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Fludarabine
Fludarabine
2D structure of fludarabine
Names
Synonyms 2-fluoroadenine arabinoside, 2-F-ara-AMP (phosphate), 2-fluoro-ara-AMP (phoshpate), 9-beta-D-arabinofuranosyl-2-fluoroadenine, CCRIS 3382 (phosphate), F-ara-A, NSC-312887 (phosphate)
Brand names Fludara, Oforta

IUPAC name
IUPAC name
(2R,3S,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Clinical information
Preg. cat.
AU: D
US: D
Legal status
AU: Prescription Only Medicine (S4)
CA: ℞-only
UK: POM
US: ℞-only
Routes Oral, IV

Salts Phosphate
Identifiers
ATC code L01BB05
ChemSpider 571392
DrugBank DB01073
PubChem 657237
MedlinePlus a692003
MeSH ID C024352
External links
DailyMed fludarabine phosphate search
Drugs.com international, monograph
Jmol 3D structure
Licensing data US FDA: link.
MSR monograph
emc fludarabine search
TGA-eBS fludarabine search
Chemical properties
Formula C10H12FN5O4
Mol. mass
Mol. mass for MFs
285.2318 g/mol
SMILES
SMILES
C1=NC2=C(N1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N=C(N=C2N)F
InChI
InChI
1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1
InChIKey
InChIKey
HBUBKKRHXORPQB-FJFJXFQQSA-N


Fludarabine is an antimetabolite adenine analogue with powerful antineoplastic (especially against slow-growing B-cell malignancies like chronic lymphocytic leukaemia and indolent non-Hodgkin lymphoma) and immunosuppressant effects (and has consequently been used to prevent graft-versus-host disease in bone marrow transplant recipients).[1][2]


External linksEdit

Reference listEdit

  1. Brayfield, A, ed. (13 December 2013). "Fludarabine Phosphate". Martindale: The Complete Drug Reference. London, UK: Pharmaceutical Press. Retrieved 16 December 2014. 
  2. Brunton, LL; Chabner, BA; Knollmann, BC, ed. (2010). "Chapter 61. Cytotoxic Agents". Goodman & Gilman's Pharmacological Basis of Therapeutics (12th ed.). New York, USA: McGraw-Hill Professional. ISBN 978-0-07-162442-8. 

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