fludarabine phosphate (CHEBI:63599)

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CHEBI:63599 - fludarabine phosphate

ChEBI ID	CHEBI:63599
ChEBI Name	fludarabine phosphate
Stars
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.
Secondary ChEBI ID	CHEBI:31616
Last Modified	22 February 2017
Downloads	Molfile

Formula	C10H13FN5O7P
Net Charge	0
Average Mass	365.214
Monoisotopic Mass	365.05366
SMILES	Nc1nc(F)nc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O
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

Wikipedia

Roles Classification

Biological Roles:

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.

Applications:

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.

antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
FAMP	DrugBank
Fludarabine monophosphate	DrugBank
Fludarabine 5'-monophosphate	DrugBank
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate)	ChemIDplus
9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphate	ChemIDplus
2-Fluoroadenine arabinoside 5'-monophosphate	ChemIDplus

Brand Name	Source
Fludara	ChEBI

Manual Xrefs	Databases
D01907	KEGG DRUG
DB01073	DrugBank
Fludarabine	Wikipedia
WO2010133629	Patent
WO2010046917	Patent
1189	DrugCentral

Registry Numbers	Sources
Reaxys:8167686	Reaxys
CAS:75607-67-9	KEGG DRUG
CAS:75607-67-9	ChemIDplus

Citations