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Compound Detail

CHEMBL258734

DANOPREVIR
🧪 Phase III
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🧪 Phase III
CC(C)(C)OC(=O)N[C@H]1CCCCC/C=C\[C@@H]2C[C@@]2(C(=O)NS(=O)(=O)C2CC2)NC(=O)[C@@H]2C[C@@H](OC(=O)N3Cc4cccc(F)c4C3)CN2C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL258734
Name DANOPREVIR
Phase Phase III
Structure Type MOL
InChI Key ZVTDLPBHTSMEJZ-JSZLBQEHSA-N

Known Names

Danoprevir R-05190591 R05190591 RO-5190591 RO5190591 RO5190591-000
6
Targets
92
Activities
4
Assay Types
12
PK Parameters
20
Publications
6
Known Names
2
Indications
1
Mechanisms

Molecular Properties

731.8
MW (Da)
3.14
ALogP
9
HBA
3
HBD
180.5
PSA (Ų)
0.38
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -vir
USAN Year 2010

Extended Properties

Molecular Formula C35H46FN5O9S
MW 731.84
Aromatic Rings 1
Heavy Atoms 51
NP-Likeness -0.24

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Hepatitis C virus serine protease, NS3/NS4A inhibitor INHIBITOR Hepatitis C virus serine protease, NS3/NS4A ✓ ✓

Indications

Hepatitis C, Chronic Hepatitis C

Activity Summary

EC50 46 meas. best 10.0
IC50 30 meas. best 9.7
Kd 12 meas. best 9.89
Ki 4 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 EC50 10.0 8.475 0.1 46
Unchecked
CHEMBL612545
 Kd 9.89 8.0292 0.1 12
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 IC50 9.7 9.7 0.2 1
Hepatitis C virus
CHEMBL379
 IC50 9.7 9.1867 0.2 3
Non-structural protein 4b
CHEMBL6066153
 IC50 9.7 9.3943 0.2 7
Unchecked
CHEMBL612545
 IC50 9.7 9.4453 0.2 19
Non-structural protein 4b
CHEMBL6066153
 Ki 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
 Ki 9.0 9.0 1.0 1
NS3 protease
CHEMBL4296325
 Ki 8.05 8.05 9.0 1
NS3 protease
CHEMBL4296313
 Ki 7.35 7.35 44.8 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1750.0 ng.hr.mL-1 Rattus norvegicus
AUC 9500.0 ng.hr.mL-1 Rattus norvegicus
AUC 90800.0 ng.hr.mL-1 Rattus norvegicus
CL 10.72 mL.min-1.kg-1 Rattus norvegicus
CL 26.3 mL.min-1.kg-1 Macaca fascicularis
CL 10.8 mL.min-1.kg-1 Homo sapiens
F 20.0 % Rattus norvegicus
F 20.0 % Rattus norvegicus
F 78.0 % Macaca mulatta
F 15.0 % Rattus norvegicus
Fu 0.00085 - Macaca fascicularis
Fu 0.00072 - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus EC50 = 0.1 nM 10.0 Antiviral activity against Hepatitis C virus genotype 1b expressing wild type NS... 22425454
Unchecked Kd = 0.13 nM 9.89 Inhibition of Hepatitis C virus genotype 1a full-length NS3 protease assessed as... 24512311
Unchecked IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 4 NS3/4A protease using Ac-DE-Dap(QXL52... 23672640
Unchecked IC50 = 0.2 nM 9.7 Inhibition of HCV6 NS3 protease 21381769
Unchecked IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 1b NS3/4A protease using Ac-DE-Dap(QXL5... 23672640
Unchecked IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 1a NS3/4A protease using Ac-DE-Dap(QXL5... 23672640
Non-structural protein 4b IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 1a NS4B 38179950
Non-structural protein 4b IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 4 NS4B 38179950
Non-structural protein 4b IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 5 NS4B 38179950
Non-structural protein 4b IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 6 NS4B 38179950
Non-structural protein 4b IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 1b NS4B 38179950
Unchecked IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 5 NS3/4A protease using Ac-DE-Dap(QXL52... 23672640
Unchecked IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus genotype 6 NS3/4A protease using Ac-DE-Dap(QXL52... 23672640
Unchecked IC50 = 0.2 nM 9.7 Inhibition of HCV 1a NS3 protease 21381769
Hepatitis C virus IC50 = 0.2 nM 9.7 Inhibition of HCV 1b NS3 protease 21381769
Unchecked IC50 = 0.2 nM 9.7 Inhibition of HCV 2b NS3 protease 21381769
Unchecked IC50 = 0.2 nM 9.7 Inhibition of HCV 3a NS3 protease 21381769
Unchecked IC50 = 0.2 nM 9.7 Inhibition of HCV4 NS3 protease 21381769
Unchecked IC50 = 0.2 nM 9.7 Inhibition of HCV5 NS3 protease 21381769
Hepatitis C virus EC50 = 0.2 nM 9.7 Antiviral activity against wild type Hepatitis C virus subtype 1b by transient r... 22471376

Literature References

PubMed DOI Target Context # Activities
18086851 10.1128/aac.01149-07 Hepatitis C virus 15
22471376 10.1021/jm201278q Hepatitis C virus 12
24512311 10.1021/jm401690f Unchecked 12
20855726 10.1128/aac.00777-10 Hepatitis C virus 10
23142614 10.1016/j.bmcl.2012.10.075 Hepatitis C virus 9
22425454 10.1016/j.bmcl.2012.02.039 Hepatitis C virus 9
23672640 10.1021/jm400164c Unchecked 9
23672640 10.1021/jm400164c Hepatitis C virus 9
38179950 10.1021/acs.jmedchem.3c01971 Non-structural protein 4b 8
32985885 10.1021/acs.jmedchem.0c01033 ADMET 7
21381769 10.1021/jm1012374 Unchecked 6
23672640 10.1021/jm400164c No relevant target 5
21041080 10.1016/j.bmcl.2010.10.007 Rattus norvegicus 4
23672640 10.1021/jm400164c Nucleic Acid 3
23672640 10.1021/jm400164c ADMET 3
23672640 10.1021/jm400164c Cytochrome P450 3A4 3
23672640 10.1021/jm400164c Liver 3
21067923 10.1016/j.bmcl.2010.10.071 Rattus norvegicus 2
21067923 10.1016/j.bmcl.2010.10.071 Hepatitis C virus 2
21041080 10.1016/j.bmcl.2010.10.007 Hepatitis C virus 2

Data from ChEMBL 36 via Core Engine