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Compound Detail

CHEMBL1110

ALOSETRON
💊 Approved Drug
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💊 Approved Drug
Cc1[nH]cnc1CN1CCc2c(c3ccccc3n2C)C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1110
Name ALOSETRON
Phase Approved
Structure Type MOL
InChI Key JSWZEAMFRNKZNL-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

A03AE01 Alosetron
6
Targets
19
Activities
2
Assay Types
12
PK Parameters
20
Publications
2
Known Names
2
Indications

Molecular Properties

294.4
MW (Da)
2.41
ALogP
3
HBA
1
HBD
53.9
PSA (Ų)
0.79
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2000
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -setron
USAN Year 1992

Extended Properties

Molecular Formula C17H18N4O
MW 294.36
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness -0.77

Indications

Digestive System Diseases Irritable Bowel Syndrome

ATC Classification

A03AE01
alosetron
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS

Activity Summary

IC50 12 meas. best 8.93
Ki 7 meas. best 9.58

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.58 9.44 0.3 2
5-hydroxytryptamine receptor 3A
CHEMBL1899
 Ki 9.3 9.3 0.5 4
Unchecked
CHEMBL612545
 IC50 8.93 8.93 1.2 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 7.19 7.19 64.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 IC50 7.0 7.0 100.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 6.22 6.22 604.7 1
Cytochrome P450 3A4
CHEMBL340
 IC50 6.22 6.22 600.0 3
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.64 5.5183 2300.0 6

Pharmacokinetic Data

Parameter Value Units Species
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 8.7 mL.min-1.kg-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 600.0 ml/min Mus musculus
F 55.0 % Homo sapiens
F 100.0 % Rattus norvegicus
F 50.0 % Homo sapiens
Fu 0.18 - Homo sapiens
MRT 2.1 hr Homo sapiens
T1/2 1.6 hr Homo sapiens
T1/2 1.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.262 nM 9.58 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT3 radioligand binding (ligand: [... -
Unchecked Ki = 0.5 nM 9.3 Binding affinity to 5-HT3R (unknown origin) assessed as inhibition constant 38516587
5-hydroxytryptamine receptor 3A Ki = 0.5 nM 9.3 Radioligand Binding Assay: The relative affinity of the various compounds for th... -
5-hydroxytryptamine receptor 3A Ki = 0.5 nM 9.3 Displacement of [9-methyl-3H]BRL-43694 from human 5-HT3A receptor after overnigh... 24755431
5-hydroxytryptamine receptor 3A Ki = 0.5 nM 9.3 Binding affinity to human 5HT3A receptor 21146988
5-hydroxytryptamine receptor 3A Ki = 0.5 nM 9.3 Binding affinity to human HT3A receptor 20889341
Unchecked IC50 = 1.164 nM 8.93 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT3 radioligand binding (ligand: [... -
5-hydroxytryptamine receptor 2B Ki = 64.0 nM 7.19 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B IC50 = 100.0 nM 7.0 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Cytochrome P450 3A4 IC50 = 600.0 nM 6.22 Inhibition of CYP3A4 (unknown origin) 24755431
Cytochrome P450 1A2 IC50 = 604.7 nM 6.22 DRUGMATRIX: CYP450, 1A2 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Cytochrome P450 3A4 IC50 = 600.0 nM 6.22 Inhibition of human CYP3A4 21146988
Cytochrome P450 3A4 IC50 = 600.0 nM 6.22 Inhibition of human CYP3A4 20889341
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 2300.0 nM 5.64 Inhibition of human ERG expressed in HEK cells by patch clamp technique 20889341
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3200.0 nM 5.5 Inhibition of human ERG channel 19534531
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3200.0 nM 5.5 Inhibition of human ERG channel 19534531
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3235.94 nM 5.49 Inhibition of human Potassium channel HERG expressed in mammalian cells 12873512
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3235.94 nM 5.49 Inhibitory concentration against potassium channel HERG 15911273
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3235.94 nM 5.49 Inhibition of human ERG expressed in CHO cells by whole cell patch clamp techniq... 18448342

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
38516587 10.1039/d3md00677h ADMET 4
- 10.6019/CHEMBL5058564 U2OS 4
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL5058564 Fibroblast 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
- 10.6019/CHEMBL5058564 HEK-293T 3
21146988 10.1016/j.bmcl.2010.11.080 5-hydroxytryptamine receptor 3A 3
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 2
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 2
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 2
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 2
- 10.6019/CHEMBL5209801 G-protein coupled receptor 35 2

Data from ChEMBL 36 via Core Engine