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Cloxacillin

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Identification
Molecular formula
C19H18ClN3O5S
CAS number
61-72-3
IUPAC name
7-[(2-amino-2-phenyl-acetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
State
State

At room temperature, cloxacillin is typically in a solid state.

Melting point (Celsius)
176.00
Melting point (Kelvin)
449.20
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
435.89g/mol
Molar mass
435.8910g/mol
Density
1.3300g/cm3
Appearence

Cloxacillin is usually available as a white to slightly yellow crystalline powder. It is practically odorless and has a bitter taste.

Comment on solubility

Solubility of 7-[(2-amino-2-phenyl-acetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (C19H18ClN3O5S)

The solubility of a compound can greatly influence its application and effectiveness, especially in pharmaceutical contexts. For the compound 7-[(2-amino-2-phenyl-acetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, we can observe several key points regarding its solubility:

  • Polarity: The presence of multiple polar functional groups (e.g., amino acids and carboxylic acids) typically enhances solubility in polar solvents such as water. However, the overall structure and molecular weight also play significant roles.
  • Hydrogen Bonding: The ability of this compound to form hydrogen bonds with water molecules can contribute positively to its solubility. The more hydrogen bond donors and acceptors present, the more likely the compound will be soluble.
  • Effect of Chlorine: The presence of a chlorine atom may affect the compound's hydrophilicity, potentially reducing solubility compared to similar non-chlorinated compounds.
  • Environmental Factors: Temperature, pH, and the presence of other ions or molecules in solution can significantly impact the solubility of this compound, changing how it behaves in biological or chemical environments.

In summary, assessing the solubility of 7-[(2-amino-2-phenyl-acetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid requires a careful analysis of its molecular structure and the properties of the solvent in question. Variations in these conditions might yield different solubility results, reinforcing the complexity of predicting solubility based solely on chemical composition.

Interesting facts

Interesting Facts about 7-[(2-amino-2-phenyl-acetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

This intriguing compound, which belongs to a class of antibiotics known as β-lactams, exhibits a unique bicyclic structure, contributing to its biological activity.

Biological Significance

Here are some notable aspects of its biological role:

  • Mechanism of Action: The compound works by inhibiting bacterial cell wall synthesis, an important target in combating bacterial infections.
  • Resistance Management: Research is ongoing to study how modifications to its structure can enhance effectiveness against antibiotic-resistant bacteria.
  • Spectrum of Activity: It has broad-spectrum activity, making it invaluable in treating various bacterial strains.

Synthetic Pathways

The synthesis of this compound involves intricate organic chemistry techniques, which can often be challenging. Some interesting steps include:

  • Multi-step Synthesis: The synthesis can include cyclization and acylation reactions, showcasing the complexity of designing effective pharmaceutical compounds.
  • Structure-Activity Relationship (SAR): Modifying functional groups can lead to various analogs, each exhibiting distinct antibacterial properties.

Applications in Medicine

Beyond its antibiotic properties, this compound is being explored for:

  • Synergistic Effects: Combining it with other antimicrobial agents may improve efficacy against stubborn infections.
  • Potential Side Effects: Understanding its pharmacokinetics is crucial for predicting possible adverse effects in patients.

This compound exemplifies the balance between structure and function that is central to medicinal chemistry. As scientists continue to explore its properties, they may unlock new therapeutic avenues, further emphasizing the importance of continued research in the field of antibiotic development.

Synonyms
108260-04-4
L-Cephalexin
Cephalexin hydrate
7-{[amino(phenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
34632-04-7
ZAIPMKNFIOOWCQ-UHFFFAOYSA-N
7-[(2-amino-2-phenylacetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CHEMBL287590
SCHEMBL10713860
DTXSID20274382
DTXSID80860169
HMS3393A04
BBL013211
STK803646
AKOS005611612
NCGC00015241-02
NCGC00015241-03
NCGC00094945-01
NCGC00094945-02
7-(D-.alpha.-Amino-.alpha.-phenylacetamido)-3-methyl-3-cephem-4-carboxylic acid monohydrate
NS00000471
(6R,7R)-7-[(R)-2-Amino-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]-oct-2-ene-2-carboxylic acid monohydrate
[6R-[6.alpha.,7.beta.(R*)]]-7-[(Aminophenylacetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[(aminophenylacetyl)amino]-3-methyl-8-oxo-, monohydrate [6R-[6.alpha.,7.beta.(R*)]]-
7-([Amino(phenyl)acetyl]amino)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid #
7-(aminophenylacetyl)amino-3-methyl-8-oxo-5-thia-1-azabicyclo(4,2,0)oct-2-ene-2-carboxylic acid
7-[2-Amino(phenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7a(2aAminoa2aphenylacetamido)a3amethyla8aoxoa5a thiaa1aazabicyclo[4.2.0]octa2aenea2acarboxylic acid