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Compound Detail

CHEMBL218394

BOCEPREVIR
💊 Approved Drug
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💊 Approved Drug
CC(C)(C)NC(=O)N[C@H](C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)NC(CC1CCC1)C(=O)C(N)=O)C2(C)C)C(C)(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL218394
Name BOCEPREVIR
Phase Approved
Structure Type MOL
InChI Key LHHCSNFAOIFYRV-DOVBMPENSA-N
Therapeutic ✓ Yes

Known Names

Boceprevir EBP 520 EBP-520 SCH 503034 Sch 50304 SCH-503034 Victrelis
17
Targets
179
Activities
4
Assay Types
30
PK Parameters
20
Publications
7
Known Names
4
Indications
1
Mechanisms

Molecular Properties

519.7
MW (Da)
1.71
ALogP
5
HBA
4
HBD
150.7
PSA (Ų)
0.36
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2011
Availability Discontinued
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product First in Class
USAN Stem -vir
USAN Year 2007

Extended Properties

Molecular Formula C27H45N5O5
MW 519.69
Aromatic Rings 0
Heavy Atoms 37
NP-Likeness 0.23

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 Virus Diseases Hepatitis C Thrombocytopenia

ATC Classification

J05AP03
boceprevir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 100 meas. best 8.0
Ki 41 meas. best 8.96
IC50 29 meas. best 7.5
Kd 9 meas. best 8.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 8.96 7.8156 1.1 32
Hepatitis C virus
CHEMBL379
 Ki 8.7 8.0333 2.0 3
Unchecked
CHEMBL612545
 Kd 8.41 6.1075 3.9 8
Non-structural protein 4b
CHEMBL6066153
 Ki 8.22 8.22 6.0 3
Hepatitis C virus
CHEMBL379
 EC50 8.0 6.389 10.0 91
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 Ki 7.85 7.85 14.0 1
NS3
CHEMBL1293269
 Ki 7.85 7.85 14.0 1
Chymase
CHEMBL4068
 IC50 7.5 7.5 32.0 1
Cathepsin K
CHEMBL268
 IC50 7.4 7.4 40.0 1
Cathepsin L2
CHEMBL3272
 IC50 7.12 7.12 75.0 1
Cathepsin S
CHEMBL2954
 IC50 6.92 6.92 120.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 6.31 5.3875 490.0 8
Procathepsin L
CHEMBL3837
 IC50 6.12 6.12 760.0 1
Cathepsin F
CHEMBL2517
 IC50 5.96 5.96 1100.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 Ki 5.93 5.93 1180.0 1
Unchecked
CHEMBL612545
 EC50 5.88 5.88 1310.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.8 5.2808 1590.0 12
Unchecked
CHEMBL612545
 IC50 5.8 5.4575 1590.0 4
SARS-CoV-2
CHEMBL4303835
 IC50 5.38 5.38 4130.0 1
Liver cytosol
CHEMBL2367378
 IC50 5.34 5.34 4580.0 1
Cathepsin B
CHEMBL4072
 IC50 5.21 5.21 6200.0 1
Replicase polyprotein 1a
CHEMBL3927
 IC50 5.18 5.18 6630.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 Kd 5.08 5.08 8370.0 1
Neutrophil elastase
CHEMBL248
 IC50 4.77 4.77 17000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1.52 uM.hr Rattus norvegicus
AUC 0.12 uM.hr Macaca mulatta
AUC 3.08 uM.hr Canis lupus familiaris
AUC 0.21 uM.hr Rattus norvegicus
AUC 1.52 uM.hr Rattus norvegicus
AUC 1.52 uM.hr Rattus norvegicus
AUC 0.14 uM.hr Rattus norvegicus
AUC 0.1 uM.hr Rattus norvegicus
AUC 0.3 uM.hr Macaca mulatta
AUC 3.1 uM.hr Canis lupus familiaris
AUC 0.14 uM.hr Rattus norvegicus
AUC 1.52 uM.hr Rattus norvegicus
AUC 0.12 uM.hr Macaca mulatta
AUC 1.52 uM.hr Rattus norvegicus
AUC 0.12 uM.hr Macaca mulatta
AUC 0.12 uM.hr Macaca mulatta
Cmax 130.0 nM Rattus norvegicus
Cmax 1.72 ug.mL-1 Homo sapiens
F 26.0 % Rattus norvegicus
F 4.0 % Macaca mulatta
F 30.0 % Canis lupus familiaris
F 34.0 % Mus musculus
F 26.0 % Rattus norvegicus
F 4.0 % Macaca mulatta
F 30.0 % Canis lupus familiaris
F 3.5 % Rattus norvegicus
F 26.0 % Rattus norvegicus
F 26.0 % Rattus norvegicus
F 4.0 % Macaca mulatta
F 34.0 % Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 1.1 nM 8.96 Inhibition of HCV 1a NS3/4A protease 20823284
Hepatitis C virus Ki = 2.0 nM 8.7 Inhibition of HCV 1b NS3/4A protease 20823284
Unchecked Ki = 2.3 nM 8.64 Inhibition of HCV 6a NS3/4A protease 20823284
Unchecked Kd = 3.9 nM 8.41 Inhibition of Hepatitis C virus genotype 3a full-length NS3 protease assessed as... 24512311
Non-structural protein 4b Ki = 6.0 nM 8.22 Binding affinity to Hepatitis C virus genotype 1a NS4B assessed as inhibition co... 38179950
Non-structural protein 4b Ki = 6.0 nM 8.22 Binding affinity to Hepatitis C virus genotype 2b NS4B assessed as inhibition co... 38179950
Non-structural protein 4b Ki = 6.0 nM 8.22 Binding affinity to Hepatitis C virus genotype 3a NS4B assessed as inhibition co... 38179950
Unchecked Ki = 7.3 nM 8.14 Inhibition of HCV 2a NS3/4A protease 20823284
Unchecked Ki = 8.6 nM 8.07 Inhibition of HCV 4a NS3/4A protease 20823284
Hepatitis C virus EC50 = 10.0 nM 8.0 Antiviral activity against Hepatitis C virus infected in human HuH7 cells assess... 24135727
Hepatitis C virus Ki = 14.0 nM 7.85 Inhibition of Hepatitis C virus genotype 1 NS3 protease 20226659
Unchecked Ki = 14.0 nM 7.85 Inhibition of HCV NS3 protease by continuous spectrophotometric assay 19481946
Unchecked Ki = 14.0 nM 7.85 Inhibition of HCV NS4A-tethered single chain NS3 serine protease by spectrophoto... 20004570
Unchecked Ki = 14.0 nM 7.85 Inhibition of HCV NS4A-tethered single chain NS3 serine protease assessed as Ac-... 20149666
Unchecked Ki = 14.0 nM 7.85 Inhibition of HCV NS3/4A serine protease by continuous spectrophotometric assay 20149655
Unchecked Ki = 14.0 nM 7.85 Inhibition of HCV NS4A tagged recombinant single chain NS3 protease after 15 min... 20303756
Hepatitis C virus serine protease, NS3/NS4A Ki = 14.0 nM 7.85 Inhibition of HCV genotype 1a NS3/4A protease using Ac-DED(Edans)EEAbu-psi[COO]A... 25456385
Unchecked Ki = 14.0 nM 7.85 Inhibition of HCV NS3/4A protease using AcDTEDVVP(Nva)-O-PAP as substrate pretre... 28501513
Unchecked Ki = 14.0 nM 7.85 Inhibition of HCV NS3/4A protease 26241789
Unchecked Ki = 14.0 nM 7.85 Inhibition of hepatitis C virus NS3 serine protease 18032054

Literature References

PubMed DOI Target Context # Activities
20176898 10.1128/aac.01452-09 Hepatitis C virus 89
21123164 10.1124/dmd.110.036996 Liver cytosol 35
24135727 10.1016/j.bmcl.2013.09.068 Hepatitis C virus 32
18936191 10.1128/aac.01081-08 Hepatitis C virus 26
21123164 10.1124/dmd.110.036996 ADMET 13
24512311 10.1021/jm401690f Unchecked 12
20855726 10.1128/aac.00777-10 Hepatitis C virus 10
34041486 10.1039/D0MD00367K Murine hepatitis virus 9
20823284 10.1128/aac.00787-10 Unchecked 7
20823284 10.1128/aac.00787-10 Hepatitis C virus 5
18625766 10.1128/aac.01534-07 Hepatitis C virus 4
18625766 10.1128/aac.01534-07 ADMET 4
19841155 10.1128/aac.00677-09 Unchecked 4
22471376 10.1021/jm201278q Hepatitis C virus 4
19841155 10.1128/aac.00677-09 Hepatitis C virus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
21123164 10.1124/dmd.110.036996 Aldo-keto reductase family 1 member C2 4
21123164 10.1124/dmd.110.036996 Aldo-keto reductase family 1 member C3 3
20302300 10.1021/jm9016027 Rhesus monkey 3
17004721 10.1021/jm060325b Rattus norvegicus 3

Data from ChEMBL 36 via Core Engine