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Compound Detail

CHEMBL222813

ZANAMIVIR
💊 Approved Drug
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💊 Approved Drug
CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(=O)O)=C[C@@H]1NC(=N)N

Basic Information

ChEMBL ID CHEMBL222813
Name ZANAMIVIR
Phase Approved
Structure Type MOL
InChI Key ARAIBEBZBOPLMB-UFGQHTETSA-N
Therapeutic ✓ Yes

Known Names

GG-167 GG167 GR 121167X GR-121167 GR-121167X Relenza Zanamivir
30
Targets
595
Activities
4
Assay Types
30
PK Parameters
20
Publications
7
Known Names
5
Indications
2
Mechanisms

Molecular Properties

332.3
MW (Da)
-3.58
ALogP
7
HBA
8
HBD
198.2
PSA (Ų)
0.18
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1999
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product
USAN Stem -vir
USAN Year 1997

Extended Properties

Molecular Formula C12H20N4O7
MW 332.31
Aromatic Rings 0
Heavy Atoms 23
NP-Likeness 1.20

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Neuraminidase inhibitor INHIBITOR Neuraminidase
Neuraminidase inhibitor INHIBITOR Neuraminidase

Indications

Influenza, Human Virus Diseases Dengue Diabetes Mellitus, Type 2 Infections

ATC Classification

J05AH01
zanamivir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

IC50 459 meas. best 10.52
EC50 105 meas. best 10.0
Ki 29 meas. best 10.22
Kd 2 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuraminidase
CHEMBL6135
IC50 10.52 8.3993 0.0 121
Influenza A virus
CHEMBL613740
IC50 10.4 8.3487 0.0 137
Neuraminidase
CHEMBL6135
Ki 10.22 9.81 0.1 4
Neuraminidase
CHEMBL3377
Ki 10.0 10.0 0.1 1
Influenza A virus
CHEMBL613740
EC50 10.0 6.5133 0.1 67
Unchecked
CHEMBL612545
Ki 9.7 8.145 0.2 10
Unchecked
CHEMBL612545
IC50 9.52 8.0245 0.3 87
Neuraminidase
CHEMBL1667685
Ki 9.4 9.4 0.4 1
Neuraminidase
CHEMBL1667683
Ki 9.3 9.3 0.5 1
Neuraminidase
CHEMBL1667686
Ki 9.3 9.3 0.5 1
Neuraminidase
CHEMBL2051
IC50 9.3 8.509 0.5 20
Neuraminidase
CHEMBL1667686
IC50 9.22 8.8467 0.6 3
Neuraminidase
CHEMBL1667685
IC50 9.15 8.1667 0.7 6
Neuraminidase
CHEMBL1287610
IC50 9.1 8.812 0.8 5
H2N2 subtype
CHEMBL612765
IC50 9.1 7.61 0.8 2
H5N1 subtype
CHEMBL613845
IC50 9.1 7.88 0.8 2
Neuraminidase
CHEMBL1667684
Ki 9.0 9.0 1.0 1
Unchecked
CHEMBL612545
Kd 8.96 8.96 1.1 1
Neuraminidase
CHEMBL1667683
IC50 8.96 8.71 1.1 3
Neuraminidase
CHEMBL1667684
IC50 8.89 8.4525 1.3 4
Influenza A virus H3N2
CHEMBL2366902
IC50 8.8 7.8167 1.6 3
Neuraminidase
CHEMBL3377
IC50 8.77 8.0258 1.7 12
Neuraminidase
CHEMBL6015
IC50 8.76 7.9257 1.7 7
Human immunodeficiency virus type 1 integrase
CHEMBL3471
IC50 8.6 8.6 2.5 1
Neuraminidase
CHEMBL1287607
IC50 8.57 8.57 2.7 1
Influenza B virus
CHEMBL613129
IC50 8.4 7.732 4.0 5
Neuraminidase
CHEMBL2046263
Kd 8.33 8.33 4.7 1
Influenza B virus
CHEMBL613129
EC50 8.21 6.5788 6.2 17
Neuraminidase
CHEMBL4295592
IC50 8.13 8.13 7.4 1
Neuraminidase
CHEMBL4295840
IC50 8.05 7.415 8.9 2
Influenza A virus (A/Puerto Rico/8/1934(H1N1))
CHEMBL612610
IC50 8.0 8.0 10.0 1
Influenza A virus H3N2
CHEMBL2366902
EC50 8.0 7.24 10.0 4
H5N1 subtype
CHEMBL613845
EC50 7.89 7.89 13.0 1
Neuraminidase
CHEMBL2046263
IC50 7.81 7.725 15.4 2
Neuraminidase
CHEMBL4295612
IC50 7.64 7.64 22.8 1
MDCK
CHEMBL614068
EC50 7.4 6.475 40.0 2
Unchecked
CHEMBL612545
EC50 7.26 6.274 55.0 5
Sialidase-3
CHEMBL3046
Ki 6.21 6.21 620.0 3
NON-PROTEIN TARGET
CHEMBL3879801
EC50 6.11 5.4033 786.0 3
NON-PROTEIN TARGET
CHEMBL3879801
IC50 6.06 6.06 880.0 1
H3N2 subtype
CHEMBL613193
EC50 5.92 5.438 1200.0 5
Neuraminidase
CHEMBL3232678
IC50 5.85 5.85 1400.0 1
Sialidase-2
CHEMBL3200
IC50 5.41 5.081 3900.0 10
Sialidase-3
CHEMBL3046
IC50 5.4 5.27 4000.0 6
Sialidase-2
CHEMBL3200
Ki 5.24 5.1225 5700.0 4
unidentified influenza virus
CHEMBL613128
EC50 4.82 4.82 15000.0 1
Sialidase-4
CHEMBL4174
Ki 4.58 4.58 26000.0 3
Sialidase-4
CHEMBL4174
IC50 4.33 4.33 47000.0 4

Pharmacokinetic Data

Parameter Value Units Species
CL 24.9 mL.min-1.kg-1 -
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 0.2 mL.min-1.kg-1 Homo sapiens
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 1.417 mL.min-1.kg-1 Rattus norvegicus
CL 31.67 mL.min-1.kg-1 Rattus norvegicus
Cmax 180.55 nM Rattus norvegicus
F 2.7 % Rattus norvegicus
F 3.7 % Rattus norvegicus
F 3.7 % Rattus norvegicus
Fu 0.86 - Homo sapiens
Fu 0.86 - Homo sapiens
MRT 2.4 hr Homo sapiens
T1/2 0.16 hr -
T1/2 2.8 hr Homo sapiens
T1/2 1.7 hr Homo sapiens
T1/2 0.25 hr Rattus norvegicus
T1/2 0.4 hr Rattus norvegicus
T1/2 1.8 hr Rattus norvegicus
T1/2 1.1 hr Rattus norvegicus
T1/2 1.8 hr Rattus norvegicus
T1/2 0.6883 hr Influenza A virus
t1/2 - - Influenza A virus
T1/2 0.4617 hr Influenza A virus
T1/2 1.213 hr Influenza A virus (A/chicken/Bangli/BBVD-563/2007(H5N1))
T1/2 1.812 hr Influenza A virus (A/Fukui/45/2004(H3N2))
T1/2 0.535 hr Influenza A virus (A/NWS/G70C(H1N9))
T1/2 0.41 hr Influenza B virus (B/Perth/211/2001)
T1/2 2.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuraminidase IC50 = 0.03 nM 10.52 Inhibition of neuraminidase in Influenza A virus A/Jena/5258/2009(H1N1) using Na... 24422530
Influenza A virus IC50 = 0.04 nM 10.4 Antiviral activity against Influenza A virus H1N1 24422530
Neuraminidase IC50 = 0.05 nM 10.3 Inhibition of neuraminidase in Influenza A virus A/HH/1580/09(H1N1) using Na-sta... 24422530
Neuraminidase Ki = 0.06 nM 10.22 Inhibition of influenza A/N1/PR/8/34 neuraminidase 18242993
Influenza A virus EC50 = 0.1 nM 10.0 Antiviral activity against Influenza A virus (A/Victoria/503/06) infected in MDC... 29397718
Neuraminidase Ki = 0.1 nM 10.0 Inhibition of influenza B/Memphis/3/89 neuraminidase 18242993
Neuraminidase Ki = 0.16 nM 9.8 Inhibition of influenza A nuraminidase N1 20873795
Influenza A virus IC50 = 0.2 nM 9.7 Antiviral activity against Influenza A virus (A/Chicken/Laos/26/2006(H5N1)) infe... 19651908
Neuraminidase IC50 = 0.2 nM 9.7 Inhibition of neuraminidase in Influenza A virus A/Rheinland-Pfalz/3911/03(H3N2)... 24422530
Influenza A virus IC50 = 0.2 nM 9.7 Antiviral activity against Influenza A virus (A/Chicken/Laos/26/2006(H5N1)) infe... 19651908
Influenza A virus IC50 = 0.2 nM 9.7 Antiviral activity against Influenza A virus (A/Chicken/Laos/26/2006(H5N1)) infe... 19651908
Influenza A virus IC50 = 0.2 nM 9.7 Antiviral activity against Influenza A virus (A/Chicken/Laos/26/2006(H5N1)) infe... 19651908
Influenza A virus IC50 = 0.2 nM 9.7 Antiviral activity against Influenza A virus (A/Chicken/Laos/26/2006(H5N1)) infe... 19651908
Unchecked Ki = 0.2 nM 9.7 Inhibition of viral Neuraminidase 21489803
Influenza A virus IC50 = 0.2 nM 9.7 Antiviral activity against Influenza A virus (A/Chicken/Laos/26/2006(H5N1)) infe... 19651908
Neuraminidase Ki = 0.2 nM 9.7 Inhibition of Influenza A virus neuraminidase 20452227
Neuraminidase IC50 = 0.29 nM 9.54 Inhibition of neuraminidase H274Y mutant in Oseltamivir-resistant Influenza A vi... 24422530
Influenza A virus IC50 = 0.3 nM 9.52 Antiviral activity against Influenza A virus (A/Chicken/Laos/26/2006(H5N1)) infe... 19651908
Influenza A virus IC50 = 0.3 nM 9.52 Antiviral activity against Influenza A virus (A/Chicken/Laos/26/2006(H5N1)) infe... 19651908
Influenza A virus IC50 = 0.3 nM 9.52 Antiviral activity against Influenza A virus (A/Chicken/Laos/26/2006(H5N1)) infe... 19651908

Literature References

PubMed DOI Target Context # Activities
19651908 10.1128/aac.00334-09 Influenza A virus 73
20585136 10.1128/aac.00581-10 Influenza A virus 60
18955520 10.1128/aac.00333-08 Neuraminidase 43
29397718 10.1021/acs.jmedchem.7b01467 Neuraminidase 39
18955520 10.1128/aac.00333-08 Unchecked 29
20695427 10.1021/jm100621s Unchecked 28
27095056 10.1021/acs.jmedchem.5b01863 Neuraminidase 16
27095056 10.1021/acs.jmedchem.5b01863 Influenza A virus 16
19349520 10.1128/aac.01667-08 Neuraminidase 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
27341624 10.1021/acs.jmedchem.6b00537 Influenza A virus 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
29965752 10.1021/acs.jmedchem.8b00929 Neuraminidase 11
18955520 10.1128/aac.00333-08 Influenza A virus 11
20047917 10.1128/aac.01311-09 Influenza A virus 10
34797984 10.1021/acs.jmedchem.1c01531 Influenza A virus 10
20194700 10.1128/aac.01608-09 Influenza A virus 9
27167096 10.1021/acs.jmedchem.6b00029 Neuraminidase 8
15006410 10.1016/j.bmcl.2003.09.102 Mus musculus 8
20070106 10.1021/jm901371v Homo sapiens 8

Data from ChEMBL 36 via Core Engine