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Compound Detail

CHEMBL49429

LIXIVAPTAN
🧪 Phase III
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🧪 Phase III
Cc1ccc(F)cc1C(=O)Nc1ccc(C(=O)N2Cc3cccn3Cc3ccccc32)c(Cl)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL49429
Name LIXIVAPTAN
Phase Phase III
Structure Type MOL
InChI Key PPHTXRNHTVLQED-UHFFFAOYSA-N

Known Names

CRTX 080 CRTX-080 CRTX080 Lixar Lixivaptan VPA 985 Vpa-985 VPA985 WAY-VPA-985
5
Targets
33
Activities
2
Assay Types
21
PK Parameters
20
Publications
9
Known Names
4
Indications
1
Mechanisms

Molecular Properties

473.9
MW (Da)
6.05
ALogP
3
HBA
1
HBD
54.3
PSA (Ų)
0.39
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Stem -vaptan
USAN Year 1999

Extended Properties

Molecular Formula C27H21ClFN3O2
MW 473.94
Aromatic Rings 4
Heavy Atoms 34
NP-Likeness -1.87

Mechanism of Action

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

Indications

Hyponatremia Polycystic Kidney Diseases Polycystic Kidney, Autosomal Dominant Heart Failure

Activity Summary

IC50 28 meas. best 9.3
Ki 5 meas. best 8.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vasopressin V2 receptor
CHEMBL3766
 IC50 9.3 8.805 0.5 4
Vasopressin V2 receptor
CHEMBL1790
 IC50 9.0 8.4164 1.0 11
Vasopressin V2 receptor
CHEMBL1790
 Ki 8.64 7.7767 2.3 3
Vasopressin V1a receptor
CHEMBL1889
 Ki 7.36 6.29 44.0 2
Vasopressin V1a receptor
CHEMBL2868
 IC50 7.09 6.605 82.0 4
Vasopressin V1a receptor
CHEMBL1889
 IC50 6.91 6.755 124.0 8
Oxytocin receptor
CHEMBL2049
 IC50 6.29 6.29 519.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 2960.0 ng.hr.mL-1 Homo sapiens
AUC 1540.0 ng.hr.mL-1 Homo sapiens
AUC 1570.0 ng.hr.mL-1 Homo sapiens
AUC 140.0 ng.hr.mL-1 Rattus norvegicus
AUC 219.0 ng.hr.mL-1 Rattus norvegicus
AUC 1530.0 ng.hr.mL-1 Rattus norvegicus
AUC 1890.0 ng.hr.mL-1 Rattus norvegicus
AUC 4700.0 ng.hr.mL-1 Canis lupus familiaris
AUC 4870.0 ng.hr.mL-1 Canis lupus familiaris
Cmax 922.06 nM Homo sapiens
Cmax 192.01 nM Rattus norvegicus
Cmax 713.17 nM Rattus norvegicus
Cmax 1601.47 nM Canis lupus familiaris
T1/2 9.77 hr Homo sapiens
T1/2 1.3 hr Rattus norvegicus
T1/2 4.2 hr Rattus norvegicus
T1/2 8.8 hr Canis lupus familiaris
Tmax 0.7 hr Homo sapiens
Tmax 0.8 hr Rattus norvegicus
Tmax 0.8 hr Rattus norvegicus
Tmax 0.8 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vasopressin V2 receptor IC50 = 0.5 nM 9.3 Displacement of P[3H]-AVP from isolated rat kidney medullary V2 receptor 10406633
Vasopressin V2 receptor IC50 = 1.0 nM 9.0 Inhibition of [3H]-AVP binding to human V2 receptor 16153837
Vasopressin V2 receptor IC50 = 1.2 nM 8.92 In vitro binding affinity to human V2 receptor 10782666
Vasopressin V2 receptor IC50 = 1.2 nM 8.92 Displacement of [3H]AVP from human vasopressin V2-receptor expressed in murine f... 10782686
Vasopressin V2 receptor IC50 = 1.2 nM 8.92 In vitro inhibition of [3H]AVP binding to human V2 receptor from murine fibrobla... 10406632
Vasopressin V2 receptor IC50 = 1.2 nM 8.92 Displacement of [3H]AVP from human V2 receptor expressed in murine fibroblast ce... 9651149
Vasopressin V2 receptor IC50 = 1.2 nM 8.92 Displacement of [3H]AVP from human vasopressin V2 receptor expressed in mouse LV... 17855087
Vasopressin V2 receptor Ki = 2.3 nM 8.64 Inhibition of [3H]AVP binding to recombinant human vasopressin V2 receptor 15125926
Vasopressin V2 receptor IC50 = 2.3 nM 8.64 Displacement of [3H]AVP from vasopressin V2 receptor of rat kidney medulla. 9651149
Vasopressin V2 receptor IC50 = 2.3 nM 8.64 Inhibition of [3H]AVP binding to Dawley rat kidney medullary vasopressin V2 rece... 12798333
Vasopressin V2 receptor IC50 = 2.3 nM 8.64 Binding affinity to rat V2 receptor 10782666
Vasopressin V2 receptor IC50 = 5.0 nM 8.3 Inhibition of [3H]Arg-vasopressin binding to recombinant human vasopressin V2 re... 12372506
Vasopressin V2 receptor IC50 = 5.0 nM 8.3 Inhibitory activity of the human V2 receptor was assessed by the accumulation of... 12639574
Vasopressin V2 receptor IC50 = 5.0 nM 8.3 Displacement of [3H]Arg-vasopressin from human recombinant vasopressin V2 recept... 17942308
Vasopressin V2 receptor Ki = 23.0 nM 7.64 Inhibition of 1 nM AVP-induced cAMP accumulation in cells expressing human vasop... 15125926
Vasopressin V1a receptor Ki = 44.0 nM 7.36 Inhibition of [3H]AVP binding to recombinant human vasopressin V1a receptor 15125926
Vasopressin V1a receptor IC50 = 82.0 nM 7.09 Displacement of (Phe-3,4,5 [3H]-) AVP from isolated rat hepatic V1a receptor 10406633
Vasopressin V2 receptor Ki = 90.0 nM 7.05 Inhibition of AVP mediated activation of human vasopressin V2 receptor expressed... 12372506
Vasopressin V2 receptor IC50 = 91.0 nM 7.04 Inhibitory activity of the human V2 receptor was assessed by the accumulation of... 12639574
Vasopressin V2 receptor IC50 = 91.0 nM 7.04 Antagonist activity at human vasopressin V2 receptor expressed in HEK293 cells a... 17942308

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL5058577 HEK-293T 304
- 10.6019/CHEMBL5724801 Fibroblast 304
9651149 10.1021/jm980179c Rattus norvegicus 24
22474055 10.1124/dmd.112.044933 Rattus norvegicus 10
22474055 10.1124/dmd.112.044933 Homo sapiens 7
- 10.6019/CHEMBL5058564 Fibroblast 6
- 10.6019/CHEMBL5058564 U2OS 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
22474055 10.1124/dmd.112.044933 Canis familiaris 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5

Data from ChEMBL 36 via Core Engine