CHEBI:681569 - clofarabine

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ChEBI Name clofarabine
ChEBI ID CHEBI:681569
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information eMolecules:29256989, eMolecules:30512527, Selleckchem:Clofarabine, ZINC000003798247
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Clofarabine is a purine nucleoside antimetabolite marketed in the United States 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. 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 for managing other cancers.
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Formula C10H11ClFN5O3
Net Charge 0
Average Mass 303.67700
Monoisotopic Mass 303.05345
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 WDDPHFBMKLOVOX-AYQXTPAHSA-N
SMILES Nc1nc(Cl)nc2n(cnc12)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F
Roles Classification
Biological Role(s): 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(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 Sources
clofarabina ChEBI
clofarabine KEGG DRUG
clofarabinum ChEBI
Synonyms Sources
(2R,3R,4S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol DrugBank
2-chloro-9-(2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)adenine ChEBI
2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine ChemIDplus
CAFdA ChEBI
Cl-F-Ara-A ChEBI
clofarabine ChEMBL
Manual Xrefs Databases
Clofarabine Wikipedia
D03546 KEGG DRUG
DB00631 DrugBank
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Registry Numbers Types Sources
123318-82-1 CAS Registry Number ChemIDplus
123318-82-1 CAS Registry Number KEGG DRUG
4882539 Beilstein Registry Number Beilstein
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Last Modified
07 June 2010