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Compound Detail

CHEMBL1729

CISAPRIDE
💊 Approved Drug
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💊 Approved Drug
COc1cc(N)c(Cl)cc1C(=O)NC1CCN(CCCOc2ccc(F)cc2)CC1OC

Basic Information

ChEMBL ID CHEMBL1729
Name CISAPRIDE
Phase Approved
Structure Type MOL
InChI Key DCSUBABJRXZOMT-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Cisaprida Cisapride R-51,619 R-51619
45
Targets
136
Activities
4
Assay Types
10
PK Parameters
20
Publications
4
Known Names
1
Indications

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
First Approval 1993
Availability Withdrawn
Chirality Racemic

Routes of Administration

Oral

Flags

Withdrawn
USAN Stem -pride
USAN Year 1983

Extended Properties

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

Indications

Digestive System Diseases

ATC Classification

A03FA02
cisapride
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 80 meas. best 9.44
Ki 46 meas. best 8.96
EC50 6 meas. best 7.26
Kd 4 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 4
CHEMBL1875
IC50 9.44 9.44 0.4 1
Cavia porcellus
CHEMBL369
Kd 9.0 9.0 1.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 8.96 8.58 1.1 2
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 8.41 8.41 3.9 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
Ki 8.21 8.21 6.1 1
Serotonin 2 (5-HT2) receptor
CHEMBL2095200
IC50 8.21 8.21 6.1 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 8.19 7.4309 6.5 34
5-hydroxytryptamine receptor 2A
CHEMBL3446
Ki 8.14 8.14 7.2 1
Alpha-1B adrenergic receptor
CHEMBL315
Ki 8.06 8.06 8.7 1
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
IC50 8.01 8.01 9.8 1
Unchecked
CHEMBL612545
IC50 8.0 6.5689 10.0 9
5-hydroxytryptamine receptor 4
CHEMBL5017
Ki 7.84 7.672 14.3 5
Alpha-1B adrenergic receptor
CHEMBL315
IC50 7.8 7.8 16.0 1
5-hydroxytryptamine receptor 4
CHEMBL1875
Ki 7.54 7.1467 29.0 3
Adrenergic receptor alpha-1
CHEMBL2094251
IC50 7.52 7.52 30.0 2
Alpha-2A adrenergic receptor
CHEMBL327
Ki 7.52 7.52 30.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 7.52 7.415 30.0 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 7.4 7.28 39.8 2
D(3) dopamine receptor
CHEMBL234
Ki 7.31 7.31 49.0 1
5-hydroxytryptamine receptor 4
CHEMBL4317
EC50 7.26 7.26 54.7 2
Rattus norvegicus
CHEMBL376
EC50 7.23 7.23 58.9 1
Serotonin 3 (5-HT3) receptor
CHEMBL2094132
Kd 7.2 6.9333 63.1 3
Cytochrome P450 2D6
CHEMBL289
IC50 7.16 7.16 70.0 1
5-hydroxytryptamine receptor 4
CHEMBL1875
EC50 7.1 7.1 79.4 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 7.03 7.03 93.0 1
Serotonin 3 (5-HT3) receptor
CHEMBL2094116
Ki 7.02 6.92 94.7 3
5-hydroxytryptamine receptor 4
CHEMBL5017
EC50 7.0 7.0 100.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 6.96 6.96 110.0 1
Unchecked
CHEMBL612545
Ki 6.96 6.35 109.0 4
Adrenergic receptor alpha-1
CHEMBL1907610
IC50 6.96 6.96 110.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.95 6.95 113.0 1
Alpha-1A adrenergic receptor
CHEMBL319
IC50 6.92 6.92 120.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
Ki 6.86 6.86 139.4 1
D(3) dopamine receptor
CHEMBL234
IC50 6.84 6.84 144.0 1
Serotonin 3 (5-HT3) receptor
CHEMBL2094132
Ki 6.82 6.82 152.0 1
D(2) dopamine receptor
CHEMBL217
Ki 6.8 6.8 158.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 6.72 6.72 189.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.69 6.69 204.0 1
D(2) dopamine receptor
CHEMBL339
Ki 6.64 6.64 227.0 2
D(2) dopamine receptor
CHEMBL217
IC50 6.64 6.485 227.0 2
5-hydroxytryptamine receptor 4
CHEMBL5017
IC50 6.56 6.56 273.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 6.52 6.52 300.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 6.42 6.42 384.0 1
D(2) dopamine receptor
CHEMBL339
IC50 6.41 6.29 390.0 2
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.4 6.4 402.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.38 6.38 418.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.28 6.28 524.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.18 6.18 666.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.12 6.12 767.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 6.11 6.11 780.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 120.7 mL.min-1.g-1 Homo sapiens
F 49.0 % Homo sapiens
T1/2 0.08333 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 1.0 hr Homo sapiens
T1/2 0.7833 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 4 IC50 = 0.362 nM 9.44 Binding Assay: The binding affinity of the compounds for a human 5-HT4 receptor ... -
Cavia porcellus Kd = 1.0 nM 9.0 The compound was evaluated for the pA2 value that was estimated using 2-methyl-5... 8176710
5-hydroxytryptamine receptor 2A Ki = 1.102 nM 8.96 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2A IC50 = 3.856 nM 8.41 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Serotonin 2 (5-HT2) receptor Ki = 6.1 nM 8.21 The ability to inhibit [3H]ketanserin binding to 5-hydroxytryptamine 2 receptor ... 1573641
Serotonin 2 (5-HT2) receptor IC50 = 6.1 nM 8.21 Concentration required for inhibition of 5-hydroxytryptamine 2 receptor using [3... 15482914
Serotonin 2 (5-HT2) receptor IC50 = 6.1 nM 8.21 Binding affinity to 5HT2 receptor 16451077
5-hydroxytryptamine receptor 2A Ki = 6.31 nM 8.2 Binding affinity to human serotonin 5-HT2A receptor 23756062
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 6.5 nM 8.19 K+ channel blocking activity in human embryonic kidney cells expressing HERG Kv1... 12190308
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 6.457 nM 8.19 Inhibition of partially open human voltage-gated potassium channel subunit Kv11.... 15745831
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 6.457 nM 8.19 Inhibition of human ERG in MCF7 cells 19110341
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 6.5 nM 8.19 Inhibition of hERG K channel 21300721
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 6.7 nM 8.17 Inhibition of human ERG channel 19534531
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 6.7 nM 8.17 Inhibition of human ERG channel 19534531
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 6.761 nM 8.17 Inhibition of human ERG 21185626
5-hydroxytryptamine receptor 2A Ki = 7.2 nM 8.14 Compound was evaluated for the binding affinity at 5- HT2 receptor 7608898
Alpha-1B adrenergic receptor Ki = 8.654 nM 8.06 DRUGMATRIX: Alpha-1B adrenergic receptor radioligand binding (ligand: prazosin) -
Serotonin 2 (5-HT2) receptor IC50 = 9.8 nM 8.01 Inhibitory activity against 5-hydroxytryptamine 2 receptor by 3H ligand binding ... 1995885
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 10.0 nM 8.0 Inhibition of wild-type human ERG expressed in HEK293 cells by whole cell patch ... 19260734
Unchecked IC50 = 10.0 nM 8.0 Inhibition of human ERG td[wt:F656A] mutant expressed in HEK293 cells by whole c... 19260734

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 470
- 10.6019/CHEMBL4295262 Unchecked 28
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19260734 10.1021/jm801236n Voltage-gated inwardly rectifying potassium channel KCNH2 8
23756062 10.1016/j.bmcl.2013.05.018 5-hydroxytryptamine receptor 4 6
8176710 10.1021/jm00035a012 Rattus norvegicus 5
15482914 10.1016/j.bmcl.2004.09.005 Unchecked 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
2139471 10.1021/jm00167a020 Mus musculus 4
2139471 10.1021/jm00167a020 Rattus norvegicus 4
19260734 10.1021/jm801236n Unchecked 4
23415087 10.1016/j.bmc.2013.01.033 Heparanase 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
20014752 10.1021/tx900326k Hepatotoxicity 3
18262683 10.1016/j.ejmech.2007.12.025 Cavia porcellus 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
- 10.1016/S0960-894X(00)80170-5 Serotonin 3 (5-HT3) receptor 3

Data from ChEMBL 36 via Core Engine