ETOPOSIDE PHOSPHATE

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Trade Names:
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: Salt Prodrug
UNII: 528XYJ8L1N
Parent Compound: ETOPOSIDE

Structure
InChI Key LIQODXNTTZAGID-OCBXBXKTSA-N
Smile COc1cc([C@@H]2c3cc4c(cc3[C@@H](O[C@@H]3O[C@@H]5CO[C@@H](C)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OP(=O)(O)O
InChI
InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C29H33O16P
Molecular Weight 668.54
AlogP 1.1
Hydrogen Bond Acceptor 14.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 7.0
Polar Surface Area 207.36
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 46.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA topoisomerase II alpha inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Transferase
- - - - 20.78
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -1.47-5.48

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Carcinoma 3 D002277 ClinicalTrials
Ganglioneuroblastoma 3 D018305 ClinicalTrials
Central Nervous System Neoplasms 3 D016543 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Neuroblastoma 3 D009447 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Lymphohistiocytosis, Hemophagocytic 2 D051359 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Rhabdomyosarcoma 2 D012208 ClinicalTrials
Medulloblastoma 2 D008527 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Leukemia, Biphenotypic, Acute 2 D015456 ClinicalTrials
Leukemia, Biphenotypic, Acute 2 D015456 ClinicalTrials
Burkitt Lymphoma 2 D002051 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Lymphoma, Mantle-Cell 2 D020522 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Neoplasms, Plasma Cell 1 D054219 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Fallopian Tube Neoplasms 1 D005185 ClinicalTrials
Ovarian Neoplasms 1 D010051 ClinicalTrials
Peritoneal Neoplasms 1 D010534 ClinicalTrials
Leukemia, Myeloid 1 D007951 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Oligodendroglioma 1 D009837 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials

Related Entries

Scaffolds

Parent

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Injury, poisoning and procedural complications
20.32
General disorders and administration site conditions
9.7
Renal and urinary disorders
7.59
Nervous system disorders
6.49
Blood and lymphatic system disorders
6.32
Infections and infestations
5.56
Respiratory, thoracic and mediastinal disorders
5.4
Vascular disorders
5.23
Gastrointestinal disorders
4.55
Investigations
3.71
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
3.54
Hepatobiliary disorders
3.37
Cardiac disorders
3.2
Surgical and medical procedures
2.95
Skin and subcutaneous tissue disorders
2.19
Metabolism and nutrition disorders
2.02

Cross References

Resources Reference
ChEBI 135867
ChEMBL CHEMBL1200645
DrugCentral 3944
FDA SRS 528XYJ8L1N
PubChem 6918092
SureChEMBL SCHEMBL13318053
ZINC ZINC000003920020
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