Iupac name for amoxicillin

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.

This lengthy name accurately reflects amoxicillin’s complex chemical structure. Understanding this nomenclature requires familiarity with stereochemistry (indicated by the S and R descriptors) and organic chemistry functional groups. The name clearly identifies the molecule’s key components, including the thiazolidine ring, the β-lactam ring, and the amino-phenyl acetyl side chain responsible for its antibiotic properties.

Note the specific stereochemistry assignments are crucial. These specify the three-dimensional arrangement of atoms, which significantly impacts the biological activity. Slight variations in the arrangement can lead to completely different molecules with different properties.

While the full IUPAC name provides unambiguous identification, simplified names, like amoxicillin, are used for practicality in everyday contexts. However, for precise scientific communication and chemical database searches, the complete IUPAC name remains indispensable.

IUPAC Name for Amoxicillin: A Detailed Explanation

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

This lengthy name precisely describes amoxicillin’s chemical structure. Let’s break it down:

Part of Name	Structural Feature
(2S,5R,6R)	Specifies the stereochemistry at carbons 2, 5, and 6 of the bicyclic ring system. These designations indicate the absolute configuration of the chiral centers.
6-[(R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino	Describes the side chain attached to carbon 6. It indicates an amino group, a 4-hydroxyphenyl group (the para-hydroxybenzene ring), and its attachment to an acetyl group. (R) denotes the stereochemistry at the chiral carbon in this side chain.
3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane	Defines the core bicyclic β-lactam structure. “3,3-dimethyl” indicates two methyl groups on carbon 3. “7-oxo” specifies a carbonyl group (ketone) at position 7. “4-thia-1-aza” denotes a sulfur atom (thia) at position 4 and a nitrogen atom (aza) at position 1. “bicyclo[3.2.0]heptane” describes the seven-membered ring system with two fused rings.
-2-carboxylic acid	Indicates a carboxylic acid group (-COOH) attached to carbon 2 of the bicyclic system, a crucial functional group for its antibiotic activity.

Understanding this detailed nomenclature allows for precise identification and differentiation from other related β-lactam antibiotics. The precise stereochemistry is particularly important as it affects the molecule’s biological activity.

Understanding Chemical Nomenclature

IUPAC nomenclature provides a systematic way to name chemical compounds, avoiding ambiguity. This system uses prefixes, suffixes, and infixes to describe the structure and functional groups present.

Understanding Prefixes and Suffixes

Prefixes indicate the number of carbon atoms (meth-, eth-, prop-, but-, etc.) or substituent groups. Suffixes define the principal functional group, such as –ane (alkanes), –ene (alkenes), –yne (alkynes), –ol (alcohols), –al (aldehydes), –oic acid (carboxylic acids).

• Example: Butane indicates a four-carbon chain with only single bonds.
• Example: Propan-2-ol indicates a three-carbon chain with a hydroxyl group (-OH) on the second carbon.

Applying the Rules: A Step-by-Step Approach

1. Identify the longest continuous carbon chain. This forms the parent name.
2. Number the carbon atoms in the chain, starting from the end closest to the highest priority functional group (e.g., carboxylic acid > alcohol > ketone > alkene > alkane).
3. Name and number any substituent groups attached to the main chain. Use prefixes to indicate the number of each substituent (di-, tri-, tetra-, etc.). Alphabetize the substituents.
4. Combine the substituent names and numbers with the parent name. Numbers are placed before the substituent name and separated by hyphens.
5. If there are multiple same substituents, use prefixes (di, tri, tetra etc.) and commas to separate numbers. Alphabetize the substituents ignoring the prefixes.

Mastering IUPAC nomenclature requires practice and familiarity with functional groups. Practice naming simple compounds, then progress to more complex structures.

The Basic Structure of Amoxicillin

Amoxicillin possesses a core β-lactam ring, a crucial element responsible for its antibiotic activity. Attached to this ring is a thiazolidine ring, contributing to its stability and unique properties. A 6-aminopenicillanic acid (6-APA) structure forms the foundation, with a p-hydroxyphenylglycine side chain differentiating it from other penicillins.

The β-Lactam Ring

This four-membered cyclic amide is the active site, inhibiting bacterial cell wall synthesis. Its strained structure makes it highly reactive, enabling it to bind to penicillin-binding proteins (PBPs) within bacteria.

The Thiazolidine Ring and 6-APA

The fused thiazolidine ring enhances the β-lactam’s stability, protecting it from degradation. The 6-APA structure provides the basic penicillin framework. The specific side chain attached to the 6-APA, the p-hydroxyphenylglycine, determines amoxicillin’s unique characteristics.

p-Hydroxyphenylglycine Side Chain

This side chain significantly impacts amoxicillin’s absorption, distribution, metabolism, and excretion. It also influences its antibacterial spectrum and resistance profile. Its presence distinguishes amoxicillin from other penicillins, modifying its interactions with bacterial targets.

Identifying Functional Groups in Amoxicillin

Amoxicillin possesses several key functional groups. First, locate the β-lactam ring: a four-membered cyclic amide. This ring is crucial for its antibiotic activity.

Next, identify the amino group (-NH₂) attached to the β-lactam ring. This group influences the molecule’s polarity and interactions with biological targets.

Observe the carboxyl group (-COOH). This contributes to amoxicillin’s acidity and its ability to form salts.

Finally, note the hydroxyl group (-OH) and the phenyl group (-C₆H₅). The hydroxyl group influences the molecule’s solubility, while the phenyl group contributes to its overall structure and interactions. Recognizing these key functional groups allows for a thorough understanding of amoxicillin’s properties and mechanism of action.

Applying IUPAC Rules for Naming

Begin by identifying the core structure. Amoxicillin’s core is a 6-aminopenicillanic acid derivative. Next, locate and name the substituents. We have a hydroxyl group at position 6 and an α-amino-p-hydroxyphenylacetyl group attached to the nitrogen atom.

Number the carbon atoms of the β-lactam ring and thiazolidine ring systematically. Remember, IUPAC nomenclature prioritizes seniority of functional groups. The carboxyl group dictates the numbering.

Now, systematically incorporate substituent names and positions into the name. The α-amino-p-hydroxyphenylacetyl group gets its own detailed description: We describe the phenyl ring first (hydroxybenzene), then place the amino group on the alpha carbon (relative to the carbonyl). The complete name reflects these details.

Finally, combine everything to yield the complete IUPAC name. This results in a rather lengthy, yet precise, name reflecting all structural aspects. Precisely following IUPAC guidelines provides unambiguous identification of the molecule.

Step-by-Step Derivation of the IUPAC Name

Let’s systematically derive the IUPAC name for amoxicillin. We’ll break down its structure piece by piece.

1. Identify the core structure: Amoxicillin is a penicillin derivative. Its core is a 6-aminopenicillanic acid.
2. Locate the substituents: Focus on the modifications to the 6-aminopenicillanic acid core. We see an α-amino group and a p-hydroxyphenyl acetyl group at position 6.
3. Name the substituents:
   • The α-amino group is simply ‘amino’.
   • The p-hydroxyphenyl acetyl group requires more attention. It’s a phenyl ring with a hydroxyl group at the para position, attached to an acetyl group (-COCH₃).
4. Assemble the name: We systematically name the substituents and their position on the core structure. The acetyl group is considered the main part of the side chain, so the phenyl group acts as a substituent on the acetyl group. Combining all the components, we get (2S,5R,6R)-6-[(R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.
5. Consider stereochemistry: Amoxicillin possesses several chiral centers, requiring stereochemical descriptors (R/S) to fully specify its configuration in the IUPAC name. These are incorporated into the complete name in the previous step.

This step-by-step process clarifies the systematic approach to naming complex molecules like amoxicillin, according to IUPAC rules.

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 chemical structure, detailing the stereochemistry at each chiral center and the arrangement of its functional groups. Understanding this nomenclature requires familiarity with IUPAC rules for naming organic compounds, particularly those concerning stereochemistry and bicyclic systems. The name incorporates prefixes and suffixes that indicate the presence of specific groups (amino, hydroxyl, carboxyl, etc.), the number of atoms in each ring, and their spatial orientation.

Note the “(2S,5R,6R)” prefix which indicates the absolute configuration of the three chiral carbon atoms within the molecule. These details are critical for distinguishing amoxicillin from its isomers, which may possess different biological activities.

While this full name is comprehensive, the simplified name “amoxicillin” is used in practical settings for convenience. However, for precise chemical communication, particularly in research contexts, the complete IUPAC name is necessary.

Common Misconceptions about the IUPAC Name

The IUPAC name for amoxicillin is quite lengthy and complex, leading to frequent misunderstandings. Many believe a single, universally accepted IUPAC name exists. This is incorrect. Different nomenclature systems yield slightly different, yet equally valid, names. You might encounter variations depending on the database or textbook consulted.

Dealing with Variations

One common source of confusion stems from the different ways chemists represent the stereochemistry of amoxicillin. Minor differences in how the absolute configuration of chiral centers is displayed can result in seemingly distinct IUPAC names. These variations are technically correct and represent the same molecule. Focus on the core structural elements: the 6-aminopenicillanic acid core and the p-hydroxyphenylglycine side chain. If the core structure is consistent, minor variations in IUPAC name presentation usually don’t signify a different compound.

Simplified vs. Complete Names

Another misconception involves the level of detail in the name. Some sources provide highly detailed names encompassing every substituent and stereochemical descriptor, while others present a more simplified version. A simplified name might omit some less relevant details while still accurately describing the compound. Context is key; a simplified name is perfectly acceptable in certain scenarios. Always consider the purpose of the name; a highly detailed name might be necessary for precise chemical synthesis, but a simpler name suffices for general identification.

Practical Applications of Knowing the IUPAC Name

Knowing 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 amoxicillin provides several benefits. First, it ensures unambiguous identification. This precision avoids confusion with similar-sounding drugs or variations in commercial names across different regions.

Pharmaceutical Research & Development

Precise nomenclature is critical in pharmaceutical research. Researchers use IUPAC names in databases and publications, facilitating accurate data analysis and collaboration. This precise naming is fundamental for documenting drug synthesis, purity testing, and stability studies. Incorrect nomenclature can lead to irreproducible results and even safety hazards.

Regulatory Compliance

Regulatory agencies, such as the FDA and EMA, require precise chemical nomenclature in drug registration documents. Using the IUPAC name ensures compliance and avoids potential delays or rejections. This accurate naming allows for transparent communication and streamlined approvals across jurisdictions.

Intellectual Property

Accurate IUPAC names are central to patent applications. Precise chemical descriptions are crucial for distinguishing new drugs from existing ones, protecting intellectual property rights and preventing patent disputes. This specificity helps companies secure exclusive rights to their innovations.