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

General Information of Drug (ID: DR1024)
Drug Name
Meperidine
Synonyms
Meperidol; Nemerol; Pethanol; Pethidin; Pethidine; Demarol; Demerol; Dolsin; Isonipecaine; Pethidineter; Pethidinum; Pethidinum [INN-Latin]; Petidina; Petidina [INN-Spanish]; Petydyna; Petydyna [Polish]; Phetidine; Piperosal; Pipersal; meperidine; 4-Piperidinecarboxylic acid, 1-methyl-4-phenyl-, ethyl ester; 57-42-1; Ethyl 1-methyl-4-phenylisonipecotate; Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate; HSDB 3116; Isonipecotic acid, 1-methyl-4-phenyl-, ethyl ester; Lydol; Methyl phenylpiperidine carbonic acid ethyl ester
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 247.33 Topological Polar Surface Area 29.5
Heavy Atom Count 18 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
4058
PubChem SID
9338 ; 841258 ; 4359668 ; 7978480 ; 8152545 ; 10527888 ; 11336158 ; 11361397 ; 11462369 ; 14823367 ; 24882043 ; 29223169 ; 46506899 ; 47736577 ; 48416212 ; 49986147 ; 50185474 ; 53789706 ; 57322120 ; 57651808 ; 85209612 ; 96025030 ; 103184537 ; 103936336 ; 104305308 ; 126407782 ; 129659418 ; 134337544 ; 134970866 ; 137003750 ; 140053016 ; 160963800 ; 175267872 ; 177513108 ; 178103795 ; 179148680 ; 184546706 ; 223440287 ; 224511988 ; 226413511 ; 241102133 ; 249933926
ChEBI ID
CHEBI:6754
CAS Number
57-42-1
TTD Drug ID
D00UYE
Formula
C15H21NO2
Canonical SMILES
CCOC(=O)C1(CCN(CC1)C)C2=CC=CC=C2
InChI
1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3
InChIKey
XADCESSVHJOZHK-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
Meperidine N-oxide DM014987
21067
Oxidation - N-demethylation 1 [5]
Meperidinic acid DM015120
101106
Unclear - Unclear 1 [5]
Methoxy-hydroxymeperidine DM018101 N. A. Unclear - Unclear 1 [5]
Normeperidine DM015006
32414
Oxidation - N-demethylation 1 [6] , [7] , [4]
p-hydrox ymeperidine DM015017
51161
Unclear - Unclear 1 [5]
N-hydroxynormeperidine DM016309
71374166
Unclear - Unclear 2 [5]
Normeperidinic acid DM014984
19259
Hydrolysis - Hydrolysis 2 [5]
p-hydroxynormeperidine DM016305
71330784
Unclear - Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013111 Meperidine Normeperidine Oxidation - N-demethylation CYP3A4 ... [6], [7], [4]
MR013115 Meperidine Meperidinic acid Unclear - Unclear Unclear [5]
MR013117 Meperidine Meperidine N-oxide Oxidation - N-demethylation Unclear [5]
MR013118 Meperidine Methoxy-hydroxymeperidine Unclear - Unclear Unclear [5]
MR013119 Meperidine p-hydrox ymeperidine Unclear - Unclear Unclear [5]
MR013116 Meperidinic acid Normeperidinic acid Hydrolysis - Hydrolysis Unclear [5]
MR013112 Normeperidine Normeperidinic acid Hydrolysis - Hydrolysis Unclear [5]
MR013113 Normeperidine N-hydroxynormeperidine Unclear - Unclear Unclear [5]
MR013114 Normeperidine p-hydroxynormeperidine Unclear - Unclear Unclear [5]
⏷ 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 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]
References
1 Meperidine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425.
3 Is meperidine the drug that just won't die? J Pediatr Pharmacol Ther. 2011 Jul;16(3):167-9.
4 Impact of cytochrome P450 variation on meperidine N-demethylation to the neurotoxic metabolite normeperidine. Xenobiotica. 2020 Feb;50(2):209-222.
5 Urinary excretion of meperidine and its metabolites
6 Meperidine and normeperidine levels following meperidine administration during labor. I. Mother
7 Effects of ethinyl estradiol on pharmacokinetics of meperidine and pentobarbital in the rat

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