Molecular Identity
Fludarabine Phosphate
[(2R,3S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
PubChem CID: 30751
Fludarabine phosphate is 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. It has a role as an antiviral agent, an antimetabolite, an antineoplastic agent, an immunosuppressive agent, a prodrug and a DNA synthesis inhibitor. It is an organofluorine compound, a purine arabinonucleoside monophosphate and a nucleoside analogue. It is functionally related to a 2-fluoroadenine.
2D Structure
Properties
C10H13FN5O7P
Molecular Formula
365.21
Molecular Weight
g/mol
365.0537
Exact Mass
Da
-3.1
XLogP
Drug-like (Lipinski: < 5)
186
TPSA
May have limited oral absorption
5
H-Bond Donors
12
H-Bond Acceptors
514
Complexity
SMILES
Canonical SMILES
SMILES: C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)COP(=O)(O)O)O)O)F)NIsomeric SMILES
SMILES: C1=NC2=C(N=C(N=C2N1[C@H]3[C@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)F)NSynonyms(20)
fludarabine phosphate75607-67-9fludaraFludarabine 5'-monophosphateOfortaFludarabine monophosphate2-F-ara-AMPNSC-3128872-Fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-9H-purin-6-amine1X9VK9O1SCNSC 312887CHEBI:635992F-ara-AMPNSC-3280029-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate)
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Fludarabine Phosphate
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