CAS Number70476-82-3
Synonyms1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracene-9,10-dione dihydrochloride; Mitoxantrone dihydrochloride; MITOXANTHRONE HYDROCHLORIDE; Mitoxantrone 2HCl; 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyéthyl)amino]éthyl}amino)anthracène-9,10-dione dichlorhydrate; MITOZANTRONE; MFCD00242943; 1,4-Dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracen-9,10-diondihydrochlorid; 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione,dihydrochloride; MITOXANTRONE HCl; 9,10-anthracenedione, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-, dihydrochloride; Mitoxantrone hydrochloride; Novantron; Onkotrone; UNII-U6USW86RD0; 1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthraquinone Dihydrochloride; EINECS 274-619-1; 1,4-D
Molecular FormulaC22H30Cl2N4O6
Molecular Weight517.40
Purity≥97 (HPLC)%
Boiling Point805.7ºC at 760 mmHg
Melting Point203-205ºC
AppearanceSolid;Dark green to Dark purple to Black powder to crystal
EINECS274-619-1
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 70476-82-3 |
| Catalog No. | 2A-9011471 |
| Chinese Name | 盐酸米托蒽醌 |
| Synonyms | 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracene-9,10-dione dihydrochloride; Mitoxantrone dihydrochloride; MITOXANTHRONE HYDROCHLORIDE; Mitoxantrone 2HCl; 1,4-dihydroxy-5,8-bis({2-[(2-hydroxyéthyl)amino]éthyl}amino)anthracène-9,10-dione dichlorhydrate; MITOZANTRONE; MFCD00242943; 1,4-Dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)anthracen-9,10-diondihydrochlorid; 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione,dihydrochloride; MITOXANTRONE HCl; 9,10-anthracenedione, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-, dihydrochloride; Mitoxantrone hydrochloride; Novantron; Onkotrone; UNII-U6USW86RD0; 1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthraquinone Dihydrochloride; EINECS 274-619-1; 1,4-D |
| Molecular Formula | C22H30Cl2N4O6 |
| Molecular Weight | 517.40 |
| Purity | ≥97 (HPLC) |
| Boiling Point | 805.7ºC at 760 mmHg |
| Melting Point | 203-205ºC |
| Appearance | Solid;Dark green to Dark purple to Black powder to crystal |
| Water Solubility | Water solubility: virtually insoluble; slightly so |
| Storage Condition | 0-10°C; avoid heating |
| Packaging | III |
| Application | Mitoxantrone dihydrochloride is an inhibitor of topoisomerase II; it can also inhibit protein kinase C (PKC) with an IC50 value of 8.5 μM. |
| EINECS | 274-619-1 |
| HTC | 2914610000 |
| PubChem ID | 24278562 |
| MDL Number | MFCD00242943 |
| SMILES | Cl[H].Cl[H].OCCNCCNc1ccc(NCCNCCO)c2C(=O)c3c(O)ccc(O)c3C(=O)c12 |
| 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 |
| InChI Key | ZAHQPTJLOCWVPG-UHFFFAOYSA-N |
| NACRES Code | NA.25 |
| UNSPSC | 12352005 |
| Hazard Symbols | 6.1(b) |
| MSDS | msds/11471_1_70476_82_3.pdf |
| Bioactivity | Mitoxantrone dihydrochloride is a topoisomerase II inhibitor; also inhibits protein kinase C (PKC) activity with an IC50 of 8.5 μM. Related Catalog Signaling Pathways >> Epigenetics >> PKC Signaling Pathways >> TGF-beta/Smad >> PKC Research Areas >> Cancer 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]. Venza I, et al. Class II-specific histone deacetylase inhibitors MC1568 and MC1575 suppress IL-8 expression in human melanoma cells. Pigment Cell Melanoma Res. 2013 Mar;26(2):193-204. [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. Chemical & Physical Properties Boiling Point 805.7ºC at 760 mmHg Melting Point 203-205ºC Molecular Formula C22H30Cl2N4O6 Molecular Weight 517.403 Flash Point 441.1ºC Exact Mass 516.154236 PSA 163.18000 LogP 2.39260 InChIKey ZAHQPTJLOCWVPG-UHFFFAOYSA-N SMILES Cl.Cl.O=C1c2c(O)ccc(O)c2C(=O)c2c(NCCNCCO)ccc(NCCNCCO)c21 |
| Use of | Mitoxantrone dihydrochloride is a topoisomerase II inhibitor; also inhibits protein kinase C (PKC) activity with an IC50 of 8.5 μM. Properties Articles61 Name mitoxantrone dihydrochloride Synonym More Synonyms Mitoxantrone 2HCl Biological Activity Description Mitoxantrone dihydrochloride is a topoisomerase II inhibitor; also inhibits protein kinase C (PKC) activity with an IC50 of 8.5 μM. Related Catalog Signaling Pathways >> Epigenetics >> PKC Signaling Pathways >> TGF-beta/Smad >> PKC Research Areas >> Cancer 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]. 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]. References [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]. Venza I, et al. Class II-specific histone deacetylase inhibitors MC1568 and MC1575 suppress IL-8 expression in human melanoma cells. Pigment Cell Melanoma Res. 2013 Mar;26(2):193-204. [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. Chemical & Physical Properties Exact Mass 516.154236 PSA 163.18000 LogP 2.39260 InChIKey ZAHQPTJLOCWVPG-UHFFFAOYSA-N |
| Tax Rebate | 9.0% |
| Supervision | none |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available |
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