SELEGILINE

First approved in 1989

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H17N
Molecular Weight	187.2808
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MEZLKOACVSPNER-GFCCVEGCSA-N

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

HIDE SMILES / InChI

Molecular Formula	C13H17N
Molecular Weight	187.2808
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugs.com/dosage/selegiline.html
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB01037 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021708s000_021336s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/18237459 | https://www.ncbi.nlm.nih.gov/pubmed/28108387

Selegiline, also known as L-deprenyl, is a substituted phenethylamine, a selective, irreversible inhibitor of Type B monoamine oxidase. Selegiline is available in pill form under many brand names (Eldepryl, Carbex, Atapryl) and is used to reduce symptoms in early-stage Parkinson's disease. Selegiline delays the time point when the L-DOPA (levodopa) treatment becomes necessary from about 11 months to about 18 months after diagnosis, which is beneficial despite not being definitive evidence of neuroprotection. The rationale for adding selegiline to levodopa is to decrease the required dose of levodopa and thus reduce the motor complications of levodopa therapy. Selegiline is also delivered via a transdermal patch (brand name, Emsam) and in this form, Selegiline is used as a treatment for the major depressive disorder. Selegiline (brand name Anipryl) is also used (at extremely high dosages relative to humans) in veterinary medicine to treat the symptoms of Cushing's disease and cognitive dysfunction (Canine Cognitive Dysfunction) in dogs. Side effects of the pill form include, in decreasing order of frequency, nausea, hallucinations, confusion, depression, loss of balance, insomnia, increased involuntary movements, agitation, arrhythmia, slow heart rate, delusions, hypertension, new or increased angina pectoris, and syncope. The main side effects of the patch form for depression included application site reactions, insomnia, diarrhea, and sore throat.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26337020	Inhibitor 8504		9.0 nM [IC50]
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26278660	Inhibitor 8504		47.9 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Parkinson's disease 232 Sources: https://www.drugs.com/dosage/selegiline.html	Primary	Approved 8583	EMSAM Approved Use Selegiline Hydrochloride Tablets USP are indicated as an adjunct in the management of Parkinsonian patients being treated with levodopa/carbidopa who exhibit deterioration in the quality of their response to this therapy. There is no evidence from controlled studies that selegiline has any beneficial effect in the absence of concurrent levodopa therapy. Evidence supporting this claim was obtained in randomized controlled clinical investigations that compared the effects of added selegiline or placebo in patients receiving levodopa/carbidopa. Selegiline was significantly superior to placebo on all three principal outcome measures employed: change from baseline in daily levodopa/carbidopa dose, the amount of 'off' time, and patient self-rating of treatment success. Beneficial effects were also observed on other measures of treatment success (e.g., measures of reduced end of dose akinesia, decreased tremor and sialorrhea, improved speech and dressing ability and improved overall disability as assessed by walking and comparison to previous state). Launch Date 2006
Major depressive disorder 179 Sources: https://www.drugs.com/dosage/selegiline.html	Primary	Approved 8583	EMSAM Approved Use Selegiline Hydrochloride Tablets USP are indicated as an adjunct in the management of Parkinsonian patients being treated with levodopa/carbidopa who exhibit deterioration in the quality of their response to this therapy. There is no evidence from controlled studies that selegiline has any beneficial effect in the absence of concurrent levodopa therapy. Evidence supporting this claim was obtained in randomized controlled clinical investigations that compared the effects of added selegiline or placebo in patients receiving levodopa/carbidopa. Selegiline was significantly superior to placebo on all three principal outcome measures employed: change from baseline in daily levodopa/carbidopa dose, the amount of 'off' time, and patient self-rating of treatment success. Beneficial effects were also observed on other measures of treatment success (e.g., measures of reduced end of dose akinesia, decreased tremor and sialorrhea, improved speech and dressing ability and improved overall disability as assessed by walking and comparison to previous state). Launch Date 2006
Bipolar depression 9 Sources: https://www.drugs.com/dosage/selegiline.html	Primary	Approved 8583	EMSAM Approved Use Selegiline Hydrochloride Tablets USP are indicated as an adjunct in the management of Parkinsonian patients being treated with levodopa/carbidopa who exhibit deterioration in the quality of their response to this therapy. There is no evidence from controlled studies that selegiline has any beneficial effect in the absence of concurrent levodopa therapy. Evidence supporting this claim was obtained in randomized controlled clinical investigations that compared the effects of added selegiline or placebo in patients receiving levodopa/carbidopa. Selegiline was significantly superior to placebo on all three principal outcome measures employed: change from baseline in daily levodopa/carbidopa dose, the amount of 'off' time, and patient self-rating of treatment success. Beneficial effects were also observed on other measures of treatment success (e.g., measures of reduced end of dose akinesia, decreased tremor and sialorrhea, improved speech and dressing ability and improved overall disability as assessed by walking and comparison to previous state). Launch Date 2006
Cocaine-related disorders 19 Sources: https://clinicaltrials.gov/ct2/show/NCT00032929	Primary	Phase III 665	EMSAM Approved Use Selegiline Hydrochloride Tablets USP are indicated as an adjunct in the management of Parkinsonian patients being treated with levodopa/carbidopa who exhibit deterioration in the quality of their response to this therapy. There is no evidence from controlled studies that selegiline has any beneficial effect in the absence of concurrent levodopa therapy. Evidence supporting this claim was obtained in randomized controlled clinical investigations that compared the effects of added selegiline or placebo in patients receiving levodopa/carbidopa. Selegiline was significantly superior to placebo on all three principal outcome measures employed: change from baseline in daily levodopa/carbidopa dose, the amount of 'off' time, and patient self-rating of treatment success. Beneficial effects were also observed on other measures of treatment success (e.g., measures of reduced end of dose akinesia, decreased tremor and sialorrhea, improved speech and dressing ability and improved overall disability as assessed by walking and comparison to previous state). Launch Date 2006
Cognitive disorders 8 Sources: https://clinicaltrials.gov/ct2/show/NCT00002154	Primary	Phase II 1147	EMSAM Approved Use Selegiline Hydrochloride Tablets USP are indicated as an adjunct in the management of Parkinsonian patients being treated with levodopa/carbidopa who exhibit deterioration in the quality of their response to this therapy. There is no evidence from controlled studies that selegiline has any beneficial effect in the absence of concurrent levodopa therapy. Evidence supporting this claim was obtained in randomized controlled clinical investigations that compared the effects of added selegiline or placebo in patients receiving levodopa/carbidopa. Selegiline was significantly superior to placebo on all three principal outcome measures employed: change from baseline in daily levodopa/carbidopa dose, the amount of 'off' time, and patient self-rating of treatment success. Beneficial effects were also observed on other measures of treatment success (e.g., measures of reduced end of dose akinesia, decreased tremor and sialorrhea, improved speech and dressing ability and improved overall disability as assessed by walking and comparison to previous state). Launch Date 2006

C_max

Value	Dose	Co-administered	Analyte	Population
8.9 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10215747	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		SELEGILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
11 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10215747	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		SELEGILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.3 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021479s005lbl.pdf	1.25 mg single, oral dose: 1.25 mg route of administration: Oral experiment type: SINGLE co-administered:		SELEGILINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
1.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10215747	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		SELEGILINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
15% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021479s005lbl.pdf	1.25 mg single, oral dose: 1.25 mg route of administration: Oral experiment type: SINGLE co-administered:		SELEGILINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
12 mg 1 times / day multiple, transdermal Highest studied dose Dose: 12 mg, 1 times / day Route: transdermal Route: multiple Dose: 12 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17568687/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17568687/	Other AEs: Headache, Infection... Other AEs: Headache (16%) Infection (15%) Back pain (6%) Diarrhea (11%) Nausea (7%) Insomnia (32%) Dry mouth (13%) Dizziness (14%) Nervousness (10%) Somnolence (5%) Anxiety (5%) Abnormal dreams (5%) Pharyngitis (7%) Application site reaction (44%) Sources: https://pubmed.ncbi.nlm.nih.gov/17568687/
12 mg 1 times / day multiple, transdermal Recommended Dose: 12 mg, 1 times / day Route: transdermal Route: multiple Dose: 12 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17568687/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17568687/	Other AEs: Headache, Infection... Other AEs: Headache (18%) Infection (9%) Back pain (3%) Diarrhea (9%) Nausea (5%) Insomnia (12%) Dry mouth (8%) Dizziness (5%) Nervousness (4%) Somnolence (3%) Anxiety (3%) Abnormal dreams (2%) Pharyngitis (3%) Application site reaction (24%) Sources: https://pubmed.ncbi.nlm.nih.gov/17568687/
2.5 mg 1 times / day multiple, oral Recommended Dose: 2.5 mg, 1 times / day Route: oral Route: multiple Dose: 2.5 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021479s003s004lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021479s003s004lbl.pdf	Other AEs: Back pain, Chest pain... Other AEs: Back pain (5%) Chest pain (2%) Pain (8%) Hypertension (3%) Constipation (4%) Diarrhea (2%) Dysphagia (2%) Dyspepsia (5%) Flatulence (2%) Nausea (11%) Stomatitis (5%) Tooth disorder (2%) Vomiting (3%) Ecchymosis (2%) Hypokalemia (2%) Leg cramps (3%) Myalgia (3%) Ataxia (3%) Depression (2%) Dizziness (11%) Dry mouth (4%) Dyskinesia (6%) Hallucinations (4%) Headache (7%) Insomnia (7%) Somnolence (3%) Tremor (3%) Dyspnea (3%) Pharyngitis (4%) Rhinitis (7%) Rash (4%) Skin disorder (6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/021479s003s004lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 879 CYP2B6 926 UGT2B10 31	P-gp 2052 CYP1A1 389 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C19 1119 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
UGT2B10 33	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/26669329/	yes [IC50 67.2 uM]
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18065502/	yes [Ki 15.6 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25656918/	yes [Ki 22 uM]

Drug as victim

Target	Modality	Activity
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/ \| https://pubmed.ncbi.nlm.nih.gov/12920164/ \| https://pubmed.ncbi.nlm.nih.gov/17495414/ \| https://pubmed.ncbi.nlm.nih.gov/15618670/	major
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/ \| https://pubmed.ncbi.nlm.nih.gov/12920164/ \| https://pubmed.ncbi.nlm.nih.gov/10862503/ \| https://pubmed.ncbi.nlm.nih.gov/15618670/	major
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/ \| https://pubmed.ncbi.nlm.nih.gov/12920164/ \| https://pubmed.ncbi.nlm.nih.gov/10862503/ \| https://pubmed.ncbi.nlm.nih.gov/15618670/	minor
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/ \| https://pubmed.ncbi.nlm.nih.gov/10862503/ \| https://pubmed.ncbi.nlm.nih.gov/17495414/ \| https://pubmed.ncbi.nlm.nih.gov/15618670/	minor
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12438524/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11602525/ \| https://pubmed.ncbi.nlm.nih.gov/12920164/	yes

PubMed

Title	Date	PubMed
The potential of dopamine agonists in drug addiction.	2002-04	11922858
Toxicokinetics of amphetamines: metabolism and toxicokinetic data of designer drugs, amphetamine, methamphetamine, and their N-alkyl derivatives.	2002-04	11897973
[Psychological and cognitive problems in Parkinson disease--therapeutic possibilities].	2002-03-06	11933648
Treatment of periodic limb movements in sleep with selegiline HCl.	2002-03	11921131
Placebo-associated improvements in motor function: comparison of subjective and objective sections of the UPDRS in early Parkinson's disease.	2002-03	11921113
Inhibition of human LDL oxidation by the neuroprotective drug l-deprenyl.	2002-03	11877901
Uncertainties in the pharmacotherapy of Parkinson's disease and how to solve them.	2002-02-15	11844927
Neuroprotective actions of selegiline.	2002-02-01	11813232
Antiapoptotic effect of (-)-deprenyl in rat kidney after ischemia-reperfusion.	2002-02	11859269
Pirlindole and dehydropirlindole protect rat cultured neuronal cells against oxidative stress-induced cell death through a mechanism unrelated to MAO-A inhibition.	2002-02	11834619
The effect of selegiline in the treatment of people with Alzheimer's disease: a meta-analysis of published trials.	2002-02	11813282
Deprenyl protects from MPTP-induced Parkinson-like syndrome and glutathione oxidation in rat striatum.	2002-01-25	11788154
Switching from bromocriptine to ropinirole in patients with advanced Parkinson's disease: open label pilot responses to three different dose-ratios.	2002-01-22	11801810
Neuroprotective and neurotoxic effects of monoamine oxidase-B inhibitors and derived metabolites under ischemia in PC12 cells.	2002-01-11	11779573
Practice parameter: initiation of treatment for Parkinson's disease: an evidence-based review: report of the Quality Standards Subcommittee of the American Academy of Neurology.	2002-01-08	11781398
Effect of repeated treatment with high doses of selegiline on behaviour, striatal dopaminergic transmission and tyrosine hydroxylase mRNA levels.	2002-01	11862330
The influence of metabolism on the MAO-B inhibitory potency of selegiline.	2002-01	11860347
Antidepressants for smoking cessation.	2002	11869562
Investigating potential anxiolytic, antidepressant and memory enhancing activity of deprenyl.	2001-12	11785779
Zonisamide has beneficial effects on Parkinson's disease patients.	2001-12	11755227
Ten-year follow-up of three different initial treatments in de-novo PD: a randomized trial.	2001-11-13	11706112
(-)-D-Deprenyl attenuates apoptosis in experimental brain ischaemia.	2001-11-02	11711036
Chronic daily administration of selegiline and EGb 761 increases brain's resistance to ischemia in mice.	2001-11-02	11640903
Role of monoamine oxidase inhibition and monoamine depletion in fenfluramine-induced neurotoxicity and serotonin release.	2001-11	11881977
The effects of oral selegiline hydrochloride on learning and training in the dog: a psychobiological interpretation.	2001-11	11642657
CYP2B6 and CYP2C19 as the major enzymes responsible for the metabolism of selegiline, a drug used in the treatment of Parkinson's disease, as revealed from experiments with recombinant enzymes.	2001-11	11602525
Incorporation of selegiline metabolites into hair after oral selegiline intake.	2001-10	11599606
Future of neuroprotection in Parkinson's disease.	2001-10	11489679
[Dopaminomimetic psychosis in Parkinson's disease: first symptom of early dementia?].	2001-09-20	11562835
Drug-induced psychotic symptoms in Parkinson's disease. Problems, management and dilemma.	2001-09	11697685
Medical treatment of canine pituitary-dependent hyperadrenocorticism (Cushing's disease).	2001-09	11570123
Simultaneous determination of selegiline-N-oxide, a new indicator for selegiline administration, and other metabolites in urine by high-performance liquid chromatography-electrospray ionization mass spectrometry.	2001-08-05	11499616
Evaluation of antiparkinsonian drugs in pharmacy records as a marker for Parkinson's disease.	2001-08	11599201
Changes in vascular alpha 1- and alpha 2-adrenoceptor responsiveness by selegiline treatment.	2001-08	11564130
[Parkinson's disease].	2001-08	11519161
Selegiline and mortality in subjects with Parkinson's disease: a longitudinal community study.	2001-07-24	11480425
Paroxysmal hypertensive crises induced by selegiline in a patient with Parkinson's disease.	2001-06	11499649
[A behavioral and neurochemical study on the mechanism of the anxiolytic effect of monoamine oxidase inhibitors].	2001-05	11481866
Do antioxidant strategies work against aging and age-associated disorders? Propargylamines: a possible antioxidant strategy.	2001-04	11795516
Eldepryl prevents 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced nigral neuronal apoptosis in mice.	2001-03	11780305
Parkinson's disease therapy: treatment of early and late disease.	2001-03	11780303
Selegiline treatment facilitates recovery after stroke.	2001	11944739
Pharmacological options for the treatment of Tourette's disorder.	2001	11772131
The effect of low oral doses of (-)-deprenyl and its metabolites on DSP-4 toxicity.	2001	11768624
[The effect of selegiline and vitamin E in the treatment of ALS: an open randomized clinical trials].	2001	11732275
Monoamine oxidase-inhibition and MPTP-induced neurotoxicity in the non-human primate: comparison of rasagiline (TVP 1012) with selegiline.	2001	11716151
Antiaging compounds: (-)deprenyl (selegeline) and (-)1-(benzofuran-2-yl)-2-propylaminopentane, [(-)BPAP], a selective highly potent enhancer of the impulse propagation mediated release of catecholamine and serotonin in the brain.	2001	11607046
Role of free radicals in the neurodegenerative diseases: therapeutic implications for antioxidant treatment.	2001	11599635
Effect of longevity treatment with (-)deprenyl on lifespan and sexual behavior in female rats.	2001	11558933
[Current strategies of pathogenetic therapy of Alzheimer's disease].	2001	11523421

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Parkinson's Disease: Recommended dose: 5 mg orally twice a day, Maximum dose: 10 mg orally per day Usual Adult Dose for Depression: Initial dose: Apply one 6 mg/24 hours transdermal patch to intact skin once every 24 hours, Maintenance dose: One 6 mg/24 hours to 12 mg/24 hours transdermal patch applied to the skin once a day, Maximum dose: 12 mg/24 hours transdermal patch applied to the skin once a day

Route of Administration: Other

In Vitro Use Guide

BEAS-2B cells were seeded in 6 cm dishes. Cells were pretreated with 100 nM selegiline for 30 min before further exposed to 2% CSM for 24 h. Total protein was extracted. Monoamine Oxidase Activity Fluorometric Assay Kit (BioVision Inc., Milpitas, CA, USA), Superoxide Dismutase (SOD) Detection kit (Nanjing Jiancheng Bioenginering Inst., China), Amplex Red Catalase Assay kit (Molecular Probes, Inc., Eugene, OR, USA) and Oxidative Glutathi-one (GSSG) Detection Kit (Nanjing Jiancheng Bioenginering Y. Cui et al. / Toxicology Letters 268 (2017) 44–50 45Inst., China) were used for MAO, SOD and CAT activities and GSH/GSSG ratio measurement, respectively.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:28:41 GMT 2025` Edited by `admin` on `Wed Apr 02 08:28:41 GMT 2025`
Record UNII	2K1V7GP655
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EMSAM

Preferred Name

English

SELEGILINE

Official Name

English

SELEGILINE [ORANGE BOOK]

Common Name

English

Selegiline [WHO-DD]

Common Name

English

SELEGILINE [VANDF]

Common Name

English

SELEGILINE [MI]

Common Name

English

selegiline [INN]

Common Name

English

BENZENEETHANAMINE, N,.ALPHA.-METHYL-N-2-PROPYNYL-, (.ALPHA.R)-

Common Name

English

(-)-(N)-METHYL-N-((1R)-1-METHYL-2-PHENYLETHYL)PROP-2-YN-1-AMINE

Common Name

English

L-SELEGILINE

Common Name

English

SELEGILINE [USAN]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175761