A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.

Annotation

an antiviral; inhibits HIV replication

DUI

D016048 MeSH Browser

CUI

M0024534

CAS

Adenosine, 2',3'-dideoxy-

Previous indexing

Dideoxynucleosides (1989); Deoxyadenosine/analogs & derivatives (1975-1989)

History note

90

Public note

90