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Compound Detail

CHEMBL2023898

DACLATASVIR
💊 Approved Drug
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💊 Approved Drug
COC(=O)N[C@H](C(=O)N1CCC[C@H]1c1ncc(-c2ccc(-c3ccc(-c4cnc([C@@H]5CCCN5C(=O)[C@@H](NC(=O)OC)C(C)C)[nH]4)cc3)cc2)[nH]1)C(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2023898
Name DACLATASVIR
Phase Approved
Structure Type MOL
InChI Key FKRSSPOQAMALKA-CUPIEXAXSA-N
Therapeutic ✓ Yes

Known Names

BMS 790052 BMS-790052 Daclatasvir EBP 883 EBP-883
8
Targets
118
Activities
2
Assay Types
30
PK Parameters
20
Publications
5
Known Names
8
Indications

Molecular Properties

738.9
MW (Da)
6.22
ALogP
8
HBA
4
HBD
174.6
PSA (Ų)
0.14
QED
2
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2014
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 C40H50N8O6
MW 738.89
Aromatic Rings 4
Heavy Atoms 54
NP-Likeness -0.41

Indications

Virus Diseases Hepatitis C Hepatitis C, Chronic Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Hepatitis B, Chronic Infections Renal Insufficiency, Chronic

ATC Classification

J05AP07
daclatasvir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 108 meas. best 11.0
IC50 10 meas. best 10.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hepatitis C virus
CHEMBL379
 EC50 11.0 9.712 0.0 66
Nonstructural protein 5A
CHEMBL3307224
 IC50 10.64 10.64 0.0 1
Unchecked
CHEMBL612545
 EC50 10.64 8.0775 0.0 4
Hepatitis C virus
CHEMBL379
 IC50 10.51 10.51 0.0 1
Nonstructural protein 5A
CHEMBL3307224
 EC50 10.49 9.2036 0.0 14
SARS-CoV-2
CHEMBL4303835
 EC50 5.96 5.96 1100.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.14 5.14 7200.0 3
Bovine viral diarrhea virus 1
CHEMBL612571
 EC50 5.05 5.05 9000.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.54 4.54 29200.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.22 4.22 59500.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 1426.06 ng.hr.mL-1 Macaca mulatta
AUC 8127.79 ng.hr.mL-1 Canis lupus familiaris
AUC 3546.67 ng.hr.mL-1 Rattus norvegicus
AUC 1611.52 ng.hr.mL-1 Rattus norvegicus
AUC 3546.67 ng.hr.mL-1 Rattus norvegicus
AUC 8127.79 ng.hr.mL-1 Canis lupus familiaris
AUC 1426.06 ng.hr.mL-1 Macaca fascicularis
AUC 3320.0 ng.hr.mL-1 Rattus norvegicus
AUC 3210.0 ng.hr.mL-1 Rattus norvegicus
Cmax 728.0 nM Rattus norvegicus
Cmax 500.0 nM Macaca mulatta
Cmax 655.04 nM Rattus norvegicus
F 38.0 % Macaca mulatta
F 108.0 % Canis lupus familiaris
F 50.0 % Rattus norvegicus
F 50.0 % Rattus norvegicus
F 108.0 % Canis lupus familiaris
F 38.0 % Macaca fascicularis
F 50.0 % Rattus norvegicus
F 58.5 % Canis lupus familiaris
F 38.0 % Macaca mulatta
F 50.0 % Rattus norvegicus
F 67.0 % Homo sapiens
F 67.0 % Homo sapiens
MRT 3.43 hr Rattus norvegicus
T1/2 0.9383 hr Homo sapiens
T1/2 1.5 hr Rattus norvegicus
T1/2 3.0 hr Macaca mulatta
T1/2 1.66 hr Rattus norvegicus
T1/2 12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hepatitis C virus EC50 = 0.01 nM 11.0 Antiviral activity against Hepatitis C virus genotype 1b in Huh-luc/neo-ET repli... 24568313
Hepatitis C virus EC50 = 0.01 nM 11.0 Antiviral activity against HCV genotype 1b by replicon assay 26850003
Hepatitis C virus EC50 = 0.01 nM 11.0 Antiviral activity against HCV 1b infected in human HuH7 cells by in vitro repli... 23466233
Hepatitis C virus EC50 = 0.012 nM 10.92 Antiviral activity against HCV4a 24521299
Hepatitis C virus EC50 = 0.012 nM 10.92 Antiviral activity against Hepatitis C virus genotype 4a replicon containing Hep... 24749835
Hepatitis C virus EC50 = 0.012 nM 10.92 Antiviral activity against HCV genotype 4a 27501244
Hepatitis C virus EC50 = 0.01767 nM 10.75 Antiviral activity against wild-type HCV J6/JFH/JC1 infected in human Huh7.5 cel... 27783522
Hepatitis C virus EC50 = 0.02119 nM 10.67 Antiviral activity against HCV 4a ED43 in human Huh7.5 cells carrying HCV subgen... 34959173
Unchecked EC50 = 0.023 nM 10.64 Inhibition of NS5A in HCV genotype-1b infected in human HuH7 cells by luciferase... 25453810
Nonstructural protein 5A IC50 = 0.023 nM 10.64 Inhibition of NS5A in HCV genotype 1b infected in human HuH7.5/Con1/SG-Neo(I)-hR... 31710479
Hepatitis C virus EC50 = 0.024 nM 10.62 Antiviral activity against HCV genotype 2a 26099532
Hepatitis C virus EC50 = 0.0257 nM 10.59 Antiviral activity against HCV GT-1b Con1 in human Huh-5-2 cells carrying HCV su... 34959173
Hepatitis C virus EC50 = 0.028 nM 10.55 Antiviral activity against Hepatitis C virus genotype 2a JFH 24749835
Hepatitis C virus EC50 = 0.028 nM 10.55 Antiviral activity against HCV genotype 1b JFH-1 infected in human HuH7 cells as... 26077493
Hepatitis C virus IC50 = 0.031 nM 10.51 Antiviral activity against HCV infected in human Huh-7 cells assessed as reducti... 33454548
Nonstructural protein 5A EC50 = 0.0324 nM 10.49 Inhibition of NS5A in HCV genotype 1a infected in HuH-Lcu-Neo cells assessed as ... 32202782
Nonstructural protein 5A EC50 = 0.032 nM 10.49 Inhibition of HCV genotype 1b NS5A infected in HuH-7-Luc/Neo-ET cells assessed a... 34790290
Hepatitis C virus EC50 = 0.033 nM 10.48 Antiviral activity against HCV5a 24521299
Hepatitis C virus EC50 = 0.033 nM 10.48 Antiviral activity against Hepatitis C virus genotype 5a replicon containing Hep... 24749835
Hepatitis C virus EC50 = 0.033 nM 10.48 Antiviral activity against HCV genotype 5a 27501244

Literature References

PubMed DOI Target Context # Activities
24521299 10.1021/jm401836p Hepatitis C virus 17
25365735 10.1021/jm501291c Hepatitis C virus 17
24749835 10.1021/jm500335h Hepatitis C virus 15
24568313 10.1021/jm4013104 Hepatitis C virus 10
27501244 10.1021/acs.jmedchem.6b00915 Hepatitis C virus 8
25453811 10.1016/j.bmcl.2014.10.056 Hepatitis C virus 7
26077493 10.1016/j.bmcl.2015.06.006 Rattus norvegicus 7
26099532 10.1016/j.bmcl.2015.06.031 Hepatitis C virus 7
32738974 10.1016/j.bmcl.2020.127361 Nonstructural protein 5A 6
32202782 10.1021/acs.jmedchem.9b02176 Nonstructural protein 5A 6
34959173 10.1016/j.ejmech.2021.114034 Hepatitis C virus 6
26099532 10.1016/j.bmcl.2015.06.031 ADMET 5
26850003 10.1016/j.bmcl.2016.01.050 Hepatitis C virus 5
30685524 10.1016/j.ejmech.2019.01.025 ADMET 5
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
24521299 10.1021/jm401836p Plasma 4
24900811 10.1021/ml300461f Hepatitis C virus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
22507961 10.1016/j.bmcl.2012.03.089 Hepatitis C virus 3
26134551 10.1016/j.ejmech.2015.06.033 Hepatitis C virus 3

Data from ChEMBL 36 via Core Engine