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A1882

6-Azauridin

Name: 6-Azauridin
Brand: SIGMA

Synonym(e):

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

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Über diesen Artikel

Empirische Formel (Hill-System):

C₈H₁₁N₃O₆

CAS-Nummer:

54-25-1

Molekulargewicht:

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

Technischer Dienst

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Unterstützung erhalten

Eigenschaften

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

Beschreibung

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.