Lamivudine

Lamivudine

Cat Number
API134678174
CAS Number
134678-17-4

For research use only. We do not supply to patients.

For pharmaceutical-grade products or other inquiries, please contact our experts.

CAS Number
134678-17-4
EINECS
603-844-3
Storage
Store at room temperature
Synonyms
Epivir; Zeffix; 4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one; (-)-2'-Deoxy-3'-thiacytidine; GR-109714X; VIROLAM
Molecular Formula
C8H11N3O3S
Molecular Weight
229.26
Smiles
C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
Appearance
White crystalline powder
Melting Point
177°C
Boiling Point
475.4±55.0°C at 760 mmHg
Relative Density
1.73±0.1
General Description
Lamivudine is a synthetic cytidine analogue with a sulfur atom replacing the oxygen in the sugar ring, belonging to the class of nucleoside reverse transcriptase inhibitors (NRTIs). Its chemical structure is 2′,3′-dideoxy-3′-thiacytidine, with a molecular weight of 229.3 Da. The molecule has a chiral center, and the (-)-enantiomer is the pharmacologically active form.
Mechanism of Action
Lamivudine is phosphorylated intracellularly to the active triphosphate, which competes with the natural substrate deoxycytidine triphosphate for incorporation into the viral DNA. Once incorporated, it acts as a chain terminator, preventing further elongation of the DNA strand. This inhibits the replication of HIV-1 and hepatitis B virus (HBV). The drug has a low affinity for host DNA polymerases, reducing its toxicity.
Application
Lamivudine is indicated for the treatment of HIV-1 infection in combination with other antiretroviral agents and for the treatment of chronic hepatitis B infection. It is effective in reducing viral load and increasing CD4 cell count in HIV patients, and in suppressing HBV DNA levels and improving liver function in HBV patients. The drug is also used for pre-exposure prophylaxis (PrEP) in combination with tenofovir disoproxil fumarate.

Lamivudine has remained a cornerstone of HIV therapy for over two decades. This review highlights its pharmacologic and virologic propertie, potent reverse transcriptase inhibition without human polymerase toxicity, that have enabled its continued use in modern combination regimens. Beyond traditional triple-drug therapy, lamivudine is now incorporated into single-tablet regimens to improve adherence and into emerging two-drug regimens designed to reduce long-term cumulative drug exposure. Its versatility and favorable safety profile make it indispensable in both resource-rich and resource-limited settings.

Fig. 1 Proportion of patients in individual studies who achieved viral load <50 copies per milliliter after 48 or 52 weeks on therapy. (Quercia R, <i>et al</i>., 2018) Fig. 1 Proportion of patients in individual studies who achieved viral load <50 copies per milliliter after 48 or 52 weeks on therapy. (Quercia R, et al., 2018)

References

  1. Quercia R, et al. Twenty-Five Years of Lamivudine: Current and Future Use for the Treatment of HIV-1 Infection. J Acquir Immune Defic Syndr. 2018;78(2):125-135.

In a double‑blind trial of 24 patients with center‑involved diabetic macular edema, oral lamivudine (150 mg twice daily) improved best‑corrected visual acuity by 9.8 letters at 4 weeks (vs. a 1.8‑letter decrease with placebo; P<0.001). At 8 weeks, lamivudine plus bevacizumab improved BCVA by 16.9 letters vs. 5.3 with placebo+bevacizumab. Lamivudine, an oral inflammasome inhibitor, significantly improves vision in DME and may be a low‑cost alternative to anti‑VEGF injections.

Fig. 2 Change in Visual Acuity. (Pereira F, <i>et al</i>., 2025) Fig. 2 Change in Visual Acuity. (Pereira F, et al., 2025)

References

  1. Pereira F, et al. Oral lamivudine in diabetic macular edema: A randomized, double-blind, placebo-controlled clinical trial. Med. 2025;6(9):100747.

Does Lamivudine require protection from light and moisture during long-term storage?

Yes, it is photosensitive and slightly hygroscopic. Store in light-resistant, tightly sealed containers with desiccant to prevent photodegradation and hydrolysis of the thiazolidine ring.

What is the recommended storage temperature for Lamivudine?

Store at controlled room temperature (15–25°C). Avoid excessive heat above 30°C, which can accelerate degradation of the nucleoside analog.

Is Lamivudine stable in solution for oral use?

Aqueous solutions are stable when protected from light and stored at room temperature.

How is the impurity lamivudine enantiomer (the R‑isomer) monitored during stability?

We use a validated chiral HPLC method to monitor enantiomeric purity, ensuring the S‑enantiomer remains above pharmacopoeial limits.
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