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 |
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 |
|---|---|---|---|---|
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 |
|---|---|---|
| Development of a high-performance liquid chromatographic-mass spectrometric assay for the specific and sensitive quantification of Ro 64-0802, an anti-influenza drug, and its pro-drug, oseltamivir, in human and animal plasma and urine. | 2000 Aug 18 |
|
| Unprepared for an influenza pandemic. | 2001 Aug 25 |
|
| Are we ready for the next flu pandemic? | 2001 Dec |
|
| Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity. | 2001 Dec 6 |
|
| Update on treatment of influenza A and B with tamiflu. | 2001 Feb 15 |
|
| [What is current opinion of antiviral therapy for the flu in 2001?]. | 2001 Jan |
|
| Prophylactic and symptomatic treatment of influenza. Current and developing options. | 2001 Jan |
|
| Zanamivir and oseltamivir: two new options for the treatment and prevention of influenza. | 2001 Mar |
|
| Experience with oseltamivir in the control of a nursing home influenza B outbreak. | 2001 Mar 1 |
|
| 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 |
|
| Synthesis of influenza neuraminidase inhibitors. | 2001 Nov |
|
| Vaccines for pneumonia and new antiviral therapies. | 2001 Nov |
|
| ACIP releases guidelines on the prevention and control of influenza. Advisory Committee on Immunization Practices. | 2001 Oct 1 |
|
| Highlights in the development of new antiviral agents. | 2002 Apr |
|
| Antiviral therapy of influenza. | 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 |
|
| Efficacy and safety of zanamivir in patients with influenza--impact of age, severity of infections and specific risk factors. | 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 |
|
| 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 |
|
| Influenza in the nursing home. | 2002 Jan 1 |
|
| Management of viral infections in immunocompromised cancer patients. | 2002 Jul 13 |
|
| [A revolutionary change in the diagnosis and treatment of influenza]. | 2002 Jun |
|
| Susceptibility of recent Canadian influenza A and B virus isolates to different neuraminidase inhibitors. | 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 |
|
| 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 |
|
| Structural studies of the resistance of influenza virus neuramindase to inhibitors. | 2002 May 23 |
|
| [Neuraminidase inhibitor permitted. The first pill against influenza]. | 2002 Oct 10 |
|
| Influenza prevention 2002-2003. | 2002 Sep 2 |
|
| Influenza diagnosis and treatment in children: a review of studies on clinically useful tests and antiviral treatment for influenza. | 2003 Feb |
|
| Synthesis and anti-influenza evaluation of orally active bicyclic ether derivatives related to zanamivir. | 2003 Feb 24 |
|
| Early administration of oral oseltamivir increases the benefits of influenza treatment. | 2003 Jan |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:25:33 GMT 2023
by
admin
on
Fri Dec 15 16:25:33 GMT 2023
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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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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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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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||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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||
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|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
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 |
|
||
|
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.
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||
|
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.
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
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 |