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Compound Detail

CHEMBL231813

TELAPREVIR
💊 Approved Drug
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💊 Approved Drug
CCC[C@H](NC(=O)[C@@H]1[C@H]2CCC[C@H]2CN1C(=O)[C@@H](NC(=O)[C@@H](NC(=O)c1cnccn1)C1CCCCC1)C(C)(C)C)C(=O)C(=O)NC1CC1

Basic Information

ChEMBL ID CHEMBL231813
Name TELAPREVIR
Phase Approved
Structure Type MOL
InChI Key BBAWEDCPNXPBQM-GDEBMMAJSA-N
Therapeutic ✓ Yes

Known Names

Incivek Incivo LY 570310 LY-570310 MP 424 MP-424 Telaprevir VRT 111950 VRT-111950 VX 950 VX-950
19
Targets
203
Activities
4
Assay Types
13
PK Parameters
20
Publications
11
Known Names
7
Indications
1
Mechanisms

Molecular Properties

679.9
MW (Da)
2.45
ALogP
8
HBA
4
HBD
179.6
PSA (Ų)
0.23
QED
1
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2011
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -vir
USAN Year 2006

Extended Properties

Molecular Formula C36H53N7O6
MW 679.86
Aromatic Rings 1
Heavy Atoms 49
NP-Likeness -0.28

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 HIV Infections Infections Thrombocytopenia Liver Diseases

ATC Classification

J05AP02
telaprevir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

EC50 116 meas. best 8.11
IC50 48 meas. best 7.58
Ki 27 meas. best 8.49
Kd 12 meas. best 8.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 8.49 7.43 3.2 19
NS3 protease
CHEMBL4296313
Ki 8.41 8.41 3.9 1
Hepatitis C virus
CHEMBL379
Ki 8.36 7.5833 4.4 3
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
Ki 8.15 8.15 7.0 1
Hepatitis C virus
CHEMBL379
EC50 8.11 6.2521 7.8 109
Unchecked
CHEMBL612545
EC50 8.1 8.1 8.0 1
Unchecked
CHEMBL612545
Kd 8.07 6.3642 8.5 12
Chymase
CHEMBL4068
IC50 7.58 7.58 26.0 1
Chymotrypsin-like elastase family member 1
CHEMBL3000
IC50 7.52 7.52 30.0 1
Internal ribosome entry site (IRES)
CHEMBL612412
Ki 7.36 7.36 44.0 1
Unchecked
CHEMBL612545
IC50 7.3 6.345 50.0 12
enterovirus D68
CHEMBL613204
EC50 7.28 6.4833 52.1 6
Hepatitis C virus
CHEMBL379
IC50 7.2 6.0133 63.0 12
NS3 protease
CHEMBL4296325
Ki 7.09 6.15 82.0 2
NS3 protease
CHEMBL4296313
IC50 6.89 6.2186 130.0 7
Cathepsin B
CHEMBL4072
IC50 6.68 5.8933 210.0 3
Cathepsin S
CHEMBL2954
IC50 6.52 6.52 300.0 1
Non-structural protein 4b
CHEMBL6066153
IC50 6.45 6.45 354.0 1
Cathepsin K
CHEMBL268
IC50 6.2 6.2 630.0 1
Neutrophil elastase
CHEMBL248
IC50 6.17 5.4567 680.0 3
Cathepsin L2
CHEMBL3272
IC50 5.87 5.87 1350.0 1
Procathepsin L
CHEMBL3837
IC50 5.46 5.46 3500.0 1
Plasminogen
CHEMBL1801
IC50 5.06 5.06 8700.0 1
Replicase polyprotein 1ab
CHEMBL4523582
IC50 4.97 4.955 10700.0 2
SARS-CoV-2
CHEMBL4303835
IC50 4.94 4.94 11552.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 19.0 uM Mus musculus
AUC 3.0 uM Mus musculus
AUC 1046.98 ng.hr.mL-1 Rattus norvegicus
AUC 2270.73 ng.hr.mL-1 Rattus norvegicus
AUC 27670.3 ng.hr.mL-1 Canis lupus familiaris
CL 54.0 mL.min-1.kg-1 Rattus norvegicus
CL 42.0 mL.min-1.kg-1 Canis lupus familiaris
Cmax 630.0 nM Rattus norvegicus
F 34.8 % Rattus norvegicus
F 25.0 % Rattus norvegicus
F 40.7 % Canis lupus familiaris
T1/2 35.0 hr -
T1/2 0.3333 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 3.2 nM 8.49 Inhibition of HCV 1a NS3/4A protease 20823284
NS3 protease Ki = 3.9 nM 8.41 Inhibition of full-length HCV NS3 protease D168V mutant 23517538
Hepatitis C virus Ki = 4.4 nM 8.36 Inhibition of HCV 1b NS3/4A protease 20823284
Unchecked Ki = 4.5 nM 8.35 Inhibition of HCV 6a NS3/4A protease 20823284
Hepatitis C virus serine protease, NS3/NS4A Ki = 7.0 nM 8.15 Binding affinity to Hepatitis C virus genotype 1H NS3-4A protease assessed as in... 37922830
Unchecked Ki = 7.0 nM 8.15 Inhibition of HCV NS3/4A protease 26241789
Unchecked Ki = 7.0 nM 8.15 Reversible inhibition of HCV NS3 protease 21381769
Hepatitis C virus EC50 = 7.8 nM 8.11 Antiviral activity against wild type HCV by qRT-PCR analysis based by Reed-Muenc... 32378892
Unchecked EC50 = 8.0 nM 8.1 Antiviral activity against HCV subtype 2a J6/JFH/JC1 infected in human Huh7.5 ce... 27783522
Unchecked Kd = 8.5 nM 8.07 Inhibition of Hepatitis C virus genotype 1b full-length NS3 protease assessed as... 24512311
Unchecked Kd = 8.6 nM 8.07 Inhibition of Hepatitis C virus genotype 1b full-length NS3 protease assessed as... 24512311
Unchecked Ki = 15.0 nM 7.82 Inhibition of HCV 2a NS3/4A protease 20823284
Unchecked Ki = 15.0 nM 7.82 Inhibition of full-length wild-type HCV NS3 protease 23517538
Hepatitis C virus EC50 = 15.0 nM 7.82 Antiviral activity against Hepatitis C virus infected in human Huh7.5 cells pret... 38179950
Unchecked Kd = 17.0 nM 7.77 Inhibition of Hepatitis C virus genotype 1a full-length NS3/NS4A protease assess... 24512311
Hepatitis C virus EC50 = 20.0 nM 7.7 Antiviral activity against wild-type HCV J6/JFH/JC1 infected in human Huh7.5 cel... 27783522
Hepatitis C virus EC50 = 22.0 nM 7.66 Antiviral activity against Hepatitis C virus infected in human Huh7.5 cells asse... 34883293
Chymase IC50 = 26.0 nM 7.58 Inhibition of human Chymase 19841155
Hepatitis C virus EC50 = 30.0 nM 7.52 Antiviral activity against HCV J6/JFH/JC-1 infected in human Huh7.5 cells assess... 29232582
Chymotrypsin-like elastase family member 1 IC50 = 30.0 nM 7.52 Inhibition of human Pancreatic elastase 1 19841155

Literature References

PubMed DOI Target Context # Activities
19894743 10.1021/jm901023f No relevant target 113
20176898 10.1128/aac.01452-09 Hepatitis C virus 89
24135727 10.1016/j.bmcl.2013.09.068 Hepatitis C virus 32
17938182 10.1128/aac.00863-07 Hepatitis C virus 30
17556358 10.1074/jbc.m610207200 Hepatitis C virus 20
19104013 10.1128/aac.00939-08 Hepatitis C virus 13
24512311 10.1021/jm401690f Unchecked 12
22471376 10.1021/jm201278q Hepatitis C virus 12
18086851 10.1128/aac.01149-07 Hepatitis C virus 12
29232582 10.1016/j.ejmech.2017.12.002 Hepatitis C virus 11
17556358 10.1074/jbc.m610207200 NS3 protease 10
20855726 10.1128/aac.00777-10 Hepatitis C virus 10
23142614 10.1016/j.bmcl.2012.10.075 Hepatitis C virus 9
20823284 10.1128/aac.00787-10 Unchecked 7
17556358 10.1074/jbc.m610207200 Unchecked 7
32378892 10.1021/acs.jmedchem.0c00232 Hepatitis C virus 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
37857371 10.1021/acs.jmedchem.3c00995 enterovirus D68 6
38179950 10.1021/acs.jmedchem.3c01971 ADMET 6
20823284 10.1128/aac.00787-10 Hepatitis C virus 5

Data from ChEMBL 36 via Core Engine