EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

3-deazauridine
2(1H)-pyridinone, 4-hydroxy-1-b-D-ribofuranosyl-

Supplier Sponsors

CAS Number: 23205-42-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:245-488-8
FDA UNII: 263CU738ZY
Nikkaji Web:J16.579D
MDL:MFCD00006522
XlogP3-AA:-1.80 (est)
Molecular Weight:243.21581000
Formula:C10 H13 N O6
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
3-DEAZAURIDINE 95%
Odor: characteristic
Use: Antimetabolite antiviral dosing regimen for hepatitis C virus or flaviviridae therapy.
Carbosynth
For experimental / research use only.
3-Deazauridine
George Uhe Company
3-Deazauridine
Glentham Life Sciences
3-Deazauridine
Santa Cruz Biotechnology
For experimental / research use only.
3-Deazauridine
Sigma-Aldrich: Aldrich
For experimental / research use only.
3-Deazauridine 98%
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :54684286
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxypyridin-2-one
Chemidplus:0023205427
RTECS:UV1148000 for cas# 23205-42-7
 
References:
 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxypyridin-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):54684286
Pubchem (sid):134995031
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
Metabolomics Database:Search
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.59.7000
ChemSpider:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
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-
 

Articles:

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.
 
Notes:
4-hydroxy-1-(beta-d-ribofuranosyl)-2-pyridinone. analog of uridine lacking a ring-nitrogen in the 3-position. functions as an antineoplastic agent.
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