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Adefovir dipivoxil

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Identification
Molecular formula
C20H32N5O8P
CAS number
106941-25-7
IUPAC name
S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] hexadecanethioate
State
State

At room temperature, Adefovir dipivoxil is a solid. It is used in the form of an oral prodrug for the treatment of hepatitis B.

Melting point (Celsius)
273.14
Melting point (Kelvin)
546.29
Boiling point (Celsius)
506.80
Boiling point (Kelvin)
780.00
General information
Molecular weight
501.22g/mol
Molar mass
501.2220g/mol
Density
2.1000g/cm3
Appearence

Adefovir dipivoxil typically appears as a white to off-white crystalline powder.

Comment on solubility

Solubility of S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] hexadecanethioate

The solubility of S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] hexadecanethioate can be quite complex due to its intricate molecular structure and the presence of functional groups that may impact its solubility profile.

Generally, the solubility can be influenced by the following factors:

  • Hydrophilicity vs. Hydrophobicity: The presence of hydrophilic groups such as phosphate and hydroxyl moieties can enhance solubility in polar solvents like water. Conversely, long hydrophobic tails such as the hexadecanethioate portion may reduce water solubility.
  • pH Level: The solubility of compounds containing acidic or basic functional groups generally varies with pH. This can lead to improved solubility under certain conditions.
  • Temperature: Increased temperature can also play a role in solubility, particularly for moderately soluble compounds.

It is essential to consider that while this compound may exhibit some solubility under specific conditions, it may not be classified as highly soluble overall. Therefore, for practical applications, understanding its solubility characteristics in different environments is crucial for optimizing its use in chemical formulations and biological systems.

Interesting facts

Interesting Facts about S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] hexadecanethioate

This complex compound showcases a fascinating interplay of organic chemistry and biochemistry, reflecting the intricate design of molecules that can have significant biological applications. Here are some engaging highlights that illustrate its importance:

  • Biological Relevance: The presence of the 6-aminopurin-9-yl moiety indicates that this compound may play a role in nucleic acid metabolism, making it a potential candidate for research in molecular biology.
  • Structure Complexity: This molecule is highly complex, featuring multiple functional groups such as phosphonooxy and hydroxy, which suggest its potential for various chemical interactions. The elaborate architecture showcases the art of synthetic organic chemistry.
  • Synthetic Pathways: The synthesis of this compound may involve multiple steps and sophisticated techniques, highlighting the challenges and creativity inherent in organic synthesis and the design of biologically active compounds.
  • Therapeutic Potential: With its unique structure, this compound may offer novel therapeutic approaches in fields such as cancer research, where targeting specific biological pathways can lead to innovative treatment strategies.
  • Phosphorylation: The compound's phosphoryl groups suggest potential activity in cellular signaling pathways, which are crucial for a myriad of cellular processes, including metabolism and signal transduction.

In conclusion, the intricate structural features of S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-2-hydroxy-3,3-dimethyl-butanoyl]amino]propanoylamino]ethyl] hexadecanethioate open doors to numerous avenues in both academic research and pharmaceutical development. Understanding such compounds may redefine our approach to therapeutics, underscoring the beauty and complexity of chemical science.

Synonyms
S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] hexadecanethioate
S-[2-[3-[[4-[[[5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] hexadecanethioate
CHEMBL3904487