CHEBI:63577 - lamivudine

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ChEBI Name lamivudine
ChEBI ID CHEBI:63577
Definition A monothioacetal that consists of cytosine having a (2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl moiety attached at position 1. An inhibitor of HIV-1 reverse transcriptase, it is used as an antiviral in the treatment of AIDS and hepatitis B.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:6366
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Formula C8H11N3O3S
Net Charge 0
Average Mass 229.25600
Monoisotopic Mass 229.052
InChI InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1
InChIKey JTEGQNOMFQHVDC-NKWVEPMBSA-N
SMILES Nc1ccn([C@@H]2CS[C@H](CO)O2)c(=O)n1
Roles Classification
Biological Role(s): HIV-1 reverse transcriptase inhibitor
An entity which inhibits the activity of HIV-1 reverse transcriptase.
antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
allergen
A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
A DNA polymerase inhibitor that interferes with the activity of reverse transcriptase, EC 2.7.7.49, a viral DNA polymerase enzyme that retroviruses need in order to reproduce.
anti-HBV agent
An antiviral agent that destroys or inhibits the replication of the hepatitis B virus.
Application(s): antiviral drug
A substance used in the prophylaxis or therapy of virus diseases.
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.
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ChEBI Ontology
Outgoing lamivudine (CHEBI:63577) has functional parent cytosine (CHEBI:16040)
lamivudine (CHEBI:63577) has role allergen (CHEBI:50904)
lamivudine (CHEBI:63577) has role anti-HBV agent (CHEBI:64951)
lamivudine (CHEBI:63577) has role antiviral drug (CHEBI:36044)
lamivudine (CHEBI:63577) has role EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor (CHEBI:59897)
lamivudine (CHEBI:63577) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
lamivudine (CHEBI:63577) has role prodrug (CHEBI:50266)
lamivudine (CHEBI:63577) is a monothioacetal (CHEBI:59793)
lamivudine (CHEBI:63577) is a nucleoside analogue (CHEBI:60783)
lamivudine (CHEBI:63577) is a oxacycle (CHEBI:38104)
lamivudine (CHEBI:63577) is a primary alcohol (CHEBI:15734)
IUPAC Name
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2(1H)-one
INN Source
lamivudine KEGG DRUG
Synonyms Sources
(-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine ChemIDplus
(-)-2'-Deoxy-3'-thiacytidine ChemIDplus
2',3'-Dideoxy-3'-thiacytidine KEGG COMPOUND
3'-Thia-2',3'-dideoxycytidine ChemIDplus
3TC KEGG COMPOUND
beta-L-2',3'-Dideoxy-3'-thiacytidine ChemIDplus
beta-L-3'-Thia-2',3'-dideoxycytidine ChemIDplus
Lamivudine KEGG COMPOUND
Brand Name Source
Epivir KEGG DRUG
Manual Xrefs Databases
1539 DrugCentral
3TC PDBeChem
C07065 KEGG COMPOUND
D00353 KEGG DRUG
DB00709 DrugBank
Lamivudine Wikipedia
LSM-5215 LINCS
WO9117159 Patent
View more database links
Registry Numbers Types Sources
134678-17-4 CAS Registry Number KEGG COMPOUND
134678-17-4 CAS Registry Number ChemIDplus
5480511 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
19 June 2018