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Amoxicillin

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

At room temperature, amoxicillin is typically found in a solid state, most commonly in crystalline powder form or as part of pharmaceutical tablets and capsules.

Melting point (Celsius)
194.50
Melting point (Kelvin)
467.70
Boiling point (Celsius)
307.60
Boiling point (Kelvin)
580.80
General information
Molecular weight
365.41g/mol
Molar mass
365.4050g/mol
Density
1.3000g/cm3
Appearence

Appearance: Amoxicillin is typically found as a white to off-white crystalline powder. It is often formulated as capsules, tablets, or a powder for suspension for pharmaceutical use.

Comment on solubility

Solubility Characteristics

The solubility of the compound 2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenyl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate can be influenced by various factors, including its molecular structure and interactions with solvents.

Key points regarding its solubility include:

  • Polarity: The presence of both hydrophilic (polar) and hydrophobic (non-polar) regions in its molecular structure may lead to variable solubility in different solvents. Compounds like this tend to be more soluble in polar solvents such as water and methanol but may show limited solubility in non-polar solvents.
  • Hydrogen Bonding: The amino group in the structure can participate in hydrogen bonding, enhancing solubility in polar environments.
  • Ionic Interactions: If the compound can ionize, it may exhibit increased solubility in ionic solutions, further influencing its overall solubility behavior.
  • Temperature Dependency: As with many organic compounds, solubility might increase with an increase in temperature, making it important to consider the conditions under which the compound is stored or used.
  • pH Sensitivity: The solubility of this compound could be affected by the pH of the solution due to the protonation or deprotonation of functional groups, particularly the amino group.

In summary, while this compound demonstrates potential solubility in polar solvents, specific conditions such as pH, temperature, and the solvent's ability to interact with the compound's functional groups will significantly influence its overall solubility profile. Understanding these factors is crucial for effectively utilizing the compound in various applications.

Interesting facts

Interesting Facts about 2,2-Dimethylpropanoyloxymethyl (2S,5R,6R)-6-[[ (2R)-2-Amino-2-phenyl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

This compound, often referred to in a more general context due to its lengthy name, is a fascinating example of complex organic chemistry and structure. Its intricate formulation offers significant insight into biochemical interactions and potential applications. Here are some remarkable aspects of this compound:

  • Structure Complexity: The compound features a bicyclic framework, indicative of a sophisticated network of bonds that allows for unique reactivity and biological compatibility.
  • Biological Relevance: Many compounds of this nature are synthesized with the intent to mimic or inhibit biological processes, particularly in the realm of drug development.
  • Chirality: The notation of (2S,5R,6R) highlights the presence of chiral centers, which are crucial for the pharmacological activity of the compound. This chirality can result in different biological responses in living organisms, making stereochemistry a vital aspect of medicinal chemistry.
  • Synthesis Pathways: The syntheses of such compounds typically employ advanced organic synthesis techniques, and their construction can encompass multiple steps involving various reagents and conditions, showcasing the creativity of chemists.
  • Potential Therapeutics: Given its structure, this compound may possess potential therapeutic attributes, possibly acting as an enzyme inhibitor or a substrate for biochemical pathways relevant to disease states.

In summary, the study of this compound unveils possibilities for advancements in medicinal chemistry, particularly in the development of innovative therapeutics. As researchers continue to explore its biological activities and synthetic strategies, it stands as a testament to the intricate beauty and complexity of organic chemistry.

Synonyms
Pivampicillin
Pivaloylampicillin
33817-20-8
Pivampicilina
Pivampicilline
Pivaloyloxymethyl ampicillinate
Pivampicillinum
Ampicillin pivaloyloxymethyl ester
Ampicillin Pivaloyl Ester
2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
MK-191
0HLM346LL7
CHEBI:8255
DTXSID1045459
DTXCID9025459
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (2S-(2alpha,5alpha,6beta(S*)))-
pivampicillina
(((2S,5R,6R)-6-((2R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-yl)carbonyloxy)methyl 2,2-dimethylpropanoate
{[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-2-yl]carbonyloxy}methyl 2,2-dimethylpropanoate
2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-(((2R)-2-amino-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
RefChem:174630
Ester, Ampicillin Pivaloyl
J01CA02
pivampicillin probenate (see probenecid)
251-688-6
Pivampicilina [INN-Spanish]
Pivampicilline [INN-French]
Pivampicillinum [INN-Latin]
Pivampicillin (INN)
PIVAMPICILLIN [INN]
2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Pivampicillin [INN:BAN]
MK 191
Pondocillin (TN)
EINECS 251-688-6
UNII-0HLM346LL7
NCGC00016823-01
CAS-33817-20-8
Prestwick0_001009
Prestwick1_001009
Prestwick2_001009
Prestwick3_001009
PIVAMPICILLIN [MI]
SCHEMBL34182
BSPBio_001137
PIVAMPICILLIN [MART.]
SPBio_003018
PIVAMPICILLIN [WHO-DD]
BPBio1_001251
orb1705386
CHEMBL3182343
GTPL12920
HMS1571I19
HMS2098I19
HMS3715I19
PIVAMPICILLIN [EP MONOGRAPH]
Tox21_110631
AKOS040744713
Tox21_110631_1
CCG-221009
DB01604
NCGC00179290-01
NCGC00179290-03
[(2,2-dimethylpropanoyl)oxy]methyl 6beta-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylate
[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, hydroxymethyl ester, pivalate (ester), D-(-)-
AB00513999
NS00007431
D08396
EN300-24137107
SR-01000872693
Q3122143
SR-01000872693-1
BRD-K32791151-001-04-0
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINOPHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2,2-DIMETHYL-1-OXOPROPOXY)METHYL ESTER (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-
HYDROXYMETHYL D-(-)-6-(2-AMINO-2-PHENYLACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE PIVALATE (ESTER)