A1882

6-Azauridin

• Synonym(e): 2-β-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione, 6-Azauracil riboside
• Empirische Formel (Hill-System): C₈H₁₁N₃O₆
• CAS-Nummer: 54-25-1
• Molekulargewicht: 245.19
• EG-Nummer: 200-199-6
• MDL-Nummer: MFCD00006472
• UNSPSC-Code: 41106305
• PubChem Substanz-ID: 24890597
• NACRES: NA.51

Eigenschaften

• Assay: ≥99% (TLC)
• Qualitätsniveau: 200
• Form: powder
• mp (Schmelzpunkt): 157-159 °C (lit.)
• Löslichkeit: water: 50 mg/mL, clear, colorless
• Lagertemp.: 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
• InChIKey: WYXSYVWAUAUWLD-SHUUEZRQSA-N

Beschreibung

Allgemeine Beschreibung

6-Azauridine is a pyrimidine nucleoside analog.

Anwendung

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. Wirkung

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.

Sicherheitshinweise

• Piktogramme: GHS08,GHS07
• Signalwort: Warning
• H-Sätze: H302 + H312 + H332,H351
• P-Sätze: P202 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
• Gefahreneinstufungen: Acute Tox. 4 Oral - Carc. 2
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves