DANOPREVIR

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Synonyms
Status
Molecule Category Free-form
UNII 911Z9PCQ5F

Structure

InChI Key ZVTDLPBHTSMEJZ-JSZLBQEHSA-N
Smiles 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
InChI
InChI=1S/C35H46FN5O9S/c1-34(2,3)50-32(45)37-27-13-8-6-4-5-7-11-22-17-35(22,31(44)39-51(47,48)24-14-15-24)38-29(42)28-16-23(19-41(28)30(27)43)49-33(46)40-18-21-10-9-12-26(36)25(21)20-40/h7,9-12,22-24,27-28H,4-6,8,13-20H2,1-3H3,(H,37,45)(H,38,42)(H,39,44)/b11-7-/t22-,23-,27+,28+,35-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C35H46FN5O9S
Molecular Weight 731.84
AlogP 3.14
Hydrogen Bond Acceptor 9.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 180.52
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 51.0

Bioactivity

Mechanism of Action Action Reference
Hepatitis C virus serine protease, NS3/NS4A inhibitor INHIBITOR PubMed PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Serine protease Serine protease PA clan Serine protease S29 family Serine protease S29 regulatory subfamily
- 0 - - -
Enzyme Protease Serine protease Serine protease PA clan Serine protease S29 family
- 0 - - -
Enzyme Protease Serine protease
- 0 - 45 -
Assay Description Organism Bioactivity Reference
Inhibition of HCV NS3 protease by FRET assay Hepatitis C virus 0.25 nM
Antiviral activity against Hepatitis C virus infected human hepatoma cells by replicon assay Hepatitis C virus 2.1 nM
Inhibition of HCV NS3 protease by FRET assay Hepatitis C virus 0.25 nM
Antiviral activity against HCV 1B infected in human Huh7 cells by firefly luciferase reporter gene assay Hepatitis C virus subtype 1b 2.1 nM
Antiviral activity against wild-type Hepatitis C virus genotype 1b N infected in human Huh7 cells Hepatitis C virus subtype 1b 0.3 nM
Inhibition of HCV genotype 1 a NS3/4A protease by FRET assay Hepatitis C virus subtype 1a 0.4 nM
Antiviral activity against HCV genotype 1a transfected in human hepatoma cell assessed as inhibition of viral replication Hepatitis C virus subtype 1a 1.0 nM
Antiviral activity against HCV genotype 1b transfected in human hepatoma cell assessed as inhibition of viral replication Hepatitis C virus subtype 1b 1.1 nM
Antiviral activity against HCV 1b infected in human Huh-7 cells after 48hrs by luciferase assay Hepatitis C virus subtype 1b 1.1 nM
Antiviral activity against HCV 1a infected in human Huh-7 cells after 48hrs by luciferase assay Hepatitis C virus subtype 1a 1.0 nM
Inhibition of HCV 1a NS3/4A protease by FRET assay Hepatitis C virus subtype 1a 0.4 nM
Antiviral activity against HCV1b Con1 harboring NS3 protease gene infected in human Huh7/Lunet cells assessed as inhibition of viral replication after 3 days by luciferase based transient-transfection assay Hepatitis C virus 0.6 nM
Antiviral activity against HCV1b harboring Q80Q polymorphism in NS3 protease gene infected in human Huh7/Lunet cells assessed as inhibition of viral replication after 3 days by luciferase based transient-transfection assay Hepatitis C virus subtype 1b 0.25 nM
Antiviral activity against HCV1b harboring Q80K polymorphism in NS3 protease gene infected in human Huh7/Lunet cells assessed as inhibition of viral replication after 3 days by luciferase based transient-transfection assay Hepatitis C virus subtype 1b 0.62 nM
Antiviral activity against HCV Hepatitis C virus 0.6 nM
Inhibition of HCV NS3 protease Hepatitis C virus 0.25 nM
Inhibition of Hepatitis C virus genotype 1a NS3/4A protease using Ac-DE-Dap(QXL520)-EE-Abu-psi-COO]-AS-C(5-FAMsp)-NH2 as substrate by FRET analysis Hepatitis C virus subtype 1a 0.4 nM
Antiviral activity against Hepatitis C virus genotype 1b infected in HuH7 cells Hepatitis C virus subtype 1b 1.1 nM
Antiviral activity against Hepatitis C virus genotype 1a infected in HuH7 cells Hepatitis C virus subtype 1a 1.0 nM
Antiviral activity against Hepatitis C virus genotype 1b expressing wild type NS3/4A protease infected in HuH7 cells Hepatitis C virus subtype 1b 0.1 nM
Antiviral activity against Hepatitis C virus genotype 1b expressing NS3/4A protease A156S mutant infected in HuH7 cells Hepatitis C virus subtype 1b 1.6 nM
Antiviral activity against Hepatitis C virus genotype 1b expressing NS3/4A protease A156T mutant infected in HuH7 cells Hepatitis C virus subtype 1b 6.8 nM
Antiviral activity against Hepatitis C virus genotype 1b expressing NS3/4A protease A156V mutant infected in HuH7 cells Hepatitis C virus subtype 1b 8.3 nM
Antiviral activity against Hepatitis C virus genotype 1b expressing NS3/4A protease D158A mutant infected in HuH7 cells Hepatitis C virus subtype 1b 48.5 nM
Antiviral activity against Hepatitis C virus genotype 1b expressing NS3/4A protease D158V mutant infected in HuH7 cells Hepatitis C virus subtype 1b 24.5 nM
Antiviral activity against Hepatitis C virus genotype 1b expressing NS3/4A protease R155K mutant infected in HuH7 cells Hepatitis C virus subtype 1b 80.8 nM
Inhibition of HCV 1a protease 1a domain Hepatitis C virus 0.7 nM
Antiviral activity against Hepatitis C virus subtype 1b by stable replicon assay Hepatitis C virus subtype 1b 1.5 nM
Antiviral activity against Hepatitis C virus subtype 1a by stable replicon assay Hepatitis C virus subtype 1a 2.0 nM
Antiviral activity against Hepatitis C virus subtype 1b harboring protease D168V mutant by transient replicon assay Hepatitis C virus subtype 1b 26.0 nM
Antiviral activity against Hepatitis C virus subtype 1b harboring protease D168A mutant by transient replicon assay Hepatitis C virus subtype 1b 39.0 nM
Antiviral activity against Hepatitis C virus subtype 1b harboring protease A156V mutant by transient replicon assay Hepatitis C virus subtype 1b 8.0 nM
Antiviral activity against Hepatitis C virus subtype 1b harboring protease A156T mutant by transient replicon assay Hepatitis C virus subtype 1b 10.0 nM
Antiviral activity against Hepatitis C virus subtype 1b harboring protease A156S mutant by transient replicon assay Hepatitis C virus subtype 1b 2.0 nM
Antiviral activity against wild type Hepatitis C virus subtype 1b by transient replicon assay Hepatitis C virus subtype 1b 0.2 nM
Antiviral activity against Hepatitis C virus subtype 1b harboring protease R155K mutant by transient replicon assay Hepatitis C virus subtype 1b 82.0 nM
Inhibition of HCV6 NS3 protease Hepatitis C virus genotype 6 0.2 nM
Inhibition of HCV4 NS3 protease Hepatitis C virus genotype 4 0.2 nM
Inhibition of HCV5 NS3 protease Hepatitis C virus genotype 5 0.2 nM
Inhibition of HCV 2b NS3 protease Hepatitis C virus subtype 2b 0.2 nM
Inhibition of HCV 3a NS3 protease Hepatitis C virus subtype 3a 0.2 nM
Antiviral activity against HCV by cell based replicon assay Hepatitis C virus 1.8 nM
Inhibition of HCV 1a NS3 protease Hepatitis C virus subtype 1a 0.2 nM
Inhibition of HCV 1b NS3 protease Hepatitis C virus subtype 1b 0.2 nM
Antiviral activity against HCV subtype 1b expressing NS3/4A R115K mutant protease infected in ET cells after 72 hrs Hepatitis C virus subtype 1b 82.0 nM
Antiviral activity against HCV subtype 1b expressing NS3/4A D168V mutant protease infected in ET cells after 72 hrs Hepatitis C virus subtype 1b 26.0 nM
Antiviral activity against HCV subtype 1b expressing NS3/4A D168A mutant protease infected in ET cells after 72 hrs Hepatitis C virus subtype 1b 39.0 nM
Antiviral activity against HCV subtype 1b expressing NS3/4A A156V mutant protease infected in ET cells after 72 hrs Hepatitis C virus subtype 1b 8.0 nM
Antiviral activity against HCV subtype 1b expressing NS3/4A A156T mutant protease infected in ET cells after 72 hrs Hepatitis C virus subtype 1b 10.0 nM
Antiviral activity against HCV subtype 1b expressing NS3/4A A156S mutant protease infected in ET cells after 72 hrs Hepatitis C virus subtype 1b 2.0 nM
Antiviral activity against HCV subtype 1b expressing wild type NS3/4A protease infected in ET cells after 72 hrs Hepatitis C virus subtype 1b 0.2 nM
Antiviral activity against HCV subtype 1b infected in human hepatoma cells Hepatitis C virus subtype 1b 1.5 nM
Antiviral activity against HCV subtype 1a infected in human hepatoma cells Hepatitis C virus subtype 1a 2.0 nM
Inhibition of HCV subtype 1a NS3/4A protease (Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]-ASC(5-FAMsp)-NH2 as substrate by FRET analysis Hepatitis C virus subtype 1a 0.7 nM
Antiviral activity against Hepatitis C virus harboring NS3/4A protease A156T mutant gene infected in human HuH7 cells assessed as inhibition of HCV subgenomic replicon replication after 72 hrs by ELISA Hepatitis C virus 0.5 nM
Antiviral activity against Hepatitis C virus harboring wild type NS3/4A protease infected in human HuH7 cells assessed as inhibition of HCV subgenomic replicon replication after 72 hrs by ELISA Hepatitis C virus 0.25 nM
Antiviral activity against Hepatitis C virus genotype 1a isolate Con1 harboring NS3/4A protease A156T mutant gene infected in human HuH7 cells assessed as inhibition of HCV replicon replication by luciferase assay Hepatitis C virus (isolate Con1) 5.7 nM
Antiviral activity against Hepatitis C virus genotype 1a isolate Con1 harboring wild type NS3/4A protease infected in human HuH7 cells assessed as inhibition of HCV replicon replication by luciferase assay Hepatitis C virus (isolate Con1) 0.24 nM
Inhibition of Hepatitis C virus genotype 1a NS3/4A protease A156T mutant expressed in Escherichia coli BL21 (DE3) cells assessed as substrate cleavage using Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]AS-C(5-FAMsp)-NH2 as substrate by plate reader analysis Hepatitis C virus subtype 1a 44.8 nM
Inhibition of Hepatitis C virus genotype 1a wild type NS3/4A protease expressed in Escherichia coli BL21 (DE3) cells assessed as substrate cleavage using Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]AS-C(5-FAMsp)-NH2 as substrate by plate reader analysis Hepatitis C virus subtype 1a 1.0 nM
Antiviral activity against Hepatitis C virus genotype 3 infected in human HuH7 cells assessed as decrease in replicon RNA level after 2 days by TaqMan Gold RT-PCR analysis Hepatitis C virus genotype 3 20.0 nM
Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH7 cells assessed as decrease in replicon RNA level after 2 days by TaqMan Gold RT-PCR analysis Hepatitis C virus subtype 1b 1.6 nM
Antiviral activity against Hepatitis C virus genotype 2 infected in human HuH7 cells assessed as decrease in replicon RNA level after 2 days by TaqMan Gold RT-PCR analysis Hepatitis C virus genotype 2 20.0 nM
Inhibition of Hepatitis C virus genotype 3a NS3/4A protease using Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]-AS-Cys(5-FAMsp)-NH2 as substrate by FRET analysis Hepatitis C virus subtype 3a 3.5 nM
Inhibition of Hepatitis C virus genotype 2b NS3/4A protease using Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]-AS-Cys(5-FAMsp)-NH2 as substrate by FRET analysis Hepatitis C virus subtype 2b 1.6 nM
Inhibition of Hepatitis C virus genotype 6 NS3/4A protease using Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]-AS-Cys(5-FAMsp)-NH2 as substrate by FRET analysis Hepatitis C virus genotype 6 0.2 nM
Inhibition of Hepatitis C virus genotype 5 NS3/4A protease using Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]-AS-Cys(5-FAMsp)-NH2 as substrate by FRET analysis Hepatitis C virus genotype 5 0.2 nM
Inhibition of Hepatitis C virus genotype 4 NS3/4A protease using Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]-AS-Cys(5-FAMsp)-NH2 as substrate by FRET analysis Hepatitis C virus genotype 4 0.2 nM
Inhibition of Hepatitis C virus genotype 1b NS3/4A protease using Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]-AS-Cys(5-FAMsp)-NH2 as substrate by FRET analysis Hepatitis C virus subtype 1b 0.2 nM
Inhibition of Hepatitis C virus genotype 1a NS3/4A protease using Ac-DE-Dap(QXL520)-EE-Abu-psi-[COO]-AS-Cys(5-FAMsp)-NH2 as substrate by FRET analysis Hepatitis C virus subtype 1a 0.2 nM
Antiviral activity against Hepatitis C virus infected in human HuH7 cells assessed as inhibition of HCV subgenomic replicon replication after 72 hrs by ELISA Hepatitis C virus 2.4 nM
Inhibition of Hepatitis C virus full-length NS3/4A protease assessed as quenched-fluorogenic RET-S1 substrate cleavage incubated for 10 mins prior to substrate addition by FRET analysis Hepatitis C virus 1.0 nM
Inhibition of Hepatitis C virus genotype 3a full-length NS3 protease assessed as overall/observed affinity by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 3a 0.52 nM
Inhibition of Hepatitis C virus genotype 1b full-length NS3/NS4A protease assessed as overall/observed affinity by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 1b 6.5 nM
Inhibition of Hepatitis C virus genotype 1b full-length NS3 protease assessed as overall/observed affinity by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 1b 1.6 nM
Inhibition of Hepatitis C virus genotype 1a full-length NS3/NS4A protease assessed as overall/observed affinity by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 1a 1.6 nM
Inhibition of Hepatitis C virus genotype 1a full-length NS3 protease assessed as overall/observed affinity by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 1a 0.13 nM
Inhibition of Hepatitis C virus genotype 3a full-length NS3 protease assessed as equilibrium dissociation constant by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 3a 21.0 nM
Inhibition of Hepatitis C virus genotype 1b full-length NS3/NS4A protease assessed as equilibrium dissociation constant by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 1b 6.5 nM
Inhibition of Hepatitis C virus genotype 1b full-length NS3 protease assessed as equilibrium dissociation constant by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 1b 1.6 nM
Inhibition of Hepatitis C virus genotype 1a full-length NS3/NS4A protease assessed as equilibrium dissociation constant by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 1a 4.0 nM
Inhibition of Hepatitis C virus genotype 1a full-length NS3 protease assessed as equilibrium dissociation constant by surface plasmon resonance biosensor-based interaction kinetic analysis Hepatitis C virus subtype 1a 2.5 nM
Inhibition of full-length HCV genotype 1a NS3 protease R155K mutant using Ac-DED(Edans)EEAbu-psi-[COO]ASK(Dabcyl)-NH2 as substrate by FRET assay Hepatitis C virus subtype 1a 9.0 nM
Antiviral activity against HCV infected in human HuH7 cells by cell based replicon assay Hepatitis C virus 11.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 3.46 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 20.22 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.06 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.06 %
Inhibition of HCV NS3/4a protease using Ac-DE-Dap(QXL520)-EE-Abu-shi-[COO]AS-C(5-FAMsp)-NH2 as substrate after 15 mins Hepatitis C virus 0.2 nM
Antiviral activity against HCV Hepatitis C virus 17.5 nM

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL258734
DrugBank DB11779
FDA SRS 911Z9PCQ5F
PubChem 11285588
SureChEMBL SCHEMBL2289034
ZINC ZINC000029058869
CONTENTS