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Encyclopedia > Lamivudine
Lamivudine
Systematic (IUPAC) name
L-2',3'-dideoxy-3'-thiacytidine
Identifiers
CAS number 134678-17-4
ATC code J05AF05
PubChem 60825
DrugBank APRD00681
Chemical data
Formula C8H11N3O3S 
Mol. mass 229.26 g/mol
Pharmacokinetic data
Bioavailability 86%
Protein binding Less than 36%
Metabolism  ?
Half life 5 to 7 hours
Excretion Renal (circa 70%)
Therapeutic considerations
Pregnancy cat.

B3(AU) C(US) Image File history File links Lamivudine. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Standard atomic weight 32. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... The kidneys are important excretory organs in vertebrates. ... The kidneys are organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses, see Australia (disambiguation). ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status

POM(UK) -only(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... A prescription drug is a licensed medicine that is regulated by legislation to require a prescription before it can be obtained. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Routes Oral

Lamivudine (2',3'-dideoxy-3'-thiacytidine, commonly called 3TC) is a potent nucleoside analog reverse transcriptase inhibitor (nRTI). In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a β-N1-glycosidic bond. ... This article needs to be cleaned up to conform to a higher standard of quality. ...


It is marketed by GlaxoSmithKline with the brand names Epivir and Epivir-HBV.


Lamivudine has been used for treatment of chronic hepatitis B at a lower dose than for treatment of HIV. It improves the seroconversion of e-antigen positive hepatitis B and also improves histology staging of the liver. Long term use of lamivudine unfortunately leads to emergence of a resistant hepatitis B virus (YMDD) mutant. Despite this, lamivudine is still used widely as it is well tolerated. “HBV” redirects here. ... Species Human immunodeficiency virus 1 Human immunodeficiency virus 2 Human immunodeficiency virus (HIV) is a retrovirus that causes acquired immunodeficiency syndrome (AIDS, a condition in humans in which the immune system begins to fail, leading to life-threatening opportunistic infections). ...

Contents

History

Lamivudine was invented by Bernard Belleau and Nghe Nguyen-Ga at the Montreal-based IAF BioChem International, Inc. laboratories in 1989. Initially designed as an antiviral agent, the drug's effectiveness for treating HIV in combination with AZT was discovered by Yung-Chi (Tommy) Cheng at Yale University. The drug was later licensed to the British pharmaceutical company Glaxo for a 14 percent royalty. Dr Bernard Belleau was a Canadian moloecular pharmacologists best known for his role in the discovery of Lamivudine, a drug used in the treatment of HIV and Hepatitis B infection. ... “Yale” redirects here. ...


Lamivudine was approved by the Food and Drug Administration (FDA) on November 17, 1995 for use with zidovudine (AZT) and again in 2002 as a once-a-day dosed medication. The fifth antiretroviral drug on the market, it was the last NRTI for three years while the approval process switched to protease inhibitors. According to the manufacturer's 2004 annual report, its patent will expire in the United States in 2010 and in Europe in 2011. “FDA” redirects here. ... 17 November is also the name of a Marxist group in Greece, coinciding with the anniversary of the Athens Polytechnic uprising. ... Year 1995 (MCMXCV) was a common year starting on Sunday (link will display full 1995 Gregorian calendar). ... Zidovudine (INN) or azidothymidine (AZT) (also called ZDV) is an antiretroviral drug, the first one approved for treatment of HIV. It is also sold under the names Retrovir® and Retrovis®, and as an ingredient in Combivir® and Trizivir®. It is an analog of thymidine. ... Protease inhibitors are a class of medication used to treat or prevent viral infections. ...


Mechanism of action

Lamivudine is an analogue of cytidine. It can inhibit both types (1 and 2) of HIV reverse transcriptase and also the reverse transcriptase of hepatitis B. It needs to be phosphorylated to its triphosphate form before it is active. 3TC-triphosphate also inhibits cellular DNA polymerase. An analog is in chemistry a chemical closely related to another usually sharing the same nucleus. ... Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a β-N1-glycosidic bond. ... Species Human immunodeficiency virus 1 Human immunodeficiency virus 2 Human immunodeficiency virus (HIV) is a retrovirus that causes acquired immunodeficiency syndrome (AIDS, a condition in humans in which the immune system begins to fail, leading to life-threatening opportunistic infections). ... In biochemistry, a reverse transcriptase, also known as RNA-dependent DNA polymerase, is a DNA polymerase enzyme that transcribes single-stranded RNA into double-stranded DNA. Normal transcription involves the synthesis of RNA from DNA, hence reverse transcription is the reverse of this. ... “HBV” redirects here. ... 3D structure of the DNA-binding helix-hairpin-helix motifs in human DNA polymerase beta A DNA polymerase is an enzyme that assists in DNA replication. ...


Lamivudine is administered orally, and it is rapidly absorbed with a bio-availability of over 80%. Some research suggests that lamivudine can cross the blood-brain barrier. Lamivudine is often given in combination with zidovudine, with which it is highly synergistic. Lamivudine treatment has been shown to restore zidovudine sensitivity of previously resistant HIV. Several mutagenicity tests show that lamivudine should not show mutagenic activity in therapeutical doses. The blood-brain barrier (BBB) is a membranic structure that acts primarily to protect the brain from chemicals in the blood, while still allowing essential metabolic function. ... Zidovudine (INN) or azidothymidine (AZT) (also called ZDV) is an antiretroviral drug, the first one approved for treatment of HIV. It is also sold under the names Retrovir® and Retrovis®, and as an ingredient in Combivir® and Trizivir®. It is an analog of thymidine. ... In biology, a mutagen (Latin, literally origin of change) is a physical or chemical agent that changes the genetic information (usually DNA) of an organism and thus increases the number of mutations above the natural background level. ...


Resistance

See also: resistance mutation

In HIV, high level resistance is associated with the M184V/I mutation in the reverse transcriptase gene. GlaxoSmithKline sought to perpetuate the fiction that the M184V mutation reduces "viral fitness", because of the finding that continued lamivudine treatment causes the HIV viral load to rebound but at a much lower level, and that withdrawal of lamivudine results in a higher viral load rebound with rapid loss of the M184V mutation; GSK therefore argued that there is theoretical benefit in continuing lamivudine treatment even in the presence of high level resistance, because the resistant virus is "less fit". The COLATE study has shown definitively that there is no benefit to continuing lamivudine treatment in patients with lamivudine resistance.[1] A better explanation of the data is that lamivudine continues to have a partial anti-viral effect even in the presence of the M184V mutation. The term resistance mutation is most commonly used to describe point mutations in virus genes that allow the virus to become resistant to treatment with a particular antiviral drug. ... In biochemistry, a reverse transcriptase, also known as RNA-dependent DNA polymerase, is a DNA polymerase enzyme that transcribes single-stranded RNA into double-stranded DNA. Normal transcription involves the synthesis of RNA from DNA, hence reverse transcription is the reverse of this. ... GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biological, and healthcare company. ...


In hepatitis B, lamivudine resistance was first described in the YMDD locus of the HBV reverse transcriptase gene. The HBV reverse transcriptase gene is 344 amino acids long and occupies codons 349 to 692 on the viral genome. The most commonly encountered resistance mutations are M204V/I/S. Other resistance mutations are L80V/I, V173L and L180M.[2]


Dosing

For adults with HIV (or children over 12), the dose is 300mg once daily, or 150mg twice a day. Lamivudine is never used on its own in the treatment of HIV.


For the treatment of adults with hepatitis B, the dose is 100mg once daily. If co-infected with HIV, then the dose is as for HIV.


Presentation

Epivir logo
  • Epivir 150 mg or 300 mg tablets (GlaxoSmithKline; US and UK) for the treatment of HIV;
  • Epivir-HBV 100 mg tablets (GlaxoSmithKline; US only) for the treatment of hepatitis B;
  • Zeffix 100 mg tablets (GlaxoSmithKline; UK only) for the treatment of hepatitis B.

Lamivudine is also available in fixed combinations with other HIV drugs: Image File history File links Lamivudine. ... Image File history File links Lamivudine. ...

Combivir is the brand name for a pharmaceutical treatment for HIV infection. ... Zidovudine (INN) or azidothymidine (AZT) (also called ZDV) is an antiretroviral drug, the first one approved for treatment of HIV. It is also sold under the names Retrovir® and Retrovis®, and as an ingredient in Combivir® and Trizivir®. It is an analog of thymidine. ... Abacavir (ABC) is extremely potent reverse transcriptase inhibitor, meant for the treatment of AIDS. ABC is capable of crossing the blood-brain barrier. ... Trizivir™ is a combination of three drugs patented by GlaxoSmithKline. ... Zidovudine (INN) or azidothymidine (AZT) (also called ZDV) is an antiretroviral drug, the first one approved for treatment of HIV. It is also sold under the names Retrovir® and Retrovis®, and as an ingredient in Combivir® and Trizivir®. It is an analog of thymidine. ... Abacavir (ABC) is extremely potent reverse transcriptase inhibitor, meant for the treatment of AIDS. ABC is capable of crossing the blood-brain barrier. ...

References

  1. ^ Fox Z, Dragsted UB, Gerstoft J, et al. (2006). "A randomized trial to evaluate continuation versus discontinuation of lamivudine in individuals failing a lamivudine-containing regimen: The COLATE trial". Antiviral Therapy 11: 761–70. PMID 17310820. 
  2. ^ Koziel MJ, Peters MG (2007). "Viral hepatitis in HIV infection". N Engl J Med 356 (14): 1445–54. 

External links


Daily Med is a website supplying drug label and other data, provided by the U.S. National Library of Medicine and National Institutes of Health. ... The United States National Library of Medicine (NLM), operated by the United States federal government, is the worlds largest medical library. ... National Institutes of Health Building 50 at NIH Clinical Center - Building 10 The National Institutes of Health (NIH) is an agency of the United States Department of Health and Human Services and is the primary agency of the United States government responsible for biomedical research. ... Daily Med is a website supplying drug label and other data, provided by the U.S. National Library of Medicine and National Institutes of Health. ... The United States National Library of Medicine (NLM), operated by the United States federal government, is the worlds largest medical library. ... National Institutes of Health Building 50 at NIH Clinical Center - Building 10 The National Institutes of Health (NIH) is an agency of the United States Department of Health and Human Services and is the primary agency of the United States government responsible for biomedical research. ...


  Results from FactBites:
 
Epivir Online, Description, Chemistry, Ingredients - Lamivudine - RxList Monographs (1050 words)
Lamivudine is a white to off-white crystalline solid with a solubility of approximately 70 mg/mL in water at 20
Intracellularly, lamivudine is phosphorylated to its active 5'-triphosphate metabolite, lamivudine triphosphate (3TC-TP).
Phenotypic analysis of baseline-matched on-therapy HIV-1 isolates from patients (n = 13) receiving lamivudine once daily showed that isolates from 12/13 patients were susceptible to zidovudine; isolates from 8/13 patients exhibited a 25- to 295-fold decrease in susceptibility to efavirenz, and isolates from 7/13 patients showed an 85- to 299-fold decrease in susceptibility to lamivudine.
lamivudine: Information from Answers.com (816 words)
Lamivudine was invented by Bernard Belleau and Nghe Nguyen-Ba at the Montreal-based IAF BioChem International, Inc. laboratories in 1989.
Lamivudine was approved by the Food and Drug Administration (FDA) on Nov 17, 1995 for use with Zidovudine (AZT) and again in 2002 as a once-a-day dosed medication.
Lamivudine is often given in combination with zidovudine, with which it is highly synergistic.
  More results at FactBites »

 
 

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