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QuickView for Didanosine (compound)

Summary
General Info

PubChem

PubChem Compound 3043

PubChem Compound 3043

Name:	Didanosine
PubChem Compound ID:	3043
Description:	A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.
Molecular formula:	C₁₀H₁₂N₄O₃
Molecular weight:	236.227 g/mol
Synonyms:	NSC612049; 2',3'-Dideoxyinosine; NCI60_004860; Inosine, 2',3'-dideoxy-; 2',3'-Dideoxyinosine, hydrate; 69655-05-6

DrugBank

Identification

Name:	Didanosine
Name (isomeric):	DB00900
Drug Type:	small molecule
Description:	A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite.
Synonyms:	DDI; Dideoxyinosine
Brand:	Videx, Videx EC
Category:	Antimetabolites, Anti-HIV Agents, Purine Nucleoside Phosphorylase inhibitor, Reverse Transcriptase Inhibitors
CAS number:	69655-05-6

Pharmacology

Indication:	For use, in combination with other antiretroviral agents, in the treatment of HIV-1 infection in adults.
Pharmacology:	Didanosine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Didanosine differs from other nucleoside analogues, as it does not have any of the regular bases, instead it has hypoxanthine attached to the sugar ring. Didanosine is phosphorylated to active metabolites that compete... show more » Didanosine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Didanosine differs from other nucleoside analogues, as it does not have any of the regular bases, instead it has hypoxanthine attached to the sugar ring. Didanosine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. Didanosine is effective against HIV, and usually used in combination with other antiviral therapy. Switching from long term AZT treatment to didanosine has been shown to be beneficial. Didanosine has weak acid stability and therefore, it is often combined with an antacid. show less «
Mechanism of Action:	Didanosine (ddI) is metabolized intracellularly by a series of cellular enzymes to its active moiety, dideoxyadenosine triphosphate (ddATP), which inhibits the HIV reverse transcriptase enzyme competitively by competing with natural dATP. It also acts as a chain terminator by its incorporation into viral DNA as the lack of a 3'-OH group in the inco... show more » Didanosine (ddI) is metabolized intracellularly by a series of cellular enzymes to its active moiety, dideoxyadenosine triphosphate (ddATP), which inhibits the HIV reverse transcriptase enzyme competitively by competing with natural dATP. It also acts as a chain terminator by its incorporation into viral DNA as the lack of a 3'-OH group in the incorporated nucleoside analogue prevents the formation of the 5' to 3' phosphodiester linkage essential for DNA chain elongation, and therefore, the viral DNA growth is terminated. show less «
Absorption:	Rapidly absorbed (bioavailability 30-40%) with peak plasma concentrations appearing within 0.5 and 1.5 hrs.
Protein binding:	Low (<5%)
Biotransformation:	Rapidly metabolized intracellularly to its active moiety, 2,3-dideoxyadenosine-5-triphosphate (ddA-TP). It is then further metabolized hepatically to yield hypoxanthine, xanthine, and uric acid.
Route of elimination:	Based on data from in vitro and animal studies, it is presumed that the metabolism of didanosine in man occurs by the same pathways responsible for the elimination of endogenous purines. Purines are eliminated by the kidneys.
Half Life:	30 minutes in plasma and more than 12 hours in intracellular environment.
Toxicity:	Side effects include pancreatitis, peripheral neuropathy, diarrhea, hyperuricemia and hepatic dysfunction
Affected organisms:	Human Immunodeficiency Virus

Interactions

Food interaction:

Avoid alcohol.

Take on empty stomach: 1 hour before or 2 hours after meals.

Drug interaction:

Trovafloxacin	Didanosine may decrease the absorption of orally administered Trovafloxacin. The Didanosine formulation contains magnesium and aluminum ions that intefere with Trovafloxacin absorption. Administer Trovafloxacin 2 hours before or 6 hours after the Didanosine dose to minimize the interaction. This interaction is not observed with enteric coated Didanosine.
Voriconazole	Didanosine may interfere with the absorption of orally administered voriconazole. Enteric coated didanosine does not exert this effect. Didanosine buffered formulations should be administered at least 2 hours from oral voriconazole administration.
Valganciclovir	The adverse/toxic effects of Didanosine, a reverse transcriptase inhibitor (nucleoside), may be enhanced by Valganciclovir. There is a significant risk of hematologic toxicity. Concomitant therapy should be avoided.
Tipranavir	Tipranavir may decrease the concentration of Didanosine.
Tobramycin	Increased risk of nephrotoxicity

Targets

Reverse transcriptase

Purine nucleoside phosphorylase

Transporters

Solute carrier family 22 member 6