pixantrone   Click here for help

GtoPdb Ligand ID: 7544

Synonyms: BBR-2778 | Pixuvri®
Approved drug
pixantrone is an approved drug (EMA and UK (2012))
Compound class: Synthetic organic
Comment: Pixantrone is an antineoplastic drug that also shows immunosuppressant activity [4-5]. It is administered clinically as pixantrone dimaleate (PubChem CID: 9937618).
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 4
Rotatable bonds 6
Topological polar surface area 123.13
Molecular weight 325.15
XLogP -0.4
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 NCCNc1ccc(c2c1C(=O)c1cnccc1C2=O)NCCN
Isomeric SMILES NCCNc1ccc(c2c1C(=O)c1cnccc1C2=O)NCCN
InChI InChI=1S/C17H19N5O2/c18-4-7-21-12-1-2-13(22-8-5-19)15-14(12)16(23)10-3-6-20-9-11(10)17(15)24/h1-3,6,9,21-22H,4-5,7-8,18-19H2
InChI Key PEZPMAYDXJQYRV-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Pixantronehas been studied as an antineoplastic for different kinds of cancer, with Phase 3 trials for solid tumours such as HER2-negative metastatic breast cancer and hematological malignancies such as non-Hodgkin lymphomas completed (see ClinicalTrials.gov for a full list of registered trials assessing this compound). In 2009 the EMA approved use of this drug under the conditions of its 'named patient' programme, for qualifying patients with multiply relapsed or refractory aggressive non-Hodgkin B-cell lymphomas. This was promoted to full approval in 2012, and indicated for previously unresponsive non-Hodgkin's B-cell lymphoma.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Pixantrone acts as a topoisomerase II poison and intercalating agent [1-3].
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
European Medicines Agency (EMA)