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Details

Stereochemistry EPIMERIC
Molecular Formula C36H42O17
Molecular Weight 746.7085
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETOPOSIDE TONIRIBATE

SMILES

[H][C@]12COC(=O)[C@]1([H])[C@H](C3=CC(OC)=C(OC(=O)OCC4COC(C)(C)O4)C(OC)=C3)C5=C(C=C6OCOC6=C5)[C@H]2O[C@@H]7O[C@]8([H])CO[C@@H](C)O[C@@]8([H])[C@H](O)[C@H]7O

InChI

InChIKey=FCWSQAKOPTZCOD-SQYSSJHTSA-N
InChI=1S/C36H42O17/c1-15-43-13-25-32(49-15)28(37)29(38)34(50-25)51-30-19-9-22-21(46-14-47-22)8-18(19)26(27-20(30)12-44-33(27)39)16-6-23(41-4)31(24(7-16)42-5)52-35(40)45-10-17-11-48-36(2,3)53-17/h6-9,15,17,20,25-30,32,34,37-38H,10-14H2,1-5H3/t15-,17?,20+,25-,26-,27+,28-,29-,30-,32-,34+/m1/s1

HIDE SMILES / InChI

Molecular Formula C36H42O17
Molecular Weight 746.7085
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 10 / 11
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
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
Coexisting true hermaphroditism and partial hydatidiform mole developing metastatic gestational trophoblastic tumors. A case report.
2002 Nov
Estrogen receptor-dependent and estrogen receptor-independent pathways for tamoxifen and 4-hydroxytamoxifen-induced programmed cell death.
2002 Nov 22
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
Inhibition of telomerase activity in malignant glioma cells correlates with their sensitivity to temozolomide.
2003 Sep 1
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
Evaluation of the combined effect of p53 codon 72 polymorphism and hotspot mutations in response to anticancer drugs.
2005 Jun 15
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
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
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
Interferonalpha enhances etoposide-induced apoptosis in human osteosarcoma U2OS cells by a p53-dependent pathway.
2008 Feb 13
[Production of reconstructed two-cell rat embryos after chemical inactivation of chromosomes in MII oocytes by etoposide].
2008 Sep-Oct
Fasting and cancer treatment in humans: A case series report.
2009 Dec 31
Pegylated liposomal doxorubicin in ovarian cancer.
2009 Jun
No attenuation of the ATM-dependent DNA damage response in murine telomerase-deficient cells.
2009 Mar 1
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
The role of an all-oral chemotherapy containing lomustine (CCNU) in advanced,fs progressive Hodgkin lymphoma: a patient-friendly palliative option which can result in long-term disease control.
2010 Feb
Preclinical pharmacology of BA-TPQ, a novel synthetic iminoquinone anticancer agent.
2010 Jul 13
Role of dephosphorylation of FOXO1 on apoptosis induced by wortmannin for non-Hodgkin's lymphoma cells.
2010 Jun
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) 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 Sat Dec 16 12:12:52 UTC 2023
Edited
by admin
on Sat Dec 16 12:12:52 UTC 2023
Record UNII
A59HL2Q48U
Record Status Validated (UNII)
Record Version
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Name Type Language
ETOPOSIDE TONIRIBATE
INN  
Official Name English
CARBONIC ACID, (2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)METHYL 4-((5R,5AR,8AR,9S)-9-((4,6-O-(1R)-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSYL)OXY)-5,5A,6,8,8A,9-HEXAHYDRO-6-OXOFURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-5-YL)-2,6-DIMETHOXYPHENYL ESTER
Systematic Name English
PROVP-16I
Common Name English
((4RS)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)METHYL4-((5R,5AR,8AR,9S)-9-((4,6-O-((1R)-ETHANE-1,1-DIYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-6-OXO-5,5A,6,8,8A,9-HEXAHYDRO-2H-FURO(3',4':6,7)NAPHTHO(2,3-D)(1,3)DIOXOL-5-YL)-2,6-DIMETHOXYPHENYL CARBONATE
Systematic Name English
etoposide toniribate [INN]
Common Name English
CAP-7.1
Common Name English
(4-((5S,5AR,8AR,9R)-5-(((2R,4AR,6R,7R,8R,8AS)-7,8-DIHYDROXY-2-METHYL-4,4A,6,7,8,8A-HEXAHYDROPYRANO(3,2-D)(1,3)DIOXIN-6-YL)OXY)-8-OXO-5A,6,8A,9-TETRAHYDRO-5H-ISOBENZOFURO(5,6-F)(1,3)BENZODIOXOL-9-YL)-2,6-DIMETHOXY-PHENYL) (2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)M
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 671318
Created by admin on Sat Dec 16 12:12:52 UTC 2023 , Edited by admin on Sat Dec 16 12:12:52 UTC 2023
Code System Code Type Description
CAS
433304-61-1
Created by admin on Sat Dec 16 12:12:52 UTC 2023 , Edited by admin on Sat Dec 16 12:12:52 UTC 2023
PRIMARY
NCI_THESAURUS
C114977
Created by admin on Sat Dec 16 12:12:53 UTC 2023 , Edited by admin on Sat Dec 16 12:12:53 UTC 2023
PRIMARY
FDA UNII
A59HL2Q48U
Created by admin on Sat Dec 16 12:12:53 UTC 2023 , Edited by admin on Sat Dec 16 12:12:53 UTC 2023
PRIMARY
PUBCHEM
101163123
Created by admin on Sat Dec 16 12:12:53 UTC 2023 , Edited by admin on Sat Dec 16 12:12:53 UTC 2023
PRIMARY
INN
10430
Created by admin on Sat Dec 16 12:12:53 UTC 2023 , Edited by admin on Sat Dec 16 12:12:53 UTC 2023
PRIMARY
EU-Orphan Drug
EU/3/14/1270
Created by admin on Sat Dec 16 12:12:52 UTC 2023 , Edited by admin on Sat Dec 16 12:12:52 UTC 2023
PRIMARY On 4 June 2014, orphan designation (EU/3/14/1270) was granted by the European Commission to CellAct Pharma GmbH, Germany, for (5R,5aR,8aR,9S)-9-[[4,6-O-[(R)-Ethylidene]-β-D-glucopyranosyl]-oxy]-5-(4-({[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]carbonyl}oxy)-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydroisobenzofuro[5,6-f][1,3]benzodioxol-6(5aH)-one for the treatment of biliary tract cancer.
SMS_ID
100000183902
Created by admin on Sat Dec 16 12:12:53 UTC 2023 , Edited by admin on Sat Dec 16 12:12:53 UTC 2023
PRIMARY
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