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Bupropion

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Also known as AmfebutamoneBupropion extended releaseBupropion slow releaseBupropioneNSC-758686rac-bupropionSID90340803SID174006913(R/S)-Bupropion

Summary

Bupropion (CHEMBL894) is an approved small-molecule antidepressant (ATC N06AX12) targeting SLC6A2 and SLC6A3; indicated across 32 conditions including major depressive disorder and depressive disorder.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N06AX12
  • Targets: 2 (SLC6A2, SLC6A3)
  • Indications: 32 conditions
  • Clinical trials: 213
  • Chemistry: 239.74 Da · C13H18ClNO

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL894
NameBupropion
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID444
ChEBICHEBI:3219
ATCN06AX12
Molecular formulaC13H18ClNO
Molecular weight239.74
InChIKeySNPPWIUOZRMYNY-UHFFFAOYSA-N

SMILES: CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C

IUPAC name: 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one

ChEBI definition: An aromatic ketone that is propiophenone carrying a tert-butylamino group at position 2 and a chloro substituent at position 3 on the phenyl ring.

Pharmacological roles (ChEBI): antidepressant.

Other ChEBI roles (chemical / environmental): environmental contaminant, xenobiotic.

Also known as: Amfebutamone, Bupropion, Bupropion extended release, Bupropion slow release, Bupropione, NSC-758686, bupropion, rac-bupropion, SID90340803, BUPROPION, SID174006913, (R/S)-Bupropion

Parent form; salt/anhydrous children: CHEMBL1698, CHEMBL1201735

Patent coverage: 10,242 distinct patent families (36,982 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 36,037 (97%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
SLC6A2NETInhibition6.360.4%P23975
SLC6A3DATInhibition6.350.2%Q01959

Broader ChEMBL bioactivity targets: 15 (assay-derived). Sample: Acetylcholine receptor; alpha1/beta1/delta/gamma, Neuronal acetylcholine receptor; alpha4/beta2, Neuronal acetylcholine receptor; alpha4/beta4, Neuronal acetylcholine receptor; alpha3/beta4, Neuronal acetylcholine receptor; alpha3/beta2, Sodium-dependent noradrenaline transporter, Sodium-dependent serotonin transporter, Histamine H1 receptor, Kappa-type opioid receptor, Sodium-dependent dopamine transporter.

Bioactivity

ChEMBL activities: 41 potent at pChembl ≥ 5 of 51 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
SLC6A36.76Ki173nMCHEMBL_ACT_27603236
SLC6A36.48IC50330nMCHEMBL_ACT_24965240
P239776.43Ki371.5nMCHEMBL_ACT_1246784
SLC6A36.36Ki441nMCHEMBL_ACT_2657847
SLC6A26.35IC50443nMCHEMBL_ACT_2990800
SLC6A36.26IC50550nMCHEMBL_ACT_15023467
SLC6A36.18IC50658nMCHEMBL_ACT_3118271
SLC6A36.18IC50660nMCHEMBL_ACT_3360058
SLC6A36.18IC50658nMCHEMBL_ACT_6312626
SLC6A36.08Ki821.4nMCHEMBL_ACT_7602723
SLC6A36.07AC50842.8nMCHEMBL_ACT_25124622
SLC6A36.06Ki871nMCHEMBL_ACT_2990786
SLC6A36.03IC50945nMCHEMBL_ACT_2990784
CHRNB26IC501000nMCHEMBL_ACT_1484931
SLC6A35.99IC501034nMCHEMBL_ACT_7602722
SLC6A35.92IC501200nMCHEMBL_ACT_18030833
SLC6A35.92IC501200nMCHEMBL_ACT_18212988
SLC6A35.92IC501200nMCHEMBL_ACT_18667291
SLC6A35.92IC501200nMCHEMBL_ACT_19448672
SLC6A25.84IC501450nMCHEMBL_ACT_708463
SLC6A25.8IC501600nMCHEMBL_ACT_24965235
SLC6A35.8IC501567nMCHEMBL_ACT_2657848
CHRNB45.75IC501800nMCHEMBL_ACT_1484934
CHRNB45.75IC501800nMCHEMBL_ACT_15023472
CHRNB45.75IC501800nMCHEMBL_ACT_3359558
ITGA55.75IC501800nMCHEMBL_ACT_6312587
SLC6A25.73IC501850nMCHEMBL_ACT_3118287
SLC6A25.73IC501850nMCHEMBL_ACT_3360043
SLC6A25.73IC501850nMCHEMBL_ACT_6312613
CYP2C195.7IC501998nMCHEMBL_ACT_7602704

Target pathways

Aggregated over 2 target gene(s): SLC6A2, SLC6A3.

Top Reactome pathways

14 total, by targets touching each:

PathwayTargetsGenes
Disease2SLC6A2, SLC6A3
Transport of small molecules2SLC6A2, SLC6A3
R-HSA-4253662SLC6A2, SLC6A3
SLC-mediated transmembrane transport2SLC6A2, SLC6A3
SLC-mediated transport of neurotransmitters2SLC6A2, SLC6A3
SLC transporter disorders2SLC6A2, SLC6A3
Disorders of transmembrane transporters2SLC6A2, SLC6A3
Neurotransmitter clearance1SLC6A3
Transmission across Chemical Synapses1SLC6A3
Neuronal System1SLC6A3
Dopamine clearance from the synaptic cleft1SLC6A3
Defective neurotransmitter clearance by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS)1SLC6A3
Defective SLC6A2 causes orthostatic intolerance (OI)1SLC6A2
Defective transport of neurotransmitters by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS)1SLC6A3

Dominant GO biological processes

GO termTargets
neurotransmitter transport2
amino acid transport2
response to xenobiotic stimulus2
obsolete monoamine transport2
sodium ion transmembrane transport2
dopamine uptake involved in synaptic transmission2
norepinephrine uptake2
transmembrane transport2
chemical synaptic transmission1
obsolete norepinephrine transport1
response to pain1
neuron cellular homeostasis1
catecholamine uptake1
neurotransmitter reuptake1
chloride transmembrane transport1

Indications & clinical

Indications

32 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
major depressive disorder4MONDO:0002009MONDO:0002009
depressive disorder4MONDO:0002050MONDO:0002050
obesity disorder3MONDO:0011122EFO:0001073
nicotine dependence3MONDO:0008575EFO:0003768
attention deficit-hyperactivity disorder3MONDO:0007743EFO:0003888
anxiety3MONDO:0011918EFO:0005230
dementia3MONDO:0001627HP:0000726
Crohn disease2MONDO:0005011EFO:0000384
cocaine dependence2MONDO:0005186EFO:0002610
drug dependence2MONDO:0005303EFO:0003890
restless legs syndrome2MONDO:0005391EFO:0004270
methamphetamine dependence2MONDO:0005419EFO:0004701
cannabis dependence2MONDO:0005689EFO:0007191
alcohol abuse2MONDO:0002046MONDO:0002046
substance-related disorder2MONDO:0002494MONDO:0002491
Huntington disease2MONDO:0007739MONDO:0007739
B-cell chronic lymphocytic leukemia1MONDO:0004948EFO:0000095
neoplasm1MONDO:0005070EFO:0000616
non-small cell lung carcinoma1MONDO:0005233EFO:0003060
physiological sexual disorder1MONDO:0002134EFO:0004714
head and neck cancer1MONDO:0005627EFO:0006859
metastatic melanoma1MONDO:0005191EFO:0002617
Alzheimer disease1MONDO:0004975MONDO:0004975
type 2 diabetes mellitus1MONDO:0005148MONDO:0005148
inborn mitochondrial metabolism disorder1MONDO:0004069MONDO:0044970
bipolar disorder1MONDO:0004985MONDO:0004985
sickle cell disease1MONDO:0011382MONDO:0011382

5 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 213.

Phase distribution

PhaseTrials
PHASE464
PHASE139
Not specified33
PHASE326
PHASE225
PHASE2/PHASE313
PHASE1/PHASE29
EARLY_PHASE14

Top trials by phase / activity

NCTPhaseStatusTitle
NCT04604509PHASE4RECRUITINGNicotine Replacement Therapy, Counseling, Varenicline, and Bupropion for Smoking Cessation, the PISCES I Trial
NCT05273996PHASE4ACTIVE_NOT_RECRUITINGPredictors of Cognitive Outcomes in Geriatric Depression
NCT06223880PHASE4RECRUITINGA Study to Evaluate the Efficacy of AXS-05 Compared to Bupropion in Preventing the Relapse of Depressive Symptoms
NCT06254001PHASE4RECRUITINGEffectiveness of Combined Tobacco Treatment in Hospitalized Subjects
NCT06620562PHASE4RECRUITINGImproving Efficacity of Sleeve Gastrectomy With Naltrexone/Bupropion Extended-release Tablet
NCT07266545PHASE4RECRUITINGRNA Editing as a Biomarker of Antidepressant Response in Unipolar and Bipolar Depression (EDIT-ANDRE)
NCT00006170PHASE4COMPLETEDBupropion and Weight Control for Smoking Cessation - 1
NCT00044434PHASE4COMPLETEDBupropion as a Smoking Cessation Aid in Alcoholics
NCT00106197PHASE4UNKNOWNHormone and Sleep Response to Antidepressant Treatment in Adolescents and Adults With Depression
NCT00132821PHASE4COMPLETEDImpact of Smoking Cessation on Sleep - 5
NCT00177567PHASE4COMPLETEDTreatment of Geriatric Bipolar Mood Disorders: A Pilot Study
NCT00178828PHASE4COMPLETEDDynamic Measures of Neurochemistry in Mood Disorders
NCT00186446PHASE4COMPLETEDTreatment of Nicotine Dependence and Acute Depression
NCT00296647PHASE4COMPLETEDSmoking Cessation Intervention: Effectiveness in Primary Care
NCT00296712PHASE4COMPLETEDAre Two Antidepressants a Good Initial Treatment for Depression?
NCT00296777PHASE4COMPLETEDTreatment of Depression Following Multiple Brain Tests
NCT00316160PHASE4COMPLETEDSexual Functioning Study With Antidepressants
NCT00320697PHASE4COMPLETEDSmoking Relapse Prevention in Schizophrenia
NCT00320723PHASE4COMPLETEDNicotine Replacement Therapy for Smoking Cessation in Schizophrenia
NCT00332644PHASE4COMPLETEDSmoking Cessation Medications: Efficacy, Mechanisms and Algorithms
NCT00404755PHASE4COMPLETEDDichotic Listening as a Predictor of Medication Response in Depression
NCT00429169PHASE4TERMINATEDParoxetine/Bupropion in Suicide Attempters/Ideators With Major Depression
NCT00449007PHASE4TERMINATEDFluoxetine and Bupropion to Treat Patients With Depression and Alcoholism
NCT00495352PHASE4COMPLETEDThe Pharmacogenetic Study , Readiness to Change, and Pharmacological Intervention for Smoking Cessation in Schizophrenia
NCT00511134PHASE4TERMINATEDStudy of Lunesta Versus Placebo for Sleep Problems Related to Smoking Cessation and Zyban
NCT00519428PHASE4COMPLETEDDoes Dual Therapy Hasten Antidepressant Response?
NCT00611975PHASE4COMPLETEDEffect of Antidepressants on Sex Hormone Levels and Sexual Functioning
NCT00770666PHASE4COMPLETEDCombination Medications vs. Patch Alone for Medically-Ill Smokers
NCT00846339PHASE4COMPLETEDPET Imaging Study on Occupancy of Dopamine D2 Receptors and Genotypes After Bupropion Administration
NCT00926835PHASE4TERMINATEDEffect of Antidepressants on the Treatment for Korean Major Depressive Disorder Patients
NCT00936299PHASE4COMPLETEDBupropion for ADHD in Adolescents With Substance Use Disorder
NCT01023659PHASE4COMPLETEDDistribution of Bupropion and Varenicline to Increase Smoking Cessation Attempts
NCT01330043PHASE4COMPLETEDExtended Treatment for Smoking Cessation
NCT01477931PHASE4COMPLETEDInterventional Study of Wellbutrin XL in Major Depressive Disorder With Atypical Features
NCT01541475PHASE4COMPLETEDNeuroimaging Study of Bupropion Treatment in Patients With Major Depressive Disorder
NCT01583023PHASE4UNKNOWNUsing Repetitive Transcranial Magnetic Stimulation (rTMS) for the Treatment of Bipolar Depression
NCT01621022PHASE4COMPLETEDBupropion Alone or Combined With Nicotine Gum
NCT01716221PHASE4COMPLETEDAn Objective Double-blind Evaluation of Bupropion and Citalopram in an Individual With Friedreich Ataxia
NCT01764867PHASE4UNKNOWNAlgorithm Guided Treatment Strategies for Major Depressive Disorder
NCT01942187PHASE4WITHDRAWNA Comparison of Medication Augmentation and PST in the Treatment of Depression in Older Adults

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 34 clinical and 116 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

585 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
AfatinibChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
AMITRIPTYLINEChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
DACOMITINIBChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
GENTIAN VIOLETChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
IdelalisibChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
OlodaterolChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
PIMAVANSERINChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
REGORAFENIBChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
TAFENOQUINEChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
UMECLIDINIUMChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
VORAPAXARChEMBL + PubChemPhase 4 (approved)SLC6A2, SLC6A3
ACETOPHENAZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
AMINOCAPROIC ACIDChEMBLPhase 4 (approved)SLC6A2, SLC6A3
AMIODARONEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
AMLODIPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
AMODIAQUINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
AMOXAPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
ARIPIPRAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
ASENAPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
ASTEMIZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
ATOMOXETINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
AZELASTINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BAZEDOXIFENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BENFLUOREXChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BENOXINATEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BENPERIDOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BENZIODARONEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BENZPHETAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BENZTROPINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BENZYDAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BENZYL BENZOATEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BEPRIDILChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BEXAROTENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BITHIONOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BOSUTINIBChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BREXPIPRAZOLEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BROMHEXINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BROMODIPHENHYDRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BROMPERIDOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3
BROMPHENIRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CABERGOLINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CALCITRIOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CANNABIDIOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CARBINOXAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CARVEDILOLChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CASPOFUNGINChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CELECOXIBChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CETIRIZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CHLORHEXIDINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CHLORPHENIRAMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CHLORPHENTERMINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CHLORPROMAZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CHLORPROTHIXENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CINACALCETChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CINNARIZINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CITALOPRAMChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CLEMASTINEChEMBLPhase 4 (approved)SLC6A2, SLC6A3
CLOMIPHENEChEMBLPhase 4 (approved)SLC6A2, SLC6A3

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot