Skip to Content
MilliporeSigma
All Photos(2)

Documents

U5377

Sigma-Aldrich

Uracil 1-β-D-arabinofuranoside

lymphoma antiproliferative

Synonym(s):

Arauridine, Spongouridin, 1-β-D-Arabinofuranosyluracil

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C9H12N2O6
CAS Number:
3083-77-0
Molecular Weight:
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)

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

Uracil ≥99.0%

Sigma-Aldrich

U0750

Uracil

Methyl sulfoxide ≥99%, FG

Sigma-Aldrich

W387520

Methyl sulfoxide

Metabolism of 1-beta-D-arabinofuranosyluracil in mouse L5178Y cells.
W E Müller et al.
Cancer research, 39(3), 1102-1107 (1979-03-01)
Zibo Li et al.
Current radiopharmaceuticals, 4(1), 24-30 (2011-12-24)
[18F]FMAU is an established PET probe used to monitor cellular proliferation. For clinical applications, a fully automated cGMP-compliant radiosynthesis would be preferred. However, the current synthesis of [18F]FMAU requires HBr activation of the sugar prior to the coupling with silylated
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
Yoon-Ok Jang et al.
BMC gastroenterology, 12, 4-4 (2012-01-11)
Clevudine is a nucleoside analog reverse transcriptase inhibitor that exhibits potent antiviral activity against hepatitis B virus (HBV) without serious side effects. However, mitochondrial myopathy has been observed in patients with chronic HBV infection taking clevudine. Moreover, the development of
[New drugs of treatment of patients with chronic hepatitis B].
Fumitaka Suzuki
Nihon rinsho. Japanese journal of clinical medicine, 69 Suppl 4, 512-514 (2011-11-22)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service