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 8228		1.34 nM [IC50]
Neuraminidase 21 Target ID: CHEMBL3377 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16125799	Inhibitor 8228		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 8360	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 9.409824E11

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
Prophylaxis and treatment of influenza virus infection.	2001	11437694
Antiviral drugs: current state of the art.	2001 Aug	11418355
Unprepared for an influenza pandemic.	2001 Aug 25	11545086
Are we ready for the next flu pandemic?	2001 Dec	11871800
Cost-effectiveness of vaccination versus treatment of influenza in healthy adolescents and adults.	2001 Dec 1	11692300
Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity.	2001 Dec 6	11728184
Adverse cutaneous reactions to influenza vaccinations and chemotherapy.	2001 Jul	11678994
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
Advances in pharmacology. New treatments for influenza: neuraminidase inhibitors.	2001 Jun	11434154
Influenza pneumonia: a descriptive study.	2001 Jun	11399696
Position statement: global neuraminidase inhibitor susceptibility network.	2001 Mar	11428241
Flu experts fear countries are unprepared for a future pandemic.	2001 May 5	11356449
Therapeutic options for the management of influenza.	2001 Oct	11764774
ACIP releases guidelines on the prevention and control of influenza. Advisory Committee on Immunization Practices.	2001 Oct 1	11601808
Antiviral drugs with extra-cellular sites of action.	2001 Sep-Oct	11590665
Antivirals for influenza: what is their role in the older patient?	2002	12390054
Antiviral therapy of influenza.	2002 Apr	12122950
Challenges and options in the management of viral infections after stem cell transplantation.	2002 Apr	11904784
The management of influenza in people of working age.	2002 Aug	12181374
DNA vaccine expressing conserved influenza virus proteins protective against H5N1 challenge infection in mice.	2002 Aug	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 Aug	12103431
Economic analysis of influenza vaccination and antiviral treatment for healthy working adults.	2002 Aug 20	12186512
Oseltamivir for influenza.	2002 Dec	12613182
Efficacy and safety of zanamivir in patients with influenza--impact of age, severity of infections and specific risk factors.	2002 Dec	12458354
Early therapy with the neuraminidase inhibitor oseltamivir maximizes its efficacy in influenza treatment.	2002 Dec	12458353
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
Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm.	2002 Dec 2	12419376
Antiviral therapy for influenza virus infections.	2002 Jan	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 Jan	11927075
The anti-influenza drug oseltamivir exhibits low potential to induce pharmacokinetic drug interactions via renal secretion-correlation of in vivo and in vitro studies.	2002 Jan	11744606
Detection of influenza virus resistance to neuraminidase inhibitors by an enzyme inhibition assay.	2002 Jan	11684315
Oseltamivir was safe and effective for prophylaxis of influenza in the frail elderly.	2002 Jan-Feb	11829565
Management of viral infections in immunocompromised cancer patients.	2002 Jul 13	12428191
Influenza in the acute hospital setting.	2002 Mar	11944184
Accumulation of defective neuraminidase (NA) genes by influenza A viruses in the presence of NA inhibitors as a marker of reduced dependence on NA.	2002 Mar 1	11865415
Experience with oseltamivir in the control of nursing home influenza A outbreak.	2002 May	12058885
Influenza surveillance with rapid diagnostic tests.	2002 May 15	11981745
Lack of pharmacokinetic interaction between the oral anti-influenza neuraminidase inhibitor prodrug oseltamivir and antacids.	2002 Oct	12392584
[Influenza: a new treatment, oseltamivir].	2002 Sep-Oct	12476676
Influenza vaccination and antiviral therapy: is there a role for concurrent administration in the institutionalised elderly?	2003	12578397
Influenza diagnosis and treatment in children: a review of studies on clinically useful tests and antiviral treatment for influenza.	2003 Feb	12586981
Antiviral drugs in the immunocompetent host: part II. Treatment of influenza and respiratory syncytial virus infections.	2003 Feb 15	12613730
Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir.	2003 Feb 24	12639555
Early administration of oral oseltamivir increases the benefits of influenza treatment.	2003 Jan	12493796
[Oral neuraminidase inhibitor and an early warning system. New weapons against influenza].	2003 Jan 23	12619232
Oseltamivir for treatment of influenza in healthy adults: pooled trial evidence and cost-effectiveness model for Canada.	2003 Mar-Apr	12641862

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 `Wed Jul 05 23:13:08 UTC 2023` Edited by `admin` on `Wed Jul 05 23:13:08 UTC 2023`
Record UNII	20O93L6F9H
Record Status	`Validated (UNII)`
Record Version

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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