Compounds > 6-methoxypurine arabinoside
Page last updated: 2024-12-07

6-methoxypurine arabinoside

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

Cross-References

ID SourceID
PubMed CID124757
CHEMBL ID157635
SCHEMBL ID6903709
MeSH IDM0190745

Synonyms (14)

Synonym
(2r,3s,4s,5r)-2-(hydroxymethyl)-5-(6-methoxypurin-9-yl)tetrahydrofuran-3,4-diol
2-hydroxymethyl-5-(6-methoxy-purin-9-yl)-tetrahydro-furan-3,4-diol
91969-06-1
6-methoxypurine arabinoside
CHEMBL157635
SCHEMBL6903709
9h-purine, 9-beta-d-arabinofuranosyl-6-methoxy-
nsc 409169
ara-m
9-(beta-arabinosyl)-6-methoxy-9-purine
6-methoxy-9-pentofuranosyl-9h-purine
DTXSID20913648
6-methoxy-9-beta-d-arabinofuranosylpurine
(2r,3s,4s,5r)-2-(hydroxymethyl)-5-(6-methoxy-9h-purin-9-yl)tetrahydrofuran-3,4-diol

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" These factors might account for the lower systemic bioavailability of these compounds."( Di- and triester prodrugs of the varicella-zoster antiviral agent 6-methoxypurine arabinoside.
Burns, CL; Chamberlain, SD; de Miranda, P; Jones, LA; Krenitsky, TA; Moorman, AR; Reynolds, DJ, 1992)		0.52
" In Long Evans rats, orally administered [8-14C]ara-M (10 mg/kg) was well absorbed but extensively metabolized to hypoxanthine arabinoside (ara-H), hypoxanthine, xanthine, uric acid, and allantoin."( Metabolic disposition and pharmacokinetics of the antiviral agent 6-methoxypurine arabinoside in rats and monkeys.
Burnette, TC; De Miranda, P; Koszalka, GW; Krenitsky, TA, 1991)		0.52

Dosage Studied

ExcerptRelevanceReference
" An unfavourable metabolic profile observed with oral dosing in the rat led to the preparation of a variety of 2',3',5'-triesters (2a-n) and several 2',3'-, 2',5'-, and 3',5'-diesters of this arabinoside (3a-n, 4a-f, and 5a-j, respectively)."( Di- and triester prodrugs of the varicella-zoster antiviral agent 6-methoxypurine arabinoside.
Burns, CL; Chamberlain, SD; de Miranda, P; Jones, LA; Krenitsky, TA; Moorman, AR; Reynolds, DJ, 1992)		0.52
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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 (13)

Assay IDTitleYearJournalArticle
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.
AID22756Ester prodrugs: stability in buffer (pH 7)1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Di- and triester prodrugs of the varicella-zoster antiviral agent 6-methoxypurine arabinoside.
AID217966In vitro for antiviral activity in secondary cultures of rabbit kidney cells infected with vaccinia virus1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
AID228918Molar potency ratio was evaluated1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion.
AID217834Concentration required to inhibit vaccinia virus induced cytopathogenic affects by 50%1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
AID85569Concentration required to inhibit HSV type 1 strain HF induced cytopathogenic affects by 50%1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
AID85703In vitro antiviral activity in secondary cultures of rabbit kidney cells infected with HSV type 1 strain HF1984Journal of medicinal chemistry, Nov, Volume: 27, Issue:11
Synthesis and antiviral activity of carbocyclic analogues of 2'-deoxyribofuranosides of 2-amino-6-substituted-purines and of 2-amino-6-substituted-8-azapurines.
AID31114Ester prodrugs: recovery of parent compound in rat urine1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Di- and triester prodrugs of the varicella-zoster antiviral agent 6-methoxypurine arabinoside.
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.
AID23550Solubility (phosphate buffered saline)1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Di- and triester prodrugs of the varicella-zoster antiviral agent 6-methoxypurine arabinoside.
AID24941Ester prodrugs: recovery of parent compound in rat urine1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Di- and triester prodrugs of the varicella-zoster antiviral agent 6-methoxypurine arabinoside.
AID25507HPLC capacity factor (k')1985Journal of medicinal chemistry, Nov, Volume: 28, Issue:11
Dog coronary artery adenosine receptor: structure of the N6-alkyl subregion.
AID24125Calculated partition coefficient (clogP)1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Di- and triester prodrugs of the varicella-zoster antiviral agent 6-methoxypurine arabinoside.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (23.08)18.7374
1990's9 (69.23)18.2507
2000's1 (7.69)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.91

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.91 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.91)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (3)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Intensified Methotrexate, Nelarabine (Compound 506U78) and Augmented BFM Therapy for Children and Young Adults With Newly Diagnosed T-cell Acute Lymphoblastic Leukemia (ALL) or T-cell Lymphoblastic Lymphoma [NCT00408005]Phase 31,895 participants (Actual)Interventional2007-01-22Active, not recruiting
Phase II Study of Hyper-CVAD Plus Nelarabine in Previously Untreated T-ALL and Lymphoblastic Lymphoma [NCT00501826]Phase 2160 participants (Anticipated)Interventional2007-07-11Recruiting
Phase I/II Study of the Combination of Low-Intensity Chemotherapy and Venetoclax (ABT-199) in Patients With Relapsed/Refractory Acute Lymphoblastic Leukemia (ALL) [NCT03808610]Phase 1/Phase 250 participants (Anticipated)Interventional2019-04-03Recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT00408005 (8) [back to overview]Disease-free Survival (DFS) for Randomized Methotrexate T-ALL Cohort (Arm I + Arm II vs. Arm III + Arm IV)
NCT00408005 (8) [back to overview]Disease-free Survival (DFS) for Randomized Methotrexate T-ALL Cohort (Arm I vs. Arm II vs. Arm III vs. Arm IV)
NCT00408005 (8) [back to overview]Disease-free Survival (DFS) for Randomized Nelarabine T-ALL Cohort (Arm I + Arm III vs. Arm II + Arm IV)
NCT00408005 (8) [back to overview]Disease-free Survival (DFS) for Randomized Nelarabine T-ALL Cohort (Arm I vs. Arm II vs. Arm III vs. Arm IV)
NCT00408005 (8) [back to overview]Cumulative Incidence of CNS Relapse for T-ALL by Risk Group
NCT00408005 (8) [back to overview]Cumulative Incidence of CNS Relapse for T-ALL by Risk Group
NCT00408005 (8) [back to overview]Disease-free Survival (DFS) for T-cell Lymphoblastic Lymphoma (T-LLy) Cohort
NCT00408005 (8) [back to overview]Disease-free Survival (DFS) for T-cell Lymphoblastic Lymphoma (T-LLy) Cohort

Disease-free Survival (DFS) for Randomized Methotrexate T-ALL Cohort (Arm I + Arm II vs. Arm III + Arm IV)

Disease Free Probability where DFS time is defined as time from randomization end of induction to first event (relapse, second malignant neoplasm, death) or date of last contact for patients who are event-free. (NCT00408005)
Timeframe: 4 years from randomization at the end of induction

Interventionpercent probability (Number)
ARM I and ARM II (Combination Chemotherapy)91.45
ARM III and ARM IV (Combination Chemotherapy)85.78

[back to top]

Disease-free Survival (DFS) for Randomized Methotrexate T-ALL Cohort (Arm I vs. Arm II vs. Arm III vs. Arm IV)

Disease-free survival defined as time from randomization end of induction to first event (relapse, second malignant neoplasm, remission death) or date of last contact for those who are event-free. (NCT00408005)
Timeframe: 4 years from randomization at the end of induction

Interventionpercent probability (Number)
ARM I (Combination Chemotherapy)91.76
ARM II (Combination Chemotherapy)90.53
ARM III (Combination Chemotherapy)86.06
ARM IV (Combination Chemotherapy)84.89

[back to top]

Disease-free Survival (DFS) for Randomized Nelarabine T-ALL Cohort (Arm I + Arm III vs. Arm II + Arm IV)

Disease Free Probability where DFS time is defined as time from randomization end of induction to first event (relapse, second malignant neoplasm, death) or date of last contact for patients who are event (NCT00408005)
Timeframe: 4 years from randomization at the end of induction

Interventionpercent probability (Number)
ARM I and ARM III (Combination Chemotherapy)82.96
ARM II and ARM IV (Combination Chemotherapy)88.30

[back to top]

Disease-free Survival (DFS) for Randomized Nelarabine T-ALL Cohort (Arm I vs. Arm II vs. Arm III vs. Arm IV)

Disease Free Probability where DFS time is defined as time from randomization end of induction to first event (relapse, second malignant neoplasm, death) or date of last contact for patients who are event-free. (NCT00408005)
Timeframe: 4 years from randomization at the end of induction

Interventionpercent probability (Number)
ARM I (Combination Chemotherapy)89.01
ARM II (Combination Chemotherapy)90.53
ARM III (Combination Chemotherapy)78.07
ARM IV (Combination Chemotherapy)86.46

[back to top]

Cumulative Incidence of CNS Relapse for T-ALL by Risk Group

Cumulative incidence of CNS relapse adjusting for DFS events, was calculated using the method Gray et. al. High risk patients receive cranial radiation and low risk patients receive no cranial radiation. (NCT00408005)
Timeframe: 4 years from randomization at the end of induction

,
Interventionpercent probability (Number)
Intermediate RiskHigh Risk
ARM II (Combination Chemotherapy)1.080
ARM IV (Combination Chemotherapy)0.853.45

[back to top]

Cumulative Incidence of CNS Relapse for T-ALL by Risk Group

Cumulative incidence of CNS relapse adjusting for DFS events, was calculated using the method Gray et. al. High risk patients receive cranial radiation and low risk patients receive no cranial radiation. (NCT00408005)
Timeframe: 4 years from randomization at the end of induction

,
Interventionpercent probability (Number)
Low RiskIntermediate RiskHigh Risk
ARM I (Combination Chemotherapy)1.851.163.64
ARM III (Combination Chemotherapy)1.929.16.52

[back to top]

Disease-free Survival (DFS) for T-cell Lymphoblastic Lymphoma (T-LLy) Cohort

Disease Free Probability where DFS time is defined as time from randomization end of induction to first event (relapse, second malignant neoplasm, death) or date of last contact for patients who are event-free. (NCT00408005)
Timeframe: 4 years from end of induction

Interventionpercent probability (Number)
High RiskInduction Failure
ARM II (Combination Chemotherapy)85.0100

[back to top]

Disease-free Survival (DFS) for T-cell Lymphoblastic Lymphoma (T-LLy) Cohort

Disease Free Probability where DFS time is defined as time from randomization end of induction to first event (relapse, second malignant neoplasm, death) or date of last contact for patients who are event-free. (NCT00408005)
Timeframe: 4 years from end of induction

Interventionpercent probability (Number)
Standard RiskHigh Risk
ARM I (Combination Chemotherapy)87.485.1

[back to top]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		1.97106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
phycoerythrin
ara-ATP: structure		1.9710
9-(2-hydroxy-3-nonyl)adenine
9-(2-hydroxy-3-nonyl)adenine: specific inhibitor of adenosine deaminase		1.9710
flucytosine
Flucytosine: A fluorinated cytosine analog that is used as an antifungal agent.. flucytosine : An organofluorine compound that is cytosine that is substituted at position 5 by a fluorine. A prodrug for the antifungal 5-fluorouracil, it is used for the treatment of systemic fungal infections.		3.1110aminopyrimidine;
nucleoside analogue;
organofluorine compound;
pyrimidine antifungal drug;
pyrimidone		prodrug
idoxuridine
[no description available]		1.9610organoiodine compound;
pyrimidine 2'-deoxyribonucleoside		antiviral drug;
DNA synthesis inhibitor
bromodeoxyuridine
Bromodeoxyuridine: A nucleoside that substitutes for thymidine in DNA and thus acts as an antimetabolite. It causes breaks in chromosomes and has been proposed as an antiviral and antineoplastic agent. It has been given orphan drug status for use in the treatment of primary brain tumors.		1.9610pyrimidine 2'-deoxyribonucleosideantimetabolite;
antineoplastic agent
2-fluoroadenosine
[no description available]		1.9610adenosines;
organofluorine compound
methylthioinosine
Methylthioinosine: 6-(Methylthio)-9-beta-D-ribofuranosylpurine. An analog of inosine with a methylthio group replacing the hydroxyl group in the 6-position.		1.9610purine ribonucleoside;
thiopurine
6-hydroxyadenosine
[no description available]		2.3720
vidarabine
adenine arabinoside : A purine nucleoside in which adenine is attached to arabinofuranose via a beta-N(9)-glycosidic bond.		2.8840beta-D-arabinoside;
purine nucleoside		antineoplastic agent;
bacterial metabolite;
nucleoside antibiotic
3-deazaadenosine
3-deazaadenosine: RN given refers to parent cpd.		1.9610
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.		1.9710
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		2.3720adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
nebularine
nebularine: structure. nebularine : A purine ribonucleoside that is 9H-purine attached to a beta-D-ribofuranosyl residue at position 9 via a glycosidic (N-glycosyl) linkage.		1.9610purine ribonucleoside;
purines D-ribonucleoside		fungal metabolite
2-aminoadenosine
[no description available]		2.3720purine nucleoside
tretazicar
tretazicar: minor descriptor (75-84); on-line & Index Medicus search AZIRIDINES (75-84)		3.1110
6-chloropurine riboside
[no description available]		2.3720
phenylisopropyladenosine
[no description available]		1.9610aromatic amine;
benzenes;
hydrocarbyladenosine;
purine nucleoside;
secondary amino compound		adenosine A1 receptor agonist;
neuroprotective agent
8-azaadenosine
[no description available]		1.9610N-glycosyl compound
n-allyladenosine
[no description available]		1.9610purine nucleoside
6-methylpurine riboside
[no description available]		1.9610
n-methyladenosine
N-methyladenosine: is a inhibitor of cell differentiation. N(6)-methyladenosine : A methyladenosine compound with one methyl group attached to N(6) of the adenine nucleobase.		1.9610methyladenosine
6-methylpurine 2'-deoxyriboside
[no description available]		3.1110
n(6),n(6)-dimethyladenosine
N(6),N(6)-dimethyladenosine : A methyladenosine compound with two methyl groups attached to N(6) of the adenine nucleobase.		1.9610hydrocarbyladenosine
carbodine
carbodine: RN given refers to (R-(1alpha,2beta,3beta,4alpha))-isomer		1.9610
n(6)-cyclopentyladenosine
[no description available]		1.9610
6-thioxanthine
6-thioxanthine: gpt/6-TXenzyme/prodrug pair is a promising alternative to the thymidine kinase gene and ganciclovir combination in the gene therapy of cancer		3.1110
n-(1-methyl-2-phenylethyl)adenosine, (s)-isomer
[no description available]		1.9610
1-aminoadenosine
1-aminoadenosine: structure		1.9610
n(6)-cyclohexyladenosine
N(6)-cyclohexyladenosine: structure given in first source; receptors, purinergic P1 agonist		1.9610
oligonucleotides
[no description available]		1.9710
acyclovir
Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.		1.97102-aminopurines;
oxopurine		antimetabolite;
antiviral drug
ganciclovir
[no description available]		3.11102-aminopurines;
oxopurine		antiinfective agent;
antiviral drug
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
hypoxanthine arabinoside
hypoxanthine arabinoside: metabolite of adenine arabinoside used in therapy of ocular herpes		2.3820
carbocyclic inosine
carbocyclic inosine: anti-Leishmanial agent; structure given in first source		1.9610
ConditionIndicatedRelationship StrengthStudiesTrials
Carcinoma, Epidermoid
[description not available]		01.9610
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
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)		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
Benign Neoplasms
[description not available]		02.9210
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		02.9210
Hepatocellular Carcinoma
[description not available]		02.3820
Cancer of Liver
[description not available]		02.3820
Experimental Hepatoma
[description not available]		01.9810
Carcinoma, Hepatocellular
A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.		02.3820
Liver Neoplasms
Tumors or cancer of the LIVER.		02.3820
Neuroretinitis
[description not available]		01.9810
Eye Infections, Viral
Infections of the eye caused by minute intracellular agents. These infections may lead to severe inflammation in various parts of the eye - conjunctiva, iris, eyelids, etc. Several viruses have been identified as the causative agents. Among these are Herpesvirus, Adenovirus, Poxvirus, and Myxovirus.		01.9810
Retinitis
Inflammation of the RETINA. It is rarely limited to the retina, but is commonly associated with diseases of the choroid (CHORIORETINITIS) and of the OPTIC DISK (neuroretinitis).		01.9810