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Product Details:

  • Product Name: Lamivudine
  • CAS #: 134678-17-4
  • Mode of Action:

    Lamivudine is a synthetic nucleoside analogue and is phosphorylated intracellularly to its active 5'-triphosphate metabolite, lamivudine triphosphate (L-TP). This nucleoside analogue is incorporated into viral DNA by HIV reverse transcriptase and HBV polymerase, resulting in DNA chain termination.

  • Pharmacodynamics:

    Lamivudine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV). Lamivudine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. The lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated.

  • Metabolism:

    The only detected metabolite of lamivudine is trans-sulfoxide.

  • IUPAC: 4-amino-1-[(2R, 5S)-2-(hydroxymethyl)-1, 3-oxathiolan-5-yl]-1, 2-dihydropyrimidin-2-one
  • ATC: J05AF05
  • PubChem: 73339
  • DrugBank: DB00709 (APRD00681)
  • Formula: C13H13N3O3
  • Molecular Mass: 229.256
  • Synonyms: Lamivudine [Usan:Ban:Inn]
  • SMILES: NC1=NC(=O)N(C=C1)[C@@H]1CS[C@H](CO)O1
  • AHFS Code: 08:18.08.20
  • General Reference:


    1. Fox Z, Dragsted UB, Gerstoft J, Phillips AN, Kjaer J, Mathiesen L, Youle M, Katlama C, Hill A, Bruun JN, Clumeck N, Dellamonica P, Lundgren JD: A randomized trial to evaluate continuation versus discontinuation of lamivudine in individuals failing a lamivudine-containing regimen: the COLATE trial. Antivir Ther. 2006;11(6):761-70. Pubmed


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