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

General Information of Drug (ID: DR5193)
Drug Name
Hydrocodone
Synonyms
HYDROCODONE; Dihydrocodeinone; Hydrocodon; Hydrocone; Hydroconum; Codinovo; Dicodid; Multacodin; Bekadid; hidrocodona; Idrocodone; Hydrocodonum; Idrocodone [DCIT]; DICO; (-)-Dihydrocodeinone; Hydrocodonum [INN-Latin]; 125-29-1; Hidrocodona [INN-Spanish]; Codeinone, dihydro-; Hydrocodone polistirex; Hydrocodone [INN:BAN]; UNII-6YKS4Y3WQ7; 4,5-alpha-Epoxy-3-methoxy-17-methylmorphinan-6-one; 6-Oxo-3-methoxy-N-methyl-4,5-epoxymorphinan; 4,5alpha-Epoxy-3-methoxy-17-methylmorphinan-6-one; HSDB 3097; EINECS 204-733-9; BRN 0094193; Bekadid; Hidrocodona; Hydrocodeinonebitartrate; Hydrocon; Anexsia (TN); Dicodid (TN); Duodin (TN); Hycet (TN); Hycodan (TN); Hycomine (TN); Hydrocodone (INN); Hydrokon (TN); Hydrovo (TN); Kolikodol (TN); Lorcet (TN); Lortab (TN); Mercodinone (TN); Norco (TN); Norgan (TN); Novahistex (TN); Orthoxycol (TN); Symtan (TN); Synkonin (TN); Vicodin (TN); Morphinan-6-one, 4,5alpha-epoxy-3-methoxy-17-methyl-(8CI); Morphinan-6-one, 4,5-epoxy-3-methoxy-17-methyl-, (5alpha)-(9CI); (5alpha)-17-methyl-3-(methyloxy)-4,5-epoxymorphinan-6-one; 3-methoxy-17-methyl-4,5alpha-epoxymorphinan-6-one; KP-201 hydrocodone prodrug
Indication Pain [ICD11: MG30-MG3Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 299.4 Topological Polar Surface Area 38.8
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5284569
ChEBI ID
CHEBI:5779
CAS Number
125-29-1
TTD Drug ID
D0X5KF
Formula
C18H21NO3
Canonical SMILES
CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3C(=O)CC4
InChI
InChI=1S/C18H21NO3/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/h3,6,11-12,17H,4-5,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1
InChIKey
LLPOLZWFYMWNKH-CMKMFDCUSA-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
Hydrocodol DM018837 N. A. Reduction - Ketone reduction 1 [4]
Hydrocodone M272 DM018833 N. A. Multi-steps Reaction - N-demethylation; O-demethylation 1 [4]
Hydrocodone N-oxide-1 DM018842 N. A. Oxidation - N-oxidation 1 [4]
Hydromorphone DM004753
5284570
Oxidation - O-demethylation 1 [4]
Norhydrocodone DM004764
13001738
Oxidation - N-demethylation 1 [4]
Hydrocodone M272 DM018833 N. A. Multi-steps Reaction - N-demethylation; O-demethylation 2 [4]
Hydrocodone M274 DM016495
102064867
Oxidation - N-demethylation 2 [4]
Hydrocodone M298 DM018840 N. A. Multi-steps Reaction - Possible combination of hydroxylation; dehydration 2 [4]
Hydrocodone M300 DM018838 N. A. Multi-steps Reaction - Possible combination of hydroxylation; dehydration 2 [4]
Hydrocodone M462 DM018836 N. A. Conjugation - Glucuronidation 2 [4]
Hydrocodone M488 DM018841 N. A. Conjugation - Glucuronidation 2 [4]
Hydromorphol DM018831 N. A. Reduction - Ketone reduction 2 [4]
Norhydrocodol DM018839 N. A. Reduction - Ketone reduction 2 [4]
Norhydrocodol DM018839 N. A. Oxidation - N-demethylation 2 [4]
Hydrocodone M274 DM016495
102064867
Oxidation - N-demethylation 3 [4]
Hydrocodone M286 DM018834 N. A. Multi-steps Reaction - Possible combination of hydroxylation; dehydration 3 [4]
Hydrocodone M450 DM018832 N. A. Conjugation - Glucuronidation 3 [4]
Hydrocodone M464 DM018835 N. A. Conjugation - Glucuronidation 3 [4]
Hydrocodone M450 DM018832 N. A. Conjugation - Glucuronidation 4 [4]
⏷ Show the Full List of 19  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR011201 Hydrocodone Hydromorphone Oxidation - O-demethylation CYP2D6 [4]
MR011205 Hydrocodone Norhydrocodone Oxidation - N-demethylation CYP3A4 [4]
MR011210 Hydrocodone Hydrocodone M272 Multi-steps Reaction - N-demethylation; O-demethylation Unclear [4]
MR011212 Hydrocodone Hydrocodol Reduction - Ketone reduction Unclear [4]
MR011218 Hydrocodone Hydrocodone N-oxide-1 Oxidation - N-oxidation Unclear [4]
MR011213 Hydrocodol Hydrocodone M300 Multi-steps Reaction - Possible combination of hydroxylation; dehydration Unclear [4]
MR011214 Hydrocodol Norhydrocodol Oxidation - N-demethylation Unclear [4]
MR011215 Hydrocodol Hydrocodone M298 Multi-steps Reaction - Possible combination of hydroxylation; dehydration Unclear [4]
MR011216 Hydrocodone M272 Hydrocodone M488 Conjugation - Glucuronidation Unclear [4]
MR014001 Hydrocodone M272 Hydrocodone M274 Oxidation - N-demethylation Unclear [4]
MR011202 Hydromorphone Hydromorphol Reduction - Ketone reduction Unclear [4]
MR011211 Hydromorphone Hydrocodone M462 Conjugation - Glucuronidation Unclear [4]
MR011206 Norhydrocodone Hydrocodone M272 Multi-steps Reaction - N-demethylation; O-demethylation Unclear [4]
MR011217 Norhydrocodone Norhydrocodol Reduction - Ketone reduction Unclear [4]
MR011207 Hydrocodone M272 Hydrocodone M274 Oxidation - N-demethylation Unclear [4]
MR014002 Hydrocodone M274 Hydrocodone M450 Conjugation - Glucuronidation Unclear [4]
MR011203 Hydromorphol Hydrocodone M274 Oxidation - N-demethylation Unclear [4]
MR011208 Hydromorphol Hydrocodone M286 Multi-steps Reaction - Possible combination of hydroxylation; dehydration Unclear [4]
MR011209 Hydromorphol Hydrocodone M464 Conjugation - Glucuronidation Unclear [4]
MR011204 Hydrocodone M274 Hydrocodone M450 Conjugation - Glucuronidation Unclear [4]
⏷ Show the Full List of 20 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_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
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7081).
2 FDA LABEL:Hydrocodone
3 CYP2D6 and CYP3A4 involvement in the primary oxidative metabolism of hydrocodone by human liver microsomes. Br J Clin Pharmacol. 2004 Mar;57(3):287-97.
4 Update on hydrocodone metabolites in rats and dogs aided with a semi-automatic software for metabolite identification Mass-MetaSite

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.