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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:
3083-77-0
Molecular Weight:
244.20
NACRES:
NA.51
PubChem Substance ID:
24900655
UNSPSC Code:
41106305
EC Number:
221-386-9
MDL number:
MFCD00065998
Beilstein/REAXYS Number:
28749
Assay:
≥98% (HPLC)
Biological source:
synthetic (organic)
Form:
powder
Solubility:
water: 50 mg/mL, clear, colorless
Storage temp.:
−20°C

Key Documents

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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

200

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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.

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).

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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Certificates of Analysis (COA)

Lot/Batch Number
0000448516
0000448516
0000467753
0000467753
0000316668

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Metabolism of 1-beta-D-arabinofuranosyluracil in mouse L5178Y cells.
W E Müller et al.
Cancer research, 39(3), 1102-1107 (1979-03-01)
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
Melissa N McCracken et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(5), 1857-1862 (2013-01-16)
Positron emission tomography (PET) reporter genes allow noninvasive whole-body imaging of transplanted cells by detection with radiolabeled probes. We used a human deoxycytidine kinase containing three amino acid substitutions within the active site (hdCK3mut) as a reporter gene in combination
Kai Chen et al.
Nuclear medicine and biology, 39(7), 1019-1025 (2012-04-17)
[(18)F]-FMAU is a PET tracer being evaluated for imaging cell proliferation. Current multi-step procedures of [(18)F]-FMAU synthesis are time-consuming, resulting in low radiochemical yield and inconvenient applications for the clinic. We have previously reported the use of Friedel-Crafts catalysts for
Richard Wiegand et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 891-892, 64-70 (2012-03-14)
A liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) assay was developed and validated for simultaneous determination of 1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl) uracil (FAU) and its active metabolite 1-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl) 5-methyluracil (FMAU) in human plasma. FAU and FMAU were extracted from plasma samples using
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