Skip to main content

Amikacin

ADVERTISEMENT
Identification
Molecular formula
C22H43N5O13
CAS number
37517-28-5
IUPAC name
N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]-2-hydroxy-ethyl]-4,5-dihydroxy-tetrahydropyran-3-yl]-5-methyl-hex-2-enamide
State
State
Amikacin, in its commercial form, is typically provided as a clear, colorless to pale yellow liquid when prepared in solution for injection. As a solid, it appears as a powder.
Melting point (Celsius)
250.00
Melting point (Kelvin)
523.15
Boiling point (Celsius)
720.15
Boiling point (Kelvin)
993.15
General information
Molecular weight
585.63g/mol
Molar mass
585.5850g/mol
Density
1.4200g/cm3
Appearence
Amikacin is typically found as a white to off-white crystalline powder. It is often supplied as the sulfate salt, which is very soluble in water.
Comment on solubility

Solubility of N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]-2-hydroxy-ethyl]-4,5-dihydroxy-tetrahydropyran-3-yl]-5-methyl-hex-2-enamide

The solubility of this complex organic compound is influenced by its intricate structure, which contains multiple hydroxyl groups capable of forming hydrogen bonds with water molecules. This property generally suggests a degree of solubility; however, the overall solubility profile can be impacted by various factors:

  • Presence of Hydrophilic Groups: The numerous hydroxyl (-OH) and acetamido groups contribute to a stronger interaction with polar solvents like water, enhancing solubility.
  • Hydrophobic Regions: Despite its hydrophilic segments, the presence of hydrophobic parts within the molecular structure may limit its solubility in water.
  • Stereochemistry: The stereochemical configuration can also affect how the molecule interacts with solvents, potentially leading to unique solubility characteristics.
  • The Role of Temperature: Increasing temperature typically increases the solubility of many compounds; thus, this factor should not be overlooked.

In conclusion, while the presence of polar functional groups indicates a potential for solubility, the overall structure of N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]-2-hydroxy-ethyl]-4,5-dihydroxy-tetrahydropyran-3-yl]-5-methyl-hex-2-enamide may lead to variable solubility, necessitating further experimental investigation to fully ascertain its behavior in different solvents.

Interesting facts

Interesting Facts about N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]-2-hydroxy-ethyl]-4,5-dihydroxy-tetrahydropyran-3-yl]-5-methyl-hex-2-enamide

This compound is a fascinating example of complex organic chemistry, predominantly showcasing the intricate relationships between various functional groups. Here are some notable insights:

  • Structural Complexity: The compound features multiple chiral centers, which are crucial for determining its biological activity. The stereochemistry plays a vital role in how the compound interacts with biological molecules, making it a subject of great interest in medicinal chemistry.
  • Potential Biological Activity: Molecules with similar structures have been studied for their potential as enzyme inhibitors, particularly concerning diseases that involve glycolytic pathways. This opens up avenues for research in drug development.
  • Natural Product Inspiration: Many complex compounds are inspired by natural products. In this case, the structural elements suggest a potential derivation from carbohydrate-like structures that are often found in nature, producing beneficial effects such as antimicrobial or antiviral properties.
  • Versatile Applications: Due to its elaborate structure, this compound might be suitable for a variety of applications beyond pharmaceuticals, such as in polymers or materials science, showcasing the breadth of organic compounds in technology.
  • Research Challenges: The synthesis of such complex molecules poses significant challenges. Each step must be carefully controlled to maintain the integrity of numerous chiral centers, making this a rich area for research and innovation in synthetic chemistry.

In summary, N-[(2S,3R,4R,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-6-[2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]-2-hydroxy-ethyl]-4,5-dihydroxy-tetrahydropyran-3-yl]-5-methyl-hex-2-enamide represents a pinnacle of chemical complexity, offering vast potential for future explorations in science and medicine.