API reference
Lamivudine
- CAS number
- 134678-17-4
- Molecular formula
- C8H11N3O3S
- Molecular weight
- 229.26 g/mol
About this molecule
Lamivudine is a synthetic nucleoside analogue with activity against hepatitis B virus (HBV) and HIV. Intracellularly, lamivudine is phosphorylated to its active metabolites, lamiduvine triphosphate (L-TP) and lamiduvine monophosphate (L-MP). In HIV, L-TP inhibits HIV-1 reverse transcriptase (RT) via DNA chain termination after incorporation of the nucleoside analogue into viral DNA. In HBV, incorporation of L-MP into viral DNA by HBV polymerase results in DNA chain termination. L-TP is a weak inhibitor of mammalian DNA polymerases alpha and beta, and mitochondrial DNA polymerase. (NCI04)
Source: NCI Thesaurus (NCIt), via PubChem.
Identifiers
- IUPAC name
- 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
- InChIKey
- JTEGQNOMFQHVDC-NKWVEPMBSA-N
- SMILES
- C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
- Other CAS numbers recorded
- 136891-12-8 · 1117764-41-6
- PubChem CID
- 60825
Also known as
lamivudine · Epivir · Zeffix · Epivir-HBV · VIROLAM · (-)-2'-Deoxy-3'-thiacytidine · 3'-Thia-2',3'-dideoxycytidine · Lamivudine teva
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