PharmGKB: The Pharmacogenomics Knowledge Base

Drug/Small Molecule:
lamivudine

2D structure

Overview

Generic Names: Lamivudine [Usan:Ban:Inn]; lamivudine
Trade Names: 3TC; Epivir; Epivir-HBV; Epzicom; Hepitec; Heptovir; Zeffix
Brand Mixtures: Combivir (Lamivudine + Zidovudine); Kivexa (Abacavir (Abacavir Sulfate) + Lamivudine); Trizivir (Abacavir (Abacavir Sulfate) + Lamivudine + Zidovudine)
PharmGKB Accession Id: PA450163

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 HIV disease. PubChem (source: Drug Bank)

Indication

For the treatment of HIV infection and chronic hepatitis B (HBV). (source: Drug Bank)

ATC Therapeutic Category

  • J05AF:Nucleoside and nucleotide reverse transcriptase inhibitors

Pharmacology, Interactions, and Contraindications

Mechanism 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. (source: Drug Bank)

Pharmacology

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. (source: Drug Bank)

Food Interactions

Take without regard to meals. Food does not decrease the extent of absorption, but it decreases the Cmax by slowing the rate of absorption. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

The only detected metabolite of lamivudine is trans-sulfoxide. (source: Drug Bank)

Protein Binding

36% (source: Drug Bank)

Absorption

Lamivudine was rapidly absorbed after oral administration in HIV-infected patients. Absolute bioavailability in adults is 86% ± 16% for the tablet and 87% ± 13% for the oral solution. (source: Drug Bank)

Isomeric SMILES Code:

C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N (source: Drug Bank)

Curated Annotations (Curated Annotation)

  1. rs2231142 at chr4:89271347 in ABCG2
    control size=7; K141 cases=6; PK=in healthy subjects, disposition of lamivudine was not significantly influenced by known functional variants
    Variant Name:
    ABCG2:421C>A; ABCG2:Q141K;
    Related Drugs:
    lamivudine
    Evidence:
    PMID:17509035
  2. rs72552713 at chr4:89271981 in ABCG2
    control size=7; X126 cases=6; PK=in healthy subjects, disposition of lamivudine was not significantly influenced by known functional variants
    Variant Name:
    ABCG2:Q126X
    Related Drugs:
    lamivudine
    Evidence:
    PMID:17509035
  3. rs2231137 at chr4:89280138 in ABCG2
    control size=7; M12 cases=6; PK=in healthy subjects, disposition of lamivudine was not significantly influenced by known functional variants
    Variant Name:
    ABCG2:V12M
    Related Drugs:
    lamivudine
    Evidence:
    PMID:17509035
Variant names are different names that have been used in the literature and other resources to refer to the same variant.

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Not annotated
ABCC4
  •   
  •   
  • PK
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
ABHD2
  •   
  • PD
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
ACVR2B
  •   
  • PD
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
CDC34
  •   
  • PD
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
EREG
  •   
  • PD
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
KHDRBS3
  •   
  • PD
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
RORA
  •   
  • PD
  •   
  • FA
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
SLC22A1
  •   
  •   
  • PK
  •   
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
SLC22A2
  •   
  •   
  • PK
  •   
  •   
Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
SLC22A3
  •   
  •   
  • PK
  •   
  •   
Publications

A list of non-curated publications that mention this drug along with other genes is available.

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
zalcitabine Uncurated Annotation Lamivudine decreases the efficacy of zalcitabine (source: Drug Bank)

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Hepatitis B
  •   
  • PD
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
HIV
  •   
  •   
  • PK
  •   
  • GN
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. Physicochemical determinants of human renal clearance

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00709
KEGG Compound ID:
C07065
KEGG Drug ID:
D00353
PubChem Compound ID:
60825
PubChem Substance ID:
197069

Common Searches

Search PubMed
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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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