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Compound Detail

CHEMBL4525964

VANIPREVIR
🧪 Phase III
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🧪 Phase III
CC[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@H](C(C)(C)C)NC(=O)OCC(C)(C)CCCCc1cccc3c1CN(C3)C(=O)O2)C(=O)NS(=O)(=O)C1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4525964
Name VANIPREVIR
Phase Phase III
Structure Type MOL
InChI Key KUQWGLQLLVFLSM-ONAXAZCASA-N

Known Names

MK-7009 MK7009 Vaniprevir
6
Targets
58
Activities
3
Assay Types
30
PK Parameters
20
Publications
3
Known Names
3
Indications
1
Mechanisms

Molecular Properties

758.0
MW (Da)
3.90
ALogP
9
HBA
3
HBD
180.5
PSA (Ų)
0.39
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -vir
USAN Year 2009

Extended Properties

Molecular Formula C38H55N5O9S
MW 757.95
Aromatic Rings 1
Heavy Atoms 53
NP-Likeness 0.09

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 Infections

Activity Summary

EC50 34 meas. best 9.57
Ki 16 meas. best 10.3
IC50 8 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 Ki 10.3 9.01 0.1 2
Non-structural protein 4b
CHEMBL6066153
 Ki 10.3 10.3 0.1 1
Unchecked
CHEMBL612545
 Ki 10.3 9.1567 0.1 9
Hepatitis C virus
CHEMBL379
 Ki 10.22 10.22 0.1 1
Hepatitis C virus
CHEMBL379
 EC50 9.57 7.9324 0.3 34
Hepatitis C virus
CHEMBL379
 IC50 8.52 8.106 3.0 5
Non-structural protein 4b
CHEMBL6066153
 IC50 8.52 8.52 3.0 1
Genome polyprotein
CHEMBL4296298
 Ki 7.66 7.2767 22.0 3
Unchecked
CHEMBL612545
 IC50 6.28 6.28 520.0 1
Cathepsin S
CHEMBL2954
 IC50 4.11 4.11 78000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 909.54 ng.hr.mL-1 Canis lupus familiaris
AUC 3941.34 ng.hr.mL-1 Pan troglodytes
AUC - ng.hr.mL-1 Rattus norvegicus
AUC 37.9 ng.hr.mL-1 Macaca mulatta
AUC 37.9 ng.hr.mL-1 Macaca mulatta
AUC - ng.hr.mL-1 Rattus norvegicus
AUC 3941.34 ng.hr.mL-1 Pan troglodytes
AUC 3107.59 ng.hr.mL-1 Canis lupus familiaris
AUC 1894.88 ng.hr.mL-1 Macaca mulatta
AUC 454.77 ng.hr.mL-1 Rattus norvegicus
AUC 909.54 ng.hr.mL-1 Canis lupus familiaris
CL 11.0 mL.min-1.kg-1 Canis lupus familiaris
CL 18.0 mL.min-1.kg-1 Macaca mulatta
CL 74.0 mL.min-1.kg-1 Rattus norvegicus
CL 74.0 mL.min-1.kg-1 Rattus norvegicus
CL 18.0 mL.min-1.kg-1 Macaca mulatta
CL 11.0 mL.min-1.kg-1 Canis lupus familiaris
CL 5.2 uM.hr Pan troglodytes
Cmax 500.0 nM Canis lupus familiaris
Cmax 900.0 nM Pan troglodytes
Cmax - nM Rattus norvegicus
Cmax 10.0 nM Macaca mulatta
Cmax 10.0 nM Macaca mulatta
Cmax - nM Rattus norvegicus
Cmax 900.0 nM Pan troglodytes
Cmax 500.0 nM Canis lupus familiaris
T1/2 1.2 hr Canis lupus familiaris
T1/2 1.3 hr Macaca mulatta
T1/2 0.9 hr Rattus norvegicus
T1/2 0.9 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Non-structural protein 4b Ki = 0.05 nM 10.3 Binding affinity to Hepatitis C virus genotype 1b NS4B assessed as inhibition co... 38179950
Hepatitis C virus serine protease, NS3/NS4A Ki = 0.05 nM 10.3 Inhibition of HCV genotype 1a NS3/4A protease using Ac-DED(Edans)EEAbu-psi[COO]A... 25456385
Unchecked Ki = 0.05 nM 10.3 Inhibition of Hepatitis C virus (isolate BK) genotype 1b NS3/4a protease express... 24900473
Unchecked Ki = 0.05 nM 10.3 Inhibition of HCV1b BK full length NS3/4A protease expressed in Escherichia coli... 20163176
Hepatitis C virus Ki = 0.06 nM 10.22 Inhibition of Hepatitis C virus genotype 1b NS3/4A protease activity 19841155
Unchecked Ki = 0.06 nM 10.22 Inhibition of HCV NS3 protease by FRET assay 20541424
Unchecked Ki = 0.07 nM 10.15 Inhibition of Hepatitis C virus genotype 1a NS3/4A protease activity 19841155
Hepatitis C virus EC50 = 0.27 nM 9.57 Antiviral activity against HCV1b harboring Q80Q polymorphism in NS3 protease gen... 20855726
Hepatitis C virus EC50 = 0.41 nM 9.39 Antiviral activity against HCV1b harboring Q80K polymorphism in NS3 protease gen... 20855726
Hepatitis C virus EC50 = 0.7 nM 9.15 Antiviral activity against HCV1b Con1 harboring NS3 protease gene infected in hu... 20855726
Unchecked Ki = 0.9 nM 9.05 Inhibition of HCV JFH-1 full length NS3/4A protease expressed in Escherichia col... 20163176
Unchecked Ki = 1.0 nM 9.0 Inhibition of Hepatitis C virus genotype 2a NS3/4A protease activity 19841155
Unchecked Ki = 1.4 nM 8.85 Inhibition of Hepatitis C virus genotype 2b NS3/4A protease activity 19841155
Hepatitis C virus EC50 = 1.6 nM 8.8 Antiviral activity against wild type Hepatitis C virus subtype 1b by transient r... 22471376
Hepatitis C virus EC50 = 1.6 nM 8.8 Antiviral activity against Hepatitis C virus genotype 1a containing NS3/con1 pro... 19841155
Hepatitis C virus EC50 = 2.9 nM 8.54 Antiviral activity against Hepatitis C virus containing NS3/4a ps40 sequence by ... 19841155
Hepatitis C virus EC50 = 2.9 nM 8.54 Antiviral activity against Hepatitis C virus containing NS3/4a ps20 sequence by ... 19841155
Hepatitis C virus IC50 = 3.0 nM 8.52 Antiviral activity against HCV 30639895
Non-structural protein 4b IC50 = 3.0 nM 8.52 Inhibition of Hepatitis C virus genotype 1b NS4B 38179950
Hepatitis C virus IC50 = 3.0 nM 8.52 Antiviral activity against HCV Con1 infected in human HuH7 cells assessed as inh... 20163176

Literature References

PubMed DOI Target Context # Activities
24135727 10.1016/j.bmcl.2013.09.068 Hepatitis C virus 30
19841155 10.1128/aac.00677-09 Hepatitis C virus 22
20855726 10.1128/aac.00777-10 Hepatitis C virus 10
19841155 10.1128/aac.00677-09 Canis familiaris 7
19841155 10.1128/aac.00677-09 Rhesus monkey 7
19841155 10.1128/aac.00677-09 Rattus norvegicus 7
20163176 10.1021/jm9015526 Canis familiaris 5
20163176 10.1021/jm9015526 Rhesus monkey 5
20163176 10.1021/jm9015526 Rattus norvegicus 5
20163176 10.1021/jm9015526 Liver 4
19841155 10.1128/aac.00677-09 Pan troglodytes 4
19841155 10.1128/aac.00677-09 Unchecked 4
20163176 10.1021/jm9015526 Hepatitis C virus 3
22471376 10.1021/jm201278q Hepatitis C virus 3
24900473 10.1021/ml300017p Genome polyprotein 3
20163176 10.1021/jm9015526 Nucleic Acid 3
24900473 10.1021/ml300017p Unchecked 2
20163176 10.1021/jm9015526 ADMET 2
20163176 10.1021/jm9015526 Pan troglodytes 2
20163176 10.1021/jm9015526 Unchecked 2

Data from ChEMBL 36 via Core Engine