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Compound Detail

CHEMBL1229

OSELTAMIVIR
💊 Approved Drug
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💊 Approved Drug
CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1229
Name OSELTAMIVIR
Phase Approved
Structure Type MOL
InChI Key VSZGPKBBMSAYNT-RRFJBIMHSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL674

Known Names

GS 4104 GS-4071 ETHYL ESTER GS-4104 GS4104 Oseltamivir RO 640796 RO-64-0796 RO-640796 RO64-0796
20
Targets
433
Activities
3
Assay Types
30
PK Parameters
20
Publications
9
Known Names
11
Indications

Molecular Properties

312.4
MW (Da)
1.29
ALogP
5
HBA
2
HBD
90.7
PSA (Ų)
0.69
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

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

Routes of Administration

Oral

Flags

Natural Product Prodrug
USAN Stem -vir
USAN Year 1998

Extended Properties

Molecular Formula C16H28N2O4
MW 312.41
Aromatic Rings 0
Heavy Atoms 22
NP-Likeness 1.02

Indications

Influenza, Human Pneumonia Purpura, Thrombocytopenic, Idiopathic Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Virus Diseases Infections Influenza in Birds Thrombocytopenia Obesity Renal Insufficiency, Chronic

ATC Classification

J05AH02
oseltamivir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

IC50 308 meas. best 10.22
EC50 108 meas. best 10.22
Ki 17 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuraminidase
CHEMBL6135
 IC50 10.22 8.139 0.1 82
Unchecked
CHEMBL612545
 EC50 10.22 8.9629 0.1 7
Neuraminidase
CHEMBL1667683
 Ki 10.0 10.0 0.1 1
Neuraminidase
CHEMBL6135
 Ki 10.0 9.525 0.1 2
Neuraminidase
CHEMBL1667686
 IC50 10.0 8.4033 0.1 3
Influenza A virus
CHEMBL613740
 IC50 9.8 7.5354 0.2 130
Neuraminidase
CHEMBL1667683
 IC50 9.7 9.61 0.2 2
Unchecked
CHEMBL612545
 IC50 9.12 7.3113 0.8 52
Influenza A virus
CHEMBL613740
 EC50 9.0 6.068 1.0 64
Neuraminidase
CHEMBL1667686
 Ki 8.96 8.96 1.1 1
Neuraminidase
CHEMBL3377
 Ki 8.96 8.96 1.1 1
Neuraminidase
CHEMBL3559643
 IC50 8.86 6.5475 1.4 4
Neuraminidase
CHEMBL1287607
 IC50 8.81 8.81 1.6 1
Influenza A virus H3N2
CHEMBL2366902
 IC50 8.52 6.734 3.0 5
Neuraminidase
CHEMBL1667685
 IC50 8.43 8.37 3.7 2
Neuraminidase
CHEMBL1667685
 Ki 8.31 8.31 4.9 1
Neuraminidase
CHEMBL3377
 IC50 8.3 8.3 5.0 1
Unchecked
CHEMBL612545
 Ki 8.22 7.39 6.0 9
Neuraminidase
CHEMBL2051
 IC50 8.15 6.706 7.1 5
Neuraminidase
CHEMBL1667684
 Ki 8.1 8.1 7.9 1
Neuraminidase
CHEMBL1667684
 IC50 7.97 7.325 10.8 2
Influenza B virus
CHEMBL613129
 EC50 7.3 5.3143 50.0 21
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.01 6.2125 98.0 4
H3N2 subtype
CHEMBL613193
 EC50 6.1 5.65 800.0 4
H2N2 subtype
CHEMBL612765
 IC50 5.84 5.84 1450.0 1
Influenza B virus
CHEMBL613129
 IC50 5.68 5.68 2100.0 1
MDCK
CHEMBL614068
 EC50 5.65 5.65 2240.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.57 4.9067 2700.0 3
Influenza A virus H3N2
CHEMBL2366902
 EC50 5.24 5.0333 5700.0 3
H5N1 subtype
CHEMBL613845
 EC50 5.22 5.22 5970.0 1
Neuraminidase
CHEMBL2051
 Ki 4.92 4.92 12100.0 1
H5N1 subtype
CHEMBL613845
 IC50 4.47 4.47 34000.0 1
unidentified influenza virus
CHEMBL613128
 IC50 4.35 4.35 45000.0 1
Sialidase
CHEMBL5189
 IC50 4.21 4.21 61100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3610.0 ng.hr.mL-1 Rattus norvegicus
AUC 24.0 ng.hr.mL-1 Canis lupus familiaris
AUC 8881.82 ng.hr.mL-1 Mus musculus
AUC 287.0 ng.hr.mL-1 Homo sapiens
AUC 280.0 ng.hr.mL-1 Homo sapiens
AUC 244.0 ng.hr.mL-1 Homo sapiens
AUC 238.0 ng.hr.mL-1 Homo sapiens
AUC 27100.0 ng.hr.mL-1 Rattus norvegicus
AUC 26900.0 ng.hr.mL-1 Rattus norvegicus
AUC 29500.0 ng.hr.mL-1 Rattus norvegicus
AUC 20300.0 ng.hr.mL-1 Rattus norvegicus
AUC 2840.0 ng.hr.mL-1 Rattus norvegicus
AUC 2830.0 ng.hr.mL-1 Rattus norvegicus
AUC 2280.0 ng.hr.mL-1 Rattus norvegicus
AUC 2810.0 ng.hr.mL-1 Rattus norvegicus
AUC 2800.0 ng.hr.mL-1 Rattus norvegicus
AUC 2510.0 ng.hr.mL-1 Rattus norvegicus
AUC 2510.0 ng.hr.mL-1 Rattus norvegicus
AUC 2510.0 ng.hr.mL-1 Rattus norvegicus
AUC 2200.0 ng.hr.mL-1 Rattus norvegicus
AUC 3810.0 ng.hr.mL-1 Rattus norvegicus
AUC 3780.0 ng.hr.mL-1 Rattus norvegicus
AUC 3060.0 ng.hr.mL-1 Rattus norvegicus
AUC 3010.0 ng.hr.mL-1 Rattus norvegicus
AUC 2710.0 ng.hr.mL-1 Rattus norvegicus
AUC 2680.0 ng.hr.mL-1 Rattus norvegicus
CL 93.9 mL.min-1.kg-1 Rattus norvegicus
CL 23.1 L/hr Homo sapiens
CL 20.4 L/hr Homo sapiens
Cmax 5281.52 nM Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuraminidase IC50 = 0.06 nM 10.22 Inhibition of Influenza Virus A/Horneburg/IDT7489/08 (H1N1) neuraminidase 20014777
Unchecked EC50 = 0.06 nM 10.22 Synergistic antiviral activity against Influenza A virus (A/WSN/33(H1N1)) infect... 29341607
Neuraminidase IC50 = 0.1 nM 10.0 Inhibition of Influenza A virus (A/duck/Laos/25/2006(H5N1)) neuraminidase by flu... 19349520
Neuraminidase IC50 = 0.1 nM 10.0 Inhibition of Influenza A virus (A/duck/Laos/25/2006(H5N1)) neuraminidase isolat... 19349520
Neuraminidase Ki = 0.1 nM 10.0 Inhibition of influenza A/N1/PR/8/34 neuraminidase 18242993
Neuraminidase Ki = 0.1 nM 10.0 Inhibition of Influenza A virus (A/Thailand/1(KAN-1)/2004(H5N1)) neuraminidase b... 19349520
Unchecked EC50 = 0.11 nM 9.96 Synergistic antiviral activity against Influenza A virus (A/WSN/33(H1N1)) infect... 29341607
Influenza A virus IC50 = 0.16 nM 9.8 Antiviral activity against Influenza A virus (A/Washington/01/2007 (H3N2)) measu... 20194700
Neuraminidase IC50 = 0.16 nM 9.8 Inhibition of Influenza Virus A/Potsdam/15/81 (H1N1) neuraminidase 20014777
Neuraminidase IC50 = 0.19 nM 9.72 Inhibition of Influenza Virus A/Brest/IDT7490/08 (H1N1) neuraminidase 20014777
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 Influenza A virus (A/Hong Kong/1/1968(H3N2)) neuraminidase by chem... 24313801
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/Vietnam/1203/2004 (H5N1)) harbor... 19651908
Neuraminidase IC50 = 0.2 nM 9.7 Inhibition of Influenza Virus A/Belzig/2/01 (H1N1) neuraminidase 20014777
Neuraminidase IC50 = 0.2 nM 9.7 Inhibition of Influenza A virus H7N3 N3 neuraminidase expressed in baculovirus u... 22342267
Influenza A virus IC50 = 0.2 nM 9.7 Antiviral activity against Influenza A virus (A/Vietnam/1203/2004 (H5N1)) infect... 19651908
Influenza A virus IC50 = 0.2 nM 9.7 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
19349520 10.1128/aac.01667-08 Influenza A virus 63
20585136 10.1128/aac.00581-10 Influenza A virus 60
19721074 10.1128/aac.01541-08 ADMET 50
18955520 10.1128/aac.00333-08 Neuraminidase 43
22584254 10.1124/dmd.112.044990 Rattus norvegicus 39
19721074 10.1128/aac.01541-08 LLC-PK1 36
17296744 10.1128/aac.01312-06 Influenza A virus 34
18955520 10.1128/aac.00333-08 Unchecked 29
20695427 10.1021/jm100621s Unchecked 28
22584254 10.1124/dmd.112.044990 ADMET 22
19015327 10.1128/aac.01276-08 Influenza A virus 22
19349520 10.1128/aac.01667-08 Neuraminidase 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
22584254 10.1124/dmd.112.044990 Homo sapiens 14
19364864 10.1128/aac.00167-09 Influenza A virus 14
28958846 10.1016/j.bmc.2017.07.006 Influenza A virus 14
29341607 10.1021/acs.jmedchem.7b01536 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
17194832 10.1128/aac.01051-06 Influenza A virus 9

Data from ChEMBL 36 via Core Engine