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Tigecycline

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Identification
Molecular formula
C29H39ClN3O8S
CAS number
220620-09-7
IUPAC name
N-[(2S)-2-chloro-1-[(3R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide
State
State

Tigecycline is generally found as a lyophilized powder for intravenous infusion. In its solid state, it is stable under standard room temperature conditions. Once reconstituted, it is stored as a liquid solution.

Melting point (Celsius)
180.00
Melting point (Kelvin)
453.15
Boiling point (Celsius)
836.00
Boiling point (Kelvin)
1 109.15
General information
Molecular weight
585.64g/mol
Molar mass
585.6410g/mol
Density
1.8270g/cm3
Appearence

Tigecycline is typically an orange powder in its pure form. It is often available in lyophilized form for reconstitution.

Comment on solubility

Solubility of N-[(2S)-2-chloro-1-[(3R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide

This compound's solubility characteristics are crucial for understanding its behavior in various environments, especially in biological systems. The complex structure suggests a potential for varied solubility depending on pH, temperature, and solvent used.

Factors Influencing Solubility

  • Polarity: The presence of multiple hydroxyl (-OH) groups contributes to overall polarity, enhancing solubility in polar solvents, particularly water.
  • Sulfanyl Group: The -S(CH3) group may impart unique interactions with surrounding molecules, potentially affecting solubility.
  • Amide Structure: The carboxamide functional group may engage in hydrogen bonding, facilitating solubility in both aqueous and organic solvents.

Overall, it can be anticipated that this compound exhibits good solubility in polar solvents while showing lower solubility in nonpolar solvents. As noted, the "hydroxyl groups significantly enhance interactions with water molecules." Thus, practical experimentation is recommended to quantify the solubility under various conditions.

Practical Implications

Understanding the solubility of this compound is essential for drug formulation and delivery, as high solubility often results in better absorption and efficacy. Therefore, studies should focus on:

  1. Comparative solubility across different pH environments.
  2. Temperature influence on solubility rates.
  3. Interaction with excipients in pharmaceutical formulations.

In conclusion, thorough investigation into the solubility profile of this compound will provide critical insights for its applications and efficacy.

Interesting facts

Interesting Facts About N-[(2S)-2-chloro-1-[(3R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide

This compound, known for its complex structure and unique chemical properties, is of great interest in the fields of medicinal chemistry and drug development. Here are some fascinating aspects:

  • Complex Structure: The compound features a pyrrolidine backbone, which is not uncommon in biologically active molecules. Its intricate stereochemistry highlights the significance of chiral centers in drug design, affecting how these molecules interact with biological targets.
  • Potential Therapeutic Applications: Compounds with similar frameworks have been explored for their potential in treating various diseases, including metabolic disorders and infections, due to their ability to modulate biological pathways.
  • Role of Sulfur: The presence of a methylsulfanyl group adds interesting properties to the molecule, such as affecting its pharmacokinetics and pharmacodynamics. Sulfur-containing compounds often exhibit unique behaviors in biological systems.
  • Natural Product Inspiration: The trihydroxy group and tetrahydropyran structure resemble motifs found in many natural products, suggesting that nature often crafts effective drug candidates that chemists can emulate.
  • Chirality Matters: Chirality, or the property of having non-superimposable mirror images, plays a crucial role in the efficacy and safety of pharmaceutical compounds. The specific stereochemistry of this compound can greatly influence its interactions within the body.

In summary, N-[(2S)-2-chloro-1-[(3R,6R)-3,4,5-trihydroxy-6-methylsulfanyl-tetrahydropyran-2-yl]propyl]-1-methyl-4-propyl-pyrrolidine-2-carboxamide encapsulates the essence of complexity in organic chemistry, serving as a reminder of the intricate interplay between molecular structure and biological activity.