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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 of PIXANTRONE DIMALEATE

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

Description
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

Curator's Comment: Known to be CNS penetrant in rodents. Human data not available.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Pixuvri

Approved Use

Pixuvri is used for the treatment of adult patients with multiply relapsed or refractory aggressive Non-Hodgkin lymphomas.

Launch Date

2012
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A phase I and pharmacokinetic study of the novel aza-anthracenedione compound BBR 2778 in patients with advanced solid malignancies.
2001 Jan
New immunosuppressants with potential implication in multiple sclerosis.
2004 Aug 15
The role of pixantrone in the treatment of non-Hodgkin's lymphoma.
2005 Aug
Effects of pixantrone on immune-cell function in the course of acute rat experimental allergic encephalomyelitis.
2005 Nov
Pixantrone can be activated by formaldehyde to generate a potent DNA adduct forming agent.
2007
Considerations with newer regimens for indolent non-Hodgkin lymphoma.
2008 Aug
Formaldehyde-activated Pixantrone is a monofunctional DNA alkylator that binds selectively to CpG and CpA doublets.
2008 Jul
CE can identify small molecules that selectively target soluble oligomers of amyloid beta protein and display antifibrillogenic activity.
2009 Apr
Pixantrone maleate for non-Hodgkin's lymphoma.
2009 Nov
Pixantrone for the treatment of aggressive non-Hodgkin lymphoma.
2010 Aug
Patents

Patents

Sample Use Guides

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 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.
Name Type Language
PIXANTRONE DIMALEATE
DASH   USAN  
USAN  
Official Name English
PIXANTRONE DIMALEATE SALT
MI  
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
WHO-DD  
Common Name English
NSC-752341
Code English
Classification Tree Code System Code
EU-Orphan Drug EU/3/09/722
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
EMA ASSESSMENT REPORTS PIXUVRI (AUTHORIZED: LYMPHOMA, NON-HODGKIN)
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
NCI_THESAURUS C582
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
Code System Code Type Description
FDA UNII
P0R64C4CR9
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
PUBCHEM
9937618
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
NCI_THESAURUS
C82398
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
CAS
144675-97-8
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
MERCK INDEX
m8898
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY Merck Index
SMS_ID
100000124199
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
EVMPD
SUB31562
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
DRUG BANK
DBSALT000141
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
NSC
752341
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
USAN
WW-63
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL167731
Created by admin on Fri Dec 15 15:25:38 GMT 2023 , Edited by admin on Fri Dec 15 15:25:38 GMT 2023
PRIMARY