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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. UK (2012)  |  EMA (2012)
IUPAC Name Click here for help
6,9-bis(2-aminoethylamino)benzo[g]isoquinoline-5,10-dione
International Nonproprietary Names Click here for help
INN number INN
8260 pixantrone
Synonyms Click here for help
BBR-2778 | Pixuvri®
Database Links Click here for help
CAS Registry No. 144510-96-3
ChEMBL Ligand CHEMBL167731
DrugCentral Ligand 4330
GtoPdb PubChem SID 187051845
PubChem CID 134019
Search Google for chemical match using the InChIKey PEZPMAYDXJQYRV-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PEZPMAYDXJQYRV
Search PubMed clinical trials pixantrone
Search PubMed titles pixantrone
Search PubMed titles/abstracts pixantrone
UniChem Compound Search for chemical match using the InChIKey PEZPMAYDXJQYRV-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PEZPMAYDXJQYRV-UHFFFAOYSA-N
Wikipedia Pixantrone