Iupac name for amoxicillin

The IUPAC name for amoxicillin is (2S,5R,6R)-6-[(R)-2-amino-2-phenylacetylamino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. This detailed nomenclature precisely describes the molecule’s structure and stereochemistry.

Understanding this name requires familiarity with chemical nomenclature conventions. The various prefixes and suffixes directly correlate to specific functional groups and chiral centers within the amoxicillin structure. For example, “(2S,5R,6R)” specifies the absolute configuration at three chiral carbon atoms. This level of detail is critical for accurate identification and differentiation from similar compounds.

While the full IUPAC name might seem complex, it provides unambiguous identification. This contrasts with the simpler, commonly used name “amoxicillin,” which is sufficient for most practical purposes but lacks the structural detail provided by the IUPAC nomenclature. Remembering the IUPAC name isn’t generally necessary for most healthcare professionals; however, grasping its underlying principles offers valuable insight into the intricacies of drug structure.

IUPAC Name for Amoxicillin: A Detailed Explanation

The IUPAC name for amoxicillin is (2S,5R,6R)-6-[(R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.

Understanding the IUPAC Name

Let’s break down this complex name into manageable parts to understand its structure:

• (2S,5R,6R): These stereochemical descriptors indicate the absolute configuration of the chiral centers within the amoxicillin molecule. They specify the 3D arrangement of atoms around specific carbon atoms.
• 6-[(R)-2-amino-2-(4-hydroxyphenyl)acetamido]: This part describes the side chain attached to the β-lactam ring at position 6. It indicates the presence of an amino group, a 4-hydroxyphenyl group (para-hydroxybenzene), and an acetamide functional group. The (R) descriptor specifies the chirality at the alpha-carbon of the side chain.
• 3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid:
• 3,3-dimethyl: This describes two methyl groups attached to the carbon at position 3.
• 7-oxo: Indicates a ketone functional group (C=O) at position 7.
• 4-thia-1-azabicyclo[3.2.0]heptane: This is the core bicyclic structure. “thia” indicates a sulfur atom, and “aza” indicates a nitrogen atom, embedded within the seven-membered ring system.
• 2-carboxylic acid: A carboxyl group (-COOH) is attached to the carbon at position 2.

Key Structural Features and Their Implications

The IUPAC name precisely reflects the molecule’s structure, highlighting its key features responsible for its antibiotic activity. The β-lactam ring, the thiazolidine ring, and the amino-hydroxyphenyl acetamide side chain are crucial for binding to bacterial enzymes and inhibiting cell wall synthesis.

1. The β-lactam ring is the primary target of bacterial enzymes. Its structural rigidity and reactivity are essential for its biological activity.
2. The thiazolidine ring provides stability and influences the molecule’s interaction with its biological target.
3. The amino-hydroxyphenyl acetamide side chain contributes to the antibiotic’s pharmacokinetic properties (how it is absorbed, distributed, metabolized, and excreted) and its effectiveness against specific bacteria.

Understanding the Amoxicillin Molecule

Amoxicillin, a common antibiotic, boasts a complex but fascinating molecular structure. Let’s explore its key components and how they contribute to its function.

Its core is a 6-aminopenicillanic acid (6-APA) nucleus. This bicyclic β-lactam ring system is the foundation for penicillin-based antibiotics. The β-lactam ring’s strained four-membered structure is crucial for its biological activity – it easily breaks open, interfering with bacterial cell wall synthesis.

• β-lactam ring: The crucial part responsible for inhibiting bacterial growth. Its instability is what makes it effective.
• Thiazolidine ring: The five-membered ring fused to the β-lactam ring. It provides stability and influences the antibiotic’s properties.
• Amino group: Located on the 6-position of the 6-APA nucleus. This group determines amoxicillin’s acidity, affecting its absorption and distribution in the body.
• p-Hydroxyphenylglycine side chain: This crucial addition to the 6-APA nucleus distinguishes amoxicillin from other penicillins. This group impacts the drug’s effectiveness against different bacteria.

The presence of the p-hydroxyphenylglycine side chain enhances amoxicillin’s effectiveness against a broader range of bacteria compared to penicillin G. This is because it improves its stability and ability to penetrate bacterial cell walls.

1. Increased stability means longer shelf life and potentially higher bioavailability.
2. Improved penetration into bacterial cells leads to greater effectiveness against certain strains.

Understanding the precise molecular structure of amoxicillin allows scientists to design more effective antibiotics and explore potential modifications for improved therapeutic outcomes. Researchers are continually investigating new variations of the 6-APA nucleus and different side chains to combat antibiotic resistance. The molecule’s structure is the key to its function and future development.

Identifying Functional Groups in Amoxicillin

Amoxicillin contains several key functional groups. First, we see a β-lactam ring, a four-membered cyclic amide crucial for its antibiotic activity. This ring is directly attached to a thiazolidine ring, a five-membered ring incorporating both sulfur and nitrogen atoms.

A Closer Look at the Substituents

Attached to the β-lactam ring is a p-hydroxyphenyl group, containing a hydroxyl (-OH) substituent on a phenyl ring. This group contributes to amoxicillin’s overall structure and properties. Finally, an amino (-NH2) group is also present on the β-lactam ring, influencing its interactions with biological targets.

Recognizing these functional groups – the β-lactam, thiazolidine, p-hydroxyphenyl, and amino groups – provides a solid foundation for understanding amoxicillin’s chemical properties and biological mechanism.

Applying IUPAC Nomenclature Rules to the Core Structure

Amoxicillin’s core is a 6-aminopenicillanic acid derivative. We begin by identifying the parent structure: penicillin-6-amine. This establishes the base name.

Next, we address the substituents. The 6-amino group remains. The crucial modification is at position 7, where we have a (2S,5R,6R)-2-amino-2-phenylacetyl group. This is a complex substituent, needing its own systematic name.

Step	Description	Result
1	Identify the phenyl acetic acid core	Phenyl acetic acid
2	Add the 2-amino substituent	2-Aminophenyl acetic acid
3	Specify stereochemistry (2S configuration at the chiral carbon)	(2S)-2-Aminophenyl acetic acid

Therefore, the complete IUPAC name incorporates this detailed substituent description. The complete name includes the stereochemical descriptors for all chiral centers in the molecule.

We then combine these parts: (2S,5R,6R)-2-amino-2-phenylacetyl-6-aminopenicillanic acid.

This precise nomenclature uniquely identifies amoxicillin’s structure.

Naming the Substituents on the Core Structure

Begin by identifying the core structure of amoxicillin: 6-aminopenicillanic acid. This provides the base name.

Next, locate and name the substituents attached to this core. The α-amino group on the side chain remains as “amino”.

The crucial substituent is the p-hydroxyphenyl acetyl group. Name this systematically as (4-hydroxyphenyl)acetyl. Note the use of parentheses to clarify the attachment point of the acetyl group.

Combine these components to form the complete IUPAC name, ensuring correct punctuation and order: (4-hydroxyphenyl)acetyl-6-aminopenicillanic acid. This directly reflects the structure’s components.

Remember to apply standard IUPAC nomenclature rules throughout the process. This includes using numerical locants to denote the position of substituents on the ring system, correctly prioritizing functional groups, and utilizing appropriate prefixes and suffixes.

Prioritizing and Ordering Substituents

First, identify all substituents on the parent chain. Then, assign each substituent a priority based on Cahn-Ingold-Prelog (CIP) rules. These rules prioritize substituents based on atomic number; higher atomic number gets higher priority.

When atoms directly attached to the chiral center are identical, examine the next atoms outward until a difference is found. Double and triple bonds are treated as if they were multiple single bonds to the same atom.

Number the parent chain to give the substituents the lowest possible locants. Use the lowest number at the first point of difference if multiple numbering schemes are possible.

List substituents alphabetically, ignoring prefixes like “di-” or “tri-“, but retaining prefixes that denote stereochemistry (R, S). Separate numbers with commas and numbers from letters with hyphens.

Finally, combine the information to write the complete IUPAC name. Consider stereochemistry (R/S or cis/trans) where applicable. Remember prefixes modify the parent chain name, not the substituents.

Example: If you have a substituent with a higher atomic number on the left side of the molecule versus a lower one on the right side, the higher-numbered substituent takes precedence.

Note: For complex molecules, using a systematic approach and carefully applying the CIP rules is crucial for accurate naming.

Combining the Substituent Names with the Core Name

To name amoxicillin using IUPAC nomenclature, we begin with the core penicillin structure, 6-aminopenicillanic acid. We then systematically add the substituent names. Amoxicillin features an α-amino-p-hydroxybenzyl group at position 6. This detailed description helps us avoid ambiguity.

Locant and Substituent Order

The position of the substituent (position 6) is indicated using a locant. The substituent name, “α-amino-p-hydroxybenzyl,” is added before the core name. Alphabetical ordering of substituents within the name is not necessary here because the substituent is attached to a specific position of the parent molecule, dictated by the penicillin structure. This clear positional designation ensures accurate naming.

Therefore, constructing the complete IUPAC name involves carefully combining the locant, the fully described substituent, and the parent structure name. The structure’s complexity requires this precise and detailed approach to avoid confusion. This method accurately reflects amoxicillin’s chemical structure.

The Complete IUPAC Name of Amoxicillin

The complete IUPAC name is quite lengthy: (2S,5R,6R)-6-[(R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.

This name precisely describes amoxicillin’s complex molecular structure. The prefixes (2S,5R,6R) and (R) indicate the stereochemistry at specific chiral centers, crucial for its biological activity. The remaining descriptors identify the various functional groups and the bicyclic ring system forming the core of the amoxicillin molecule. Understanding this detailed nomenclature allows for accurate identification and distinguishes amoxicillin from structurally related compounds.

Note that while this is the complete IUPAC name, simplified or shorthand versions are often used in practice for brevity and ease of communication within the scientific community.

Practical Applications and Importance of the IUPAC Name

Use the IUPAC name, (2S,5R,6R)-6-[(R)-2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, for unambiguous identification in databases, research publications, and pharmaceutical manufacturing.

Pharmaceutical Regulation and Quality Control

Regulatory bodies rely on the IUPAC name to ensure the precise identity of amoxicillin in drug production. This rigorous nomenclature prevents substitution with similar-sounding but structurally different compounds, guaranteeing patient safety and efficacy. Discrepancies lead to immediate rejection of batches.

Precise Communication Among Scientists

The IUPAC name provides a universal language for chemists and researchers globally. This eliminates any ambiguity, streamlining collaboration and the exchange of research data. This precision is vital for efficient clinical trials and drug development. Accurate record-keeping becomes straightforward.

Chemical Synthesis and Patents

Patent applications and chemical synthesis procedures explicitly utilize the IUPAC name. This specificity protects intellectual property and facilitates replication of results. The name guarantees the correct compound is being synthesized and studied, preventing errors and intellectual property disputes.

Data Management and Analysis

Databases containing chemical information, such as PubChem or ChemSpider, utilize the IUPAC name for indexing and searching. This accurate naming system allows scientists to easily locate and analyze data related to amoxicillin, supporting further research and development.