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

General Information of Drug (ID: DR0833)
Drug Name
Hydromorphone
Synonyms
Hydromorfona; Hydromorfona [Spanish]; Hydromorphon; Hydromorphone [INN:BAN]; Hydromorphonum; Hydromorphonum [INN-Latin]; Idromorfone; Idromorfone [DCIT]; Laudacon; Laudicon; Morphinone, dihydro-; Novolaudon; Palladone; hydromorphone; Dihydromorfinon; Dihydromorfinon [Czech]; Dihydromorphinone; Dilaudid; Dilaudid Oros; Dilaudid-hp; Dimorphone; Hidromorfona; Hidromorfona [INN-Spanish]; 4,5-Epoxy-3-hydroxy-17-methylmorphinan-6-one; 466-99-9; 6-Deoxy-7,8-dihydro-6-oxomorphine; 7,8-Dihydromorphinone; DiMo
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 285.34 Topological Polar Surface Area 49.8
Heavy Atom Count 21 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5284570
PubChem SID
9254 ; 81990 ; 7979546 ; 11039353 ; 14751077 ; 14873177 ; 39317885 ; 46508700 ; 48416092 ; 49993162 ; 50070721 ; 56394822 ; 57359121 ; 77568926 ; 96024740 ; 103557031 ; 104098728 ; 129640116 ; 134222944 ; 134337767 ; 134974682 ; 137005111 ; 139157539 ; 160963675 ; 175268533 ; 178103661 ; 179116727 ; 184536600 ; 198992261 ; 223798795 ; 226394766 ; 250134622 ; 252350812
ChEBI ID
ChEBI:5790
CAS Number
466-99-9
TTD Drug ID
D04JHN
Formula
C17H19NO3
Canonical SMILES
CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(=O)CC4
InChI
1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1
InChIKey
WVLOADHCBXTIJK-YNHQPCIGSA-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
Hydromorphone-3-glucuronide DM004778
20727855
Conjugation - Glucuronidation 1 [7] , [8] , [6]
Norhydromorphone DM004777
10355824
Oxidation - N-demethylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005137 Hydromorphone Norhydromorphone Oxidation - N-demethylation CYP3A4 ... [2]
MR005138 Hydromorphone Hydromorphone-3-glucuronide Conjugation - Glucuronidation UGT1A3 ... [7], [8], [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[6]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[6]
⏷ Show the Full List of 6  DME(s)
References
1 Hydromorphone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Role of individual human cytochrome P450 enzymes in the in vitro metabolism of hydromorphone. Xenobiotica. 2004 Apr;34(4):335-44.;
3 Effect of cytochrome P450 2D1 inhibition on hydrocodone metabolism and its behavioral consequences in rats. J Pharmacol Exp Ther. 1997 Mar;280(3):1374-82.
4 Capillary electrophoresis contributions to the hydromorphone metabolism in man. Electrophoresis. 2006 Jun;27(12):2444-57.
5 Is maternal opioid use hazardous to breast-fed infants? Clin Toxicol (Phila). 2012 Jan;50(1):1-14.
6 Opioid therapies and cytochrome p450 interactions. J Pain Symptom Manage. 2012 Dec;44(6 Suppl):S4-14.
7 Hydromorphone
8 Opioid pharmacokinetic drug-drug interactions. Am J Manag Care. 2011 Sep;17 Suppl 11:S276-87.

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