Bupropion
 |
|
-bupropion_ball-and-stick_xtal_2009.png)
1 : 1 mixture (racemate)
|
|
| Clinical data | |
|---|---|
| Pronunciation |
/bjuːˈproʊ.pi.ɒn/ bew-PROH-pee-on |
| Trade names | Wellbutrin, Elontril, Zyban |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a695033 |
| License data | |
| Pregnancy category |
|
| Dependence liability |
none to very low |
| Addiction liability |
none to very low |
| Routes of administration |
Medical: oral Recreational: insufflation, intravenous |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Protein binding | 84% (bupropion), 77% (hydroxybupropion metabolite), 42% (threohydrobupropion metabolite) |
| Metabolism | Hepatic (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 | |
|
|
| Synonyms | 3-Chloro-N-tert-butyl-β-keto-α-methylphenethylamine; 3-Chloro-N-tert-butylcathinone; bupropion hydrochloride; amfebutamone |
| 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 (Jmol) | |
|
|
|
|
  (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The most important side effect is an increase in risk for epileptic seizures, which caused the drug to be withdrawn from the market for some time and then caused the recommended dosage to be reduced.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 or sexual dysfunction. 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.
...
Wikipedia