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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Bupropion (DB01156)

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Weight

Average: 239.741
Monoisotopic: 239.10769191

Chemical Formula

C₁₃H₁₈ClNO

Synonyms

• Amfebutamone
• Bupropion

External IDs

• 34841-39-9

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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

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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		••••••••••••			••••••• •••••••• •••••••• ••••••• •••• ••••••• •••••••• •••••••

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Associated Therapies

• Smoking, Cessation
• Weight Loss

Contraindications & Blackbox Warnings

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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	inhibitor	Humans
ASodium-dependent noradrenaline transporter	inhibitor	Humans
UNeuronal acetylcholine receptor subunit alpha-3	antagonist	Humans
U5-hydroxytryptamine receptor 3A	negative modulator	Humans

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.

Hover over products below to view reaction partners

• Bupropion
  • S-Hydroxybupropion
    • S,S-Hydroxybupropion
      • S,S-Hydroxybupropion glucuronide
  • S-4'-hydroxybupropion
    • S-4'-hydroxybupropion sulfate
    • S-4'-hydroxybupropion glucuronide
    • R,S-erythro-4'-hydroxy-hydrobupropion
    • S,S-threo-4'-hydroxy-hydrobupropion
  • R-Hydroxybupropion
    • R,R-Hydroxybupropion
      • R,R-Hydroxybupropion glucuronide
  • R-4'-hydroxybupropion
    • R-4'-hydroxybupropion sulfate
    • R-4'-hydroxybupropion glucuronide
    • R,S-erythro-4'-hydroxy-hydrobupropion
    • R,R-threo-4'-hydroxy-hydrobupropion
  • R,R-threohydrobupropion
    • R,R-threohydrobupropion glucuronide
    • R,R-threo-4'-hydroxy-hydrobupropion
  • S,S-threohydrobupropion
    • S,S-threohydrobupropion glucuronide
    • S,S-threo-4'-hydroxy-hydrobupropion
  • R,S-erythrohydrobupropion
    • R,S-erythrohydrobupropion glucuronide
    • R,S-erythro-4'-hydroxy-hydrobupropion
  • S,R-erythrohydrobupropion
    • S,R-erythrohydrobupropion glucuronide
    • S,R-erythro-4'-hydroxy-hydrobupropion
  • (2R)-2-(tert-butylamino)-1-(3-chlorophenyl)-3-hydroxypropan-1-one

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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1,2-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

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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

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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
Aplenzin	Tablet, extended release	522 mg/1	Oral	Bausch Health US, LLC	2008-04-23	Not applicable
Aplenzin	Tablet, extended release	348 mg/1	Oral	sanofi-aventis U.S. LLC	2009-03-30	2017-03-31
Aplenzin	Tablet, extended release	348 mg/1	Oral	Bausch Health US, LLC	2008-04-23	Not applicable
Aplenzin	Tablet, extended release	174 mg/1	Oral	sanofi-aventis U.S. LLC	2009-03-30	2017-03-31

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Ava-bupropion SR	Tablet, extended release	100 mg	Oral	Avanstra Inc	2011-09-19	2014-08-21
Ava-bupropion SR	Tablet, extended release	150 mg	Oral	Avanstra Inc	2011-09-19	2014-08-21
Budeprion	Tablet, extended release	150 mg/1	Oral	bryant ranch prepack	2008-05-30	Not applicable
Budeprion	Tablet, extended release	150 mg/1	Oral	Teva	2008-05-30	2013-01-31
Budeprion SR	Tablet, extended release	100 mg/1	Oral	Teva	2004-02-19	2014-10-31

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
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
Contrave	Bupropion hydrochloride (90 mg) + Naltrexone hydrochloride (8 mg)	Tablet, extended release	Oral	Bausch Health, Canada Inc.	2018-03-16	Not applicable
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
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

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
Appbutamone-D	Bupropion hydrochloride (75 mg/1) + Tyrosine (100 mg/1)	Kit	Oral	Physician Therapeutics Llc	2011-07-07	Not applicable

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

N06AX12 — Bupropion

• N06AX — Other antidepressants
• N06A — ANTIDEPRESSANTS
• N06 — PSYCHOANALEPTICS
• N — NERVOUS SYSTEM

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 / Hydrocarbon derivatives

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Substituents

Alkyl-phenylketone / Alpha-aminoketone / Amine / Aromatic homomonocyclic compound / Aryl alkyl ketone / Aryl chloride / Aryl halide / Benzenoid / Benzoyl / Chlorobenzene / Halobenzene / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxide / Organochloride / Organohalogen compound / Organonitrogen compound / Organopnictogen compound / Phenylpropane / Secondary aliphatic amine / Secondary amine

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
14. Slemmer JE, Martin BR, Damaj MI: Bupropion is a nicotinic antagonist. J Pharmacol Exp Ther. 2000 Oct;295(1):321-7. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
24. Dailymed: Contrave (bupropion + naltrexone) [Link]
25. FDA Approved Drug Products: Wellbutrin XL® extended-release tablets [Link]
26. FDA Approved Drug Products: Wellbutrin immediate-release tablets [Link]
27. FDA Approved Drug Products: AUVELITY (dextromethorphan hydrobromide and bupropion hydrochloride) extended-release tablets, for oral use [Link]
28. 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

RxNav

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
CA2524300	No	2008-10-28	2023-08-08
CA2168364	No	2001-09-18	2014-07-29
US7569610	No	2009-08-04	2026-06-27
US7662407	No	2010-02-16	2026-06-27
US7241805	No	2007-07-10	2026-06-27
US7649019	No	2010-01-19	2026-06-27
US7645802	No	2010-01-12	2026-06-27
US7671094	No	2010-03-02	2026-06-27
US7572935	No	2009-08-11	2026-06-27
US7585897	No	2009-09-08	2026-06-27
US6096341	No	2000-08-01	2018-10-30
US7674479	No	2010-03-09	2027-06-25
US8722085	No	2014-05-13	2027-11-08
US8318788	No	2012-11-27	2027-11-08
US7462626	No	2008-12-09	2024-07-20
US8815889	No	2014-08-26	2024-07-20
US9107837	No	2015-08-18	2027-06-04
US9125868	No	2015-09-08	2027-11-08
US8916195	No	2014-12-23	2030-02-02
US9248123	No	2016-02-02	2032-01-13
US8088786	No	2012-01-03	2029-02-03
US7375111	No	2008-05-20	2025-03-26
US10231964	No	2019-03-19	2034-07-02
US10307376	No	2019-06-04	2027-11-08
US10835527	No	2020-11-17	2034-07-02
US10828294	No	2020-11-10	2034-07-02
US11139056	No	2021-10-05	2033-06-05
US10403170	No	2019-09-03	2033-06-05
US9633575	No	2017-04-25	2033-06-25
US11033543	No	2021-06-15	2031-01-10
US11278544	No	2004-04-21	2024-04-21
US11324741	No	2009-05-29	2029-05-29
US11382874	No	2014-11-05	2034-11-05
US11364233	No	2014-11-05	2034-11-05
US9457025	No	2016-10-04	2034-11-05
US10058518	No	2018-08-28	2034-11-05
US9278095	No	2016-03-08	2034-11-05
US9867819	No	2018-01-16	2034-11-05
US9168234	No	2015-10-27	2034-11-05
US9861595	No	2018-01-09	2034-11-05
US8569328	No	2013-10-29	2033-10-29
US9700553	No	2017-07-11	2034-11-05
US11357744	No	2014-11-05	2034-11-05
US11344544	No	2014-11-05	2034-11-05
US9486450	No	2016-11-08	2034-11-05
US9474731	No	2016-10-25	2034-11-05
US9375429	No	2016-06-28	2034-11-05
US9421176	No	2016-08-23	2034-11-05
US9408815	No	2016-08-09	2034-11-05
US9763932	No	2017-09-19	2034-11-05
US11311534	No	2014-11-05	2034-11-05
US9205083	No	2015-12-08	2034-11-05
US9707191	No	2017-07-18	2034-11-05
US10898453	No	2021-01-26	2034-11-05
US11433067	No	2014-11-05	2034-11-05
US9700528	No	2017-07-11	2034-11-05
US9370513	No	2016-06-21	2034-11-05
US9457023	No	2016-10-04	2034-11-05
US9238032	No	2016-01-19	2034-11-05
US11096937	No	2021-08-24	2034-11-05
US11298352	No	2014-11-05	2034-11-05
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US11185515	No	2021-11-30	2034-11-05
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US11285118	No	2014-11-05	2034-11-05
US10596167	No	2020-03-24	2034-11-05
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US9314462	No	2016-04-19	2034-11-05
US9198905	No	2015-12-01	2034-11-05
US11426401	No	2014-11-05	2034-11-05
US11426370	No	2014-11-05	2034-11-05
US11419867	No	2014-11-05	2034-11-05
US10772850	No	2020-09-15	2034-11-05
US10940124	No	2021-03-09	2040-01-07
US11273134	No	2014-11-05	2034-11-05
US11253491	No	2014-11-05	2034-11-05
US11234946	No	2014-11-05	2034-11-05
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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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-000l-5900000000-1b5fb2e947791614a61d
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-001i-0910000000-fa2592b7296c7561333c
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0900000000-c10af1c8e3619fe0bffc
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-0490000000-55448af4d9a8ce866a88
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0900000000-2883ba18321a8b8228a1
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0159-0900000000-7d6cad849706146ddab3
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0159-0900000000-0fca8999746b69ee4fc1
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0900000000-b64f8d2b50bede574f63
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0900000000-2edefa63d5f6f1b08db7
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0006-0490000000-b8ea1de058a84547700d
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0910000000-6f471b9150fb1b7f6fcc
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-0159-0900000000-cc966137ee3283828af7
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-00lr-0900000000-7f86f38f740aa41b244b
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0900000000-e7f2cfdbabbd35a9b643
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0900000000-4daf0e10db1e5f2750bf
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-001i-0900000000-f77a450be176593153d2
MS/MS Spectrum - , positive	LC-MS/MS	splash10-00m0-0910000000-d2eb7265b058766459c9
MS/MS Spectrum - , positive	LC-MS/MS	splash10-001i-0910000000-fa2592b7296c7561333c
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-001i-0900000000-4d831e97d7e7dfff141b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00lr-0930000000-f64a441f96fcbc31635d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-1090000000-db11bfab011796b39e03
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01c4-3900000000-5123eb40ce9e13b14c3c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9000000000-24c9b44a47c3f313b9eb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9100000000-712ad711a04a0710b359
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9800000000-3fc7d4e56fe399a55b0b
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	155.6424387	predicted	DarkChem Lite v0.1.0
[M-H]-	154.0548	predicted	DeepCCS 1.0 (2019)
[M+H]+	155.8345387	predicted	DarkChem Lite v0.1.0
[M+H]+	156.4128	predicted	DeepCCS 1.0 (2019)
[M+Na]+	155.7454387	predicted	DarkChem Lite v0.1.0
[M+Na]+	162.50597	predicted	DeepCCS 1.0 (2019)

Targets

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Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	2900	N/A	N/A	A29502
IC 50 (nM)	1567	N/A	N/A	A29507
IC 50 (nM)	945	N/A	N/A	A29503
IC 50 (nM)	658	N/A	N/A	A29504 / A29506
IC 50 (nM)	660	N/A	N/A	A29505
Ki (nM)	784	N/A	N/A	A27351
Ki (nM)	1800	N/A	N/A	A27351
Ki (nM)	950	N/A	N/A	A27351
Ki (nM)	560	N/A	N/A	A27351
Ki (nM)	520	N/A	N/A	A4334
Ki (nM)	562	N/A	N/A	A18262
Ki (nM)	441	N/A	N/A	A29507
Ki (nM)	871	N/A	N/A	A29503

Details

Binding Properties1. Sodium-dependent dopamine transporter

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]

Binding Properties

×

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	1450	N/A	N/A	A29502
IC 50 (nM)	443	N/A	N/A	A29503
IC 50 (nM)	1850	N/A	N/A	A29504 / A29505 / A29506
Ki (nM)	>10000	N/A	N/A	A4334 / A18262
Ki (nM)	6970	N/A	N/A	A29503

Details

Binding Properties2. Sodium-dependent noradrenaline transporter

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. [Article]
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. [Article]
3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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. [Article]
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. [Article]
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. [Article]

Details3. Neuronal acetylcholine receptor subunit alpha-3

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. [Article]
2. Slemmer JE, Martin BR, Damaj MI: Bupropion is a nicotinic antagonist. J Pharmacol Exp Ther. 2000 Oct;295(1):321-7. [Article]

Details4. 5-hydroxytryptamine receptor 3A

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. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55