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User:Mr. Ibrahem/Bupropion

< User:Mr. Ibrahem
Not to be confused with Buprenorphine.
Mr. Ibrahem/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
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		Medical: By mouth
Recreational: by mouth, insufflation, intravenous
Drug classAntidepressants
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding84% (bupropion), 77% (hydroxybupropion metabolite), 42% (threohydrobupropion metabolite)[3]
MetabolismLiver (mostly CYP2B6-mediated hydroxylation, but with some contributions from CYP1A2, CYP2A6, CYP2C9, CYP3A4, CYP2E1 and CYP2C19)[3][6][4][7]
Elimination half-life12–30 hours[4][5]
ExcretionKidney (87%; 0.5% unchanged), faecal (10%)[3][6][4]
Identifiers
  • (RS)-2-(tert-Butylamino)-1-(3-chlorophenyl)propan-1-one
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, sold under the brand names Wellbutrin and Zyban among others, is a medication primarily used to treat major depressive disorder and to support stopping smoking.[8] It is a moderately effective antidepressant on its own, but it is also used as an add-on medication in cases of incomplete response to first-line SSRI antidepressants.[8][10] Bupropion is taken in tablet form and is available only by prescription in industrialized countries.[8]

Common side effects include a dry mouth, difficulty sleeping, agitation, and headaches.[8] Serious side effects include an increased risk for epileptic seizures and suicide.[8] In comparison to some other antidepressants, bupropion may have a lower rate of sexual dysfunction or sleepiness and may result in weight loss.[11] It is unclear if its use during pregnancy or breastfeeding is safe.[8][2]

Bupropion is an atypical antidepressant.[12] It acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) and a nicotinic receptor antagonist.[11][13][13][14] Chemically, it is an aminoketone that belongs to the class of substituted cathinones and is similar to phenethylamines.[1][15]

Bupropion was first made by chemist Nariman Mehta in 1969, and patented by Burroughs Wellcome in 1974.[16] It was first approved for medical use in the United States in 1985.[8] It was originally called by the generic name amfebutamone, before being renamed in 2000.[17] It is on the World Health Organization's List of Essential Medicines.[18] In the United States, the wholesale cost per dose is less than US$0.50 as of 2018.[19] In 2017, it was the 23rd most commonly prescribed medication in the United States, with more than 24 million prescriptions.[20][21]

References edit

  1. ^ a b "Compound Summary". Bupropion. 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. {{cite encyclopedia}}: |work= ignored (help)
  2. ^ a b c "Bupropion Use During Pregnancy". Drugs.com. Archived from the original on 24 December 2018. Retrieved 24 December 2018.
  3. ^ 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.
  4. ^ a b c "Wellbutrin SR- bupropion hydrochloride tablet, film coated". DailyMed. 5 November 2019. Archived from the original on 4 June 2020. Retrieved 6 May 2020.
  5. ^ Brunton, L; Chabner, B; Knollman, B (2010). Goodman and Gilman's The Pharmacological Basis of Therapeutics (12th ed.). New York: McGraw-Hill Professional. ISBN 978-0-07-162442-8.[page needed]
  6. ^ a b "Prexaton Bupropion hydrochloride Product Information". TGA eBusiness Services. Ascent Pharma Pty Ltd. 2 October 2012. Archived from the original on 22 February 2017. Retrieved 22 October 2013.
  7. ^ Zhu AZ, Zhou Q, Cox LS, Ahluwalia JS, Benowitz NL, Tyndale RF (September 2014). "Gene variants in CYP2C19 are associated with altered in vivo bupropion pharmacokinetics but not bupropion-assisted smoking cessation outcomes". Drug Metabolism and Disposition. 42 (11): 1971–7. doi:10.1124/dmd.114.060285. PMC 4201132. PMID 25187485.
  8. ^ a b c d e f g h i "Bupropion Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. 5 February 2018. Archived from the original on 15 July 2018. Retrieved 15 July 2018.
  9. ^ "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 20 September 2020. Retrieved 9 September 2020.
  10. ^ Schwasinger-Schmidt, TE; Macaluso, M (8 September 2018). "Other Antidepressants". Handbook of Experimental Pharmacology. 250: 325–355. doi:10.1007/164_2018_167. ISBN 978-3-030-10948-6. PMID 30194544.
  11. ^ a b Fava M, Rush AJ, Thase ME, et al. (2005). "15 years of clinical experience with bupropion HCl: from bupropion to bupropion SR to bupropion XL". Prim Care Companion J Clin Psychiatry. 7 (3): 106–13. doi:10.4088/pcc.v07n0305. PMC 1163271. PMID 16027765.
  12. ^ Sweetman, Sean (2011). Martindale: The Complete Drug Reference (37th ed.). p. 402. ISBN 9780853699828.
  13. ^ a b Dwoskin, Linda P. (29 January 2014). Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse. Elsevier Science. pp. 177–216. ISBN 978-0-12-420177-4. Archived from the original on 4 June 2020. Retrieved 5 August 2020.
  14. ^ Tasman, Allan; Kay, Jerald; Lieberman, Jeffrey A.; First, Michael B.; Maj, Mario (11 October 2011). Psychiatry. John Wiley & Sons. ISBN 978-1-119-96540-4. Archived from the original on 8 June 2020. Retrieved 5 August 2020.
  15. ^ Dye, Leslie R.; Murphy, Christine; Calello, Diane P.; Levine, Michael D.; Skolnik, Aaron (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 August 2020.
  16. ^ 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.
  17. ^ 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.
  18. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  19. ^ "NADAC as of 2018-12-19". Centers for Medicare and Medicaid Services. Archived from the original on 19 December 2018. Retrieved 22 December 2018.
  20. ^ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
  21. ^ "Bupropion - Drug Usage Statistics". ClinCalc. 23 December 2019. Archived from the original on 8 July 2020. Retrieved 11 April 2020.
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