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.
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2D Structure
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Physico-chemical Properties
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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
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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
1. Baldwin SA, Yao SY, Hyde RJ, Ng AM, Foppolo S, Barnes K, Ritzel MW, Cass CE, Young JD. (2005)
Functional characterization of novel human and mouse equilibrative nucleoside transporters (hENT3 and mENT3) located in intracellular membranes.
J Biol Chem, 280 (16): 15880-7. [PMID:15701636]
2. Larráyoz IM, Fernández-Nistal A, Garcés A, Gorraitz E, Lostao MP. (2006)
Characterization of the rat Na+/nucleoside cotransporter 2 and transport of nucleoside-derived drugs using electrophysiological methods.
Am J Physiol, Cell Physiol, 291 (6): C1395-404. [PMID:16837649]
3. Tseng WC, Derse D, Cheng YC, Brockman RW, Bennett Jr LL. (1982)
In vitro biological activity of 9-beta-D-arabinofuranosyl-2-fluoroadenine and the biochemical actions of its triphosphate on DNA polymerases and ribonucleotide reductase from HeLa cells.
Mol Pharmacol, 21 (2): 474-7. [PMID:7048062]