Page last updated: 2024-11-06

1-beta-d-arabinofuranosylcytosine 5'-monophosphate

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

Description

1-beta-d-arabinofuranosylcytosine 5'-monophosphate (ara-CMP) is a nucleotide analog of cytidine monophosphate (CMP) that has been extensively studied for its antiviral and anticancer properties. Its synthesis involves the modification of the sugar moiety of cytidine, replacing the hydroxyl group at the 2' position with a hydrogen atom, resulting in an arabinose sugar instead of a ribose sugar. Ara-CMP has been shown to inhibit DNA polymerase, a key enzyme involved in DNA replication, thereby disrupting cell growth and division. This inhibition is particularly effective against viruses like herpes simplex virus and cytomegalovirus, as well as certain types of cancer cells. The compound's ability to interfere with DNA synthesis makes it a promising candidate for treating various diseases. Extensive research into its mechanisms of action, its potential therapeutic applications, and its safety profile continue to be conducted to optimize its use in medicine.'

1-beta-D-arabinofuranosylcytosine 5'-monophosphate: RN given refers to dihydrogen phosphate [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65177
CHEMBL ID596186
SCHEMBL ID11217191
MeSH IDM0083607

Synonyms (51)

Synonym
phosphoric acid mono-[(2r,3s,4s,5r)-5-(4-amino-2-oxo-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester
[(2r,3s,4s,5r)-5-(4-amino-2-oxo-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
aracmp
aracytidine 5'-monophosphate
7075-11-8
1-.beta.-d-arabinofuranosylcytosine 5'-phosphate
aracytidine 5'-phosphate
2(1h)-pyrimidinone, 4-amino-1-(5-o-phosphono-.beta.-d-arabinofuranosyl)-
cytosine arabinoside 5'mp
nsc-99445
cytosine arabinoside 5'-phosphate
cytosine beta-d-arabinofuranoside 5'-monophosphate, >=99%
1-beta-d-arabinofuranosylcytosine 5'-phosphate
ara-5'-cmp
DB02456
cytosine arabinose-5'-phosphate
bdbm31913
1-beta-d-arabinofuranosylcytosine 5-monophosphate
[(2r,3s,4s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
ara-cytidine monophosphate
CHEMBL596186
cytarabine 5'-phosphate
cytosine beta-d-arabinofuranoside 5'-monophosphate
arabinosylcytosine 5'-monophosphate
cytosine arabinoside 5'-monophosphate
1beta-arabino-furanosylcytosine-5'-monophosphoric acid, d-
2(1h)-pyrimidinone, 4-amino-1-(5-o-phosphono-beta-d-arabinofuranosyl)-
unii-y73692ghi4
cytosine, 1-beta-d-arabinofuranosyl-, 5'-(dihydrogen phosphate)
ara 5'-cmp
nsc 99445
y73692ghi4 ,
1-beta-d-arabinofuranosylcytosine 5'-monophosphate
cytarabine 5'-monophosphate
AKOS015899632
((2r,3s,4s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
DTXSID60221012
SCHEMBL11217191
phosphoric acid mono-((2r,3s,4s,5r)-5-(4-amino-2-oxo-2h-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl) ester
4-amino-1-(5-o-phosphono-.beta.-d-arabinofuranosyl)-2(1h)-pyrimidinone
cytosine, 1-.beta.-d-arabinofuranosyl-, 5'-(dihydrogen phosphate)
((2r,3s,4s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl)methyl dihydrogen phosphate
1-.beta.-d-arabinofuranosylcytosine 5'-monophosphate
mfcd00069771
cytidin-5'-monophosphat
4-amino-1-(5-o-phosphono-beta-d-arabinofuranosyl)pyrimidin-2(1h)-one
Q27294330
cytosine-beta-d-arabinofuranoside-5'-monophosphoric acid
4-amino-1-(5-o-phosphono-beta-d-arabinofuranosyl)-2(1h)-pyrimidinone
CS-0455093
{[(2r,3s,4s,5r)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" In fact, when the optimum dosage of 75 (mumol/kg)/day x 5 was used, the administration of ara-C alone was followed by an increased life span (ILS) of 45%."( Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
Hong, CI; Nechaev, A; West, CR, 1979
)
0.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Activation 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 (4)

Processvia Protein(s)Taxonomy
ubiquinone biosynthetic process2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
isoprenoid biosynthetic process2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
terpenoid biosynthetic process2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
isopentenyl diphosphate biosynthetic process, methylerythritol 4-phosphate pathway2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
protein binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
zinc ion binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase activity2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
lyase activity2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
manganese ion binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
identical protein binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
metal ion binding2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseEscherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1135054Antitumor activity against mouse L1210 cells allografted in C3D2F1/J mouse assessed as increase in life span at 24.2 mg/kg, ip qd administered for 5 days relative to control1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
AID1135047Antitumor activity against mouse L1210 cells allografted in C3D2F1/J mouse assessed as median survival time at 24.2 mg/kg, ip qd administered for 5 days (Rvb = 10 days)1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
AID1135087Cytotoxicity against mouse L1210 cells assessed as growth inhibition measured at 72 hrs in presence of 100 uM prednisolone by trypan blue exclusion assay1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
AID1135044Antitumor activity against mouse L1210 cells allografted in C3D2F1/J mouse assessed as median survival time at 50 mg/kg, ip qd administered for 5 days (Rvb = 9 days)1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
AID1135058Toxicity in C3D2F1/J mouse allografted with mouse L1210 cells assessed as body weight change at 50 mg/kg, ip qd administered for 5 days measured on day 8 (Rvb = 1.81 +/- 0.79 g)1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
AID1135062Toxicity in C3D2F1/J mouse allografted with mouse L1210 cells assessed as body weight change at 24.2 mg/kg, ip qd administered for 5 days measured on day 8 (Rvb = 1.81 +/- 0.79 g)1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
AID1135086Cytotoxicity against mouse L1210 cells assessed as growth inhibition measured at 72 hrs in presence of 5 uM prednisolone by trypan blue exclusion assay1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
AID1135042Cytotoxicity against mouse L1210 cells assessed as growth inhibition measured at 72 hrs by trypan blue exclusion assay1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
AID1135050Antitumor activity against mouse L1210 cells allografted in C3D2F1/J mouse assessed as increase in life span at 50 mg/kg, ip qd administered for 5 days relative to control1979Journal of medicinal chemistry, Nov, Volume: 22, Issue:11
Nucleoside conjugates as potential antitumor agents. 2. Synthesis and biological activity of 1-(beta-D-arabinofuranosyl)cytosine conjugates of prednisolone and prednisone.
AID1799187SPR Biosensor Assay from Article 10.1021/jm801475n: \\A structure-based approach to ligand discovery for 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase: a target for antimicrobial therapy.\\2009Journal of medicinal chemistry, Apr-23, Volume: 52, Issue:8
A structure-based approach to ligand discovery for 2C-methyl-D-erythritol-2,4-cyclodiphosphate synthase: a target for antimicrobial therapy.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (17)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (41.18)18.7374
1990's6 (35.29)18.2507
2000's4 (23.53)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: 11.35

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 Index11.35 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.24 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.35)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies1 (5.88%)4.05%
Observational0 (0.00%)0.25%
Other16 (94.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]