Bupropion
Identification
- Summary
Bupropion is a norepinephrine and dopamine reuptake inhibitor used in the treatment of major depressive disorder (MDD), seasonal affective disorder (SAD), and as an aid to smoking cessation.
- Brand Names
- Aplenzin, Auvelity, Budeprion, Contrave, Forfivo, Wellbutrin, Zyban
- Generic Name
- Bupropion
- DrugBank Accession Number
- DB01156
- Background
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).8,12
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,9,10 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.8,16 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.10,11
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.15,1,14 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).13
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.7 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.28
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.24 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.24,20,22 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.21
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 239.741
Monoisotopic: 239.10769191 - Chemical Formula
- C13H18ClNO
- Synonyms
- Amfebutamone
- Bupropion
- External IDs
- 34841-39-9
Pharmacology
- Indication
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.28
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Attention deficit/hyperactivity disorder (adhd) ••• ••••• ••••• Treatment of Major depressive disorder •••••••••••• Used in combination to treat Major depressive disorder (mdd) Combination Product in combination with: Dextromethorphan (DB00514) •••••••••••• ••••••••••• ••••••••• ••••••• •••••••• ••••••• Used in combination to treat Obesity Combination Product in combination with: Naltrexone (DB00704) •••••••••••• Prevention of Seasonal affective disorder •••••••••••• ••••••• •••••••• •••••••• ••••••• •••• ••••••• •••••••• ••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Bupropion is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitors, or other known antidepressant agents. Compared to classical tricyclic antidepressants, Bupropion is a relatively weak inhibitor of the neuronal uptake of norepinephrine and dopamine. In addition, Bupropion does not inhibit monoamine oxidase. Bupropion has been found to be essentially inactive at the serotonin transporter (SERT)(IC50 >10 000 nM),12 however both bupropion and its primary metabolite hydroxybupropion have been found to block the function of cation-selective serotonin type 3A receptors (5-HT3ARs).
Bupropion produces dose-related central nervous system (CNS) stimulant effects in animals, as evidenced by increased locomotor activity, increased rates of responding in various schedule-controlled operant behaviour tasks, and, at high doses, induction of mild stereotyped behaviour Label. Due to these stimulant effects and selective activity at dopamine and norepinephrine receptors, bupropion has been identified as having an abuse potential.Label,17 Bupropion has a similar structure to the controlled substance Cathinone, and has been identified as having mild amphetamine-like activity, particularly when inhaled or injected.17
Bupropion is also known to lower the seizure threshold, making any pre-existing seizure conditions a contraindication to its use. This risk is exacerbated when bupropion is combined with other drugs or substances that lower the seizure threshold, such as cocaine, or in clinical situations that would increase the risk of a seizure such as abrupt alcohol or benzodiazepine withdrawal.Label As norepinephrine has been shown to have anticonvulsant properties, bupropion's inhibitory effects on NET are thought to contribute to its pro-convulsant activity.17
Bupropion has been shown to increase blood pressure and pose a risk for exacerbation of unmanaged or pre-existing hypertension,18,Label however, clinical trials of bupropion in smokers with CVD have not identified an increased incidence of CV events including stroke or heart attack.19 In clinical trials, the mean increase in systolic blood pressure associated with the use of bupropion was found to be 1.3 mmHg.Label
- Mechanism of action
Bupropion is a norepinephrine/dopamine-reuptake inhibitor (NDRI) that 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).8,12
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,9,10 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.8,16 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.10,11
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 (AChR), thereby blunting the effects of nicotine.15,1,14 Furthermore, the stimulatory effects produced by bupropion in the central nervous system are similar to nicotine's effects, making low doses of bupropion a suitable option as a nicotine substitute.23
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.24 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.24,20,22 This combination was also found to reduce food intake when injected directly into the ventral tegmental area of the mesolimbic circuit in mice, which is an area associated with the regulation of reward pathways.24
Target Actions Organism ASodium-dependent dopamine transporter inhibitorHumans ASodium-dependent noradrenaline transporter inhibitorHumans UNeuronal acetylcholine receptor subunit alpha-3 antagonistHumans U5-hydroxytryptamine receptor 3A negative modulatorHumans - Absorption
Bupropion is currently available in 3 distinct, but bioequivalent formulations: immediate release (IR), sustained-release (SR), and extended-release (XL).
Immediate Release Formulation In humans, following oral administration of bupropion hydrochloride tablets, peak plasma bupropion concentrations are usually achieved within 2 hours. IR formulations provide a short duration of action and are therefore generally dosed three times per day.
Sustained Release Formulation In humans, following oral administration of bupropion hydrochloride sustained-release tablets (SR), peak plasma concentration (Cmax) of bupropion is usually achieved within 3 hours. SR formulations provide a 12-hour extended release of medication and are therefore generally dosed twice per day.
Extended Release Formulation Following single oral administration of bupropion hydrochloride extended-release tablets (XL) to healthy volunteers, the median time to peak plasma concentrations for bupropion was approximately 5 hours. The presence of food did not affect the peak concentration or area under the curve of bupropion. XL formulations provide a 24-hour extended release of medication and are therefore generally dosed once per day/
In a trial comparing chronic dosing with bupropion hydrochloride extended-release tablets (SR) 150 mg twice daily to bupropion immediate-release formulation 100 mg 3 times daily, the steady state Cmax for bupropion after bupropion hydrochloride sustained-release tablets (SR) administration was approximately 85% of those achieved after bupropion immediate-release formulation administration. Exposure (AUC) to bupropion was equivalent for both formulations. Bioequivalence was also demonstrated for all three major active metabolites (i.e., hydroxybupropion, threohydrobupropion and erythrohydrobupropion) for both Cmax and AUC. Thus, at steady state, bupropion hydrochloride sustained-release tablets (SR) given twice daily, and the immediate-release formulation of bupropion given 3 times daily, are essentially bioequivalent for both bupropion and the 3 quantitatively important metabolites.Label
Furthermore, in a study comparing 14-day dosing with bupropion hydrochloride extended-release tablets (XL), 300 mg once-daily to the immediate-release formulation of bupropion at 100 mg 3 times daily, equivalence was demonstrated for peak plasma concentration and area under the curve for bupropion and the three metabolites (hydroxybupropion, threohydrobupropion, and erythrohydrobupropion). Additionally, in a study comparing 14-day dosing with bupropion hydrochloride extended-release tablets (XL) 300 mg once daily to the sustained-release formulation of bupropion at 150 mg 2 times daily, equivalence was demonstrated for peak plasma concentration and area under the curve for bupropion and the three metabolites.Label
Bupropion hydrochloride extended-release tablets (SR) can be taken with or without food. Bupropion Cmax and AUC were increased by 11% to 35% and 16% to 19%, respectively, when bupropion hydrochloride extended-release tablets (SR) was administered with food to healthy volunteers in three trials. The food effect is not considered clinically significant.Label
Following a single-dose administration of bupropion hydrochloride extended-release tablets (SR) in humans, Cmax of bupropion's metabolite hydroxybupropion occurs approximately 6 hours post-dose and is approximately 10 times the peak level of the parent drug at steady state. The elimination half-life of hydroxybupropion is approximately 20 (±5) hours and its AUC at steady state is about 17 times that of bupropion. The times to peak concentrations for the erythrohydrobupropion and threohydrobupropion metabolites are similar to that of the hydroxybupropion metabolite. However, their elimination half-lives are longer, 33(±10) and 37 (±13) hours, respectively, and steady-state AUCs are 1.5 and 7 times that of bupropion, respectively.Label
- Volume of distribution
Not Available
- Protein binding
In vitro tests show that bupropion is 84% bound to human plasma proteins at concentrations up to 200 mcg per mL. The extent of protein binding of the hydroxybupropion metabolite is similar to that for bupropion, whereas the extent of protein binding of the threohydrobupropion metabolite is about half that seen with bupropion.Label
- Metabolism
Bupropion is extensively metabolized in humans. Three metabolites are active: hydroxybupropion, which is formed via hydroxylation of the tert-butyl group of bupropion, and the amino-alcohol isomers, threohydrobupropion and erythrohydrobupropion, which are formed via reduction of the carbonyl group. In vitro findings suggest that CYP2B6 is the principal isoenzyme involved in the formation of hydroxybupropion, while cytochrome P450 enzymes are not involved in the formation of threohydrobupropion. Hydroxybupropion has been shown to have the same affinity as bupropion for the norepinephrine transporter (NET) but approximately 50% of its antidepressant activity despite reaching concentrations of ~10-fold higher than that of the parent drug.23
Oxidation of the bupropion side chain results in the formation of a glycine conjugate of meta-chlorobenzoic acid, which is then excreted as the major urinary metabolite. The potency and toxicity of the metabolites relative to bupropion have not been fully characterized. However, it has been demonstrated in an antidepressant screening test in mice that hydroxybupropion is one-half as potent as bupropion, while threohydrobupropion and erythrohydrobupropion are 5-fold less potent than bupropion. This may be of clinical importance because the plasma concentrations of the metabolites are as high as or higher than those of bupropion.Label
Bupropion and its metabolites exhibit linear kinetics following chronic administration of 300 to 450 mg per day.
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- Route of elimination
Bupropion is extensively metabolized in humans. Oxidation of the bupropion side chain results in the formation of a glycine conjugate of metachlorobenzoic acid, which is then excreted as the major urinary metabolite. Following oral administration of 200 mg of 14C-bupropion in humans, 87% and 10% of the radioactive dose were recovered in the urine and feces, respectively. However, the fraction of the oral dose of bupropion excreted unchanged was only 0.5%, a finding consistent with the extensive metabolism of bupropion.
- Half-life
24 hours
- Clearance
Not Available
- Adverse Effects
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- Toxicity
Symptoms of overdose include seizures, hallucinations, loss of consciousness, tachycardia, and cardiac arrest.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details D(2) dopamine receptor --- (C;C) C Allele, homozygous Effect Directly Studied The presence of this genotype in DRD2 is associated with improved therapeutic response to bupropion. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Bupropion is combined with 1,2-Benzodiazepine. Abacavir Abacavir may decrease the excretion rate of Bupropion which could result in a higher serum level. Abametapir The serum concentration of Bupropion can be increased when it is combined with Abametapir. Abatacept The metabolism of Bupropion can be increased when combined with Abatacept. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Bupropion. - Food Interactions
- Avoid alcohol. Co-administration with alcohol may result in neuropsychiatric adverse effects and potentiation of CNS depressant effects.
- Take with or without food. Co-administration with food does not significantly affect pharmacokinetics.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Bupropion hydrobromide E70G3G5863 905818-69-1 WSTCENNATOVXKQ-UHFFFAOYSA-N Bupropion hydrochloride ZG7E5POY8O 31677-93-7 HEYVINCGKDONRU-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Elontril / Forfivo / Prexaton / Voxra
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aplenzin Tablet, extended release 522 mg/1 Oral sanofi-aventis U.S. LLC 2009-03-30 2017-03-31 US Aplenzin Tablet, extended release 522 mg/1 Oral Bausch Health US, LLC 2008-04-23 Not applicable US Aplenzin Tablet, extended release 348 mg/1 Oral sanofi-aventis U.S. LLC 2009-03-30 2017-03-31 US Aplenzin Tablet, extended release 348 mg/1 Oral Bausch Health US, LLC 2008-04-23 Not applicable US Aplenzin Tablet, extended release 174 mg/1 Oral sanofi-aventis U.S. LLC 2009-03-30 2017-03-31 US - Generic Prescription Products
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Auvelity Bupropion hydrochloride (105 mg/1) + Dextromethorphan hydrobromide monohydrate (45 mg/1) Tablet, multilayer, extended release Oral Axsome Therapeutics, Inc. 2022-08-18 Not applicable US Contrave Bupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1) Tablet, film coated, extended release Oral Takeda Pharmaceuticals America, Inc. 2014-09-10 2019-08-15 US Contrave Bupropion hydrochloride (90 mg) + Naltrexone hydrochloride (8 mg) Tablet, extended release Oral Bausch Health, Canada Inc. 2018-03-16 Not applicable Canada Contrave Bupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1) Tablet, film coated, extended release Oral A-S Medication Solutions 2014-09-10 2018-09-30 US Contrave Extended-Release Bupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1) Tablet, extended release Oral Nalpropion Pharmaceuticals LLC 2014-10-22 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Appbutamone Bupropion hydrochloride (75 mg/1) + Tyrosine (100 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US Appbutamone-D Bupropion hydrochloride (75 mg/1) + Tyrosine (100 mg/1) Kit Oral Physician Therapeutics Llc 2011-07-07 Not applicable US
Categories
- ATC Codes
- A08AA62 — Bupropion and naltrexone
- A08AA — Centrally acting antiobesity products
- A08A — ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
- A08 — ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Agents that reduce seizure threshold
- Aminoketone Antidepressants
- Antidepressive Agents
- Antidepressive Agents Indicated for Depression
- Antiobesity Preparations, Excl. Diet Products
- Central Nervous System Agents
- Central Nervous System Depressants
- Centrally Acting Antiobesity Products
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strong)
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dopamine Agents
- Dopamine And Norepinephrine Reuptake Inhibitors
- Dopamine Uptake Inhibitors
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Increased Dopamine Activity
- Increased Norepinephrine Activity
- Ketones
- Miscellaneous Antidepressants
- Nervous System
- Neurotransmitter Uptake Inhibitors
- Norepinephrine Uptake Inhibitors
- OCT2 Inhibitors
- Photosensitizing Agents
- Psychoanaleptics
- Psychotropic Drugs
- Smoking Cessation Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbonyl compounds
- Direct Parent
- Alkyl-phenylketones
- Alternative Parents
- Phenylpropanes / Benzoyl derivatives / Aryl alkyl ketones / Chlorobenzenes / Aryl chlorides / Alpha-amino ketones / Dialkylamines / Organopnictogen compounds / Organochlorides / Organic oxides show 1 more
- Substituents
- Alkyl-phenylketone / Alpha-aminoketone / Amine / Aromatic homomonocyclic compound / Aryl alkyl ketone / Aryl chloride / Aryl halide / Benzenoid / Benzoyl / Chlorobenzene show 12 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- secondary amino compound, monochlorobenzenes, propanone, aromatic ketone (CHEBI:3219)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 01ZG3TPX31
- CAS number
- 34911-55-2
- InChI Key
- SNPPWIUOZRMYNY-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
- SMILES
- CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1
References
- Synthesis Reference
Shalabi AR, Walther D, Baumann MH, Glennon RA: Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release. ACS Chem Neurosci. 2017 Jun 21;8(6):1397-1403. doi: 10.1021/acschemneuro.7b00055. Epub 2017 Feb 27. [PubMed:28220701]
US3819706- General References
- Fryer JD, Lukas RJ: Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J Pharmacol Exp Ther. 1999 Jan;288(1):88-92. [Article]
- Fava M, Rush AJ, Thase ME, Clayton A, Stahl SM, Pradko JF, Johnston JA: 15 years of clinical experience with bupropion HCl: from bupropion to bupropion SR to bupropion XL. Prim Care Companion J Clin Psychiatry. 2005;7(3):106-13. [Article]
- Thase ME, Haight BR, Richard N, Rockett CB, Mitton M, Modell JG, VanMeter S, Harriett AE, Wang Y: Remission rates following antidepressant therapy with bupropion or selective serotonin reuptake inhibitors: a meta-analysis of original data from 7 randomized controlled trials. J Clin Psychiatry. 2005 Aug;66(8):974-81. [Article]
- Authors unspecified: Annual report on the results of treatment in gynecological cancer. Twenty-first volume. Statements of results obtained in patients treated in 1982 to 1986, inclusive 3 and 5-year survival up to 1990. Int J Gynaecol Obstet. 1991 Sep;36 Suppl:1-315. [Article]
- Thase ME, Clayton AH, Haight BR, Thompson AH, Modell JG, Johnston JA: A double-blind comparison between bupropion XL and venlafaxine XR: sexual functioning, antidepressant efficacy, and tolerability. J Clin Psychopharmacol. 2006 Oct;26(5):482-8. [Article]
- Richter T, Schwab M, Eichelbaum M, Zanger UM: Inhibition of human CYP2B6 by N,N',N''-triethylenethiophosphoramide is irreversible and mechanism-based. Biochem Pharmacol. 2005 Feb 1;69(3):517-24. doi: 10.1016/j.bcp.2004.10.008. Epub 2004 Dec 15. [Article]
- Trivedi MH, Fava M, Wisniewski SR, Thase ME, Quitkin F, Warden D, Ritz L, Nierenberg AA, Lebowitz BD, Biggs MM, Luther JF, Shores-Wilson K, Rush AJ: Medication augmentation after the failure of SSRIs for depression. N Engl J Med. 2006 Mar 23;354(12):1243-52. doi: 10.1056/NEJMoa052964. [Article]
- Stahl SM, Pradko JF, Haight BR, Modell JG, Rockett CB, Learned-Coughlin S: A Review of the Neuropharmacology of Bupropion, a Dual Norepinephrine and Dopamine Reuptake Inhibitor. Prim Care Companion J Clin Psychiatry. 2004;6(4):159-166. [Article]
- John Rush A, Jain SB: Clinical Implications of the STAR*D Trial. Handb Exp Pharmacol. 2018 Sep 11. doi: 10.1007/164_2018_153. [Article]
- Patel K, Allen S, Haque MN, Angelescu I, Baumeister D, Tracy DK: Bupropion: a systematic review and meta-analysis of effectiveness as an antidepressant. Ther Adv Psychopharmacol. 2016 Apr;6(2):99-144. doi: 10.1177/2045125316629071. Epub 2016 Feb 18. [Article]
- Ashton AK, Rosen RC: Bupropion as an antidote for serotonin reuptake inhibitor-induced sexual dysfunction. J Clin Psychiatry. 1998 Mar;59(3):112-5. [Article]
- Shalabi AR, Walther D, Baumann MH, Glennon RA: Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release. ACS Chem Neurosci. 2017 Jun 21;8(6):1397-1403. doi: 10.1021/acschemneuro.7b00055. Epub 2017 Feb 27. [Article]
- Cahill K, Stevens S, Perera R, Lancaster T: Pharmacological interventions for smoking cessation: an overview and network meta-analysis. Cochrane Database Syst Rev. 2013 May 31;(5):CD009329. doi: 10.1002/14651858.CD009329.pub2. [Article]
- Slemmer JE, Martin BR, Damaj MI: Bupropion is a nicotinic antagonist. J Pharmacol Exp Ther. 2000 Oct;295(1):321-7. [Article]
- Johnston AJ, Ascher J, Leadbetter R, Schmith VD, Patel DK, Durcan M, Bentley B: Pharmacokinetic optimisation of sustained-release bupropion for smoking cessation. Drugs. 2002;62 Suppl 2:11-24. doi: 10.2165/00003495-200262002-00002. [Article]
- Pandhare A, Pappu AS, Wilms H, Blanton MP, Jansen M: The antidepressant bupropion is a negative allosteric modulator of serotonin type 3A receptors. Neuropharmacology. 2017 Feb;113(Pt A):89-99. doi: 10.1016/j.neuropharm.2016.09.021. Epub 2016 Sep 24. [Article]
- Ahern TH, Javors MA, Eagles DA, Martillotti J, Mitchell HA, Liles LC, Weinshenker D: The effects of chronic norepinephrine transporter inactivation on seizure susceptibility in mice. Neuropsychopharmacology. 2006 Apr;31(4):730-8. doi: 10.1038/sj.npp.1300847. [Article]
- Roose SP, Dalack GW, Glassman AH, Woodring S, Walsh BT, Giardina EG: Cardiovascular effects of bupropion in depressed patients with heart disease. Am J Psychiatry. 1991 Apr;148(4):512-6. doi: 10.1176/ajp.148.4.512. [Article]
- Benowitz NL, Pipe A, West R, Hays JT, Tonstad S, McRae T, Lawrence D, St Aubin L, Anthenelli RM: Cardiovascular Safety of Varenicline, Bupropion, and Nicotine Patch in Smokers: A Randomized Clinical Trial. JAMA Intern Med. 2018 May 1;178(5):622-631. doi: 10.1001/jamainternmed.2018.0397. [Article]
- Wang GJ, Tomasi D, Volkow ND, Wang R, Telang F, Caparelli EC, Dunayevich E: Effect of combined naltrexone and bupropion therapy on the brain's reactivity to food cues. Int J Obes (Lond). 2014 May;38(5):682-8. doi: 10.1038/ijo.2013.145. Epub 2013 Aug 8. [Article]
- Greenway FL, Fujioka K, Plodkowski RA, Mudaliar S, Guttadauria M, Erickson J, Kim DD, Dunayevich E: Effect of naltrexone plus bupropion on weight loss in overweight and obese adults (COR-I): a multicentre, randomised, double-blind, placebo-controlled, phase 3 trial. Lancet. 2010 Aug 21;376(9741):595-605. doi: 10.1016/S0140-6736(10)60888-4. Epub 2010 Jul 29. [Article]
- Reece AS: Hypothalamic opioid-melanocortin appetitive balance and addictive craving. Med Hypotheses. 2011 Jan;76(1):132-7. doi: 10.1016/j.mehy.2010.09.002. [Article]
- Arias HR: Is the inhibition of nicotinic acetylcholine receptors by bupropion involved in its clinical actions? Int J Biochem Cell Biol. 2009 Nov;41(11):2098-108. doi: 10.1016/j.biocel.2009.05.015. Epub 2009 Jun 2. [Article]
- Dailymed: Contrave (bupropion + naltrexone) [Link]
- FDA Approved Drug Products: Wellbutrin XL® extended-release tablets [Link]
- FDA Approved Drug Products: Wellbutrin immediate-release tablets [Link]
- FDA Approved Drug Products: AUVELITY (dextromethorphan hydrobromide and bupropion hydrochloride) extended-release tablets, for oral use [Link]
- The Canadian Network for Mood and Anxiety Treatments (CANMAT) task force recommendations for the management of patients with mood disorders and comorbid attention-deficit/hyperactivity disorder [File]
- External Links
- Human Metabolome Database
- HMDB0001510
- KEGG Drug
- D07591
- KEGG Compound
- C06860
- PubChem Compound
- 444
- PubChem Substance
- 46506896
- ChemSpider
- 431
- BindingDB
- 50048392
- 42347
- ChEBI
- 3219
- ChEMBL
- CHEMBL894
- Therapeutic Targets Database
- DAP000052
- PharmGKB
- PA448687
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Bupropion
- FDA label
- Download (88.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Dementia / Depression / Geriatric Depression / Late Life Depression (LLD) / Major Depressive Disorder (MDD) / Major depressive disorder, recurrent episode / Mild Cognitive Impairment (MCI) / Treatment-Refractory Depression 1 4 Active Not Recruiting Treatment Obesity 3 4 Active Not Recruiting Treatment Obesity / Type 2 Diabetes Mellitus 1 4 Completed Not Available Roux-en-Y Gastric Bypass 1 4 Completed Not Available Smoking, Cessation 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Actavis Group
- American Nutriceuticals Inc.
- Amerisource Health Services Corp.
- Anchen Pharmaceuticals Inc.
- Apotex Inc.
- AQ Pharmaceuticals Inc.
- A-S Medication Solutions LLC
- Atlantic Biologicals Corporation
- Biovail Pharmaceuticals
- Bryant Ranch Prepack
- BTA Pharmaceuticals
- Cardinal Health
- Catalent Pharma Solutions
- CMIC-VPS Corp.
- Comprehensive Consultant Services Inc.
- Corepharma LLC
- Coupler Enterprises Inc.
- Dept Health Central Pharmacy
- Direct Dispensing Inc.
- Direct Pharmaceuticals Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- DSM Corp.
- Eon Labs
- GlaxoSmithKline Inc.
- Global Pharmaceuticals
- Golden State Medical Supply Inc.
- Heartland Repack Services LLC
- Impax Laboratories Inc.
- Innoviant Pharmacy Inc.
- Jackson Medical Inc.
- Kaiser Foundation Hospital
- Keltman Pharmaceuticals Inc.
- Lake Erie Medical and Surgical Supply
- Major Pharmaceuticals
- Mckesson Corp.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- PD-Rx Pharmaceuticals Inc.
- Pharmacy Service Center
- Pharmpak Inc.
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Professional Co.
- Rebel Distributors Corp.
- Remedy Repack
- Resource Optimization and Innovation LLC
- Sandoz
- Sanofi-Aventis Inc.
- Southwood Pharmaceuticals
- Spectrum Chemicals and Laboratory Products
- Stat Rx Usa
- Sun Pharmaceutical Industries Ltd.
- Teva Pharmaceutical Industries Ltd.
- Tya Pharmaceuticals
- UDL Laboratories
- Vangard Labs Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet, extended release Oral 174 mg/1 Tablet, extended release Oral 522 mg/1 Tablet, extended release Oral 348 mg/1 Kit Oral Tablet, multilayer, extended release Oral Tablet, film coated, extended release Oral 150 mg/1 Tablet, extended release Oral 450 mg Tablet, delayed release Oral 150 MG Tablet, delayed release Oral 300 MG Tablet Occlusive dressing technique 150 mg/1 Tablet Oral 100 mg/1 Tablet Oral 75 mg/1 Tablet, extended release Oral 100 mg/1 Tablet, extended release Oral 200 mg/1 Tablet, film coated Occlusive dressing technique 75 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, film coated Oral 75 mg/1 Tablet, film coated, extended release Occlusive dressing technique 150 mg/1 Tablet, film coated, extended release Oral 100 mg/1 Tablet, film coated, extended release Oral 200 mg/1 Tablet Oral 150 mg/1 Tablet Oral 300 mg/1 Tablet, extended release Oral 150 mg/1 Tablet, extended release Oral 300 mg/1 Tablet, film coated, extended release Oral 300 mg/1 Tablet Oral 150 MG Tablet Oral 300 MG Tablet Tablet 150 MG Tablet 300 MG Tablet Oral 150.000 mg Tablet, film coated, extended release Oral Tablet, extended release Oral 450 mg/1 Tablet, film coated, extended release Oral 450 mg/1 Tablet Oral Tablet, extended release Oral Tablet, extended release Oral 100 mg Tablet Oral 150.00 mg Tablet, film coated Oral 150 mg/1 Tablet, film coated Oral 200 mg/1 Tablet, film coated Oral 150 mg Tablet, extended release Oral 300 mg Tablet, extended release Oral Tablet, extended release Oral 150 mg - Prices
Unit description Cost Unit Aplenzin er 522 mg tablet 16.74USD tablet Bupropion hydrochloride powder 10.2USD g Wellbutrin XL 300 mg 24 Hour tablet 9.03USD tablet Wellbutrin xl 300 mg tablet 8.68USD tablet Wellbutrin SR 200 mg 12 Hour tablet 7.57USD tablet Aplenzin er 348 mg tablet 7.36USD tablet Wellbutrin sr 200 mg tablet 7.27USD tablet Wellbutrin XL 150 mg 24 Hour tablet 6.84USD tablet Wellbutrin xl 150 mg tablet 6.58USD tablet Aplenzin er 174 mg tablet 5.58USD tablet BuPROPion HCl 300 mg 24 Hour tablet 4.96USD tablet Wellbutrin SR 150 mg 12 Hour tablet 4.07USD tablet BuPROPion HCl 200 mg 12 Hour tablet 3.99USD tablet Wellbutrin sr 150 mg tablet 3.92USD tablet Zyban 150 mg 12 Hour tablet 3.88USD tablet Wellbutrin SR 100 mg 12 Hour tablet 3.8USD tablet Zyban sr 150 mg tablet 3.73USD tablet Wellbutrin sr 100 mg tablet 3.66USD tablet Wellbutrin 100 mg tablet 3.62USD tablet BuPROPion HCl 150 mg 12 Hour tablet 3.02USD tablet Wellbutrin 75 mg tablet 2.71USD tablet BuPROPion HCl (Smoking Deter) 150 mg 12 Hour tablet 2.01USD tablet Wellbutrin Xl 300 mg Extended-Release Tablet 1.12USD tablet Bupropion hcl 100 mg tablet 0.98USD tablet Wellbutrin Sr 150 mg Sustained-Release Tablet 0.96USD tablet Bupropion hcl 75 mg tablet 0.74USD tablet Wellbutrin Xl 150 mg Extended-Release Tablet 0.56USD tablet Pms-Bupropion Sr 150 mg Sustained-Release Tablet 0.53USD tablet Ratio-Bupropion Sr 150 mg Sustained-Release Tablet 0.53USD tablet Sandoz Bupropion Sr 150 mg Sustained-Release Tablet 0.53USD tablet Sandoz Bupropion Sr 100 mg Sustained-Release Tablet 0.35USD tablet Ratio-Bupropion Sr 100 mg Sustained-Release Tablet 0.35USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5358970 No 1994-10-25 2013-08-12 US CA2524300 No 2008-10-28 2023-08-08 Canada CA2168364 No 2001-09-18 2014-07-29 Canada US7569610 No 2009-08-04 2026-06-27 US US7662407 No 2010-02-16 2026-06-27 US US7241805 No 2007-07-10 2026-06-27 US US7649019 No 2010-01-19 2026-06-27 US US7645802 No 2010-01-12 2026-06-27 US US7671094 No 2010-03-02 2026-06-27 US US7572935 No 2009-08-11 2026-06-27 US US7585897 No 2009-09-08 2026-06-27 US US6096341 No 2000-08-01 2018-10-30 US US7674479 No 2010-03-09 2027-06-25 US US8722085 No 2014-05-13 2027-11-08 US US8318788 No 2012-11-27 2027-11-08 US US7462626 No 2008-12-09 2024-07-20 US US8815889 No 2014-08-26 2024-07-20 US US9107837 No 2015-08-18 2027-06-04 US US9125868 No 2015-09-08 2027-11-08 US US8916195 No 2014-12-23 2030-02-02 US US9248123 No 2016-02-02 2032-01-13 US US8088786 No 2012-01-03 2029-02-03 US US7375111 No 2008-05-20 2025-03-26 US US10231964 No 2019-03-19 2034-07-02 US US10307376 No 2019-06-04 2027-11-08 US US10835527 No 2020-11-17 2034-07-02 US US10828294 No 2020-11-10 2034-07-02 US US11139056 No 2021-10-05 2033-06-05 US US10403170 No 2019-09-03 2033-06-05 US US9633575 No 2017-04-25 2033-06-25 US US11033543 No 2021-06-15 2031-01-10 US US11278544 No 2004-04-21 2024-04-21 US US11324741 No 2009-05-29 2029-05-29 US US11382874 No 2014-11-05 2034-11-05 US US11364233 No 2014-11-05 2034-11-05 US US9457025 No 2016-10-04 2034-11-05 US US10058518 No 2018-08-28 2034-11-05 US US9278095 No 2016-03-08 2034-11-05 US US9867819 No 2018-01-16 2034-11-05 US US9168234 No 2015-10-27 2034-11-05 US US9861595 No 2018-01-09 2034-11-05 US US8569328 No 2013-10-29 2033-10-29 US US9700553 No 2017-07-11 2034-11-05 US US11357744 No 2014-11-05 2034-11-05 US US11344544 No 2014-11-05 2034-11-05 US US9486450 No 2016-11-08 2034-11-05 US US9474731 No 2016-10-25 2034-11-05 US US9375429 No 2016-06-28 2034-11-05 US US9421176 No 2016-08-23 2034-11-05 US US9408815 No 2016-08-09 2034-11-05 US US9763932 No 2017-09-19 2034-11-05 US US11311534 No 2014-11-05 2034-11-05 US US9205083 No 2015-12-08 2034-11-05 US US9707191 No 2017-07-18 2034-11-05 US US10898453 No 2021-01-26 2034-11-05 US US11433067 No 2014-11-05 2034-11-05 US US9700528 No 2017-07-11 2034-11-05 US US9370513 No 2016-06-21 2034-11-05 US US9457023 No 2016-10-04 2034-11-05 US US9238032 No 2016-01-19 2034-11-05 US US11096937 No 2021-08-24 2034-11-05 US US11298352 No 2014-11-05 2034-11-05 US US10966941 No 2021-04-06 2034-11-05 US US11298351 No 2014-11-05 2034-11-05 US US11090300 No 2021-08-17 2034-11-05 US US10894047 No 2021-01-19 2034-11-05 US US10064857 No 2018-09-04 2034-11-05 US US11291665 No 2014-11-05 2034-11-05 US US10780066 No 2020-09-22 2034-11-09 US US10780064 No 2020-09-22 2040-01-07 US US11291638 No 2014-11-05 2034-11-05 US US10786469 No 2020-09-29 2034-11-05 US US11253492 No 2014-11-05 2034-11-05 US US10881657 No 2021-01-05 2034-11-05 US US10874663 No 2020-12-29 2034-11-05 US US10799497 No 2020-10-13 2034-11-05 US US11058648 No 2021-07-13 2034-11-05 US US11273133 No 2014-11-05 2034-11-05 US US10864209 No 2020-12-15 2034-11-05 US US10806710 No 2020-10-20 2034-11-05 US US10881624 No 2021-01-05 2034-11-05 US US10786496 No 2020-09-29 2034-11-05 US US11020389 No 2021-06-01 2034-11-05 US US11185515 No 2021-11-30 2034-11-05 US US10945973 No 2021-03-16 2034-11-05 US US10966942 No 2021-04-06 2040-01-07 US US11285146 No 2014-11-05 2034-11-05 US US11285118 No 2014-11-05 2034-11-05 US US10596167 No 2020-03-24 2034-11-05 US US11439636 No 2014-11-05 2034-11-05 US US9314462 No 2016-04-19 2034-11-05 US US9198905 No 2015-12-01 2034-11-05 US US11426401 No 2014-11-05 2034-11-05 US US11426370 No 2014-11-05 2034-11-05 US US11419867 No 2014-11-05 2034-11-05 US US10772850 No 2020-09-15 2034-11-05 US US10940124 No 2021-03-09 2040-01-07 US US11273134 No 2014-11-05 2034-11-05 US US11253491 No 2014-11-05 2034-11-05 US US11234946 No 2014-11-05 2034-11-05 US US10548857 No 2020-02-04 2034-11-05 US US11229640 No 2014-11-05 2034-11-05 US US10874665 No 2020-12-29 2034-11-05 US US10933034 No 2021-03-02 2034-11-05 US US10251879 No 2019-04-09 2034-11-05 US US10925842 No 2021-02-23 2040-01-07 US US10092561 No 2018-10-09 2034-11-05 US US10894046 No 2021-01-19 2034-11-05 US US11191739 No 2021-12-07 2034-11-05 US US10874664 No 2020-12-29 2034-11-05 US US10080727 No 2018-09-25 2034-11-05 US US11197839 No 2021-12-14 2034-11-05 US US11147808 No 2021-10-19 2034-11-05 US US11207281 No 2021-12-28 2034-11-05 US US11141416 No 2021-10-12 2034-11-05 US US11141388 No 2021-10-12 2034-11-05 US US11213521 No 2014-11-05 2034-11-05 US US11129826 No 2021-09-28 2034-11-05 US US11123343 No 2021-09-21 2034-11-05 US US10966974 No 2021-04-06 2034-11-05 US US10512643 No 2019-12-24 2034-11-05 US US10463634 No 2019-11-05 2034-11-05 US US10105361 No 2018-10-23 2034-11-05 US US10105327 No 2018-10-23 2034-11-05 US US10092560 No 2018-10-09 2034-11-05 US US9968568 No 2018-05-15 2034-11-05 US US11510918 No 2014-11-05 2034-11-05 US US11478468 No 2014-11-05 2034-11-05 US US11497721 No 2014-11-05 2034-11-05 US US11524008 No 2014-11-05 2034-11-05 US US11524007 No 2014-11-05 2034-11-05 US US11517542 No 2014-11-05 2034-11-05 US US11517543 No 2014-11-05 2034-11-05 US US11541048 No 2014-11-05 2034-11-05 US US11541021 No 2014-11-05 2034-11-05 US US11534414 No 2014-11-05 2034-11-05 US US11596627 No 2014-11-05 2034-11-05 US US11617728 No 2014-11-05 2034-11-05 US US11617747 No 2014-11-05 2034-11-05 US US11730706 No 2023-01-23 2043-01-23 US US11717518 No 2023-01-20 2043-01-20 US US11752144 No 2023-02-23 2043-02-23 US US11779579 No 2014-11-05 2034-11-05 US US11844797 No 2023-04-20 2043-04-20 US US11839612 No 2023-03-02 2043-03-02 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 233-234 °C Not Available water solubility 312 mg/ml Not Available logP 3.6 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0693 mg/mL ALOGPS logP 3.28 ALOGPS logP 3.27 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 18.61 Chemaxon pKa (Strongest Basic) 8.22 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 29.1 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 67.7 m3·mol-1 Chemaxon Polarizability 26.12 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.975 Caco-2 permeable + 0.8866 P-glycoprotein substrate Non-substrate 0.733 P-glycoprotein inhibitor I Non-inhibitor 0.8738 P-glycoprotein inhibitor II Non-inhibitor 0.9343 Renal organic cation transporter Non-inhibitor 0.8814 CYP450 2C9 substrate Non-substrate 0.785 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.574 CYP450 1A2 substrate Non-inhibitor 0.7499 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.8993 CYP450 3A4 inhibitor Non-inhibitor 0.7743 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5141 Ames test Non AMES toxic 0.9233 Carcinogenicity Non-carcinogens 0.5609 Biodegradation Not ready biodegradable 0.9892 Rat acute toxicity 2.4363 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9684 hERG inhibition (predictor II) Non-inhibitor 0.8886
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 155.6424387 predictedDarkChem Lite v0.1.0 [M-H]- 154.0548 predictedDeepCCS 1.0 (2019) [M+H]+ 155.8345387 predictedDarkChem Lite v0.1.0 [M+H]+ 156.4128 predictedDeepCCS 1.0 (2019) [M+Na]+ 155.7454387 predictedDarkChem Lite v0.1.0 [M+Na]+ 162.50597 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Monoamine transmembrane transporter activity
- Specific Function
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A3
- Uniprot ID
- Q01959
- Uniprot Name
- Sodium-dependent dopamine transporter
- Molecular Weight
- 68494.255 Da
References
- Miller DK, Sumithran SP, Dwoskin LP: Bupropion inhibits nicotine-evoked [(3)H]overflow from rat striatal slices preloaded with [(3)H]dopamine and from rat hippocampal slices preloaded with [(3)H]norepinephrine. J Pharmacol Exp Ther. 2002 Sep;302(3):1113-22. [Article]
- Meyer JH, Goulding VS, Wilson AA, Hussey D, Christensen BK, Houle S: Bupropion occupancy of the dopamine transporter is low during clinical treatment. Psychopharmacology (Berl). 2002 Aug;163(1):102-5. Epub 2002 Jul 13. [Article]
- Kugaya A, Seneca NM, Snyder PJ, Williams SA, Malison RT, Baldwin RM, Seibyl JP, Innis RB: Changes in human in vivo serotonin and dopamine transporter availabilities during chronic antidepressant administration. Neuropsychopharmacology. 2003 Feb;28(2):413-20. Epub 2002 Jul 19. [Article]
- Learned-Coughlin SM, Bergstrom M, Savitcheva I, Ascher J, Schmith VD, Langstrom B: In vivo activity of bupropion at the human dopamine transporter as measured by positron emission tomography. Biol Psychiatry. 2003 Oct 15;54(8):800-5. [Article]
- Szabo Z, Argyelan M, Kanyo B, Pavics L, Janka Z: [Change of dopamine transporter activity (DAT) during the action of bupropion (in depression)]. Neuropsychopharmacol Hung. 2004 Jun;6(2):79-81. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [Article]
- Stahl SM, Pradko JF, Haight BR, Modell JG, Rockett CB, Learned-Coughlin S: A Review of the Neuropharmacology of Bupropion, a Dual Norepinephrine and Dopamine Reuptake Inhibitor. Prim Care Companion J Clin Psychiatry. 2004;6(4):159-166. [Article]
- Shalabi AR, Walther D, Baumann MH, Glennon RA: Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release. ACS Chem Neurosci. 2017 Jun 21;8(6):1397-1403. doi: 10.1021/acschemneuro.7b00055. Epub 2017 Feb 27. [Article]
- Simonsen U, Comerma-Steffensen S, Andersson KE: Modulation of Dopaminergic Pathways to Treat Erectile Dysfunction. Basic Clin Pharmacol Toxicol. 2016 Oct;119 Suppl 3:63-74. doi: 10.1111/bcpt.12653. [Article]
- Mortensen OV, Amara SG: Gain of function mutants reveal sites important for the interaction of the atypical inhibitors benztropine and bupropion with monoamine transporters. J Neurochem. 2006 Sep;98(5):1531-40. doi: 10.1111/j.1471-4159.2006.04060.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Norepinephrine:sodium symporter activity
- Specific Function
- Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A2
- Uniprot ID
- P23975
- Uniprot Name
- Sodium-dependent noradrenaline transporter
- Molecular Weight
- 69331.42 Da
References
- Bondarev ML, Bondareva TS, Young R, Glennon RA: Behavioral and biochemical investigations of bupropion metabolites. Eur J Pharmacol. 2003 Aug 1;474(1):85-93. [Article]
- Mitchell HA, Ahern TH, Liles LC, Javors MA, Weinshenker D: The effects of norepinephrine transporter inactivation on locomotor activity in mice. Biol Psychiatry. 2006 Nov 15;60(10):1046-52. Epub 2006 Aug 7. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Stahl SM, Pradko JF, Haight BR, Modell JG, Rockett CB, Learned-Coughlin S: A Review of the Neuropharmacology of Bupropion, a Dual Norepinephrine and Dopamine Reuptake Inhibitor. Prim Care Companion J Clin Psychiatry. 2004;6(4):159-166. [Article]
- Shalabi AR, Walther D, Baumann MH, Glennon RA: Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release. ACS Chem Neurosci. 2017 Jun 21;8(6):1397-1403. doi: 10.1021/acschemneuro.7b00055. Epub 2017 Feb 27. [Article]
- Mortensen OV, Amara SG: Gain of function mutants reveal sites important for the interaction of the atypical inhibitors benztropine and bupropion with monoamine transporters. J Neurochem. 2006 Sep;98(5):1531-40. doi: 10.1111/j.1471-4159.2006.04060.x. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Ligand-gated ion channel activity
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name
- CHRNA3
- Uniprot ID
- P32297
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-3
- Molecular Weight
- 57479.54 Da
References
- Fryer JD, Lukas RJ: Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J Pharmacol Exp Ther. 1999 Jan;288(1):88-92. [Article]
- Slemmer JE, Martin BR, Damaj MI: Bupropion is a nicotinic antagonist. J Pharmacol Exp Ther. 2000 Oct;295(1):321-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Negative modulator
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gate...
- Gene Name
- HTR3A
- Uniprot ID
- P46098
- Uniprot Name
- 5-hydroxytryptamine receptor 3A
- Molecular Weight
- 55279.835 Da
References
- Pandhare A, Pappu AS, Wilms H, Blanton MP, Jansen M: The antidepressant bupropion is a negative allosteric modulator of serotonin type 3A receptors. Neuropharmacology. 2017 Feb;113(Pt A):89-99. doi: 10.1016/j.neuropharm.2016.09.021. Epub 2016 Sep 24. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- Curator comments
- Information in the literature is limited regarding this enzyme action, however the product monograph suggests it is a minor substrate of CYP2C9.
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Health Canada Product Monograph: Bupropion sustained-release tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Faucette SR, Hawke RL, Lecluyse EL, Shord SS, Yan B, Laethem RM, Lindley CM: Validation of bupropion hydroxylation as a selective marker of human cytochrome P450 2B6 catalytic activity. Drug Metab Dispos. 2000 Oct;28(10):1222-30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Walsky RL, Astuccio AV, Obach RS: Evaluation of 227 drugs for in vitro inhibition of cytochrome P450 2B6. J Clin Pharmacol. 2006 Dec;46(12):1426-38. [Article]
- Lewis DF, Modi S, Dickins M: Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. [Article]
- Hesse LM, Venkatakrishnan K, Court MH, von Moltke LL, Duan SX, Shader RI, Greenblatt DJ: CYP2B6 mediates the in vitro hydroxylation of bupropion: potential drug interactions with other antidepressants. Drug Metab Dispos. 2000 Oct;28(10):1176-83. [Article]
- Jefferson JW, Pradko JF, Muir KT: Bupropion for major depressive disorder: Pharmacokinetic and formulation considerations. Clin Ther. 2005 Nov;27(11):1685-95. [Article]
- Foley KF, DeSanty KP, Kast RE: Bupropion: pharmacology and therapeutic applications. Expert Rev Neurother. 2006 Sep;6(9):1249-65. [Article]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Foley KF, DeSanty KP, Kast RE: Bupropion: pharmacology and therapeutic applications. Expert Rev Neurother. 2006 Sep;6(9):1249-65. [Article]
- Kotlyar M, Brauer LH, Tracy TS, Hatsukami DK, Harris J, Bronars CA, Adson DE: Inhibition of CYP2D6 activity by bupropion. J Clin Psychopharmacol. 2005 Jun;25(3):226-9. [Article]
- Sager JE, Tripathy S, Price LS, Nath A, Chang J, Stephenson-Famy A, Isoherranen N: In vitro to in vivo extrapolation of the complex drug-drug interaction of bupropion and its metabolites with CYP2D6; simultaneous reversible inhibition and CYP2D6 downregulation. Biochem Pharmacol. 2017 Jan 1;123:85-96. doi: 10.1016/j.bcp.2016.11.007. Epub 2016 Nov 9. [Article]
- Flockhart Table of Drug Interactions [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Antagonist
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23511.38 Da
References
- Ferry DG, Caplan NB, Cubeddu LX: Interaction between antidepressants and alpha 1-adrenergic receptor antagonists on the binding to alpha 1-acid glycoprotein. J Pharm Sci. 1986 Feb;75(2):146-9. doi: 10.1002/jps.2600750208. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Bergen AW, Javitz HS, Krasnow R, Michel M, Nishita D, Conti DV, Edlund CK, Kwok PY, McClure JB, Kim RB, Hall SM, Tyndale RF, Baker TB, Benowitz NL, Swan GE: Organic cation transporter variation and response to smoking cessation therapies. Nicotine Tob Res. 2014 Dec;16(12):1638-46. doi: 10.1093/ntr/ntu161. Epub 2014 Aug 20. [Article]
- FDA Center for Drug Evaluation and Research: Clinical Pharmacology and Biopharmaceutical Review(s) [File]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55