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Compound Detail

CHEMBL3545363

GLECAPREVIR
💊 Approved Drug
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💊 Approved Drug
CC(C)(C)[C@@H]1NC(=O)O[C@@H]2CCC[C@H]2OC/C=C/C(F)(F)c2nc3ccccc3nc2O[C@@H]2C[C@@H](C(=O)N[C@]3(C(=O)NS(=O)(=O)C4(C)CC4)C[C@H]3C(F)F)N(C2)C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3545363
Name GLECAPREVIR
Phase Approved
Structure Type MOL
InChI Key MLSQGNCUYAMAHD-ITNVBOSISA-N
Therapeutic ✓ Yes

Known Names

A-1282576 A-1282576.0 A-12825760 ABT-493 Glecaprevir Glecaprevir component of mavyret
5
Targets
22
Activities
3
Assay Types
6
PK Parameters
11
Publications
6
Known Names
6
Indications
1
Mechanisms

Molecular Properties

838.9
MW (Da)
3.86
ALogP
11
HBA
3
HBD
195.2
PSA (Ų)
0.28
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2017
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral
USAN Stem -vir
USAN Year 2015

Extended Properties

Molecular Formula C38H46F4N6O9S
MW 838.88
Aromatic Rings 2
Heavy Atoms 58
NP-Likeness 0.40

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 Stress Disorders, Post-Traumatic Kidney Diseases Liver Diseases Renal Insufficiency, Chronic

Activity Summary

Ki 10 meas. best 10.3
IC50 7 meas. best 8.42
EC50 5 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 Ki 10.3 9.8 0.1 2
Hepatitis C virus NS5B RNA-dependent RNA polymerase
CHEMBL5375
 Ki 10.28 10.28 0.1 1
Non-structural protein 4b
CHEMBL6066153
 Ki 10.2 9.73 0.1 6
Hepatitis C virus
CHEMBL379
 EC50 9.7 8.636 0.2 5
Non-structural protein 4b
CHEMBL6066153
 IC50 8.42 7.74 3.8 7
Unchecked
CHEMBL612545
 Ki 7.05 7.05 90.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 18455.36 ng.hr.mL-1 Rattus norvegicus
F 90.0 % Rattus norvegicus
F 95.0 % Canis lupus familiaris
T1/2 6.0 hr Homo sapiens
T1/2 2.8 hr Rattus norvegicus
T1/2 0.6 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus serine protease, NS3/NS4A Ki = 0.05 nM 10.3 Inhibition of HCV GT-1a NS3/4a protease using Ac-DE-D(Edans)-EE-Abu-c-[COO]-AS-K... 34405680
Hepatitis C virus NS5B RNA-dependent RNA polymerase Ki = 0.053 nM 10.28 Binding affinity to Hepatitis C virus genotype 2a NS5B polymerase assessed as in... 38179950
Non-structural protein 4b Ki = 0.063 nM 10.2 Binding affinity to Hepatitis C virus genotype 1b NS4B assessed as inhibition co... 38179950
Non-structural protein 4b Ki = 0.075 nM 10.12 Binding affinity to Hepatitis C virus genotype 1a NS4B assessed as inhibition co... 38179950
Non-structural protein 4b Ki = 0.092 nM 10.04 Binding affinity to Hepatitis C virus genotype 4a NS4B assessed as inhibition co... 38179950
Non-structural protein 4b Ki = 0.11 nM 9.96 Binding affinity to Hepatitis C virus genotype 6a NS4B assessed as inhibition co... 38179950
Hepatitis C virus EC50 = 0.2 nM 9.7 Antiviral activity against HCV genotype 1b harboring D168A mutant infected in hu... 34405680
Hepatitis C virus EC50 = 0.2 nM 9.7 Antiviral activity against HCV genotype 1b infected in human Huh7 cells incubate... 34405680
Hepatitis C virus EC50 = 0.24 nM 9.62 Antiviral activity against HCV assessed as inhibition of RNA replication 38179950
Hepatitis C virus serine protease, NS3/NS4A Ki = 0.5 nM 9.3 Inhibition of HCV GT-3a NS3/4a protease using Ac-DE-D(Edans)-EE-Abu-c-[COO]-AS-K... 34405680
Non-structural protein 4b Ki = 0.92 nM 9.04 Binding affinity to Hepatitis C virus genotype 4a NS4B assessed as inhibition co... 38179950
Non-structural protein 4b Ki = 0.96 nM 9.02 Binding affinity to Hepatitis C virus genotype 3a NS4B assessed as inhibition co... 38179950
Non-structural protein 4b IC50 = 3.8 nM 8.42 Inhibition of Hepatitis C virus genotype 2b NS4B 38179950
Non-structural protein 4b IC50 = 4.4 nM 8.36 Inhibition of Hepatitis C virus genotype 1a NS4B 38179950
Non-structural protein 4b IC50 = 6.1 nM 8.21 Inhibition of Hepatitis C virus genotype 4a NS4B 38179950
Non-structural protein 4b IC50 = 8.1 nM 8.09 Inhibition of Hepatitis C virus genotype 5a NS4B 38179950
Non-structural protein 4b IC50 = 8.9 nM 8.05 Inhibition of Hepatitis C virus genotype 1b NS4B 38179950
Non-structural protein 4b IC50 = 11.3 nM 7.95 Inhibition of Hepatitis C virus genotype 6a NS4B 38179950
Hepatitis C virus EC50 = 30.0 nM 7.52 Antiviral activity against HCV genotype 3a infected in human Huh7.5 cells incuba... 34405680
Unchecked Ki = 90.0 nM 7.05 Inhibition of HCV NS3/4a protease D168A mutant using Ac-DE-D(Edans)-EE-Abu-c-[CO... 34405680

Literature References

PubMed DOI Target Context # Activities
38179950 10.1021/acs.jmedchem.3c01971 Non-structural protein 4b 13
38179950 10.1021/acs.jmedchem.3c01971 ADMET 5
32881503 10.1021/acs.jmedchem.0c00956 No relevant target 4
34405680 10.1021/acs.jmedchem.1c00554 Hepatitis C virus 4
30685524 10.1016/j.ejmech.2019.01.025 ADMET 3
32881503 10.1021/acs.jmedchem.0c00956 ADMET 3
34405680 10.1021/acs.jmedchem.1c00554 Hepatitis C virus serine protease, NS3/NS4A 2
30685524 10.1016/j.ejmech.2019.01.025 Hepatitis C virus serine protease, NS3/NS4A 1
34405680 10.1021/acs.jmedchem.1c00554 Unchecked 1
38179950 10.1021/acs.jmedchem.3c01971 Hepatitis C virus NS5B RNA-dependent RNA polymerase 1
38179950 10.1021/acs.jmedchem.3c01971 Hepatitis C virus 1

Data from ChEMBL 36 via Core Engine