PIXANTRONE


Synonyms	BBR 2778 BBR-2778 Pixantrone
Status
Molecule Category	UNKNOWN
ATC	L01DB11
UNII	F5SXN2KNMR
EPA CompTox	DTXSID10162744


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	PEZPMAYDXJQYRV-UHFFFAOYSA-N
Smiles	NCCNc1ccc(NCCN)c2c1C(=O)c1ccncc1C2=O
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

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C17H19N5O2
Molecular Weight	325.37
AlogP	0.6
Hydrogen Bond Acceptor	7.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	6.0
Polar Surface Area	123.13
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	24.0

Bioactivity

Mechanism of Action	Action	Reference
DNA cross-linking agent	CROSS-LINKING AGENT	PubMed PubMed

Assay Description	Organism	Bioactivity
Tested in vitro for cytotoxic activity against Human colon Adenocarcinoma sensitive cell line (LoVo)	Homo sapiens	0.24 ug.mL-1
Tested in vitro for cytotoxic activity against Doxorubicin resistant Human colon Adenocarcinoma sensitive cell line	Homo sapiens	7.2 ug.mL-1
PubChem BioAssay. Increased HeLa cells with 2N DNA content-IC50. (Class of assay: confirmatory)	None	42.0 nM
PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmatory)	None	42.06 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory)	None	46.5 nM
PubChem BioAssay. Increased HeLa cells with 4N DNA content-IC50. (Class of assay: confirmatory)	None	48.29 nM

Cross References

Resources	Reference
ChEBI	135945
ChEMBL	CHEMBL167731
DrugBank	DB06193
DrugCentral	4330
FDA SRS	F5SXN2KNMR
Guide to Pharmacology	7544
PubChem	134019
SureChEMBL	SCHEMBL7825
ZINC	ZINC000001535903

CONTENTS


PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains. Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).