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Cloxacillin

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Identification
Molecular formula
C19H17ClN3O5S
CAS number
61-72-3
IUPAC name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-phenoxypropanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

At room temperature, cloxacillin is commonly found in its sodium salt form, which is a solid. It is stable under normal conditions and is often reconstituted in water for pharmaceutical use.

Melting point (Celsius)
175.00
Melting point (Kelvin)
448.15
Boiling point (Celsius)
241.80
Boiling point (Kelvin)
514.95
General information
Molecular weight
435.91g/mol
Molar mass
435.9050g/mol
Density
1.3000g/cm3
Appearence

Cloxacillin typically appears as a white to off-white crystalline powder. It may also be found in a microcrystalline form and is often used in its sodium salt form for medical applications.

Comment on solubility

Solubility of (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-phenoxypropanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

The solubility of the compound (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-phenoxypropanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is influenced by various factors, primarily due to its unique structural features. To analyze its solubility behavior, consider the following points:

  • Polarity: The presence of polar functional groups such as carboxylic acid and amide functionalities often enhances solubility in polar solvents like water.
  • Hydrophobic Regions: Conversely, the dimethyl and phenoxy groups contribute to hydrophobic characteristics, potentially reducing solubility in aqueous environments.
  • pH Influence: The solubility may vary significantly with pH due to ionization of the carboxylic acid group, which can become deprotonated at higher pH levels, thereby increasing solubility.
  • Temperature Effects: Higher temperatures typically increase solubility for many compounds, and this bicyclic structure may also follow that trend.

In summary, the solubility of this compound is a complex interplay between its polar and non-polar characteristics. Understanding this behavior is crucial for applications in pharmaceutical formulations where solubility affects bioavailability.

Interesting facts

Interesting Facts about (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[[(2R)-2-phenoxypropanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

This compound, known for its complex structure and unique properties, is a fascinating subject of study within the field of chemistry. Here are some notable aspects:

  • Structure and Chiral Centers: The compound features multiple chiral centers, specifically at positions 2, 5, and 6. This chirality contributes to its potential biological activity and specificity in interaction with biological systems.
  • Functional Groups: It possesses a range of functional groups, including a thia (sulfur-containing) segment, an amide, and a carboxylic acid. Each group plays a crucial role in the compound's reactivity and the types of reactions it can undergo.
  • Potential Biological Activity: Compounds with similar structural frameworks are often investigated for their pharmacological properties, leading to potential applications in drug development. Understanding how this compound interacts at the molecular level could unveil new therapeutic avenues.
  • Importance in Organic Synthesis: The synthesis of such intricate compounds often involves advanced organic reactions, showcasing the creativity and complexity inherent in synthetic organic chemistry. This can serve as a teaching tool for students exploring reaction mechanisms and the principles of stereochemistry.
  • Research and Development: Ongoing research into compounds like this one may yield insights that contribute to advancements in medicinal chemistry, agrochemicals, or other fields where bioactive compounds play a key role.

As you delve deeper into the chemistry of this compound, consider its implications beyond just molecular structure. The intersection of chemistry with biology, medicine, and environmental science opens vast opportunities for innovation.

Synonyms
SCHEMBL3863
NS00069544