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Flucloxacillin

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Identification
Molecular formula
C19H17ClFN3O5S
CAS number
1847-24-1
IUPAC name
(2S,5R,6R)-6-[[3-(2-chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

At room temperature, Flucloxacillin exists in a solid crystalline state, most often encountered as a sodium salt for medicinal purposes.

Melting point (Celsius)
152.00
Melting point (Kelvin)
425.20
Boiling point (Celsius)
273.15
Boiling point (Kelvin)
546.30
General information
Molecular weight
456.89g/mol
Molar mass
456.8920g/mol
Density
1.4000g/cm3
Appearence

Flucloxacillin is typically found in the form of a white or almost white crystalline powder. It is usually provided as a sodium salt for better solubility.

Comment on solubility

Solubility Characteristics

The compound (2S,5R,6R)-6-[[3-(2-chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid exhibits intriguing solubility properties due to its complex structure. Its solubility can be influenced by several factors including:

  • Polarity: Polar functional groups can enhance solubility in aqueous environments, while non-polar portions may resist dissolution in water.
  • pH Sensitivity: The presence of carboxylic acid moieties may lead to variations in solubility under different pH conditions, often becoming more soluble at higher pH values when deprotonated.
  • Organic Solvents: Such compounds often show increased solubility in organic solvents like ethanol, dimethyl sulfoxide (DMSO), or acetonitrile compared to water.
  • Temperature Effects: Typically, solubility increases with temperature, allowing for better dissolution of solid compounds.

Given the intricate configuration, it is crucial to conduct experimental solubility tests under varying conditions to determine its practical solubility profile, as theoretical assessments may not fully capture real-world interactions. It is often noted that "solubility is a dynamic equilibrium," reflecting how environmental conditions can dramatically impact solubility outcomes.

In summary, the solubility of this compound is expected to be:

  • Variable, depending on the solvent used.
  • Potentially enhanced under basic conditions.
  • Sample-specific, requiring empirical testing for best results.

Understanding these solubility aspects is essential for applications in pharmaceuticals and materials science.

Interesting facts

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

This complex molecule represents a fascinating area of study in both medicinal chemistry and pharmacology. The compound is notable for its structural features that contribute to its biological activity. Here are some intriguing aspects:

  • Structural Diversity: The compound possesses a bicyclic structure, characterized by its unique ring system which is pivotal for its biological interactions.
  • Isomer Variability: With specific stereochemistry denoted by the (2S,5R,6R) configuration, this compound emphasizes the importance of stereochemistry in drug design and efficacy.
  • Isolated Functionalities: The presence of an isoxazole ring contributes to the compound's potential as a pharmacophore, while the carboxylic acid functionality plays a critical role in its interaction with biological targets.
  • Fluorine's Role: The incorporation of fluorine in the aromatic ring is significant as it can enhance the compound's metabolic stability and bioavailability, making it a subject of study in the quest for more effective therapeutic agents.
  • Targeted Applications: This compound may exhibit antimicrobial properties, making it a candidate for research aimed at developing new antibiotics.

In summary, the intricate design and structure of this compound invite extensive research into its potential therapeutic applications. The continuous exploration within the realm of organic chemistry may unveil even more compelling uses for this compound in treating various ailments.

Synonyms
Flucloxacillin
FLOXACILLIN
5250-39-5
Floxapen
Floxacillin [USAN]
Flucloxacilina [INN-Spanish]
Flucloxacilline [INN-French]
Flucloxacillinum [INN-Latin]
3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolylpenicillin
Floxapen (TN)
Floxacillin (USAN)
Flucloxacillin (INN)
Flucloxacillin [INN]
CHEBI:5098
(2S,5R,6R)-6-[[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
EINECS 226-051-0
UNII-43B2M34G2V
FLOXACILLIN [MI]
FLUCLOXACILLIN [MART.]
FLUCLOXACILLIN [WHO-DD]
(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
DTXSID8023056
BRL2039
Fluorochloroxacillin
(2S,5R,6R)-6-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6beta-[3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido]-2,2-dimethylpenam-3alpha-carboxylic acid
Flucloxacilina (INN-Spanish)
Flucloxacilline (INN-French)
Flucloxacillinum (INN-Latin)
FLUCLOXACILLIN (MART.)
MFIPC
flucloxacillina
Flucloxin
Galfloxin
Rimaflox
(2S,5R,6R)-6-(((3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazol-4-yl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-6-((3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-6-(3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
6beta-(3-(2-chloro-6-fluorophenyl)-5-methyl-1,2-oxazole-4-carboxamido)-2,2-dimethylpenam-3alpha-carboxylic acid
Fluclomix-250
Fluclomix-500
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
Zoxin 250
Zoxin 500
DTXCID203056
J01CF05
226-051-0
flucloxacilina
Flucloxacilline
Flucloxacillinum
flucloxacillin sodium
BRL 2039
Flucloxacillin-Sodium
BRL-2039
1847-24-1
43B2M34G2V
6-(3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
Floxacillin sodium anhydrous
Flucloxacillin sodium anhydrous
NSC-277175
6-[3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolecarboxamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Floxapen sodium salt
FK 900 sodium
BRL 2039 sodium
Epitope ID:117416
SCHEMBL3823
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S(2alpha,5alpha,6beta))
CHEMBL222645
GTPL10910
5250-39-5 (acid)
HY-A0246
BDBM50370590
AF45048
DB00301
NCGC00485420-01
(2S,5R,6R)-6-({[3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-[[[3-(2-Chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[[3-(2-chloro-6-fluorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-,(2S,5R,6R)-
DA-63472
NCI60_002254
CS-0017591
NS00081140
D04196
EN300-19766067
Q1994556
BRD-K27871792-001-01-8
BRD-K27871792-236-01-0
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((3-(2-CHLORO-6-FLUOROPHENYL)-5-METHYL-4-ISOXAZOLYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S(2.ALPHA.,5.ALPHA.,6.BETA.))