Lamivudine

Lamivudine

Clinical data
Trade names	Epivir, others
AHFS/Drugs.com	Monograph
MedlinePlus	a696011
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	By mouth
ATC code	J05AF05 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	86%
Protein binding	Less than 36%
Biological half-life	5 to 7 hours
Excretion	Kidney (circa 70%)
Identifiers
IUPAC name 4-Amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one
Synonyms	(−)-L-2′,3′-dideoxy-3′-thiacytidine
CAS Number	134678-17-4 Y
PubChem (CID)	73339
DrugBank	DB00709 Y
ChemSpider	66068 Y
UNII	2T8Q726O95 Y
KEGG	D00353 Y
ChEMBL	CHEMBL141 N
NIAID ChemDB	000388
PDB ligand ID	3TC (PDBe, RCSB PDB)
ECHA InfoCard	100.132.250
Chemical and physical data
Formula	C8H11N3O3S
Molar mass	229.26 g/mol
3D model (Jmol)	Interactive image
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?)

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 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.

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 first approved for use in the United States in 1995. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world as of 2014 is about 0.06 USD per day. As of 2015 the cost for a typical month of medication in the United States is more than 200 USD.