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Compound Detail

CHEMBL100116

PENTAZOCINE
💊 Approved Drug
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💊 Approved Drug
CC(C)=CCN1CCC2(C)c3cc(O)ccc3CC1C2C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL100116
Name PENTAZOCINE
Phase Approved
Structure Type MOL
InChI Key VOKSWYLNZZRQPF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Dl-pentazocine NIH-7958 NSC-107430 Pentazocina Pentazocine Pentazocine civ WIN 20,228 WIN-20228
7
Targets
38
Activities
4
Assay Types
0
PK Parameters
20
Publications
8
Known Names
2
Indications

Molecular Properties

285.4
MW (Da)
3.88
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.83
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1967
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -azocine
USAN Year 1963

Extended Properties

Molecular Formula C19H27NO
MW 285.43
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 1.75

Indications

Pain Bipolar Disorder

ATC Classification

N02AD01
pentazocine
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

Ki 30 meas. best 8.66
IC50 4 meas. best 6.55
EC50 3 meas. best 7.4
Kd 1 meas. best 8.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
 Ki 8.66 8.39 2.2 2
Mu-type opioid receptor
CHEMBL233
 Ki 8.57 8.53 2.7 6
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Kd 8.54 8.54 2.9 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Ki 8.51 8.272 3.1 15
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 8.33 8.125 4.7 2
Kappa-type opioid receptor
CHEMBL237
 EC50 7.4 7.4 40.0 1
Mu-type opioid receptor
CHEMBL233
 EC50 7.21 7.21 61.0 2
Delta-type opioid receptor
CHEMBL236
 Ki 7.21 7.21 62.0 1
Mu-type opioid receptor
CHEMBL233
 IC50 6.55 6.55 280.0 4
Sigma intracellular receptor 2
CHEMBL4105864
 Ki 5.83 5.83 1465.0 1
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 5.83 5.7967 1465.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 2.2 nM 8.66 Binding affinity to kappa opioid receptor (unknown origin) 33111525
Mu-type opioid receptor Ki = 2.7 nM 8.57 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Mu-type opioid receptor Ki = 2.7 nM 8.57 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Mu-type opioid receptor Ki = 2.7 nM 8.57 Opioid Receptor Binding Assay: The Ki (binding affinity) for μ opioid receptors ... -
Mu-type opioid receptor Ki = 2.7 nM 8.57 Opioid Receptor Binding Assay: The Ki (binding affinity) for μ opioid receptors ... -
Sigma non-opioid intracellular receptor 1 Kd = 2.9 nM 8.54 Binding affinity to sigma1 receptor in Hartley guinea pig brain cortex membranes... 31129453
Sigma non-opioid intracellular receptor 1 Ki = 3.1 nM 8.51 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain me... 36919956
Mu-type opioid receptor Ki = 3.2 nM 8.49 Binding affinity to MOR (unknown origin) assessed as inhibition constant by radi... 36179400
Sigma non-opioid intracellular receptor 1 Ki = 3.93 nM 8.41 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain me... 34902734
Mu-type opioid receptor Ki = 3.9 nM 8.41 Binding affinity to mu opioid receptor (unknown origin) 33111525
Sigma non-opioid intracellular receptor 1 Ki = 4.3 nM 8.37 Displacement of [3H]-(+)-pentazocine from Dunkin-Hartley guinea pig brain cortex... 35016113
Sigma non-opioid intracellular receptor 1 Ki = 4.7 nM 8.33 Binding affinity to sigma 1 receptor (unknown origin) assessed as inhibition con... 35724925
Sigma non-opioid intracellular receptor 1 Ki = 4.7 nM 8.33 Displacement of [3H]-(+)-pentazocine from sigma-1 receptor in guinea pig brain m... 33372782
Sigma non-opioid intracellular receptor 1 Ki = 4.7 nM 8.33 Displacement of [3H]-(+)-pentazocine from sigma1 receptor in guinea pig brain me... 32435401
Sigma non-opioid intracellular receptor 1 Ki = 5.4 nM 8.27 Displacement of [3H]-(+)-pentazocine from sigma1 receptor in guinea pig brain co... 30350997
Sigma non-opioid intracellular receptor 1 Ki = 5.4 nM 8.27 Displacement of [3H]-(+)-Pentazocine from sigma1 receptor in guinea pig brain co... -
Sigma non-opioid intracellular receptor 1 Ki = 5.4 nM 8.27 Displacement of [3H]-(+)-pentazocine from sigma1 receptor in guinea pig brain me... 30543421
Sigma non-opioid intracellular receptor 1 Ki = 5.4 nM 8.27 Displacement of [3H]-pentazocine from guinea pig brain sigma 1 receptor incubate... 34046612
Sigma non-opioid intracellular receptor 1 Ki = 5.4 nM 8.27 Displacement of [3H]-(+)-pentazocine from sigma1 receptor in guinea pig brain me... 35033825
Sigma non-opioid intracellular receptor 1 Ki = 5.7 nM 8.24 Displacement of [3H]-pentazocine from sigma1 receptor in guinea pig brain membra... 33148494

Literature References

PubMed DOI Target Context # Activities
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
- 10.1007/s00044-012-0298-1 Mus musculus 4
36179400 10.1016/j.ejmech.2022.114785 Kappa-type opioid receptor 2
34046612 10.1039/d0md00307g Sigma non-opioid intracellular receptor 1 1
34902734 10.1016/j.ejmech.2021.114038 Sigma non-opioid intracellular receptor 1 1
33901806 10.1016/j.ejmech.2021.113443 Sigma non-opioid intracellular receptor 1 1
33372782 10.1021/acs.jmedchem.0c01964 Sigma non-opioid intracellular receptor 1 1
33148494 10.1016/j.ejmech.2020.112950 Sigma non-opioid intracellular receptor 1 1
33111525 10.1021/acs.jmedchem.0c01192 Kappa-type opioid receptor 1
33111525 10.1021/acs.jmedchem.0c01192 Mu-type opioid receptor 1
33111525 10.1021/acs.jmedchem.0c01192 Sigma intracellular receptor 2 1
33111525 10.1021/acs.jmedchem.0c01192 Sigma non-opioid intracellular receptor 1 1
32435401 10.1021/acsmedchemlett.9b00661 Sigma intracellular receptor 2 1
32435401 10.1021/acsmedchemlett.9b00661 Sigma non-opioid intracellular receptor 1 1
31129453 10.1016/j.ejmech.2019.05.034 Sigma non-opioid intracellular receptor 1 1
30543421 10.1021/acs.jmedchem.8b01609 Sigma non-opioid intracellular receptor 1 1
30025348 10.1016/j.ejmech.2018.07.026 Sigma non-opioid intracellular receptor 1 1
30143421 10.1016/j.bmcl.2018.08.016 PANC-1 1
30143421 10.1016/j.bmcl.2018.08.016 SH-SY5Y 1
- 10.1039/C6MD00441E Sigma non-opioid intracellular receptor 1 1

Data from ChEMBL 36 via Core Engine