fludarabine   Click here for help

GtoPdb Ligand ID: 4802

Synonyms: 2-F-Ara-A | CCRIS 3382 | F-Ara-A | Fludara®
Approved drug
fludarabine is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Fludarabine is a chemotherapy drug used to treat blood cancers.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 2
Topological polar surface area 139.54
Molecular weight 285.09
XLogP -1.17
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OCC1OC(C(C1O)O)n1cnc2c1nc(F)nc2N
Isomeric SMILES OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1cnc2c1nc(F)nc2N
InChI InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of B-cell chronic lymphocytic leukemia in adult patients.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The active metabolite is believed to be 2-fluoro-ara-ATP, which appears to act, at least in part, by inhibiting DNA polymerase α, ribonucleotide reductase and DNA primase. This combination of actions inhibits DNA synthesis and leads to cell death.