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 |
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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 |
---|---|---|---|
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% |
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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 |
---|---|---|
Etoposide-induced hypersensitivity reactions. Report of two cases. | 1985 Dec |
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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 |
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Bone morphogenetic protein-2 promotes osteoblast apoptosis through a Smad-independent, protein kinase C-dependent signaling pathway. | 2001 Aug 3 |
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Adult Gaucher disease in association with primary malignant bone tumors. | 2001 Feb 1 |
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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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Expression of P-glycoprotein and multidrug resistance associated protein in Ehrlich ascites tumor cells after fractionated irradiation. | 2001 Nov 15 |
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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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High-dose chemotherapy and autologous peripheral blood stem cell rescue in a patient with pleuropulmonary blastoma. | 2003 Jan |
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Relapse in the skull after myeloablative therapy for high-risk neuroblastoma. | 2003 Jan-Feb |
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[Tumor staging with PET/CT. Detection of a second tumor]. | 2004 Jan |
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Primary mediastinal large B-cell lymphoma (PMLBCL): long-term results from a retrospective multicentre Italian experience in 138 patients treated with CHOP or MACOP-B/VACOP-B. | 2004 Jan 26 |
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Phase I dose escalation study of carboplatin to a fixed dose of irinotecan as first-line treatment of small cell lung cancer. | 2004 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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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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Small cell lung cancer: an update on therapeutic aspects. | 2006 Jan-Mar |
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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 |
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BRCA1- and BRCA2-deficient cells are sensitive to etoposide-induced DNA double-strand breaks via topoisomerase II. | 2007 Aug 1 |
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Therapy-associated genetic aberrations in patients treated for non-Hodgkin lymphoma. | 2008 Apr |
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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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[Production of reconstructed two-cell rat embryos after chemical inactivation of chromosomes in MII oocytes by etoposide]. | 2008 Sep-Oct |
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Fasting and cancer treatment in humans: A case series report. | 2009 Dec 31 |
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Pegylated liposomal doxorubicin in ovarian cancer. | 2009 Jun |
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2-Arylbenzimidazoles as antiviral and antiproliferative agents--Part 2. | 2009 Nov |
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Helicobacter pylori counteracts the apoptotic action of its VacA toxin by injecting the CagA protein into gastric epithelial cells. | 2009 Oct |
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Bevacizumab in combination with sequential high-dose chemotherapy in solid cancer, a feasibility study. | 2010 Dec |
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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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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 |
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 15 15:34:11 UTC 2023
by
admin
on
Fri Dec 15 15:34:11 UTC 2023
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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 Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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NDF-RT |
N0000000176
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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WHO-VATC |
QL01CB01
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WHO-ESSENTIAL MEDICINES LIST |
8.2
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NCI_THESAURUS |
C1331
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LIVERTOX |
NBK548102
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WHO-ATC |
L01CB01
Created by
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1112
Created by
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33419-42-0
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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CHEMBL44657
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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3835
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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PRIMARY | |||
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1268808
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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PRIMARY | |||
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C491
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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6517
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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251-509-1
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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PRIMARY | |||
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6PLQ3CP4P3
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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PRIMARY | |||
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4179
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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PRIMARY | RxNorm | ||
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D005047
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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PRIMARY | |||
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m5199
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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PRIMARY | Merck Index | ||
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100000082091
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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36462
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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SUB07337MIG
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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4911
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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ETOPOSIDE
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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DTXSID5023035
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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DB00773
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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ETOPOSIDE
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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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 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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PRIMARY | |||
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6PLQ3CP4P3
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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PRIMARY | |||
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141540
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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Etoposide
Created by
admin on Fri Dec 15 15:34:11 UTC 2023 , Edited by admin on Fri Dec 15 15:34:11 UTC 2023
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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 -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> SUBSTRATE |
Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
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||
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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 |
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Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
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||
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IMPURITY -> PARENT |
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||
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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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