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Compound Detail

CHEMBL1698

BUPROPION HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
CC(NC(C)(C)C)C(=O)c1cccc(Cl)c1.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1698
Name BUPROPION HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key HEYVINCGKDONRU-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL894
Active Moiety CHEMBL894

Known Names

Amfebutamone hydrochloride Bupropion hcl Bupropion hydrochloride Bupropion hydrochloride component of auvelity Bupropion hydrochloride component of contrave BW 323 BW-323 BW323 Forfivo xl Mysimba NSC-315851 Wellbutrin +5 more
3
Targets
5
Activities
1
Assay Types
0
PK Parameters
20
Publications
17
Known Names
17
Indications
2
Mechanisms

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
USAN Year 1974

Extended Properties

Molecular Formula C13H19Cl2NO
MW 276.21
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness -0.88

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Dopamine transporter inhibitor INHIBITOR Sodium-dependent dopamine transporter ✓ ✓
Norepinephrine transporter inhibitor INHIBITOR Sodium-dependent noradrenaline transporter ✓ ✓

Indications

Depressive Disorder Depressive Disorder Depressive Disorder, Major Mood Disorders Seasonal Affective Disorder Seasonal Affective Disorder Bipolar Disorder Bipolar Disorder Lung Neoplasms Neoplasms Smoking Smoking Cessation Tobacco Use Disorder Alcoholism Feeding and Eating Disorders Obesity Hepatolenticular Degeneration

Drug Warnings

Black Box Warning
psychiatric toxicity
Country: United States
Black Box Warning
cardiotoxicity
Country: United States

Activity Summary

IC50 5 meas. best 5.91

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sodium-dependent dopamine transporter
CHEMBL338
 IC50 5.91 5.91 1230.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.2 5.0333 6309.6 3
Sodium-dependent noradrenaline transporter
CHEMBL222
 IC50 4.9 4.9 12600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sodium-dependent dopamine transporter IC50 = 1230.0 nM 5.91 Compound was tested for its ability to inhibit the neurotransmitter dopamine-DA ... -
Plasmodium falciparum IC50 = 6309.57 nM 5.2 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Sodium-dependent noradrenaline transporter IC50 = 12600.0 nM 4.9 Inhibition of the Norepinephrine transporter (NET, SLC6A2) as assessed by GPCR-m... 34112854

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
34112854 10.1038/s41598-021-91700-7 Sodium-dependent noradrenaline transporter 1
- 10.6019/CHEMBL4513141 Acinetobacter baumannii 1
- 10.6019/CHEMBL4513141 Pseudomonas aeruginosa 1
- 10.6019/CHEMBL4513141 Klebsiella pneumoniae 1
- 10.6019/CHEMBL4513141 Escherichia coli 1
- 10.6019/CHEMBL4513141 Cryptococcus neoformans 1
- 10.6019/CHEMBL4513141 Candida albicans 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.1016/S0960-894X(97)10053-1 Sodium-dependent dopamine transporter 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 4 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 3 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 1
23956101 10.1093/toxsci/kft176 Bile salt export pump 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
20553011 10.1021/tx1000865 Hepatotoxicity 1

Data from ChEMBL 36 via Core Engine