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Compound Detail

CHEMBL74656

REL-CISAPRIDE
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COc1cc(N)c(Cl)cc1C(=O)N[C@H]1CCN(CCCOc2ccc(F)cc2)C[C@H]1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL74656
Name REL-CISAPRIDE
Phase Preclinical
Structure Type MOL
InChI Key DCSUBABJRXZOMT-RBBKRZOGSA-N
7
Targets
29
Activities
3
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

465.9
MW (Da)
3.36
ALogP
6
HBA
2
HBD
86.0
PSA (Ų)
0.44
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H29ClFN3O4
MW 465.95
Aromatic Rings 2
Heavy Atoms 32
NP-Likeness -1.13

Activity Summary

IC50 23 meas. best 8.7
EC50 3 meas. best 7.7
Ki 3 meas. best 7.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 8.7 7.1894 2.0 18
5-hydroxytryptamine receptor 4
CHEMBL1875
 EC50 7.7 7.4 19.9 2
5-hydroxytryptamine receptor 4
CHEMBL5017
 Ki 7.7 7.7 20.0 1
5-hydroxytryptamine receptor 4
CHEMBL1875
 Ki 7.0 7.0 100.0 2
5-hydroxytryptamine receptor 4
CHEMBL4317
 EC50 6.99 6.99 102.3 1
5-hydroxytryptamine receptor 4
CHEMBL1875
 IC50 6.32 6.32 483.0 1
A2780
CHEMBL614004
 IC50 5.28 5.28 5267.0 1
HUVEC
CHEMBL613979
 IC50 4.86 4.86 13900.0 1
Unchecked
CHEMBL612545
 IC50 4.36 4.335 43810.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 142.0 ng.hr.mL-1 Rattus norvegicus
Cmax 223.2 nM Rattus norvegicus
T1/2 0.7833 hr Rattus norvegicus
T1/2 47.0 hr Rattus norvegicus
T1/2 1.48 hr Rattus norvegicus
Tmax 0.25 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 2.0 nM 8.7 Inhibition of human ERG potassium channel transfected in CHO cells by automated ... 35649164
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 13.1 nM 7.88 Inhibition of hERG expressed in HEK293 cells 34048243
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 15.0 nM 7.82 Inhibition of human ERK potassium channel by automated patch clamp electrophysio... 35922963
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 15.0 nM 7.82 Inhibition of human ERG by whole-cell automated Syncro-patch assay 38598688
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 17.0 nM 7.77 Inhibition of hERG channel expressed in HEK293 cells at -80 mV holding potential... 35390713
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 17.0 nM 7.77 Inhibition of hERG in HEK293 cells by whole-cell patch clamp electrophysiologica... 37651874
5-hydroxytryptamine receptor 4 EC50 = 19.95 nM 7.7 Agonist activity at human 5HT4C receptor expressed at 100 fold physiological-lev... 22683222
5-hydroxytryptamine receptor 4 Ki = 20.0 nM 7.7 Displacement of [3H]GR113808 from serotonin 5-HT4 receptor in Dunkin-Hartley gui... 30108781
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 22.0 nM 7.66 Inhibition of human ERG potassium channel expressed in CHO cells by automated pa... 35797898
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 31.2 nM 7.51 Inhibition of human ERG potassium channel by manual patch-clamp electrophysiolog... 35737669
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 31.55 nM 7.5 Inhibition of human ERG 35091071
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 32.0 nM 7.5 Inhibition of human ERG expressed in CHO cells at -80 mV holding potential by au... 35679690
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 42.0 nM 7.38 Inhibition of hERG expressed in CHO cells 38996652
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 56.0 nM 7.25 Inhibition of hERG expressed in CHO cells at -80 mV holding potential by automat... 34922191
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 70.0 nM 7.16 Inhibition of human ERG expressed in CHO cells at -80 mV holding potential measu... 31099559
5-hydroxytryptamine receptor 4 EC50 = 79.43 nM 7.1 Agonist activity at human recombinant 5HT4c receptor expressed in HEK293 cells a... 22959244
5-hydroxytryptamine receptor 4 Ki = 100.0 nM 7.0 Displacement of [3H]GR113808 from human recombinant 5HT4C receptor expressed in ... 22683222
5-hydroxytryptamine receptor 4 Ki = 100.0 nM 7.0 Displacement of [3H]GR113808 from human recombinant 5HT4c receptor expressed in ... 22959244
5-hydroxytryptamine receptor 4 EC50 = 102.33 nM 6.99 Agonist activity at 5-HT4 receptor in rat esophageal thoracic muscularis mucosae... 26761776
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 170.0 nM 6.77 Inhibition of hERG channel assessed as prolongation of QT interval by patch clam... 35635004

Literature References

PubMed DOI Target Context # Activities
26761776 10.1016/j.ejmech.2015.12.006 Rattus norvegicus 6
35737669 10.1021/acs.jmedchem.2c00608 Unchecked 3
22959244 10.1016/j.bmcl.2012.08.051 5-hydroxytryptamine receptor 4 3
22683222 10.1016/j.bmcl.2012.05.034 5-hydroxytryptamine receptor 4 3
30108781 10.1039/C6MD00458J 5-hydroxytryptamine receptor 4 3
26761776 10.1016/j.ejmech.2015.12.006 5-hydroxytryptamine receptor 4 2
26761776 10.1016/j.ejmech.2015.12.006 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37651874 10.1016/j.ejmech.2023.115742 Voltage-gated inwardly rectifying potassium channel KCNH2 1
33395621 10.1016/j.ejmech.2020.113096 Voltage-gated inwardly rectifying potassium channel KCNH2 1
33246105 10.1016/j.bmcl.2020.127710 Voltage-gated inwardly rectifying potassium channel KCNH2 1
31099559 10.1021/acs.jmedchem.9b00518 Voltage-gated inwardly rectifying potassium channel KCNH2 1
31158742 10.1016/j.ejmech.2019.05.051 Voltage-gated inwardly rectifying potassium channel KCNH2 1
30698430 10.1021/acs.jmedchem.8b01750 Voltage-gated inwardly rectifying potassium channel KCNH2 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
22959244 10.1016/j.bmcl.2012.08.051 Unchecked 1
22959244 10.1016/j.bmcl.2012.08.051 Rattus norvegicus 1
22959244 10.1016/j.bmcl.2012.08.051 Liver microsomes 1
22959244 10.1016/j.bmcl.2012.08.051 Voltage-gated inwardly rectifying potassium channel KCNH2 1
22683222 10.1016/j.bmcl.2012.05.034 Liver microsomes 1
22683222 10.1016/j.bmcl.2012.05.034 Voltage-gated inwardly rectifying potassium channel KCNH2 1

Data from ChEMBL 36 via Core Engine