ETOPOSIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1983)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L01CB01
UNII: 6PLQ3CP4P3

Structure
InChI Key VJJPUSNTGOMMGY-MRVIYFEKSA-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)c1O
InChI
InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C29H32O13
Molecular Weight 588.56
AlogP 1.34
Hydrogen Bond Acceptor 13.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 5.0
Polar Surface Area 160.83
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 42.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 0.6 - EXP
Henry's Law Constant 1.75E-30 atm-m3/mole EST
Atmospheric OH Rate Constant 3.05E-10 cm3/molecule-sec EST
Melting Point 236-251 deg C EXP
Water Solubility 58.7 mg/L EST
Vapor Pressure 5.35E-23 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA topoisomerase II inhibitor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - - 3.074
Enzyme Isomerase
810-56000 4700-120000 - - 0.7-100
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PIKK family
- - - - 25-53
Enzyme Oxidoreductase
- 3187 - - -
Enzyme Transferase
- - - - 12.33-19.23
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -34.06-1.94
Epigenetic regulator Writer Histone acetyltransferase SRC family
- 1153 - - -
Transcription factor
- - 210000 - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 4180 - 13500 8.5-92.89
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 7.5
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- - - 276000-768000 1
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- - - 756000 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Lung Neoplasms 4 D008175 ClinicalTrials
Lung Neoplasms 4 D008175 ClinicalTrials
Lymphoma, Mantle-Cell 3 D020522 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Sarcoma, Ewing 3 D012512 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Myelodysplastic Syndromes 3 D009190 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Lymphoma, T-Cell, Peripheral 3 D016411 ClinicalTrials
Leukemia, Monocytic, Acute 3 D007948 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Leukemia, Myelomonocytic, Acute 3 D015479 ClinicalTrials
Burkitt Lymphoma 3 D002051 ClinicalTrials
Carcinoma 3 D002277 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 3 D016403 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Neuroblastoma 3 D009447 ClinicalTrials
Ependymoma 3 D004806 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Medulloblastoma 3 D008527 ClinicalTrials
Brain Neoplasms 3 D001932 ClinicalTrials
Testicular Neoplasms 3 D013736 ClinicalTrials
Leukemia, Lymphoid 3 D007945 ClinicalTrials
Testicular Neoplasms 3 D013736 ClinicalTrials
Neuroectodermal Tumors, Primitive 3 D018242 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Sarcoma, Myeloid 3 D023981 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Adenocarcinoma of Lung 3 D000077192 ClinicalTrials
Myeloproliferative Disorders 3 D009196 ClinicalTrials
Adrenal Cortex Neoplasms 3 D000306 ClinicalTrials
Leukemia, Erythroblastic, Acute 3 D004915 ClinicalTrials
Ganglioneuroblastoma 3 D018305 ClinicalTrials
Myeloproliferative Disorders 3 D009196 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Anemia, Refractory, with Excess of Blasts 3 D000754 ClinicalTrials
Mediastinal Neoplasms 3 D008479 ClinicalTrials
Central Nervous System Neoplasms 3 D016543 ClinicalTrials
Hepatoblastoma 3 D018197 ClinicalTrials
Carcinoma, Embryonal 3 D018236 ClinicalTrials
Endodermal Sinus Tumor 3 D018240 ClinicalTrials
Choriocarcinoma 3 D002822 ClinicalTrials
Endodermal Sinus Tumor 3 D018240 ClinicalTrials
Leukemia, Myelomonocytic, Chronic 3 D015477 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Brain Neoplasms 3 D001932 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Teratoma 3 D013724 ClinicalTrials
Kidney Neoplasms 3 D007680 ClinicalTrials
Seminoma 3 D018239 ClinicalTrials
Ependymoma 3 D004806 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 3 D009373 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Ovarian Neoplasms 3 D010051 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials
Hodgkin Disease 3 D006689 ClinicalTrials
Lymphohistiocytosis, Hemophagocytic 3 D051359 ClinicalTrials
Ependymoma 3 D004806 ClinicalTrials
Choroid Plexus Neoplasms 3 D016545 ClinicalTrials
Lymphoma, Follicular 3 D008224 ClinicalTrials
Wilms Tumor 3 D009396 ClinicalTrials
Leukemia-Lymphoma, Adult T-Cell 3 D015459 ClinicalTrials
Granuloma, Lethal Midline 3 D006103 ClinicalTrials
Sex Cord-Gonadal Stromal Tumors 3 D018312 ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma 3 D054218 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Wilms Tumor 3 D009396 ClinicalTrials
Retinoblastoma 3 D012175 ClinicalTrials
Gestational Trophoblastic Disease 3 D031901 ClinicalTrials
Leukemia, Biphenotypic, Acute 3 D015456 ClinicalTrials
Stomach Neoplasms 3 D013274 ClinicalTrials
Testicular Neoplasms 3 D013736 ClinicalTrials
Colorectal Neoplasms 3 D015179 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 3 D009373 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Osteosarcoma 3 D012516 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Carcinoma, Squamous Cell 3 D002294 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Thymus Neoplasms 3 D013953 ClinicalTrials
Rhabdomyosarcoma 3 D012208 ClinicalTrials
Leukemia, Megakaryoblastic, Acute 3 D007947 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Leukemia, Basophilic, Acute 3 D015471 ClinicalTrials
Anemia, Refractory 3 D000753 ClinicalTrials
Neoplasms, Plasma Cell 2 D054219 ClinicalTrials
Astrocytoma 2 D001254 ClinicalTrials
Lymphoma, T-Cell 2 D016399 ClinicalTrials
Neuromyelitis Optica 2 D009471 ClinicalTrials
Myasthenia Gravis 2 D009157 ClinicalTrials
Astrocytoma 2 D001254 ClinicalTrials
Carcinoma, Islet Cell 2 D018273 ClinicalTrials
Polyradiculoneuropathy, Chronic Inflammatory Demyelinating 2 D020277 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Carcinoma, Hepatocellular 2 D006528 ClinicalTrials
Rhabdomyosarcoma, Embryonal 2 D018233 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Oligodendroglioma 2 D009837 ClinicalTrials
Oligodendroglioma 2 D009837 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Opsoclonus-Myoclonus Syndrome 2 D053578 ClinicalTrials
Oropharyngeal Neoplasms 2 D009959 ClinicalTrials
Astrocytoma 2 D001254 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Carcinoma, Large Cell 2 D018287 ClinicalTrials
Carcinoid Tumor 2 D002276 ClinicalTrials
Neutropenia 2 D009503 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Lymphoma, Large-Cell, Anaplastic 2 D017728 ClinicalTrials
Carcinoma, Neuroendocrine 2 D018278 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 2 D020529 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Esthesioneuroblastoma, Olfactory 2 D018304 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Thymoma 2 D013945 ClinicalTrials
Lymphoma, B-Cell, Marginal Zone 2 D018442 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Gliosarcoma 2 D018316 ClinicalTrials
Carcinoma, Merkel Cell 2 D015266 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Hematologic Diseases 2 D006402 ClinicalTrials
Rhabdomyosarcoma, Alveolar 2 D018232 ClinicalTrials
Acquired Immunodeficiency Syndrome 2 D000163 ClinicalTrials
Paraganglioma 2 D010235 ClinicalTrials
Stiff-Person Syndrome 2 D016750 ClinicalTrials
Optic Nerve Glioma 2 D020339 ClinicalTrials
Waldenstrom Macroglobulinemia 2 D008258 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Oligodendroglioma 2 D009837 ClinicalTrials
Castleman Disease 2 D005871 ClinicalTrials
Sarcoma, Kaposi 1 D012514 ClinicalTrials
Lymphoma, Primary Effusion 1 D054685 ClinicalTrials
Fallopian Tube Neoplasms 1 D005185 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 1 D054437 ClinicalTrials
Leukemia, Plasma Cell 1 D007952 ClinicalTrials
Neuroendocrine Tumors 1 D018358 ClinicalTrials
Neoplasms, Neuroepithelial 1 D018302 ClinicalTrials
Peritoneal Neoplasms 1 D010534 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 1 D015464 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Blood and lymphatic system disorders Leukopenia 91.0
Blood and lymphatic system disorders Neutropenia 88.0
Blood and lymphatic system disorders Anaemia 72.0
General disorders and administration site conditions Asthenia 39.0
General disorders and administration site conditions Discomfort 39.0
General disorders and administration site conditions Feeling abnormal 39.0
General disorders and administration site conditions Ill-defined disorder 39.0
General disorders and administration site conditions Malaise 39.0
Gastrointestinal disorders Nausea 37.0
Gastrointestinal disorders Vomiting 37.0
Skin and subcutaneous tissue disorders Alopecia 33.0
Investigations Body temperature increased 24.0
General disorders and administration site conditions Chills 24.0
Blood and lymphatic system disorders Thrombocytopenia 23.0
General disorders and administration site conditions Decreased appetite 16.0
General disorders and administration site conditions Mucosal inflammation 11.0
Gastrointestinal disorders Constipation 8.0
Gastrointestinal disorders Abdominal pain 7.0
Gastrointestinal disorders Gastrointestinal pain 7.0
Gastrointestinal disorders Diarrhoea 6.0
Gastrointestinal disorders Dysgeusia 6.0
Cardiac disorders Dizziness 5.0
General disorders and administration site conditions Extravasation 5.0
Vascular disorders Phlebitis 5.0
General disorders and administration site conditions Asthenia 3.0
Gastrointestinal disorders Mouth ulceration 2.0
Gastrointestinal disorders Stomatitis 2.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Blood and lymphatic system disorders
14.05
General disorders and administration site conditions
10.53
Infections and infestations
10.18
Respiratory, thoracic and mediastinal disorders
7.05
Injury, poisoning and procedural complications
6.75
Vascular disorders
6.58
Gastrointestinal disorders
6.57
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
5.99
Nervous system disorders
5.76
Cardiac disorders
3.75
Metabolism and nutrition disorders
3.07
Renal and urinary disorders
2.92
Skin and subcutaneous tissue disorders
2.77
Investigations
2.7
Hepatobiliary disorders
2.05

Cross References

Resources Reference
CAS NUMBER 33419-42-0
ChEBI 4911
ChEMBL CHEMBL44657
DrugBank DB00773
DrugCentral 1112
FDA SRS 6PLQ3CP4P3
Human Metabolome Database HMDB14911
Guide to Pharmacology 6815
KEGG C01576
PDB EVP
PharmGKB PA449552
PubChem 36462
SureChEMBL SCHEMBL4259
ZINC ZINC000003938684
CONTENTS