OSELTAMIVIR PHOSPHATE

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Trade Names	OSELTAMIVIR PHOSPHATE TAMIFLU
Synonyms	Agucort Oseltamivir (as phosphate) Oseltamivir phosphate Oseltamiviri phosphas RO 64-0796/002 RO-64-0796-002 Tamiflu
Status
Molecule Category	Salt-form
UNII	4A3O49NGEZ
EPA CompTox	DTXSID0044230
Parent Compound:	OSELTAMIVIR


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	PGZUMBJQJWIWGJ-ONAKXNSWSA-N
Smiles	CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1.O=P(O)(O)O
InChI	InChI=1S/C16H28N2O4.H3O4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19;1-5(2,3)4/h9,12-15H,5-8,17H2,1-4H3,(H,18,19);(H3,1,2,3,4)/t13-,14+,15+;/m0./s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C16H31N2O8P
Molecular Weight	410.4
AlogP	1.29
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	7.0
Polar Surface Area	90.65
Molecular species	BASE
Aromatic Rings	0.0
Heavy Atoms	22.0

Bioactivity

Mechanism of Action	Action	Reference
Neuraminidase inhibitor	INHIBITOR	DailyMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Hydrolase	-	800	-	860	100

Assay Description	Organism	Bioactivity	Reference
Inhibition of Influenza A virus (A/RI/5+/1957(H2N2)) recombinant neuraminidase using MUNANA as substrate at 100 uM after 30 mins	Influenza A virus (A/RI/5+/1957(H2N2))	100.0 %
Inhibition of Influenza A virus (A/RI/5+/1957(H2N2)) recombinant neuraminidase using MUNANA as substrate after 30 mins	Influenza A virus (A/RI/5+/1957(H2N2))	800.0 nM
Antiviral activity against Influenza A virus A/WSN/33 (H1N1) infected in MDCK cells assessed as inhibition of virus-induced cell death at 100 uM after 36 hrs by CellTiter-Glo luminescent cell viability assay	Influenza A virus (A/WSN/1933(H1N1))	78.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-4.97 %
Inhibition of influenza A virus chicken/Nakorn-Patom/Thailand/CU-K2-2004 Neuraminidase N1 at pH 7.4 by DIANA assay	influenza A virus	860.0 nM
Antiviral activity against amantadine-resistant Influenza A virus (A/chicken/Hubei/327/2004(H5N1)) infected in MDCK cells after 40 mins by crystal violet staining-based plaque reduction assay	influenza A virus	340.0 nM
Antiviral activity against amantadine-sensitive Influenza A virus (A/chicken/Hubei/327/2004(H5N1)) infected in MDCK cells after 40 mins by crystal violet staining-based plaque reduction assay	influenza A virus	390.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	0.5153 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.01 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.01 %
Antiviral activity against Influenza A virus A/WSN/33(H1N1) infected in MDCK cells assessed as s reduction in cytopathic effect after 40 hrs incubation by CellTiter-Glo assay relative to control	Influenza A virus	86.5 %
Antiviral activity against Influenza A virus (A/WSN/1933(H1N1)) infected in MDCK cells assessed as inhibition of virus-induced cytopathic effect at 100 uM measured after 40 hrs incubation by inverted microscpic imaging analysis	Influenza A virus	80.0 %

Cross References

Resources	Reference
ChEBI	7799
ChEMBL	CHEMBL1200340
FDA SRS	4A3O49NGEZ
KEGG	C08093
PubChem	78000
SureChEMBL	SCHEMBL8730
ZINC	ZINC03929508

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).