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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

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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

eCl@ss:

32119108

Assay:

≥99% (TLC)

Form:

powder

Solubility:

water: 50 mg/mL, clear, colorless

Storage temp.:

2-8°C

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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.

Signal Word

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 (personal protective equipment)

dust mask type N95 (US), Eyeshields, Gloves

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