File:Bupropion_structure.svg · Wikimedia Commons · See Wikimedia Commons
bupropion
Sign in to saveAlso known as amfebutamone, BW-323
Bupropion, formerly called amfebutamone, and sold under the brand name Wellbutrin among others, is an atypical antidepressant that is indicated in the treatment of major depressive disorder and seasonal affective disorder and to support smoking cessation. A norepinephrine–dopamine reuptake inhibitor (NDRI), it is also popular as an add-on medication in the cases of "incomplete response" to the first-line selective serotonin reuptake inhibitor (SSRI) antidepressant. Bupropion has several features that distinguish it from other antidepressants: It does not usually cause sexual dysfunction, it is
Key facts
- Drug.index2_label
- as HCl
- Drug.CAS_number
- 34911-55-2
- Drug.Verifiedfields
- correct
- Drug.Watchedfields
- correct
- Drug.verifiedrevid
- 852547309
- Drug.image
- Racemic-Bupropion-2D-Skeletal.png
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.alt
- Skeletal formula of bupropion
- Drug.imageL
- (S)-Bupropion 3D-Ball-and-Stick Model generated with BIOVIA Discovery Visual Studio.png
- Drug.widthL
- 150
- Drug.imageR
- R-Isomer-Bupropion-3D-Ball-and-Stick.png
- Drug.widthR
- 150
- Drug.pronounce
- Bupropion: Amfebutamone:
- Drug.tradename
- Wellbutrin, Zyban, others
- Drug.MedlinePlus
- a695033
- Drug.DailyMedID
- Bupropion
- Drug.pregnancy_AU
- B2
via Wikipedia infobox
Chemical data
- Formula
- C13H18ClNO
- Molecular weight
- 239.74 g/mol
- IUPAC name
- 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
- SMILES
- CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C
- InChIKey
- SNPPWIUOZRMYNY-UHFFFAOYSA-N
- XLogP
- 3.2
- Polar surface area
- 29.1 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
6,368 papers- Use of bupropion in combination with serotonin reuptake inhibitors.Biological psychiatry · 2006
- Pharmacokinetic and pharmacodynamic of bupropion: integrative overview of relevant clinical and forensic aspects.Drug metabolism reviews · 2019
- Bupropion and Anxiety: A Brief Review.Human psychopharmacology · 2025
- Bupropion-myth-busting!CNS spectrums · 2022
- Dextromethorphan/Bupropion: First Approval.CNS drugs · 2022
via PubMed
Wikidata facts
- Mass
- 239.107692
- Image
- Bupropion.svg
Show 6 more facts
- chemical formula
- C₁₃H₁₈ClNO
- Commons category
- Bupropion
- World Health Organisation international non-proprietary name
- bupropion
- canonical SMILES
- CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C
- defined daily dose
- 0.3
- stylized name
- buPROPion
Sources (11)
via Wikidata · CC0
~39 min read
Article
27 sectionsContents
- Medical uses
- Depression
- Smoking cessation
- Attention deficit hyperactivity disorder
- Sexual dysfunction
- Weight loss
- Other uses
- Available forms
- Contraindications
- Side effects
- Psychiatric
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Synthesis
- Analogues
- History
- Society and culture
- Recreational use
- Legal status
- Brand names
- Research
- See also
- References
Bupropion, formerly called amfebutamone, and sold under the brand name Wellbutrin among others, is an atypical antidepressant that is indicated in the treatment of major depressive disorder and seasonal affective disorder and to support smoking cessation. A norepinephrine–dopamine reuptake inhibitor (NDRI), it is also popular as an add-on medication in the cases of "incomplete response" to the first-line selective serotonin reuptake inhibitor (SSRI) antidepressant. Bupropion has several features that distinguish it from other antidepressants: It does not usually cause sexual dysfunction, it is not associated with weight gain or sleepiness, and it is more effective than SSRIs at improving symptoms of hypersomnia and fatigue. Bupropion, particularly the immediate-release formulation, carries a higher risk of seizure than many other antidepressants; hence, caution is recommended in patients with a history of seizure disorder. The medication is taken by mouth.
Common adverse effects of bupropion with the greatest difference from placebo are dry mouth, nausea, constipation, insomnia, anxiety, tremor, and excessive sweating. Raised blood pressure is notable. Rare but serious side effects include seizures, liver toxicity, psychosis, and risk of overdose. Bupropion use during pregnancy may be associated with increased likelihood of congenital heart defects.