OSELTAMIVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H28N2O4
Molecular Weight	312.4045
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1

InChI

InChIKey=VSZGPKBBMSAYNT-RRFJBIMHSA-N

InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C16H28N2O4
Molecular Weight	312.4045
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11270942
Curator's Comment: Description was created based on several sources, including http://www.fda.gov/downloads/drugs/drugsafety/informationbydrugclass/ucm147992.pdf

Oseltamivir phosphate is an ethyl ester prodrug requiring ester hydrolysis for conversion to the active form, oseltamivir carboxylate. Oseltamivir carboxylate is an inhibitor of influenza virus neuraminidase affecting release of viral particles. Oseltamivir is a well tolerated orally active neuraminidase inhibitor which significantly reduces the duration of symptomatic illness and hastens the return to normal levels of activity when initiated promptly in patients with naturally acquired influenza.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neuraminidase 21 Target ID: CHEMBL2051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16125799	Inhibitor 8504		1.34 nM [IC50]
Neuraminidase 21 Target ID: CHEMBL3377 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16125799	Inhibitor 8504		13.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Influenza virus infections 34 Sources: http://www.fda.gov/downloads/drugs/drugsafety/informationbydrugclass/ucm147992.pdf	Primary		Approved 8583	TAMIFLU Approved Use TAMIFLU is indicated for the treatment of uncomplicated acute illness due to influenza infection in patients 1 year and older who have been symptomatic for no more than 2 days. Launch Date 1999

C_max

Value	Dose	Analyte	Population
441 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED
551 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
230 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	50 mg 2 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
439 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	100 mg 2 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1132 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2458 μg/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
348 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021087s062lbl.pdf	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
6069 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED
6218 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
2107 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	50 mg 2 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
3845 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	100 mg 2 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
8612 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
20317 μg × h/L REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2719 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021087s062lbl.pdf	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
8.2 h REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED
6.87 h REVIEW https://pubmed.ncbi.nlm.nih.gov/10628898/	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED
8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021087s062lbl.pdf	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OSELTAMIVIR ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
97% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021087s062lbl.pdf	75 mg 2 times / day multiple, oral dose: 75 mg route of administration: Oral experiment type: MULTIPLE co-administered:		OSELTAMIVIR ACID plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1000 mg single, oral Highest studied dose Dose: 1000 mg Route: oral Route: single Dose: 1000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10934667	healthy, 18-55 Health Status: healthy Age Group: 18-55 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/10934667	Sources: https://pubmed.ncbi.nlm.nih.gov/10934667
500 mg 2 times / day multiple, oral Highest studied dose Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10934667	healthy, 18-55 Health Status: healthy Age Group: 18-55 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/10934667	Sources: https://pubmed.ncbi.nlm.nih.gov/10934667
450 mg 2 times / day multiple, oral Higher than recommended Dose: 450 mg, 2 times / day Route: oral Route: multiple Dose: 450 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20189775	healthy, 33.9±11.52 Health Status: healthy Age Group: 33.9±11.52 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/20189775	Sources: https://pubmed.ncbi.nlm.nih.gov/20189775
75 mg 2 times / day multiple, oral Recommended Dose: 75 mg, 2 times / day Route: oral Route: multiple Dose: 75 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf	Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (rare) Vomiting (rare) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf

AEs

AE	Significance	Dose	Population
Nausea	rare Disc. AE	75 mg 2 times / day multiple, oral Recommended Dose: 75 mg, 2 times / day Route: oral Route: multiple Dose: 75 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf
Vomiting	rare Disc. AE	75 mg 2 times / day multiple, oral Recommended Dose: 75 mg, 2 times / day Route: oral Route: multiple Dose: 75 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf	unhealthy Health Status: unhealthy Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:73139	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:73139
ChemicalBook	CB6501589	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6501589
MolPort	MolPort-028-767-189	https://www.molport.com/shop/molecule-link/MolPort-028-767-189
ZINC	ZINC000003929509	http://zinc15.docking.org/substances/ZINC000003929509

PubMed

Title	Date	PubMed
Oseltamivir for treatment of influenza in healthy adults: pooled trial evidence and cost-effectiveness model for Canada.	2003-03-19	12641862
Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir.	2003-02-24	12639555
Antiviral drugs in the immunocompetent host: part II. Treatment of influenza and respiratory syncytial virus infections.	2003-02-15	12613730
Influenza diagnosis and treatment in children: a review of studies on clinically useful tests and antiviral treatment for influenza.	2003-02	12586981
Logistic issues and potential prescribing costs associated with use of neuraminidase inhibitors for the treatment of influenza in primary care.	2003-02	12562975
[Oral neuraminidase inhibitor and an early warning system. New weapons against influenza].	2003-01-23	12619232
The treatment of influenza with antiviral drugs.	2003-01-07	12515786
Early administration of oral oseltamivir increases the benefits of influenza treatment.	2003-01	12493796
Influenza vaccination and antiviral therapy: is there a role for concurrent administration in the institutionalised elderly?	2003	12578397
Neuraminidase inhibitors in pediatric patients: potential place in influenza therapy.	2003	12529164
[Influenza: a new treatment, oseltamivir].	2002-12-13	12476676
Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm.	2002-12-02	12419376
Oseltamivir for influenza.	2002-12	12613182
Efficacy and safety of zanamivir in patients with influenza--impact of age, severity of infections and specific risk factors.	2002-12	12458354
Early therapy with the neuraminidase inhibitor oseltamivir maximizes its efficacy in influenza treatment.	2002-12	12458353
Neuraminidase inhibitors in the management of influenza--experience of an outpatient practice.	2002-12	12458352
Problems of case and disease management in outpatient treatment of influenza.	2002-12	12458346
[New diagnostic possibilities and medications. Fit for influenza?].	2002-11-28	12532540
[Effectiveness of oseltamivir treatment against influenza type A and type B infection in children].	2002-11	12508478
Characterization of 2 influenza A(H3N2) clinical isolates with reduced susceptibility to neuraminidase inhibitors due to mutations in the hemagglutinin gene.	2002-10-15	12355356
[Neuraminidase inhibitor permitted. The first pill against influenza].	2002-10-10	12474367
Lack of pharmacokinetic interaction between the oral anti-influenza neuraminidase inhibitor prodrug oseltamivir and antacids.	2002-10	12392584
Current strategies for management of influenza in the elderly population.	2002-09-15	12203171
Influenza prevention 2002-2003.	2002-09-02	12205427
Cost-effectiveness of newer treatment strategies for influenza.	2002-09	12361816
Summaries for patients. Influenza vaccination or antiviral treatment for healthy working adults: an economic analysis.	2002-08-20	12186536
Economic analysis of influenza vaccination and antiviral treatment for healthy working adults.	2002-08-20	12186512
The management of influenza in people of working age.	2002-08	12181374
DNA vaccine expressing conserved influenza virus proteins protective against H5N1 challenge infection in mice.	2002-08	12141964
The H274Y mutation in the influenza A/H1N1 neuraminidase active site following oseltamivir phosphate treatment leave virus severely compromised both in vitro and in vivo.	2002-08	12103431
Management of viral infections in immunocompromised cancer patients.	2002-07-13	12428191
Influenza.	2002-06	12230692
[A revolutionary change in the diagnosis and treatment of influenza].	2002-06	12227179
Susceptibility of recent Canadian influenza A and B virus isolates to different neuraminidase inhibitors.	2002-06	12062387
Influenza vaccination for healthy children.	2002-06	12015463
Structural studies of the resistance of influenza virus neuramindase to inhibitors.	2002-05-23	12014958
Influenza surveillance with rapid diagnostic tests.	2002-05-15	11981745
Gateways to clinical trials.	2002-05-01	11980386
Influenza virus carrying neuraminidase with reduced sensitivity to oseltamivir carboxylate has altered properties in vitro and is compromised for infectivity and replicative ability in vivo.	2002-05	12062393
Experience with oseltamivir in the control of nursing home influenza A outbreak.	2002-05	12058885
Evidence-based emergency medicine/systematic review abstract. Use of the neuraminidase inhibitor class of antiviral drugs for treatment of healthy adults with an acute influenza-like illness.	2002-05	11973564
Prevention and control of influenza. Recommendations of the Advisory Committee on Immunization Practices (ACIP).	2002-04-12	12002171
Highlights in the development of new antiviral agents.	2002-04	12370077
Antiviral therapy of influenza.	2002-04	12122950
Use of oseltamivir during influenza outbreaks in Ontario nursing homes, 1999-2000.	2002-04	11982659
Influenza in the acute hospital setting.	2002-03	11944184
Antiviral therapy for influenza virus infections.	2002-01	12118841
Is oral oseltamivir safe and effective for the prevention of influenza and its complications in frail elderly long-term care residents who have received influenza vaccine?	2002-01	11927075
Antivirals for influenza: what is their role in the older patient?	2002	12390054
Utilization of alpha-1-acid glycoprotein levels in the serum as a parameter for in vivo assay of influenza virus inhibitors.	2001-11	12018681

Patents

Sample Use Guides

In Vivo Use Guide

The recommended oral dose of TAMIFLU (oseltamivir phosphate) for treatment of influenza in adults and adolescents 13 years and older is 75 mg twice daily for 5 days. Treatment should begin within 2 days of onset of symptoms of influenza.

Route of Administration: Oral

In Vitro Use Guide

Oseltamivir also showed moderate antiviral activity in Madine-Darby canine kidney cells of about 83% against influenza A/HK (H3N2) virus at the concentration of 100 μg/ml.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:07:13 GMT 2025` Edited by `admin` on `Mon Mar 31 18:07:13 GMT 2025`
Record UNII	20O93L6F9H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OSELTAMIVIR

Official Name

English

GS 4104

Preferred Name

English

oseltamivir [INN]

Common Name

English

GS4104

Code

English

OSELTAMIVIR [EMA EPAR]

Common Name

English

OSELTAMIVIR [VANDF]

Common Name

English

RO-640796

Code

English

RO 640796

Code

English

Oseltamivir [WHO-DD]

Common Name

English

RO-64-0796

Code

English

GS-4104

Code

English

ETHYL (3R,4R,5S)-4-ACETAMIDO-5-AMINO-3-(1-ETHYLPROPOXY)-1-CYCLOHEXENE-1-CARBOXYLATE

Systematic Name

English

RO64-0796

Code

English

OSELTAMIVIR [HSDB]

Common Name

English

GS-4071 ETHYL ESTER

Code

English

OSELTAMIVIR [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C281