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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-6-[(5-methyl-3-phenyl-isoxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State
Cloxacillin at room temperature appears as a solid. It is stable under normal temperatures and pressures.
Melting point (Celsius)
160.00
Melting point (Kelvin)
433.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
435.88g/mol
Molar mass
435.8950g/mol
Density
1.3300g/cm3
Appearence
Cloxacillin is a white or almost white, crystalline powder. It is not soluble in water, but slightly soluble in methanol and ethanol.
Comment on solubility

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

The solubility of the compound C19H17ClN3O5S exhibits notable characteristics influenced by its complex structure. Understanding its solubility can aid in predicting its behavior in various environments:

  • Hydrophilicity and Hydrophobicity: The presence of carboxylic acid and amino groups suggests potential for hydrogen bonding, which can enhance solubility in polar solvents such as water.
  • Significance of Side Chains: The bulky isoxazole moiety and aromatic phenyl group tend to impart hydrophobic characteristics, potentially reducing overall solubility in aqueous solutions.
  • Impact of Cl Substituent: The presence of the chlorine atom can further complicate solubility dynamics, often favoring solubility in organic solvents over water.
  • pH Dependency: The solubility may also vary significantly with pH, particularly due to the carboxylic acid functionality which can be ionized at higher pH levels.

In summary, while the compound may display some solubility in water, its overall solubility profile is likely to be more favorable in organic solvents. Therefore, it is crucial to consider the specific conditions, including solvent type and pH, when assessing the solubility of this complex chemical compound.

Interesting facts

Exploring (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-isoxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

This intriguing compound presents a unique structure that captures the interest of chemists and biochemists alike. It features a bicyclic framework, which is notable for its potential applications in pharmaceuticals and organic synthesis.

Key Characteristics

  • Stereochemistry: The configuration of this compound is significant; its specific stereochemical arrangement might influence its biological activity and interaction with target proteins.
  • Functional Groups: With the incorporation of an isoxazole moiety, this compound could exhibit interesting electronic properties, making it a candidate for further investigation into drug development.
  • Thia Aspects: The presence of sulfur within the bicyclic structure introduces unpredictability and can modulate reactivity and stability in various conditions.

Potential Applications

Aside from its structural complexity, (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-isoxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is being studied because:

  • It may act as a novel therapeutic agent.
  • Its unique attributes could allow for innovative formulations in medicinal chemistry.
  • It holds promise in the exploration of enzyme inhibitors due to its amine and carbonyl functionalities.

As scientists continue to delve into its properties and potential applications, this compound highlights the beauty of chemical diversity and the endless possibilities that arise from the intricate dance of atoms.

Synonyms
oxacillin
Oxazocillin
66-79-5
Oxazocilline
Oxacilina
MPI-penicillin
Oxacilline
Ossacillina
Oxacillinum
Prostaphlyn
Bactocill
Prostaphlin
MPi-PC
OXACILLIN SODIUM
5-Methyl-3-phenyl-4-isoxazolyl-penicillin
Oxacilina [INN-Spanish]
Oxacilline [INN-French]
Oxacillinum [INN-Latin]
CHEBI:7809
(5-methyl-3-phenyl-4-isoxazolyl)penicillin
EINECS 200-635-5
UNII-UH95VD7V76
Oxacillin (INN)
Penicillin, (5-methyl-3-phenyl-4-isoxazolyl)-
UH95VD7V76
(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid
(2S,5R,6R)-3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
DTXSID8023397
Methylphenylisoxazolyl Penicillin
Ossacillina [DCIT]
OXACILLIN [INN]
Oxacilina (INN-Spanish)
Oxacilline (INN-French)
Oxacillinum (INN-Latin)
Oxacillin [INN:BAN]
OXACILLIN (MART.)
OXACILLIN [MART.]
1173-88-2
(2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-phenyl-1,2-oxazole-4-amido)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-[[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]amino]-7-oxo-, (2S,5R,6R)-
Penicillin, Methylphenylisoxazolyl
Oxacilina (TN)
MPI-penicillin; MPi-PC
oxacillina
Oxacillin,(S)
(2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-isoxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2S-(2alpha,5alpha,6beta))-
OXACILLIN [MI]
OXACILLIN [VANDF]
CHEMBL819
Epitope ID:181859
OXACILLIN [WHO-DD]
SCHEMBL3817
DTXCID403397
GTPL10943
HY-B0925A
J01CF04
phenylisoxazole-4-carboxamido)-7-
BDBM50350483
DB00713
2,2-dimethyl-6beta-(5-methyl-3-phenyl-1,2-oxazole-4-carboxamido)penam-3alpha-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(5-methyl-3-phenyl-4-isoxazolecarboxamide)-7-oxo-
DA-76502
5-Methyl-3-phenyl-4-isooxazolylpenicillin
oxo-4-thia-1-azabicyclo[3.2.0]heptane-
CS-0013715
NS00000572
C07334
D08307
(2S,5R,6R)-3,3-dimethyl-6-(5-methyl-3-
EN300-19766050
Q418725
BRD-K96786677-236-01-6
BRD-K96786677-236-02-4
BRD-K96786677-323-02-0
200-635-5
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-6-(((5-METHYL-3-PHENYL-4-ISOXAZOLYL)CARBONYL)AMINO)-7-OXO-,(2S,5R,6R)-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2S-(2.alpha.,5.alpha.,6.beta.))-