Pixantrone Dimaleate

ChemicalBook > CAS DataBase List > Pixantrone Dimaleate

Product Name: Pixantrone Dimaleate
CAS No.: 144675-97-8
Chemical Name: Pixantrone Dimaleate
Synonyms: Pixantrone maleate;CS-1295;Bbr 2778;Dimalate salt;BBR 2778 dimaleate;Pixatrone dimaleate;Pixantrone Dimaleate;Pixantrone dimaleate (BBR-2778);Pixantrone-dimaleate, BBR2778 dimaleate;6,9-Bis((2-aminoethyl)amino)benzo[g]isoquinoline-5,10-dione maleate
CBNumber: CB41245169
Molecular Formula: C21H23N5O6
Formula Weight: 441.44
MOL File: 144675-97-8.mol

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Pixantrone Dimaleate Property

Melting point:: 192°
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
solubility: DMSO:30.0(Max Conc. mg/mL);53.8(Max Conc. mM)
H2O:5.0(Max Conc. mg/mL);9.0(Max Conc. mM)
form: A crystalline solid

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

H310Fatal in contact with skin

H330Fatal if inhaled

H370Causes damage to organs

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P262Do not get in eyes, on skin, or on clothing.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P350IF ON SKIN: Gently wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P307+P311IF exposed: call a POISON CENTER or doctor/physician.

P310Immediately call a POISON CENTER or doctor/physician.

P320Specific treatment is urgent (see … on this label).

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P361Remove/Take off immediately all contaminated clothing.

P363Wash contaminated clothing before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 20055
Product name: Pixantrone (maleate)
Purity: ≥95%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 20055
Product name: Pixantrone (maleate)
Purity: ≥95%
Packaging: 5mg
Price: $93
Updated: 2024/03/01

Cayman Chemical

Product number: 20055
Product name: Pixantrone (maleate)
Purity: ≥95%
Packaging: 10mg
Price: $169
Updated: 2024/03/01

Cayman Chemical

Product number: 20055
Product name: Pixantrone (maleate)
Purity: ≥95%
Packaging: 25mg
Price: $343
Updated: 2024/03/01

TRC

Product number: P552500
Product name: PixantroneDimaleate
Packaging: 10mg
Price: $150
Updated: 2021/12/16

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Pixantrone Dimaleate Chemical Properties,Usage,Production

Description

Pixantrone dimaleate was approved by European Medicine Agency (EMA) on May 10, 2012. It was developed and marketed as Pixuvri® by Cell Therapeutics in EU. (CTI Life Sciences).
Pixantrone dimaleate is a DNA intercalating agent indicated as monotherapy for the treatment of adult patients with multiply relapsed or refractory aggressive Non-Hodgkin B-cell Lymphomas (NHL).
Pixuvri® is available as lyophilised powder for infusion, containing 29 mg of free Pixantrone. The recommended dose is 50 mg/m2 of pixantrone on days 1, 8 and 15 of each 28-day cycle for up to 6 cycles.

Chemical Properties

Blue Solid

Occurrence

Pixantrone dimaleate, also known as BBR 2778, was first synthesized by Professors Krapcho and Hacker at the University of Vermont. The University of Vermont and the Boehringer Mannheim Italia research center co-identified the in vitro tumor cell cytotoxicity.

Uses

Pixantrone is an antineoplastic drug belonging to group of antitumor antibiotics. Pixantrone is an anlogue of Mitoxantrone (M373425) and is just as potent in the treatment of multiple sclerosis with f ewer toxic effects on cardiac tissue. Studies suggest that Pixantrone significantly reduces amyloid beta (A beta(1-42)) neurotoxicity, a mechanism implicated in Alzheimer's disease.

Preparation

The manufacturing scale synthesis of pixantrone dimaleate relies on several process modifications from the original synthesis reported by Krapcho in 1994. This modified procedure has provided active pharmaceutical ingredient (API) in high purity (>99%) and is acceptable for use in pharmaceutical applications (Scheme 25). Beginning with pyridine 3,4-dicarboxylic acid (129), generation of the corresponding anhydride 130 proceeded in 76% yield upon treatment with refluxing Ac2O. Next, an AlCl3-promoted Friedel–Crafts reaction of 1,4-difluorobenzene (131) with 130 under reflux conditions provided a mixture of nicotinic acid isomers 132a/132b in 84% yield, which were carried directly to the next step. Cyclization with fuming H2SO4 yielded the desired difluorobenzo-isoquinoline-dione core 133, which was further functionalized with ethylenediamine (134) to provide the free base of pixantrone. Subjection of the pixantrone free base to aqueous acetic anhydride and maleic acid provided pixantrone dimaleate (XX) in 92% yield over 3 steps.

Synthesis of pixantrone dimaleate

Biological Activity

Pixantrone (BBR 2778) is an aza-anthracenedione with enhanced antitumor activity due to its DNA-intercalating and topoisomerase II-poisoning activity. Pixantrone shows no signs of acute or delayed cardiotoxicity seen with anthracyclines mitoxantrone and doxorubicin (DOX), while exhibiting comparable in vivo efficacy against solid tumors in mice. Tests conducted on human myocardial strips ex vivo shows that not only pixantrone does not form superoxide anion and hydrogen peroxide (O2?? and H2O2) seen with DOX due to redox activation, pixantrone and its metabolites, especially N-dealkylated, show competitive inhibition against DOX reduction. While mitoxantrone does not form O2?? and H2O2 on its own, it synergizes with DOX to form more O2?? and H2O2, whose formation and subsequent production of the long-lived metabolite doxorubicinol contribute to DOX cardiotoxicity.

References

[1] A. PAUL KRAPCHO. 6,9-Bis[(aminoalkyl)amino]benzo[g]isoquinoline-5,10-diones. A Novel Class of Chromophore-Modified Antitumor Anthracene-9,10-diones: Synthesis and Antitumor Evaluations[J]. Journal of Medicinal Chemistry, 1994, 37 6: 828-837. DOI:10.1021/jm00032a018.
[2] 170. Krapcho, A. P.; Hacker, M. P.; Cavalletti, E.; Giuliani, F. C. US Patent 5587382 A,1996.
[3] Spinelli, S.; Didomenico, R. WO Patent 9526189 A1, 1995.
[4] Krapcho, P. A. EP Patent 503537 A1, 1992

Pixantrone Dimaleate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Pixantrone Dimaleate manufacturers

Career Henan Chemical Co

Product: Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-aminoethyl)amino)-, (2Z)-2- butenedioate (1:2) 144675-97-8
Price: US $2.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 100kg
Release date: 2018-12-24

144675-97-8, Pixantrone DimaleateRelated Search:

CIS-BUTENEDIOIC ANHYDRIDE Chlorphenamine maleate Pixantrone Impurity B BENZ[G]ISOQUINOLINE-5,10-DIONE

Benz(g)isoquinoline-5,10-dione, 6,9-bis((2-aminoethyl)amino)-, (2Z)-2- butenedioate (1:2)

Bbr 2778

Pixantrone maleate

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

CS-1295

Pixantrone-dimaleate, BBR2778 dimaleate

Pixatrone dimaleate

BBR 2778 dimaleate

6,9-Bis((2-aminoethyl)amino)benzo[g]isoquinoline-5,10-dione maleate

Dimalate salt

Pixantrone dimaleate (BBR-2778)

6,9-Bis((2-aminoethyl)amino)benzo[g]isoquinoline-5,10-dione dimaleate

Pixantrone Dimaleate

144675-97-8

146675-97-8

C17H19N5O22C4H4O4

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