CAS 117091-64-2|Etoposide 4'-Phosphate
Introduction：Basic information about CAS 117091-64-2|Etoposide 4'-Phosphate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Etoposide 4'-Phosphate | ||
|---|---|---|---|
| CAS Number | 117091-64-2 | Molecular Weight | 666.522 |
| Density | 1.55 g/cm3 | Boiling Point | 907.7±75.0 °C at 760 mmHg |
| Molecular Formula | C29H33O16P | Melting Point | / |
| MSDS | / | Flash Point | 502.7±37.1 °C |
Names
| Name | Etoposide Phosphate |
|---|---|
| Synonym | More Synonyms |
Etoposide 4'-Phosphate BiologicalActivity
| Description | Etoposide phosphate (BMY-40481) is a potent anti-cancer chemotherapy agent and a selective topoisomerase II inhibitor to prevent re-ligation of DNA strands. Etoposide phosphate is the phosphate ester prodrug of etoposide and is considered as active equivalent to Etoposide. Etoposide phosphate induces cell cycle arrest, apoptosis, and autophagy[1][2]. |
|---|---|
| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerSignaling Pathways >>Cell Cycle/DNA Damage >>TopoisomeraseSignaling Pathways >>Autophagy >>AutophagyResearch Areas >>Neurological Disease |
| Target | Topoisomerase II |
| In Vitro | Etoposide phosphate is a water-soluble derivative and probable prodrug of etoposide characterized by the presence of a phosphate group in position 4' of the E ring of the etoposide molecule[1]. Etoposide phosphate (0-1 μM; 72 hours) inhibits HCT116 FBXW+/+, FBXW-/- and p53-/- as a dose-dependent manner, exhibits IC50 values of 0.945 μM; 0.375 μM; and 1.437 μM, respectively[2]. Etoposide phosphate (25 μM; 6 hours) delays p53 recover in FBXW7-deficient cells. In addition, FBXW7 expression is disappeared in FBXW7-/- cells[2]. Cell Viability Assay[2] Cell Line: FBXW+/+, FBXW-/- and p53-/- cell Concentration: 0.025 μM, 0.05 μM, 0.075 μM, 0.1 μM, 0.2 μM, 0.4 μM, 0.6 μM, 0.8 μM, 1 μM Incubation Time: 72 hours Result: Inhibited HCT116 FBXW+/+, FBXW-/- and p53-/- cell growth as a concentration manner. Western Blot Analysis[2] Cell Line: HCT116 FBXW7+/+ or FBXW7-/- cells Concentration: 25 μM Incubation Time: 6 hours Result: Exhibited that the recovery of p53 levels after DNA damage is mediated by FBXW7. |
| In Vivo | Etoposide phosphate (intravenous injection; 50, 100, or 150 mg/kg; single dose) has clinical symptomology of progressive ataxia, impaired righting reflex, and splaying and paresis of fore- and hindlimbs at day 8 in female CD-1 mice[3]. Animal Model: Female CD-1 mice[3] Dosage: 50, 100, or 150 mg/kg Administration: Intravenous injection; single dose Result: Observed degeneration of dorsal root ganglion cells and axonal degeneration of their distal and proximal processes in peripheral nerves, dorsal spinal roots, and dorsal funiculi of the spinal cord at all doses under light microscopy (LM). |
| References | [1]. Witterland AH, et al. Etoposide phosphate, the water soluble prodrug of etoposide. Pharm World Sci. 1996 Oct;18(5):163-70. [2]. Cui D, et al. FBXW7 Confers Radiation Survival by Targeting p53 for Degradation.Cell Rep. 2020 Jan 14;30(2):497-509.e4. [3]. Bregman CL, et al. Etoposide- and BMY-40481-induced sensory neuropathy in mice.Toxicol Pathol. 1994 Sep-Oct;22(5):528-35. [4]. SUMMARY OF PRODUCT CHARACTERISTICS |
Chemical & Physical Properties
| Density | 1.55 g/cm3 |
|---|---|
| Boiling Point | 907.7±75.0 °C at 760 mmHg |
| Molecular Formula | C29H33O16P |
| Molecular Weight | 666.522 |
| Flash Point | 502.7±37.1 °C |
| Exact Mass | 666.136047 |
| PSA | 217.17000 |
| LogP | -1.28 |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| InChIKey | LIQODXNTTZAGID-STKZERGVSA-N |
| SMILES | COc1cc(C2c3cc4c(cc3C(OC3OC5COC(C)OC5C(O)C3O)C3COC(=O)C23)OCO4)cc(OC)c1OP(=O)(O)O |
| Storage condition | 20°C |
Safety Information
| Hazard Codes | F |
|---|
Synonyms
| Etoposide phosphate |
| Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5-[3,5-dimethoxy-4-(phosphonooxy)phenyl]-9-[[4,6-O-[(1R)-ethylidene]-β-D-glucopyranosyl]oxy]-5,8,8a,9-tetrahydro-, ion(2-), (5R,5aR)- |
| 4-[(5R,5aR)-9-{[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxyphenyl phosphate |
| 4-[(5R,5aR)-9-{[(2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-methylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxyphenylphosphat |
| 4-[(5R,5aR)-9-({4,6-O-[(1R)-Ethylidene]-β-D-glucopyranosyl}oxy)-6-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl]-2,6-dimethoxyphenyl phosphate |
