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Merck
CN

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:
54-25-1
Molecular Weight:
245.19
NACRES:
NA.51
PubChem Substance ID:
24890597
UNSPSC Code:
41106305
EC Number:
200-199-6
MDL number:
MFCD00006472
Assay:
≥99% (TLC)
Form:
powder
Solubility:
water: 50 mg/mL, clear, colorless
Storage temp.:
2-8°C

Key Documents

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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

200

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

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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Certificates of Analysis (COA)

Lot/Batch Number
0000358751
0000307720
0000307720
0000358751
SLCR3524

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S Briolant et al.
Antiviral research, 61(2), 111-117 (2003-12-13)
Chikungunya virus (CHIKV) and Semliki Forest virus (SFV) were used in our laboratory to screen active antiviral compounds against viruses of the Alphavirus genus. Antiviral activity was estimated by the reduction of the cytopathic effect of each alphavirus on infected
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
Visualisation of ribosomal RNA (rRNA) synthesis in eukaryotic cells in culture
Haukenes G and Kalland KH
Methods in Cell Science : An Official Journal of the Society for In Vitro Biology, 19(4), 295-302 (1998)
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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