Chemical Structure:
C13H18O2
Mechanism of Action:
Ibuprofen is a non-selective COX inhibitor, which reduces the synthesis of prostaglandins.
Structural Activity Relationship (SAR) of Ibuprofen
1.Propionic Acid Derivative:
Ibuprofen is a derivative of propionic acid, which is critical for its NSAID activity. The carboxylic acid group is essential for binding to the COX enzymes.
2.Isobutyl Group:
The isobutyl group attached to the alpha carbon of the propionic acid is important for the drug's anti-inflammatory activity. Alterations in this part of the molecule can affect the potency and selectivity of the drug.
3.Aromatic Ring:
The presence of an aromatic ring (benzene ring) is a common feature in many NSAIDs, including ibuprofen. Substitutions on this ring can influence pharmacological activity and metabolic stability.
4.Chirality:
Ibuprofen is a chiral molecule, and it is usually administered as a racemic mixture. The S-enantiomer is considered the more active form in terms of COX inhibition.
Synthesis of Ibuprofen
The synthesis of ibuprofen can be represented through the following chemical reaction pathway:
1.Friedel-Crafts Acylation:
Isobutylbenzene + Acetyl Chloride → (AlCl3) → 2-Acetyl-1-methyl-4-isobutylbenzene
2.Conversion to Hydrazide:
2-Acetyl-1-methyl-4-isobutylbenzene + Hydrazine → 2-(4-Isobutylphenyl) propanehydrazide
3.Oxidation:
2-(4-Isobutylphenyl) propanehydrazide → (Oxidizing Agent) → Ibuprofen
This pathway is a simplified representation. In actual synthesis, each step involves specific conditions such as temperature control, use of catalysts, and purification techniques to ensure the production of high-purity ibuprofen.
Uses:
Used for pain relief, anti-inflammatory purposes, and fever reduction. Commonly used in conditions like arthritis, menstrual cramps, and various types of mild to moderate pain.
Side Effects:
Includes gastrointestinal discomfort, potential cardiovascular risks in long-term use, and renal issues.