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

General Information of Drug (ID: DR0500)
Drug Name
Dihydrocodeine
Synonyms
Dehacodin; Didrate; Dihidrocodeina [INN-Spanish]; Dihydrin; Dihydrocodeine [INN:BAN]; Dihydrocodeine [INN]; Dihydrocodeinum [INN-Latin]; Dihydrokodein [Czech]; Dihydroneopine; Diidrocodeina [DCIT]; Drocode; Hydrocodeine; Codhydrine; Cohydrin; DIHYDROCODEINE; Hydrocodin; Nadeine; Novicodin; Novicondin; Paracodin; Paracodine; Parzone; Rapacodin; alpha-Hydrocodol; (-)-Dihydrocodeine; 125-28-0; 6-alpha-Hydrocodol; 6alpha-Hydrocodol; 7,8-Dihydrocodeine; 8,14-Dihydroneopine; EINECS 204-732-3; NSC 231319; UNII-N9I9HDB855; Codeine, 7,8-dihydro-
Indication Anaesthesia [ICD11: 8E22] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 301.4 Topological Polar Surface Area 41.9
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5284543
PubChem SID
7979086 ; 11039338 ; 14751770 ; 14922962 ; 39317861 ; 46506478 ; 48415896 ; 49992976 ; 57359107 ; 79356041 ; 96024528 ; 123090163 ; 129105931 ; 134224170 ; 134975551 ; 137225019 ; 142842435 ; 143309001 ; 160964796 ; 175266000 ; 179116652 ; 184595582 ; 223365929 ; 224980825 ; 226412911
ChEBI ID
CHEBI:135276
CAS Number
125-28-0
TTD Drug ID
D0T6RC
Formula
C18H23NO3
Canonical SMILES
CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(CC4)O
InChI
1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
InChIKey
RBOXVHNMENFORY-DNJOTXNNSA-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
6-alpha-hydromorphol DM004754
5359421
Oxidation - O-demethylation 1 [3] , [5]
DHNC DM006599
625501
Oxidation - N-demethylation 1 [6] , [4]
Dihydrocodeine-6-glucuronide DM006597 N. A. Conjugation - Glucuronidation 1 [3] , [4]
Nordihydrocodeine DM006600
10016922
Unclear 1 [3]
DHM-glucuronides DM006596 N. A. Conjugation - Glucuronidation 2 [3]
DHNCG DM006598 N. A. Conjugation - Glucuronidation 2 [6]
DHNCG DM006598 N. A. Oxidation - N-demethylation 2 [6] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007115 Dihydrocodeine Dihydromorphine Oxidation - O-demethylation CYP2D6 [3], [5]
MR007117 Dihydrocodeine Dihydrocodeine-6-glucuronide Conjugation - Glucuronidation UGT2B4 ... [3], [4]
MR007119 Dihydrocodeine DHNC Oxidation - N-demethylation Unclear [6], [4]
MR007121 Dihydrocodeine Nordihydrocodeine Unclear CYP3A4 [3]
MR007120 DHNC DHNCG Conjugation - Glucuronidation Unclear [6]
MR007118 Dihydrocodeine-6-glucuronide DHNCG Oxidation - N-demethylation Unclear [6], [4]
MR007116 Dihydromorphine DHM-glucuronides Conjugation - Glucuronidation Unclear [3]
⏷ Show the Full List of 7 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
[3]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
References
1 ClinicalTrials.gov (NCT00547885) Randomized Controlled Double Blind Trial of Short vs Long Acting Dihydrocodeine in Chronic Non-malignant Pain.
2 The role of active metabolites in dihydrocodeine effects. Int J Clin Pharmacol Ther. 2003 Mar;41(3):95-106.
3 Pharmacokinetics of dihydrocodeine and its active metabolite after single and multiple oral dosing. Br J Clin Pharmacol. 1999 Sep;48(3):317-22.
4 Adult and infant pharmacokinetic profiling of dihydrocodeine using physiologically based pharmacokinetic modeling. Biopharm Drug Dispos. 2019 Nov;40(9):350-357.
5 Dihydrocodeine: safety concerns
6 Metabolism and pharmacokinetics of dihydrocodeine in dog

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