Etoposide phosphate

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.

Product information

CAS Number: 117091-64-2

Molecular Weight: 668.54

Formula: C29H33O16P

Synonym:

BMY-40481 disodium)

Chemical Name: {4-[(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}-12-oxo-4, 6, 13-trioxatetracyclo[7.7.0.0, .0, ]hexadeca-1(9), 2, 7-trien-10-yl]-2, 6-dimethoxyphenoxy}phosphonic acid

Smiles: C[C@H]1O[C@@H]2[C@@H](CO1)O[C@@H](O[C@H]1[C@H]3COC(=O)[C@@H]3[C@@H](C3=CC4OCOC=4C=C31)C1C=C(OC)C(OP(O)(O)=O)=C(C=1)OC)[C@H](O)[C@H]2O

InChiKey: LIQODXNTTZAGID-OCBXBXKTSA-N

InChi: InChI=1S/C29H33O16P/c1-11-38-9-20-27(42-11)23(30)24(31)29(43-20)44-25-14-7-17-16(40-10-41-17)6-13(14)21(22-15(25)8-39-28(22)32)12-4-18(36-2)26(19(5-12)37-3)45-46(33,34)35/h4-7,11,15,20-25,27,29-31H,8-10H2,1-3H3,(H2,33,34,35)/t11-,15+,20-,21-,22+,23-,24-,25-,27-,29+/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Etoposide phosphate disodium 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. Etoposide phosphate disodium (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. Etoposide phosphate disodium (25 μM; 6 hours) delays p53 recover in FBXW7-deficient cells. In addition, FBXW7 expression is disappeared in FBXW7-/- cells.

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.

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

Products are for research use only. Not for human use.