A1882

6-Azauridine

• Sinonimo/i: 2-β-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione, 6-Azauracil riboside
• Formula empirica (notazione di Hill): C₈H₁₁N₃O₆
• Numero CAS: 54-25-1
• Peso molecolare: 245.19
• Numero CE: 200-199-6
• Numero MDL: MFCD00006472
• Codice UNSPSC: 41106305
• ID PubChem: 24890597
• NACRES: NA.51

Proprietà

• Saggio: ≥99% (TLC)
• Stato: powder
• Punto di fusione: 157-159 °C (lit.)
• Solubilità: water: 50 mg/mL, clear, colorless
• Temperatura di conservazione: 2-8°C
• Stringa SMILE: 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; WYXSYVWAUAUWLD-SHUUEZRQSA-N

Descrizione

Descrizione generale

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

Applicazioni

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]

Azioni biochim/fisiol

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]

Informazioni sulla sicurezza

• Pittogrammi: GHS08,GHS07
• Avvertenze: Warning
• Indicazioni di pericolo: H302 + H312 + H332,H351
• Consigli di prudenza: P202 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
• Classi di pericolo: Acute Tox. 4 Oral - Carc. 2
• Codice della classe di stoccaggio: 11 - Combustible Solids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): Not applicable
• Punto d’infiammabilità (°C): Not applicable
• Dispositivi di protezione individuale: dust mask type N95 (US), Eyeshields, Gloves