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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL84
CHEMBL84
Compound Name TOPOTECAN
ChEMBL Synonyms HYCAMTIN | Hycamptin | POTACTASOL | SK-S-104864-A | SK&F S-104864-A | Topotecan | TOPOTECAN | TOPOTECAN HYDROCHLORIDE
Max Phase 4 (Approved)
Trade Names TOPOTECAN | TOPOTECAN HYDROCHLORIDE | POTACTASOL | Hycamptin | HYCAMTIN
Molecular Formula C23H23N3O5

Additional synonyms for CHEMBL84 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC[C@@]1(O)C(=O)OCC2=C1C=C3N(Cc4cc5c(CN(C)C)c(O)ccc5nc34)C2= ...
Download SMILES
Standard InChI InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)1 ...
Download InChI
Standard InChI Key UCFGDBYHRUNTLO-QHCPKHFHSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Orange Book
  • 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


CHEMBL84

Molecule Features

CHEMBL84 compound icon
Drug Type:Natural Product-derived Rule of Five:Y 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 I, mitochondrial inhibitor DNA topoisomerase I, mitochondrial DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome2ClinicalTrials
Wilms TumorD009396Orphanet:654Nephroblastoma2ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
AstrocytomaD001254EFO:0002499anaplastic astrocytoma1ClinicalTrials
Breast NeoplasmsD001943EFO:0003869breast neoplasm2ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma1ClinicalTrials
DiseaseD004194EFO:0000408disease1ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma1ClinicalTrials
Fallopian Tube NeoplasmsD005185EFO:1000251Fallopian Tube Carcinoma2ClinicalTrials
Genital Neoplasms, FemaleD005833EFO:1001331Genital neoplasm, female1ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia2ClinicalTrials
Peritoneal NeoplasmsD010534EFO:1001100peritoneal neoplasm2ClinicalTrials
CarcinomaD002277EFO:0000313carcinoma1ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Lung NeoplasmsD008175EFO:0001071lung carcinoma3ClinicalTrials
OligodendrogliomaD009837EFO:0000630oligoastrocytoma1ClinicalTrials
OligodendrogliomaD009837EFO:0002501anaplastic oligodendroglioma1ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001416cervical adenocarcinoma3ClinicalTrials
Ovarian NeoplasmsD010051Orphanet:398934Malignant epithelial tumor of ovary3ClinicalTrials
ClinicalTrials
Uterine Cervical NeoplasmsD002583EFO:0001061cervical carcinoma3ClinicalTrials
ClinicalTrials
Uterine NeoplasmsD014594EFO:0003859uterine neoplasm2ClinicalTrials
GliosarcomaD018316EFO:1001465gliosarcoma2ClinicalTrials
Meningeal NeoplasmsD008577EFO:0003851meningeal neoplasm1ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma2ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma3ClinicalTrials
RetinoblastomaD012175Orphanet:790Retinoblastoma3ClinicalTrials
Brain NeoplasmsD001932EFO:0003833brain neoplasm1ClinicalTrials
LymphomaD008223EFO:0000574lymphoma2ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma2ClinicalTrials
Rectal NeoplasmsD012004EFO:1000657rectum cancer1ClinicalTrials
SarcomaD012509EFO:0000691sarcoma3ClinicalTrials
Sarcoma, EwingD012512EFO:0000174Ewing sarcoma3ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme1ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma3ClinicalTrials
ClinicalTrials
Mediastinal NeoplasmsD008479EFO:0007362mediastinal cancer2ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia3ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma3ClinicalTrials
ClinicalTrials
Ovarian NeoplasmsD010051EFO:0003893ovarian neoplasm3ClinicalTrials
ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma3ClinicalTrials
ClinicalTrials
Colonic NeoplasmsD003110EFO:1001950colon carcinoma2ClinicalTrials
Endometrial NeoplasmsD016889EFO:0004230endometrial neoplasm2ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer2ClinicalTrials
Neuroectodermal Tumors, PrimitiveD018242EFO:0005235primitive neuroectodermal tumor3ClinicalTrials

Clinical Data

ClinicalTrials.gov TOPOTECAN
The Cochrane Collaboration TOPOTECAN

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 CHEMBL84. 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
CHEMBL1781 DNA topoisomerase I Homo sapiens 1.000
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 1.000

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1781 DNA topoisomerase I Homo sapiens 1.000
CHEMBL5990 Breast cancer type 1 susceptibility protein Homo sapiens 1.000
CHEMBL2524 Alpha-galactosidase A Homo sapiens 0.984
CHEMBL4261 Hypoxia-inducible factor 1 alpha Homo sapiens 0.981
CHEMBL3251 Nuclear factor NF-kappa-B p105 subunit Homo sapiens 0.738

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
421.5 421.1638 1.85 3 104.89 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
8 2 0 8 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
8.92 7.65 .32 -.32 3 31 0.49

Structural Alerts

There are 2 structural alerts for CHEMBL84. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XX - Other antineoplastic agents
L01XX17 - topotecan

ChemSpider ChemSpider:UCFGDBYHRUNTLO-QHCPKHFHSA-N
DailyMed topotecan hydrochloride
PubChem SID: 164339428
Wikipedia Topotecan

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL84



ACToR 123948-87-8
BindingDB 50034026 50008935
Brenda 4873 154401 153416
ChEBI 63632
DrugBank DB01030
DrugCentral 2707
eMolecules 29542583
EPA CompTox Dashboard DTXSID3042685
FDA SRS 7M7YKX2N15
Guide to Pharmacology 7101
Human Metabolome Database HMDB0015164
IBM Patent System C491BF277F0255BBF4C32FABEE2718CE
KEGG Ligand C11158
LINCS LSM-5662
MolPort MolPort-003-850-580
Nikkaji J362.027A J2.256.757H J2.256.755A
PDBe TTC
PharmGKB PA451729
PubChem 60700
PubChem: Thomson Pharma 14807035 14904851
SureChEMBL SCHEMBL3836
ZINC ZINC000001611274

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