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.^[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]

^ ^a ^b ^c ^d ^e Dwoskin 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).

[Dwoskin_2014-1] Dwoskin 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_2012-2] 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_2019-3] 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.

[Jefferson_2005-4] Cite error: The named reference Jefferson_2005 was invoked but never defined (see the help page).

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