Substance
ID:353869
Names and Identifiers
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
F-ara-AFludarabine des-phosphate2-Fluoroadenine-9-β-D-arabinofuranoside9-β-D-Arabinofuranosyl-2-fluoroadenine
Registration numbers
EC Number
CAS Number
MDL Number
Beilstein Number
Properties
Safety Information
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
European Hazard Symbols
Harmful (Xn)RTECS
AU6207000
MSDS Link
Storage Temperature
2-8°C
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
GHS Hazard statements
H302
Risk Statements
22
GHS Signal Word
Warning
German water hazard class
3
Physical Property
Solubility
DMF: soluble20 mg/mL, clear, faintly yellow
Product Information
Purity
≥98.0% (HPLC)
Empirical Formula (Hill Notation)
C10H12FN5O4
Molecule Details
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
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
Molecular Spectra
No Data Available
Click here to submit data
References
No Data Available
Click here to submit data