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Compound Detail

CHEMBL972

SELEGILINE
💊 Approved Drug
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💊 Approved Drug
C#CCN(C)[C@H](C)Cc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL972
Name SELEGILINE
Phase Approved
Structure Type MOL
InChI Key MEZLKOACVSPNER-GFCCVEGCSA-N
Therapeutic ✓ Yes

Known Names

Emsam L-selegiline Selegilina Selegiline
12
Targets
262
Activities
3
Assay Types
17
PK Parameters
20
Publications
4
Known Names
9
Indications
1
Mechanisms

Molecular Properties

187.3
MW (Da)
2.18
ALogP
1
HBA
0
HBD
3.2
PSA (Ų)
0.65
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1989
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Topical

Flags

Black Box Warning Natural Product
USAN Stem -giline
USAN Year 1992

Extended Properties

Molecular Formula C13H17N
MW 187.29
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -0.95

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Monoamine oxidase B inhibitor INHIBITOR Amine oxidase [flavin-containing] B ✓ ✓

Indications

Depressive Disorder, Major Parkinson Disease Borderline Personality Disorder Cocaine-Related Disorders Depressive Disorder Prostatic Neoplasms Tobacco Use Disorder Amphetamine-Related Disorders Schizophrenia

ATC Classification

N04BD01
selegiline
Level 1: NERVOUS SYSTEM
Level 2: ANTI-PARKINSON DRUGS

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States

Activity Summary

IC50 217 meas. best 10.77
Ki 44 meas. best 8.48
Kd 1 meas. best 7.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Amine oxidase [flavin-containing] B
CHEMBL2039
 IC50 10.77 7.5383 0.0 95
Amine oxidase [flavin-containing] B
CHEMBL2993
 IC50 8.56 7.4447 2.8 17
Amine oxidase [flavin-containing] B
CHEMBL2039
 Ki 8.48 6.7143 3.3 14
Monoamine oxidase
CHEMBL2095196
 IC50 7.89 7.0575 13.0 4
Amine oxidase [flavin-containing] A
CHEMBL3358
 IC50 7.75 6.131 18.0 10
Amine oxidase [flavin-containing] B
CHEMBL2039
 Kd 7.23 7.23 58.9 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 IC50 7.17 4.5013 67.2 67
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 6.76 6.76 172.0 1
Alpha-synuclein
CHEMBL6152
 IC50 6.57 6.57 270.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
 IC50 6.42 6.42 376.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 6.17 6.17 674.0 1
Amine oxidase [flavin-containing] B
CHEMBL2756
 Ki 6.01 6.01 970.0 4
Amine oxidase [flavin-containing] B
CHEMBL2756
 IC50 6.0 6.0 1000.0 2
Unchecked
CHEMBL612545
 Ki 6.0 5.8967 1000.0 3
Cytochrome P450 2B1
CHEMBL3335
 Ki 5.98 5.98 1050.0 1
Amine oxidase [flavin-containing] B
CHEMBL2993
 Ki 5.87 5.87 1350.0 4
Unchecked
CHEMBL612545
 IC50 5.79 5.79 1614.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 IC50 5.75 5.75 1798.0 1
Amine oxidase [flavin-containing] A
CHEMBL1951
 Ki 5.44 4.8043 3600.0 7
Amine oxidase [flavin-containing] A
CHEMBL3254
 Ki 5.42 5.17 3800.0 4
Amine oxidase [flavin-containing] A
CHEMBL3358
 Ki 4.98 4.7333 10566.0 3
Amine oxidase [flavin-containing] A
CHEMBL3254
 IC50 4.42 4.42 38018.9 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 1387.03 ng.hr.mL-1 Mus musculus
AUC 242.02 ng.hr.mL-1 Mus musculus
CL 20.0 mL.min-1.kg-1 Homo sapiens
CL 19.8 mL.min-1.kg-1 Homo sapiens
CL 20.0 mL.min-1.kg-1 Homo sapiens
CL 20.0 mL.min-1.kg-1 Homo sapiens
Cmax 22526.56 nM Mus musculus
Cmax 3037.54 nM Mus musculus
F 20.0 % Homo sapiens
Fu 0.13 - Homo sapiens
Fu 0.13 - Homo sapiens
MRT 1.6 hr Homo sapiens
T1/2 1.3 hr Homo sapiens
T1/2 0.29 hr Mus musculus
T1/2 0.56 hr Mus musculus
Tmax 0.0833 hr Mus musculus
Tmax 0.0833 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Amine oxidase [flavin-containing] B IC50 = 0.017 nM 10.77 Inhibition of human MAO-B using p-tyramine as substrate incubated for 15 mins by... 35772321
Amine oxidase [flavin-containing] B IC50 = 0.017 nM 10.77 Inhibition of human monoamine oxidase B 20875743
Amine oxidase [flavin-containing] B IC50 = 1.3 nM 8.89 Inhibition of human recombinant MAO-B expressed in insect cells by Amplex Red as... 24169316
Amine oxidase [flavin-containing] B IC50 = 1.3 nM 8.89 Inhibition of human recombinant MAO-B using benzylamine hydrochloride as substra... 23810676
Amine oxidase [flavin-containing] B IC50 = 2.76 nM 8.56 In vitro ability to inhibit Monoamine oxidase B activity in rat whole brain in v... 11591508
Amine oxidase [flavin-containing] B Ki = 3.3 nM 8.48 Inhibition of human recombinant soluble MAO-B expressed in Pichia pastoris incub... 25600407
Amine oxidase [flavin-containing] B Ki = 3.9 nM 8.41 Inhibition of human recombinant microsomal MAO-B expressed in Pichia pastoris in... 25600407
Amine oxidase [flavin-containing] B IC50 = 3.9 nM 8.41 Inhibition of human MAO-B expressed in baculovirus infected insect cell membrane... 29477889
Amine oxidase [flavin-containing] B IC50 = 5.5 nM 8.26 Inhibition of human recombinant MAO-B expressed in baculovirus infected BTI-TN-5... 30522087
Amine oxidase [flavin-containing] B IC50 = 5.5 nM 8.26 Inhibition of human recombinant MAO-B expressed in baculovirus infected BTI-TN-5... 31265934
Amine oxidase [flavin-containing] B IC50 = 6.13 nM 8.21 Inhibition of recombinant human MAO-B expressed in baculovirus-infected insect c... 23631427
Amine oxidase [flavin-containing] B IC50 = 6.13 nM 8.21 Inhibition of human MAO-B 24139167
Amine oxidase [flavin-containing] B IC50 = 6.11 nM 8.21 Inhibition of Sprague-Dawley rat liver MAO-B using p-tyramine as substrate prein... 30522087
Amine oxidase [flavin-containing] B IC50 = 6.8 nM 8.17 Irreversible inhibition of human MAOB 30404719
Amine oxidase [flavin-containing] B IC50 = 6.7 nM 8.17 Inhibition of MAO-B in rat liver homogenate using [14C]-phenylethylamine as subs... 24813882
Amine oxidase [flavin-containing] B IC50 = 6.74 nM 8.17 Inhibition of MAO-B in mitochondria-enriched Sprague-Dawley rat liver fractions ... 23631427
Amine oxidase [flavin-containing] B IC50 = 6.9 nM 8.16 Inhibition of N-terminal FLAG-tagged human recombinant MAO-B expressed in Sf9 ce... 37086699
Amine oxidase [flavin-containing] B IC50 = 7.0 nM 8.15 Inhibition of human recombinant MAO-B expressed in baculovirus infected BTI-TN-5... 30016860
Amine oxidase [flavin-containing] B IC50 = 7.0 nM 8.15 Inhibition of human MAO-B 32920430
Amine oxidase [flavin-containing] B IC50 = 7.0 nM 8.15 Inhibition of MAOB 18181565

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
30016860 10.1021/acs.jmedchem.7b01588 ADMET 17
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
1433183 10.1021/jm00098a017 Mus musculus 10
23474901 10.1016/j.ejmech.2013.02.009 Mus musculus 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
8487255 10.1021/jm00061a006 Amine oxidase [flavin-containing] B 7
30016860 10.1021/acs.jmedchem.7b01588 Mus musculus 6
25600407 10.1016/j.bmc.2014.12.063 Amine oxidase [flavin-containing] B 5
19256501 10.1021/jm801441s No relevant target 5
31917923 10.1021/acs.jmedchem.9b01886 Amine oxidase [flavin-containing] B 5
6864731 10.1021/jm00361a017 Monoamine oxidase 5
8941389 10.1021/jm960477e Unchecked 4
18426954 10.1124/dmd.108.020479 ADMET 4
22385498 10.1021/jm201692d Rattus norvegicus 4
7490728 10.1021/jm00024a006 Amine oxidase [flavin-containing] A 3
18666768 10.1021/jm800132g Amine oxidase [flavin-containing] B 3
20014752 10.1021/tx900326k Hepatotoxicity 3

Data from ChEMBL 36 via Core Engine