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Compound Detail

CHEMBL2063090

GRAZOPREVIR ANHYDROUS
💊 Approved Drug
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💊 Approved Drug
C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@H](C(C)(C)C)NC(=O)O[C@@H]1C[C@H]1CCCCCc1nc3ccc(OC)cc3nc1O2)C(=O)NS(=O)(=O)C1CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2063090
Name GRAZOPREVIR ANHYDROUS
Phase Approved
Structure Type MOL
InChI Key OBMNJSNZOWALQB-NCQNOWPTSA-N
Therapeutic ✓ Yes

Known Names

Grazoprevir anhydrous Grazoprevir anhydrous component of zepatier MK-5172 MK-5172 ANHYDROUS
6
Targets
72
Activities
3
Assay Types
4
PK Parameters
20
Publications
4
Known Names
2
Indications
1
Mechanisms

Molecular Properties

766.9
MW (Da)
3.30
ALogP
11
HBA
3
HBD
195.2
PSA (Ų)
0.35
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2016
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -vir
USAN Year 2013

Extended Properties

Molecular Formula C38H50N6O9S
MW 766.92
Aromatic Rings 2
Heavy Atoms 54
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 Hepatitis C

Activity Summary

IC50 32 meas. best 11.0
Ki 23 meas. best 10.7
EC50 17 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 IC50 11.0 10.0713 0.0 8
Unchecked
CHEMBL612545
 IC50 11.0 9.4879 0.0 14
Unchecked
CHEMBL612545
 Ki 10.7 9.0533 0.0 3
NS3
CHEMBL1293269
 Ki 10.4 9.585 0.0 14
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 Ki 10.15 9.1233 0.1 3
NS3 protease
CHEMBL4296325
 IC50 10.15 9.05 0.1 4
Genome polyprotein
CHEMBL4296298
 Ki 9.85 8.6833 0.1 3
Hepatitis C virus
CHEMBL379
 EC50 9.7 8.4747 0.2 17
Hepatitis C virus
CHEMBL379
 IC50 8.15 8.14 7.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 536.84 ng.hr.mL-1 Rattus norvegicus
F 13.0 % Canis lupus familiaris
F 1.0 % Rattus norvegicus
T1/2 31.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus serine protease, NS3/NS4A IC50 = 0.01 nM 11.0 Inhibition of Hepatitis C virus NS3-4A protease genotype 1a 37922830
Hepatitis C virus serine protease, NS3/NS4A IC50 = 0.01 nM 11.0 Inhibition of Hepatitis C virus NS3-4A protease genotype 1b 37922830
Unchecked IC50 = 0.01 nM 11.0 Inhibition of HCV genotype 1b NS3/4A protease assessed as substrate cleavage usi... 27994759
Unchecked Ki = 0.02 nM 10.7 Inhibition of Hepatitis C virus (isolate BK) genotype 1b NS3/4a protease express... 24900473
Unchecked IC50 = 0.02 nM 10.7 Inhibition of HCV genotype 1a NS3/4A protease assessed as substrate cleavage usi... 27994759
Unchecked IC50 = 0.02 nM 10.7 Inhibition of Hepatitis C virus genotype 1b NS3/4A protease assessed as substrat... 24900818
Hepatitis C virus serine protease, NS3/NS4A IC50 = 0.021 nM 10.68 Inhibition of HCV genotype 1b NS3/4A protease R155K mutant using Ac-C(Eu)DDMEEAb... 26819676
NS3 Ki = 0.04 nM 10.4 Inhibition of HCV subtype 1b NS3 protease D168E mutant pre-incubated for 30 mins... -
NS3 Ki = 0.05 nM 10.3 Inhibition of HCV subtype 1b NS3 protease A156S mutant pre-incubated for 30 mins... -
Hepatitis C virus serine protease, NS3/NS4A IC50 = 0.06 nM 10.22 Inhibition of HCV genotype 1b NS3/4A protease R155K mutant assessed as substrate... 27994759
Unchecked IC50 = 0.062 nM 10.21 Inhibition of Hepatitis C virus NS3-4 protease genotype 4 37922830
NS3 protease IC50 = 0.07 nM 10.15 Inhibition of Hepatitis C virus genotype 1b NS3/4A protease R155K mutant assesse... 24900818
NS3 Ki = 0.07 nM 10.15 Inhibition of HCV subtype 1b NS3 protease R155K mutant pre-incubated for 30 mins... -
Hepatitis C virus serine protease, NS3/NS4A Ki = 0.07 nM 10.15 Inhibition of Hepatitis C virus (isolate BK) genotype 1b NS3/4a protease R155K m... 24900473
Hepatitis C virus serine protease, NS3/NS4A IC50 = 0.08 nM 10.1 Inhibition of Hepatitis C virus NS3-4A protease genotype 2a 37922830
NS3 Ki = 0.08 nM 10.1 Inhibition of HCV subtype 1b NS3 protease D168G mutant pre-incubated for 30 mins... -
Unchecked IC50 = 0.105 nM 9.98 Inhibition of HCV genotype 1b NS3/4A protease D168Y mutant using Ac-C(Eu)DDMEEAb... 26819676
NS3 Ki = 0.12 nM 9.92 Inhibition of HCV subtype 1b NS3 protease D168Q mutant pre-incubated for 30 mins... -
NS3 Ki = 0.13 nM 9.89 Inhibition of HCV subtype 1b NS3 protease R155N mutant pre-incubated for 30 mins... -
Unchecked IC50 = 0.14 nM 9.85 Inhibition of HCV genotype 2a NS3/4A protease assessed as substrate cleavage usi... 27994759

Literature References

PubMed DOI Target Context # Activities
27994759 10.1021/acsmedchemlett.6b00321 Unchecked 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
26819676 10.1021/acsmedchemlett.5b00425 Unchecked 6
27994759 10.1021/acsmedchemlett.6b00321 Hepatitis C virus 5
37922830 10.1016/j.ejmech.2023.115919 Hepatitis C virus serine protease, NS3/NS4A 5
26819676 10.1021/acsmedchemlett.5b00425 Hepatitis C virus 5
34405680 10.1021/acs.jmedchem.1c00554 Hepatitis C virus 4
24900818 10.1021/ml400466p NS3 protease 4
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
24900473 10.1021/ml300017p Genome polyprotein 3
30685524 10.1016/j.ejmech.2019.01.025 ADMET 3
37922830 10.1016/j.ejmech.2023.115919 Unchecked 3
24900818 10.1021/ml400466p Unchecked 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
24900473 10.1021/ml300017p Unchecked 2
24900818 10.1021/ml400466p Hepatitis C virus 2
34405680 10.1021/acs.jmedchem.1c00554 Hepatitis C virus serine protease, NS3/NS4A 2
24900473 10.1021/ml300017p Hepatitis C virus 2
24900473 10.1021/ml300017p Hepatitis C virus serine protease, NS3/NS4A 1

Data from ChEMBL 36 via Core Engine