TOPOTECAN

Search structure
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L01CE01
UNII: 7M7YKX2N15

Structure
InChI Key UCFGDBYHRUNTLO-QHCPKHFHSA-N
Smile CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c(CN(C)C)c(O)ccc3nc2-1
InChI
InChI=1S/C23H23N3O5/c1-4-23(30)16-8-18-20-12(9-26(18)21(28)15(16)11-31-22(23)29)7-13-14(10-25(2)3)19(27)6-5-17(13)24-20/h5-8,27,30H,4,9-11H2,1-3H3/t23-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C23H23N3O5
Molecular Weight 421.45
AlogP 1.85
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 3.0
Polar Surface Area 104.89
Molecular species BASE
Aromatic Rings 3.0
Heavy Atoms 31.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) -0.880 - EST
Atmospheric OH Rate Constant 2.92E-10 cm3/molecule-sec EST

Pharmacology

Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 1521.1 - - -
Enzyme Hydrolase
- - - -
Enzyme Isomerase
54-71.3 21-22880 26.5 - 31.98-92.85
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -45.36--4.69
Transcription factor
12 60 - - 82.8
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 17.3
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 61000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 1300 - - 50

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Ganglioneuroblastoma 3 D018305 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Retinoblastoma 3 D012175 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Uterine Cervical Neoplasms 3 D002583 ClinicalTrials
Small Cell Lung Carcinoma 3 D055752 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Neuroblastoma 3 D009447 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Uterine Neoplasms 2 D014594 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Carcinoma, Ovarian Epithelial 2 D000077216 ClinicalTrials
Sarcoma, Ewing 2 D012512 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Rhabdomyosarcoma 2 D012208 ClinicalTrials
Medulloblastoma 2 D008527 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Mediastinal Neoplasms 2 D008479 ClinicalTrials
Central Nervous System Neoplasms 2 D016543 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Gliosarcoma 2 D018316 ClinicalTrials
Peritoneal Neoplasms 2 D010534 ClinicalTrials
Fallopian Tube Neoplasms 2 D005185 ClinicalTrials
Wilms Tumor 2 D009396 ClinicalTrials
Endometrial Neoplasms 2 D016889 ClinicalTrials
Wilms Tumor 2 D009396 ClinicalTrials
Colonic Neoplasms 2 D003110 ClinicalTrials
Sarcoma, Clear Cell 1 D018227 ClinicalTrials
Carcinoma, Small Cell 1 D018288 ClinicalTrials
Glioma 1 D005910 ClinicalTrials
Lymphoma 1 D008223 ClinicalTrials
Paraganglioma 1 D010235 ClinicalTrials
Rectal Neoplasms 1 D012004 ClinicalTrials
Meningitis, Aseptic 1 D008582 ClinicalTrials
Desmoplastic Small Round Cell Tumor 1 D058405 ClinicalTrials
Carcinoma, Renal Cell 1 D002292 ClinicalTrials
Liposarcoma, Myxoid 1 D018208 ClinicalTrials
Oligodendroglioma 1 D009837 ClinicalTrials
Fibrosarcoma 1 D005354 ClinicalTrials
Astrocytoma 1 D001254 ClinicalTrials
Oligodendroglioma 1 D009837 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Genital Neoplasms, Female 1 D005833 ClinicalTrials
Neoplasms, Plasma Cell 1 D054219 ClinicalTrials
Meningeal Neoplasms 1 D008577 ClinicalTrials
Fibroma 1 D005350 ClinicalTrials
Triple Negative Breast Neoplasms 1 D064726 ClinicalTrials
Histiocytoma 1 D051642 ClinicalTrials
Severe Acute Respiratory Syndrome 1 D045169 ClinicalTrials
Myoepithelioma 1 D009208 ClinicalTrials

Related Entries

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 123948-87-8
ChEBI 63632
ChEMBL CHEMBL84
DrugBank DB01030
DrugCentral 2707
EPA CompTox DTXSID3042685
FDA SRS 7M7YKX2N15
Human Metabolome Database HMDB15164
Guide to Pharmacology 7101
KEGG C11158
PDB TTC
PharmGKB PA451729
PubChem 60700
SureChEMBL SCHEMBL3836
ZINC ZINC000001611274
CONTENTS