Zidovudine

zidovudine
IUPAC name: see chemistry section Synonyms: see below Formula: C10H13N5O4
Uses:	antiviral drug HIV
Properties:	reverse transcriptase inhibitor
Hazards:	see drug interactions
Mass (g/mol): CAS #: 267.2413 30516-87-1

Zidovudine is an antiviral drug used primarily for the treatment of HIV/AIDS.

Mechanism of action

Zidovudine is a nucleoside-based reverse transcriptase inhibitor that is structurally analogous to thymidine, a normal base in DNA. After phosphorylation, it becomes incorporated into viral DNA where it acts as a DNA chain terminator. The viral DNA chain is terminated because the 3'-hydroxy group needed for the formation of a phosphordiester bond is missing, having been replaced by an azido group. It also inhibits the HIV RT by binding with it and thus competing with natural substrates.

Chemistry

The IUPAC chemical name for zidovudine is 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione and it has chemical formula C₁₀H₁₃N₅O₄, giving it a molecular mass of 267.2413 g/mol. It is dideoxynucleoside in which the usual 3'-hydroxy group has been replaced by an azido group, making incapable of forming normal phosphodiester bonds required for normal DNA.