Etoposide
- CAS No.
- 33419-42-0
- Chemical Name:
- Etoposide
- Synonyms
- epe;vepesid;VP-16;Toposar;Celltop;epec;nk171;e[qr];Etopl;lastet
- CBNumber:
- CB8270005
- Molecular Formula:
- C29H32O13
- Molecular Weight:
- 588.56
- MOL File:
- 33419-42-0.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/4/23 19:22:53
| Melting point | 236-251 °C (lit.) |
|---|---|
| Boiling point | 563.9°C (rough estimate) |
| alpha | D20 -110.5° (c = 0.6 in chloroform) |
| Density | 1.2966 (rough estimate) |
| refractive index | -110.5 ° (C=0.6, CHCl3) |
| storage temp. | 2-8°C |
| solubility | DMSO: 30 mg/mL |
| form | powder |
| pka | 9.8(at 25℃) |
| color | white |
| Water Solubility | Insoluble in water. |
| Merck | 14,3886 |
| BCS Class | 4 |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months |
| IARC | 1 (Vol. 76, 100A) 2012, 1 (Vol. 76, 100A) 2012 |
| EPA Substance Registry System | Etoposide (33419-42-0) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H350-H361d-H412 | |||||||||
| Precautionary statements | P201-P280-P301+P312+P330-P308+P313 | |||||||||
| Hazard Codes | T,Xi | |||||||||
| Risk Statements | 45-22-36/37/38 | |||||||||
| Safety Statements | 53-45-36/37-26 | |||||||||
| RIDADR | 3249 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | KC0190000 | |||||||||
| HazardClass | 6.1(a) | |||||||||
| PackingGroup | II | |||||||||
| HS Code | 29389090 | |||||||||
| Toxicity | LD50 oral in rabbit: 147mg/kg | |||||||||
| NFPA 704 |
|
Etoposide price More Price(13)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | SRP2017 | GAL4 [(1-147) + VP16 (411-490)] from Saccharomyces cerevisiae human herpesvirus 2 recombinant, expressed in E. coli, ≥80% (SDS-PAGE) | 33419-42-0 | 10μG | ₹40796.8 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | SRP2017 | GAL4 [(1-147) + VP16 (411-490)] from Saccharomyces cerevisiae human herpesvirus 2 recombinant, expressed in E. coli, ≥80% (SDS-PAGE) | 33419-42-0 | 500μG | ₹1797560.2 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | E1383 | Etoposide synthetic, 95.0-105.0%, powder | 33419-42-0 | 25MG | ₹9883.23 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | E1383 | Etoposide synthetic, 95.0-105.0%, powder | 33419-42-0 | 100MG | ₹27863.55 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | E1383 | Etoposide synthetic, 95.0-105.0%, powder | 33419-42-0 | 250MG | ₹54265.73 | 2022-06-14 | Buy |
Etoposide Chemical Properties,Uses,Production
Description
Etoposide is a plant alkaloid and an inhibitor of topoisomerase II (IC50 = 60.3 μM). It inhibits proliferation of a variety of adenocarcinoma cells (IC50s = 0.005-12,200 μM) and human umbilical vein endothelial (HUVEC) cells (IC50 = 0.249 μM). It reduces tumor growth in an Ma human embryonal carcinoma mouse xenograft model when administered at a dose of 25 mg/kg, an effect that is enhanced by concomitant administration of the immunosuppressant cyclosporin A . Etoposide also inhibits nuclear receptor coactivator 3 (IC50 = 2.48 μM). Formulations containing etoposide have been used in combination therapy in the treatment of cancer.
Chemical Properties
White or almost white, crystalline powder, slightly hygroscopic
Uses
Etoposide is used for germinogenic tumors, ovarian, stomach, and lung cancer, Hodgkin’s disease, and non-Hodgkin’s lymphoma for both monotherapy and in combination therapy.
Indications
Etoposide (VePesid) is a semisynthetic derivative of
podophyllotoxin that is produced in the roots of the
American mandrake, or May apple. Unlike podophyllotoxin
and vinca alkaloids, etoposide does not bind to microtubules.
It forms a complex with the enzyme topoisomerase
II, which results in a single-strand breakage of
DNA. It is most lethal to cells in the S- and G2-phases of
the cell cycle. Drug resistance to etoposide is thought to
be caused by decreased cellular drug accumulation.
Etoposide is most useful against testicular and ovarian
germ cell cancers, lymphomas, small cell lung cancers,
and acute myelogenous and lymphoblastic
leukemia.Toxicities include mild nausea, alopecia, allergic
reaction, phlebitis at the injection site, and bone
marrow toxicity.
Clinical Use
Etoposide is utilized in the treatment of small cell lung cancer and in combination with other agents in refractory testicular cancer.
Safety Profile
Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion and inhalation: agranulocytosis, aplastic anemia, and other changes in bone marrow. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and fumes.
Metabolism
The drug is more than 96% protein bound, undergoes biphasic elimination, and has a terminal half-life of 4 to 11 hours. Approximately 35 to 45% of a dose is eliminated via the kidneys, with less than 6% excreted in feces. The drug should be used with caution in patients with renal or liver disease.
References
Hande, K. R. "Etoposide: four decades of development of a topoisomerase II inhibitor." European Journal of Cancer34.10(1998):1514.
Noda, K, et al. "Irinotecan plus cisplatin compared with etoposide plus cisplatin for extensive small-cell lung cancer." New England Journal of Medicine 346.2(2002):85-91.
Etoposide Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| GLP Pharma Standards | +91 9866074638 | Hyderabad, India | 1644 | 58 | Inquiry |
| Medi Pharma Drug House | +919930911911 | Mumbai, India | 143 | 58 | Inquiry |
| Cipla Ltd | +912224826000 | Maharashtra, India | 133 | 58 | Inquiry |
| Zyphars Biopharmaceuticals Pvt. Ltd | +91-8007587007 +91-8007587007 | Mumbai, India | 14 | 58 | Inquiry |
| Basil Drugs AND Pharmaceuticals Pvt Ltd | +91-2249700250 +91-9619320820 | Mumbai, India | 108 | 58 | Inquiry |
| BDR Pharmaceuticals International Pvt Ltd | +91-2240560560 +91-7718884418 | Maharashtra, India | 206 | 58 | Inquiry |
| Mac Chem Products (India) Pvt Ltd (Naprod Group) | +91-9727753234 +91-7770016606 | Maharashtra, India | 37 | 58 | Inquiry |
| Aspen Biopharma Labs Pvt Ltd | +91-9248058660 +91-9248058662 | Telangana, India | 234 | 58 | Inquiry |
| Sakar Healthcare | +91-8976292690 +91-9967572302 | Gujarat, India | 47 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
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MES-012 BMY-40481, Etoposide 4'-Dihydrogenphosphate, VP-16-213 Etoposide , 98.0%(LC) Etoposide for system suitability GAL4 [(1-147) + VP16 (411-490)] from Saccharomyces cerevisiae human herpesvirus 2 Etoposide, >=98% (5R,5aR,8aR,9S)-9-[[4,6-O-(1R)-Ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one (5R,5AR,8aR,9S)-9-(((2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dio VP-16-213 epipodophyllotoxin,4’-demethyl-,4,6-o-ethylidene-beta-d-glucopyranoside epipodophyllotoxin,4’-demethyl-,9-(4,6-o-ethylidene-beta-d-glucopyranoside) lastet nk171 nsc141540 nsc-141540 4'-DEMETHYLEPIPODOPHYLLOTOXIN 9-(4,6-O-ETHYLIDENE-BETA-D-GLUCOPYRANOSIDE) 4-demethylepipodophyllotoxin-beta-d-ethylideneglucoside Etoposide4-O--D-Galactopyranoside Furo3,4:6,7naphtho2,3-d-1,3-dioxol-6(5aH)-one, 9-4,6-O-(1R)-ethylidene-.beta.-D-glucopyranosyloxy-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)- 4'-demethylepipodophyllotoxin 9-(4,6-o-ethylidene-β-d-glucopyranoside) Etoposide(α-tipe) 4'-Demethyl-1-O-[4,6-O-(ethylidene)-β-D-glucopyranosyl]epipodophyllotoxin 4'-Demethylepipodophyllotoxin ethylidene-β-D-glucoside Epipodophyllotoxin VP 16213 Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-β-D-glucopyranoside (8CI) Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[(4,6-O-ethylidene-β-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-[5α,5aβ,8aα,9β(R*)]]- Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 9-[[4,6-O-(1R)-ethylidene-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)- trans-Etoposide VP 16 (pharmaceutical) VP 16-123 Zuyeyidal Etoposide USP26 Etoposide (FDA) USP24 BP98 Etoposide BP2000 ETOPOSIDE, MM(CRM STANDARD) ETOPOSIDE, EP STANDARD ETOPOSIDE, USP STANDARD ETOPOSIDE, RESOLUTION MIXTURE USP STANDARD ETOPOSIDE, USP 99+% Etoposide,Usp28 DEMETHYLEPIPODOPHYLLOTOXIN-BETA-D-ETHYLIDENEGLUCOSIDE ETOPOSIDE (VEPESID) Etoposide (contains ca. 5% Ethanol) Etoposide (VP-16) (5R,5aα,9S)-9-[[4-O,6-O-[(R)-Ethylidene]-β-D-glucopyranosyl]oxy]-5,8,8aβ,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one Etoposide - In combination with Cisplatin and Bleomycin 9-((4,6-O-Ethylidene-beta-D-glucopyranosyl)oxy)-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one [5R-[5alpha,5abeta,8aalpha,9beta(R*)]]-9-[(4,6-O-Ethylidene-beta-D-glucopyranosyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one 9-((4,6-O-Ethylidine-Beta-D-Glucopyranosyl)Oxy)- [5R-[5α,5aβ,8aα,9β(R*)]]-9-[(4,6-0-Ethylidene-α-D-glucopyransoyl)oxy]-5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3',4':6,7]naptho[2,3-d]-1,3-dioxol-6-(5aH)-one Etoposide,4′-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-β-D-glucopyranoside), VP-16-213 Etoposide (300 mg) Etoposide Resolution Mixture (30 mg) Etoposide Resolution Mixture Etoposide, USP (10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-Methyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-10-(4-hydroxy-3,5-diMethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one (5R,5aR,8aR,9S)-