Page last updated: 2024-10-15

allopurinol riboside

Description

allopurinol riboside : A nucleoside analogue that is allopurinol with a beta-D-ribofuranosyl moiety at the 1-position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID135407110
CHEMBL ID1688966
CHEMBL ID603304
CHEBI ID74074
SCHEMBL ID6912039
SCHEMBL ID11673117
SCHEMBL ID11672972
MeSH IDM0077495

Synonyms (41)

Synonym
nsc-138437
allopurinol riboside
16220-07-8
allopurinol ribonucleoside
allopurinol-1-ribonucleoside
4-hydroxy[3,4-d]pyrazolopyrimidine riboside
1-.beta.-d-ribofuranosylpyrazolo[3,4-d]pyrimidine-4-one
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2h-pyrazolo[3,4-d]pyrimidin-4-one
nsc-252629
1h-pyrazolo[3,4-d]pyrimidin-4-ol, 1-.beta.-d-ribofuranosyl-
(2r,3s,4r,5r)-2-(hydroxymethyl)-5-(4-hydroxypyrazolo[3,4-d]pyrimidin-1-yl)tetrahydrofuran-3,4-diol
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5h-pyrazolo[3,4-d]pyrimidin-4-one
1-(.beta.-d-ribofuranosyl)-1,5-dihydro-4h- pyrazolo-[3,4-d]pyrimidin-4-one
nsc 138437
1,5-dihydro-1-beta-d-ribofuranosyl-4h-pyrazolo(3,4-d)pyrimidin-4-one
4-hydroxy(3,4-d)pyrazolopyrimidine riboside
4-hydroxy-1beta-d-ribofuranosylpyrazolo(3,4-d)pyrimidine
4h-pyrazolo(3,4-d)pyrimidin-4-one, 1,5-dihydro-1-beta-d-ribofuranosyl-
chebi:74074 ,
CHEMBL1688966 ,
wzs8452sec ,
unii-wzs8452sec
SCHEMBL6912039
1-(beta-d-ribofuranosyl)-1,7-dihydro-4h-pyrazolo[3,4-d]pyrimidin-4-one
chembl603304
bdbm50366805
4h-pyrazolo(3,4-d)pyrimidin-4-one, 1,5-dihydro-1-.beta.-d-ribofuranosyl-
4-hydroxy-1h-pyrazolo[3,4-d]pyrimidine riboside
KFQUAMTWOJHPEJ-DAGMQNCNSA-N
SCHEMBL11673117
SCHEMBL11672972
1-beta-d-ribofuranosyl-1h-pyrazolo[3,4-d]pyrimidine-4-one
HY-101397
CS-6408
1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1h-pyrazolo[3,4-d]pyrimidin-4(5h)-one
Q27144387
4h-pyrazolo[3,4-d]pyrimidin-4-one, 1,5-dihydro-1-beta-d-ribofuranosyl-
MS-23785
8-aza-7-deazainosine
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5h-pyrazolo[3,4-d]pyrimidin-4-one
AKOS040740689

Research Excerpts

Overview

Allopurinol riboside is an experimental agent for the treatment of leishmaniasis and American trypanosomiasis.

ExcerptReference
"Allopurinol riboside is an experimental agent for the treatment of leishmaniasis and American trypanosomiasis. "( Effects of probenecid on the pharmacokinetics of allopurinol riboside.
Shapiro, TA; Were, JB, 1993
)

Pharmacokinetics

ExcerptReference
"6 hours after administration, has an elimination half-life of 3 hours, and steady-state concentrations in the therapeutic range."( Pharmacokinetics and metabolism of allopurinol riboside.
Danso, K; Desjardins, RE; Nelson, DJ; Pamplin, CL; Shapiro, TA; Were, JB, 1991
)
" In this randomized, crossover evaluation in healthy volunteers, probenecid reduces the renal clearance of allopurinol riboside, extends the half-life of allopurinol riboside in plasma, and triples the levels of allopurinol riboside in plasma."( Effects of probenecid on the pharmacokinetics of allopurinol riboside.
Shapiro, TA; Were, JB, 1993
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
nucleoside analogueAn analogue of a nucleoside, being an N-glycosyl compound in which the nitrogen-containing moiety is a modified nucleotide base. They are commonly used as antiviral products to prevent viral replication in infected cells.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Purine nucleoside phosphorylaseHomo sapiens (human)Ki1,900.00000.00000.52897.0000AID164753; AID164755
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (17)

Processvia Protein(s)Taxonomy
inosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
urate biosynthetic processPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of T cell proliferationPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of alpha-beta T cell differentiationPurine nucleoside phosphorylaseHomo sapiens (human)
allantoin metabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
nucleobase-containing compound metabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
inosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
deoxyinosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
deoxyadenosine catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
purine ribonucleoside salvagePurine nucleoside phosphorylaseHomo sapiens (human)
IMP catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
nicotinamide riboside catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
immune responsePurine nucleoside phosphorylaseHomo sapiens (human)
nucleotide biosynthetic processPurine nucleoside phosphorylaseHomo sapiens (human)
response to xenobiotic stimulusPurine nucleoside phosphorylaseHomo sapiens (human)
positive regulation of interleukin-2 productionPurine nucleoside phosphorylaseHomo sapiens (human)
purine-containing compound salvagePurine nucleoside phosphorylaseHomo sapiens (human)
dAMP catabolic processPurine nucleoside phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
nucleoside bindingPurine nucleoside phosphorylaseHomo sapiens (human)
purine nucleobase bindingPurine nucleoside phosphorylaseHomo sapiens (human)
purine-nucleoside phosphorylase activityPurine nucleoside phosphorylaseHomo sapiens (human)
protein bindingPurine nucleoside phosphorylaseHomo sapiens (human)
phosphate ion bindingPurine nucleoside phosphorylaseHomo sapiens (human)
identical protein bindingPurine nucleoside phosphorylaseHomo sapiens (human)
guanosine phosphorylase activityPurine nucleoside phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
extracellular regionPurine nucleoside phosphorylaseHomo sapiens (human)
cytoplasmPurine nucleoside phosphorylaseHomo sapiens (human)
cytosolPurine nucleoside phosphorylaseHomo sapiens (human)
secretory granule lumenPurine nucleoside phosphorylaseHomo sapiens (human)
extracellular exosomePurine nucleoside phosphorylaseHomo sapiens (human)
ficolin-1-rich granule lumenPurine nucleoside phosphorylaseHomo sapiens (human)
cytoplasmPurine nucleoside phosphorylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID218222Virus rating was determined by comparing cytopathic effect against vero cells after infection with Herpes simplex virus-11984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Synthesis and biological activity of certain 3,4-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides.
AID164753Compound was evaluated for its binding affinity against Toxoplasma gondii purine nucleoside phosphorylase from cystic strain ME 49 (value indicates competitive inhibition)2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
Benzimidazole-4,7-diones as inhibitors of protozoal (Toxoplasma gondii) purine nucleoside phosphorylase.
AID97435Increase in life span of tumor L1210 leukemic mice 1-5 days after 400 mg/kg administered1981Journal of medicinal chemistry, Oct, Volume: 24, Issue:10
Pyrazolopyrimidine nucleosides. 12. Synthesis and biological activity of certain pyrazolo[3,4-d]pyrimidine nucleosides related to adenosine.
AID218225Virus rating was determined by comparing cytopathic effect against vero cells after infection with Vesicular stomatitis virus1984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Synthesis and biological activity of certain 3,4-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides.
AID29732Toxic level was determined; Non toxic1984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Synthesis and biological activity of certain 3,4-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides.
AID1753481Cytotoxicity against human MRC-5 SV2 cells assessed as reduction in cell growth measured after 3 days by resazurin dye based fluorometric analysis2021Journal of medicinal chemistry, 04-08, Volume: 64, Issue:7
Revisiting Pyrazolo[3,4-
AID98469Toxicity against L1210 leukemic cells 1-5 days after administration of 400 mg/kg of the compound; nt= No higher dose tested1981Journal of medicinal chemistry, Oct, Volume: 24, Issue:10
Pyrazolopyrimidine nucleosides. 12. Synthesis and biological activity of certain pyrazolo[3,4-d]pyrimidine nucleosides related to adenosine.
AID164751Inhibition of Toxoplasma gondii purine nucleoside phosphorylase from virulent strain RH at 4 mM2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
Benzimidazole-4,7-diones as inhibitors of protozoal (Toxoplasma gondii) purine nucleoside phosphorylase.
AID101045Concentration in the culture media that produced 50% inhibition of the leishmania tropica growth; Range is 76-1901984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Synthesis and biological activity of certain 3,4-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides.
AID1753482Selectivity index, ratio of CC50 for human MRC-5 SV2 cells to IC50 for antitrypanosomal activity against nifurtimox-sensitive Trypanosoma cruzi Tulahuen CL2 infected in human MRC-5 SV2 cells2021Journal of medicinal chemistry, 04-08, Volume: 64, Issue:7
Revisiting Pyrazolo[3,4-
AID164747Inhibition of Toxoplasma gondii purine nucleoside phosphorylase from cystic strain ME 49 at 1 mM2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
Benzimidazole-4,7-diones as inhibitors of protozoal (Toxoplasma gondii) purine nucleoside phosphorylase.
AID1753484Cytotoxicity against Swiss mouse peritoneal macrophages assessed as cell detachment, lysis and granulation measured after 5 days by microscopic analysis2021Journal of medicinal chemistry, 04-08, Volume: 64, Issue:7
Revisiting Pyrazolo[3,4-
AID1753483Antileishmanial activity against amastigote form of Leishmania infantum MHOM/MA(BE)/67 infected in Swiss mouse peritoneal macrophages assessed as reduction in parasite growth treated at 2 hrs post-infection and measured after 5 days by Giemsa staining bas2021Journal of medicinal chemistry, 04-08, Volume: 64, Issue:7
Revisiting Pyrazolo[3,4-
AID218223Virus rating was determined by comparing cytopathic effect against vero cells after infection with Parainfluenza type 3 (para 3)1984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Synthesis and biological activity of certain 3,4-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides.
AID164755Compound was evaluated for its binding affinity against Toxoplasma gondii purine nucleoside phosphorylase of virulent strain RH (value indicates competitive inhibition)2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
Benzimidazole-4,7-diones as inhibitors of protozoal (Toxoplasma gondii) purine nucleoside phosphorylase.
AID164748Inhibition of Toxoplasma gondii purine nucleoside phosphorylase from cystic strain ME 49 at 4 mM2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
Benzimidazole-4,7-diones as inhibitors of protozoal (Toxoplasma gondii) purine nucleoside phosphorylase.
AID218224Virus rating was determined by comparing cytopathic effect against vero cells after infection with Vaccinia virus1984Journal of medicinal chemistry, Sep, Volume: 27, Issue:9
Synthesis and biological activity of certain 3,4-disubstituted pyrazolo[3,4-d]pyrimidine nucleosides.
AID53010In vitro minimum inhibitory concentration for Eimeria tenella in embryonic chick liver cells1982Journal of medicinal chemistry, Sep, Volume: 25, Issue:9
Pyrazolo[3,4-d]pyrimidine ribonucleosides as anticoccidials. 2. Synthesis and activity of some nucleosides of 4-(alkylamino)-1H-pyrazolo[3, 4-d]pyrimidines.
AID1753480Antitrypanosomal activity against nifurtimox-sensitive Trypanosoma cruzi Tulahuen CL2 infected in human MRC-5 SV2 cells assessed as inhibition of parasite growth measured after 7 days by spectrophotometric analysis2021Journal of medicinal chemistry, 04-08, Volume: 64, Issue:7
Revisiting Pyrazolo[3,4-
AID51084Compound tested in vivo for anti-coccidial activity which cleared number of chicks from parasite at 400 ppm in the diet1982Journal of medicinal chemistry, Sep, Volume: 25, Issue:9
Pyrazolo[3,4-d]pyrimidine ribonucleosides as anticoccidials. 2. Synthesis and activity of some nucleosides of 4-(alkylamino)-1H-pyrazolo[3, 4-d]pyrimidines.
AID1753485Selectivity index, ratio of CC50 for Swiss mouse peritoneal macrophages to IC50 for antileishmanial activity against amastigote form of Leishmania infantum MHOM/MA(BE)/67 infected in Swiss mouse peritoneal macrophages2021Journal of medicinal chemistry, 04-08, Volume: 64, Issue:7
Revisiting Pyrazolo[3,4-
AID164750Inhibition of Toxoplasma gondii purine nucleoside phosphorylase from virulent strain RH at 1 mM2002Bioorganic & medicinal chemistry letters, Mar-25, Volume: 12, Issue:6
Benzimidazole-4,7-diones as inhibitors of protozoal (Toxoplasma gondii) purine nucleoside phosphorylase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

TimeframeStudies, This Drug (%)All Drugs %
pre-199030 (75.00)18.7374
1990's4 (10.00)18.2507
2000's2 (5.00)29.6817
2010's2 (5.00)24.3611
2020's2 (5.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (10.00%)5.53%
Reviews1 (2.50%)6.00%
Case Studies3 (7.50%)4.05%
Observational0 (0.00%)0.25%
Other32 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]