Chemical: Drug
bupropion

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Clinical Variants that meet the highest level of criteria, manually curated by PharmGKB, are shown below.

To see more Clinical Variants with lower levels of criteria, click the button at the bottom of the page.

Disclaimer: The PharmGKB's clinical annotations reflect expert consensus based on clinical evidence and peer-reviewed literature available at the time they are written and are intended only to assist clinicians in decision-making and to identify questions for further research. New evidence may have emerged since the time an annotation was submitted to the PharmGKB. The annotations are limited in scope and are not applicable to interventions or diseases that are not specifically identified.

The annotations do not account for individual variations among patients, and cannot be considered inclusive of all proper methods of care or exclusive of other treatments. It remains the responsibility of the health-care provider to determine the best course of treatment for a patient. Adherence to any guideline is voluntary, with the ultimate determination regarding its application to be made solely by the clinician and the patient. PharmGKB assumes no responsibility for any injury or damage to persons or property arising out of or related to any use of the PharmGKB clinical annotations, or for any errors or omissions.

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The table below contains information about pharmacogenomic variants on PharmGKB. Please follow the link in the "Variant" column for more information about a particular variant. Each link in the "Variant" column leads to the corresponding PharmGKB Variant Page. The Variant Page contains summary data, including PharmGKB manually curated information about variant-drug pairs based on individual PubMed publications. The PMIDs for these PubMed publications can be found on the Variant Page.

The tags in the first column of the table indicate what type of information can be found on the corresponding Variant Page.

Links in the "Gene" column lead to PharmGKB Gene Pages.

List of all variant annotations for bupropion

Gene ? Variant?
(147)
Alternate Names ? Chemicals ? Alleles ?
(+ chr strand)
Function ? Amino Acid?
Translation
No VIP available No VIP available VA APOE E4 N/A N/A N/A
No VIP available CA VA CYP2B6 *1 N/A N/A N/A
No VIP available CA No VIP available CYP2B6 *2 N/A N/A N/A
No VIP available CA VA CYP2B6 *4 N/A N/A N/A
No VIP available CA VA CYP2B6 *5 N/A N/A N/A
VIP CA VA CYP2B6 *6 N/A N/A N/A
No VIP available No VIP available VA CYP2B6 *6B N/A N/A N/A
No VIP available CA VA CYP2B6 *18 N/A N/A N/A
No VIP available CA VA CYP2B6 *22 N/A N/A N/A
No VIP available CA VA CYP2C19 *1 N/A N/A N/A
No VIP available CA VA CYP2C19 *2 N/A N/A N/A
No VIP available No VIP available VA CYP2C19 *3 N/A N/A N/A
No VIP available No VIP available VA CYP2C19 *17 N/A N/A N/A
No VIP available CA VA
rs11746641 NC_000005.10:g.175439088T>G, NC_000005.9:g.174866091T>G, NG_011802.1:g.10073A>C
T > G
SNP
No VIP available CA VA
rs11749035 NC_000005.10:g.175456049C>T, NC_000005.9:g.174883052C>T
C > T
SNP
No VIP available No Clinical Annotations available VA
rs12721655 NC_000019.10:g.41004377A>G, NC_000019.9:g.41510282A>G, NG_007929.1:g.18079A>G, NM_000767.4:c.415A>G, NP_000758.1:p.Lys139Glu, XM_005258569.1:c.415A>G, XM_005258569.3:c.415A>G, XM_005258570.1:c.415A>G, XM_005258571.1:c.295A>G, XM_006723050.2:c.415A>G, XM_011526546.1:c.415A>G, XM_011526547.1:c.415A>G, XM_011526548.1:c.415A>G, XM_011526549.1:c.-145A>G, XM_011526550.1:c.295A>G, XP_005258626.1:p.Lys139Glu, XP_005258627.1:p.Lys139Glu, XP_005258628.1:p.Lys99Glu, XP_006723113.1:p.Lys139Glu, XP_011524848.1:p.Lys139Glu, XP_011524849.1:p.Lys139Glu, XP_011524850.1:p.Lys139Glu, XP_011524852.1:p.Lys99Glu, rs56006122
A > G
SNP
K139E
No VIP available CA VA
rs165599 NC_000022.10:g.19956781G>A, NC_000022.11:g.19969258G>A, NG_011526.1:g.32519G>A, NG_023326.1:g.52529C>T, NM_000754.3:c.*522G>A, NM_001135161.1:c.*522G>A, NM_001135162.1:c.*522G>A, NM_007310.2:c.*522G>A, XM_005261229.1:c.*522G>A, XM_005261242.1:c.2764-2049C>T, XM_006724243.1:c.2782-2049C>T, XM_006724246.2:c.2536-2049C>T, XM_011529886.1:c.*522G>A, XM_011530179.1:c.2749-2049C>T, XM_011530182.1:c.1348-2049C>T, rs58966983
G > A
SNP
rs1799732 NC_000011.10:g.113475529_113475530insG, NC_000011.9:g.113346251_113346252insG, NG_008841.1:g.4750_4751insC, NM_000795.3:c.-486_-485insC, NM_016574.3:c.-486_-485insC, XM_005271425.1:c.-32+128_-32+129insC, XR_948023.1:n.528_529insC, rs143987432, rs144707848, rs72523179, rs72566141
- > G
indel
rs1800497 NC_000011.10:g.113400106G>A, NC_000011.9:g.113270828G>A, NG_012976.1:g.17316G>A, NM_178510.1:c.2137G>A, NP_848605.1:p.Glu713Lys, XM_011542736.1:c.2170G>A, XM_011542737.1:c.2140G>A, XM_011542738.1:c.1948G>A, XP_011541038.1:p.Glu724Lys, XP_011541039.1:p.Glu714Lys, XP_011541040.1:p.Glu650Lys, rs117686243, rs4134623, rs4245144, rs59538675
G > A
SNP
E713K
No VIP available CA VA
rs1969624 NC_000003.11:g.45734818T>C, NC_000003.12:g.45693326T>C, NM_001319072.1:c.-24+3829T>C, NM_001319073.1:c.-278+2939T>C, NM_014016.4:c.32+3829T>C, XM_005264965.1:c.-24+3829T>C, XM_011533499.1:c.-24+3829T>C, XM_011533500.1:c.-24+2939T>C, XR_245103.1:n.142+3829T>C, XR_940392.1:n.142+3829T>C, rs17328736, rs58249512
T > C
SNP
No VIP available No Clinical Annotations available VA
rs2056527 NC_000003.11:g.152707929T>C, NC_000003.12:g.152990140T>C, rs58134442
T > C
SNP
No VIP available CA VA
rs2168631 NC_000005.10:g.175448999G>A, NC_000005.9:g.174876002G>A, NG_011802.1:g.162C>T, rs59556958
G > A
SNP
No VIP available CA VA
rs2245705 NC_000003.11:g.45749722T>C, NC_000003.12:g.45708230T>C, NM_001319072.1:c.151-1268T>C, NM_001319073.1:c.25-1268T>C, NM_014016.4:c.334-1268T>C, XM_005264965.1:c.151-1268T>C, XM_011533499.1:c.151-1268T>C, XM_011533500.1:c.151-1268T>C, XR_245103.1:n.444-1268T>C, XR_940392.1:n.444-1268T>C, rs56439728, rs61193957
T > C
SNP
No VIP available CA VA
rs2251954 NC_000003.11:g.45731784T>C, NC_000003.12:g.45690292T>C, NM_001319072.1:c.-24+795T>C, NM_001319073.1:c.-317-56T>C, NM_014016.4:c.32+795T>C, NR_033947.1:n.-1410A>G, XM_005264965.1:c.-24+795T>C, XM_011533499.1:c.-24+795T>C, XM_011533500.1:c.-63-56T>C, XR_245103.1:n.142+795T>C, XR_940392.1:n.142+795T>C, rs3774665, rs60407120
T > C
SNP
No VIP available CA VA
rs2279343 NC_000019.10:g.41009358A>G, NC_000019.9:g.41515263A>G, NG_007929.1:g.23060A>G, NM_000767.4:c.785A>G, NP_000758.1:p.Lys262Arg, XM_005258569.1:c.785A>G, XM_005258569.3:c.785A>G, XM_005258570.1:c.785A>G, XM_005258571.1:c.365-2940A>G, XM_006723050.2:c.785A>G, XM_011526546.1:c.785A>G, XM_011526547.1:c.785A>G, XM_011526548.1:c.485-2940A>G, XM_011526549.1:c.194A>G, XM_011526550.1:c.365-2940A>G, XP_005258626.1:p.Lys262Arg, XP_005258627.1:p.Lys262Arg, XP_006723113.1:p.Lys262Arg, XP_011524848.1:p.Lys262Arg, XP_011524849.1:p.Lys262Arg, XP_011524851.1:p.Lys65Arg
A > G
SNP
K262R
No VIP available CA VA
rs2717162 NC_000018.10:g.77256371T>C, NC_000018.9:g.74968327T>C, NG_009223.1:g.11320T>C, NM_001480.3:c.732+148T>C, rs57387914
T > C
SNP
No VIP available CA VA
rs2742390 NC_000003.11:g.45756722G>A, NC_000003.12:g.45715230G>A, NM_001319072.1:c.394+1151G>A, NM_001319073.1:c.268+1151G>A, NM_014016.4:c.577+1151G>A, XM_005264965.1:c.394+1151G>A, XM_011533499.1:c.394+1151G>A, XM_011533500.1:c.394+1151G>A, XR_245103.1:n.687+1151G>A, XR_940392.1:n.687+1151G>A, rs17263686, rs61051571
G > A
SNP
No VIP available CA VA
rs2742417 NC_000003.11:g.45731451C>T, NC_000003.12:g.45689959C>T, NM_001319072.1:c.-24+462C>T, NM_001319073.1:c.-317-389C>T, NM_014016.4:c.32+462C>T, NR_033947.1:n.-1077G>A, XM_005264965.1:c.-24+462C>T, XM_011533499.1:c.-24+462C>T, XM_011533500.1:c.-63-389C>T, XR_245103.1:n.142+462C>T, XR_940392.1:n.142+462C>T, rs56457125, rs57741455
C > T
SNP
No VIP available CA VA
rs2742421 NC_000003.11:g.45732515T>G, NC_000003.12:g.45691023T>G, NM_001319072.1:c.-24+1526T>G, NM_001319073.1:c.-278+636T>G, NM_014016.4:c.32+1526T>G, XM_005264965.1:c.-24+1526T>G, XM_011533499.1:c.-24+1526T>G, XM_011533500.1:c.-24+636T>G, XR_245103.1:n.142+1526T>G, XR_940392.1:n.142+1526T>G, rs3774662, rs60315361
T > G
SNP
No VIP available CA VA
rs2742423 NC_000003.11:g.45733430A>G, NC_000003.12:g.45691938A>G, NM_001319072.1:c.-24+2441A>G, NM_001319073.1:c.-278+1551A>G, NM_014016.4:c.32+2441A>G, XM_005264965.1:c.-24+2441A>G, XM_011533499.1:c.-24+2441A>G, XM_011533500.1:c.-24+1551A>G, XR_245103.1:n.142+2441A>G, XR_940392.1:n.142+2441A>G, rs58317800
A > G
SNP
No VIP available CA VA
rs2742435 NC_000003.11:g.45740863G>A, NC_000003.12:g.45699371G>A, NM_001319072.1:c.-23-4067G>A, NM_001319073.1:c.-277-4067G>A, NM_014016.4:c.33-4067G>A, XM_005264965.1:c.-23-4067G>A, XM_011533499.1:c.-23-4067G>A, XM_011533500.1:c.-23-4067G>A, XR_245103.1:n.143-4067G>A, XR_940392.1:n.143-4067G>A, rs17328981, rs61726216
G > A
SNP
VIP No Clinical Annotations available No Variant Annotations available
rs28399499 NC_000019.10:g.41012316T>C, NC_000019.9:g.41518221T>C, NG_007929.1:g.26018T>C, NM_000767.4:c.983T>C, NP_000758.1:p.Ile328Thr, XM_005258569.1:c.983T>C, XM_005258569.3:c.983T>C, XM_005258570.1:c.983T>C, XM_005258571.1:c.383T>C, XM_006723050.2:c.983T>C, XM_011526546.1:c.983T>C, XM_011526547.1:c.983T>C, XM_011526548.1:c.503T>C, XM_011526549.1:c.392T>C, XM_011526550.1:c.383T>C, XP_005258626.1:p.Ile328Thr, XP_005258627.1:p.Ile328Thr, XP_005258628.1:p.Ile128Thr, XP_006723113.1:p.Ile328Thr, XP_011524848.1:p.Ile328Thr, XP_011524849.1:p.Ile328Thr, XP_011524850.1:p.Ile168Thr, XP_011524851.1:p.Ile131Thr, XP_011524852.1:p.Ile128Thr
T > C
SNP
I328T
No VIP available No Clinical Annotations available VA
rs2868177 NC_000007.13:g.75589903A>G, NC_000007.14:g.75960585A>G, NG_008930.1:g.50484A>G, NM_000941.2:c.188+6405A>G, NW_003871064.1:g.3489821A>G, XM_005250459.1:c.188+6405A>G, XM_005250461.1:c.-264+6405A>G, XM_005277600.1:c.188+6405A>G, XM_005277602.1:c.-264+6405A>G, rs10375158, rs59093849, rs61116122
A > G
SNP
rs3211371 NC_000019.10:g.41016810C>T, NC_000019.9:g.41522715C>T, NG_007929.1:g.30512C>T, NM_000767.4:c.1459C>T, NP_000758.1:p.Arg487Cys, XM_005258569.1:c.*48C>T, XM_005258569.3:c.*48C>T, XM_005258570.1:c.*214C>T, XM_005258571.1:c.859C>T, XM_006723050.2:c.*143C>T, XM_011526547.1:c.*214C>T, XM_011526548.1:c.979C>T, XM_011526549.1:c.868C>T, XM_011526550.1:c.859C>T, XP_005258628.1:p.Arg287Cys, XP_011524850.1:p.Arg327Cys, XP_011524851.1:p.Arg290Cys, XP_011524852.1:p.Arg287Cys, rs12721654, rs28399500, rs33995163, rs58951873
C > T
SNP
R487C
No VIP available No Clinical Annotations available VA
rs3745274 NC_000019.10:g.41006936G>T, NC_000019.9:g.41512841G>T, NG_007929.1:g.20638G>T, NM_000767.4:c.516G>T, NP_000758.1:p.Gln172His, XM_005258569.1:c.516G>T, XM_005258569.3:c.516G>T, XM_005258570.1:c.516G>T, XM_005258571.1:c.364+2490G>T, XM_006723050.2:c.516G>T, XM_011526546.1:c.516G>T, XM_011526547.1:c.516G>T, XM_011526548.1:c.484+2490G>T, XM_011526549.1:c.-75-1G>T, XM_011526550.1:c.364+2490G>T, XP_005258626.1:p.Gln172His, XP_005258627.1:p.Gln172His, XP_006723113.1:p.Gln172His, XP_011524848.1:p.Gln172His, XP_011524849.1:p.Gln172His, rs56308434, rs57685583
G > T
SNP
Q172H
No VIP available CA VA
rs4803381 NC_000019.10:g.40851439T>C, NC_000019.9:g.41357344T>C, NG_008377.1:g.4009A>G, NM_000762.5:c.-1013A>G, XM_005258568.1:c.-1013A>G, rs12985612, rs150298687, rs60981283, rs7260262, rs73553054
T > C
SNP
VIP No Clinical Annotations available No Variant Annotations available
rs6277 NC_000011.10:g.113412737G>A, NC_000011.9:g.113283459G>A, NG_008841.1:g.67543C>T, NM_000795.3:c.957C>T, NM_016574.3:c.870C>T, NP_000786.1:p.Pro319=, NP_057658.2:p.Pro290=, XM_005271425.1:c.957C>T, XM_005271426.1:c.954C>T, XP_005271482.1:p.Pro319=, XP_005271483.1:p.Pro318=, rs1071576, rs1075651, rs17413837, rs3189090
G > A
SNP
P319P
No VIP available CA VA
rs6702335 NC_000001.10:g.29411250A>G, NC_000001.11:g.29084738A>G, NG_013344.1:g.202648A>G, NM_001166005.1:c.2185-13069A>G, NM_001166007.1:c.1396-13069A>G, NM_004437.3:c.1459-13069A>G, NM_203342.2:c.1516-13069A>G, NM_203343.2:c.1918-13069A>G, XM_005245753.1:c.2185-11417A>G, XM_005245754.1:c.2182-11417A>G, XM_005245755.1:c.2143-11417A>G, XM_005245756.1:c.2086-11417A>G, XM_005245757.1:c.2080-11417A>G, XM_005245758.1:c.2077-11417A>G, XM_005245759.1:c.2023-11417A>G, XM_005245760.1:c.2236-13069A>G, XM_005245761.1:c.2185-13069A>G, XM_005245762.1:c.2185-11417A>G, XM_005245763.1:c.2143-13069A>G, XM_005245764.1:c.2086-13069A>G, XM_005245765.1:c.2080-13069A>G, XM_005245768.1:c.2184+19580A>G, XM_005245769.1:c.2023-13069A>G, XM_005245770.1:c.2020-13069A>G, XM_005245771.1:c.1558-11417A>G, XM_005245774.1:c.2022+19580A>G, XM_006710434.1:c.2221-11417A>G, XM_006710439.1:c.2221-13069A>G, XM_011540956.1:c.2236-11417A>G, XM_011540957.1:c.2233-11417A>G, XM_011540958.1:c.2236-11417A>G, XM_011540959.1:c.2194-11417A>G, XM_011540960.1:c.2137-11417A>G, XM_011540961.1:c.2131-11417A>G, XM_011540962.1:c.2074-11417A>G, XM_011540964.1:c.1609-11417A>G
A > G
SNP
No VIP available No Clinical Annotations available VA
rs737865 NC_000022.10:g.19930121A>G, NC_000022.11:g.19942598A>G, NG_011526.1:g.5859A>G, NG_011835.1:g.4239T>C, NM_000754.3:c.-92+701A>G, NM_001282512.1:c.-795T>C, NM_006440.4:c.-795T>C, XM_005261214.1:c.-795T>C, XM_005261216.1:c.-795T>C, XM_005261217.1:c.-795T>C, XM_005261229.1:c.-386+701A>G, XM_011529887.1:c.-92+701A>G, XM_011529890.1:c.-386+701A>G, XM_011529891.1:c.-386+423A>G, rs386609682, rs59045144
A > G
SNP
Alleles, Functions, and Amino Acid Translations are all sourced from dbSNP 147

Overview

Generic Names
  • Amfebutamone
  • Bupropion Hcl
Trade Names
  • Wellbatrin
  • Wellbutrin
  • Wellbutrin SR
  • Wellbutrin XL
  • Zyban
Brand Mixture Names

PharmGKB Accession Id

PA448687

Type(s):

Drug

Description

A unicyclic, aminoketone antidepressant. The mechanism of its therapeutic actions is not well understood, but it does appear to block dopamine uptake. The hydrochloride is available as an aid to smoking cessation treatment.

Source: Drug Bank

Pharmacogenetics

Pharmacokinetics

Bupropion undergoes metabolic transformation to an active metabolite, 4-hydroxybupropion, which is formed almost exclusively via CYP2B6 [Article:17009913] and CYP2B6 VIP page. In in vitro studies using a panel of cDNA-expressed P450 isoforms, cDNA-expressed CYP2E1 and CYP3A4 catalyzed bupropion hydroxylation to 4-hydroxybupropion at the second and third highest rates, but significant lower than cDNA-expressed CYP2B6 (3- and 30-fold lower rates, respectively) [Article:10997944]. A study in human liver microsomes suggests that CYP3A4 does not significantly catalyze bupropion hydroxylation [Article:11454731]. The amino-alcohol isomers threohydrobupropion and erythrohydrobupropion are other metabolites of bupropion, which are formed via reduction of the carbonyl group [Article:18420781]. Bupropion is moderate inhibitor of CYP2D6 [Articles:18691982, 10997936]. In studies using human liver microsomes or human hepatocytes, erythrohydrobupropion and threohydrobupropion were more potent CYP2D6 inhibitors than bupropion or hydroxybupropion [Articles:18420781, 20208386]. Bupropion was reported to cause clinically significant inhibition of the metabolism of several CYP2D6 substrates including desipramine, dextromethorphan, and venlafaxine [Article:20208386]. A study using human hepatocytes concludes that multiple doses of bupropion are not likely to induce CYP2B6, CYP3A4 or CYP2E1 in vivo [Article:14604466].

In vitro studies using an ATPase assay in membranes expressing human P-glycoprotein 1 (ABCB1) found that bupropion, hydroxybupropion, threohydrobupropion, and erythrohydrobupropion have only very weak affinity for P-glycoprotein [Article:18239278].

Pharmacodynamics

Bupropion hydrochloride is a noradrenergic/dopaminergic antidepressant. The mechanism of action underlying the antidepressant effect of bupropion is still not well understood but maybe partially related to inhibition of presynaptic dopamine (SLC6A3) and norepinephrine reuptake transporters (SLC6A2). A study in rats found that bupropion rapidly, reversibly, and dose-dependently increased vesicular dopamine uptake; an effect also associated with vesicle monoamine transporter type-2 (SLC18A2) redistribution [Article:16005476]. Animal studies (rat and mice) showed that bupropion blocks nicotine activation of alpha(3)beta(2), alpha(4)beta(2), and alpha(7) neuronal acetylcholine nicotinic receptors (CHRNs) with some degree of selectivity [Article:10991997]. In vitro studies with several human muscle and neuronal nicotinic acetylcholine receptor types confirmed these interactions [Articles:15322260, 19334677, 19897080]. Bupropion is approved as a non-nicotine pharmacotherapy for the treatment of nicotine dependence [Article:16939383]. In vitro experiments, which investigated the effect of antidepressants on SREBP-controlled lipid biosynthesis, demonstrated that bupropion is able to activate the transcription factors SREBF1 and SREBF2 [Article:16324787]. The study results may also be relevant for drug-induced metabolic side effects [Article:16324787]. Bupropion increased the expression of the immediate early gene c-Fos (FOS) in cell culture [Article:12112414] and rat brain [Article:7865498].

Pharmacogenomics

The association of polymorphisms in several genes and smoking cessation following bupropion therapy are investigated in a number of studies reviewed in [Article:19028511] and [Article:19475569]. According to a recent review only a few candidate genes or regions were analyzed more than twice [Article:19475569]. Variants in the following genes were associated with treatment response to bupropion for smoking cessation: D2 dopamine receptor (DRD2) [Articles:14668077, 15492764, 16123753]; dopamine transporter (SLC6A3) [Articles:14570538, 17264803, 18197080], catechol-O-methyltransferase (COMT) [Articles:16876132, 1819708], norepinephrine transporter (SLC6A2) [Article:1819708], neuronal nicotinic acetylcholine receptor beta 2 (CHRNB2) [Article:18593715], neuronal acetylcholine receptor subunit alpha-5 (CHRNA5) [Article:18165968], neuronal acetylcholine receptor subunit alpha-2 (CHRNA2) [Article:18165968], and choline O-acetyltransferase (CHAT) [Article:18165968]. For additional information see Clinical Annotations tab and PGx Research tab for bupropion.

Source: PharmGKB

Indication

For the treatment of depression and as aid to smoking cessation.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

Bupropion selectively inhibits the neuronal reuptake of dopamine, norepinephrine, and serotonin; actions on dopaminergic systems are more significant than imipramine or amitriptyline whereas the blockade of norepinephrine and serotonin reuptake at the neuronal membrane is weaker for bupropion than for tricyclic antidepressants. The increase in norepinephrine may attenuate nicotine withdrawal symptoms and the increase in dopamine at neuronal sites may reduce nicotine cravings and the urge to smoke. Bupropion exhibits moderate anticholinergic effects.

Source: Drug Bank

Pharmacology

Bupropion, an antidepressant of the aminoketone class and a non-nicotine aid to smoking cessation, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Compared to classical tricyclic antidepressants, Bupropion is a relatively weak inhibitor of the neuronal uptake of norepinephrine, serotonin, and dopamine. In addition, Bupropion does not inhibit monoamine oxidase. Bupropion produces dose-related central nervous system (CNS) stimulant effects in animals, as evidenced by increased locomotor activity, increased rates of responding in various schedule-controlled operant behavior tasks, and, at high doses, induction of mild stereotyped behavior.

Source: Drug Bank

Food Interaction

Avoid St.John's Wort.|Avoid alcohol.|Take without regard to meals.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Reduction of the carbonyl groupand/or hydroxylation of the tert-butyl group of bupropion.

Source: Drug Bank

Protein Binding

84 %

Source: Drug Bank

Absorption

For sustained release, peak plasma concentrations are achieved within 3 hours.

Source: Drug Bank

Half-Life

24 hours

Source: Drug Bank

Toxicity

Symptoms of overdose include seizures, hallucinations, loss of consciousness, tachycardia, and cardiac arrest.

Source: Drug Bank

Route of Elimination

Bupropion is extensively metabolized in humans. Oxidation of the bupropion side chain results in the formation of a glycine conjugate of metachlorobenzoic acid, which is then excreted as the major urinary metabolite. Following oral administration of 200 mg of 14C-bupropion in humans, 87% and 10% of the radioactive dose were recovered in the urine and feces, respectively. However, the fraction of the oral dose of bupropion excreted unchanged was only 0.5%, a finding consistent with the extensive metabolism of bupropion.

Source: Drug Bank

Chemical Properties

Chemical Formula

C13H18ClNO

Source: Drug Bank

Isomeric SMILES

CC(C(=O)c1cccc(c1)Cl)NC(C)(C)C

Source: OpenEye

Canonical SMILES

CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1

Source: Drug Bank

Average Molecular Weight

239.741

Source: Drug Bank

Monoisotopic Molecular Weight

239.10769191

Source: Drug Bank

SMILES

CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1

Source: Drug Bank

InChI String

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

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

Curated Information ?

Drug Targets

Gene Description
CHRNA3 (source: Drug Bank)
SLC6A2 (source: Drug Bank)
SLC6A3 (source: Drug Bank)

Drug Interactions

Interaction Description
bupropion - carbamazepine Carbamazepine decreases the effect of bupropion (source: Drug Bank)
bupropion - carbamazepine Carbamazepine decreases the effect of bupropion (source: Drug Bank)
bupropion - cyclosporine Decreases the effect of cyclosporine (source: Drug Bank)
bupropion - cyclosporine Decreases the effect of cyclosporine (source: Drug Bank)
bupropion - isocarboxazid Possible severe adverse reaction with this combination (source: Drug Bank)
bupropion - isocarboxazid Possible severe adverse reaction with this combination (source: Drug Bank)
bupropion - phenelzine Possible severe adverse reaction with this combination (source: Drug Bank)
bupropion - phenelzine Possible severe adverse reaction with this combination (source: Drug Bank)
bupropion - rasagiline Possible severe adverse reaction with this combination (source: Drug Bank)
bupropion - rifabutin Rifampin reduces bupropion levels (source: Drug Bank)
bupropion - rifabutin Rifampin reduces bupropion levels (source: Drug Bank)
bupropion - rifampin Rifampin reduces bupropion levels (source: Drug Bank)
bupropion - rifampin Rifampin reduces bupropion levels (source: Drug Bank)
bupropion - ritonavir Ritonavir increases the effect and toxicity of bupropion (source: Drug Bank)
bupropion - ritonavir Ritonavir increases the effect and toxicity of bupropion (source: Drug Bank)
bupropion - thioridazine Inceases the effect and toxicity of thioridazine (source: Drug Bank)
bupropion - thioridazine Inceases the effect and toxicity of thioridazine (source: Drug Bank)
bupropion - tranylcypromine Possible severe adverse reaction with this combination (source: Drug Bank)
bupropion - tranylcypromine Possible severe adverse reaction with this combination (source: Drug Bank)
carbamazepine - bupropion Decreases the effect of bupropion (source: Drug Bank)
carbamazepine - bupropion Decreases the effect of bupropion (source: Drug Bank)
cyclosporine - bupropion Bupropion decreases the effect of cyclosporine (source: Drug Bank)
cyclosporine - bupropion Bupropion decreases the effect of cyclosporine (source: Drug Bank)
isocarboxazid - bupropion Possible severe adverse reaction with this combination (source: Drug Bank)
isocarboxazid - bupropion Possible severe adverse reaction with this combination (source: Drug Bank)
phenelzine - bupropion Possible severe adverse reaction with this combination (source: Drug Bank)
phenelzine - bupropion Possible severe adverse reaction with this combination (source: Drug Bank)
rasagiline - bupropion Possible severe adverse reaction with this combination (source: Drug Bank)
rifabutin - bupropion Rifampin reduces bupropion levels (source: Drug Bank)
rifabutin - bupropion Rifampin reduces bupropion levels (source: Drug Bank)
rifampin - bupropion Rifampin reduces bupropion levels (source: Drug Bank)
rifampin - bupropion Rifampin reduces bupropion levels (source: Drug Bank)
thioridazine - bupropion Bupropion increases the effect and toxicity of thioridazine (source: Drug Bank)
thioridazine - bupropion Bupropion increases the effect and toxicity of thioridazine (source: Drug Bank)
thiotepa - bupropion Thiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Bupropion, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Bupropion if Thiotepa is initiated, discontinued or dose changed. (source: Drug Bank)
tranylcypromine - bupropion The MAO inhibitor, Tranylcypromine, may increase the central neurotoxic effects of the Bupropion. These agents should not be administered within 14 days of each other. (source: Drug Bank)
triprolidine - bupropion The CNS depressants, Triprolidine and Bupropion, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy. (source: Drug Bank)
triprolidine - bupropion The CNS depressants, Triprolidine and Bupropion, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy. (source: Drug Bank)
zuclopenthixol - bupropion Bupropion, a strong CYP2D6 inhibitor, may increase the serum concentration of zuclopenthixol by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zuclopenthixol if bupropion is initiated, discontinued or dose changed. (source: Drug Bank)

Curated Information ?

Relationships from National Drug File - Reference Terminology (NDF-RT)

May Treat
Contraindicated With

Publications related to bupropion: 64

No Dosing Guideline available No Drug Label available No Clinical Annotation available VA No VIP available No VIP available
Pharmacokinetics of bupropion and its pharmacologically active metabolites in pregnancy. Drug metabolism and disposition: the biological fate of chemicals. 2016. Fokina Valentina M, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available VA No VIP available No VIP available
Effects of the selected cytochrome P450 oxidoreductase genetic polymorphisms on cytochrome P450 2B6 activity as measured by bupropion hydroxylation. Pharmacogenetics and genomics. 2015. Lv Jinfeng, et al. PubMed
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
CYP2B6 rs2279343 polymorphism is associated with smoking cessation success in bupropion therapy. European journal of clinical pharmacology. 2015. Tomaz Paulo Roberto Xavier, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Genome-wide association studies in pharmacogenomics of antidepressants. Pharmacogenomics. 2015. Lin Eugene, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Serotonergic gene variation in substance use pharmacotherapy: a systematic review. Pharmacogenomics. 2015. Bauer Isabelle E, et al. PubMed
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
Drug Metabolizing Enzyme and Transporter Gene Variation, Nicotine Metabolism, Prospective Abstinence, and Cigarette Consumption. PloS one. 2015. Bergen Andrew W, et al. PubMed
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
Gene Variants in CYP2C19 are Associated with Altered In Vivo Bupropion Pharmacokinetics but not Bupropion Assisted Smoking Cessation Outcomes. Drug metabolism and disposition: the biological fate of chemicals. 2014. Zhu Andy Z X, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available VA No VIP available No VIP available
Association of CHRNA5-A3-B4 SNP rs2036527 with smoking cessation therapy response in African American smokers. Clinical pharmacology and therapeutics. 2014. Zhu Andy Z X, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Factors associated with discontinuation of bupropion and counseling among African American light smokers in a randomized clinical trial. Annals of behavioral medicine : a publication of the Society of Behavioral Medicine. 2013. Nollen Nicole L, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
An efficient early phase 2 procedure to screen medications for efficacy in smoking cessation. Psychopharmacology. 2013. Perkins Kenneth A, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Influence of a Dopamine Pathway Additive Genetic Efficacy Score on Smoking Cessation: Results from Two Randomized Clinical Trials of Bupropion. Addiction (Abingdon, England). 2013. David Sean P, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Sensitivity and Specificity of A Procedure for Early Human Screening of Novel Smoking Cessation Medications. Addiction (Abingdon, England). 2013. Perkins Kenneth A, et al. PubMed
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Influence of CYP2B6 genetic variants on plasma and urine concentrations of bupropion and metabolites at steady state. Pharmacogenetics and genomics. 2013. Benowitz Neal L, et al. PubMed
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
CYP2B6 and Bupropion's Smoking-Cessation Pharmacology: The Role of Hydroxybupropion. Clinical pharmacology and therapeutics. 2012. Zhu A Z X, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Cytochrome P450-mediated drug metabolism in the brain. Journal of psychiatry & neuroscience : JPN. 2012. Miksys Sharon, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
The DRD4 Exon III VNTR, Bupropion, and Associations With Prospective Abstinence. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco. 2012. Bergen Andrew W, et al. PubMed
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APOE ɛ4, an Alzheimer's disease susceptibility allele, and smoking cessation. The pharmacogenomics journal. 2012. Ashare R L, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Predictors of cessation in African American light smokers enrolled in a bupropion clinical trial. Addictive behaviors. 2012. Faseru Babalola, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Differential Effects of Nicotine Treatment and Ethanol Self-administration on CYP2A6, CYP2B6 and Nicotine Pharmacokinetics in African Green Monkeys. The Journal of pharmacology and experimental therapeutics. 2012. Ferguson Charmaine S, et al. PubMed
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Pharmacogenetic association of the galanin receptor (GALR1) SNP rs2717162 with smoking cessation. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2012. Gold Allison B, et al. PubMed
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Pharmacogenomic study of side-effects for antidepressant treatment options in STAR*D. Psychological medicine. 2012. Clark S L, et al. PubMed
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
DRD1 associations with smoking abstinence across slow and normal nicotine metabolizers. Pharmacogenetics and genomics. 2012. Lee Wonho, et al. PubMed
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Complex drug interactions of the HIV protease inhibitors 3: effect of simultaneous or staggered dosing of digoxin and ritonavir, nelfinavir, rifampin, or bupropion. Drug metabolism and disposition: the biological fate of chemicals. 2012. Kirby Brian J, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Pharmacogenetics of smoking cessation: role of nicotine target and metabolism genes. Human genetics. 2012. Gold Allison B, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Bupropion for Smoking Cessation in African American Light Smokers: A Randomized Controlled Trial. Journal of the National Cancer Institute. 2012. Cox Lisa Sanderson, et al. PubMed
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Smoking Cessation Pharmacogenetics: Analysis of Varenicline and Bupropion in Placebo-Controlled Clinical Trials. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2011. King David P, et al. PubMed
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Polymorphic variants of cytochrome P450 2B6 (CYP2B6.4-CYP2B6.9) exhibit altered rates of metabolism for bupropion and efavirenz: a charge-reversal mutation in the K139E variant (CYP2B6.8) impairs formation of a functional cytochrome p450-reductase complex. The Journal of pharmacology and experimental therapeutics. 2011. Zhang Haoming, et al. PubMed
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Gender-stratified gene and gene-treatment interactions in smoking cessation. The pharmacogenomics journal. 2011. Lee W, et al. PubMed
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THE DYNAMICS OF THE URGE-TO-SMOKE FOLLOWING SMOKING CESSATION VIA PHARMACOTHERAPY. Addiction (Abingdon, England). 2011. Javitz Harold S, et al. PubMed
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Effects of pregnane X receptor (NR1I2) and CYP2B6 genetic polymorphisms on the induction of bupropion hydroxylation by rifampin. Drug metabolism and disposition: the biological fate of chemicals. 2011. Chung Jae Yong, et al. PubMed
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Breaking Barriers in the Genomics and Pharmacogenetics of Drug Addiction. Clinical pharmacology and therapeutics. 2010. Ho M K, et al. PubMed
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Design, baseline characteristics, and retention of African American light smokers into a randomized trial involving biological data. Trials. 2011. Cox Lisa Sanderson, et al. PubMed
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PharmGKB summary: very important pharmacogene information for CYP2B6. Pharmacogenetics and genomics. 2010. Thorn Caroline F, et al. PubMed
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Dopamine D4 receptor gene variation moderates the efficacy of bupropion for smoking cessation. The pharmacogenomics journal. 2010. Leventhal A M, et al. PubMed
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Coprescription of tamoxifen and medications that inhibit CYP2D6. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2010. Sideras Kostandinos, et al. PubMed
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Composite functional genetic and comedication CYP2D6 activity score in predicting tamoxifen drug exposure among breast cancer patients. Journal of clinical pharmacology. 2010. Borges Silvana, et al. PubMed
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Prospective association of dopamine-related polymorphisms with smoking cessation in general care. Pharmacogenomics. 2010. Breitling Lutz P, et al. PubMed
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Substrate specificity, regulation, and polymorphism of human cytochrome P450 2B6. Current drug metabolism. 2009. Mo Sui-Lin, et al. PubMed
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When is pharmacogenetic testing for antidepressant response ready for the clinic? A cost-effectiveness analysis based on data from the STAR*D study. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2009. Perlis Roy H, et al. PubMed
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A systems biology network model for genetic association studies of nicotine addiction and treatment. Pharmacogenetics and genomics. 2009. Thomas Paul D, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Drug discovery. Repurposing with a difference. Science (New York, N.Y.). 2009. Boguski Mark S, et al. PubMed
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Functional pharmacogenetics/genomics of human cytochromes P450 involved in drug biotransformation. Analytical and bioanalytical chemistry. 2008. Zanger Ulrich M, et al. PubMed
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Identification of pharmacogenetic markers in smoking cessation therapy. American journal of medical genetics. Part B, Neuropsychiatric genetics : the official publication of the International Society of Psychiatric Genetics. 2008. Heitjan Daniel F, et al. PubMed
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Toward personalized therapy for smoking cessation: a randomized placebo-controlled trial of bupropion. Clinical pharmacology and therapeutics. 2008. Patterson F, et al. PubMed
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Nicotinic acetylcholine receptor beta2 subunit gene implicated in a systems-based candidate gene study of smoking cessation. Human molecular genetics. 2008. Conti David V, et al. PubMed
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Machine learning methods and docking for predicting human pregnane X receptor activation. Chemical research in toxicology. 2008. Khandelwal Akash, et al. PubMed
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An in vitro mechanistic study to elucidate the desipramine/bupropion clinical drug-drug interaction. Drug metabolism and disposition: the biological fate of chemicals. 2008. Reese Melinda J, et al. PubMed
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Aberrant splicing caused by single nucleotide polymorphism c.516G>T [Q172H], a marker of CYP2B6*6, is responsible for decreased expression and activity of CYP2B6 in liver. The Journal of pharmacology and experimental therapeutics. 2008. Hofmann Marco H, et al. PubMed
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Bupropion efficacy for smoking cessation is influenced by the DRD2 Taq1A polymorphism: analysis of pooled data from two clinical trials. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco. 2007. David Sean P, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Selective induction of human hepatic cytochromes P450 2B6 and 3A4 by metamizole. Clinical pharmacology and therapeutics. 2007. Saussele T, et al. PubMed
No Dosing Guideline available No Drug Label available CA No Variant Annotation available No VIP available No VIP available
Pharmacogenetic clinical trial of sustained-release bupropion for smoking cessation. Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco. 2007. David Sean P, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Polymorphic CYP2B6: molecular mechanisms and emerging clinical significance. Pharmacogenomics. 2007. Zanger Ulrich M, et al. PubMed
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Catechol-O-methyltransferase (COMT) gene variants predict response to bupropion therapy for tobacco dependence. Biological psychiatry. 2007. Berrettini Wade H, et al. PubMed
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Bupropion: pharmacology and therapeutic applications. Expert review of neurotherapeutics. 2006. Foley Kevin F, et al. PubMed
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Role of functional genetic variation in the dopamine D2 receptor (DRD2) in response to bupropion and nicotine replacement therapy for tobacco dependence: results of two randomized clinical trials. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2006. Lerman Caryn, et al. PubMed
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
A natural CYP2B6 TATA box polymorphism (-82T--> C) leading to enhanced transcription and relocation of the transcriptional start site. Molecular pharmacology. 2005. Zukunft Jörg, et al. PubMed
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Dopamine receptor DRD2 genotype and smoking cessation outcome following treatment with bupropion SR. The pharmacogenomics journal. 2005. Swan G E, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Multiple novel nonsynonymous CYP2B6 gene polymorphisms in Caucasians: demonstration of phenotypic null alleles. The Journal of pharmacology and experimental therapeutics. 2004. Lang Thomas, et al. PubMed
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Pharmacogenetic determinants of interindividual variability in bupropion hydroxylation by cytochrome P450 2B6 in human liver microsomes. Pharmacogenetics. 2004. Hesse Leah M, et al. PubMed
No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
Bupropion and 4-OH-bupropion pharmacokinetics in relation to genetic polymorphisms in CYP2B6. Pharmacogenetics. 2003. Kirchheiner Julia, et al. PubMed
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Pharmacogenetic investigation of smoking cessation treatment. Pharmacogenetics. 2002. Lerman Caryn, et al. PubMed
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Validation of bupropion hydroxylation as a selective marker of human cytochrome P450 2B6 catalytic activity. Drug metabolism and disposition: the biological fate of chemicals. 2000. Faucette S R, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
CYP2B6 mediates the in vitro hydroxylation of bupropion: potential drug interactions with other antidepressants. Drug metabolism and disposition: the biological fate of chemicals. 2000. Hesse L M, et al. PubMed
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Comparative tolerability profiles of the newer versus older antidepressants. Drug safety : an international journal of medical toxicology and drug experience. 1994. Rudorfer M V, et al. PubMed

LinkOuts

Web Resource:
Wikipedia
National Drug Code Directory:
0179-0022-44
DrugBank:
DB01156
ChEBI:
3219
KEGG Compound:
C06860
KEGG Drug:
D07591
PubChem Compound:
444
PubChem Substance:
178415
46506896
Drugs Product Database (DPD):
2260239
ChemSpider:
431
Therapeutic Targets Database:
DAP000052
FDA Drug Label at DailyMed:
76e29f61-4f1e-4426-9865-b88dea3d0bb4

Clinical Trials

These are trials that mention bupropion and are related to either pharmacogenetics or pharmacogenomics.

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NURSA Datasets

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