CHEBI:31536 - emtricitabine

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ChEBI Name emtricitabine
ChEBI ID CHEBI:31536
Definition An organofluorine compound that is 5-fluorocytosine substituted at the 1 position by a 2-(hydroxymethyl)-1,3-oxathiolan-5-yl group (2R,5S configuration). It is used in combination therapy for the treatment of HIV-1 infection.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:174911
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Formula C8H10FN3O3S
Net Charge 0
Average Mass 247.24700
Monoisotopic Mass 247.043
InChI InChI=1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1
InChIKey XQSPYNMVSIKCOC-NTSWFWBYSA-N
SMILES Nc1nc(=O)n(cc1F)[C@@H]1CS[C@H](CO)O1
Roles Classification
Biological Role(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
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ChEBI Ontology
Outgoing emtricitabine (CHEBI:31536) has role antiviral drug (CHEBI:36044)
emtricitabine (CHEBI:31536) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
emtricitabine (CHEBI:31536) is a monothioacetal (CHEBI:59793)
emtricitabine (CHEBI:31536) is a nucleoside analogue (CHEBI:60783)
emtricitabine (CHEBI:31536) is a organofluorine compound (CHEBI:37143)
emtricitabine (CHEBI:31536) is a pyrimidone (CHEBI:38337)
Incoming Descovy (CHEBI:133007) has part emtricitabine (CHEBI:31536)
Genvoya (CHEBI:90922) has part emtricitabine (CHEBI:31536)
Odefsey (CHEBI:133010) has part emtricitabine (CHEBI:31536)
IUPAC Name
4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one
Synonyms Sources
(−)-(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine ChEBI
(−)-2'-deoxy-5-fluoro-3'-thiacytidine ChemIDplus
(−)-β-2',3'-dideoxy-5-fluoro-3'-thiacytidine ChEBI
(−)-cis-4-amino-5-fluoro-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one ChEBI
(−)-FTC ChemIDplus
(2R-cis)-4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone ChemIDplus
4-amino-5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one ChEMBL
4-Amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-1H-pyrimidin-2-one ChEMBL
5-fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine ChemIDplus
EMTRICITABINE ChEMBL
Emtricitabine KEGG COMPOUND
Manual Xrefs Databases
1003 DrugCentral
C12599 KEGG COMPOUND
D01199 KEGG DRUG
DB00879 DrugBank
Emtricitabine Wikipedia
ETV PDBeChem
US5538975 Patent
WO9214743 Patent
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Registry Numbers Types Sources
143491-57-0 CAS Registry Number KEGG COMPOUND
143491-57-0 CAS Registry Number ChemIDplus
5908714 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017
General Comment
2011-03-17 An analogue of cytidine, emtricitabine is a nucleoside reverse transcriptase inhibitor, with antiretroviral activity against HIV, and is used with other antiretrovirals in combination therapy of HIV infection. It is also active against hepatitis B virus.