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Didanosine

July 24, 2017
Common Name

Didanosine 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A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen.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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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 2',3' DideoxyinosineMeSH Bristol-myers brand OF didanosineMeSH DdI (antiviral)MeSH Bristol myers squibb brand OF didanosineMeSH 2',3'-DideoxyinosineMeSH Bristol myers brand OF didanosineMeSH Bristol-myers squibb brand OF didanosineMeSH VidexMeSH

Chemical Formlia

C10H12N4O3 Average Molecliar Weight

236.2273 Monoisotopic Molecliar Weight

236.09094027 IUPAC Name

9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one Traditional Name

didanosine CAS Registry Number

69655-05-6 SMILES

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

InChI Identifier

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

InChI Key

BXZVVICBKDXVGW-NKWVEPMBSA-N Chemical Taxonomy Description

This 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. Kingdom

Organic compounds Super Class

Nucleosides, nucleotides, and analogues Class

Purine nucleosides Sub Class

Purine 2,3-dideoxyribonucleosides Direct Parent

Purine 2,3-dideoxyribonucleosides Alternative Parents

  • Hypoxanthines
  • 6-oxopurines
  • Pyrimidones
  • N-substituted imidazoles
  • Vinylogous amides
  • Tetrahydrofurans
  • Heteroaromatic compounds
  • Oxacyclic compounds
  • Azacyclic compounds
  • Primary alcohols
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • purine 2',3'-dideoxyribonucleoside (CHEBI:490877 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-HIV Agents
  • Antimetabolites
  • Purine Nucleoside Phosphorylase inhibitor
  • Reverse Transcriptase Inhibitors

    • Application

  • Pharmaceutical

    • Cellliar locations

    Not Available Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point160 – 163 °CNot Available Boiling PointNot AvailableNot Available Water Solubility6.58e+00 g/LNot Available LogP-0.2Not Available

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-000i-0090000000-fed0a8ffc5839fe73fe1View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-000i-0490000000-0ac04c4f4e817e6da391View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-000i-0920000000-14a23956c10d3f6e7e9aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-000i-0900000000-de4599cfceaa46089291View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-000i-1900000000-10d07c81e3fc72fcfef2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-000i-1900000000-84e8bb1bea77e6b5bfcaView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-000i-0900000000-6a0516d1b3cec255e050View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-000i-0900000000-fd0dfb766f1c628d170dView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-000i-0900000000-3d9e0ecfaf77d867a9d9View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-000i-0900000000-e0e7d0c808e14d842dbbView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-000i-1900000000-9d4b77c3e99e9f9a2c2aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-000i-1900000000-2bb63f71ec2e92ce075dView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

    Not Available Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Didanosine Action PathwaySMP00739Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00900

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00900

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-4 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00900 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    45864 KEGG Compound ID

    C06953 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Didanosine NuGOwiki Link

    HMDB15037 Metagene Link

    HMDB15037 METLIN ID

    Not Available PubChem Compound

    50599 PDB ID

    2DI ChEBI ID

    490877

    Product: Dictamine

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in 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
    Molecular weight:
    32117.69
    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 ]

    Transporters

    General function:
    Involved in ion 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). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3-azido- 3-deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
    Gene Name:
    SLC22A6
    Uniprot ID:
    Q4U2R8
    Molecular weight:
    61815.8
    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 ]

    PMID: 20442301

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