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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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	Inhibitor 8,504		1.34 nM [IC50]
Neuraminidase 21	Inhibitor 8,504		13.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Influenza virus infections 34	Primary		Approved 8,583	TAMIFLU

C_max

Value	Dose	Analyte	Population
441 μg/L	150 mg single, oral	OSELTAMIVIR ACID plasma	Homo sapiens
551 μg/L	150 mg single, oral	OSELTAMIVIR ACID plasma	Homo sapiens
230 μg/L	50 mg 2 times / day steady-state, oral	OSELTAMIVIR ACID plasma	Homo sapiens
439 μg/L	100 mg 2 times / day steady-state, oral	OSELTAMIVIR ACID plasma	Homo sapiens
1132 μg/L	200 mg 2 times / day steady-state, oral	OSELTAMIVIR ACID plasma	Homo sapiens
2458 μg/L	500 mg 2 times / day steady-state, oral	OSELTAMIVIR ACID plasma	Homo sapiens
348 ng/mL	75 mg 2 times / day multiple, oral	OSELTAMIVIR ACID plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
6069 μg × h/L	150 mg single, oral	OSELTAMIVIR ACID plasma	Homo sapiens
6218 μg × h/L	150 mg single, oral	OSELTAMIVIR ACID plasma	Homo sapiens
2107 μg × h/L	50 mg 2 times / day steady-state, oral	OSELTAMIVIR ACID plasma	Homo sapiens
3845 μg × h/L	100 mg 2 times / day steady-state, oral	OSELTAMIVIR ACID plasma	Homo sapiens
8612 μg × h/L	200 mg 2 times / day steady-state, oral	OSELTAMIVIR ACID plasma	Homo sapiens
20317 μg × h/L	500 mg 2 times / day steady-state, oral	OSELTAMIVIR ACID plasma	Homo sapiens
2719 ng × h/mL	75 mg 2 times / day multiple, oral	OSELTAMIVIR ACID plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
8.2 h	150 mg single, oral	OSELTAMIVIR ACID plasma	Homo sapiens
6.87 h	150 mg single, oral	OSELTAMIVIR ACID plasma	Homo sapiens
8 h	75 mg 2 times / day multiple, oral	OSELTAMIVIR ACID plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
97%	75 mg 2 times / day multiple, oral		OSELTAMIVIR ACID plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
1000 mg single, oral Highest studied dose	healthy, 18-55
500 mg 2 times / day multiple, oral Highest studied dose	healthy, 18-55
450 mg 2 times / day multiple, oral Higher than recommended	healthy, 33.9±11.52
75 mg 2 times / day multiple, oral Recommended	unhealthy	Disc. AE: Nausea, Vomiting...

Showing 1 to 4 of 4 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Nausea	rare Disc. AE	75 mg 2 times / day multiple, oral Recommended	unhealthy
Vomiting	rare Disc. AE	75 mg 2 times / day multiple, oral Recommended	unhealthy

Showing 1 to 2 of 2 entries

Previous1Next

Sourcing

Sourcing

Show entries

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

Showing 1 to 4 of 4 entries

Previous1Next

PubMed

Show entries

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	11043756
Pharmacokinetics and dosage recommendations for an oseltamivir oral suspension for the treatment of influenza in children.	2001	11310719
Oseltamivir: a review of its use in influenza.	2001	11270942
Are we ready for the next flu pandemic?	2001 Dec	11871800
Management of influenza in patients with asthma or chronic obstructive pulmonary disease.	2001 Dec	11770690

Showing 1 to 5 of 21 entries

Previous1 2 3 4 5Next

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
Record UNII	K6106LV5Q8
Record Status	`Validated (UNII)`
Record Version

Show entries

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

Showing 1 to 5 of 14 entries

Previous1 2 3Next

Show entries

Code System

Code

Type

Description

RXCUI

1546279

PRIMARY

RxNorm

FDA UNII

K6106LV5Q8

PRIMARY

CHEBI

73139

PRIMARY

DRUG BANK

DB02600

PRIMARY

CAS

187227-45-8

PRIMARY

Showing 1 to 5 of 8 entries

Previous1 2Next

Show entries

Related Record

Type

Details


					R9HH0NDE2E

INFLUENZA A VIRUS WHOLE

TARGET ORGANISM->INHIBITOR

Amount:


					R9HH0NDE2E

INFLUENZA A VIRUS WHOLE

TARGET ORGANISM->INHIBITOR

Amount:

Showing 1 to 2 of 2 entries

Previous1Next

Show entries

Related Record

Type

Details


					4A3O49NGEZ

OSELTAMIVIR PHOSPHATE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

WEIGHT PERCENT [<0.3] % (limits)
PEAK VALUE

Showing 1 to 1 of 1 entries

Previous1Next

Show entries

Related Record

Type

Details


					K6106LV5Q8

OSELTAMIVIR ACID

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound