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Compound Detail

CHEMBL73234

CARBETAPENTANE
💊 Approved Drug
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💊 Approved Drug
CCN(CC)CCOCCOC(=O)C1(c2ccccc2)CCCC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL73234
Name CARBETAPENTANE
Phase Approved
Structure Type MOL
InChI Key CFJMRBQWBDQYMK-UHFFFAOYSA-N

Known Names

Pentoxiverina Pentoxyverine Sedotussin
11
Targets
24
Activities
3
Assay Types
0
PK Parameters
20
Publications
3
Known Names
1
Indications

Molecular Properties

333.5
MW (Da)
3.40
ALogP
4
HBA
0
HBD
38.8
PSA (Ų)
0.49
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Routes of Administration

Oral

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C20H31NO3
MW 333.47
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness -0.85

Indications

Cough

ATC Classification

R05DB05
pentoxyverine
Level 1: RESPIRATORY SYSTEM
Level 2: COUGH AND COLD PREPARATIONS

Activity Summary

Ki 13 meas. best 7.96
EC50 7 meas. best 6.12
IC50 4 meas. best 7.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Sigma non-opioid intracellular receptor 1
CHEMBL3602
 Ki 7.96 7.7025 11.0 4
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 7.71 7.3 19.5 2
Lysosomal Pro-X carboxypeptidase
CHEMBL2335
 IC50 7.5 7.5 32.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
 Ki 7.12 7.12 76.0 2
Muscarinic acetylcholine receptor M2
CHEMBL211
 Ki 6.78 6.78 167.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.12 5.4671 765.0 7
Sigma 2 receptor
CHEMBL613288
 Ki 6.05 6.05 894.0 1
Solute carrier family 22 member 1
CHEMBL5685
 IC50 5.81 5.81 1550.0 1
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 5.71 5.71 1953.0 1
Sodium-dependent dopamine transporter
CHEMBL338
 Ki 5.51 5.51 3090.0 2
Unchecked
CHEMBL612545
 IC50 5.33 5.22 4655.6 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Sigma non-opioid intracellular receptor 1 Ki = 11.0 nM 7.96 Tested for its binding affinity towards sigma-1 site in presence of [3H]- -(+)3 ... 8057277
Sigma non-opioid intracellular receptor 1 Ki = 11.0 nM 7.96 Tested for its binding affinity towards sigma-1 site in presence of [3H]- dextro... 8057277
Sigma non-opioid intracellular receptor 1 Ki = 19.5 nM 7.71 Binding affinity against Sigma receptor type 1 was determined by the displacemen... 12801223
Lysosomal Pro-X carboxypeptidase IC50 = 32.0 nM 7.5 Inhibition of [3H]- (+) - pentazocine binding to PCP receptor obtained from tiss... 9484497
Sigma non-opioid intracellular receptor 1 Ki = 32.0 nM 7.5 Tested for its binding affinity towards sigma-1 site in presence of [3H]- - (+) ... 8057277
Sigma non-opioid intracellular receptor 1 Ki = 41.0 nM 7.39 Tested for its binding affinity towards sigma-1 site in rat brain using E3H1-(+)... 8057277
Muscarinic acetylcholine receptor M1 Ki = 76.0 nM 7.12 Binding affinity to muscarinic acetylcholine receptor M1 (unknown origin) 33111525
Muscarinic acetylcholine receptor M1 Ki = 76.0 nM 7.12 Binding affinity towards muscarinic m1 receptor 8057277
Sigma non-opioid intracellular receptor 1 Ki = 129.0 nM 6.89 Binding affinity to sigma-1 receptor (unknown origin) 33111525
Muscarinic acetylcholine receptor M2 Ki = 167.0 nM 6.78 Binding affinity towards muscarinic m2 receptor 8057277
NON-PROTEIN TARGET EC50 = 765.0 nM 6.12 Antiproliferative activity against mouse neural precursor cells by MTT assay 17417631
Sigma 2 receptor Ki = 894.0 nM 6.05 Tested for its binding affinity towards sigma-2 site in rat brain using [3H]DTG ... 8057277
Solute carrier family 22 member 1 IC50 = 1550.0 nM 5.81 Inhibition of human OCT1 expressed in HEK293 cells assessed as decrease in uptak... 28230985
NON-PROTEIN TARGET EC50 = 1730.0 nM 5.76 Antiproliferative activity against human GBM2 cells by MTT assay 17417631
Sigma intracellular receptor 2 Ki = 1953.0 nM 5.71 Binding affinity to sigma-2 receptor (unknown origin) 33111525
NON-PROTEIN TARGET EC50 = 2040.0 nM 5.69 Antiproliferative activity against mouse neural precursor cells by colony format... 17417631
NON-PROTEIN TARGET EC50 = 2083.0 nM 5.68 Antiproliferative activity against mouse medulloblastoma cells harboring heteroz... 17417631
Sodium-dependent dopamine transporter Ki = 3090.0 nM 5.51 Binding affinity against dopamine transporter was determined by the displacement... 12801223
Sodium-dependent dopamine transporter Ki = 3090.3 nM 5.51 Binding affinity to dopamine transporter (DAT) using [3H]WIN-35428 as a radiolig... 11063611
Unchecked IC50 = 4655.58 nM 5.33 PubChem BioAssay. tonic K+ channel activity under 0.1 mM glucose conditions in I... -

Literature References

PubMed DOI Target Context # Activities
31158845 10.1038/s41586-019-1291-3 ADMET 541
- 10.5281/zenodo.13943903 ADMET 89
17417631 10.1038/nchembio873 NON-PROTEIN TARGET 8
8057277 10.1021/jm00041a006 Sigma non-opioid intracellular receptor 1 5
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
17417631 10.1038/nchembio873 Unchecked 2
1956032 10.1021/jm00115a002 Rattus norvegicus 2
8057277 10.1021/jm00041a006 Unchecked 1
28230985 10.1021/acs.jmedchem.6b01317 Solute carrier family 22 member 1 1
18027916 10.1021/jm070524a Sphingomyelin phosphodiesterase 1
11063611 10.1021/jm990472s Sodium-dependent dopamine transporter 1
12801223 10.1021/jm030008u Sodium-dependent dopamine transporter 1
8057277 10.1021/jm00041a006 Muscarinic acetylcholine receptor M2 1
8057277 10.1021/jm00041a006 Muscarinic acetylcholine receptor M1 1
8057277 10.1021/jm00041a006 Glutamate NMDA receptor 1
8057277 10.1021/jm00041a006 Sigma 2 receptor 1
12873507 10.1016/s0960-894x(03)00535-3 NON-PROTEIN TARGET 1
9484497 10.1021/jm970059p Lysosomal Pro-X carboxypeptidase 1
12801223 10.1021/jm030008u Unchecked 1

Data from ChEMBL 36 via Core Engine