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MedKoo Cat#: 317608 | Name: Didanosine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Didanosine (2′,3′-dideoxyinosine, ddI, DDI) marketed under the trade names Videx and Videx EC. It is an antiretroviral medication used to treat HIV/AIDS in combination with other medications as part of highly active antiretroviral therapy (HAART). It is of the reverse transcriptase inhibitor class. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system. (Source: https://en.wikipedia.org/wiki/Didanosine).

Chemical Structure

Didanosine
CAS#69655-05-6

Theoretical Analysis

MedKoo Cat#: 317608

Name: Didanosine

CAS#: 69655-05-6

Chemical Formula: C10H12N4O3

Exact Mass: 236.0909

Molecular Weight: 236.23

Elemental Analysis: C, 50.84; H, 5.12; N, 23.72; O, 20.32

Price and Availability

Size Price Availability Quantity
250mg USD 150.00 Ready to ship
500mg USD 225.00 Ready to ship
1g USD 350.00 Ready to ship
2g USD 550.00 Ready to ship
5g USD 950.00 Ready to ship
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Related CAS #
No Data
Synonym
Didanosine; 2',3'-Dideoxyinosine; 69655-05-6; DIDEOXYINOSINE; Videx; Videx EC
IUPAC/Chemical Name
9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
InChi Key
BXZVVICBKDXVGW-NKWVEPMBSA-N
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
SMILES Code
C1C[C@@H](O[C@@H]1CO)N2C=NC3=C2NC=NC3=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot# C20B02B05
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Didanosine(Videx) is a reverse transcriptase inhibitor with an IC50 of 0.49 μM.
In vitro activity:
Dissociated DRG cells and organotypic DRG explants from embryonic 15-day-old Wistar rats were cultured for 3 days and then exposed to didanoside (ddI) (1 microg/ml, 5 microg/ml, 10 microg/ml, and 20 microg/ml) for another 3 days and 6 days, respectively. Neurons cultured continuously in medium served as normal controls. The diameter of the neuronal cell body and neurite length were measured in dissociated DRG cell cultures. Neuronal ultrastructural changes were observed in both culture models. ddI induced dose-dependent decreases in neurite number, length of the longest neurite in each neuron, and total neurite length per neuron in dissociated DRG cell cultures with 3 days treatment. There were no morphological changes seen in organotypic DRG cultures even with longer exposure time (6 days). But ddI induced ultrastructural changes in both culture models. Ultrastructural abnormalities included loss of cristae in mitochondria, clustering of microtubules and neurofilaments, accumulation of glycogen-like granules, and emergence of large dense particles between neurites or microtubules. Lysosome-like large particles emerged inconstantly in neurites. ddI induced a neurite retraction or neurite loss in a dose-dependent manner in dissociated DRG neurons, suggesting that ddI may partially contribute to developing peripheral neuropathy. Cytoskeletal rearrangement and ultrastructural abnormalities caused by ddI in both culture models may have a key role in neurite degeneration. Reference: Cell Biol Toxicol. 2008 Jan;24(1):113-21. https://doi.org/10.1007/s10565-007-9021-2
In vivo activity:
Whether or not ddI affects the in vivo genotoxicity of AZT by breeding C57Bl/6N/Tk+/- female mice with C3H/HeNMTV male mice and treating the offspring daily on postnatal days 1-8 was evaluated with 200 mg/kg ddI alone or in combination with 200 mg/kg AZT. One day after the last dose, bone marrow polychromatic erythrocytes (PCEs) were obtained to assess the induction of micronuclei; 3 weeks following treatment, the induction of mutants was determined in the hypoxanthine-guanine phosphoribosyltransferase (Hprt) and Tk genes of splenic T lymphocytes from B6C3F1/Tk+/- mice. The mixture of AZT and ddI, but not ddI alone, caused a significant increase in micronucleated PCEs. When assessed 3 weeks after dosing, ddI did not induce mutations in the Hprt or Tk genes. The mixture of AZT and ddI also did not induce mutations in the Hprt gene, but did induce a significant increase in Tk mutants, similar to that observed previously with AZT alone. The induction of mutations in the Tk gene by the mixture of AZT and ddI was associated with loss of the wild-type Tk+ allele. These data indicate that, under the conditions of this experiment, ddI is not mutagenic in neonatal B6C3F1/Tk+/- mice and that it does not potentiate the mutagenicity of AZT. Reference: Mutagenesis. 2004 Jul;19(4):307-11. https://academic.oup.com/mutage/article-lookup/doi/10.1093/mutage/geh033
Solvent mg/mL mM comments
Solubility
DMSO 62.5 264.57
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 236.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Liu H, Liu Z, Yang X, Huang F, Ma C, Li Z. Neurotoxicity caused by didanosine on cultured dorsal root ganglion neurons. Cell Biol Toxicol. 2008 Jan;24(1):113-21. doi: 10.1007/s10565-007-9021-2. Epub 2007 Jul 6. PMID: 17619152.
In vivo protocol:
1. Von Tungeln LS, Dobrovolsky VN, Bishop ME, Shaddock JG, Heflich RH, Beland FA. Frequency of Tk and Hprt lymphocyte mutants and bone marrow micronuclei in mice treated neonatally with zidovudine and didanosine. Mutagenesis. 2004 Jul;19(4):307-11. doi: 10.1093/mutage/geh033. PMID: 15215330.
1: Pavia-Ruz N, Rossouw M, Sáez-Llorens X, Bunupuradah T, Taylor M, Yang R, Sevinsky H, Krystal M, Lataillade M, Seekins D, Biguenet S. Efavirenz Capsule Sprinkle and Liquid Formulations with Didanosine and Emtricitabine in HIV-1-Infected Infants and Children 3 Months to 6 Years of Age: Study AI266-922. Pediatr Infect Dis J. 2015 Sep 15. [Epub ahead of print] PubMed PMID: 26379163. 2: Stotts M, Chisholm P, Nurutdinova D, Maddur H. A Case of Non-Cirrhotic Portal Hypertension Associated With Chronic Didanosine Therapy. ACG Case Rep J. 2015 Jan 16;2(2):119-20. doi: 10.14309/crj.2015.24. eCollection 2015 Jan. PubMed PMID: 26157933; PubMed Central PMCID: PMC4435383. 3: Cunha RD, Abreu CM, Sousa AK, Mabombo VC, Nijhuis M, de Jong D, Tanuri A. Short Communication: In Vitro Accumulation of Drug Resistance Mutations in Chimeric Infectious Clones Containing Subtype B or C Reverse Transcriptase and Selected with Tenofovir or Didanosine. AIDS Res Hum Retroviruses. 2015 Aug;31(8):851-8. doi: 10.1089/AID.2014.0324. Epub 2015 Jul 16. PubMed PMID: 26075306. 4: Ferreira da Silva C, Severino P, Martins F, Santana MH, Souto EB. Didanosine-loaded chitosan microspheres optimized by surface-response methodology: a modified "Maximum Likelihood Classification" approach formulation for reverse transcriptase inhibitors. Biomed Pharmacother. 2015 Mar;70:46-52. doi: 10.1016/j.biopha.2014.12.047. Epub 2015 Jan 13. PubMed PMID: 25776478. 5: Gómez-Rubio J, Bárcena-Atalaya AB, Macías-García L, Lozano de León-Naranjo F. [Non-cirrhotic portal hypertension associated with didanosine: An unusual cause of gastrointestinal bleeding]. Med Clin (Barc). 2015 Jul 6;145(1):45. doi: 10.1016/j.medcli.2014.09.014. Epub 2014 Dec 13. Spanish. PubMed PMID: 25510631. 6: Seremeta KP, Tur MI, Pérez SM, Höcht C, Taira C, López Hernández OD, Sosnik A. Spray-dried didanosine-loaded polymeric particles for enhanced oral bioavailability. Colloids Surf B Biointerfaces. 2014 Nov 1;123:515-23. doi: 10.1016/j.colsurfb.2014.09.055. Epub 2014 Oct 6. PubMed PMID: 25444665. 7: Severino P, Da Silva CF, Dalla Costa TC, Silva H, Chaud MV, Santana MH, Souto EB. In vivo absorption of didanosine formulated in pellets composed of chitosan microspheres. In Vivo. 2014 Nov-Dec;28(6):1045-50. PubMed PMID: 25398797. 8: Dziuban EJ, Raizes E, Koumans EH. A farewell to didanosine: harm reduction and cost savings by eliminating use of didanosine. Int J STD AIDS. 2015 Oct;26(12):903-6. doi: 10.1177/0956462414554433. Epub 2014 Oct 2. PubMed PMID: 25281538; PubMed Central PMCID: PMC4677683. 9: Sun R, Eriksson S, Wang L. Down-regulation of mitochondrial thymidine kinase 2 and deoxyguanosine kinase by didanosine: implication for mitochondrial toxicities of anti-HIV nucleoside analogs. Biochem Biophys Res Commun. 2014 Jul 25;450(2):1021-6. doi: 10.1016/j.bbrc.2014.06.098. Epub 2014 Jun 26. PubMed PMID: 24976398. 10: Steegen K, Levin L, Ketseoglou I, Bronze M, Papathanasopoulos MA, Carmona S, Stevens W. High-level cross-resistance to didanosine observed in South African children failing an abacavir- or stavudine-based 1st-line regimen. PLoS One. 2014 May 9;9(5):e97067. doi: 10.1371/journal.pone.0097067. eCollection 2014. PubMed PMID: 24816790; PubMed Central PMCID: PMC4016228.