Pharmacophore and polarity of aspirin and ibuprofen?

In summary, the conversation discusses the topic of the pharmacophore of aspirin and ibuprofen, as well as their chemical structures, synthesis, mechanism of action, and side effects. There is also a mention of wanting to know about the polarity of both molecules. It is noted that the functional groups in aspirin are a benzene ring, carboxylic acid group, and ester group, but it is unclear how this relates to the pharmacophore. The attempt at a solution mentions that the acetyl group in aspirin irreversibly inhibits COX 1 and 2, and that ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) and a propionic acid derivative, but
  • #1
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Homework Statement


I need to know the pharmacophore of aspirin (acetylsalicylic acid) and ibuprofen. There is a task where I have to compare these two drugs' structure, synthesis, mechanism of action and side effects.
Specifically, it says to include,
  • "The chemical structure of the drug including the pharmacophore (group of atoms which confers the pharmacological activity)"

Homework Equations


I would also like to know about the polarity of the aspirin molecule, and the ibuprofen molecule.
Information regarding these topics would be greatly appreciated :)

The Attempt at a Solution


I've read that the acetyl group in aspirin attached to the serine active site in the body to irreversibly inhibit COX 1 and 2. I know that the functional groups in aspirin are a benzene ring, carboxylic acid group and an ester group, but I'm not too sure how this relates to the pharmacophore.
I haven't been able to find the pharmacophore of aspirin and ibuprofen with research.
 
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  • #2
I know ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) and is an propionic acid derivative, but I'm not sure how this relates to the pharmacophore either. I would also like to know about the polarity of the aspirin molecule, and the ibuprofen molecule.
 

1. What is a pharmacophore?

A pharmacophore is a molecular framework or pattern that represents the essential structural and chemical features of a molecule that are responsible for its biological activity.

2. How does aspirin and ibuprofen differ in terms of polarity?

Aspirin and ibuprofen have different functional groups, which results in differences in their polarity. Aspirin has a carboxylic acid group, making it more polar than ibuprofen which has a simple alcohol group.

3. How do the pharmacophores of aspirin and ibuprofen contribute to their analgesic effects?

The pharmacophores of both aspirin and ibuprofen contain functional groups that interact with specific receptors in the body, leading to their analgesic effects. Aspirin's pharmacophore contains an acetyl group that inhibits the enzyme cyclooxygenase, while ibuprofen's pharmacophore contains an isobutyl group that blocks the production of prostaglandins.

4. Are there any similarities between the pharmacophores of aspirin and ibuprofen?

Yes, both aspirin and ibuprofen have aromatic rings in their pharmacophores, which contribute to their anti-inflammatory properties by interacting with receptors in the body.

5. How do the pharmacophores of aspirin and ibuprofen affect their side effects?

The pharmacophores of both aspirin and ibuprofen play a role in their side effects. Aspirin's acetyl group can lead to gastrointestinal irritation and bleeding, while ibuprofen's isobutyl group can cause liver and kidney damage. However, the location and strength of these functional groups in the pharmacophores can also determine the severity of these side effects.

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