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

General Information of Drug (ID: DR1221)
Drug Name
Oxycodone hydrochloride
Synonyms
Ossicodone [DCIT]; Oxanest; Oxicodona; Oxicodona [INN-Spanish]; Oxicon; Oxicone; Oxycodeinone; Oxycodon; Oxycodone [USAN:INN:BAN]; Oxycodonum; Oxycodonum [INN-Latin]; Oxyfast; Pancodine; Percobarb; Percodan; Roxicodone; Supendol; Supendol [Canada]; oxycodone; (-)-14-Hydroxydihydrocodeinone; 76-42-6; OxyIR; Codeinone, dihydrohydroxy-; Dihydro-14-hydroxycodeinone; Dihydrohydroxycodeinone; Dihydrohydroxycondeinone; Dihydrone; Dihydroxycodeinone; Diphydrone; Endine (Australia); Endone; Eubine [France]; Eucodalum; Dihydrone hydrochloride; Dihydrooxycodeinone hydrochloride; Dihydroxycodeinone hydrochloride; MUZQPDBAOYKNLO-RKXJKUSZSA-N; Oxecta (TN); Oxycodone Hcl; Oxycodone hydrochloride; Oxycodone hydrochloride (USP); Oxycodone hydrochloride solution; Oxycontin (TN); Roxicodone (TN); oxycodone monohydrochloride; 124-90-3; 14-Hydroxydihydrocodeinone hydrochloride; 4,5alpha-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one hydrochloride; AKOS024457896; API0009028; CHEBI:7859; CHEMBL1200890; DTXSID80924674; SCHEMBL30095
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 351.8 Topological Polar Surface Area 59
Heavy Atom Count 24 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5462350
ChEBI ID
CHEBI:7859
CAS Number
124-90-3
TTD Drug ID
D07WPQ
Formula
C18H22ClNO4
Canonical SMILES
CN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)OC)O4)O.Cl
InChI
1S/C18H21NO4.ClH/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10;/h3-4,13,16,21H,5-9H2,1-2H3;1H/t13-,16+,17+,18-;/m1./s1
InChIKey
MUZQPDBAOYKNLO-RKXJKUSZSA-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
6beta-Oxycodol DM001126
14368120
Reduction - Reduction 1 [3]
Alpha-Oxycodol DM001125
69087507
Reduction - Reduction 1 [3]
Noroxycodone DM001122
5489120
Oxidation - N-Demethylation 1 [3] , [5] , [6]
Zanubrutinib Metabolite M5 DM003074
5284604
Oxidation - O-Demethylation 1 [3] , [7] , [6] , [8]
6beta-Oxymorphol DM001141
21779240
Reduction - 6-Ketoreduction 2 [9]
Beta-Noroxycodol DM001124
131770022
Reduction - 6-Ketoreduction 2 [9]
Hydromorphinol DM001119
5463858
Reduction - 6-Ketoreduction 2 [9]
Nor-6alpha-Oxycodol DM001123
129839794
Reduction - 6-Ketoreduction 2 [9]
Zanubrutinib Metabolite M2 DM001121
5497189
Oxidation - N-Demethylation 2 [3] , [5]
Zanubrutinib Metabolite M2 DM001121
5497189
Oxidation - N-Demethylation 2 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001881 Oxycodone hydrochloride Noroxycodone Oxidation - N-Demethylation CYP3A4 ... [3], [5], [6]
MR001882 Oxycodone hydrochloride Alpha-Oxycodol Reduction - Reduction Unclear [3]
MR001883 Oxycodone hydrochloride 6beta-Oxycodol Reduction - Reduction Unclear [3]
MR001884 Oxycodone hydrochloride Oxymorphone Oxidation - O-Demethylation CYP2D6 [3], [7], [6], [8]
MR001878 Noroxycodone Noroxymorphone Oxidation - N-Demethylation CYP3A4 ... [3], [5]
MR001879 Noroxycodone Nor-6alpha-Oxycodol Reduction - 6-Ketoreduction Unclear [9]
MR001880 Noroxycodone Beta-Noroxycodol Reduction - 6-Ketoreduction Unclear [9]
MR001885 Oxymorphone Hydromorphinol Reduction - 6-Ketoreduction Unclear [9]
MR001886 Oxymorphone Noroxymorphone Oxidation - N-Demethylation CYP3A4 ... [9]
MR001887 Oxymorphone 6beta-Oxymorphol Reduction - 6-Ketoreduction Unclear [9]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
References
1 Oxymorphone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolism and disposition of prescription opioids: a review. Forensic Sci Rev. 2015 Jul;27(2):115-45.
3 Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54.
4 Human Fetal Liver Metabolism of Oxycodone Is Mediated by CYP3A7
5 Enzalutamide Reduces Oxycodone Exposure in Men with Prostate Cancer. Clin Pharmacokinet. 2023 May 10. doi: 10.1007/s40262-023-01255-1.
6 Impact of genetic variation in CYP2C19, CYP2D6, and CYP3A4 on oxycodone and its metabolites in a large database of clinical urine drug tests. Pharmacogenomics J. 2022 Feb;22(1):25-32. doi: 10.1038/s41397-021-00253-5.
7 Zhx2 Is a Candidate Gene Underlying Oxymorphone Metabolite Brain Concentration Associated with State-Dependent Oxycodone Reward. J Pharmacol Exp Ther. 2022 Aug;382(2):167-180. doi: 10.1124/jpet.122.001217.
8 Association of CYP2D6 genotype predicted phenotypes with oxycodone requirements and side effects in children undergoing surgery. Ann Transl Med. 2022 Dec;10(23):1262. doi: 10.21037/atm-2022-58.
9 DrugBank(Pharmacology-Metabolism)Oxycodone hydrochloride

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