U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H28N2O4.ClH
Molecular Weight 348.865
Optical Activity ( - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OSELTAMIVIR HYDROCHLORIDE

SMILES

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

InChI

InChIKey=OHEGLAHLLCJYPX-ONAKXNSWSA-N
InChI=1S/C16H28N2O4.ClH/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);1H/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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

CNS Penetrant
2588
Curator's Comment: CNS penetration of oseltamivir and oseltamivir carboxylate is low in Japanese and Caucasian adults. Emerging data support the idea that oseltamivir and oseltamivir carboxylate have limited potential to induce or exacerbate CNS adverse events in individuals with influenza.

Originator

Gilead Sciences
24
Curator's Comment: Oseltamivir was invented and patented by Californian company Gilead Sciences in 1996. Swiss pharmaceutical company Hoffmann-La Roche (Roche) then purchased the rights to develop and market the drug worldwide under the trade name Tamiflu.

Approval Year

1999
175
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 1.34 nM [IC50]
Inhibitor
8504
 13.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Identifying research priorities on infections in older adults: proceedings of an interdisciplinary workshop.
2001
Pharmacokinetics and dosage recommendations for an oseltamivir oral suspension for the treatment of influenza in children.
2001
Antiviral drugs: current state of the art.
2001 Aug
Cost-effectiveness of vaccination versus treatment of influenza in healthy adolescents and adults.
2001 Dec 1
Perspectives on antiviral use during pandemic influenza.
2001 Dec 29
Update on treatment of influenza A and B with tamiflu.
2001 Feb 15
Neuraminidase inhibitors: zanamivir and oseltamivir.
2001 Jan
Adverse cutaneous reactions to influenza vaccinations and chemotherapy.
2001 Jul
Influenza pneumonia: a descriptive study.
2001 Jun
Zanamivir and oseltamivir: two new options for the treatment and prevention of influenza.
2001 Mar
Cyclopentane neuraminidase inhibitors with potent in vitro anti-influenza virus activities.
2001 Mar
Flu experts fear countries are unprepared for a future pandemic.
2001 May 5
Utilization of alpha-1-acid glycoprotein levels in the serum as a parameter for in vivo assay of influenza virus inhibitors.
2001 Nov
ACIP releases guidelines on the prevention and control of influenza. Advisory Committee on Immunization Practices.
2001 Oct 1
Antiviral drugs with extra-cellular sites of action.
2001 Sep-Oct
Antivirals for influenza: what is their role in the older patient?
2002
Antiviral therapy of influenza.
2002 Apr
Use of oseltamivir during influenza outbreaks in Ontario nursing homes, 1999-2000.
2002 Apr
Prevention and control of influenza. Recommendations of the Advisory Committee on Immunization Practices (ACIP).
2002 Apr 12
DNA vaccine expressing conserved influenza virus proteins protective against H5N1 challenge infection in mice.
2002 Aug
Oseltamivir for influenza.
2002 Dec
Early therapy with the neuraminidase inhibitor oseltamivir maximizes its efficacy in influenza treatment.
2002 Dec
Neuraminidase inhibitors in the management of influenza--experience of an outpatient practice.
2002 Dec
Problems of case and disease management in outpatient treatment of influenza.
2002 Dec
Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm.
2002 Dec 2
Detection of influenza virus resistance to neuraminidase inhibitors by an enzyme inhibition assay.
2002 Jan
Gateways to clinical trials.
2002 Jan-Feb
Oseltamivir was safe and effective for prophylaxis of influenza in the frail elderly.
2002 Jan-Feb
Management of viral infections in immunocompromised cancer patients.
2002 Jul 13
[A revolutionary change in the diagnosis and treatment of influenza].
2002 Jun
Influenza vaccination for healthy children.
2002 Jun
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
[Pneumonia diagnosis in the practice on the test-bench: how much diagnosis is necessary?].
2002 Mar 15
Experience with oseltamivir in the control of nursing home influenza A outbreak.
2002 May
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 May
[Effectiveness of oseltamivir treatment against influenza type A and type B infection in children].
2002 Nov
[New diagnostic possibilities and medications. Fit for influenza?].
2002 Nov 28
Lack of pharmacokinetic interaction between the oral anti-influenza neuraminidase inhibitor prodrug oseltamivir and antacids.
2002 Oct
Characterization of 2 influenza A(H3N2) clinical isolates with reduced susceptibility to neuraminidase inhibitors due to mutations in the hemagglutinin gene.
2002 Oct 15
Influenza prevention 2002-2003.
2002 Sep 2
Influenza vaccination and antiviral therapy: is there a role for concurrent administration in the institutionalised elderly?
2003
Neuraminidase inhibitors in pediatric patients: potential place in influenza therapy.
2003
Logistic issues and potential prescribing costs associated with use of neuraminidase inhibitors for the treatment of influenza in primary care.
2003 Feb
Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir.
2003 Feb 24
Oseltamivir for treatment of influenza in healthy adults: pooled trial evidence and cost-effectiveness model for Canada.
2003 Mar-Apr
Patents

Patents

7531687
4
EP2005945A2
4
US20100210868
4
US20100222427
4

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 Apr 02 11:28:02 GMT 2025
Edited
by admin
on Wed Apr 02 11:28:02 GMT 2025
Record UNII
XSC4R7KWN6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-CYCLOHEXENE-1-CARBOXYLIC ACID, 4-(ACETYLAMINO)-5-AMINO-3-(1-ETHYLPROPOXY)-, ETHYL ESTER, MONOHYDROCHLORIDE, (3R-(3.ALPHA.,4.BETA.,5.ALPHA.))-
Preferred Name English
OSELTAMIVIR HYDROCHLORIDE
Common Name English
1-CYCLOHEXENE-1-CARBOXYLIC ACID, 4-(ACETYLAMINO)-5-AMINO-3-(1-ETHYLPROPOXY)-, ETHYL ESTER, HYDROCHLORIDE (1:1), (3R,4R,5S)-
Systematic Name English
Code System Code Type Description
PUBCHEM
9928295
Created by admin on Wed Apr 02 11:28:02 GMT 2025 , Edited by admin on Wed Apr 02 11:28:02 GMT 2025
PRIMARY
CAS
204255-09-4
Created by admin on Wed Apr 02 11:28:02 GMT 2025 , Edited by admin on Wed Apr 02 11:28:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID90942607
Created by admin on Wed Apr 02 11:28:02 GMT 2025 , Edited by admin on Wed Apr 02 11:28:02 GMT 2025
PRIMARY
FDA UNII
XSC4R7KWN6
Created by admin on Wed Apr 02 11:28:02 GMT 2025 , Edited by admin on Wed Apr 02 11:28:02 GMT 2025
PRIMARY
Related Record Type Details
Structure of OSELTAMIVIR
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of OSELTAMIVIR
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966