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

General Information of Drug (ID: DR1127)
Drug Name
Naloxone
Synonyms
Nalone; Nalossone; Nalossone [DCIT]; Naloxona; Naloxona [INN-Spanish]; Naloxone [INN:BAN]; Naloxonum; Naloxonum [INN-Latin]; Narcan; Narcanti; Narcon; l-Naloxone; n-Allylnoroxymorphone; naloxone; (-)-Naloxone; 1-N-Allyl-14-hydroxynordihydromorphinone; EN 1530 base; N-Allyl-noroxymorphone; 1-N-Allyl-7,8-dihydro-14-hydroxynormorphinone; 17-Allyl-4,5-alpha-epoxy-3,14-dihydroxymorphinan-6-one; 17-Allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one; 465-65-6; HSDB 3279; UNII-36B82AMQ7N; l-N-Allyl-14-hydroxynordihydromorphinone
Indication Opiate dependence [ICD11: 6C43] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 327.4 Topological Polar Surface Area 70
Heavy Atom Count 24 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5284596
PubChem SID
9461 ; 113816 ; 841983 ; 7980073 ; 11039368 ; 11466139 ; 11467259 ; 11485797 ; 14777335 ; 14924176 ; 16463984 ; 25663897 ; 39317902 ; 46508816 ; 47588898 ; 47588899 ; 47662178 ; 47736369 ; 47959634 ; 48334383 ; 48416308 ; 49698350 ; 49993151 ; 50070720 ; 50104484 ; 53788675 ; 56312594 ; 56312596 ; 56352924 ; 57288792 ; 57359133 ; 74711224 ; 85787517 ; 92309116 ; 93166268 ; 96024937 ; 103170037 ; 103915330 ; 124886932 ; 126688739 ; 129442197 ; 134337424 ; 134974167 ; 135650684 ; 135651185 ; 137001357 ; 139076562 ; 144205559 ; 160964517 ; 162183031
ChEBI ID
CHEBI:7459
CAS Number
465-65-6
TTD Drug ID
D0RN5A
Formula
C19H21NO4
Canonical SMILES
C=CCN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O
InChI
1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1
InChIKey
UZHSEJADLWPNLE-GRGSLBFTSA-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
Naloxol DM004528
44230574
Reduction - 6-ketoreduction 1 [6]
Naloxone 3-Glucuronide DM004527
101539035
Conjugation - Glucuronidation 1 [7]
Naloxone Metabolite M10 DM018634 N. A. Unclear - Unclear 1 [8]
Naloxone Metabolite M21 DM015475
5748372
Unclear - Unclear 1 [8]
Naloxone Metabolite M23 DM018632 N. A. Unclear - Unclear 1 [8]
Naloxone Metabolite M26 DM018635 N. A. Unclear - Unclear 1 [8]
Naloxone Metabolite M31 DM018633 N. A. Unclear - Unclear 1 [8]
Naloxone Metabolite M4 DM018629 N. A. Unclear - Unclear 1 [8]
Naloxone Metabolite M7 DM018631 N. A. Unclear - Unclear 1 [8] , [4]
Zanubrutinib Metabolite M2 DM001121
5497189
Unclear - Unclear 1 [8]
Zanubrutinib Metabolite M5 DM003074
5284604
Unclear - Unclear 1 [8]
Naloxone Metabolite M12 DM018630 N. A. Unclear - Unclear 2 [8]
Naloxone Metabolite M35 DM015925
15605738
Unclear - Unclear 2 [8]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010785 Naloxone Naloxone Metabolite M2 Unclear - Unclear Unclear [8]
MR010787 Naloxone Naloxone Metabolite M4 Unclear - Unclear Unclear [8]
MR010789 Naloxone Naloxone Metabolite M21 Unclear - Unclear Unclear [8]
MR010790 Naloxone Naloxone Metabolite M7 Unclear - Unclear UGT2B7 [8], [4]
MR010791 Naloxone Naloxone Metabolite M23 Unclear - Unclear Unclear [8]
MR010792 Naloxone Naloxone Metabolite M5 Unclear - Unclear Unclear [8]
MR010793 Naloxone Naloxone Metabolite M31 Unclear - Unclear Unclear [8]
MR010794 Naloxone Naloxone Metabolite M10 Unclear - Unclear Unclear [8]
MR010795 Naloxone Naloxone Metabolite M26 Unclear - Unclear Unclear [8]
MR010796 Naloxone Naloxone 3-Glucuronide Conjugation - Glucuronidation Unclear [7]
MR010797 Naloxone Naloxol Reduction - 6-ketoreduction Unclear [6]
MR010786 Naloxone Metabolite M2 Naloxone Metabolite M35 Unclear - Unclear Unclear [8]
MR010788 Naloxone Metabolite M4 Naloxone Metabolite M12 Unclear - Unclear Unclear [8]
⏷ Show the Full List of 13 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [5]
⏷ Show the Full List of 10  DME(s)
References
1 Naloxone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Buprenorphine in cancer pain. Support Care Cancer. 2005 Nov;13(11):878-87.
3 Metabolic interaction between morphine and naloxone in human liver. A common pathway of glucuronidation? Drug Metab Dispos. 1989 Mar-Apr;17(2):218-20.
4 PBPK Modeling as a Tool for Predicting and Understanding Intestinal Metabolism of Uridine 5'-Diphospho-glucuronosyltransferase Substrates
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 Metabolites of naloxone in human urine
7 Effect of naloxone-3-glucuronide and N-methylnaloxone on the motility of the isolated rat colon after morphine
8 Optimization of Mass Spectrometry Imaging for Drug Metabolism and Distribution Studies in the Zebrafish Larvae Model: A Case Study with the Opioid Antagonist Naloxone

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