U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H32O13
Molecular Weight 588.5577
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETOPOSIDE

SMILES

C[C@]1([H])OC[C@]2([H])[C@]([H])([C@@]([H])([C@]([H])([C@@]([H])(O2)O[C@]3([H])c4cc5c(cc4[C@@]([H])(c6cc(c(c(c6)OC)O)OC)[C@]7([H])[C@]3([H])COC7=O)OCO5)O)O)O1

InChI

InChIKey=VJJPUSNTGOMMGY-MRVIYFEKSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf

Etoposide (trade name Etopophos) is a semisynthetic derivative of podophyllotoxin that exhibits antitumor activity. It has been in clinical use for more than two decades and remains one of the most highly prescribed anticancer drugs in the world. The primary cytotoxic target for etoposide is topoisomerase II. This ubiquitous enzyme regulates DNA under- and over winding, and removes knots and tangles from the genome by generating transient double-stranded breaks in the double helix. Etoposide kills cells by stabilizing a covalent enzyme-cleaved DNA complex (known as the cleavage complex) that is a transient intermediate in the catalytic cycle of topoisomerase II. The accumulation of cleavage complexes in treated cells leads to the generation of permanent DNA strand breaks, which trigger recombination/repair pathways, mutagenesis, and chromosomal translocations. If these breaks overwhelm the cell, they can initiate death pathways. Thus, etoposide converts topoisomerase II from an essential enzyme to a potent cellular toxin that fragments the genome. Although the topoisomerase II-DNA cleavage complex is an important target for cancer chemotherapy, there also is evidence that topoisomerase II-mediated DNA strand breaks induced by etoposide and other agents can trigger chromosomal translocations that lead to specific types of leukemia. Etopophos (etoposide phosphate) is indicated in the management of the following neoplasms: Refractory Testicular Tumors-and for Small Cell Lung Cancer. The in vitro cytotoxicity observed for etoposide phosphate is significantly less than that seen with etoposide, which is believed due to the necessity for conversion in vivo to the active moiety, etoposide, by dephosphorylation. The mechanism of action is believed to be the same as that of etoposide.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.800000000000000044 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ETOPOPHOS PRESERVATIVE FREE

Approved Use

ETOPOPHOS for Injection is indicated in the management of the following neoplasms: Refractory Testicular Tumors-ETOPOPHOS for Injection in combination therapy with other approved chemotherapeutic agents in patients with refractory testicular tumors who have already received appropriate surgical, chemotherapeutic, and radiotherapeutic therapy. Small Cell Lung Cancer-ETOPOPHOS for Injection in combination with other approved chemotherapeutic agents as first-line treatment in patients with small cell lung cancer.

Launch Date

437270400000
Primary
ETOPOPHOS PRESERVATIVE FREE

Approved Use

ETOPOPHOS for Injection is indicated in the management of the following neoplasms: Refractory Testicular Tumors-ETOPOPHOS for Injection in combination therapy with other approved chemotherapeutic agents in patients with refractory testicular tumors who have already received appropriate surgical, chemotherapeutic, and radiotherapeutic therapy. Small Cell Lung Cancer-ETOPOPHOS for Injection in combination with other approved chemotherapeutic agents as first-line treatment in patients with small cell lung cancer.

Launch Date

832291200000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.7 μg/mL
80 mg/m² other, intravenous
dose: 80 mg/m²
route of administration: Intravenous
experiment type: OTHER
co-administered:
ETOPOSIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
18.66 μg/mL
95 mg/m² other, intravenous
dose: 95 mg/m²
route of administration: Intravenous
experiment type: OTHER
co-administered:
ETOPOSIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2707 μg × min/mL
80 mg/m² other, intravenous
dose: 80 mg/m²
route of administration: Intravenous
experiment type: OTHER
co-administered:
ETOPOSIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
5806 μg × min/mL
95 mg/m² other, intravenous
dose: 95 mg/m²
route of administration: Intravenous
experiment type: OTHER
co-administered:
ETOPOSIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.37 h
80 mg/m² other, intravenous
dose: 80 mg/m²
route of administration: Intravenous
experiment type: OTHER
co-administered:
ETOPOSIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
0.32 h
95 mg/m² other, intravenous
dose: 95 mg/m²
route of administration: Intravenous
experiment type: OTHER
co-administered:
ETOPOSIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
ETOPOSIDE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
25 mg/m2 3 times / day multiple, oral
Highest studied dose
Dose: 25 mg/m2, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg/m2, 3 times / day
Sources:
unhealthy, 1.1-17
Health Status: unhealthy
Age Group: 1.1-17
Sex: M+F
Sources:
DLT: Neutropenia, Thrombocytopenia...
Dose limiting toxicities:
Neutropenia (grade 4, 25%)
Thrombocytopenia (grade 4, 12.5%)
Leukopenia (grade 4, 12.5%)
Diarrhea (grade 3, 12.5%)
Diarrhea (grade 4, 12.5%)
Sources:
20 mg/m2 3 times / day multiple, oral
MTD
Dose: 20 mg/m2, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg/m2, 3 times / day
Sources:
unhealthy, 1.1-17
Health Status: unhealthy
Age Group: 1.1-17
Sex: M+F
Sources:
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 4, 14%)
Sources:
175 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 175 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 175 mg/m2, 1 times / day
Sources:
unhealthy, 39-72
Health Status: unhealthy
Age Group: 39-72
Sex: M+F
Sources:
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 4, 28.6%)
Sources:
175 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 175 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 175 mg/m2, 1 times / day
Sources:
unhealthy, 39-72
Health Status: unhealthy
Age Group: 39-72
Sex: M+F
Sources:
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 3, 14.3%)
Sources:
220 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 220 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 220 mg/m2, 1 times / day
Sources:
unhealthy, 39-72
Health Status: unhealthy
Age Group: 39-72
Sex: M+F
Sources:
DLT: Neutropenia, Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 3, 25%)
Neutropenia (grade 4, 25%)
Sources:
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
DLT: Leukopenia, Neutropenia...
Disc. AE: Nausea and vomiting, Fatigue...
Dose limiting toxicities:
Leukopenia (grade 4, 12%)
Neutropenia (grade 4, 25%)
Leukopenia (grade 3, 29%)
Neutropenia (grade 3, 20%)
Thrombocytopenia (grade 4, 4%)
AEs leading to
discontinuation/dose reduction:
Nausea and vomiting (3%)
Fatigue (1%)
Neutropenic sepsis (grade 5, 2%)
Bleeding (grade 5, 1%)
Sources:
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Disc. AE: Myelosuppression...
AEs leading to
discontinuation/dose reduction:
Myelosuppression (severe)
Sources:
AEs

AEs

AESignificanceDosePopulation
Diarrhea grade 3, 12.5%
DLT
25 mg/m2 3 times / day multiple, oral
Highest studied dose
Dose: 25 mg/m2, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg/m2, 3 times / day
Sources:
unhealthy, 1.1-17
Health Status: unhealthy
Age Group: 1.1-17
Sex: M+F
Sources:
Leukopenia grade 4, 12.5%
DLT
25 mg/m2 3 times / day multiple, oral
Highest studied dose
Dose: 25 mg/m2, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg/m2, 3 times / day
Sources:
unhealthy, 1.1-17
Health Status: unhealthy
Age Group: 1.1-17
Sex: M+F
Sources:
Thrombocytopenia grade 4, 12.5%
DLT
25 mg/m2 3 times / day multiple, oral
Highest studied dose
Dose: 25 mg/m2, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg/m2, 3 times / day
Sources:
unhealthy, 1.1-17
Health Status: unhealthy
Age Group: 1.1-17
Sex: M+F
Sources:
Diarrhea grade 4, 12.5%
DLT, Disc. AE
25 mg/m2 3 times / day multiple, oral
Highest studied dose
Dose: 25 mg/m2, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg/m2, 3 times / day
Sources:
unhealthy, 1.1-17
Health Status: unhealthy
Age Group: 1.1-17
Sex: M+F
Sources:
Neutropenia grade 4, 25%
DLT
25 mg/m2 3 times / day multiple, oral
Highest studied dose
Dose: 25 mg/m2, 3 times / day
Route: oral
Route: multiple
Dose: 25 mg/m2, 3 times / day
Sources:
unhealthy, 1.1-17
Health Status: unhealthy
Age Group: 1.1-17
Sex: M+F
Sources:
Neutropenia grade 4, 14%
DLT
20 mg/m2 3 times / day multiple, oral
MTD
Dose: 20 mg/m2, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg/m2, 3 times / day
Sources:
unhealthy, 1.1-17
Health Status: unhealthy
Age Group: 1.1-17
Sex: M+F
Sources:
Neutropenia grade 4, 28.6%
DLT
175 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 175 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 175 mg/m2, 1 times / day
Sources:
unhealthy, 39-72
Health Status: unhealthy
Age Group: 39-72
Sex: M+F
Sources:
Neutropenia grade 3, 14.3%
DLT
175 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 175 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 175 mg/m2, 1 times / day
Sources:
unhealthy, 39-72
Health Status: unhealthy
Age Group: 39-72
Sex: M+F
Sources:
Neutropenia grade 3, 25%
DLT
220 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 220 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 220 mg/m2, 1 times / day
Sources:
unhealthy, 39-72
Health Status: unhealthy
Age Group: 39-72
Sex: M+F
Sources:
Neutropenia grade 4, 25%
DLT
220 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 220 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 220 mg/m2, 1 times / day
Sources:
unhealthy, 39-72
Health Status: unhealthy
Age Group: 39-72
Sex: M+F
Sources:
Fatigue 1%
Disc. AE
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
Nausea and vomiting 3%
Disc. AE
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
Neutropenia grade 3, 20%
DLT
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
Leukopenia grade 3, 29%
DLT
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
Leukopenia grade 4, 12%
DLT
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
Neutropenia grade 4, 25%
DLT
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
Thrombocytopenia grade 4, 4%
DLT
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
Bleeding grade 5, 1%
Disc. AE
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
Neutropenic sepsis grade 5, 2%
Disc. AE
60 mg/m2 1 times / day multiple, oral
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources:
unhealthy, 39-83
Health Status: unhealthy
Age Group: 39-83
Sex: F
Sources:
Myelosuppression severe
Disc. AE
100 mg/m2 1 times / day multiple, intravenous
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
slight
weak [Ki 756 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
weak (co-administration study)
Comment: Ketoconazole increased the area under the plasma concentration-time curve (AUC) of oral etoposide by a median of 20%
major
yes (pharmacogenomic study)
Comment: UGT1A1*28 and UGT1A1*6 mutations might be regarded as predictors for etoposide-induced grade 4 neutropenia.
minor
minor
minor
minor
no
no
no
no
no
no
no
no
no
no
no
yes
yes
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
Etoposide-induced hypersensitivity reactions. Report of two cases.
1985 Dec
Expression of p21 and bcl-2 proteins and p53 mRNA in surgically resected preparations of non-small cell lung cancer (stage IIIA) after etoposide and cisplatin chemotherapy.
2001
High-dose chemotherapy with peripheral blood stem cell transplantation for patients with advanced ovarian cancer.
2001 Apr
Bone morphogenetic protein-2 promotes osteoblast apoptosis through a Smad-independent, protein kinase C-dependent signaling pathway.
2001 Aug 3
Adult Gaucher disease in association with primary malignant bone tumors.
2001 Feb 1
High-dose chemotherapy as a consolidation approach in advanced ovarian cancer: long-term results.
2001 May
Irinotecan: future directions in small-cell lung cancer.
2001 May
Pro-oxidant and antioxidant mechanisms of etoposide in HL-60 cells: role of myeloperoxidase.
2001 Nov 1
Expression of P-glycoprotein and multidrug resistance associated protein in Ehrlich ascites tumor cells after fractionated irradiation.
2001 Nov 15
Treatment of gestational trophoblastic tumors.
2002 Apr
Alpha-CD25 antibody treatment in a child with hemophagocytic lymphohistiocytosis.
2002 Feb
EBNA1 may prolong G(2)/M phase and sensitize HER2/neu-overexpressing ovarian cancer cells to both topoisomerase II-targeting and paclitaxel drugs.
2003 Aug 1
Oral melphalan as a treatment for platinum-resistant ovarian cancer.
2003 Jun 16
Phase I/II trial of weekly cisplatin, etoposide, and irinotecan chemotherapy for metastatic lung cancer: JCOG 9507.
2003 Mar 24
Phase I dose escalation study of carboplatin to a fixed dose of irinotecan as first-line treatment of small cell lung cancer.
2004 Jun
High-throughput technology: green fluorescent protein to monitor cell death.
2005
Long-term results of autologous stem cell transplantation for Hodgkin's disease (HD) and low-/intermediate-grade B non-Hodgkin's lymphoma (NHL): a report from the Austrian Stem Cell Transplantation Registry (ASCTR).
2005 Jul
Prognostic value of the age-adjusted International Prognostic Index in chemosensitive recurrent or refractory non-Hodgkin's lymphomas treated with high-dose BEAM therapy and autologous stem cell transplantation.
2005 Jun
HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC).
2005 Jun 9
Use of preclinical models to improve treatment of retinoblastoma.
2005 Oct
Adenine nucleotides inhibit proliferation of the human lung adenocarcinoma cell line LXF-289 by activation of nuclear factor kappaB1 and mitogen-activated protein kinase pathways.
2006 Aug
Bcl-XL is qualitatively different from and ten times more effective than Bcl-2 when expressed in a breast cancer cell line.
2006 Aug 23
[Pulmonary and pleural manifestations of multiple myeloma].
2006 Dec
Randomized phase III trial comparing irinotecan/cisplatin with etoposide/cisplatin in patients with previously untreated extensive-stage disease small-cell lung cancer.
2006 May 1
Signaling from p53 to NF-kappaB determines the chemotherapy responsiveness of neuroblastoma.
2006 Nov
BRCA1- and BRCA2-deficient cells are sensitive to etoposide-induced DNA double-strand breaks via topoisomerase II.
2007 Aug 1
Curative surgery after neoadjuvant chemotherapy in metastatic poorly differentiated neuroendocrine carcinoma.
2007 Dec
Dielectrophoretic detection of membrane morphology changes in Jurkat T-cells undergoing etoposide-induced apoptosis.
2007 Feb
Modulation of topoisomerase IIalpha expression by a DNA sequence-specific polyamide.
2007 Jan
Incidence and risk factors of central nervous system recurrence in aggressive lymphoma--a survey of 1693 patients treated in protocols of the German High-Grade Non-Hodgkin's Lymphoma Study Group (DSHNHL).
2007 Jan
The N-terminus and alpha-5, alpha-6 helices of the pro-apoptotic protein Bax, modulate functional interactions with the anti-apoptotic protein Bcl-xL.
2007 May 23
Expression of CYP3A4 as a predictor of response to chemotherapy in peripheral T-cell lymphomas.
2007 Nov 1
A Contribution to solve the problem of the need for consolidative radiotherapy after intensive chemotherapy in advanced stages of Hodgkin's lymphoma--analysis of a quality control program initiated by the radiotherapy reference center of the German Hodgkin Study Group (GHSG).
2007 Nov 15
In vivo targeting of dead tumor cells in a murine tumor model using a monoclonal antibody specific for the La autoantigen.
2007 Sep 15
Upregulation of bfl-1 is a potential mechanism of chemoresistance in B-cell chronic lymphocytic leukaemia.
2007 Sep 17
Therapy-associated genetic aberrations in patients treated for non-Hodgkin lymphoma.
2008 Apr
Glassy cell carcinoma of the uterine cervix responsive to neoadjuvant intraarterial chemotherapy.
2008 Dec
Interferonalpha enhances etoposide-induced apoptosis in human osteosarcoma U2OS cells by a p53-dependent pathway.
2008 Feb 13
Treatment experiences of testicular cancer in Hispanic patients with Down's syndrome at the National Cancer Institute of Mexico.
2008 Nov
Haematopoietic stem cell transplantation for autoimmune disorders.
2008 Nov
[Production of reconstructed two-cell rat embryos after chemical inactivation of chromosomes in MII oocytes by etoposide].
2008 Sep-Oct
[Diabetes insipidus followed, after 4 years, with dysarthria and mild right-sided hemiparesis--the first clinical signs of Erdheim-Chester disease. Description and depiction of a case with a review of information on the disease].
2009 Dec
Fasting and cancer treatment in humans: A case series report.
2009 Dec 31
Palonosetron in prevention of nausea and vomiting after highly emetogenic chemotherapy before haematopoietic stem cell transplantation-single center experience.
2009 Oct
Biological characteristics and treatment outcomes of metastatic or recurrent neuroendocrine tumors: tumor grade and metastatic site are important for treatment strategy.
2010 Aug 23
Mitochondrial fission and cristae disruption increase the response of cell models of Huntington's disease to apoptotic stimuli.
2010 Dec
Cellular responses to etoposide: cell death despite cell cycle arrest and repair of DNA damage.
2010 Feb
Preclinical pharmacology of BA-TPQ, a novel synthetic iminoquinone anticancer agent.
2010 Jul 13
Outpatient reduced-intensity allogeneic stem cell transplantation for patients with refractory or relapsed lymphomas compared with autologous stem cell transplantation using a simplified method.
2010 Oct
Management of non-gestational ovarian choriocarcinoma: laparoscopy can be essential. Report of two cases.
2010 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: the recommended dose of VePesid (Etoposide) Capsules is two times the IV dose rounded to the nearest 50 mg
50 to 100 mg/m2/day on days 1 through 5 to 100 mg/m2/day on days 1, 3, and 5 (testicular cancer)
Route of Administration: Intravenous
In Vitro Use Guide
Apoptosis of thymocytes has been investigated by morphological, biochemical and cytometric techniques, both in non-perturbed conditions and after exposure to the topoisomerase-II inhibitor etoposide in vitro. At low (0.1 to 10 uM) etoposide concentrations apoptotic cells had cytoplasm patterns similar to naturally occurring apoptotic thymocytes, whereas at high (50 to 100 uM) concentrations extensive organelle damage took place.
Name Type Language
ETOPOSIDE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
ETOPOSIDE [EP]
Common Name English
(5R,5AR,8AR,9S)-9-((4,6-O-((1R)-ETHANE-1,1-DIYL)-.ALPHA.-D-GLUCOPYRANOSYL)OXY)-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDRO(2)BENZOFURO(5,6-F)(1,3)BENZODIOXOL-6(5AH)-ONE
Systematic Name English
ETOPOSIDE [MART.]
Common Name English
ETOPOSIDE [HSDB]
Common Name English
VEPESID
Brand Name English
VP-16-213
Code English
ETOPOSIDE [USP-RS]
Common Name English
ETOPOSIDE [WHO-DD]
Common Name English
TOPOSAR
Brand Name English
ETOPOSIDE [USP MONOGRAPH]
Common Name English
ETOPOSIDE [USP]
Common Name English
ETOPOSIDUM [WHO-IP LATIN]
Common Name English
NSC-141540
Code English
ETOPOSIDE [ORANGE BOOK]
Common Name English
ETOPOSIDE [VANDF]
Common Name English
ETOPOSIDE [MI]
Common Name English
ETOPOSIDE [INN]
Common Name English
SINTOPOZID
Common Name English
ETOPOSIDE [USAN]
Common Name English
FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE-, 9-((4,6-O-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSYL)OXY)5,8,8A,9-TETRAHYDRO-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL), (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.BETA.(R*)))-
Common Name English
ETOPOSIDE [WHO-IP]
Common Name English
ETOPOSIDE [IARC]
Common Name English
4'-DEMETHYLEPIPODOPHYLLOTOXIN 9-(4,6-O-(R)-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSIDE)
Common Name English
ETOPOSIDE IMPURITY C [EP]
Common Name English
ETOPOSIDE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175609
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
NDF-RT N0000000176
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
WHO-VATC QL01CB01
Created by admin on Fri Jun 25 20:58:42 UTC 2021 , Edited by admin on Fri Jun 25 20:58:42 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Fri Jun 25 20:58:42 UTC 2021 , Edited by admin on Fri Jun 25 20:58:42 UTC 2021
NCI_THESAURUS C1331
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
LIVERTOX 389
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
WHO-ATC L01CB01
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
Code System Code Type Description
DRUG CENTRAL
1112
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
CAS
33419-42-0
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
ChEMBL
CHEMBL44657
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
INN
3835
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
USP_CATALOG
1268852
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY USP-RS
NCI_THESAURUS
C491
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
HSDB
6517
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
ECHA (EC/EINECS)
251-509-1
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
RXCUI
4179
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY RxNorm
MESH
D005047
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
MERCK INDEX
M5199
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY Merck Index
PUBCHEM
36462
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
EVMPD
SUB07337MIG
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
WIKIPEDIA
ETOPOSIDE
Created by admin on Fri Jun 25 20:58:42 UTC 2021 , Edited by admin on Fri Jun 25 20:58:42 UTC 2021
PRIMARY
EPA CompTox
33419-42-0
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
DRUG BANK
DB00773
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ETOPOSIDE
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY Description: A white or almost white, crystalline powder.Solubility: Practically insoluble in water; sparingly soluble in methanol R; slightly soluble in ethanol (~750 g/l) TS and dichloromethane R.Category: Cytotoxic drug.Storage: Etoposide should be kept in a tightly closed container.Labelling: The designation Etoposide for parenteral use indicates that the substance complies with the additional requirementsand may be used for parenteral administration. Expiry date.Additional information:. CAUTION - Etoposide must be handled with care, avoiding contact with the skin and inhalation of airborne particles.Requirement: Etoposide contains not less than 98.0% and not more than the equivalent of 102.0% of C29H32O13, calculated with reference to the dried substance.
IUPHAR
6815
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
FDA UNII
6PLQ3CP4P3
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
LACTMED
Etoposide
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY
USP_CATALOG
1268808
Created by admin on Fri Jun 25 20:58:41 UTC 2021 , Edited by admin on Fri Jun 25 20:58:41 UTC 2021
PRIMARY USP-RS