Page last updated: 2024-12-06

isoguanosine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Isoguanosine is a synthetic nucleoside analog that exhibits antiviral activity against various viruses, including HIV, hepatitis B, and herpes simplex virus. It is structurally similar to guanosine but has an altered base structure, leading to its distinct biological properties. Its antiviral mechanism involves inhibiting viral DNA polymerase, preventing viral replication. Isoguanosine has also been studied for its potential therapeutic applications in cancer treatment due to its ability to induce apoptosis in cancer cells. The compound's unique chemical structure and biological activities make it a valuable tool for drug development research and a potential candidate for novel antiviral and anticancer therapies.'

Cross-References

ID SourceID
PubMed CID13873258
MeSH IDM0051817
PubMed CID65085
CHEMBL ID1688963
CHEBI ID3927
SCHEMBL ID2773634
MeSH IDM0051817

Synonyms (50)

Synonym
isoguanosine
9h-purin-2-ol, 6-amino-9-beta-d-ribofuranosyl-
adenosine, 1,2-dihydro-2-oxo-
isoguanine, 9-beta-d-ribofuranosyl-
isoguanosine (van)
1,2-dihydro-2-oxoadenosine
nsc 12161
isoguanosine (7ci,8ci)
crotonosid
isoguanine, 9-.beta.-d-ribofuranosyl-
isoguanine riboside
2-hydroxyadenosine
PDSP1_000998
PDSP2_000982
1818-71-9
crotonoside
C08432
6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1h-purin-2-one
2-oxoado (isoguanosine)
bdbm82031
cas_1818-71-9
chebi:3927 ,
CHEMBL1688963
S9275
AKOS015969770
ccris 8240
6v7fte1z1v ,
unii-6v7fte1z1v
6-amino-9-((2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-3h-purin-2(9h)-one;9-?-d-ribofuranosylisoguanine
SCHEMBL2773634
6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1h-purin-2-one
MIKUYHXYGGJMLM-UUOKFMHZSA-N
2-oxo-3-hydroadenosine
AC-33996
mfcd04971989
6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,9-dihydro-2h-purin-2-one
AS-59704
crotonoside, >=95% (hplc)
(2r,3r,4s,5r)-2-(6-amino-2-hydroxy-9h-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
6-amino-9-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,9-dihydro-2h-purin-2-one
HY-N0071
F12745
Q27106249
2,3-dihydro-2-oxoadenosine
9h-purin-2-ol, 6-amino-9-.beta.-d-ribofuranosyl-(6c
CCG-267276
CS-0007114
h5f ,
6-azanyl-9-[(2r,3r,4s,5r)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]-1h-purin-2-one
BP-58626
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
purine nucleoside
[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 (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki0.09400.00011.20929.9700AID32503
Adenosine receptor A2bRattus norvegicus (Norway rat)Ki0.33000.00061.353610.0000AID33732
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki0.33000.00021.494010.0000AID33732
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A2aHomo sapiens (human)EC50 (µMol)0.07940.00030.708110.0000AID30506
Adenosine receptor A2bHomo sapiens (human)EC50 (µMol)0.07940.00030.946110.0000AID30506
Adenosine receptor A1Cavia porcellus (domestic guinea pig)EC50 (µMol)1.14810.01261.93385.6234AID32147
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (61)

Processvia Protein(s)Taxonomy
synaptic transmission, dopaminergicAdenosine receptor A2aHomo sapiens (human)
response to amphetamineAdenosine receptor A2aHomo sapiens (human)
regulation of DNA-templated transcriptionAdenosine receptor A2aHomo sapiens (human)
phagocytosisAdenosine receptor A2aHomo sapiens (human)
apoptotic processAdenosine receptor A2aHomo sapiens (human)
inflammatory responseAdenosine receptor A2aHomo sapiens (human)
cellular defense responseAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
cell-cell signalingAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, cholinergicAdenosine receptor A2aHomo sapiens (human)
central nervous system developmentAdenosine receptor A2aHomo sapiens (human)
blood coagulationAdenosine receptor A2aHomo sapiens (human)
sensory perceptionAdenosine receptor A2aHomo sapiens (human)
locomotory behaviorAdenosine receptor A2aHomo sapiens (human)
blood circulationAdenosine receptor A2aHomo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A2aHomo sapiens (human)
response to xenobiotic stimulusAdenosine receptor A2aHomo sapiens (human)
response to inorganic substanceAdenosine receptor A2aHomo sapiens (human)
positive regulation of glutamate secretionAdenosine receptor A2aHomo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmissionAdenosine receptor A2aHomo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A2aHomo sapiens (human)
response to purine-containing compoundAdenosine receptor A2aHomo sapiens (human)
response to caffeineAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
positive regulation of urine volumeAdenosine receptor A2aHomo sapiens (human)
vasodilationAdenosine receptor A2aHomo sapiens (human)
eating behaviorAdenosine receptor A2aHomo sapiens (human)
negative regulation of vascular permeabilityAdenosine receptor A2aHomo sapiens (human)
negative regulation of neuron apoptotic processAdenosine receptor A2aHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, sleepAdenosine receptor A2aHomo sapiens (human)
negative regulation of alpha-beta T cell activationAdenosine receptor A2aHomo sapiens (human)
astrocyte activationAdenosine receptor A2aHomo sapiens (human)
neuron projection morphogenesisAdenosine receptor A2aHomo sapiens (human)
positive regulation of protein secretionAdenosine receptor A2aHomo sapiens (human)
negative regulation of inflammatory responseAdenosine receptor A2aHomo sapiens (human)
regulation of mitochondrial membrane potentialAdenosine receptor A2aHomo sapiens (human)
membrane depolarizationAdenosine receptor A2aHomo sapiens (human)
regulation of calcium ion transportAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
inhibitory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
prepulse inhibitionAdenosine receptor A2aHomo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2aHomo sapiens (human)
positive regulation of long-term synaptic potentiationAdenosine receptor A2aHomo sapiens (human)
positive regulation of apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
positive regulation of chronic inflammatory response to non-antigenic stimulusAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A2bHomo sapiens (human)
positive regulation of vascular endothelial growth factor productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
positive regulation of chemokine productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of interleukin-6 productionAdenosine receptor A2bHomo sapiens (human)
mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
positive regulation of mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
relaxation of vascular associated smooth muscleAdenosine receptor A2bHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2bHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
vasodilationAdenosine receptor A2bHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A2aHomo sapiens (human)
protein bindingAdenosine receptor A2aHomo sapiens (human)
calmodulin bindingAdenosine receptor A2aHomo sapiens (human)
lipid bindingAdenosine receptor A2aHomo sapiens (human)
enzyme bindingAdenosine receptor A2aHomo sapiens (human)
type 5 metabotropic glutamate receptor bindingAdenosine receptor A2aHomo sapiens (human)
identical protein bindingAdenosine receptor A2aHomo sapiens (human)
protein-containing complex bindingAdenosine receptor A2aHomo sapiens (human)
alpha-actinin bindingAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2bHomo sapiens (human)
protein bindingAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor activityAdenosine receptor A2bHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A2aHomo sapiens (human)
intermediate filamentAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2aHomo sapiens (human)
membraneAdenosine receptor A2aHomo sapiens (human)
dendriteAdenosine receptor A2aHomo sapiens (human)
axolemmaAdenosine receptor A2aHomo sapiens (human)
asymmetric synapseAdenosine receptor A2aHomo sapiens (human)
presynaptic membraneAdenosine receptor A2aHomo sapiens (human)
neuronal cell bodyAdenosine receptor A2aHomo sapiens (human)
postsynaptic membraneAdenosine receptor A2aHomo sapiens (human)
presynaptic active zoneAdenosine receptor A2aHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A2bHomo sapiens (human)
presynapseAdenosine receptor A2bHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2bHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID32503Inhibition of binding of [3H]N6-cyclohexyladenosine to adenosine A1 receptor of rat whole brain membranes.1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
C2,N6-disubstituted adenosines: synthesis and structure-activity relationships.
AID232382Ratio of EC50 stim-QRS (conduction block) and EC50 for vasodilation of coronary arteries1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor.
AID180086Cardiovascular response in conscious hypertensive rats after administration of compound expressed as percent reduction in heart rate; NT= Not tested1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Synthesis and pharmacological evaluation of a series of analogues of 1-methylisoguanosine.
AID584547Antibacterial activity against Bacillus anthracis Sterne 34F2 infected in mouse J774A.1 cells assessed as protection against bacteria-induced cytotoxicity using propidium iodide staining after 3 hrs measured every hours for up to 7 hrs2010Antimicrobial agents and chemotherapy, Dec, Volume: 54, Issue:12
Testing nucleoside analogues as inhibitors of Bacillus anthracis spore germination in vitro and in macrophage cell culture.
AID112318Effective peroral dose hypothermic activity in mice1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Synthesis and pharmacological evaluation of a series of analogues of 1-methylisoguanosine.
AID193961Antiallergic activity of compound (10 mg/kg, iv) was assessed by the inhibition of passive paw anaphylaxis in rats; NT= Not tested1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Synthesis and pharmacological evaluation of a series of analogues of 1-methylisoguanosine.
AID32147Prolongation of the stimulus-QRS interval by 50% of the maximum response at the Adenosine A1 receptor in langendorff guinea pig heart preparation1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor.
AID584546Inhibition of inosine/L-alanine-induced Bacillus anthracis Sterne 34F2 spore germination pretreated for 15 mins before inosine/L-alanine challenge2010Antimicrobial agents and chemotherapy, Dec, Volume: 54, Issue:12
Testing nucleoside analogues as inhibitors of Bacillus anthracis spore germination in vitro and in macrophage cell culture.
AID171636Cardiovascular response in conscious hypertensive rats after administration of compound expressed as percent reduction in blood pressure; NT= Not tested1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Synthesis and pharmacological evaluation of a series of analogues of 1-methylisoguanosine.
AID33732Inhibition of [3H]NECA binding to Adenosine A2 receptor of rat striatal membranes1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
C2,N6-disubstituted adenosines: synthesis and structure-activity relationships.
AID232472Selectivity ratio for A1 receptor to that of A2 receptor in vitro in rat tissues1989Journal of medicinal chemistry, Aug, Volume: 32, Issue:8
C2,N6-disubstituted adenosines: synthesis and structure-activity relationships.
AID112313Effective peroral dose for muscle relaxation in mice1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Synthesis and pharmacological evaluation of a series of analogues of 1-methylisoguanosine.
AID612651Activity of recombinant human ADAL1 expressed in Escherichia coli by UV-spectrophotometry2011Journal of medicinal chemistry, Aug-25, Volume: 54, Issue:16
Adenosine deaminase-like protein 1 (ADAL1): characterization and substrate specificity in the hydrolysis of N(6)- or O(6)-substituted purine or 2-aminopurine nucleoside monophosphates.
AID193962Antiinflammatory activity of 100mg/Kg, po compound was assessed by inhibition of carrageenan-induced edema in rats; NA= No activity1981Journal of medicinal chemistry, Aug, Volume: 24, Issue:8
Synthesis and pharmacological evaluation of a series of analogues of 1-methylisoguanosine.
AID584550Cytotoxicity against mouse J774A1 cells2010Antimicrobial agents and chemotherapy, Dec, Volume: 54, Issue:12
Testing nucleoside analogues as inhibitors of Bacillus anthracis spore germination in vitro and in macrophage cell culture.
AID30506Coronary arteries vasodilation at the Adenosine A2 receptor in langendorff guinea pig heart preparation1991Journal of medicinal chemistry, Apr, Volume: 34, Issue:4
2-Alkoxyadenosines: potent and selective agonists at the coronary artery A2 adenosine receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (43)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (16.28)18.7374
1990's8 (18.60)18.2507
2000's14 (32.56)29.6817
2010's10 (23.26)24.3611
2020's4 (9.30)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.42

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.42 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other41 (100.00%)84.16%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]