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Substance Name: Dideoxyadenosine
RN: 4097-22-7
UNII: 4Q86AH641A
InChIKey: WVXRAFOPTSTNLL-NKWVEPMBSA-N

Note

  • A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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

Molecular Formula

  • C10-H13-N5-O2

Molecular Weight

  • 235.246
 

Classification Codes

  • Anti-Infective Agents
  • Antimetabolites
  • Antiviral Agents
  • Mutation Data
  • Noxae
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Names and Synonyms

Name of Substance

  • Dideoxyadenosine

MeSH Heading

  • Dideoxyadenosine

Synonyms

  • 2',3'-Dideoxyadenosine
  • 5-26-16-00256 (Beilstein Handbook Reference)
  • Adenosine, 2',3'-dideoxy-
  • BRN 0619924
  • CCRIS 428
  • D2A
  • DDA
  • ddAdo
  • Dideoxyadenosine
  • EINECS 223-853-2
  • NSC 98700
  • NSC-98700
  • UNII-4Q86AH641A

Systematic Names

  • 2',3'-Dideoxyadenosine
  • Adenosine, 2',3'-dideoxy-
  • Dideoxyadenosine

Registry Numbers

CAS Registry Number

  • 4097-22-7

FDA UNII

  • 4Q86AH641A

System Generated Number

  • 0004097227

Structure Descriptors

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

InChIKey

WVXRAFOPTSTNLL-NKWVEPMBSA-N

Smiles

n1(c2c(c(ncn2)N)nc1)[C@@H]1O[C@H](CO)CC1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 500mg/kg (500mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 19, Pg. 424, 1981.
mouse LD50 oral 5gm/kg (5000mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 19, Pg. 424, 1981.
mouse LD50 subcutaneous 1320mg/kg (1320mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 19, Pg. 424, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 184-186 deg C   EXP
log P (octanol-water) -0.25 (none)   EXP
Water Solubility 2280 mg/L 25 EST
Vapor Pressure 3.50E-11 mm Hg 25 EST
Henry's Law Constant 8.32E-20 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.27E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.