U5377
Uracil 1-β-D-arabinofuranoside
≥98% (HPLC), synthetic (organic), powder
Synonym(s):
Arauridine, Spongouridin, 1-β-D-Arabinofuranosyluracil
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About This Item
Empirical Formula (Hill Notation):
C9H12N2O6
CAS Number:
Molecular Weight:
244.20
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
221-386-9
MDL number:
Beilstein/REAXYS Number:
28749
Assay:
≥98% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
water: 50 mg/mL, clear, colorless
Storage temp.:
−20°C
Product Name
Uracil 1-β-D-arabinofuranoside, lymphoma antiproliferative
SMILES string
OC[C@H]1O[C@H]([C@@H](O)[C@@H]1O)N2C=CC(=O)NC2=O
InChI key
DRTQHJPVMGBUCF-CCXZUQQUSA-N
InChI
1S/C9H12N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h1-2,4,6-8,12,14-15H,3H2,(H,10,13,16)/t4-,6-,7+,8-/m1/s1
biological source
synthetic (organic)
assay
≥98% (HPLC)
form
powder
solubility
water: 50 mg/mL, clear, colorless
storage temp.
−20°C
Quality Level
General description
1-β-d-arabinofuranosyluracil (Ara-U) is the detoxification product or metabolite of 1-β-d-arabinofuranosylcytosine (Ara-C). Uracil 1-β-D-arabinofuranoside is the human metabolite of a cytostatic agent called cytarabine (CYT).
Application
Uracil 1-β-D-arabinofuranoside may be used as a reference compound in the analysis of cytostatics and metabolites in hospital wastewater by hydrophilic interaction chromatography/tandem mass spectrometry to demonstrate its analytical possibilities and limitations. It may also be used as a standard for chemical analysis to investigate the ecotoxicity and genotoxicity of cytotoxic antineoplastic drugs, like cytarabine (CYT) and their metabolites, like uracil-1-β-d-arabinofuranoside (AraU).
Biochem/physiol Actions
1-β-D-Arabinofuranosyluracil (ara-U) is capable of inhibiting proliferation of L5178Y mouse lymphoma cells at 17 μM concentration.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Radka Zounkova et al.
Chemosphere, 81(2), 253-260 (2010-07-14)
In spite of growing scientific concern about pharmaceuticals in the environment, there is still a lack of information especially with regard to their metabolites. The present study investigated ecotoxicity and genotoxicity of three widely used cytostatic agents 5-fluorouracil (5-FU), cytarabine
Lubomira Kovalova et al.
Journal of chromatography. A, 1216(7), 1100-1108 (2009-01-13)
A method for solid phase extraction and HPLC-MS/MS of the cytostatics 5-fluorouracil, cytarabine, and gemcitabine and human metabolites uracil 1-beta-d-arabinofuranoside and 2',2'-difluorodeoxyuridine in wastewater was established. Wastewater samples from a Swiss hospital were analyzed for 5-fluorouracil, gemcitabine and 2',2'-difluorodeoxyuridine. The
P Linssen et al.
Journal of chromatography, 223(2), 371-378 (1981-05-08)
A method is described for the determination of 1-beta-D-arabinofuranosylcytosine (Ara-C) and its metabolite 1-beta-D-arabinofuranosyluracil (Ara-U) in human plasma. After deproteinization of the plasma sample, separation is performed by reversed-phase liquid chromatography. For Ara-C concentrations exceeding 0.05 mg/l and for Ara-U
Metabolism of 1-beta-D-arabinofuranosyluracil in mouse L5178Y cells.
W E Müller et al.
Cancer research, 39(3), 1102-1107 (1979-03-01)
Jia Hu et al.
Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban, 31(5), 693-695 (2011-11-01)
In this study, a novel technique for the preparation of (125)I-5-trimethylstannyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) urail (FIAU) was developed, (125)I-FIAU biodistribution profile was detected in Kunming mice and the possibility of using FTAU radio-labeling for reporter gene imaging was explored. 5-trimethylstannyl-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) urail (FTAU) was
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