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Cloxacillin

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Identification
Molecular formula
C19H17ClN3O5S
CAS number
61-72-3
IUPAC name
(2S,5R,6R)-6-[[3-(2-chlorophenyl)-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, cloxacillin is typically in a solid state, specifically as a crystalline powder.

Melting point (Celsius)
178.00
Melting point (Kelvin)
451.15
Boiling point (Celsius)
186.00
Boiling point (Kelvin)
459.15
General information
Molecular weight
435.88g/mol
Molar mass
435.8840g/mol
Density
1.5000g/cm3
Appearence

Cloxacillin is typically a white to off-white crystalline powder. It may also be found in powdered form for reconstitution or in capsules for oral administration.

Comment on solubility

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

The solubility of the compound C19H17ClN3O5S can be influenced by various factors, including its unique structure and the presence of polar and non-polar functional groups. Here are some key points to consider regarding its solubility:

  • Polarity: The presence of polar groups like carboxylic acid and carbonyls typically enhances solubility in polar solvents, such as water.
  • Hydrophobic Regions: The compound also contains aromatic and isoxazole moieties which may limit its solubility in polar solvents due to hydrophobic interactions.
  • Solvent Dependence: It’s crucial to note that solubility may vary significantly depending on the solvent used; it may exhibit better solubility in organic solvents like ethanol or dimethyl sulfoxide (DMSO).
  • Temperature Influence: Higher temperatures generally increase solubility, allowing for more significant interaction with the solvent molecules.

In summary, while the structural attributes of this compound suggest a potential for solubility in various solvents, the actual solubility profile would need to be evaluated experimentally. Understanding this can provide crucial insights for its applications and formulations.

Interesting facts

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

This compound, often referred to in scientific literature as a novel antimicrobial agent, has garnered attention for its unique structure and potential therapeutic applications. Here are some intriguing facts:

  • Structural Complexity: The intricate arrangement of its bicyclic core and functional groups reflects a sophisticated approach to drug design, demonstrating how modifying small molecular components can yield compounds with distinct biological properties.
  • Potential Antimicrobial Activity: The presence of the isoxazole group is significant because compounds containing this moiety are often known for their antimicrobial activities, making this compound a candidate for further exploration in fighting infections.
  • Chlorophenyl Substitution: The inclusion of a chlorophenyl group is interesting as it can influence the lipophilicity and bioavailability of the compound, affecting how it interacts within biological systems and enhances its antimicrobial properties.
  • Chirality Matters: The indications of specific stereoisomerism (2S, 5R, 6R) highlight the importance of chirality in pharmacodynamics and pharmacokinetics. This particular stereochemistry could substantially affect the efficacy and safety profile of the compound.
  • Research Potential: Ongoing research is likely to explore the mechanisms of action, potential resistance pathways, and the compound's metabolic fate within organisms, which will deepen our understanding of its therapeutic applications.

In conclusion, the compound's multifaceted nature—characterized by its unique architecture and potential therapeutic uses—makes it a fascinating topic within medicinal chemistry. As scientists continue to investigate its properties, we may unearth more about its role in the development of new and effective treatment options.

Synonyms
cloxacillin
61-72-3
Cloxacilina
Cloxacilline
Cloxacillinum
Methocillin S
Syntarpen
Chloroxacillin
Clossacillina
Cloxacillin sodium
Tegopen
BRL 1621
Methylchlorphenylisoxazoryl-penicillin
Cloxacilina [INN-Spanish]
Cloxacilline [INN-French]
Cloxacillinum [INN-Latin]
Clossacillina [DCIT]
(3-(o-Chlorophenyl)-5-methyl-4-isoxazolyl)penicillin
CHEBI:49566
HSDB 3042
UNII-O6X5QGC2VB
O6X5QGC2VB
EINECS 200-514-7
6-(3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid
Cloxacillin (INN)
(2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6-(((3-(2-Chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
CHEMBL891
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(O-chlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-
DTXSID5022853
BRL1621
(2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CLOXACILLIN [INN]
Cloxacilina (INN-Spanish)
Cloxacilline (INN-French)
Cloxacillinum (INN-Latin)
Cloxacillin [INN:BAN]
CLOXACILLIN (MART.)
CLOXACILLIN [MART.]
(2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(3-(o-chlorophenyl)-S-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-
Spectrum 001345
Tegopen (sodium monohydrate)
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
CXN
Orbenin (TN)
MCIPC
cloxacillina
P-25 (sodium monohydrate)
CloxacillinNa
Cloxapen (sodium monohydrate)
BRL-1621 (sodium monohydrate)
(2S,5R,6R)-6-(((3-(2-chlorophenyl)-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-chlorophenyl)-5-methylisoxazole-4-carboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Cloxacillin ,(S)
cloxacillinum natricum
Spectrum_001345
CLOXACILLIN [MI]
Prestwick0_000186
Prestwick1_000186
Prestwick2_000186
Prestwick3_000186
Spectrum2_001143
Spectrum3_000360
Spectrum4_000296
Spectrum5_000783
CLOXACILLIN [HSDB]
Epitope ID:120363
CLOXACILLIN [VANDF]
SCHEMBL2953
BSPBio_000111
BSPBio_002059
CLOXACILLIN [WHO-DD]
KBioGR_000852
KBioSS_001825
DivK1c_000736
SPBio_001065
SPBio_002032
BPBio1_000123
DTXCID502853
GTPL11126
HY-B0466A
KBio1_000736
KBio2_001825
KBio2_004393
KBio2_006961
KBio3_001279
J01CF02
NINDS_000736
BCP24144
BDBM50022788
DB01147
IDI1_000736
(2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-isoxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SBI-0051319.P003
Cloxacillin 1000 microg/mL in Acetonitrile
CS-0028411
NS00000114
C06923
D07733
EN300-708784
Q422219
BRD-K01244426-236-05-5
BRD-K01244426-236-08-9
BRD-K01244426-236-12-1
BRD-K01244426-323-07-7
OXACILLIN SODIUM MONOHYDRATE IMPURITY E [EP IMPURITY]
6-(3-o-Chlorophenyl-5-methylisoxazol-4-ylamido) penicillanic acid
6-(3-o-Chlorophenyl-5-methylisoxazol-4-ylamido)penicillanic acid
(2S,5R,6R)-6-(3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-{[3-(2-Chloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
2,2-dimethyl-6beta-(((5-methyl-3-(2-chlorophenyl)isoxazol-4-yl)carbonyl)amino)penam-3alpha-carboxylic acid
200-514-7
6-{[3-(2-Chloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid