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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16101488Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16101488
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16101488 |
0.8 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ETOPOPHOS PRESERVATIVE FREE Approved UseETOPOPHOS 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 Date4.37270413E11 |
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Primary | ETOPOPHOS PRESERVATIVE FREE Approved UseETOPOPHOS 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 Date8.3229121E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3% |
ETOPOSIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse 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%) Sources: Page: p.1455Thrombocytopenia (grade 4, 12.5%) Leukopenia (grade 4, 12.5%) Diarrhea (grade 3, 12.5%) Diarrhea (grade 4, 12.5%) |
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%) Sources: Page: p.203Neutropenia (grade 4, 25%) |
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%) AEs leading toNeutropenia (grade 4, 25%) Leukopenia (grade 3, 29%) Neutropenia (grade 3, 20%) Thrombocytopenia (grade 4, 4%) discontinuation/dose reduction: Nausea and vomiting (3%) Sources: Page: p.407Fatigue (1%) Neutropenic sepsis (grade 5, 2%) Bleeding (grade 5, 1%) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/ |
slight | |||
weak [Ki 756 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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% |
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major | yes (pharmacogenomic study) Comment: UGT1A1*28 and UGT1A1*6 mutations might be regarded as predictors for etoposide-induced grade 4 neutropenia. Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/ |
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minor | ||||
minor | ||||
minor | ||||
minor | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
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Transcriptional activation of short interspersed elements by DNA-damaging agents. | 2001 Jan |
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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 |
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Pro-oxidant and antioxidant mechanisms of etoposide in HL-60 cells: role of myeloperoxidase. | 2001 Nov 1 |
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Treatment of gestational trophoblastic tumors. | 2002 Apr |
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The importance of drug scheduling and recovery phases in determining drug activity. Improving etoposide efficacy in BCR-ABL-positive CML cells. | 2002 Apr |
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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 |
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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 |
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High-dose chemotherapy and autologous peripheral blood stem cell rescue in a patient with pleuropulmonary blastoma. | 2003 Jan |
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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 |
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Carbonylation of glycolytic proteins is a key response to drug-induced oxidative stress and apoptosis. | 2004 Mar |
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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 |
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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 |
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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 |
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HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC). | 2005 Jun 9 |
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Use of preclinical models to improve treatment of retinoblastoma. | 2005 Oct |
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Sequential oral 9-nitrocamptothecin and etoposide: a pharmacodynamic- and pharmacokinetic-based phase I trial. | 2006 Aug |
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[Pulmonary and pleural manifestations of multiple myeloma]. | 2006 Dec |
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Prevalence and rupture rate of cerebral aneurysms discovered during intra-arterial chemotherapy of brain tumors. | 2006 Feb |
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Genotoxic risks to nurses from contamination of the work environment with antineoplastic drugs in Japan. | 2006 Nov |
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Curative surgery after neoadjuvant chemotherapy in metastatic poorly differentiated neuroendocrine carcinoma. | 2007 Dec |
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Ethylenediaminetetraacetic acid affects subcellular expression of clusterin protein in human colon adenocarcinoma COLO 205 cell line. | 2007 Jan |
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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 |
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In vivo targeting of dead tumor cells in a murine tumor model using a monoclonal antibody specific for the La autoantigen. | 2007 Sep 15 |
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Therapy-associated genetic aberrations in patients treated for non-Hodgkin lymphoma. | 2008 Apr |
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Glassy cell carcinoma of the uterine cervix responsive to neoadjuvant intraarterial chemotherapy. | 2008 Dec |
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Impaired DNA double-strand break repair contributes to chemoresistance in HIF-1 alpha-deficient mouse embryonic fibroblasts. | 2008 Dec |
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Treatment experiences of testicular cancer in Hispanic patients with Down's syndrome at the National Cancer Institute of Mexico. | 2008 Nov |
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Haematopoietic stem cell transplantation for autoimmune disorders. | 2008 Nov |
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Etoposide induces MLL rearrangements and other chromosomal abnormalities in human embryonic stem cells. | 2009 Sep |
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Chemotherapy resistance in metastatic breast cancer: the evolving role of ixabepilone. | 2010 |
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Bevacizumab in combination with sequential high-dose chemotherapy in solid cancer, a feasibility study. | 2010 Dec |
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XAF1 expression and regulatory effects of somatostatin on XAF1 in prostate cancer cells. | 2010 Dec 11 |
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A novel podophyllotoxin derivative (YB-1EPN) induces apoptosis and down-regulates express of P-glycoprotein in multidrug resistance cell line KBV200. | 2010 Feb 10 |
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Preclinical pharmacology of BA-TPQ, a novel synthetic iminoquinone anticancer agent. | 2010 Jul 13 |
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Role of dephosphorylation of FOXO1 on apoptosis induced by wortmannin for non-Hodgkin's lymphoma cells. | 2010 Jun |
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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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9116336
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
Edited
Fri Jun 25 20:58:41 UTC 2021
by
admin
on
Fri Jun 25 20:58:41 UTC 2021
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Record UNII |
6PLQ3CP4P3
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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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
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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
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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
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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
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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
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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
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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
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Code System | Code | Type | Description | ||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | USP-RS | ||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | RxNorm | ||
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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
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PRIMARY | |||
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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
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PRIMARY | Merck Index | ||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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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. | ||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | USP-RS |
Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
BINDING
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT | |||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |