Lamivudine

Lamivudine
Clinical data
Trade namesEpivir, Epivir-HBV, Zeffix, others[1]
Other names(−)-L-2′,3′-dideoxy-3′-thiacytidine
AHFS/Drugs.comMonograph
MedlinePlusa696011
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability86%
Protein bindingLess than 36%
Elimination half-life5 to 7 hours
ExcretionKidney (circa 70%)
Identifiers
IUPAC name
  • 2',3'-dideoxy-3'-thiacytidine 4-Amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.132.250
Chemical and physical data
FormulaC8H11N3O3S
Molar mass229.25 g·mol−1
3D model (JSmol)
SMILES
  • O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H](SC2)CO
InChI
  • 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+/m1/s1 Y
  • Key:JTEGQNOMFQHVDC-RQJHMYQMSA-N Y
 NY (what is this?)  (verify)

Lamivudine, commonly called 3TC, is an antiretroviral medication used to prevent and treat HIV/AIDS.[1] It is also used to treat chronic hepatitis B when other options are not possible.[1] It is effective against both HIV-1 and HIV-2.[1] It is typically used in combination with other antiretrovirals such as zidovudine, dolutegravir, and abacavir.[1] Lamivudine may be included as part of post-exposure prevention in those who have been potentially exposed to HIV.[1] Lamivudine is taken by mouth as a liquid or tablet.[1]

Common side effects include nausea, diarrhea, headaches, feeling tired, and cough.[1] Serious side effects include liver disease, lactic acidosis, and worsening hepatitis B among those already infected.[1] It is safe for people over three months of age and can be used during pregnancy.[1] The medication can be taken with or without food.[1] Lamivudine is a nucleoside reverse transcriptase inhibitor and works by blocking the HIV reverse transcriptase and hepatitis B virus polymerase.[1]

Lamivudine was patented in 1995 and approved for use in the United States in 1995.[7][8] It is on the World Health Organization's List of Essential Medicines.[9] It is available as a generic medication.[1]

  1. ^ a b c d e f g h i j k l m "Lamivudine". The American Society of Health-System Pharmacists. Archived from the original on 2 June 2016. Retrieved 31 July 2016.
  2. ^ "3TC (lamivudine, Epivir)". Catie. 2014. Retrieved 22 August 2022.
  3. ^ "Epivir- lamivudine tablet, film coated Epivir- lamivudine solution". DailyMed. 1 August 2020. Retrieved 28 November 2020.
  4. ^ "Epivir HBV- lamivudine tablet, film coated Epivir HBV- lamivudine solution". DailyMed. 17 August 2020. Retrieved 28 November 2020.
  5. ^ Cite error: The named reference Epivir EPAR was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Zeffix EPAR was invoked but never defined (see the help page).
  7. ^ Therapy of Viral Infections Volume 15 of Topics in Medicinal Chemistry. Springer. 2015. p. 6. ISBN 9783662467596. Archived from the original on 15 August 2016.
  8. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 506. ISBN 9783527607495.
  9. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
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