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Compound Detail

CHEMBL607

MEPERIDINE
💊 Approved Drug
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💊 Approved Drug
CCOC(=O)C1(c2ccccc2)CCN(C)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL607
Name MEPERIDINE
Phase Approved
Structure Type MOL
InChI Key XADCESSVHJOZHK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

IDS-NP-001 Isonipecaine Meperidine Meperidol Pethanol Pethidine Pethidine dbl Pethidineter Petidina Renaudin
10
Targets
14
Activities
3
Assay Types
11
PK Parameters
20
Publications
10
Known Names
4
Indications

Molecular Properties

247.3
MW (Da)
2.21
ALogP
3
HBA
0
HBD
29.5
PSA (Ų)
0.77
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1942
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -eridine

Extended Properties

Molecular Formula C15H21NO2
MW 247.34
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.56

Indications

Pain Ischemic Stroke Sciatica Scoliosis

ATC Classification

N02AB02
pethidine
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02AB52
pethidine, combinations excl. psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02AB72
pethidine, combinations with psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

IC50 9 meas. best 6.5
Ki 3 meas. best 6.38
EC50 2 meas. best 6.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 IC50 6.5 6.5 315.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 6.49 4.9133 323.6 3
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 6.38 6.38 412.0 1
Mu-type opioid receptor
CHEMBL4354
 Ki 6.35 6.35 451.0 1
Opioid receptors; mu/kappa/delta
CHEMBL2095181
 IC50 6.3 5.35 500.0 2
Opioid receptor
CHEMBL2095192
 IC50 6.3 6.3 500.0 1
Opioid receptor
CHEMBL2094129
 EC50 6.16 6.16 700.0 1
Kappa-type opioid receptor
CHEMBL237
 IC50 5.62 5.62 2370.0 1
Mu-type opioid receptor
CHEMBL233
 EC50 5.03 5.03 9400.0 1
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 4.75 4.75 17800.0 1
Solute carrier family 22 member 1
CHEMBL5685
 IC50 4.65 4.65 22250.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 4.9 mL.min-1.kg-1 Homo sapiens
CL 43.0 mL.min-1.kg-1 Canis lupus familiaris
CL 253.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.0 mL.min-1.kg-1 Macaca
CL 4.9 mL.min-1.kg-1 Homo sapiens
CL 17.0 mL.min-1.kg-1 Homo sapiens
F 79.0 % Homo sapiens
Fu 0.42 - Homo sapiens
Fu 0.42 - Homo sapiens
MRT 6.4 hr Homo sapiens
T1/2 7.9 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor IC50 = 315.0 nM 6.5 Binding affinity against mu-opiate receptor (human) using [3H]DAMGO radioligand 11585443
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 323.59 nM 6.49 Inhibitory concentration against potassium channel HERG 15911273
Sodium-dependent serotonin transporter Ki = 412.0 nM 6.38 Displacement of [3H]paroxetine from serotonin transporter (SERT) 10612583
Mu-type opioid receptor Ki = 451.0 nM 6.35 Binding affinity against mu opioid receptor was determined in brain membrane pre... 9873439
Opioid receptors; mu/kappa/delta IC50 = 500.0 nM 6.3 Inhibition of Opioid receptors with [3H]naloxone binding in the absence of NaCl 6106064
Opioid receptor IC50 = 500.0 nM 6.3 Tested for displacement of radioligand [3H]-Naloxone from opiate receptor 8410989
Opioid receptor EC50 = 700.0 nM 6.16 Displacement of radiolabeled dihydromorphine from opioid receptor in rat brain h... 109618
Kappa-type opioid receptor IC50 = 2370.0 nM 5.62 Binding affinity against opioid receptor kappa 1 using [3H]- U-69,593 radioligan... 11585443
Mu-type opioid receptor EC50 = 9400.0 nM 5.03 Agonist activity at human cloned mu opioid receptor by [35S]GTPgammaS binding as... 19168350
Sodium-dependent dopamine transporter Ki = 17800.0 nM 4.75 Displacement of [3H]WIN-35428 from dopamine transporter (DAT) 10612583
Solute carrier family 22 member 1 IC50 = 22250.0 nM 4.65 Inhibition of human OCT1 expressed in HEK293 cells assessed as reduction in ASP+... 31597043
Opioid receptors; mu/kappa/delta IC50 = 40000.0 nM 4.4 Inhibition of Opioid receptors binding by inhibiting specific [3H]naloxone bindi... 6106064
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 74131.02 nM 4.13 Inhibition of human ERG 21185626
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 75857.76 nM 4.12 Inhibition of human ERG channel in HEK293 cells by voltage-clamp method 18262683

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15920768 10.1002/jps.20373 ADMET 8
31597043 10.1021/acs.jmedchem.9b01301 Solute carrier family 22 member 1 4
628000 10.1021/jm00201a004 Mus musculus 4
18426954 10.1124/dmd.108.020479 ADMET 4
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
3007760 10.1021/jm00154a018 Opioid receptor 3
20014752 10.1021/tx900326k Hepatotoxicity 3
6106064 10.1021/jm00183a005 Opioid receptors; mu/kappa/delta 3
18579259 10.1016/j.ejmech.2008.04.022 Mus musculus 2
22931300 10.1021/tx300075j Liver microsomes 2
19445515 10.1021/jm900403j Homo sapiens 2
10891117 10.1021/jm0000564 ADMET 2
10891117 10.1021/jm0000564 No relevant target 2
2845084 10.1021/jm00118a028 Mus musculus 2
14971904 10.1021/jm030408h ADMET 2
853506 10.1021/jm00215a016 Mus musculus 2
853506 10.1021/jm00215a016 Rattus norvegicus 2

Data from ChEMBL 36 via Core Engine