Molecular Identity
Lamivudine
4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
PubChem CID: 60825
Lamivudine is 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. It has a role as an antiviral drug, a prodrug, an allergen, a HIV-1 reverse transcriptase inhibitor, an EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor and an anti-HBV agent. It is a primary alcohol, an oxacycle, a monothioacetal and a nucleoside analogue. It is functionally related to a cytosine.
2D Structure
Properties
C8H11N3O3S
Molecular Formula
229.26
Molecular Weight
g/mol
229.0521
Exact Mass
Da
-0.9
XLogP
Drug-like (Lipinski: < 5)
113
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
4
H-Bond Acceptors
331
Complexity
SMILES
Canonical SMILES
SMILES: C1C(OC(S1)CO)N2C=CC(=NC2=O)NIsomeric SMILES
SMILES: C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)NSynonyms(20)
lamivudine134678-17-4EpivirZeffixEpivir-HBV4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one(-)-2'-Deoxy-3'-thiacytidineGR-109714XVIROLAM(-)-BCH-189GR109714X3'-Thia-2',3'-dideoxycytidineLamivudine tevabeta-L-2',3'-Dideoxy-3'-thiacytidinebeta-L-3'-Thia-2',3'-dideoxycytidine
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Lamivudine
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