Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H28N2O4.H3O4P |
| Molecular Weight | 410.3997 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OP(O)(O)=O.CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1
InChI
InChIKey=PGZUMBJQJWIWGJ-ONAKXNSWSA-N
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
| 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 | H3O4P |
| Molecular Weight | 97.9952 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
http://www.fda.gov/downloads/drugs/drugsafety/informationbydrugclass/ucm147992.pdf
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2051 |
1.34 nM [IC50] | ||
Target ID: CHEMBL3377 |
13.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TAMIFLU Approved UseTAMIFLU 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 Date1999 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
441 μg/L |
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 |
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 |
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 |
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 |
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 |
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 |
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 | Co-administered | Analyte | Population |
|---|---|---|---|---|
6069 μg × h/L |
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 |
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 |
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 |
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 |
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 |
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 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
8.2 h |
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 |
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 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
97% |
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 |
healthy, 18-55 |
|
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: |
healthy, 18-55 |
|
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: |
healthy, 33.9±11.52 Health Status: healthy Age Group: 33.9±11.52 Sex: M+F Sources: |
|
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: |
unhealthy Health Status: unhealthy Sex: M+F Sources: |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (rare) Sources: Vomiting (rare) |
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: |
unhealthy Health Status: unhealthy Sex: M+F Sources: |
| 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: |
unhealthy Health Status: unhealthy Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Influence of treatment schedule and viral challenge dose on the in vivo influenza virus-inhibitory effects of the orally administered neuraminidase inhibitor GS 4104. | 1999 Jul |
|
| 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 |
|
| Are we ready for the next flu pandemic? | 2001 Dec |
|
| Cost-effectiveness of vaccination versus treatment of influenza in healthy adolescents and adults. | 2001 Dec 1 |
|
| Treatment of influenza with neuraminidase inhibitors: virological implications. | 2001 Dec 29 |
|
| [What is current opinion of antiviral therapy for the flu in 2001?]. | 2001 Jan |
|
| Symptom pathogenesis during acute influenza: interleukin-6 and other cytokine responses. | 2001 Jul |
|
| Advances in pharmacology. New treatments for influenza: neuraminidase inhibitors. | 2001 Jun |
|
| Position statement: global neuraminidase inhibitor susceptibility network. | 2001 Mar |
|
| 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 |
|
| New, azide-free transformation of epoxides into 1,2-diamino compounds: synthesis of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu). | 2001 Mar 23 |
|
| Utilization of alpha-1-acid glycoprotein levels in the serum as a parameter for in vivo assay of influenza virus inhibitors. | 2001 Nov |
|
| Vaccines for pneumonia and new antiviral therapies. | 2001 Nov |
|
| Oseltamivir: a clinical and pharmacological perspective. | 2001 Oct |
|
| Antivirals for influenza: what is their role in the older patient? | 2002 |
|
| Highlights in the development of new antiviral agents. | 2002 Apr |
|
| Antiviral therapy of influenza. | 2002 Apr |
|
| Use of oseltamivir during influenza outbreaks in Ontario nursing homes, 1999-2000. | 2002 Apr |
|
| Challenges and options in the management of viral infections after stem cell transplantation. | 2002 Apr |
|
| Prevention and control of influenza. Recommendations of the Advisory Committee on Immunization Practices (ACIP). | 2002 Apr 12 |
|
| 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 |
|
| Oseltamivir for influenza. | 2002 Dec |
|
| Neuraminidase inhibitors for the treatment and prevention of influenza. | 2002 Feb |
|
| Antiviral therapy for influenza virus infections. | 2002 Jan |
|
| 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 |
|
| 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 |
|
| Oseltamivir was safe and effective for prophylaxis of influenza in the frail elderly. | 2002 Jan-Feb |
|
| Susceptibility of recent Canadian influenza A and B virus isolates to different neuraminidase inhibitors. | 2002 Jun |
|
| 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 May |
|
| Experience with oseltamivir in the control of nursing home influenza A outbreak. | 2002 May |
|
| Influenza surveillance with rapid diagnostic tests. | 2002 May 15 |
|
| [New diagnostic possibilities and medications. Fit for influenza?]. | 2002 Nov 28 |
|
| Characterization of 2 influenza A(H3N2) clinical isolates with reduced susceptibility to neuraminidase inhibitors due to mutations in the hemagglutinin gene. | 2002 Oct 15 |
|
| Cost-effectiveness of newer treatment strategies for influenza. | 2002 Sep |
|
| 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 |
|
| Influenza diagnosis and treatment in children: a review of studies on clinically useful tests and antiviral treatment for influenza. | 2003 Feb |
|
| Logistic issues and potential prescribing costs associated with use of neuraminidase inhibitors for the treatment of influenza in primary care. | 2003 Feb |
|
| Antiviral drugs in the immunocompetent host: part II. Treatment of influenza and respiratory syncytial virus infections. | 2003 Feb 15 |
Sample Use Guides
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:27:32 GMT 2025
by
admin
on
Mon Mar 31 18:27:32 GMT 2025
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| Record UNII |
4A3O49NGEZ
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C281
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| Code System | Code | Type | Description | ||
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DTXSID0044230
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SUB12544MIG
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m8256
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KK-62
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C29305
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1479304
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CHEMBL1229
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4A3O49NGEZ
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7799
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78000
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100000091466
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4A3O49NGEZ
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204255-11-8
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OSELTAMIVIR PHOSPHATE
Created by
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PRIMARY | Description: A white to off-white powder. Solubility: Freely soluble in water and in methanol. Category: Antiviral. Storage: Oseltamivir phosphate should be kept in a well-closed container, protected from light. Additional information: Oseltamivir phosphate may show polymorphism. Definition: Oseltamivir phosphate contains not less than 97.5% and not more than 102.0% of oseltamivir phosphate (C16H28N2O4, H3PO4) using Assay method A, and not less than 98.5% and not more than 101.0% of oseltamivir phosphate (C16H28N2O4, H3PO4) using Assay method B, both calculated with reference to the anhydrous substance. | ||
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259275
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7798
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DB00198
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| Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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PARENT -> SALT/SOLVATE |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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IMPURITY -> PARENT |
Use the chromatogram obtained with solution (4) to identify the peaks due to impurities A, B, C and D. The impurity peaks are eluted at the following relative retention with reference to oseltamivir phosphate (retention time about 19 minutes): impurity A about 0.16. The test is not valid unless the resolution between the peaks due to impurities A and B and that between the peaks due to impurities C and D is at least 1.3.
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
|
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
Use the chromatogram obtained with solution (4) to identify the peaks due to impurities A, B, C and D. The impurity peaks are eluted at the following relative retention with reference to oseltamivir phosphate (retention time about 19 minutes): impurity C about 0.51. The test is not valid unless the resolution between the peaks due to impurities A and B and that between the peaks due to impurities C and D is at least 1.3.
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
Use the chromatogram obtained with solution (4) to identify the peaks due to impurities A, B, C and D. The impurity peaks are eluted at the following relative retention with reference to oseltamivir phosphate (retention time about 19 minutes): impurity B about 0.17. The test is not valid unless the resolution between the peaks due to impurities A and B and that between the peaks due to impurities C and D is at least 1.3.
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
Use the chromatogram obtained with solution (4) to identify the peaks due to impurities A, B, C and D. The impurity peaks are eluted at the following relative retention with reference to oseltamivir phosphate (retention time about 19 minutes): impurity D about 0.55. The test is not valid unless the resolution between the peaks due to impurities A and B and that between the peaks due to impurities C and D is at least 1.3.
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
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ACTIVE MOIETY |