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Compound Detail

CHEMBL1092581

NESBUVIR
🧪 Phase II
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🧪 Phase II
CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N(CCO)S(C)(=O)=O)c(C3CC3)cc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1092581
Name NESBUVIR
Phase Phase II
Structure Type MOL
InChI Key WTDWVLJJJOTABN-UHFFFAOYSA-N

Known Names

Hcv 796 HCV-796 HCV796 Nesbuvir
4
Targets
70
Activities
2
Assay Types
5
PK Parameters
20
Publications
4
Known Names
1
Indications
1
Mechanisms

Molecular Properties

446.5
MW (Da)
3.23
ALogP
5
HBA
2
HBD
99.8
PSA (Ų)
0.58
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Stem -vir
USAN Year 2007

Extended Properties

Molecular Formula C22H23FN2O5S
MW 446.50
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.68

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
RNA-directed RNA polymerase inhibitor INHIBITOR RNA-directed RNA polymerase ✓ ✓

Indications

Hepatitis C

Activity Summary

EC50 58 meas. best 8.62
IC50 12 meas. best 9.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 IC50 9.1 7.1233 0.8 9
Hepatitis C virus
CHEMBL379
 EC50 8.62 7.2088 2.4 51
Nonstructural protein 5A
CHEMBL3307224
 EC50 8.3 7.96 5.0 2
RNA-directed RNA polymerase
CHEMBL4296320
 EC50 8.05 7.702 9.0 5
Unchecked
CHEMBL612545
 IC50 8.0 7.7 10.0 2
RNA-directed RNA polymerase
CHEMBL4296320
 IC50 6.8 6.8 160.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1610.0 ng.hr.mL-1 Rattus norvegicus
CL 10.4 mg/ml/kg Rattus norvegicus
F 73.0 % Rattus norvegicus
T1/2 1.7 hr Hepatitis C virus subtype 1b
T1/2 2.73 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus IC50 = 0.8 nM 9.1 Inhibition of Hepatitis C virus con1 NS5B RNA-dependent RNA polymerase 22516671
Hepatitis C virus EC50 = 2.4 nM 8.62 Antiviral activity against Hepatitis C virus genotype 1b Con1 infected in human ... 18936191
Hepatitis C virus EC50 = 3.2 nM 8.49 Antiviral activity against Hepatitis C virus isolate Con1 transfected with NS5B ... 18694956
Hepatitis C virus EC50 = 4.0 nM 8.4 Antiviral activity against Hepatitis C virus GT-1a harboring wild type NS5B poly... 19273674
Hepatitis C virus EC50 = 4.0 nM 8.4 Antiviral activity against Hepatitis C virus genotype 1b infected in human Huh-M... 18625766
Hepatitis C virus EC50 = 5.0 nM 8.3 Antiviral activity against Hepatitis C virus genotype 1a assessed as inhibition ... 22516671
Nonstructural protein 5A EC50 = 5.0 nM 8.3 Inhibition of HCV genotype 1a NS5A polymerase L31V/Y93H double mutant infected i... 29422387
Hepatitis C virus EC50 = 6.0 nM 8.22 Antiviral activity against Hepatitis C virus GT-1b harboring wild type NS5B poly... 19273674
Hepatitis C virus EC50 = 6.0 nM 8.22 Antiviral activity against Hepatitis C virus GT-1b harboring NS5B polymerase C31... 19273674
Hepatitis C virus EC50 = 7.0 nM 8.15 Antiviral activity against Hepatitis C virus GT-1a harboring NS5B polymerase M41... 19273674
Hepatitis C virus EC50 = 8.0 nM 8.1 Antiviral activity against Hepatitis C virus GT-1a harboring NS5B polymerase L39... 19273674
Hepatitis C virus EC50 = 9.0 nM 8.05 Antiviral activity against Hepatitis C virus genotype 1b Con1 harboring NS3 V158... 18936191
RNA-directed RNA polymerase EC50 = 9.0 nM 8.05 Inhibition of NS5B polymerase in HCV genotype 1b infected human HuH7 replicon ce... 29422387
Hepatitis C virus EC50 = 9.0 nM 8.05 Antiviral activity against Hepatitis C virus genotype 1b assessed as inhibition ... 22516671
Unchecked IC50 = 10.0 nM 8.0 Inhibition of Hepatitis C virus genotype 1 NS5B RNA-dependent RNA polymerase 22516671
RNA-directed RNA polymerase EC50 = 12.0 nM 7.92 Inhibition of HCV genotype 1b NS5B polymerase infected in human HuH7 replicon ce... 29422387
Hepatitis C virus EC50 = 13.0 nM 7.89 Antiviral activity against Hepatitis C virus genotype 1b Con1 harboring NS5B I42... 18936191
Hepatitis C virus EC50 = 13.0 nM 7.89 Antiviral activity against Hepatitis C virus genotype 1b Con1 harboring NS3 V170... 18936191
Hepatitis C virus EC50 = 14.0 nM 7.85 Antiviral activity against Hepatitis C virus genotype 1b Con1 infected in human ... 18936191
Hepatitis C virus EC50 = 15.0 nM 7.82 Antiviral activity against Hepatitis C virus genotype 1b Con1 harboring NS3 K583... 18936191

Literature References

PubMed DOI Target Context # Activities
18936191 10.1128/aac.01081-08 Hepatitis C virus 26
18694956 10.1128/aac.00533-08 Hepatitis C virus 16
19273674 10.1128/aac.01598-08 Hepatitis C virus 11
24900232 10.1021/ml100128h Hepatitis C virus 7
23672667 10.1021/jm400317w Hepatitis C virus 7
20219368 10.1016/j.bmcl.2010.02.054 Hepatitis C virus 5
29422387 10.1016/j.bmcl.2018.01.029 Rattus norvegicus 5
29422387 10.1016/j.bmcl.2018.01.029 RNA-directed RNA polymerase 5
24900232 10.1021/ml100128h Unchecked 5
18285474 10.1128/aac.01317-07 Hepatitis C virus 4
18625766 10.1128/aac.01534-07 Hepatitis C virus 4
18625766 10.1128/aac.01534-07 ADMET 4
22516671 10.1016/j.bmc.2012.03.049 Hepatitis C virus 4
29422387 10.1016/j.bmcl.2018.01.029 Nonstructural protein 5A 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
23672667 10.1021/jm400317w RNA-directed RNA polymerase 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
29422387 10.1016/j.bmcl.2018.01.029 ADMET 2
20516274 10.1128/aac.00289-10 Hepatitis C virus 2
35868125 10.1016/j.ejmech.2022.114595 Hepatitis C virus 2

Data from ChEMBL 36 via Core Engine