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

General Information of Drug (ID: DR0661)
Drug Name
Ethylmorphine
Synonyms
Codethyline; DIONINE; Dionin; Ethomorphine; Ethyl morphine; Ethylmorphine; Ethylmorphine (BAN); Ethylmorphine [BAN]; Morphine 3-ethyl ether; Morphine, ethyl-; RWO67D87EU; (4R,4aR,7S,7aR,12bS)-9-ethoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol; 3-O-Ethylmorphine; 76-58-4; AC1Q37UW; CHEBI:4902; DEA No. 9190; EINECS 200-970-7; Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-ethoxy-17-methyl-; NCGC00168251-01; UNII-RWO67D87EU
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 313.4 Topological Polar Surface Area 41.9
Heavy Atom Count 23 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5359271
PubChem SID
9740 ; 11653625 ; 24894676 ; 39383741 ; 46505092 ; 49992909 ; 50113064 ; 57361891 ; 78090903 ; 96024624 ; 117442635 ; 134224401 ; 134971681 ; 136183691 ; 137005109 ; 137201797 ; 140040172 ; 144206163 ; 160687929 ; 160964725 ; 164788459 ; 198959733 ; 202826782 ; 223439637 ; 226413171 ; 241138150 ; 250135382
ChEBI ID
CHEBI:4902
CAS Number
76-58-4
TTD Drug ID
D0N5QC
Formula
C19H23NO3
Canonical SMILES
CCOC1=C2C3=C(CC4C5C3(CCN4C)C(O2)C(C=C5)O)C=C1
InChI
1S/C19H23NO3/c1-3-22-15-7-4-11-10-13-12-5-6-14(21)18-19(12,8-9-20(13)2)16(11)17(15)23-18/h4-7,12-14,18,21H,3,8-10H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1
InChIKey
OGDVEMNWJVYAJL-LEPYJNQMSA-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
Ethylmorphine-6-glucuronide DM003886
15764785
Unclear 1 [1]
Morphine DM003208
60053788
Oxidation - N-dealkylation 1 [7] , [8] , [9] , [10]
Norethylmorphine DM003883
5464196
Unclear 1 [7]
Morphine glucuronide DM003209
5360621
Unclear 2 [11]
Morphine-3-glucuronide DM003210 N. A. Conjugation - Glucuronidation 2 [12] , [9] , [10]
Norethylmorphine-6-glucuronide DM003885 N. A. Unclear 2 [1]
Normorphine DM003211
5462508
Unclear 2 [1]
Normorphine-3-glucuronide DM003881
163143
Conjugation - Glucuronidation 2 [7]
Normorphine-3-glucuronide DM003881
163143
Unclear 3 [1]
Normorphine-6-glucuronide DM003882
5492315
Unclear 3 [1]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012868 Ethylmorphine Morphine Oxidation - N-dealkylation Unclear [7], [8], [9], [10]
MR012872 Ethylmorphine Norethylmorphine Unclear Unclear [7]
MR012878 Ethylmorphine Ethylmorphine-6-glucuronide Unclear Unclear [1]
MR012869 Morphine Normorphine Unclear Unclear [1]
MR012874 Morphine Morphine-3-glucuronide Conjugation - Glucuronidation Unclear [12], [9], [10]
MR012875 Morphine Morphine-6-glucuronide Unclear CYP2D6 [11]
MR012873 Norethylmorphine Normorphine Unclear Unclear [1]
MR012876 Norethylmorphine Normorphine-3-glucuronide Conjugation - Glucuronidation Unclear [7]
MR012877 Norethylmorphine Norethylmorphine-6-glucuronide Unclear Unclear [1]
MR012870 Normorphine Normorphine-3-glucuronide Unclear Unclear [1]
MR012871 Normorphine Normorphine-6-glucuronide Unclear Unclear [1]
⏷ Show the Full List of 11 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
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
Docosahexaenoic acid omega-hydroxylase (CYP4F11) DME0616 Homo sapiens
CP4FB_HUMAN
1.14.14.1
[6]
References
1 Biotransformation and pharmacokinetics of ethylmorphine after a single oral dose. Br J Clin Pharmacol. 1995 Jun;39(6):611-20.
2 Inhibitory monoclonal antibody to human cytochrome P450 2B6. Biochem Pharmacol. 1998 May 15;55(10):1633-40.
3 A sensitive LC-MS/MS assay for the determination of dextromethorphan and metabolites in human urine--application for drug interaction studies assessing potential CYP3A and CYP2D6 inhibition. J Pharm Biomed Anal. 2002 Aug 22;30(1):113-24.
4 Metabolic activation of aromatic amines by human pancreas. Carcinogenesis. 1997 May;18(5):1085-92.
5 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
6 Expression and characterization of human cytochrome P450 4F11: putative role in the metabolism of therapeutic drugs and eicosanoids. Toxicol Appl Pharmacol. 2004 Sep 15;199(3):295-304.
7 Ethylmorphine metabolism in isolated rat hepatocytes
8 Urinary excretion of codeine, ethylmorphine, and their metabolites: relation to the CYP2D6 activity
9 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.
10 Metabolism and pharmacokinetics of morphine in neonates: A review
11 Aniline and its metabolites generate free radicals in yeast
12 Metabolism of vitamin E in sheep

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