oseltamivir (CHEBI:7798)

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ChEBI Name	oseltamivir

ChEBI ID	CHEBI:7798

Definition	A cyclohexenecarboxylate ester that is the ethyl ester of oseltamivir acid. An antiviral prodrug (it is hydrolysed to the active free carboxylic acid in the liver), it is used to slow the spread of influenza.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:42582

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Formula

C16H28N2O4

Net Charge

Average Mass

312.40450

Monoisotopic Mass

312.20491

InChI

InChI=1S/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1

InChIKey

VSZGPKBBMSAYNT-RRFJBIMHSA-N

SMILES

CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1

Roles Classification
Chemical Role(s):	environmental contaminant Any minor or unwanted substance introduced into the environment that can have undesired effects. Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

Biological Role(s):	EC 3.2.1.18 (exo-alpha-sialidase) inhibitor An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell. xenobiotic A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means. antiviral drug A substance used in the prophylaxis or therapy of virus diseases.

Application(s):	prodrug A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. EC 3.2.1.18 (exo-alpha-sialidase) inhibitor An antiviral drug targeted at influenza viruses. Its mode of action consists of blocking the function of the viral neuraminidase protein (EC 3.2.1.18), thus preventing the virus from budding from the host cell. antiviral drug A substance used in the prophylaxis or therapy of virus diseases.

ChEBI Ontology
Outgoing	oseltamivir (CHEBI:7798) has role antiviral drug (CHEBI:36044) oseltamivir (CHEBI:7798) has role EC 3.2.1.18 (exo-α-sialidase) inhibitor (CHEBI:52425) oseltamivir (CHEBI:7798) has role environmental contaminant (CHEBI:78298) oseltamivir (CHEBI:7798) has role prodrug (CHEBI:50266) oseltamivir (CHEBI:7798) has role xenobiotic (CHEBI:35703) oseltamivir (CHEBI:7798) is a acetamides (CHEBI:22160) oseltamivir (CHEBI:7798) is a amino-acid ester (CHEBI:46668) oseltamivir (CHEBI:7798) is a cyclohexenecarboxylate ester (CHEBI:37529) oseltamivir (CHEBI:7798) is a primary amino compound (CHEBI:50994)

Incoming	oseltamivir phosphate (CHEBI:7799) has part oseltamivir (CHEBI:7798)

IUPAC Name

ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Synonyms	Sources
(−)-oseltamivir	ChEBI
1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R-(3α,4β,5α))-	ChemIDplus
Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate	ChemIDplus
GS-4104	ChemIDplus
HSDB 7433	ChemIDplus
Oseltamivir	KEGG COMPOUND

Last Modified

22 February 2017

General Comment
2014-10-29	Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag