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Compound Detail

CHEMBL1241348

FALDAPREVIR
🧪 Phase III
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🧪 Phase III
C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H](Oc2cc(-c3csc(NC(=O)C(C)C)n3)nc3c(Br)c(OC)ccc23)CN1C(=O)[C@@H](NC(=O)OC1CCCC1)C(C)(C)C)C(=O)O

Basic Information

ChEMBL ID CHEMBL1241348
Name FALDAPREVIR
Phase Phase III
Structure Type MOL
InChI Key LLGDPTDZOVKFDU-XUHJSTDZSA-N

Known Names

BI 201335 BI-201335 BI201335 Faldaprevir
8
Targets
32
Activities
3
Assay Types
23
PK Parameters
20
Publications
4
Known Names
5
Indications
1
Mechanisms

Molecular Properties

869.8
MW (Da)
6.30
ALogP
11
HBA
4
HBD
198.4
PSA (Ų)
0.14
QED
3
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -vir
USAN Year 2012

Extended Properties

Molecular Formula C40H49BrN6O9S
MW 869.84
Aromatic Rings 3
Heavy Atoms 57
NP-Likeness -0.10

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

Hepatitis C Hepatitis C, Chronic Virus Diseases HIV Infections Renal Insufficiency

ATC Classification

J05AP04
faldaprevir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 14 meas. best 8.52
Ki 12 meas. best 9.01
IC50 6 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Non-structural protein 4b
CHEMBL6066153
Ki 9.01 9.01 1.0 1
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
Ki 8.92 8.735 1.2 2
Unchecked
CHEMBL612545
Ki 8.92 8.0675 1.2 8
Hepatitis C virus
CHEMBL379
Ki 8.55 8.55 2.8 1
Hepatitis C virus
CHEMBL379
EC50 8.52 7.7657 3.0 14
Non-structural protein 4b
CHEMBL6066153
IC50 8.52 8.52 3.0 1
Unchecked
CHEMBL612545
IC50 8.52 8.52 3.0 1
Sterol O-acyltransferase 2
CHEMBL2856
IC50 5.62 5.62 2400.0 1
Serine/threonine protein phosphatase PP2B-alpha catalytic subunit
CHEMBL5278
IC50 5.05 5.05 9000.0 1
Cathepsin B
CHEMBL4072
IC50 4.58 4.58 26000.0 1
Cathepsin E
CHEMBL1681627
IC50 4.52 4.52 30000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 12177.76 ng.hr.mL-1 Canis lupus familiaris
AUC 7219.67 ng.hr.mL-1 Macaca mulatta
AUC 1417.84 ng.hr.mL-1 Rattus norvegicus
AUC 11307.92 ng.hr.mL-1 Canis lupus familiaris
AUC 7219.67 ng.hr.mL-1 Macaca mulatta
AUC 1348.25 ng.hr.mL-1 Rattus norvegicus
AUC 1348.25 ng.hr.mL-1 Rattus norvegicus
AUC 11307.92 ng.hr.mL-1 Canis lupus familiaris
AUC 34793.6 ng.hr.mL-1 Rattus norvegicus
CL 20.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 3800.0 nM Canis lupus familiaris
Cmax 2000.0 nM Macaca mulatta
Cmax 410.0 nM Rattus norvegicus
Cmax 400.0 nM Rattus norvegicus
F 40.0 % Rattus norvegicus
MRT 2.6 hr Macaca mulatta
MRT 3.7 hr Canis lupus familiaris
MRT 3.18 hr Rattus norvegicus
T1/2 3.217 hr Homo sapiens
T1/2 1.2 hr Rattus norvegicus
Tmax 0.83 hr Canis lupus familiaris
Tmax 2.0 hr Macaca mulatta
Tmax 1.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Non-structural protein 4b Ki = 0.97 nM 9.01 Binding affinity to Hepatitis C virus genotype 1b NS4B assessed as inhibition co... 38179950
Hepatitis C virus serine protease, NS3/NS4A Ki = 1.2 nM 8.92 Inhibition of HCV genotype 1a NS3/4A protease using Ac-DED(Edans)EEAbu-psi[COO]A... 25456385
Unchecked Ki = 1.2 nM 8.92 Inhibition of Hepatitis C virus genotype 1a full length NS3/2K-NS4A protease usi... 24900813
Unchecked Ki = 1.2 nM 8.92 Inhibition of HCV 1a NS3/4A protease 20823284
Unchecked Ki = 1.8 nM 8.74 Inhibition of HCV 4a NS3/4A protease 20823284
Hepatitis C virus Ki = 2.8 nM 8.55 Inhibition of HCV 1b NS3/4A protease 20823284
Hepatitis C virus serine protease, NS3/NS4A Ki = 2.8 nM 8.55 Inhibition of HCV genotype 1b NS3/4A protease 25456385
Non-structural protein 4b IC50 = 3.0 nM 8.52 Inhibition of Hepatitis C virus genotype 1b NS4B 38179950
Unchecked IC50 = 3.0 nM 8.52 Inhibition of HCV NS3 protease 20715823
Hepatitis C virus EC50 = 3.0 nM 8.52 Antiviral activity against HCV Con1 by cell based-luciferase reporter gene assay 20715823
Hepatitis C virus EC50 = 3.1 nM 8.51 Antiviral activity against HCV 1b infected in Huh7 cells assessed as inhibition ... 20823284
Hepatitis C virus EC50 = 3.1 nM 8.51 Antiviral activity against HCV genotype 1b 30639895
Hepatitis C virus EC50 = 3.1 nM 8.51 Antiviral activity against HCV genotype 1b 25456385
Hepatitis C virus EC50 = 3.1 nM 8.51 Antiviral activity against Hepatitis C virus genotype 1b isolate Con1 harboring ... 23506530
Unchecked Ki = 5.8 nM 8.24 Binding affinity to HCV 5a NS3/4A protease 20823284
Unchecked Ki = 6.1 nM 8.21 Inhibition of HCV 6a NS3/4A protease 20823284
Hepatitis C virus EC50 = 6.5 nM 8.19 Antiviral activity against HCV genotype 1a 30639895
Hepatitis C virus EC50 = 6.5 nM 8.19 Antiviral activity against HCV genotype 1a 25456385
Hepatitis C virus EC50 = 6.5 nM 8.19 Antiviral activity against Hepatitis C virus genotype 1b infected in human HuH7 ... 24900813
Hepatitis C virus EC50 = 6.5 nM 8.19 Antiviral activity against Hepatitis C virus genotype 1a isolate H77 harboring w... 23506530

Literature References

PubMed DOI Target Context # Activities
20823284 10.1128/aac.00787-10 Unchecked 28
38179950 10.1021/acs.jmedchem.3c01971 ADMET 8
20823284 10.1128/aac.00787-10 Hepatitis C virus 5
20823284 10.1128/aac.00787-10 Rhesus monkey 5
20823284 10.1128/aac.00787-10 Rattus norvegicus 5
20823284 10.1128/aac.00787-10 Canis familiaris 5
23506530 10.1021/jm400121t Hepatitis C virus 4
20823284 10.1128/aac.00787-10 Neutrophil elastase 3
20823284 10.1128/aac.00787-10 Voltage-gated L-type calcium channel 3
20823284 10.1128/aac.00787-10 Neprilysin 3
25456385 10.1016/j.bmc.2014.10.010 Hepatitis C virus serine protease, NS3/NS4A 2
20823284 10.1128/aac.00787-10 Cathepsin E 2
20823284 10.1128/aac.00787-10 Caco-2 2
20823284 10.1128/aac.00787-10 Cathepsin B 2
20823284 10.1128/aac.00787-10 Liver microsomes 2
20823284 10.1128/aac.00787-10 Sterol O-acyltransferase 2 2
20823284 10.1128/aac.00787-10 Angiotensin-converting enzyme 2
20823284 10.1128/aac.00787-10 Serine/threonine protein phosphatase PP2B-alpha catalytic subunit 2
25456385 10.1016/j.bmc.2014.10.010 Hepatitis C virus 2
20823284 10.1128/aac.00787-10 ADMET 2

Data from ChEMBL 36 via Core Engine