mitoxantrone Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
antineoplastics; anthraquinone derivatives 1821 65271-80-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mitoxantrone
  • mitoxantrone hydrochloride
  • dihydroxyanthraquinone
  • mitoxanthrone
  • mitozantrone
  • nimitoxantron
  • mitoxantrone dihydrochloride
  • mitoxantrone HCl
An anthracenedione-derived antineoplastic agent.
  • Molecular weight: 444.49
  • Formula: C22H28N4O6
  • CLOGP: 2.30
  • LIPINSKI: 1
  • HAC: 10
  • HDO: 8
  • TPSA: 163.18
  • ALOGS: -2.78
  • ROTB: 12

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
Dec. 23, 1987 FDA

FDA Adverse Event Reporting System

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Febrile neutropenia 1343.30 75.58 330 2187 25982 4610493
Neutropenia 675.62 75.58 221 2296 47729 4588746
Acute myeloid leukaemia 667.20 75.58 147 2370 6898 4629577
Myelodysplastic syndrome 644.73 75.58 143 2374 6915 4629560
Sepsis 454.16 75.58 160 2357 42679 4593796
Thrombocytopenia 371.21 75.58 142 2375 47531 4588944
Bone marrow failure 342.16 75.58 97 2420 12641 4623834
Pneumonia 283.70 75.58 148 2369 102667 4533808
Pyrexia 272.26 75.58 146 2371 106998 4529477
Infection 246.41 75.58 98 2419 36044 4600431
Second primary malignancy 239.31 75.58 54 2463 2774 4633701
Differentiation syndrome 233.53 75.58 39 2478 389 4636086
Septic shock 232.91 75.58 77 2440 16689 4619786
Pancytopenia 217.89 75.58 81 2436 24772 4611703
Acute promyelocytic leukaemia 202.49 75.58 35 2482 435 4636040
Leukaemia recurrent 199.11 75.58 37 2480 708 4635767
Respiratory failure 195.28 75.58 79 2438 30247 4606228
Product use in unapproved indication 194.82 75.58 75 2442 25198 4611277
Acute lymphocytic leukaemia recurrent 176.70 75.58 33 2484 649 4635826
Colitis 173.25 75.58 55 2462 10444 4626031
Mucosal inflammation 165.01 75.58 54 2463 11289 4625186
Febrile bone marrow aplasia 157.44 75.58 36 2481 1956 4634519
Multiple organ dysfunction syndrome 138.46 75.58 54 2463 18702 4617773
Off label use 133.71 75.58 100 2417 129013 4507462
Leukopenia 127.36 75.58 53 2464 21683 4614792
Hypotension 124.72 75.58 75 2442 67325 4569150
Cardiac failure 118.93 75.58 54 2463 27234 4609241
Haemophagocytic lymphohistiocytosis 116.73 75.58 31 2486 3128 4633347
Bacteraemia 113.40 75.58 32 2485 4048 4632427
Cardiomyopathy 112.78 75.58 35 2482 6149 4630326
Fungal infection 112.03 75.58 37 2480 7932 4628543
Aspergillus infection 111.33 75.58 29 2488 2714 4633761
Cardiotoxicity 109.04 75.58 29 2488 2941 4633534
Mucormycosis 104.95 75.58 24 2493 1301 4635174
Acute lymphocytic leukaemia 102.14 75.58 23 2494 1163 4635312
Neoplasm recurrence 100.52 75.58 22 2495 975 4635500
Bronchopulmonary aspergillosis 99.39 75.58 27 2490 2967 4633508
Haematotoxicity 93.10 75.58 26 2491 3163 4633312
Hepatitis B 87.27 75.58 24 2493 2759 4633716
Anaemia 86.43 75.58 61 2456 71499 4564976
Clostridium bacteraemia 84.35 75.58 13 2504 73 4636402
Bacterial sepsis 83.62 75.58 20 2497 1318 4635157
Malignant neoplasm progression 79.89 75.58 42 2475 28994 4607481
Lower respiratory tract infection fungal 77.21 75.58 13 2504 136 4636339
Disease progression 76.61 75.58 46 2471 40965 4595510
Candida infection 76.11 75.58 25 2492 5256 4631219

Pharmacologic Action:

SourceCodeDescription
ATC L01DB07 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES
Anthracyclines and related substances
FDA EPC N0000175609 Topoisomerase Inhibitor
FDA MoA N0000000176 Topoisomerase Inhibitors
MeSH PA D000700 Analgesics
MeSH PA D000970 Antineoplastic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35610 antineoplastic agent
MeSH PA D059005 Topoisomerase II Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute myeloid leukemia, disease indication 91861009
Relapsing remitting multiple sclerosis indication 426373005 DOID:2378
Metastatic Prostate Carcinoma indication
Follicular non-Hodgkin's lymphoma off-label use 308121000
Metastatic Breast Carcinoma off-label use
Progressive Diffuse Large B-Cell Lymphoma off-label use
Mycosis contraindication 3218000 DOID:1564
Viral disease contraindication 34014006 DOID:934
Chronic heart failure contraindication 48447003
Hepatic failure contraindication 59927004
Acute infectious disease contraindication 63171007
Leukopenia contraindication 84828003 DOID:615
Left heart failure contraindication 85232009
Bacterial infectious disease contraindication 87628006
Radiation oncology AND/OR radiotherapy contraindication 108290001
Acute disease of cardiovascular system contraindication 128487001
Seizure disorder contraindication 128613002
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.37 acidic
pKa2 10.7 acidic
pKa3 9.13 Basic
pKa4 8.52 Basic
pKa5 4.01 Basic
pKa6 1.49 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA topoisomerase 2-alpha Enzyme INHIBITOR IC90 5.96 WOMBAT-PK CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel Ki 5.53 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.31 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 5.73 DRUG MATRIX
Muscarinic acetylcholine receptor M1 GPCR Ki 6.74 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 7.11 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 7.05 DRUG MATRIX
Epidermal growth factor receptor Kinase IC50 5.27 DRUG MATRIX
Tyrosine-protein kinase Fyn Kinase IC50 5.90 DRUG MATRIX
Receptor tyrosine-protein kinase erbB-2 Kinase IC50 5.69 DRUG MATRIX
ATP-binding cassette sub-family G member 2 Transporter Kact 5.15 WOMBAT-PK
Multidrug resistance-associated protein 1 Transporter IC50 6.29 WOMBAT-PK
Canalicular multispecific organic anion transporter 1 Transporter WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 5.84 WOMBAT-PK
Solute carrier family 22 member 3 Transporter IC50 4.22 CHEMBL
Solute carrier family 22 member 1 Transporter IC50 4.36 CHEMBL
Solute carrier family 22 member 2 Transporter IC50 4.13 CHEMBL
Tyrosine-protein kinase BTK Kinase IC50 6 CHEMBL
Serine/threonine-protein kinase pim-1 Kinase IC50 7.29 CHEMBL
Multidrug and toxin extrusion protein 2 Transporter IC50 6.28 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 6.72 CHEMBL
DNA-3-methyladenine glycosylase Enzyme IC50 5.60 CHEMBL
Arachidonate 15-lipoxygenase Enzyme IC50 5.75 DRUG MATRIX
Integrase Enzyme IC50 5.42 CHEMBL
Dual specificity tyrosine-phosphorylation-regulated kinase 1A Unclassified AC50 5.02 CHEMBL

External reference:

IDSource
4019842 VUID
N0000147929 NUI
C0026259 UMLSCUI
D02166 KEGG_DRUG
108791001 SNOMEDCT_US
386913001 SNOMEDCT_US
4019842 VANDF
7005 RXNORM
d00306 MMSL
004828 NDDF
BZ114NVM5P UNII
4922 INN_ID
CHEMBL58 ChEMBL_ID
70476-82-3 SECONDARY_CAS_RN
MIX PDB_CHEM_ID
DB01204 DRUGBANK_ID
CHEBI:50729 CHEBI
CHEMBL1417019 ChEMBL_ID
D008942 MESH_DESCRIPTOR_UI
4212 PUBCHEM_CID
7242 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
mitoXANTRONE HUMAN PRESCRIPTION DRUG LABEL 1 0703-4680 INJECTION, SOLUTION, CONCENTRATE 2 mg INTRAVENOUS ANDA 15 sections
mitoXANTRONE HUMAN PRESCRIPTION DRUG LABEL 1 0703-4685 INJECTION, SOLUTION, CONCENTRATE 2 mg INTRAVENOUS ANDA 15 sections
mitoXANTRONE HUMAN PRESCRIPTION DRUG LABEL 1 0703-4686 INJECTION, SOLUTION, CONCENTRATE 2 mg INTRAVENOUS ANDA 15 sections
Mitoxantrone HUMAN PRESCRIPTION DRUG LABEL 1 61703-343 INJECTION, SOLUTION, CONCENTRATE 2 mg INTRAVENOUS ANDA 16 sections
Mitoxantrone HUMAN PRESCRIPTION DRUG LABEL 1 63323-132 INJECTION, SOLUTION 2 mg INTRAVENOUS ANDA 15 sections