Compound Detail
CHEMBL429736
RETOSIBAN 🧪 Phase III
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🧪 Phase III
CC[C@H](C)[C@@H]1C(=O)N[C@H](C2Cc3ccccc3C2)C(=O)N1[C@@H](C(=O)N1CCOCC1)c1coc(C)n1
Basic Information
| ChEMBL ID | CHEMBL429736 |
| Name | RETOSIBAN |
| Phase | Phase III |
| Structure Type | MOL |
| InChI Key | PLVGDGRBPMVYPB-FDUHJNRSSA-N |
3
Targets
6
Activities
2
Assay Types
11
PK Parameters
15
Publications
5
Known Names
1
Indications
1
Mechanisms
Molecular Properties
494.6
MW (Da)
2.04
ALogP
6
HBA
1
HBD
105.0
PSA (Ų)
0.66
QED
0
Ro5 Violations
6
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Oxytocin receptor antagonist | ANTAGONIST | Oxytocin receptor | ✓ | ✓ |
Indications
Premature Birth
Activity Summary
Ki 5 meas. best 9.2
IC50 1 meas. best 6.75
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Oxytocin receptor CHEMBL2049 | Ki | 9.2 | 8.945 | 0.6 | 4 |
| Rattus norvegicus CHEMBL376 | IC50 | 6.75 | 6.75 | 180.0 | 1 |
| Vasopressin V2 receptor CHEMBL1790 | Ki | 6.02 | 6.02 | 950.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| AUC | 5470.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 1800.0 | ng.hr.mL-1 | Rattus norvegicus |
| AUC | 45.0 | ng.hr.mL-1 | Macaca fascicularis |
| CL | 19.0 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 26.0 | mL.min-1.kg-1 | Macaca fascicularis |
| CL | 3.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 6.0 | mL.min-1.g-1 | Macaca fascicularis |
| F | 100.0 | % | Rattus norvegicus |
| F | 100.0 | % | Rattus norvegicus |
| F | 10.0 | % | Macaca fascicularis |
| T1/2 | 1.4 | hr | Rattus norvegicus |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Oxytocin receptor | Ki | = | 0.63 | nM | 9.2 | Displacement of [3H]-oxytocin from oxytocin receptor in human uterus tissue | 20550119 |
| Oxytocin receptor | Ki | = | 0.65 | nM | 9.19 | Binding affinity to human oxytocin receptor | 18032036 |
| Oxytocin receptor | Ki | = | 1.0 | nM | 9.0 | Binding affinity to human oxytocin receptor | 18032036 |
| Oxytocin receptor | Ki | = | 4.1 | nM | 8.39 | Binding affinity to recombinant oxytocin receptor | 18032036 |
| Rattus norvegicus | IC50 | = | 180.0 | nM | 6.75 | Decrease in oxytocin-induced uterine contractions in iv dosed non-pregnant Sprag... | 18032036 |
| Vasopressin V2 receptor | Ki | = | 950.0 | nM | 6.02 | Binding affinity to human vasopressin V2 receptor | 18032036 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| 18032036 | 10.1016/j.bmcl.2007.11.008 | Rattus norvegicus | 7 |
| 18032036 | 10.1016/j.bmcl.2007.11.008 | Unchecked | 4 |
| 18032036 | 10.1016/j.bmcl.2007.11.008 | Oxytocin receptor | 3 |
| 22239250 | 10.1021/jm201287w | Cynomolgus monkey | 3 |
| 20550119 | 10.1021/jm901812z | Unchecked | 2 |
| 18032036 | 10.1016/j.bmcl.2007.11.008 | Serum | 1 |
| 18032036 | 10.1016/j.bmcl.2007.11.008 | No relevant target | 1 |
| 18032036 | 10.1016/j.bmcl.2007.11.008 | Cytochrome P450 3A4 | 1 |
| 18032036 | 10.1016/j.bmcl.2007.11.008 | Vasopressin V1a receptor | 1 |
| 18032036 | 10.1016/j.bmcl.2007.11.008 | Vasopressin V1b receptor | 1 |
| 18032036 | 10.1016/j.bmcl.2007.11.008 | Vasopressin V2 receptor | 1 |
| 20550119 | 10.1021/jm901812z | Oxytocin receptor | 1 |
| 20550119 | 10.1021/jm901812z | Rattus norvegicus | 1 |
| 22239250 | 10.1021/jm201287w | Liver microsomes | 1 |
| 22239250 | 10.1021/jm201287w | ADMET | 1 |
Data from ChEMBL 36 via Core Engine