Compounds > 8-azaadenosine
Page last updated: 2024-12-07

8-azaadenosine

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

8-Azaadenosine is a synthetic nucleoside analog of adenosine that has been studied for its potential therapeutic applications. It exhibits various pharmacological effects, including inhibition of adenosine deaminase, an enzyme responsible for degrading adenosine. This inhibition leads to increased adenosine levels, which in turn can modulate various physiological processes, such as immune responses, neurotransmission, and cardiovascular function. 8-Azaadenosine has also been shown to possess antiviral activity against certain viruses, such as HIV. It is also investigated for its potential in treating various diseases, including cancer and inflammatory disorders. Its synthesis typically involves the modification of adenosine with an azide group at the 8-position. '

Cross-References

ID SourceID
PubMed CID96410
CHEMBL ID174661
CHEBI ID2310
SCHEMBL ID115636
MeSH IDM0042651

Synonyms (28)

Synonym
(2r,3r,4s,5r)-2-(7-aminotriazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
8-aza-adenosine
3h-v-triazolo[4,5-d]pyrimidine,7-amino-3-beta-d- ribofuranosyl-
8-azaadenosine
10299-44-2
3h-1,2,3-triazolo(4,5-d)pyrimidin-7-amine, 3-beta-d-ribofuranosyl-
3h-v-triazolo(4,5-d)pyrimidine, 7-amino-3-beta-d-ribofuranosyl-
3-beta-d-ribofuranosyl-3h-1,2,3-triazolo(4,5-d)pyrimidin-7-amine
nsc 72961
(2r,3r,4s,5r)-2-(7-aminotriazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)oxolane-3,4-diol
chebi:2310 ,
CHEMBL174661
SCHEMBL115636
7-amino-3-beta-d-ribofuranosyl-3h-1,2,3-triazolo[4,5-d]pyrimidine
OAUKGFJQZRGECT-UUOKFMHZSA-N
7-amino-3-beta-d-ribofuranosyl-(3h)-1,2,3-triazolo[4,5-d]pyrimidine
AKOS030530872
3h-1,2,3-triazolo[4,5-d]pyrimidin-7-amine,3-b-d-ribofuranosyl-
(2r,3r,4s,5r)-2-(7-amino-3h-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Q27105620
3-?-d-ribofuranosyl-3h-1,2,3-triazolo[4,5-d]pyrimidin-7-amine
E78375
BS-49010
HY-115686
CS-0120652
(2r,3r,4s,5r)-2-{7-amino-3h-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl}-5-(hydroxymethyl)oxolane-3,4-diol
PD124471
Z2417560404

Research Excerpts

Compound-Compound Interactions

ExcerptReferenceRelevance
"The toxicology and metabolism of 8-azaadenosine (8-azaAdo) were examined both as a single agent and in combination with the adenosine deaminase inhibitor, 2'-deoxycoformycin (dCF)."( Biochemical pharmacology and toxicology of 8-azaadenosine alone and in combination with 2'-deoxycoformycin (pentostatin).
Calabresi, P; Chu, SH; Crabtree, GW; Dexter, DL; Diamond, I; Farineau, DM; Ghoda, LY; McGowan, DL; Parks, RE; Spremulli, EN, 1982)		0.81
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-glycosyl compoundA glycosyl compound arising formally from the elimination of water from a glycosidic hydroxy group and an H atom bound to a nitrogen atom, thus creating a C-N bond.
[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)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
adenosine catabolic processAdenosine deaminase Bos taurus (cattle)
cell adhesionAdenosine deaminase Bos taurus (cattle)
nucleotide metabolic processAdenosine deaminase Bos taurus (cattle)
purine ribonucleoside monophosphate biosynthetic processAdenosine deaminase Bos taurus (cattle)
inosine biosynthetic processAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
adenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
protein bindingAdenosine deaminase Bos taurus (cattle)
zinc ion bindingAdenosine deaminase Bos taurus (cattle)
2'-deoxyadenosine deaminase activityAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
lysosomeAdenosine deaminase Bos taurus (cattle)
cytoplasmic vesicle lumenAdenosine deaminase Bos taurus (cattle)
anchoring junctionAdenosine deaminase Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1131379Cytotoxicity against human Hep2 cells assessed as growth inhibition1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Analogues of 8-azainosine.
AID1131383Resistance ratio of ED50 for hypoxanthine-guanine phosphoribosyl transferase/adenosine kinase deficient 6-mercaptopurine/6-(methylthio)purine ribonucleoside-resistant human Hep2 cells to ED50 for wild type human Hep2 cells1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Analogues of 8-azainosine.
AID228915Coronary vasoactivity as molar potency ratio (MPR), the quotient of ED50 of adenosine by that of the test nucleoside1984Journal of medicinal chemistry, Jul, Volume: 27, Issue:7
Biological activity and a modified synthesis of 8-amino-3-beta-D-ribofuranosyl-1,2,4-triazolo[4,3-a]pyrazine, an isomer of formycin.
AID79401Cytotoxicity against H.Ep cells1983Journal of medicinal chemistry, Oct, Volume: 26, Issue:10
Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds.
AID1131382Resistance ratio of ED50 for adenine phosphoribosyltransferase/adenosine kinase deficient 2-fluoro adenine/2-fluoro adenosine-resistant human Hep2 cells to ED50 for wild type human Hep2 cells1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Analogues of 8-azainosine.
AID1131384Antitumor activity against mouse L1210 cells allografted in ip dosed BD2F1 mouse assessed as increase in life span administered 1 to 9 days measured on day 10 to 12 relative to control1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Analogues of 8-azainosine.
AID1131381Resistance ratio of ED50 for adenosine kinase deficient 6-(methylthio)purine ribonucleoside-resistant human Hep2 cells to ED50 for wild type human Hep2 cells1977Journal of medicinal chemistry, Jan, Volume: 20, Issue:1
Analogues of 8-azainosine.
AID33815Kinetic parameter in calf intestine adenosine deaminase.1983Journal of medicinal chemistry, Oct, Volume: 26, Issue:10
Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds.
AID79402Cytotoxicity against H.Ep cells in the presence of 0.1 ug/mL pentostatin.1983Journal of medicinal chemistry, Oct, Volume: 26, Issue:10
Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds.
AID22612Kinetic parameter in calf intestine adenosine deaminase.1983Journal of medicinal chemistry, Oct, Volume: 26, Issue:10
Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (72.73)18.7374
1990's0 (0.00)18.2507
2000's1 (9.09)29.6817
2010's1 (9.09)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.34

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 Index21.34 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.34)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
tubercidin
Tubercidin: An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids.. tubercidin : An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus.		7.3620antibiotic antifungal agent;
N-glycosylpyrrolopyrimidine;
ribonucleoside		antimetabolite;
antineoplastic agent;
bacterial metabolite
2-chloroadenosine
5-chloroformycin A: structure given in first source		2.3110purine nucleoside
2-fluoroadenosine
[no description available]		1.9610adenosines;
organofluorine compound
vidarabine
adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.		1.9610beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
3-deazaadenosine
3-deazaadenosine: RN given refers to parent cpd.		1.9610
coformycin
[no description available]		7.3620coformycinsEC 3.5.4.4 (adenosine deaminase) inhibitor
vidarabine phosphate
Vidarabine Phosphate: An adenosine monophosphate analog in which ribose is replaced by an arabinose moiety. It is the monophosphate ester of VIDARABINE with antiviral and possibly antineoplastic properties.		1.9610
ribavirin
Rebetron: Rebetron is tradename		1.96101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		3.5890adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
2-aminoadenosine
[no description available]		1.9610purine nucleoside
6-methoxypurine arabinoside
[no description available]		1.9610
8-chloroadenosine
8-chloroadenosine: active metabolite of 8-chloro-cyclic adenosine 3',5'-monophosphate		7.3110
pentostatin
Pentostatin: A potent inhibitor of ADENOSINE DEAMINASE. The drug induces APOPTOSIS of LYMPHOCYTES, and is used in the treatment of many lymphoproliferative malignancies, particularly HAIRY CELL LEUKEMIA. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity.. pentostatin : A member of the class of coformycins that is coformycin in which the hydroxy group at position 2' is replaced with a hydrogen. It is a drug used for the treatment of hairy cell leukaemia.		7.3620coformycinsantimetabolite;
antineoplastic agent;
Aspergillus metabolite;
bacterial metabolite;
EC 3.5.4.4 (adenosine deaminase) inhibitor
formycin
[no description available]		7.3620formycinantineoplastic agent
azaguanine
Azaguanine: One of the early purine analogs showing antineoplastic activity. It functions as an antimetabolite and is easily incorporated into ribonucleic acids.. 8-azaguanine : A triazolopyrimidine that consists of 3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidine bearing amino and oxo substituents at positions 5 and 7 respectively.		1.9610nucleobase analogue;
triazolopyrimidines		antimetabolite;
antineoplastic agent;
EC 2.4.2.1 (purine-nucleoside phosphorylase) inhibitor
formycins
Formycins: Pyrazolopyrimidine ribonucleosides isolated from Nocardia interforma. They are antineoplastic antibiotics with cytostatic properties.		2.6530
ConditionIndicatedRelationship StrengthStudiesTrials
Carcinoma, Epidermoid
[description not available]		02.3620
Leukemia L 1210
[description not available]		02.6530
Carcinoma, Squamous Cell
A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)		02.3620
Cancer of Larynx
[description not available]		01.9610
Leukemia P388
An experimental lymphocytic leukemia originally induced in DBA/2 mice by painting with methylcholanthrene.		01.9610
Experimental Leukemia
[description not available]		01.9610
Laryngeal Neoplasms
Cancers or tumors of the LARYNX or any of its parts: the GLOTTIS; EPIGLOTTIS; LARYNGEAL CARTILAGES; LARYNGEAL MUSCLES; and VOCAL CORDS.		01.9610
Blood Pressure, Low
[description not available]		01.9610
Hypotension
Abnormally low BLOOD PRESSURE that can result in inadequate blood flow to the brain and other vital organs. Common symptom is DIZZINESS but greater negative impacts on the body occur when there is prolonged depravation of oxygen and nutrients.		01.9610
Acute Liver Injury, Drug-Induced
[description not available]		01.9610
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		01.9610
Cancer of Colon
[description not available]		01.9610
Experimental Neoplasms
[description not available]		01.9610
Colonic Neoplasms
Tumors or cancer of the COLON.		01.9610