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Adefovir dipivoxil

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Identification
Molecular formula
C20H32N5O8P
CAS number
142340-99-6
IUPAC name
S-[2-[3-[[4-[[[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] octadec-9-enethioate
State
State

Under standard conditions of temperature and pressure, the compound exists as a solid. It is stable under normal temperatures and pressures in a pharmaceutical context.

Melting point (Celsius)
99.00
Melting point (Kelvin)
372.15
Boiling point (Celsius)
90.00
Boiling point (Kelvin)
363.15
General information
Molecular weight
501.48g/mol
Molar mass
501.4810g/mol
Density
1.5000g/cm3
Appearence

Adefovir dipivoxil appears as a white to off-white crystalline powder. It is odorless and is typically handled as a powder for pharmaceutical formulation purposes.

Comment on solubility

Solubility of S-[2-[3-[[4-[[[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] octadec-9-enethioate (C20H32N5O8P)

The solubility of S-[2-[3-[[4-[[[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] octadec-9-enethioate is an intriguing aspect of its chemical characteristics. Below are some key points to consider:

  • Polarity: This compound has multiple functional groups, including amines, hydroxyls, and phosphate moieties. These groups often increase the polarity of the molecule, potentially enhancing its solubility in polar solvents such as water.
  • Hydrophobic Region: The presence of the long hydrocarbon chain (octadec-9-enethioate) introduces a hydrophobic section to the compound, which could limit solubility in highly polar solvents. This dual nature may allow for solubility in a range of organic solvents.
  • pH Dependence: The solubility may greatly vary with pH due to ionization of the functional groups, especially the amino and phosphono groups. This can result in different solubility profiles in varying environments.
  • Interaction with Preserving Agents: The complex structure may interact with various preserving agents or excipients in drug formulations, which could also affect overall solubility and stability.

In conclusion, while the complex formation of the compound suggests potential for solubility in a variety of environments, definitive solubility data would depend on specific conditions such as temperature, solvent composition, and pH. As such, conducting further experiments will be essential to elucidate its solubility profile comprehensively.

Interesting facts

Interesting Facts about S-[2-[3-[[4-[[[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] octadec-9-enethioate

This remarkable compound is a fascinating subject of study due to its complex structure and potential applications in biomedical research. Here are some notable aspects:

  • Biological Significance: The presence of a purine base in its structure suggests that this compound may play a role in cellular processes, like nucleic acid metabolism and signaling mechanisms.
  • Phosphorylation: It contains multiple phosphonate groups, which are crucial for the energy transfer processes in living organisms. They are essential for the functioning of ATP and similar high-energy molecules.
  • Potential Therapeutic Uses: Given its structure, this compound may have potential as a pharmaceutical agent, particularly in areas related to cancer and viral infections, leveraging its unique chemical properties.
  • Synthetic Pathways: The intricate synthetic routes to produce this compound can provide valuable insights into organic synthesis and the development of complex molecules in medicinal chemistry.
  • Structural Diversity: The compound showcases the concept of 'molecular diversity,' a principle that is integral in drug discovery, where variations in molecular structure lead to differences in biological activity.

As a chemistry student or scientist, delving into the characteristics and potential applications of such compounds can ignite a passionate interest in the development of novel therapeutic agents that can impact human health and disease.

In summary, the structural complexity and functional diversity of this compound highlight the captivating interplay of chemistry in biological systems and open avenues for future research breakthroughs.

Synonyms
Oleoyl coenzyme A potassium salt
Oleyl-CoA
1716-06-9
G85491