clofarabine   Click here for help

GtoPdb Ligand ID: 6802

Synonyms: CAFdA | Cl-F-araA | Clolar® | Evoltra®
Approved drug PDB Ligand
clofarabine is an approved drug (FDA (2004), EMA (2009))
Compound class: Synthetic organic
Comment: A DNA polymerase (α/δ/ε) inhibitor, DNA and ribonucleoside-diphosphate reductase (RR1) inhibitor.
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 7
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 119.31
Molecular weight 303.05
XLogP 0.04
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OCC1OC(C(C1O)F)n1cnc2c1nc(Cl)nc2N
Isomeric SMILES OC[C@H]1O[C@H]([C@H]([C@@H]1O)F)n1cnc2c1nc(Cl)nc2N
InChI InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4+,6-,9-/m1/s1
No information available.
Summary of Clinical Use Click here for help
Used to treat paediatric patients with relapsed or refractory acute lymphoblastic leukemia (ALL) which has failed to respond to at least two other types of treatment.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
A purine nucleoside antimetabolite. Clofarabine is metabolized by 2'-deoxycytidine kinase (DCK) and is finally phosphorylated to its corresponding triphosphate form in cells. The phosphorylated drug exerts its cttotoxic effects by inhibiting ribonucleotide reductase and DNA polymerases, thereby causing deoxyribonucleotide depletion and inhibition of DNA synthesis.The drug is also used as a substrate by DNA polymerases and is incorporated into DNA causing premature chain termination.
External links Click here for help