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U5377

Sigma-Aldrich

Uracil 1-β-D-arabinofuranoside

lymphoma antiproliferative

Sinónimos:

Arauridine, Spongouridin, 1-β-D-Arabinofuranosyluracil

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About This Item

Fórmula empírica (notación de Hill):
C9H12N2O6
Número de CAS:
3083-77-0
Peso molecular:
244.20
Beilstein/REAXYS Number:
28749
EC Number:
221-386-9
MDL number:
MFCD00065998
UNSPSC Code:
41106305
PubChem Substance ID:
24900655
NACRES:
NA.51

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@H]([C@@H](O)[C@@H]1O)N2C=CC(=O)NC2=O

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

InChI key

DRTQHJPVMGBUCF-CCXZUQQUSA-N

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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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
Metabolism of 1-beta-D-arabinofuranosyluracil in mouse L5178Y cells.
W E Müller et al.
Cancer research, 39(3), 1102-1107 (1979-03-01)
Hwi Young Kim et al.
PloS one, 7(11), e50377-e50377 (2012-12-05)
Modeling of short-term viral dynamics of hepatitis B with traditional biphasic model might be insufficient to explain long-term viral dynamics. The aim was to develop a novel method of mathematical modeling to shed light on the dissociation between early and
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
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
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