Zalcitabine

zalcitabine
IUPAC name: see chemistry section Synonyms: dideoxycytidine (ddC) Formula: C9H13N3O3
Uses:	HIV/AIDS
Properties:	RT inhibitor, cytosine analog, DNA terminator
Hazards:	see drug interactions
Mass (g/mol): CAS #: 211.2178 7481-89-2

Zalcitabine, or dideoxycytidine (DDC or DDCYD), is a dideoxynucleoside antiviral drug that is an analog of the natural DNA base cytosine. The lack of 3'-hydroxyl group makes it a viral DNA chain terminator. It also inhibits HIV-1 reverse transcriptase by binding to it and competing with the natural substrate deoxycytidine triphosphate (dCTP). The related drug lamivudine, which has a sulfur atom in place of the 3'-carbon present in zalcitabine, supresses viruses in a similar manner.

Chemistry

Its IUPAC chemical name of zalcitabine is 4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one, but it is also called dideoxycytidine (ddC), and it has molecular formula C₉H₁₃N₃O₃ giving it a molecular mass of 211.2178 g/mol. It is a structural analog of the natural base deoxycytosine which used in DNA, but zalcitabine lacks the 3'-hydroxy group.

External links

• Zalcitabine - FDA approved drug information (drug label) from DailyMed (U.S. National Library of Medicine).
• Template:MedMaster
• Template:DrugBank