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

Details

Stereochemistry ABSOLUTE
Molecular Formula C29H32O13
Molecular Weight 588.5566
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETOPOSIDE

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C3=CC(OC)=C(O)C(OC)=C3)C4=CC5=C(OCO5)C=C4[C@H]2O[C@]6([H])O[C@]7([H])CO[C@@H](C)O[C@@]7([H])[C@H](O)[C@H]6O

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

Molecular Formula C29H32O13
Molecular Weight 588.5566
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

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
0.8 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

4.37270413E11
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

8.3229121E11
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: Page: p.1455
unhealthy, 1.1-17
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 1.1-17
Sex: M+F
Population Size: 8
Sources: Page: p.1455
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: Page: p.1455
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: Page: p.1455
unhealthy, 1.1-17
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 1.1-17
Sex: M+F
Population Size: 7
Sources: Page: p.1455
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 4, 14%)
Sources: Page: p.1455
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: Page: p.203
unhealthy, 39-72
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 7
Sources: Page: p.203
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 4, 28.6%)
Sources: Page: p.203
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: Page: p.203
unhealthy, 39-72
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 7
Sources: Page: p.203
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 3, 14.3%)
Sources: Page: p.203
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: Page: p.203
unhealthy, 39-72
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 8
Sources: Page: p.203
DLT: Neutropenia, Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 3, 25%)
Neutropenia (grade 4, 25%)
Sources: Page: p.203
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
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: Page: p.407
100 mg/m2 1 times / day multiple, intravenous (max)
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Testicular cancer
Sources: Page: p.1
Disc. AE: Myelosuppression...
AEs leading to
discontinuation/dose reduction:
Myelosuppression (severe)
Sources: Page: p.1
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: Page: p.1455
unhealthy, 1.1-17
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 1.1-17
Sex: M+F
Population Size: 8
Sources: Page: p.1455
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: Page: p.1455
unhealthy, 1.1-17
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 1.1-17
Sex: M+F
Population Size: 8
Sources: Page: p.1455
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: Page: p.1455
unhealthy, 1.1-17
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 1.1-17
Sex: M+F
Population Size: 8
Sources: Page: p.1455
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: Page: p.1455
unhealthy, 1.1-17
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 1.1-17
Sex: M+F
Population Size: 8
Sources: Page: p.1455
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: Page: p.1455
unhealthy, 1.1-17
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 1.1-17
Sex: M+F
Population Size: 8
Sources: Page: p.1455
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: Page: p.1455
unhealthy, 1.1-17
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 1.1-17
Sex: M+F
Population Size: 7
Sources: Page: p.1455
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: Page: p.203
unhealthy, 39-72
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 7
Sources: Page: p.203
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: Page: p.203
unhealthy, 39-72
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 7
Sources: Page: p.203
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: Page: p.203
unhealthy, 39-72
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 8
Sources: Page: p.203
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: Page: p.203
unhealthy, 39-72
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 8
Sources: Page: p.203
Fatigue 1%
Disc. AE
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
Nausea and vomiting 3%
Disc. AE
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
Neutropenia grade 3, 20%
DLT
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
Leukopenia grade 3, 29%
DLT
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
Leukopenia grade 4, 12%
DLT
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
Neutropenia grade 4, 25%
DLT
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
Thrombocytopenia grade 4, 4%
DLT
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
Bleeding grade 5, 1%
Disc. AE
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
Neutropenic sepsis grade 5, 2%
Disc. AE
60 mg/m2 1 times / day multiple, oral (max)
Recommended
Dose: 60 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg/m2, 1 times / day
Sources: Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources: Page: p.407
Myelosuppression severe
Disc. AE
100 mg/m2 1 times / day multiple, intravenous (max)
Recommended
Dose: 100 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 100 mg/m2, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Testicular cancer
Sources: Page: p.1
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
High-dose chemotherapy with peripheral blood stem cell transplantation for patients with advanced ovarian cancer.
2001 Apr
Adult Gaucher disease in association with primary malignant bone tumors.
2001 Feb 1
Transcriptional activation of short interspersed elements by DNA-damaging agents.
2001 Jan
Irinotecan: future directions in small-cell lung cancer.
2001 May
Langerhans cell histiocytosis.
2001 Nov
The importance of drug scheduling and recovery phases in determining drug activity. Improving etoposide efficacy in BCR-ABL-positive CML cells.
2002 Apr
Chemoresistant or aggressive lymphoma predicts for a poor outcome following reduced-intensity allogeneic progenitor cell transplantation: an analysis from the Lymphoma Working Party of the European Group for Blood and Bone Marrow Transplantation.
2002 Dec 15
Alpha-CD25 antibody treatment in a child with hemophagocytic lymphohistiocytosis.
2002 Feb
Urate-oxidase in the prevention and treatment of metabolic complications in patients with B-cell lymphoma and leukemia, treated in the Société Française d'Oncologie Pédiatrique LMB89 protocol.
2002 May
Estrogen receptor-dependent and estrogen receptor-independent pathways for tamoxifen and 4-hydroxytamoxifen-induced programmed cell death.
2002 Nov 22
High-dose chemotherapy and autologous peripheral blood stem cell rescue in a patient with pleuropulmonary blastoma.
2003 Jan
Oral melphalan as a treatment for platinum-resistant ovarian cancer.
2003 Jun 16
Primary mediastinal large B-cell lymphoma (PMLBCL): long-term results from a retrospective multicentre Italian experience in 138 patients treated with CHOP or MACOP-B/VACOP-B.
2004 Jan 26
Phase I dose escalation study of carboplatin to a fixed dose of irinotecan as first-line treatment of small cell lung cancer.
2004 Jun
Carbonylation of glycolytic proteins is a key response to drug-induced oxidative stress and apoptosis.
2004 Mar
High-throughput technology: green fluorescent protein to monitor cell death.
2005
Increased expression of the E3-ubiquitin ligase receptor subunit betaTRCP1 relates to constitutive nuclear factor-kappaB activation and chemoresistance in pancreatic carcinoma cells.
2005 Feb 15
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
Sequential oral 9-nitrocamptothecin and etoposide: a pharmacodynamic- and pharmacokinetic-based phase I trial.
2006 Aug
[Pulmonary and pleural manifestations of multiple myeloma].
2006 Dec
Resveratrol at high doses acts as an apoptotic inducer in endothelial cells.
2006 Feb
Prevalence and rupture rate of cerebral aneurysms discovered during intra-arterial chemotherapy of brain tumors.
2006 Feb
Small cell lung cancer: an update on therapeutic aspects.
2006 Jan-Mar
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
Modulation of topoisomerase IIalpha expression by a DNA sequence-specific polyamide.
2007 Jan
Ethylenediaminetetraacetic acid affects subcellular expression of clusterin protein in human colon adenocarcinoma COLO 205 cell line.
2007 Jan
Expression of CYP3A4 as a predictor of response to chemotherapy in peripheral T-cell lymphomas.
2007 Nov 1
Impaired DNA double-strand break repair contributes to chemoresistance in HIF-1 alpha-deficient mouse embryonic fibroblasts.
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
Primary sinonasal choriocarcinoma.
2009 Apr
No attenuation of the ATM-dependent DNA damage response in murine telomerase-deficient cells.
2009 Mar 1
Helicobacter pylori counteracts the apoptotic action of its VacA toxin by injecting the CagA protein into gastric epithelial cells.
2009 Oct
XAF1 expression and regulatory effects of somatostatin on XAF1 in prostate cancer cells.
2010 Dec 11
Cellular responses to etoposide: cell death despite cell cycle arrest and repair of DNA damage.
2010 Feb
A novel podophyllotoxin derivative (YB-1EPN) induces apoptosis and down-regulates express of P-glycoprotein in multidrug resistance cell line KBV200.
2010 Feb 10
Preclinical pharmacology of BA-TPQ, a novel synthetic iminoquinone anticancer agent.
2010 Jul 13
The epidemiology of bone cancer in 0 - 39 year olds in northern England, 1981 - 2002.
2010 Jul 6
Evaluation of pyridoacridine alkaloids in a zebrafish phenotypic assay.
2010 Jun 2
Mixed germ cell tumor metastatic to the skin: case report and literature review.
2010 Mar 23
Activation of P53 in HepG2 cells as surrogate to detect mutagens and promutagens in vitro.
2010 Oct 5
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) 35 mg/m2/day for 4 days to 50 mg/m2/day for 5 days (small cell lung 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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:03:33 UTC 2023
Edited
by admin
on Wed Jul 05 23:03:33 UTC 2023
Record UNII
6PLQ3CP4P3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETOPOSIDE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official 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
TOPOSAR
Brand Name English
ETOPOSIDE [USP MONOGRAPH]
Common Name English
ETOPOSIDUM [WHO-IP LATIN]
Common Name English
NSC-141540
Code English
Etoposide [WHO-DD]
Common Name English
ETOPOSIDE [ORANGE BOOK]
Common Name English
ETOPOSIDE [JAN]
Common Name English
ETOPOSIDE [VANDF]
Common Name English
ETOPOSIDE [MI]
Common Name English
etoposide [INN]
Common Name English
SINTOPOZID
Common Name English
ETOPOSIDE [USP IMPURITY]
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 [EP IMPURITY]
Common Name English
ETOPOSIDE [EP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175609
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
NDF-RT N0000000176
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
WHO-VATC QL01CB01
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
NCI_THESAURUS C1331
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
LIVERTOX NBK548102
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
WHO-ATC L01CB01
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
Code System Code Type Description
DRUG CENTRAL
1112
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
CAS
33419-42-0
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL44657
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
INN
3835
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
RS_ITEM_NUM
1268808
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
NCI_THESAURUS
C491
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
HSDB
6517
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
251-509-1
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
DAILYMED
6PLQ3CP4P3
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
RXCUI
4179
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY RxNorm
MESH
D005047
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
MERCK INDEX
M5199
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY Merck Index
SMS_ID
100000082091
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
PUBCHEM
36462
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
EVMPD
SUB07337MIG
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
CHEBI
4911
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
WIKIPEDIA
ETOPOSIDE
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID5023035
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
DRUG BANK
DB00773
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ETOPOSIDE
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
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 Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
FDA UNII
6PLQ3CP4P3
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
NSC
141540
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
LACTMED
Etoposide
Created by admin on Wed Jul 05 23:03:33 UTC 2023 , Edited by admin on Wed Jul 05 23:03:33 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDING
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
PLASMA; URINE
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY