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Sofosbuvir

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Identification
Molecular formula
C22H29FN3O9
CAS number
1190307-88-0
IUPAC name
5-bromo-1-[(2R,4S,5R)-5-ethyl-4-hydroxy-tetrahydrofuran-2-yl]-5-fluoro-6-methoxy-hexahydropyrimidine-2,4-dione
State
State

At room temperature, Sofosbuvir is typically a solid compound that is used in tablet form in pharmaceutical applications for the treatment of hepatitis C.

Melting point (Celsius)
119.00
Melting point (Kelvin)
392.15
Boiling point (Celsius)
400.00
Boiling point (Kelvin)
673.15
General information
Molecular weight
529.45g/mol
Molar mass
529.4500g/mol
Density
1.4809g/cm3
Appearence

Sofosbuvir is an off-white to light yellow crystalline solid. It is formulated as pills for oral administration. The compound is practically insoluble in the pH range of 1.0 to 7.5, but freely soluble in acetonitrile.

Comment on solubility

Solubility of 5-bromo-1-[(2R,4S,5R)-5-ethyl-4-hydroxy-tetrahydrofuran-2-yl]-5-fluoro-6-methoxy-hexahydropyrimidine-2,4-dione

The solubility of a compound is influenced by various factors, including its molecular structure, functional groups, and the solvent used. In the case of 5-bromo-1-[(2R,4S,5R)-5-ethyl-4-hydroxy-tetrahydrofuran-2-yl]-5-fluoro-6-methoxy-hexahydropyrimidine-2,4-dione, we can observe several interesting aspects:

  • Polar Functional Groups: The presence of hydroxyl (-OH) and methoxy (-OCH3) groups suggests potential for hydrogen bonding with water, contributing to solubility.
  • Aliphatic Chains: The ethyl group may enhance lipophilicity, potentially affecting solubility in non-polar solvents.
  • Bromo and Fluoro Substituents: These halogen substituents introduce electronegative elements that could influence the compound’s interaction with various solvents.

While the specific solubility behavior of this compound is not widely documented, it would be expected to be:

  • Moderately soluble in polar solvents (e.g., water, ethanol) due to hydrogen bonding capabilities.
  • Less soluble in non-polar solvents (e.g., hexane, benzene) given the hydrophilic nature of its functional groups.

In conclusion, the intricate balance of polar and non-polar characteristics in 5-bromo-1-[(2R,4S,5R)-5-ethyl-4-hydroxy-tetrahydrofuran-2-yl]-5-fluoro-6-methoxy-hexahydropyrimidine-2,4-dione indicates a nuanced solubility profile that warrants further investigation.

Interesting facts

Interesting Facts about 5-bromo-1-[(2R,4S,5R)-5-ethyl-4-hydroxy-tetrahydrofuran-2-yl]-5-fluoro-6-methoxy-hexahydropyrimidine-2,4-dione

The compound named 5-bromo-1-[(2R,4S,5R)-5-ethyl-4-hydroxy-tetrahydrofuran-2-yl]-5-fluoro-6-methoxy-hexahydropyrimidine-2,4-dione is a fascinating member of the pyrimidine family, notable for its complex structure and potential applications in medicinal chemistry. Here are some key insights about this compound:

  • Synthetic Utility: Its intricate structure provides opportunities for synthesis through various organic transformations, making it an interesting subject for both synthetic chemists and students.
  • Biological Activity: Compounds like this one are often studied for their biological activities, including antimicrobial, anti-inflammatory, and anticancer properties, offering avenues for pharmaceutical development.
  • Stereochemistry: The stereochemical centers present in the structure lend to its potential chiral specificity, which can influence the pharmacokinetics and pharmacodynamics of the compound.
  • Fluorine Substitution: The presence of fluorine in the structure is significant; fluorinated compounds often exhibit enhanced metabolic stability, making them a focal point in drug design.

As noted by many researchers, "the design of bioactive compounds requires a balance between structural complexity and biological efficacy." This statement rings particularly true for our compound, showcasing how intricate design can lead to valuable therapeutic agents.

In summary, the multi-faceted nature of 5-bromo-1-[(2R,4S,5R)-5-ethyl-4-hydroxy-tetrahydrofuran-2-yl]-5-fluoro-6-methoxy-hexahydropyrimidine-2,4-dione positions it as a subject of interest in various fields, including organic chemistry, medicinal chemistry, and pharmaceutical sciences. Its potential applications could significantly impact future research and therapeutic strategies.