ASUNAPREVIR

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Synonyms
Status
Molecule Category UNKNOWN
ATC J05AP06
UNII S9X0KRJ00S

Structure

InChI Key XRWSZZJLZRKHHD-WVWIJVSJSA-N
Smiles C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H](Oc2ncc(OC)c3ccc(Cl)cc23)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1
InChI
InChI=1S/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C35H46ClN5O9S
Molecular Weight 748.3
AlogP 3.85
Hydrogen Bond Acceptor 10.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 11.0
Polar Surface Area 182.33
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 51.0

Bioactivity

Mechanism of Action Action Reference
Hepatitis C virus serine protease, NS3/NS4A inhibitor INHIBITOR 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
- 1-1 - - -
Enzyme Protease Serine protease Serine protease PA clan Serine protease S29 family
- 1-1 - - -
Unclassified protein
1-4 - - - -
Assay Description Organism Bioactivity Reference
Antiviral activity against HCV genotype 1b Con1 expressing NS3 protease infected in human Huh7.5 cells assessed as reduction in viral RNA replication by luciferase reporter gene assay Hepatitis C virus (isolate Con1) 3.0 nM
Inhibition of HCV genotype 1a NS3 protease using RET S1 as substrate incubated for 1 min followed by substrate addition measured after 15 mins by FRET assay Hepatitis C virus subtype 1a 1.0 nM
Inhibition of recombinant full length HCV genotype 3a S52 NS3/4A protease preincubated for 30 mins followed by substrate addition measured by FRET assay Hepatitis C virus S52 488.0 nM
Inhibition of recombinant full length HCV genotype 2b HC-J8 NS3/4A protease preincubated for 30 mins followed by substrate addition measured by FRET assay Hepatitis C virus subtype 2b 100.0 nM
Inhibition of recombinant full length HCV genotype 2b HC-J8 NS3 protease in genotype 2a replicon cells by luciferase reporter gene assay Hepatitis C virus subtype 2b 621.0 nM
Inhibition of recombinant full length HCV genotype 1a H77 NS3/4A protease preincubated for 30 mins followed by substrate addition measured by FRET assay Hepatitis C virus (isolate H77) 0.6 nM
Inhibition of recombinant full length HCV genotype 1b J4L6S NS3/4A protease preincubated for 30 mins followed by substrate addition measured by FRET assay Hepatitis C virus subtype 1b 0.4 nM
Inhibition of recombinant full length HCV genotype 2a HC-J6 NS3/4A protease preincubated for 30 mins followed by substrate addition measured by FRET assay Hepatitis C virus subtype 2a 26.0 nM
Inhibition of recombinant full length HCV genotype 4a ED43 NS3/4A protease preincubated for 30 mins followed by substrate addition measured by FRET assay Hepatitis C virus ED43 2.1 nM
Inhibition of recombinant full length HCV genotype 5a SA13 NS3/4A protease preincubated for 30 mins followed by substrate addition measured by FRET assay Hepatitis C virus SA13 3.4 nM
Inhibition of recombinant full length HCV genotype 6a HK-6A NS3/4A protease preincubated for 30 mins followed by substrate addition measured by FRET assay Hepatitis C virus subtype 6a 1.3 nM
Inhibition of recombinant full length HCV genotype 4a ED43 NS3 protease in genotype 1b con1 replicon cells by luciferase reporter gene assay Hepatitis C virus ED43 1.7 nM
Antiviral activity against HCV genotype 1a H77 in HCV replicon cells assessed as reduction in viral RNA replication by luciferase reporter gene assay Hepatitis C virus (isolate H77) 4.0 nM
Antiviral activity against HCV genotype 2a JHF-1 in HCV replicon cells assessed as reduction in viral RNA replication by luciferase reporter gene assay Hepatitis C virus JFH-1 217.0 nM
Inhibition of HCV NS3/4A protease Hepatitis C virus 2.6 nM
Inhibition of recombinant full length HCV genotype 1a NS3/4A protease (1027 to 1711 residues) expressed in Escherichia coli strain BL21 (DE3) using RET S1 as substrate incubated for 1 min followed by substrate addition measured after 15 mins by FRET assay Hepatitis C virus subtype 1a 1.0 nM
Antiviral activity against HCV genotype 1b Con1 infected in human HuH7.5 cells assessed as inhibition of viral replication after 4 days by luciferase reporter gene assay Hepatitis C virus (isolate Con1) 6.0 nM
Inhibition of HCV genotype 1b Con1 NS3 protease infected in human HuH7 replicon cells assessed as reduction in viral replication after 4 days by luciferase reporter gene assay Hepatitis C virus (isolate Con1) 1.2 nM
Inhibition of HCV genotype 1a H77 NS3 protease infected in human HuH7 replicon cells assessed as reduction in viral replication after 4 days by luciferase reporter gene assay Hepatitis C virus (isolate H77) 4.0 nM
Inhibition of N-terminal poly-His tagged recombinant HCV genotype 1a NS3/4A protease expressed in Escherichia coli BL21(DE3) pLysS using HCV-FRET peptide substrate by FRET assay Hepatitis C virus subtype 1a 1.0 nM
Antiviral activity against HCV genotype 1b infected in human Huh7.5 replicon cells assessed as reduction in viral replication incubated for 4 days by luciferase reporter gene assay Hepatitis C virus subtype 1b 6.0 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 -7.9 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.548 %
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 0.23 % 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 0.23 %
Antiviral activity against HCV Hepatitis C virus 1.0 nM
Inhibition of recombinant full length NS3/4A protease in Hepatitis C virus subtype 3a infected in human HuH7 cells using Ac-Asp-Glu-Asp (EDANS)-Glu-Glu-Abu-(COO) Ala-Ser-Lys (DABCYL)-NH2 as substrate by FRET assay Hepatitis C virus subtype 3a 395.0 nM
Inhibition of recombinant full length NS3/4A protease in Hepatitis C virus subtype 1a replicon infected in human HuH7 cells preincubated for 3 days followed by substrate addition and measured after 2 hrs by renilla luciferase reporter gene assay Hepatitis C virus subtype 1a 4.0 nM
Inhibition of recombinant full length NS3/4A protease in Hepatitis C virus subtype 1b replicon infected in human HuH7 cells preincubated for 3 days followed by substrate addition and measured after 2 hrs by renilla luciferase reporter gene assay Hepatitis C virus subtype 1b 1.2 nM
Inhibition of recombinant full length NS3/4A protease in Hepatitis C virus subtype 2a replicon infected in human HuH7 cells preincubated for 3 days followed by substrate addition and measured after 2 hrs by renilla luciferase reporter gene assay Hepatitis C virus subtype 2a 217.0 nM
Inhibition of recombinant full length NS3/4A protease in Hepatitis C virus subtype 3a replicon infected in human HuH7 cells preincubated for 3 days followed by substrate addition and measured after 2 hrs by renilla luciferase reporter gene assay Hepatitis C virus subtype 3a 407.0 nM
Inhibition of recombinant full length NS3/4A R155K mutant protease in Hepatitis C virus subtype 1a replicon infected in human HuH7 cells preincubated for 3 days followed by substrate addition and measured after 2 hrs by renilla luciferase reporter gene assay Hepatitis C virus subtype 1a 150.0 nM
Inhibition of recombinant full length NS3/4A D168V mutant protease in Hepatitis C virus subtype 1b replicon infected in human HuH7 cells preincubated for 3 days followed by substrate addition and measured after 2 hrs by renilla luciferase reporter gene assay Hepatitis C virus subtype 1b 187.0 nM

Related Entries

Cross References

Resources Reference
ChEBI 134723
ChEMBL CHEMBL2105735
DrugBank DB11586
DrugCentral 4889
FDA SRS S9X0KRJ00S
Guide to Pharmacology 10882
PDB 2R9
PharmGKB PA166128168
PubChem 16076883
SureChEMBL SCHEMBL2630655
ZINC ZINC000085540202
CONTENTS