nelarabine   Click here for help

GtoPdb Ligand ID: 7090

Synonyms: 506U78 | Arranon® | Atriance®
Approved drug
nelarabine is an approved drug (FDA (2005), EMA (2007))
Compound class: Synthetic organic
Comment: This compound is a prodrug. The active metabolite is its 5'-triphosphate, ara-GTP.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 5
Rotatable bonds 3
Topological polar surface area 149.5
Molecular weight 297.11
XLogP 0.41
No. Lipinski's rules broken 0
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Canonical SMILES OCC1OC(C(C1O)O)n1cnc2c1[nH]c(=N)nc2OC
Isomeric SMILES OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1cnc2c1[nH]c(=N)nc2OC
InChI InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1
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Summary of Clinical Use Click here for help
Used to treat T-cell acute lymphoblastic leukemia (T-ALL) and T-cell lymphoblastic lymphoma (T-LBL), especially in patients with relapsed disease or who are unresponsive to other chemotherapies.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The incorporation of the active compound metabolised from nelarabine, inhibits DNA synthesis and causes cell death.
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