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Related CAS#:
65271-80-9 1189974-82-0
70476-82-3 89991-52-6
97729-56-1 137132-70-8
1195810-93-5

65271-80-9

65271-80-9 structure
65271-80-9 structure
  • Name: Mitoxantrone
  • Chemical Name: mitoxantrone
  • CAS Number: 65271-80-9
  • Molecular Formula: C22H28N4O6
  • Molecular Weight: 444.481
  • Catalog: API Antineoplastic agents Anti-tumor adjuvant
  • Create Date: 2018-06-23 20:03:41
  • Modify Date: 2024-01-02 21:17:23
  • Mitoxantrone is a topoisomerase II inhibitor; also inhibits protein kinase C (PKC) activity with an IC50 of 8.5 μM.
Name mitoxantrone
Synonyms 1,4-Dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-anthraquinone
mitoxanthrone
1,4-Dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracen-9,10-dion
UNII-BZ114NVM5P
MFCD00242942
PharmasubstanceEP4
1,4-dihydroxy-5,8-bis({2-[(2-hydroxyéthyl)amino]éthyl}amino)anthracène-9,10-dione
DHAQ
1,4-dihydroxy-5,8-bis[[2-(2-hydroxy-ethylamino)ethyl]amino]anthraquinone
9,10-Anthracenedione, 1,4-dihydroxy-5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-
dihydroxyanthraquinone
1,4-dehydroxy-5,8-bis[[[2-(2-hydroxyethyl)amino]ethyl]amino]-9,19-antracenedion
9,10-Anthracenedione, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-
MITOXANTRONUM AND THE INTERMEDIATES
1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione
1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthraquinone
1,4-bis-[2-(2-hydroxyethylamino)ethylamino]-5,8-dihydroxy-9,10-anthracenedione
1,4-bis[2-(2-hydroxyethylamino)ethylamino]-5,8-dihydroxyanthraquinone
Mitoxantrone
[3H]-Mitoxantrone
MITOXANTRONUM
Description Mitoxantrone is a topoisomerase II inhibitor; also inhibits protein kinase C (PKC) activity with an IC50 of 8.5 μM.
Related Catalog
Target

PKC:8.5 μM (IC50)

Topoisomerase II
In Vitro Mitoxantrone inhibits PKC in a competitive manner with respect to histone H1, and its Ki value is 6.3 μM and in a non-competitive manner with respect to phosphatidylserine and ATP[1]. Treatment of B-CLL cells for 48 h with mitoxantrone (0.5 μg/mL) induces a decrease in cell viability. Mitoxantrone induces DNA fragmentation and the proteolytic cleavage of poly(ADP-ribose) polymerase (PARP), demonstrating that the cytotoxic effect of mitoxantrone is due to induction of apoptosis[2]. Mitoxantrone shows cytotoxicity to human breast carcinoma cell lines MDA-MB-231 and MCF-7 with IC50 values of 18 and 196 nM, respectively[3].
In Vivo Mitoxantrone given IP at the optimal dose (1.6 mg/kg/day; as a free base) produces a statistically significant number of 60-day survivors (curative effect) in mice with IP implanted L1210 leukemia. In SC implanted Lewis lung carcinoma, mitoxantrone and ADM administered IV also shows effective antitumor activities and produces a 60% and a 45% ILS, respectively.[4].
Cell Assay The human breast carcinoma cell lines MDA-MB-231 and MCF-7 are seeded in standard 96-well plates. One day after seeding, the culture medium is changed and replaced by medium containing different concentration of Mitoxantrone (10-5 to 5 μM) with or without DHA (30 μM) during 7 days. Viability of cells are measured as a whole by the tetrazolium salt assay[3].
Animal Admin Mice: Mitoxantrone is tested for antitumor activity against experimental tumors in mice and the results are compared with those of seven antitumor antibiotics. The drugs are given IP or IV, in general on days 1, 5, and 9 following tumor inoculation. Mitoxantrone is given IP at the optimal dose (1.6 mg/kg/day; as a free base)[4].
References

[1]. Takeuchi N, et al. Inhibitory effect of mitoxantrone on activity of protein kinase C and growth of HL60 cells. J Biochem. 1992 Dec;112(6):762-7.

[2]. Bellosillo B, et al. Mitoxantrone, a topoisomerase II inhibitor, induces apoptosis of B-chronic lymphocytic leukaemia cells. Br J Haematol. 1998 Jan;100(1):142-6.

[3]. Vibet S, et al. Differential subcellular distribution of mitoxantrone in relation to chemosensitization in two human breast cancer cell lines. Drug Metab Dispos. 2007 May;35(5):822-8.

[4]. Fujimoto S, et al. Antitumor activity of mitoxantrone against murine experimental tumors: comparative analysis against various antitumor antibiotics. Cancer Chemother Pharmacol. 1982;8(2):157-62.
Density 1.5±0.1 g/cm3
Boiling Point 805.7±65.0 °C at 760 mmHg
Melting Point 170-174ºC
Molecular Formula C22H28N4O6
Molecular Weight 444.481
Flash Point 441.1±34.3 °C
Exact Mass 444.200897
PSA 163.18000
LogP 0.45
Vapour Pressure 0.0±3.0 mmHg at 25°C
Index of Refraction 1.709
Storage condition -20°C Freezer

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CB5748500
CHEMICAL NAME :
Anthraquinone, 5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-di hydroxy-
CAS REGISTRY NUMBER :
65271-80-9
LAST UPDATED :
199612
DATA ITEMS CITED :
22
MOLECULAR FORMULA :
C22-H28-N4-O6
MOLECULAR WEIGHT :
444.54
WISWESSER LINE NOTATION :
L C666 BV IVJ DQ GQ KM2M2Q NM2M2Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
7100 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
20910 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
86500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
16 mg/kg/6W-I
TOXIC EFFECTS :
Cardiac - EKG changes not diagnostic of specified effects Liver - other changes Blood - changes in leukocyte (WBC) count
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
Sex chromosome loss and nondisjunction
TYPE OF TEST :
DNA damage

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
100 ng/L
REFERENCE :
PAACA3 Proceedings of the American Association for Cancer Research. (Waverly Press, 428 E. Preston St., Baltimore, MD 21202) V.1- 1954- Volume(issue)/page/year: 26,217,1985
Hazard Codes T,T+
Risk Phrases R46
Safety Phrases 53-36/37/39-45-22
RIDADR 3077.0
WGK Germany 3
RTECS CB5748500
Hazard Class 9.0
Precursor  3

DownStream  0


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