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.

nelarabine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key IXOXBSCIXZEQEQ-UHTZMRCNSA-N
No information available.
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.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)