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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 NOVANTRONE | MITOXANTRONE | MITOXANTRONE HYDROCHLORIDE | Novantrone | Mitoxantrone Dihcl | CL 232,315 | MITOZANTRONE | Mitoxantrone Dihydrochloride
Max Phase 4 (Approved)
Trade Names MITOXANTRONE HYDROCHLORIDE | Novantrone | 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
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma2ClinicalTrials
ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ClinicalTrials
ATC
ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
ClinicalTrials
Multiple SclerosisD009103EFO:0003885multiple sclerosis3ClinicalTrials
ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma3ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia3ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000196metastatic prostate cancer3ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma3ClinicalTrials
Sarcoma, MyeloidD023981EFO:1001052myeloid sarcoma3ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia1ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials
Sarcoma, MyeloidD023981EFO:1000286Granulocytic Sarcoma3ClinicalTrials
Leukemia, Promyelocytic, AcuteD015473EFO:0000224acute promyelocytic leukemia3ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells3ClinicalTrials
Multiple Sclerosis, Chronic ProgressiveD020528EFO:0003840chronic progressive multiple sclerosis3ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-LymphomaD054218EFO:1001830precursor T-cell lymphoblastic leukemia-lymphoma1ClinicalTrials
Multiple Sclerosis, Relapsing-RemittingD020529EFO:0003929relapsing-remitting multiple sclerosis2ClinicalTrials
PainD010146EFO:0003843pain3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials

Clinical Data

ClinicalTrials.gov MITOXANTRONE
The Cochrane Collaboration MITOXANTRONE

Metabolites for CHEMBL58

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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 0.920
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.891
CHEMBL1163101 Serine/threonine-protein kinase/endoribonuclease IRE1 Homo sapiens 0.815
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.744
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 0.698
CHEMBL2916 Telomerase reverse transcriptase Homo sapiens 0.555
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 0.541
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.483
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.397
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 0.386
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.357
CHEMBL3587 Dual specificity mitogen-activated protein kinase kinase 1 Homo sapiens 0.326
CHEMBL261 Carbonic anhydrase I Homo sapiens 0.316
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 0.259
CHEMBL3242 Carbonic anhydrase XII Homo sapiens 0.253



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1806 DNA topoisomerase II alpha Homo sapiens 1.000
CHEMBL3729 Carbonic anhydrase IV Homo sapiens 0.986
CHEMBL3969 Carbonic anhydrase VB Homo sapiens 0.971
CHEMBL3623 Quinone reductase 1) Homo sapiens 0.967
CHEMBL4789 Carbonic anhydrase VA Homo sapiens 0.960
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.907
CHEMBL3025 Carbonic anhydrase VI Homo sapiens 0.826
CHEMBL5990 Breast cancer type 1 susceptibility protein Homo sapiens 0.810
CHEMBL1947 Thyroid hormone receptor beta-1 Homo sapiens 0.795
CHEMBL3308 Caspase-6 Homo sapiens 0.778
CHEMBL205 Carbonic anhydrase II Homo sapiens 0.754
CHEMBL2885 Carbonic anhydrase III Homo sapiens 0.721
CHEMBL2326 Carbonic anhydrase VII Homo sapiens 0.683
CHEMBL3510 Carbonic anhydrase XIV Homo sapiens 0.677
CHEMBL1163101 Serine/threonine-protein kinase/endoribonuclease IRE1 Homo sapiens 0.632
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.598
CHEMBL2916 Telomerase reverse transcriptase Homo sapiens 0.551
CHEMBL5619 DNA-(apurinic or apyrimidinic site) lyase Homo sapiens 0.544
CHEMBL5973 Carbonic anhydrase 15 Mus musculus 0.498
CHEMBL3471 Human immunodeficiency virus type 1 integrase Human immunodeficiency virus 1 0.496

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
444.5 444.2009 -0.14 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 0.14

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 11262 127071 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
MolPort MolPort-003-849-239
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
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