Hydroxybupropion

Hydroxybupropion
Clinical data
Other names	BW 306U; 6-Hydroxybupropion
ATC code	None;
Pharmacokinetic data
Elimination half-life	15–25 hours
Identifiers
	IUPAC name (±)-1-(3-Chlorophenyl)-2-[(1-hydroxy-2-methyl-2-propanyl)amino]-1-propanone;
CAS Number	357399-43-0 ;
PubChem CID	446;
ChemSpider	433;
UNII	V94F513635;
ChEBI	CHEBI:166487;
ChEMBL	ChEMBL3544616;
CompTox Dashboard (EPA)	DTXSID101002894 ;
Chemical and physical data
Formula	C13H18ClNO2
Molar mass	255.74 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1cc(Cl)ccc1)C(NC(C)(C)CO)C;
	InChI InChI=1S/C13H18ClNO2/c1-9(15-13(2,3)8-16)12(17)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3; Key:AKOAEVOSDHIVFX-UHFFFAOYSA-N;

Hydroxybupropion (code name BW 306U), or 6-hydroxybupropion, is the major active metabolite of the antidepressant and smoking cessation drug bupropion. It is formed from bupropion by the liver enzyme CYP2B6 during first-pass metabolism. With oral bupropion treatment, hydroxybupropion is present in plasma at area under the curve concentrations that are as many as 16 to 20 times greater than those of bupropion itself, demonstrating extensive conversion of bupropion into hydroxybupropion in humans. As such, hydroxybupropion is likely to play a very important role in the effects of oral bupropion, which could accurately be thought of as functioning largely as a prodrug to hydroxybupropion.

Hydroxybupropion has two chiral centers and is a mixture of four possible enantiomers. In humans however, presumably due to steric hindrance, only (2R,3R)-hydroxybupropion and (2S,3S)-hydroxybupropion are formed.

Other metabolites of bupropion besides hydroxybupropion include threohydrobupropion and erythrohydrobupropion.