Substance
ID:184437
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
PubChem SID
Properties
Pharmacology Properties
Gene Information
human ... ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)
Safety Information
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
RTECS
AU6207000
GHS Signal Word
Warning
European Hazard Symbols
Harmful (Xn)Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
German water hazard class
3
Storage Temperature
2-8°C
Molecule Details
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
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
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References
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