CHEBI:63599 - fludarabine phosphate

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ChEBI Name fludarabine phosphate
ChEBI ID CHEBI:63599
Definition A purine arabinonucleoside monophosphate having 2-fluoroadenine as the nucleobase. A prodrug, it is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. Once incorporated into DNA, 2-fluoro-ara-ATP functions as a DNA chain terminator. It is used for the treatment of adult patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to, or whose disease has progressed during, treatment with at least one standard alkylating-agent containing regimenas.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Anonymous
Secondary ChEBI IDs CHEBI:31616
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Formula C10H13FN5O7P
Net Charge 0
Average Mass 365.21170
Monoisotopic Mass 365.054
InChI InChI=1S/C10H13FN5O7P/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,14,15)(H2,19,20,21)/t3-,5-,6+,9-/m1/s1
InChIKey GIUYCYHIANZCFB-FJFJXFQQSA-N
SMILES Nc1nc(F)nc2n(cnc12)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O
Roles Classification
Biological Role(s): DNA synthesis inhibitor
Any substance that inhibits the synthesis of DNA.
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.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antiviral agent
A substance that destroys or inhibits replication of viruses.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
immunosuppressive agent
An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing fludarabine phosphate (CHEBI:63599) has functional parent 2-fluoroadenine (CHEBI:72457)
fludarabine phosphate (CHEBI:63599) has role antimetabolite (CHEBI:35221)
fludarabine phosphate (CHEBI:63599) has role antineoplastic agent (CHEBI:35610)
fludarabine phosphate (CHEBI:63599) has role antiviral agent (CHEBI:22587)
fludarabine phosphate (CHEBI:63599) has role DNA synthesis inhibitor (CHEBI:59517)
fludarabine phosphate (CHEBI:63599) has role immunosuppressive agent (CHEBI:35705)
fludarabine phosphate (CHEBI:63599) has role prodrug (CHEBI:50266)
fludarabine phosphate (CHEBI:63599) is a nucleoside analogue (CHEBI:60783)
fludarabine phosphate (CHEBI:63599) is a organofluorine compound (CHEBI:37143)
fludarabine phosphate (CHEBI:63599) is a purine arabinonucleoside monophosphate (CHEBI:37514)
IUPAC Name
2-fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)-9H-purin-6-amine
Synonyms Sources
2-Fluoro-ARA AMP ChemIDplus
2-Fluoroadenine arabinoside 5'-monophosphate ChemIDplus
2F-ara-AMP ChEBI
9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphate ChemIDplus
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate) ChemIDplus
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphate ChemIDplus
FAMP DrugBank
Fludarabine 5'-monophosphate DrugBank
Fludarabine monophosphate DrugBank
Brand Name Source
Fludara ChEBI
Manual Xrefs Databases
1189 DrugCentral
D01907 KEGG DRUG
DB01073 DrugBank
Fludarabine Wikipedia
WO2010046917 Patent
WO2010133629 Patent
View more database links
Registry Numbers Types Sources
75607-67-9 CAS Registry Number ChemIDplus
75607-67-9 CAS Registry Number KEGG DRUG
8167686 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017