Page last updated: 2024-11-04

arabinofuranosylcytosine triphosphate

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Description

Arabinofuranosylcytosine Triphosphate: A triphosphate nucleotide analog which is the biologically active form of CYTARABINE. It inhibits nuclear DNA synthesis. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID314
CHEMBL ID296272
CHEBI ID181445
SCHEMBL ID6115643
MeSH IDM0001640
PubMed CID25774
CHEMBL ID3417290
SCHEMBL ID4289439
MeSH IDM0001640

Synonyms (55)

Synonym
smr001565530
CHEBI:181445
[5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
30811-80-4
nsc-120953
nsc120953
NCI60_042226
cytosine arabinoside monophosphate
cytosine, 5'-(dihydrogen phosphate)
mls002701948 ,
nsc99445 ,
FT-0655251
FT-0665428
CHEMBL296272
[5-(4-amino-2-oxohydropyrimidinyl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
FT-0624322
STL454992
4-imino-1-(5-o-phosphonopentofuranosyl)-1,4-dihydropyrimidin-2-ol
SCHEMBL6115643
AKOS024275782
STL454151
4-imino-1-(5-o-phosphonopentofuranosyl)-3,4-dihydropyrimidin-2(1h)-one
4-amino-1-(5-o-phosphonopentofuranosyl)pyrimidin-2(1h)-one
STL452942
686299-78-5
(5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
BCP33637
cytidine-5'-monophosphate;cytidine monophosphate
DTXSID70861605
(5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyldihydrogenphosphate
[[(2r,3s,4s,5r)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphono hydrogen phosphate
phosphoric acid tri-[(2r,3s,4s,5r)-5-(4-amino-2-oxo-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester
cytosine, 1-beta-d-arabinofuranosyl-, triphosphate
cytosine arabinoside 5'-triphosphate
cytarabine triphosphate
arabinofuranosylcytosine triphosphate
cytosine, 1-beta-d-arabinofuranosyl-, 5'-(tetrahydrogen triphosphate)
ara-ctp
2(1h)-pyrimidinone, 4-amino-1-(5-o-(hydroxy((hydroxy(phosphonooxy)phosphinyl)oxy)phosphinyl)-beta-d-arabinofuranosyl)-
13191-15-6
[[(2r,3s,4s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
s78sfw950o ,
unii-s78sfw950o
SCHEMBL4289439
cytidine triphos-phate
CHEMBL3417290
cytarabine-triphosphate
DTXSID40927388
Q4783465
hf4 ,
4-amino-1-{5-o-[(s)-hydroxy{[(r)-hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl]-beta-d-arabinofuranosyl}pyrimidin-2(1h)-one
HY-115740
CS-0255130
AKOS040756641
ara-cytidine-5'-triphosphate (ara-ctp)

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"1 to 100 microM), involved a temperature-dependent process, could not be mimicked by addition of hematopoietic growth factors, and was not related to neutralization of toxic or inhibitory substances in high-density medium."( In vitro effects of bryostatin 1 on the metabolism and cytotoxicity of 1-beta-D-arabinofuranosylcytosine in human leukemia cells.
Boise, L; Grant, S; Howe, C; McCrady, C; Pettit, GR; Turner, A; Westin, E, 1991
)
0.28

Pharmacokinetics

ExcerptReferenceRelevance
" In contrast to ara-C triphosphate, dFdCTP is eliminated with biphasic kinetics that exhibit a terminal half-life that approaches the cell cycle time."( Pharmacokinetics of the 5'-triphosphates of arabinosylcytosine and 2',2'-difluorodeoxycytidine in L1210 cells.
Grindey, GB; Plunkett, W, 1987
)
0.27
" Pharmacokinetic and pharmacodynamic interactions between CdA and ara-C during therapy were investigated."( Chlorodeoxyadenosine and arabinosylcytosine in patients with acute myelogenous leukemia: pharmacokinetic, pharmacodynamic, and molecular interactions.
Chucrallah, A; Estey, E; Gandhi, V; Keating, MJ; Plunkett, W, 1996
)
0.29
" Pharmacokinetic and pharmacodynamic studies were performed on specimens from 20 patients."( Pharmacokinetic and pharmacodynamic studies of fludarabine and cytosine arabinoside administered as loading boluses followed by continuous infusions after a phase I/II study in pediatric patients with relapsed leukemias. The Children's Cancer Group.
Avramis, VI; Kowck, R; Krailo, MD; Liu-Mares, W; Ramilo-Torno, LV; Reaman, GH; Sato, JK; Sharpe, A; Wiersma, S, 1998
)
0.3
"Provide pharmacokinetic data for orally administered CO and determine accumulation and functional consequences of Ara-CTP within peripheral blood leukocytes."( Oral cytarabine ocfosfate pharmacokinetics and assessment of leukocyte biomarkers in normal dogs.
Dickinson, PJ; Knych, HK; Kol, A; Pypendop, BH; Questa, M; Rodrigues, CA; Vernau, KM; Vernau, W; Zwueste, DM,
)
0.13

Compound-Compound Interactions

ExcerptReferenceRelevance
"To identify the optimal schedule for infusion of cytarabine (ara-C) given with cladribine (2-CdA) to pediatric patients with acute myeloid leukemia (AML), and to compare the effects of the two schedules on the pharmacokinetics of ara-C triphosphate (ara-CTP) in leukemic cells."( Interim comparison of a continuous infusion versus a short daily infusion of cytarabine given in combination with cladribine for pediatric acute myeloid leukemia.
Behm, FG; Crews, KR; Gandhi, V; Plunkett, W; Pui, CH; Raimondi, SC; Razzouk, BI; Ribeiro, RC; Rubnitz, JE; Srivastava, DK; Stewart, CF; Tong, X, 2002
)
0.31
"Intracellular accumulation of ara-CTP is increased when 2-CdA is given with ara-C, but no schedule-dependent differences in this effect were seen."( Interim comparison of a continuous infusion versus a short daily infusion of cytarabine given in combination with cladribine for pediatric acute myeloid leukemia.
Behm, FG; Crews, KR; Gandhi, V; Plunkett, W; Pui, CH; Raimondi, SC; Razzouk, BI; Ribeiro, RC; Rubnitz, JE; Srivastava, DK; Stewart, CF; Tong, X, 2002
)
0.31

Bioavailability

ExcerptReferenceRelevance
" ALS-8176 (71), the 3',5'-di-O-isobutyryl prodrug of 2c, demonstrated good oral bioavailability and a high level of 2c-TP in vivo."( Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.
Beigelman, L; Blatt, LM; Chanda, SM; Deval, J; Dyatkina, N; Fung, A; Hong, J; Jin, Z; Liu, J; Prhavc, M; Serebryany, V; Smith, DB; Stevens, SK; Symons, JA; Tam, Y; Taylor, J; Wang, G; Zhang, Q, 2015
)
0.42

Dosage Studied

ExcerptRelevanceReference
"The dose-response relationship between extracellular concentration of cytosine arabinoside (ara-C) and intracellular formation of the putative active metabolites of ara-C [ara-C incorporation into DNA and intracellular pools of ara-C in triphosphate form (ara-CTP)] was investigated in blast cells obtained from patients with acute nonlymphocytic leukemia (ANLL) by exposing these cells in vitro to 10, 100, or 1,000 nmol/L of ara-C."( Metabolism of ara-C by blast cells from patients with ANLL.
Akman, SA; Joneckis, CC; Ross, DD; Schiffer, CA; Thompson, BW, 1986
)
0.27
" We therefore, attempted to improve the complete remission rate in patients with low ara-CTP levels by decreasing the intermittent ara-C dosing interval, thereby raising the minimum ara-CTP level in leukemic cells between doses."( Pharmacologically directed ara-C therapy for refractory leukemia.
Danhauser, L; Estey, E; Iacoboni, S; Keating, MJ; Liliemark, JO; Plunkett, W, 1985
)
0.27
"Twenty-seven patients with B-cell chronic lymphocytic leukemia (CLL) or a related lymphoid malignancy were treated with high-dose cytosine arabinoside (ara-C) at a dosage of 3 gm/m2 administered over 2 hours every 12 hours at one to four doses per course, which were repeated at 4-week intervals."( High-dose cytosine arabinoside in chronic lymphocytic leukemia: a clinical and pharmacologic analysis.
Estey, E; Hagemeister, FB; Hall, R; Kantarjian, HM; Keating, MJ; McLaughlin, P; Plunkett, W; Robertson, LE, 1993
)
0.29
" These in vitro studies support our hypothesis that enhanced metabolism of ara-C in DS cells may be a contributing factor to the superior survival rate of DS children with AML and is possibly based on a gene dosage effect of genes localized to chromosome 21 including cystathionine-beta-synthase."( Enhanced metabolism of 1-beta-D-arabinofuranosylcytosine in Down syndrome cells: a contributing factor to the superior event free survival of Down syndrome children with acute myeloid leukemia.
Buck, SA; Gurney, JG; Matherly, LH; Ravindranath, Y; Stout, ML; Taub, JW, 1996
)
0.29
" It is worthwhile to compare literature data to assess an optimal dosage of ara-C in pediatric patients."( Pharmacology of intracellular cytosine-arabinoside-5'-triphosphate in malignant cells of pediatric patients with initial or relapsed leukemia and in normal lymphocytes.
Cinatl, J; Hollatz, G; Koehl, U; Kornhuber, B; Kreuter, J; Mutschler, E; Rohrbach, E; Schwabe, D; Visschedyk, K, 2007
)
0.34
" This study, conducted within a clinical setting, aimed to assess ara-CTP levels in circulating peripheral blasts from non-M3 AML patients receiving cytarabine at one of three dosing levels, using a novel biosensor assay."( Intracellular cytarabine triphosphate in circulating blasts post-treatment predicts remission status in patients with acute myeloid leukemia.
Anderson, E; Foulstone, E; Greenwood, R; Heywood, J; Hull, J; Mehta, P; Preston, A; Protheroe, R; Rees, B; Salisbury, V, 2019
)
0.51
" Optimal dosing protocols for immunomodulation in dogs have not been defined."( Oral cytarabine ocfosfate pharmacokinetics and assessment of leukocyte biomarkers in normal dogs.
Dickinson, PJ; Knych, HK; Kol, A; Pypendop, BH; Questa, M; Rodrigues, CA; Vernau, KM; Vernau, W; Zwueste, DM,
)
0.13
" Application of functional and active metabolite assessment is feasible and may provide more relevant data to determine optimal dosing regimens for Ara-C-based treatments."( Oral cytarabine ocfosfate pharmacokinetics and assessment of leukocyte biomarkers in normal dogs.
Dickinson, PJ; Knych, HK; Kol, A; Pypendop, BH; Questa, M; Rodrigues, CA; Vernau, KM; Vernau, W; Zwueste, DM,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrimidine ribonucleoside monophosphate
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TDP1 proteinHomo sapiens (human)Potency0.90480.000811.382244.6684AID686978; AID686979
67.9K proteinVaccinia virusPotency16.01050.00018.4406100.0000AID720579; AID720580
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency0.00520.00419.984825.9290AID504444
gemininHomo sapiens (human)Potency0.45530.004611.374133.4983AID624296; AID624297
Guanine nucleotide-binding protein GHomo sapiens (human)Potency7.94331.995325.532750.1187AID624287
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1224817Assays to identify small molecules inhibitory for eIF4E expression2015Chemistry & biology, Jul-23, Volume: 22, Issue:7
Internal Ribosome Entry Site-Based Bicistronic In Situ Reporter Assays for Discovery of Transcription-Targeted Lead Compounds.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745846Firefly Luciferase Counterscreen for Inhibitors of ATXN expression
AID1745848Confirmatory qHTS for Inhibitors of ATXN expression
AID1745847CMV-Luciferase Counterscreen for Inhibitors of ATXN expression
AID1745850Viability Counterscreen for Confirmatory qHTS for Inhibitors of ATXN expression
AID1745849Viability Counterscreen for CMV-Luciferase Assay of Inhibitors of ATXN expression
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1200152Inhibition of human mitochondrial RNA polymerase assessed as 13-mer product using [33P]RNA/DNA primer/templates used by agarose gel electrophoresis2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.
AID1200153Binding affinity to human mitochondrial RNA polymerase assessed as compound incorporation using [33P]RNA/DNA primer/templates used by agarose gel electrophoresis2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Discovery of 4'-chloromethyl-2'-deoxy-3',5'-di-O-isobutyryl-2'-fluorocytidine (ALS-8176), a first-in-class RSV polymerase inhibitor for treatment of human respiratory syncytial virus infection.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (266)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990117 (43.98)18.7374
1990's90 (33.83)18.2507
2000's41 (15.41)29.6817
2010's14 (5.26)24.3611
2020's4 (1.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.53

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 Index12.53 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.53)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials12 (4.49%)5.53%
Reviews0 (0.00%)6.00%
Reviews14 (5.24%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies5 (1.87%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
Other236 (88.39%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]