CFB

2-CHLORO-9-(2-DEOXY-2-FLUORO-B -D-ARABINOFURANOSYL)-9H-PURIN-6-AMINE

Created: 2005-07-14
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count31
Chiral Atom Count4
Bond Count33
Aromatic Bond Count10
2D diagram of CFB
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Chemical Component Summary

Name2-CHLORO-9-(2-DEOXY-2-FLUORO-B -D-ARABINOFURANOSYL)-9H-PURIN-6-AMINE
SynonymsCLOFARABINE
Systematic Name (OpenEye OEToolkits)(2R,3R,4S,5R)-5-(6-amino-2-chloro-purin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
FormulaC10 H11 Cl F N5 O3
Molecular Weight303.677
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04Clc1nc(c2ncn(c2n1)C3OC(C(O)C3F)CO)N
SMILESCACTVS3.341Nc1nc(Cl)nc2n(cnc12)[CH]3O[CH](CO)[CH](O)[CH]3F
SMILESOpenEye OEToolkits1.5.0c1nc2c(nc(nc2n1C3C(C(C(O3)CO)O)F)Cl)N
Canonical SMILESCACTVS3.341 Nc1nc(Cl)nc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3F
Canonical SMILESOpenEye OEToolkits1.5.0 c1nc2c(nc(nc2n1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)F)Cl)N
InChIInChI1.03 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
InChIKeyInChI1.03 WDDPHFBMKLOVOX-AYQXTPAHSA-N

Drug Info: DrugBank

DrugBank IDDB00631 
NameClofarabine
Groups
  • approved
  • investigational
DescriptionClofarabine is a purine nucleoside antimetabolite that is being studied in the treatment of cancer. It is marketed as Clolar in the U.S. and Canada, or Evoltra in Europe, Australia, and New Zealand. Clofarabine is used in paediatrics to treat a type of leukaemia called relapsed or refractory acute lymphoblastic leukaemia (ALL), only after at least two other types of treatment have failed. It is not known if the drug extends life expectancy. Its potential use in acute myeloid leukaemia (AML) and juvenile myelomonocytic leukaemia (JMML) has been investigated.
Synonyms
  • 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine
  • Clofarabine
  • CAFdA
  • 2-chloro-9-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)adenine
  • Cl-F-Ara-A
Brand Names
  • Evoltra
  • Ivozall
  • Clofarabine
  • Clolar
IndicationFor the treatment of pediatric patients 1 to 21 years old with relapsed or refractory acute lymphocytic (lymphoblastic) leukemia after at least two prior regimens. It is designated as an orphan drug by the FDA for this use.
Categories
  • Adenine Nucleotides
  • Antimetabolites
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Arabinonucleosides
ATC-CodeL01BB06
CAS number123318-82-1

Drug Targets

NameTarget SequencePharmacological ActionActions
DNA-unknownother/unknown
DNA polymerase alpha catalytic subunitMAPVHGDDSLSDSGSFVSSRARREKKSKKGRQEALERLKKAKAGEKYKYE...unknowninhibitor
Ribonucleoside-diphosphate reductase large subunitMHVIKRDGRQERVMFDKITSRIQKLCYGLNMDFVDPAQITMKVIQGLYSG...unknowninhibitor
Deoxycytidine kinaseMATPPKRSCPSFSASSEGTRIKKISIEGNIAAGKSTFVNILKQLCEDWEV...unknownsubstrate
ATP-binding cassette sub-family G member 2MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1750
PubChem 119182
ChEMBL CHEMBL1750
ChEBI CHEBI:681569