Key Documents

View All Documentation

A1882

6-Azauridine

Name: 6-Azauridine
Brand: SIGMA

Synonym(s):

2-β-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione, 6-Azauracil riboside

Select a Size

Change View

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

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

assay

≥99% (TLC)

Quality Segment

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

Description

General description

6-Azauridine is a pyrimidine nucleoside analog.

Application

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

6-Azauridine (AzUrd) blocks the conversion of orotic acid into UMP and it is used in antiviral studies.

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

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

0000559904

0000358751

0000307720

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Global Trade Item Number

SKU	GTIN
A1882-1G	04061826687710
A1882-5G	04061833045312