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Name
Bupropion
Accession Number
DB01156  (APRD00621)
Type
Small Molecule
Groups
Approved
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).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 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.25

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

Structure
Thumb
Synonyms
  • Amfebutamone
  • Bupropion
External IDs
34841-39-9
Product Ingredients
IngredientUNIICASInChI Key
Bupropion hydrobromideE70G3G5863905818-69-1WSTCENNATOVXKQ-UHFFFAOYSA-N
Bupropion hydrochlorideZG7E5POY8O31677-93-7HEYVINCGKDONRU-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Bupropion XLTablet, extended releaseOralActavis Pharma Company2016-05-03Not applicableCanada
Act Bupropion XLTablet, extended releaseOralActavis Pharma Company2016-05-03Not applicableCanada
AplenzinTablet, extended release348 mg/1OralValeant Pharmaceuticals North America LLC2008-04-23Not applicableUs
AplenzinTablet, extended release174 mg/1OralValeant Pharmaceuticals North America LLC2008-04-23Not applicableUs
AplenzinTablet, extended release522 mg/1OralSanofi Aventis2009-03-302018-09-26Us
AplenzinTablet, extended release348 mg/1OralSanofi Aventis2009-03-302018-09-26Us
AplenzinTablet, extended release522 mg/1OralValeant Pharmaceuticals North America LLC2008-04-23Not applicableUs
AplenzinTablet, extended release174 mg/1OralSanofi Aventis2009-03-302018-09-26Us
Aplenzin ERTablet, extended release348 mg/1OralStat Rx USA2009-03-30Not applicableUs
Bupropion HCl SRTablet, extended releaseOralValeant Canada Lp Valeant Canada S.E.C.Not applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ava-bupropion SRTablet, extended releaseOralAvanstra Inc2011-09-192014-08-21Canada
Ava-bupropion SRTablet, extended releaseOralAvanstra Inc2011-09-192014-08-21Canada
BudeprionTablet, extended release150 mg/1OralTeva2008-05-302013-01-31Us
BudeprionTablet, extended release150 mg/1Oralbryant ranch prepack2008-05-30Not applicableUs
Budeprion SRTablet, extended release100 mg/1OralTeva2004-02-192014-10-31Us0093 550120180907 15195 65j61g
Budeprion SRTablet, extended release150 mg/1OralCardinal Health2004-03-222012-02-29Us00093 5502 01 nlmimage10 742dba1d
Budeprion SRTablet, extended release150 mg/1Oralbryant ranch prepack2004-03-23Not applicableUs63629 287320180907 15195 eiqila
Budeprion SRTablet, extended release100 mg/1OralCardinal Health2004-01-282012-03-31Us00093 5501 01 nlmimage10 cf2d679b
Budeprion SRTablet, extended release150 mg/1OralTeva2004-03-232015-01-31Us0093 550220180907 15195 1xj1wgn
Budeprion XLTablet, film coated, extended release150 mg/1OralStat Rx USA2006-12-14Not applicableUs10370 0101 50 nlmimage10 a03fd01e
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ContraveBupropion hydrochloride (90 mg) + Naltrexone hydrochloride (8 mg)Tablet, extended releaseOralValeant Canada Lp Valeant Canada S.E.C.2018-03-16Not applicableCanada
ContraveBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, film coated, extended releaseOralTakeda2014-09-10Not applicableUs
ContraveBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, film coated, extended releaseOralA-S Medication Solutions2014-09-10Not applicableUs
Contrave Extended-ReleaseBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, extended releaseOralPD-Rx Pharmaceuticals, Inc.2014-10-22Not applicableUs
Contrave Extended-ReleaseBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, extended releaseOralNalpropion Pharmaceuticals, Inc.2014-10-22Not applicableUs
Contrave Extended-ReleaseBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, extended releaseOralA-S Medication Solutions2014-10-22Not applicableUs
Naltrexone Hydrochloride and Bupropion Hydrochloride Extended-ReleaseBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, extended releaseOralAbbvie2014-10-222017-12-29Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AppbutamoneBupropion hydrochloride (75 mg/1) + Tyrosine (100 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
Appbutamone-DBupropion hydrochloride (75 mg/1) + Tyrosine (100 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUs
International/Other Brands
Elontril / Forfivo / Prexaton / Voxra
Categories
UNII
01ZG3TPX31
CAS number
34911-55-2
Weight
Average: 239.741
Monoisotopic: 239.10769191
Chemical Formula
C13H18ClNO
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

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.25

Associated Conditions
Associated Therapies
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 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

TargetActionsOrganism
ASodium-dependent dopamine transporter
inhibitor
Humans
ASodium-dependent noradrenaline transporter
inhibitor
Humans
UNeuronal acetylcholine receptor subunit alpha-3
antagonist
Humans
U5-hydroxytryptamine receptor 3A
negative modulator
Humans
Additional Data Available
Adverse Effects

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Contraindications

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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.

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
Toxicity

Symptoms of overdose include seizures, hallucinations, loss of consciousness, tachycardia, and cardiac arrest.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
D(2) dopamine receptor---(C;C)C Allele, homozygousEffect Directly StudiedThe presence of this genotype in DRD2 is associated with improved therapeutic response to bupropion.Details

Interactions

Drug Interactions
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.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Bupropion.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Bupropion.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Bupropion is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,5-DinitrocatecholThe risk or severity of adverse effects can be increased when Bupropion is combined with 3,5-Dinitrocatechol.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Bupropion is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Bupropion is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Bupropion is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Bupropion.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Bupropion is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Bupropion.
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    Severity

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Food Interactions
  • Avoid alcohol.
  • Avoid St.John's Wort.
  • Take without regard to meals.

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
  1. 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. [PubMed:9862757]
  2. 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. [PubMed:16027765]
  3. 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. [PubMed:16086611]
  4. 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. [PubMed:1684162]
  5. 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. [PubMed:16974189]
  6. 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. [PubMed:15652242]
  7. 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. [PubMed:16554526]
  8. 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. [PubMed:15361919]
  9. John Rush A, Jain SB: Clinical Implications of the STAR*D Trial. Handb Exp Pharmacol. 2018 Sep 11. doi: 10.1007/164_2018_153. [PubMed:30203327]
  10. 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. [PubMed:27141292]
  11. Ashton AK, Rosen RC: Bupropion as an antidote for serotonin reuptake inhibitor-induced sexual dysfunction. J Clin Psychiatry. 1998 Mar;59(3):112-5. [PubMed:9541153]
  12. 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]
  13. 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. [PubMed:23728690]
  14. Slemmer JE, Martin BR, Damaj MI: Bupropion is a nicotinic antagonist. J Pharmacol Exp Ther. 2000 Oct;295(1):321-7. [PubMed:10991997]
  15. 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. [PubMed:12109932]
  16. 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. [PubMed:27671323]
  17. 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. [PubMed:16052243]
  18. 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. [PubMed:1900980]
  19. 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. [PubMed:29630702]
  20. 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. [PubMed:23924756]
  21. 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. [PubMed:20673995]
  22. 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. [PubMed:20926200]
  23. 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. [PubMed:19497387]
  24. Dailymed: Contrave (bupropion + naltrexone) [Link]
  25. 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
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
ATC Codes
A08AA62 — Bupropion and naltrexoneN06AX12 — Bupropion
AHFS Codes
  • 28:16.04.92 — Miscellaneous Antidepressants
FDA label
Download (88.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingPreventionCurrent Smokers / Head and Neck Squamous Cell Carcinoma (HNSCC) / Hypopharyngeal Squamous Cell Carcinoma / Laryngeal Squamous Cell Carcinoma / Nasopharyngeal Carcinoma / Oral Cavity Squamous Cell Carcinoma / Oropharyngeal Squamous Cell Carcinoma1
0CompletedBasic ScienceCocaine Use Disorders1
0CompletedTreatmentStress Disorders, Posttraumatic / Tobacco Use Disorders1
0RecruitingTreatmentMajor Depressive Disorder (MDD) / Unipolar Depression1
1CompletedNot AvailableHealthy Volunteers6
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of Bupropion / Pharmacokinetics of Isavuconazole1
1CompletedNot AvailableHeart Repolarization1
1CompletedNot AvailableNicotine Dependence / Tobacco Dependence1
1CompletedBasic ScienceAlzheimer's Disease (AD) / Metabolism1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Substance-Related Disorders1
1CompletedBasic ScienceSmoking / Tobacco Smoking Behavior1
1CompletedDiagnosticDrug Drug Interaction (DDI)1
1CompletedDiagnosticHealthy Volunteers1
1CompletedDiagnosticMethamphetamine Dependence1
1CompletedDiagnosticNicotine Dependence1
1CompletedOtherHealthy Volunteers1
1CompletedOtherLeukemia, Lymphocytic, Chronic, B-Cell1
1CompletedPreventionDepression / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentAdvanced Solid Tumors1
1CompletedTreatmentDepression2
1CompletedTreatmentHealthy Volunteers6
1CompletedTreatmentHealthy Volunteers / Type 2 Diabetes Mellitus1
1CompletedTreatmentMajor Depressive Disorder (MDD)2
1CompletedTreatmentMoods Disorders1
1CompletedTreatmentPulmonary Tuberculosis (TB) / Tuberculosis Infection1
1CompletedTreatmentSmoking1
1CompletedTreatmentTobacco Use Disorders1
1RecruitingTreatmentAdvanced Solid Tumors / Metastatic Melanoma1
1TerminatedNot AvailableDepressive Disorders1
1TerminatedTreatmentCocaine-Related Disorders1
1Unknown StatusBasic ScienceSubstance-Related Disorders1
1Unknown StatusDiagnosticAmphetamine-Related Disorders1
1, 2CompletedNot AvailableAcute Coronary Syndromes (ACS) / Depression1
1, 2CompletedTreatmentBipolar Disorder (BD)1
1, 2CompletedTreatmentHypoactive Sexual Desire Disorder (DSM-IV-TR Defined) / Sexual Interest/Arousal Disorder (DSM-5 Defined)1
1, 2CompletedTreatmentMajor Depressive Disorder (MDD) / Partner Relational Disorder (V61.10)1
1, 2CompletedTreatmentMethamphetamine Use Disorder1
1, 2CompletedTreatmentNicotine Dependence / Smoking1
1, 2TerminatedTreatmentHead and Neck Carcinoma1
1, 2WithdrawnSupportive CareLung Cancer Non-Small Cell Cancer (NSCLC)1
2Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)1
2Active Not RecruitingTreatmentNicotine Dependence / Smoking1
2CompletedNot AvailableBladder Cancers / Cervical Cancers / Esophageal Cancers / Head and Neck Carcinoma / Leukemias / Liver Cancer / Lung Cancers / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach / Renal Cancers / Tobacco Use Disorders1
2CompletedBasic ScienceBMI >30 kg/m21
2CompletedOtherDepression1
2CompletedTreatmentAdolescent Methamphetamine Abuse1
2CompletedTreatmentAlcohol Abuse1
2CompletedTreatmentAlcohol Dependence / Smoking1
2CompletedTreatmentAmphetamine Dependence / Methamphetamine / Methamphetamine Dependence / Pharmacogenetics / Substance Abuse1
2CompletedTreatmentAmphetamine-Related Disorders1
2CompletedTreatmentApathy / Huntington's Disease (HD)1
2CompletedTreatmentBMI >27 kg/m2 / BMI >30 kg/m2 / Nicotine Dependence1
2CompletedTreatmentBMI >30 kg/m23
2CompletedTreatmentBinge Drinking1
2CompletedTreatmentBipolar Disorder (BD) / Depressive Disorders1
2CompletedTreatmentCessation, Smoking1
2CompletedTreatmentCessation, Smoking / Nicotine Dependence / Smoking, Cigarette1
2CompletedTreatmentCessation, Smoking / Pregnancy1
2CompletedTreatmentCessation, Smoking / Schizophrenic Disorders1
2CompletedTreatmentDependence, Cocaine / Major Depressive Disorder (MDD)1
2CompletedTreatmentDepression1
2CompletedTreatmentDepressive Disorders1
2CompletedTreatmentErectile Dysfunction / Hypoactive Sexual Desire Disorder (HSDD) / Sexual Dysfunctions, Psychological1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Substance Abuse1
2CompletedTreatmentMajor Depressive Disorder (MDD)1
2CompletedTreatmentMarijuana Abuse1
2CompletedTreatmentMarijuana Abuse / Substance-Related Disorders1
2CompletedTreatmentMethamphetamine1
2CompletedTreatmentMethamphetamine Dependence1
2CompletedTreatmentNicotine Dependence1
2CompletedTreatmentNicotine Dependence / Nicotine Use Disorder1
2CompletedTreatmentSchizophrenia and Disorders With Psychotic Features / Tobacco Use Disorders1
2CompletedTreatmentSchizophrenic Disorders / Tobacco Use Cessation / Tobacco Use Disorders1
2CompletedTreatmentSchizophrenic Disorders / Tobacco Use Disorders1
2CompletedTreatmentSeasonal Affective Disorder (SAD)1
2CompletedTreatmentSmoking Lapse Behavior1
2CompletedTreatmentSmoking, Cigarette1
2CompletedTreatmentTobacco Use Disorders2
2Not Yet RecruitingTreatmentAnhedonia / Cessation, Smoking / Cessation, Tobacco / Smoking (Tobacco) Addiction / Tobacco Smoking Behavior1
2Not Yet RecruitingTreatmentCessation, Smoking / Nicotine Dependence / Smoking, Cigarette1
2RecruitingSupportive CareCarcinoma, Breast / Cervical Carcinoma / One to five years postmenopausal / Ovarian Carcinoma / Uterine Corpus Cancer / Vaginal Carcinoma / Vulvar Carcinoma1
2RecruitingTreatmentAlcohol Dependence / Alcohol Use Disorder (AUD)1
2Unknown StatusTreatmentTobacco Use Cessation / Tobacco Use Disorders1
2, 3Active Not RecruitingTreatmentCessation, Smoking / Tobacco Use Disorders1
2, 3CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Dependence, Cocaine / Opioid-Related Disorders1
2, 3CompletedTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m21
2, 3CompletedTreatmentCrohn's Disease (CD)1
2, 3CompletedTreatmentDepression / Suicide, Attempted1
2, 3CompletedTreatmentNicotine Dependence / Nicotine Withdrawal1
2, 3CompletedTreatmentOrgasmic Disorder1
2, 3CompletedTreatmentPost Traumatic Stress Disorder (PTSD) / Smoking1
2, 3CompletedTreatmentRestless Legs Syndrome (RLS)1
2, 3CompletedTreatmentSmoking1
2, 3Enrolling by InvitationTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m22
2, 3RecruitingTreatmentAgitation in Patients With Dementia of the Alzheimer's Type / Alzheimer's Disease (AD) / Psychomotor Agitation1
2, 3RecruitingTreatmentBinge Eating Disorder (BED) / BMI >30 kg/m22
2, 3RecruitingTreatmentBinge Eating Disorder (BED)1
2, 3RecruitingTreatmentDependence, Cocaine / Substance Abuse1
2, 3TerminatedTreatmentNicotine Dependence / Smoking, Cigarette1
2, 3TerminatedTreatmentTobacco Dependence1
2, 3Unknown StatusTreatmentTobacco Use Disorders1
3Active Not RecruitingTreatmentCessation, Smoking1
3Active Not RecruitingTreatmentMajor Depressive Disorder (MDD)1
3Active Not RecruitingTreatmentNicotine Dependence / Tobacco Use1
3CompletedNot AvailableUnipolar Depression1
3CompletedPreventionCessation, Smoking1
3CompletedPreventionLung Cancers1
3CompletedTreatmentAcute Coronary Syndromes (ACS) / Myocardial Infarction / Smoking1
3CompletedTreatmentApathy in Dementia1
3CompletedTreatmentAttention Deficit Disorder (ADD)1
3CompletedTreatmentBMI >27 kg/m2 / BMI >30 kg/m23
3CompletedTreatmentBMI >27 kg/m2 / BMI >30 kg/m2 / Type 2 Diabetes Mellitus1
3CompletedTreatmentCessation, Smoking1
3CompletedTreatmentDepression / Major Depressive Disorder (MDD)1
3CompletedTreatmentDepression / Major Depressive Disorder (MDD) / Unipolar Depression1
3CompletedTreatmentDepressive Disorders / Major Depressive Disorder (MDD)1
3CompletedTreatmentEpilepsies / Major Depressive Disorder (MDD)1
3CompletedTreatmentMajor Depressive Disorder (MDD)5
3CompletedTreatmentMethamphetamine Use Disorder1
3CompletedTreatmentNicotine Dependence3
3CompletedTreatmentSeasonal Affective Disorder (SAD)1
3CompletedTreatmentSmokeless Tobacco1
3CompletedTreatmentSmoking1
3CompletedTreatmentSmoking / Tobacco Use Disorders1
3CompletedTreatmentTobacco Use Disorders3
3Not Yet RecruitingTreatmentCessation, Smoking / Human Immunodeficiency Virus (HIV) / Opioid Dependence1
3RecruitingSupportive CareAnatomic Stage I Breast Cancer AJCC v8 / Anatomic Stage IA Breast Cancer AJCC v8 / Anatomic Stage IB Breast Cancer AJCC v8 / Anatomic Stage II Breast Cancer AJCC v8 / Anatomic Stage IIA Breast Cancer AJCC v8 / Anatomic Stage IIB Breast Cancer AJCC v8 / Anatomic Stage III Breast Cancer AJCC v8 / Anatomic Stage IIIA Breast Cancer AJCC v8 / Anatomic Stage IIIB Breast Cancer AJCC v8 / Anatomic Stage IIIC Breast Cancer AJCC v8 / Cancer Fatigue / Cancer Survivors / Complete Remission / Prognostic Stage I Breast Cancer AJCC v8 / Prognostic Stage IA Breast Cancer AJCC v8 / Prognostic Stage IB Breast Cancer AJCC v8 / Prognostic Stage II Breast Cancer AJCC v8 / Prognostic Stage IIA Breast Cancer AJCC v8 / Prognostic Stage IIB Breast Cancer AJCC v8 / Prognostic Stage III Breast Cancer AJCC v8 / Prognostic Stage IIIA Breast Cancer AJCC v8 / Prognostic Stage IIIB Breast Cancer AJCC v8 / Prognostic Stage IIIC Breast Cancer AJCC v81
3RecruitingTreatmentBMI >30 kg/m21
3RecruitingTreatmentBipolar I Disorder1
3RecruitingTreatmentCessation, Smoking1
3RecruitingTreatmentDepression / Major Depressive Disorder (MDD) / Treatment Resistant Depression (TRD)1
3RecruitingTreatmentTreatment Resistant Major Depressive Disorder1
3TerminatedPreventionLung Cancers1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentBMI >27 kg/m2 / BMI >30 kg/m21
3Unknown StatusTreatmentAlcohol-Related Disorders / Cessation, Smoking1
3WithdrawnTreatmentDepressive Disorder, Treatment-Resistant1
4Active Not RecruitingTreatmentBMI >30 kg/m21
4Active Not RecruitingTreatmentCessation, Smoking / Nicotine Addiction / Smoking, Cigarette1
4CompletedNot AvailableCessation, Smoking1
4CompletedNot AvailableRoux En Y Gastric Bypass1
4CompletedBasic ScienceDepression1
4CompletedBasic ScienceNicotine Dependence1
4CompletedBasic ScienceType 2 Diabetes Mellitus1
4CompletedHealth Services ResearchHealthy Volunteers1
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedPreventionCerebrovascular Diseases / Cessation, Smoking1
4CompletedSupportive CareFriedreich's Ataxia1
4CompletedTreatmentAlcohol Dependence / Smoking1
4CompletedTreatmentApathy / Depression / Sexual Dysfunctions / Side Effects1
4CompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Cannabis Use Disorders / Nicotine Dependence1
4CompletedTreatmentBipolar Disorder (BD)1
4CompletedTreatmentBladder Cancers / Cervical Cancers / Esophageal Cancers / Head and Neck Carcinoma / Leukemias / Liver Cancer / Lung Cancers / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach / Renal Cancers / Tobacco Use Disorders1
4CompletedTreatmentBreast Cancer / Major Depressive Disorder (MDD)1
4CompletedTreatmentCardiovascular Heart Disease / Myocardial Infarction / Smoking / Unstable Angina Pectoris1
4CompletedTreatmentCessation, Smoking3
4CompletedTreatmentCessation, Smoking / Schizophrenic Disorders1
4CompletedTreatmentCessation, Smoking / Smoking / Tobacco Use Disorders1
4CompletedTreatmentCigarette-smoking / Obese / Schizophrenic Disorders1
4CompletedTreatmentDepression1
4CompletedTreatmentDepression / Dysthymic Disorder / Major Depressive Disorder (MDD)1
4CompletedTreatmentDepression / Suicidal Thoughts1
4CompletedTreatmentDysthymic Disorder1
4CompletedTreatmentDysthymic Disorder / Major Depressive Disorder (MDD)2
4CompletedTreatmentFatigue / Inflammatory Bowel Diseases (IBD) / Sleep Disturbances1
4CompletedTreatmentFocus of This Study Was to Determine if Bupropion Works Better for Smoking Cessation Alone or in Combination With Nicotine Gum as Needed / Tobacco Dependence1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHomelessness / Tobacco Use Disorders1
4CompletedTreatmentMajor Depressive Disorder (MDD)6
4CompletedTreatmentNicotine Dependence1
4CompletedTreatmentNicotine Dependence / Substance Abuse / Substance Dependence / Tobacco Dependence1
4CompletedTreatmentPregnancy Related / Tobacco Use Disorders1
4CompletedTreatmentPsychotic Disorder NOS / Schizophrenic Disorders / Tobacco-Use Disorder1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders / Smokers1
4CompletedTreatmentSchizophrenic Disorders / Smoking, Cigarette1
4CompletedTreatmentSchizophrenic Disorders / Tobacco Dependence1
4CompletedTreatmentSleep disorders and disturbances / Tobacco Use Cessation1
4CompletedTreatmentSmoking2
4CompletedTreatmentSmoking / Tobacco Dependence1
4CompletedTreatmentTobacco Dependence1
4CompletedTreatmentTobacco Use Disorders2
4Not Yet RecruitingPreventionPostpartum Smoking Relapse1
4Not Yet RecruitingTreatmentDiagnosis and Treatment of Depression1
4Not Yet RecruitingTreatmentMajor Depressive Disorder (MDD)1
4Not Yet RecruitingTreatmentPost Traumatic Stress Disorder (PTSD) / Smoking1
4RecruitingBasic ScienceMajor Depressive Disorder (MDD)1
4RecruitingDiagnosticAsthma / Asthma: [Nos] or [Attack] / Major Depressive Disorder (MDD)1
4RecruitingTreatmentBMI >30 kg/m2 / Schizophrenic Disorders / Type 2 Diabetes Mellitus1
4RecruitingTreatmentCessation, Smoking / Mental Illnesses / Tobacco Smoking Behavior / Tobacco Use Disorders1
4RecruitingTreatmentDepression1
4RecruitingTreatmentDepressive Disorders1
4RecruitingTreatmentGeriatric Depression / Late Life Depression (LLD) / Major Depressive Disorder (MDD) / Treatment Resistant Depression (TRD) / Treatment-Refractory Depression1
4TerminatedTreatmentBMI >30 kg/m2 / Cardiovascular Heart Disease1
4TerminatedTreatmentBipolar Disorder (BD) / Depression1
4TerminatedTreatmentDepression1
4TerminatedTreatmentEnd Stage Renal Disease (ESRD) / Major Depressive Disorder (MDD)1
4TerminatedTreatmentInsomnia / Nicotine Dependence1
4TerminatedTreatmentMajor Depressive Disorder (MDD)1
4TerminatedTreatmentNicotine Dependence / Schizophrenic Disorders1
4TerminatedTreatmentTobacco Use Disorders1
4Unknown StatusTreatmentAlcohol Dependence / Depression / Suicidal Behaviour1
4Unknown StatusTreatmentBipolar Disorder (BD)1
4Unknown StatusTreatmentDepression2
4Unknown StatusTreatmentMajor Depressive Disorder (MDD)1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD) / Nicotine Dependence1
4WithdrawnTreatmentDepressive Disorder Not Otherwise Specified (NOS) / Dysthymic Disorder / Major Depressive Disorder (MDD)1
4WithdrawnTreatmentDepressive illness1
4WithdrawnTreatmentWeight Regain Post Bariatric Surgery1
Not AvailableActive Not RecruitingOtherMajor Depressive Disorder (MDD)1
Not AvailableActive Not RecruitingTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) / Nicotine Dependence1
Not AvailableActive Not RecruitingTreatmentAlcohol Drinking / Cessation, Smoking1
Not AvailableActive Not RecruitingTreatmentHead and Neck Carcinoma / Lung Cancers1
Not AvailableActive Not RecruitingTreatmentNicotine Dependence / Smokeless Tobacco1
Not AvailableCompletedNot AvailableCancer and Tobacco Abuse1
Not AvailableCompletedNot AvailableCessation, Smoking / Depressive Disorders / Pregnancy1
Not AvailableCompletedNot AvailableDepressive Disorders1
Not AvailableCompletedNot AvailableDepressive Disorders / Malignancies1
Not AvailableCompletedNot AvailableMajor Depressive Disorder (MDD)1
Not AvailableCompletedBasic ScienceDepression1
Not AvailableCompletedPreventionBMI >27 kg/m2 / BMI >30 kg/m2 / Breast Cancer1
Not AvailableCompletedPreventionBipolar Disorder (BD) / Depression / Psychotic Disorder NOS / Schizophrenic Disorders1
Not AvailableCompletedPreventionCancer Survivors / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableCompletedScreeningAcute Coronary Syndromes (ACS) / Depressive Symptomatology1
Not AvailableCompletedTreatmentAlcohol Drinking / Attention Deficit Disorder (ADD) / Cessation, Smoking / Depression1
Not AvailableCompletedTreatmentAttention Deficit Disorder With Hyperactivity (ADHD) / Substance Use Disorder (SUD)1
Not AvailableCompletedTreatmentBinge Eating Disorder (BED)1
Not AvailableCompletedTreatmentBipolar Disorder (BD)1
Not AvailableCompletedTreatmentCessation, Smoking / Health Behavior / Lifestyle-related Condition1
Not AvailableCompletedTreatmentCocaine-Related Disorders1
Not AvailableCompletedTreatmentGambling / Pathological Gambling1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentHomeless Persons / Smoking1
Not AvailableCompletedTreatmentMarijuana Abuse / Smoking, Cigarette1
Not AvailableCompletedTreatmentMethamphetamine Use Disorder1
Not AvailableCompletedTreatmentNicotine Dependence1
Not AvailableCompletedTreatmentNicotine Dependence / Tobacco Use Disorders1
Not AvailableCompletedTreatmentPeriodontitis1
Not AvailableCompletedTreatmentPost Traumatic Stress Disorder (PTSD) / Smoking1
Not AvailableCompletedTreatmentSmoking1
Not AvailableCompletedTreatmentTobacco Use Disorders2
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableEnrolling by InvitationNot AvailableCessation, Smoking1
Not AvailableRecruitingNot AvailableDepression1
Not AvailableRecruitingNot AvailableDepression / Suicidal Thoughts1
Not AvailableRecruitingBasic ScienceAdverse Effect of Drug Therapy Metabolism Medications (Diagnosis)1
Not AvailableRecruitingTreatmentAntidepressant Drug Adverse Reaction / Depression1
Not AvailableRecruitingTreatmentCessation, Smoking / Genetic Predisposition1
Not AvailableRecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Smoking1
Not AvailableTerminatedNot AvailableSmoking1
Not AvailableUnknown StatusNot AvailableMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusDiagnosticTobacco Use Disorders1
Not AvailableUnknown StatusTreatmentCessation, Smoking1
Not AvailableUnknown StatusTreatmentCessation, Smoking / Smoking1
Not AvailableUnknown StatusTreatmentMajor Depressive Disorder (MDD)1
Not AvailableUnknown StatusTreatmentTreatment Resistant Depression (TRD)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
FormRouteStrength
Tablet, extended releaseOral174 mg/1
Tablet, extended releaseOral522 mg/1
Tablet, extended releaseOral348 mg/1
KitOral
Tablet, film coated, extended releaseOral150 mg/1
TabletOcclusive dressing technique150 mg/1
TabletOral100 mg/1
TabletOral300 mg/1
TabletOral75 mg/1
Tablet, extended releaseOral100 mg/1
Tablet, extended releaseOral150 mg/1
Tablet, extended releaseOral200 mg/1
Tablet, film coatedOcclusive dressing technique75 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral75 mg/1
Tablet, film coated, extended releaseOcclusive dressing technique150 mg/1
Tablet, film coated, extended releaseOral100 mg/1
Tablet, film coated, extended releaseOral200 mg/1
TabletOral150 mg/1
Tablet, extended releaseOral300 mg/1
Tablet, film coated, extended releaseOral300 mg/1
Tablet, film coated, extended releaseOral
Tablet, extended releaseOral450 mg/1
Tablet, film coated, extended releaseOral450 mg/1
Tablet, extended releaseOral
Tablet, extended releaseOral
Tablet, extended releaseOral100 mg
Tablet, extended releaseOral150 mg
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral200 mg/1
Tablet, extended releaseOral300 mg
Prices
Unit descriptionCostUnit
Aplenzin er 522 mg tablet16.74USD tablet
Bupropion hydrochloride powder10.2USD g
Wellbutrin XL 300 mg 24 Hour tablet9.03USD tablet
Wellbutrin xl 300 mg tablet8.68USD tablet
Wellbutrin SR 200 mg 12 Hour tablet7.57USD tablet
Aplenzin er 348 mg tablet7.36USD tablet
Wellbutrin sr 200 mg tablet7.27USD tablet
Wellbutrin XL 150 mg 24 Hour tablet6.84USD tablet
Wellbutrin xl 150 mg tablet6.58USD tablet
Aplenzin er 174 mg tablet5.58USD tablet
BuPROPion HCl 300 mg 24 Hour tablet4.96USD tablet
Wellbutrin SR 150 mg 12 Hour tablet4.07USD tablet
BuPROPion HCl 200 mg 12 Hour tablet3.99USD tablet
Wellbutrin sr 150 mg tablet3.92USD tablet
Zyban 150 mg 12 Hour tablet3.88USD tablet
Wellbutrin SR 100 mg 12 Hour tablet3.8USD tablet
Zyban sr 150 mg tablet3.73USD tablet
Wellbutrin sr 100 mg tablet3.66USD tablet
Wellbutrin 100 mg tablet3.62USD tablet
BuPROPion HCl 150 mg 12 Hour tablet3.02USD tablet
Wellbutrin 75 mg tablet2.71USD tablet
BuPROPion HCl (Smoking Deter) 150 mg 12 Hour tablet2.01USD tablet
Wellbutrin Xl 300 mg Extended-Release Tablet1.12USD tablet
Bupropion hcl 100 mg tablet0.98USD tablet
Wellbutrin Sr 150 mg Sustained-Release Tablet0.96USD tablet
Bupropion hcl 75 mg tablet0.74USD tablet
Wellbutrin Xl 150 mg Extended-Release Tablet0.56USD tablet
Pms-Bupropion Sr 150 mg Sustained-Release Tablet0.53USD tablet
Ratio-Bupropion Sr 150 mg Sustained-Release Tablet0.53USD tablet
Sandoz Bupropion Sr 150 mg Sustained-Release Tablet0.53USD tablet
Sandoz Bupropion Sr 100 mg Sustained-Release Tablet0.35USD tablet
Ratio-Bupropion Sr 100 mg Sustained-Release Tablet0.35USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5358970No1994-10-252013-08-12Us
CA2524300No2008-10-282023-08-08Canada
CA2168364No2001-09-182014-07-29Canada
US7569610No2009-08-042026-06-27Us
US7662407No2010-02-162026-06-27Us
US7241805No2007-07-102026-06-27Us
US7649019No2010-01-192026-06-27Us
US7645802No2010-01-122026-06-27Us
US7671094No2010-03-022026-06-27Us
US7572935No2009-08-112026-06-27Us
US7585897No2009-09-082026-06-27Us
US6096341No2000-08-012018-10-30Us
US7674479No2010-03-092027-06-25Us
US8722085No2014-05-132027-11-08Us
US8318788No2012-11-272027-11-08Us
US7462626No2008-12-092024-07-20Us
US8815889No2014-08-262024-07-20Us
US9107837No2015-08-182027-06-04Us
US9125868No2015-09-082027-11-08Us
US8916195No2014-12-232030-02-02Us
US9248123No2016-02-022032-01-13Us
US8088786No2012-01-032029-02-03Us
US7375111No2008-05-202025-03-26Us
US10231964No2014-07-022034-07-02Us
US10307376No2007-11-082027-11-08Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)233-234 °CNot Available
water solubility312 mg/mlNot Available
logP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0693 mg/mLALOGPS
logP3.28ALOGPS
logP3.27ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)18.29ChemAxon
pKa (Strongest Basic)8.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.7 m3·mol-1ChemAxon
Polarizability25.93 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.975
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.733
P-glycoprotein inhibitor INon-inhibitor0.8738
P-glycoprotein inhibitor IINon-inhibitor0.9343
Renal organic cation transporterNon-inhibitor0.8814
CYP450 2C9 substrateNon-substrate0.785
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.574
CYP450 1A2 substrateNon-inhibitor0.7499
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorNon-inhibitor0.7743
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5141
Ames testNon AMES toxic0.9233
CarcinogenicityNon-carcinogens0.5609
BiodegradationNot ready biodegradable0.9892
Rat acute toxicity2.4363 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9684
hERG inhibition (predictor II)Non-inhibitor0.8886
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-c10af1c8e3619fe0bffc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0490000000-55448af4d9a8ce866a88
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-2883ba18321a8b8228a1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-0900000000-7d6cad849706146ddab3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-0900000000-0fca8999746b69ee4fc1
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-b64f8d2b50bede574f63
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-2edefa63d5f6f1b08db7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-0490000000-b8ea1de058a84547700d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0910000000-6f471b9150fb1b7f6fcc
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0159-0900000000-cc966137ee3283828af7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00lr-0900000000-7f86f38f740aa41b244b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-e7f2cfdbabbd35a9b643
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-4daf0e10db1e5f2750bf
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-001i-0900000000-f77a450be176593153d2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00m0-0910000000-d2eb7265b058766459c9
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0910000000-fa2592b7296c7561333c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-4d831e97d7e7dfff141b

Taxonomy

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 / Phenylpropane / Benzoyl / Aryl alkyl ketone / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Benzenoid
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary amino compound, monochlorobenzenes, propanone, aromatic ketone (CHEBI:3219)

Targets

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
  1. 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. [PubMed:12183670]
  2. 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. [PubMed:12185406]
  3. 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. [PubMed:12589396]
  4. 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. [PubMed:14550679]
  5. 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. [PubMed:15787205]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. 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. [PubMed:9537821]
  8. 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. [PubMed:15361919]
  9. 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]
  10. 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. [PubMed:27541930]
  11. 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. [PubMed:16923164]
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
  1. 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. [PubMed:12909199]
  2. 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. [PubMed:16893531]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  4. 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. [PubMed:15361919]
  5. 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]
  6. 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. [PubMed:16923164]
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
  1. 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. [PubMed:9862757]
  2. Slemmer JE, Martin BR, Damaj MI: Bupropion is a nicotinic antagonist. J Pharmacol Exp Ther. 2000 Oct;295(1):321-7. [PubMed:10991997]
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
  1. 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. [PubMed:27671323]

Enzymes

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
  1. 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. [PubMed:17101742]
  2. 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. [PubMed:11996013]
  3. 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. [PubMed:10997936]
  4. Jefferson JW, Pradko JF, Muir KT: Bupropion for major depressive disorder: Pharmacokinetic and formulation considerations. Clin Ther. 2005 Nov;27(11):1685-95. [PubMed:16368442]
  5. Foley KF, DeSanty KP, Kast RE: Bupropion: pharmacology and therapeutic applications. Expert Rev Neurother. 2006 Sep;6(9):1249-65. [PubMed:17009913]
  6. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
  7. 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
  1. Foley KF, DeSanty KP, Kast RE: Bupropion: pharmacology and therapeutic applications. Expert Rev Neurother. 2006 Sep;6(9):1249-65. [PubMed:17009913]
  2. 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. [PubMed:15876900]
  3. 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. [PubMed:27836670]
  4. Flockhart Table of Drug Interactions [Link]
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
  1. Bupropion monograph [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
  1. 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. [PubMed:10997944]

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
  1. 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. [PubMed:2870173]

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
  1. 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. [PubMed:25143296]
  2. FDA Center for Drug Evaluation and Research: Clinical Pharmacology and Biopharmaceutical Review(s) [File]

Drug created on June 13, 2005 07:24 / Updated on December 07, 2019 14:29