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
References
1. Adnan N, Buck DP, Evison BJ, Cutts SM, Phillips DR, Collins JG. (2010)
DNA binding by pixantrone.
Org Biomol Chem, 8 (23): 5359-66. [PMID:20865205]
2. De Isabella P, Palumbo M, Sissi C, Capranico G, Carenini N, Menta E, Oliva A, Spinelli S, Krapcho AP, Giuliani FC et al.. (1995)
Topoisomerase II DNA cleavage stimulation, DNA binding activity, cytotoxicity, and physico-chemical properties of 2-aza- and 2-aza-oxide-anthracenedione derivatives.
Mol Pharmacol, 48 (1): 30-8. [PMID:7623772]
3. Evison BJ, Mansour OC, Menta E, Phillips DR, Cutts SM. (2007)
Pixantrone can be activated by formaldehyde to generate a potent DNA adduct forming agent.
Nucleic Acids Res, 35 (11): 3581-9. [PMID:17483512]
4. Marolda R, Ruocco C, Cordiglieri C, Toscani C, Antozzi C, Mantegazza R, Baggi F. (2013)
Differential targeting of immune-cells by Pixantrone in experimental myasthenia gravis.
J Neuroimmunol, 258 (1-2): 41-50. [PMID:23523328]
5. Mazzanti B, Biagioli T, Aldinucci A, Cavaletti G, Cavalletti E, Oggioni N, Frigo M, Rota S, Tagliabue E, Ballerini C et al.. (2005)
Effects of pixantrone on immune-cell function in the course of acute rat experimental allergic encephalomyelitis.
J Neuroimmunol, 168 (1-2): 111-7. [PMID:16120465]