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Compound Detail

CHEMBL490672

FILIBUVIR
🧪 Phase III
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🧪 Phase III
CCc1cc(CC[C@]2(C3CCCC3)CC(O)=C(Cc3nc4nc(C)cc(C)n4n3)C(=O)O2)cc(CC)n1

Basic Information

ChEMBL ID CHEMBL490672
Name FILIBUVIR
Phase Phase III
Structure Type MOL
InChI Key SLVAPEZTBDBAPI-GDLZYMKVSA-N

Known Names

Filibuvir PF-00868554 PF-868554
3
Targets
27
Activities
2
Assay Types
12
PK Parameters
20
Publications
3
Known Names
2
Indications
1
Mechanisms

Molecular Properties

503.6
MW (Da)
5.12
ALogP
8
HBA
1
HBD
102.5
PSA (Ų)
0.43
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -vir
USAN Year 2008

Extended Properties

Molecular Formula C29H37N5O3
MW 503.65
Aromatic Rings 3
Heavy Atoms 37
NP-Likeness -0.38

Mechanism of Action

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

Indications

Hepatitis C Hepatitis C, Chronic

Activity Summary

EC50 25 meas. best 7.73
IC50 2 meas. best 8.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus NS5B RNA-dependent RNA polymerase
CHEMBL5375
IC50 8.15 8.15 7.0 1
Unchecked
CHEMBL612545
IC50 8.15 8.15 7.0 1
Hepatitis C virus
CHEMBL379
EC50 7.73 7.452 18.7 25

Pharmacokinetic Data

Parameter Value Units Species
CL 27.0 mL.min-1.kg-1 Macaca mulatta
CL 20.0 mL.min-1.kg-1 Rattus norvegicus
CL 21.0 mL.min-1.kg-1 Rattus norvegicus
CL 0.93 mL.min-1.kg-1 Canis lupus familiaris
CL 21.0 mL.min-1.kg-1 Macaca fascicularis
F 75.0 % Rattus norvegicus
F 49.0 % Canis lupus familiaris
T1/2 2.5 hr Rattus norvegicus
T1/2 4.4 hr Canis lupus familiaris
T1/2 2.1 hr Macaca fascicularis
Tmax 0.94 hr Rattus norvegicus
Tmax 1.0 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus NS5B RNA-dependent RNA polymerase IC50 = 7.0 nM 8.15 Inhibition of Hepatitis C virus NS5B polymerase 36708678
Unchecked IC50 = 7.0 nM 8.15 Inhibition of HCV 1b isolate BK NS5B Cdelta21 polymerase 19209845
Hepatitis C virus EC50 = 18.7 nM 7.73 Antiviral activity against Hepatitis C virus 1b RO-8 expressing NS5B assessed as... 24069953
Hepatitis C virus EC50 = 20.8 nM 7.68 Antiviral activity against Hepatitis C virus 1b RO-7 expressing NS5B assessed as... 24069953
Hepatitis C virus EC50 = 21.3 nM 7.67 Antiviral activity against Hepatitis C virus 1b RO-2 expressing NS5B assessed as... 24069953
Hepatitis C virus EC50 = 22.0 nM 7.66 Antiviral activity against Hepatitis C virus 1a RO-35 expressing NS5B assessed a... 24069953
Hepatitis C virus EC50 = 23.5 nM 7.63 Antiviral activity against Hepatitis C virus 1b RO-9 expressing NS5B assessed as... 24069953
Hepatitis C virus EC50 = 25.0 nM 7.6 Antiviral activity against Hepatitis C virus 1a RO-34 expressing NS5B assessed a... 24069953
Hepatitis C virus EC50 = 25.5 nM 7.59 Antiviral activity against Hepatitis C virus 1b RO-4 expressing NS5B assessed as... 24069953
Hepatitis C virus EC50 = 26.0 nM 7.58 Antiviral activity against Hepatitis C virus 1a RO-32 expressing NS5B assessed a... 24069953
Hepatitis C virus EC50 = 28.5 nM 7.54 Antiviral activity against Hepatitis C virus 1b RO-3 expressing NS5B assessed as... 24069953
Hepatitis C virus EC50 = 33.0 nM 7.48 Antiviral activity against Hepatitis C virus genotype 1a infected in human HuH7.... 23768906
Hepatitis C virus EC50 = 34.4 nM 7.46 Antiviral activity against Hepatitis C virus 1a RO-33 expressing NS5B assessed a... 24069953
Hepatitis C virus EC50 = 37.0 nM 7.43 Antiviral activity against Hepatitis C virus 1a RO-24 expressing NS5B assessed a... 24069953
Hepatitis C virus EC50 = 39.3 nM 7.41 Antiviral activity against Hepatitis C virus 1b RO-1 expressing NS5B assessed as... 24069953
Hepatitis C virus EC50 = 38.8 nM 7.41 Antiviral activity against Hepatitis C virus 1a RO-28 expressing NS5B assessed a... 24069953
Hepatitis C virus EC50 = 39.7 nM 7.4 Antiviral activity against Hepatitis C virus 1b RO-10 expressing NS5B assessed a... 24069953
Hepatitis C virus EC50 = 41.0 nM 7.39 Antiviral activity against HCV 1b Con1 isolate in human Huh7.5 cells assessed as... 19209845
Hepatitis C virus EC50 = 41.0 nM 7.39 Antiviral activity against Hepatitis C virus genotype 1b 1389 infected in human ... 22386565
Hepatitis C virus EC50 = 41.0 nM 7.39 Antiviral activity against HCV assessed as reduction in viral growth 36708678

Literature References

PubMed DOI Target Context # Activities
24069953 10.1021/jm401266k Hepatitis C virus 20
19209845 10.1021/jm8014537 Canis familiaris 5
19209845 10.1021/jm8014537 Rattus norvegicus 5
19209845 10.1021/jm8014537 Cynomolgus monkey 3
19209845 10.1021/jm8014537 ADMET 2
23768906 10.1016/j.bmcl.2013.05.037 Hepatitis C virus 2
19209845 10.1021/jm8014537 No relevant target 1
36708678 10.1016/j.ejmech.2023.115136 Hepatitis C virus 1
36708678 10.1016/j.ejmech.2023.115136 Hepatitis C virus NS5B RNA-dependent RNA polymerase 1
24144213 10.1021/jm401420j Hepatitis C virus 1
22386565 10.1016/j.bmc.2012.01.031 Hepatitis C virus 1
19209845 10.1021/jm8014537 Liver microsomes 1
19209845 10.1021/jm8014537 Cytochrome P450 2D6 1
19209845 10.1021/jm8014537 Cytochrome P450 2C19 1
19209845 10.1021/jm8014537 Cytochrome P450 2C9 1
19209845 10.1021/jm8014537 Cytochrome P450 3A4 1
19209845 10.1021/jm8014537 Cytochrome P450 2C8 1
19209845 10.1021/jm8014537 Cytochrome P450 1A2 1
19209845 10.1021/jm8014537 Hepatocyte 1
19209845 10.1021/jm8014537 Hepatitis C virus 1

Data from ChEMBL 36 via Core Engine