Mitoxantrone free base | CAS#65271-80-9

MedKoo Cat#: 100972 | Name: Mitoxantrone free base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mitoxantrone is an anthraquinone that intercalates in DNA and inhibits topoisomerase II (IC50 = 5.3 μM), thus inhibiting cell proliferation. It also inhibits HIV-1 integrase (IC50 = 3.8 μM). Mitoxantrone is exported from cells in an ATP- and glutathione-dependent manner by multidrug resistance protein-1.4 Formulations containing mitoxantrone have been used in the treatment of cancer and multiple sclerosis.

Chemical Structure

Mitoxantrone free base

CAS#65271-80-9 (free base)

Theoretical Analysis

MedKoo Cat#: 100972

Name: Mitoxantrone free base

CAS#: 65271-80-9 (free base)

Chemical Formula: C22H28N4O6

Exact Mass: 444.2009

Molecular Weight: 444.49

Elemental Analysis: C, 59.45; H, 6.35; N, 12.61; O, 21.60

Price and Availability

Size	Price	Availability
100mg	USD 285.00	2 Weeks
250mg	USD 550.00	2 Weeks
1g	USD 1,250.00	2 Weeks

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Related CAS #

70476-82-3 (HCl) 65271-80-9 (free base) 70711-41-0 (diacetate)

Synonym

Mitoxantrone free base, DHAQ; CL-232325; CL 232325; CL232325; Mitozantrone; Mitoxantrone HCl; Mitoxantrone dihydrchloride; US brand name: Novantrone. Foreign brand names: Mitroxone; Neotalem; Onkotrone; Pralifan.

IUPAC/Chemical Name

1,4-dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)anthracene-9,10-dione

InChi Key

O=C1C2=C(C(NCCNCCO)=CC=C2NCCNCCO)C(C3=C(O)C=CC(O)=C13)=O

InChi Code

InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32/h1-4,23-30H,5-12H2

SMILES Code

O=C1C2=C(C(NCCNCCO)=CC=C2NCCNCCO)C(C3=C(O)C=CC(O)=C13)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Mitoxantrone is a potent topoisomerase II inhibitor. Mitoxantrone also inhibits protein kinase C (PKC) activity with an IC50 of 8.5 μM.

In vitro activity:

Kinetic studies demonstrated that mitoxantrone inhibited PKC in a competitive manner with respect to histone H1, and its Ki value was 6.3 microM (Ki values of daunorubicin and doxorubicin were 0.89 and 0.15 mM, respectively), and in a non-competitive manner with respect to phosphatidylserine and ATP. Inhibition of phosphorylation by mitoxantrone was observed with various substrates including S6 peptide, myelin basic protein and its peptide substrate derived from the amino-terminal region. Reference: J Biochem. 1992 Dec;112(6):762-7. https://pubmed.ncbi.nlm.nih.gov/1295884/

In vivo activity:

Mitoxantrone demonstrated an EC(50) of 0.25 μM against cowpox and 0.8 μM against monkeypox. Intraperitoneal treatment of cowpox virus-challenged C57Bl/6 mice with 0.5 mg/kg mitoxantrone resulted in 25% survival and a significant increase in survival time. Reference: Antiviral Res. 2012 Feb;93(2):305-308. https://pubmed.ncbi.nlm.nih.gov/22182595/

	Solvent	mg/mL	mM
Solubility
	DMSO	62.5	140.61

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 444.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. da Silva RAG, Wong JJ, Antypas H, Choo PY, Goh K, Jolly S, Liang C, Tay Kwan Sing L, Veleba M, Hu G, Chen J, Kline KA. Mitoxantrone targets both host and bacteria to overcome vancomycin resistance in Enterococcus faecalis. Sci Adv. 2023 Feb 22;9(8):eadd9280. doi: 10.1126/sciadv.add9280. Epub 2023 Feb 22. PMID: 36812322; PMCID: PMC9946351. 2. Takeuchi N, Nakamura T, Takeuchi F, Hashimoto E, Yamamura H. Inhibitory effect of mitoxantrone on activity of protein kinase C and growth of HL60 cells. J Biochem. 1992 Dec;112(6):762-7. doi: 10.1093/oxfordjournals.jbchem.a123972. PMID: 1295884. 3. Altmann SE, Smith AL, Dyall J, Johnson RF, Dodd LE, Jahrling PB, Paragas J, Blaney JE. Inhibition of cowpox virus and monkeypox virus infection by mitoxantrone. Antiviral Res. 2012 Feb;93(2):305-308. doi: 10.1016/j.antiviral.2011.12.001. Epub 2011 Dec 11. PMID: 22182595; PMCID: PMC3272698. 4. Fujimoto S, Ogawa M. Antitumor activity of mitoxantrone against murine experimental tumors: comparative analysis against various antitumor antibiotics. Cancer Chemother Pharmacol. 1982;8(2):157-62. doi: 10.1007/BF00255476. PMID: 7105379.

In vitro protocol:

In vivo protocol:

1. Altmann SE, Smith AL, Dyall J, Johnson RF, Dodd LE, Jahrling PB, Paragas J, Blaney JE. Inhibition of cowpox virus and monkeypox virus infection by mitoxantrone. Antiviral Res. 2012 Feb;93(2):305-308. doi: 10.1016/j.antiviral.2011.12.001. Epub 2011 Dec 11. PMID: 22182595; PMCID: PMC3272698. 2. Fujimoto S, Ogawa M. Antitumor activity of mitoxantrone against murine experimental tumors: comparative analysis against various antitumor antibiotics. Cancer Chemother Pharmacol. 1982;8(2):157-62. doi: 10.1007/BF00255476. PMID: 7105379.

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