3-deazauridine
2(1H)-pyridinone, 4-hydroxy-1-b-D-ribofuranosyl-
Identification
| Name | 3-deazauridine |
| CAS Number | 23205-42-7 |
| EINECS | 245-488-8 |
| FDA UNII | 263CU738ZY |
| Molecular Formula | C10 H13 N O6 |
| Molecular Weight | 243.21581000 |
| MDL Number | MFCD00006522 |
| Nikkaji Number | J16.579D |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 528.01 °C. @ 760.00 mm Hg (est) |
| Flash Point | 524.00 °F. TCC ( 273.10 °C. ) (est) |
| logP (o/w) | -1.693 (est) |
| Soluble in | water, 1e+006 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for 3-deazauridine usage levels up to | not for fragrance use. |
| Recommendation for 3-deazauridine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
3-
deazuridine
1-[(2R,3R,4S,5R)-3,4-
dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxypyridin-2-one
4-
hydroxy-1-beta-D-ribofuranosyl-2(1H)-pyridinone
4-
hydroxy-1-beta-D-ribofuranosyl-2(1H)-pyridone
2(1H)-
pyridinone, 4-hydroxy-1-b-D-ribofuranosyl-
2(1H)-
pyridinone, 4-hydroxy-1-beta-D-ribofuranosyl-
PubMed:
Constitutive activation of the ATM/BRCA1 pathway prevents DNA damage-induced apoptosis in 5-azacytidine-resistant cell lines.
PubMed:
Discovery of novel ribonucleoside analogs with activity against human immunodeficiency virus type 1.
PubMed:
Synthesis of C3-arylated-3-deazauridine derivatives with potent anti-HSV-1 activities.
PubMed:
Introduction of a fluorine atom at C3 of 3-deazauridine shifts its antimetabolic activity from inhibition of CTP synthetase to inhibition of orotidylate decarboxylase, an early event in the de novo pyrimidine nucleotide biosynthesis pathway.
PubMed:
3-Deazauridine enhances the antileukemic action of 5-aza-2'-deoxycytidine and targets drug-resistance due to deficiency in deoxycytidine kinase.
PubMed:
Synthesis and biological evaluation of 3,3-difluoropyridine-2,4(1H,3H)-dione and 3-deaza-3-fluorouracil base and nucleoside derivatives.
PubMed:
Synthesis of methylene- and difluoromethylenephosphonate analogues of uridine-4-phosphate and 3-deazauridine-4-phosphate.
PubMed:
The 1.48 A resolution crystal structure of the homotetrameric cytidine deaminase from mouse.
PubMed:
Electrophysiological characterization and modeling of the structure activity relationship of the human concentrative nucleoside transporter 3 (hCNT3).
PubMed:
3-Deazauridine triggers dose-dependent apoptosis in myeloid leukemia cells and enhances retinoic acid-induced granulocytic differentiation of HL-60 cells.
PubMed:
Correlation of nucleoside and nucleobase transporter gene expression with antimetabolite drug cytotoxicity.
PubMed:
Potentiation of the anti-HIV activity of zalcitabine and lamivudine by a CTP synthase inhibitor, 3-deazauridine.
PubMed:
Role of antimetabolites of purine and pyrimidine nucleotide metabolism in tumor cell differentiation.
PubMed:
Possible involvement of DNA methylation in 5-azacytidine-induced neuronal cell apoptosis.
PubMed:
The IMP dehydrogenase inhibitor mycophenolic acid antagonizes the CTP synthetase inhibitor 3-deazauridine in MOLT-3 human leukemia cells: a central role for phosphoribosyl pyrophosphate.
PubMed:
Gemcitabine: a modulator of intracellular nucleotide and deoxynucleotide metabolism.
PubMed:
Antiviral studies of feline infectious peritonitis virus in vitro.
PubMed:
Inhibition of CTP synthetase induces differentiation of HL-60 cells and down-regulation of the c-myc oncogene.
PubMed:
Enhancement of anti-neoplastic activity of cytosine arabinoside against human HL-60 myeloid leukemic cells by 3-deazauridine.
PubMed:
Biological activity of 3-deazauridine nucleoside analogue: a theoretical study.
PubMed:
Modulation of cytosine arabinoside toxicity by 3-deazauridine in a murine leukemia model.
PubMed:
Synthesis of two cyclopentenyl-3-deazapyrimidine carbocyclic nucleosides related to cytidine and uridine.
PubMed:
Synthesis, antitumor activity, and antiviral activity of 3-substituted 3-deazacytidines and 3-substituted 3-deazauridines.
PubMed:
Antiviral and cytotoxicity evaluation of 3-nitro-3-deazauridine.
PubMed:
Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro.
PubMed:
Dual effects of pyrazofurin and 3-deazauridine upon pyrimidine and purine biosynthesis in mouse L1210 leukemia.
PubMed:
Chemotherapy of L1210 and L1210/ARA-C leukemia with 5-aza-2'-deoxycytidine and 3-deazauridine.
PubMed:
A newly developed immunofluorescent assay for determining the Pichinde virus-inhibitory effects of selected nucleoside analogues.
PubMed:
Cyclopentenylcytosine. A carbocyclic nucleoside with antitumor and antiviral properties.
PubMed:
2',3'-Dideoxycytidine: regulation of its metabolism and anti-retroviral potency by natural pyrimidine nucleosides and by inhibitors of pyrimidine nucleotide synthesis.
PubMed:
Inhibitory effects of antiviral compounds on respiratory syncytial virus replication in vitro.
PubMed:
Synergistic activity of purine metabolism inhibitors in cultured human tumor cells.
PubMed:
Role of uridine triphosphate in the phosphorylation of 1-beta-D-arabinofuranosylcytosine by Ehrlich ascites tumor cells.
PubMed:
Effect of deoxycytidine on the in vitro response of human leukemia cells to inhibitors of de novo pyrimidine biosynthesis.
PubMed:
Homogeneous uridine kinase from Ehrlich ascites tumor: substrate specificity and inhibition by bisubstrate analogs.
PubMed:
The effect of 3-deazauridine and dipyridamole on uridine utilization by mice.
PubMed:
Approaches to overcome in vivo anti-cancer drug resistance.
PubMed:
3-Deazauridine (NSC 126849): an interesting modulator of biochemical response.
PubMed:
Analysis of candidate anticancer drugs by thermospray high-performance liquid chromatography-mass spectrometry and by high-resolution mass spectrometry.
PubMed:
Uridine kinase from Ehrlich ascites carcinoma. Purification and properties of homogeneous enzyme.
PubMed:
Effects of pyrimidine antagonists on sialic acid regeneration in HL-60 cells.
PubMed:
Synthesis of optically active beta-lactams using the photochemical reaction of 3-deazauridines.
PubMed:
Effect of uridine on response of 5-azacytidine-resistant human leukemic cells to inhibitors of de novo pyrimidine synthesis.
PubMed:
Regulation of pyrimidine biosynthesis in cultured L1210 cells by 3-deazauridine.
PubMed:
Pleiotropic mutants of Chinese hamster cells with altered cytidine 5'-triphosphate synthetase.
PubMed:
Cytotoxic and biochemical effects of thymidine and 3-deazauridine on human tumor cells.
PubMed:
Specificity and sodium dependence of the active nucleoside transport system in choroid plexus.
PubMed:
Transport of uridine and 3-deazauridine in cultured human lymphoblastoid cells.
PubMed:
Quantitative determination of nucleosides and their phosphate esters--1. The acidic nucleosides, 3-deazauridine and 6-azauridine.
PubMed:
Induction of differentiation of human acute myelogenous leukemia cells: therapeutic implications.
PubMed:
Labelling of the thymidine and deoxycytidine bases of DNA by [2-14C]deoxycytidine in cultured L1210 cells.
PubMed:
Effect of 3-deazauridine on the metabolism, toxicity, and antitumor activity of azacitidine in mice bearing L1210 leukemia sensitive and resistant to cytarabine.
PubMed:
Kinetics of deamination of 5-aza-2'-deoxycytidine and cytosine arabinoside by human liver cytidine deaminase and its inhibition by 3-deazauridine, thymidine or uracil arabinoside.
PubMed:
Hemodynamic effects of potentially useful antineoplastic agents.
PubMed:
Synthesis of diazaphenoxathiin nucleosides from 3-deazauridine and their chemical properties.
PubMed:
Sample preparation and estimation of plasma concentration of 3-deazauridine by high-performance liquid chromatography.
PubMed:
Synthesis of pyridazine analogues of the naturally occurring nucleosides cytidine, uridine, deoxycytidine, and deoxyuridine.
PubMed:
Phase II study of 3-deazauridine in advanced colorectal adenocarcinoma.
PubMed:
Synthetic studies on 3-deazauridine derivatives.
PubMed:
Drug control of Ara-C-resistant tumor cells.
PubMed:
Phase I trial and pharmacokinetics of a daily x 5 schedule of 3-deazauridine.
PubMed:
Inhibition of rotaviruses by selected antiviral substances: mechanisms of viral inhibition and in vivo activity.
PubMed:
Optical activity and electronic absorption spectra of some simple nucleosides related to cytidine and uridine: all-valence-shell molecular orbital calculations.
PubMed:
Induction of differentiation of human promyelocytic leukemia cells (HL-60) by nucleosides and methotrexate.
PubMed:
Inhibition of bluetongue and Colorado tick fever orbiviruses by selected antiviral substances.
PubMed:
Cell cycle arrest as a basis of enhancement of 1-beta-D-arabinofuranosylcytosine anabolism in human lymphoblastoid RPMI 6410 cells cultured with 3-deazauridine.
PubMed:
Phase I--II study of 3-deazauridine in adults with acute leukemia.
PubMed:
In vivo cellular kinetic and pharmacological studies of 1-beta-D-arabinofuranosylcytosine and 3-deazauridine chemotherapy for relapsing acute leukemia.
PubMed:
Simultaneous determination of 1-beta-D-arabinofuranosylcytosine 5'-triphosphate and 3-deazauridine 5'-triphosphate in human leukemia cells by high-performance liquid chromatography.
PubMed:
Altered 5-azacytidine metabolism following 3-deazauridine treatment of L5178Y and human myeloblasts.
PubMed:
Phosphorylation of nucleosides catalyzed by a mammalian enzyme other than uridine-cytidine kinase.
PubMed:
Molecular orbital studies on the structure of nucleoside analogs. III. Conformation of 3-deazapyrimidine nucleosides.
PubMed:
Cytidine and deoxycytidylate deaminase inhibition by uridine analogs.
PubMed:
Phase I study of 3-deazauridine in the treatment of adults with solid tumors.
PubMed:
Intracellular nucleotide pools and their significance in antimetabolite therapy.
PubMed:
Penetration of 3-deazauridine into human brain, intracerebral tumor, and cerebrospinal fluid.
PubMed:
Synergistic action of 5-aza-2'-deoxycytidine and 3-deazauridine on L1210 leukemic cells and EMT6 tumor cells.
PubMed:
Drug sequence-dependent toxicity and small bowel mucosal injury in mice treated with low doses of 3-deazauridine and 1-beta-D-arabinofuranosylcytosine.
PubMed:
Enzyme pattern-directed chemotherapy. Effects of antipyrimidine combinations on the ribonucleotide content of hepatomas.
PubMed:
Biochemical and pharmacological effects of the fermentation-derived antitumor agent, (alphaS,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (AT-125).
PubMed:
High-pressure liquid chromatographic analysis of 3-deazauridine-5'-triphosphate in human cancer cells.
PubMed:
Pharmacokinetics and disposition of 3-deazauridine in humans.
PubMed:
Ara-C metabolism: implications for drug resistance and drug interactions.
PubMed:
The regulation of thymidylate biosynthesis in Novikoff hepatoma cells and the effects of amethopterin, 5-fluorodeoxyuridine, and 3-deazauridine.
PubMed:
Conformation of pyridazine nucleosides: the molecular structure of 4-hydroxy-1-(beta-D-ribofuranosyl)pyridazin-6-one (3-deaza-6-azauridine).
PubMed:
Formation of 1-beta-D-arabinofuranosylcytosine diphosphate choline in neoplastic and normal cells.
PubMed:
Formation of 1-beta-D-arabinofuranosylcytosine diphosphate choline in cultured human leukemic RPMI 6410 cells.
PubMed:
The disposition of 3-deazauridine in mice.
PubMed:
Toxicity of combinations of arabinosylcytosine and 3-deazauridine toward neoplastic cells in culture.
PubMed:
Multiple basis of combination chemotherapy.
PubMed:
Selective inhibition of RNA tumor virus replication in vitro and evaluation of candidate antiviral agents in vivo.
PubMed:
Effects of 2-deoxy-D-glucose and 3 deazauridine individually and in combination on the replication of Japanese B encephalitis virus.
PubMed:
Enzyme pattern-directed chemotherapy: synergistic interaction of 3-deazauridine with D-galactosamine.
PubMed:
Nucleic acid related compounds. 17.3-Deazuridine. Stannous chloride catalysis of cis-diol vs. phenolic base methylation with diazomethane.
PubMed:
The effects of nucleoside analogs on cutaneous neoplasms.
PubMed:
The mechanism of action of 3-deazauridine in tumor cells sensitive and resistant to arabinosylcytosine.
PubMed:
The structure of nucleosides in relation to their biological and and biochemical activity: a summary.
PubMed:
Synthesis and biological activity of 4-beta-Iribofuranosyl-1,3-dihydroxybenzene ("1,3-dideazauridine").
PubMed:
Cytidine 5'-triphosphate synthetase as a target for inhibition by the antitumor agent 3-deazauridine.
PubMed:
Prevention by testosterone of the intestinal toxicity caused by the antitumor agent 3-deazauridine.
PubMed:
Inhibition of gross leukemia virus-induced plaque formation in XC cells by 3-deazauridine.
PubMed:
3-Deazauridine: inhibition of ribonucleic acid virus-induced cytopathogenic effects in vitro.
PubMed:
3-Deazauridine: crystal structure and conformation.
PubMed:
Codon-anticodon interaction studied with oligonucleotides containing 3 -deazauridine, 4 -deoxyuridine or 3 -deaza- 4 -deoxyuridine. II. Ribosome binding of oligonucleotides and phenylalanyl-tRNA.
PubMed:
Codon-anticodon interaction studied with oligonucleotides containing 3 -deazauridine, 4 -deoxyuridine or 3 -deaza- 4 -deoxyuridine. I. Synthesis by primer-dependent polynucleotide phosphorylase of oligonucleotides containing modofied nucleosides.
PubMed:
Inhibition of RNA virus replication in vitro by 3-deazacytidine and 3-deazauridine.
PubMed:
Studies on the mode of action of 3-deazapyrimidines. 1. Metabolism of 3-deazauridine and 3-deazacytidine in microbial and tumor cells.