Page last updated: 2024-10-15

9-arabinofuranosylguanine

Description

9-arabinofuranosylguanine: RN given refers to (beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

9-beta-D-arabinofuranosylguanine : A purine nucleoside in which guanine is attached to arabinofuranose via a beta-N(9)-glycosidic bond. It inhibits DNA synthesis and causes cell death. [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 CID135499520
CHEMBL ID240933
CHEBI ID73141
SCHEMBL ID11529318
SCHEMBL ID34912
MeSH IDM0092272

Synonyms (52)

Synonym
guanine, 9-(beta-d-arabinofuranosyl)-
6h-purin-6-one, 2-amino-9-beta-d-arabinofuranosyl-1,9-dihydro-
nsc 76352
9-arabinofuranosylguanine
9-(beta-d-arabinofuranosyl)guanine
2-amino-9-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1h-purin-6-one
guanine arabinoside
arag
38819-10-2
CHEMBL240933 ,
chebi:73141 ,
2-amino-9-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one
9-beta-d-arabinofuranosylguanine
bdbm50206506
HMS3263D20
SCHEMBL11529318
unii-0z99wx0gpf
0z99wx0gpf ,
AKOS016003883
ara-g hydrate
LP01219
2-amino-9-(beta-d-arabinofuranosyl)-1,9-dihydro-6h-purin-6-one
9-beta-arabinosylguanine
CCG-222523
SCHEMBL34912
J-700337
NCGC00261904-01
tox21_501219
NYHBQMYGNKIUIF-FJFJXFQQSA-N
2-amino-6-hydroxy-9-(beta-d-arabinofuranosyl)purine
2-amino-9-((2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1h-purin-6(9h)-one
9-b-d-arabinofuranosylguanine
AC-32194
A2739
guanine 9-beta-d-arabinofuranoside
mfcd00065486
ara-g hydrate, >=98% (hplc), solid
Q27140338
DS-14591
6h-purin-6-one,2-amino-9-b-d-arabinofuranosyl-1,9-dihydro-
BCP12606
9-.beta.-d-arabinofuranosylguanine
araguanosine
ara-guanosine
2-amino-6-hydroxy-9-(.beta.-d-arabinofuranosyl)purine
nelarabine metabolite (ara-guanosine)
DTXSID301019130
SDCCGSBI-0633806.P001
NCGC00487230-02
H10558
cid 65412
AKOS040755534

Pharmacokinetics

ExcerptReference
" Parallel plasma and cellular pharmacokinetic studies were conducted."( Compound GW506U78 in refractory hematologic malignancies: relationship between cellular pharmacokinetics and clinical response.
Ayres, M; Du, M; Gandhi, V; Keating, MJ; Kisor, DF; Kurtzberg, J; Mitchell, BS; Nowak, BJ; Plunkett, W; Rodriguez, CO, 1998
)
" The harmonic mean half-life (t1/2) of nelarabine in pediatric and adult patients was 14."( Pharmacokinetics of nelarabine and 9-beta-D-arabinofuranosyl guanine in pediatric and adult patients during a phase I study of nelarabine for the treatment of refractory hematologic malignancies.
Ernst, T; Gandhi, V; Hodge, JP; Keating, MJ; Kisor, DF; Kurtzberg, J; Mitchell, B; Plunkett, W, 2000
)
" The terminal half-life of nelarabine in plasma was 25+/-5."( Plasma and cerebrospinal fluid pharmacokinetics of nelarabine in nonhuman primates.
Berg, SL; Blaney, SM; Brueckner, C; Dauser, R; McGuffey, L; Nuchtern, JG, 2007
)

Dosage Studied

ExcerptReference
" Hence, dosing regimens that achieve high plasma levels of ara-G during therapy may increase cellular levels of ara-GTP."( Pharmacological and biochemical strategies to increase the accumulation of arabinofuranosylguanine triphosphatein primary human leukemia cells.
Estey, E; Gandhi, V; Keating, MJ; Legha, JK; Rodriguez, CO, 1997
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
DNA synthesis inhibitorAny substance that inhibits the synthesis of DNA.
[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 (2)

ClassDescription
beta-D-arabinoside
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)
Thymidine kinase, cytosolicHomo sapiens (human)IC50 (µMol)500.00000.01601.21053.0000AID306718
Thymidine kinaseHuman herpesvirus 3 strain DumasIC50 (µMol)500.00003.20003.20003.2000AID306722
Thymidine kinaseHuman alphaherpesvirus 1 (Herpes simplex virus type 1)IC50 (µMol)500.00000.15004.81679.0000AID306720
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (10)

Processvia Protein(s)Taxonomy
nucleobase-containing compound metabolic processThymidine kinase 2, mitochondrialHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase 2, mitochondrialHomo sapiens (human)
nucleotide biosynthetic processThymidine kinase 2, mitochondrialHomo sapiens (human)
pyrimidine nucleoside salvageThymidine kinase 2, mitochondrialHomo sapiens (human)
deoxycytidine metabolic processThymidine kinase 2, mitochondrialHomo sapiens (human)
thymidine metabolic processThymidine kinase 2, mitochondrialHomo sapiens (human)
DNA biosynthetic processThymidine kinase 2, mitochondrialHomo sapiens (human)
nucleobase-containing compound metabolic processThymidine kinase, cytosolicHomo sapiens (human)
deoxyribonucleoside monophosphate biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine metabolic processThymidine kinase, cytosolicHomo sapiens (human)
thymidine biosynthetic processThymidine kinase, cytosolicHomo sapiens (human)
protein homotetramerizationThymidine kinase, cytosolicHomo sapiens (human)
DNA synthesis involved in mitotic DNA replicationThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
deoxycytidine kinase activityThymidine kinase 2, mitochondrialHomo sapiens (human)
thymidine kinase activityThymidine kinase 2, mitochondrialHomo sapiens (human)
ATP bindingThymidine kinase 2, mitochondrialHomo sapiens (human)
nucleoside kinase activityThymidine kinase 2, mitochondrialHomo sapiens (human)
deoxynucleoside kinase activityThymidine kinase 2, mitochondrialHomo sapiens (human)
thymidine kinase activityThymidine kinase, cytosolicHomo sapiens (human)
protein bindingThymidine kinase, cytosolicHomo sapiens (human)
ATP bindingThymidine kinase, cytosolicHomo sapiens (human)
zinc ion bindingThymidine kinase, cytosolicHomo sapiens (human)
identical protein bindingThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
mitochondrionThymidine kinase 2, mitochondrialHomo sapiens (human)
mitochondrial matrixThymidine kinase 2, mitochondrialHomo sapiens (human)
cytoplasmThymidine kinase 2, mitochondrialHomo sapiens (human)
nucleusThymidine kinase, cytosolicHomo sapiens (human)
cytosolThymidine kinase, cytosolicHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1347059CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347057CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID306719Inhibition of human TK2 assessed as [methyl-3H]dThd phosphorylation2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity.
AID306718Inhibition of human TK1 assessed as [methyl-3H]dThd phosphorylation2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity.
AID306724Inhibition of Drosophila melanogaster dGK assessed as [methyl-3H]dThd phosphorylation2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity.
AID306722Inhibition of VZV TK assessed as [methyl-3H]dThd phosphorylation2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity.
AID306721Inhibition of Drosophila melanogaster dNK assessed as [methyl-3H]dThd phosphorylation2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity.
AID306720Inhibition of HSV1 TK assessed as [methyl-3H]dThd phosphorylation2007Bioorganic & medicinal chemistry, Apr-15, Volume: 15, Issue:8
Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (63)

TimeframeStudies, This Drug (%)All Drugs %
pre-199013 (20.63)18.7374
1990's16 (25.40)18.2507
2000's18 (28.57)29.6817
2010's11 (17.46)24.3611
2020's5 (7.94)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 (%)
Trials2 (3.08%)5.53%
Reviews2 (3.08%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other61 (93.85%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Imaging of T-Cell Activation With [18F]-AraG in Advanced Non-Small Cell Lung Cancer (NSCLC) Patients Undergoing PD-1/PD-L1-Directed Therapy[NCT04186988]Early Phase 10 participants (Actual)Interventional2019-11-05Withdrawn(stopped due to Unable to recruit to study.)
[information is prepared from clinicaltrials.gov, extracted Sep-2024]