A1882

6-Azauridine

• Sinónimos: 2-β-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione, 6-Azauracil riboside
• Fórmula empírica (notación de Hill): C₈H₁₁N₃O₆
• Número de CAS: 54-25-1
• Peso molecular: 245.19
• Número CE: 200-199-6
• Número MDL: MFCD00006472
• Código UNSPSC: 41106305
• ID de la sustancia en PubChem: 24890597
• NACRES: NA.51

Propiedades

• Ensayo: ≥99% (TLC)
• Formulario: powder
• mp: 157-159 °C (lit.)
• solubilidad: water: 50 mg/mL, clear, colorless
• temp. de almacenamiento: 2-8°C
• cadena SMILES: 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
• Clave InChI: WYXSYVWAUAUWLD-SHUUEZRQSA-N

Descripción

Descripción general

6-Azauridine is a pyrimidine nucleoside analog.[1]

Aplicación

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[2]
• as an antiviral agent to study its inhibition effect and cytotoxic potential on foot and mouth disease virus[3]
• to screen for anticryptosporidial activity[1]
• 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)[4]
• as a reference compound for comparing the antiviral activity and cytotoxic activity against viral host cell lines[5]

Acciones bioquímicas o fisiológicas

6-azauridine is a prodrug, upon conversion to 6-aza-UMP, inhibits uridine monophosphate synthase (UMPS).[2] It is a broad spectrum anti-metabolite.[3] It interferes with pyrimidine biosynthesis and affects the cellular nucleic acid levels. It is considered as a antineoplastic metabolite.[6] It inhibits RNA viruses like chikungunya virus, semliki forest virus, and human coronavirus.[3] It significantly inhibits the growth of Cryptosporidium parasites.[1]

Información de seguridad

• Pictogramas: GHS08,GHS07
• Palabra de señalización: Warning
• Frases de peligro: H302 + H312 + H332,H351
• Consejos de prudencia: P202 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
• Clasificaciones de peligro: Acute Tox. 4 Oral - Carc. 2
• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable
• Equipo de protección personal: dust mask type N95 (US), Eyeshields, Gloves