OSELTAMIVIR ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H24N2O4
Molecular Weight	284.3514
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(CC)O[C@@H]1C=C(C[C@H](N)[C@H]1NC(C)=O)C(O)=O

InChI

InChIKey=NENPYTRHICXVCS-YNEHKIRRSA-N

InChI=1S/C14H24N2O4/c1-4-10(5-2)20-12-7-9(14(18)19)6-11(15)13(12)16-8(3)17/h7,10-13H,4-6,15H2,1-3H3,(H,16,17)(H,18,19)/t11-,12+,13+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C14H24N2O4
Molecular Weight	284.3514
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 8504		1.34 nM [IC50]
Neuraminidase 21 Target ID: CHEMBL3377 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16125799	Inhibitor 8504		13.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Influenza virus infections 34 Sources: http://www.fda.gov/downloads/drugs/drugsafety/informationbydrugclass/ucm147992.pdf	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

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

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	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

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	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

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
Antiviral drugs: current state of the art.	2001 Aug	11418355
Management of influenza in patients with asthma or chronic obstructive pulmonary disease.	2001 Dec	11770690
Perspectives on antiviral use during pandemic influenza.	2001 Dec 29	11779387
Systematic structure-based design and stereoselective synthesis of novel multisubstituted cyclopentane derivatives with potent antiinfluenza activity.	2001 Dec 6	11728184
Oral oseltamivir treatment of influenza in children.	2001 Feb	11224828
Update on treatment of influenza A and B with tamiflu.	2001 Feb 15	11237078
[What is current opinion of antiviral therapy for the flu in 2001?].	2001 Jan	11218299
Experience with oseltamivir in the control of a nursing home influenza B outbreak.	2001 Mar 1	11260987
Utilization of alpha-1-acid glycoprotein levels in the serum as a parameter for in vivo assay of influenza virus inhibitors.	2001 Nov	12018681
Synthesis of influenza neuraminidase inhibitors.	2001 Nov	11899618
Therapeutic options for the management of influenza.	2001 Oct	11764774
Antivirals for influenza: what is their role in the older patient?	2002	12390054
Antiviral therapy of influenza.	2002 Apr	12122950
DNA vaccine expressing conserved influenza virus proteins protective against H5N1 challenge infection in mice.	2002 Aug	12141964
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
Influenza B infection associated with encephalitis: treatment with oseltamivir.	2002 Feb	11840091
Gateways to clinical trials.	2002 Jan-Feb	11980386
Susceptibility of recent Canadian influenza A and B virus isolates to different neuraminidase inhibitors.	2002 Jun	12062387
Influenza vaccination for healthy children.	2002 Jun	12015463
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	12062393
Experience with oseltamivir in the control of nursing home influenza A outbreak.	2002 May	12058885
[New diagnostic possibilities and medications. Fit for influenza?].	2002 Nov 28	12532540
Lack of pharmacokinetic interaction between the oral anti-influenza neuraminidase inhibitor prodrug oseltamivir and antacids.	2002 Oct	12392584
Current strategies for management of influenza in the elderly population.	2002 Sep 15	12203171
Antiviral drugs in the immunocompetent host: part II. Treatment of influenza and respiratory syncytial virus infections.	2003 Feb 15	12613730
[Oral neuraminidase inhibitor and an early warning system. New weapons against influenza].	2003 Jan 23	12619232

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 `Mon Mar 31 22:35:09 GMT 2025` Edited by `admin` on `Mon Mar 31 22:35:09 GMT 2025`
Record UNII	K6106LV5Q8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OSELTAMIVIR ACID

Common Name

English

GS 4071

Preferred Name

English

1-CYCLOHEXENE-1-CARBOXYLIC ACID, 4-(ACETYLAMINO)-5-AMINO-3-(1-ETHYLPROPOXY)-, (3R,4R,5S)-

Systematic Name

English

RO-640802

Code

English

OSELTAMIVIR PHOSPHATE IMPURITY, OSELTAMIVIR ACID- [USP IMPURITY]

Common Name

English

OSELTAMIVIR ACID, (-)-

Common Name

English

OSELTAMIVIR FREE ACID

Common Name

English

(3R,4R,5S)-4-ACETYLAMINO-5-AMINO-3-(1-ETHYLPROPOXY)-1-CYCLOHEXENE-1-CARBOXYLIC ACID

Systematic Name

English

OSELTAMIVIR CARBOXYLATE

Common Name

English

OSELTAMIVIR PHOSPHATE IMPURITY C [EP IMPURITY]

Common Name

English

(3R,4R,5S)-4-ACETAMIDO-5-AMINO-3-(1-ETHYLPROPOXY)CYCLOHEX-1-ENE-1-CARBOXYLIC ACID

Systematic Name

English

GS-4071

Code

English

RO-64-0802

Code

English

GS4071

Code

English

Code System Code Type Description

RXCUI

1546279