SELEGILINE HYDROCHLORIDE

First approved in 1989

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C13H17N.ClH
Molecular Weight	223.742
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IYETZZCWLLUHIJ-UTONKHPSSA-N

InChI=1S/C13H17N.ClH/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13;/h1,5-9,12H,10-11H2,2-3H3;1H/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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Selegiline effects on cocaine-induced changes in medial temporal lobe metabolism and subjective ratings of euphoria.	1999 Jun	10327427
Selegiline-induced postural hypotension in Parkinson's disease: a longitudinal study on the effects of drug withdrawal.	1999 Mar	10091617
Sleep attacks and Parkinson's disease treatment.	2000 Apr 15	10776750
Sleep attacks (sleep episodes) with pergolide.	2000 Apr 15	10776749
Workshop IV: drug treatment guidelines for the long-term management of Parkinson's disease.	2000 Sep	11199819
Adverse drug reactions to selegiline: a review of the French pharmacovigilance database.	2000 Sep-Oct	11154095
Selegiline treatment facilitates recovery after stroke.	2001	11944739
The effect of low oral doses of (-)-deprenyl and its metabolites on DSP-4 toxicity.	2001	11768624
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
Anti-apoptotic and apoptotic action of (-)-deprenyl and its metabolites.	2001	11261744
Selective inhibition of MAO-B through chronic low-dose (R)-deprenyl treatment in C57BL/6 mice has no effect on basal neostriatal dopamine levels.	2001 Apr	11259132
Attenuation of paraquat-induced dopaminergic toxicity on the substantia nigra by (-)-deprenyl in vivo.	2001 Apr 1	11264021
Evaluation of antiparkinsonian drugs in pharmacy records as a marker for Parkinson's disease.	2001 Aug	11599201
Possible applications for dopaminergic agents following traumatic brain injury: part 2.	2001 Feb	11277855
The economic consequences of a drug-drug interaction.	2001 Feb	11199940
Selegiline and mortality in subjects with Parkinson's disease: a longitudinal community study.	2001 Jul 24	11468339
The frissonnant mutant mouse, a model of dopamino-sensitive, inherited motor syndrome.	2001 Jun	11442353
[Dopaminomimetic psychosis in Parkinson's disease: first symptom of early dementia?].	2001 Jun 1-15	11562835
Freezing of gait in PD: prospective assessment in the DATATOP cohort.	2001 Jun 26	11425939
Parkinson's disease therapy: treatment of early and late disease.	2001 Mar	11780303
L-dopa and selegiline for tyrosine hydroxylase deficiency.	2001 Mar	11241071
[A behavioral and neurochemical study on the mechanism of the anxiolytic effect of monoamine oxidase inhibitors].	2001 May	11481866
[Parkinson patients. Normal life expectancy with selegiline?].	2001 May 28	11434273
Practice parameter: management of dementia (an evidence-based review). Report of the Quality Standards Subcommittee of the American Academy of Neurology.	2001 May 8	11342679
Role of monoamine oxidase inhibition and monoamine depletion in fenfluramine-induced neurotoxicity and serotonin release.	2001 Nov	11881977
Ten-year follow-up of three different initial treatments in de-novo PD: a randomized trial.	2001 Nov 13	11706112
(-)-D-Deprenyl attenuates apoptosis in experimental brain ischaemia.	2001 Nov 2	11711036
Incorporation of selegiline metabolites into hair after oral selegiline intake.	2001 Oct	11599606
The potential of dopamine agonists in drug addiction.	2002 Apr	11922858
Antiapoptotic effect of (-)-deprenyl in rat kidney after ischemia-reperfusion.	2002 Feb	11859269
The effect of selegiline in the treatment of people with Alzheimer's disease: a meta-analysis of published trials.	2002 Feb	11813282
The influence of metabolism on the MAO-B inhibitory potency of selegiline.	2002 Jan	11860347
Uncertainties in the pharmacotherapy of Parkinson's disease and how to solve them.	2002 Jan-Feb	11844927
Placebo-associated improvements in motor function: comparison of subjective and objective sections of the UPDRS in early Parkinson's disease.	2002 Mar	11921113
[Psychological and cognitive problems in Parkinson disease--therapeutic possibilities].	2002 Mar 6	11933648

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 `Mon Mar 31 17:52:56 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:56 GMT 2025`
Record UNII	6W731X367Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SELEGILINE HYDROCHLORIDE

Official Name

English

ELDEPRYL

Preferred Name

English

Selegiline hydrochloride [WHO-DD]

Common Name

English

SELEGILINE HYDROCHLORIDE [MI]

Common Name

English

(-)-(R)-N,.ALPHA.-DIMETHYL-N-2-PROPYNYLPHENETHYLAMINE HYDROCHLORIDE

Systematic Name

English

SELEGILINE HYDROCHLORIDE [JAN]

Common Name

English

SELEGILINE HYDROCHLORIDE [USAN]

Common Name

English

L-DEPRENYL

Common Name

English

SELEGILINE HYDROCHLORIDE [USP MONOGRAPH]

Common Name

English

SELEGILINE HCL

Common Name

English

ZELAPAR

Brand Name

English

BENZENEETHANAMINE, N,.ALPHA.-DIMETHYL-N-2-PROPYNYL-, HYDROCHLORIDE, (R)-

Systematic Name

English

NSC-759259

Code

English

SELEGILINE HYDROCHLORIDE [GREEN BOOK]

Common Name

English

SELEGILINE HYDROCHLORIDE [HSDB]

Common Name

English

SELEGILINE HYDROCHLORIDE [VANDF]

Common Name

English

SELEGILINE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

SELEGILINE HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

SELEGILINE HYDROCHLORIDE [USP-RS]

Common Name

English

SELEGILINE HYDROCHLORIDE [MART.]

Common Name

English

ENSAM

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667