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Bupropion
Substituted cathinone medication mainly for depression and smoking cessation

Bupropion, formerly known as amfebutamone and sold under brand names like Wellbutrin, is an atypical antidepressant used to treat major depressive disorder, seasonal affective disorder, and aid smoking cessation. It acts as a norepinephrine–dopamine reuptake inhibitor and nicotinic receptor antagonist, with fewer sexual side effects and less weight gain compared to SSRIs. Common adverse effects include dry mouth, insomnia, and anxiety, but it carries a higher risk of seizures especially in susceptible individuals. First approved in 1985, it ranks among the most prescribed drugs in the US and is listed on the WHO’s Essential Medicines. The FDA also approved a dextromethorphan/bupropion combo for rapid antidepressant effects in 2022.

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Medical uses

Depression

The evidence overall supports the effectiveness of bupropion over placebo for the treatment of depression.373839 Some peer-reviewed studies suggest the quality of evidence is low.4041 Some meta-analyses report that bupropion has an at-most small effect size for depression.42434445 One meta-analysis reported a large effect size.46 However, there were methodological limitations with this meta-analysis, including using a subset of only five trials for the effect size calculation, substantial variability in effect sizes between the selected trials—which led the authors to state that their findings in this area should be interpreted with "extreme caution"—and general lack of inclusion of unpublished trials in the meta-analysis.47 Unpublished trials are more likely to be negative in findings,4849 and other meta-analyses have included unpublished trials.50515253 Evidence suggests that the effectiveness of bupropion for depression is similar to that of other antidepressants.545556

Over the autumn and winter months, bupropion prevents the development of depression in those who have recurring seasonal affective disorder: 15% of participants on bupropion experienced a major depressive episode vs. 27% of those on placebo.57 Bupropion also improves depression in bipolar disorder, with the efficacy and risk of an affective switch being similar to other antidepressants.58

Bupropion has several features that distinguish it from other antidepressants: for instance, unlike the majority of antidepressants, it does not usually cause sexual dysfunction, and the occurrence of sexual side effects is not different from placebo.5960 Bupropion treatment is not associated with weight gain; on the contrary, the majority of studies observed significant weight loss in bupropion-treated participants.61 Bupropion treatment also is not associated with the sleepiness that may be produced by other antidepressants.62 Bupropion is more effective than selective serotonin reuptake inhibitors (SSRIs) at improving symptoms of hypersomnia and fatigue in depressed patients.63 Bupropion is effective in the treatment of anxious depression and, contrary to common belief, does not exacerbate anxiety in this context.6465 The effectiveness of bupropion for anxious depression is equivalent to that of SSRIs in the case of depression with low or moderate anxiety, whereas SSRIs show a modest effectiveness advantage in terms of response rates for depression with high anxiety.66

The addition of bupropion to a prescribed SSRI is a common strategy when people do not respond to the SSRI,67 and it is supported by clinical trials;68 however, it appears to be inferior to the addition of atypical antipsychotic aripiprazole.69

Smoking cessation

Prescribed as an aid for smoking cessation, bupropion reduces the severity of craving for nicotine and withdrawal symptoms707172 such as depressed mood, irritability, difficulty concentrating, and increased appetite.73 Initially, bupropion slows the weight gain that often occurs in the first weeks after quitting smoking. With time, however, this effect becomes negligible.74

The bupropion treatment course lasts for seven to twelve weeks, with the patient halting the use of tobacco about ten days into the course.7576 After the course, the effectiveness of bupropion for maintaining abstinence from smoking declines over time, from 37% of tobacco abstinence at 3 months to 20% at one year.77 It is unclear whether extending bupropion treatment helps to prevent relapse of smoking.78

Overall, six months after the therapy, bupropion increases the likelihood of quitting smoking by approximately 1.6-fold as compared to placebo. In this respect, bupropion is as effective as nicotine replacement therapy but inferior to varenicline. Combining bupropion and nicotine replacement therapy does not improve the quitting rate.79

In children and adolescents, the use of bupropion for smoking cessation does not appear to offer any significant benefits.80 The evidence for its use to aid smoking cessation in pregnant women is insufficient.81

Attention deficit hyperactivity disorder

In the United States, the treatment of attention deficit hyperactivity disorder (ADHD) is not an approved indication of bupropion, and it is not mentioned in the 2019 guideline on ADHD treatment from the American Academy of Pediatrics.82 Systematic reviews of bupropion for the treatment of ADHD in both adults and children note that bupropion may be effective for ADHD but warn that this conclusion has to be interpreted with caution, because clinical trials were of low quality due to small sizes and risk of bias.83848586 Similarly to atomoxetine, bupropion has a delayed onset of action for ADHD, and several weeks of treatment are required for therapeutic effects.8788 This is in contrast to stimulants, such as amphetamine and methylphenidate, which have an immediate onset of effect in the condition.89

Sexual dysfunction

Bupropion is less likely than other antidepressants to cause sexual dysfunction.90 A range of studies indicate that bupropion not only produces fewer sexual side effects than other antidepressants but can actually help to alleviate sexual dysfunction91 including sexual dysfunction induced by SSRI antidepressants.92 There have also been small studies suggesting that bupropion or a bupropion/trazodone combination may improve some measures of sexual function in women who have hypoactive sexual desire disorder (HSDD) and are not depressed.93 According to an expert consensus recommendation from the International Society for the Study of Women's Sexual Health, bupropion can be considered as an off-label treatment for HSDD despite limited safety and efficacy data.94 Likewise, a 2022 systematic review and meta-analysis of bupropion for sexual desire disorder in women reported that although data were limited, bupropion appeared to be dose-dependently effective for the condition.95

Weight loss

Bupropion, when used for treating long-term weight gain over six to twelve months, results in an average weight loss of 2.7 kilograms (6.0 lb) over placebo.96 This is not much different from the weight loss produced by several other weight-loss medications such as sibutramine or orlistat.97 The combination drug naltrexone/bupropion has been approved by the US Food and Drug Administration (FDA) for the treatment of obesity.9899

Other uses

Bupropion is not effective in the treatment of cocaine dependence,100 but it is showing promise in reducing drug use in treating amphetamine-type stimulant use and cravings.101102 Based on studies indicating that bupropion lowers the level of the inflammatory mediator TNF-alpha, there have been suggestions that it might be useful in treating inflammatory bowel disease, psoriasis, and other autoimmune conditions, but very little clinical evidence is available.103104105 Bupropion is not effective in treating chronic low back pain.106 The drug may be useful in the treatment of excessive daytime sleepiness (EDS) and narcolepsy.107108109110

Bupropion has been used to treat disorders of diminished motivation, like apathy, abulia, and akinetic mutism.111112 Accordingly, the drug has been found to increase effort expenditure and improve motivational deficits in animal models.113 However, only limited benefits of bupropion in the treatment of apathy have been observed in clinical trials in various conditions.114

Bupropion has been used in the treatment of postural orthostatic tachycardia syndrome (POTS).115116

Available forms

See also: Naltrexone/bupropion and Dextromethorphan/bupropion

Bupropion is available as an oral tablet in several different formulations.117118 It is mainly formulated as the hydrochloride salt119120 but also as the hydrobromide salt.121 In addition to single-drug formulations, bupropion is formulated in combinations including naltrexone/bupropion (Contrave) for obesity and dextromethorphan/bupropion (Auvelity) for depression.122123

Contraindications

The US Food and Drug Administration (FDA) prescription label advises that bupropion should not be prescribed to individuals with epilepsy or other conditions that lower the seizure threshold, such as anorexia nervosa, bulimia nervosa, or benzodiazepine or alcohol withdrawal. It should be avoided in individuals who are taking monoamine oxidase inhibitors (MAOIs). The label recommends that caution should be exercised when treating people with liver damage, severe kidney disease, and severe hypertension, and in children, adolescents, and young adults due to the increased risk of suicidal ideation.124

Side effects

See also: List of side effects of bupropion

The common adverse effects of bupropion with the greatest difference from placebo are dry mouth, nausea, constipation, insomnia, anxiety, tremor, and excessive sweating.125126 Bupropion has the highest incidence of insomnia of all second-generation antidepressants, apart from desvenlafaxine.127 It is also associated with about 20% increased risk of headache.128

Bupropion raises blood pressure in some people. One study showed an average rise of 6 mm Hg in systolic blood pressure in 10% of patients.129 The prescribing information notes that hypertension, sometimes severe, is observed in some people taking bupropion, both with and without pre-existing hypertension.130131 The safety of bupropion in people with cardiovascular conditions and its general cardiovascular safety profile remains unclear due to the lack of data.132133

Seizure is a rare but serious adverse effect of bupropion. It is strongly dose-dependent: for the immediate release preparation, the seizure incidence is 0.4% at the dose 300–450 mg per day; the incidence climbs almost ten-fold for the higher than recommended dose of 600 mg.134135 For comparison, the incidence of unprovoked seizure in the general population is 0.07–0.09%, and the risk of seizure for a variety of other antidepressants is generally 0–0.5% at the recommended doses.136

Cases of liver toxicity leading to death or liver transplantation have been reported for bupropion. It is considered to be one of several antidepressants with a greater risk of hepatotoxicity.137

The prescribing information warns about bupropion triggering an angle-closure glaucoma attack.138 On the other hand, bupropion may decrease the risk of development of open angle glaucoma.139

Bupropion use by mothers in the first trimester of pregnancy is associated with a 23% increase in the odds of congenital heart defects in their children.140

Bupropion has rarely been associated with instances of Stevens–Johnson syndrome.141142

Bupropion has not been associated with QT prolongation at therapeutic doses but has been associated with QT prolongation in overdose.143144145

Psychiatric

The US Food and Drug Administration (FDA) requires all antidepressants, including bupropion, to carry a boxed warning stating that antidepressants may increase the risk of suicide in people younger than 25. This warning is based on a statistical analysis conducted by the FDA which found a 2-fold increase in suicidal thought and behavior in children and adolescents, and a 1.5-fold increase in the 18–24 age group.146 For this analysis the FDA combined the results of 295 trials of 11 antidepressants to obtain statistically significant results. Considered in isolation, bupropion was not statistically different from placebo.147

Bupropion prescribed for smoking cessation results in a 25% increase in the risk of psychiatric side effects, in particular, anxiety (about 40% increase) and insomnia (about 80% increase). The evidence is insufficient to determine whether bupropion is associated with suicides or suicidal behavior.148

In rare cases, bupropion-induced psychosis may develop. It is associated with higher doses of bupropion; many cases described are at higher than recommended doses. Concurrent antipsychotic medication appears to be protective.149 In most cases the psychotic symptoms are eliminated by reducing the dose, ceasing treatment or adding antipsychotic medication.150151

Although studies are lacking, a handful of case reports suggest that abrupt discontinuation of bupropion may cause antidepressant discontinuation syndrome.152

Overdose

Bupropion is considered moderately dangerous in overdose.153154 According to an analysis of US National Poison Data System, adjusted for the number of prescriptions, bupropion and venlafaxine are the two new-generation antidepressants (i.e., non-tricyclic antidepressants) that result in the highest mortality and morbidity.155 For significant overdoses, seizures have been reported in about a third of all cases; other serious effects include hallucinations, loss of consciousness, and abnormal heart rhythms. When bupropion was one of several kinds of pills taken in an overdose, fever, muscle rigidity, muscle damage, hypertension or hypotension, stupor, coma, and respiratory failure have been reported. While most people recover, some people have died, having had multiple uncontrolled seizures and myocardial infarction.156

Interactions

Since bupropion is metabolized to hydroxybupropion by the enzyme CYP2B6, drug interactions with CYP2B6 inhibitors are possible: this includes such medications as paroxetine, sertraline, norfluoxetine (active metabolite of fluoxetine), diazepam, clopidogrel, and orphenadrine. The expected result is an increase of bupropion and a decrease in hydroxybupropion blood concentration. The reverse effect (decrease of bupropion and increase of hydroxybupropion) can be expected with CYP2B6 inducers such as carbamazepine, clotrimazole, rifampicin, ritonavir, St John's wort, and phenobarbital.157 Indeed, carbamazepine decreases exposure to bupropion by 90% and increases exposure to hydroxybupropion by 94%.158 Ritonavir, lopinavir/ritonavir, and efavirenz have been shown to decrease levels of bupropion and/or its metabolites.159 Ticlopidine and clopidogrel, both potent CYP2B6 inhibitors, have been found to considerably increase bupropion levels as well as decrease levels of its metabolite hydroxybupropion.160

Bupropion and its metabolites are inhibitors of CYP2D6, with hydroxybupropion responsible for most of the inhibition. Additionally, bupropion and its metabolites may decrease the expression of CYP2D6 in the liver. The end effect is a significant slowing of the clearance of other drugs metabolized by this enzyme.161 For instance, bupropion has been found to increase area-under-the-curve of desipramine, a CYP2D6 substrate, by 5-fold.162 Bupropion has also been found to increase levels of atomoxetine by 5.1-fold, while decreasing the exposure to its main metabolite by 1.5-fold.163 As another example, the ratio of dextromethorphan (a drug that is mainly metabolized by CYP2D6) to its major metabolite dextrorphan increased approximately 35-fold when it was administered to people being treated with 300 mg/day bupropion.164 When people on bupropion are given MDMA, about 30% increase of exposure to both drugs is observed, with enhanced mood but decreased heart rate effects of MDMA.165166 Interactions with other CYP2D6 substrates, such as metoprolol, imipramine, nortriptyline,167 venlafaxine,168 and nebivolol169 have also been reported. However, in a notable exception, bupropion does not seem to affect the concentrations of CYP2D6 substrates fluoxetine and paroxetine.170171 Bupropion prevents norepinephrine and dopamine release induced by methamphetamine and has been found to reduce the subjective and sympathomimetic effects of methamphetamine in humans.172173174

Bupropion lowers the seizure threshold, and therefore can potentially interact with other medications that also lower it, such as antipsychotics, tricyclic antidepressants, theophylline, and systemic corticosteroids.175 The prescribing information recommends minimizing the use of alcohol, since in rare cases bupropion reduces alcohol tolerance.176

Caution should be observed when combining bupropion with a monoamine oxidase inhibitor (MAOI), as it may result in hypertensive crisis.177

Pharmacology

Pharmacodynamics

Bupropion binding and activity178179180
SiteValue (nM)TypeSpecies
DATTooltip Dopamine transporter173–1,800372–2,780330–2,900550–2,170KiKiIC50IC50HumanRatHumanRat
NETTooltip Norepinephrine transporter3,640–52,000940–1,900443–3,2401,400–1,900KiKiIC50IC50HumanRatHumanRat
SERTTooltip Serotonin transporter9,100–>100,0001,000–>10,00047,000–>100,00015,600KiKiIC50IC50HumanRatHumanRat
α1/1A-AdR4,200–16,000KiHuman
α2/2A-AdR>10,000–81,000KiHuman
H16,600–>10,000KiHuman
σ1580–2,100IC50Rodent
α1-nACh7,600–28,000IC50Human
α3β2-nACh1,000IC50Human
α3β4-nACh1,800IC50Human
α4β2-nACh12,000IC50Human
α4β4-nACh12,000–14,000IC50Human
α7-nACh7,900–50,000IC50Human
α/β/δ/γ-nACh7,900IC50Human
hERGTooltip human Ether-à-go-go-Related Gene34,000–69,000IC50Human
Notes: (1) Values are in nanomolar (nM) units. The smaller the value, the more avidly the drug binds to or affects the site. (2) Affinities (Ki) were >10,000 nM at a variety of other sites (5-HT1, 5-HT2, β-adrenergic, D1, D2, mACh, nACh, GABAA). More: 181182183184185186

The mechanism of action of bupropion in the treatment of depression and for other indications is unclear.187 However, it is thought to be related to the fact that bupropion is a norepinephrine–dopamine reuptake inhibitor (NDRI) and negative allosteric modulator of several nicotinic acetylcholine receptors.188 Bupropion does not act as a norepinephrine–dopamine releasing agent.189 Pharmacological actions of bupropion, to a substantial degree, are due to its active metabolites hydroxybupropion, threo-hydrobupropion, and erythro-hydrobupropion that are present in the blood plasma at comparable or much higher levels.190 In fact, bupropion could accurately be conceptualized as a prodrug of these metabolites.191 Overall action of these metabolites, and particularly one enantiomer S,S-hydroxybupropion, is also characterized by inhibition of norepinephrine and dopamine reuptake and nicotinic inhibition (see the chart on the right).192 Bupropion has no meaningful direct activity at a variety of receptors, including α- and β-adrenergic, dopamine, serotonin, histamine, and muscarinic acetylcholine receptors.193

The occupancy of dopamine transporter (DAT) by bupropion (300 mg/day) and its metabolites in the human brain as measured by several positron emission tomography (PET) studies is approximately 20%, with a mean occupancy range of about 14 to 26%.194195196197 For comparison, the NDRI methylphenidate at therapeutic doses is thought to occupy greater than 50% of DAT sites.198 In accordance with its low DAT occupancy, no measurable dopamine release in the human brain was detected with bupropion (one 150 mg dose) in a PET study.199200201202 Bupropion has also been shown to increase striatal VMAT2, though it is unknown if this effect is more pronounced than other DRIs.203 These findings raise questions about the role of dopamine reuptake inhibition in the pharmacology of bupropion, and suggest that other actions may be responsible for its therapeutic effects.204205206207 No data are available on occupancy of the norepinephrine transporter (NET) by bupropion and its metabolites.208209 However, due to the increased exposure of hydroxybupropion over bupropion itself, which has higher affinity for the NET than the DAT,210 bupropion's overall pharmacological profile in humans may end up making it effectively more of a norepinephrine reuptake inhibitor than a dopamine reuptake inhibitor.211212 Accordingly, the clinical effects of bupropion are more consistent with noradrenergic activity than with dopaminergic actions.213214

Bupropion has been claimed to be a sigma σ1 receptor agonist.215216 Its antidepressant-like effects in rodents depend on σ1 receptor activation.217218219 They are enhanced and inhibited by σ1 receptor agonists and antagonists, respectively.220221222 However, no data on the binding or functional effects of bupropion at the human sigma receptors seem to be available.223224225 In any case, bupropion has been reported to bind to rodent σ1 receptors with IC50Tooltip half-maximal inhibitory concentration values of 580 to 2,100 nM.226 In contrast to many other phenethylamines and amphetamines,227 bupropion is not an agonist of the trace amine-associated receptor 1 (TAAR1).228229230231

Bupropion has been found to have a mixture of anti-inflammatory and pro-inflammatory activity through modulation of the immune system.232233234235236237238 One such mechanism underlying these effects may be reduced levels of the pro-inflammatory cytokine tumor necrosis factor alpha (TNFα).239240241 The catecholaminergic actions of bupropion may be involved in its immunomodulatory effects.242

Pharmacology of bupropion and its metabolites
 BupropionR,R-HydroxybupropionS,S-HydroxybupropionThreo-hydrobupropionErythro-hydrobupropion
Exposure and half-life
AUC relativeto bupropion243244123.80.611.22.5
Half-life2451.04 h19 h15 h31 h22 h
Inhibition IC50 (μM) in human cells, unless noted otherwise (Lesser values indicate greater potency.)
DAT, uptake2460.66inactive0.6347 (rat)247no data
NET, uptake2481.859.90.2416 (rat)249no data
SERT, uptake250inactiveinactiveinactive67 (rat)251no data
α3β4 nicotinic2521.86.51114 (rat)253no data
α4β2 nicotinic25412313.3no datano data
α1β1γδ nicotinic2557.97.628no datano data
5-HT3A25625787 (mouse)113no datano datano data

Pharmacokinetics

After oral administration, bupropion is rapidly and completely absorbed reaching the peak blood plasma concentration after 1.5 hours (tmax). Sustained-release (SR) and extended-release (XL) formulations have been designed to slow down absorption resulting in tmax of 3 hours and 5 hours, respectively.258 Absolute bioavailability of bupropion is unknown but is presumed to be low, at 5–20%, due to the first-pass metabolism. As for the relative bioavailability of the formulations, XL formulation has lower bioavailability (68%) compared to SR formulation and immediate release bupropion.259

Bupropion is metabolized in the body by a variety of pathways. The oxidative pathways are by cytochrome P450 isoenzymes CYP2B6 leading to R,R- and S,S-hydroxybupropion and, to a lesser degree, CYP2C19 leading to 4'-hydroxybupropion. The reductive pathways are by 11β-hydroxysteroid dehydrogenase type 1 in the liver and AKR7A2/AKR7A3 in the intestine leading to threo-hydrobupropion and by yet unknown enzyme leading to erythro-hydrobupropion.260

The metabolism of bupropion is highly variable: the effective doses of bupropion received by persons who ingest the same amount of the drug may differ by as much as 5.5 times (with a half-life of 12–30 hours), while the effective doses of hydroxybupropion may differ by as much as 7.5 times (with a half-life of 15–25 hours).261262263 Based on this, some researchers have advocated monitoring of the blood level of bupropion and hydroxybupropion.264

The metabolism of bupropion also seems to follow biphasic pharmacokinetics: the redistribution alpha phase with half-life of about 1 hour265 precedes the metabolism beta phase of about 12-30 hours. This might explain why abuse is unfeasible due to a short "high", as well as support the use of extended-release formulas to maintain a consistent concentration of bupropion.

The metabolism of bupropion is highly species-dependent.266267268 As an example, oral bupropion results in hydroxybupropion levels that are 16-fold higher than those of bupropion itself in humans, whereas in rats, oral bupropion results in levels of bupropion that are 3.4-fold higher than those of hydroxybupropion.269 The species-dependent metabolism of bupropion is thought to be involved in species differences in its pharmacodynamic effects.270271272 For example, bupropion produces psychostimulant-like and reinforcing effects in rodents, whereas oral bupropion at therapeutic doses seems to have much less or no potential for such effects in humans.273

Chemistry

Bupropion is an aminoketone that belongs to the class of substituted cathinones and the more general class of substituted phenethylamines.274275 It is also known structurally as 3-chloro-N-tert-butyl-β-keto-α-methylphenethylamine, 3-chloro-N-tert-butyl-β-ketoamphetamine, or 3-chloro-N-tert-butylcathinone. The clinically used bupropion is racemic, which is a mixture of two enantiomers: S-bupropion and R-bupropion. Although the optical isomers on bupropion can be separated, they rapidly racemize under physiological conditions.276277

Bupropion is a small-molecule compound with the molecular formula C13H18ClNO and a molecular weight of 239.74 g/mol.278279 It is a highly lipophilic compound,280 with an experimental log P of 3.6.281282 Pharmaceutically, bupropion is used mainly as the hydrochloride salt but also to a lesser extent as the hydrobromide salt.283284285

A number of analogues of bupropion exist, such as hydroxybupropion, radafaxine, and manifaxine, among others.286 These compounds are norepinephrine–dopamine reuptake inhibitors (NDRIs) similarly to bupropion.287 The analogues of bupropion with the N-tert-butyl group removed or replaced with an N-methyl group, 3-chlorocathinone (3-CC) and 3-chloromethcathinone (3-CMC; clophedrone), respectively, are potent serotonin–norepinephrine–dopamine releasing agents (SNDRAs).288289290 They have been encountered as cathinone designer and recreational drugs.291292 The analogue of bupropion with the N-tert-butyl group replaced with an N-cyclopropyl group is 3-chloro-N-cyclopropylcathinone (3Cl-CpC; PAL-433, RTI-6037-39).293294295 It is a hybrid serotonin releasing agent (SRA) and serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI) and was being investigated for potential treatment of cocaine dependence.296297298

There have been reported cases of false-positive urine amphetamine tests in persons taking bupropion.299300301

Synthesis

It is synthesized in two chemical steps starting from 3'-chloro-propiophenone. The alpha position adjacent to the ketone is first brominated followed by nucleophilic displacement of the resulting alpha-bromoketone with t-butylamine and treated with hydrochloric acid to give bupropion as the hydrochloride salt in 75–85% overall yield.302303

3'-chloro-propiophenone3'-chloro-2-bromopropiophenonebupropion hydrochlorideThis diagram shows the synthesis of bupropion via 3'-chloro-propiophenone.

History

Bupropion was invented by Nariman Mehta of Burroughs Wellcome (now GlaxoSmithKline) in 1969, and the US patent for it was granted in 1974.304 It was approved by the US Food and Drug Administration (FDA) as an antidepressant on 30 December 1985, and marketed under the name Wellbutrin.305306 However, a significant incidence of seizures at the originally recommended dosage (400–600 mg/day) caused the withdrawal of the drug in 1986. Subsequently, the risk of seizures was found to be highly dose-dependent, and bupropion was re-introduced to the market in 1989 with a lower maximum recommended daily dose of 450 mg/day.307

In 1996, the US Food and Drug Administration (FDA) approved a sustained-release formulation of alcohol-resistant bupropion called Wellbutrin SR, a tablet intended to be taken twice a day (as compared with three times a day for immediate-release Wellbutrin).308 In 2003, the FDA approved another sustained-release formulation called Wellbutrin XL, a hard-shelled tablet intended for once-daily dosing.309 Wellbutrin SR and XL are available in generic form in the United States and Canada. In 1997, bupropion was approved by the FDA for use as a smoking cessation aid under the name Zyban.310311 In 2006, Wellbutrin XL was similarly approved as a treatment for seasonal affective disorder.312313

In October 2007, two providers of consumer information on nutritional products and supplements, ConsumerLab.com and The People's Pharmacy, released the results of comparative tests of different brands of bupropion.314 The People's Pharmacy received multiple reports of increased side effects and decreased efficacy of generic bupropion, which prompted it to ask ConsumerLab.com to test the products in question. The tests showed that "one of a few generic versions of Wellbutrin XL 300 mg, sold as Budeprion XL 300 mg, didn't perform the same as the brand-name pill in the lab."315 The FDA investigated these complaints and concluded that Budeprion XL is equivalent to Wellbutrin XL in regard to bioavailability of bupropion and its main active metabolite hydroxybupropion. The FDA also said that coincidental natural mood variation is the most likely explanation for the apparent worsening of depression after the switch from Wellbutrin XL to Budeprion XL.316 On 3 October 2012, however, the FDA reversed this opinion, announcing that "Budeprion XL 300 mg fails to demonstrate therapeutic equivalence to Wellbutrin XL 300 mg."317 The FDA did not test the bioequivalence of any of the other generic versions of Wellbutrin XL 300 mg, but requested that the four manufacturers submit data on this question to the FDA by March 2013.318 As of October 2013[update] the FDA has made determinations on the formulations from some manufacturers not being bioequivalent.319

In April 2008, the FDA approved a formulation of bupropion as a hydrobromide salt instead of a hydrochloride salt, to be sold under the name Aplenzin by Sanofi-Aventis. It is an extended-release tablet intended for once-daily use.320321322 It was approved on the basis of bioequivalence with Wellbutrin XL.323

In 2009, the FDA issued a health advisory warning that the prescription of bupropion for smoking cessation has been associated with reports of unusual behavior changes, agitation, and hostility. Some people, according to the advisory, have become depressed or have had their depression worsen, have had thoughts about suicide or dying, or have attempted suicide.324 This advisory was based on a review of anti-smoking products that identified 75 reports of "suicidal adverse events" for bupropion over ten years.325 Based on the results of follow-up trials this warning was removed in 2016.326

In 2012, the US Justice Department announced that GlaxoSmithKline had agreed to plead guilty and pay a $3 billion fine, in part for promoting the unapproved use of Wellbutrin for weight loss and sexual dysfunction.327

In 2017, the European Medicines Agency (EMA) recommended suspending a number of nationally approved medicines due to misrepresentation of bioequivalence study data by Micro Therapeutic Research Labs in India.328 The products recommended for suspension included several 300 mg modified-release bupropion tablets.329

Following EMA's call for an industry-wide review of medicines for the possible presence of nitrosamines,330 GlaxoSmithKline paused batch release and distribution of bupropion 150 mg tablets in November 2022. In July 2023, EMA raised the acceptable daily intake of nitrosamine impurities, leading GlaxoSmithKline to announce that distribution of bupropion 150 mg tablets would resume "across the EU and Europe" by the end of 2023.331

Society and culture

Recreational use

Recreational use of bupropion is uncommon.332 While bupropion demonstrates some potential for recreational use, this potential is less than that of other commonly used stimulants, being limited by features of its pharmacology.333 Case reports describe the recreational use of bupropion as producing a "high" similar to cocaine or amphetamine usage but with less intensity. There have been some anecdotal and case-study reports of bupropion abuse, but the bulk of evidence indicates that the subjective effects of bupropion when taken orally are markedly different from those of addictive stimulants such as cocaine or amphetamine.334 However, bupropion, by non-conventional routes of administration like injection or insufflation, has been reported to be used recreationally in the United States and Canada, notably in prisons.335336337338

Legal status

In Russia bupropion is banned as a narcotic drug, due to it being a derivative of methcathinone.339 In Australia, France, and the UK, smoking cessation is the only licensed use of bupropion, and no generics are marketed.340341342

Brand names

Brand names include Wellbutrin,343344 Aplenzin,345 Budeprion, Buproban, buprapan, Forfivo, Voxra, Zyban,346 Bupron, Bupisure, Bupep, Smoquite, Elontril, Oribion and Buxon.

Research

Bupropion has been studied limitedly in the treatment of social anxiety disorder.347348349

See also

References

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