2-Fluoroadenine-9-β-D-arabinofuranoside

• Catalog No.: 46455
• CAS Number: 21679-14-1
• M. F.: C10H12FN5O4
• M. W.: 285.2317832
• Purity: ≥98.0% (HPLC)

SYNONYMS

• IUPAC name: (2R,3S,4S,5R)-2-(6-amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: fludarabine
• Synonyms: Fludarabine des-phosphate; F-ara-A; 9-β-D-Arabinofuranosyl-2-fluoroadenine

DATABASE IDS

• MDL Number: MFCD00132942
• Beilstein Number: 1225932
• CAS Number: 21679-14-1
• EC Number: 244-525-5

PROPERTIES

• Empirical Formula (Hill Notation): C10H12FN5O4
• Purity: ≥98.0% (HPLC)
• Solubility: DMF: soluble20 mg/mL, clear, faintly yellow
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• European Hazard Symbols: Harmful (Xn)
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Risk Statements: 22
• RTECS: AU6207000
• Storage Temperature: 2-8°C
• German water hazard class: 3

DETAILS

Description (English)

Other Notes
Inhibitor of nucleic acid synthesis. Action on RNA metabolism2
Warning
The name fludarabine refers to 9-β-D-arabinofuranosyl-2-fluoroadenine 5′-phosphate, but is sometimes erroneously used for this compound, which lacks the phosphate.
Biochem/physiol Actions
Fludarabine (the 5′-phosphate) is a prodrug that is converted to F-ara-A, which enters cells and accumulates primarily as the 5′-triphosphate. F-ara-A interferes with DNA synthesis and repair and induces apoptosis of cancer cells. F-ara-A also strongly inhibits DNA methylation, particularly methylation of cytosine in CpG dinucleotide sequences.1

Description (简体中文)

Other Notes
Inhibitor of nucleic acid synthesis. Action on RNA metabolism2
Warning
The name fludarabine refers to 9-β-D-arabinofuranosyl-2-fluoroadenine 5′-phosphate, but is sometimes erroneously used for this compound, which lacks the phosphate.
Biochem/physiol Actions
Fludarabine (the 5′-phosphate) is a prodrug that is converted to F-ara-A, which enters cells and accumulates primarily as the 5′-triphosphate. F-ara-A interferes with DNA synthesis and repair and induces apoptosis of cancer cells. F-ara-A also strongly inhibits DNA methylation, particularly methylation of cytosine in CpG dinucleotide sequences.1