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Cefepime

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Identification
Molecular formula
C19H24N6O5S2
CAS number
88040-23-7
IUPAC name
(6R,7R)-3-[(4-carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
State
State

At room temperature, cefepime is in a solid state, appearing as a crystalline powder. It is usually stored as a powder for reconstitution in a laboratory or clinical setting.

Melting point (Celsius)
197.00
Melting point (Kelvin)
470.15
Boiling point (Celsius)
645.80
Boiling point (Kelvin)
918.95
General information
Molecular weight
480.57g/mol
Molar mass
480.5740g/mol
Density
1.6402g/cm3
Appearence

Cefepime appears as a white to pale yellow crystalline powder. It has a characteristic smell that is sulfurous due to the presence of the thiophene and thioether components in its structure.

Comment on solubility

Solubility of (6R,7R)-3-[(4-carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

The solubility of this intricate compound can be influenced by several factors due to its complex structure. Understanding its solubility characteristics is essential for applications in pharmaceuticals and chemical analysis. Here are some aspects to consider:

  • Polarity: This compound features multiple functional groups, which typically enhances solubility in polar solvents.
  • Hydrogen Bonding: With the presence of amide and carboxylic acid groups, the potential for hydrogen bonding is significant, likely increasing solubility in aqueous solutions.
  • pH Sensitivity: Its solubility may vary with pH, as ionization of the carboxylic acid group can improve solubility in alkaline conditions.
  • Solvent Compatibility: This compound may display different solubility profiles in various solvents, including water, ethanol, or DMSO, depending on molecular interactions.

In conclusion, while specific experimental data is crucial for definitive statements, the structural features suggest high solubility in polar solvents, particularly under conditions that favor ionization. Thus, experimental solubility studies are highly recommended for precise quantification.

Interesting facts

Insights into (6R,7R)-3-[(4-carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

This compound, often referred to for its complex structure and potential biomedical applications, showcases the sophistication of organic chemistry. With its unique bicyclic framework and multiple functional groups, it exemplifies how diverse chemical libraries can be used to develop therapeutic agents. Here are some fascinating aspects of this compound:

  • Structural Diversity: The incorporation of a pyridin-1-ium moiety and a thienyl-acetyl group adds intriguing chemical properties. Such moieties can enhance solubility and bioactivity, making them pivotal in drug design.
  • Pharmacological Potential: Compounds of this nature have garnered interest in medicinal chemistry, particularly in antibiotic or anti-cancer research. The thiazolidine and thia ring systems could be key to enzyme inhibition pathways.
  • Synthetic Challenge: The synthesis of this compound emphasizes the creativity and precision required in fine organic synthesis. The necessity to control stereochemistry, as indicated by its (6R,7R) configuration, highlights the importance of regioselectivity in achieving desired activity.
  • Application in Research: In laboratory settings, derivatives of such compounds are often studied for their interaction with biological macromolecules. Understanding how they bind to proteins or enzymes can reveal mechanisms of action or resistance.

In summary, the elegance of (6R,7R)-3-[(4-carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid lies in its intricate structure and vast potential in scientific advancement. As we explore such compounds, we unlock the possibilities for innovation in chemical synthesis and therapeutic development.

Synonyms
(6R,7R)-3-[(4-carbamoyl-1-pyridin-1-iumyl)methyl]-8-oxo-7-[(1-oxo-2-thiophen-2-ylethyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-3-[(4-carbamoylpyridin-1-ium-1-yl)methyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SPBio_002982
Prestwick0_000996
Prestwick1_000996
Prestwick2_000996
Prestwick3_000996
BSPBio_001091
BPBio1_001201
CHEBI:95238
PD063127
SBI-0207044.P001
SR-01000872745
SR-01000872745-1
BRD-K15514357-001-05-6
Q27167071
4-carbamoyl-1-{[(6R,7R)-2-carboxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium