PIXANTRONE DIMALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H19N5O2.2C4H4O4
Molecular Weight	557.5094
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.NCCNC1=CC=C(NCCN)C2=C1C(=O)C3=C(C=NC=C3)C2=O

InChI

InChIKey=SVAGFBGXEWPNJC-SPIKMXEPSA-N

InChI=1S/C17H19N5O2.2C4H4O4/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;2*5-3(6)1-2-4(7)8/h1-3,6,9,21-22H,4-5,7-8,18-19H2;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C17H19N5O2
Molecular Weight	325.3651
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/002055/WC500127970.pdf
Curator's Comment: description was created based on several sources, including: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002055/WC500127968.pdf | https://www.medicines.org.uk/emc/PIL.30473.latest.pdf

Pixantrone is a novel anthracenedione. It is a weak inhibitor of topoisomerase II. Pixantrone directly alkylates DNA forming stable DNA adducts and cross-strand breaks. Pixuvri is approved for the treatment of adult patients with multiply relapsed or refractory aggressive Non-Hodgkin lymphomas. It is used for patients whose cancer does not respond or has returned after they have received other chemotherapy treatments. The most frequent AE were seen in the blood (mainly neutropaenia), gastrointestinal (nausea, abdominal pain, constipation) and respiratory systems (cough, dyspnea). No drug-drug interaction studies have been submitted and no drug interactions have been reported in human subjects

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002055/WC500127968.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/26660439	Inhibitor 8297
DNA topoisomerase II beta 14 Target ID: CHEMBL3396 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002055/WC500127968.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/26660439	Inhibitor 8297
DNA 278 Target ID: CHEMBL2311221 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002055/WC500127968.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/26660439	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Non-Hodgkin's lymphoma 79 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002055/WC500127968.pdf	Primary	Approved 8429	Pixuvri Approved Use Pixuvri is used for the treatment of adult patients with multiply relapsed or refractory aggressive Non-Hodgkin lymphomas. Launch Date 1.33652165E12
Diffuse large B-cell lymphoma 20 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27093976	Primary	Phase III 656	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11205916	Primary	Phase II 1132	Unknown Approved Use Unknown
Acute myelogenous leukemia 19 Sources: https://clinicaltrials.gov/ct2/show/NCT00106600	Primary	Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pixantrone (Novuspharma).	2003 May	12789604
Pixantrone: a novel aza-anthracenedione in the treatment of non-Hodgkin's lymphomas.	2007 Oct	17922631
Considerations with newer regimens for indolent non-Hodgkin lymphoma.	2008 Aug	18952543
Formaldehyde-activated Pixantrone is a monofunctional DNA alkylator that binds selectively to CpG and CpA doublets.	2008 Jul	18413664

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose is 50 mg/m^2 of pixantrone on day 1, 8 and 15 of each 28-day cycle for up to 6 cycles.

Route of Administration: Intravenous

In Vitro Use Guide

In separate 72-hour growth-inhibitory assays using direct cell counting, the etoposide-resistant K/VP.5 cells were 21.6-fold cross-resistant to pixantrone, yielding IC50 values of 0.04 and 0.85 uM for K562 and K/VP.5 cells, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:25:38 UTC 2023` Edited by `admin` on `Fri Dec 15 15:25:38 UTC 2023`
Record UNII	P0R64C4CR9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIXANTRONE DIMALEATE

Official Name

English

PIXANTRONE DIMALEATE SALT

Common Name

English

BBR 2778 DIMALEATE

Code

English

Pixantrone maleate [WHO-DD]

Common Name

English

PIXANTRONE DIMALEATE SALT [MI]

Common Name

English

PIXUVRI

Brand Name

English

PIXANTRONE DIMALEATE [USAN]

Common Name

English

6,9-Bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5,10-dione (2Z)-but-2-enedioate (1:2)

Systematic Name

English

BENZ(G)ISOQUINOLINE-5,10-DIONE, 6,9-BIS((2-AMINOETHYL)AMINO)-, (2Z)-2-BUTENEDIOATE (1:2)

Systematic Name

English

BBR-2778 DIMALEATE

Code

English

PIXANTRONE MALEATE

Common Name

English

NSC-752341

Code

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/09/722