Lamivudine

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

"3TC" redirects here. For the three-coach British electric trains sometimes known as 3TC, see British Rail Class 438. For the format of cricket, see 3TeamCricket.

Lamivudine
Clinical data
Trade namesEpivir, Epivir-HBV, Zeffix, others
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
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability86%
Protein bindingLess than 36%
Elimination half-life5 to 7 hours
ExcretionKidney (circa 70%)
Identifiers
  • 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=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)

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

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

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