Identification
NameDidanosine
Accession NumberDB00900  (APRD00240, DB02392)
TypeSmall Molecule
GroupsApproved
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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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. [PubChem]

Structure
Thumb
Synonyms
2,3-Dideoxyinosine
9-((2R,5S)-5-(Hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one
9-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-ol
9-[(2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-one
DDI
DdIno
Didanosina
Didanosine
Didanosinum
Dideoxyinosine
External IDs BMY-40900 / DDI
Product Ingredients Not Available
Product Images
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
VidexPowder, for solution10 mg/mLOralBristol Myers Squibb1991-10-09Not applicableUs
VidexPowder, for solution10 mg/mLOralBristol Myers Squibb1991-10-09Not applicableUs
Videx Chewable Dispersible Tab 100mgTablet100 mgOralBristol Myers Squibb1991-12-312008-03-27Canada
Videx Chewable Dispersible Tab 150mgTablet150 mgOralBristol Myers Squibb1991-12-312007-05-01Canada
Videx Chewable Dispersible Tab 25mgTablet25 mgOralBristol Myers Squibb1991-12-312007-01-02Canada
Videx Chewable Dispersible Tab 50mgTablet50 mgOralBristol Myers Squibb1991-12-312005-08-01Canada
Videx ECCapsule, delayed release250 mgOralBristol Myers Squibb2002-01-02Not applicableCanada
Videx ECCapsule, delayed release200 mg/1OralBristol Myers Squibb2000-10-31Not applicableUs
Videx ECCapsule, delayed release125 mgOralBristol Myers Squibb2002-01-02Not applicableCanada
Videx ECCapsule, delayed release400 mgOralBristol Myers Squibb2002-01-02Not applicableCanada
Videx ECCapsule, delayed release250 mg/1OralBristol Myers Squibb2000-10-31Not applicableUs
Videx ECCapsule, delayed release200 mgOralBristol Myers Squibb2002-01-02Not applicableCanada
Videx ECCapsule, delayed release125 mg/1OralBristol Myers Squibb2000-10-31Not applicableUs
Videx ECCapsule, delayed release400 mg/1OralBristol Myers Squibb2000-10-31Not applicableUs
Videx Pediatric Powder Sol 4g/bottPowder, for solution4 gOralBristol Myers Squibb1999-07-012007-06-28Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DidanosineCapsule, delayed release125 mg/1OralMylan Pharmaceuticals2010-06-282016-10-13Us
DidanosineCapsule, delayed release400 mg/1OralAmerincan Health Packaging2009-12-082015-12-29Us
DidanosineCapsule, delayed release200 mg/1OralAurobindo Pharma2008-09-24Not applicableUs
DidanosineCapsule, delayed release250 mg/1OralAmerincan Health Packaging2009-12-082015-12-29Us00555 0589 01 nlmimage10 172f8b9c
DidanosineCapsule, delayed release400 mg/1OralMylan Pharmaceuticals2010-06-282016-10-13Us
DidanosineCapsule, delayed release pellets200 mg/1OralTeva2004-12-15Not applicableUs00555 0588 01 nlmimage10 77303ba1
DidanosineCapsule, delayed release pellets250 mg/1OralPhysicians Total Care, Inc.2007-12-13Not applicableUs
DidanosineCapsule, delayed release200 mg/1OralMylan Pharmaceuticals2010-06-282016-10-13Us
DidanosineCapsule, delayed release250 mg/1OralAmerincan Health Packaging2009-12-082015-12-29Us
DidanosineCapsule, delayed release250 mg/1OralAurobindo Pharma2008-09-24Not applicableUs
DidanosineCapsule, delayed release pellets250 mg/1OralTeva2004-12-15Not applicableUs
DidanosineCapsule, delayed release pellets250 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
DidanosineCapsule, delayed release125 mg/1OralAurobindo Pharma2008-09-24Not applicableUs
DidanosineCapsule, delayed release250 mg/1OralMylan Pharmaceuticals2010-06-282016-10-13Us
DidanosineCapsule, delayed release400 mg/1OralAmerincan Health Packaging2009-12-082015-12-29Us
DidanosineCapsule, delayed release400 mg/1OralAurobindo Pharma2008-09-24Not applicableUs
DidanosineCapsule, delayed release pellets400 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs00555 0590 01 nlmimage10 0e2f871c
DidanosineCapsule, delayed release pellets400 mg/1OralTeva2004-12-15Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIK3GDH6OH08
CAS number69655-05-6
WeightAverage: 236.2273
Monoisotopic: 236.09094027
Chemical FormulaC10H12N4O3
InChI KeyBXZVVICBKDXVGW-NKWVEPMBSA-N
InChI
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
IUPAC Name
9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
SMILES
OC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O
Pharmacology
Indication

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

Structured Indications
Pharmacodynamics

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.

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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Reverse transcriptase/RNaseHProteinyes
inhibitor
Human immunodeficiency virus 1Q72547 details
Purine nucleoside phosphorylaseProteinunknownNot AvailableHumanP00491 details
Related Articles
Absorption

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

Volume of distributionNot Available
Protein binding

Low (<5%)

Metabolism

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.

SubstrateEnzymesProduct
Didanosine
Not Available
HypoxanthineDetails
Didanosine
Not Available
Uric acidDetails
Didanosine
Not Available
XanthineDetails
Didanosine
Not Available
2,3-dideoxyadenosine-5-triphosphateDetails
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.

ClearanceNot Available
Toxicity

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

Affected organisms
  • Human Immunodeficiency Virus
Pathways
PathwayCategorySMPDB ID
Didanosine Action PathwayDrug actionSMP00739
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
2-HYDROXY-1,4-NAPHTHOQUINONEDidanosine can cause a decrease in the absorption of 2-HYDROXY-1,4-NAPHTHOQUINONE resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
AllopurinolThe serum concentration of Didanosine can be increased when it is combined with Allopurinol.Approved
Amphotericin BDidanosine can cause a decrease in the absorption of Amphotericin B resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
AnidulafunginDidanosine can cause a decrease in the absorption of Anidulafungin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
ArtemetherDidanosine can cause a decrease in the absorption of Artemether resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Didanosine.Approved, Investigational
Bafilomycin A1Didanosine can cause a decrease in the absorption of Bafilomycin A1 resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
Benzoic AcidDidanosine can cause a decrease in the absorption of Benzoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
BifonazoleDidanosine can cause a decrease in the absorption of Bifonazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ButenafineDidanosine can cause a decrease in the absorption of Butenafine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ButoconazoleDidanosine can cause a decrease in the absorption of Butoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CandicidinDidanosine can cause a decrease in the absorption of Candicidin resulting in a reduced serum concentration and potentially a decrease in efficacy.Withdrawn
Capric acidDidanosine can cause a decrease in the absorption of Decanoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
CaspofunginDidanosine can cause a decrease in the absorption of Caspofungin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CeruleninDidanosine can cause a decrease in the absorption of Cerulenin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ChloroxineDidanosine can cause a decrease in the absorption of Chloroxine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CiclopiroxDidanosine can cause a decrease in the absorption of Ciclopirox resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
CinoxacinThe serum concentration of Didanosine can be decreased when it is combined with Cinoxacin.Approved, Withdrawn
CiprofloxacinThe serum concentration of Didanosine can be decreased when it is combined with Ciprofloxacin.Approved, Investigational
ClotrimazoleDidanosine can cause a decrease in the absorption of Clotrimazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
CordycepinDidanosine can cause a decrease in the absorption of Cordycepin resulting in a reduced serum concentration and potentially a decrease in efficacy.Investigational
CyclosporineDidanosine can cause a decrease in the absorption of Cyclosporine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational, Vet Approved
DarunavirThe serum concentration of Didanosine can be decreased when it is combined with Darunavir.Approved
EconazoleDidanosine can cause a decrease in the absorption of Econazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
EfinaconazoleDidanosine can cause a decrease in the absorption of Efinaconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
EnoxacinThe serum concentration of Didanosine can be decreased when it is combined with Enoxacin.Approved
EthanolThe risk or severity of adverse effects can be increased when Ethanol is combined with Didanosine.Approved
FebuxostatThe serum concentration of Didanosine can be increased when it is combined with Febuxostat.Approved
FleroxacinThe serum concentration of Didanosine can be decreased when it is combined with Fleroxacin.Approved
FluconazoleDidanosine can cause a decrease in the absorption of Fluconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
FlucytosineDidanosine can cause a decrease in the absorption of Flucytosine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
FlumequineThe serum concentration of Didanosine can be decreased when it is combined with Flumequine.Withdrawn
GanciclovirThe risk or severity of adverse effects can be increased when Ganciclovir is combined with Didanosine.Approved, Investigational
GatifloxacinThe serum concentration of Didanosine can be decreased when it is combined with Gatifloxacin.Approved, Investigational
GemifloxacinThe serum concentration of Didanosine can be decreased when it is combined with Gemifloxacin.Approved, Investigational
GlyphosateDidanosine can cause a decrease in the absorption of Glyphosate resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
GrepafloxacinThe serum concentration of Didanosine can be decreased when it is combined with Grepafloxacin.Withdrawn
GriseofulvinDidanosine can cause a decrease in the absorption of Griseofulvin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
HaloproginDidanosine can cause a decrease in the absorption of Haloprogin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Withdrawn
HexetidineDidanosine can cause a decrease in the absorption of Hexetidine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
HydroxyureaThe risk or severity of adverse effects can be increased when Hydroxyurea is combined with Didanosine.Approved
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Didanosine.Approved
IsoconazoleDidanosine can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ItraconazoleDidanosine can cause a decrease in the absorption of Itraconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
KetoconazoleDidanosine can cause a decrease in the absorption of Ketoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
LevofloxacinThe serum concentration of Didanosine can be decreased when it is combined with Levofloxacin.Approved, Investigational
LomefloxacinThe serum concentration of Didanosine can be decreased when it is combined with Lomefloxacin.Approved
LopinavirThe serum concentration of Didanosine can be decreased when it is combined with Lopinavir.Approved
MethadoneThe serum concentration of Didanosine can be decreased when it is combined with Methadone.Approved
MevastatinDidanosine can cause a decrease in the absorption of Mevastatin resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
MicafunginDidanosine can cause a decrease in the absorption of Micafungin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
MiconazoleDidanosine can cause a decrease in the absorption of Miconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational, Vet Approved
MiltefosineDidanosine can cause a decrease in the absorption of Miltefosine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
MoxifloxacinThe serum concentration of Didanosine can be decreased when it is combined with Moxifloxacin.Approved, Investigational
MyxothiazolDidanosine can cause a decrease in the absorption of Myxothiazol resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
NaftifineDidanosine can cause a decrease in the absorption of Naftifine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Nalidixic AcidThe serum concentration of Didanosine can be decreased when it is combined with Nalidixic Acid.Approved
NatamycinDidanosine can cause a decrease in the absorption of Natamycin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
NitroxolineDidanosine can cause a decrease in the absorption of Nitroxoline resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
NorfloxacinThe serum concentration of Didanosine can be decreased when it is combined with Norfloxacin.Approved
NystatinDidanosine can cause a decrease in the absorption of Nystatin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
OfloxacinThe serum concentration of Didanosine can be decreased when it is combined with Ofloxacin.Approved
OxiconazoleDidanosine can cause a decrease in the absorption of Oxiconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
PazufloxacinThe serum concentration of Didanosine can be decreased when it is combined with Pazufloxacin.Investigational
PefloxacinThe serum concentration of Didanosine can be decreased when it is combined with Pefloxacin.Approved
PentamidineDidanosine can cause a decrease in the absorption of Pentamidine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
PosaconazoleDidanosine can cause a decrease in the absorption of Posaconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational, Vet Approved
PrulifloxacinThe serum concentration of Didanosine can be decreased when it is combined with Prulifloxacin.Investigational
RadicicolDidanosine can cause a decrease in the absorption of Radicicol resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
RibavirinThe risk or severity of adverse effects can be increased when Ribavirin is combined with Didanosine.Approved
RilpivirineRilpivirine can cause a decrease in the absorption of Didanosine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
RosoxacinThe serum concentration of Didanosine can be decreased when it is combined with Rosoxacin.Approved
Salicylhydroxamic AcidDidanosine can cause a decrease in the absorption of Salicylhydroxamic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
Salicylic acidDidanosine can cause a decrease in the absorption of Salicylic acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
SertaconazoleDidanosine can cause a decrease in the absorption of Sertaconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SinefunginDidanosine can cause a decrease in the absorption of Sinefungin resulting in a reduced serum concentration and potentially a decrease in efficacy.Experimental
SirolimusDidanosine can cause a decrease in the absorption of Sirolimus resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
SparfloxacinThe serum concentration of Didanosine can be decreased when it is combined with Sparfloxacin.Approved
StavudineThe risk or severity of adverse effects can be increased when Stavudine is combined with Didanosine.Approved, Investigational
SulconazoleDidanosine can cause a decrease in the absorption of Sulconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
TavaboroleDidanosine can cause a decrease in the absorption of Tavaborole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
TemafloxacinThe serum concentration of Didanosine can be decreased when it is combined with Temafloxacin.Withdrawn
Tenofovir disoproxilThe therapeutic efficacy of Didanosine can be decreased when used in combination with Tenofovir.Approved, Investigational
TerbinafineDidanosine can cause a decrease in the absorption of Terbinafine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational, Vet Approved
TerconazoleDidanosine can cause a decrease in the absorption of Terconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
TeriflunomideThe serum concentration of Didanosine can be increased when it is combined with Teriflunomide.Approved
ThymolDidanosine can cause a decrease in the absorption of Thymol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
TioconazoleDidanosine can cause a decrease in the absorption of Tioconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
TipranavirThe serum concentration of Didanosine can be decreased when it is combined with Tipranavir.Approved, Investigational
TolnaftateDidanosine can cause a decrease in the absorption of Tolnaftate resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
TrimetrexateDidanosine can cause a decrease in the absorption of Trimetrexate resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
TrovafloxacinThe serum concentration of Didanosine can be decreased when it is combined with Trovafloxacin.Approved, Withdrawn
ValganciclovirThe risk or severity of adverse effects can be increased when Valganciclovir is combined with Didanosine.Approved, Investigational
VoriconazoleDidanosine can cause a decrease in the absorption of Voriconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Food Interactions
  • Avoid alcohol.
  • Take on empty stomach: 1 hour before or 2 hours after meals.
References
Synthesis Reference

Bandi Parthasaradhi Reddy, Kura Rathnakar Reddy, Rapolu Raji Reddy, Dasari Muralidhara Reddy, Kesireddy Subash Chander Reddy, "Novel Process for the Preparation of Didanosine Using Novel Intermediates." U.S. Patent US20080293938, issued November 27, 2008.

US20080293938
General ReferencesNot Available
External Links
ATC CodesJ05AF02 — Didanosine
AHFS Codes
  • 08:18.08.20
PDB Entries
FDA labelDownload (86.1 KB)
MSDSDownload (36.5 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentChronic Hepatitis C Infection / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections22
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infections, Cytomegalovirus1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi s Sarcoma (KS)1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAIDS-Related Dementia Complex / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAids / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAntiretroviral Naive / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentEncephalopathies / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections34
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi s Sarcoma (KS)1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Progressive Multifocal Leukoencephalopathy1
2SuspendedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2Unknown StatusTreatmentMalignant Lymphomas1
2WithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections2
3CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHIV Disease / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections14
3TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections3
3Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
4CompletedDiagnosticCardiovascular Disease (CVD) / HIV-Associated Lipodystrophy Syndrome1
4CompletedTreatmentHIV Disease1
4CompletedTreatmentHemophilia A / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections4
4Unknown StatusTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections20
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Progressive Multifocal Leukoencephalopathy1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis1
Not AvailableRecruitingNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableWithdrawnTreatmentHuman Immunodeficiency Virus (HIV) Infections / Viral Hepatitis B1
Pharmacoeconomics
Manufacturers
  • Aurobindo pharma ltd
  • Barr laboratories inc
  • Matrix laboratories ltd
  • Bristol myers squibb co
  • Bristol myers squibb co pharmaceutical research institute
Packagers
Dosage forms
FormRouteStrength
Capsule, delayed release pelletsOral200 mg/1
Capsule, delayed release pelletsOral250 mg/1
Capsule, delayed release pelletsOral400 mg/1
Powder, for solutionOral10 mg/mL
TabletOral100 mg
TabletOral150 mg
TabletOral25 mg
TabletOral50 mg
Capsule, delayed releaseOral125 mg
Capsule, delayed releaseOral125 mg/1
Capsule, delayed releaseOral200 mg
Capsule, delayed releaseOral200 mg/1
Capsule, delayed releaseOral250 mg
Capsule, delayed releaseOral250 mg/1
Capsule, delayed releaseOral400 mg
Capsule, delayed releaseOral400 mg/1
Powder, for solutionOral4 g
Prices
Unit descriptionCostUnit
Videx 4 gm Solution 200ml Bottle124.51USD bottle
Videx 2 gm Solution 100ml Bottle58.4USD bottle
Videx EC 400 mg Delayed Release Capsule14.75USD capsule
Videx ec 400 mg capsule14.18USD capsule
Didanosine 400 mg Delayed Release Capsule12.78USD capsule
Videx EC 250 mg Delayed Release Capsule9.44USD capsule
Videx ec 250 mg capsule9.08USD capsule
Didanosine 250 mg Delayed Release Capsule8.18USD capsule
Videx ec 200 mg capsule7.12USD capsule
Didanosine 200 mg Delayed Release Capsule6.42USD capsule
Videx ec 125 mg capsule4.45USD capsule
Videx 4 gm pediatric solution0.6USD ml
Videx 2 gm pediatric solution0.55USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2072573 No1996-05-282011-01-03Canada
CA2332922 No2008-02-122018-08-04Canada
US5880106 No1995-01-222012-01-22Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)160-163 °CPhysProp
water solubility15.8 mg/mLNot Available
logP-1.24SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility6.58 mg/mLALOGPS
logP-0.99ALOGPS
logP-0.35ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)6.94ChemAxon
pKa (Strongest Basic)2.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.74 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.59 m3·mol-1ChemAxon
Polarizability22.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.996
Blood Brain Barrier+0.823
Caco-2 permeable-0.9019
P-glycoprotein substrateNon-substrate0.5948
P-glycoprotein inhibitor INon-inhibitor0.945
P-glycoprotein inhibitor IINon-inhibitor0.6378
Renal organic cation transporterNon-inhibitor0.8049
CYP450 2C9 substrateNon-substrate0.8065
CYP450 2D6 substrateNon-substrate0.7777
CYP450 3A4 substrateNon-substrate0.5234
CYP450 1A2 substrateNon-inhibitor0.6934
CYP450 2C9 inhibitorNon-inhibitor0.9064
CYP450 2D6 inhibitorNon-inhibitor0.9145
CYP450 2C19 inhibitorNon-inhibitor0.8646
CYP450 3A4 inhibitorNon-inhibitor0.9608
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7288
Ames testAMES toxic0.8682
CarcinogenicityNon-carcinogens0.9094
BiodegradationNot ready biodegradable0.8478
Rat acute toxicity2.0874 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9451
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0090000000-fed0a8ffc5839fe73fe1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0490000000-0ac04c4f4e817e6da391View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0920000000-14a23956c10d3f6e7e9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0900000000-de4599cfceaa46089291View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-1900000000-10d07c81e3fc72fcfef2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-1900000000-84e8bb1bea77e6b5bfcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-6a0516d1b3cec255e050View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-fd0dfb766f1c628d170dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-3d9e0ecfaf77d867a9d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-e0e7d0c808e14d842dbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-1900000000-9d4b77c3e99e9f9a2c2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-1900000000-2bb63f71ec2e92ce075dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine 2',3'-dideoxyribonucleosides. These are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at positions 2 and 3.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleosides
Sub ClassPurine 2',3'-dideoxyribonucleosides
Direct ParentPurine 2',3'-dideoxyribonucleosides
Alternative ParentsHypoxanthines / 6-oxopurines / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Tetrahydrofurans / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Primary alcohols
SubstituentsPurine 2',3'-dideoxyribonucleoside / 6-oxopurine / Hypoxanthine / Purinone / Imidazopyrimidine / Purine / Pyrimidone / N-substituted imidazole / Pyrimidine / Heteroaromatic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorspurine 2',3'-dideoxyribonucleoside (CHEBI:490877 )

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
yes
Actions
inhibitor
General Function:
Rna-dna hybrid ribonuclease activity
Specific Function:
Not Available
Gene Name:
pol
Uniprot ID:
Q72547
Uniprot Name:
Reverse transcriptase/RNaseH
Molecular Weight:
65223.615 Da
References
  1. Faulds D, Brogden RN: Didanosine. A review of its antiviral activity, pharmacokinetic properties and therapeutic potential in human immunodeficiency virus infection. Drugs. 1992 Jul;44(1):94-116. [PubMed:1379914 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Purine-nucleoside phosphorylase activity
Specific Function:
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate.
Gene Name:
PNP
Uniprot ID:
P00491
Uniprot Name:
Purine nucleoside phosphorylase
Molecular Weight:
32117.69 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Uniprot Name:
Serum albumin
Molecular Weight:
69365.94 Da
References
  1. Bocedi A, Notaril S, Narciso P, Bolli A, Fasano M, Ascenzi P: Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. [PubMed:15814459 ]
  2. Bocedi A, Notari S, Menegatti E, Fanali G, Fasano M, Ascenzi P: Allosteric modulation of anti-HIV drug and ferric heme binding to human serum albumin. FEBS J. 2005 Dec;272(24):6287-96. [PubMed:16336266 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Uniprot Name:
Solute carrier family 22 member 6
Molecular Weight:
61815.78 Da
References
  1. Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nucleoside transmembrane transporter activity
Specific Function:
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs).
Gene Name:
SLC29A1
Uniprot ID:
Q99808
Uniprot Name:
Equilibrative nucleoside transporter 1
Molecular Weight:
50218.805 Da
References
  1. Yao SY, Ng AM, Sundaram M, Cass CE, Baldwin SA, Young JD: Transport of antiviral 3'-deoxy-nucleoside drugs by recombinant human and rat equilibrative, nitrobenzylthioinosine (NBMPR)-insensitive (ENT2) nucleoside transporter proteins produced in Xenopus oocytes. Mol Membr Biol. 2001 Apr-Jun;18(2):161-7. [PubMed:11463208 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nucleoside transmembrane transporter activity
Specific Function:
Mediates equilibrative transport of purine, pyrimidine nucleosides and the purine base hypoxanthine. Very less sensitive than SLC29A1 to inhibition by nitrobenzylthioinosine (NBMPR), dipyridamole, dilazep and draflazine.
Gene Name:
SLC29A2
Uniprot ID:
Q14542
Uniprot Name:
Equilibrative nucleoside transporter 2
Molecular Weight:
50112.335 Da
References
  1. Yao SY, Ng AM, Sundaram M, Cass CE, Baldwin SA, Young JD: Transport of antiviral 3'-deoxy-nucleoside drugs by recombinant human and rat equilibrative, nitrobenzylthioinosine (NBMPR)-insensitive (ENT2) nucleoside transporter proteins produced in Xenopus oocytes. Mol Membr Biol. 2001 Apr-Jun;18(2):161-7. [PubMed:11463208 ]
Drug created on June 13, 2005 07:24 / Updated on July 21, 2017 17:46