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Amoxicillin

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Identification
Molecular formula
C16H19N3O5S
CAS number
26787-78-0
IUPAC name
(6R,7R)-3-(acetoxymethyl)-7-[[(2R)-2-amino-2-phenyl-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
State
State

At room temperature, amoxicillin is typically found in a solid state as it is commonly formulated in tablets or capsules for oral administration. It can also be formulated as a powder for suspension in liquid.

Melting point (Celsius)
200.00
Melting point (Kelvin)
473.15
Boiling point (Celsius)
220.00
Boiling point (Kelvin)
493.15
General information
Molecular weight
365.40g/mol
Molar mass
365.4030g/mol
Density
1.3000g/cm3
Appearence

Amoxicillin typically appears as a white to off-white crystalline powder. It is slightly soluble in water and has no odor.

Comment on solubility

Solubility Insights for (6R,7R)-3-(acetoxymethyl)-7-[[(2R)-2-amino-2-phenyl-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

The solubility of (6R,7R)-3-(acetoxymethyl)-7-[[(2R)-2-amino-2-phenyl-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid can be considered in various contexts:

  • Polarity: The presence of functional groups such as carboxylic acids and acetoxymethyl may enhance solubility in polar solvents.
  • Hydrogen Bonding: Due to its amino and carboxylic acid groups, this compound can engage in hydrogen bonding, which typically increases solubility in water.
  • pH Influence: Solubility is likely to vary with pH; in more acidic conditions, the carboxylic group may remain protonated, affecting solubility.
  • Solvent Compatibility: While it may dissolve well in polar solvents, its behavior in non-polar solvents could be quite different, reflecting a low solubility.
  • Temperature Effects: Increasing the temperature may improve solubility, a common trait for many organic compounds.

In summary, understanding the solubility of this compound involves examining factors such as polarity, interaction with solvents, and environmental conditions. As with many complex organic molecules, the interplay of these factors plays a critical role in determining the solubility profile.

Interesting facts

Interesting Facts about (6R,7R)-3-(Acetoxymethyl)-7-[[2R)-2-amino-2-phenyl-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

This complex compound boasts a rich tapestry of attributes that make it fascinating to chemists and pharmacologists alike. Often noted for its intricate structure, the compound belongs to a class of beta-lactam antibiotics, which are crucial in medical science for combating bacterial infections. Here are some key aspects that highlight its significance:

  • Antibiotic Properties: This compound exhibits robust activity against a variety of Gram-positive bacteria, making it a potential candidate in the fight against antibiotic-resistant strains.
  • Structural Complexity: The bicyclic structure, featuring a thiazolidine ring, along with the acetylamino side chain, contributes to its biological activity and specificity.
  • Mechanism of Action: It works by inhibiting the synthesis of bacterial cell walls, a vital process for the growth and replication of bacteria, effectively halting infections.
  • Research and Development: Ongoing studies are aimed at optimizing its efficacy and reducing side effects, showcasing the importance of medicinal chemistry in drug development.
  • Historical Context: The discovery of beta-lactam antibiotics revolutionized the treatment of bacterial infections since the mid-20th century, saving countless lives.

In the words of renowned scientist Paul Ehrlich, “The future лечит” – which translates to "The future heals." The ongoing exploration of compounds like this one exemplifies the potential impact of chemistry on global health and medicine. As research progresses, we uncover more about how such compounds can be tailored for optimal therapeutic effects while minimizing risks, thus continuing the legacy of innovation in pharmaceutical sciences.

Synonyms
Cefaloglycin
CEPHALOGLYCIN
Cephaloglycine
D-Cephaloglycine
Cephaoglycin acid
Cefaloglycine
Cephaloglycin anhydrous
Cefaloglicina
3577-01-3
Cefaloglycinum
Kefglycin
D-(-)-Cephaloglycin
Kafocin
Lilly 39435
7-(D-alpha-Aminophenyl-acetamido)cephalosporanic acid
7-(2-D-alpha-Aminophenylacetamido)cephalosporanic acid
Cefaloglycine [INN-French]
Cefaloglycinum [INN-Latin]
Cefaloglicina [INN-Spanish]
Kefocin
CHEBI:34613
HD2D469W6U
Cefaloglycin dihydrate
Cephaloglycin anhdyous
HSDB 3214
EINECS 222-696-7
UNII-HD2D469W6U
7-(D-2-Amino-2-phenylacetamido)-3-acetoxymethyl-delta(sup3)-cephem-4-carboxylic acid
7-(2-Amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid acetate (ester)
DTXSID4022781
7-(D-2-Amino-2-phenylacetamido)-3-acetoxymethyl-delta(sup 3)-cephem-4-carboxylic acid
3-((Acetyloxy)methyl)-7-((aminophenylacetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-((aminophenylacetyl)amino)-8-oxo-, (6R-(6alpha,7beta(R*)))-
7-(2-Amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)octane-2-carboxylic acid, acetate inner salt
Cefaloglycine (INN-French)
Cefaloglycinum (INN-Latin)
Cefaloglicina (INN-Spanish)
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-, acetate (ester), D-
3-acetoxymethyl-7beta-[(2R)-2-amino-2-phenylacetamido]-3,4-didehydrocepham-4-carboxylic acid
(6R,7R)-3-(acetoxymethyl)-7-{[(2R)-2-amino-2-phenylacetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7-((R)-2-AMINO-2-PHENYLACETAMIDO)-3-(HYDROXYMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID ACETATE (ESTER)
(6R,7R)-3-(acetoxymethyl)-7-(((2R)-2-amino-2-phenylacetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
3-acetoxymethyl-7beta-((2R)-2-amino-2-phenylacetamido)-3,4-didehydrocepham-4-carboxylic acid
7-(D-alpha-Aminophenylacetamido)-cephalosporanic acid dihydrate
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid, 3-((acetyloxy)methyl)-7-((aminophenylacetyl)amino)-8-oxo-, (6R-(6alpha,7beta(R*))), dihydrate
DTXCID402781
7-(D-ALPHA-AMINOPHENYLACETAMIDO)CEPHALOSPORANIC ACID
222-696-7
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-((AMINOPHENYLACETYL)AMINO)-8-OXO-, (6R-(6AL///
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(2-AMINO-2-PHENYLACETAMIDO)-3-(HYDROXYMETHYL)-8-OXO-, ACETATE (ES///
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-((AMINOPHENYLACETYL)AMINO)-8-OXO-, (6R-(6alpha,7beta(R*)))
39435
7-(2-amino-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo
Cefaloglycin (JAN)
Cefaloglycin [INN]
(6R,7R)-3-(acetyloxymethyl)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cephaloglycin dihydrate
CEG
CEFALOGLYCIN [JAN]
(6R,7R)-3-[(acetyloxy)methyl]-7-[(2R)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,3-[(acetyloxy)methyl]-7-[[(2R)-aminophenylacetyl]amino]-8-oxo-,(6R,7R)-
CEPHALOGLYCIN [MI]
Epitope ID:174844
SCHEMBL2947
CEPHALOGLYCIN [HSDB]
CEFALOGLYCIN [WHO-DD]
CHEMBL1200971
GTPL12193
DB00689
NCGC00521078-02
(6R,7R)-3-[(acetyloxy)methyl]-7-{[(2R)-2-amino-2-phenylacetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
DA-62180
HY-16137
CS-0006156
NS00011574
D01949
EN300-19734691
Q5057214
7-(2-AMINO-2-PHENYLACETAMIDO)-3-(HYDROXYMETHYL)-8-OXO-5 -THIA-1-AZABICYCLO
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-((AMINOPHENYLACETYL)AMINO)-8-OXO-, (6R-(6.ALPHA.,7.BETA.(R*)))