Description

Buy Hydroxybupropion (BW 306U) Cas 357399-43-0

Hydroxybupropion (code name BW 306U), or 6-hydroxybupropion, is the major active metabolite of the antidepressant and smoking cessation drug bupropion.^[1] It is formed from bupropion by the liver enzyme CYP2B6 during first-pass metabolism.^[1] 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,^[1][2] demonstrating extensive conversion of bupropion into hydroxybupropion in humans.^[1] 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.^[1] Hydroxybupropion has two chiral centers and is a mixture of four possible enantiomers.^[3][4][5] In humans, however, presumably due to steric hindrance, only (2R,3R)-hydroxybupropion and (2S,3S)-hydroxybupropion are formed.^[3][4][5] Other metabolites of bupropion besides hydroxybupropion include threohydrobupropion and erythrohydrobupropion.^[6][7]

Pharmacology of bupropion and its metabolites

	Bupropion	R,R- Hydroxy bupropion	S,S- Hydroxy bupropion	Threo- hydro bupropion	Erythro- hydro bupropion
Exposure and half-life
AUC relative to bupropion[8][9]	1	23.8	0.6	11.2	2.5
Half-life[10]	10.8 h	19 h	15 h	31 h	22 h
Inhibition IC50 (μM) in human cells, unless noted otherwise
DAT, uptake[11]	0.66	inactive	0.63	47 (rat)[12]	no data
NET, uptake[11]	1.85	9.9	0.24	16 (rat)[12]	no data
SERT, uptake[11]	inactive	inactive	inactive	67 (rat)[12]	no data
α3β4 nicotinic[11]	1.8	6.5	11	14 (rat)[13]	no data
α4β2 nicotinic[14]	12	31	3.3	no data	no data
α1β1γδ nicotinic[14]	7.9	7.6	28	no data	no data

Compared to bupropion, hydroxybupropion is similar in its potency as a norepinephrine reuptake inhibitor (IC₅₀ = 1.7 μM), but is substantially weaker as a dopamine reuptake inhibitor (IC₅₀ = >10 μM).^[14] Like bupropion, hydroxybupropion is also a non-competitive antagonist of nACh receptors, such as α₄β₂ and α₃β₄, but is even more potent in comparison.^{[1][14][15][16][17]}