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
Molecular Formula C29H32O13
Molecular Weight 588.5577
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.

CNS Activity

Approval Year

1983
37
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7687
 0.8 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
7968
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
Approved
7968
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8431968
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8431968
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8431968
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8431968
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8431968
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/8431968
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%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
Page: p.1455
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 4, 14%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
unhealthy, 39-72
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 7
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 4, 28.6%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
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:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
unhealthy, 39-72
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 7
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
DLT: Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 3, 14.3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
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:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
unhealthy, 39-72
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
DLT: Neutropenia, Neutropenia...
Dose limiting toxicities:
Neutropenia (grade 3, 25%)
Neutropenia (grade 4, 25%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Testicular cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf
Page: p.1
Disc. AE: Myelosuppression...
AEs leading to
discontinuation/dose reduction:
Myelosuppression (severe)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/8021737
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:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
unhealthy, 39-72
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 7
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
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:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
unhealthy, 39-72
n = 7
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 7
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
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:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
unhealthy, 39-72
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
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:
https://pubmed.ncbi.nlm.nih.gov/7799021
Page: p.203
unhealthy, 39-72
n = 8
Health Status: unhealthy
Condition: Cancer
Age Group: 39-72
Sex: M+F
Population Size: 8
Sources:
https://pubmed.ncbi.nlm.nih.gov/7799021
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://pubmed.ncbi.nlm.nih.gov/9469322
Page: p.407
unhealthy, 39-83
n = 97
Health Status: unhealthy
Condition: Ovarian carcinoma
Age Group: 39-83
Sex: F
Population Size: 97
Sources:
https://pubmed.ncbi.nlm.nih.gov/9469322
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Testicular cancer
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1469

OverviewOther

Other InhibitorOther SubstrateOther Inducer
MRP2
341
OATP1B1
353

P-gp
1222

CYP2E1
567

CYP1A2
892

CYP3A5
346

CYP2B6
575

CYP2A6
452

UGT1A1
358

UGT1A8
242

UGT1A3
358

UGT1A4
294

UGT1A6
258

UGT1A7
197

UGT1A9
327

UGT1A10
247

UGT2B4
213

UGT2B7
329

UGT2B15
165

UGT2B17
184

Abcc2
3

Abcc3
3

MRP2
172

MRP3
46
CYP3A5
72
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP3A5
119
 slight
MRP2
421
 weak [Ki 756 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1469
 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%
UGT1A1
358
 major
yes (pharmacogenomic study)
Comment: UGT1A1*28 and UGT1A1*6 mutations might be regarded as predictors for etoposide-induced grade 4 neutropenia.
CYP1A2
892
 minor
CYP2E1
567
 minor
UGT1A3
358
 minor
UGT1A8
242
 minor
CYP2A6
452
 no
CYP2B6
575
 no
UGT1A10
247
 no
UGT1A4
294
 no
UGT1A6
258
 no
UGT1A7
197
 no
UGT1A9
327
 no
UGT2B15
165
 no
UGT2B17
184
 no
UGT2B4
213
 no
UGT2B7
329
 no
Abcc2
3
 yes
Abcc3
3
 yes
ETOPOSIDE GLUCURONIDE
3
CYP3A5
346
 yes
MRP2
172
 yes
MRP3
46
 yes
ETOPOSIDE GLUCURONIDE
3
OATP1B1
353
 yes
P-gp
1222
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:4911
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4911
MolPort
MolPort-006-069-121
https://www.molport.com/shop/molecule-link/MolPort-006-069-121
Selleck Chemicals
Etopophos
http://www.selleckchem.com/products/Etopophos.html
ZINC
ZINC000003938684
http://zinc15.docking.org/substances/ZINC000003938684
eMolecules
32278021
https://www.emolecules.com/cgi-bin/more?vid=32278021
eMolecules
537894
https://www.emolecules.com/cgi-bin/more?vid=537894
PubMed

PubMed

TitleDatePubMed
Transcriptional activation of short interspersed elements by DNA-damaging agents.
2001 Jan
Comparison of 'sequential' versus 'standard' chemotherapy as re-induction treatment, with or without cyclosporine, in refractory/relapsed acute myeloid leukaemia (AML): results of the UK Medical Research Council AML-R trial.
2001 Jun
Pro-oxidant and antioxidant mechanisms of etoposide in HL-60 cells: role of myeloperoxidase.
2001 Nov 1
Treatment of gestational trophoblastic tumors.
2002 Apr
The importance of drug scheduling and recovery phases in determining drug activity. Improving etoposide efficacy in BCR-ABL-positive CML cells.
2002 Apr
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
Expression of p21 and bcl-2 proteins in paraffin-embedded preparations of non-small cell lung cancer in stage IIIA after Etoposide and Cisplatin induced chemotherapy.
2003
High-dose chemotherapy and autologous peripheral blood stem cell rescue in a patient with pleuropulmonary blastoma.
2003 Jan
Preliminary results of the multicenter trial GPOH-HD 95 for the treatment of Hodgkin's disease in children and adolescents: analysis and outlook.
2003 May-Jun
Carbonylation of glycolytic proteins is a key response to drug-induced oxidative stress and apoptosis.
2004 Mar
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
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
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
Prevalence and rupture rate of cerebral aneurysms discovered during intra-arterial chemotherapy of brain tumors.
2006 Feb
Genotoxic risks to nurses from contamination of the work environment with antineoplastic drugs in Japan.
2006 Nov
Curative surgery after neoadjuvant chemotherapy in metastatic poorly differentiated neuroendocrine carcinoma.
2007 Dec
Ethylenediaminetetraacetic acid affects subcellular expression of clusterin protein in human colon adenocarcinoma COLO 205 cell line.
2007 Jan
Effect of structural modification at the 4, 3', and 2' positions of doxorubicin on topoisomerase II poisoning, apoptosis, and cytotoxicity in human melanoma cells.
2007 May-Jun
In vivo targeting of dead tumor cells in a murine tumor model using a monoclonal antibody specific for the La autoantigen.
2007 Sep 15
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
Impaired DNA double-strand break repair contributes to chemoresistance in HIF-1 alpha-deficient mouse embryonic fibroblasts.
2008 Dec
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
Etoposide induces MLL rearrangements and other chromosomal abnormalities in human embryonic stem cells.
2009 Sep
Chemotherapy resistance in metastatic breast cancer: the evolving role of ixabepilone.
2010
Bevacizumab in combination with sequential high-dose chemotherapy in solid cancer, a feasibility study.
2010 Dec
XAF1 expression and regulatory effects of somatostatin on XAF1 in prostate cancer cells.
2010 Dec 11
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
Role of dephosphorylation of FOXO1 on apoptosis induced by wortmannin for non-Hodgkin's lymphoma cells.
2010 Jun
Reduced-dose craniospinal radiotherapy followed by high-dose chemotherapy and autologous stem cell rescue for children with newly diagnosed high-risk medulloblastoma or supratentorial primitive neuroectodermal tumor.
2010 Jun
Activation of P53 in HepG2 cells as surrogate to detect mutagens and promutagens in vitro.
2010 Oct 5
Patents

Patents

JP2000191546A
3
JP2003175058A
11
JP2003503157A
4
JP2006502184A
39
JP2006523607A
9
JP2008510795A
78
JP2009531296A
20
JP2010530906A
9
JP2011501962A
9
JP2011525178A
21
JP2011528275A
425
JP2012500104A
106
JP4397691B2
22
JP4663232B2
15
JP4744875B2
28
JP4758063B2
4
JPH00597675A
7
JPH02292295A
3
JPH09221495A
3
JPS6461423A
3

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 Fri Jun 25 20:58:41 UTC 2021
Edited
by admin
on Fri Jun 25 20:58:41 UTC 2021
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
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
Related Record Type Details
DNA TOPOISOMERASE 2-ALPHA
TARGET -> INHIBITOR
BINDING
MRP-3
TRANSPORTER -> SUBSTRATE
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
MRP-2
TRANSPORTER -> INHIBITOR
MRP-2
TRANSPORTER -> SUBSTRATE
MRP-1
TRANSPORTER -> SUBSTRATE
Related Record Type Details
Structure of ETOPOSIDE GLUCURONIDE
METABOLITE -> PARENT
URINE
Structure of ETOPOSIDE SULFATE CONJUGATE
METABOLITE -> PARENT
Related Record Type Details
Structure of (5R,5AR,8AR,9S)-9-ETHOXY-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDRO(2)BENZOFURO(5,6-F)(1,3)BENZODIOXOL-6(5AH)-ONE
IMPURITY -> PARENT
Structure of ETOPOSIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of (5R,5AR,8AR,9S)-5-(4-(((BENZYLOXY)CARBONYL)OXY)-3,5-DIMETHOXYPHENYL)-9-((4,6-O-((1R)-ETHANE-1,1-DIYL)-2,3-DI-O-FORMYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-5,8,8A,9-TETRAHYDRO(2)BENZOFURO(5,6-F)(1,3)BENZODIOXOL-6(5AH)-ONE
IMPURITY -> PARENT
Structure of LIGNAN P
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 5,8,8A,9-TETRAHYDRO-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-9-METHOXY-FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE, (5R-(5.ALPHA.,5A.BETA.,8A.ALPHA.,9.BETA.))-
IMPURITY -> PARENT
DEMETHYLEPIPODOPHYLLOTOXIN DIMER
IMPURITY -> PARENT
Structure of (5R,5AR,8AR,9S)-9-((2,3-BIS-O-(DICHLOROACETYL)-4,6-O-((1S)-ETHANE-1,1-DIYL)-.BETA.-L-GLUCOPYRANOSYL)OXY)-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-5,8,8A,9-TETRAHYDRO(2)BENZOFURO(5,6-F)(1,3)BENZODIOXOL-6(5AH)-ONE
IMPURITY -> PARENT
Structure of ETOPOSIDE DESACCHARODIMER
IMPURITY -> PARENT
Related Record Type Details
Structure of ETOPOSIDE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966