Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H32O13 |
Molecular Weight | 588.5566 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12COC(=O)[C@]1([H])[C@H](C3=CC(OC)=C(O)C(OC)=C3)C4=CC5=C(OCO5)C=C4[C@H]2O[C@]6([H])O[C@]7([H])CO[C@@H](C)O[C@@]7([H])[C@H](O)[C@H]6O
InChI
InChIKey=VJJPUSNTGOMMGY-MRVIYFEKSA-N
InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
Molecular Formula | C29H32O13 |
Molecular Weight | 588.5566 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
|||
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 |
---|---|---|---|
OverviewOther
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% |
|||
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/ |
|||
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 |
---|---|---|
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 |
|
Bone morphogenetic protein-2 promotes osteoblast apoptosis through a Smad-independent, protein kinase C-dependent signaling pathway. | 2001 Aug 3 |
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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 |
|
High-dose chemotherapy as a consolidation approach in advanced ovarian cancer: long-term results. | 2001 May |
|
Langerhans cell histiocytosis. | 2001 Nov |
|
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 |
|
Estrogen receptor-dependent and estrogen receptor-independent pathways for tamoxifen and 4-hydroxytamoxifen-induced programmed cell death. | 2002 Nov 22 |
|
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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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 |
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Relapse in the skull after myeloablative therapy for high-risk neuroblastoma. | 2003 Jan-Feb |
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Oral melphalan as a treatment for platinum-resistant ovarian cancer. | 2003 Jun 16 |
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Phase I/II trial of weekly cisplatin, etoposide, and irinotecan chemotherapy for metastatic lung cancer: JCOG 9507. | 2003 Mar 24 |
|
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 |
|
Pregnancy outcome after prenatal exposure to bleomycin, etoposide and cisplatin for malignant ovarian germ cell tumors: report of 2 cases. | 2005 Mar-Apr |
|
Use of preclinical models to improve treatment of retinoblastoma. | 2005 Oct |
|
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 |
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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 |
|
Genotoxic risks to nurses from contamination of the work environment with antineoplastic drugs in Japan. | 2006 Nov |
|
BRCA1- and BRCA2-deficient cells are sensitive to etoposide-induced DNA double-strand breaks via topoisomerase II. | 2007 Aug 1 |
|
Curative surgery after neoadjuvant chemotherapy in metastatic poorly differentiated neuroendocrine carcinoma. | 2007 Dec |
|
Dielectrophoretic detection of membrane morphology changes in Jurkat T-cells undergoing etoposide-induced apoptosis. | 2007 Feb |
|
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 |
|
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 |
|
Upregulation of bfl-1 is a potential mechanism of chemoresistance in B-cell chronic lymphocytic leukaemia. | 2007 Sep 17 |
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Glassy cell carcinoma of the uterine cervix responsive to neoadjuvant intraarterial chemotherapy. | 2008 Dec |
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Interferonalpha enhances etoposide-induced apoptosis in human osteosarcoma U2OS cells by a p53-dependent pathway. | 2008 Feb 13 |
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Ifosfamide, epirubicin and etoposide rituximab in refractory or relapsed B-cell lymphoma: analysis of remission induction and stem cell mobilization. | 2008 Jul |
|
Haematopoietic stem cell transplantation for autoimmune disorders. | 2008 Nov |
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[Production of reconstructed two-cell rat embryos after chemical inactivation of chromosomes in MII oocytes by etoposide]. | 2008 Sep-Oct |
|
Primary sinonasal choriocarcinoma. | 2009 Apr |
|
[Diabetes insipidus followed, after 4 years, with dysarthria and mild right-sided hemiparesis--the first clinical signs of Erdheim-Chester disease. Description and depiction of a case with a review of information on the disease]. | 2009 Dec |
|
Fasting and cancer treatment in humans: A case series report. | 2009 Dec 31 |
|
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 |
|
Chemotherapy resistance in metastatic breast cancer: the evolving role of ixabepilone. | 2010 |
|
Mitochondrial fission and cristae disruption increase the response of cell models of Huntington's disease to apoptotic stimuli. | 2010 Dec |
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Cellular responses to etoposide: cell death despite cell cycle arrest and repair of DNA damage. | 2010 Feb |
|
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 |
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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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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
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 Dec 16 17:28:39 UTC 2022
by
admin
on
Fri Dec 16 17:28:39 UTC 2022
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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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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175609
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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NDF-RT |
N0000000176
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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WHO-VATC |
QL01CB01
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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WHO-ESSENTIAL MEDICINES LIST |
8.2
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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NCI_THESAURUS |
C1331
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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LIVERTOX |
NBK548102
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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WHO-ATC |
L01CB01
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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Code System | Code | Type | Description | ||
---|---|---|---|---|---|
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1112
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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33419-42-0
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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CHEMBL44657
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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3835
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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1268808
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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C491
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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6517
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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251-509-1
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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6PLQ3CP4P3
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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4179
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | RxNorm | ||
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D005047
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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M5199
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | Merck Index | ||
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36462
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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SUB07337MIG
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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4911
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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ETOPOSIDE
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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DTXSID5023035
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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DB00773
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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ETOPOSIDE
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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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 Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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6PLQ3CP4P3
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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141540
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY | |||
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Etoposide
Created by
admin on Fri Dec 16 17:28:39 UTC 2022 , Edited by admin on Fri Dec 16 17:28:39 UTC 2022
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PRIMARY |
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 |
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
PLASMA; URINE
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PRODRUG -> METABOLITE ACTIVE |
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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 |
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