Page last updated: 2024-11-05

normeperidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Normeperidine is a major metabolite of meperidine, a synthetic opioid analgesic. It is produced in the body through the enzymatic demethylation of meperidine by cytochrome P450 enzymes. Normeperidine has been shown to have analgesic effects, although it is weaker than meperidine. It is also associated with neurotoxicity, particularly in patients with renal insufficiency. Studies on normeperidine are important for understanding the metabolism and potential adverse effects of meperidine. Its neurotoxicity has led to concern regarding its accumulation in patients with impaired renal function, highlighting the need for careful monitoring and dose adjustments in such individuals. Further research is ongoing to elucidate the mechanisms of normeperidine's neurotoxicity and to develop strategies for mitigating its adverse effects.'

normeperidine: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID32414
CHEMBL ID1052
SCHEMBL ID341796
MeSH IDM0043476

Synonyms (42)

Synonym
CHEMBL1052 ,
isonipecotic acid, 4-phenyl-, ethyl ester
nsc-23821
ethyl 4-phenylisonipecotate
4-phenyl-4-carbethoxypiperidine
4-carbethoxy-4-phenylpiperidine
ethyl 4-phenylpiperidine-4-carboxylate
isonipecotic acid, 4-phenyl-, ethyl ester (6ci,7ci,8ci)
4-piperidinecarboxylic acid, 4-phenyl-, ethyl ester
4-phenylpiperidine-4-carboxylic acid ethyl ester
77-17-8
4-(ethoxycarbonyl)-4-phenylpiperidine
NCGC00160433-01
normeperidine
4-phenyl-piperidine-4-carboxylic acid ethyl ester
bdbm50071692
STK689062
AKOS005601310
norpethidine
pethidine - intermediate-b
nordolsin
einecs 201-008-9
ethyl-4-phenylpiperidine-4-carboxylate
dea no. 9233
unii-jg096pmw2n
jg096pmw2n ,
pethidine intermediate b
pethidine-intermediate-b, ethyl-4-phenylpiperidine-4-carboxylate
ids-np-003
n-desmethylmeperidine
SCHEMBL341796
ethyl 4-phenyl-4-piperidinecarboxylate #
DTXSID50227806
4-ethoxycarbonyl-4-phenylpiperidine
ethyl 4-phenyl-4-piperidinecarboxylate
4-phenyl-4-carboethoxy-piperidine
W-104326
norpethidine (normeperidine) 0.1 mg/ml in methanol
norpethidine (normeperidine)
FT-0721754
AS-37791
Q7053200

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" No apparent ethnic differences were found in the tmax and Cmax of norpethidine which emerged as the major metabolite in the plasma in the three races."( Pethidine pharmacokinetics after intramuscular dose: a comparison in Caucasian, Chinese and Nepalese patients.
Aun, CS; Chan, K; Houghton, IT; Lau, OW; Lowe, DM; Wong, YC,
)
0.13
"Open-label, crossover, pharmacokinetic study."( The effect of ritonavir on the pharmacokinetics of meperidine and normeperidine.
Bertz, RJ; Davey, R; Kress, DR; Pau, A; Piscitelli, SC, 2000
)
0.54
" We estimated the apparent pharmacokinetic parameters for meperidine in oral fluid and plasma and determined the ratio and correlation between oral fluid and plasma concentrations."( Pharmacokinetics of meperidine (pethidine) in rabbit oral fluid: correlation with plasma concentrations after controlled administration.
Cao, J; Du, Y; Jia, J; Liang, W; Sun, JH; Wang, YJ; Wang, YY; Wei, ZW; Wu, B; Yun, KM, 2018
)
0.48

Bioavailability

ExcerptReferenceRelevance
"3 h and 14 min, respectively), but systemic bioavailability was similar."( CSF and plasma pharmacokinetics of pethidine and norpethidine in man after epidural and intrathecal administration of pethidine.
Bondesson, U; Boréus, LO; Hansdottir, V; Hedner, T; Mellstrand, T; Nordberg, G, 1988
)
0.27
" Systemic clearance of meperidine was smaller and bioavailability and half-life greater in the cirrhotic patients than in the normal subjects."( Presystemic metabolism of meperidine to normeperidine in normal and cirrhotic subjects.
Benowitz, NL; Jacob, P; Pond, SM; Rigod, J; Tong, T, 1981
)
0.53

Dosage Studied

ExcerptRelevanceReference
" Caution may be required on multiple dosing of pethidine in Asian patients due to the possible accumulation of the parent drug and its toxic metabolite, norpethidine."( Pethidine pharmacokinetics after intramuscular dose: a comparison in Caucasian, Chinese and Nepalese patients.
Aun, CS; Chan, K; Houghton, IT; Lau, OW; Lowe, DM; Wong, YC,
)
0.13
" The results suggest that in patients requiring repeated meperidine dosage the drug should be taken parenterally rather than orally to allow maximal analgesia and minimal formation of normeperidine."( Presystemic metabolism of meperidine to normeperidine in normal and cirrhotic subjects.
Benowitz, NL; Jacob, P; Pond, SM; Rigod, J; Tong, T, 1981
)
0.72
" Patients with normal renal function rarely manifest seizure activity when given meperidine, but if the drug is used in large doses at frequent dosing intervals, seizures may occur."( Meperidine-induced generalized seizures with normal renal function.
Marinella, MA, 1997
)
0.3
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorHomo sapiens (human)IC50 (µMol)1.10000.00010.813310.0000AID152064
Mu-type opioid receptorMus musculus (house mouse)Ki1.30000.00000.12281.3000AID149068
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMu-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
sensory perceptionMu-type opioid receptorHomo sapiens (human)
negative regulation of cell population proliferationMu-type opioid receptorHomo sapiens (human)
sensory perception of painMu-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
behavioral response to ethanolMu-type opioid receptorHomo sapiens (human)
positive regulation of neurogenesisMu-type opioid receptorHomo sapiens (human)
negative regulation of Wnt protein secretionMu-type opioid receptorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeMu-type opioid receptorHomo sapiens (human)
calcium ion transmembrane transportMu-type opioid receptorHomo sapiens (human)
cellular response to morphineMu-type opioid receptorHomo sapiens (human)
regulation of cellular response to stressMu-type opioid receptorHomo sapiens (human)
regulation of NMDA receptor activityMu-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayMu-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
G-protein alpha-subunit bindingMu-type opioid receptorHomo sapiens (human)
G protein-coupled receptor activityMu-type opioid receptorHomo sapiens (human)
beta-endorphin receptor activityMu-type opioid receptorHomo sapiens (human)
voltage-gated calcium channel activityMu-type opioid receptorHomo sapiens (human)
protein bindingMu-type opioid receptorHomo sapiens (human)
morphine receptor activityMu-type opioid receptorHomo sapiens (human)
G-protein beta-subunit bindingMu-type opioid receptorHomo sapiens (human)
neuropeptide bindingMu-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
endosomeMu-type opioid receptorHomo sapiens (human)
endoplasmic reticulumMu-type opioid receptorHomo sapiens (human)
Golgi apparatusMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
axonMu-type opioid receptorHomo sapiens (human)
dendriteMu-type opioid receptorHomo sapiens (human)
perikaryonMu-type opioid receptorHomo sapiens (human)
synapseMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
neuron projectionMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorMus musculus (house mouse)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID149068Opioid binding affinity was evaluated using [3H]DAMGO as radioligand1998Bioorganic & medicinal chemistry letters, Sep-22, Volume: 8, Issue:18
Selective alpha-1a adrenergic receptor antagonists. Effects of pharmacophore regio- and stereochemistry on potency and selectivity.
AID152064Inhibitory concentration against Opioid receptor mu 1 using [3H]DAMGO ligand1999Journal of medicinal chemistry, Nov-18, Volume: 42, Issue:23
Design and synthesis of novel alpha(1)(a) adrenoceptor-selective antagonists. 2. Approaches to eliminate opioid agonist metabolites via modification of linker and 4-methoxycarbonyl-4-phenylpiperidine moiety.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (86)

TimeframeStudies, This Drug (%)All Drugs %
pre-199048 (55.81)18.7374
1990's21 (24.42)18.2507
2000's7 (8.14)29.6817
2010's8 (9.30)24.3611
2020's2 (2.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.62

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index36.62 (24.57)
Research Supply Index4.62 (2.92)
Research Growth Index4.49 (4.65)
Search Engine Demand Index53.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.62)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (6.38%)5.53%
Reviews0 (0.00%)6.00%
Case Studies14 (14.89%)4.05%
Observational1 (1.06%)0.25%
Other73 (77.66%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]