13/01/2017 Bupropion ­ Wikipedia Bupropion From Wikipedia, the free encyclopedia Bupropion is a medication primarily used as an antidepressant Bupropion and smoking cessation aid.[6][7][8] It is marketed as Wellbutrin and Zyban among other trade names. It is one of the most frequently prescribed antidepressants in the United States and Canada,[9] although in many countries this is an off­label use.[10] It is an effective antidepressant on its own, but is also popular as an add­on medication in cases of incomplete response to first­ line SSRI antidepressants.[11] Bupropion is taken in tablet form and is available only by prescription in most countries.[9] The most important side effect is an increase in risk for epileptic seizures, which caused the drug to be withdrawn from the market for some time and then caused the recommended dosage to be reduced.[11] In comparison to many other antidepressants, it does not cause as much weight gain or sexual dysfunction.[11] Bupropion acts as an norepinephrine­dopamine reuptake inhibitor (NDRI). It is an atypical antidepressant, different from most commonly prescribed antidepressants such as selective 1 : 1 mixture (racemate) serotonin reuptake inhibitors (SSRIs).[10] Clinical data Pronunciation /bjuːˈproʊ.pi.ɒn/ Bupropion is known to affect several different biological bew­ᐟᐣᐝᐏ­pee­on targets.[11][12] It often is described as a norepinephrine­dopamine Trade names Wellbutrin, Elontril, Zyban reuptake inhibitor (NDRI), and is also a nicotinic antagonist.[12][13] However, bupropion does not appear to have AHFS/Drugs.com Monograph (https://www.drugs. significant dopaminergic actions in humans under normal com/monograph/bupropion­hydr clinical circumstances.[12][14] Chemically, bupropion belongs to ochloride.html) the class of aminoketones and is similar in structure to MedlinePlus a695033 (https://medlineplus.go stimulants such as cathinone and amfepramone, and to v/druginfo/meds/a695033.html) [11] phenethylamines in general. License data US FDA: Bupropion (htt p://www.accessdata.fda.g Bupropion was first made by Nariman Mehta and patented by Burroughs Wellcome in 1969, which later became part of what ov/scripts/cder/drugsatfd is now GlaxoSmithKline. It was first approved for medical use a/index.cfm?fuseaction=S in the United States in 1989. It was originally called by the earch.SearchAction&Sear generic name amfebutamone, before being renamed in 2000.[15] chTerm=Bupropion&Sear chType=BasicSearch) Pregnancy AU: B2 category Contents US: C (Risk not ruled out) Dependence none to very low 1 Medical uses liability 1.1 Depression Addiction none to very low 1.2 Smoking cessation liability 1.3 Attention deficit hyperactivity disorder Routes of Medical: oral https://en.wikipedia.o1rg.4/wikSi/Beuxpuroaplio dnysfunction 1/16 13/01/2017 Bupropion ­ Wikipedia 1.4 Sexual dysfunction administration Recreational: insufflation, 1.5 Obesity intravenous 1.6 Other uses 2 Contraindications ATC code N06AX12 (WHO (http://www.w 3 Side effects hocc.no/atc_ddd_index/?code=N 3.1 Psychiatric 06AX12)) 4 Overdose Legal status 5 Interactions 6 Pharmacology Legal status AU: S4 (Prescription 6.1 Pharmacodynamics only) 6.1.1 Dopaminergic activity CA: ℞­only 6.1.2 Antinicotinic and other activities UK: POM (Prescription 6.2 Pharmacokinetics 7 Chemistry only) 7.1 Synthesis US: ℞­only 8 History Pharmacokinetic data 8.1 Issue with generic bioequivalence 9 Society and culture Protein binding 84% (bupropion), 77% 9.1 Names (hydroxybupropion metabolite), 9.2 Recreational use 42% (threohydrobupropion 10 References metabolite)[1] 11 External links Metabolism Hepatic (mostly CYP2B6­ mediated hydroxylation, but Medical uses with some contributions from CYP1A2, CYP2A6, CYP2C9, CYP3A4, CYP2E1 and Depression CYP2C19)[1][2][3][4] Bupropion is one of the most widely prescribed antidepressants, Biological half­ 12–30 hours[3][5] and the available evidence indicates that it is effective in clinical life depression[16] — as effective as several other widely prescribed Excretion Renal (87%; 0.5% unchanged), drugs, including fluoxetine (Prozac) and paroxetine (Paxil),[17] Faecal (10%)[1][2][3] although trends favoring the efficacy of escitalopram (Lexapro), Identifiers sertraline (Zoloft) and venlafaxine (Effexor) over bupropion IUPAC name have been observed.[17] Mirtazapine (Remeron), on the other Synonyms 3­Chloro­N­tert­butyl­β­keto­α­ hand is significantly more effective than bupropion.[17] methylphenethylamine; Bupropion has several features that distinguish it from other antidepressants: for instance, unlike the majority of 3­Chloro­N­tert­butylcathinone; bupropion hydrochloride; antidepressants, it does not usually cause sexual dysfunction.[18] Bupropion treatment also is not associated with the sleepiness or amfebutamone weight gain that may be produced by other antidepressants.[19] CAS Number 34911­55­2 (http://www.commo nchemistry.org/ChemicalDetail.a In depressed people who experience symptoms of sleepiness and spx?ref=34911­55­2) fatigue, bupropion has been found to be more effective than selective serotonin reuptake inhibitors (SSRIs) in alleviating PubChem (CID) 444 (https://pubchem.ncbi.nlm.n ih.gov/summary/summary.cgi?ci these symptoms.[20] There appears to be a modest advantage for the SSRIs over bupropion in the treatment of anxious d=444) depression.[21] IUPHAR/BPS 7135 (http://www.guidetopharm acology.org/GRAC/LigandDispla yForward?ligandId=7135) https://en.wikipedia.org/wiki/Bupropion 2/16 13/01/2017 Bupropion ­ Wikipedia According to surveys, the addition to a prescribed SSRI is a DrugBank DB01156 (https://www.drugban common strategy when people do not respond to the SSRI, even k.ca/drugs/DB01156) [22] though this is not an officially approved indication. The ChemSpider 431 (http://www.chemspider.co addition of bupropion to an SSRI (most commonly fluoxetine or sertraline) may result in an improvement in some people who m/Chemical­Structure.431.html) have an incomplete response to the first­line antidepressant.[22] UNII 01ZG3TPX31 (http://fdasis.nlm. Bupropion was approved by the U.S. Food and Drug nih.gov/srs/srsdirect.jsp?regno=0 Administration (FDA), in 2006, for the prevention of seasonal 1ZG3TPX31) affective disorder.[23] In some countries (including Australia, KEGG New Zealand and the UK) this is an off­label use.[24][25] D07591 (http://www.kegg.jp/ent ry/D07591) Smoking cessation ChEBI CHEBI:3219 (https://www.ebi.a c.uk/chebi/searchId.do?chebiId= The next most common use is as an aid for smoking CHEBI:3219) cessation.[26][27] Bupropion reduces the severity of nicotine ChEMBL CHEMBL894 (https://www.ebi. cravings and withdrawal symptoms.[28] Bupropion is helpful for ac.uk/chembldb/index.php/comp smoking cessation in smokers with no history of depression; thus, the effectiveness of bupropion is not due to its ound/inspect/CHEMBL894) antidepressant effect. A typical bupropion treatment course lasts Chemical and physical data up to twelve weeks, with the people halting the use of tobacco Formula C H ClNO about ten days into the course. Bupropion approximately 13 18 doubles the chance of quitting smoking successfully.[28] The Molar mass 239.74 g/mol effectiveness of bupropion is comparable to nicotine 3D model (Jmol) Interactive image (http://chemap replacement therapy, but less effective than varenicline.[28] ps.stolaf.edu/jmol/jmol.php?mod el=O%3DC%28C%28C%29N In Australia and the UK smoking cessation is the only licensed C%28C%29%28C%29C%29C [24][25] use of bupropion. 1%3DCC%3DCC%28Cl%29%3 DC1) Attention deficit hyperactivity disorder SMILES Bupropion has been used as a treatment for attention deficit InChI [29] hyperactivity disorder (ADHD) since at least 2004, with (what is this?) (verify) reports of positive results in both minors and adults.[30] In a double­blind study of children, while aggression and hyperactivity as rated by the children's teachers were significantly improved in comparison to placebo, parents and clinicians could not distinguish between the effects of bupropion and placebo.[30] The 2007 guideline on the ADHD treatment from American Academy of Child and Adolescent Psychiatry notes that the evidence for bupropion is "far weaker" than for the FDA­approved treatments. Its effect may also be "considerably less than of the approved agents ... Thus it may be prudent for the clinician to recommend a trial of behavior therapy at this point, before moving to these second­line agents."[31] Similarly, the Texas Department of State Health Services guideline recommends considering bupropion or a tricyclic antidepressant as a fourth­line treatment after trying two different stimulants and atomoxetine.[32] Wellbutrin XL Sexual dysfunction https://en.wikipedia.org/wiki/Bupropion 3/16 13/01/2017 Bupropion ­ Wikipedia Bupropion is one of few antidepressants that do not cause sexual dysfunction.[33] A range of studies demonstrate that bupropion not only produces fewer sexual side effects than other antidepressants, but can actually help to alleviate sexual dysfunction.[34] According to a survey of psychiatrists, it is the drug of choice for the treatment of SSRI­induced sexual dysfunction, although this is not an indication approved by the U.S. Food and Drug Administration. There have also been a few studies suggesting that bupropion can improve sexual function in women who are not depressed, if they have hypoactive sexual desire disorder (HSDD).[35] Obesity Bupropion, when used for treating obesity over a period of 6 to 12 months, may result in weight loss of 2.7 kg over placebo.[36] This is not much different