lamivudine (CHEBI:63577)

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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

Average Mass

229.25600

Monoisotopic Mass

229.05211

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, or part thereof, 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.

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

Last Modified

19 June 2018