structure of Etoposide Impurity B

Etoposide Impurity B

CAS No.: 100007-56-5
M. Wt: 588.55700
M. Fa: C29H32O13
InChI Key: VJJPUSNTGOMMGY-KOUFYDGNSA-N

Names and Identifiers of Etoposide Impurity B

CAS Number

100007-56-5

IUPAC Name

(5S,5aR,8aS,9R)-5-[[(4aR,6R,7S,8R,8aR)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

InChI

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-/m0/s1

InChIKey

VJJPUSNTGOMMGY-KOUFYDGNSA-N

Canonical SMILES

CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O

Isomeric SMILES

CC1OC[C@@H]2[C@H](O1)[C@@H]([C@@H]([C@@H](O2)O[C@H]3[C@H]4COC(=O)[C@H]4[C@@H](C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O

Physical and chemical properties of Etoposide Impurity B

Acidity coefficient

9.94±0.40(Predicted)

Boiling Point

798.1±60.0 °C(Predicted)

Density

1.55±0.1 g/cm3(Predicted)

Exact Mass

588.18400

LogP

1.33860

Molecular Formula

C29H32O13

Molecular Weight

588.55700

PSA

160.83000

Applications of Etoposide Impurity B

Cis-Etoposide is primarily used in oncology for treating various cancers, including:

  • Testicular Cancer: Effective as part of combination chemotherapy regimens.
  • Small Cell Lung Cancer: Often used in conjunction with other agents like carboplatin.
  • Lymphomas: Demonstrates activity against both Hodgkin and non-Hodgkin lymphoma.
  • Other Malignancies: Utilized in treatment protocols for bladder, stomach, and prostate cancers.

Biological Activity of Etoposide Impurity B

The biological activity of cis-Etoposide is characterized by its ability to induce apoptosis in cancer cells. The compound's mechanism of action involves the formation of a stable complex with topoisomerase II and DNA, preventing the enzyme from resealing the DNA breaks it creates. This leads to increased levels of DNA damage, triggering cellular pathways that result in apoptosis. Etoposide's effectiveness varies with dosage and schedule; it is more potent at specific concentrations and during particular phases of the cell cycle.