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CHEBI:681569 - clofarabine

ChEBI IDCHEBI:681569
ChEBI Nameclofarabine
Stars
DefinitionA purine nucleoside analogue consisting of a 6-amino-2-chloropurin-9-yl group attached to the 1β position of 2'-deoxy-2'-fluoro-D-arabinofuranose. It is metabolized intracellularly to the active 5'-triphosphate metabolite, which inhibits DNA synthesisis and so stops the growth of cancer cells. Clofarabine is used as an antimetabolite antineoplastic agent in the treatment of relapsed or refractory acute lymphoblastic leukaemia.
Last Modified7 June 2010
DownloadsMolfile
FormulaC10H11ClFN5O3
Net Charge0
Average Mass303.681
Monoisotopic Mass303.05345
SMILESNc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F
InChIInChI=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
InChIKeyWDDPHFBMKLOVOX-AYQXTPAHSA-N
Wikipedia
Roles Classification
Biological Role:
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
clofarabine (CHEBI:681569) has role antimetabolite (CHEBI:35221)
clofarabine (CHEBI:681569) has role antineoplastic agent (CHEBI:35610)
clofarabine (CHEBI:681569) is a adenosines (CHEBI:22260)
clofarabine (CHEBI:681569) is a organofluorine compound (CHEBI:37143)
IUPAC Name 
2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine
INNs  Source
clofarabineKEGG DRUG
clofarabinaChEBI
clofarabinumChEBI
Synonyms  Source
clofarabineChEMBL
2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenineChemIDplus
CAFdAChEBI
2-chloro-9-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)adenineChEBI
(2R,3R,4S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-olDrugBank
Cl-F-Ara-AChEBI
Manual XrefsDatabases
D03546KEGG DRUG
DB00631DrugBank
ClofarabineWikipedia
Registry NumbersSources
Beilstein:4882539Beilstein
CAS:123318-82-1KEGG DRUG
CAS:123318-82-1ChemIDplus
Citations