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Cloxacillin

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Identification
Molecular formula
C19H18ClN3O5S1
CAS number
61-72-3
IUPAC name
(2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

Cloxacillin is generally found in a solid state at room temperature, usually supplied in capsule form, or as a lyophilized powder for reconstitution.

Melting point (Celsius)
174.00
Melting point (Kelvin)
447.15
Boiling point (Celsius)
250.00
Boiling point (Kelvin)
523.15
General information
Molecular weight
435.92g/mol
Molar mass
435.9160g/mol
Density
1.3000g/cm3
Appearence

Cloxacillin typically appears as a white to yellowish-white crystalline powder. It is often in the form of a sodium salt, which enhances its solubility in water.

Comment on solubility

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

The solubility of this complex compound can be influenced by various factors, including its structure and functional groups. Understanding its solubility characteristics is essential for applications in pharmaceuticals and biotechnology.

Factors Influencing Solubility

  • Polarity: The presence of polar functional groups, such as carboxylic acids and amines, can enhance the solubility in polar solvents like water.
  • Hydrogen Bonding: This compound may form hydrogen bonds with solvents, further affecting its solubility properties.
  • Molecular Size: Larger molecules often have lower solubility due to increased hydrophobic interactions.

While specific solubility data may be limited, compounds of similar structure typically exhibit moderate solubility in aqueous and organic solvents. For optimal solubility, researchers often explore the following:

  • pH adjustments
  • The use of solubilizing agents
  • Temperature variations

In conclusion, understanding the solubility of (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is crucial for its practical application, particularly in drug formulation and delivery. Consideration of the compound's unique structural features is essential for predicting its solubility behavior.

Interesting facts

Interesting Facts About (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

This compound, often referred to in the field as a member of the class of thia-β-lactams, exhibits some remarkable characteristics that are of great interest in medicinal chemistry. Here are several key points about this intriguing molecule:

  • Biosynthetic Potential: Its complex structure suggests potential biosynthetic pathways, making it a subject of interest for those researching natural product synthesis.
  • Structure-Activity Relationship (SAR): The unique bicyclic framework contributes to its biological activity, making it a prime candidate for studies in pharmacology to understand how structural changes can impact function.
  • Antibacterial Properties: Compounds with similar structures have shown promising antibacterial properties, opening up avenues for developing new antibiotics amidst rising antibiotic resistance.
  • Stereochemistry Importance: The specified stereochemistry (2S, 5R, 6R) plays a crucial role in the biological activity of the compound, as the spatial arrangement of atoms can significantly influence how the compound interacts with biological targets.

The compound's potential as a therapeutic agent makes it an attractive focus for ongoing research. As Dr. Robert H. Grubbs said, “Chemistry is the study of matter, but I prefer to see it as the study of change.” This compound exemplifies that notion, showcasing how even minute alterations in molecular structure can lead to profound changes in activity and application.

In conclusion, the exploration of (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid not only enhances our understanding of complex organic molecules, but also contributes to the greater fight against infectious diseases through potential therapeutic applications.

Synonyms
CYCLACILLIN
ciclacillin
Vastcillin
3485-14-1
Cyclapen
Aminocyclohexylpenicillin
Cyclapen-W
Ciclacilline
Ciclacillinum
Ciclacilina
(1-Aminocyclohexyl)penicillin
6-(1-Aminocyclohexanecarboxamido)penicillanic acid
6-(1-Aminocyclohexylcarboxamido)penicillanic acid
NSC88789
NSC-88789
(2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
DTXSID9022861
CHEBI:31444
72ZJ154X86
DTXCID002861
(2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6beta-(1-aminocyclohexanecarboxamido)-2,2-dimethylpenam-3alpha-carboxylic acid
CICLACILLIN (MART.)
CICLACILLIN [MART.]
(2S,5R,6R)-6-(((1-aminocyclohexyl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2S,5R,6R)-6-((1-Aminocyclohexanecarbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
222-470-8
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((1-aminocyclohexyl)carbonyl)amino)-3,3-dimethyl-7-oxo-,(2S-(2alpha,5alpha,6beta))-
Ciclacillum
Bastcillin
Citosarin
Syngacillin
Ultracillin
Calthor
Vipicil
Wyvital
Orfilina
Wy-4508
Ciclacilina [INN-Spanish]
Ciclacilline [INN-French]
Ciclacillinum [INN-Latin]
Aminocyclohexyl penicillin
Cyclacillin [USAN]
WY 4508
AC 98
Penicillin, (aminocyclohexyl)-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
Ciclacillin [INN]
Cyclacillin (USAN)
Noblicil
Peamezin
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((1-aminocyclohexyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
6-(1-Aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
NCGC00016629-01
CAS-3485-14-1
(2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6-(1-Aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
AC-PC
Vastcillin (TN)
Cyclapen-W (TN)
MLS002694856
EINECS 222-470-8
NSC 88789
WY4508
Cyclacillin [USAN:USP]
BRN 0938663
UNII-72ZJ154X86
CYCLACILLIN [MI]
Prestwick0_001120
Prestwick1_001120
Prestwick2_001120
Prestwick3_001120
CICLACILLIN [JAN]
Ciclacillin (JP18/INN)
CYCLACILLIN [VANDF]
C-12104
SCHEMBL33900
BSPBio_001260
CICLACILLIN [WHO-DD]
SPBio_003120
BPBio1_001385
GTPL4817
CHEMBL1200356
CYCLACILLIN [ORANGE BOOK]
HMS1571O22
Tox21_110534
BDBM50350474
DB01000
NCGC00179238-01
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(1-aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-
DA-70129
HY-16158
NCI60_041965
AB00514059
CS-0006169
D01334
EN300-19766309
Q5119441
BRD-K89046952-001-03-4
WLN: T45 ANV ESTJ F1 F1 GVQ CMV- AL6TJ AZ
(2S,5R,6R)-6-(1-Aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-[(1-aminocyclohexane)amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid