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Wellbutrin XL

Bupropion
Skeletal formula of bupropion
Ball-and-stick model of the (S) isomer of the bupropion molecule
1 : 1 mixture (racemate)
Clinical data
Pronunciation /bjuːˈpr.pi.ɒn/
bew-PROH-pee-on
Trade names Wellbutrin, Elontril, Zyban
Synonyms Amfebutamone; 3-Chloro-N-tert-butyl-β-keto-α-methylphenethylamine;
3-Chloro-N-tert-butylcathinone;
Bupropion hydrochloride
AHFS/Drugs.com Monograph
MedlinePlus a695033
License data
Pregnancy
category
  • AU: B2
  • US: C (Risk not ruled out)
Dependence
liability
None to very low
Addiction
liability
None to very low
Routes of
administration
Medical: by mouth
Recreational: by mouth, insufflation, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 84% (bupropion), 77% (hydroxybupropion metabolite), 42% (threohydrobupropion metabolite)
Metabolism Liver (mostly CYP2B6-mediated hydroxylation, but with some contributions from CYP1A2, CYP2A6, CYP2C9, CYP3A4, CYP2E1 and CYP2C19)
Biological half-life 12–30 hours
Excretion Renal (87%; 0.5% unchanged), faecal (10%)
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
Formula C13H18ClNO
Molar mass 239.74 g/mol
3D model (JSmol)
 NYesY (what is this?)  

Bupropion is a medication primarily used as an antidepressant and smoking cessation aid. 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, although in many countries this is an off-label use. It is an effective antidepressant on its own, but is also popular as an add-on medication in cases of incomplete response to first-line SSRI antidepressants. Bupropion is taken in tablet form and is available only by prescription in most countries.

The most important side effect is an increase in risk for epileptic seizures, which caused the drug to be withdrawn from the market for some time and then caused the recommended dosage to be reduced. In comparison to many other antidepressants, it does not cause as much weight gain, sexual dysfunction, or sleepiness. Bupropion acts as an norepinephrine-dopamine reuptake inhibitor (NDRI). It is an atypical antidepressant, different from most commonly prescribed antidepressants such as selective serotonin reuptake inhibitors (SSRIs).

Bupropion is known to affect several different biological targets. It often is described as a norepinephrine-dopamine reuptake inhibitor (NDRI), and is also a nicotinic antagonist. However, bupropion does not appear to have significant dopaminergic actions in humans under normal clinical circumstances. Chemically, bupropion belongs to the class of aminoketones and is similar in structure to stimulants such as cathinone and amfepramone, and to phenethylamines in general.


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