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Merck

U5377

Sigma-Aldrich

Uracil 1-β-D-arabinofuranosid

lymphoma antiproliferative

Synonym(e):

Arauridine, Spongouridin, 1-β-D-Arabinofuranosyluracil

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About This Item

Empirische Formel (Hill-System):
C9H12N2O6
CAS-Nummer:
Molekulargewicht:
244.20
Beilstein:
28749
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
41106305
PubChem Substanz-ID:
NACRES:
NA.51

Biologische Quelle

synthetic (organic)

Qualitätsniveau

Assay

≥98% (HPLC)

Form

powder

Löslichkeit

water: 50 mg/mL, clear, colorless

Lagertemp.

−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

InChIKey

DRTQHJPVMGBUCF-CCXZUQQUSA-N

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Allgemeine Beschreibung

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).

Anwendung

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. Wirkung

1-β-D-Arabinofuranosyluracil (ara-U) is capable of inhibiting proliferation of L5178Y mouse lymphoma cells at 17 μM concentration.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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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)
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)

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