A1882

6-Azauridine

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

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 (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.[1] It inhibits RNA viruses like chikungunya virus, semliki forest virus, and human coronavirus. It significantly inhibits the growth of Cryptosporidium parasites.

Safety Information

• pictograms: GHS08,GHS07
• signalword: Warning
• hcodes: H302 + H312 + H332,H351
• pcodes: P202 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
• 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