Page last updated: 2024-11-13

3-deazauridine

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

Description

3-Deazauridine: 4-Hydroxy-1-(beta-D-ribofuranosyl)-2-pyridinone. Analog of uridine lacking a ring-nitrogen in the 3-position. Functions as an antineoplastic agent. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID54684286
CHEMBL ID491887
CHEBI ID183851
SCHEMBL ID352974
SCHEMBL ID16179302
MeSH IDM0023213

Synonyms (32)

Synonym
3-deazuridine
2(1h)-pyridinone, 4-hydroxy-1-beta-d-ribofuranosyl-
2(1h)-pyridone, 4-hydroxy-1-beta-d-ribofuranosyl-
einecs 245-488-8
4-hydroxy-1-beta-d-ribofuranosyl-2(1h)-pyridinone
4-hydroxy-1-beta-d-ribofuranosyl-2(1h)-pyridone
nsc 126849
3-deazauridine
2(1h)-pyridinone, 4-hydroxy-1-b-d-ribofuranosyl-
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-hydroxy-pyridin-2-one
CHEMBL491887
1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxypyridin-2-one
CHEBI:183851
23205-42-7
2(1h)-pyridinone, 4-hydroxy-1-beta-d-ribofuranosyl- (9ci)
BMSE001022
263cu738zy ,
unii-263cu738zy
SCHEMBL352974
1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-4-hydroxypyridin-2(1h)-one;4-hydroxy-1-?-d-ribofuranosyl-2(1h)pyridone
2(1h)-pyridinone, 4-hydroxy-1-beta-d-ribofuranosyl
SCHEMBL16179302
AKOS027327918
J-015032
A900718
1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-hydroxypyridin-2(1h)-one
F12665
mfcd00006522
Q27254037
DTXSID80945889
1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-4-hydroxypyridin-2(1h)-one
PD064029

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" This drug combination was severely toxic when 3-deazauridine was administered 2 to 8 hr prior to 1-beta-D-arabinofuranosylcytosine; most mice treated in this way died within 3 days of the last treatment."( Drug sequence-dependent toxicity and small bowel mucosal injury in mice treated with low doses of 3-deazauridine and 1-beta-D-arabinofuranosylcytosine.
Jakobs, ES; Lauzon, GJ; Paterson, AR; Weinstein, WM, 1979
)
0.73
" 3N-3DU exhibited comparable toxicity to ribavirin in KB cells, was 4-fold less toxic in WISH cells and 4-fold more toxic in LLC-MK2 cells."( Antiviral and cytotoxicity evaluation of 3-nitro-3-deazauridine.
Allen, LB; Cook, PD; Holland, CS; Kehoe, MJ; McNamara, DJ; Teepe, AG, 1989
)
0.53

Pharmacokinetics

ExcerptReferenceRelevance
"The uridine analog 3-deazauridine has been given to 19 patients in a phase I and pharmacokinetic study."( Phase I trial and pharmacokinetics of a daily x 5 schedule of 3-deazauridine.
Bruno, S; Creaven, PJ; Henderson, ES; Mittelman, A; Priore, RL; Rustum, YM; Solomon, JK, 1982
)
0.83
[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]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID97414In vivo percent increase in life span (%ILS) of mice bearing L1210 leukemia at a dose of 400 mg/kg1982Journal of medicinal chemistry, Jul, Volume: 25, Issue:7
Synthesis of pyridazine analogues of the naturally occurring nucleosides cytidine, uridine, deoxycytidine, and deoxyuridine.
AID719257Cytotoxicity against african green monkey Vero cells after 3 days by neutral red dye method2012Bioorganic & medicinal chemistry letters, Dec-15, Volume: 22, Issue:24
Synthesis of C3-arylated-3-deazauridine derivatives with potent anti-HSV-1 activities.
AID98851Compound was tested for percent increase in life span against L1210 lymphoid leukemia1987Journal of medicinal chemistry, Feb, Volume: 30, Issue:2
Synthesis and antitumor activity of fluorine-substituted 4-amino-2(1H)-pyridinones and their nucleosides. 3-Deazacytosines.
AID96814In vitro inhibitory activity against growth of L1210 mouse leukemia cells at 10E-4 M concentration; IA means Inactive1982Journal of medicinal chemistry, Jul, Volume: 25, Issue:7
Synthesis of pyridazine analogues of the naturally occurring nucleosides cytidine, uridine, deoxycytidine, and deoxyuridine.
AID719255Antiviral activity against Herpes simplex virus type 1 infected in Vero cells at 0.01 ID50/cells assessed as protection against virus-induced cytopathic effect after 3 days by neutral red dye method2012Bioorganic & medicinal chemistry letters, Dec-15, Volume: 22, Issue:24
Synthesis of C3-arylated-3-deazauridine derivatives with potent anti-HSV-1 activities.
AID131144Compound was tested for antitumor activity against L1210 /ara-C leukemia in athymic mice at dose 50 mg/kg administered intraperitoneally1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID131142Compound was tested for antitumor activity against L1210 /ara-C leukemia in athymic mice at dose 12.5 mg/kg administered intraperitoneally1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID227703The antiviral index is defined as MCC/MIC1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis, antitumor activity, and antiviral activity of 3-substituted 3-deazacytidines and 3-substituted 3-deazauridines.
AID131145Compound was tested for antitumor activity against L1210 leukemia in athymic mice at dose 100 mg/kg administered intraperitoneally1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID131154Compound was tested for antitumor activity against human LOX melanoma tumor xenografts in athymic mice at dose 300 mg/kg administered intraperitoneally1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID131157Compound was tested for antitumor activity against human MX-1 mammary tumor xenografts in athymic mice at dose 200 mg/kg administered subrenal capsule1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID131158Compound was tested for antitumor activity against human MX-1 mammary tumor xenografts in athymic mice at dose 300 mg/kg administered subrenal capsule1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID200196The minimum inhibitory concentration (MIC) required to inhibit rhinovirus type 34 induced cytopathic effect (CPE) on WISH cells1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis, antitumor activity, and antiviral activity of 3-substituted 3-deazacytidines and 3-substituted 3-deazauridines.
AID131146Compound was tested for antitumor activity against L1210 leukemia in athymic mice at dose 25 mg/kg administered intraperitoneally1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID131147Compound was tested for antitumor activity against L1210 leukemia in athymic mice at dose 50 mg/kg administered intraperitoneally1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID349905Cytostatic activity against human CEM cells after 3 days by Coulter counting analysis2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
Synthesis and biological evaluation of 3,3-difluoropyridine-2,4(1H,3H)-dione and 3-deaza-3-fluorouracil base and nucleoside derivatives.
AID719256Ratio of acyclovir EC50 to compound EC50 for Herpes simplex virus type 12012Bioorganic & medicinal chemistry letters, Dec-15, Volume: 22, Issue:24
Synthesis of C3-arylated-3-deazauridine derivatives with potent anti-HSV-1 activities.
AID131153Compound was tested for antitumor activity against human LOX melanoma tumor xenografts in athymic mice at dose 200 mg/kg administered intraperitoneally1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID131143Compound was tested for antitumor activity against L1210 /ara-C leukemia in athymic mice at dose 25 mg/kg administered intraperitoneally1988Journal of medicinal chemistry, Sep, Volume: 31, Issue:9
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
AID495977Cytotoxicity against human HepG2 cells at 3 uM after 48 hrs2010Antimicrobial agents and chemotherapy, Jan, Volume: 54, Issue:1
Cellular pharmacology of the anti-hepatitis B virus agent beta-L-2',3'-didehydro-2',3'-dideoxy-N4-hydroxycytidine: relevance for activation in HepG2 cells.
AID100633In vitro inhibition of L1210 leukemia cell growth1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis, antitumor activity, and antiviral activity of 3-substituted 3-deazacytidines and 3-substituted 3-deazauridines.
AID216254The minimum cytotoxic concentration (MCC) reducing cell viability on WISH cells1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis, antitumor activity, and antiviral activity of 3-substituted 3-deazacytidines and 3-substituted 3-deazauridines.
AID349903Cytostatic activity against mouse L1210 cells after 2 days by Coulter counting analysis2009Journal of medicinal chemistry, May-14, Volume: 52, Issue:9
Synthesis and biological evaluation of 3,3-difluoropyridine-2,4(1H,3H)-dione and 3-deaza-3-fluorouracil base and nucleoside derivatives.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (75)

TimeframeStudies, This Drug (%)All Drugs %
pre-199060 (80.00)18.7374
1990's7 (9.33)18.2507
2000's3 (4.00)29.6817
2010's4 (5.33)24.3611
2020's1 (1.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 19.18

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 Index19.18 (24.57)
Research Supply Index4.37 (2.92)
Research Growth Index4.26 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.18)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (3.85%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other75 (96.15%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]