topological Polar Surface Area

3.24 Ų

Computed by RDKit

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No similar natural compounds found for this drug.