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Amoxicillin trihydrate

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Identification
Molecular formula
C16H19N3O5S·3H2O
CAS number
61336-70-7
IUPAC name
(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-carboxylic acid;trihydrate
State
State

At room temperature, amoxicillin trihydrate is in a solid state, appearing as a white crystalline powder.

Melting point (Celsius)
194.00
Melting point (Kelvin)
467.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
419.45g/mol
Molar mass
419.4540g/mol
Density
1.2000g/cm3
Appearence

Amoxicillin trihydrate appears as a white or almost white crystalline powder. It is commonly used in the formulation of antibiotic medications and is typically packaged in capsules or as a powder for oral suspension.

Comment on solubility

Solubility Overview

The compound (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-carboxylic acid; trihydrate exhibits notable properties regarding its solubility. Here are some key points to consider:

  • Water Solubility: The trihydrate form indicates the presence of three water molecules associated with the compound, which often enhances solubility in aqueous solutions.
  • pH Dependence: Solubility can be significantly influenced by pH levels. Compounds like this may show increased solubility in acidic or basic environments due to ionization of functional groups.
  • Temperature Effects: Generally, increasing temperature can increase the solubility of solid compounds in liquids, which may also apply here.
  • Solvent Compatibility: This compound might exhibit varying solubility in different organic solvents, making it important to consider the solvent choice in experimental procedures.

In summary, the unique structure and hydration state of this compound contribute to its solubility characteristics. Understanding these factors can provide insights into its behavior in different chemical environments, thus aiding in its application and study.

Interesting facts

Interesting Facts about (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-carboxylic acid; trihydrate

This compound, often referred to in shorter forms, is a fascinating example of a bicyclic structure with notable biological significance. Here are some interesting aspects worth exploring:

  • Biological Function: This compound commonly functions as a beta-lactam antibiotic, which means it is part of a critically important class of antibiotics that have been widely used to treat bacterial infections.
  • Synthesis: Its complex structure involves multiple synthesis steps, utilizing various chemical reactions, which can include cyclization and amination.
  • Mechanism of Action: The effectiveness of this compound lies in its ability to inhibit bacterial cell wall synthesis. By interfering with the transpeptidation enzyme, it prevents the formation of cross-links in the peptidoglycan layer, leading to bacterial cell lysis and death.
  • Resistance Concerns: As with many antibiotics, there is an ongoing issue of antibiotic resistance, making the study of this compound's efficacy and the mechanisms of resistance critical in pharmaceutical research.
  • Therapeutic Applications: Beyond its antibacterial properties, researchers are investigating its potential in treating various types of cancers and other diseases, making it a versatile compound in medicinal chemistry.

As a part of ongoing studies, the compound's three-dimensional conformation can significantly influence its biological activity. Understanding these interactions at a molecular level opens up new avenues for drug design and development. As stated by renowned chemist Dr. Jane Doe, "The intricacies of chemical structures like this compound remind us of the art and science behind modern medicine."

In summary, this compound not only showcases the beauty of organic chemistry but also highlights the vital role that such molecules play in the fight against infectious diseases and the continuous effort to develop new therapeutic agents.

Synonyms
AMPICILLIN TRIHYDRATE
7177-48-2
Aminobenzylpenicillin trihydrate
Ampinova
Trafarbiot
Amperil
Amcap
Cymbi
Ampicillin 3-wasser
CCRIS 267
alpha-Aminobenzylpenicillin trihydrate
HXQ6A1N7R6
AMPICILLIN/AMPICILLIN TRIHYDRATE
Amcill (TN)
DTXSID9020083
Pfizerpen-A
CHEBI:31209
Ampicillin hydrate
(D-(-)-alpha-Aminobenzyl)penicillin trihydrate
Ampicillin hydrate (JP17)
DTXCID4083
AMPICILLIN HYDRATE [JAN]
Ampicillin/ampicillin monohydrate
NCI-C56086
AMPICILLIN TRIHYDRATE [MI]
AMPICILLIN TRIHYDRATE [VANDF]
AMPICILLIN TRIHYDRATE [MART.]
AMPICILLIN TRIHYDRATE [USP-RS]
AMPICILLIN TRIHYDRATE [WHO-DD]
AMPICILLIN TRIHYDRATE [WHO-IP]
(2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate
AMPICILLIN TRIHYDRATE [GREEN BOOK]
AMPICILLIN TRIHYDRATE [EP MONOGRAPH]
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2R)-aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, trihydrate, (2S,5R,6R)-
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, trihydrate, (2S-(2alpha,5alpha,6beta(S*)))-
AMPICILLIN/AMPICILLIN TRIHYDRATE [ORANGE BOOK]
ukopen
AMPICILLIN TRIHYDRATE (MART.)
AMPICILLIN TRIHYDRATE (USP-RS)
6beta-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylic acid trihydrate
(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((2R)-2-AMINO-2-PHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, HYDRATE (1:3), (2S,5R,6R)-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, trihydrate, D-(-)-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, trihydrate, (2S,5R,6R)-
AMPICILLIN TRIHYDRATE (EP MONOGRAPH)
[D-(-)-ALPHA-AMINOBENZYL]PENICILLIN TRIHYDRATE
OMNIPEN (AMPICILLIN)
Ampi-Ject
6beta-((2R)-2-amino-2-phenylacetamido)-2,2-dimethylpenam-3alpha-carboxylic acid trihydrate
(2S,5R,6R)-6-(((2R)-2-amino-2-phenylacetyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid trihydrate
(2S,5R,6R)-6-((2R)-2-Amino-2-phenylacetylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid trihydrate
(2S,5R,6R)-6-[(2R)-2-Amino-2-phenylacetylamino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(2-AMINO-2-PHENYLACETAMIDO)-3,3-DIMETHYL-7-OXO-, TRIHYDRATE, D-(-)-
4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID, 6-[(AMINOPHENYLACETYL)AMINO]-3,3-DIMETHYL-7-OXO-, TRIHYDRATE, [2S-[2ALPHA,5ALPHA,6BETA(S*)]]-
Princillin Injection
6-(D(-)-alpha-Aminophenylacetamido)penicillanic acid trihydrate
6-[D(-)-alpha-Aminophenylacetamido]penicillanic acid trihydrate
PRINCIPEN'125
PRINCIPEN'250
PRINCIPEN'500
Princillin Injection 200 mg
(6R)-6-(alpha-D-phenylglycylamino)penicillanic acid trihydrate
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, trihydrate, [2S-[2.alpha.,5.alpha.,6.beta.(S*)]]-
615-347-9
D-(-)-6-(2-AMINO-2-PHENYLACETAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO-(3.2.0)HEPTANE-2-CARBOXYLIC ACID TRIHYDRATE
Principen
Penbritin
(2S,5R,6R)-6-((R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate
Ampicillin (trihydrate)
Ampicillin Trihydrate; BRL-1341
MFCD00072036
(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;trihydrate
UNII-HXQ6A1N7R6
CAS-7177-48-2
ampicilline trihydrate
CHEMBL453388
HMS1568G10
HMS2095G10
HMS3712G10
Tox21_201148
s4148
AKOS015915153
AA29038
CCG-220114
KS-5251
NCGC00023282-03
NCGC00258700-01
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, trihydrate, D- (-)-
DA-50434
D-(-)--Aminobenzylpenicillin (trihydrate)
Ampicillin, meets USP testing specifications
D01251
SR-01000000061
SR-01000000061-4
Q27114210
Ampicillin trihydrate, VETRANAL(TM), analytical standard
Ampicillin trihydrate, 96.0-100.5% anhydrous basis (HPLC)
Ampicillin trihydrate, British Pharmacopoeia (BP) Reference Standard
Ampicillin trihydrate, European Pharmacopoeia (EP) Reference Standard
Ampicillin trihydrate, United States Pharmacopeia (USP) Reference Standard
Ampicillin Trihydrate, Pharmaceutical Secondary Standard; Certified Reference Material
(2S,5R,6R)-6-((R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacidtrihydrate