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46455 Sigma-Aldrich

2-Fluoroadenine-9-β-D-arabinofuranoside

≥98.0% (HPLC)

Synonym: 9-β-D-Arabinofuranosyl-2-fluoroadenine, F-ara-A, Fludarabine des-phosphate

  • CAS Number 21679-14-1

  • Empirical Formula (Hill Notation) C10H12FN5O4

  • Molecular Weight 285.23

  •  Beilstein Registry Number 1225932

  •  EC Number 244-525-5

  •  MDL number MFCD00132942

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Properties

InChI Key   HBUBKKRHXORPQB-FJFJXFQQSA-N
assay   ≥98.0% (HPLC)
solubility   DMF: 20 mg/mL, clear, faintly yellow
storage temp.   2-8°C

Description

Other Notes

Inhibitor of nucleic acid synthesis. Action on RNA metabolism

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
AU6207000

Documents

Certificate of Analysis

Protocols & Articles
Peer-Reviewed Papers
15

References

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Description

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F2773 2-Fluoroadenine-9-β-D-arabinofuranoside, DNA synthesis and methylation inhibitor

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