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

General Information of Drug (ID: DR0905)
Drug Name
Ketobemidone
Synonyms
Ketobemidone HCl; Ketobemidone hydrochloride; Ketobimedon hydrochloride; Ketogan (TN); Cliradon hydrochloride; LS-123062; SCHEMBL9706814; U9U6LTV80K; 1-Methyl-4-(m-hydroxyphenyl)piperidine-4-ethylketone hydrochloride; 1-Propanone, 1-(4-(m-hydroxyphenyl)-1-methyl-4-piperidyl)-, hydrochloride; 1-[4-(3-hydroxyphenyl)-1-methylpiperidin-4-yl]propan-1-one hydrochloride(1:1); 5965-49-1; AC1L2YOJ; AC1Q5G7W; D08101; DTXSID00208327; EINECS 227-749-8; UNII-U9U6LTV80K
Indication Anaesthesia [ICD11: 8E22] Phase 4 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 283.79 Topological Polar Surface Area 40.5
Heavy Atom Count 19 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
80069
CAS Number
5965-49-1
TTD Drug ID
D04BCW
Formula
C15H22ClNO2
Canonical SMILES
CCC(=O)C1(CCN(C)CC1)c2cccc(O)c2.OC(=O)C(=O)O
InChI
1S/C15H21NO2.C2H2O4/c1-3-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12;3-1(4)2(5)6/h4-6,11,17H,3,7-10H2,1-2H3;(H,3,4)(H,5,6)
InChIKey
HYDFAZFVKRXNJX-UHFFFAOYSA-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
Dihydroxy ketobemidone DM002577
85992903
Unclear 1 [4]
Ketobemidone N-oxide metabolite DM002585
86008574
Oxidation - N-Oxidation 1 [5]
Norketobemidone DM002581
161154
Oxidation - N-Demethylation 1 [4] , [2]
Reduced ketobemidone DM002584
12639376
Reduction - Reduction 1 [3]
Dihydroxy norketobemidone DM002582 N. A. Oxidation - 4'-Hydroxylation 2 [4]
M-hydroxymethoxy ketobemidone DM002580
86251463
Unclear 2 [4]
Norketobemidone glucuronide metabolite DM002583
101498937
Unclear 2 [6]
p-hydroxymethoxy ketobemidone DM002578
85992904
Unclear 2 [4]
p-hydroxymethoxy ketobemidone glucuronide metabolite DM002579 N. A. Unclear 3 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001335 Ketobemidone Dihydroxy ketobemidone Unclear COX-1 [4]
MR001336 Ketobemidone Norketobemidone Oxidation - N-Demethylation CYP2C9 ... [4], [2]
MR001337 Ketobemidone Reduced ketobemidone Reduction - Reduction COX-1 [3]
MR001338 Ketobemidone Ketobemidone N-oxide metabolite Oxidation - N-Oxidation COX-1 [5]
MR001330 Dihydroxy ketobemidone p-hydroxymethoxy ketobemidone Unclear Unclear [4]
MR001331 Dihydroxy ketobemidone M-hydroxymethoxy ketobemidone Unclear Unclear [4]
MR001333 Norketobemidone Dihydroxy norketobemidone Oxidation - 4'-Hydroxylation Unclear [4]
MR001334 Norketobemidone Norketobemidone glucuronide metabolite Unclear Unclear [6]
MR001332 p-hydroxymethoxy ketobemidone p-hydroxymethoxy ketobemidone glucuronide metabolite Unclear Unclear [6]
⏷ Show the Full List of 9 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 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[3]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[4]
⏷ Show the Full List of 7  DME(s)
References
1 ClinicalTrials.gov (NCT03023462) Effectiveness of a Quadratus Lumborum 3 Block vs. a TAP-block for Inguinal Hernia Repair.
2 Ketobemidone is a substrate for cytochrome P4502C9 and 3A4, but not for P-glycoprotein. Xenobiotica. 2005 Aug;35(8):785-96.
3 DrugBank(Pharmacology-Metabolism)Ketobemidone hydrochloride
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Quantitative determination of the urinary excretion of ketobemidone and four of its metabolites after intravenous and oral administration in man Drug Metab Dispos. 1981 Jul-Aug;9(4):376-80.
6 In vivo investigation of brain and systemic ketobemidone metabolism Analyst. 2010 Feb;135(2):405-13. doi: 10.1039/b917940b.

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