Wellbutrin XL

Bupropion

1 : 1 mixture (racemate)
Clinical data
Pronunciation	/bjuːˈproʊ.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	US FDA: Bupropion
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	N06AX12 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
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
IUPAC name (RS)-2-(tert-Butylamino)-1-(3-chlorophenyl)propan-1-one
CAS Number	34911-55-2 Y[PubChem]
PubChem CID	444
IUPHAR/BPS	7135
DrugBank	DB01156 Y
ChemSpider	431 Y
UNII	01ZG3TPX31
KEGG	D07591 Y
ChEBI	CHEBI:3219 Y
ChEMBL	CHEMBL894 Y
Chemical and physical data
Formula	C13H18ClNO
Molar mass	239.74 g/mol
3D model (JSmol)	Interactive image
SMILES O=C(C(C)NC(C)(C)C)C1=CC=CC(Cl)=C1
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 Y Key:SNPPWIUOZRMYNY-UHFFFAOYSA-N Y
NY (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The most important side effect is an increase in risk for epileptic seizures, which caused the drug to be withdrawn from the market for some time and then caused the recommended dosage to be reduced.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.