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CAS 4097-22-7

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Dideoxyadenosine

Description:
Dideoxyadenosine, also known as 2',3'-dideoxyadenosine (ddA), is a nucleoside analog that plays a significant role in antiviral therapy, particularly in the treatment of HIV. Its chemical structure is characterized by the absence of hydroxyl groups at the 2' and 3' positions of the ribose sugar, which distinguishes it from the natural nucleoside adenosine. This modification inhibits the action of reverse transcriptase, an enzyme critical for viral replication, thereby preventing the synthesis of viral DNA from RNA. Dideoxyadenosine is typically administered in its phosphate form, which is more biologically active. The compound is soluble in water and exhibits a relatively low toxicity profile, although it can lead to side effects such as mitochondrial toxicity. Its mechanism of action and structural properties make it a valuable tool in molecular biology and pharmacology, particularly in the development of antiretroviral therapies. As a research compound, it is also utilized in various biochemical assays and studies related to nucleic acid metabolism.
Formula:C10H13N5O2
InChI:InChI=1S/C10H13N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2,(H2,11,12,13)/t6-,7+/m0/s1
InChI key:InChIKey=WVXRAFOPTSTNLL-NKWVEPMBSA-N
SMILES:NC1=C2C(N(C=N2)[C@@H]3O[C@H](CO)CC3)=NC=N1
Synonyms:
  • 2,3-Dideoxyadenosine
  • Acerola
  • Adenosine, 2',3'-dideoxy-
  • Adenosine, 2′,3′-dideoxy-
  • DDA
  • Dideoxyadenosine
  • NSC 98700
  • Nqz-047
  • [5-(6-amino-9H-purin-9-yl)tetrahydrofuran-2-yl]methanol
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