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Details

Stereochemistry ACHIRAL
Molecular Formula C17H19N5O2
Molecular Weight 325.3651
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIXANTRONE

SMILES

NCCNC1=CC=C(NCCN)C2=C1C(=O)C3=C(C=NC=C3)C2=O

InChI

InChIKey=PEZPMAYDXJQYRV-UHFFFAOYSA-N
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

HIDE SMILES / InChI

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
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

1.33652165E12
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
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
A phase I and pharmacokinetic study of the novel aza-anthracenedione compound BBR 2778 in patients with advanced solid malignancies.
2001 Jan
Phase I study of BBR 2778, a new aza-anthracenedione, in advanced or refractory non-Hodgkin's lymphoma.
2001 May
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
Effects of pixantrone on immune-cell function in the course of acute rat experimental allergic encephalomyelitis.
2005 Nov
Diagnosis and management of lymphoma.
2006 Jul
EXTEND PIX301: a phase III randomized trial of pixantrone versus other chemotherapeutic agents as third-line monotherapy in patients with relapsed, aggressive non-Hodgkin's lymphoma.
2006 Sep
Pixantrone can be activated by formaldehyde to generate a potent DNA adduct forming agent.
2007
A phase I/II trial of pixantrone (BBR2778), methylprednisolone, cisplatin, and cytosine arabinoside (PSHAP) in relapsed/refractory aggressive non-Hodgkin's lymphoma.
2007 Feb
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

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:42:32 UTC 2023
Edited
by admin
on Sat Dec 16 16:42:32 UTC 2023
Record UNII
F5SXN2KNMR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIXANTRONE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
pixantrone [INN]
Common Name English
BBR2778
Code English
BENZ(G)ISOQUINOLINE-5,10-DIONE, 6,9-BIS((2-AMINOETHYL)AMINO)-
Systematic Name English
PIXANTRONE [USAN]
Common Name English
6,9-Bis[(2-aminoethyl)amino]benzo[g]isoquinoline-5,10-dione
Systematic Name English
PIXANTRONE [MART.]
Common Name English
PIXANTRONE [MI]
Common Name English
BBR-2778
Code English
Pixantrone [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC L01DB11
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
NCI_THESAURUS C582
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
WHO-VATC QL01DB11
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C26663
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
DRUG CENTRAL
4330
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
SMS_ID
100000084758
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
DRUG BANK
DB06193
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
PUBCHEM
134019
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
WIKIPEDIA
PIXANTRONE
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
USAN
PP-22
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID10162744
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
MESH
C086548
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
EVMPD
SUB21304
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
INN
8260
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL167731
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
FDA UNII
F5SXN2KNMR
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
CAS
144510-96-3
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY
MERCK INDEX
m8898
Created by admin on Sat Dec 16 16:42:33 UTC 2023 , Edited by admin on Sat Dec 16 16:42:33 UTC 2023
PRIMARY Merck Index
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SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY