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 826.79 62.64 202 1394 18773 3365490
Myelodysplastic syndrome 605.38 62.64 126 1470 5521 3378742
Neutropenia 582.93 62.64 173 1423 33213 3351050
Acute myeloid leukaemia 459.64 62.64 99 1497 5074 3379189
Thrombocytopenia 249.28 62.64 93 1503 35175 3349088
Sepsis 234.65 62.64 87 1509 32286 3351977
Pyrexia 169.19 62.64 91 1505 81024 3303239
Pancytopenia 163.67 62.64 58 1538 18762 3365501
Septic shock 163.25 62.64 52 1544 12132 3372131
Acute promyelocytic leukaemia 150.89 62.64 25 1571 291 3383972
Bone marrow failure 150.81 62.64 45 1551 8442 3375821
Acute promyelocytic leukaemia differentiation syndrome 137.13 62.64 22 1574 206 3384057
Infection 136.25 62.64 55 1541 25347 3358916
Pneumonia 132.95 62.64 74 1522 70069 3314194
Respiratory failure 123.69 62.64 50 1546 23091 3361172
Mucosal inflammation 114.80 62.64 36 1560 7947 3376316
Colitis 114.57 62.64 35 1561 7086 3377177
Acute lymphocytic leukaemia 108.12 62.64 22 1574 832 3383431
Leukaemia recurrent 97.91 62.64 19 1577 561 3383702
Hepatitis B 95.03 62.64 24 1572 2409 3381854
Bacteraemia 90.89 62.64 24 1572 2871 3381392
Clostridium bacteraemia 89.88 62.64 13 1583 55 3384208
Acute lymphocytic leukaemia recurrent 84.96 62.64 16 1580 401 3383862
Cardiomyopathy 78.27 62.64 24 1572 4902 3379361
Multiple organ dysfunction syndrome 72.96 62.64 30 1566 14380 3369883
Off label use 70.66 62.64 45 1551 53932 3330331
Bacterial sepsis 70.12 62.64 16 1580 1041 3383222
Ameloblastoma 69.91 62.64 9 1587 11 3384252
Histiocytosis haematophagic 68.93 62.64 18 1578 2058 3382205
Hypotension 64.08 62.64 41 1555 49473 3334790

Pharmacologic Action:

SourceCodeDescription
ATC L01DB07 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES
Anthracyclines and related substances
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
MeSH PA D059005 Topoisomerase II Inhibitors
MeSH PA D059003 Topoisomerase Inhibitors
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35610 antineoplastic agent
FDA EPC N0000175609 Topoisomerase Inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acute myeloid leukemia, disease indication 91861009 DOID:9119
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 DOID:104
Radiation oncology AND/OR radiotherapy contraindication 108290001
Acute disease of cardiovascular system contraindication 128487001
Seizure disorder contraindication 128613002 DOID:1826
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
7242 IUPHAR_LIGAND_ID
D02166 KEGG_DRUG
CHEMBL58 ChEMBL_ID
386913001 SNOMEDCT_US
4019842 VANDF
7005 RXNORM
108791001 SNOMEDCT_US
d00306 MMSL
N0000005740 NDFRT
N0000147929 NDFRT
004828 NDDF
4212 PUBCHEM_CID
CHEMBL1417019 ChEMBL_ID
BZ114NVM5P UNII
4922 INN_ID
DB01204 DRUGBANK_ID
D008942 MESH_DESCRIPTOR_UI
70476-82-3 SECONDARY_CAS_RN
CHEBI:50729 CHEBI
MIX PDB_CHEM_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