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Pronunciation | /bjuːˈproʊpiɒn/ bew-PROH-pee-on am-fa-BEW-teh-moan |
Trade names | Wellbutrin, Zyban, others |
Other names | Amfebutamone; 3-Chloro-N-tert-butyl-β-keto-α-methylphenethylamine; 3-Chloro-N-tert-butyl-β-ketoamphetamine; 3-Chloro-N-tert-butylcathinone |
AHFS/Drugs.com | Monograph |
MedlinePlus | a695033 |
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Routes of administration | Oral (swallowed by mouth)[2][3] |
Drug class | NDRI antidepressants |
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Pharmacokinetic data | |
Bioavailability | Unknown[2] |
Protein binding | Bupropion: 84%[14] Hydroxybupropion: 77%[14] Threohydrobupropion: 42%[14] |
Metabolism | Liver, intestines (CYP2B6, others)[2] |
Metabolites | • Hydroxybupropion • Threohydrobupropion • Erythrohydrobupropion • Others |
Elimination half-life | Bupropion: 11–21 h[15][2] Hydroxybupropion: 20 h[2] Threohydrobupropion: 37 h[2] Erythrohydrobupropion: 33 h[2] |
Excretion | Urine: 87% (0.5% unchanged)[2] Feces: 10%[2] |
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Chemical and physical data | |
Formula | C13H18ClNO |
Molar mass | 239.74 g·mol−1 |
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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] The medication is taken by mouth.[2][3]
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 likelihood of congenital heart defects.[28]
Bupropion acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) and a nicotinic receptor antagonist.[2] 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.[34][35]
Bupropion was invented by Nariman Mehta, who worked at Burroughs Wellcome, in 1969.[36] It was first approved for medical use in the United States in 1985.[37] 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.[38][39] It is on the World Health Organization's List of Essential Medicines.[40]
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