Clofarabine

Title: Clofarabine
CAS Registry Number: 123318-82-1
CAS Name: 2-Chloro-9-(2-deoxy-2-fluoro-b-D-arabinofuranosyl)-9H-purin-6-amine
Additional Names: 2-chloro-9-(2-deoxy-2-fluoro-b-D-arabinofuranosyl)adenine; 2-chloro-2¢-arabinofluoro-2¢-deoxyadenosine; Cl-F-ara-A
Trademarks: Clolar (Genzyme)
Molecular Formula: C10H11ClFN5O3
Molecular Weight: 303.68
Percent Composition: C 39.55%, H 3.65%, Cl 11.67%, F 6.26%, N 23.06%, O 15.81%
Literature References: Second generation purine nucleoside analog; antimetabolite that inhibits DNA synthesis and resists deamination by adenosine deaminase. Prepn: K. A. Watanabe et al., EP 219829; eidem, US 4918179 (1987, 1990 both to Sloan-Kettering Inst. Cancer Res.); J. A. Montgomery et al., J. Med. Chem. 35, 397 (1992). Improved synthesis: W. E. Bauta et al., Org. Process Res. Dev. 8, 889 (2004). Antineoplastic activity: W. R. Waud et al., Nucleosides Nucleotides Nucleic Acids 19, 447 (2000). Clinical pharmacology: H. M. Kantarjian et al,. J. Clin. Oncol. 21, 1167 (2003). Clinical pharmacokinetics: V. Gandhi et al., Clin. Cancer Res. 9, 6335 (2003). Clinical evaluation in acute leukemia: H. Kantarjian et al., Blood 102, 2379 (2003); in pediatric patients: S. Jeha et al., ibid. 103, 784 (2004). Review of development: A. Sternberg, Curr. Opin. Invest. Drugs 4, 1479-1487 (2003); of mechanism of action and clinical experience: S. Faderl et al., Cancer 103, 1985-1995 (2005).
Properties: Crystals from water, mp 225-227° (Montgomery). Also reported as crystals from methanol, mp 237° (Bauta). uv max (water): 212, 263 nm (e 22500, 15989).
Melting point: mp 225-227° (Montgomery); crystals from methanol, mp 237° (Bauta)
Absorption maximum: uv max (water): 212, 263 nm (e 22500, 15989)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Purine Analogs.
Clofenamide Clofencet Clofentezine Clofibrate Clofibric Acid

Clofarabine
Clofarabine2.png
Systematic (IUPAC) name
5-(6-amino-2-chloro-purin-9-yl) -4-fluoro-2- (hydroxymethyl)oxolan-3-ol
Clinical data
Trade names Clolar, Evoltra
AHFS/Drugs.com monograph
MedlinePlus a607012
Legal status Prescription only
Routes Intravenous
Identifiers
CAS number 123318-82-1 YesY
ATC code L01BB06
PubChem CID 119182
DrugBank DB00631
ChemSpider 106472 YesY
UNII 762RDY0Y2H YesY
KEGG D03546 YesY
ChEBI CHEBI:681569 YesY
ChEMBL CHEMBL1750 YesY
Chemical data
Formula C10H11ClFN5O3 
Mol. mass 303.677 g/mol
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Clofarabine is a purine nucleoside antimetabolite marketed in the U.S. and Canada as Clolar. In Europe and Australia/New Zealand the product is marketed under the name Evoltra. It is FDA-approved for treating relapsed or refractory acute lymphoblastic leukaemia (ALL) in children after at least two other types of treatment have failed. It is not known if it extends life expectancy. Some investigations of effectiveness in cases of acute myeloid leukaemia (AML) and juvenile myelomonocytic leukaemia (JMML) have been carried out. Ongoing trials are assessing its efficacy, if any, for managing other cancers.