Lamivudine

Products

We are here to help in anything you need. Please use our online system or send an email to .

Lamivudine

Inquiry

Catalog Number	PR134678174
CAS	134678-17-4
Description	A reverse transcriptase inhibitor and zalcitabine analog in which a sulfur atom replaces the 3' carbon of the pentose ring. It is used to treat Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B (HBV).
Synonyms	Epivir; Zeffix; Heptovir; Epivir-HBV
IUPAC Name	4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
Molecular Weight	229.26
Molecular Formula	C8H11N3O3S
InChI	JTEGQNOMFQHVDC-NKWVEPMBSA-N
InChI Key	InChI=1S/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m0/s1
Drug Categories	Agents Causing Muscle Toxicity; Anti-HIV Agents; Anti-Infective Agents; Anti-Retroviral Agents; Antiinfectives for Systemic Use; Antiviral Agents; Antivirals for Systemic Use; Antivirals used in combination for the treatment of HIV infections; BCRP/ABCG2 Substrates; Deoxycytidine; Deoxyribonucleosides; Dideoxynucleosides; Direct Acting Antivirals; Drugs that are Mainly Renally Excreted; Enzyme Inhibitors; Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor; Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor; Nucleic Acid Synthesis Inhibitors; Nucleic Acids, Nucleotides, and Nucleosides; Nucleoside and Nucleotide Reverse Transcriptase Inhibitors; Nucleoside Reverse Transcriptase Inhibitors; Nucleosides; OAT1/SLC22A6 Substrates; OCT1 substrates; OCT2 Substrates; P-glycoprotein substrates; Pyrimidine Nucleosides; Pyrimidines; Reverse Transcriptase Inhibitors
Drug Interactions	Abemaciclib-Abemaciclib may decrease the excretion rate of Lamivudine which could result in a higher serum level. Aceclofenac-Aceclofenac may decrease the excretion rate of Lamivudine which could result in a higher serum level. Acemetacin-Acemetacin may decrease the excretion rate of Lamivudine which could result in a higher serum level. Acetaminophen-Acetaminophen may decrease the excretion rate of Lamivudine which could result in a higher serum level. Acetazolamide-Acetazolamide may increase the excretion rate of Lamivudine which could result in a lower serum level and potentially a reduction in efficacy.
Half-Life	5 to 7 hours (healthy or HBV-infected patients)
Isomeric SMILES	C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
Type	Small Molecule
Therapeutic Category	Antivirals

Pharmacology

Indications

Lamivudine is primarily indicated for use in combination with other antiretroviral agents in the management of HIV infection and chronic hepatitis B (HBV). It is specifically employed alongside dolutegravir for the treatment of HIV-1 in patients aged 12 years and older who weigh at least 25 kg.

Pharmacodynamics

Lamivudine functions as a nucleoside reverse transcriptase inhibitor (NRTI) with demonstrable efficacy against Human Immunodeficiency Virus Type 1 (HIV-1) and hepatitis B virus (HBV). The drug undergoes phosphorylation to form active metabolites, which then compete with natural substrates for integration into viral DNA. This competitive inhibition effectively halts the activity of the HIV reverse transcriptase enzyme, thereby terminating DNA chain synthesis. The absence of a 3'-OH group in the incorporated nucleoside analogues impedes the crucial formation of a 5' to 3' phosphodiester linkage needed for DNA chain elongation.

Absorption

Lamivudine is efficiently absorbed following oral administration in individuals infected with HIV. The mean absolute bioavailability was established at 86% ± 16% for the 150-mg tablet and 87% ± 13% for the oral solution among 12 adult patients. A peak serum concentration (Cmax) of 1.5 ± 0.5 mcg/mL was observed when a dose of 2 mg/kg was administered twice daily to HIV-1 patients. It should be noted that the drug's absorption rate decreases when taken with food compared to a fasted state.

Metabolism

The metabolism of lamivudine constitutes a minor elimination pathway. Within humans, the sole identified metabolite is the trans-sulfoxide derivative, formed through sulfotransferase-mediated biotransformation.

Mechanism of Action

Lamivudine functions as a synthetic nucleoside analogue that undergoes intracellular phosphorylation to form its active metabolite, lamivudine triphosphate (L-TP). This metabolite is subsequently incorporated into viral DNA by the enzymes HIV reverse transcriptase and HBV polymerase. The incorporation of L-TP into viral DNA effectively leads to the termination of the DNA chain, thereby inhibiting viral replication.

It should be noted that our service is only used for research, not for clinical use.