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 | H3O4P |
Molecular Weight | 97.9952 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/11270942Curator's Comment: Description was created based on several sources, including
http://www.fda.gov/downloads/drugs/drugsafety/informationbydrugclass/ucm147992.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18676886
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16125799 |
1.34 nM [IC50] | ||
Target ID: CHEMBL3377 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16125799 |
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 Date9.409824E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 |
---|---|---|---|---|
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 |
|
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 |
|
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 |
|
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 Dose: 1000 mg Route: oral Route: single Dose: 1000 mg Sources: Page: p.841 |
healthy, 18-55 n = 6 Health Status: healthy Age Group: 18-55 Sex: M Population Size: 6 Sources: 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: Page: p.841 |
healthy, 18-55 n = 6 Health Status: healthy Age Group: 18-55 Sex: M Population Size: 6 Sources: 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: 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: 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: Page: p.10 |
unhealthy n = 1171 Health Status: unhealthy Condition: Influenza Sex: M+F Population Size: 1171 Sources: Page: p.10 |
Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (rare) Sources: Page: p.10Vomiting (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: Page: p.10 |
unhealthy n = 1171 Health Status: unhealthy Condition: Influenza Sex: M+F Population Size: 1171 Sources: 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: Page: p.10 |
unhealthy n = 1171 Health Status: unhealthy Condition: Influenza Sex: M+F Population Size: 1171 Sources: Page: p.10 |
PubMed
Title | Date | PubMed |
---|---|---|
Impact of patient characteristics on the risk of influenza/ILI-related complications. | 2001 |
|
Are we ready for the next flu pandemic? | 2001 Dec |
|
Treatment of influenza with neuraminidase inhibitors: virological implications. | 2001 Dec 29 |
|
Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity. | 2001 Dec 6 |
|
Adverse cutaneous reactions to influenza vaccinations and chemotherapy. | 2001 Jul |
|
Antiviral agents for influenza, hepatitis C and herpesvirus, enterovirus and rhinovirus infections. | 2001 Jul 16 |
|
Utilization of alpha-1-acid glycoprotein levels in the serum as a parameter for in vivo assay of influenza virus inhibitors. | 2001 Nov |
|
Synthesis of influenza neuraminidase inhibitors. | 2001 Nov |
|
Oseltamivir: a clinical and pharmacological perspective. | 2001 Oct |
|
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 |
|
Summaries for patients. Influenza vaccination or antiviral treatment for healthy working adults: an economic analysis. | 2002 Aug 20 |
|
Oseltamivir for influenza. | 2002 Dec |
|
Early therapy with the neuraminidase inhibitor oseltamivir maximizes its efficacy in influenza treatment. | 2002 Dec |
|
Design, synthesis, and neuraminidase inhibitory activity of GS-4071 analogues that utilize a novel hydrophobic paradigm. | 2002 Dec 2 |
|
Influenza B infection associated with encephalitis: treatment with oseltamivir. | 2002 Feb |
|
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 |
|
Influenza in the nursing home. | 2002 Jan 1 |
|
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 |
|
Influenza. | 2002 Jun |
|
[A revolutionary change in the diagnosis and treatment of influenza]. | 2002 Jun |
|
Influenza vaccination for healthy children. | 2002 Jun |
|
Influenza in the acute hospital setting. | 2002 Mar |
|
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 |
|
Influenza surveillance with rapid diagnostic tests. | 2002 May 15 |
|
Structural studies of the resistance of influenza virus neuramindase to inhibitors. | 2002 May 23 |
|
[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 |
|
Characterization of 2 influenza A(H3N2) clinical isolates with reduced susceptibility to neuraminidase inhibitors due to mutations in the hemagglutinin gene. | 2002 Oct 15 |
|
Current strategies for management of influenza in the elderly population. | 2002 Sep 15 |
|
Influenza prevention 2002-2003. | 2002 Sep 2 |
|
[Influenza: a new treatment, oseltamivir]. | 2002 Sep-Oct |
|
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 |
|
Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir. | 2003 Feb 24 |
|
[Oral neuraminidase inhibitor and an early warning system. New weapons against influenza]. | 2003 Jan 23 |
|
Oseltamivir for treatment of influenza in healthy adults: pooled trial evidence and cost-effectiveness model for Canada. | 2003 Mar-Apr |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22192867
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
Edited
Fri Dec 16 20:07:37 UTC 2022
by
admin
on
Fri Dec 16 20:07:37 UTC 2022
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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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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C281
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DTXSID0044230
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SUB12544MIG
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M8256
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PRIMARY | Merck Index | ||
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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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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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||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
|
||
|
PARENT -> SALT/SOLVATE |
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.
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
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.
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
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.
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
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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Related Record | Type | Details | ||
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ACTIVE MOIETY |