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Cloxacillin

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Identification
Molecular formula
C19H17Cl2N3O5S
CAS number
61-72-3
IUPAC name
(2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl-isoxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

Cloxacillin is a crystalline solid at room temperature.

Melting point (Celsius)
184.00
Melting point (Kelvin)
457.00
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
435.85g/mol
Molar mass
435.8460g/mol
Density
1.3000g/cm3
Appearence

Cloxacillin is typically found as a white or almost white crystalline powder. It is practically insoluble in water, soluble in methanol, and slightly soluble in ethanol.

Comment on solubility

Solubility of (2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-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 complex organic compounds like (2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl-isoxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid can often be quite variable and is influenced by several factors:

  • Polarity: The presence of functional groups such as carboxylic acids can enhance hydrophilicity, making the compound more soluble in polar solvents like water.
  • Size and structure: Larger molecular frameworks may impede solubility due to steric hindrance, while a more compact structure can improve it.
  • Interactions: Hydrogen bonding capabilities can significantly affect solubility; stronger interactions with the solvent usually result in higher solubility.

Quotes from the literature suggest: “The solubility of a drug in a given solvent is a fundamental property that often determines its bioavailability and therapeutic efficacy.” Therefore, understanding the solubility profile of this compound is crucial.

In conclusion, the solubility of this compound would need to be assessed experimentally to establish its practical applications in pharmaceuticals, as theoretical predictions alone may not capture the full complexity of solute-solvent interactions.

Interesting facts

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

This intriguing compound is part of a class of chemicals that showcase the complexity and beauty of organic synthesis. Its structure reveals several notable aspects:

  • Chirality and Configuration: The specification of (2S,5R,6R) indicates multiple chiral centers, stressing the importance of stereochemistry in biological activity. This stereochemical arrangement affects how the compound interacts with biological targets.
  • Functional Groups: The presence of an isoxazole ring and a carbonyl group signifies potential pharmacological activity. Compounds featuring isoxazole derivatives have been investigated for their medicinal properties, including anti-inflammatory and antimicrobial effects.
  • Hybrid Structure: The bicyclic system (the 1-azabicyclo[3.2.0] framework) enhances the molecular rigidity, often correlating with increased bioactivity. Such bicyclic structures are common in various natural products and pharmaceuticals.

The compound potentially acts as a potent inhibitor or modulator in specific biochemical pathways. The distinctive feature of incorporating a thio- (sulfur-containing) group into the bicyclic system could also influence its interaction with enzymes or receptors, opening pathways for targeted therapeutic uses.

In the broader context of medicinal chemistry, this compound's design exemplifies the delicate balance between molecular complexity and biological efficacy. As a scientist or student, one could explore:

  1. The synthesis process, which might involve multi-step reactions that require a deep understanding of reagents and reaction conditions.
  2. Experimental assays to determine its biological activity, contributing to the fields of drug discovery and development.
  3. Structure-activity relationship (SAR) studies to optimize its pharmacological properties, potentially leading to novel therapeutic agents.

In conclusion, the study of (2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl-isoxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid not only presents unique challenges but also signifies the exciting potential of complex organic molecules in the realm of pharmaceuticals.

Synonyms
dicloxacillin
3116-76-5
Dicloxacycline
Dicloxacilina
Dicloxacilline
Dicloxacilin
Dicloxacillinum
Diclossacillina
Dicloxacilina [INN-Spanish]
Dicloxacilline [INN-French]
Dicloxacillinum [INN-Latin]
Maclicine
BRL 1702
R-13423
Methyldichlorophenylisoxazolylpenicillin
CHEBI:4511
HSDB 3222
UNII-COF19H7WBK
COF19H7WBK
EINECS 221-488-3
3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolylpenicillin
6-(3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-
6-(3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
Dicloxaciclin
DTXSID1022924
Dichloroxacillin
(2S,5R,6R)-6-({[3-(2,6-dichlorophenyl)-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
Dicloxacilina (INN-Spanish)
Dicloxacilline (INN-French)
Dicloxacillinum (INN-Latin)
DICLOXACILLIN (MART.)
DICLOXACILLIN [MART.]
(2S,5R,6R)-6-(3-(2,6-DICHLOROPHENYL)-5-METHYL-4-ISOXAZOLECARBOXAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE
6beta-{[3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl]carboxamido}-2,2-dimethylpenam-3alpha-carboxylic acid
Dicloxacillina
(2S,5R,6R)-6-(((3-(2,6-dichlorophenyl)-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
6beta-((3-(2,6-dichlorophenyl)-5-methyl-1,2-oxazol-4-yl)carboxamido)-2,2-dimethylpenam-3alpha-carboxylic acid
DTXCID202924
J01CF01
221-488-3
Dynapen
Diclossacillina [DCIT]
BRL-1702
(2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-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-(2,6-dichlorophenyl)-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-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
Dicloxacillin [USAN:INN:BAN]
Dicloxacillin (USAN/INN)
Spectrum_000932
Prestwick0_000450
Prestwick1_000450
Prestwick2_000450
Prestwick3_000450
Spectrum2_000981
Spectrum3_000386
Spectrum4_000507
Spectrum5_000869
DICLOXACILLIN [MI]
CHEMBL893
Epitope ID:181860
DICLOXACILLIN [INN]
DICLOXACILLIN [HSDB]
DICLOXACILLIN [USAN]
SCHEMBL23955
BSPBio_000500
BSPBio_002171
DICLOXACILLIN [VANDF]
KBioGR_001053
KBioSS_001412
DivK1c_000658
SPBio_001041
SPBio_002439
DICLOXACILLIN [WHO-DD]
BPBio1_000550
GTPL12261
HY-B1459A
KBio1_000658
KBio2_001412
KBio2_003980
KBio2_006548
KBio3_001391
NINDS_000658
BDBM50350476
AKOS016010072
DB00485
IDI1_000658
(2S,5R,6R)-6-({[3-(2,6-dichlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SBI-0051342.P003
CS-0013566
NS00126885
C06950
D02348
EN300-708779
H37401
Q2313471
BRD-K05673000-236-12-1
BRD-K05673000-323-02-8
BRD-K05673000-323-12-7
3-(2,6-Dichlorophenyl)-5-methyl-4-isooxazolylpenicillin
(2S,5R,6R)-6-[[3-(2,6-dichlorophenyl)-5-methyl1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid