Chemical: Drug
didanosine

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PharmGKB contains no Clinical Variants that meet the highest level of criteria.

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The table below contains information about pharmacogenomic variants on PharmGKB. Please follow the link in the "Variant" column for more information about a particular variant. Each link in the "Variant" column leads to the corresponding PharmGKB Variant Page. The Variant Page contains summary data, including PharmGKB manually curated information about variant-drug pairs based on individual PubMed publications. The PMIDs for these PubMed publications can be found on the Variant Page.

The tags in the first column of the table indicate what type of information can be found on the corresponding Variant Page.

Links in the "Gene" column lead to PharmGKB Gene Pages.

List of all variant annotations for didanosine

Gene ? Variant?
(147)
Alternate Names ? Chemicals ? Alleles ?
(+ chr strand)
Function ? Amino Acid?
Translation
No VIP available CA VA
rs11191561 NC_000010.10:g.104869531C>G, NC_000010.11:g.103109774C>G, NG_042272.1:g.88533G>C, NM_001134373.2:c.176-3068G>C, NM_012229.4:c.176-3068G>C, XM_005269632.1:c.176-3068G>C, XM_005269632.3:c.176-3068G>C, XM_005269633.1:c.176-3068G>C, XM_005269633.3:c.176-3068G>C, XM_005269634.1:c.176-3068G>C, XM_005269634.3:c.176-3068G>C, XM_005269635.1:c.176-3068G>C, XM_005269635.3:c.176-3068G>C, XM_005269636.1:c.176-3068G>C, XM_005269636.3:c.176-3068G>C, XM_005269637.1:c.89-3068G>C, XM_005269637.3:c.89-3068G>C, XM_005269638.1:c.80-3068G>C, XM_005269638.3:c.80-3068G>C, XM_005269639.1:c.89-3068G>C, XM_005269639.3:c.89-3068G>C, XM_005269640.1:c.-399+1971G>C, XM_005269640.3:c.-399+1971G>C, XM_005269641.1:c.-399+1971G>C, XM_005269641.3:c.-399+1971G>C, XM_005269642.1:c.-399+1971G>C, XM_005269642.3:c.-399+1971G>C, XM_005269643.1:c.-398-3068G>C, XM_005269643.3:c.-398-3068G>C, XM_005269644.1:c.-423+1971G>C, XM_005269644.3:c.-423+1971G>C, XM_005269645.1:c.-423+1971G>C, XM_005269645.3:c.-423+1971G>C, XM_005269646.1:c.-423+1971G>C, XM_005269646.3:c.-423+1971G>C, XM_006717721.2:c.-399+1971G>C, XM_006717722.2:c.-280-3973G>C, XM_006717723.2:c.-280-3973G>C, XM_006717724.2:c.-304-3973G>C, XM_011539534.1:c.176-3068G>C, XM_011539535.1:c.67+1971G>C, XM_011539536.1:c.83-3068G>C, XM_011539537.1:c.176-3068G>C, rs52823845, rs56602986
C > G
SNP
No VIP available CA VA
rs11598702 NC_000010.10:g.104897985T>C, NC_000010.11:g.103138228T>C, NG_042272.1:g.60079A>G, NM_001134373.2:c.175+1178A>G, NM_012229.4:c.175+1178A>G, XM_005269632.1:c.175+1178A>G, XM_005269632.3:c.175+1178A>G, XM_005269633.1:c.175+1178A>G, XM_005269633.3:c.175+1178A>G, XM_005269634.1:c.175+1178A>G, XM_005269634.3:c.175+1178A>G, XM_005269635.1:c.175+1178A>G, XM_005269635.3:c.175+1178A>G, XM_005269636.1:c.175+1178A>G, XM_005269636.3:c.175+1178A>G, XM_005269637.1:c.88+1178A>G, XM_005269637.3:c.88+1178A>G, XM_005269638.1:c.79+1178A>G, XM_005269638.3:c.79+1178A>G, XM_005269639.1:c.88+1178A>G, XM_005269639.3:c.88+1178A>G, XM_005269640.1:c.-460+1178A>G, XM_005269640.3:c.-460+1178A>G, XM_005269641.1:c.-460+1178A>G, XM_005269641.3:c.-460+1178A>G, XM_005269642.1:c.-460+1178A>G, XM_005269642.3:c.-460+1178A>G, XM_005269643.1:c.-398-31522A>G, XM_005269643.3:c.-398-31522A>G, XM_005269644.1:c.-484+1178A>G, XM_005269644.3:c.-484+1178A>G, XM_005269645.1:c.-484+1178A>G, XM_005269645.3:c.-484+1178A>G, XM_005269646.1:c.-483-26423A>G, XM_005269646.3:c.-483-26423A>G, XM_006717721.2:c.-459-26423A>G, XM_006717722.2:c.-281+1178A>G, XM_006717723.2:c.-281+1178A>G, XM_006717724.2:c.-305+1178A>G, XM_011539534.1:c.175+1178A>G, XM_011539535.1:c.-1974A>G, XM_011539536.1:c.-43+1178A>G, XM_011539537.1:c.175+1178A>G, rs17728547, rs52826896, rs61084912
T > C
SNP
No VIP available CA VA
rs1429376 NC_000002.11:g.31588561A>C, NC_000002.12:g.31365695A>C, NG_008871.1:g.54051T>G, NM_000379.3:c.2457-151T>G, XM_011533095.1:c.2454-151T>G, XM_011533096.1:c.2457-151T>G, rs60163542
A > C
SNP
No VIP available CA VA
rs1594160 NC_000002.11:g.31578969A>C, NC_000002.12:g.31356103A>C, NG_008871.1:g.63643T>G, NM_000379.3:c.2632-5880T>G, XM_011533095.1:c.2629-5880T>G, XM_011533096.1:c.2632-5880T>G, rs4372951, rs4951979, rs59084801, rs60115556
A > C
SNP
Alleles, Functions, and Amino Acid Translations are all sourced from dbSNP 147

Overview

Generic Names
  • DDI
  • Dideoxyinosine
Trade Names
  • Videx
  • Videx EC
Brand Mixture Names

PharmGKB Accession Id

PA449301

Type(s):

Drug

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.

Source: Drug Bank

Indication

For use, in combination with other antiretroviral agents, in the treatment of HIV-1 infection in adults.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

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 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.

Source: Drug Bank

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 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.

Source: Drug Bank

Food Interaction

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

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

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.

Source: Drug Bank

Protein Binding

Low (<5%)

Source: Drug Bank

Absorption

Rapidly absorbed (bioavailability 30-40%) with peak plasma concentrations appearing within 0.5 and 1.5 hrs.

Source: Drug Bank

Half-Life

30 minutes in plasma and more than 12 hours in intracellular environment.

Source: Drug Bank

Toxicity

Side effects include pancreatitis, peripheral neuropathy, diarrhea, hyperuricemia and hepatic dysfunction

Source: Drug Bank

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.

Source: Drug Bank

Chemical Properties

Chemical Formula

C10H12N4O3

Source: Drug Bank

Isomeric SMILES

C1C[C@@H](O[C@@H]1CO)N2C=NC3=C2NC=NC3=O

Source: Drug Bank

OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O

Source: Drug Bank

Canonical SMILES

OC[C@@H]1CC[C@@H]

Source: Drug Bank

Average Molecular Weight

236.2273

Source: Drug Bank

Monoisotopic Molecular Weight

236.09094027

Source: Drug Bank

SMILES

OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O

Source: Drug Bank

InChI String

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

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

Curated Information ?

Drug Interactions

Interaction Description
didanosine - ganciclovir The antiviral agent increases the effect and toxicity of didanosine (source: Drug Bank)
didanosine - ganciclovir The antiviral agent, didanosine, may increase the effect and toxicity of didanosine. (source: Drug Bank)
didanosine - tenofovir Tenofovir increases the effect and toxicity of didanosine (source: Drug Bank)
didanosine - tenofovir Tenofovir increases the effect and toxicity of didanosine (source: Drug Bank)
didanosine - tipranavir Didanosine EC levels may be reduced (source: Drug Bank)
didanosine - tipranavir Didanosine EC levels may be reduced (source: Drug Bank)
didanosine - valganciclovir The antiviral agent increases the effect and toxicity of didanosine (source: Drug Bank)
didanosine - valganciclovir The antiviral agent, valganiclovir, may increase the effect and toxicity of didanosine. (source: Drug Bank)
didanosine - zalcitabine Additive toxicities (peripheral neuropathy) (source: Drug Bank)
didanosine - zalcitabine Additive toxicities (peripheral neuropathy) (source: Drug Bank)
ganciclovir - didanosine The antiviral agent increases the effect and toxicity of didanosine (source: Drug Bank)
ganciclovir - didanosine The antiviral agent, ganciclovir, may increase the effect and toxicity of didanosine. (source: Drug Bank)
tipranavir - didanosine Tipranavir decreases the concentration of Didanosine. (source: Drug Bank)
trovafloxacin - didanosine 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. (source: Drug Bank)
valganciclovir - didanosine 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. (source: Drug Bank)
valganciclovir - didanosine 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. (source: Drug Bank)
voriconazole - didanosine 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. (source: Drug Bank)

Curated Information ?

Relationships from National Drug File - Reference Terminology (NDF-RT)

May Treat
Contraindicated With

Publications related to didanosine: 3

No Dosing Guideline available No Drug Label available CA VA No VIP available No VIP available
Genetic determinants of idiopathic noncirrhotic portal hypertension in HIV-infected patients. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America. 2013. Vispo Eugenia, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
The Dual Role of Pharmacogenetics in HIV Treatment: Mutations and Polymorphisms Regulating Antiretroviral Drug Resistance and Disposition. Pharmacological reviews. 2012. Michaud Veronique, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
HIV-1 antiretroviral drug therapy. Cold Spring Harbor perspectives in medicine. 2012. Arts Eric J, et al. PubMed

LinkOuts

Web Resource:
Wikipedia
National Drug Code Directory:
0087-6632-41
DrugBank:
DB00900
PDB:
2DI
ChEBI:
490877
KEGG Compound:
C06953
KEGG Drug:
D00296
PubChem Compound:
50599
PubChem Substance:
189028
46506255
Drugs Product Database (DPD):
2244596
ChemSpider:
45864
HET:
2DI
Therapeutic Targets Database:
DNC000528
FDA Drug Label at DailyMed:
d4401ca0-98ae-af38-84c7-2f615d0706b9

Clinical Trials

These are trials that mention didanosine and are related to either pharmacogenetics or pharmacogenomics.

No trials loaded.

NURSA Datasets

provided by nursa.org

No NURSA datasets available.

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Sources for PharmGKB drug information: DrugBank, PubChem.