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Details

Stereochemistry ACHIRAL
Molecular Formula C17H19N5O2.2C4H4O4
Molecular Weight 557.5094
Optical Activity UNSPECIFIED
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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
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
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Topoisomerase II DNA cleavage stimulation, DNA binding activity, cytotoxicity, and physico-chemical properties of 2-aza- and 2-aza-oxide-anthracenedione derivatives.
1995 Jul
Bbr 2778, an aza-anthracenedione endowed with preclinical anticancer activity and lack of delayed cardiotoxicity.
2001 Nov-Dec
Characterization of anthracenediones and their photoaffinity analogs.
2002 Mar 15
Solid-state characterization of a novel chemotherapeutic drug.
2003 Mar
Pixantrone (Novuspharma).
2003 May
A comparison of the benefits of mitoxantrone and other recent therapeutic approaches in multiple sclerosis.
2004 Apr
New immunosuppressants with potential implication in multiple sclerosis.
2004 Aug 15
Pixantrone (BBR2778): a new immunosuppressant in multiple sclerosis with a low cardiotoxicity.
2004 Aug 15
Pixantrone (BBR2778) reduces the severity of experimental allergic encephalomyelitis.
2004 Jun
The role of pixantrone in the treatment of non-Hodgkin's lymphoma.
2005 Aug
Compared benefit of approved and experimental immunosuppressive therapeutic approaches in multiple sclerosis.
2007 Jun
Pixantrone (BBR 2778) has reduced cardiotoxic potential in mice pretreated with doxorubicin: comparative studies against doxorubicin and mitoxantrone.
2007 Jun
Pixantrone: a novel aza-anthracenedione in the treatment of non-Hodgkin's lymphomas.
2007 Oct
Considerations with newer regimens for indolent non-Hodgkin lymphoma.
2008 Aug
Pixantrone (BBR2778) reduces the severity of experimental autoimmune myasthenia gravis in Lewis rats.
2008 Feb 15
Synthesis and antitumor evaluation of bis aza-anthracene-9,10-diones and bis aza-anthrapyrazole-6-ones.
2008 Feb 28
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: a promising drug in the treatment of non-Hodgkin lymphomas.
2009 May
Pixantrone maleate for non-Hodgkin's lymphoma.
2009 Nov
Pixantrone for the treatment of aggressive non-Hodgkin lymphoma.
2010 Aug
DNA binding by pixantrone.
2010 Dec 7
Lymphoma researchers in search of molecular targets.
2010 Jul 21
Can anthracycline therapy for pediatric malignancies be less cardiotoxic?
2010 Nov
New anthracenedione derivatives with improved biological activity by virtue of stable drug-DNA adduct formation.
2010 Oct 14
Differential targeting of immune-cells by Pixantrone in experimental myasthenia gravis.
2013 May 15
Patents

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 Mon Oct 21 20:47:29 UTC 2019
Edited
by admin
on Mon Oct 21 20:47:29 UTC 2019
Record UNII
P0R64C4CR9
Record Status Validated (UNII)
Record Version
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Name Type Language
PIXANTRONE DIMALEATE
DASH   USAN  
USAN  
Official Name English
PIXANTRONE DIMALEATE SALT
MI  
Common Name English
BBR 2778 DIMALEATE
Code English
PIXANTRONE DIMALEATE SALT [MI]
Common Name English
PIXANTRONE MALEATE [WHO-DD]
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
Classification Tree Code System Code
EU-Orphan Drug EU/3/09/722
Created by admin on Mon Oct 21 20:47:29 UTC 2019 , Edited by admin on Mon Oct 21 20:47:29 UTC 2019
EMA ASSESSMENT REPORTS PIXUVRI (AUTHORIZED: LYMPHOMA, NON-HODGKIN)
Created by admin on Mon Oct 21 20:47:29 UTC 2019 , Edited by admin on Mon Oct 21 20:47:29 UTC 2019
NCI_THESAURUS C582
Created by admin on Mon Oct 21 20:47:29 UTC 2019 , Edited by admin on Mon Oct 21 20:47:29 UTC 2019
Code System Code Type Description
PUBCHEM
9937618
Created by admin on Mon Oct 21 20:47:29 UTC 2019 , Edited by admin on Mon Oct 21 20:47:29 UTC 2019
PRIMARY
NCI_THESAURUS
C82398
Created by admin on Mon Oct 21 20:47:29 UTC 2019 , Edited by admin on Mon Oct 21 20:47:29 UTC 2019
PRIMARY
CAS
144675-97-8
Created by admin on Mon Oct 21 20:47:29 UTC 2019 , Edited by admin on Mon Oct 21 20:47:29 UTC 2019
PRIMARY
MERCK INDEX
M8898
Created by admin on Mon Oct 21 20:47:29 UTC 2019 , Edited by admin on Mon Oct 21 20:47:29 UTC 2019
PRIMARY Merck Index
EVMPD
SUB31562
Created by admin on Mon Oct 21 20:47:29 UTC 2019 , Edited by admin on Mon Oct 21 20:47:29 UTC 2019
PRIMARY
ChEMBL
CHEMBL167731
Created by admin on Mon Oct 21 20:47:29 UTC 2019 , Edited by admin on Mon Oct 21 20:47:29 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY