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Compound Detail

CHEMBL1259059

SOFOSBUVIR
💊 Approved Drug
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💊 Approved Drug
CC(C)OC(=O)[C@H](C)N[P@](=O)(OC[C@H]1O[C@@H](n2ccc(=O)[nH]c2=O)[C@](C)(F)[C@@H]1O)Oc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1259059
Name SOFOSBUVIR
Phase Approved
Structure Type MOL
InChI Key TTZHDVOVKQGIBA-IQWMDFIBSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL486231

Known Names

GS-7977 GS7977 PSI-7977 Psi-7977, gs-7977 Sofosbuvir Sofosbuvir component of epclusa Sofosbuvir component of harvoni Sofosbuvir component of vosevi Sovaldi
14
Targets
80
Activities
3
Assay Types
16
PK Parameters
20
Publications
9
Known Names
8
Indications
1
Mechanisms

Molecular Properties

529.5
MW (Da)
1.66
ALogP
10
HBA
3
HBD
158.2
PSA (Ų)
0.31
QED
1
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2013
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning First in Class Prodrug
USAN Stem -fos-; -vir
USAN Year 2012

Extended Properties

Molecular Formula C22H29FN3O9P
MW 529.46
Aromatic Rings 2
Heavy Atoms 36
NP-Likeness 0.24

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 Virus Diseases Infections Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Hepatitis B, Chronic Lymphoma

ATC Classification

J05AP08
sofosbuvir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

EC50 57 meas. best 7.53
IC50 21 meas. best 7.7
Ki 2 meas. best 4.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 IC50 7.7 7.235 20.0 8
Hepatitis C virus
CHEMBL379
 EC50 7.53 6.8653 29.4 36
RNA-directed RNA polymerase
CHEMBL4296320
 EC50 7.47 7.0183 34.0 12
NS5
CHEMBL4523952
 EC50 6.92 5.715 120.0 2
Unchecked
CHEMBL612545
 EC50 6.82 6.82 150.0 1
dengue virus type 2
CHEMBL613966
 EC50 6.4 5.8767 400.0 3
West Nile virus
CHEMBL613730
 IC50 5.92 5.845 1200.0 2
Zika virus
CHEMBL4296612
 IC50 5.7 5.59 2000.0 3
dengue virus type 2
CHEMBL613966
 IC50 5.42 5.3775 3800.0 4
Yellow fever virus
CHEMBL613731
 EC50 5.38 5.38 4200.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 5.14 5.14 7300.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.08 5.08 8400.0 1
Nonstructural protein 5
CHEMBL4295629
 IC50 4.83 4.83 14700.0 1
Cereblon isoform 4
CHEMBL3763007
 Ki 4.66 4.615 22000.0 2
HepG2
CHEMBL395
 IC50 4.35 4.35 45000.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.22 4.22 60000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 0.238 L/min Homo sapiens
CL 40.0 mL.min-1.kg-1 Canis lupus familiaris
CL 71.67 mL.min-1.kg-1 Homo sapiens
CL 71.67 mL.min-1.kg-1 Homo sapiens
F 9.9 % Canis lupus familiaris
F 92.0 % Homo sapiens
Fu 0.323 - Canis lupus familiaris
Fu 0.563 - Homo sapiens
T1/2 0.8017 hr Homo sapiens
T1/2 3.85 hr Homo sapiens
T1/2 28.2 hr Homo sapiens
T1/2 15.3 hr Homo sapiens
T1/2 0.4 hr Homo sapiens
T1/2 2.0 hr Homo sapiens
Tmax 0.5 hr Homo sapiens
Tmax 12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus IC50 = 20.0 nM 7.7 Antiviral activity against HCV genotype 2a/k infected in human HuH7 cells assess... 28595015
Hepatitis C virus IC50 = 28.0 nM 7.55 Antiviral activity against HCV infected in human Huh7-J17 cells assessed as inhi... 28601004
Hepatitis C virus EC50 = 29.4 nM 7.53 Antiviral activity against wild type HCV by qRT-PCR analysis based by Reed-Muenc... 32378892
Hepatitis C virus EC50 = 30.0 nM 7.52 Antiviral activity against HCV by replicon assay 35123007
Hepatitis C virus EC50 = 30.0 nM 7.52 Antiviral activity against HCV subtype 1b infected in human HuH-7-Luc/Neo-ET cel... 32919013
RNA-directed RNA polymerase EC50 = 34.0 nM 7.47 Inhibition of NS5B polymerase in wild type HCV genotype 1b infected in human Huh... 30653317
Hepatitis C virus IC50 = 40.0 nM 7.4 Antiviral activity against HCV genotype 2b infected in human HuH7 cells assessed... 28595015
RNA-directed RNA polymerase EC50 = 43.0 nM 7.37 Inhibition of NS5B polymerase in HCV genotype 2a infected in human HuH7 replicon... 30653317
RNA-directed RNA polymerase EC50 = 44.0 nM 7.36 Inhibition of NS5B polymerase in HCV genotype 1b/5a chimeric replicon infected i... 30653317
Hepatitis C virus EC50 = 46.0 nM 7.34 Antiviral activity against HCV J6/JFH/JC1 infected in human Huh7.5 cells assesse... 32378892
Hepatitis C virus EC50 = 50.0 nM 7.3 Antiviral activity against HCV genotype 1b subgenomic replicon infected in human... 30655167
Hepatitis C virus EC50 = 53.0 nM 7.28 Antiviral activity against HCV genotype 1b Con1 over expressing CES1 infected in... 31740203
RNA-directed RNA polymerase EC50 = 58.0 nM 7.24 Inhibition of NS5B polymerase in HCV genotype 1b/4a chimeric replicon infected i... 30653317
Hepatitis C virus IC50 = 60.0 nM 7.22 Antiviral activity against HCV genotype 1a infected in human HuH7 cells assessed... 28595015
Hepatitis C virus IC50 = 60.0 nM 7.22 Antiviral activity against HCV genotype 1b infected in human HuH7 cells assessed... 28595015
RNA-directed RNA polymerase EC50 = 61.0 nM 7.21 Inhibition of NS5B polymerase in HCV genotype 1a infected in human HuH7 replicon... 30653317
Hepatitis C virus EC50 = 62.0 nM 7.21 Antiviral activity against HCV genotype 1b Con1 expressing wild type NS5B infect... 31740203
RNA-directed RNA polymerase EC50 = 64.0 nM 7.19 Inhibition of NS5B polymerase in HCV genotype 1b/3a chimeric replicon infected i... 30653317
RNA-directed RNA polymerase EC50 = 64.26 nM 7.19 Inhibition of Hepatitis C virus genotype 1b NS5B RNA-dependent-RNA polymerase as... 29681484
Hepatitis C virus EC50 = 64.0 nM 7.19 Antiviral activity against wild-type HCV J6/JFH/JC1 infected in human Huh7.5 cel... 27783522

Literature References

PubMed DOI Target Context # Activities
30653317 10.1021/acs.jmedchem.8b01300 RNA-directed RNA polymerase 14
30653317 10.1021/acs.jmedchem.8b01300 Unchecked 12
28595015 10.1021/acs.jmedchem.7b00067 Hepatitis C virus 12
28595015 10.1021/acs.jmedchem.7b00067 HepG2 11
31740203 10.1016/j.bmc.2019.115208 Hepatitis C virus 11
30653317 10.1021/acs.jmedchem.8b01300 HepG2 8
31740203 10.1016/j.bmc.2019.115208 ADMET 8
20845908 10.1021/jm100863x Hepatitis C virus 8
34273661 10.1016/j.ejmech.2021.113683 ADMET 8
28601004 10.1016/j.ejmech.2017.05.051 Unchecked 5
35050619 10.1021/acs.jmedchem.1c01637 Hepatitis C virus 4
34273661 10.1016/j.ejmech.2021.113683 Unchecked 4
27181575 10.1021/acs.jmedchem.6b00382 Hepatitis C virus 4
32046903 10.1016/j.bmcl.2020.126986 ADMET 4
32378892 10.1021/acs.jmedchem.0c00232 Hepatitis C virus 4
34273661 10.1016/j.ejmech.2021.113683 Zika virus 3
32378892 10.1021/acs.jmedchem.0c00232 Unchecked 3
24345201 10.1021/jm4015422 Hepatitis C virus 3
30653317 10.1021/acs.jmedchem.8b01300 ADMET 3
34273661 10.1016/j.ejmech.2021.113683 dengue virus type 2 3

Data from ChEMBL 36 via Core Engine