User:Mr. Ibrahem/Bupropion
From Wikipedia, the free encyclopedia
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][9] Bupropion is taken in tablet form and is available only by prescription in industrialized countries.[8]
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Pronunciation | /bjuːˈproʊpiɒn/ bew-PROH-pee-on |
Trade names | Wellbutrin, Zyban, others |
Other names | Amfebutamone; 3-Chloro-N-tert-butyl-β-keto-α-methylphenethylamine; 3- Chloro-N-tert-butyl-β-ketoamphetamine; Bupropion hydrochloride[1] |
AHFS/Drugs.com | Monograph |
MedlinePlus | a695033 |
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Routes of administration | Medical: By mouth Recreational: by mouth, insufflation, intravenous |
Drug class | Antidepressants |
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Protein binding | 84% (bupropion), 77% (hydroxybupropion metabolite), 42% (threohydrobupropion metabolite)[3] |
Metabolism | Liver (mostly CYP2B6-mediated hydroxylation, but with some contributions from CYP1A2, CYP2A6, CYP2C9, CYP3A4, CYP2E1 and CYP2C19)[3][4][5][6] |
Elimination half-life | 12–30 hours[5][7] |
Excretion | Kidney (87%; 0.5% unchanged), faecal (10%)[3][4][5] |
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Formula | C13H18ClNO |
Molar mass | 239.74 g·mol−1 |
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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.[10] It is unclear if its use during pregnancy or breastfeeding is safe.[8][2]
Bupropion is an atypical antidepressant.[11] It acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) and a nicotinic receptor antagonist.[10][12][12][13] Chemically, it is an aminoketone that belongs to the class of substituted cathinones and is similar to phenethylamines.[1][14]
Bupropion was first made by chemist Nariman Mehta in 1969, and patented by Burroughs Wellcome in 1974.[15] 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.[16] It is on the World Health Organization's List of Essential Medicines.[17] In the United States, the wholesale cost per dose is less than US$0.50 as of 2018[update].[18] In 2017, it was the 23rd most commonly prescribed medication in the United States, with more than 24 million prescriptions.[19][20]