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Details

Stereochemistry ACHIRAL
Molecular Formula C22H28N4O6
Molecular Weight 444.4809
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MITOXANTRONE

SMILES

OCCNCCNC1=CC=C(NCCNCCO)C2=C1C(=O)C3=C(C2=O)C(O)=CC=C3O

InChI

InChIKey=KKZJGLLVHKMTCM-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H28N4O6
Molecular Weight 444.4809
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Mitoxantrone (NOVANTRONE) is a synthetic antineoplastic anthracenedione. 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. Mitoxantrone 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. NOVANTRONE is indicated for reducing neurologic disability and/or the frequency of clinical relapses in patients with secondary (chronic) progressive, progressive relapsing, or worsening relapsing-remitting multiple sclerosis (i.e., patients whose neurologic status is significantly abnormal between relapses). NOVANTRONE in combination with corticosteroids is indicated as initial chemotherapy for the treatment of patients with pain related to advanced hormone-refractory prostate cancer. NOVANTRONE in combination with other approved drug(s) is indicated in the initial therapy of acute nonlymphocytic leukemia (ANLL) in adults. This category includes myelogenous, promyelocytic, monocytic, and erythroid acute leukemias.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NOVANTRONE
Primary
NOVANTRONE
Primary
NOVANTRONE

Cmax

ValueDoseCo-administeredAnalytePopulation
6.429 mg/L
90 mg/m² single, intravenous
MITOXANTRONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
5.195 mg × h/L
90 mg/m² single, intravenous
MITOXANTRONE plasma
Homo sapiens
1922 ng × h/mL
40 mg/m² single, intravenous
MITOXANTRONE plasma
Homo sapiens
1.26 μg × h/mL
12 mg/m² 1 times / 3 weeks multiple, intravenous
MITOXANTRONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
37.1 h
40 mg/m² single, intravenous
MITOXANTRONE plasma
Homo sapiens
19.83 h
12 mg/m² 1 times / 3 weeks multiple, intravenous
MITOXANTRONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
22%
MITOXANTRONE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dosage of NOVANTRONE (Mitoxantrone) is 12 mg/m2 given as a short (approximately 5 to 15 minutes) intravenous infusion every 3 months.
Route of Administration: Intravenous
In Vitro Use Guide
Treatment of B-CLL cells for 48 h with mitoxantrone (0.5 ug/ml) induced a decrease in cell viability as determined by MTT assay.
Substance Class Chemical
Record UNII
BZ114NVM5P
Record Status Validated (UNII)
Record Version