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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
Supplier Information
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Formula Source
C16H28N2O4 ChEBI
Net Charge 0
Average Mass 312.40450
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): 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.
environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
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.
View more on the ChEBI Ontology
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
INNs Sources
oséltamivir ChEBI
oseltamivir ChEBI
oseltamivir ChemIDplus
oseltamivirum ChEBI
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
Brand Names Sources
Agucort KEGG DRUG
Tamiflu ChEBI
Database Links Databases
C08092 KEGG COMPOUND
D08306 KEGG DRUG
DB00198 DrugBank
HMDB14343 HMDB
Oseltamivir Wikipedia
US5763483 Patent
View more database links
Registry Numbers Types Sources
196618-13-0 CAS Registry Number KEGG COMPOUND
196618-13-0 CAS Registry Number ChemIDplus
8003908 Reaxys Registry Number Reaxys
8003908 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11075941 PubMed citation CiteXplore
11270942 PubMed citation CiteXplore
11825310 PubMed citation CiteXplore
17912363 PubMed citation CiteXplore
18559644 PubMed citation CiteXplore
18936828 PubMed citation CiteXplore
19355841 PubMed citation CiteXplore
19439487 PubMed citation CiteXplore
19557131 PubMed citation CiteXplore
19884755 PubMed citation CiteXplore
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
 
Last Modified
03 noviembre 2014

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