Mitoxantrone
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Basic information
- CAS
65271-80-9- Standard SMILES
O=C1c2c(O)ccc(O)c2C(=O)c2c(NCCNCCO)ccc(NCCNCCO)c21- InChIKey
KKZJGLLVHKMTCM-UHFFFAOYSA-N- Molecular formula
- C22H28N4O6
- Average molar mass
- 444.5 g/mol
- Monoisotopic mass
- 444.20088462
Overview
Mitoxantrone is a dihydroxyanthraquinone that is 1,4-dihydroxy-9,10-anthraquinone which is substituted by 6-hydroxy-1,4-diazahexyl groups at positions 5 and 8. It has a role as an analgesic and an antineoplastic agent.
Names & identifiers
- Preferred name
- Mitoxantrone
- IUPAC
- 1,4-dihydroxy-5,8-bis[2-(2-hydroxyethylamino)ethylamino]anthracene-9,10-dione
- English name
- Mitoxantrone
- Molecular formula
- C22H28N4O6
- Molecular weight
- 444.48
Names & synonyms
mitoxantrone65271-80-9MitozantroneMitoxanthroneDHAQMitoxantronMitoxantronaMitoxantronumMisostolNSC-279836NSC 279836BZ114NVM5P
Show more names
itoxantronedihydroxyanthraquinoneNSC-27983MitoxantroneBasePharmasubstanceEP4
NSC2798361,4-Bis(2-(2-hydroxyethylamino)ethyl)amino)-5,8-dihydroxyanthraquinone1,4-Dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedioneDTXSID40469471,4-DIHYDROXY-5,8-BIS({2-[(2-HYDROXYETHYL)AMINO]ETHYL}AMINO)-9,10-ANTHRACENEDIONECHEBI:50729L01DB07Ralenova
Database identifiers
- CAS
65271-80-9- PubChem CID
- 4212
- DTXSID
DTXSID4046947- ChEMBL
CHEMBL58- ChEBI
CHEBI:50729- UNII
- BZ114NVM5P
- EC Number
- 833-758-3
- Nikkaji
- J19.969I、J710.751J
Properties
Computed structural propertiesFilling in
- XLogP
- 1
- Topological polar surface area
- 163 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 12
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 571
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP
-3.1
0.07
Solubility7.34e-01 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Antineoplastic Agents
Physical DescriptionLiquid
Collision Cross Section198.57 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 170 · 170-1740C
- Boiling point
- 554.47 °C · 554.47°C (rough estimate)
- Density
- 1.3049 · 1.3049 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory InformationHazard Traits - Carcinogenicity
Hazard Classes and CategoriesCarc. 2 (100%)
Toxicology
Health EffectsCardiomyopathy is a particularly concerning effect as it is irreversible. [Wikipedia]
Hepatotoxicity
Chemotherapy with mitoxantrone alone is associated with serum enzyme elevations in up to 40% of patients, but these elevations are generally mild-to-moderate in severity, transient and not accompanied by symptoms or jaundice. Higher rates of liver enzyme elevations have been reported with combination chemotherapeutic regimens that include mitoxantrone. In high doses, mitoxantrone has been associated with a high rate of jaundice, but the degree of hyperbilirubinemia has been mild, transient and not associated with significant serum enzyme elevations or evidence of hepatitis. Rare instances of acute liver injury have been reported in patients taking mitoxantrone, including a single case of drug-rash with eosinophilia and systemic symptoms (DRESS). The latency to onset was 8 weeks and the pattern of serum enzyme elevations was cholestatic and later mixed. Immunoallergic features were prominent and appeared to respond to corticosteroid therapy. Other drugs were being taken and the association with mitoxantrone was not definite (Case 1). Thus, idiosyncratic and clinically apparent liver injury from mitoxantrone may occur but is quite rare.
Chemistry & industry
Pharmacology
ATC Code
L01DB07
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Protein Binding78%
PharmacodynamicsMitoxantrone has been shown in vitro to inhibit B cell, T cell, and macrophage proliferation and impair antigen presentation, as well as the secretion of interferon gamma, TNFa, and IL-2.
Mechanism of Action
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.
Biological Half-Life75 hours
Metabolism/Metabolites
Hepatic
Hepatic Half Life: 75 hours
FDA Pharmacological Classification
BZ114NVM5P
MITOXANTRONE
Established Pharmacologic Class [EPC] - Topoisomerase Inhibitor
Mechanisms of Action [MoA] - Topoisomerase Inhibitors
Mitoxantrone is a Topoisomerase Inhibitor. The mechanism of action of mitoxantrone is as a Topoisomerase Inhibitor.
MITOXANTRONE
MeSH Pharmacological Classification
Compounds capable of relieving pain without the loss of CONSCIOUSNESS.
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.
Related reactions
22 records
Compound notes
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