Product Name

Lamivudine

CAS Number

134678-17-4

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Product Name:
Lamivudine
CAS Number:
134678-17-4
Indication:
For the treatment of HIV infection and chronic hepatitis B (HBV).
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
InChi:
JTEGQNOMFQHVDC-NKWVEPMBSA-N
General Reference:
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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