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Clofarabine
Clofarabine
2D structure of clofarabine
Clofarabine
3D structure of clofarabine
Names
Synonyms Cl-F-Ara-A
Brand names Clolar, Evoltra

IUPAC name
IUPAC name
(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
Clinical information
Preg. cat.
AU: D
US: D
Legal status
AU: Prescription Only Medicine (S4)
CA: ℞-only
UK: POM
US: ℞-only
Routes Intravenous


Identifiers
ATC code L01BB06
ChemSpider 106472
DrugBank DB00631
PubChem 119182
MedlinePlus a607012
MeSH ID C068329
PDB IDs
PDBs
2A7Q (RCSB, PDBe; X-ray)
External links
DailyMed clofarabine search
Drugs.com international, monograph
Jmol 3D structure
Licensing data EU EMA: link.
US FDA: link.
MSR monograph
emc clofarabine search
TGA-eBS clofarabine search
Chemical properties
Formula C10H11ClFN5O3
Mol. mass
Mol. mass for MFs
303.677 g/mol
SMILES
SMILES
c1nc2c(nc(nc2n1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)F)Cl)N
InChI
InChI
InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4+,6-,9-/m1/s1
InChIKey
InChIKey
WDDPHFBMKLOVOX-AYQXTPAHSA-N


Clofarabine is a fairly recently approved (so called "second-generation") purine antimetabolite that is used in the management of acute lymphoblastic leukaemia[note 1] that is resistant to at least two prior therapies although it may also be used in the management of acute myeloid leukaemia (which is an unapproved use).[1][2][3] Its principle side effects include: myelosuppression, cytokine release effects (including hypotension, oedema, weight gain, tachycardia, capillary leak syndrome, organ dysfunction and systemic inflammatory response syndrome), digestive complaints (e.g., nausea, vomiting, diarrhoea, abdominal pain, oral mucositis and loss of appetite), electrolyte abnormalities (e.g., hypokalaemia, hypophosphataemia), skin reactions (e.g., rashes and hand-foot syndrome), etc.[1][2] It acts via four major mechanisms (after intracellular phosphorylation):[1][2][3]



External linksEdit

NotesEdit

  1. First FDA approved for paediatric ALL in December 2004; first TGA approved in September 2009.

Reference listEdit

  1. 1.0 1.1 1.2 Brunton, LL; Chabner, BA; Knollmann, BC, ed. (2010). Goodman & Gilman's Pharmacological Basis of Therapeutics (12th ed.). New York, USA: McGraw-Hill Professional. ISBN 978-0-07-162442-8. 
  2. 2.0 2.1 2.2 Kantarjian, HM; Jeha, S; Gandhi, V; Wess, M; Faderl, S (October 2007). "Clofarabine: past, present, and future.". Leukemia & Lymphoma 48 (10): 1922–30. PMID 17852710. doi:10.1080/10428190701545644. 
  3. 3.0 3.1 "EVOLTRA®" (PDF). TGA eBusiness Services. Melbourne, Australia: Hospira Pty Ltd. 21 June 2012. Retrieved 4 December 2014. 


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