An antiviral nucleoside analog and inhibitor of reverse transcriptase
Related Products
Active Metabolite(s)
383732',3'-Dideoxyadenosine-5'-O-triphosphate (sodium salt)
Labeled Version(s)
30078Didanosine-d2
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Didanosine

Item No. 23715

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2',3'-dideoxy-inosine
CAS Number
69655-05-6
Synonyms
  • ddl
  • 2′,3′-Dideoxyinosine
  • NSC 612049
Molecular Formula
C10H12N4O3
Formula Weight
236.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
0.1 M HCl: 10 mg/mlDMSO: 10 mg/ml
λmax
246 nm
SMILES
OC[C@@H]1CC[C@H](N2C=NC3=C2N=CNC3=O)O1
InChi Code
InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1
InChi Key
BXZVVICBKDXVGW-NKWVEPMBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Product Description

    Didanosine is an antiviral nucleoside analog and an inhibitor of reverse transcriptase.1 It undergoes cellular amination and phosphorylation to its active triphosphate form, 2',3'-dideoxyadenosine 5'-triphosphate (ddATP; Item No. 17460). Didanosine inhibits human T cell leukemia virus type 1 (HTLV-1) reverse transcriptase activity (IC50 = 30 nM).2 It inhibits the replication of HIV-1 clinical isolates containing various mutations in the gene encoding reverse transcriptase, pol, in isolated human peripheral blood mononuclear cells (PBMCs; IC50s = 0.3-11.1 μM).3 Didanosine inhibits proliferation and differentiation of primary human skeletal muscle cells (IC50s = 1 and 0.1 mM, respectively), as well as decreases the activities of mitochondrial complex IV, also known as cytochrome c oxidase, and mitochondrial complex II, also known as succinate dehydrogenase, in the same cells when used at a concentration of 1 mM.4 In vivo, didanosine protects mice from HIV infection (EC50 = 13.7 mg/kg).5 Formulations containing didanosine have been used in the treatment of HIV-1 infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Perry, C.M., and Noble, S. Didanosine: An updated review of its use in HIV infection. Drugs 58(6), 1099-1135 (1999).

    2. Anantharaman, V., and Moen, L.K. Effects of nucleoside analogs on native and site-directed mutants of HTLV type 1 reverse transcriptase. Bioorg. Chem. 28(5), 293-305 (2000).

    3. Eron, J.J., Chow, Y.-K., Caliendo, A.M., et al. pol Mutations conferring zidovudine and didanosine resistance with different effects in vitro yield multiply resistant human immunodeficiency virus type 1 isolates in vivo. Antimicrob. Agents Chemother. 37(7), 1480-1487 (1993).

    4. Benbrik, E., Chariot, P., Bonavaud, S., et al. Cellular and mitochondrial toxicity of zidovudine (AZT), didanosine (ddI) and zalcitabine (ddC) on cultured human muscle cells. J. Neurol. Sci. 149(1), 19-25 (1997).

    5. Kaneshima, H., Shih, C.C., Namikawa, R., et al. Human immunodeficiency virus infection of human lymph nodes in the SCID-hu mouse. Proc. Natl. Acad. Sci. USA 88(10), 4523-4527 (1991).