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 8297		1.34 nM [IC50]
Neuraminidase 21 Target ID: CHEMBL3377 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16125799	Inhibitor 8297		13.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Influenza virus infections 33 Sources: http://www.fda.gov/downloads/drugs/drugsafety/informationbydrugclass/ucm147992.pdf	Primary		Approved 8429	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
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
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
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
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
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
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
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
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 Page: p.841	healthy, 18-55 n = 6 Health Status: healthy Age Group: 18-55 Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/10934667 Page: p.841	Sources: https://pubmed.ncbi.nlm.nih.gov/10934667 Page: p.841
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 Page: p.841	healthy, 18-55 n = 6 Health Status: healthy Age Group: 18-55 Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/10934667 Page: p.841	Sources: https://pubmed.ncbi.nlm.nih.gov/10934667 Page: p.841
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 Page: p.464	healthy, 33.9±11.52 n = 99 Health Status: healthy Age Group: 33.9±11.52 Sex: M+F Population Size: 99 Sources: https://pubmed.ncbi.nlm.nih.gov/20189775 Page: p.464	Sources: https://pubmed.ncbi.nlm.nih.gov/20189775 Page: p.464
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 Page: p.10	unhealthy n = 1171 Health Status: unhealthy Condition: Influenza Sex: M+F Population Size: 1171 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf Page: p.10	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 Page: p.10

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 Page: p.10	unhealthy n = 1171 Health Status: unhealthy Condition: Influenza Sex: M+F Population Size: 1171 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf Page: p.10
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 Page: p.10	unhealthy n = 1171 Health Status: unhealthy Condition: Influenza Sex: M+F Population Size: 1171 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/021087s057lbl.pdf Page: p.10

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
Identifying research priorities on infections in older adults: proceedings of an interdisciplinary workshop.	2001	11532199
Oseltamivir: a review of its use in influenza.	2001	11270942
Unprepared for an influenza pandemic.	2001 Aug 25	11545086
Management of influenza in patients with asthma or chronic obstructive pulmonary disease.	2001 Dec	11770690
Treatment of influenza with neuraminidase inhibitors: virological implications.	2001 Dec 29	11779389
[What is current opinion of antiviral therapy for the flu in 2001?].	2001 Jan	11218299
Symptom pathogenesis during acute influenza: interleukin-6 and other cytokine responses.	2001 Jul	11424113
Antiviral agents for influenza, hepatitis C and herpesvirus, enterovirus and rhinovirus infections.	2001 Jul 16	11556411
Experience with oseltamivir in the control of a nursing home influenza B outbreak.	2001 Mar 1	11260987
Vaccines for pneumonia and new antiviral therapies.	2001 Nov	11680115
Therapeutic options for the management of influenza.	2001 Oct	11764774
Highlights in the development of new antiviral agents.	2002 Apr	12370077
Use of oseltamivir during influenza outbreaks in Ontario nursing homes, 1999-2000.	2002 Apr	11982659
Prevention and control of influenza. Recommendations of the Advisory Committee on Immunization Practices (ACIP).	2002 Apr 12	12002171
Oseltamivir for influenza.	2002 Dec	12613182
Neuraminidase inhibitors in the management of influenza--experience of an outpatient practice.	2002 Dec	12458352
Problems of case and disease management in outpatient treatment of influenza.	2002 Dec	12458346
Management of viral infections in immunocompromised cancer patients.	2002 Jul 13	12428191
[A revolutionary change in the diagnosis and treatment of influenza].	2002 Jun	12227179
Influenza vaccination for healthy children.	2002 Jun	12015463
Influenza in the acute hospital setting.	2002 Mar	11944184
Structural studies of the resistance of influenza virus neuramindase to inhibitors.	2002 May 23	12014958
[Neuraminidase inhibitor permitted. The first pill against influenza].	2002 Oct 10	12474367
Characterization of 2 influenza A(H3N2) clinical isolates with reduced susceptibility to neuraminidase inhibitors due to mutations in the hemagglutinin gene.	2002 Oct 15	12355356
The treatment of influenza with antiviral drugs.	2003 Jan 7	12515786

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 `Fri Dec 15 15:44:25 GMT 2023` Edited by `admin` on `Fri Dec 15 15:44:25 GMT 2023`
Record UNII	20O93L6F9H
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

OSELTAMIVIR

Official 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

GS 4104

Code

English

OSELTAMIVIR [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C281