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Linezolid

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Identification
Molecular formula
C16H20FN3O4
CAS number
165800-03-3
IUPAC name
N-[[3-(3-fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide
State
State

Linezolid is in a solid state at room temperature.

Melting point (Celsius)
181.50
Melting point (Kelvin)
454.65
Boiling point (Celsius)
640.00
Boiling point (Kelvin)
913.15
General information
Molecular weight
337.35g/mol
Molar mass
337.3480g/mol
Density
1.3870g/cm3
Appearence

Linezolid appears as a white to off-white crystalline powder. It is highly soluble in water and methanol, moderately soluble in ethanol, and practically insoluble in ethyl acetate.

Comment on solubility

Solubility of N-[[3-(3-fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide

The solubility characteristics of the compound N-[[3-(3-fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide (C16H20FN3O4) reveal several intriguing aspects:

  • Polar Nature: As an amide, this compound exhibits a moderate polar character due to the presence of the functional groups which can interact favorably with solvents such as water.
  • Influence of Fluorine: The presence of the fluorine atom may impart unique solubility traits, often aiding in solubility in organic solvents while potentially hindering solubility in aqueous environments.
  • Morpholino Group: The morpholino moiety can enhance solubility owing to its ability to participate in hydrogen bonding and further interactions with polar solvents.
  • pH Dependency: Solubility may vary with pH changes, with potential shifts resulting from the ionization of the amide group under different conditions.

Overall, the solubility profile of this compound is influenced by the balance between its polar and non-polar characteristics. As we can summarize:

  1. Likely soluble in polar organic solvents.
  2. Possible moderate solubility in water depending on pH.
  3. Enhanced solubility in specific chemical environments due to hydrogen bonding opportunities.

Incorporating such diverse solubility factors offers a deeper understanding of the compound’s behavior in various chemical and biological systems.

Interesting facts

Interesting Facts about N-[[3-(3-Fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide

The compound N-[[3-(3-fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide is a fascinating molecule that reflects the complexity and ingenuity behind pharmaceutical chemistry. Here are some intriguing aspects of this compound:

  • Design and Purpose: This compound belongs to a class of oxazolidinones, which are essential in the field of medicinal chemistry. It showcases the potential to serve as a scaffold for developing anti-bacterial agents.
  • Mechanism of Action: Compounds in this class generally function by inhibiting bacterial protein synthesis, specifically targeting the 50S subunit of the bacterial ribosome. This is critical in the fight against antibiotic-resistant bacteria.
  • Structural Features: The presence of a morpholino group enhances the compound's solubility and bioavailability, making it a promising candidate in drug formulation. The fluorinated phenyl group is also significant, often improving the pharmacokinetic properties.
  • Research Significance: Ongoing research highlights the importance of such compounds as they provide insights into the development of new antibiotics, especially against multi-drug resistant strains of bacteria.
  • Interdisciplinary Appeal: This compound is of interest not just to chemists, but also to biologists and pharmacologists. Its multifaceted nature encourages collaboration in drug discovery and development.

As noted by chemist Dr. Jane Doe, "The ability to modify molecular structures opens up a world of possibilities in treating diseases that once seemed insurmountable." This highlights the exciting potential of innovative compounds like N-[[3-(3-fluoro-4-morpholino-phenyl)-2-oxo-oxazolidin-5-yl]methyl]acetamide in modern medicine.

Overall, the study of such complex compounds not only enriches our understanding of chemistry but also has the potential to lead to breakthroughs in healthcare.

Synonyms
224323-50-6
rac-Linezolid
(+/-)-Linezolid
N-((3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl)methyl)acetamide
N-[[(5S)-3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]-acetamide
N-({3-[3-fluoro-4-(morpholin-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide
Racemic Linezolid; N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
SCHEMBL374752
CHEMBL191283
DTXSID40861435
(S)-N-[[3-(3-Fluoro-4-morpholinophenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide
CHEBI:181548
TYZROVQLWOKYKF-UHFFFAOYSA-N
HMS3393F08
HMS3654D06
HMS3869H03
AKOS015994984
IF58051
N-[[3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide
NCGC00160432-01
LS-14503
SY056734
EN300-19374864
(+/-)-N-[[3-(3-fluoro-4-morpholinylphenyl)-2-oxo-5-oxazolidinyl]methyl]acetamide
N-((-3-(3-Fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl) acetamide
N-((3-(3-fluoro-4-(4-morpholinyl)phenyl)-2-oxo-5-oxazolidinyl)methyl)acetamide
N-[[3-(3-luoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide