Structure via PubChem · Public domain (PubChem)
lamivudine
Sign in to saveAlso known as Heptovir, beta-L-2',3'-Dideoxy-3'-thiacytidine, (-)-1-((2R,5S)-2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine, 2',3'-Dideoxy-3'-thiacytidine, 3'-Thia-2',3'-dideoxycytidine, beta-L-3'-Thia-2',3'-dideoxycytidine, (-)-2'-Deoxy-3'-thiacytidine, 3TC
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.
Key facts
- Drug.Verifiedfields
- changed
- Drug.verifiedrevid
- 477168974
- Drug.image
- Lamivudine structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 155
- Drug.tradename
- Epivir, Epivir-HBV, Zeffix, others
- Drug.MedlinePlus
- a696011
- Drug.DailyMedID
- Lamivudine
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- J05
- Drug.ATC_suffix
- AF05
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.legal_CA
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.bioavailability
- 86%
- Drug.protein_bound
- Less than 36%
via Wikipedia infobox
Chemical data
- Formula
- C8H11N3O3S
- Molecular weight
- 229.26 g/mol
- IUPAC name
- 4-amino-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
- SMILES
- C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
- InChIKey
- JTEGQNOMFQHVDC-NKWVEPMBSA-N
- XLogP
- -0.9
- Polar surface area
- 113 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
11,587 papers- Dolutegravir/Lamivudine Single-Tablet Regimen: A Review in HIV-1 Infection.Drugs · 2020
- Lamivudine.The Journal of the Association of Nurses in AIDS Care : JANAC · 1996
- Lamivudine/zidovudine/abacavir: triple combination tablet.Drugs · 2003
- Dolutegravir/lamivudine (Dovato)--a two-drug complete regimen for HIV-1 infection.The Medical letter on drugs and therapeutics · 2019
- Lamivudine for the treatment of HIV.Expert opinion on drug metabolism & toxicology · 2010
via PubMed
Wikidata facts
- Mass
- 229.052
Show 8 more facts
- chemical formula
- C₈H₁₁N₃O₃S
- defined daily dose
- 0.3
- Commons category
- Lamivudine
- canonical SMILES
- C1C(OC(S1)CO)N2C=CC(=NC2=O)N
- isomeric SMILES
- C1[C@H](O[C@H](S1)CO)N2C=CC(=NC2=O)N
- World Health Organisation international non-proprietary name
- lamivudine
- MCN code
- 2934.99.93
- stylized name
- lamiVUDine
Sources (7)
via Wikidata · CC0
~8 min read
Article
7 sectionsContents
- Medical uses
- Resistance
- Side effects
- Mechanism of action
- History
- Formulations
- References
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.
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.