Mitoxantrone HCl
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MedKoo CAT#: 100650

CAS#: 70476-82-3 (HCl salt); 65271-80-9 (free base).

Description: Mitoxantrone hydrochloride is the hydrochloride salt of an anthracenedione antibiotic with antineoplastic activity. Mitoxantrone intercalates into and crosslinks DNA, thereby disrupting DNA and RNA replication. This agent also binds to topoisomerase II, resulting in DNA strand breaks and inhibition of DNA repair. Mitoxantrone is less cardiotoxic compared to doxorubicin. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).


Price and Availability

Size
Price

100mg
USD 120
1g
USD 350
10g
USD 1650
100g
USD 4950
Size
Price

200mg
USD 150
2g
USD 550
20g
USD 2650
200g
USD 7950
Size
Price

500mg
USD 250
5g
USD 950
50g
USD 3950
500g
Ask price

Mitoxantrone hydrochloride, purity > 98%, is in stock. The same day shipping out after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100650
Name: Mitoxantrone HCl
CAS#: 70476-82-3 (HCl salt); 65271-80-9 (free base).
Chemical Formula: C22H28N4O6
Exact Mass:
Molecular Weight: 444.48
Elemental Analysis: C, 59.45; H, 6.35; N, 12.60; O, 21.60


Synonym: 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 dihydrochloride

InChi Key: ZAHQPTJLOCWVPG-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H28N4O6.2ClH/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;2*1H

SMILES Code: O=C1C2=C(C(NCCNCCO)=CC=C2NCCNCCO)C(C3=C(O)C=CC(O)=C13)=O.[H]Cl.[H]Cl


Technical Data

Appearance:
Black solid powder

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

Certificate of Analysis:

Safety Data Sheet (MSDS):

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, not in water

Shelf Life:
>2 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).

Harmonized System Code:
293490


Additional Information

 
NOVANTRONE® (mitoxantrone hydrochloride) is a synthetic antineoplastic anthracenedione for intravenous use. The molecular formula is C22H28N4O6•2HCl and the molecular weight is 517.41. It is supplied as a concentrate that MUST BE DILUTED PRIOR TO INJECTION. The concentrate is a sterile, nonpyrogenic, dark blue aqueous solution containing mitoxantrone hydrochloride equivalent to 2 mg/mL mitoxantrone free base, with sodium chloride (0.80% w/v), sodium acetate (0.005% w/v), and acetic acid (0.046% w/v) as inactive ingredients. The solution has a pH of 3.0 to 4.5 and contains 0.14 mEq of sodium per mL. The product does not contain preservatives.
 
 
Mitoxantrone, a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. It has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity. NOVANTRONE® has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen pre sentation, as well as the secretion of interferon gamma, TNFα, and IL-2.
Mitoxantrone, a DNA-reactive agent that intercalates into deoxyribonucleic acid (DNA) through hydrogen bonding, causes crosslinks and strand breaks. Mitoxantrone also interferes with ribonucleic acid (RNA) and is a potent inhibitor of topoisomerase II, an enzyme responsible for uncoiling and repairing damaged DNA. It has a cytocidal effect on both proliferating and nonproliferating cultured human cells, suggesting lack of cell cycle phase specificity. NOVANTRONE® has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen pre sentation, as well as the secretion of interferon gamma, TNFα, and IL-2.
Mitoxantrone is used in the treatment of certain types of cancer, mostly metastatic breast cancer, acute myeloid leukemia, and non-Hodgkin's lymphoma. The combination of mitoxantrone and prednisone is approved as a second-line treatment for metastatic hormone-refractory prostate cancer. This combination has been the first line of treatment, until recently, when combination of docetaxel and prednisone has been shown to improve survival and disease-free period. Mitoxantrone is also used to treat multiple sclerosis (MS), most notably the subset known as secondary progressive MS. Mitoxantrone will not cure multiple sclerosis, but is effective in slowing the progression of secondary progressive MS and extending the time between relapses in relapsing-remitting MS and progressive relapsing MS.
Mitoxantrone
is used in the treatment of certain types of cancer, mostly metastatic breast cancer, acute myeloid leukemia, and non-Hodgkin's lymphoma. The combination of mitoxantrone and prednisone is approved as a second-line treatment for metastatic hormone-refractory prostate cancer. This combination has been the first line of treatment, until recently, when combination of docetaxel and prednisone has been shown to improve survival and disease-free period. Mitoxantrone is also used to treat multiple sclerosis (MS), most notably the subset known as secondary progressive MS. Mitoxantrone will not cure multiple sclerosis, but is effective in slowing the progression of secondary progressive MS and extending the time between relapses in relapsing-remitting MS and progressive relapsing MS.


References

1: Cocco E, Marrosu MG. The current role of mitoxantrone in the treatment of multiple sclerosis. Expert Rev Neurother. 2014 Jun;14(6):607-16. doi: 10.1586/14737175.2014.915742. Epub 2014 May 16. Review. PubMed PMID: 24834466.

2: Szwed M. [Mitoxantrone - an anthraquinone antibiotic with antitumor activity applied for the treatment of multiple sclerosis]. Postepy Hig Med Dosw (Online). 2014 Feb 21;68:198-208. Review. Polish. PubMed PMID: 24662788.

3: Martinelli Boneschi F, Vacchi L, Rovaris M, Capra R, Comi G. Mitoxantrone for multiple sclerosis. Cochrane Database Syst Rev. 2013 May 31;5:CD002127. doi: 10.1002/14651858.CD002127.pub3. Review. PubMed PMID: 23728638.

4: Chan A, Lo-Coco F. Mitoxantrone-related acute leukemia in MS: an open or closed book? Neurology. 2013 Apr 16;80(16):1529-33. doi: 10.1212/WNL.0b013e31828cf891. Review. PubMed PMID: 23589639.

5: Marriott JJ, Miyasaki JM, Gronseth G, O'Connor PW; Therapeutics and Technology Assessment Subcommittee of the American Academy of Neurology. Evidence Report: The efficacy and safety of mitoxantrone (Novantrone) in the treatment of multiple sclerosis: Report of the Therapeutics and Technology Assessment Subcommittee of the American Academy of Neurology. Neurology. 2010 May 4;74(18):1463-70. doi: 10.1212/WNL.0b013e3181dc1ae0. Review. PubMed PMID: 20439849; PubMed Central PMCID: PMC2871006.

6: Martinelli V, Radaelli M, Straffi L, Rodegher M, Comi G. Mitoxantrone: benefits and risks in multiple sclerosis patients. Neurol Sci. 2009 Oct;30 Suppl 2:S167-70. doi: 10.1007/s10072-009-0142-7. Review. PubMed PMID: 19882368.

7: Komori M, Kondo T, Tanaka M. [Mitoxantrone for the treatment of patients with multiple sclerosis]. Brain Nerve. 2009 May;61(5):575-80. Review. Japanese. PubMed PMID: 19514518.

8: Neuhaus O, Kieseier BC, Hartung HP. Pharmacokinetics and pharmacodynamics of the interferon-betas, glatiramer acetate, and mitoxantrone in multiple sclerosis. J Neurol Sci. 2007 Aug 15;259(1-2):27-37. Epub 2007 Mar 27. Review. PubMed PMID: 17391705.

9: Collins R, Trowman R, Norman G, Light K, Birtle A, Fenwick E, Palmer S, Riemsma R. A systematic review of the effectiveness of docetaxel and mitoxantrone for the treatment of metastatic hormone-refractory prostate cancer. Br J Cancer. 2006 Aug 21;95(4):457-62. Epub 2006 Aug 1. Review. PubMed PMID: 16880788; PubMed Central PMCID: PMC2360673.

10: Fox EJ. Management of worsening multiple sclerosis with mitoxantrone: a review. Clin Ther. 2006 Apr;28(4):461-74. Review. PubMed PMID: 16750460.

11: Murray TJ. The cardiac effects of mitoxantrone: do the benefits in multiple sclerosis outweigh the risks? Expert Opin Drug Saf. 2006 Mar;5(2):265-74. Review. PubMed PMID: 16503747.

12: Morrissey SP, Le Page E, Edan G. Mitoxantrone in the treatment of multiple sclerosis. Int MS J. 2005 Nov;12(3):74-87. Review. PubMed PMID: 16417821.

13: Neuhaus O, Kieseier BC, Hartung HP. Mitoxantrone in multiple sclerosis. Adv Neurol. 2006;98:293-302. Review. PubMed PMID: 16400840.

14: Martinelli Boneschi F, Rovaris M, Capra R, Comi G. Mitoxantrone for multiple sclerosis. Cochrane Database Syst Rev. 2005 Oct 19;(4):CD002127. Review. Update in: Cochrane Database Syst Rev. 2013;5:CD002127. PubMed PMID: 16235298.

15: Neuhaus O, Kieseier BC, Hartung HP. Therapeutic role of mitoxantrone in multiple sclerosis. Pharmacol Ther. 2006 Jan;109(1-2):198-209. Epub 2005 Aug 10. Review. PubMed PMID: 16095713.

16: Neuhaus O, Kieseier BC, Hartung HP. Mitoxantrone (Novantrone) in multiple sclerosis: new insights. Expert Rev Neurother. 2004 Jan;4(1):17-26. Review. PubMed PMID: 15853611.

17: Hagemeister F, Cabanillas F, Coleman M, Gregory SA, Zinzani PL. The role of mitoxantrone in the treatment of indolent lymphomas. Oncologist. 2005 Feb;10(2):150-9. Review. PubMed PMID: 15709217.

18: Cohen BA, Mikol DD. Mitoxantrone treatment of multiple sclerosis: safety considerations. Neurology. 2004 Dec 28;63(12 Suppl 6):S28-32. Review. PubMed PMID: 15623667.

19: Rizvi SA, Zwibel H, Fox EJ. Mitoxantrone for multiple sclerosis in clinical practice. Neurology. 2004 Dec 28;63(12 Suppl 6):S25-7. Review. PubMed PMID: 15623666.

20: Jeffery DR, Herndon R. Review of mitoxantrone in the treatment of multiple sclerosis. Neurology. 2004 Dec 28;63(12 Suppl 6):S19-24. Review. PubMed PMID: 15623665.