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Compound Detail

CHEMBL1255891

NARLAPREVIR
🧪 Phase III
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🧪 Phase III
CCCC[C@H](NC(=O)[C@@H]1[C@@H]2[C@H](CN1C(=O)[C@@H](NC(=O)NC1(CS(=O)(=O)C(C)(C)C)CCCCC1)C(C)(C)C)C2(C)C)C(=O)C(=O)NC1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1255891
Name NARLAPREVIR
Phase Phase III
Structure Type MOL
InChI Key RICZEKWVNZFTNZ-LFGITCQGSA-N

Known Names

Narlaprevir SCH 900518 SCH-900518
5
Targets
14
Activities
3
Assay Types
0
PK Parameters
15
Publications
3
Known Names
4
Indications
1
Mechanisms

Molecular Properties

708.0
MW (Da)
3.62
ALogP
7
HBA
4
HBD
170.8
PSA (Ų)
0.21
QED
1
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -vir
USAN Year 2009

Extended Properties

Molecular Formula C36H61N5O7S
MW 707.98
Aromatic Rings 0
Heavy Atoms 49
NP-Likeness 0.08

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 Virus Diseases Hepatitis C, Chronic Liver Diseases

ATC Classification

J05AP14
narlaprevir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

Ki 6 meas. best 9.15
EC50 4 meas. best 7.4
IC50 4 meas. best 5.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.15 8.51 0.7 4
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 Ki 8.22 8.22 6.0 1
Hepatitis C virus
CHEMBL379
 Ki 8.15 8.15 7.0 1
Hepatitis C virus
CHEMBL379
 EC50 7.4 7.4 40.0 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 5.66 5.345 2200.0 4
SARS-CoV-2
CHEMBL4303835
 EC50 5.11 5.0133 7700.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.7 nM 9.15 Inhibition of Hepatitis C virus genotype 1a NS3 protease 20308381
Unchecked Ki = 3.0 nM 8.52 Inhibition of Hepatitis C virus genotype 2a NS3 protease 20308381
Hepatitis C virus serine protease, NS3/NS4A Ki = 6.0 nM 8.22 Inhibition of HCV NS3/4a protease using Ac-DE-Dap(QXL520)-EE-Abu-shi-[COO]AS-C(5... 30639895
Unchecked Ki = 6.0 nM 8.22 Binding affinity to Hepatitis C virus NS2B-NS3 protease assessed as inhibition c... 37922830
Unchecked Ki = 7.0 nM 8.15 Inhibition of Hepatitis C virus genotype 3a NS3 protease 20308381
Hepatitis C virus Ki = 7.0 nM 8.15 Inhibition of Hepatitis C virus genotype 1b NS3 protease 20308381
Hepatitis C virus EC50 = 40.0 nM 7.4 Antiviral activity against HCV 30639895
Replicase polyprotein 1ab IC50 = 2200.0 nM 5.66 Inhibition of SARS-CoV-2 MPro using Dabcyl-KTSAVLQSGFRKME-Edans as substrate pre... 37659195
Replicase polyprotein 1ab IC50 = 5730.0 nM 5.24 Inhibition of SARS-CoV-2 MPro 33191083
Replicase polyprotein 1ab IC50 = 5727.96 nM 5.24 Inhibition of SARS-CoV-2 MPro 33191083
Replicase polyprotein 1ab IC50 = 5700.0 nM 5.24 Inhibition of SARS-CoV-2 3CLpro 38365209
SARS-CoV-2 EC50 = 7700.0 nM 5.11 Antiviral activity against SARS-CoV-2 infected in african green monkey Vero E6 c... 37659195
SARS-CoV-2 EC50 = 7700.0 nM 5.11 Antiviral activity against SARS-CoV-2 infected in African green monkey Vero E6 e... 37659195
SARS-CoV-2 EC50 = 15000.0 nM 4.82 Antiviral activity against SARS-CoV-2 Omicron B.1.1.7 Alpha infected in human 29... 37659195

Literature References

PubMed DOI Target Context # Activities
20308381 10.1128/aac.00135-10 Hepatitis C virus 28
20308381 10.1128/aac.00135-10 Unchecked 3
37659195 10.1016/j.ejmech.2023.115772 SARS-CoV-2 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
33191083 10.1016/j.bmc.2020.115860 Replicase polyprotein 1ab 2
20308381 10.1128/aac.00135-10 ADMET 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
30639895 10.1016/j.ejmech.2018.12.045 Hepatitis C virus serine protease, NS3/NS4A 1
30639895 10.1016/j.ejmech.2018.12.045 Hepatitis C virus 1
38365209 10.1021/acs.jmedchem.3c02248 Replicase polyprotein 1ab 1
37659195 10.1016/j.ejmech.2023.115772 Replicase polyprotein 1ab 1
37922830 10.1016/j.ejmech.2023.115919 Unchecked 1

Data from ChEMBL 36 via Core Engine