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Compound Detail

CHEMBL297884

CILUPREVIR
🧪 Phase II
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🧪 Phase II
COc1ccc2c(O[C@@H]3C[C@H]4C(=O)N[C@]5(C(=O)O)C[C@H]5/C=C\CCCCC[C@H](NC(=O)OC5CCCC5)C(=O)N4C3)cc(-c3csc(NC(C)C)n3)nc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL297884
Name CILUPREVIR
Phase Phase II
Structure Type MOL
InChI Key PJZPDFUUXKKDNB-KNINVFKUSA-N

Known Names

BILN 2061 ZW BILN-2061 BILN-2061-ZW Ciluprevir
7
Targets
151
Activities
4
Assay Types
10
PK Parameters
20
Publications
4
Known Names
1
Mechanisms

Molecular Properties

774.9
MW (Da)
6.05
ALogP
11
HBA
4
HBD
181.3
PSA (Ų)
0.19
QED
3
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -vir
USAN Year 2004

Extended Properties

Molecular Formula C40H50N6O8S
MW 774.94
Aromatic Rings 3
Heavy Atoms 55
NP-Likeness 0.04

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 ✓ ✓

Activity Summary

EC50 107 meas. best 9.4
Ki 20 meas. best 10.05
IC50 12 meas. best 9.1
Kd 12 meas. best 8.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NS3
CHEMBL1293269
 Ki 10.05 9.09 0.1 3
Unchecked
CHEMBL612545
 Ki 10.05 8.916 0.1 10
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 Ki 9.52 9.52 0.3 1
Hepatitis C virus
CHEMBL379
 Ki 9.52 9.2933 0.3 3
Hepatitis C virus
CHEMBL379
 EC50 9.4 7.8925 0.4 106
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 IC50 9.1 9.1 0.8 1
Unchecked
CHEMBL612545
 IC50 9.05 7.955 0.9 8
Hepatitis C virus
CHEMBL379
 IC50 9.0 9.0 1.0 2
Unchecked
CHEMBL612545
 Kd 8.89 7.66 1.3 12
NS3 protease
CHEMBL4296325
 Ki 7.62 7.27 24.0 2
NS3 protease
CHEMBL4296313
 Ki 6.7 6.7 200.0 1
NS3
CHEMBL1293269
 IC50 5.52 5.52 3000.0 1
ADMET
CHEMBL612558
 EC50 4.3 4.3 50000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 9686.75 ng.hr.mL-1 Rattus norvegicus
Cmax 2500.0 nM Rattus norvegicus
F 42.0 % Rattus norvegicus
F 7.0 % Macaca mulatta
F 36.0 % Canis lupus familiaris
F 13.0 % Rattus norvegicus
T1/2 1.3 hr Rattus norvegicus
T1/2 7.0 hr Macaca mulatta
T1/2 4.2 hr Canis lupus familiaris
T1/2 0.8 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NS3 Ki = 0.089 nM 10.05 Inhibition of HCV genotype-1a NS3 protease 29477077
Unchecked Ki = 0.089 nM 10.05 Inhibition of full-length wild-type HCV NS3 protease 23517538
Hepatitis C virus serine protease, NS3/NS4A Ki = 0.3 nM 9.52 Inhibition of HCV genotype 1a NS3/4A protease using Ac-DED(Edans)EEAbu-psi[COO]A... 25456385
Unchecked Ki = 0.3 nM 9.52 Inhibition of Hepatitis C virus genotype 1a full length NS3/2K-NS4A protease usi... 24900813
Unchecked Ki = 0.3 nM 9.52 Inhibition of HCV 1a NS3 protease 21381769
Hepatitis C virus Ki = 0.3 nM 9.52 Inhibition of Hepatitis C virus genotype 1b NS3/4A protease activity 19841155
Unchecked Ki = 0.3 nM 9.52 Inhibition of HCV NS3 protease by FRET assay 20541424
Unchecked Ki = 0.3 nM 9.52 Inhibition of full length HCV NS3/4A protease 18722116
NS3 Ki = 0.3 nM 9.52 Inhibition of HCV 1a NS3 protease 17113777
Hepatitis C virus EC50 = 0.4 nM 9.4 Antiviral activity against Hepatitis C virus subtype 1b expressing NS3 F43I muta... 20176898
Hepatitis C virus EC50 = 0.4 nM 9.4 Antiviral activity against Hepatitis C virus subtype 1b expressing NS3 F43V muta... 20176898
Hepatitis C virus EC50 = 0.4 nM 9.4 Antiviral activity against Hepatitis C virus subtype 1b expressing NS3 F43S and ... 20176898
Hepatitis C virus EC50 = 0.5 nM 9.3 Antiviral activity against Hepatitis C virus subtype 1b expressing NS3 S138T mut... 20176898
Hepatitis C virus EC50 = 0.5 nM 9.3 Antiviral activity against Hepatitis C virus subtype 1b by stable replicon assay 22471376
Hepatitis C virus Ki = 0.66 nM 9.18 Inhibition of HCV 1b NS3 protease 21381769
Unchecked Ki = 0.66 nM 9.18 Inhibition of HCV NS3 protease by FRET assay 18194867
Hepatitis C virus Ki = 0.66 nM 9.18 Inhibition of HCV 1b NS3 protease 17113777
Hepatitis C virus EC50 = 0.7 nM 9.15 Antiviral activity against Hepatitis C virus subtype 1b expressing NS3 T54A muta... 20176898
Hepatitis C virus serine protease, NS3/NS4A IC50 = 0.8 nM 9.1 Inhibition of full length Hepatitis C virus genotype 1b Con1 NS3/4A by FRET assa... 25155387
Hepatitis C virus EC50 = 0.8 nM 9.1 Antiviral activity against Hepatitis C virus subtype 1b expressing NS3 Q80L muta... 20176898

Literature References

PubMed DOI Target Context # Activities
20176898 10.1128/aac.01452-09 Hepatitis C virus 89
18086851 10.1128/aac.01149-07 Hepatitis C virus 22
17908950 10.1128/aac.00723-07 Hepatitis C virus 17
24512311 10.1021/jm401690f Unchecked 12
22471376 10.1021/jm201278q Hepatitis C virus 9
19104013 10.1128/aac.00939-08 Hepatitis C virus 8
15027850 10.1021/jm0342414 Rattus norvegicus 6
19841155 10.1128/aac.00677-09 Hepatitis C virus 4
17371824 10.1128/aac.01004-06 Hepatitis C virus 4
18625766 10.1128/aac.01534-07 Hepatitis C virus 4
18625766 10.1128/aac.01534-07 ADMET 4
19896376 10.1016/j.bmcl.2009.10.070 Hepatitis C virus 3
19226162 10.1021/jm8010965 Hepatitis C virus 3
21381769 10.1021/jm1012374 Hepatitis C virus 3
23517538 10.1021/jm301887f NS3 protease 3
19841155 10.1128/aac.00677-09 Unchecked 3
21381769 10.1021/jm1012374 Rhesus monkey 2
22366653 10.1016/j.bmcl.2012.01.017 Hepatitis C virus 2
21381769 10.1021/jm1012374 Canis familiaris 2
21440437 10.1016/j.bmcl.2011.03.014 Hepatitis C virus 2

Data from ChEMBL 36 via Core Engine