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Record Information
Version1.0
Creation Date2014-09-11 05:16:31 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003743
Identification
Common NameDidanosine
ClassSmall Molecule
DescriptionA dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Anti-HIV Agent
  • Antimetabolite
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Reverse Transcriptase Inhibitor
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
2,3-DideoxyinosineChEBI
9-((2R,5S)-5-(Hydroxymethyl)-tetrahydrofuran-2-yl)-1H-purin-6(9H)-oneChEBI
9-((2R,5S)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-oneChEBI
9-((2S,5R)-5-Hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-olChEBI
9-[(2R,5S)-5-(Hydroxymethyl)tetrahydrofuran-2-yl]-1,9-dihydro-6H-purin-6-oneChEBI
DDIChEBI
DdInoChEBI
DidanosinaChEBI
DidanosinumChEBI
DideoxyinosineChEBI
VidexKegg
2',3' DideoxyinosineHMDB
Bristol-myers brand OF didanosineHMDB
DdI (antiviral)HMDB
Bristol myers squibb brand OF didanosineHMDB
2',3'-DideoxyinosineHMDB
Bristol myers brand OF didanosineHMDB
Bristol-myers squibb brand OF didanosineHMDB
Chemical FormulaC10H12N4O3
Average Molecular Mass236.227 g/mol
Monoisotopic Mass236.091 g/mol
CAS Registry Number69655-05-6
IUPAC Name9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
Traditional Namedidanosine
SMILESOC[C@@H]1CC[C@@H](O1)N1C=NC2=C1NC=NC2=O
InChI IdentifierInChI=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 KeyBXZVVICBKDXVGW-NKWVEPMBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine 2',3'-dideoxyribonucleosides. Purine 2',3'-dideoxyribonucleosides 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 Parents
Substituents
  • Purine 2',3'-dideoxyribonucleoside
  • 6-oxopurine
  • Hypoxanthine
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Tetrahydrofuran
  • Vinylogous amide
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Alcohol
  • Organopnictogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point160-163°C
Boiling PointNot Available
Solubility15.8 mg/mL
Predicted Properties
PropertyValueSource
Water Solubility6.58 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.59 m³·mol⁻¹ChemAxon
Polarizability22.9 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-056u-9670000000-b8e1fdd18fda2c412cefView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-005c-7090000000-ed6dc7eca7c11c73693aView in MoNA
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, Positivesplash10-000i-0920000000-a89fd678ed8a8c16acccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-a1a5b268d419fff83602View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-1900000000-32bbc23c752210d7cd6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-383b44cf919dd28ff3bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2940000000-309e7293be866f0e29aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052u-3900000000-0828603c96a200af867aView in MoNA
Toxicity Profile
Route of ExposureRapidly absorbed (bioavailability 30-40%) with peak plasma concentrations appearing within 0.5 and 1.5 hrs.
Mechanism of ToxicityDidanosine (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.
MetabolismRapidly 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 ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesFor use, in combination with other antiretroviral agents, in the treatment of HIV-1 infection in adults.
Minimum Risk LevelNot Available
Health EffectsSide effects include pancreatitis, peripheral neuropathy, diarrhea, hyperuricemia and hepatic dysfunction.
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00900
HMDB IDHMDB0015037
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB ID2DI
Wikipedia LinkDidanosine
Chemspider ID45864
ChEBI ID490877
PubChem Compound ID50599
Kegg Compound IDC06953
YMDB IDNot Available
ECMDB IDNot Available
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.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10386939
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1619614
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17046264
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18549801
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=29438107