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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL44657
CHEMBL44657
Compound Name ETOPOSIDE
ChEMBL Synonyms ETOPOSIDE | VEPESID | TOPOSAR | VP-16-213
Max Phase 4 (Approved)
Trade Names VEPESID | ETOPOSIDE | TOPOSAR
Molecular Formula C29H32O13

Additional synonyms for CHEMBL44657 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1cc(cc(OC)c1O)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](O[C@@H]4O[C ...
Download SMILES
Standard InChI InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41- ...
Download InChI
Standard InChI Key VJJPUSNTGOMMGY-MRVIYFEKSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Open TG-GATEs
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • 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


CHEMBL44657

Molecule Features

CHEMBL44657 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

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

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Adrenocortical CarcinomaD018268EFO:0003093adrenocortical carcinoma3ClinicalTrials
Autoimmune DiseasesD001327EFO:0005140autoimmune disease2ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma3ClinicalTrials
GliosarcomaD018316EFO:1001465gliosarcoma2ClinicalTrials
HIV InfectionsD015658EFO:0000180HIV-1 infection3ClinicalTrials
Hematologic DiseasesD006402HP:0001871abnormality of blood and blood-forming tissues2ClinicalTrials
Lymphohistiocytosis, HemophagocyticD051359Orphanet:158038Primary hemophagocytic lymphohistiocytosis3ClinicalTrials
Lymphoma, AIDS-RelatedD016483EFO:1001365Lymphoma, AIDS-Related2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma3ClinicalTrials
RetinoblastomaD012175Orphanet:790Retinoblastoma3ClinicalTrials
Anemia, RefractoryD000753EFO:0003802refractory anemia2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
LeukemiaD007938EFO:0000565leukemia3ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
Leukemia, Myelomonocytic, AcuteD015479EFO:0000223acute myelomonocytic leukemia3ClinicalTrials
Leukemia, Plasma CellD007952EFO:0006475plasma cell leukemia1ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma3ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma3ClinicalTrials
ThymomaD013945EFO:1000581Thymoma2ClinicalTrials
Carcinoma, Merkel CellD015266EFO:1001471Merkel cell skin cancer2ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma3ClinicalTrials
Multiple Sclerosis, Relapsing-RemittingD020529EFO:0003929relapsing-remitting multiple sclerosis2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
DailyMed
OligodendrogliomaD009837EFO:0000632oligodendroglioma1ClinicalTrials
Rhabdomyosarcoma, EmbryonalD018233EFO:0000437embryonal rhabdomyosarcoma2ClinicalTrials
Thymus NeoplasmsD013953EFO:0002626thymus neoplasm3ClinicalTrials
Wilms TumorD009396Orphanet:654Nephroblastoma3ClinicalTrials
AstrocytomaD001254EFO:0002499anaplastic astrocytoma1ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma3ClinicalTrials
EpendymomaD004806EFO:1000028ependymoma3ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer3ClinicalTrials
Leukemia, Basophilic, AcuteD015471EFO:0003029acute basophilic leukemia3ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome3ClinicalTrials
OsteosarcomaD012516EFO:0000637osteosarcoma3ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma2ClinicalTrials
Rhabdomyosarcoma, AlveolarD018232EFO:0000248alveolar rhabdomyosarcoma2ClinicalTrials
SarcomaD012509EFO:0000691sarcoma3ClinicalTrials
Sarcoma, MyeloidD023981EFO:1001052myeloid sarcoma3ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma3ClinicalTrials
Carcinoma, Renal CellD002292EFO:0002890renal carcinoma3ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000708squamous cell lung carcinoma3ClinicalTrials
Colorectal NeoplasmsD015179EFO:0005842colorectal cancer3ClinicalTrials
Gestational Trophoblastic DiseaseD031901Orphanet:59305Gestational trophoblastic neoplasm3ClinicalTrials
Leukemia, Biphenotypic, AcuteD015456EFO:0000209T-cell acute lymphoblastic leukemia1ClinicalTrials
Lymphoma, Large-Cell, AnaplasticD017728EFO:0003032anaplastic large cell lymphoma2ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma3ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma3ClinicalTrials
Neoplasms, Germ Cell and EmbryonalD009373EFO:0000514germ cell tumor3ClinicalTrials
OligodendrogliomaD009837EFO:0000630oligoastrocytoma1ClinicalTrials
Sarcoma, KaposiD012514EFO:0000558Kaposi's sarcoma1ClinicalTrials
Testicular NeoplasmsD013736EFO:0004281testicular neoplasm3ClinicalTrials
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma3ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma2ClinicalTrials
HistiocytomaD051642EFO:0005561histiocytoma3ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia2ClinicalTrials
Leukemia, Megakaryoblastic, AcuteD007947EFO:0003025acute megakaryoblastic leukaemia3ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0003027acute myeloblastic leukemia without maturation3ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells3ClinicalTrials
Lymphoma, T-Cell, PeripheralD016411EFO:0000211unspecified peripheral T-cell lymphoma2ClinicalTrials
Neuroectodermal Tumors, PrimitiveD018242EFO:0005235primitive neuroectodermal tumor3ClinicalTrials
RhabdomyosarcomaD012208EFO:0002918rhabdomyosarcoma3ClinicalTrials
Brain NeoplasmsD001932EFO:0003833brain neoplasm0ClinicalTrials
Choroid Plexus NeoplasmsD016545EFO:0007206choroid plexus cancer3ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma3ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma3ClinicalTrials
NeutropeniaD0095032ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma3ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
DiseaseD004194EFO:0000408disease1ClinicalTrials
GliomaD005910EFO:0005543glioma3ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia2ClinicalTrials
Leukemia, Monocytic, AcuteD007948EFO:0000221acute monocytic leukemia3ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
Sarcoma, EwingD012512EFO:0000174Ewing sarcoma3ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma3ClinicalTrials
Testicular NeoplasmsD013736EFO:0005088testicular carcinoma3ClinicalTrials

Clinical Data

ClinicalTrials.gov ETOPOSIDE
The Cochrane Collaboration ETOPOSIDE

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 CHEMBL44657. 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
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 1.000
CHEMBL3394 Tubulin beta chain Bos taurus 1.000
CHEMBL4372 Anthrax lethal factor Bacillus anthracis 0.998
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.997
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.955
CHEMBL2717 Phosphodiesterase 11A Homo sapiens 0.847



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1743121 Solute carrier organic anion transporter family member 1B3 Homo sapiens 1.000
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 1.000
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.817
CHEMBL1973 Tyrosinase Homo sapiens 0.745
CHEMBL1293237 Bloom syndrome protein Homo sapiens 0.342
CHEMBL1697668 Solute carrier organic anion transporter family member 1B1 Homo sapiens 0.267

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
588.6 588.1843 1.34 5 160.83 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
13 3 2 13 3 2


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.94 - .28 .27 2 42 0.43

Structural Alerts

There are 2 structural alerts for CHEMBL44657. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01C - PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS
L01CB - Podophyllotoxin derivatives
L01CB01 - etoposide

ChemSpider ChemSpider:VJJPUSNTGOMMGY-MRVIYFEKSA-N
DailyMed etoposide
PubChem SID: 164339423 SID: 56463308
Wikipedia Etoposide

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL44657



ACToR 121471-01-0
Atlas etoposide
BindingDB 50127140
Brenda 49045 98367 92457 154445 21602 153455 147647 774
ChEBI 4911
DrugBank DB00773
DrugCentral 1112
eMolecules 32278021 537894
FDA SRS 6PLQ3CP4P3
Guide to Pharmacology 6815
Human Metabolome Database HMDB0014911
IBM Patent System 3CEF3C0AD6607B3D03CAE02F8800C115
KEGG Ligand C01576
LINCS LSM-6348
MolPort MolPort-006-069-121
NIH Clinical Collection SAM001246880
Nikkaji J3.178J
PDBe EVP
PharmGKB PA449552
PubChem 36462
PubChem: Drugs of the Future 12013288
PubChem: Thomson Pharma 14886949 14935915
Selleck Etopophos
SureChEMBL SCHEMBL4259
ZINC ZINC000003938684

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