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Compound Detail

CHEMBL1200340

OSELTAMIVIR PHOSPHATE
💊 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.O=P(O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1200340
Name OSELTAMIVIR PHOSPHATE
Phase Approved
Structure Type MOL
InChI Key PGZUMBJQJWIWGJ-ONAKXNSWSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL1229
Active Moiety CHEMBL674

Known Names

Agucort Ebilfumin Oseltamivir (as phosphate) Oseltamivir phosphate Oseltamiviri phosphas RO 64-0796/002 RO-64-0796-002 RO-64-0796/002 Tamiflu
6
Targets
24
Activities
3
Assay Types
27
PK Parameters
20
Publications
9
Known Names
3
Indications
2
Mechanisms

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

Prodrug
USAN Stem -vir
USAN Year 1998

Extended Properties

Molecular Formula C16H31N2O8P
MW 410.40
Aromatic Rings 0
Heavy Atoms 22
NP-Likeness 1.02

Mechanism of Action

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

Indications

Influenza, Human Kidney Failure, Chronic Virus Diseases

Activity Summary

IC50 13 meas. best 6.1
EC50 9 meas. best 6.47
Ki 2 meas. best 6.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Influenza A virus
CHEMBL613740
 EC50 6.47 5.5163 340.0 8
Neuraminidase
CHEMBL3232678
 IC50 6.1 6.1 800.0 1
Neuraminidase
CHEMBL2051
 Ki 6.07 6.07 860.0 1
Influenza A virus
CHEMBL613740
 IC50 5.96 5.4386 1100.0 7
Unchecked
CHEMBL612545
 Ki 5.7 5.7 2000.0 1
Influenza B virus
CHEMBL613129
 IC50 4.63 4.63 23450.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.34 4.34 45600.0 1
Unchecked
CHEMBL612545
 EC50 4.17 4.17 67000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 308.0 ng.hr.mL-1 Homo sapiens
AUC 7.6 ng.hr.mL-1 Homo sapiens
AUC 313.0 ng.hr.mL-1 Homo sapiens
AUC - - Homo sapiens
AUC 5540.0 ng.hr.mL-1 Homo sapiens
AUC 157.0 ng.hr.mL-1 Homo sapiens
AUC 5950.0 ng.hr.mL-1 Homo sapiens
AUC - - Homo sapiens
CL 25.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 368.11 nM Homo sapiens
Cmax 7.682 nM Homo sapiens
Cmax 1741.3 nM Homo sapiens
Cmax 60.82 nM Homo sapiens
Cmax 96.03 nM Rattus norvegicus
F 4.3 % Rattus norvegicus
T1/2 7.0 hr Rattus norvegicus
T1/2 1.8 hr Homo sapiens
t1/2 - - Homo sapiens
T1/2 5.4 hr Homo sapiens
t1/2 - - Homo sapiens
T1/2 1.6 hr Rattus norvegicus
T1/2 10.6 hr Rattus norvegicus
Tmax 1.0 hr Homo sapiens
Tmax 3.5 hr Homo sapiens
Tmax 5.0 hr Homo sapiens
Tmax 8.0 hr Homo sapiens
Tmax 4.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Influenza A virus EC50 = 340.0 nM 6.47 Antiviral activity against amantadine-resistant Influenza A virus (A/chicken/Hub... 31559005
Influenza A virus EC50 = 390.0 nM 6.41 Antiviral activity against amantadine-sensitive Influenza A virus (A/chicken/Hub... 31559005
Neuraminidase IC50 = 800.0 nM 6.1 Inhibition of Influenza A virus (A/RI/5+/1957(H2N2)) recombinant neuraminidase u... 24613627
Neuraminidase Ki = 860.0 nM 6.07 Inhibition of influenza A virus chicken/Nakorn-Patom/Thailand/CU-K2-2004 Neurami... 31128993
Influenza A virus IC50 = 1100.0 nM 5.96 Antiinfluenza activity against influenza A virus H3N2 infected in MDCK cells ass... 22341943
Influenza A virus IC50 = 1820.0 nM 5.74 Antiviral activity against Influenza A virus A/WSN/33 assessed as inhibition of ... 31425909
Influenza A virus IC50 = 1820.0 nM 5.74 Antiviral activity against Influenza A virus A/WSN/33(H1N1) infected in MDCK cel... 31635892
Influenza A virus IC50 = 1820.0 nM 5.74 Antiviral activity against Influenza A virus (A/WSN/1933(H1N1)) infected in MDCK... 34795865
Influenza A virus IC50 = 1820.0 nM 5.74 Antiviral activity against influenza A virus A/WSN/33(H1N1) infected in MDCK cel... 37354741
Influenza A virus EC50 = 2010.0 nM 5.7 Antiviral activity against Influenza A virus A/WSN/33(H1N1) strain infected in M... 34905383
Unchecked Ki = 2000.0 nM 5.7 Inhibition of Influenza A virus (A/California/07/2009(H1N1)) Neuraminidase N1 at... 31128993
Influenza A virus EC50 = 2250.0 nM 5.65 Antiviral activity against Influenza A virus A/Aichi/8/68(H3N2) strain infected ... 34905383
Influenza A virus EC50 = 4620.0 nM 5.33 Antiviral activity against Influenza A virus A/California/7/2009(H1N1) strain in... 34905383
Influenza A virus EC50 = 11600.0 nM 4.94 Antiviral activity against Influenza A virus A/Puerto Rico/8/34(H1N1) strain inf... 34905383
Influenza A virus EC50 = 12500.0 nM 4.9 Antiviral activity against Influenza A virus A/WSN/33(H1N1) infected in MDCK cel... 26866456
Influenza A virus IC50 = 15500.0 nM 4.81 Antiinfluenza activity against influenza A virus H1N1 infected in MDCK cells ass... 22341943
Influenza A virus EC50 = 18500.0 nM 4.73 Antiviral activity against Influenza A virus A/Virginia/ATCC2/2009(H1N1) strain ... 34905383
Influenza B virus IC50 = 23450.0 nM 4.63 Antiviral activity against Influenza B virus B/Yamagata/16/88(BY) infected in MD... 31425909
NON-PROTEIN TARGET IC50 = 45600.0 nM 4.34 Antiviral activity against Influenza A virus A/WSN/33 (H1N1) infected in MDCK ce... 24957203
Influenza A virus IC50 = 45600.0 nM 4.34 Antiviral activity against Influenza A virus A/WSN/33(H1N1) infected in dog MDCK... 26841168

Literature References

PubMed DOI Target Context # Activities
18676886 10.1128/aac.00327-08 ADMET 34
20047917 10.1128/aac.01311-09 Influenza A virus 26
22490229 10.1124/dmd.111.044263 Solute carrier family 15 member 1 9
23330908 10.1021/jm3009713 Rattus norvegicus 7
34905383 10.1021/acs.jmedchem.1c01527 Influenza A virus 6
37354741 10.1016/j.ejmech.2023.115562 Influenza A virus 4
22490229 10.1124/dmd.111.044263 Komagataella pastoris 4
20047917 10.1128/aac.01311-09 Influenza B virus 3
31425909 10.1016/j.ejmech.2019.111622 Influenza B virus 3
34795865 10.1021/acsmedchemlett.1c00374 Influenza A virus 3
28433779 10.1016/j.ejmech.2017.04.015 Unchecked 2
31425909 10.1016/j.ejmech.2019.111622 Influenza A virus 2
26866456 10.1016/j.ejmech.2016.01.005 Influenza A virus 2
31635892 10.1016/j.bmc.2019.115147 Influenza B virus 2
31559005 10.1039/C8MD00474A Matrix protein 2 2
24957203 10.1021/np500253m NON-PROTEIN TARGET 2
24613627 10.1016/j.bmc.2014.02.014 Neuraminidase 2
22341943 10.1016/j.bmcl.2012.01.056 Unchecked 2
31559005 10.1039/C8MD00474A Influenza A virus 2
22341943 10.1016/j.bmcl.2012.01.056 Influenza A virus 2

Data from ChEMBL 36 via Core Engine