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A1882

Sigma-Aldrich

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:
54-25-1
Molecular Weight:
245.19
EC Number:
200-199-6
MDL number:
MFCD00006472
UNSPSC Code:
41106305
PubChem Substance ID:
24890597
NACRES:
NA.51

Assay

≥99% (TLC)

form

powder

mp

157-159 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

storage temp.

2-8°C

SMILES string

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2N=CC(=O)NC2=O

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

InChI key

WYXSYVWAUAUWLD-SHUUEZRQSA-N

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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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

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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
Enhanced inhibition of foot-and-mouth disease virus by combinations of porcine interferon-alpha and antiviral agents
Kim SM, et al.
Antiviral research, 96(2), 213-220 (2012)
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
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