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65271-80-9

Basic Information
CAS No.: 65271-80-9
Name: Mitoxantrone
Article Data: 14
Molecular Structure:
Molecular Structure of 65271-80-9 (Mitoxantrone)
Formula: C22H28N4O6
Molecular Weight: 444.488
Synonyms: 1,4-Bis[(2-(2-hydroxyethylamino)ethyl)amino]-5,8-dihydroxyanthraquinone;1,4-Dihydroxy-5,8-bis-[[2-[(2-hydroxyethyl)amino]ethyl]amino]anthraquinone;1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione;DHAQ;Dihydroxyanthraquinone;Mitoxanthrone;Mitozantrone;NSC 279836;Novantron;Ralenova;
EINECS: 274-619-1
Density: 1.45 g/cm3
Melting Point: 170-174 °C
Boiling Point: 805.743 °C at 760 mmHg
Flash Point: 441.098 °C
Appearance: Dark blue crystalline solid
Hazard Symbols: VeryT+
Risk Codes: 46-61-26/27/28
Safety: 53-36/37/39-45-22
PSA: 163.18000
LogP: 0.78860
Synthetic route
131401-54-2

1,4-Difluoro-5,8-dihydroxyanthracene-9,10-dione

111-41-1

2-(2-Aminoethylamino)ethanol

65271-80-9

novantrone

Conditions
ConditionsYield
With pyridine38%
81-59-4

1,4,5,8-tetrahydroxy-2,3-dihydro-9,10-anthracenedione

111-41-1

2-(2-Aminoethylamino)ethanol

65271-80-9

novantrone

Conditions
ConditionsYield
In 1,4-dioxane at 53℃; for 2.2h; Temperature; Inert atmosphere;38%
131401-54-2

1,4-Difluoro-5,8-dihydroxyanthracene-9,10-dione

111-41-1

2-(2-Aminoethylamino)ethanol

A

65271-80-9

novantrone

B

134529-38-7

6-Fluoro-8,11-dihydroxy-4-(2-hydroxy-ethyl)-1,2,3,4-tetrahydro-1,4-diaza-benzo[a]anthracene-7,12-dione

Conditions
ConditionsYield
In pyridine for 50h; Ambient temperature;A 30%
B 11%
70476-74-3

5,8-Dihydroxy-1,4-bis-[2-(2-hydroxy-ethylamino)-ethylamino]-2,3-dihydro-anthraquinone

65271-80-9

novantrone

Conditions
ConditionsYield
With chloranil In 2-methoxy-ethanol

Daunorubicin+ Mitoxantrone

B

65271-80-9

novantrone

Conditions
ConditionsYield
In water-d2 at 44.85℃; pH=7.1; Equilibrium constant;
65271-80-9

novantrone

8,11-dihydroxy-4-(2-hydroxyethyl)-6-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-1,2,3,4,7,12-hexahydronaphtho-[2,3-f]-chinoxaline-7,12-dione

Conditions
ConditionsYield
With potassium hydroxide In methanol for 5h; Heating;85%
With potassium hydroxide In methanol for 1h; Heating;82%
With sodium nitrite In water Kinetics; Further Variations:; pH-values; Oxidation;
133-89-1

UDP-glucose

65271-80-9

novantrone

1295578-41-4

mitoxantrone-4'-β-D-glucoside

Conditions
ConditionsYield
With OleD ASP enzyme In dimethyl sulfoxide at 20℃; for 27h; pH=8; aq. buffer; Enzymatic reaction;33%
65271-80-9

novantrone

Daunorubicin+ Mitoxantrone

Conditions
ConditionsYield
In water-d2 at 44.85℃; pH=7.1; Equilibrium constant; Thermodynamic data;
65271-80-9

novantrone

1,4-Bis[2-[N-(2-hydroxyethyl)trifluoroacetamido]-ethylamino]-5,8-dihydroxyanthraquinone

Conditions
ConditionsYield
In methanol; ethyl trifluoroacetate,
In methanol; ethyl trifluoroacetate,
65271-80-9

novantrone

A

C22H24N4O7

B

C22H22N4O8

C

C22H22N4O7

D

8,11-dihydroxy-4-(2-hydroxyethyl)-6-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-1,2,3,4,7,12-hexahydronaphtho-[2,3-f]-chinoxaline-7,12-dione

Conditions
ConditionsYield
With dihydrogen peroxide; horseradish peroxidase at 20℃; for 48h; pH=7.2; aq. phosphate buffer; Enzymatic reaction;
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Specification

The Mitoxantrone, with the CAS registry number 65271-80-9, is also known as 9,10-Anthracenedione,1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-. It belongs to the product categories of Pharmaceutical material and intermeidates; Intermediates & Fine Chemicals; Pharmaceuticals. This chemical's molecular formula is C22H28N4O6 and molecular weight is 444.48. What's more, its systematic name is 1,4-Dihydroxy-5,8-bis({2-[(2-hydroxyethyl)amino]ethyl}amino)-9,10-anthraquinone. Its classification codes are: (1)Analgesics; (2)Antineoplastic agents; (3)Central Nervous System Agents; (4)DNA topoisomerase II inhibitor; (5)Mutation data; (6)Peripheral Nervous System Agents; (7)Sensory System Agents. This chemical has been used in the treatment of certain types of cancer, acute myeloid leukemia, mostly metastatic breast cancer, and non-Hodgkin's lymphoma. It's also used for treating multiple sclerosis (MS), the subset known as secondary progressive MS.

Physical properties of Mitoxantrone are: (1)ACD/LogP: 1.548; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): -2.52; (4)ACD/LogD (pH 7.4): -1.58; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 10; (10)#H bond donors: 8; (11)#Freely Rotating Bonds: 16; (12)Polar Surface Area: 163.18 Å2; (13)Index of Refraction: 1.709; (14)Molar Refractivity: 119.707 cm3; (15)Molar Volume: 306.522 cm3; (16)Polarizability: 47.456×10-24cm3; (17)Surface Tension: 84.50 dyne/cm; (18)Density: 1.45 g/cm3; (19)Flash Point: 441.098 °C; (20)Enthalpy of Vaporization: 122.835 kJ/mol; (21)Boiling Point: 805.743 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation of Mitoxantrone: this chemical can be prepared by 2-(2-amino-ethylamino)-ethanol and 1,4-difluoro-5,8-dihydroxy-anthraquinone at the ambient temperature. This reaction will need solvent pyridine with the reaction time of 50 hours. The yield is about 30%.

Mitoxantrone can be prepared by 2-(2-amino-ethylamino)-ethanol and 1,4-difluoro-5,8-dihydroxy-anthraquinone at the ambient temperature

Uses of Mitoxantrone: it can be used to produce 8,11-dihydroxy-4-(2-hydroxy-ethyl)-6-[2-(2-hydroxy-ethylamino)-ethylamino]-1,2,3,4-tetrahydro-1,4-diaza-benzo[a]anthracene-7,12-dione by heating. It will need reagent KOH and solvent methanol with the reaction time of 5 hours. The yield is about 85%.

Mitoxantrone can be used to produce 8,11-dihydroxy-4-(2-hydroxy-ethyl)-6-[2-(2-hydroxy-ethylamino)-ethylamino]-1,2,3,4-tetrahydro-1,4-diaza-benzo[a]anthracene-7,12-dione by heating

When you are using this chemical, please be cautious about it as the following:
This chemical is very toxic by inhalation, in contact with skin and if swallowed. It may cause heritable genetic damage and may cause harm to the unborn child. You should not breathe dust. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible). It should be avoid exposure, and you must obtain special instructions before use.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2c1c(c(NCCNCCO)ccc1NCCNCCO)C(=O)c3c2c(O)ccc3O
(2)Std. InChI: 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
(3)Std. InChIKey: KKZJGLLVHKMTCM-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 7100ug/kg (7.1mg/kg)   Huaxi Yike Daxue Xuebao. Journal of West China University of Medical Sciences. Vol. 20, Pg. 303, 1989.
mouse LD50 intravenous 6600ug/kg (6.6mg/kg)   Huaxi Yike Daxue Xuebao. Journal of West China University of Medical Sciences. Vol. 20, Pg. 303, 1989.
mouse LD50 subcutaneous 20910ug/kg (20.91mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 unreported 86500ug/kg (86.5mg/kg)   Cancer Research. Vol. 46, Pg. 2703, 1986.
rabbit LD50 intrapleural 2mg/kg (2mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: FIBROSIS (INTERSTITIAL)
Lung. Vol. 174, Pg. 373, 1996.