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Compound Detail

CHEMBL2374220

LEDIPASVIR
💊 Approved Drug
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💊 Approved Drug
COC(=O)N[C@H](C(=O)N1CC2(CC2)C[C@H]1c1nc(-c2ccc3c(c2)C(F)(F)c2cc(-c4ccc5[nH]c([C@@H]6[C@H]7CC[C@H](C7)N6C(=O)[C@@H](NC(=O)OC)C(C)C)nc5c4)ccc2-3)c[nH]1)C(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2374220
Name LEDIPASVIR
Phase Approved
Structure Type MOL
InChI Key VRTWBAAJJOHBQU-KMWAZVGDSA-N
Therapeutic ✓ Yes

Known Names

GS-5885 Ledipasvir Ledipasvir acetonate Ledipasvir component of harvoni
2
Targets
36
Activities
2
Assay Types
30
PK Parameters
20
Publications
4
Known Names
6
Indications
1
Mechanisms

Molecular Properties

889.0
MW (Da)
8.61
ALogP
8
HBA
4
HBD
174.6
PSA (Ų)
0.11
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

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

Routes of Administration

Oral

Flags

First in Class
USAN Stem -vir
USAN Year 2012

Extended Properties

Molecular Formula C49H54F2N8O6
MW 889.02
Aromatic Rings 5
Heavy Atoms 65
NP-Likeness -0.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Nonstructural protein 5A inhibitor INHIBITOR Nonstructural protein 5A ✓ ✓

Indications

Hepatitis C Hepatitis C, Chronic Infections Severe Acute Respiratory Syndrome Hepatitis B, Chronic Lymphoma

Activity Summary

EC50 34 meas. best 10.57
IC50 2 meas. best 7.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 EC50 10.57 10.202 0.0 5
Nonstructural protein 5A
CHEMBL3307224
 EC50 10.51 7.5923 0.0 26
Nonstructural protein 5A
CHEMBL3307224
 IC50 7.68 7.535 21.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 7697.14 ng.hr.mL-1 Homo sapiens
AUC 6265.81 ng.hr.mL-1 Homo sapiens
AUC 4710.92 ng.hr.mL-1 Homo sapiens
AUC 3562.3 ng.hr.mL-1 Homo sapiens
AUC 2415.47 ng.hr.mL-1 Homo sapiens
AUC 1987.85 ng.hr.mL-1 Homo sapiens
AUC 617.87 ng.hr.mL-1 Homo sapiens
AUC 496.07 ng.hr.mL-1 Homo sapiens
AUC 217.81 ng.hr.mL-1 Homo sapiens
AUC 124.46 ng.hr.mL-1 Homo sapiens
CL 2.833 mL.min-1.kg-1 Macaca fascicularis
CL 2.167 mL.min-1.kg-1 Canis lupus familiaris
CL 7.167 mL.min-1.kg-1 Rattus norvegicus
Cmax 242.0 nM Homo sapiens
Cmax 133.0 nM Homo sapiens
Cmax 82.2 nM Homo sapiens
Cmax 21.3 nM Homo sapiens
Cmax 6.75 nM Homo sapiens
F 53.0 % Canis lupus familiaris
F 41.1 % Macaca fascicularis
F 32.5 % Rattus norvegicus
F 76.0 % Homo sapiens
MRT 12.9 hr Macaca fascicularis
MRT 9.2 hr Canis lupus familiaris
MRT 6.19 hr Rattus norvegicus
T1/2 39.5 hr Homo sapiens
T1/2 44.2 hr Homo sapiens
T1/2 37.2 hr Homo sapiens
T1/2 42.4 hr Homo sapiens
T1/2 45.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus EC50 = 0.027 nM 10.57 Antiviral activity against HCV genotype 1b Con1 infected in human HuH7 cells ass... 24320933
Hepatitis C virus EC50 = 0.027 nM 10.57 Antiviral activity against HCV genotype 1b Con1 infected in human HuH7 cells ass... 24320933
Hepatitis C virus EC50 = 0.031 nM 10.51 Antiviral activity against HCV genotype 1a H77 infected in human HuH7 cells asse... 24320933
Nonstructural protein 5A EC50 = 0.031 nM 10.51 Inhibition of NS5A in HCV genotype 1a H77 infected in human HuH7 replicon cells ... 31230974
Nonstructural protein 5A EC50 = 0.031 nM 10.51 Inhibition of NS5A in wild type HCV genotype 1a infected in human HuH7 replicon ... 31230974
Nonstructural protein 5A EC50 = 0.15 nM 9.82 Inhibition of NS5A in HCV genotype 5a SA13 infected in human HuH7 replicon cells... 31230974
Hepatitis C virus EC50 = 0.21 nM 9.68 Antiviral activity against HCV genotype 1a H77 infected in human HuH7 cells asse... 24320933
Hepatitis C virus EC50 = 0.21 nM 9.68 Antiviral activity against HCV genotype 1a H77 infected in human HuH7 cells asse... 24320933
Nonstructural protein 5A EC50 = 0.39 nM 9.41 Inhibition of NS5A in HCV genotype 4a ED43 infected in human HuH7 replicon cells... 31230974
Nonstructural protein 5A EC50 = 1.1 nM 8.96 Inhibition of NS5A in HCV genotype 6a HK6 infected in human HuH7 replicon cells ... 31230974
Nonstructural protein 5A EC50 = 1.9 nM 8.72 Inhibition of NS5A M28T mutant in HCV genotype 1a infected in human HuH7 replico... 31230974
Nonstructural protein 5A EC50 = 5.7 nM 8.24 Inhibition of NS5A Q30H mutant in HCV genotype 1a infected in human HuH7 replico... 31230974
Nonstructural protein 5A EC50 = 7.2 nM 8.14 Inhibition of NS5A Y93H mutant in HCV genotype 1b infected in human HuH7 replico... 31230974
Nonstructural protein 5A EC50 = 17.0 nM 7.77 Inhibition of NS5A L31M mutant in HCV genotype 1a infected in human HuH7 replico... 31230974
Nonstructural protein 5A EC50 = 19.6 nM 7.71 Inhibition of NS5A Q30R mutant in HCV genotype 1a infected in human HuH7 replico... 31230974
Nonstructural protein 5A EC50 = 21.0 nM 7.68 Inhibition of NS5A in HCV genotype 2a JFH1 infected in human HuH7 replicon cells... 31230974
Nonstructural protein 5A IC50 = 21.0 nM 7.68 Inhibition of NS5A in HCV genotype 2a JFH-1 by cell based luciferase reporter ge... 31710479
Nonstructural protein 5A IC50 = 41.0 nM 7.39 Inhibition of NS5A in HCV genotype 3a by cell based luciferase reporter gene ass... 31710479
Nonstructural protein 5A EC50 = 49.6 nM 7.3 Inhibition of NS5A Y93C mutant in HCV genotype 1a infected in human HuH7 replico... 31230974
Nonstructural protein 5A EC50 = 52.0 nM 7.28 Inhibition of NS5A Y93H mutant in HCV genotype 1a infected in human HuH7 replico... 31230974

Literature References

PubMed DOI Target Context # Activities
31230974 10.1016/j.bmcl.2019.04.027 Nonstructural protein 5A 31
24320933 10.1021/jm401499g Homo sapiens 25
24320933 10.1021/jm401499g Hepatitis C virus 10
24320933 10.1021/jm401499g Rattus norvegicus 6
24320933 10.1021/jm401499g Canis familiaris 6
24320933 10.1021/jm401499g Plasma 5
24320933 10.1021/jm401499g Cynomolgus monkey 5
24320933 10.1021/jm401499g NON-PROTEIN TARGET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
24320933 10.1021/jm401499g Liver microsome 3
30685524 10.1016/j.ejmech.2019.01.025 ADMET 3
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
31710479 10.1021/acs.jmedchem.9b01562 Nonstructural protein 5A 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
- 10.1101/2020.04.21.054387 SARS-CoV-2 1

Data from ChEMBL 36 via Core Engine