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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-[(3-oxo-3-phenoxy-2-phenyl-propanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State
Cloxacillin is typically in a solid state at room temperature. It is available as a powder and in capsule form for medical use.
Melting point (Celsius)
178.00
Melting point (Kelvin)
451.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
436.89g/mol
Molar mass
436.8910g/mol
Density
1.4201g/cm3
Appearence

Cloxacillin appears as a white crystalline powder. It is often supplied as sodium cloxacillin, which appears similar and is highly soluble in water, forming a clear solution.

Comment on solubility

Solubility Insights

(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(3-oxo-3-phenoxy-2-phenyl-propanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is a complex molecule. Its solubility can significantly influence its behavior in biochemical environments. Below are some key points regarding the solubility of this compound:

  • Polarity: The presence of polar functional groups, such as carboxylic acids and amides, often enhances solubility in polar solvents like water.
  • Hydrophobic regions: The inclusion of hydrophobic phenyl and phenoxy groups may lead to limited solubility in hydrophilic environments, potentially resulting in a more favorable solubility in organic solvents.
  • Environmental factors: Solubility can be influenced by temperature, pH, and the presence of co-solvents which can either enhance or inhibit solvation.
  • Complexation: The ability of this compound to form complexes with other biomolecules may also impact solubility and, by extension, bioavailability.

Understanding the solubility of this compound is crucial for applications in medicinal chemistry and pharmacology, as it can dictate the compound's therapeutic efficacy and dosage form development.

Interesting facts

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

This complex compound, renowned for its multi-functional properties, belongs to a fascinating class of organic molecules known as bioactive compounds. Here are some captivating aspects surrounding this chemical:

  • Structural Complexity: The compound showcases a unique bicyclic structure, containing both azabicyclo and thia functionalities. This 3D arrangement contributes significantly to its biological activity.
  • Biological Significance: Compounds of this nature often exhibit antimicrobial and anti-inflammatory properties, making them potential candidates for pharmaceutical development. Such bioactivity arises from their ability to interact with various biological targets.
  • Chirality: With stereocenters present in its structure, this compound can exist in different stereoisomer forms. The specified configuration (2S, 5R, 6R) suggests that only certain isomers may display desired biological efficacy, which is a vital consideration in drug design.
  • Functional Groups: The compound contains key functional groups, such as ketones and amides, that contribute to its reactivity and interaction mechanisms. These groups play a pivotal role in forming hydrogen bonds and ionic interactions in biological systems.
  • Mechanistic Studies: Researchers are continuously investigating the mechanisms underlying the biological activity of such compounds. Understanding how these molecules affect cellular processes can lead to innovative therapies for various diseases.

In summary, the structure and properties of (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(3-oxo-3-phenoxy-2-phenyl-propanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid not only highlight the intricacies of organic chemistry but also underscore the exciting potential of complex organic compounds in the field of medicine.

Synonyms
Carfecillin
Carbenicillin phenyl
Carfecilina
Carfecilline
Carbenicillin phenyl ester
Carfecillinum
27025-49-6
9UU4XDB74X
6-(2-Phenoxycarbonyl-2-phenylacetamido)penicillansaeure
CHEBI:3414
BRL 3475
Carfecillin Sodium Salt
DTXSID10891704
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-((2-phenoxycarbonyl)-2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((1,3-dioxo-3-phenoxy-2-phenylpropyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
Carphecillin
2,2-dimethyl-6beta-[(3-oxo-3-phenoxy-2-phenylpropanoyl)amino]penam-3alpha-carboxylic acid
2,2-dimethyl-6beta-((3-oxo-3-phenoxy-2-phenylpropanoyl)amino)penam-3alpha-carboxylic acid
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-((3-oxo-3-(phenoxy)-2-phenylpropanoyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[3-oxo-3-(phenoxy)-2-phenylpropanoyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Salt, Carfecillin Sodium
Sodium Salt, Carfecillin
RefChem:123716
BRL3475
DTXCID201030832
248-171-2
Carfecillin [INN]
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(3-oxo-3-phenoxy-2-phenylpropanoyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Carfecilina [INN-Spanish]
Carfecilline [INN-French]
Carfecillinum [INN-Latin]
EINECS 248-171-2
UNII-9UU4XDB74X
BRN 1095507
CARFECILLIN [JAN]
CARFECILLIN [WHO-DD]
6-((1,3-Dioxo-3-phenoxy-2-phenylpropyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid (2S-(2alpha,5alpha,6beta))-
SCHEMBL150615
CHEMBL1095283
GTPL12288
NZDASSHFKWDBBU-KVMCETHSSA-N
DB13506
Malonamic acid, N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenyl-, 1-phenyl ester
NS00011615
Q5039237
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((1,3-DIOXO-3-PHENOXY-2-PHENYLPROPYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))
N-(2-CARBOXY-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPT-6-YL)-2-PHENYLMALONAMIC ACID 1-PHENYL ESTER