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Etoposide

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Identification
Molecular formula
C29H32Cl2O13P
CAS number
33419-42-0
IUPAC name
(13-methyl-17-phosphonooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl) N,N-bis(2-chloroethyl)carbamate
State
State

At room temperature, etoposide is commonly found as a liquid solution or in capsule form for pharmaceutical use. The compound itself, when pure, is a white to off-white crystalline powder, which may be hygroscopic, tending to absorb moisture from the air.

Melting point (Celsius)
231.50
Melting point (Kelvin)
504.70
Boiling point (Celsius)
293.80
Boiling point (Kelvin)
566.95
General information
Molecular weight
588.54g/mol
Molar mass
588.5610g/mol
Density
1.4600g/cm3
Appearence

Etoposide is typically supplied as a clear to slightly yellow liquid solution containing the active ingredient. It is commercially available in both liquid form for injection and in capsule forms for oral administration. The appearance may vary depending on the formulation and manufacturer.

Comment on solubility

Solubility of (13-methyl-17-phosphonooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl) N,N-bis(2-chloroethyl)carbamate

The solubility of the compound with the formula C29H32Cl2O13P can be characterized as quite complex due to its intricate molecular structure and the presence of multiple functional groups. Understanding the solubility behavior may rely on various factors:

  • Polarity: The presence of polar functional groups such as the phosphorus-containing moiety and carbamate suggests that the compound may exhibit some degree of solubility in polar solvents, like water or alcohols.
  • Chlorinated Presence: The two chlorine atoms within the structure could influence hydrophobic interactions, potentially leading to limited solubility in non-polar solvents.
  • Structural Factors: The bulky and complex ring system may create steric hindrance, which can negatively impact solubility. Generally, larger and more complex molecules tend to be less soluble.
  • pH Dependence: Depending on the pH of the solution, the ionization of the carbamate unit could further influence solubility behavior; carbamates can behave differently in acidic versus basic conditions.

In conclusion, while the exact solubility characteristics of this compound under varying conditions may require empirical testing, the interplay of polarity, structural complexity, and environmental factors suggests a moderate to limited solubility in common solvents. Understanding the solubility profile is crucial for applications in various chemical and biological contexts.

Interesting facts

Interesting Facts about (13-Methyl-17-phosphonooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl) N,N-bis(2-chloroethyl)carbamate

This compound is a fascinating example of how intricate organic chemistry can be, merging elements of medicinal chemistry and organophosphate chemistry. Its structure reflects the complex relationship between chemical functionality and biological activity.

Key Characteristics:

  • Unique Structure: With multiple rings and substituents, the molecular architecture of this compound contributes to its potential biological activity and therapeutic applications.
  • Phosphono Group: The presence of a phosphono group suggests potential for influencing various biochemical pathways, making it a candidate for investigational studies in pharmacology.
  • Chloroethyl Substituents: The N,N-bis(2-chloroethyl) component could indicate functionality related to alkylation, which is important in the context of antitumor agents.

The compound's design hints at its application in areas such as targeted therapy or as a pesticide, illustrating the duality of compounds in influencing both health and agriculture. As with many compounds in this category, optimizing the balance between efficacy and safety is paramount. The ability to manipulate the structure further allows chemists to explore new derivatives with tailored functions.

Additionally, the synthesis and characterization of such compounds present significant challenges and opportunities for innovation within the field. As one researcher insightfully noted, "In the world of chemical compounds, every structural modification can lead to a surprising enhancement in potency." This reality underscores the exciting possibility of discovering new properties through synthetic chemistry.

Overall, (13-methyl-17-phosphonooxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl) N,N-bis(2-chloroethyl)carbamate serves as a compelling reminder of the intricate dance between structure and function in chemistry.

Synonyms
SCHEMBL1649356
DTXSID20859890
DS-002554
NS00021174
17-(phosphonooxy)estra-1,3,5(10)-trien-3-yl bis(2-chloroethyl)carbamate
Estra-1,3,5(10)-triene-3,17β-diol 3-[bis(2-chloroethyl)carbamate] 17-(dihydrogen phosphate)