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Amoxicillin

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Identification
Molecular formula
C16H19N3O5S
CAS number
26787-78-0
IUPAC name
(2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
State
State

At room temperature, amoxicillin is a solid in the form of a crystalline powder.

Melting point (Celsius)
158.00
Melting point (Kelvin)
431.00
Boiling point (Celsius)
597.20
Boiling point (Kelvin)
870.40
General information
Molecular weight
365.40g/mol
Molar mass
365.4040g/mol
Density
1.6000g/cm3
Appearence

Form: Crystalline powder

Color: White to off-white

Comment on solubility

Solubility of (2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]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-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid can be influenced by a variety of factors, including:

  • Molecular Structure: The presence of various functional groups and the overall 3D orientation contribute significantly to how well the compound can dissolve in solvents.
  • Polarity: This compound likely exhibits polar characteristics due to the amino and carboxylic acid groups, which can enhance solubility in polar solvents such as water.
  • Hydrogen Bonding: The potential for hydrogen bonding with water molecules may increase its solubility compared to less polar compounds.
  • Temperature: Solubility generally increases with temperature for many compounds, thus altering conditions may yield different results.

However, the specific solubility of this compound may be limited due to factors like:

  • Chemical Stability: Certain structural elements may lead to instability in solution, limiting solubility.
  • Crystallinity: Highly crystalline forms of compounds may dissolve less readily than amorphous forms.

In conclusion, while this compound may possess a decent solubility profile due to its structural features, comprehensive experimental data is essential to accurately define solubility under various conditions. Understanding these nuances reminds us that "solubility is not just a property but an interplay of various chemical phenomena."

Interesting facts

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

This complex compound is a member of the β-lactam antibiotics, a fascinating class of molecules which has transformed the field of medicine. Here are some notable points regarding this compound:

  • Structure Complexity: The compound features a unique bicyclic structure that contributes significantly to its biological activity. Its intricate arrangement showcases the elegance of organic chemistry.
  • Mechanism of Action: Like many β-lactams, this compound may exert its antibacterial effects by inhibiting cell wall synthesis. This prevents the growth and replication of bacteria, making it an essential component of antibiotic therapy.
  • Research Applications: Its role in the study of antibiotic resistance is pivotal. Researchers are investigating various structural modifications to enhance efficacy and combat resistant bacterial strains.
  • Synergistic Effects: The compound's potential for use in combination therapies is an area of active research, exploring how it interacts with other antibiotics for improved therapeutic outcomes.
  • Nomenclature Puzzle: The systematic name of this compound reflects its complex stereochemistry and functional groups, emphasizing the importance of precision in chemical nomenclature.

As a scientist or student, understanding such compounds deepens appreciation for the intricacies of biological systems and the continual evolution of medicinal chemistry. The journey of studying compounds like this can reveal not only their structures but also their profound impacts on healthcare and the mechanisms through which they exert their effects in living organisms.

"In every compound lies a story waiting to be explored."

Synonyms
L-Amoxicillin
26889-93-0
Amoxicillin, L-
UNII-623M8I9SZN
623M8I9SZN
Amoxicillin trihydrate impurity B [EP]
(2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Amoxicillin trihydrate impurity B
DTXSID30181396
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2S)-amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-(p-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-, stereoisomer
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((amino(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta(R*)))-
AMOXICILLIN SODIUM IMPURITY B [EP IMPURITY]
AMOXICILLIN TRIHYDRATE IMPURITY B [EP IMPURITY]
BENZYLPENICILLIN SODIUM IMPURITY C [EP IMPURITY]
BENZYLPENICILLIN POTASSIUM IMPURITY C [EP IMPURITY]
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINO(4-HYDROXYPHENYL)ACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(R*)))-
AMOXICILLIN SODIUM IMPURITY B (EP IMPURITY)
AMOXICILLIN TRIHYDRATE IMPURITY B (EP IMPURITY)
BENZYLPENICILLIN SODIUM IMPURITY C (EP IMPURITY)
BENZYLPENICILLIN POTASSIUM IMPURITY C (EP IMPURITY)
(2S,5R,6R)-6-(((2S)-2-amino-2-(4-hydroxyphenyl)acetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
(2s,5r,6r)-6-{[(2s)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
RefChem:112262
DTXCID40103887
(2S,5R,6R)-6-((S)-2-amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
(2S,5R,6R)-6-[[(2S)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (L-Amoxicillin)
Amoxicillin EP Impurity B
CAS-26787-78-0
Spectrum_000048
Spectrum2_000145
Spectrum3_000300
Spectrum4_000148
Spectrum5_000810
BSPBio_001840
KBioGR_000596
KBioSS_000428
DivK1c_000231
SPECTRUM1500120
SPBio_000250
orb1703737
CHEMBL1367635
SCHEMBL29683845
CHEBI:95232
HMS500L13
KBio1_000231
KBio2_000428
KBio2_002996
KBio2_005564
KBio3_001340
NINDS_000231
HMS1920C17
HMS2091I17
Pharmakon1600-01500120
CCG-38922
NSC755870
AKOS030238945
FA63616
NSC-755870
IDI1_000231
NCGC00016797-01
NCGC00178966-01
CS-0108031
NS00076249
F83935
AB00051914_02
F988681
SR-05000001561
SR-05000001561-1
BRD-K08635111-001-04-8
Q27167062
(2S,5R,6R)-6-((S)-2-Amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (Amoxicillin Impurity)
(2S,5R,6R)-6-((S)-2-Amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid(AmoxicillinImpurity)