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Compound Detail

CHEMBL60542

(+)-PENTAZOCINE
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CC(C)=CCN1CC[C@]2(C)c3cc(O)ccc3C[C@H]1[C@H]2C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL60542
Name (+)-PENTAZOCINE
Phase Preclinical
Structure Type MOL
InChI Key VOKSWYLNZZRQPF-CCKFTAQKSA-N
17
Targets
144
Activities
4
Assay Types
6
PK Parameters
20
Publications
0
Known Names

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
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

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

Activity Summary

Ki 130 meas. best 8.79
IC50 11 meas. best 8.52
Kd 2 meas. best 7.94
EC50 1 meas. best 7.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 Ki 8.79 8.3655 1.6 56
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 8.77 8.1541 1.7 27
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 IC50 8.52 7.5733 3.0 3
Unchecked
CHEMBL612545
 Ki 8.51 6.3255 3.1 20
Mu-type opioid receptor
CHEMBL233
 Ki 8.49 8.49 3.2 1
Zinc finger protein 664
CHEMBL4105757
 Ki 8.27 8.27 5.4 1
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 Ki 8.22 7.2333 6.0 6
Mu-type opioid receptor
CHEMBL270
 Ki 8.16 6.965 6.9 2
Kappa-type opioid receptor
CHEMBL237
 Ki 8.12 8.12 7.6 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 IC50 8.12 8.1 7.6 2
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Kd 7.94 7.7 11.6 2
Opioid receptor
CHEMBL2094129
 IC50 7.9 7.395 12.5 4
Kappa-type opioid receptor
CHEMBL237
 EC50 7.4 7.4 40.0 1
Delta-type opioid receptor
CHEMBL236
 Ki 7.21 7.21 62.0 1
Kappa-type opioid receptor
CHEMBL3952
 Ki 7.12 7.12 75.0 1
PC-3
CHEMBL390
 Ki 7.06 7.06 86.9 1
Muscarinic acetylcholine receptor M1
CHEMBL276
 Ki 6.65 6.65 225.0 1
Muscarinic acetylcholine receptor M2
CHEMBL309
 Ki 6.28 6.28 525.0 1
Sigma 2 receptor
CHEMBL613288
 Ki 6.25 5.9088 562.0 8
Opioid receptor
CHEMBL2094129
 Ki 6.19 5.905 651.0 2
Sigma 2 receptor
CHEMBL613288
 IC50 5.68 5.68 2100.0 1
5637
CHEMBL612565
 IC50 5.46 5.46 3500.0 1
Glutamate NMDA receptor
CHEMBL1907608
 Ki 5.38 5.38 4190.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 23.0 mL.min-1.kg-1 Homo sapiens
CL 23.0 mL.min-1.kg-1 Homo sapiens
F 18.0 % Homo sapiens
Fu 0.39 - Homo sapiens
MRT 2.5 hr Homo sapiens
T1/2 2.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sigma non-opioid intracellular receptor 1 Ki = 1.62 nM 8.79 Displacement of [3H]-(+)-pentazocine from sigma1 receptor in guinea pig brain me... 25468036
Sigma non-opioid intracellular receptor 1 Ki = 1.7 nM 8.77 Tested for binding affinity against sigma 1 receptor 8164264
Sigma non-opioid intracellular receptor 1 Ki = 2.1 nM 8.68 The compound was evaluated for affinity at sigma-1 site by inhibition of [3H](+)... 8027978
Sigma non-opioid intracellular receptor 1 Ki = 2.1 nM 8.68 Binding affinity for Sigma opioid receptor type 1 in guinea pig brain homogenate... -
Sigma non-opioid intracellular receptor 1 Ki = 2.2 nM 8.66 Displacement of [3H]-(+)-pentazocine from sigma 1 receptor in guinea pig brain m... 27396684
Sigma non-opioid intracellular receptor 1 Ki = 2.2 nM 8.66 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain me... 17967001
Sigma non-opioid intracellular receptor 1 Ki = 2.41 nM 8.62 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain me... 19053780
Sigma non-opioid intracellular receptor 1 Ki = 2.62 nM 8.58 Displacement of (+)-[3H]pentazocine from Dunkin guinea pig brain sigma 1 recepto... 24697311
Sigma non-opioid intracellular receptor 1 Ki = 2.62 nM 8.58 Displacement of [3H]-pentazocine from sigma 1 receptor from guinea pig brain mem... 21744858
Sigma non-opioid intracellular receptor 1 Ki = 2.7 nM 8.57 Inhibition of [3H]pentazocine binding to Sigma receptor type 1 in guinea pig bra... 12747784
Sigma non-opioid intracellular receptor 1 Ki = 2.8 nM 8.55 Displacement of [3H](+)-pentazocine from sigma 1 receptor in guinea pig brain me... 16366605
Sigma non-opioid intracellular receptor 1 IC50 = 3.0 nM 8.52 Compound was evaluated for the binding affinity towards Sigma receptor type 1 us... 7783132
Sigma non-opioid intracellular receptor 1 Ki = 3.0 nM 8.52 Displacement of (+)-[3H]-pentazocine from sigma 1 receptor in Dunkin guinea pig ... 24161678
Sigma non-opioid intracellular receptor 1 Ki = 3.0 nM 8.52 Displacement of [3H]-(+)-pentazocine from sigma 1 receptor in Dunkin guinea pig ... 21229979
Sigma non-opioid intracellular receptor 1 Ki = 3.05 nM 8.52 In vitro binding affinity at opioid sigma-1 receptor in guinea pig brain membran... 15084129
Sigma non-opioid intracellular receptor 1 IC50 = 3.0 nM 8.52 Binding affinity towards sigma receptor binding site 1 using [3H](+)-pentazocine 7783131
Sigma non-opioid intracellular receptor 1 Ki = 3.1 nM 8.51 Binding affinity to sigma 1 receptor 23641311
Sigma non-opioid intracellular receptor 1 Ki = 3.09 nM 8.51 Displacement of [3H]-pentazocine from sigma 1 receptor in guinea pig brain after... 21684636
Sigma non-opioid intracellular receptor 1 Ki = 3.09 nM 8.51 Displacement of (+)-[3H]pentazocine from sigma-1 receptor in guinea pig brain me... 24821398
Sigma non-opioid intracellular receptor 1 Ki = 3.1 nM 8.51 Displacement of [3H]-(+)-pentazocine from recombinant human sigma1 receptor expr... 30904383

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
26717207 10.1016/j.ejmech.2015.12.014 Sigma non-opioid intracellular receptor 1 10
7359514 10.1021/jm00175a013 Rattus norvegicus 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3656354 10.1021/jm00393a017 Mus musculus 5
12036376 10.1021/jm010501a Sigma non-opioid intracellular receptor 1 5
6103962 10.1021/jm00179a005 Mus musculus 4
23385092 10.1016/j.ejmech.2012.12.057 Rattus norvegicus 4
817021 10.1021/jm00226a003 Rattus norvegicus 4
7359514 10.1021/jm00175a013 Mus musculus 4
17328523 10.1021/jm0611197 Unchecked 4
19481931 10.1016/j.bmcl.2009.05.055 Rattus norvegicus 4
26186150 10.1016/j.ejmech.2015.07.002 Rattus norvegicus 4
18426954 10.1124/dmd.108.020479 ADMET 4
1322987 10.1021/jm00093a014 Unchecked 3
22405287 10.1016/j.ejmech.2012.02.030 Mus musculus 3
7783132 10.1021/jm00011a020 Sigma non-opioid intracellular receptor 1 3
7636861 10.1021/jm00015a023 Sigma non-opioid intracellular receptor 1 3
22795833 10.1016/j.ejmech.2012.06.011 Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine