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Ketorolac is a nonsteroidal anti-inflammatory drug (NSAID) that is widely used for the management of moderate to severe pain in different medical applications. The chemical structure of Ketorolac is derived from pyrrolizine carboxylic acid, which is composed of two chiral centers. The drug is available in injectable and oral forms, and it is used for analgesia, anti-inflammatory, and antipyretic purposes. Ketorolac’s mechanism of action involves inhibition of COX-1 and COX-2, which suppresses prostaglandin synthesis that causes swelling, fever, and pain.

Ketorolac Chemical Structure

The chemical structure of Ketorolac contains a pyrrolizine ring in the middle, which is a 6-membered ring with one nitrogen and one carbonyl group attached to the side chain. The side chain possesses an enolic carboxylic acid moiety that is crucial for the drug’s activity and interaction with COX enzymes. The enolic carboxylic acid moiety is responsible for Ketorolac’s acidity and determines the drug’s solubility and chemical reactivity.

Ketorolac Synthesis and SAR Analysis

Ketorolac is synthesized by reacting α,2-dimethyl-3-benzoylbenzeneacetic acid with 2-amino-2-(hydroxymethyl)-1,3-propanediol in the presence of potassium carbonate. The reaction yields 5-(aminomethyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, which is then acetylated with acetic anhydride to obtain Ketorolac.

The structure-activity relationship (SAR) analysis of Ketorolac suggests that the drug’s potency and selectivity are determined by the chemical structure of the side chain. The carboxylic acid moiety promotes the drug’s interaction with COX enzymes, while the benzoyl group enhances the drug’s lipophilicity and penetration into tissues. The presence of a methyl group on the pyrrolizine ring’s nitrogen atom increases the drug’s selectivity for COX-1 over COX-2. The substitution of the benzoyl group with a halogen atom reduces the drug’s potency, while the replacement of the pyrrolizine ring with a cyclooxygenase inhibitor template decreases the drug’s selectivity.

Ketorolac is a potent and effective NSAID that offers a wide range of therapeutic benefits. The drug’s chemical structure determines its potency and selectivity, and its mechanism of action involves the suppression of prostaglandin synthesis. Ketorolac is available in injectable and oral forms, and it is widely used for the treatment of moderate to severe pain.

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