Peringatan Keamanan

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

Bupropion

DB01156

small molecule approved

Deskripsi

Bupropion (also known as the brand name product Wellbutrin®) is a norepinephrine/dopamine-reuptake inhibitor (NDRI) used most commonly for the management of Major Depressive Disorder (MDD), Seasonal Affective Disorder (SAD), and as an aid for smoking cessation. Bupropion exerts its pharmacological effects by weakly inhibiting the enzymes involved in the uptake of the neurotransmitters norepinephrine and dopamine from the synaptic cleft, therefore prolonging their duration of action within the neuronal synapse and the downstream effects of these neurotransmitters. More specifically, bupropion binds to the norepinephrine transporter (NET) and the dopamine transporter (DAT).A6399,A178810

Bupropion was originally classified as an "atypical" antidepressant because it does not exert the same effects as the classical antidepressants such as Monoamine Oxidase Inhibitors (MAOIs), Tricyclic Antidepressants (TCAs), or Selective Serotonin Reuptake Inhibitors (SSRIs). While it has comparable effectiveness to typical first-line options for the treatment of depression such as SSRIs,A178798,A178804 bupropion is a unique option for the treatment of MDD as it lacks any clinically relevant serotonergic effects, typical of other mood medications, or any effects on histamine or adrenaline receptors.A6399,A178840 Lack of activity at these receptors results in a more tolerable side effect profile; bupropion is less likely to cause sexual side effects, sedation, or weight gain as compared to SSRIs or TCAs, for example.A178804,A178807

When used as an aid to smoking cessation, bupropion is thought to confer its anti-craving and anti-withdrawal effects by inhibiting dopamine reuptake, which is thought to be involved in the reward pathways associated with nicotine, and through the antagonism of the nicotinic acetylcholinergic receptor.A178825,A1966,A16508 A Cochrane Review of meta-analyses of available treatment modalities for smoking cessation found that abstinence rates approximately doubled when bupropion was used as compared to placebo, and was found to have similar rates of smoking cessation as nicotine replacement therapy (NRT).A178816

Bupropion is sometimes used as an add-on agent to first-line treatments of depression such as selective serotonin reuptake inhibitor (SSRI) medications when there is a treatment-failure or only partial response.A178789 Bupropion is also used off-label for the management of Attention/Deficit-Hyperactivity Disorder (ADHD) in adults with comorbid bipolar depression to avoid mood destabilization caused by typical stimulant medications used for the treatment of ADHD.F4624

When used in combination with naltrexone in the marketed product Contrave? for chronic weight management, the two components are thought to have effects on areas of the brain involved in the regulation of food intake. This includes the hypothalamus, which is involved in appetite regulation, and the mesolimbic dopamine circuit, which is involved in reward pathways.L6562 Studies have shown that the combined activity of bupropion and naltrexone increase the firing rate of hypothalamic pro-opiomelanocortin (POMC) neurons and blockade of opioid receptor-mediated POMC auto-inhibition, which are associated with a reduction in food intake and increased energy expenditure.L6562,A179038,A179050 The combination of naltrexone and bupropion was shown to result in a statistically significant weight loss, with a mean change in body weight of -6.3% compared to -1.3% for placebo.A179047

Struktur Molekul 2D

Berat 239.741
Wujud solid

Peta Jejaring Molekuler
Legenda: Obat • Target • Gen • Enzim • (Panah → menunjukkan arah efek / relasi) • Transporter • Carrier

Profil Farmakokinetik

Waktu Paruh (Half-Life) 24 hours
Volume Distribusi -
Klirens (Clearance) -

Absorpsi

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.FDA 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.FDA 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.FDA 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.FDA Label

Metabolisme

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.A179062 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.FDA Label Bupropion and its metabolites exhibit linear kinetics following chronic administration of 300 to 450 mg per day.

Rute Eliminasi

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.

Farmakogenomik

1 Varian
DRD2 (rs1800497)

The presence of this genotype in DRD2 is associated with improved therapeutic response to bupropion.

Interaksi Makanan

2 Data
  • 1. Avoid alcohol. Co-administration with alcohol may result in neuropsychiatric adverse effects and potentiation of CNS depressant effects.
  • 2. Take with or without food. Co-administration with food does not significantly affect pharmacokinetics.

Interaksi Obat

1638 Data
Fluvoxamine The risk or severity of adverse effects can be increased when Bupropion is combined with Fluvoxamine.
Buprenorphine Bupropion may increase the central nervous system depressant (CNS depressant) activities of Buprenorphine.
Doxylamine Doxylamine may increase the central nervous system depressant (CNS depressant) activities of Bupropion.
Dronabinol The serum concentration of Bupropion can be increased when it is combined with Dronabinol.
Droperidol Droperidol may increase the central nervous system depressant (CNS depressant) activities of Bupropion.
Hydrocodone Bupropion may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
Hydroxyzine Hydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Bupropion.
Magnesium sulfate The therapeutic efficacy of Bupropion can be increased when used in combination with Magnesium sulfate.
Methotrimeprazine Bupropion may increase the central nervous system depressant (CNS depressant) activities of Methotrimeprazine.
Metyrosine Bupropion may increase the sedative activities of Metyrosine.
Minocycline Minocycline may increase the central nervous system depressant (CNS depressant) activities of Bupropion.
Mirtazapine Bupropion may increase the central nervous system depressant (CNS depressant) activities of Mirtazapine.
Nabilone Nabilone may increase the central nervous system depressant (CNS depressant) activities of Bupropion.
Paraldehyde Bupropion may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
Perampanel Perampanel may increase the central nervous system depressant (CNS depressant) activities of Bupropion.
Rufinamide The risk or severity of adverse effects can be increased when Rufinamide is combined with Bupropion.
Sodium oxybate Bupropion may increase the central nervous system depressant (CNS depressant) activities of Sodium oxybate.
Suvorexant Bupropion may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
Tapentadol Tapentadol may increase the central nervous system depressant (CNS depressant) activities of Bupropion.
Thalidomide Bupropion may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Zolpidem Bupropion may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Citalopram The risk or severity of adverse effects can be increased when Bupropion is combined with Citalopram.
Choline The excretion of Choline can be decreased when combined with Bupropion.
Dofetilide The excretion of Dofetilide can be decreased when combined with Bupropion.
Reserpine The excretion of Reserpine can be decreased when combined with Bupropion.
Metformin The excretion of Metformin can be decreased when combined with Bupropion.
Norepinephrine The excretion of Norepinephrine can be decreased when combined with Bupropion.
Pramipexole The excretion of Pramipexole can be decreased when combined with Bupropion.
Prazosin The excretion of Prazosin can be decreased when combined with Bupropion.
Cimetidine The metabolism of Bupropion can be decreased when combined with Cimetidine.
Cisplatin The excretion of Cisplatin can be decreased when combined with Bupropion.
Oxaliplatin The excretion of Oxaliplatin can be decreased when combined with Bupropion.
Epinephrine The excretion of Epinephrine can be decreased when combined with Bupropion.
Lamivudine The excretion of Lamivudine can be decreased when combined with Bupropion.
Ranitidine The excretion of Ranitidine can be decreased when combined with Bupropion.
Amantadine The excretion of Amantadine can be decreased when combined with Bupropion.
Dopamine The excretion of Dopamine can be decreased when combined with Bupropion.
Memantine The excretion of Memantine can be decreased when combined with Bupropion.
Varenicline The excretion of Varenicline can be decreased when combined with Bupropion.
Histamine The excretion of Histamine can be decreased when combined with Bupropion.
Dalfampridine The excretion of Dalfampridine can be decreased when combined with Bupropion.
Agmatine The excretion of Agmatine can be decreased when combined with Bupropion.
Linagliptin The excretion of Linagliptin can be decreased when combined with Bupropion.
Nafamostat The excretion of Nafamostat can be decreased when combined with Bupropion.
Choline salicylate The excretion of Choline salicylate can be decreased when combined with Bupropion.
Gentamicin The excretion of Gentamicin can be decreased when combined with Bupropion.
Methadone The risk or severity of adverse effects can be increased when Methadone is combined with Bupropion.
Atomoxetine The metabolism of Atomoxetine can be decreased when combined with Bupropion.
Brexpiprazole The metabolism of Brexpiprazole can be decreased when combined with Bupropion.
Ritonavir The metabolism of Bupropion can be increased when combined with Ritonavir.
Eliglustat The metabolism of Eliglustat can be decreased when combined with Bupropion.
Iloperidone The metabolism of Iloperidone can be decreased when combined with Bupropion.
Tetrabenazine The metabolism of Tetrabenazine can be decreased when combined with Bupropion.
Tranylcypromine The risk or severity of adverse effects can be increased when Tranylcypromine is combined with Bupropion.
Phenelzine The risk or severity of adverse effects can be increased when Phenelzine is combined with Bupropion.
Selegiline The risk or severity of adverse effects can be increased when Selegiline is combined with Bupropion.
Moclobemide The risk or severity of adverse effects can be increased when Moclobemide is combined with Bupropion.
Isocarboxazid The risk or severity of adverse effects can be increased when Isocarboxazid is combined with Bupropion.
Rasagiline The risk or severity of adverse effects can be increased when Rasagiline is combined with Bupropion.
Pargyline The risk or severity of adverse effects can be increased when Pargyline is combined with Bupropion.
Minaprine The risk or severity of adverse effects can be increased when Minaprine is combined with Bupropion.
Iproniazid The risk or severity of adverse effects can be increased when Iproniazid is combined with Bupropion.
Nialamide The risk or severity of adverse effects can be increased when Nialamide is combined with Bupropion.
Pirlindole The risk or severity of adverse effects can be increased when Pirlindole is combined with Bupropion.
Toloxatone The risk or severity of adverse effects can be increased when Toloxatone is combined with Bupropion.
Hydracarbazine The risk or severity of adverse effects can be increased when Hydracarbazine is combined with Bupropion.
Methylene blue The risk or severity of adverse effects can be increased when Methylene blue is combined with Bupropion.
Benmoxin The risk or severity of adverse effects can be increased when Benmoxin is combined with Bupropion.
Mebanazine The risk or severity of adverse effects can be increased when Mebanazine is combined with Bupropion.
Octamoxin The risk or severity of adverse effects can be increased when Octamoxin is combined with Bupropion.
Pheniprazine The risk or severity of adverse effects can be increased when Pheniprazine is combined with Bupropion.
Phenoxypropazine The risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Bupropion.
Pivhydrazine The risk or severity of adverse effects can be increased when Pivhydrazine is combined with Bupropion.
Safrazine The risk or severity of adverse effects can be increased when Safrazine is combined with Bupropion.
Caroxazone The risk or severity of adverse effects can be increased when Caroxazone is combined with Bupropion.
Furazolidone The risk or severity of adverse effects can be increased when Furazolidone is combined with Bupropion.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Bupropion.
Harmaline The risk or severity of adverse effects can be increased when Harmaline is combined with Bupropion.
Brofaromine The risk or severity of adverse effects can be increased when Brofaromine is combined with Bupropion.
Procaine The risk or severity of adverse effects can be increased when Procaine is combined with Bupropion.
Procarbazine The risk or severity of adverse effects can be increased when Procarbazine is combined with Bupropion.
Linezolid The risk or severity of adverse effects can be increased when Linezolid is combined with Bupropion.
Safinamide The risk or severity of adverse effects can be increased when Safinamide is combined with Bupropion.
Clorgiline The risk or severity of adverse effects can be increased when Clorgiline is combined with Bupropion.
Efavirenz The metabolism of Bupropion can be increased when combined with Efavirenz.
Phenindione The risk or severity of adverse effects can be increased when Bupropion is combined with Phenindione.
Coumarin The risk or severity of adverse effects can be increased when Bupropion is combined with Coumarin.
Tioclomarol The risk or severity of adverse effects can be increased when Bupropion is combined with Tioclomarol.
4-hydroxycoumarin The risk or severity of adverse effects can be increased when Bupropion is combined with 4-hydroxycoumarin.
Ethyl biscoumacetate The risk or severity of adverse effects can be increased when Bupropion is combined with Ethyl biscoumacetate.
Clorindione The risk or severity of adverse effects can be increased when Bupropion is combined with Clorindione.
Diphenadione The risk or severity of adverse effects can be increased when Bupropion is combined with Diphenadione.
(R)-warfarin The risk or severity of adverse effects can be increased when Bupropion is combined with (R)-warfarin.
(S)-Warfarin The risk or severity of adverse effects can be increased when Bupropion is combined with (S)-Warfarin.
Paroxetine The risk or severity of adverse effects can be increased when Bupropion is combined with Paroxetine.
Mifepristone The serum concentration of Bupropion can be increased when it is combined with Mifepristone.
Ioflupane I-123 Bupropion may decrease effectiveness of Ioflupane I-123 as a diagnostic agent.
Vortioxetine The risk or severity of adverse effects can be increased when Bupropion is combined with Vortioxetine.
Azelastine Bupropion may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
Brimonidine Brimonidine may increase the central nervous system depressant (CNS depressant) activities of Bupropion.

Target Protein

Sodium-dependent dopamine transporter SLC6A3
Sodium-dependent serotonin transporter SLC6A4
Sodium-dependent noradrenaline transporter SLC6A2
Neuronal acetylcholine receptor subunit alpha-3 CHRNA3
5-hydroxytryptamine receptor 3A HTR3A

Referensi & Sumber

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
Artikel (PubMed)
  • PMID: 9862757
    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.
  • PMID: 16027765
    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.
  • PMID: 16086611
    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.
  • PMID: 1684162
    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.
  • PMID: 16974189
    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.
  • PMID: 15652242
    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.
  • PMID: 16554526
    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.
  • PMID: 15361919
    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.
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