fludarabine phosphate (CHEBI:63599)

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

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:

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.

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.

antiviral agent A substance that destroys or inhibits replication of viruses.

Applications:

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

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.

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
2F-ara-AMP	ChEBI
2-Fluoroadenine arabinoside 5'-monophosphate	ChemIDplus
2-Fluoro-ARA AMP	ChemIDplus
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

Brand Name	Source
Fludara	ChEBI

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

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

Citations