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 16–20 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] Other metabolites of bupropion besides hydroxybupropion include threohydrobupropion and erythrohydrobupropion.[3][4]
^ abcdeDwoskin LP (29 January 2014). Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse. Elsevier Science. pp. 177–216. ISBN 978-0-12-420177-4. Archived from the original on 4 June 2020. Retrieved 25 October 2016.
^Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 612–. ISBN 978-1-60913-345-0. Archived from the original on 11 December 2021. Retrieved 25 October 2016.
^Costa R, Oliveira NG, Dinis-Oliveira RJ (August 2019). "Pharmacokinetic and pharmacodynamic of bupropion: integrative overview of relevant clinical and forensic aspects". Drug Metabolism Reviews. 51 (3): 293–313. doi:10.1080/03602532.2019.1620763. PMID 31124380. S2CID 163167323.
^Cite error: The named reference Jefferson_2005 was invoked but never defined (see the help page).
Hydroxybupropion (code name BW 306U), or 6-hydroxybupropion, is the major active metabolite of the antidepressant and smoking cessation drug bupropion...
(developmental code GW-353,162; also known as (2S,3S)-hydroxybupropion or (S,S)-hydroxybupropion) is a norepinephrine–dopamine reuptake inhibitor (NDRI)...
bupropion and decrease of hydroxybupropion blood concentration. The reverse effect (decrease of bupropion and increase of hydroxybupropion) can be expected with...
2R)-erythrohydrobupropion. Other metabolites of bupropion include hydroxybupropion and threohydrobupropion. Information on the pharmacological actions...
(1S,2S)-threohydrobupropion. Other metabolites of bupropion include hydroxybupropion and erythrohydrobupropion. Information on the pharmacological actions...
more potent NRI and likely NRA due to bupropion's major metabolite hydroxybupropion) Cocaine Fluorenol (extremely weak) Medifoxamine (relatively weak)...
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