ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL58
CHEMBL58
Compound Name MITOXANTRONE
ChEMBL Synonyms Mitoxantrone Dihydrochloride | Mitoxantrone Dihcl | MITOXANTRONE | MITOZANTRONE | CL 232,315 | Novantrone | MITOXANTRONE HYDROCHLORIDE
Max Phase 4 (Approved)
Trade Names MITOXANTRONE HYDROCHLORIDE | Novantrone
Molecular Formula C22H28N4O6

Additional synonyms for CHEMBL58 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES OCCNCCNc1ccc(NCCNCCO)c2C(=O)c3c(O)ccc(O)c3C(=O)c12
Standard InChI InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-1 ...
Download InChI
Standard InChI Key KKZJGLLVHKMTCM-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Metabolism Pathways
  • DrugMatrix
  • HeCaToS Compounds
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL58

Molecule Features

CHEMBL58 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:N Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
DNA inhibitor DNA DailyMed
DNA topoisomerase II alpha inhibitor DNA topoisomerase II alpha DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
NEOPLASMSD009369EFO:0000616NEOPLASM4ATC
ClinicalTrials
ClinicalTrials
MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVED020528EFO:0003840CHRONIC PROGRESSIVE MULTIPLE SCLEROSIS3ClinicalTrials
LYMPHOMAD008223EFO:0000574LYMPHOMA1ClinicalTrials
LYMPHOMA, NON-HODGKIND008228EFO:0005952NON-HODGKINS LYMPHOMA1ClinicalTrials
PROSTATIC NEOPLASMSD011471EFO:0001663PROSTATE CARCINOMA2ClinicalTrials

Clinical Data

ClinicalTrials.gov MITOXANTRONE
The Cochrane Collaboration MITOXANTRONE

Metabolites for CHEMBL58

Open in full screen

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL58. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.903
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.811
CHEMBL1163101 Serine/threonine-protein kinase/endoribonuclease IRE1 Homo sapiens 0.666
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.654
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 0.580
CHEMBL2916 Telomerase reverse transcriptase Homo sapiens 0.383
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 0.380
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.317
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.292
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 0.278



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1806 DNA topoisomerase II alpha Homo sapiens 1.000
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.988
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 0.955
CHEMBL3623 Quinone reductase 1) Homo sapiens 0.946
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 0.933
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.861
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.798
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.782
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 0.732
CHEMBL5990 Breast cancer type 1 susceptibility protein Homo sapiens 0.708
CHEMBL2885 Carbonic anhydrase III Homo sapiens 0.594
CHEMBL2916 Telomerase reverse transcriptase Homo sapiens 0.568
CHEMBL3471 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 0.560
CHEMBL5815 C-C chemokine receptor type 9 Homo sapiens 0.499
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.437
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.429
CHEMBL5973 Carbonic anhydrase 15 Mus musculus 0.392
CHEMBL2980 Arachidonate 5-lipoxygenase Bos taurus 0.293
CHEMBL1163101 Serine/threonine-protein kinase/endoribonuclease IRE1 Homo sapiens 0.291
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.248

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
444.5 444.2009 0.07 12 163.18 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
10 8 1 10 8 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
7.08 9.27 1.55 -1.58 2 32 0.17

Structural Alerts

There are 11 structural alerts for CHEMBL58. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01D - CYTOTOXIC ANTIBIOTICS AND RELATED SUBSTANCES
L01DB - Anthracyclines and related substances
L01DB07 - mitoxantrone

ChemSpider ChemSpider:KKZJGLLVHKMTCM-UHFFFAOYSA-N
DailyMed mitoxantrone hydrochloride
PubChem SID: 11111482 SID: 11111483 SID: 142727 SID: 162108252 SID: 50111146 SID: 85856281 SID: 90341083 SID: 92763439
Wikipedia Mitoxantrone

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL58



ACToR 65271-80-9 137635-96-2
BindingDB 67690
Brenda 127071 11262 132934 8142 125891
ChEBI 50729
DrugBank DB01204
DrugCentral 1821
eMolecules 742146
EPA CompTox Dashboard DTXSID4046947
FDA SRS BZ114NVM5P
Guide to Pharmacology 7242
Human Metabolome Database HMDB0015335
IBM Patent System 7A197FB534BEBFC5900E6CDDEFFDC931
KEGG Ligand C11195
LINCS LSM-2481
Mcule MCULE-5513787065
Nikkaji J19.969I
PDBe MIX
PharmGKB PA450526
PubChem 4212
PubChem: Thomson Pharma 14857298
SureChEMBL SCHEMBL3000
ZINC ZINC000003794794

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/KKZJGLLVHKMTCM-UHFFFAOYSA-N spacer
spacer