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Compound Detail

CHEMBL2105735

ASUNAPREVIR
💊 Approved Drug
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💊 Approved Drug
C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H](Oc2ncc(OC)c3ccc(Cl)cc23)CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)C(=O)NS(=O)(=O)C1CC1

Basic Information

ChEMBL ID CHEMBL2105735
Name ASUNAPREVIR
Phase Approved
Structure Type MOL
InChI Key XRWSZZJLZRKHHD-WVWIJVSJSA-N

Known Names

Asunaprevir BMS 650032 BMS-650032 BMS650032 Sunvepra
6
Targets
47
Activities
2
Assay Types
30
PK Parameters
20
Publications
5
Known Names
4
Indications
1
Mechanisms

Molecular Properties

748.3
MW (Da)
3.85
ALogP
10
HBA
3
HBD
182.3
PSA (Ų)
0.29
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2014
Availability Unknown
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -vir
USAN Year 2011

Extended Properties

Molecular Formula C35H46ClN5O9S
MW 748.30
Aromatic Rings 2
Heavy Atoms 51
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

Virus Diseases Hepatitis C Hepatitis C, Chronic Infections

ATC Classification

J05AP06
asunaprevir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

IC50 24 meas. best 9.7
EC50 23 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 9.7 8.3262 0.2 13
Hepatitis C virus
CHEMBL379
IC50 9.52 8.34 0.3 8
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
IC50 9.0 9.0 1.0 2
Human immunodeficiency virus type 1 integrase
CHEMBL3471
IC50 9.0 9.0 1.0 1
Hepatitis C virus
CHEMBL379
EC50 9.0 7.9682 1.0 11
NS3
CHEMBL1293269
EC50 8.92 8.66 1.2 2
Unchecked
CHEMBL612545
EC50 8.92 7.2067 1.2 9
Human immunodeficiency virus 1
CHEMBL378
EC50 8.22 8.22 6.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 748.3 ng.hr.mL-1 Rattus norvegicus
AUC 1646.26 ng.hr.mL-1 Canis lupus familiaris
AUC 486.39 ng.hr.mL-1 Macaca fascicularis
AUC 748.3 ng.hr.mL-1 Rattus norvegicus
AUC 897.96 ng.hr.mL-1 Rattus norvegicus
AUC 1646.26 ng.hr.mL-1 Canis lupus familiaris
AUC 486.39 ng.hr.mL-1 Macaca fascicularis
AUC 404.08 ng.hr.mL-1 Mus musculus
AUC 748.3 ng.hr.mL-1 Rattus norvegicus
AUC 1646.26 ng.hr.mL-1 Canis lupus familiaris
AUC 306.8 ng.hr.mL-1 Macaca fascicularis
CL 38.0 mL.min-1.kg-1 Rattus norvegicus
CL 18.7 mL.min-1.kg-1 Canis lupus familiaris
CL 19.5 mL.min-1.kg-1 Macaca fascicularis
CL 38.0 mL.min-1.kg-1 Rattus norvegicus
CL 38.0 mL.min-1.kg-1 Rattus norvegicus
CL 38.0 mL.min-1.kg-1 Rattus norvegicus
CL 18.7 mL.min-1.kg-1 Canis lupus familiaris
CL 19.5 mL.min-1.kg-1 Macaca fascicularis
CL 57.3 ml.min/kg Mus musculus
CL 38.0 ml.min/kg Rattus norvegicus
CL 18.7 ml.min/kg Canis lupus familiaris
CL 18.3 ml.min/kg Macaca fascicularis
F 12.0 % Rattus norvegicus
F 61.0 % Canis lupus familiaris
F 18.0 % Macaca fascicularis
F 12.0 % Rattus norvegicus
F 12.0 % Rattus norvegicus
F 14.0 % Rattus norvegicus
F 61.0 % Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.2 nM 9.7 Inhibition of Hepatitis C virus NS3 protease 37922830
Hepatitis C virus IC50 = 0.3 nM 9.52 Inhibition of HCV genotype 1b 27501244
Unchecked IC50 = 0.4 nM 9.4 Inhibition of recombinant full length HCV genotype 1b J4L6S NS3/4A protease prei... 27564532
Unchecked IC50 = 0.6 nM 9.22 Inhibition of recombinant full length HCV genotype 1a H77 NS3/4A protease preinc... 27564532
Hepatitis C virus IC50 = 0.7 nM 9.15 Inhibition of HCV genotype 1a 27501244
Hepatitis C virus IC50 = 0.9 nM 9.05 Inhibition of HCV genotype 6a 27501244
Hepatitis C virus EC50 = 1.0 nM 9.0 Antiviral activity against HCV 30639895
Unchecked IC50 = 1.0 nM 9.0 Inhibition of HCV genotype 1a NS3 protease using RET S1 as substrate incubated f... 27564532
Hepatitis C virus serine protease, NS3/NS4A IC50 = 1.0 nM 9.0 Inhibition of recombinant full length HCV genotype 1a NS3/4A protease (1027 to 1... 29456803
Hepatitis C virus serine protease, NS3/NS4A IC50 = 1.0 nM 9.0 Inhibition of N-terminal poly-His tagged recombinant HCV genotype 1a NS3/4A prot... 29650290
Unchecked IC50 = 1.0 nM 9.0 Inhibition of HCV NS3/4A protease 31740056
Human immunodeficiency virus type 1 integrase IC50 = 1.0 nM 9.0 Inhibition of HIV-1 integrase 38781921
NS3 EC50 = 1.2 nM 8.92 Inhibition of HCV genotype 1b Con1 NS3 protease infected in human HuH7 replicon ... 29162454
Hepatitis C virus EC50 = 1.2 nM 8.92 Antiviral activity against HCV genotype 1b 27501244
Unchecked EC50 = 1.2 nM 8.92 Inhibition of recombinant full length NS3/4A protease in Hepatitis C virus subty... 33226226
Unchecked IC50 = 1.3 nM 8.89 Inhibition of recombinant full length HCV genotype 6a HK-6A NS3/4A protease prei... 27564532
Hepatitis C virus IC50 = 1.6 nM 8.8 Inhibition of HCV genotype 4a 27501244
Unchecked EC50 = 1.7 nM 8.77 Inhibition of recombinant full length HCV genotype 4a ED43 NS3 protease in genot... 27564532
Hepatitis C virus IC50 = 1.7 nM 8.77 Inhibition of HCV genotype 5a 27501244
Hepatitis C virus EC50 = 1.8 nM 8.74 Antiviral activity against HCV genotype 4a 27501244

Literature References

Data from ChEMBL 36 via Core Engine