ETOPOSIDE TONIRIBATE

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(=CC(OC)=C1OC(=O)OCC2COC(C)(C)O2)[C@H]3[C@@H]4[C@H](COC4=O)[C@H](O[C@@H]5O[C@@H]6CO[C@@H](C)O[C@H]6[C@H](O)[C@H]5O)C7=C3C=C8OCOC8=C7

InChI

InChIKey=FCWSQAKOPTZCOD-SQYSSJHTSA-N

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

HIDE SMILES / InChI

Molecular Formula	C36H42O17
Molecular Weight	746.7085
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	10 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
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
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16101488	Inhibitor 8504		0.8 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Refractory testicular tumors 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf	Primary		Approved 8583	ETOPOPHOS PRESERVATIVE FREE Approved Use ETOPOPHOS for Injection is indicated in the management of the following neoplasms: Refractory Testicular Tumors-ETOPOPHOS for Injection in combination therapy with other approved chemotherapeutic agents in patients with refractory testicular tumors who have already received appropriate surgical, chemotherapeutic, and radiotherapeutic therapy. Small Cell Lung Cancer-ETOPOPHOS for Injection in combination with other approved chemotherapeutic agents as first-line treatment in patients with small cell lung cancer. Launch Date 1983
Small-cell lung cancer 41 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf	Primary		Approved 8583	ETOPOPHOS PRESERVATIVE FREE Approved Use ETOPOPHOS for Injection is indicated in the management of the following neoplasms: Refractory Testicular Tumors-ETOPOPHOS for Injection in combination therapy with other approved chemotherapeutic agents in patients with refractory testicular tumors who have already received appropriate surgical, chemotherapeutic, and radiotherapeutic therapy. Small Cell Lung Cancer-ETOPOPHOS for Injection in combination with other approved chemotherapeutic agents as first-line treatment in patients with small cell lung cancer. Launch Date 1996

C_max

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

T_1/2

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

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf			ETOPOSIDE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

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: https://pubmed.ncbi.nlm.nih.gov/8021737	unhealthy, 1.1-17 Health Status: unhealthy Age Group: 1.1-17 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8021737	DLT: Neutropenia, Thrombocytopenia... Dose limiting toxicities: Neutropenia (grade 4, 25%) Thrombocytopenia (grade 4, 12.5%) Leukopenia (grade 4, 12.5%) Diarrhea (grade 3, 12.5%) Diarrhea (grade 4, 12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/8021737
20 mg/m2 3 times / day multiple, oral MTD Dose: 20 mg/m2, 3 times / day Route: oral Route: multiple Dose: 20 mg/m2, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8021737	unhealthy, 1.1-17 Health Status: unhealthy Age Group: 1.1-17 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/8021737	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 14%) Sources: https://pubmed.ncbi.nlm.nih.gov/8021737
175 mg/m2 1 times / day multiple, intravenous MTD Dose: 175 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 175 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7799021	unhealthy, 39-72 Health Status: unhealthy Age Group: 39-72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7799021	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 28.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/7799021
175 mg/m2 1 times / day multiple, intravenous MTD Dose: 175 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 175 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7799021	unhealthy, 39-72 Health Status: unhealthy Age Group: 39-72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7799021	DLT: Neutropenia... Dose limiting toxicities: Neutropenia (grade 3, 14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/7799021
220 mg/m2 1 times / day multiple, intravenous MTD Dose: 220 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 220 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7799021	unhealthy, 39-72 Health Status: unhealthy Age Group: 39-72 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7799021	DLT: Neutropenia, Neutropenia... Dose limiting toxicities: Neutropenia (grade 3, 25%) Neutropenia (grade 4, 25%) Sources: https://pubmed.ncbi.nlm.nih.gov/7799021
60 mg/m2 1 times / day multiple, oral Recommended Dose: 60 mg/m2, 1 times / day Route: oral Route: multiple Dose: 60 mg/m2, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9469322	unhealthy, 39-83 Health Status: unhealthy Age Group: 39-83 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/9469322	DLT: Leukopenia, Neutropenia... Disc. AE: Nausea and vomiting, Fatigue... Dose limiting toxicities: Leukopenia (grade 4, 12%) Neutropenia (grade 4, 25%) Leukopenia (grade 3, 29%) Neutropenia (grade 3, 20%) Thrombocytopenia (grade 4, 4%) AEs leading to discontinuation/dose reduction: Nausea and vomiting (3%) Fatigue (1%) Neutropenic sepsis (grade 5, 2%) Bleeding (grade 5, 1%) Sources: https://pubmed.ncbi.nlm.nih.gov/9469322
100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf	Disc. AE: Myelosuppression... AEs leading to discontinuation/dose reduction: Myelosuppression (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020457s013lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 499	OATP1B1 503 P-gp 2052 CYP2E1 729 CYP1A2 1197 CYP3A5 446 CYP2B6 776 CYP2A6 626 UGT1A1 479 UGT1A8 323 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A9 423 UGT1A10 331 UGT2B4 278 UGT2B7 456 UGT2B15 236 UGT2B17 237 Abcc2 3 Abcc3 3 MRP2 252 MRP3 58	CYP3A5 92

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A5 201	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	slight
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12134946/	weak [Ki 756 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf	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% Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2002/019557s028lbl.pdf
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	major		yes (pharmacogenomic study) Comment: UGT1A128 and UGT1A16 mutations might be regarded as predictors for etoposide-induced grade 4 neutropenia. Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/
CYP1A2 1197	substrate 4014 Sources: https://jpet.aspetjournals.org/content/286/3/1294.long	minor
CYP2E1 729	substrate 4014 Sources: https://jpet.aspetjournals.org/content/286/3/1294.long	minor
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	minor
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	minor
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	no
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17151191/	no
Abcc2 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20028753/	yes
Abcc3 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20028753/	yes	ETOPOSIDE GLUCURONIDE 3
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15319341/	yes
MRP2 252	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3372834/	yes
MRP3 58	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11581266/	yes	ETOPOSIDE GLUCURONIDE 3
OATP1B1 503	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3372834/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/7850926/	yes

Sourcing

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

PubMed

Title	Date	PubMed
Outpatient reduced-intensity allogeneic stem cell transplantation for patients with refractory or relapsed lymphomas compared with autologous stem cell transplantation using a simplified method.	2010-10	20490794
Biological characteristics and treatment outcomes of metastatic or recurrent neuroendocrine tumors: tumor grade and metastatic site are important for treatment strategy.	2010-08-23	20731845
Preclinical pharmacology of BA-TPQ, a novel synthetic iminoquinone anticancer agent.	2010-07-13	20714427
Role of dephosphorylation of FOXO1 on apoptosis induced by wortmannin for non-Hodgkin's lymphoma cells.	2010-06	19757185
Cellular responses to etoposide: cell death despite cell cycle arrest and repair of DNA damage.	2010-02	20041303
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.	2010-02	19901016
Chemotherapy resistance in metastatic breast cancer: the evolving role of ixabepilone.	2010	21050423
Fasting and cancer treatment in humans: A case series report.	2009-12-31	20157582
[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].	2009-12	20070034
Etoposide induces MLL rearrangements and other chromosomal abnormalities in human embryonic stem cells.	2009-09	19587093
Pegylated liposomal doxorubicin in ovarian cancer.	2009-06	19707541
No attenuation of the ATM-dependent DNA damage response in murine telomerase-deficient cells.	2009-03-01	19071232
[Production of reconstructed two-cell rat embryos after chemical inactivation of chromosomes in MII oocytes by etoposide].	2008-10-31	18959199
Therapy-associated genetic aberrations in patients treated for non-Hodgkin lymphoma.	2008-04	18324966
A Contribution to solve the problem of the need for consolidative radiotherapy after intensive chemotherapy in advanced stages of Hodgkin's lymphoma--analysis of a quality control program initiated by the radiotherapy reference center of the German Hodgkin Study Group (GHSG).	2007-11-15	17703895
Upregulation of bfl-1 is a potential mechanism of chemoresistance in B-cell chronic lymphocytic leukaemia.	2007-09-17	17726463
In vivo targeting of dead tumor cells in a murine tumor model using a monoclonal antibody specific for the La autoantigen.	2007-09-15	17875784
BRCA1- and BRCA2-deficient cells are sensitive to etoposide-induced DNA double-strand breaks via topoisomerase II.	2007-08-01	17671173
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.	2007-05-23	17519046
Modulation of topoisomerase IIalpha expression by a DNA sequence-specific polyamide.	2007-01	17237293
[Pulmonary and pleural manifestations of multiple myeloma].	2006-12	17163315
Bcl-XL is qualitatively different from and ten times more effective than Bcl-2 when expressed in a breast cancer cell line.	2006-08-23	16928273
Adenine nucleotides inhibit proliferation of the human lung adenocarcinoma cell line LXF-289 by activation of nuclear factor kappaB1 and mitogen-activated protein kinase pathways.	2006-08	16911524
Randomized phase III trial comparing irinotecan/cisplatin with etoposide/cisplatin in patients with previously untreated extensive-stage disease small-cell lung cancer.	2006-05-01	16648503
Use of preclinical models to improve treatment of retinoblastoma.	2005-10	16231976
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).	2005-07	15726362
Evaluation of the combined effect of p53 codon 72 polymorphism and hotspot mutations in response to anticancer drugs.	2005-06-15	15958617
HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC).	2005-06-09	15946380
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.	2005-06	16019530
High-throughput technology: green fluorescent protein to monitor cell death.	2005	15901932
Phase I dose escalation study of carboplatin to a fixed dose of irinotecan as first-line treatment of small cell lung cancer.	2004-06	15249718
Inhibition of telomerase activity in malignant glioma cells correlates with their sensitivity to temozolomide.	2003-09-01	12942127
EBNA1 may prolong G(2)/M phase and sensitize HER2/neu-overexpressing ovarian cancer cells to both topoisomerase II-targeting and paclitaxel drugs.	2003-08-01	12893273
Oral melphalan as a treatment for platinum-resistant ovarian cancer.	2003-06-16	12799622
Phase I/II trial of weekly cisplatin, etoposide, and irinotecan chemotherapy for metastatic lung cancer: JCOG 9507.	2003-03-24	12644814
Estrogen receptor-dependent and estrogen receptor-independent pathways for tamoxifen and 4-hydroxytamoxifen-induced programmed cell death.	2002-11-22	12244117
Coexisting true hermaphroditism and partial hydatidiform mole developing metastatic gestational trophoblastic tumors. A case report.	2002-11	12447683
Detection of topoisomerase inhibitor-induced DNA strand breaks and apoptosis by the alkaline comet assay.	2002-09-26	12297143
Treatment of gestational trophoblastic tumors.	2002-04	12057074
Alpha-CD25 antibody treatment in a child with hemophagocytic lymphohistiocytosis.	2002-02	11813188
Expression of P-glycoprotein and multidrug resistance associated protein in Ehrlich ascites tumor cells after fractionated irradiation.	2001-11-15	11704330
Pro-oxidant and antioxidant mechanisms of etoposide in HL-60 cells: role of myeloperoxidase.	2001-11-01	11691792
Langerhans cell histiocytosis.	2001-11	11903153
Bone morphogenetic protein-2 promotes osteoblast apoptosis through a Smad-independent, protein kinase C-dependent signaling pathway.	2001-08-03	11395480
High-dose chemotherapy as a consolidation approach in advanced ovarian cancer: long-term results.	2001-05	11438815
Irinotecan: future directions in small-cell lung cancer.	2001-05	14725724
High-dose chemotherapy with peripheral blood stem cell transplantation for patients with advanced ovarian cancer.	2001-04	11315259
Adult Gaucher disease in association with primary malignant bone tumors.	2001-02-01	11169926
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	11820594
Etoposide-induced hypersensitivity reactions. Report of two cases.	1985-12	3830414

Patents

Sample Use Guides

In Vivo Use Guide

50 to 100 mg/m2/day on days 1 through 5 to 100 mg/m2/day on days 1, 3, and 5 (testicular cancer) 35 mg/m2/day for 4 days to 50 mg/m2/day for 5 days (small cell lung cancer)

Route of Administration: Intravenous

In Vitro Use Guide

Apoptosis of thymocytes has been investigated by morphological, biochemical and cytometric techniques, both in non-perturbed conditions and after exposure to the topoisomerase-II inhibitor etoposide in vitro. At low (0.1 to 10 uM) etoposide concentrations apoptotic cells had cytoplasm patterns similar to naturally occurring apoptotic thymocytes, whereas at high (50 to 100 uM) concentrations extensive organelle damage took place.

Substance Class	Chemical Created by `admin` on `Tue Apr 01 18:44:14 GMT 2025` Edited by `admin` on `Tue Apr 01 18:44:14 GMT 2025`
Record UNII	A59HL2Q48U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETOPOSIDE TONIRIBATE

Official Name

English

(4-((5S,5AR,8AR,9R)-5-(((2R,4AR,6R,7R,8R,8AS)-7,8-DIHYDROXY-2-METHYL-4,4A,6,7,8,8A-HEXAHYDROPYRANO(3,2-D)(1,3)DIOXIN-6-YL)OXY)-8-OXO-5A,6,8A,9-TETRAHYDRO-5H-ISOBENZOFURO(5,6-F)(1,3)BENZODIOXOL-9-YL)-2,6-DIMETHOXY-PHENYL) (2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)M

Preferred Name

English

CARBONIC ACID, (2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)METHYL 4-((5R,5AR,8AR,9S)-9-((4,6-O-(1R)-ETHYLIDENE-.BETA.-D-GLUCOPYRANOSYL)OXY)-5,5A,6,8,8A,9-HEXAHYDRO-6-OXOFURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-5-YL)-2,6-DIMETHOXYPHENYL ESTER

Systematic Name

English

PROVP-16I

Common Name

English

((4RS)-2,2-DIMETHYL-1,3-DIOXOLAN-4-YL)METHYL4-((5R,5AR,8AR,9S)-9-((4,6-O-((1R)-ETHANE-1,1-DIYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-6-OXO-5,5A,6,8,8A,9-HEXAHYDRO-2H-FURO(3',4':6,7)NAPHTHO(2,3-D)(1,3)DIOXOL-5-YL)-2,6-DIMETHOXYPHENYL CARBONATE

Systematic Name

English

etoposide toniribate [INN]

Common Name

English

CAP-7.1

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

671318