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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL58
CHEMBL58
Compound Name MITOXANTRONE
ChEMBL Synonyms CL-232315 | Novantrone | Mitoxantrone | Mitoxantrone HCl | Mitoxantrone Dihcl | Mitoxantrone Dihydrochloride
Max Phase 4 (Approved)
Trade Names Novantrone | Mitoxantrone HCl
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

Mechanism of Action

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

Indications for CHEMBL58

MESH Heading MESH ID EFO ID EFO Term Max phase for indication
LEUKEMIA, MYELOID, ACUTED015470EFO:0000222ACUTE MYELOID LEUKEMIA3
LEUKEMIA, PROMYELOCYTIC, ACUTED015473EFO:0000224ACUTE PROMYELOCYTIC LEUKEMIA3
LYMPHOMAD008223EFO:0000574LYMPHOMA1
MULTIPLE SCLEROSIS, CHRONIC PROGRESSIVED020528EFO:0003840CHRONIC PROGRESSIVE MULTIPLE SCLEROSIS3
NEOPLASMSD009369EFO:0000616NEOPLASM1
PROSTATIC NEOPLASMSD011471EFO:0001663PROSTATE CARCINOMA2

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

Clinical Data

Number of clinical trials registered at clinicaltrials.gov
Number of reviews at The Cochrane Collaboration
Number of entries at British National Formulary

Structural Alerts

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

Alternate Forms of Compound in ChEMBL


CHEMBL58

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 0.893
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.451
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 0.263
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.253
CHEMBL2916 Telomerase reverse transcriptase Homo sapiens 0.229

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1806 DNA topoisomerase II alpha Homo sapiens 1.000
CHEMBL3623 Quinone reductase 1) Homo sapiens 0.941
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 0.939
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.924
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 0.913
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.829
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.764
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 0.724
CHEMBL5990 Breast cancer type 1 susceptibility protein Homo sapiens 0.697
CHEMBL2885 Carbonic anhydrase III Homo sapiens 0.572
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.562
CHEMBL3471 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 0.543
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.465
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 0.451
CHEMBL261 Carbonic anhydrase I Homo sapiens 0.402
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.378
CHEMBL5973 Carbonic anhydrase 15 Mus musculus 0.349
CHEMBL3594 Carbonic anhydrase IX Homo sapiens 0.314
CHEMBL2916 Telomerase reverse transcriptase Homo sapiens 0.281
CHEMBL2980 Arachidonate 5-lipoxygenase Bos taurus 0.278

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

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
ChEBI 50729
DrugBank DB01204
eMolecules 742146
EPA CompTox Dashboard DTXSID4046947
FDA SRS BZ114NVM5P
Guide to Pharmacology 7242
Human Metabolome Database HMDB15335
IBM Patent System 7A197FB534BEBFC5900E6CDDEFFDC931
KEGG Ligand C11195
LINCS LSM-2481
Mcule MCULE-5513787065
Nikkaji J19.969I
PDBe MIX
PubChem 4212
PubChem: Thomson Pharma 14857298
SureChEMBL SCHEMBL3000

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