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

General Information of Drug (ID: DR0816)
Drug Name
Hydrocodone bitartrate
Synonyms
Hydrocodon; Hydrocodone [INN:BAN]; Hydrocodone polistirex; Hydrocodonum; Hydrocodonum [INN-Latin]; Hydrocone; Hydroconum; Idrocodone; Idrocodone [DCIT]; Multacodin; hidrocodona; (-)-Dihydrocodeinone; 125-29-1; 4,5-alpha-Epoxy-3-methoxy-17-methylmorphinan-6-one; 4,5alpha-Epoxy-3-methoxy-17-methylmorphinan-6-one; 6-Oxo-3-methoxy-N-methyl-4,5-epoxymorphinan; BRN 0094193; DICO; EINECS 204-733-9; HSDB 3097; UNII-6YKS4Y3WQ7; Bekadid; Codeinone, dihydro-; Codinovo; Dicodid; Dihydrocodeinone; HYDROCODONE; Hidrocodona [INN-Spanish]; HYDROCODONE BITARTRATE; OJHZNMVJJKMFGX-RNWHKREASA-N; SCHEMBL154972; .codon; 143-71-5; API0002943; CHEMBL2062267; MFCD00078557
Indication Neuropathic pain [ICD11: 8E43] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 449.4 Topological Polar Surface Area 154
Heavy Atom Count 32 Rotatable Bond Count 4
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
20831824
CAS Number
143-71-5
Formula
C22H27NO9
Canonical SMILES
CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(=O)CC4.C(C(C(=O)O)O)(C(=O)O)O
InChI
1S/C18H21NO3.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h3,6,11-12,17H,4-5,7-9H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t11-,12+,17-,18-;/m0./s1
InChIKey
OJHZNMVJJKMFGX-RNWHKREASA-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-hydrocodol DM004757
5284543
Reduction - 6-ketoreduction 1 [6] , [4]
Hydromorphone DM004753
5284570
Oxidation - O-demethylation 1 [4]
Norhydrocodone DM004764
13001738
Oxidation - N-demethylation 1 [4]
6-alpha-hydromorphol DM004754
5359421
Oxidation - O-demethylation 2 [7]
6-alpha-hydromorphol DM004754
5359421
Reduction - 6-ketoreduction 2 [7]
6-beta-hydrocodol DM004758
5492898
Reduction - 6-ketoreduction 2 [7]
Hydromorphone glucuronide conjugate DM004763 N. A. Conjugation - O-glucuronidation 2 [7]
6-alpha-hydromorphol glucuronide conjugate 1 DM004760
53987586
Conjugation - O-glucuronidation 3 [7]
6-beta-hydrocodol glucuronide conjugate DM004762 N. A. Conjugation - O-glucuronidation 3 [7]
6-beta-hydromorphol DM004755
9814448
Oxidation - O-demethylation 3 [7]
6-beta-hydromorphol DM004755
9814448
Reduction - 6-ketoreduction 3 [7]
6-alpha-hydromorphol glucuronide conjugate 2 DM004761
53777337
Conjugation - O-glucuronidation 4 [7]
6-beta-hydromorphol glucuronide conjugate 1 DM004756 N. A. Conjugation - O-glucuronidation 4 [7]
6-beta-hydromorphol DM004755
9814448
Conjugation - O-glucuronidation 5 [7]
6-beta-hydromorphol glucuronide conjugate 2 DM004759 N. A. Conjugation - O-glucuronidation 5 [7]
⏷ Show the Full List of 15  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005109 Hydrocodone bitartrate Hydromorphone Oxidation - O-demethylation CYP2D6 ... [4]
MR005114 Hydrocodone bitartrate 6-alpha-hydrocodol Reduction - 6-ketoreduction Unclear [6], [4]
MR005115 Hydrocodone bitartrate 6-beta-hydrocodol Reduction - 6-ketoreduction Unclear [7]
MR005123 Hydrocodone bitartrate Norhydrocodone Oxidation - N-demethylation CYP3A4 [4]
MR005118 6-alpha-hydrocodol 6-alpha-hydromorphol Oxidation - O-demethylation CYP2D6 ... [7]
MR005110 Hydromorphone 6-alpha-hydromorphol Reduction - 6-ketoreduction Unclear [7]
MR005111 Hydromorphone 6-beta-hydromorphol Reduction - 6-ketoreduction Unclear [7]
MR005122 Hydromorphone Hydromorphone glucuronide conjugate Conjugation - O-glucuronidation Unclear [7]
MR005119 6-alpha-hydromorphol 6-alpha-hydromorphol glucuronide conjugate 1 Conjugation - O-glucuronidation Unclear [7]
MR005120 6-alpha-hydromorphol 6-alpha-hydromorphol glucuronide conjugate 2 Conjugation - O-glucuronidation Unclear [7]
MR005116 6-beta-hydrocodol 6-beta-hydromorphol Oxidation - O-demethylation CYP2D6 ... [7]
MR005121 6-beta-hydrocodol 6-beta-hydrocodol glucuronide conjugate Conjugation - O-glucuronidation Unclear [7]
MR005112 6-beta-hydromorphol 6-beta-hydromorphol glucuronide conjugate 1 Conjugation - O-glucuronidation Unclear [7]
MR005113 6-beta-hydromorphol 6-beta-hydromorphol Conjugation - O-glucuronidation Unclear [7]
MR005117 6-beta-hydromorphol 6-beta-hydromorphol glucuronide conjugate 2 Conjugation - O-glucuronidation Unclear [7]
⏷ Show the Full List of 15 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
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[5]
References
1 Hydrocodone Bitartrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 FDA label of Hydrocodone bitartrate. The 2020 official website of the U.S. Food and Drug Administration.
3 The effect of CYP2D6 drug-drug interactions on hydrocodone effectiveness. Acad Emerg Med. 2014 Aug;21(8):879-85.
4 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.
5 Pharmacokinetic drug interactions of morphine, codeine, and their derivatives: theory and clinical reality, Part II. Psychosomatics. 2003 Nov-Dec;44(6):515-20.
6 Comparative metabolism of hydrocodone in man, rat, guinea pig, rabbit, and dog
7 DrugBank(Pharmacology-Metabolism):Hydrocodone bitartrate

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