2-Fluoroadenine-9-β-D-arabinofuranoside

• Catalog No.: F2773
• CAS Number: 21679-14-1
• M. F.: C10H12FN5O4
• M. W.: 285.2317832

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
• PubChem SID: 24894830
• EC Number: 244-525-5

PROPERTIES

• Gene Information: human ... ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)
• 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)

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