| Pharmaceutical Information |
| Drug Name |
Bupropion hydrobromide |
| Drug ID |
BADD_D00313 |
| Description |
Bupropion (also known as the brand name product Wellbutrin®) is a norepinephrine/dopamine-reuptake inhibitor (NDRI) used most commonly for the management of Major Depressive Disorder (MDD), Seasonal Affective Disorder (SAD), and as an aid for smoking cessation. Bupropion exerts its pharmacological effects by weakly inhibiting the enzymes involved in the uptake of the neurotransmitters norepinephrine and dopamine from the synaptic cleft, therefore prolonging their duration of action within the neuronal synapse and the downstream effects of these neurotransmitters. More specifically, bupropion binds to the norepinephrine transporter (NET) and the dopamine transporter (DAT).[A6399,A178810]
Bupropion was originally classified as an "atypical" antidepressant because it does not exert the same effects as the classical antidepressants such as Monoamine Oxidase Inhibitors (MAOIs), Tricyclic Antidepressants (TCAs), or Selective Serotonin Reuptake Inhibitors (SSRIs). While it has comparable effectiveness to typical first-line options for the treatment of depression such as SSRIs,[A178798,A178804] bupropion is a unique option for the treatment of MDD as it lacks any clinically relevant serotonergic effects, typical of other mood medications, or any effects on histamine or adrenaline receptors.[A6399,A198804] Lack of activity at these receptors results in a more tolerable side effect profile; bupropion is less likely to cause sexual side effects, sedation, or weight gain as compared to SSRIs or TCAs, for example.[A178804,A178807]
When used as an aid to smoking cessation, bupropion is thought to confer its anti-craving and anti-withdrawal effects by inhibiting dopamine reuptake, which is thought to be involved in the reward pathways associated with nicotine, and through the antagonism of the nicotinic acetylcholinergic receptor.[A178825,A1966,A16508] A Cochrane Review of meta-analyses of available treatment modalities for smoking cessation found that abstinence rates approximately doubled when bupropion was used as compared to placebo, and was found to have similar rates of smoking cessation as [nicotine] replacement therapy (NRT).[A178816]
Bupropion is sometimes used as an add-on agent to first-line treatments of depression such as selective serotonin reuptake inhibitor (SSRI) medications when there is a treatment-failure or only partial response.[A178789] Bupropion is also used off-label for the management of Attention/Deficit-Hyperactivity Disorder (ADHD) in adults with comorbid bipolar depression to avoid mood destabilization caused by typical stimulant medications used for the treatment of ADHD.[F4624]
When used in combination with [naltrexone] in the marketed product ContraveⓇ for chronic weight management, the two components are thought to have effects on areas of the brain involved in the regulation of food intake. This includes the hypothalamus, which is involved in appetite regulation, and the mesolimbic dopamine circuit, which is involved in reward pathways.[L6562] Studies have shown that the combined activity of bupropion and [naltrexone] increase the firing rate of hypothalamic pro-opiomelanocortin (POMC) neurons and blockade of opioid receptor-mediated POMC auto-inhibition, which are associated with a reduction in food intake and increased energy expenditure.[L6562,A179038,A179050] The combination of naltrexone and bupropion was shown to result in a statistically significant weight loss, with a mean change in body weight of -6.3% compared to -1.3% for placebo.[A179047] |
| Indications and Usage |
Bupropion is indicated for the treatment of major depressive disorder (MDD), seasonal affective disorder (SAD), and as an aid to smoking cessation.
When used in combination with [naltrexone] as the marketed product ContraveⓇ, bupropion is indicated as an adjunct to a reduced-calorie diet and increased physical activity for chronic weight management in adults with an initial body mass index (BMI) of: 30 kg/m^2 or greater (obese) or 27 kg/m^2 or greater (overweight) in the presence of at least one weight-related comorbid condition (e.g., hypertension, type 2 diabetes mellitus, or dyslipidemia).
Bupropion is also used off-label as a first-line treatment in patients with ADHD and comorbid bipolar disorder when used as an adjunct to mood stabilizers.[F4624] |
| Marketing Status |
approved |
| ATC Code |
N06AX12 |
| DrugBank ID |
DB01156
|
| KEGG ID |
D07938
|
| MeSH ID |
D016642
|
| PubChem ID |
11984562
|
| TTD Drug ID |
D0X4ZR
|
| NDC Product Code |
0187-5812; 0187-5811; 66651-929; 65372-1166; 0187-5810; 12666-0006; 66651-930 |
| UNII |
E70G3G5863
|
| Synonyms |
Bupropion | Amfebutamone | (+-)-1-(3-Chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone | Wellbutrin | Zyban (Anti-Smoking) | Zyban (Bupropion) | Bupropion, (+-)-Isomer | Bupropion Hydrochloride | Bupropion Hydrochloride, (+-)-Isomer | Quomen | Zyntabac |
|
| Chemical Information |
| Molecular Formula |
C13H19BrClNO |
| CAS Registry Number |
905818-69-1 |
| SMILES |
CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C.Br |
| Chemical Structure |
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| ADRs Induced by Drug |
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