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6-Azauridine

SIGMA/A1882

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

CAS Number: 54-25-1
Empirical Formula (Hill Notation): C8H11N3O6
Molecular Weight: 245.19
EC Number: 200-199-6
MDL Number: MFCD00006472
Linear Formula: C8H11N3O6
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-A1882-1G 1 g
 $86.10
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45-A1882-5G 5 g
 $481.00
1/EA		 Add To Favorites
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A1882-1G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A1882-5G

 

assay ≥99% (TLC)
form powder
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
mp 157-159 °C (lit.)
Quality Level 200 
SMILES string OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2N=CC(=O)NC2=O
solubility water: 50 mg/mL, clear, colorless
storage temp. 2-8°C
Application: 6-Azauridine (AzUrd) blocks the conversion of orotic acid into UMP and it is used in antiviral studies.
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
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.
General description: 6-Azauridine is a pyrimidine nucleoside analog.
Packaging: 1, 5 g in poly bottle
Purity ≥99% (TLC)
mp 157-159 °C (lit.)
Storage Temp. 2-8°C
UNSPSC 41106305

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