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Compound Detail

CHEMBL501849

SIMEPREVIR
💊 Approved Drug
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💊 Approved Drug
COc1ccc2c(O[C@@H]3C[C@H]4C(=O)N[C@]5(C(=O)NS(=O)(=O)C6CC6)C[C@H]5/C=C\CCCCN(C)C(=O)[C@@H]4C3)cc(-c3nc(C(C)C)cs3)nc2c1C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL501849
Name SIMEPREVIR
Phase Approved
Structure Type MOL
InChI Key JTZZSQYMACOLNN-VDWJNHBNSA-N
Therapeutic ✓ Yes

Known Names

Simeprevir TMC 435 TMC 435350 TMC-435 TMC-435350 Tmc435 TMC435350
7
Targets
109
Activities
3
Assay Types
29
PK Parameters
20
Publications
7
Known Names
4
Indications

Molecular Properties

750.0
MW (Da)
5.25
ALogP
10
HBA
2
HBD
156.9
PSA (Ų)
0.29
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

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

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -vir
USAN Year 2010

Extended Properties

Molecular Formula C38H47N5O7S2
MW 749.96
Aromatic Rings 3
Heavy Atoms 52
NP-Likeness -0.12

Indications

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

ATC Classification

J05AP05
simeprevir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 84 meas. best 9.52
Ki 13 meas. best 9.44
IC50 12 meas. best 8.61

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 EC50 9.52 7.29 0.3 82
Hepatitis C virus serine protease, NS3/NS4A
CHEMBL2095231
 Ki 9.44 9.37 0.4 2
Unchecked
CHEMBL612545
 Ki 9.44 9.31 0.4 7
Hepatitis C virus
CHEMBL379
 Ki 9.4 9.3667 0.4 3
NS3
CHEMBL1293269
 Ki 9.3 9.3 0.5 1
Replicase polyprotein 1ab
CHEMBL4523582
 IC50 8.61 6.0375 2.5 4
Unchecked
CHEMBL612545
 EC50 8.09 8.09 8.1 1
Unchecked
CHEMBL612545
 IC50 8.0 7.8557 10.0 7
Cathepsin S
CHEMBL2954
 IC50 6.1 6.1 800.0 1
SARS-CoV
CHEMBL4303836
 EC50 5.85 5.85 1400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3907.29 ng.hr.mL-1 Rattus norvegicus
AUC 2092.39 ng.hr.mL-1 Rattus norvegicus
AUC 7740.0 ng.hr.mL-1 Rattus norvegicus
AUC 1740.0 ng.hr.mL-1 Rattus norvegicus
AUC 1750.0 ng.hr.mL-1 Rattus norvegicus
CL 8.417 mL.min-1.kg-1 Rattus norvegicus
CL 6.0 mL.min-1.g-1 Homo sapiens
CL 38.33 mL.min-1.kg-1 Rattus norvegicus
CL 38.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 730.0 nM Rattus norvegicus
Cmax 1906.77 nM Rattus norvegicus
F 11.0 % Rattus norvegicus
F 44.0 % Rattus norvegicus
F 100.0 % Canis lupus familiaris
F 44.0 % Rattus norvegicus
F 62.0 % Homo sapiens
T1/2 2.8 hr Rattus norvegicus
T1/2 2.6 hr Rattus norvegicus
T1/2 4.0 hr Rattus norvegicus
T1/2 5.1 hr Canis lupus familiaris
T1/2 4.0 hr Rattus norvegicus
T1/2 10.0 hr Homo sapiens
T1/2 41.0 hr Homo sapiens
T1/2 4.1 hr Macaca fascicularis
T1/2 1.5 hr Rattus norvegicus
Tmax 3.0 hr Rattus norvegicus
Tmax 8.0 hr Rattus norvegicus
Tmax 2.0 hr Rattus norvegicus
Vd 5.3 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus EC50 = 0.3 nM 9.52 Antiviral activity against HCV subtype 1b expressing NS3/4A A156S mutant proteas... 23142614
Hepatitis C virus serine protease, NS3/NS4A Ki = 0.36 nM 9.44 Inhibition of HCV genotype 1a NS3/4A protease using Ac-DED(Edans)EEAbu-psi[COO]A... 25456385
Unchecked Ki = 0.36 nM 9.44 Inhibition of Hepatitis C virus genotype 1a full-length NS3/4A protease 24446688
Unchecked Ki = 0.36 nM 9.44 Inhibition of HCV NS3 protease by FRET assay 20541424
Unchecked Ki = 0.36 nM 9.44 Inhibition of recombinant full length HCV NS3/4A protease 18678486
Hepatitis C virus Ki = 0.4 nM 9.4 Inhibition of HCV 1b NS3 protease 21381769
Unchecked Ki = 0.4 nM 9.4 Inhibition of Hepatitis C virus subtype 1a NS3/4A protease 20176898
Hepatitis C virus Ki = 0.4 nM 9.4 Inhibition of HCV 1b isolate con1 NS3/4A protease using RetS1 as a substrate by ... 19171797
Hepatitis C virus serine protease, NS3/NS4A Ki = 0.5 nM 9.3 Enzymatic Assay: The aim of this in vitro assay was to measure the inhibition of... -
NS3 Ki = 0.5 nM 9.3 Inhibition Assay: The inhibition of full-length hepatitis C NS3 protease enzyme ... -
Unchecked Ki = 0.5 nM 9.3 Inhibition of HCV 1a NS3 protease 21381769
Hepatitis C virus Ki = 0.5 nM 9.3 Inhibition of Hepatitis C virus subtype 1b NS3/4A protease 20176898
Unchecked Ki = 0.5 nM 9.3 Inhibition of HCV 1a H77 NS3/4A protease using RetS1 as a substrate by fluoresce... 19171797
Hepatitis C virus EC50 = 1.0 nM 9.0 Antiviral activity against HCV subtype 1b expressing wild type NS3/4A protease i... 23142614
Hepatitis C virus EC50 = 1.0 nM 9.0 Antiviral activity against HCV subtype 1b infected in human hepatoma cells 23142614
Unchecked Ki = 1.4 nM 8.85 Inhibition of Hepatitis C virus genotype 1b NS3/4A protease 24446688
Hepatitis C virus EC50 = 1.4 nM 8.85 Antiviral activity against HCV 1b infected in human Huh-7 cells after 48hrs by l... 21067923
Hepatitis C virus EC50 = 1.4 nM 8.85 Ratio of EC50 Hepatitis C virus in presence of 40% human serum to EC50 for Hepat... 19171797
Hepatitis C virus EC50 = 1.4 nM 8.85 Ratio of EC50 Hepatitis C virus in presence of 1 mg/ml AAG to EC50 for Hepatitis... 19171797
Hepatitis C virus EC50 = 1.7 nM 8.77 Ratio of EC50 Hepatitis C virus in presence of 40 mg/ml HAS to EC50 for Hepatiti... 19171797

Literature References

PubMed DOI Target Context # Activities
20176898 10.1128/aac.01452-09 Hepatitis C virus 101
19171797 10.1128/aac.01058-08 Hepatitis C virus 19
24446688 10.1021/jm401507s Hepatitis C virus 14
19171797 10.1128/aac.01058-08 ADMET 14
20855726 10.1128/aac.00777-10 Hepatitis C virus 10
23142614 10.1016/j.bmcl.2012.10.075 Hepatitis C virus 9
19171797 10.1128/aac.01058-08 Unchecked 9
18678486 10.1016/j.bmcl.2008.07.088 Rattus norvegicus 8
19171797 10.1128/aac.01058-08 Rattus norvegicus 7
24446688 10.1021/jm401507s Unchecked 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
20176898 10.1128/aac.01452-09 Unchecked 6
19171797 10.1128/aac.01058-08 Plasma 5
30685524 10.1016/j.ejmech.2019.01.025 ADMET 5
24144360 10.1021/jm401396p Hepatitis C virus 5
21381769 10.1021/jm1012374 Hepatitis C virus 3
21381769 10.1021/jm1012374 Rattus norvegicus 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 3
37659195 10.1016/j.ejmech.2023.115772 Replicase polyprotein 1ab 2
18678486 10.1016/j.bmcl.2008.07.088 ADMET 2

Data from ChEMBL 36 via Core Engine