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bupropion

File:Bupropion_structure.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ834280· pop 48· linked from 3,580 articles

Also 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

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 sections
Contents
  • 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.

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