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Bupropion

Not to be confused with Buprenorphine or Buspirone.

Bupropion
Skeletal formula of bupropion
Ball-and-stick model of the (S) isomer of the bupropion molecule
1 : 1 mixture (racemate)
Clinical data
Pronunciation/bjuːˈproʊpiɒn/
bew-PROH-pee-on
am-fa-BEW-teh-moan
Trade namesWellbutrin, Zyban, others
Other namesAmfebutamone; 3-Chloro-N-tert-butyl-β-keto-α-methylphenethylamine;
3-Chloro-N-tert-butyl-β-ketoamphetamine;
Bupropion hydrochloride[1]
AHFS/Drugs.comMonograph
MedlinePlusa695033
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classNDRI antidepressants
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability5-20% (estimate)
Protein bindingBupropion: 84%[13]
Hydroxybupropion: 77%[13]
Threohydrobupropion: 42%[13]
MetabolismLiver, intestines[15]
Metabolites• Hydroxybupropion
• Threohydrobupropion
• Erythrohydrobupropion
• Others
Elimination half-lifeBupropion: 11–21 h[14][15]
Hydroxybupropion: 20 h[15]
Threohydrobupropion: 37 h[15]
Erythrohydrobupropion: 33 h[15]
ExcretionUrine: 87% (0.5% unchanged)[15]
Feces: 10%[15]
Identifiers
  • (RS)-2-(tert-Butylamino)-1-(3-chlorophenyl)propan-1-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18ClNO
Molar mass239.74 g·mol−1
3D model (JSmol)
  • O=C(C(C)NC(C)(C)C)C1=CC=CC(Cl)=C1
  • InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3 checkY
  • Key:SNPPWIUOZRMYNY-UHFFFAOYSA-N checkY
  (verify)

Bupropion, formerly called amfebutamone,[16] and sold under the brand name Wellbutrin among others, is an atypical antidepressant primarily used to treat major depressive disorder and to support smoking cessation.[17][18] 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.[18][19] Bupropion has several features that distinguish it from other antidepressants: it does not usually cause sexual dysfunction,[18] it is not associated with weight gain[18] and sleepiness,[20] and it is more effective than SSRIs at improving symptoms of hypersomnia and fatigue.[21] 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.[22]

Common adverse effects of bupropion with the greatest difference from placebo are dry mouth, nausea, constipation, insomnia, anxiety, tremor, and excessive sweating.[23][failed verification] Raised blood pressure is notable.[24] Rare but serious side effects include seizures,[23] liver toxicity,[25] psychosis,[26] and risk of overdose.[27] Bupropion use during pregnancy may be associated with increased odds of congenital heart defects.[28]

Bupropion acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) and a nicotinic receptor antagonist.[15] However, its effects on dopamine are weak and clinical significance is contentious.[29][30][31][32][33] Chemically, bupropion is an aminoketone that belongs to the class of substituted cathinones and more generally that of substituted amphetamines and substituted phenethylamines.[1][34]

Bupropion was invented by Nariman Mehta, who worked at Burroughs Wellcome, in 1969.[35] It was first approved for medical use in the United States in 1985.[36] Bupropion was originally called by the generic name amfebutamone, before being renamed in 2000.[16] In 2021, it was the eighteenth most commonly prescribed medication in the United States, with more than 29 million prescriptions.[37][38] It is on the World Health Organization's List of Essential Medicines.[39]

  1. ^ a b "Bupropion". PubChem. United States National Library of Medicine – National Center for Biotechnology Information. 28 July 2018. Archived from the original on 29 July 2018. Retrieved 29 July 2018.
  2. ^ "Bupropion Use During Pregnancy". Drugs.com. Archived from the original on 24 December 2018. Retrieved 24 December 2018.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ "TGA eBS - Product and Consumer Medicine Information Licence". Archived from the original on 7 December 2016. Retrieved 9 January 2023.
  5. ^ Brazilian Health Regulatory Agency (Anvisa) (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 3 August 2023.
  6. ^ "Wellbutrin Product information". Health Canada. 25 April 2012. Archived from the original on 9 January 2023. Retrieved 9 January 2023.
  7. ^ "Zyban Product information". Health Canada. 25 April 2012. Archived from the original on 9 January 2023. Retrieved 9 January 2023.
  8. ^ "Zyban 150 mg prolonged release tablets - Summary of Product Characteristics (SmPC)". (emc). 21 April 2022. Archived from the original on 9 January 2023. Retrieved 9 January 2023.
  9. ^ Cite error: The named reference Wellbutrin SR FDA label was invoked but never defined (see the help page).
  10. ^ "Wellbutrin XL- bupropion hydrochloride tablet, extended release". DailyMed. 4 March 2022. Archived from the original on 9 January 2023. Retrieved 9 January 2023.
  11. ^ Cite error: The named reference Aplenzin FDA label was invoked but never defined (see the help page).
  12. ^ "Bupropion hydrochloride EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 18 August 2022. Retrieved 7 March 2023.
  13. ^ a b c "Zyban 150 mg prolonged release film-coated tablets – Summary of Product Characteristics (SPC)". electronic Medicines Compendium. GlaxoSmithKline UK. 1 August 2013. Archived from the original on 20 July 2017. Retrieved 22 October 2013.
  14. ^ Cite error: The named reference pmid27255113 was invoked but never defined (see the help page).
  15. ^ a b c d e f g h Cite error: The named reference pmid31124380 was invoked but never defined (see the help page).
  16. ^ a b World Health Organization (2000). "International nonproprietary names for pharmaceutical substances (INN) : proposed international nonproprietary names : list 83". WHO Drug Information. 14 (2). hdl:10665/58135.
  17. ^ Sweetman S (2011). Martindale: The Complete Drug Reference (37th ed.). Pharmaceutical Press. p. 402. ISBN 9780853699828.
  18. ^ a b c d Cite error: The named reference pmid27141292 was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference pmid27591914 was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference Dhillon was invoked but never defined (see the help page).
  21. ^ Cite error: The named reference pmid16848671 was invoked but never defined (see the help page).
  22. ^ Steinert T, Fröscher W (July 2018). "Epileptic Seizures Under Antidepressive Drug Treatment: Systematic Review". Pharmacopsychiatry. 51 (4): 121–135. doi:10.1055/s-0043-117962. PMID 28850959. S2CID 22436728.
  23. ^ a b Cite error: The named reference WellbutrinPI was invoked but never defined (see the help page).
  24. ^ Cite error: The named reference pmid15705013 was invoked but never defined (see the help page).
  25. ^ Cite error: The named reference pmid24362450 was invoked but never defined (see the help page).
  26. ^ Cite error: The named reference Buproprion-induced psychosis was invoked but never defined (see the help page).
  27. ^ Cite error: The named reference pmid28135844 was invoked but never defined (see the help page).
  28. ^ Cite error: The named reference pmid33354752 was invoked but never defined (see the help page).
  29. ^ Cite error: The named reference pmid33977870 was invoked but never defined (see the help page).
  30. ^ Cite error: The named reference pmid24484978 was invoked but never defined (see the help page).
  31. ^ Cite error: The named reference pmid28965364 was invoked but never defined (see the help page).
  32. ^ Cite error: The named reference DeBattista2022 was invoked but never defined (see the help page).
  33. ^ Cite error: The named reference pmid35068363 was invoked but never defined (see the help page).
  34. ^ Dye LR, Murphy C, Calello DP, Levine MD, Skolnik A (2017). Case Studies in Medical Toxicology: From the American College of Medical Toxicology. Springer. p. 85. ISBN 9783319564494. Archived from the original on 29 August 2021. Retrieved 5 June 2020.
  35. ^ Mehta NB (25 June 1974). "United States Patent 3,819,706: Meta-chloro substituted α-butylamino-propiophenones". USPTO. Archived from the original on 7 November 2017. Retrieved 2 June 2008.
  36. ^ Cite error: The named reference approvals was invoked but never defined (see the help page).
  37. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  38. ^ "Bupropion - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  39. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

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