A1882
6-Azauridine
Synonym(s):
2-β-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione, 6-Azauracil riboside
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About This Item
Empirical Formula (Hill Notation):
C8H11N3O6
CAS Number:
Molecular Weight:
245.19
NACRES:
NA.51
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
200-199-6
MDL number:
Assay:
≥99% (TLC)
Form:
powder
Solubility:
water: 50 mg/mL, clear, colorless
Storage temp.:
2-8°C
InChI key
WYXSYVWAUAUWLD-SHUUEZRQSA-N
InChI
1S/C8H11N3O6/c12-2-3-5(14)6(15)7(17-3)11-8(16)10-4(13)1-9-11/h1,3,5-7,12,14-15H,2H2,(H,10,13,16)/t3-,5-,6-,7-/m1/s1
SMILES string
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2N=CC(=O)NC2=O
assay
≥99% (TLC)
form
powder
mp
157-159 °C (lit.)
solubility
water: 50 mg/mL, clear, colorless
storage temp.
2-8°C
Quality Level
General description
6-Azauridine is a pyrimidine nucleoside analog.
Application
6-Azauridine (AzUrd) blocks the conversion of orotic acid into UMP and it is used in antiviral studies.
6-Azauridine has been used:
- in uridine monophosphate synthase (UMPS) activity assay
- as an antiviral agent to study its inhibition effect and cytotoxic potential on foot and mouth disease virus
- to screen for anticryptosporidial activity
- in the pretreatment of HeLa cells to study its effect on inhibition of cellular uridine synthesis before and during chase with 5-bromouridine 5′-triphosphate (BrUTP)
- as a reference compound for comparing the antiviral activity and cytotoxic activity against viral host cell lines
Biochem/physiol Actions
6-azauridine is a prodrug, upon conversion to 6-aza-UMP, inhibits uridine monophosphate synthase (UMPS). It is a broad spectrum anti-metabolite. It interferes with pyrimidine biosynthesis and affects the cellular nucleic acid levels. It is considered as a antineoplastic metabolite. It inhibits RNA viruses like chikungunya virus, semliki forest virus, and human coronavirus. It significantly inhibits the growth of Cryptosporidium parasites.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Krzysztof Pyrc et al.
Antimicrobial agents and chemotherapy, 50(6), 2000-2008 (2006-05-26)
Human coronavirus NL63 (HCoV-NL63), a recently discovered member of the Coronaviridae family, has spread worldwide and is associated with acute respiratory illness in young children and elderly and immunocompromised persons. Further analysis of HCoV-NL63 pathogenicity seems warranted, in particular because
Donald F Smee et al.
Journal of virological methods, 246, 51-57 (2017-04-01)
Studies were conducted to determine the performance of four dyes in assessing antiviral activities of compounds against three RNA viruses with differing cytopathogenic properties. Dyes included alamarBlue
S Bhasin et al.
The American journal of physiology, 243(3), E234-E239 (1982-09-01)
Ketonemic states complicating late pregnancy are accompanied by lower brain weights in the newborn. Potential mechanisms whereby ketone bodies might inhibit cell proliferation were therefore examined in the fetal rat brain slice by measuring their impact on the de novo
Takashi Kobayashi et al.
Physical chemistry chemical physics : PCCP, 12(19), 5140-5148 (2010-05-07)
Excited state characteristics of 6-azauridine (6AUd), which is known as a medicine against psoriasis and neoplastic, were investigated with laser plash photolysis, time-resolved thermal lensing, and near IR single photon counting method. The triplet-triplet absorption spectrum of 6AUd was observed
Jean Marc Crance et al.
Antiviral research, 58(1), 73-79 (2003-04-30)
Ribavirin, interferon-alpha (IFN-alpha), 6-azauridine and glycyrrhizin were tested in vitro for their antiviral activities against 11 pathogenic flaviviruses belonging to principal antigenic complexes or individual serogroups of medical importance: dengue, Japanese encephalitis, mammalian tick-borne and yellow fever virus (YFV) groups.
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