Bupropion

Overview

Description
A medication used treat mood disorders, such as depression, and nicotine addiction.
Description
A medication used treat mood disorders, such as depression, and nicotine addiction.
DrugBank ID
DB01156
Type
Small Molecule
US Approved
YES
Other Approved
YES
Clinical Trials
Phase 0
7
Phase 1
83
Phase 2
96
Phase 3
81
Phase 4
120
Therapeutic Categories
  • Aminoketone Antidepressants
  • Antidepressive Agents Indicated for Depression

Identification

Summary

Bupropion is a norepinephrine and dopamine reuptake inhibitor used in the treatment of major depressive disorder (MDD), seasonal affective disorder (SAD), and as an aid to smoking cessation.

Brand Names
Aplenzin, Auvelity, Budeprion, Contrave, Forfivo, Wellbutrin, Zyban
Generic Name
Bupropion
DrugBank Accession Number
DB01156
Background

Bupropion (also known as the brand name product Wellbutrin®) is a norepinephrine/dopamine-reuptake inhibitor (NDRI) used most commonly for the management of Major Depressive Disorder (MDD), Seasonal Affective Disorder (SAD), and as an aid for smoking cessation. Bupropion exerts its pharmacological effects by weakly inhibiting the enzymes involved in the uptake of the neurotransmitters norepinephrine and dopamine from the synaptic cleft, therefore prolonging their duration of action within the neuronal synapse and the downstream effects of these neurotransmitters. More specifically, bupropion binds to the norepinephrine transporter (NET) and the dopamine transporter (DAT).8,12

Bupropion was originally classified as an "atypical" antidepressant because it does not exert the same effects as the classical antidepressants such as Monoamine Oxidase Inhibitors (MAOIs), Tricyclic Antidepressants (TCAs), or Selective Serotonin Reuptake Inhibitors (SSRIs). While it has comparable effectiveness to typical first-line options for the treatment of depression such as SSRIs,9,10 bupropion is a unique option for the treatment of MDD as it lacks any clinically relevant serotonergic effects, typical of other mood medications, or any effects on histamine or adrenaline receptors.8,16 Lack of activity at these receptors results in a more tolerable side effect profile; bupropion is less likely to cause sexual side effects, sedation, or weight gain as compared to SSRIs or TCAs, for example.10,11

When used as an aid to smoking cessation, bupropion is thought to confer its anti-craving and anti-withdrawal effects by inhibiting dopamine reuptake, which is thought to be involved in the reward pathways associated with nicotine, and through the antagonism of the nicotinic acetylcholinergic receptor.15,1,14 A Cochrane Review of meta-analyses of available treatment modalities for smoking cessation found that abstinence rates approximately doubled when bupropion was used as compared to placebo, and was found to have similar rates of smoking cessation as nicotine replacement therapy (NRT).13

Bupropion is sometimes used as an add-on agent to first-line treatments of depression such as selective serotonin reuptake inhibitor (SSRI) medications when there is a treatment-failure or only partial response.7 Bupropion is also used off-label for the management of Attention/Deficit-Hyperactivity Disorder (ADHD) in adults with comorbid bipolar depression to avoid mood destabilization caused by typical stimulant medications used for the treatment of ADHD.28

When used in combination with naltrexone in the marketed product ContraveⓇ for chronic weight management, the two components are thought to have effects on areas of the brain involved in the regulation of food intake. This includes the hypothalamus, which is involved in appetite regulation, and the mesolimbic dopamine circuit, which is involved in reward pathways.24 Studies have shown that the combined activity of bupropion and naltrexone increase the firing rate of hypothalamic pro-opiomelanocortin (POMC) neurons and blockade of opioid receptor-mediated POMC auto-inhibition, which are associated with a reduction in food intake and increased energy expenditure.24,20,22 The combination of naltrexone and bupropion was shown to result in a statistically significant weight loss, with a mean change in body weight of -6.3% compared to -1.3% for placebo.21

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 239.741
Monoisotopic: 239.10769191
Chemical Formula
C13H18ClNO
Synonyms
  • Amfebutamone
  • Bupropion
External IDs
  • 34841-39-9

Pharmacology

Indication

Bupropion is indicated for the treatment of major depressive disorder (MDD), seasonal affective disorder (SAD), and as an aid to smoking cessation.

When used in combination with naltrexone as the marketed product ContraveⓇ, bupropion is indicated as an adjunct to a reduced-calorie diet and increased physical activity for chronic weight management in adults with an initial body mass index (BMI) of: 30 kg/m^2 or greater (obese) or 27 kg/m^2 or greater (overweight) in the presence of at least one weight-related comorbid condition (e.g., hypertension, type 2 diabetes mellitus, or dyslipidemia).

Bupropion is also used off-label as a first-line treatment in patients with ADHD and comorbid bipolar disorder when used as an adjunct to mood stabilizers.28

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAttention deficit/hyperactivity disorder (adhd)••• ••••••••••
Treatment ofMajor depressive disorder••••••••••••
Used in combination to treatMajor depressive disorder (mdd)Combination Product in combination with: Dextromethorphan (DB00514)••••••••••••••••••••••• •••••••••••••••• •••••••• •••••••
Used in combination to treatObesityCombination Product in combination with: Naltrexone (DB00704)••••••••••••
Prevention ofSeasonal affective disorder••••••••••••••••••• •••••••• •••••••• ••••••• •••• ••••••• •••••••• •••••••
Associated Therapies
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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

TargetActionsOrganism
ASodium-dependent dopamine transporter
inhibitor
Humans
ASodium-dependent serotonin 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.

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Route of elimination

Bupropion is extensively metabolized in humans. Oxidation of the bupropion side chain results in the formation of a glycine conjugate of metachlorobenzoic acid, which is then excreted as the major urinary metabolite. Following oral administration of 200 mg of 14C-bupropion in humans, 87% and 10% of the radioactive dose were recovered in the urine and feces, respectively. However, the fraction of the oral dose of bupropion excreted unchanged was only 0.5%, a finding consistent with the extensive metabolism of bupropion.

Half-life

24 hours

Clearance

Not Available

Adverse Effects
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Toxicity

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

Pathways
Not Available
Pharmacogenomic Effects/ADRs
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
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Bupropion is combined with 1,2-Benzodiazepine.
AbacavirAbacavir may decrease the excretion rate of Bupropion which could result in a higher serum level.
AbametapirThe serum concentration of Bupropion can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Bupropion can be increased when combined with Abatacept.
AbrocitinibThe 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
IngredientUNIICASInChI Key
Bupropion hydrobromideE70G3G5863905818-69-1WSTCENNATOVXKQ-UHFFFAOYSA-N
Bupropion hydrochlorideZG7E5POY8O31677-93-7HEYVINCGKDONRU-UHFFFAOYSA-N
Product Images
International/Other Brands
Elontril / Forfivo / Prexaton / Voxra
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AplenzinTablet, extended release522 mg/1OralSanofi Aventis Deutschland Gmb H2009-03-302017-03-31US flag
AplenzinTablet, extended release522 mg/1OralBausch Health, Canada Inc.2008-04-23Not applicableUS flag
AplenzinTablet, extended release348 mg/1OralSanofi Aventis Deutschland Gmb H2009-03-302017-03-31US flag
AplenzinTablet, extended release348 mg/1OralBausch Health, Canada Inc.2008-04-23Not applicableUS flag
AplenzinTablet, extended release174 mg/1OralSanofi Aventis Deutschland Gmb H2009-03-302017-03-31US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ava-bupropion SRTablet, extended release100 mgOralAvanstra Inc2011-09-192014-08-21Canada flag
Ava-bupropion SRTablet, extended release150 mgOralAvanstra Inc2011-09-192014-08-21Canada flag
BudeprionTablet, extended release150 mg/1Oralbryant ranch prepack2008-05-30Not applicableUS flag
BudeprionTablet, extended release150 mg/1OralTeva Italia S.R.L.2008-05-302013-01-31US flag
Budeprion SRTablet, extended release100 mg/1OralTeva Italia S.R.L.2004-02-192014-10-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AuvelityBupropion hydrochloride (105 mg/1) + Dextromethorphan hydrobromide monohydrate (45 mg/1)Tablet, multilayer, extended releaseOralAxsome Therapeutics, Inc.2022-08-18Not applicableUS flag
ContraveBupropion hydrochloride (90 mg) + Naltrexone hydrochloride (8 mg)Tablet, extended releaseOralBausch Health, Canada Inc.2018-03-16Not applicableCanada flag
ContraveBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, film coated, extended releaseOralA-S Medication Solutions2014-09-102018-09-30US flag
ContraveBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, film coated, extended releaseOralTakeda Pharma A/S2014-09-102019-08-15US flag
Contrave Extended-ReleaseBupropion hydrochloride (90 mg/1) + Naltrexone hydrochloride (8 mg/1)Tablet, extended releaseOralA-S Medication Solutions2014-10-22Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AppbutamoneBupropion hydrochloride (75 mg/1) + Tyrosine (100 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag
Appbutamone-DBupropion hydrochloride (75 mg/1) + Tyrosine (100 mg/1)KitOralPhysician Therapeutics Llc2011-07-07Not applicableUS flag

Categories

ATC Codes
N06AX62 — Bupropion and dextromethorphanA08AA62 — Bupropion and naltrexoneN06AX12 — Bupropion
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Alkyl-phenylketones
Alternative Parents
Phenylpropanes / Benzoyl derivatives / Aryl alkyl ketones / Chlorobenzenes / Aryl chlorides / Alpha-amino ketones / Dialkylamines / Organopnictogen compounds / Organochlorides / Organic oxides
show 1 more
Substituents
Alkyl-phenylketone / Alpha-aminoketone / Amine / Aromatic homomonocyclic compound / Aryl alkyl ketone / Aryl chloride / Aryl halide / Benzenoid / Benzoyl / Chlorobenzene
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
secondary amino compound, monochlorobenzenes, propanone, aromatic ketone (CHEBI:3219)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
01ZG3TPX31
CAS number
34911-55-2
InChI Key
SNPPWIUOZRMYNY-UHFFFAOYSA-N
InChI
InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3
IUPAC Name
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
SMILES
CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1

References

Synthesis Reference

Shalabi AR, Walther D, Baumann MH, Glennon RA: Deconstructed Analogues of Bupropion Reveal Structural Requirements for Transporter Inhibition versus Substrate-Induced Neurotransmitter Release. ACS Chem Neurosci. 2017 Jun 21;8(6):1397-1403. doi: 10.1021/acschemneuro.7b00055. Epub 2017 Feb 27. [PubMed:28220701]

US3819706
General References
  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]
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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableActive Not RecruitingPreventionNon-Small Cell Lung Carcinoma / Squamous Cell Carcinoma of the Head and Neck (SCCHN)1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableBreastfeeding1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableCancer and Tobacco Abuse1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableCancer / Depressive Disorder1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableDepressive Disorder1somestatusstop reasonjust information to hide

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, multilayer, extended releaseOral
Tablet, film coated, extended releaseOral150 mg/1
Tablet, extended releaseOral450 mg
Tablet, delayed releaseOral150 MG
Tablet, delayed releaseOral300 MG
TabletOcclusive dressing technique150 mg/1
TabletOral100 mg/1
TabletOral75 mg/1
Tablet, extended releaseOral100 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
TabletOral300 mg/1
Tablet, extended releaseOral150 mg/1
Tablet, extended releaseOral300 mg/1
Tablet, film coated, extended releaseOral300 mg/1
TabletOral150 MG
TabletOral300 MG
Tablet
Tablet150 MG
Tablet300 MG
TabletOral150.000 mg
Tablet, film coated, extended releaseOral
Tablet, extended releaseOral450 mg/1
Tablet, film coated, extended releaseOral450 mg/1
TabletOral
Tablet, extended releaseOral
Tablet, extended releaseOral100 mg
TabletOral150.00 mg
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral150 mg
Tablet, extended releaseOral300 mg
Tablet, extended releaseOral
Tablet, extended releaseOral150 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
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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)18.61Chemaxon
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
Polarizability26.12 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-MSsplash10-000l-5900000000-1b5fb2e947791614a61d
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-001i-0910000000-fa2592b7296c7561333c
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-0930000000-f64a441f96fcbc31635d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1090000000-db11bfab011796b39e03
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01c4-3900000000-5123eb40ce9e13b14c3c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-24c9b44a47c3f313b9eb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9100000000-712ad711a04a0710b359
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9800000000-3fc7d4e56fe399a55b0b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[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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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Mediates sodium- and chloride-dependent transport of dopamine (PubMed:10375632, PubMed:11093780, PubMed:1406597, PubMed:15505207, PubMed:19478460, PubMed:8302271). Also mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (By similarity). Regulator of light-dependent retinal hyaloid vessel regression, downstream of OPN5 signaling (By similarity)
Specific Function
amine binding
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]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin transporter that cotransports serotonin with one Na(+) ion in exchange for one K(+) ion and possibly one proton in an overall electroneutral transport cycle. Transports serotonin across the plasma membrane from the extracellular compartment to the cytosol thus limiting serotonin intercellular signaling (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Essential for serotonin homeostasis in the central nervous system. In the developing somatosensory cortex, acts in glutamatergic neurons to control serotonin uptake and its trophic functions accounting for proper spatial organization of cortical neurons and elaboration of sensory circuits. In the mature cortex, acts primarily in brainstem raphe neurons to mediate serotonin uptake from the synaptic cleft back into the pre-synaptic terminal thus terminating serotonin signaling at the synapse (By similarity). Modulates mucosal serotonin levels in the gastrointestinal tract through uptake and clearance of serotonin in enterocytes. Required for enteric neurogenesis and gastrointestinal reflexes (By similarity). Regulates blood serotonin levels by ensuring rapid high affinity uptake of serotonin from plasma to platelets, where it is further stored in dense granules via vesicular monoamine transporters and then released upon stimulation (PubMed:17506858, PubMed:18317590). Mechanistically, the transport cycle starts with an outward-open conformation having Na1(+) and Cl(-) sites occupied. The binding of a second extracellular Na2(+) ion and serotonin substrate leads to structural changes to outward-occluded to inward-occluded to inward-open, where the Na2(+) ion and serotonin are released into the cytosol. Binding of intracellular K(+) ion induces conformational transitions to inward-occluded to outward-open and completes the cycle by releasing K(+) possibly together with a proton bound to Asp-98 into the extracellular compartment. Na1(+) and Cl(-) ions remain bound throughout the transport cycle (PubMed:10407194, PubMed:12869649, PubMed:21730057, PubMed:27049939, PubMed:27756841, PubMed:34851672). Additionally, displays serotonin-induced channel-like conductance for monovalent cations, mainly Na(+) ions. The channel activity is uncoupled from the transport cycle and may contribute to the membrane resting potential or excitability (By similarity)
Specific Function
actin filament binding
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Mediates sodium- and chloride-dependent transport of norepinephrine (also known as noradrenaline) (PubMed:2008212, PubMed:8125921). Can also mediate sodium- and chloride-dependent transport of dopamine (PubMed:11093780, PubMed:8125921)
Specific Function
actin binding
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]
  7. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General 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
Specific Function
acetylcholine binding
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Negative modulator
General Function
Forms serotonin (5-hydroxytryptamine/5-HT3)-activated cation-selective channel complexes, which when activated cause fast, depolarizing responses in neurons
Specific Function
excitatory extracellular ligand-gated monoatomic ion channel activity
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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Information in the literature is limited regarding this enzyme action, however the product monograph suggests it is a minor substrate of CYP2C9.
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
Specific Function
(R)-limonene 6-monooxygenase activity
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Health Canada Product Monograph: Bupropion sustained-release tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids (PubMed:10553002, PubMed:18577768). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10553002, PubMed:18577768). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates fatty acids specifically at the omega-1 position displaying the highest catalytic activity for saturated fatty acids (PubMed:10553002, PubMed:18577768). May be involved in the oxidative metabolism of xenobiotics (Probable)
Specific Function
4-nitrophenol 2-monooxygenase activity
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids (PubMed:12865317, PubMed:21289075). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:21289075). Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2 (PubMed:12865317, PubMed:21289075). Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs (PubMed:11695850, PubMed:22909231). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850)
Specific Function
anandamide 11,12 epoxidase activity
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. [Article]
  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. [Article]
  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. [Article]
  4. Jefferson JW, Pradko JF, Muir KT: Bupropion for major depressive disorder: Pharmacokinetic and formulation considerations. Clin Ther. 2005 Nov;27(11):1685-95. [Article]
  5. Foley KF, DeSanty KP, Kast RE: Bupropion: pharmacology and therapeutic applications. Expert Rev Neurother. 2006 Sep;6(9):1249-65. [Article]
  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. [Article]
  7. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function
anandamide 11,12 epoxidase activity
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. [Article]
  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. [Article]
  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. [Article]
  4. Flockhart Table of Drug Interactions [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Antagonist
General Function
Functions as a 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 the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction
Specific Function
Not Available
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23539.43 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. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Electrogenic voltage-dependent transporter that mediates the transport of a variety of organic cations such as endogenous bioactive amines, cationic drugs and xenobiotics (PubMed:9260930, PubMed:9687576). Functions as a Na(+)-independent, bidirectional uniporter (PubMed:21128598, PubMed:9687576). Cation cellular uptake or release is driven by the electrochemical potential, i.e. membrane potential and concentration gradient (PubMed:15212162, PubMed:9260930, PubMed:9687576). However, may also engage electroneutral cation exchange when saturating concentrations of cation substrates are reached (By similarity). Predominantly expressed at the basolateral membrane of hepatocytes and proximal tubules and involved in the uptake and disposition of cationic compounds by hepatic and renal clearance from the blood flow (PubMed:15783073). Implicated in monoamine neurotransmitters uptake such as histamine, dopamine, adrenaline/epinephrine, noradrenaline/norepinephrine, serotonin and tyramine, thereby supporting a physiological role in the central nervous system by regulating interstitial concentrations of neurotransmitters (PubMed:16581093, PubMed:17460754, PubMed:9687576). Also capable of transporting dopaminergic neuromodulators cyclo(his-pro), salsolinol and N-methyl-salsolinol, thereby involved in the maintenance of dopaminergic cell integrity in the central nervous system (PubMed:17460754). Mediates the bidirectional transport of acetylcholine (ACh) at the apical membrane of ciliated cell in airway epithelium, thereby playing a role in luminal release of ACh from bronchial epithelium (PubMed:15817714). Also transports guanidine and endogenous monoamines such as vitamin B1/thiamine, creatinine and N-1-methylnicotinamide (NMN) (PubMed:12089365, PubMed:15212162, PubMed:17072098, PubMed:24961373, PubMed:9260930). Mediates the uptake and efflux of quaternary ammonium compound choline (PubMed:9260930). Mediates the bidirectional transport of polyamine agmatine and the uptake of polyamines putrescine and spermidine (PubMed:12538837, PubMed:21128598). Able to transport non-amine endogenous compounds such as prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) (PubMed:11907186). Also involved in the uptake of xenobiotic 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP) (PubMed:12395288, PubMed:16394027). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
Specific Function
acetylcholine transmembrane transporter activity
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. [Article]
  2. FDA Center for Drug Evaluation and Research: Clinical Pharmacology and Biopharmaceutical Review(s) [File]

Drug created at June 13, 2005 13:24 / Updated at November 06, 2024 19:54