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Compound Detail

CHEMBL4594444

PECAVAPTAN
🧪 Phase II
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🧪 Phase II
C[C@H](O)c1nc(Cn2nc(-c3ccc(Cl)cc3)n(C[C@H](O)C(F)(F)F)c2=O)nn1-c1cccc(Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4594444
Name PECAVAPTAN
Phase Phase II
Structure Type MOL
InChI Key AZXOTZCWQDJCLY-SJCJKPOMSA-N

Known Names

Bay 1753011 BAY-1753011 Pecavaptan
4
Targets
10
Activities
2
Assay Types
0
PK Parameters
20
Publications
3
Known Names
1
Indications
2
Mechanisms

Molecular Properties

543.3
MW (Da)
3.62
ALogP
9
HBA
2
HBD
111.0
PSA (Ų)
0.37
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Chemical Probe
USAN Stem -vaptan

Extended Properties

Molecular Formula C22H19Cl2F3N6O3
MW 543.33
Aromatic Rings 4
Heavy Atoms 36
NP-Likeness -1.43

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Vasopressin V1a receptor antagonist ANTAGONIST Vasopressin V1a receptor ✓ ✓
Vasopressin V2 receptor antagonist ANTAGONIST Vasopressin V2 receptor ✓ ✓

Indications

Heart Failure

Activity Summary

IC50 5 meas. best 8.77
Ki 5 meas. best 9.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vasopressin V1a receptor
CHEMBL1889
 Ki 9.3 9.09 0.5 2
Vasopressin V2 receptor
CHEMBL1790
 Ki 9.22 9.22 0.6 1
Vasopressin V2 receptor
CHEMBL1790
 IC50 8.77 8.77 1.7 1
Vasopressin V1a receptor
CHEMBL1889
 IC50 8.44 8.305 3.6 2
Oxytocin receptor
CHEMBL2049
 Ki 8.3 8.295 5.1 2
Oxytocin receptor
CHEMBL2049
 IC50 7.81 7.81 15.5 1
Vasopressin V1b receptor
CHEMBL1921
 IC50 5.0 5.0 10000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vasopressin V1a receptor Ki = 0.5 nM 9.3 Inhibition of Vasopressin V1A at 10.0 µM in the Eurofins-Panlabs selectivity sc... -
Vasopressin V2 receptor Ki = 0.6 nM 9.22 Radiometric AVPR2 binding assay (Eurofins #287610) -
Vasopressin V1a receptor Ki = 1.33 nM 8.88 Inhibition of Vasopressin V1A at 10 µM in the Eurofins-Panlabs radioligand bindi... -
Vasopressin V2 receptor IC50 = 1.7 nM 8.77 Assay with bioluminescence detection (AVPR). (The vasopressin receptor cells rea... -
Vasopressin V1a receptor IC50 = 3.6 nM 8.44 Assay with bioluminescence detection (AVPR1). (The vasopressin receptor cells re... -
Oxytocin receptor Ki = 5.06 nM 8.3 Inhibition of Oxytocin at 1 µM in the Eurofins-Panlabs radioligand binding assay... -
Oxytocin receptor Ki = 5.1 nM 8.29 Radiometric OXTR binding assay (Eurofins #260900) -
Vasopressin V1a receptor IC50 = 6.74 nM 8.17 Inhibition of Vasopressin V1A at 10 µM in the Eurofins-Panlabs radioligand bindi... -
Oxytocin receptor IC50 = 15.5 nM 7.81 Inhibition of Oxytocin at 1 µM in the Eurofins-Panlabs radioligand binding assay... -
Vasopressin V1b receptor IC50 = 10000.0 nM 5.0 Inhibition of Vasopressin V1B at 10 µM in the Eurofins-Panlabs radioligand bindi... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5463729 Unchecked 26
- 10.6019/CHEMBL5463729 Oxytocin receptor 8
- 10.6019/CHEMBL5463729 Vasopressin V1b receptor 7
- 10.6019/CHEMBL5463729 Vasopressin V1a receptor 5
- 10.6019/CHEMBL5463729 Tyrosine-protein kinase Lck 3
- 10.6019/CHEMBL5463729 Insulin receptor 3
- 10.6019/CHEMBL5463729 Epidermal growth factor receptor 3
- 10.6019/CHEMBL5463729 Voltage-dependent L-type calcium channel subunit alpha-1C 3
- 10.6019/CHEMBL5463729 Mitogen-activated protein kinase 14 2
- 10.6019/CHEMBL5463729 Tyrosine-protein kinase HCK 2
- 10.6019/CHEMBL5463729 Mitogen-activated protein kinase 1 2
- 10.6019/CHEMBL5463729 Protein kinase C alpha type 2
- 10.6019/CHEMBL5463729 Receptor tyrosine-protein kinase erbB-2 2
- 10.6019/CHEMBL5463729 Vasopressin V2 receptor 2
- 10.6019/CHEMBL5463729 MAP kinase-activated protein kinase 2 2
- 10.6019/CHEMBL5463729 Cyclin-dependent kinase 5/CDK5 activator 1 2
- 10.6019/CHEMBL5463729 Tyrosine-protein kinase Fyn 2
- 10.6019/CHEMBL5463729 Insulin-like growth factor 1 receptor 2
- 10.6019/CHEMBL5463729 Ribosomal protein S6 kinase beta-1 2
- 10.6019/CHEMBL5463729 D(2) dopamine receptor 2

Data from ChEMBL 36 via Core Engine