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Cefuroxime Axetil

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Identification
Molecular formula
C20H22N4O10S
CAS number
64544-07-6
IUPAC name
1-isopropoxycarbonyloxyethyl 7-[[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
State
State
Cefuroxime axetil is a solid at room temperature and is usually formulated for oral administration as an ester prodrug, providing enhanced oral bioavailability.
Melting point (Celsius)
216.00
Melting point (Kelvin)
489.15
Boiling point (Celsius)
500.00
Boiling point (Kelvin)
773.00
General information
Molecular weight
512.54g/mol
Molar mass
512.5410g/mol
Density
1.5000g/cm3
Appearence
Cefuroxime axetil is typically a white to off-white crystalline powder. It is almost odorless and has a bitter taste.
Comment on solubility

Solubility of 1-isopropoxycarbonyloxyethyl 7-[[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

This complex compound, with the chemical formula C20H22N4O10S, exhibits specific solubility characteristics that are essential for its use in various applications.

Key Points on Solubility:

  • Solvent Interaction: The solubility of the compound is influenced by its functional groups, particularly the presence of polar groups that can interact favorably with solvents like water or alcohols, possibly enhancing its overall solubility.
  • Polarity: Given the mix of polar and non-polar elements in the structure, the compound may show variable solubility in different solvents.
  • pH Dependency: The solubility may also depend on the pH of the medium surrounding it, especially due to the presence of amino and carboxylate functionalities, which can ionize in certain pH ranges.
  • Temperature Influence: Higher temperatures often increase the solubility of organic compounds; thus, testing at various temperatures could yield interesting insights.

In summary, while this compound's solubility profile is complex due to its rich functional composition, factors such as solvent choice, temperature, and pH play crucial roles. As a general guideline, one might expect moderate to low solubility in water, but enhanced solubility could be observed in organic solvents, a common trend for many larger, multi-functional compounds of this nature.

Interesting facts

Interesting Facts about 1-Isopropoxycarbonyloxyethyl 7-[[2-(2-Aminothiazol-4-yl)-2-methoxyimino-acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

This compound is a fascinating example of complex organic chemistry, exhibiting both structural sophistication and potential pharmaceutical applications. Here are some intriguing aspects of this compound:

  • Structural Complexity: The compound features a bicyclic structure, characteristic of many biologically active molecules. Its unique arrangement of atoms contributes to its potential efficacy in various chemical reactions.
  • Pharmaceutical Potential: Compounds with thiazole and oxime functionalities often show promising biological activity. This particular structure suggests that it might be studied for its antimicrobial or antiviral properties, much like other related compounds in medicinal chemistry.
  • Multifunctional Groups: The presence of various functional groups, including isopropoxy, methoxy, and thiazole, indicates diverse reactivity and potential for targeted synthesis in drug development.
  • Importance of Chirality: The specific stereochemical arrangement in the bicyclic framework implies that chirality could play a significant role in its bioactivity. This makes it an interesting subject for enantioselective synthesis and study.
  • Cross-disciplinary Relevance: Research on this compound spans multiple disciplines, requiring knowledge of organic chemistry, medicinal chemistry, and pharmacology. Its study exemplifies how a single molecule can bridge gaps between basic and applied science.

In conducting research on such compounds, scientists often remark, “The complexity of a molecule can reveal much about its properties.” Indeed, the exploration of 1-isopropoxycarbonyloxyethyl 7-[[2-(2-aminothiazol-4-yl)-2-methoxyimino-acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate might unfold new avenues in therapeutic applications, as researchers continue to uncover the intricacies of molecular interactions and reactivity.

Synonyms
cefpodoxime proxetil
87239-81-4
1-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
U-76,252;CS-807
DTXSID80861095
HMS3374C02
HMS3393M14
BCP12056
ZINC15449381
DB-056986
1-({[(Propan-2-yl)oxy]carbonyl}oxy)ethyl 7-[2-(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetamido]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
1-[(isopropoxycarbonyl)oxy]ethyl 7-[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate