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Compound Detail

CHEMBL894

BUPROPION
💊 Approved Drug
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💊 Approved Drug
CC(NC(C)(C)C)C(=O)c1cccc(Cl)c1

Basic Information

ChEMBL ID CHEMBL894
Name BUPROPION
Phase Approved
Structure Type MOL
InChI Key SNPPWIUOZRMYNY-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Amfebutamone Bupropion Bupropion extended release Bupropion slow release Bupropione NSC-758686
15
Targets
56
Activities
2
Assay Types
30
PK Parameters
20
Publications
6
Known Names
20
Indications

Molecular Properties

239.8
MW (Da)
3.30
ALogP
2
HBA
1
HBD
29.1
PSA (Ų)
0.82
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1974

Extended Properties

Molecular Formula C13H18ClNO
MW 239.75
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness -0.88

Indications

Depressive Disorder Depressive Disorder Depressive Disorder, Major Anxiety Attention Deficit Disorder with Hyperactivity Dementia Depressive Disorder, Treatment-Resistant Obesity Schizophrenia Smoking Cessation Tobacco Use Disorder Alcoholism Amphetamine-Related Disorders Cocaine-Related Disorders Crohn Disease Huntington Disease Marijuana Abuse Restless Legs Syndrome Substance-Related Disorders Substance-Related Disorders

ATC Classification

N06AX12
bupropion
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

IC50 47 meas. best 6.48
Ki 9 meas. best 6.76

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL238
Ki 6.76 6.315 173.0 4
Sodium-dependent dopamine transporter
CHEMBL238
IC50 6.48 6.0246 330.0 13
Sodium-dependent dopamine transporter
CHEMBL338
Ki 6.43 6.43 371.5 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 6.35 5.714 443.0 10
Rattus norvegicus
CHEMBL376
IC50 6.05 5.835 900.0 2
Neuronal acetylcholine receptor; alpha3/beta2
CHEMBL2109234
IC50 6.0 6.0 1000.0 1
Unchecked
CHEMBL612545
Ki 5.85 5.85 1425.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
IC50 5.75 5.75 1800.0 3
Integrin alpha-5/Neuronal acetylcholine receptor subunit alpha-3/Neuronal acetylcholine receptor subunit beta-2/Neuronal acetylcholine receptor subunit beta-4
CHEMBL3885595
IC50 5.75 5.75 1800.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 5.7 5.7 1998.3 1
Unchecked
CHEMBL612545
IC50 5.63 5.63 2315.6 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.44 5.3 3642.0 2
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
IC50 5.1 4.7 7900.0 2
Acetylcholine receptor; alpha1/beta1/delta/gamma
CHEMBL1907588
IC50 5.1 5.1 7900.0 2
Neuronal acetylcholine receptor; alpha4/beta4
CHEMBL1907591
IC50 4.92 4.87 12000.0 2
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
IC50 4.92 4.92 12000.0 3
Sodium-dependent serotonin transporter
CHEMBL228
Ki 4.88 4.88 13311.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 4.33 4.33 47000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 4.16 4.16 69000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 404.0 ng.hr.mL-1 Homo sapiens
AUC 274.0 ng.hr.mL-1 Homo sapiens
AUC 356.0 ng.hr.mL-1 Homo sapiens
AUC 13.4 ng.hr.mL-1 Homo sapiens
AUC 16.1 ng.hr.mL-1 Homo sapiens
AUC 12.2 ng.hr.mL-1 Homo sapiens
AUC 13.4 ng.hr.mL-1 Homo sapiens
AUC 7330.0 ng.hr.mL-1 Homo sapiens
AUC 10950.0 ng.hr.mL-1 Homo sapiens
AUC 5829.0 ng.hr.mL-1 Homo sapiens
AUC 8120.0 ng.hr.mL-1 Homo sapiens
AUC 9.1 ng.hr.mL-1 Homo sapiens
AUC 10.6 ng.hr.mL-1 Homo sapiens
AUC 8.4 ng.hr.mL-1 Homo sapiens
AUC 9.0 ng.hr.mL-1 Homo sapiens
AUC 7560.0 ng.hr.mL-1 Homo sapiens
AUC 11330.0 ng.hr.mL-1 Homo sapiens
AUC 6100.0 ng.hr.mL-1 Homo sapiens
AUC 8470.0 ng.hr.mL-1 Homo sapiens
AUC 318.0 ng.hr.mL-1 Homo sapiens
AUC 423.0 ng.hr.mL-1 Homo sapiens
AUC 713.0 ng.hr.mL-1 Homo sapiens
AUC 866.0 ng.hr.mL-1 Homo sapiens
AUC 1030.0 ng.hr.mL-1 Homo sapiens
AUC 1290.0 ng.hr.mL-1 Homo sapiens
AUC 303.0 ng.hr.mL-1 Homo sapiens
AUC 1.05 ng.hr.mL-1 Homo sapiens
AUC 1.15 ng.hr.mL-1 Homo sapiens
AUC 1.06 ng.hr.mL-1 Homo sapiens
AUC 1.13 ng.hr.mL-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter Ki = 173.0 nM 6.76 Uptake Assay Protocol: DAT: This protocol was designed to measure inhibition of ... -
Sodium-dependent dopamine transporter IC50 = 330.0 nM 6.48 Inhibition of dopamine transporter (unknown origin) assessed as inhibition of do... 36174836
Sodium-dependent dopamine transporter Ki = 371.54 nM 6.43 Binding affinity to dopamine transporter (DAT) using [3H]WIN-35428 as a radiolig... 11063611
Sodium-dependent dopamine transporter Ki = 441.0 nM 6.36 Displacement of [3H]WIN-35428 from human dopamine transporter expressed in mouse... 19442525
Sodium-dependent noradrenaline transporter IC50 = 443.0 nM 6.35 Inhibition of [3H]norepinephrine reuptake at human NET expressed in HEK293 cells 19821577
Sodium-dependent dopamine transporter IC50 = 550.0 nM 6.26 Inhibition of DAT (unknown origin) assessed as transporter-mediated dopamine reu... 24901260
Sodium-dependent dopamine transporter IC50 = 658.0 nM 6.18 Inhibition of [3H]dopamine uptake at human DAT expressed in HEK293 cells 20158204
Sodium-dependent dopamine transporter IC50 = 658.0 nM 6.18 Inhibition of human DAT expressed in HEK293 cells assessed as inhibition of [3H]... 21058665
Sodium-dependent dopamine transporter IC50 = 660.0 nM 6.18 Inhibition of [3H]dopamine reuptake at human DAT expressed in HEK293 cells after... 20509659
Sodium-dependent dopamine transporter Ki = 821.4 nM 6.08 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Sodium-dependent dopamine transporter Ki = 871.0 nM 6.06 Displacement of [125I]RTI55 from cloned human DAT expressed in HEK293 cells 19821577
Rattus norvegicus IC50 = 900.0 nM 6.05 In vitro inhibition of dopamine (DA) uptake in synaptosomal preparation of rat b... 8558500
Sodium-dependent dopamine transporter IC50 = 945.0 nM 6.03 Inhibition of [3H]dopamine reuptake at human DAT expressed in HEK293 cells 19821577
Neuronal acetylcholine receptor; alpha3/beta2 IC50 = 1000.0 nM 6.0 Inhibitory concentration against Nicotinic acetylcholine receptor alpha3-beta2 16033252
Sodium-dependent dopamine transporter IC50 = 1033.8 nM 5.99 DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) -
Sodium-dependent dopamine transporter IC50 = 1200.0 nM 5.92 Inhibition of [3H]-5-dopamine reuptake in human DAT expressed in HEK293 cells by... 27647372
Sodium-dependent dopamine transporter IC50 = 1200.0 nM 5.92 Inhibition of [3H]-5-dopamine reuptake in human DAT expressed in HEK293 cells by... 28274674
Sodium-dependent dopamine transporter IC50 = 1200.0 nM 5.92 Inhibition of re-uptake of [3H]-DA at human DAT expressed in HEK293 cells by liq... 28807575
Sodium-dependent dopamine transporter IC50 = 1200.0 nM 5.92 Inhibition of human DAT expressed in HEK293 cells assessed as reduction in [3H]-... 30007567
Unchecked Ki = 1425.0 nM 5.85 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -

Literature References

Data from ChEMBL 36 via Core Engine