A1882

6-アザウリジン

• 別名: 2-β-D-リボフラノシル-1,2,4-トリアジン-3,5(2H,4H)-ジオン, 6-アザウラシルリボシド
• 実験式（ヒル表記法）: C₈H₁₁N₃O₆
• CAS番号: 54-25-1
• 分子量: 245.19
• EC Number: 200-199-6
• MDL番号: MFCD00006472
• UNSPSCコード: 41106305
• PubChem Substance ID: 24890597
• NACRES: NA.51

特性

• アッセイ: ≥99% (TLC)
• フォーム: powder
• mp: 157-159 °C (lit.)
• 溶解性: water: 50 mg/mL, clear, colorless
• 保管温度: 2-8°C
• SMILES記法: 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

詳細

詳細

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

アプリケーション

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]

生物化学的／生理学的作用

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]

安全性情報

• ピクトグラム: GHS08,GHS07
• シグナルワード: Warning
• 危険有害性情報: H302 + H312 + H332,H351
• 注意書き: P202 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312 - P308 + P313
• 危険有害性の分類: Acute Tox. 4 Oral - Carc. 2
• 保管分類コード: 11 - Combustible Solids
• WGK: WGK 3
• 引火点(°F): Not applicable
• 引火点(℃): Not applicable
• 個人用保護具 (PPE): dust mask type N95 (US), Eyeshields, Gloves