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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)

Quality Level

200

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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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)
Joo-Hyung Choi et al.
Journal of veterinary science, 19(6), 788-797 (2018-10-12)
In many countries, vaccines are used for the prevention of foot-and-mouth disease (FMD). However, because there is no protection against FMD immediately after vaccination, research and development on antiviral agents is being conducted to induce protection until immunological competence is
Jason Paragas et al.
Antiviral research, 62(1), 21-25 (2004-03-18)
Crimean-Congo hemorrhagic fever virus (CCHFV) is a tick-borne virus that is emerging as a significant human pathogen in many regions of the world, including Africa, Asia, and Europe. In this report, we describe a simple screening method for discovering new
Drug repurposing screen reveals FDA-approved inhibitors of human HMG-CoA reductase and isoprenoid synthesis that block Cryptosporidium parvum growth
Bessoff K, et al.
Antimicrobial agents and chemotherapy, 57(4), 1804-1814 (2013)
Physiologic medium rewires cellular metabolism and reveals uric acid as an endogenous inhibitor of UMP synthase
Cantor JR, et al.
Cell, 169(2), 258-272 (2017)
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