Compound Detail
CHEMBL426559
LAROPIPRANT 💊 Approved Drug
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💊 Approved Drug
CS(=O)(=O)c1cc(F)cc2c3c(n(Cc4ccc(Cl)cc4)c12)[C@@H](CC(=O)O)CC3
Basic Information
| ChEMBL ID | CHEMBL426559 |
| Name | LAROPIPRANT |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | NXFFJDQHYLNEJK-CYBMUJFWSA-N |
| Therapeutic | ✓ Yes |
10
Targets
16
Activities
3
Assay Types
0
PK Parameters
20
Publications
3
Known Names
8
Indications
1
Mechanisms
Molecular Properties
435.9
MW (Da)
4.39
ALogP
4
HBA
1
HBD
76.4
PSA (Ų)
0.64
QED
0
Ro5 Violations
5
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| Availability | Withdrawn |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Prostanoid DP receptor antagonist | ANTAGONIST | Prostaglandin D2 receptor | ✓ | ✓ |
Indications
Diabetes Mellitus, Type 2 Hypercholesterolemia Hyperlipidemia, Familial Combined Hyperlipidemias Hyperlipoproteinemia Type II Lipid Metabolism Disorders Flushing Rosacea
Drug Warnings
Withdrawn
General Warning
Higher frequency of non-fatal but serious side effects
Activity Summary
Ki 10 meas. best 9.24
IC50 4 meas. best 10.05
Kd 2 meas. best 10.52
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Prostaglandin D2 receptor CHEMBL4427 | Kd | 10.52 | 10.52 | 0.0 | 1 |
| Prostaglandin D2 receptor CHEMBL4427 | IC50 | 10.05 | 9.1 | 0.1 | 3 |
| Prostaglandin D2 receptor CHEMBL4427 | Ki | 9.24 | 9.24 | 0.6 | 1 |
| Thromboxane A2 receptor CHEMBL2069 | Ki | 8.53 | 8.53 | 3.0 | 1 |
| Thromboxane A2 receptor CHEMBL2069 | Kd | 7.96 | 7.96 | 10.9 | 1 |
| Prostaglandin E2 receptor EP2 subtype CHEMBL1881 | Ki | 6.87 | 6.87 | 136.0 | 1 |
| Translocator protein CHEMBL5742 | Ki | 6.54 | 6.54 | 286.4 | 1 |
| Prostaglandin D2 receptor 2 CHEMBL5071 | Ki | 6.13 | 6.13 | 745.0 | 1 |
| Thromboxane A2 receptor CHEMBL2069 | IC50 | 6.11 | 6.11 | 770.0 | 1 |
| Prostaglandin E2 receptor EP3 subtype CHEMBL3710 | Ki | 6.05 | 6.05 | 892.0 | 1 |
| D(3) dopamine receptor CHEMBL234 | Ki | 5.95 | 5.95 | 1122.2 | 1 |
| Prostaglandin E2 receptor EP1 subtype CHEMBL1811 | Ki | 5.94 | 5.94 | 1160.0 | 1 |
| Prostacyclin receptor CHEMBL1995 | Ki | 5.18 | 5.18 | 6628.0 | 1 |
| Prostaglandin F2-alpha receptor CHEMBL1987 | Ki | 5.0 | 5.0 | 9991.0 | 1 |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| - | 10.6019/CHEMBL5724696 | TERT-RPE1 | 24 |
| - | 10.6019/CHEMBL5724696 | U2OS | 24 |
| - | 10.6019/CHEMBL4689842 | HEK-293T | 10 |
| - | 10.6019/CHEMBL4689842 | U2OS | 8 |
| - | 10.6019/CHEMBL4689842 | Fibroblast | 6 |
| 17300164 | 10.1021/jm0603668 | Prostaglandin D2 receptor | 5 |
| 37468498 | 10.1038/s41467-023-40064-9 | Thromboxane A2 receptor | 5 |
| 17300164 | 10.1021/jm0603668 | Ovis aries | 4 |
| 37468498 | 10.1038/s41467-023-40064-9 | Prostaglandin G/H synthase 1 | 3 |
| 37468498 | 10.1038/s41467-023-40064-9 | Alpha-1A adrenergic receptor | 3 |
| 37468498 | 10.1038/s41467-023-40064-9 | Gamma-aminobutyric acid receptor subunit alpha-1 | 3 |
| 17300164 | 10.1021/jm0603668 | Unchecked | 3 |
| 37468498 | 10.1038/s41467-023-40064-9 | Muscarinic acetylcholine receptor M1 | 3 |
| 17300164 | 10.1021/jm0603668 | Thromboxane A2 receptor | 3 |
| - | 10.6019/CHEMBL5209801 | N-formyl peptide receptor 2 | 2 |
| - | 10.6019/CHEMBL5209801 | Alpha-2A adrenergic receptor | 2 |
| - | 10.6019/CHEMBL5209801 | G-protein coupled receptor 35 | 2 |
| - | 10.6019/CHEMBL5209801 | Type-1 angiotensin II receptor | 2 |
| - | 10.6019/CHEMBL5209801 | C5a anaphylatoxin chemotactic receptor 1 | 2 |
| - | 10.6019/CHEMBL5209801 | Glucagon-like peptide 1 receptor | 2 |
Data from ChEMBL 36 via Core Engine