3DChem.com - Chemistry, Structures & 3D Molecules a visual and interactive website showcasing the beautiful world of chemistry

Lamivudine (Molecule of the Month for April 2007)

Epivir, 3TC, 2',3'-dideoxy-3'-thiacytidine



Lamivudine is a potent reverse transcriptase inhibitor of the class nucleoside analog reverse transcriptase inhibitor (NARTI). Lamivudine has been used for treatment of chronic hepatitis B at a lower dose than for treatment of HIV. Lamivudine was approved by the Food and Drug Administration in 1995 for use with Zidovudine (AZT). When HIV infects a cell, reverse transcriptase copies the viral single stranded RNA genome into a double-stranded viral DNA. The viral DNA is then integrated into the host chromosomal DNA which then allows host cellular processes, such as transcription and translation to reproduce the virus. RTIs block reverse transcriptase's enzymatic function and prevent completion of synthesis of the double-stranded viral DNA thus preventing HIV from multiplying.

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.

In HIV, high level resistance is associated with the M184V/I mutation in the reverse transcriptase gene of the HIV virus. Lamivudine though continues to have a partial anti-viral effect even in the presence of the M184V mutation.

Formal Chemical Name (IUPAC)
4-amino-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one

References

http://en.wikipedia.org/wiki/Lamivudine

Picture of Lamivudine 3D model

click on the picture of  Lamivudine above to interact
with the 3D model of the
Lamivudine structure
(this will open a new browser window)

Picture of Lamivudine

C8 H11 N3 O3 S



Update by Karl Harrison
(Molecule of the Month for April 2007 )

Stacks Image 34 All the images on this web site are are made available with a Creative Commons Attribution license and so can be used as long as the attribution
© Karl Harrison 3DChem.com is written with the image. High resolution images and illustrations are available on request.