Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0247)
Drug Name
Bupropion
Synonyms
Bupropion SR; Bupropion [INN:BAN]; Elontril; SNPPWIUOZRMYNY-UHFFFAOYSA-N; Wellbatrin; AMFEBUTAMONE HCl; Amfebutamon; Amfebutamona; Amfebutamona [INN-Spanish]; Amfebutamone; Amfebutamonum [INN-Latin]; amfebutamonum; bupropion; (+-)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone; (+-)-Bupropion; 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]propan-1-one; 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one; 34841-39-9; 34911-55-2; BRN 2101062; CHEBI:3219; CHEMBL894; Zyban; alpha-(tert-butylamino)-m-chloropropiophenone
Indication Nicotine dependence [ICD11: 6C4A] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 239.74 Topological Polar Surface Area 29.1
Heavy Atom Count 16 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
444
PubChem SID
9078 ; 794792 ; 4652643 ; 8150639 ; 11342225 ; 11362408 ; 11364557 ; 11367119 ; 11369681 ; 11371567 ; 11374307 ; 11377843 ; 11407107 ; 11466277 ; 11467397 ; 11485553 ; 11485993 ; 11487810 ; 11489475 ; 11490460 ; 11492429 ; 11495477 ; 15196401 ; 17425136 ; 24438813 ; 46386681 ; 46506896 ; 47217436 ; 47440956 ; 47515983 ; 47515984 ; 47589662 ; 47960423 ; 48335208 ; 48415666 ; 49681731 ; 49698964 ; 49832545 ; 50023786 ; 50105235 ; 51091903 ; 53786854 ; 56313588 ; 57320212 ; 79472453 ; 85209446 ; 85788458 ; 90340803 ; 92308360 ; 92308810
ChEBI ID
ChEBI:3219
CAS Number
34841-39-9
TTD Drug ID
D0X4ZR
Formula
C13H18ClNO
Canonical SMILES
CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C
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
InChIKey
SNPPWIUOZRMYNY-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
(2R)-2-(tert-butylamino)-1-(3-chlorophenyl)-3-hydroxypropan-1-one DM000699
21923343
Oxidation - Hydroxylation 1 [2]
R,R-threohydrobupropion DM000690
9943534
Reduction - Ketoreduction 1 [2]
R,S-erythrohydrobupropion DM000694
9899562
Reduction - Ketoreduction 1 [2]
R-4'-hydroxybupropion DM000686
49849377
Oxidation - Hydroxylation 1 [2]
S,R-erythrohydrobupropion DM000696
9813542
Reduction - Ketoreduction 1 [2]
S,S-threohydrobupropion DM000692 N. A. Reduction - Ketoreduction 1 [2]
S-4'-hydroxybupropion DM000681
154699773
Oxidation - Hydroxylation 1 [2]
S-hydroxybupropion DM000675
9879135
Oxidation - Hydroxylation 1 [2]
R,R-hydroxybupropion DM000679
9943908
Unclear 2 [2]
R,R-threo-4'-hydroxy-hydrobupropion DM000689
155535833
Oxidation - 4'-Hydroxylation 2 [2]
R,R-threo-4'-hydroxy-hydrobupropion DM000689
155535833
Reduction - Ketoreduction 2 [2]
R,R-threohydrobupropion glucuronide DM000691 N. A. Conjugation - Glucuronidation 2 [2]
R,S-erythro-4'-hydroxy-hydrobupropion DM000684 N. A. Oxidation - 4'-Hydroxylation 2 [2]
R,S-erythro-4'-hydroxy-hydrobupropion DM000684 N. A. Reduction - Ketoreduction 2 [2]
R,S-erythrohydrobupropion glucuronide DM000695 N. A. Conjugation - Glucuronidation 2 [2]
R-4'-hydroxybupropion glucuronide DM000688 N. A. Conjugation - Glucuronidation 2 [2]
R-4'-hydroxybupropion sulfate DM000687 N. A. Conjugation - Sulfation 2 [2]
S,R-erythro-4'-hydroxy-hydrobupropion DM000698
155519228
Oxidation - 4'-Hydroxylation 2 [2]
S,R-erythrohydrobupropion glucuronide DM000697 N. A. Conjugation - Glucuronidation 2 [2]
S,S-hydroxybupropion DM000676
9795056
Unclear 2 [2]
S,S-threo-4'-hydroxy-hydrobupropion DM000685 N. A. Oxidation - 4'-Hydroxylation 2 [2]
S,S-threo-4'-hydroxy-hydrobupropion DM000685 N. A. Reduction - Ketoreduction 2 [2]
S,S-threohydrobupropion glucuronide DM000693 N. A. Conjugation - Glucuronidation 2 [2]
S-4'-hydroxybupropion glucuronide DM000683 N. A. Conjugation - Glucuronidation 2 [2]
S-4'-hydroxybupropion sulfate DM000682 N. A. Conjugation - Sulfation 2 [2]
R,R-hydroxybupropion glucuronide DM000680 N. A. Conjugation - Glucuronidation 3 [2]
S,S-hydroxybupropion glucuronide DM000677 N. A. Conjugation - Glucuronidation 3 [2]
⏷ Show the Full List of 27  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000513 Bupropion S-hydroxybupropion Oxidation - Hydroxylation CYP2B6 ... [2]
MR000514 Bupropion S-4'-hydroxybupropion Oxidation - Hydroxylation CYP2C19 [2]
MR000515 Bupropion R-4'-hydroxybupropion Oxidation - Hydroxylation CYP2C19 [2]
MR000516 Bupropion R,R-threohydrobupropion Reduction - Ketoreduction HSD11B1 ... [2]
MR000517 Bupropion S,S-threohydrobupropion Reduction - Ketoreduction HSD11B1 ... [2]
MR000518 Bupropion R,S-erythrohydrobupropion Reduction - Ketoreduction HSD11B1 ... [2]
MR000519 Bupropion S,R-erythrohydrobupropion Reduction - Ketoreduction HSD11B1 ... [2]
MR000520 Bupropion (2R)-2-(tert-butylamino)-1-(3-chlorophenyl)-3-hydroxypropan-1-one Oxidation - Hydroxylation CYP2C19 [2]
MR000505 R,R-threohydrobupropion R,R-threo-4'-hydroxy-hydrobupropion Oxidation - 4'-Hydroxylation CYP2C19 [2]
MR000506 R,R-threohydrobupropion R,R-threohydrobupropion glucuronide Conjugation - Glucuronidation UGT1A9 ... [2]
MR000509 R,S-erythrohydrobupropion R,S-erythro-4'-hydroxy-hydrobupropion Oxidation - 4'-Hydroxylation CYP2C19 [2]
MR000510 R,S-erythrohydrobupropion R,S-erythrohydrobupropion glucuronide Conjugation - Glucuronidation UGT1A9 ... [2]
MR000501 R-4'-hydroxybupropion R,S-erythro-4'-hydroxy-hydrobupropion Reduction - Ketoreduction HSD11B1 ... [2]
MR000502 R-4'-hydroxybupropion R-4'-hydroxybupropion sulfate Conjugation - Sulfation Unclear [2]
MR000503 R-4'-hydroxybupropion R-4'-hydroxybupropion glucuronide Conjugation - Glucuronidation Unclear [2]
MR000504 R-4'-hydroxybupropion R,R-threo-4'-hydroxy-hydrobupropion Reduction - Ketoreduction HSD11B1 ... [2]
MR000495 R-hydroxybupropion R,R-hydroxybupropion Unclear Unclear [2]
MR000511 S,R-erythrohydrobupropion S,R-erythrohydrobupropion glucuronide Conjugation - Glucuronidation UGT1A9 ... [2]
MR000512 S,R-erythrohydrobupropion S,R-erythro-4'-hydroxy-hydrobupropion Oxidation - 4'-Hydroxylation CYP2C19 [2]
MR000507 S,S-threohydrobupropion S,S-threo-4'-hydroxy-hydrobupropion Oxidation - 4'-Hydroxylation CYP2C19 [2]
MR000508 S,S-threohydrobupropion S,S-threohydrobupropion glucuronide Conjugation - Glucuronidation UGT2B4 ... [2]
MR000497 S-4'-hydroxybupropion S-4'-hydroxybupropion sulfate Conjugation - Sulfation Unclear [2]
MR000498 S-4'-hydroxybupropion S-4'-hydroxybupropion glucuronide Conjugation - Glucuronidation Unclear [2]
MR000499 S-4'-hydroxybupropion R,S-erythro-4'-hydroxy-hydrobupropion Reduction - Ketoreduction HSD11B1 ... [2]
MR000500 S-4'-hydroxybupropion S,S-threo-4'-hydroxy-hydrobupropion Reduction - Ketoreduction HSD11B1 ... [2]
MR000493 S-hydroxybupropion S,S-hydroxybupropion Unclear Unclear [2]
MR000496 R,R-hydroxybupropion R,R-hydroxybupropion glucuronide Conjugation - Glucuronidation UGT2B4 ... [2]
MR000494 S,S-hydroxybupropion S,S-hydroxybupropion glucuronide Conjugation - Glucuronidation UGT2B7 [2]
⏷ Show the Full List of 28 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aflatoxin B1 aldehyde reductase member 3 (AKR7A3) DMEN017 Homo sapiens
ARK73_HUMAN
Not Available [2]
Corticosteroid 11-beta-dehydrogenase 1 (HSD11B1) DME0199 Homo sapiens
DHI1_HUMAN
1.1.1.146
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [7]
⏷ Show the Full List of 14  DME(s)
References
1 Bupropion was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 DrugBank(Pharmacology-Metabolism)Bupropion
3 Laparoscopic Roux-en-Y gastric bypass surgery influenced pharmacokinetics of several drugs given as a cocktail with the highest impact observed for CYP1A2, CYP2C8 and CYP2E1 substrates. Basic Clin Pharmacol Toxicol. 2019 Aug;125(2):123-132.
4 Product Monograph of Wellbutrin SR(Bupropion Hydrochloride).
5 In vitro to in vivo extrapolation of the complex drug-drug interaction of bupropion and its metabolites with CYP2D6; simultaneous reversible inhibition and CYP2D6 downregulation. Biochem Pharmacol. 2017 Jan 1;123:85-96.
6 Validation of bupropion hydroxylation as a selective marker of human cytochrome P450 2B6 catalytic activity. Drug Metab Dispos. 2000 Oct;28(10):1222-30.
7 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.

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