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Entecavir

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Identification
Molecular formula
C12H15FN4O3
CAS number
142217-69-4
IUPAC name
4-amino-5-fluoro-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
State
State

Entecavir is typically found in solid state at room temperature, commonly in the form of tablets or powder.

Melting point (Celsius)
220.50
Melting point (Kelvin)
493.65
Boiling point (Celsius)
707.10
Boiling point (Kelvin)
980.25
General information
Molecular weight
295.27g/mol
Molar mass
295.2690g/mol
Density
1.8990g/cm3
Appearence

Entecavir is a white to off-white powder that is freely soluble in water. It has no characteristic odor and appears crystalline under a microscope.

Comment on solubility

Solubility of 4-amino-5-fluoro-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

The solubility of this compound is influenced by its complex molecular structure, which contains both hydrophilic and hydrophobic characteristics. Generally, the presence of the hydroxyl groups in the tetrahydrofuran moiety tends to enhance solubility in polar solvents, making it more conducive to dissolve in water compared to similar compounds lacking these functional groups.

Key factors affecting solubility include:

  • Polarity of the solvent: The more polar the solvent, the better the solubility of this compound.
  • Hydrogen bonding: The ability to form hydrogen bonds with water can significantly improve its solubility.
  • Temperature: Increased temperatures often boost the solubility of many compounds.

However, it is important to note that while this compound may be soluble in aqueous solutions, its actual solubility can vary widely based on concentration, pH, and the presence of other ions or molecules in the solution. As such, one might encounter a scenario where, despite its potential for solubility, precipitation occurs under certain conditions.

In summary, understanding the solubility profile of 4-amino-5-fluoro-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one is crucial for its practical applications in pharmaceuticals and related fields, where solubility plays a vital role in bioavailability and efficacy.

Interesting facts

Interesting Facts about 4-amino-5-fluoro-1-[(2R,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one

This compound, often referred to in research contexts as a type of antiviral agent, showcases the intricate nature of medicinal chemistry. Here are some compelling aspects of this fascinating molecule:

  • Antiviral Activity: The structure of this compound is designed to exhibit strong activity against various viral infections, making it a candidate for therapeutic applications, particularly in combating diseases like influenza and other viral pathogens.
  • Targeting Viral Enzymes: Its mechanism of action typically involves inhibiting viral enzymes, thereby disrupting the replication cycle of viruses. This characteristic is crucial for its efficacy as an antiviral therapy.
  • Chiral Centers: The specific configuration of the molecule has two chiral centers, which is fundamental to its biological activity. The (2R,5R) designation indicates the spatial arrangement of atoms and significantly impacts how the compound interacts with biological systems.
  • Chemical Development: The journey of creating this compound involves advanced synthetic techniques in organic chemistry, showcasing the creativity and precision required in designing molecules for medicinal use.
  • Importance of Hydroxymethyl Group: The hydroxymethyl substituent plays a crucial role in enhancing the compound's solubility and biological activity, making it a focal point in discussions about structure-activity relationships in drug design.

As a chemistry student or a researcher, grasping the significance of this compound in the realm of pharmaceuticals opens up a wider understanding of how molecular modifications can lead to improvements in drug efficacy and safety. It highlights the beauty of combining synthetic chemistry with biological insight, a core principle in the development of new therapeutics.

In the words of renowned chemist Linus Pauling, “The best way to have a good idea is to have lots of ideas.” This compound embodies that philosophy, blending various aspects of chemistry to create a potential life-saving medication.

Synonyms
SCHEMBL207023