Chemicals and Drugs

Dideoxyadenosine

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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.

Chemical Identity

Chemical Information

Molecular Formula
C10H13N5O2
Molecular Weight
235.24 g/mol
CAS Registry No.
4097-22-7
IUPAC Name
[(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methanol
InChIKey
WVXRAFOPTSTNLL-NKWVEPMBSA-N
SMILES
C1C[C@@H](O[C@@H]1CO)N2C=NC3=C(N=CN=C32)N
MeSH Unique ID
D016048
Source
PubChem CID 20039

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

3 entry terms
  • 2',3'-Dideoxyadenosine
  • ddA (Antiviral)
  • 2',3' Dideoxyadenosine

MeSH Record

Aspects Covered

25 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

Indexing Annotation

an antiviral; inhibits HIV replication

MeSH Record

History Note

90

MeSH Record

Previous Indexing

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

MeSH Hierarchy

Tree Numbers

  1. D03w.633.100.759.590.138w.325.105
  2. D13.570w.230w.229.105
  3. D13.570w.230w.500.105
  4. D13.570w.583.138w.325.105

AMA Style

References

  1. National Library of Medicine. Dideoxyadenosine. Medical Subject Headings (MeSH). 2026. Unique ID D016048. http://id.nlm.nih.gov/mesh/2026/D016048
  2. Dideoxyadenosine. In: Wikidata. https://www.wikidata.org/wiki/Q27163127
  3. Dideoxyadenosine. In: PubChem Compound. CID 20039. https://pubchem.ncbi.nlm.nih.gov/compound/20039