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Ampicillin

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Identification
Molecular formula
C16H19N3O4S
CAS number
69-53-4
IUPAC name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(1R,2S)-2-(methylamino)-1-phenyl-propan-1-ol
State
State

At room temperature, ampicillin is a solid. It is usually available in the form of a powder for oral suspension and capsules. In its standard form, it can be dissolved in water to make an injectable solution. The state may slightly vary as it is often compounded with other binders or fillers for different pharmaceutical applications.

Melting point (Celsius)
214.00
Melting point (Kelvin)
487.15
Boiling point (Celsius)
295.65
Boiling point (Kelvin)
568.80
General information
Molecular weight
349.40g/mol
Molar mass
349.4040g/mol
Density
1.2800g/cm3
Appearence

Ampicillin typically appears as a white to off-white crystalline powder. It is stable under normal conditions and soluble in water, though it may appear as a suspension when mixed with some liquid formulations. Its precise appearance can vary slightly based on hydration and formulation specifics.

Comment on solubility

Solubility Characteristics

The solubility of the compound (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is influenced by its complex structure and the presence of both polar and non-polar functional groups. Here are some key points to consider:

  • Solubility in Water: This compound may exhibit limited solubility in water due to the presence of hydrophobic groups, particularly the phenyl and thia moieties.
  • Solubility in Organic Solvents: It is likely more soluble in organic solvents such as methanol, ethanol, and dimethyl sulfoxide (DMSO) because these solvents can interact favorably with its non-polar characteristics.
  • pH Dependence: The carboxylic acid group in the structure can influence solubility based on pH. In alkaline conditions, it ionizes, which may enhance its solubility in water.

On the other hand, the second component of the compound, (1R,2S)-2-(methylamino)-1-phenyl-propan-1-ol, also shows interesting solubility traits:

  • Water Solubility: This compound is likely to have moderate solubility in water due to the presence of the methylamino group, which allows for hydrogen bonding with water molecules.
  • Organic Solvents: Similar to the previous compound, it may demonstrate good solubility in organic solvents, benefiting from its hydrophobic phenyl group.

In summary, the solubility of these compounds is largely determined by the balance of their hydrophilic and hydrophobic regions, enhancing their behavior in a variety of solvents, and making it essential to consider solvent selection for applications or formulations.

Interesting facts

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

This intriguing compound is notable for its complex structure, which embodies the principles of stereochemistry beautifully. Here are some fascinating insights:

  • Stereochemical Significance: The configuration of the various chiral centers plays a crucial role in determining the biological activity of the compound. Its specific stereoisomers can lead to different interactions in biological systems.
  • Pharmacological Relevance: This compound belongs to a class of compounds known for their potential therapeutic applications, particularly in the field of antimicrobial agents. Understanding its mechanism of action can pave the way for novel medicinal discoveries.
  • Structural Intricacies: The bicyclic structure contributes to the compound's stability and functionality, making it a key subject of study in synthetic organic chemistry.
  • Thia-Analog Insights: The presence of sulfur in its thiazolidine ring opens avenues for reactivity and modification, contributing to the diversity of scaffolds in drug design.

Biological Implications

With its unique molecular architecture, this compound can interact with various biological targets, influencing pathways related to disease states. Its synthesis and subsequent modifications may lead to derivatives with enhanced efficacy and reduced side effects.

Exploring (1R,2S)-2-(Methylamino)-1-phenyl-propan-1-ol

This compound represents a fascinating study in the world of amines and their derivatives. Here are some critical points about it:

  • Chirality Matters: The presence of chiral centers in this molecule underscores the importance of chirality in medicinal chemistry, affecting both potency and safety profiles.
  • Potential as a Precursor: This amine can serve as a starting material for synthesizing various pharmaceuticals, especially in developing compounds that impact the central nervous system.
  • Structure-Activity Relationships: Researchers often investigate how alterations in structure impact activity, providing valuable insights for future drug design.
  • Cross-Disciplinary Studies: This compound links chemistry with pharmacology and neuroscience, emphasizing the importance of interdisciplinary approaches in modern science.

Applications in Research

The exploration of such compounds is pivotal in advancing our understanding of drug action mechanisms. They offer a promising pathway for developing novel therapeutic agents focused on correcting imbalances in neurotransmitter systems.

Synonyms
Tersavin
7177-45-9
Ephedrine penicillin
Penicillin G ephedrine salt
EINECS 230-538-3
DTXSID10992427
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6- (2-phenylacetamido)-, compd with ephedrine (1:1)
6-[(1-Hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid--2-(methylamino)-1-phenylpropan-1-ol (1/1)