You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameSelegiline
Accession NumberDB01037  (APRD00525)
TypeSmall Molecule
GroupsApproved, Investigational, Vet Approved
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]

Structure
Thumb
Synonyms
(−)-selegiline
L-Deprenalin
Selegilina
Selegilinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-selegilinetablet5 mgoralDominion Pharmacal1998-09-17Not applicableCanada
Eldeprylcapsule5 mg/1oralMylan Specialty2012-07-02Not applicableUs
Eldepryl - 5mg Tabtablet5 mgoralDraxis Health Inc.1997-09-022004-09-23Canada
Eldepryl Tab 5mgtablet5 mgoralDeprenyl Research Ltd.1990-12-311997-07-10Canada
Emsampatch12 mg/24htransdermalMylan Specialty2006-02-27Not applicableUs
Emsampatch9 mg/24htransdermalMylan Specialty2006-02-27Not applicableUs
Emsampatch6 mg/24htransdermalMylan Specialty2006-02-27Not applicableUs
Med Selegilinetablet5 mgoralMedican Pharma Incorporated1999-06-302011-03-29Canada
Mylan-selegilinetablet5 mgoralMylan Pharmaceuticals Ulc1997-04-09Not applicableCanada
Nu-selegilinetablet5 mgoralNu Pharm Inc1997-05-282012-09-04Canada
PMS-selegilinetablet5 mgoralPharmascience Inc1998-06-04Not applicableCanada
Selegilinetablet5 mgoralPharmel Inc1998-09-03Not applicableCanada
Selegiline-5tablet5 mgoralPro Doc Limitee1998-03-252010-07-13Canada
Teva-selegilinetablet5 mgoralTeva Canada Limited1994-12-31Not applicableCanada
Zelapartablet, orally disintegrating1.25 mg/1oralValeant Pharmaceuticals North America LLC2006-06-14Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-selegilinetablet5 mgoralApotex Inc1997-02-13Not applicableCanada
Selegiline Hydrochloridecapsule5 mg/1oralCarilion Materials Management2006-11-04Not applicableUs
Selegiline Hydrochloridetablet5 mg/1oralMylan Pharmaceuticals Inc.2010-03-08Not applicableUs
Selegiline Hydrochloridecapsule5 mg/1oralDAVA Pharmaceuticals, Inc.2006-11-04Not applicableUs
Selegiline Hydrochloridetablet5 mg/1oralApotex Corp.1997-07-06Not applicableUs
Selegiline Hydrochloridecapsule5 mg/1oralApotex Corp.1997-07-15Not applicableUs
Selegiline Hydrochloridetablet5 mg/1oralGolden State Medical Supply, Inc.2013-04-02Not applicableUs
Selegiline Hydrochloridecapsule5 mg/1oralGolden State Medical Supply, Inc.2006-11-04Not applicableUs
Selegiline Hydrochloridecapsule5 mg/1oralLake Erie Medical DBA Quality Care Products LLC1997-07-15Not applicableUs
Selegiline Hydrochloridecapsule5 mg/1oralA S Medication Solutions1997-07-15Not applicableUs
Selegiline Hydrochloridetablet5 mg/1oralLibertas Pharma, Inc.2014-05-24Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CarbexNot Available
JumexNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Selegiline Hydrochloride
14611-52-0
Thumb
  • InChI Key: IYETZZCWLLUHIJ-UTONKHPSSA-N
  • Monoisotopic Mass: 223.112777288
  • Average Mass: 223.742
DBSALT000260
Categories
UNII2K1V7GP655
CAS number14611-51-9
WeightAverage: 187.2808
Monoisotopic: 187.136099549
Chemical FormulaC13H17N
InChI KeyInChIKey=MEZLKOACVSPNER-UHFFFAOYSA-N
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
IUPAC Name
methyl(1-phenylpropan-2-yl)(prop-2-yn-1-yl)amine
SMILES
CC(CC1=CC=CC=C1)N(C)CC#C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationMonotherapy 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.
PharmacodynamicsDopamine 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.
Mechanism of actionAlthough 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.
Related Articles
AbsorptionRapidly absorbed from the gastrointestinal tract.
Volume of distributionNot Available
Protein binding> 99.5%
MetabolismNot Available
Route of eliminationNot Available
Half life1.2-2 hours
ClearanceNot Available
ToxicityLD50=63 mg/kg (rats, IV)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9788
Blood Brain Barrier+0.9809
Caco-2 permeable+0.8453
P-glycoprotein substrateNon-substrate0.543
P-glycoprotein inhibitor INon-inhibitor0.9632
P-glycoprotein inhibitor IINon-inhibitor0.9779
Renal organic cation transporterInhibitor0.5327
CYP450 2C9 substrateNon-substrate0.7993
CYP450 2D6 substrateSubstrate0.6987
CYP450 3A4 substrateNon-substrate0.5671
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9341
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9285
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9285
Ames testNon AMES toxic0.889
CarcinogenicityNon-carcinogens0.6567
BiodegradationNot ready biodegradable0.9767
Rat acute toxicity2.9199 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8869
hERG inhibition (predictor II)Non-inhibitor0.8269
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral5 mg
Capsuleoral5 mg/1
Patchtransdermal12 mg/24h
Patchtransdermal6 mg/24h
Patchtransdermal9 mg/24h
Tabletoral5 mg/1
Tablet, orally disintegratingoral1.25 mg/1
Prices
Unit descriptionCostUnit
Emsam 30 12 mg/24hr Patches Box627.1USD box
Emsam 30 6 mg/24hr Patches Box627.1USD box
Emsam 30 9 mg/24hr Patches Box627.1USD box
Selegiline hcl powder127.3USD g
Eldepryl 30 5 mg capsule Box89.55USD box
Emsam 12 mg/24 hours patch20.1USD patch
Emsam 6 mg/24 hours patch20.1USD patch
Emsam 9 mg/24 hours patch20.1USD patch
Zelapar 1.25 mg odt tablet8.33USD tablet
Selegiline HCl 5 mg capsule2.4USD capsule
Selegiline hcl 5 mg tablet2.1USD tablet
Apo-Selegiline 5 mg Tablet1.33USD tablet
Mylan-Selegiline 5 mg Tablet1.33USD tablet
Novo-Selegiline 5 mg Tablet1.33USD tablet
Nu-Selegiline 5 mg Tablet1.33USD tablet
Pms-Selegiline 5 mg Tablet1.33USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5648093 No1994-07-152014-07-15Us
US6423342 No1996-03-012016-03-01Us
US7070808 No1998-05-102018-05-10Us
US7150881 No1998-06-122018-06-12Us
US7638140 No1998-05-102018-05-10Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point141-142 °CNot Available
logP2.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0254 mg/mLALOGPS
logP3.08ALOGPS
logP2.85ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)8.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity61.35 m3·mol-1ChemAxon
Polarizability22.48 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Silvia Ott-Dembrowski, Richard Cyrus, Jorg Schmidt, Hans Waiblinger, “Preparation of selegiline.” U.S. Patent US5847216, issued March, 1962.

US5847216
General References
  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:1658311 ]
  2. 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:16034956 ]
  3. Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. [PubMed:6441926 ]
  4. 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:7995016 ]
  5. 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:11978145 ]
  6. 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:18311418 ]
  7. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [PubMed:19300583 ]
External Links
ATC CodesN04BD01
AHFS Codes
  • 28:92.00
  • 92:00.00
PDB Entries
FDA labelDownload (189 KB)
MSDSDownload (73.9 KB)
Interactions
Drug Interactions
Drug
AcepromazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Acepromazine.
AcetophenazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Acetophenazine.
AltretamineAltretamine may increase the orthostatic hypotensive activities of Selegiline.
AmisulprideThe risk or severity of adverse effects can be increased when Selegiline is combined with Amisulpride.
AmitriptylineSelegiline may increase the serotonergic activities of Amitriptyline.
AmphetamineSelegiline may increase the hypertensive activities of Amphetamine.
ApraclonidineThe risk or severity of adverse effects can be increased when Selegiline is combined with Apraclonidine.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Selegiline.
AtomoxetineSelegiline may increase the central neurotoxic activities of Atomoxetine.
AtropineSelegiline may increase the hypertensive activities of Atropine.
BenzquinamideThe risk or severity of adverse effects can be increased when Selegiline is combined with Benzquinamide.
BetahistineThe serum concentration of Betahistine can be increased when it is combined with Selegiline.
BezafibrateThe risk or severity of adverse effects can be increased when Selegiline is combined with Bezafibrate.
BrimonidineThe risk or severity of adverse effects can be increased when Selegiline is combined with Brimonidine.
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Selegiline.
BupropionSelegiline may increase the hypertensive activities of Bupropion.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Selegiline.
CarbamazepineThe risk or severity of adverse effects can be increased when Carbamazepine is combined with Selegiline.
CarphenazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Carphenazine.
CathinoneSelegiline may increase the hypertensive activities of Cathinone.
ChlormezanoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Chlormezanone.
ChlorotrianiseneThe serum concentration of Selegiline can be increased when it is combined with Chlorotrianisene.
ChlorpromazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Chlorpromazine.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Selegiline is combined with Chlorprothixene.
ClozapineThe risk or severity of adverse effects can be increased when Selegiline is combined with Clozapine.
CyclobenzaprineCyclobenzaprine may increase the serotonergic activities of Selegiline.
CyproheptadineSelegiline may increase the anticholinergic activities of Cyproheptadine.
DabrafenibThe serum concentration of Selegiline can be decreased when it is combined with Dabrafenib.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Selegiline.
DexmethylphenidateSelegiline may increase the hypertensive activities of Dexmethylphenidate.
DextromethorphanSelegiline may increase the serotonergic activities of Dextromethorphan.
DienogestThe serum concentration of Selegiline can be increased when it is combined with Dienogest.
DiethylpropionSelegiline may increase the hypertensive activities of Diethylpropion.
DomperidoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Domperidone.
DoxapramSelegiline may increase the hypertensive activities of Doxapram.
DroperidolThe risk or severity of adverse effects can be increased when Selegiline is combined with Droperidol.
EpinephrineSelegiline may increase the hypertensive activities of Epinephrine.
EthanolThe risk or severity of adverse effects can be increased when Ethanol is combined with Selegiline.
EtonogestrelThe serum concentration of Selegiline can be increased when it is combined with Etonogestrel.
FencamfamineThe risk or severity of adverse effects can be increased when Selegiline is combined with Fencamfamine.
FlupentixolThe risk or severity of adverse effects can be increased when Selegiline is combined with Flupentixol.
FluphenazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Fluphenazine.
FluspirileneThe risk or severity of adverse effects can be increased when Selegiline is combined with Fluspirilene.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Selegiline.
GranisetronGranisetron may increase the serotonergic activities of Selegiline.
HaloperidolThe risk or severity of adverse effects can be increased when Selegiline is combined with Haloperidol.
HydrocodoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Hydrocodone.
HydromorphoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Hydromorphone.
Insulin HumanSelegiline may increase the hypoglycemic activities of Insulin Regular.
Ioflupane I 123Selegiline may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
IsomethepteneThe risk or severity of adverse effects can be increased when Selegiline is combined with Isometheptene.
L-TryptophanThe risk or severity of adverse effects can be increased when L-Tryptophan is combined with Selegiline.
LevodopaThe risk or severity of adverse effects can be increased when Levodopa is combined with Selegiline.
LevonordefrinSelegiline may increase the hypertensive activities of Levonordefrin.
LevonorgestrelThe serum concentration of Selegiline can be increased when it is combined with Levonorgestrel.
LinezolidThe risk or severity of adverse effects can be increased when Selegiline is combined with Linezolid.
LithiumThe risk or severity of adverse effects can be increased when Selegiline is combined with Lithium.
LoxapineThe risk or severity of adverse effects can be increased when Selegiline is combined with Loxapine.
LumacaftorThe serum concentration of Selegiline can be decreased when it is combined with Lumacaftor.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Selegiline.
Medroxyprogesterone AcetateThe serum concentration of Selegiline can be increased when it is combined with Medroxyprogesterone Acetate.
MequitazineSelegiline may increase the anticholinergic activities of Mequitazine.
MesoridazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Mesoridazine.
MethadoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Methadone.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Methotrimeprazine.
MethyldopaThe risk or severity of adverse effects can be increased when Selegiline is combined with Methyldopa.
Methylene blueSelegiline may increase the serotonergic activities of Methylene blue.
MethylphenidateSelegiline may increase the hypertensive activities of Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Selegiline is combined with Metoclopramide.
MianserinSelegiline may increase the neurotoxic activities of Mianserin.
MidodrineSelegiline may increase the hypertensive activities of Midodrine.
MirtazapineSelegiline may increase the central neurotoxic activities of Mirtazapine.
MoclobemideThe risk or severity of adverse effects can be increased when Selegiline is combined with Moclobemide.
MolindoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Molindone.
MorphineThe risk or severity of adverse effects can be increased when Selegiline is combined with Morphine.
MoxonidineSelegiline may increase the hypotensive activities of Moxonidine.
NevirapineThe metabolism of Selegiline can be increased when combined with Nevirapine.
NorepinephrineSelegiline may increase the hypertensive activities of Norepinephrine.
NorethisteroneThe serum concentration of Selegiline can be increased when it is combined with Norethindrone.
OlanzapineThe risk or severity of adverse effects can be increased when Selegiline is combined with Olanzapine.
OndansetronThe risk or severity of adverse effects can be increased when Selegiline is combined with Ondansetron.
OrciprenalineThe risk or severity of adverse effects can be increased when Selegiline is combined with Orciprenaline.
OxcarbazepineOxcarbazepine may increase the serotonergic activities of Selegiline.
OxycodoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Oxycodone.
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Selegiline.
PaliperidoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Paliperidone.
ParoxetineSelegiline may increase the serotonergic activities of Paroxetine.
PerphenazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Perphenazine.
PethidineSelegiline may increase the serotonergic activities of Pethidine.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Selegiline.
PholcodinePholcodine may increase the serotonergic activities of Selegiline.
PimozideThe risk or severity of adverse effects can be increased when Selegiline is combined with Pimozide.
PipamperoneThe therapeutic efficacy of Pipamperone can be decreased when used in combination with Selegiline.
PiperacetazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Piperacetazine.
PizotifenSelegiline may increase the anticholinergic activities of Pizotifen.
ProchlorperazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Prochlorperazine.
PromazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Promazine.
QuazepamThe serum concentration of Selegiline can be increased when it is combined with Quazepam.
QuetiapineThe risk or severity of adverse effects can be increased when Selegiline is combined with Quetiapine.
RemoxiprideThe risk or severity of adverse effects can be increased when Selegiline is combined with Remoxipride.
ReserpineThe risk or severity of adverse effects can be increased when Selegiline is combined with Reserpine.
RisperidoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Risperidone.
SertindoleThe risk or severity of adverse effects can be increased when Selegiline is combined with Sertindole.
SufentanilSufentanil may increase the serotonergic activities of Selegiline.
SulpirideThe risk or severity of adverse effects can be increased when Selegiline is combined with Sulpiride.
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Selegiline.
Tedizolid PhosphateTedizolid Phosphate may increase the serotonergic activities of Selegiline.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Selegiline.
TetryzolineSelegiline may increase the hypertensive activities of Tetryzoline.
ThioridazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Thioridazine.
ThiothixeneThe risk or severity of adverse effects can be increased when Selegiline is combined with Thiothixene.
TiclopidineThe metabolism of Selegiline can be decreased when combined with Ticlopidine.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Selegiline.
TolcaponeThe risk or severity of adverse effects can be increased when Tolcapone is combined with Selegiline.
TramadolTramadol may increase the neuroexcitatory activities of Selegiline.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Selegiline.
TrazodoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Trazodone.
TrifluoperazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Trifluoperazine.
TriflupromazineThe risk or severity of adverse effects can be increased when Selegiline is combined with Triflupromazine.
VenlafaxineSelegiline may increase the serotonergic activities of Venlafaxine.
ZiprasidoneThe risk or severity of adverse effects can be increased when Selegiline is combined with Ziprasidone.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Selegiline is combined with Zuclopenthixol.
Food Interactions
  • Food increases the oral bioavailability by 3-5 fold.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Primary amine oxidase activity
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular Weight:
58762.475 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Chrisp P, Mammen GJ, Sorkin EM: Selegiline. A review of its pharmacology, symptomatic benefits and protective potential in Parkinson's disease. Drugs Aging. 1991 May;1(3):228-48. [PubMed:1794016 ]
  3. Heinonen EH, Myllyla V: Safety of selegiline (deprenyl) in the treatment of Parkinson's disease. Drug Saf. 1998 Jul;19(1):11-22. [PubMed:9673855 ]
  4. Authors unspecified: Selegiline: a second look. Six years later: too risky in Parkinson's disease. Prescrire Int. 2002 Aug;11(60):108-11. [PubMed:12199263 ]
  5. 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:16034956 ]
  6. Magyar K, Tothfalusi L: Pharmacokinetic aspects of deprenyl effects. Pol J Pharmacol Pharm. 1984 Jul-Aug;36(4):373-84. [PubMed:6441926 ]
  7. 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:7995016 ]
  8. 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:11978145 ]
  9. Patkar AA, Pae CU, Masand PS: Transdermal selegiline: the new generation of monoamine oxidase inhibitors. CNS Spectr. 2006 May;11(5):363-75. [PubMed:16641841 ]
  10. Azzaro AJ, Ziemniak J, Kemper E, Campbell BJ, VanDenBerg C: Pharmacokinetics and absolute bioavailability of selegiline following treatment of healthy subjects with the selegiline transdermal system (6 mg/24 h): a comparison with oral selegiline capsules. J Clin Pharmacol. 2007 Oct;47(10):1256-67. Epub 2007 Aug 22. [PubMed:17715422 ]
  11. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [PubMed:19300583 ]
  12. Baker GB, Sowa B, Todd KG: Amine oxidases and their inhibitors: what can they tell us about neuroprotection and the development of drugs for neuropsychiatric disorders? J Psychiatry Neurosci. 2007 Sep;32(5):313-5. [PubMed:17823646 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
inhibitor
General Function:
Serotonin binding
Specific Function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular Weight:
59681.27 Da
References
  1. Patkar AA, Pae CU, Masand PS: Transdermal selegiline: the new generation of monoamine oxidase inhibitors. CNS Spectr. 2006 May;11(5):363-75. [PubMed:16641841 ]
  2. Azzaro AJ, Ziemniak J, Kemper E, Campbell BJ, VanDenBerg C: Pharmacokinetics and absolute bioavailability of selegiline following treatment of healthy subjects with the selegiline transdermal system (6 mg/24 h): a comparison with oral selegiline capsules. J Clin Pharmacol. 2007 Oct;47(10):1256-67. Epub 2007 Aug 22. [PubMed:17715422 ]
  3. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [PubMed:19300583 ]
  4. Baker GB, Sowa B, Todd KG: Amine oxidases and their inhibitors: what can they tell us about neuroprotection and the development of drugs for neuropsychiatric disorders? J Psychiatry Neurosci. 2007 Sep;32(5):313-5. [PubMed:17823646 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. 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:18311418 ]
  2. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [PubMed:19300583 ]
  3. Benetton SA, Fang C, Yang YO, Alok R, Year M, Lin CC, Yeh LT: P450 phenotyping of the metabolism of selegiline to desmethylselegiline and methamphetamine. Drug Metab Pharmacokinet. 2007 Apr;22(2):78-87. [PubMed:17495414 ]
  4. Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [PubMed:17101742 ]
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Benetton SA, Fang C, Yang YO, Alok R, Year M, Lin CC, Yeh LT: P450 phenotyping of the metabolism of selegiline to desmethylselegiline and methamphetamine. Drug Metab Pharmacokinet. 2007 Apr;22(2):78-87. [PubMed:17495414 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 Da
References
  1. Lee KC, Chen JJ: Transdermal selegiline for the treatment of major depressive disorder. Neuropsychiatr Dis Treat. 2007;3(5):527-37. [PubMed:19300583 ]
  2. Benetton SA, Fang C, Yang YO, Alok R, Year M, Lin CC, Yeh LT: P450 phenotyping of the metabolism of selegiline to desmethylselegiline and methamphetamine. Drug Metab Pharmacokinet. 2007 Apr;22(2):78-87. [PubMed:17495414 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. [PubMed:12438524 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on May 31, 2016 02:12